CHEMISTRY OF

ISOCYANATE

PRESENTED BY BIKASH DUTTA

Isocyanates
Types of Isocyanate:
•Aromatic Isocyanate
•Aliphatic Isocyanate
•Alicyclic Isocynate.
Reactivity of Aromatic Isocyanate is faster than
Aliphatic Isocyanate however Aromatic
Isocyanate is more carcinogenic.
Isocyanates:
COMMON ISOCYANATES
Types of Polyisocyanate
Isocyanates are always made in polymerized
Form since the monomeric isocyanates are highly
Vaporizable leading to handling & safety related
issues
- Biuret
- Isocyanurate (Trimer)
- Uretdione (Dimer)
- Allophanate
Reactivity of isocyanates
RESONANCE OF ISOCYANATES

The isocyanate group bears cumulated double bond

sequence as R-N=C=O, wherein the reactivity of
isocyanate is governed by the positive character(F 1) of the
carbon atom , which is susceptible to attack by
nucleophiles, and oxygen and nitrogen by
electrophiles( where R = Alkyl Group)

If R is an aromatic group, the negative charge gets

delocalized into R (Fig 2), thus, the aromatic
isocyanates are more reactive than aliphatic or
cycloaliphatic isocyanates.
PUR chemistry
O

C+ H-O R
R N

Catalyst used:
DBTDL

C
R N O R

H Urethane linkage
Function Of DBTL
The excellent catalytical performance of DBTL is based on its Lewis Acid properties. The literature
shows that complexation of the tin center in the DBTL to the NCO-group is one of the key steps in
the catalysis of the urethane reaction.

Catalysis of the PU reaction By DBTL

Alternatives to DBTL
There are numerous metal compounds have been evaluated in the past as catalysts for the
urethane forming reaction.

The driving forces for the replacement are the ongoing toxicological discussions. Latest since

the ban of the tributyltin compounds from use in antifouling paints.

The following catalysts show some potential as DBTL replacement products:

-Dioctyltindilaurate – (DOTL)
- Bismuth Octoate - (Bi-OC)

DOTL is chemically quite close to DBTL. The only difference is the chain length of the alkyl
groups attached to the tin center. It can be expected that due to the very similar chemistry the
catalytical performance is quite close to DBTL. Currently DOTL is not regarded as a dangerous
material, but this may change in the future.

From the toxicological point of view Bismuth products are generally recognized as low
toxic materials
Reaction with Moisture
Isocyanates react with water to form carbon di oxide and amine:

The carbon dioxide functions as a blowing agent. Isocyanates also

react with amines to give ureas
Relation b/w %OH and OH
value
56100
OH value =
Equivalent wt

1700
%OH =
Equivalent wt

OH value
%OH =
33
Cross Linking Ratio
PUR chemistry

Amt of
Amt of solid resin x %OH x mol. wt. of NCO moiety
isocyanate
required for % NCO x mol. wt. of OH moiety
100% CR
Mol wt of NCO moiety = 42
Mol wt of OH moiety = 17
Factor = 2.47

Amt of
Amt of solid resin x %OH x 2.47
isocyanate
required for % NCO
100% CR
 PUR Chemistry………….

% OH of the mix Resin A & B

[(amt solid resin A) x (%OH of resin A)] + [(amt of solid resin B) x (%OH of resin B)]
% OH mix =
[amt solid resin A+ amt of solid resin B]

%NCO of the mix Isocyanate A & B

[(amt of isocyanate A) x (%NCO of A)] + [(amt of isocyanate B) x (%NCO of B)]

% NCO mix =
100
Calculation of cross linking ratio
from mixing ratio
Details of the product
Amt of resin %N.V. of resin %OH/ %NCO S.G. of paint
Part A 23 0.51 4.5 1.61

Part B 51 0.6 19.8 0.99

Mixing ratio 3 1
Amount of each component by wt 4.83 0.99

Amt of each component/100 gm part A 100 20.49

Hence, practical amount of Isocyanate = (20.49 x 60)/100 gm

= 12.29 gm
 Calculation of cross linking
ratio
from mixing ratio …….cont.
Amt of resin %N.V. of resin %OH/ %NCO
Part A 23 0.51 4.5
Part B 51 0.9 19.8

Amt of
Amt of solid resin x %OH x 2.47
isocyanate
required for % NCO
100% CR
23 x 0.51 x 4.5 x 2.47

19.8
= 6.58
Practical amt of isocyanate
Actual cross linking = = 12.29/6.58 = 1.89
Theoretical amt of isocyanate
End Of Slides

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