7 Chemical Depolymerization of Polyurethane Foam via
Ammonolysis and Aminolysis
Maharashtra Institute of Technology, Aurangabad, Maharashtra, India
7.1 Introduction
Chemical recycling of polymers is generally car-
ried out to recover valuable monomers or precur-
sors of the monomers from expensive engineering
plastics. For such recovery using chemical depo-
lymerization, almost uniform composition and
sufficient purity of the polymer are required.
Polyurethanes (PUs) are also considered to have
potential ability to retrieve monomers from expen-
sive polymers. Among different methods of recy-
cling, ammonolysis and aminolysis are relatively
less explored in contrast to the widely used meth-
ods like glycolysis and acidolysis. The ammonoly-
sis method involves the use of ammonia in the
depolymerizing reaction, whereas the aminolysis
method involves the use of amines or alkanola-
mines to yield polyols from PU scrap foams (PUF).
For depolymerization of PU, low molecular
weight diols and water are generally used as cleav-
ing agents. The complex mixtures of different com-
pounds in the resulting mixture may be used
directly for the manufacturing of lower quality PU.
Otherwise, such mixtures may also be used for the
same after the treatment with propylene oxide or
ethylene oxide.1,2
Table 7.1 Comparative Analysis of Reaction Conditions and Constituents of Products for Different
Depolymerization Methods Used for PU Recycling
Categories of
Comparison Hydrolysis
Temperature High temperature
Pressure High pressure
Product Original polyols
Isocyanate
derivatives
Recycling of Polyurethane Foams. DOI: https://doi.org/10.1016/B978-0-323-51133-9.00007-3
© 2018 Elsevier Inc. All rights reserved.
Subhendu Bhandari and Prashant Gupta
7.2 Aminolysis of PU Foam
In a broad perspective, “chemolysis” process of
recycling involves depolymerization of a polymer
through de-cross-linking or chain scission by using
different chemicals. Polyester-based PUs decom-
pose easier than polyether-based PUs. Different
depolymerization methods have been proposed,
which include glycolysis, alcoholysis, and aminoly-
sis,3 as well as possible combination, e.g., hydro-
glycolysis.4,5 However, these processes differ in the
reagents used, processing conditions, steps
involved, as well as the quality of the end products.
Among different chemolysis processes, aminolysis
process is different from the other chemical recy-
cling processes, e.g., hydrolysis, glycolysis, metha-
nolysis, etc., in terms of the types of reagents used
for depolymerization as well as the composition of
the final product. The comparative analysis of the
reaction conditions and products of different meth-
ods of PU recycling has been shown in Table 7.1.
In hydrolysis process, water is used for depolymeri-
zation. However, this type of depolymerization do
not take place at atmospheric pressure and room
temperature, rather, it requires relatively higher
pressure and temperature in comparison to the other
Glycolysis Aminolysis
High temperature Room temperature
Atmospheric pressure Atmospheric pressure
Original polyols Original polyols
Isocyanate-containing Distributed ureas
polyols
77
78
processes. For hydrolysis of PU, pressure is gener-
ally maintained at 230 psi (i.e., 16 bar), whereas
temperature needs to reach beyond 200°C. For the
use of water at elevated temperature, superheated
steam is used in this process. In this process ure-
thane linkages are hydrolyzed which were also
reported in some patents.6,7 Original polyols and
amine precursors (derivatives of isocyanates) are
obtained from hydrolysis process. Unlike hydrolysis
process, glycolysis can be accomplished at atmo-
spheric pressure although requirement of tempera-
ture ranges from 180°C to 240°C. This process
recovers original polyols as well as the polyols con-
taining isocyanates. In comparison to both these
two processes, aminolysis is advantageous, viz.,
Figure 7.1 Chemical structures of different amines and alkanolamines commonly used for aminolysis of PUF.
RECYCLING OF POLYURETHANE FOAMS
necessary processing condition that involves atmo-
spheric pressure as well as relatively much lower
temperature.8 Nevertheless, glycolysis involves the
use of glycols to yield amines, whereas aminolysis
involves gradual consumption of amines.
Therefore, with the increase of [foam]:[amine
decomposer] ratio, total amine number of recycled
product decreases in case of aminolysis while com-
pared to glycolysis.9
In the process of aminolysis, amines, ammonia,10
or alkanolamines11,12 is used. Commonly used
amines and alkanolamines for aminolysis of PUs
are shown in Fig. 7.1. While ammonia is used indi-
vidually or in the presence of water, the reaction
results in complex mixtures. The blend of mono
7: CHEMICAL DEPOLYMERIZATION OF POLYURETHANE FOAM VIA AMMONOLYSIS AND AMINOLYSIS 79

and polyamines may also be used instead of single
amine in order to recover polyols with improved
purity.13,14
On the other hand, the use of alkanolamine
requires drastic reaction conditions and the reaction
is slower compared to the use of ammonia because
of the less basicity of its nitrogen group. However,
for the use of amines, reaction time is compara-
tively less than the use of alkanolamine and the
required reaction conditions are also less drastic.15
The amines used in aminolysis include dibutyla-
mine and ethanolamine which react with PUs to
yield polyol and substituted urea.16 The schematic
representation of the depolymerization reaction by
using amines has been represented in Fig. 7.2.
Urethane or urea type adducts of methylene
diphenyl isocyanate (MDI) with monoethylene
amine (MEA) can be synthesized in presence of
excess amount of MEA (Fig. 7.3). Further reaction
of MDI
MEA adduct with excess amount of MEA

Figure 7.2 Reaction scheme for the use of amines in the process of aminolysis of PUs.16

Figure 7.3 Schematic representation of decomposition of urethane bond by using MEA.16

80
yields methylene diphenyl amine (MDA) and 2-
hydroxyethylcarbamic acid 2-aminoethylester by
breaking urethane bonds of foam by the -OH group
of MEA.16 Again, on reaction with urethane
groups, MEA initially forms an intermediate associ-
ation which in turn yields MDI
MEA urethane
adduct. However, in decomposition of MDI
MEA
adduct, alcoholysis prevails rather than aminolysis.
Similar adduct may also be formed for other types
of isocyanates and alkanolamines. For examples,
adduct of toluene diisocyanate (TDI) and diethano-
lamine (DEA) may form during recycling of PU
foam (PUF).17
Van der Waal18 proposed a modified method of
aminolysis involving two steps. In the first step,
depolymerization is carried out to yield a highly
concentrated emulsion
dispersion of ureas, carba-
mates, polyols, and amines. The dispersion is then
alkoxylated in the next step of the method to yield
high-functional polyol by removing any aromatic
Figure 7.4 Metal oxide catalyzed aminolytic degradation reactions of PU.16
RECYCLING OF POLYURETHANE FOAMS
amine. The first step, i.e., depolymerization may
further be categorized into the following stages:
• Metal oxide catalyzed breakdown of polymer
chain by reaction with alkanolamine
This stage of depolymerization involves
reaction of urethane and urea with alkanola-
mine in the presence of a metal hydroxide cat-
alyst (e.g., KOH) at elevated temperature (ca.
120°C). The reaction of alkanolamine with PU
yields carbamate polyols and original polyol,
whereas the reaction of alkanolamine with
urea yields carbamate polyols and amines. The
mechanism of such depolymerization has been
shown schematically in Fig. 7.4.
• Hydrolysis of PU
Water present in the reaction medium
hydrolyzes urea and PU. Hydrolysis of urea
yields amines, whereas hydrolysis of urethane
yields amine and polyol (Fig. 7.5).
7: CHEMICAL DEPOLYMERIZATION OF POLYURETHANE FOAM
• Reaction with metal oxide
Apart from having catalytic effect of metal
hydroxide in depolymerization of polymer, it
may also undergo reaction with PU/urea to
yield original polyol and aromatic amines. The
mechanism concerned to reaction of metal
oxide has been shown in Fig. 7.6.
• Aromatic amine catalyzed depolymerization of
PU
The aromatic amines formed in the above-
mentioned reactions also catalyze depolymeri-
zation of PU which yields urea, carbamate
polyol, amine, and the original polyol
(Fig. 7.7).
In the first step of the recycling process, for the
ratio PUF to alkanolamine (w/w) up to 12:1, the
resulting product found was a nonhomogeneous
and unstable phase-separated liquid. However,
stable emulsion was obtained at a weight ratio
higher than 12:1. Dispersion of solid material was
identified distinctly beyond weight ratio of 30:1.
Figure 7.5 Hydrolysis reaction of urea and urethane by water present in the reaction medium.16
Figure 7.6 Reaction of metal oxide with PU and urea.16
VIA AMMONOLYSIS AND AMINOLYSIS 81
In the second step, the resulting emulsion of the
previous step containing amine was reacted with
alkylene oxide to yield polyol. According to the
suggested mechanism, alkoxylation, primary or sec-
ondary amines and hydroxyl-containing fragments
react with propylene oxide (Fig. 7.8).
The tandem process of aminolysis was devel-
oped by Dow Benelux. The process has similarity
to the split-phase glycolysis process regarding the
types of polyols recovered. Both rigid as well as
flexible foam base polyols can be recovered
through this process. In the Dow process, PU scrap
is dissolved in an aqueous solution of
alkanolamine-KOH solution at ca. 120°C resulting
in formation of a high concentration emulsion con-
taining polyols, amines, urea, and carbamates. The
proportion of alkanolamine is typically varied from
1:50 to 1:15 with respect to the weight of PU scrap.
Thus, a very high volume ( . 1 m3) of PU can be
dissolved in 1 L of alkanolamine. The yielded mix-
ture consists of (1) alkoxylated aromatic amines,
(2) alkoxylated carbamates, and (3) alkoxylated
82 RECYCLING OF POLYURETHANE FOAMS

Figure 7.7 Aromatic amine catalyzed depolymerization of PU.16

Figure 7.8 Alkoxylation of amine and hydroxyl-containing fragments.16

Table 7.2 Effect of Temperature on Aminolysis of PUF

Change of Temperature Parameter Effect

Increase Time for solubilization of foam Decrease
Increase Reaction rate Increase
Increase Viscosity Increase
Increase Total amine number No significant change

polyols (used as the base material for the synthesis
of PUF).19
Aminolysis of PUF may or may not involve the
use of catalyst. Moreover, the rate of depolymeriza-
tion of PUF also exhibit good correlation to the
basicity of the degrading reagent. For example,
among different alkylamines, diethylenetriamine
(DETA) is a stronger base in comparison to triethy-
lenetetramine (TETA) and triethylenepentamine
(TEPA). Therefore, the use of DETA influences
depolymerization rate towards faster, reducing vis-
cosity of aminolyzed material and more complete-
ness in comparison to TETA and TEPA.9,20,21
The increase of reaction temperature decreases
time to solubilize the foam, therefore increasing
reaction rate. Moreover, viscosity increases greatly
with the increase of reaction temperature, whereas
total amine number does not change significantly
(Table 7.2).
The rate of thermal decomposition of PU
depends on the basicity of the amine solvents. For
example, rate of dissociation for some amine sol-
vents follows the decreasing order: di-n-butylamine
. ethanolamine  lauryl amine  HMDA .
benzylamine. Alike acidic medium, the presence of
amine, i.e., basicity of the solvent medium also
7: CHEMICAL DEPOLYMERIZATION OF POLYURETHANE FOAM
accelerates decomposition reaction nearly to the
same extent.21
Potassium hydroxide may be used to catalyze
depolymerization reaction. It may be used during
the course of induction for the use of alkanola-
mines. However, KOH may be replaced by NaOH
along with using DETA as degrading agent at 180°
C for 70 minutes.13 For that case, viscosity of the
aminolyzed product decreases with the increase of
the amount of NaOH used. 4,40 -methylenediamine
(MDA) may be obtained from depolymerization by
NaOH catalyzed reaction of DETA or by the reac-
tion of NaOH itself. With the increase of the
amount of NaOH, consumption of MDA increases,
i.e., its concentration decreases.
An important insight regarding the depolymeri-
zation of PU using alkanolamine was contributed
by Kanaya et al.16 In their investigation, MDI-
based PUF was recycled using alkanolamine at
150°C without using any catalyst which yielded
phase-separated product. The upper layer consisted
of polyether polyol, whereas methylene diphenyl
amine and alkanolamine derivatives like 2-
carboxyethyl carbamic acid were found to be pres-
ent in the lower layer. Monoethanolamine (MEA)
was used as alkanolamine which is expected to
undergo aminolysis reaction predominantly over
alcoholysis since amine group is more basic in
nature compared to hydroxyl group. However, the
investigation revealed that alcoholysis was predom-
inant over aminolysis because the C-O bond associ-
ated with MEA which is involved in the H-bonding
with urethane group dissociates much easier than
the H-bonding between the nitrogen of the amine
group and the carbonyl group of the urethane.
Apart from the conventional methods, some dif-
ferent approaches were also studied by the
researchers. Low molecular weight urethanes
derived from catechin was found to decompose fas-
ter at elevated temperature by both aminolytic as
well as hydrolytic cleavage without using any cata-
lyst.22 Sakai et al.23 investigated about aminolysis
of PUFs derived from wattle tannin (WT) and tri-
methylolpropane (TMP) by addition of small
amount of aniline during hydrolysis. Chopped PUF
particles were added to a solution containing 30 mL
acetonitrile, and 55 mM water and 10 mM aniline.
The presence of small amount of aniline acceler-
ated decomposition of WT-PUF, whereas such
influence of aniline was found to be negligible for
the case of TMP-PUF.
VIA AMMONOLYSIS AND AMINOLYSIS 83
Apart from using different decomposing ingredi-
ents, modification of recycling process condition
may also have significant effect on the yield prod-
uct. Such a modified process was suggested by
Fukaya et al.,17 which involves partial decomposi-
tion of PU by alkanolamine followed by reheating
in an extruder. According to this process, DEA is
sprayed on smashed PUF before feeding into
extruder. The heating temperature is maintained at
250°C
280°C for 4 to 6 hours. The viscous brown
material is soon cooled to room temperature fol-
lowed by reheating in drying oven. Reheating at
175°C
200°C yields a product of stable viscosity
regardless of the amount of decomposing agent or
extrusion condition. An intermediate adduct formed
between TDI and DEA is found to be responsible
for the instability of viscosity of the discharged
material. At the initial stage of reheating, the inter-
mediate adduct decomposes to yield TDI which in
turn facilitates the decomposition of PU. However,
for reheating at 200°C for beyond 4 hours or at
temperature beyond 225°C resulted in increase of
viscosity.
PUF may be recycled using a mixture of amine
and polyol in the presence of DEA as decomposing
agent24; however, heterocyclic compounds may be
produced as a by-product (Fig. 7.9). After initial
decomposition, the yielded products may be further
decomposed to yield amines and reclaimed PU.
Reclaimed PU elastomer may be obtained to the
maximum extent of 80% of the total decomposed
material which is advantageous in comparison to
reclamation to PUF containing a maximum of 5%
polyol content. After reclamation, molecular weight
of the polyol per hydroxyl group (B342) for the
unrefined polyol may be further improved to B921
after refining in comparison to the value of 1000
for the virgin polyol. Moreover, the combination of
the obtained unrefined and refined polyol, i.e., the
unrefined: refined polyol ratio may be increased to
improve hardness and tensile strength as well as to
decrease elongation at break.
Apart from the above-mentioned routes, different
combinations of several amines with glycols25 may
also be used for aminolytic cleavage of PUs. Such
a work was patented by Behrendt et al.,26 where a
small amount of secondary aliphatic amine, e.g.,
dibutylamine with more than one glycol or further
polyether alcohol, was added. The recycled polyols
can be used in existing formulations between 15 wt
% (in high resilience foam) to and 50 wt% (in shoe
84
Figure 7.9 Schematic representation of reclamation of PUF by using DEA.24
soles).27 In this process, maintaining the recycling
temperature in between 180°C and 220°C for the
duration of 15
30 minutes facilitates significant
suppression of splitting of ureas.
7.3 Ammonolysis of PU Foam
Ammonolytic cleaving is mostly used industrially
for manufacturing of melamine, urea, ethanolamine
from ethylene oxide, methylamine from methyl
alcohol, etc. Ammonia may be used in ammonolysis
process in the form of aqueous, liquid, anhydrous, or
supercritical ammonia. Du Pont Company has iden-
tified ammonolytic cleavage as the best method of
depolymerization of scrap carpets. In this process,
RECYCLING OF POLYURETHANE FOAMS
plastic scraps are molten and reacted to ammonia
and suitable catalyst (e.g., phosphate) at elevated
temperature and pressure. Ammonolysis has been
investigated so far mostly for nylon.19,28,29
However, only a few studies were reported on this
method for recycling of PUs. This process was first
reported in a patent in 1955.30 According to two
patents of McDonnell Douglas Corporation,31,32
ammonia may also be used as a co-reagent during
the alcoholysis of PUs. Ammonolysis may also be
accomplished simultaneously with other depolymer-
ization methods like glycolysis and alcoholysis.
According to the patent of Sheratte,10 the reclaiming
process was divided into two steps. In the first step,
simultaneous glycolysis and ammonolysis by using
polyol, glycol, ammonium hydroxide, and ammonia
7: CHEMICAL DEPOLYMERIZATION OF POLYURETHANE FOAM
resulted in a mixture of polyols where amines were
found to be either phase-separated or processed fur-
ther. The second step involved reaction of the mate-
rial with ammonia.
Decomposition temperature for ammonolytic
decomposition of PUs in the presence of concen-
trated ammonia water (ammonium hydroxide) may
vary from 100°C to 25°C. The weight ratio of
ammonium hydroxide to PU may vary widely
within the range from 0.1% to ca. 30%.33 Strongly
basic catalysts may be used to increase the depo-
lymerization reaction rate.34 An interesting process
of ammonolytic cleavage of PU was developed by
Lentz et al.,35 where supercritical ammonia was
used for depolymerization. Nucleophilicity of
ammonia is greater as compared to water or gly-
cols. In supercritical ammonia, its presence in
excess of molar mass in comparison to urethane
favors forward reaction of depolymerization.
Aminolysis reaction converts carbonic acid deriva-
tives into urea, whereas ester and carboxylic acid
derivatives are converted to amides. However,
hydroxyl and ether groups remain unaffected by
ammonia. Low boiling point materials exhibit
improved solubility and reactivity in supercritical
conditions. Ammonia reaches its critical point at
132.45°C and 112.8 bar, i.e., 11.28 MPa with a den-
sity of 0.235 g/cm3. While using ammonia under
supercritical condition, both depolymerization reac-
tions of PUF as well as separation of the polyols
Figure 7.10 Schematic flow diagram of the process of ammonolytic cleavage of PU and polyol separation by
using supercritical ammonia.35
VIA AMMONOLYSIS AND AMINOLYSIS 85
take place. The flow diagram of this process is
shown in Fig. 7.10. In a reactor of 50 mL volume,
the ammonolysis reaction was carried out at 139°C
and 140 bar for a reaction time of 2 hours and
extraction time of 90 minutes. In this process evap-
orated ammonia can be reused after liquefaction.
Two different PU materials were used as the start-
ing materials: (1) a solid elastomer based on methy-
lenebis(phenyl isocyanate) (MDI), trifunctional
polyether triol and 1,4-butanediol as chain extender
and (2) a flexible foam with diol replaced by water.
For both cases, the mole ration of [isocyanate]:
[chain extender, or water]:[polyol] was maintained
at 5:4:0.66. Stoichiometry of the ammonolytic
depolymerization reaction has been shown in
Fig. 7.11.
Phosgenation of the amine results in the forma-
tion of corresponding diisocyanate, which may be
used together with the polyols for PU recovery.
Higher amount of polyol was found in the degrada-
tion product while water was used instead of chain
extender. After completion of depolymerization
reaction, diamine and diols can be separated by pre-
cipitation or distillation, urea may be extracted by
water, whereas polyols remain in the residue inside
the reactor. Since the use of supercritical ammonia
does not yield chain extender and diamines with
prominent phase separation, distillation was sug-
gested as a possible method of separation because
of the differences of respective boiling points.
86
Figure 7.11 Stoichiometry of ammonolytic depolymerization of PU.35
7.4 Conclusion
Among different methods of recycling of PUF,
ammonolysis and aminolysis are relatively less
explored. These methods involve the use of ammo-
nia (ammonolysis), amines, or alkanolamines (ami-
nolysis) for depolymerization process. These
methods may be applicable solely or in combina-
tion with other depolymerization methods. Since
less investigated, still scopes are there for further
modification and improvement of the methods
towards improvement of conversion of the reaction
and quality of the recycled product as well.
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