US 20110098384A1

( 19) United Sta tes

( 12) Pa tent Applica tion Publica tion ( 10) Pub. N o. : US 2011/0098384 A1
B lount ( 43) Pub. D a te: Apr. 28, 2011
( 5 4) PROD UCTION OF AMIN O LIGN IN AN D ( 5 2) us . Cl. . . . . . . . . . . . 5 24/35 ; 5 30/5 05 ; 5 30/5 01; 5 27 /400;
AMIN O LIGN IN CELLULOSE RESIN S AN D 5 24/7 2
( 7 6 )
( 21)
( 22)
( 6 3)
( 5 1)
AD HESIVES
Inv entor: D a v id H. B lount; Sa n D ieg o; CA
( Us )
Appl. N o. : 12/6 5 8, 429
Filed: Feb. 12, 2010
Rela ted US. Applica tion D a ta
Continua tion- in- pa rt of a pplica tion N o. 12/5 89, 399;
?led on Oct. 23; 2009.
Publica tion Cla s s i?ca tion
Int. Cl.
C07 G 1/00 ( 2006 . 01)
C08L 97 /00 ( 2006 . 01)
C08L 1/00 ( 2006 . 01)
( 5 7 ) AB STRACT
Fla me reta rda nt a nd W a ter res is ta nt products a re produced
f rom bio- ba s ed ma teria ls s uch a s lig nin cellulos e conta ining
ma teria ls . Th e lig nin cellulos e ma teria ls a re modi?ed by th e
meth od of delig ni?ca tion. Th e meth od of th is inv ention uti
liZ es a n a mino compound in a n a queous s olution to rea ct W ith
th e lig nin in th e lig nin cellulos e a nd th e a mino lig nin a nd
f reed lig nin becomes W a ter s oluble. Th e a mino compound
a ls o rea cts W ith th e non- W a ter s oluble lig nin s till a tta ch ed to
th e cellulos e a nd a ls o to th e cellulos e th a t is produced. Oth er
products a re produced in th is meth od s uch a s ca rboh ydra tes ;
h emi- cellulos e; ros ins ; W a x es ; a lcoh ols a nd oth er products .
Th e a mino lig nin; lig nin; a mino lig nin a nd a mino cellulos e is
rea cted W ith ma ny org a nic a nd inorg a nic compounds s uch a s
a ldeh ydes ; polyis ocya na tes ; epox ies ; polyca rbox ylic a cids ;
v eg eta ble oils a nd ma ny oth er compounds to produce res ins
a nd a dh es iv es W h ich ma y be us ed to produce products s uch a s
molded products ; pa rticleboa rd; plyW ood; AB S; etc. W h ich
a re ?a me reta rda nt a nd W a ter res is ta nt.
US 2011/0098384 A1
PROD UCTION OF AMIN O LIGN IN AN D
AMIN O LIGN IN CELLULOSE RESIN S AN D
AD HESIVES
[ 0001] Th is a pplica tion is a continua tion in pa rt of a pplica
tion Ser. N o. 12/5 89, 399.
TECHN ICAL FIELD
[ 0002] Th e inv ention concerns urea a nd oth er a mino com
pounds utiliz ed in a n a queous s olution to brea k th e lig nin
cellulos e bond a nd rea ct th e a mino compound W ith th e lig nin
a nd W ith th e lig nin a tta ch ed to th e cellulos e to produce a mino
lig nin, a mino cellulos e, lig nin a nd a mino lig nin cellulos e
a long W ith oth er products s uch a s ca rboh ydra tes , h emi- cellu
los e, W a x es , ros ins , a lcoh ols , a g a r a nd oth er products . Th e
a queous s olution conta ining a mino lig nin, lig nin, ca rboh y
dra tes , h emi- cellulos e a nd oth er compounds a re s epa ra ted
f rom th e a mino lig nin cellulos e, a mino cellulos e a nd lig nin
cellulos e by ?ltra tion. Th e a mino lig nin a nd th e oth er W a ter
s oluble compounds in th e a queous s olution ma y be recov ered
by ev a pora ting of f th e W a ter. Th e a mino lig nin a nd lig nin a re
da rk broW n in color a nd a re th ermopla s tic compound W h ich
W ill rea ct W ith ma ny compounds to produce compounds ,
a dh es iv es a nd res inous ma teria ls . Th is inv ention rela tes to a
nov el a nd economica l proces s to brea k th e lig nin cellulos e
bond a nd rea ct th e lig nin W ith th e a mino delig ni?ca tion com
pounds th en rea ct th e a mino lig nin, a mino cellulos e a nd
a mino lig nin cellulos e W ith org a nic a nd inorg a nic com
pounds . Th e a mino compounds a ls o rea cts W ith s ome of th e
lig nin s till a tta ch ed to th e lig nin cellulos e a nd a ls o in th is
proces s s ome lig nin, ch emica lly a ctiv e lig nin cellulos e, ca r
boh ydra tes a nd oth er products a re produced.
B ACKGROUN D
[ 0003] Th e us e of a mino compounds rea cted W ith a lde
h ydes is W ell k noW in th e Art to produce a minopla s ts f or us e
a s a n a dh es iv e a nd res ins but th e a minopla s ts W ill not produce
delig ni?ca tion of th e lig nin f rom lig nin cellulos e pla nts . Th e
nov el proces s of th is inv ention to produce delig ni?ca tion of
lig nin cellulos e pla nts a nd produce a mino lig nin, a mino cel
lulos e a nd a mino lig nin cellulos e, h emi- cellulos e, ca rboh y
dra tes a nd oth er products by th e us e of a mino compounds in
a n a queous s olution a s th e delig ni?ca tion compounds is
nov el. Urea , g ua nidine compounds or combina tion urea a nd
oth er a mino compounds W h en h ea ted in a n a queous s olution
conta ining pa rticles of lig nin cellulos e it produces a delig ni
?ca tion of th e lig nin f rom th e lig nin cellulos e by th e urea
rea cts W ith lig nin a nd W ith s ome of th e a mino compound is
rea cted W ith th e lig nin a tta ch ed to th e lig nin cellulos e to
produce a mino lig nin cellulos e a nd a mino cellulos e. Th ere is
a ls o s ome h emi- cellulos e, ca rboh ydra tes , ros in a nd oth er
compounds f ound in th e a queous s olution conta ining th e
lig nin a nd a mino lig nin. Th e a mino s a lt of lig nin is produced
by th e nov el meth od of mix ing a n a mino compound, pref er
a ble urea a nd/or g ua nidine compounds , in W a ter W ith pa r
ticles of lig nin cellulos e pla nts W h ich is th en s oa k ed a t a mbi
ent tempera ture a nd pres s ure f or 12 to 24 h ours or h ea ted a t
a mbient or elev a ted pres s ure a t 100 deg ree C. to 15 0 deg ree C.
f or 0. 5 to 4 h ours or long er th ereby rea cting th e a mino com
pound W ith lig nin a nd brea k ing th e lig nin cellulos e bond a nd
th e a mino compound rea cts W ith cellulos e a nd th e lig nin th a t
is s till a tta ch ed to th e cellulos e to produce a mino cellulos e
Apr. 28, 2011
a nd a mino lig nin cellulos e. Th e a mino lig nin, ca rboh ydra tes ,
h emi- cellulos e, lig nin a nd oth er compounds a re s oluble in
W a ter a nd is s epa ra ted f rom th e a mino s a lt of lig nin cellulos e,
a mino cellulos e a nd lig nin cellulos e by ?ltra tion. Th e ca rbo
h ydra tes ma y be s epa ra ted f rom th e W a ter s oluble a mino
lig nin a nd lig nin by us ing a n org a nic s olv ent in W h ich th e
a mino lig nin is s oluble a nd th e ca rboh ydra tes a re not.
[ 0004] Th ere a re ma ny pa tents a nd a rticles rela ted to th e us e
of urea f orma ldeh yde combined W ith lig nin s ulf a te a nd Kra f t
lig nin but th e urea is not utiliZ ed f or delig ni?ca tion a s in th is
inv ention. Some pa tents s uch a U8. Pa t. N os . 2, 36 6 , 26 5 ,
2, 6 22, 97 9 a nd 3, 994, 86 0 us e lig nin s ulf ona te a s a n a dditiv e to
a minopla s t a nd ph enopla s ts . I h a v e not f ound a ny a rticle or
pa tents th a t utiliZ e a mino compounds f or delig ni?ca tion a nd
rea ct a n a mino compound to produce a mino lig nin in th e
proces s of delig ni?ca tion. W h en urea is rea cted W ith th e
k noW types of lig nin s uch a s lig nin s ulf ona te, Kra f t lig nin
( a lk a li proces s ) a completely dif f erent s a lt of lig nin is f ormed
s uch a s urea s a lt of lig nin s ulf ona te. Th e Kra f t lig nin h a s to be
modi?ed in order f or it to be ch emica lly a ctiv e.
SUMMARY
[ 0005 ] In one a s pect, th e inv ention compris es th e delig ni
?ca tion of bioma s s cons is ting of lig nin conta ining pla nts by
a n a mino compound s uch a s urea a nd/or g ua nidine com
pounds in a n a queous s olution by th e proces s of th e a mino
compound rea cting W ith th e lig nin in lig nin conta ining pla nts
a nd th e a mino lig nin compounds become W a ter s oluble a nd
th e a mino compound rea ct W ith s ome of th e lig nin s till
a tta ch ed to th e cellulos e a nd cellulos e W h ich is not W a ter
s oluble. In th is delig ni?ca tion proces s th ere a re oth er com
pounds W h ich become W a ter s oluble or s epa ra tes f rom th e
lig nin cellulos e s uch a s ca rboh ydra tes s uch a s g lucos e, a lco
h ols , ros ins , W a x es , g ums , oils , a g a r, turpentine, res ins , rub
ber la tex , dyes , h emi- cellulos e, etc.
[ 0006 ] In a noth er a s pect, th e inv ention compris es th e
ev a pora tion of th e W a ter f rom th e a queous s olution produced
by th e delig ni?ca tion of th e lig nin cellulos e to recov er th e
a mino lig nin, lig nin, ca rboh ydra tes , s ug a rs , h emi- cellulos e
a nd oth er products in th e a queous s olution. Th e ca rboh y
dra tes a nd th e oth er compounds W h ich a re not s oluble in
certa in org a nic s olv ents s uch a s s ome a lcoh ols , a cetones ,
k etones , etc. , a re s epa ra ted f rom th e a mino lig nin, lig nin a nd
oth er compounds W h ich a re s oluble in certa in org a nic s ol
v ents . Th e ca rboh ydra tes a re us ef ul to produce a lcoh ol, a s
ca ttle f eed, etc.
[ 0007 ] In a noth er a s pect, th e inv ention compris es th e rea c
tion of th e a mino lig nin, a mino cellulos e a nd a mino lig nin
cellulos e tog eth er W ith org a nic compound or inorg a nic com
pounds to produce a dh es iv e a nd res ins to us e in th e produc
tion of pa rticleboa rd, plyW ood, OSB a nd oth er W ood prod
ucts .
[ 0008] In a noth er a s pect, th e inv ention compris es th e rea c
tion of W a ter s oluble a mino lig nin W ith org a nic compounds
a nd/or inorg a nic compounds to produce a dh es iv e a nd res ins
to us e in th e production of pa rticleboa rd, plyW ood, W ood
molded products , g lued W ood product, etc.
[ 0009] In a noth er a s pect, th e inv ention compris es th e rea c
tion of th e non- W a ter s oluble a mino lig nin cellulos e a nd
a mino cellulos e W ith org a nic compounds a nd inorg a nic com
pounds to produce a dh es iv e, res ins a nd to brea k doW n th e
a mino lig nin cellulos e, a mino cellulos e a nd lig nin cellulos e
by minera l a cids , by enZ ymes or ba cteria into ca rboh ydra tes
US 2011/0098384 A1
to be us ed f or th e production of a lcoh ol by mea ns of f ermen
ta tion us ing yea s t or oth er meth ods .
[ 0010] In a noth er a s pect, th e inv ention compris es a dding
th e a mino lig nin res ins to lig nin cellulos e pla nts s uch a s
s a W dus t a nd compres s a nd cure th e res in by h ea t a nd/or
ca ta lys t.
[ 0011] Th e obj ect of th is inv ention is to utiliZ e lig nin con
ta ining pla nt f or deli g ni?ca tion of th e lig nin conta ining pla nts
by rea cting W ith a n a mino compound to produce a mino lig
nin, a mino cellulos e a nd a mino lig nin cellulos e th en rea ct
th em W ith a n org a nic or inorg a nic compound to produce
a dh es iv es a nd res ins a nd recov er th e ca rboh ydra tes a nd oth er
products f ound in lig nin cellulos e pla nts .
[ 0012] Th e obj ect of th e pres ent inv ention is to prov ide a
nov el proces s to produce a mino lig nin, a mino cellulos e,
a mino lig nin cellulos e res inous products , ca rboh ydra tes ,
a lcoh ol, ros in, W a x es , h emi- cellulos e, g ums , a g a r, turpentine,
res ins , rubber la tex , dyes , etc. , f rom cellulos e- conta ining
pla nts . Anoth er obj ect is to produce nov el a mino lig nin,
a mino lig nin- cellulos e a nd a mino cellulos e res inous products
W h ich a re h ig h ly rea ctiv e. Still a noth er obj ect is to produce
ca rboh ydra tes W h ich ca n be f ermented to produce eth a nol.
Anoth er obj ect is to produce nov el poly( f urf uryl a lcoh ol
a mino lig nin) , poly( f urf uryl a lcoh ol a mino cellulos e) a nd
poly( f urf uryl a lcoh ol a mino lig nin cellulos e) ) res inous prod
ucts . Still a noth er obj ect is to produce a mino lig nin, a mino
cellulos e a nd a mino lig nin cellulos e res inous product W h ich
W ill rea ct ch emica lly W ith a ldeh ydes to produce nov el poly
( a ldeh yde a mino lig nin cellulos e) , poly( a ldeh yde a mino lig
nin) a nd poly( a ldeh yde a mino cellulos e) res inous products
a nd f oa ms . Anoth er obj ect is to produce a mino lig nin, a mino
cellulos e a nd a mino lig nin cellulos e polymers th a t W ill rea ct
W ith a ldeh yde compounds a nd ph enol compounds to produce
nov el poly( ph enopla s t a mino lig nin) , poly( ph enopla s t a mino
cellulos e) a nd poly( ph enopla s t a mino lig nin cellulos e) res ins
a nd f oa ms . Anoth er obj ect is to produce lig nin cellulos e poly
mers a nd a mino lig nin cellulos e th a t W ill rea ct W ith polyis o
cya na te compounds a nd polyureth a ne prepolymers to pro
duce nov el poly( polyis ocya na te a mino lig nin cellulos e) , poly
( polyis ocya na te a mino cellulos e) a nd poly( ureth a ne a mino
lig nin- cellulos e) res ins a nd cellula r products . Anoth er obj ect
is to produce a mino lig nin, a mino cellulos e a nd a mino lig nin
cellulos e polymers th a t W ill rea ct W ith polyureth a ne prepoly
mers a nd ox ida ted s ilicon compounds to produce nov el poly
( ureth a ne a mino lig nins ilica te) , poly( ureth a ne a mino cellu
los e s ilica te) a nd poly( ureth a ne a mino lig nin cellulos e
s ilica te) res ins a nd cellula r s olid products .
Component A
[ 0013] Suita ble cellulos e- conta ining pla nts include, but a re
not limited to, trees , e. g . , s pruce, pine, h emlock , ?r, oa k , a s h ,
la rch , birch , a s pen, popla r, ceda r, beech , ma ple, W a lnut,
cypres s , redW ood, ch erry, elm, ch es tnut, h ick ory, locus t,
s yca more, tulip, tupelo, butternut, a pple, a lder, ma g nolia ,
dog W ood, ca ta lpa , box W ood, cra bW ood, ma h og a ny, g reen
h ea rt, la nceW ood, letterW ood, mora , prima v era , purpleh ea rt,
ros e. - W ood, tea k , s a tinW ood, ma ng rov e, W a ttle, ora ng e,
lemon, log W ood, f us tic, os a g e ora ng e, s a ppa nW ood, B ra Z il
W ood, ba rW ood, ca mW ood, s a nda lW ood, rubber, g utta , mes
quite, a nd s h rubs , e. g . , olea nder, cypres s , j unipers , a ca nth us ,
pyra ca nth a , lig us trum, la ta na , boug a inv illea , a Z a lea , f eij oa ,
ilex , f us cia , h ibis cus , da tura , h olly, h ydra ng ea , j a s mine, euca
lyptus , cottonea s ter, x ylos ma , rh odeodendron, ca s tor bea n,
eug enia , euonymus , f a ts h edera , a ra lia , etc. , a nd a g ricultura l
Apr. 28, 2011
pla nts , e. g . , cotton, cotton s ta lk s , com s ta lk s , com cobs ,
W h ea t s tra W , oa t s tra W , rice s tra W , ca ne s ug a r ( ba g a s s e) , s oy
bea n s ta lk s , pea nut pla nts , pea v ines , s ug a r beet W a s te, s or
g h um s ta lk s toba cco s ta lk s , ma iZ e s ta lk s , ba rley s tra W , buck
W h ea t s tra W , quinoa s ta lk s , ca s s a ya , pota to pla nts , leg ume
v ines a nd s ta lk s , v eg eta ble inedible portion, etc. , W eeds ,
g ra s s es , v ines , k elp, ?oW ers a nd a lg a e. W ood ?bers a re th e
pref erred lig nin cellulos e conta ining ma teria ls . Th e W a s te
products of a g ricultura l pla nts W h ich conta in cellulos e ma y
be a ir- dried, th en g round into s ma ll pa rticles a nd us ed in th is
inv ention. Commercia l W a s te products conta ining cellulos e,
e. g . , pa per, cotton cloth , ba g a s s e W a llboa rd, W ood products ,
etc. , ma y be us ed in th is inv ention. Lig nin cellulos e- conta in
ing pla nts W h ich h a v e been pa rtia lly decompos ed, s uch a s
h umus , pea t a nd certa in s of t broW n coa l, ma y be us ed in th is
inv ention. Oth er products of lig nin cellulos e conta ining
pla nts ma y be recov ered in th e proces s of th is inv ention s uch
a s W a x es , g ums , oils , s ug a rs , W ood a lcoh ol, a g a r, ros in, tur
pentine, res ins , rubber la tex , dyes , etc. Th e lig nin cellulos e is
utiliZ ed in th e a mount of 5 0 to 100 pa rts by W eig h t pref era ble
in s ma ll pa rticles s uch a s s a W dus t.
Component B
[ 0014] Any s uita ble a mino compound ma y be us ed in th is
inv ention s uch a s urea , th iourea , a lk yl- s ubs tituted th iourea ,
a lk yls ubs tituted urea s , mela mine, a niline, g ua nidine, a mi
nog ua nidine, mela mine cya nura te, biuret, cya nuric a cid,
s cch a rin, urea condens a tes s uch a s urea - cya ndia mide, urea
a minog ua nidine condens a te, urea g ua nidine condens a te, urea
polya mine condens a te, cya melide, urea - mela mine conden
s a te, urea - dicya ndia mide, urea cya nog ua nidine condens a te,
urea cya na te condens a tes a nd a minoph os ph a tes W ith f ree
N H2, s ulf on- a mides , toluene s ulf ona mide, a liph a tic a nd a ro
ma tic polya mines a nd mix tures th ereof . Urea a nd g ua nidines
a re th e pref erred a mino compounds f or delig ni?ca tion of th e
lig nin cellulos e but ma y be utiliZ ed W ith oth er a mino com
pounds . Th e a mino compounds a re utiliZ ed in th e a mount of
10- 100 pa rts by W eig h t W h en us ed a s a delig ni?ca tion com
pound or a s compound to rea ct W ith th e delig ni?ca tion com
pounds of lig nin cellulos e. Urea is th e pref erred a mino com
pound.
Component C
[ 0015 ] W a ter is utiliZ ed in th e delig ni?ca tion proces s a nd
ma y be utiliZ ed in th e a mount of 1 to 5 00 pa rts by W eig h t.
Component D
[ 0016 ] Any s uita ble inorg a nic or org a nic compound in th e
a mount of 25 to 100 pa rts by W eig h t th a t W ill rea ct W ith th e
a mino lig nin, a mino cellulos e, a mino lig nin cellulos e, lig nin,
lig nin cellulos e, cellulos e or ca rboh ydra tes ma y be utiliZ ed in
th is inv ention. Suita ble rea ctiv e compounds include but not
limited to th e f olloW ing compounds :
[ 0017 ] Any s uita ble s a lt f orming compound ma y be us ed in
th is inv ention. Any s uita ble a lk a li compound ma y be us ed in
th is inv ention. Alk a li meta l compounds a re pref erred s uch a s
a lk a li meta l ox ides , a lk a li meta l h ydrox ide, a lk a li meta l s ili
ca tes a nd mix tures th ereof . Mix tures of s odium h ydrox ide
a nd ca lcium h ydrox ide ma y be us ed. Suita ble a lk a li meta l
h ydrox ides include s odium h ydrox ide, pota s s ium h ydrox ide
a nd mix tures th ereof . Sodium h ydrox ide is th e pref erred
a lk a li compound.
US 2011/0098384 A1
[ 0018] Any s uita ble a cidic s a lt f orming compound ma y be
us ed. Suita ble a cidic s a lt f orming compounds include min
era l a cids , org a nic a cid, org a nic a cid h a lides , h ydrog en con
ta ining a cid s a lts , e. g . , s odium h ydrog en s ui a te, pota s s ium
h ydrog en s ulf a te, s odium dih ydro g en ph os ph a te, a mmonium
s ulf a te, a mmonia polyph os ph a te, urea ph os ph a te, mela mine
ph os ph a te a nd mix tures th ereof . Minera l a cids a re pref erred
es pecia lly s ulf uric a cid a nd h ydroch loric a cid.
[ 0019] Any s uita ble a ldeh yde ma y be us ed in th is inv ention,
s uch a s f orma ldeh yde, a ceta ldeh yde, butyl a ldeh yde, ch lora l,
a crolein, f urf ura l, benZ a ldeh yde, crotona ldeh yde, propiona l
deh yde, penta na ls , h ex a na ls , h epta na ls , octa na ls a nd th ere
s imple s ubs titution products , s emi- a ceta te a nd f ull a ceta ls ,
pa ra f orma ldeh yde a nd mix tures th ereof . Compounds con
ta ining a ctiv e a ldeh yde g roups s uch a s h ex a meth ylenetetra
mine ma y be us ed.
[ 0020] Any s uita ble ph enol compound ma y be us ed in th is
inv ention s uch a s ph enol, p- cres ol, o- cres ol, m- cres ol,
cres ylic a cid, x ylenols , res orcinol, ca s h eW nut s h ell liquids ,
a na cordol, p- tert- butyl ph enol, B is ph enol A, creos ote oil, 2, 6
dimeth ylph enol a nd mix tures th ereof . Ph enol is th e pref erred
ph enol compound a nd f orma ldeh yde is th e pref erred a lde
h yde W h en us ed W ith a ph enol compound. Any s uita ble th er
mo s etting ph enol- f orma ldeh yde a nd urea - f orma ldeh yde res
ins ma y be us ed in th is inv ention. Any s uita ble mix ture of th e
a mino compounds a nd ph enol compounds W ith a n a ldeh yde
ma y be us ed in th is inv ention.
[ 0021] Any s uita ble bio ba s ed compounds ma y be us e in
th is inv ention s uita ble bio ba s ed compounds include but not
limited to v eg eta ble oils s uch a s s oy bea n oil, cottons eed oil,
s a f ?oW er oil, pea nut oil, s un ?oW er oil, pea nut oil, ca nola oil,
corn oil, pa lm oil, ra pes eed oil, a nd mix tures th ereof , s oy
protein, s oy milk , lig nin, s odium lig nin s ulf ona te, s odium
cellulos e, h emi- cellulos e, s ug a r, corn s yrup, mola s s es a nd
mix tures th ereof . Any oil- conta ining s eeds nuts a nd k ernels in
W h ich th e oil ca n be remov ed a nd produces s uita ble oil th a t
ca n be us ed in th is inv ention ma y be obta ined f rom a pricot
s tones , a v oca do, biliba ry, bora g e, s ting ing nettle, bea ch nuts ,
copra , ca s h eW nut, ca lendula , g roundnut, s purg e, rubber s eed,
ros e h ip, h emp, h a z elnut, ra s pberry, elderberry, bla ck curra nt,
cof f ee, coria nder, lins eed, ca ra W a y s eed ma ca da mia nut,
a lmonds , melon s eed, poppy, nutmeg , ev ening primros e,
neem s eed, nig er s eed, red pepper, bra Z il nut, pa s s ion f ruit,
peca n, pis ta ch io, s ea buck h orn, mus ta rd s eed, s es a me s eed,
troph o pla nt, toma to s eed, g ra pe s eed, ?a x s eed, W a lnut a nd
citrus s eed. Veg eta ble f a ts a nd proteins ma y a ls o be us ed. Soy
bea n oil a nd modi?ed s oy oil a re pref erred.
[ 0022] Any s uita ble a cid compound, inorg a nic or org a nic,
ma y be us ed, a nd a s a n a cid ca ta lys t, including th os e W h ich
a ls o h a v e a ch a in building f unction s uch a s s ulph urous a cid,
s ulph uric a cid, h ypoph os ph orous a cid, ph os ph inic a cids ,
ph os ph onous a cids a nd ph os ph onic a cid, g lycolic a cid, la ctic
a cid, s uccinic a cid, ta rta ric a cid, ox a lic a cid, ph th a lic a cid,
trimellitic a cid a nd th e lik e. Furth er ex a mples of a cids ma y be
f ound in Germa n Pa tent N o. 1, 17 8, 5 86 a nd in US. Pa t. N o.
3, 480, 5 92. Acids s uch a s h ydroch loric, ?uoroboric a cid,
a mido- s ulph onic a cid, ph os ph oric a cid a nd its deriv a tiv es ,
a cetic a cid, propionic a cid, etc. , ma y be us ed. Inorg a nic
h ydrog en- conta ining s a lts ma y be us ed s uch a s s odium
h ydrog en s ulph a te, pota s s ium h ydrog en s ulph a te, s odium
dih ydrog en ph os ph a te, pota s s ium dih ydro g en ph os ph a te a nd
mix tures th ereof . Th e a cid compounds ma y be us ed to rea ct
W ith th e a lk a li meta l a toms in th e lig nin cellulos e- conta ining
pla nt polymer to produce a s a lt. Th e a cid compounds ma y
Apr. 28, 2011
a ls o be us ed a s a ca ta lys t in th e rea ctions to produce poly
( a minopla s t a mino lig nin cellulos e) a nd poly( a minopla s t
a mino lig nin) res inous products , a nd f oa m poly( ph enopla s t
a mino lig nin cellulos e) res inous products a nd f oa m a nd poly
( a minopla s t a mino lig nin cellulos e ph enopla s t) res inous a nd
f oa med products .
[ 0023] Any s uita ble ox ida ted s ilicon compound ma y be
us ed in th is inv ention s uch a s s ilica , e. g . , h ydra ted s ilica ,
s ilicof ormic a cid, s ilica s ol, etc. , a lk a li meta l s ilica tes , a lk a
line ea rth meta l s ilica tes , na tura l Silica tes W ith f ree s ilicic
a cid g roups a nd mix tures th ereof . Th e h ydra ted s ilica
includes v a rious s ilicon a cids s uch a s s ilicic a cid g el, orth o
s ilicic a cid, ela s ilicic a cid, monos ila ndiol, polys ilicof ormic
a cid, etc. Hydra ted s ilica is th e pref erred ox ida ted s ilicon
compound.
[ 0024] Any s uita ble org a nic polyis ocya na te ma y be us ed
a ccording to th e inv ention, including a liph a tic, cycio
a liph a tic, a ra liph a tic, a roma tic a nd h eterocyclic polyis ocya n
a tes . Suita ble polyis ocya na tes , f or ex a mple, a rylene polyis o
cya na tes s uch a s tolylene, meta ph enylene;
4- ch loroph enylene- 1, 3 - ; meth ylene- bis - ( ph enylene- 4 - ) ;
biph enylene- 4, 4' - ; 3, 3- dimeth yl- ox y- biph enylene- 4, 4' - ; 3, 3'
diph enylbiph enylene- 4, 4' - ; na ph th a lene- 1, 5 - a nd tetra h y
drona ph th a lene- l, 5 - diis ocya na tes a nd triph enylmeth a ne tri
is ocya na te; a lk ylene polyis ocya na tes s uch a s eth ylene,
eth ylidene; propylene- 1, 2- ; butylene- 1, 4- ; butylene- 1, 3- ;
h ex ylene- 1, 6 - ; deca meth ylene- 1, 10; cycloh ex ylene- 1, 2;
cycloh ex ylene- 1, 4- ; a nd. meth ylene- bis - ( cycloh ex yl- 4, 4' - )
diis ocya na tes .
[ 0025 ] It is g enera lly pref erred to us e commercia lly rea dily
a v a ila ble polyis ocya na tes , e. g . , tolylene- 2, 4- a nd - 2, 6 - diis o
cya na te a nd a ny mix tures of th es e is omers , ( TD I ) , polyph e
nyl- polymeth ylene- is ocya na tes obta ined by a niline- f orma l
deh yde condens a tion f olloW ed by ph os g ena tion ( crude
MD I ) , PMD I a nd polyis ocya na tes W h ich conta in ca rbodi
imide g roups , ureth a ne g roups , a lloph a na te g roups , is ocya
nura te g roups , urea g roups , imide g roups or biuret g roups ,
( modi?ed polyis ocya na tes ) . Inorg a nic polyis ocya na tes a re
a ls o s uita ble a ccording to th e inv ention. Suita ble polyis ocy
a na tes W h ich ma y be us ed a ccording to th e inv ention a re
des cribed, e. g . , by W . Sief k en in J us tus Liebig s Anna len der
Ch emie, 5 6 2, pa g es 7 5 to 136 .
[ 0026 ] Solutions of dis tilla tion res idues a ccumula ting dur
ing th e production of tolylene diis ocya na te, diph enyl meth
a ne diis ocya na te or h ex a - eth ylene diis ocya na te, in mono
meric polyis ocya na tes or in org a nic s olv ents a nd mix tures
th ereof ma y be us ed in th is proces s . Ph os g ena tion products of
condens a tes of a niline or a nilines a lk yl s ubs tituted on th e
nucleus , W ith a ldeh ydes or k etones , ma y be us ed in th is inv en
tion.
[ 0027 ] Org a nic polyh ydrox yl compounds ( polyols ) a nd
org a nic compounds W ith h ydrox yl ra dica ls ma y be us ed in
th is inv ention or ?rs t rea cted W ith polyis ocya na tes or ma y be
?rs t rea cted W ith a polyis ocya na te to produce is ocya na te
termina ted polyureth a ne prepolymers a nd th en a ls o us ed in
th is inv ention.
[ 0028] Rea ction products of f rom 5 0 to 99 mols of a roma tic
diis ocya na tes W ith f rom 1 to 5 0 mols of conv entiona l org a nic
compounds ma y be us ed.
[ 0029] Th e h ydrox yl g roup conta ining polyes ters ma y be
us ed in th is inv ention, f or ex a mple, rea ction products of poly
h ydric a lcoh ols , pref era bly, dih ydric a lcoh ols , W ith th e
US 2011/0098384 A1
optiona l a ddition of trih ydric a lcoh ols , a nd polyba s ic, pref
era bly diba s ic ca rbox ylic a cid ins tea d of f ree polyca rbox ylic
a cids , th e corres ponding
polyca rbox ylic a cid a nh ydrides or corres ponding polyca r
box ylic a cid es ters of loW er a lcoh ols or th eir mix tures ma y be
us ed f or prepa ring th e polyes ters . Th e polyca rbox ylic a cid
ma y be a liph a tic, cycloa liph a tic, a roma tic a nd/or h eterocy
clic a nd ma y be s ubs tituted, e. g . , W ith h a log en a toms a nd ma y
be uns a tura ted. Ex a mples include: s uccinic a cid, a dipic a cid,
s eba cic a cid, s uberic a cid, a Z ela ic a cid, ph th a lic a cid, ph th a lic
a cid a nh ydride, is oph th a lic a cid, tetra h ydro- ph th a lic a cid
a nh ydride, trimellitic a cid, h ex a h ydroph th a lic a cid a nh y
dride, tetra ch loroph th a lic a cid a nh ydride, endometh ylene tet
ra h ydroph th a lic a cid a nh ydride, g luta ric a cid a nh ydride,
f uma ric a cid, ma leic a cid, ma leic a cid a nh ydride, dimeric a nd
trimeric f a tty a cids s uch a s oleic a cid, optiona lly mix ed W ith
monomeric f a tty a cids , dimeth yltereph th a la te a nd bis - g lycol
tereph th a la te.
[ 0030] Any s uita ble polyh ydric a lcoh ol ma y be us ed s uch
a s , f or ex a mple, eth ylene g lycol; propylene- 1, 2- a nd - 1, 3
g lycol, butylene- 1, 4- a nd - 2, 3- g lycol; h ex a ne- 1, 6 - diol;
octa ne- 1, 8- diol; neopenth l g lycol; cycloh ex a nedimeth a nol
( 1A- bis - h ydrox ymeth ylcyclo- h ex a ne) ; 2 meth yl propa ne- 1,
3- diol; g lycerol; trimeth ylol propa ne; h ex a ne- 1, 2, 6 - triol;
buta ne- 1, 2, 4 triol; trimeth yloleth a ne; penta eryth ritol; quini
tol; a nnitol a nd s orbitol; meth ylg lycos ide; dieth ylene g lycol;
tri- eth ylene g lycol; tetra eth ylene g lycol; polyeth ylene g ly
cols ; dipropylene g lycol; polypropylene g lycols ; dibutylene
g lycol a nd polybutylene g lycols . Th e polyes ters ma y a ls o
conta in a proportion of ca rbox yl end g roups . Polyes ters of
la ctones , s uch a s ca prola ctone, or h ydrox yca rbox ylic a cids
s uch a s co- h ydrox yca proic a cid, ma y a ls o be us ed.
[ 0031] Th e polyeth ers W ith a t lea s t 2, g enera lly f rom 2 to 8
a nd pref era bly 2 or 3, h ydrox yl g roups us ed a ccording to th e
inv ention a re k noW n a nd ma y be prepa red, e. g . , by th e poly
meriZ a tion of epox ides , e. g . , eth ylene ox ide, propylene ox ide,
butyleneox ide, tetra h ydrof ura n, s tyrene ox ide or epich loro
h ydrin, ea ch W ith its elf , e. g . , in th e pres ence of B F- ' or by
a ddition of th es e epox ides , optiona lly a s mix tures or s ucces
s iv ely, to s ta rting components W h ich conta in rea ctiv e h ydro
g en a toms s uch a s a lcoh ols or a mines , e. g . , W a ter, eth ylene
g lycol; propylene- 1, 3 or 1- 2- g lycol; trimeth ylolpropa ne; 4, 4
dih ydrox ydiph enylpropa ne, a niline, a mmonia , eth a nola mine
or eth ylenedia mine. Sucros e polyeth ers ma y a ls o be us ed
a ccording to th e inv ention.
[ 0032] It is f requently pref erred to us e polyeth ers W h ich
conta in predomina ntly prima ry OH g roups , ( up to 90% by
W eig h t, ba s ed on th e tota l OH g roups conta ined in th e poly
eth er) . Poly eth ers modi?ed W ith v inyl polymers s uch a s
th os e W h ich ma y be obta ined by polymeriz ing s tyrene or
a crylonitrile in th e pres ence of , polyeth ers , ( US. Pa t. N os .
3, 383, 35 1; 3, 304, 27 3; 3, 5 23, 093 a nd 3, 110, 6 95 ; a nd Germa n
Pa tent N o. 1, 15 2, 5 36 ) a nd polybuta dienes W h ich conta in OH
g roups a re a ls o s uita ble. B y polyth ioeth ers a re mea nt, in
pa rticula r, th e condens a tion products of th iodig lycol W ith
its elf a nd/or W ith oth er g lycols , di- ca rbox ylic a cids , f orma l
deh yde, a minoca rbox ylic a cids or a mino a lcoh ols . Th e prod
ucts obta ined a re polyth io- mix ed eth ers or polyth io- eth er
es ter a mides , depending on th e co- component. Th e polya c
eta ls us ed ma y be, f or ex a mple, th e compounds W h ich ma y be
obta ined f rom g lycols , e. g . , dieth ylene, trieth ylene g lycol,
4, 4- dih ydrox ydiph enylmeth ylmeth a ne, h ex a nediol, a nd
f orma ldeh yde. polya ceta ls s uita ble f or th e inv ention ma y a ls o
be prepa red by th e polymeriZ a tion of cyclic a ceta ls .
Apr. 28, 2011
[ 0033] Th e polyca rbona tes W ith h ydrox yl g roups us ed ma y
be of th e k ind, e. g . , W h ich ma y be prepa red by rea cting diols ,
e. g . , propa ne- 1, 3- diol; buta ne- 1, 4- diol; a nd/or h ex a ne- 1, 6
diol or dieth ylene g lycol; trieth ylene g lycol or tetra eth ylene
g lycol, W ith dia rylca rbona tes , e. g . , di- ph enylca rbona tes or
ph os g ene.
[ 0034] Th e polyes tera mides a nd polya mides include, e. g . ,
th e predomina ntly linea r condens a tes obta ined f rom polyv a
lent s a tura ted a nd uns a tura ted ca rbox ylic a cids or th eir a nh y
drides a nd polyv a lent s a tura ted a nd uns a tura ted a mino a lco
h ols , dia mines , polya mines a nd mix tures th ereof .
[ 0035 ] Polyh ydrox yl compounds W h ich a lrea dy conta in
ureth a ne or urea g roups , modi?ed or unmodi?ed na tura l poly
ols , e. g . , ca s tor oil, ca rboh ydra tes a nd s ta rch es , ma y a ls o be
us ed. Additiona l products of a lk ylene ox ides W ith ph enol
f orma ldeh yde res ins a re a ls o s uita ble f or th e purpos e of th e
inv ention.
[ 0036 ] If th e polyis ocya na tes or th e prepolymer W h ich con
ta ins N CO g roups h a v e a v is cos ity a bov e 2000 cP a t 25 C, it
ma y be a dv a nta g eous to reduce th e v is cos ity th ereof by mix
ing it W ith a loW - v is cos ity org a nic polyis ocya na te a nd/or a n
inert bloW ing a g ent or s olv ent. Inorg a nic polyis ocya na tes a nd
is ocya na te- termina ted polyureth a ne s ilica te prepolymers
ma y a ls o be us ed in th is inv ention.
[ 0037 ] W h en a n a queous s olution of a mino lig nin or a
mix ture of a mino lig nin a nd a mino lig nin cellulos e polymer is
being us ed to rea ct W ith , or a s a curing a g ent f or, polyis ocy
a na tes , it is a dv a nta g eous in certa in ca s es to us e ca ta lys ts s uch
a s tertia ry a mines , e. g . , trieth yla mine, tributyla mine, N - me
th yl- morph oline, N - eth yl- ra orph oline, tetra meth ylenedi
a mine, penta meth yldieth ylenea mine, trieth a nola mine, triis o
proph a nola mine, org a no- meta llic compound, e. g . , tin
a ceta te, tin octoa te, tin eth yl h ex oa te, dibutyl tin dia ceta te,
di- butyl tin dila ura te a nd mix tures th ereof in th e a mount of
0. 1 to 10 pa rts by W eig h t.
[ 0038] Oth er ex a mples of ca ta lys ts W h ich ma y be us ed
a ccording to th e inv ention a nd deta ils of th eir a ction a re
des cribed in Kuns ts tof f - Ha ndbuch , Volume VII, publis h ed by
VieW eg a nd Hoch tlen, Ca rl- Ha ns er- Verla g , Munich , 196 6 ,
e. g . , on pa g es 96 a nd 102. Sila - a mines a re s uita ble ca ta lys ts ,
e. g . , 2, 2- 4- trimeth yl- 2- s ila morph oline or 1, 3- dieth yl a mi
nometh yl tetra meth yl dis ilox a ne. Suita ble ca ta lys ts a re a ls o
tetra a lk yl a mmonium h ydrox ides , a lk a li ph enola tes , a lk a li
meta l h ydrox ides , a lk a li ph enola tes , a lk a li- a lcoh ola tes a nd
h ex a h ydrotria Z ines .
[ 0039] Suita ble ?a me- res is ta nt compounds ma y be us ed
W h ich conta in h a log en or ph os ph orus , e. g . , tributylph os
ph a te; tris ( 2, 3- dich loropropyl) - ph os ph a te; polyox ypropyle
nech lorometh ylph os ph ona te; cres yldiph enyl- ph os ph a te; tri
cres ylph os ph a te; tris - ( beta - ch loroeth yl) - ph os ph a te; tris - ( 2,
3- dich loropropyl) - ph os ph a te; triph enyl- ph os ph a te;
a mmonium ph os ph a te; perch lorina ted diph enyl; perch lori
na ted tereph enyl; h ex a bromo- cyclodeca ne; tribromoph enol;
dibromopropyldiene; h ex a bromobenZ ene; octa bromodiph e
nyleth er; penta bromotoluol; poly- tribromos tyrol; tris - ( bro
mocres yl) - ph os ph a te; tetra bromobis - ph enol A: tetra bro
moph th a lic a cid a nh ydride; octa bromodiph enyl; tri
( dibromopropyl) - ph os ph a te; ca lcium h ydrog en ph os ph a te;
s odium or pota s s ium dih ydrog en ph os ph a te; dis odium or
dipota s s ium h ydrog en ph os ph a te; a mmonium ch loride;
ph os ph oric a cid; polyv inylch loride tetomers ch loropa ra ?ins
a s W ell, a mino ph os ph orus compounds , a s f urth er ph os ph orus
a nd/or h a log en- conta ining ?a me- res is ta nt compounds a s
th ey a re des cribed, e. g . , in Kuns ts tof f - Ha ndbuch , Volume
US 2011/0098384 A1
VII, Munich 196 6 , pa g es 110- 111, W h ich is incorpora ted
h erein by ref erence. Th e org a nic h a log en- conta ining compo
nents Eire, h oW ev er, pref erred in th e polyureth a ne- cellulos e
a nd polyureth a ne- cellulo s e- s ilica te cellula r s olid products . In
th e production of a mino lig nin a ldeh yde, a mino lig nin cellu
los e a ldeh yde a nd ph enol- a mino lig nin a ldeh yde a nd a mino
lig nin cellulos e cellula r s olid products , ph os ph oric a cid ma y
be us ed to rea ct W ith th e a mino a toms , th ereby producing a n
a mino h ydrog en ph os ph a te W h ich ma y be. us ed a s th e ?a me
res is ta nt compound. Alk a li meta l s ilica tes ma y be us ed a s
?a me- res is ta nt compounds .
[ 0040] Any s uita ble W a ter- binding a g ent ma y be us ed in
th is inv ention s uch a s h ydra ulic cement, burnt lime, g yps um
a nd s ynth etic a nh ydrites . Hydra ulic cements s uch a s Portla nd
cement, quick - s etting cement, morta r cement, bla s t- f urna ce
Portla nd cement, s ulph a te- res is ta nt cement, brick cement,
mild- bumt cement, na tura l cement, lime cement, g yps um
cement, ca lcium s ulf a te cement, poZ Z ola n cement, etc. , con
ta in ox ida ted s ilicon compounds a nd ma y be us ed in th is
inv ention. Th ere a re ma ny dif f erent k inds of cement W h ich
ma y be us ed; in g enera l, a ny mix ture of ?ne g round lime,
a lumina a nd s ilica th a t W ill s et to a h a rd product by a dmix ture
of W a ter W h ich combines ch emica lly W ith th e oth er ing redi
ents to f orm a h ydra te ma y be us ed. Th e a bov e s uita ble
compound ma y be us ed a s a mix ture th ereof .
[ 0041] An a dditiona l pref erred proces s , a bout 0. 5 to 5 pa rts
by W eig h t of a n a ldeh yde a re mix ed a nd rea cted W ith 1 pa rt by
W eig h t of th e mix ture of a mino lig nin, lig nin, a mino cellulos e
a nd a mino lig nin cellulos e res inous products , produced in th is
inv ention, th e rea ction ma y ta k e pla ce in a n a queous s olution
a t a pH of 0. 8 to 10 or a pH of 3 to 7 , to produce poly( a ldeh yde
a mino lig nin) , poly( a ldeh yde a mino cellulos e) , poly( a lde
h yde lig nin) a nd poly( a ldeh yde a mino lig nin cellulos e) res
inous product.
[ 0042] In a n a dditiona l pref erred proces s , 0. 5 to 5 pa rts by
W eig h t of a n a ldeh yde, 1 to 5 pa rts by W eig h t of a n a mino
compound, a nd 4 pa rts by W eig h t of th e mix ture of a n a mino
lig nin cellulos e, a mino cellulos e, a mino lig nin, lig nin, a nd
lig nin cellulos e, produced by th e proces s of th is inv ention, a re
mix ed a nd th e res ulta nt mix ture is rea cted, th e rea ction ma y
ta k e pla ce in a n a queous s olution W ith a pH of 8 to 10 or a pH
of 3 to 7 , th ereby producing a poly( a ldeh yde- a mino lig nin
cellulos e a mino lig nin a mino cellulos e) res inous product.
W h en s a W dus t utiliZ ed a s th e lig nin cellulos e a nd in th is
meth od of delig ni?ca tion th e products produced a re rea cted
W ith f orma ldeh yde in a n a queous medium W ith pH 8- 10, a
th ermopla s tic res in is produced th en th e rema ining lig nin
cellulos e a nd mois t res in is mix ed W ith a a cidic compound
a nd poured into a mold th en cured by h ea t to f orm a W a ter
res is ta nt a nd ?a me reta rda nt pa rticle boa rd.
[ 0043] In a n a dditiona l pref erred proces s , 0. 5 to 5 pa rts by
W eig h t of a ph enol compound, 0. 5 to 5 pa rts by W eig h t of a n
a ldeh yde a nd 2 pa rts by W eig h t of th e a mino lig nin res inous
product produced by th e proces s of th is inv ention a re mix ed
a nd th e res ulta nt mix ture is rea cted, th e rea ction ma y ta k e
pla ce in a n a queous s olution W ith a pH of 8 to 12 or a pH of 3
to 7 , th ereby producing a poly( a ldeh yde- ph enol- a mino lig
nin) res inous product.
[ 0044] In a n a dditiona l pref erred proces s , 0. 5 to 5 pa rts by
W eig h t of a t lea s t one th ermos etting res in of th e cla s s cons is t
ing of th e th ermos etting urea f orma ldeh yde res ins a nd
mela mine- f orma ldeh yde res ins , 2 pa rts by W eig h t of th e
a mino lig nin res inous product produced in th is inv ention a nd
5 pa rts by W eig h t of s ilica a re mix ed th en rea cted under, h ea t
Apr. 28, 2011
( 220 to 300 F) a nd pres s ure ( 15 0 to 25 0 ps i) f or 1 to 10
minutes th ereby producing a n a minopla s t a mino lig nin s ili
ca te res inous product.
[ 0045 ] In a n a dditiona l pref erred proces s , 0. 5 to 5 pa rts by
W eig h t of a th ermos etting ph enol- a ldeh yde res in s elected
f rom th e g roup cons is ting of ph enol- f orma ldeh yde res in,
ph enol- res orcinol- f orma ldeh yde res in, res orcinol- f orma lde
h yde res in a nd mix tures th ereof a nd 2 pa rts by W eig h t of
a mino lig nin res inous product a s produced in th is inv ention
a re mix ed a nd rea cted by h ea t ( 220 F to 300 F) a nd pres s ure
( 15 0 to 25 0 ps i) f or 1 to 10 minutes th ereby producing a
ph enopla s t a mino lig nin res inous product. Pa ra f orma ldeh yde
ma y a ls o be a dded W ith th e th ermos etting ph enol- a ldeh yde
res in in a n a mount of 0. 5 to 3 pa rts by W eig h t.
[ 0046 ] In a n a dditiona l pref erred proces s , 0. 5 to 5 pa rts by
W eig h t of a n a ldeh yde, 1 to 5 pa rts by W eig h t of a n a mino
compound, 1 to 5 pa rts by W eig h t of a ph enol compound a nd
tW o pa rts by W eig h t of th e a mino lig nin res inous product,
produced by th e proces s of th is inv ention, a re mix ed; th e
res ulta nt mix ture is rea cted, th e rea ction ma y ta k e pla ce in a n
a queous s olution W ith a pH of 8 to 12 or a pH of 3 to 7 , th ereby
producing a ph enopla s t a mino lig nin a minopla s t res inous
product.
[ 0047 ] In a n a dditiona l pref erred proces s , 2 pa rts by W eig h t
of th e mix ture of a mino lig nin, a mino cellulos e a nd a mino
lig nin cellulos e res inous product, produced by th e proces s of
th is inv ention, a nd 1 to 4 pa rts by W eig h t of a n org a nic
polyis ocya na te a re mix ed, th en a g ita ted f or 10 to 6 0 minutes
a t a tempera ture betW een 20 C to 7 00 C. , th ereby producing a
poly( polyis ocya na te a mino lig nin a mino cellulos e a mino lig
nin cellulos e) prepolymer; th en 10% to 100% by W eig h t of a
curing a g ent, ba s ed on th e W eig h t of th e prepolymer, is a dded
to th e poly( polyis ocya na te a mino lig nin a mino cellulos e
a mino lig nin cellulos e) prepolymer W h ile a g ita ting a t 20 C to
80 C f or 5 to 20 minutes , th ereby producing a cellula r s olid or
s olid poly( polyis ocya na te a mino lig nin a mino cellulos e
a mino lig nin cellulos e) product.
[ 0048] In a n a dditiona l pref erred proces s , 1 to 3 pa rts by
W eig h t of th e a mino lig nin, a mino cellulos e a nd a mino lig nin
cellulos e mix ture, a s produced by th e proces s of th is inv en
tion, 1 to 3 pa rts by W eig h t of a polyol, 1 to 10 pa rts by W eig h t
of a W a ter- binding a g ent, 1 to 10 pa rts by W eig h t of a ?ller, 1
to 3 pa rts by W eig h t of a n org a nic polyis ocya na te, up to 10%
by W eig h t of a ?ller, 1 to 3 pa rts by W eig h t of a n org a nic
polyis ocya na te, up to 10% by W eig h t of a n a mine ca ta lys t a nd
up to 5 0% by W eig h t of a n inert v ola tile bloW ing a g ent,
percenta g e ba s ed on th e W eig h t of th e rea cta nts ( a mino lig nin,
a mino cellulos e a nd a mino lig nin- cellulos e, polyol a nd poly
is ocya na te) a re mix ed a nd th e res ulta nt mix ture is rea cted
th ereby producing a polyureth a ne a mino lig nin a mino cellu
los e a mino lig nin cellulos e f oa med product; th e f oa med prod
uct is th en emerg ed in W a ter f or 1 to 3 h ours th ereby curing th e
W a ter- binding a g ent.
[ 0049] In a n a dditiona l pref erred proces s , 1 to 3 pa rts by
W eig h t of th e a mino lig nin product, a s a product of th is
inv ention, 1 to 3 pa rts by W eig h t of a polyol, 1 to 3 pa rts by
W eig h t of a n a lk a li meta l s ilica te s uch a s s odium a nd pota s
s ium s ilica te, up to 5 % by W eig h t of a n emuls if ying a g ent a nd
up to 10% by W eig h t of a n a mine ca ta lys t a re mix ed to f orm
a n emuls ion th en mix ed W ith a mix ture of 3 pa rts by W eig h t of
PMD I th ereby producing a poly( ureth a ne a mino lig nin a lk a li
meta l s ilica te) f oa m.
[ 005 0] In a n a dditiona l pref erred proces s , 1 to 3 pa rts by
W eig h t of th e mix ture of a mino lig nin, a mino lig nin- cellulo s e,
US 2011/0098384 A1
a mino cellulos e, lig nin, lig nin cellulos e a nd s ug a rs a s pro
duced in th e proces s of th is inv ention, 3 pa rts by W eig h t of a n
is ocya na te- termina ted poly- ureth a ne prepolymer, up to 10%
by W eig h t of a mine ca ta lys t, up to 20% by W eig h t of a f oa m
s ta biliz er, up to 5 0% by W eig h t of a n inert v ola tile blow ing
a g ent, up to 100% by W eig h t of a curing a g ent a nd up to 3
pa rts by W eig h t of a polyol a re mix ed; th e res ulta nt mix ture is
a lloW ed to rea ct th ereby producing a polyureth a ne rig id f oa m.
[ 005 1] In a n a dditiona l pref erred proces s , 1 to 3 pa rts by
W eig h t of th e a mino lig nin, a mino lig nin- cellulos e, lig nin,
lig nin cellulos e a nd a mino cellulos e mix ture a s produced by
th e proces s of th is inv ention a nd 1 to 3 pa rts by W eig h t of
f urf uryl a lcoh ol a re mix ed, th en a n a cid compound is a dded
until th e pH is 2 to 6 , a s tes ted in W a ter, is th oroug h ly mix ed
a nd th e res ulta nt mix ture a lloW ed to rea ct th ereby producing
a poly( f urf uryl a lcoh ol a mino lig nin a mino cellulos e a mino
lig nin cellulos e) res inous product.
[ 005 2] Rea dily v ola tile bloW ing a g ents , e. g . , dich lorodif
luorometh a ne in th e a mount of 10 to 5 0 pa rts by W eig h t, s uch
a s trich loro?uorometh a ne, buta ne, is obutylene or v inyl ch lo
ride, ma y be us ed to produce cellula r s olid products in th is
inv ention. In a ddition, th e liquid rea ction mix tures ca n be
ex pa nded into a f oa m by th e introduction of g a s es , optiona lly
under pres s ure, s uch a s a ir, meth a ne, CF, noble g a s es a nd
ca rbon diox ide, th e res ulting f oa m being introduced into th e
required mold a nd h a rdened th erein. Th e res ulta nt f oa m ma y
optiona lly conta in f oa m s ta biliZ ers s uch a s s urf a cta nts , f oa m
f ormers , emuls i?ers a nd, if des ired, oth er org a nic or inor
g a nic ?llers or diluents ma y initia lly be conv erted by bloW ing
g a s into a f oa m a nd th e res ulting f oa m s ubs equently mix ed in
a mix er W ith th e oth er components , th e res ulting mix ture
being a lloW ed to h a rden. Ins tea d of bloW ing a g ents , it is a ls o
pos s ible to us e inorg a nic or org a nic, ?nely div ided h olloW
bodies s uch a s ex pa nded h olloW bea ds of g la s s , pla s tic, s tra W ,
ex pa nded da y, a nd th e lik e, f or producing f oa ms . Th e f oa ms
obta ina ble in th is W a y ca n be us ed eith er in th eir dry or th eir
mois t f orm if des ired a f ter a compa cting or tempering pro
ces s , optiona lly ca rried out under pres s ure, a s ins ula ting
ma teria ls , ca v ity ?lling s , pa ck a g ing ma teria ls , building ma te
ria ls , etc. Th ey ca n a ls o be us ed in th e f orm of s a ndW ich
elements , f or ex a mple, W ith meta l cov ering la yers , in h ous e,
v eh icle a nd a ircra f t cons truction. It is a ls o pos s ible to intro
duce into th e f oa ming rea ction mix tures , prov iding th ey a re
s till f ree- ?ow ing , org a nic a nd/ or org a nic f oa ma ble or a lrea dy
f oa med pa rticles , f or ex a mple, ex pa nded da y, ex pa nded g la s s ,
W ood, popcorn, cork , h olloW bea ds of pla s tics , f or ex a mple,
v inyl ch loride polymers , polyeth ylene, s tyrene polymers or
f oa m pa rticles th ereof or ev en, f or ex a mple, polys ulph one,
polyepox ide, polyureth a ne, urea f orma ldeh yde, ph enol f orm
a ldeh yde, polyimide polymers , urea s ilica te f orma ldeh yde
polymers , ph enol s ilica te f orma ldeh yde, epox y s ilica te poly
mers , polyis ocya na te s ilica te polymers , polyureth a ne s ilica te
polymers or th e rea ction mix ture ma y be a lloW ed to f oa m
th roug h inters titia l s pa ced pa rticles in pa ck ed v olumes of
th es e pa rticles a nd, in th is W a y, to produce ins ula ting ma teri
a ls . Combina tions of ex pa nded cla y, g la s s or s la te W ith th e
rea ction mix ture, a ccording to th e inv ention, a re es pecia lly
pref erred.
[ 005 3] It is a ls o pos s ible to introduce into th e f oa ming
rea ction mix tures , prov iding th ey a re s till f ree- ?ow ing , a t a
pre- determined tempera ture, a bloW ing a g ent W h ich is
ca pa ble of ev a pora tion or of g a s f orma tion a t th es e tempera
tures , f or ex a mple, a h a log ena ted h ydroca rbon. Th e liquid
mix ture f ormed ca n be us ed not only f or producing unif orm
Apr. 28, 2011
f oa ms or nonunif orm f oa ms conta ining f oa med or unf oa med
?llers , but it ca n a ls o be us ed to f oa m th roug h a ny g iv en W ebs ,
W ov en f a brics , la ttices , s tructura l elements or oth er perme
a ble s tructures of f oa med ma teria ls , res ulting in th e f orma tion
of compos ite f oa ms W ith s pecia l properties , f or ex a mple,
f a v ora ble ?a me beh a v ior, W h ich ma y optiona lly be directly
us ed a s s tructura l elements in th e building , f umiture or
v eh icle a nd a ircra f t indus tries .
[ 005 4] Th e cellula r s olid products ( f oa ms ) a ccording to th e
inv ention ca n be a dded to s oil in th e f orm of crumbs , option
a lly in a dmix tures W ith f ertiliz ers a nd pla nt- protection
a g ents , in order to improv e its a g ra ria n cons is tency. Since th e
h a rdened f oa ms obta ined by th e proces s a ccording to th e
inv ention ca n s h oW cons idera ble poros ity a f ter drying , th ey
a re s uita ble f or us e a s drying a g ents beca us e th ey ca n a bs orb
W a ter; h oW ev er, th ey ca n a ls o be ch a rg ed W ith a ctiv e s ub
s ta nces or us ed a s ca ta lys t s upports or ?lters a nd a bs orbents .
On th e oth er h a nd, th e f oa ms ca n be s ubs equently la cquered,
meta lliZ ed, coa ted, la mina ted, g a lv a niZ ed, s ubj ected to v a por
depos ition, bonded or ?ock ed in eith er th eir mois t or dry f orm
or in impreg na ted f orm. Th e molding s ca n be f urth er pro
ces s ed in th eir mois t or dried f orm, f or ex a mple, by s a W ing ,
milling , drilling , pla ning , polis h ing a nd oth er ma ch ining
tech niques . Th e optiona lly ?lled molding ca n be f urth er
modi?ed in th eir properties by th e- trea tment, ox ida tion pro
ces s es , h ot- pres s ing , s intering proces s es or s urf a ce melting or
oth er cons olida tion proces s es . Suita ble mold ma teria ls
include inorg a nic a nd/ or org a nic f oa med or unf oa med ma te
ria ls s uch a s meta ls , f or ex a mple, iron, nick el, ?ne s teel,
la - coa ted a luminum, porcela in, g la s s , W ood, pla s tics s uch a s
PVC, polyeth ylene, epox ide res ins , AB S, polyca rbona te, etc.
[ 005 5 ] Fillers in th e f orm of pa rticula te or poW dered ma te
ria ls ca n be a dditiona lly incorpora ted into th e liquid mix tures
of th e f oa ma ble or res inous rea cta nts f or a number of a ppli
ca tions .
[ 005 6 ] Suita ble ?llers include s olid inorg a nic or org a nic
s ubs ta nces , f or ex a mple, in th e f orm of poW ders , g ra nula te,
W ire, ?bers , dumb bells , crys ta llites , s pira ls , rods , bea ds ,
h olloW bea ds , f oa m pa rticles , W ebs , pieces of W ov en f a bric,
k nit f a brics , ribbons , pieces of ?lm, etc. , f or ex a mple, of
dolomite, ch a lk , a lumina , a s bes tos , ba s ic s ilica s , s a nd, ta l
cum, iron ox ide, a luminum ox ide a nd ox ide h ydra te, Z eolites ,
ca lcium s ilica tes , ba s a lt W ool or poW der, g la s s ?bers , C- ?
bers , g ra ph ite, ca rbon bla ck , A 1- , Fe- , Cu- , Ag - poW der,
molybdenum s ulph ite, s teel W ool, bronZ e or copper cloth ,
s ilicon poW der, ex pa nded cla y, polybuta diene, polyis oprene,
polytetra ?uoroeth ylene, a liph a tic a nd a roma tic polyes ters ,
mela mine- urea or ph enol res ins , polya ceta l res ins , polyep
ox ides , polyh yda ntoins , poly urea , polyeth ers , polyure
th a nes , polyimides , polys ulph ones , polyca rbona tes , a nd, of
cours e, a ny copolymers a s W ell. Inorg a nic ?llers a re pre
f erred.
[ 005 7 ] Genera lly, th e compos ite ma teria ls a ccording to th e
inv ention ca n be ?lled W ith cons idera ble qua ntities of ?llers
W ith out los ing th eir v a lua ble property s pectrum. Th e a mount
of ?llers ca n ex ceed th e a mount of th e rea cta nts . In s pecia l
ca s es , th e f oa med products of th e pres ent inv ention a ct a s a
binder f or s uch ?llers . 10 to 200 pa rts by W eig h t of a ?ller ma y
be a dd.
[ 005 8] B a s ica lly, th e production of th e cellula r s olid prod
ucts a ccording to th e inv ention is ca rried out by mix ing th e
rea cta nts in one or more s ta g es in a continuous ly- or intermit
tently- opera ted mix ing a ppa ra tus a nd th en a lloW ing th e
res ulting mix ture to f oa m a nd s olidif y, us ua lly outs ide th e
US 2011/0098384 A1
mix ing a ppa ra tus in molds , or on s uita ble ma teria ls . Th e
rea ction tempera ture required f or th is , W h ich ma y be f rom 0 C
to 200 C a nd pref era bly f rom 200 C to 16 0 C, ma y eith er be
a ch iev ed by h ea ting one or more of th e rea cta nts bef ore th e
mix ing proces s or by h ea ting th e mix ing a ppa ra tus its elf or,
a lterna tiv ely, by h ea ting th e rea ction mix ture a f ter th e com
ponents h a v e been mix ed. Combina tions of th es e or oth er
meth ods of a dj us ting th e rea ction tempera ture ma y, of cours e,
a ls o be employed. In mos t ca s es , s u?icient h ea t is ev olv ed
during th e rea ction to ena ble th e rea ction tempera ture to ris e
to v a lues a bov e 5 0 C a f ter th e rea ction or f oa ming h a s beg un.
[ 005 9] In pa rticula r, h oW ev er, th e proces s a ccording to th e
inv ention is s uita ble f or in s itu f oa ming on th e building s ite.
Any h olloW f orms obta ined by mea ns of s h uttering in th e
conv entiona l W a y ma y be ?lled up a nd us ed f or f oa ming in
th is W a y.
[ 006 0] Th e a mino lig nin, a mino cellulos e, lig nin a nd a mino
lig nin cellulos e res inous product a s produced in th is inv ention
ma y be pre- rea cted W ith a n a ldeh yde, a t a pH of 7 to 12, to
produce a liquid of a mino lig nin a ldeh yde, th en pla ced in a
mix ing ch a mber, optiona lly a dding a bloW ing a g ent, emuls i
?er, f oa m s ta biliZ er, ?ller, ?a me- reta rda nt a nd oth er a ddi
tiv es , th en ra pidly mix ed W ith a n a cid compound a nd th en
pumped or bloW n by compres s ed a ir into a mold s uch a s a
W a ll. ceiling , etc. , W h ile ex pa nding , th ereby producing a cel
lula r s olid product, us ef ul f or s ound a nd th erma l ins ula tion.
Th e f oa ming components ma y a ls o be pumped into a la rg e
mold to ex pa nd a nd h a rden into a cellula r product. Th e cel
lula r product ma y be s a W ed, drilled, pla ned or na iled. Th e
f oa ming components ma y be f oa med up a nd h a rdened W h ile
th e f orm of droplets or ma y be dis pers ed, e. g in petroleum
h ydroca rbons or W h ile th ey a re under condition of f ree f a ll.
Foa m bea ds a re obta ined in th is W a y. Th e f oa med products
produced by th es e meth ods ma y a ls o be a dded in a crumbly
f orm to protectiv e a g ents s o a s to improv e th e a g ricultura l
cons is tency of th e s oil. Foa ms W h ich h a v e a h ig h W a ter con
tent ma y be us ed a s s ubs tra tes f or th e propa g a tion of s eed
ling s , s h oots a nd pla nts or f or cut ?oW ers . Th e mix tures ma y
be s pra yed on terra in W h ich is impa s s ible or too loos e, s uch a s
dunes or ma rs h es , to s treng th en s uch terra in s o th a t it W ill be
?rm enoug h to W a lk on W ith in a s h ort time, a nd W ill be
protected a g a ins t eros ion. Th e f oa ming mix tures ma y a ls o be
us ed underg round in ca v es , mines , tunnels , etc. , by s pra ying
th e f oa ming mix ture onto W ire mes h , ?berg la s s cloth , W ov en
f a brics or directly on th e W a lls , to produce protectiv e la yers to
prev ent a ccidents . It is a ls o pos s ible to introduce into th e
roa ming rea ction mix tures , prov iding th ey a re s till f ree
?oW ing , org a nic a nd/or org a nic f oa ma ble or a lrea dy f oa med
pa rticles s uch a s ex pa nded cla y, ex pa nded g la s s , W ood, pop
corn, cork , h olloW bea ds of pla s tics , f or ex a mple, v inyl ch lo
ride polymers , polyeth ylene, s tyrene polymers or f oa m pa r
ticles th ereof or ev en, f or ex a mple, polys ulph one,
polyepox ide, polyureth a ne, urea f orma ldeh yde ph enol f orm
a ldeh yde, polyimide polymers , or to a lloW th e rea ction mix
tures to f oa m th roug h inters titia l s pa ce in pa ck ed v olumes of
th es e pa rticles , a nd in th is W a y to produce ins ula ting ma teria ls
W h ich a re dis ting uis h ed by ex cellent ?a me beh a v ior. Combi
na tions of ex pa nded cla y, g la s s , or s la te W ith th e rea ction
mix tures , a ccording to th e inv ention, a re es pecia lly pref erred.
[ 006 1] Th e urea lig nin- cellulos e res inous a nd urea lig nin
product, poly( a ldeh yde urea lig nin- cellulos e) res inous prod
uct, poly( urea lig nin a minopla s t a mino lig nin cellulos e) res
inous product, poly( a mino lig nin ph enopla s t a mino lig nin
cellulos e) a nd poly( a mino lig nin a minopla s t a mino lig nin
Apr. 28, 2011
cellulos e ph enopla s t) res inous produced ma y us e a s a th er
mos etting res inous a dh es iv e us ef ul pa rticula rly a s plyW ood,
AB S, f or lumber la mina ting a dh es iv e, etc. Th e a dh es iv e ma y
be cured by h ea t ( 25 0 C to 300 C) a nd pres s ure ( 110 to 26 0
ps i) . Th e a dh es iv e res inous products W ill a ls o cure by th e
pres ence of a n a lk a li or a cetic ca ta lys t or by us ing h ex a meth
ylene or pa ra f orma ldeh yde.
[ 006 2] Th es e poly( polyis ocya na te a mino lig nin cellulos e) ,
polyureth a ne a mino lig nin cellulos e, polyureth a ne a mino lig
nin, polyureth a ne a mino cellulos e, polyureth a ne lig nin- cel
lulos e s ilica te a nd poly( polyis ocya na te a mino lig nin cellu
los e s ilica te) cellula r products a re s oluble in org a nic s olv ents
a nd ma y be utiliZ ed a s pa ints , v a rnis h es , a dh es iv es , ?llers ,
ca ulk ing ma teria l, etc.
D ETAILED D ESCRIPTION OF THE IN VEN TION
[ 006 3] Lig nin is a complex h ydroph obic netW ork of ph e
nylpropa noid units W h ich v a ries in its s ubunit compos ition
a nd intermolecula r link a g e. Th es e complex ph enolic a re
th oug h t to include 4- h ydrox ycinna myl a lcoh ol, conif eryl
a lcoh ol a nd s ina pyl a lcoh ol. In dif f erent pla nts th e lig nin v a ry
in compos ition. Mos t lig nin conta in ph enyl type h ydrox yl
ra dica ls , a cid ra dica ls , uns a tura ted ra dica ls a nd epox y ra di
ca ls a nd oth er ra dica ls W h en th e lig nin is s epa ra ted f rom th e
cellulos e. Th e ph enyl type h ydrox yl ra dica ls a re rea cted W ith
th e iN HZ on th e a mino compound a nd s epa ra tes f rom th e
cellulos e to produce a n a mino lig nin. Some of th e a mino
compounds rea ct W ith th e lig nin W h ich is s till a tta ch ed to th e
cellulos e a nd W ith cellulos e. Th e a mino ph enyl type h ydrox yl
compounds , a mino cellulos e, a mino lig nin cellulos e a nd th e
ph enyl type h ydrox y compounds on th e lig nin cellulos e a re
ch emica lly a ctiv e a nd W ill rea ct W ith a ldeh ydes , org a nic
a cids , inorg a nic a cids , k etones , a mines , polya mines , a mino
compounds , epox y compounds , polyepox y, polys ulf one,
polyimines , ph enopla s ts , a minopla s ts , polyes ters , polyeth ers
a nd polyth ioeth ers conta ining 40H ra dicles , v eg eta ble oils ,
f a ts , ca rboh ydra tes , s oy ?our, proteins , s ta rch , W h ea t ?ours ,
cellulos e, a lcoh ols , polyca rbox ylic a cids , polya lcoh ols , poly
is ocya na tes , polyca rbona tes W ith 40H ra dicles , epich loro
h ydrin, s ubs tituted compounds , f urf urol, f urf uryl a lcoh ol,
org a nic a nd inorg a nic ph os ph orus compounds , s ome uns a t
ura ted org a nic compounds , a lk a li meta l compounds , a lk a li
meta l ea rth compounds a nd oth er compounds .
[ 006 4] In g enera l, th e lig nin cellulos e bond is brok en by
s oa k ing in a n a queous s olution of th e lis ted a mino com
pounds W ith urea , pref era ble urea a nd or g ua nidine type com
pounds , a t a mbient tempera ture f or 12 to 24 h ours or by
h ea ting th e bioma s s conta ining lig nin cellulos e pla nt pa rticles
in a n a queous s olution of lis ted a mino compounds a t a mbient
pres s ure a t 100 deg ree C. f or 1- 4 h ours or a t 15 0 deg ree C.
under pres s ure f or 0. 5 to 4 h ours th ereby brea k ing th e lig nin
cellulos e bond by th e proces s of th e a mino compounds rea cts
W ith th e lig nin to f orm a mino lig nin a nd th e a mino compound
rea ct W ith s ome of th e lig nin s till a tta ch ed to th e cellulos e a nd
cellulos e producing a mino- lig nin- cellulos e, a mino cellulos e
a nd s ome of th e ph enyl h ydrox yl ra dica l on th e lig nin cellu
los e a re a ls o ch emica lly a ctiv e. Th e a mino lig nin is W a ter
s oluble a nd f orm a n a queous s olution of a mino lig nin. Th e
a queous a mino lig nin, lig nin, ca rboh ydra tes , h emi- cellulos e
s olution a re remov ed f rom th e a mino lig nin cellulos e, lig nin
cellulos e a nd a mino cellulos e by compres s ion, ?ltra tion or
a ny s uita ble mea ns . W a ter is remov ed f rom th e a queous
a mino s a lt of lig nin s olution until a th ick s olution is f ormed or
f urth er dried until g ra nules a re f ormed. Th e urea lig nin ma y
US 2011/0098384 A1
be utiliz ed to produce a mino lig nin a ldeh yde res ins or ma y be
rea cted W ith epox y compounds , f urf urol, f urf uryl a lcoh ol or
polyca rbox yl a cids a nd oth er lis ted compounds to produce
res ins a nd a dh es iv es . Th e a mino- lig nin- cellulos e, a mino cel
lulos e a nd lig nin cellulos e h a s ma ny us es s uch a s pa per pro
duction, h ydrolyZ ed to ca rboh ydra tes , in production of ?ber
boa rd, plyW ood, molded obj ects , f ertiliz er, a nima l f eed a nd
oth er us es .
[ 006 5 ] Th e a mino of lig nin, h emi- cellulos e, ca rboh ydra tes ,
a mino lig nin cellulos e, a mino cellulos e a nd lig nin cellulos e
mix ture W ith mos t of th e W a ter ev a pora ted of f is mix ed W ith
a nd a ldeh yde s uch a s a queous f orma ldeh yde, pH a dj us ted to
7 - 8 W ith a ba s ic compound s uch a s a mmonia th en h ea ted until
th e W a ter is ev a pora ted of f , th en a a cidic compound s uch a s
urea s ulf a te is a dded until th e pH 4- 6 is obta ined th en f urth er
h ea ting th e mix ture to a bout 100- 25 0 deg ree C. a t a mbient to
elev a ted pres s ure to ef f ect polymeriz a tion to f orm a h a rd,
s trong , W a ter res is ta nt, ?re res is ta nt, th ermos etting ma teria l.
A ba s ic ca ta lys t ma y be a dded to th e a mino lig nin, a mino
cellulos e a nd a mino lig nin cellulos e mix ture until th e pH is
a bout 8, th en a queous f orma ldeh yde is a dded, th en h ea ted
until th e W a ter is ev a pora ted to f orm a th ermopla s tic res in. An
a cid ca ta lys t is a dded to th e mix ture until th e pH is a bout 4- 5
th en f urth er h ea ted until th e it s olidi?es to f orm a h a rd, s trong ,
W a ter res is ta nt, ?re res is ta nt, th ermos etting ma teria l.
[ 006 6 ] Th e h emi- cellulos e, a mino lig nin cellulos e, a mino
cellulos e a nd modi?ed lig nin cellulos e produced by th is
inv ention a re h ydrolyZ ed to ca rboh ydra tes by a cid h ydrolys is
us ing 7 0% s ulf uric a cid or 40% h ydroch loric a cid. Th e con
centra ted a cid is a dd to th e dried a mino- lig nin- cellulos e in th e
ra tio of 1- 2 pa rts by W eig h t of a cid to 1 pa rt W eig h t of th e
a mino- lig nin- cellulos e th en h ea ted to a loW tempera ture of
5 0- 7 0 deg ree C. f or 1- 6 h ours to produce a mix ture of ca rbo
h ydra tes , a mino s a lt of th e a cid, lig nin cellulos e a nd cellulos e.
Th e cellulos e a nd lig nin cellulos e th a t W a s not h ydrolyZ ed is
s epa ra ted by pres s ing a nd ?ltering th en retrea ted by rea cting
th e lig nin W ith a n a mino compound in a n a queous s olution to
produce a W a ter s oluble a mino s a lt of lig nin W h ich is remov ed
f rom th e cellulos e by pres s ing a nd ?ltering . Th e cellulos e is
th en dried a nd retrea ted W ith th e a cid. Th e a queous s olution of
ca rboh ydra tes a nd s ulf uric a cid a re trea ted to s epa ra te th e
ca rboh ydra tes f rom th e s ulf uric a cid by v ia ion ex ch a ng e a nd
th en th e s ulf uric a cid is re- concentra ted v ia multiple ef f ect
ev a pora tors . W h en h ydroch loric a cid is utiliZ ed th e rema ining
s olid cellulos e a nd lig nin cellulos e a re remov ed f rom th e
a queous s olution of ca rboh ydra tes a nd a mino ch loride by
pres s ing a nd ?ltering th en retrea ted. Th e ca rboh ydra tes a nd
a mino ch loride is recov ered by ev a pora ting th e a queous
h ydroch loric a cid under v a cuum to depres s th e boiling point.
Th e a cid lef t in th e ca rboh ydra te a nd a mino ch loride is na tu
ra liZ ed W ith ca lcium h ydrox ide. Th e ca rboh ydra te ma y be
conv erted into a lcoh ol by yea s t or a ny oth er s uita ble mea nA
dilute a cid h ydrolys is proces s us ing s ulf uric or h ydroch loric
a cid ma y be utiliZ ed to h ydrolyZ e th e a mino- lig nin- cellulos e
into ca rboh ydra tes . Th e a mino- lig nin- cellulos e is s oa k ed in
30- 40% s ulf uric or h ydroch loric a cid f or 1- 4 h ours th en W a ter
is ev a pora ted until th e a cid is more concentra ted up to 40 to
7 0% th en f urth er rea cted f or 1- 4 h ours . Th e ca rboh ydra tes ,
a cid a nd a mino s a lt is ?lter by pres s ing or ?ltering a nd th e
cellulos e a nd lig nin cellulos e res idue is retrea ted.
[ 006 7 ] Th e obj ect of th e pres ent inv ention is to prov ide a
nov el proces s f or delig ni?ca tion of lig nin cellulos e a nd pro
duce a mino lig nin, a mino cellulos e, a mino lig nin cellulos e
res inous products , cellulos e, s ug a rs , h emi- cellulos e, ca rbo
Apr. 28, 2011
h ydra tes a nd W a x es , turpentine, a lcoh ols , a g a r, reins , rubber
la tex , dyes , etc. f rom lig nin cellulos e conta ining pla nts .
Anoth er obj ect is to produce nov el a mino lig nin, lig nin,
a mino lig nin- cellulos e, lig nin cellulos e products W h ich a re
h ig h ly ch emica lly rea ctiv e. Still a noth er obj ect is to product
ca rboh ydra tes ( s ug a rs ) W h ich ca n be f ermented to produce
eth a nol. Anoth er obj ect is to rea ct products produced by th e
delig ni?ca tion of lig nin cellulos e by a n a queous urea to rea ct
W ith a n a ldeh yde to produce a res inous product W h ich is cured
by h ea t a nd/or a n a cidic compound to produce a ?a me reta r
da nt, W a ter res is ta nt, h a rd, toug h res inous product. Still
a noth er obj ect is to produce a mino lig nin, a mino lig nin cel
lulos e a nd a mino cellulos e res inous product W h ich W ill rea ct
ch emica lly W ith a ldeh ydes to produce nov el poly( a ldeh yde
a mino lig nin) , poly( a mino lig nin cellulos e) a nd poly( a lde
h yde a mino cellulos e) res inous product a nd f oa ms . Anoth er
obj ect is to produce nov el a mino lig nin, a mino lig nin cellu
los e, a mino cellulos e polymers th a t W ill rea ct W ith a ldeh ydes
a nd a mino compounds to produce nov el poly( a minopla s t
a mino lig nin) , poly( a minopla s t a mino lig nin cellulos e) , poly
( a minopla s t cellulos e) res ins a nd f oa ms . Anoth er obj ect is to
produce a mino lig nin, a mino cellulos e, lig nin cellulos e a nd
a mino lig nin cellulos e polymers th a t W ill rea ct W ith a ldeh yde
compounds a nd ph enol compounds to produce nov el poly
( ph enopla s t a mino lig nin) , poly( ph enopla s t a mino lig nin cel
lulos e) a nd poly( ph enopla s t a mino cellulos e) res ins a nd
f oa ms . Anoth er obj ect is to produce a mino lig nin, a mino
lig nin cellulos e, a mino cellulos e, ca rboh ydra tes , lig nin a nd
lig nin cellulos e polymers th a t W ill rea ct W ith polyis ocya na te
compounds a nd polyureth a ne prepolymers to produce nov el
poly( polyis ocya na te a mino lig nin) , poly( polyis ocya na te
a mino lig nin cellulos e) , poly( polyis ocya na te a mino cellu
los e) a nd poly( ureth a ne lig nin cellulos e) res ins a nd cellula r
products . Anoth er obj ect is to produce a mino lig nin, a mino
lig nin cellulos e, lig nin, a mino cellulos e, lig nin cellulos e
polymers th a t W ill rea ct W ith polyureth a ne prepolymers a nd
ox ida ted s ilicon compounds to produce nov el poly( ureth a ne
a mino lig nin cellulos e s ilica te) res ins a nd cellula r s olid prod
ucts . Anoth er obj ect is to produce a mino lig nin, a mino lig nin
cellulos e, a mino cellulos e, lig nin a nd lig nin cellulos e th a t
W ill rea ct W ith rea ctiv e org a nic compounds to produce poly
mers , res ins a nd a dh es iv e. Anoth er obj ect is to ch emica lly
rea ct th e a mino lig nin, a mino cellulos e, lig nin, a mino lig nin
cellulos e a nd lig nin cellulos e compounds a nd res inous prod
ucts of th is inv ention W ith oth er org a nic ch emica ls W h ich
conta in one or more h ydrox yl, a ldeh yde, a cetic, epox y, a nh y
dride, eth er, a mino, a mine, k etone, uns a tura ted, s ubs tituted,
is ocya na te, ph os ph orus a nd oth er ra dica ls . Anoth er obj ect is
to rea ct th e a mino lig nin W ith bio- ba s ed compounds s uch a s
v eg eta ble oils a nd proteins , s ug a rs , ?ours , lig nin, cellulos e
a nd h emi- cellulos e. Anoth er obj ect is to rea ct th e a mino lig
nin, lig nin, a mino cellulos e, a mino lig nin cellulos e W ith a lk a li
meta l compounds .
[ 006 8] Th e f oa med products produced by th es e meth ods
ma y a ls o be a dded in a crumbly f orm to s oil, optiona lly W ith
th e a ddition of f ertiliZ ers a nd pla nt- protectiv e a g ents s o a s to
improv e th e a g ricultura l cons is tency of th e s oil. Foa ms W h ich
h a v e a h ig h W a ter content ma y be us ed a s s ubs tra tes f or th e
propa g a tion of s eedling s , s h oots a nd pla nts or f or cut ?oW ers .
Th e mix tures ma y be s pra yed on terra in W h ich is impa s s ible
or too loos e, s uch a s dunes or ma rs h es , to s treng th en s uch
terra in s o th a t it W ill be ?rm enoug h to W a lk on W ith in a s h ort
time, a nd W ill be protected a g a ins t eros ion. Th e f oa ming
mix tures ma y a ls o be us ed underg round in ca v es , mines ,
US 2011/0098384 A1
tunnels , etc. , by s pra ying th e f oa ming mix ture onto W ire
mes h , ?berg la s s cloth , W ov en f a brics or directly on th e W a lls ,
to produce protectiv e la yers to prev ent a ccident. It is a ls o
pos s ible to introduce into th e roa ming rea ction mix tures ,
prov iding th ey a re s till f ree- ?ow ing , org a nic a nd/or org a nic
f oa ma ble or a lrea dy f oa med pa rticles s uch a s ex pa nded cla y,
ex pa nded g la s s , W ood, popcorn, cork , h olloW bea ds of pla s
tics , f or ex a mple, v inyl ch loride polymers , polyeth ylene, s ty
rene polymers or f oa m pa rticles th ereof or ev en, f or ex a mple,
polys ulph one, polyepox ide, polyureth a ne, urea f orma lde
h yde ph enol f orma ldeh yde, polyimide polymers , or to a lloW
th e rea ction mix tures to f oa m th roug h inters titia l s pa ce in
pa ck ed v olumes of th es e pa rticles , a nd in th is W a y to produce
ins ula ting ma teria ls W h ich a re dis ting uis h ed by ex cellent
?a me beh a v ior. Combina tions of ex pa nded cla y, g la s s , or
s la te W ith th e rea ction mix tures , a ccording to th e inv ention
a re es pecia lly pref erred.
[ 006 9] Th e a mino lig nin, a mino cellulos e a nd a mino lig nin
cellulos e res inous product, poly( a ldeh yde a mino lig nin
a mino cellulos e) res inous product, poly( a minopla s t a mino
lig nin a mino lig nin cellulos e) res inous product, poly( ph eno
pla s t a mino lig nin a mino lig nin cellulos e) a nd poly( a mino
pla s t a mino lig nin a mino cellulos e ph enopla s t) res inous pro
duced ma y be us ed a s a th ermos etting res inous a dh es iv e
us ef ul pa rticula rly a s a n a dh es iv e f or plyW ood a nd la mina ting
lumba r. Th e a dh es iv e ma y be cured by h ea t ( 25 0 C to 400 C)
a nd pres s ure ( 1 10 to 26 0 ps i) . Th e a dh es iv e res inous products
W ill a ls o cure by th e pres ence of a n a lk a li or a cetic ca ta lys t or
by us ing h ex a meth ylene or pa ra f or' ma ldeh yde.
[ 007 0] Th es e poly( polyis ocya na te a mino lig nin cellulos e) ,
polyureth a ne a mino lig nin, polyureth a ne a mino cellulos e,
polyureth a ne cellulos e, polyureth a ne a mino lig nin cellulos e
s ilica te a nd poly( polyis ocya na te a mino lig nin cellulos e s ili
ca te) cellula r products a re s oluble in org a nic s olv ents a nd
ma y be utiliZ ed a s pa ints , v a rnis h es , a dh es iv es , ?llers , ca ulk
ing ma teria l, etc.
D ESCRIPTION OF PREFERRED
EMB OD IMEN TS
[ 007 1] My inv ention W ill be illus tra ted in deta il by th e
s peci?c ex a mples W h ich f olloW , it being unders tood th a t
th es e pref erred embodiments a re illus tra tiv e of , but not lim
ited to, procedures W h ich ma y be us ed in th e production of
a mino lig nin, a mino cellulos e, a mino lig nin cellulos e a dh e
s iv e a nd res inous product a nd ca rboh ydra tes .
[ 007 2] Th e f olloW ing ex a mples illus tra te th e inv ention.
Unles s oth erW is e des ig na ted, a ll cons tituents a re des ig na ted
on th e ba s is of pa rts by W eig h t.
Ex a mple 1
[ 007 3] 80 pa rts by W eig h t of ?r s a W dus t a nd 30 pa rts by
W eig h t of urea W ere a dded to 25 0 pa rts by W eig h t of W a ter
th en th e mix ture W a s h ea ted to th e boiling point of W a ter a t
a mbient pres s ure f or 1 h our. Th e W a ter h a d a broW n color a f ter
5 minutes of h ea ting . A mix ture of urea lig nin a nd urea lig nin
cellulos e a long W ith urea cellulos e, lig nin, h emi- cellulos e,
ca rboh ydra tes , W a x es , a lcoh ol, a nd oth er products a re pro
duced. Th e a queous mix ture W a s pres s ed a nd ?ltered f rom th e
urea lig nin cellulos e, a mino cellulos e a nd lig nin cellulos e
th en th e urea lig nin cellulos e, urea cellulos e a nd lig nin cel
lulos e W a s re- W a s h ed W ith W a ter, pres s ed a nd ?ltered to
remov e more W a ter s oluble compounds . Th e urea lig nin cel
lulos e, urea cellulos e a nd lig nin cellulos e a re dried, W eig h ed
Apr. 28, 2011
a nd h a s los t 25 % of th e ?r orig ina l W eig h t. Th e da rk broW n
a queous s olution is ev a pora ted by h ea ting to a th ick s olution
or is f urth er dried to g ra nules W h ich W eig h ed 32 pa rts by
W eig h t.
[ 007 4] Th e a bov e urea lig nin cellulos e, urea cellulos e a nd
lig nin cellulos e W a s re- trea ted by a dding 30 pa rts by W eig h t of
urea a nd 25 0 pa rts by W eig h t of W a ter th en boiling f or 1 h our.
Th e a queous s olution of urea lig nin, lig nin, h emi- cellulos e
a nd ca rboh ydra tes W ere ?ltered of f th en th e urea lig nin cel
lulos e, a mino cellulos e a nd lig nin cellulos e W a s W a s h ed th en
pres s ed a nd ?ltered, th e urea lig nin a nd oth er compound s uch
h emi- cellulos e, ca rboh ydra tes W a s ?ltered of f . Th e da rk
broW n a queous s olution W a s ev a pora ted a nd 30 pa rts by
W eig h t of da rk broW n dry g ra nules W a s obta ined.
Ex a mple 2
[ 007 5 ] Ex a mple 1 is modi?ed W h ere in a dif f erent a mount
a nd type of a mino compound is utiliZ ed in pla ce of th e urea
a nd s elected f rom th e lis t beloW :
a . 20 pa rts by W eig h t of urea b. 40 pa rts by W eig h t of urea
c. 5 0 pa rts by W eig h t of urea d. 6 0 pa rts by W eig h t of urea
e. 80 pa rts by W eig h t of urea f . 30 pa rts by W eig h t of g ua nidine
g . 20 pa rts by W eig h t W ith 20 pa rts by W eig h t of urea
h . 20 pa rts by W eig h t of urea W ith 10 pa rts by W eig h t Of l' H6 l3IH1H6
i. 25 pa rts by W eig h t of urea 15 pa rts by W eig h t of g ua nidine ca rbona te
j . 30 pa rts by W eig h t of urea W ith s uf ?cient a mmonia to a dj us t pH to 7 . 5
k . 30 pa rts by W eig h t of urea 1. 20 pa rts by W eig h t of urea
cya nura te polya mine condens a te
Ex a mple 3
[ 007 6 ] Ex a mple 1 is modi?ed W h erein a noth er g round up
lig nin cellulos e pla nt is us ed in pla ce of ?r s a W dus t a nd
s elected f rom th e lis t beloW :
s pruce, pine, h emlock , oa k , a s h , la rch , birch , a s pen, popla r,
ceda r, beech , ma ple, W a lnut, cypres s , redW ood, ch erry, elm,
ch es tnut, h ick ory, locus t, s yca more, tulip, tupelo, butternut,
a pple, a lder, ma g nolia , dog W ood, ca ta lpa , box W ood, cra b
W ood, ma h og a ny, g reenh ea r t, la nceW ood, letterW ood, mora ,
prima v era , purpleh ea rt, ros e. - W ood, tea k , s a tinW ood, ma n
g rov e, W a ttle, ora ng e, lemon, log W ood, f us tic, os a g e ora ng e,
s a ppa nW ood, B ra Z ilW ood, ba rW ood, ca mW ood, s a nda lW ood,
rubber, g utta , mes quite, a nd s h rubs , e. g . , olea nder, cypres s ,
j unipers , a ca nth us , pyra ca nth a , lig us trum, la ta na , boug a in
v illea , a Z a lea , f eij oa , ilex , f us cia , h ibis cus , da tura , h olly,
h ydra ng ea , j a s mine, euca lyptus , cottonea s ter, x ylos ma ,
rh odeodendron, ca s tor bea n, eug enia , euonymus , f a ts h edera ,
a ra lia , etc. , a nd a g ricultura l pla nts , e. g . , cotton, cotton s ta lk s ,
corn s ta lk s , corn cobs , W h ea t s tra W , oa t s tra W , rice s tra W , ca ne
s ug a r ( ba g a s s e) , s oybea n s ta lk s , pea nut pla nts , pea v ines ,
s ug a r beet W a s te, s org h um s ta lk s toba cco s ta lk s , ma iZ e
s ta lk s , ba rley s tra W , buck W h ea t s tra W , quinoa s ta lk s , ca s s a ya ,
pota to pla nts , leg ume v ines a nd s ta lk s , v eg eta ble inedible
portion, etc. , W eeds , g ra s s es , v ines , k elp, ?oW ers , a lg a e,
pa per, cotton cloth , ba g a s s e W a llboa rd, W ood products ,
h umus , pea t, certa in s of t broW n coa l a nd mix tures th ereof .
Ex a mple 4
[ 007 7 ] 90 pa rts by W eig h t of th e mix ture of urea lig nin, urea
lig nin cellulos e, lig nin cellulos e, urea cellulos e, h emi- cellu
los e a nd ca rboh ydra tes in a n a queous s olution produced in
Ex a mple 1 a re mix ed W ith a n a queous s olution of f orma lde
US 2011/0098384 A1
h yde ( 37 %) in th e ra tio 2 moles of f orma ldeh yde to 1 mol of
th e urea , a nd a queous a mmonia is a dded until a pH of 7 . 5 is
obta ined. Th e mix ture is h ea ted until a ll of th e f ree w a ter is
ev a pora ted, th en a mmonium s ulf a te pow der is a dded to pro
duce a n a cidic pH 5 w h en h ea ted, th en th e res ins a re com
pres s ed in a mold a nd h ea ted to cure th e res in, ev a pora te th e
res t of th e w a ter a nd produce a w a ter res is ta nt, ?re res is ta nt,
h a rd a nd s trong pa rticle boa rd.
Ex a mple 5
[ 007 8] Urea in th e a mount of 40 pa rts by w eig h t is a dded
w ith 40 pa rts by w eig h t of s pruce s a w dus t into w a ter th en
boiled f or 30 minutes th ereby producing pa rtia l delig ni?ca
tion of th e s a w dus t to produce urea lig nin, lig nin, urea lig nin
cellulos e, lig nin cellulos e, urea cellulos e, ca rboh ydra tes a nd
oth er products . 7 0 pa rts by w eig h of a queous f orma ldeh yde
( 37 %) a nd a queous a mmonia a dded to th e a queous mix ture
until th e pH 7 . 5 th en h ea ted until th e f ree w a ter is ev a pora ted,
th en 5 pa rts by w eig h t of a cidic urea ph os ph a te pow der is a dd
a nd mix ed, th en h ea ted a t 300 F. until th e mix ture becomes
s olid a nd th en th e rema ining w a ter is ev a pora ted th ereby
producing a w a ter res is ta nt, ?re res is ta nt, h a rd a nd s trong
pa rticle boa rd.
Ex a mple 6
[ 007 9] Ex a mple 5 is modi?ed w h erein a noth er compound
is a dded w ith th e f orma ldeh yde a nd s elected f rom th e g roup
below :
a . 10 pa rts by w eig h t of s oy ?ow er b. 10 pa rts by w eig h t Of l' H6 l3IH1H6
c. 15 pa rts by w eig h t of ph enol d. 10 pa rts by W eig h of w h ea t ?our
e. 10 pa rts by w eig h t of biuret f . 5 pa rts by Of l' H6 l3IH1H6 ph os ph a te
g . 10 pa rts by w eig h t of h . 5 pa rts by w eig h t of oa t s tra w
dicya ndia lnide pow der
i. 5 pa rts by w eig h t of s ta rch j . dimela rnine ph os ph a te
Ex a mple 7
[ 0080] 10 pa rts by w eig h t of dried urea lig nin produced in
ex a mple 1 a nd 30 pa rts by w eig h t of a queous f orma ldeh yde
( 37 %) a re mix ed th en 5 pa rts by w eig h t of s oy ?our is g ra du
a lly a dded a nd mix ed in. Th e mix ture is th en h ea ted until th e
s olution th ick ens to f orm a n a dh es iv e. Th e s oy ?our urea
lig nin f orma ldeh yde res in is th en cured by a dding s uf ?cient
a cidic urea ph os ph a te to produce a n a cetic pH 5 in th e mix ture
w h en th e mix ture is h ea ted. It cures into a s olid res inous
product. Th is th ick a dh es iv e conta ining th e curing a g ent ma y
be a pplied to tw o pieces of boa rds th en cla mped a nd it w ill
cure to f orm a s trong g lued j oint.
Ex a mple 8
[ 0081] 30 pa rts by w eig h t of th e mois t dried mix ture of urea
lig nin, lig nin, urea lig nin cellulos e, lig nin cellulos e, urea
cellulos e a nd ca rboh ydra te mix ture produced in ex a mple 1
a nd 30 pa rts by w eig h t of polymeric MD I a re mix ed a nd
pa ck ed into a mold. Th e mix ture cures in a bout a n h our or ca n
be cured f a s ter us ing h ea t to f orm a w a ter res is ta nt, s trong ,
s olid pa rticleboa rd or molded obj ect.
Ex a mple 9
[ 0082] Ex a mple 8 is modi?ed w h erein th e w a ter s oluble
mix ture of ex a mple 1 is ?ltered of f a nd th e non- w a ter s oluble
Apr. 28, 2011
portion conta ining 10 pa rts by w eig h t of urea lig nin cellulos e,
urea cellulos e a nd lig nin cellulos e pa rtia lly dried till only
mois t th en mix ed w ith th e 10 pa rts by w eig h t of polymeric
MD I. Th ereby producing a s olid ureth a ne urea lig nin cellu
los e res inous product.
Ex a mple 10
[ 0083] Ex a mple 8 is modi?ed w h erein a blow ing a g ent,
dich lorodi?uorometh a ne, 2 pa rts by w eig h t, 0. 5 pa rts by
w eig h t of s ilicone s urf a cta nt a nd 0. 1 pa rt by w eig h t of a mine
ca ta lys t, dimeth yleth a nol- a mino, is a dded to th e mix ture th en
molded th ereby producing a rig id f oa m boa rd w h en cured
ma y be us ed a s a n ins ula ting s iding .
Ex a mple 11
[ 0084] An a queous s olution conta ining 40 pa rts by w eig h t
of urea a nd 40 pa rts by w eig h t of pine s a w dus t is boiled f or 2
h ours . Th e s olid urea lig nin cellulos e, urea cellulos e a nd
lig nin cellulos e a re pres s ed a nd th en th e w a ter s oluble urea
lig nin, lig nin, ca rboh ydra tes , h emi- cellulos e, turpentine a nd
oth er products a re ?ltered of f . Th e urea lig nin a re us ed to
produce a dh es iv es a nd res inous products . Th e urea lig nin
cellulos e a nd lig nin cellulos e ma y be retrea ted w ith delig ni
?ca tion a g ent s uch a s urea to produce more urea lig nin, lig nin,
urea cellulos e, ros in, ca rboh ydra tes a nd th e non- w a ter
s oluble rema ining urea lig nin cellulos e, lig nin cellulos e a nd
urea cellulos e ma y be us ed to produce pa per, ca rboh ydra tes
a nd a lcoh ol.
[ 0085 ] 20 pa rts by w eig h t of th e dried urea lig nin produced
a bov e is mix ed w ith 10 pa rts by w eig h t of s oy oil th en h ea ted
w h ile a g ita ting up to th e boiling point of th e s oy oil f or 30
minutes to 2 h ours or until th e mix ture s olidi?es w h en cooled
th ereby producing a urea lig nin s oy oil res inous product.
Ex a mple 12
[ 0086 ] Ex a mples 4, 5 , 6 a nd 7 a re modi?ed w h erein a noth er
a ldeh yde is us ed in pla ce of f orma ldeh yde a nd s elected f rom
th e lis t below or mix tures th ereof :
a ceta ldeh yde, butyl a ldeh yde, ch lora l, a crolein, f urf ura l, ben
Z a ldeh yde, crotona ldeh yde, propiona ldeh yde, penta na ls ,
h ex a na ls , h epta na ls , octa na ls a nd th ere s imple s ubs titution
products , s emi- a ceta te a nd f ull a ceta ls , pa ra f orma ldeh yde
a nd h ex a meth ylene tetra mine.
Ex a mple 13
[ 0087 ] 30 pa rts by w eig h t of th e s olid urea lig nin cellulos e,
urea cellulos e a nd lig nin cellulos e produced in ex a mple 1 a re
mix ed in w a ter conta ining 10 pa rts by w eig h t of s odium
h ydrox ide th en h ea ted until th e w a ter h a s ev a pora ted, th en 15
pa rts by w eig h t of epich loroh ydrin is a dded a nd mix ed th en
h ea ted to j us t below th e boiling point of epich loroh ydrin until
a th ick urea lig nin cellulos e epox y compound is f ormed th en
5 pa rts by w eig h t of dieth ylenetria mine is a dded, mix ed a nd
rea cted th ereby producing a cured lig nin cellulos e epox y
res in.
Ex a mple 14
[ 0088] 30 pa rts by w eig h t of urea lig nin in a nd a queous
s olution produced in ex a mple 1 a re mix ed w ith 15 pa rts by
w eig h t of s odium h ydrox ide th en h ea ted till th e w a ter ev a po
ra te th ereby producing a s odium s a lt of urea lig nin w h ich is
th en mix ed w ith 10 pa rts by w eig h t of epich loroh ydrin. Th e
US 2011/0098384 A1
mix ture is h ea ted to j us t below th e boiling point of epich lo
roh ydrin until a th ick mix ture is f ormed th ereby producing a n
urea lig nin epox y compound W h ich ma y be us ed a s a n a dh e
s iv e or a res inous product.
Ex a mple 15
[ 0089] Ex a mples 8, 9, 13 a nd 14 a re modi?ed W h erein a
?ller in th e a mount of 10 pa rts by W eig h t is a dded to th e
mix ture bef ore it is cured a nd s elected f rom th e lis t beloW a nd
mix tures th ereof :
in th e f orm of poW ders , g ra nula te, W ire, ?bers , dumb bells ,
crys ta llites , s pira ls , rods , bea ds , h olloW bea ds , f oa m pa rticles ,
W ebs , pieces of W ov en f a bric, k nit f a brics , ribbons , pieces of
?lm, etc. , f or ex a mple, of dolomite, ch a lk , a lumina , a s bes tos ,
ba s ic s ilica s , s a nd, ta lcum, iron ox ide, a luminum ox ide a nd
ox ide h ydra te, Z eolites , ca lcium s ilica tes , ba s a lt W ool or poW
der, g la s s ?bers , C- ?bers , g ra ph ite, ca rbon bla ck , A 1- , Fe- ,
Cu- , Ag - poW der, molybdenum s ulph ite, s teel W ool, bronZ e or
copper cloth , s ilicon poW der, ex pa nded cla y pa - nitrile, polyb
uta diene, polyis oprene, polytetra ?uoroeth ylene, a liph a tic
a nd a roma tic polyes ters , mela mine- urea or ph enol res ins ,
polya ceta l res ins , polyepox ides , polyh yda ntoins , poly urea ,
polyeth ers , polyureth a nes , polyimides , polya mides , polys ul
ph ones , polyca rbona tes , a nd copolymers .
Ex a mple 16
[ 0090] Ex a mple 1 1 is modi?ed W h erein a noth er pla nt oil is
us ed in pla ce of th e s oy oil a nd s elected f rom th e lis t beloW or
mix tures th ereof :
modi?ed s oy oil, cotton s eed oil, s a f ?oW er oil, corn oil, pa lm
oil, s un ?oW er oil, ca nola oil, ra pes eed oil, lins eed oil, a v o
ca do oil, bea ch nut oil, copra oil, h emp oil, h a Z elnut oil,
ra s pberry oil, cof f ee oil, ca s h eW oil, elderberry oil a nd
a lmonds oil.
Ex a mple 17
[ 0091] 25 pa rts by W eig h t of dry a mino lig nin poW der pro
duce in ex a mple 1 is mix ed 10 pa rts by W eig h t of s uccinic a cid
th e h ea ted to a bov e th e melting point of s uccinic a cid f or 0. 5
to 3 h ours th ereby producing a n a mino lig nin s uccinic poly
es ter res in W h ich ma y be us ed a s a n a dh es iv e or a molding
res in.
Ex a mple 18
[ 0092] Ex a mple 17 is modi?ed W h ere in a polyca rbox ylic
a cid or a nh ydride or mix ture th ereof a nd s elected f rom th e lis t
beloW ma y be us ed in pla ce of s uccinic a cid f or prepa ring
a mino lig nin polyes ters :
a dipic a cid, s eba cic a cid, s uberic a cid, a Z ela ic a cid, ph th a lic
a cid, ph th a lic a cid a nh ydride, is oph th a lic a cid, tetra h ydro
ph th a lic a cid a nh ydride, trimellitic a cid, h ex a h ydroph th a lic
a cid a nh ydride, tetra ch loroph th a lic a cid a nh ydride, endom
eth ylene tetra h ydroph th a lic a cid a nh ydride, g luta ric a cid
a nh ydride, f uma ric a cid, ma leic a cid, ma leic a cid a nh ydride,
dimeric a nd trimeric f a tty a cids s uch a s oleic a cid, optiona lly
mix ed W ith monomeric f a tty a cids , dimeth yltereph th a la te,
bis - g lycol tereph th a la te a nd mix ture th ereof a nd th e a mino
compound is urea .
Ex a mple 19
[ 0093] About 25 pa rts by W eig h t of g lycerol a nd 5 0 pa rts by
W eig h t of dry a mino lig nin produced in ex a mple 1 1 a re mix ed
Apr. 28, 2011
th en h ea ted to j us t beloW th e boiling point of g lycerol f or 1 to
4 h ours th ereby producing a a mino lig nin polyh ydric res in
W h ich is th en mix ed W ith 7 0 pa rts by W eig h t of polymeric
MD I a nd rea cted a nd poured into a mold th ereby producing a
polyureth a ne s olid product.
Ex a mple 20
[ 0094] Ex a mple 19 is modi?ed W h erein a noth er polyh ydric
compound is us ed in pla ce of g lycerol a nd s elected f rom th e
lis t beloW :
eth ylene g lycol; propylene- 1, 2- a nd - 1, 3- g lycol, butylene- 1,
4- a nd - 2, 3- g lycol; h ex a ne- 1, 6 - diol; octa ne- 1, 8- diol; neo
penth l g lycol; cycloh ex a nedimeth a nol- ( 1A- bis - h ydrox ym
eth ylcyclo- h ex a ne) ; 2 meth yl propa ne- 1, 3- diol; g lycerol;
trimeth ylol propa ne; h ex a ne- 1, 2, 6 - triol; buta ne- 1, 2, 4 triol;
trimeth yloleth a ne; penta eryth ritol; quinitol; a nnitol a nd s or
bitol; meth ylg lycos ide; dieth ylene g lycol; tri- eth ylene g ly
col; tetra eth ylene g lycol; polyeth ylene g lycols ; dipropylene
g lycol; polypropylene g lycols ; dibutylene g lycol; polybuty
lene g lycols ; trimeth ylolpropa ne; 4, 4- dih ydrox ydiph enyl
propa ne, a niline, a mmonia , eth a nola mine or eth ylenedi
a mine, s ucros e, s ta rch , s oy ?our, ca s tor oil, ca rboh ydra tes a nd
mix tures th ereof . Th e a mino lig nin is a urea lig nin.
Ex a mple 21
[ 0095 ] 25 pa rts by W eig h t of th e dry urea lig nin produced in
ex a mple 1 1 is mix ed W ith 10 pa rts by W eig h t of dieth ylen
etria mine th en h ea ted up to th e boiling point of dieth ylenetri
a mine f or 1 to 4 h ours th ereby producing a dieth ylenetria mine
urea lig nin. One pa rt by W eig h t of th e dieth ylenetria mine
a mino lig nin is mix ed a nd rea cted W ith a n epox y res in th ereby
producing a s olid epox y res in.
Ex a mple 22
[ 0096 ] Anoth er polya mine is us ed in pla ce of dieth ylenetri
a mine in ex a mple 21 a nd s elected f rom th e g roup beloW ;
eth yldia mine, tetra eth ylenepenta mine, tetra eth ylenedia mine,
propyldia mine, trieth ylenetetra mine, tetra meth ylenedi
a mine, penta meth ylenedia mine, h ex a meth ylenedia mine, a nd
mix tures th ereof .
Ex a mple 23
[ 0097 ] 25 pa rts by W eig h t of th e dry urea lig nin produced in
ex a mple 11 is mix ed W ith 10 pa rts by W eig h t of ph enol th en
h ea ted up to th e boiling point of th e ph enol f or 1 to 4 h ours
th ereby producing a ph enol a mino lig nin W h ich ma y be uti
liZ ed to rea ct W ith a n a ldeh yde to produce a poly( ph enopla s t
a mino lig nin) res in or a dh es iv e f or producing plyW ood, OB S,
pa rticleboa rd, etc.
Ex a mple 24
[ 0098] Anoth er ph enol compound ma y be us ed in pla ce of
ph enol in ex a mple 23 a nd s elected f rom th e g roup beloW ;
ph enol, p- cres ol, o- cres ol, m- cres ol, cres ylic a cid, x ylenols ,
res orcinol, ca s h eW nut s h ell liquids , a na cordol, p- tert- butyl
ph enol, B is ph enol A, creos ote oil, 2, 6 dimeth ylph enol a nd
mix tures th ereof . Ph enol is th e pref erred ph enol compound
a nd f orma ldeh yde is th e pref erred a ldeh yde W h en us ed W ith a
ph enol compound. Any s uita ble th ermos etting ph enol- f orm
a ldeh yde a nd urea - f orma ldeh yde res ins ma y be us ed in th is
US 2011/0098384 A1
inv ention. Any s uita ble mix ture of th e a mino compounds a nd
ph enol compounds W ith a n a ldeh yde ma y be us ed in th is
inv ention.
Ex a mple 25
[ 0099] Ex a mple 7 is modi?ed W h erein a noth er ?our is us ed
in pla ce of s oy ?our a nd s elected f rom th e lis t beloW ;
W h ea t ?our, oa t ?our, cellulos e ?our, s ta rch , corn mea l, linen
?our, ba rley ?our a nd mix tures th ereof .
Ex a mple 26
[ 0100] 20 pa rts by W eig h t of g round rice s ta lk s a nd 15 pa rts
by W eig h t of urea W a s a dded to W a ter th en boiled f or 1 h our
th en 6 0 pa rts by W eig h t of a queous f orma ldeh yde ( 37 %) a nd
a queous a mmonia to a dj us t th e pH 8- 10 th en boiled till a ll of
th e f ree W a ter W a s ev a pora ted th ere by producing a th ermo
pla s tic res in, th en s uf ?cient a mmonia s ulf a te W a s a dded to
a dj us t th e pH 5 - 6 a nd th en pla ced into a mold a nd h ea ted to
300 deg rees F. until th e th ermopla s tic res in h a rdened into a
th errnos etting res in.
Ex a mple 27
[ 0101] Ex a mple 26 is modi?ed W h erein a noth er lig nin cel
lulos e pla nt is us ed in pla ce of g round rice s ta lk s a nd th e
g round lig nin cellulos e is s elected f rom th e lis t beloW :
s pruce, pine, h emlock , oa k , a s h , la rch , birch , a s pen, popla r,
ceda r, beech , ma ple, W a lnut, cypres s , redW ood, ch erry, elm,
ch es tnut, h ick ory, locus t, s yca more, tulip, tupelo, butternut,
a pple, a lder, ma g nolia , dog W ood, ca ta lpa , box W ood, cra b
W ood, ma h og a ny, g reenh ea rt, la nceW ood, letterW ood, mora ,
prima v era , purpleh ea rt, ros e. - W ood, tea k , s a tinW ood, ma n
g rov e, W a ttle, ora ng e, lemon, log W ood, f us tic, os a g e ora ng e,
s a ppa nW ood, B ra Z ilW ood, ba rW ood, ca mW ood, s a nda lW ood,
rubber, g utta , mes quite, a nd s h rubs , e. g . , olea nder, cypres s ,
j unipers , a ca nth us , pyra ca nth a , lig us trum, la ta na , boug a in
v illea , a Z a lea , f eij oa , ilex , f us cia , h ibis cus , da tum, h olly,
h ydra ng ea , j a s mine, euca lyptus , cottonea s ter, x ylos ma ,
rh odeodendron, ca s tor bea n, eug enia , euonymus , f a ts h edera ,
a ra lia , etc. , a nd a g ricultura l pla nts , e. g . , cotton, cotton s ta lk s ,
corn s ta lk s , corn cobs , W h ea t s tra W , oa t s tra W , rice s tra W , ca ne
s ug a r ( ba g a s s e) , s oybea n s ta lk s , pea nut pla nts , pea v ines ,
s ug a r beet W a s te, s org h um s ta lk s toba cco s ta lk s , ma iZ e
s ta lk s , ba rley s tra W , buck W h ea t s tra W , quinoa s ta lk s , ca s s a ya ,
pota to pla nts , leg ume v ines a nd s ta lk s , v eg eta ble inedible
portion, etc. , W eeds , g ra s s es , v ines , k elp, ?oW ers , a lg a e,
pa per, cotton cloth , ba g a s s e W a llboa rd, W ood products ,
h umus , pea t, certa in s of t broW n coa l a nd mix tures th ereof .
1 cla im:
1. A meth od f or delig ni?ca tion of lig nin cellulos e a nd
rea cting th e delig ni?ca tion compounds W ith a n rea ctiv e
org a nic or inorg a nic ch emica l by th e meth od compris ing th e
s teps of :
A) a dding 5 0 to 100 pa rts by W eig h t of lig nin cellulos e
pa rticles ;
B ) a dding 10 to 100 pa rts by W eig h t of a n a mino compound
s elected f rom th e g roup cons is ting of urea , g ua nidine,
a minog ua nidine, g ua nidine ca rbona te a nd urea mix ed
W ith oth er a mino compounds a nd mix ture th ereof ;
C) a dding W a ter;
th en h ea t th e mix ture a t a mbient or elev a ted pres s ure, a t
a mbient or up to 15 0 deg ree C. f or 0. 5 to 24 h ours
th ereby producing a mix ture of a mino lig nin, a mino
Apr. 28, 2011
lig nin cellulos e, a mino cellulos e, lig nin cellulos e, lig
nin, ca rboh ydra tes , h emi- cellulos e, res ins , ros ins a nd
a lcoh ols ;
D ) a dding 25 to 100 pa rts by W eig h t of ch emica lly a ctiv e
org a nic a nd/inorg a nic compound to one or a mix ture of
th e compounds produced in s tep C th en rea ct th e com
pounds by mix ing th e compounds of s tep C W ith a nd
ch emica lly a ctiv e org a nic a nd/or inorg a nic compound
s elected f rom th e lis t beloW a t a mbient or elev a ted pres
s ure a nd a t a mbient tempera ture up to th e boiling point
of th e ch emica lly a ctiv e org a nic a nd/or inorg a nic com
pound f or 1 to 4 h ours ; lis ted ch emica lly a ctiv e ch emi
ca ls cons is t of a ldeh ydes , org a nic a cids , inorg a nic a cids ,
k etones , a mines , polya mines , a mino compounds , epox y
compounds , polyepox y, polys ulf one, polyimines , ph e
nopla s ts , a minopla s ts , polyes ters , polyeth ers a nd poly
th ioeth ers conta ining iOH ra dicles , v eg eta ble oils ,
f a ts , ca rboh ydra tes , s oy ?our, proteins , s ta rch , W h ea t
?ours , cellulos e, a lcoh ols , polyca rbox ylic a cids , polya l
coh ols , polyis ocya na tes , polyca rbona tes W ith 40H
ra dicles , epich loroh ydrin, org a nic s ubs tituted com
pounds , f urf urol, f urf uryl a lcoh ol, org a nic ph os ph orus
compounds , s ome uns a tura ted org a nic compounds ,
a lk a li meta l compounds , a lk a li meta l ea rth compounds
a nd mix tures th ereof .
2. A meth od in a ccorda nce W ith cla im 1 W h erein th e a mino
compound is a mix ture of urea a nd a n a mino compound
s elected f rom th e g roup cons is ting of th iourea , a lk yl- s ubs ti
tuted th iourea , a lk yl s ubs tituted urea s , mela mine, a niline,
g ua nidine, a mino g ua nidine, mela mine cya nura te, biuret, cya
nuric a cid, s a cch a rin, urea condens a tes s uch a s urea - cya ndia
mide, urea - a minoinog ua nidine condens a te, urea g ua nidine
condens a te, urea polya mine condens a te, cya melide, urea
mela mine condens a te, urea - dicya ndia mide, urea cya n
og ua nidine condens a te, urea cya na te condens a tes a nd a mi
noph os ph a tes W ith f ree N H2, toluene s ulf ona mide, a liph a tic
a nd a roma tic polya mines a nd mix tures th ereof .
3. A meth od a ccorda nce W ith cla im 1 W h erein th e W a ter
s oluble compounds , a mino lig nin, lig nin, ca rboh ydra tes ,
a lcoh ols , ros ins , a nd h emi- cellulos e a re ?ltered f rom th e non
W a ter s oluble s olid compounds , a mino lig nin cellulos e, cel
lulos e a nd lig nin cellulos e.
4. A meth od a ccorda nce W ith cla im 1 W h erein 5 0 to 100
pa rts by W eig h t of th e mois t mix ture of a mino lig nin, a mino
lig nin cellulos e, lig nin, lig nin cellulos e, ca rboh ydra tes , h emi
cellulos e, res ins , ros ins a nd a lcoh ol is mix ed a nd rea cted W ith
25 to 100 pa rts by W eig h t of polyis ocya na te th ereby produc
ing a s olid res inous product.
5 . A meth od a ccorda nce W ith cla im 3 W h erein th e 5 0 to 100
pa rts by W eig h t of mois t W a ter s oluble mix ture of a mino
lig nin, lig nin, ca rboh ydra tes , a lcoh ols , ros ins a nd h emi- cel
lulos e is mix ed a nd rea cted W ith 25 to 100 pa rts by W eig h t of
PMD I th ereby producing a micro cellula r f oa m product.
6 . A meth od a ccorda nce W ith cla im 4 W h erein 10 to 5 0
pa rts by W eig h t of a bloW ing a g ent, 0. 1 to 5 pa rts by W eig h t of
a s ilicone s urf a cta nt a nd 0. 1 to 10 pa rts by W eig h t of a ure
th a ne ca ta lys t W a s a dded to th e mix ture bef ore f oa ming
s ta rted th ereby producing a rig id polyureth a ne f oa m.
7 . A meth od a ccorda nce W ith cla im 1 W h erein th e a queous
mix ture, produced in th e delig ni?ca tion of lig nin cellulos e,
a mino lig nin, lig nin, a mino cellulos e, a mino lig nin cellulos e
a nd lig nin cellulos e a re rea cted W ith 25 to 100 pa rts by W eig h t
of a n a ldeh yde by h ea ting th e mix ture a nd ev a pora ting th e
US 2011/0098384 A1
W a ter a nd continue h ea ting th e mix ture until it s olidi?es
th ereby producing a poly( a ldeh yde a mino lig nin a mino lig nin
cellulos e res inous product.
8. A meth od a ccorda nce W ith cla im 7 W h erein th e a ldeh yde
is f orma ldeh yde.
9. A meth od a ccorda nce W ith cla im 1 W h erein th e a mino
lig nin in th e a mount of 5 0 to 100 pa rts by W eig h t pa rts by
W eig h t of is ch emica lly rea cted W ith a ch emica lly a ctiv e
compound in th e a mount of 25 to 100 pa rts by W eig h t a nd
s elected f rom th e g roup cons is ting of a ldeh ydes , org a nic
a cids , inorg a nic a cids , k etones , a mines , polya mines , a mino
compounds , epox y compounds , polyepox y, polys ulf one,
polyimines , ph enopla s ts , a minopla s ts , polyes ters , polyeth ers
a nd polyth ioeth ers conta ining 40H ra dicles , v eg eta ble oils ,
f a ts , ca rboh ydra tes , s oy ?our, proteins , s ta rch , W h ea t ?ours ,
cellulos e, a lcoh ols , polyca rbox ylic a cids , polya lcoh ols , poly
is ocya na tes , polyca rbona tes W ith iOH ra dicles , epich loro
h ydrin, org a nic s ubs tituted compounds , f urf urol, f urf uryl
a lcoh ol, org a nic ph os ph orus compounds , a lk a li meta l com
pounds , a lk a li meta l ea rth compounds a nd mix tures th ereof .
10. A meth od to produce ?a me reta rda nt, W a ter res is ta nt,
a mino lig nin cellulos e th ermopla s tic a nd th ermos etting res
inous products by th e meth od of a dding , mix ing , h ea ting a nd
rea cting th e f olloW ing components :
a ) lig nin cellulos e pa rticles , 5 0 to 100 pa rts by W eig h t,
b) urea a nd/or g ua nidine compounds , 10 to 100 pa rts by
W eig h t,
c) W a ter, mix th en h ea t a nd th en a dd
d) a ldeh yde, 25 to 100 pa rts by W eig h t,
e) ba s ic compound to a dj us t pH 7 - 10 th en h ea t
th ereby producing a n a mino lig nin cellulos e a ldeh yde th er
mopla s tic res inous product th en a dd a n
f ) a cidic compound to a dj us t th e pH to 3- 6 a nd h ea t
th ereby producing a n a mino lig nin cellulos e th ermos etting
res inous product.
11. A meth od a ccording to cla im 10 W h erein th e a ldeh yde
is f orma ldeh yde.
12. A meth od to produce a mino lig nin res ins a nd a dh es iv es
res ins by th e meth od of a dding , mix ing , h ea ting a nd rea cting
th e f olloW ing components :
a ) lig nin cellulos e pa rticles , in th e a mount of 5 0 to 100
pa rts by W eig h t,
b) urea , in th e a mount of 10 to 100 pa rts by W eig h t
c) W a ter, mix th en h ea t a nd rea ct th ereby producing W a ter
s oluble urea lig nin, lig nin, ca rboh ydra tes , res ins , a lco
h ol, h emi- cellulos e a nd non- W a ter s oluble urea lig nin
cellulos e, urea cellulos e a nd lig nin cellulos e, th en ?lter
of f th e a queous s olution a nd a dd to it
d) a ldeh yde, 25 to 100 pa rts by W eig h t,
e) ba s ic compound to a dj us t th e pH to 7 - 10 th en h ea t
th ereby producing a th ermopla s tic a ldeh yde urea lig nin
res in or a dh es iv e th en a dding a
f ) a cidic compound to a dj us t th e pH to 3- 6 th en h ea t th e
a ldeh yde urea lig nin res in or a dh es iv e th ereby producing
a th ermopla s tic urea lig nin res in.
13. A meth od a ccording to cla ims 7 , 10 a nd 12 W h erein th e
a ldeh yde is s elected f rom th e g roup cons is ting of f orma lde
h yde, a ceta ldeh yde, butyl a ldeh yde, ch lora l, a crolein, f ur
Apr. 28, 2011
f ura l, benZ a ldeh yde, crotona ldeh yde, propiona ldeh yde, pen
ta na ls , h ex a na ls , h epta na ls , octa na ls a nd th ere s imple
s ubs titution products , s emi- a ceta te a nd f ull a ceta ls ,
pa ra f orma ldeh yde, h ex a meth ylene tetra meth ylene a nd mix
tures th ereof .
14. A meth od a ccording to cla im 1 W h erein 2- 5 pa rts by
W eig h t of a mino lig nin produced by th e meth od of th is inv en
tion is mix ed W ith a nd rea cted W ith 2 pa rts by W eig h t of
s odium h ydrox ide th en 2 pa rts by W eig h t of epich loroh ydrin
a re a dded a nd mix ed, th e mix ture is h ea ted to j us t beloW th e
boiling point of epich loroh ydrin f or 1- 2 h ours a nd rea cted
th ereby producing a a mino liquid epox y compound th en a dd
a nd mix 1 pa rt by W eig h t of a n epox y h a rdner cons is ting of a
polya mine compound th ereby producing a a n a mino lig nin
polyepox y res inous product.
15 . A meth od a ccording to cla ims 4 a nd 6 W h erein th e
polyis ocya na te is s elected f rom th e g roup cons is ting of
tolylene- 2, 4- a nd - 2, 6 - diis ocya na te a nd a ny mix tures of th es e
dimers , ( TD I ) , polyph enyl- polymeth ylene- is ocya na tes
obta ined by a niline- f orma ldeh yde condens a tion f olloW ed by
ph os g ena tion ( crude MD I ) , PMD I, polyis ocya na tes W h ich
conta in ca rbodiimide g roups , ureth a ne g roups , a lloph a na te
g roups , is ocya nura te g roups , urea g roups , imide g roups or
biuret g roups , inorg a nic polyis ocya na tes , polyis ocya na te
prepolymers a nd mix tures th ereof .
16 . A meth od a ccording to cla im 1 W h erein th e a mino
lig nin, a mino lig nin cellulos e, a mino cellulos e a nd lig nin
cellulos e is a dded, mix ed, a nd rea cted a ph enol compound
a nd a n a ldeh yde th ereby producing a poly( ph enopla s t a mino
lig nin cellulos e) res in.
18. A meth od a ccording to cla im 16 W h erein th e ph enol
compound is s elected f rom th e g roup cons is ting of ph enol,
p- cres ol, o- cres ol, m- cres ol, cres ylic a cid, x ylenols , res orci
nol, ca s h eW nut s h ell liquids , a na cordol, p- tert- butyl ph enol,
B is ph enol A, creos ote oil, 2, 6 dimeth ylph enol a nd mix tures
th ereof a nd th e a ldeh yde g roup is s elected f rom th e g roup
cons is ting of f orma ldeh yde, a ceta ldeh yde, butyl a ldeh yde,
ch lora l, a crolein, f urf ura l, benZ a ldeh yde, crotona ldeh yde,
propiona ldeh yde, penta na ls , h ex a na ls , h epta na ls , octa na ls
a nd th ere s imple s ubs titution products , s emi- a ceta te a nd f ull
a ceta ls , pa ra f orma ldeh yde, h ex a meth ylene tetra meth ylene
a nd mix tures th ereof .
19. A meth od a ccording to cla im 1 W h erein th e a mino
lig nin is a dded, mix ed a nd rea cted W ith a polyca rbox ylic a cid
s elected f rom th e g roup cons is ting of a dipic a cid, s eba cic
a cid, s uberic a cid, a Z ela ic a cid, ph th a lic a cid, ph th a lic a cid
a nh ydride, is oph th a lic a cid, tetra h ydro- ph th a lic a cid a nh y
dride, trimellitic a cid, h ex a h ydroph th a lic a cid a nh ydride, tet
ra ch loroph th a lic a cid a nh ydride, endometh ylene tetra h ydro
ph th a lic a cid a nh ydride, g luta ric a cid a nh ydride, f uma ric
a cid, ma leic a cid, ma leic a cid a nh ydride, dimeric a nd trimeric
f a tty a cids s uch a s oleic a cid, a nd mix ture th ereof .
20. A meth od a ccording to cla im 1 W h erein th e a mino
lig nin, a mino lig nin cellulos e, a mino cellulos e a nd lig nin
cellulos e is a dded, mix ed a nd rea cted W ith a n f urf uryl a lcoh ol
th ereby producing poly( f urf uryl a lcoh ol a mino lig nin a mino
lig nin cellulos e) res in.
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