Open Journal of Polymer Chemistry, 2011, 1, 1-9
doi:10.4236/ojpchem.2011.11001 Published Online November 2011 (
Copyright © 2011 SciRs. OJPChem
Organosoluble and Thermally Stable of Benzazole-
Containing Poly(Imide-Urea)s: One-Pot Synthesis and
Hojjat Toiserkani1,2*
1Department of Chemistry, College of Sciences, Hormozgan University, Bandar Abbas, Iran.
2College of Oil Engineering, Hormozgan University, Bandar Abbas, Iran.
E-mail: *
Received October 12, 2011; revised November 10, 2011; accepted November 18, 2011
The preparation of new types of poly(imide-urea)s (PIUs) with high thermal stability and improved solubility
was investigated. Three series of aromatic poly(imide-urea)s (PIUOa-c, PIUSa-c, and PIUNa-c) bearing pen-
dent benzoxazole, benzothiazole or benzimidazole rings were prepared by one-pot polycondensation reaction
of three bis(imide-carboxylic acid)s, 2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzoxazole (1O), 2-[3,5-bis(N-
trimellitimidoyl)-phenyl]benzothiazole (1S), or 2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzimidazole (1N)
with various kinds of aromatic diamines (a-c). The effects of the benzazole pendent groups on the polymer
properties such as solubility and thermal stability were investigated by comparison of the polymers. All of
the resulting polymers exhibited excellent solubility in common polar solvents. The glass transition tem-
perature of the polymers determined by DSC thermograms were in the range 192˚C - 236˚C. The tempera-
tures at 10% weight loss from their TGA curves were found to be in the range 390˚C - 441˚C in nitrogen.
Keywords: Poly(Imide-Urea)s, Structure-Property Relation, Thermal Properties, Benzazole Pendent Groups
1. Introduction
Aromatic polyimides (PIs) are well known as materials
of high performance were developed in the early 1960s
and since then have been of great technological impor-
tance because of their outstanding thermal stability and
chemical resistance, together with their balanced electric
and mechanical properties [1,2]. Because many of them
are insoluble and infusible, however, their applications in
some fields were limited. It is well known that the poor
properties of PIs have a close connection with its chemi-
cal composition and chain structure, in other words, the
chemical composition and chain structure of PIs will be a
head ingredient leading them to infusible within proc-
essing temperature and insoluble in organic solvents.
Thus, incorporating new functionalities to make polyim-
ides more tractable without decreasing their many desir-
able properties has become one important target of
polyimides’ chemistry [3,4]. So far, many efforts on
chemical modifications of polyimides structure have
been made to enhance their processability and solubility
while other advantageous polymer properties are retained
either by introducing flexible linkages, bulky groups, or
molecular asymmetry into the polymer backbone [5-19].
Among these approaches, the method of incorporating
bulky, rigid benzazole hetero rings as pendent groups
into the polymer backbone has become very attractive
[20-23]. The advantages of this method include two main
parts: (1) close chain packing and intermolecular interac-
tions of the resulting polyimide are restricted, and this
results in relatively high polymer solubility, and (2) the
main chain rigidity of the polyimide can be maintained
by restricting the segmental mobility, in addition, these
benzazole hetero rings are thermally stable, and these
allow the polyimide to have a high glass-transition tem-
perature (Tg) and excellent thermal properties.
As reported in our previous publications [22,23], three
bis(imide-carboxylic acid)s, 2-[3,5-bis(N-trimellitimi-
doyl)-phenyl]benzoxazole (1O), 2-[3,5-bis(N-trimelliti-
midoyl)-phenyl]benzothiazole (1S), and 2-[3,5-bis(N-tri-
mellitimidoyl)-phenyl]benzimidazole (1N) were synthe-
sized via a two-stage procedure that included the con-
densation reaction between 2-aminophenol, 2-amino-
thiophenol, or m-phenylenediamine and 3,5-diamino-
benzoic acid in the presence of polyphosphoric acid
(PPA) in 190˚C, followed by their reaction two mole
equivalents of trimellitic anhydride in refluxing glacial
acetic acid, and were used to prepare aromatic poly(amide-
imide)s containing benzazole hetero rings pendent
groups in the backbones.
Because of the bulky heat-resistant structure of the
components 1O, 1S, and 1N as pendent groups, the result-
ing polymers exhibited reduced chain-packing efficiency
and intermolecular interactions such as hydrogen bond-
ing. Therefore, several organosoluble poly(amide-im-
ide)s with moderate Tgs and high thermal stability could
be achieved by the incorporation of the benzazole pen-
dent units in the main chain. These results prompted us
to use bis(imide-carboxylic acid) monomers (1O, 1S, and
1N), and to study the properties of the poly(imide-urea)s
obtained by direct polycondensation of them with aro-
matic diamines (a-c).
2. Experimental
2.1. Materials
Diphenyl azidophosphate (DPAP) purchased from Merck
and used as received. Dimethyl sulfoxide (DMSO,
Merck) and triethylamine (TEA, Merck) were purified
by distillation under reduced pressure over calcium hy-
dride and stored over 4-Å molecular sieves. 2,6-Diami-
nopyridine (a, Merck) was purified by sublimation be-
fore use. Aromatic diamines including 5-(2-benzoxazo-
le)-1,3-phenylenediamine (b, mp 226˚C - 230˚C), and
5-(2-benzothiazo le)-1,3-phenylenediamine (c, mp 167˚C
-171˚C) were prepared in our laboratory according to the
method previously reported [22].
2.2. Synthesis of the Monomer
Bis(imide-carboxylic acid) monomers 1O, 1S, and 1N were
synthesized by the condensation of 5-(2-benzoxazole)-1,3-
phenylenediamine, 5-(2-benzothiazole)-1,3-phenylenediamine,
and 5-(2-benzimidazole)-1,3-phenylenediamine, with two
mole equivalents of trimellitic anhydride in glacial acetic
acid, respectively, according to our previous works [22,23].
2.3. Synthesis of Poly(Imide-Urea)s (PIUs)
The general procedure to prepare the poly(imide-urea)s
is as follows: into a 50 mL two-neck round-bottom flask
equipped with a drying tube-capped reflux condenser,
magnetic stirrer, and dropping funnel were placed bis
(imide-carboxylic acid) 1O (0.172 g, 0.30 mmol) in
DMSO (2.0 mL). Then, DPAP (0.7 mL) and triethyl-
amine (0.8 mL) were added to the initial contents of the
flask. The final mixture was stirred 2 h at about 10˚C and
then for 3 h at 70˚C until evolution of nitrogen gas
stopped. 2,6-Diaminopyridine (a) (0.032 g, 0.30 mmol)
in DMSO (2.5 mL) was added dropwise to the initial
reaction mixture, and the final mixture was heated for 12
h at 90˚C. The viscous polymer solution obtained was
trickled on stirred methanol to give rise to a crude pre-
cipitate, which was collected by filtration, washed thor-
oughly with methanol, hot water, and ether, respectively,
and dried under reduced pressure at 40˚C to afford 0.103
g (51%) of PIUOa as dark brown powder.
The inherent viscosity of the poly(imide-urea)s ob-
tained in N,N -dimethylacetamide (DMAc) was 0.22 dL/g,
measured at a concentration of 0.5 g/dL at 30˚C .
FT-IR (KBr, cm–1): 3352, 3190 (br, m), 1778 (sh, w),
1724 (sh, s), 1677 (sh, s), 1616 (sh, m), 1595 (sh, w),
1502 (sh, m), 1449 (sh, m), 1349 (sh, s), 1206 (sh, w),
1163 (sh, w), 1096 (sh, m), 1035 (sh, w), 924 (sh, w),
893 (sh, w), 763 (sh, w), 725 (sh, m), 675 (sh, w).
1H-NMR (DMSO-d6; δ, ppm): 8.81 ppm (4H of ureylene
linkages), 7.44 - 8.46 ppm (separate peak blocks, 16H of
aromatic rings). Elemental analysis: calculated for
C36H20N8O7 (676)n: C, 63.72%; H, 2.27%; N, 16.51%.
Found: C, 63.21%; H, 2.24%; N, 16.09%.
The above one-pot polyaddition reaction was chosen
as a procedure for preparation of the other PIUs.
2.4. Measurements
Inherent viscosities (ηinh) of polymers were determined
for solution of 0.5 g/dL in DMAc at 30˚C using a
Canon-Fenske viscometer. 1H-NMR spectra were re-
corded on a Bruker AV-500 FT-NMR spectrometer in
DMSO-d6 at 25˚C with frequencies of 500.13 MHz.
FT-IR spectra were recorded on a Bruker Tensor-27
spectrometer for the measurement of infrared absorption
spectra for monomers and polymers. The spectra of sol-
ids were obtained using KBr pellets. Melting points (mp)
were determined with a Buchi 535 melting point appara-
tus. Thermogravimetric analyses (TGA) was conducted
with a Du Pont 2000 thermal analysis under nitrogen
atmosphere (20 cm3/min) at a heating rate of 20˚C /min.
Differential scanning calorimeter (DSC) was recorded on
a Perkin Elmer pyris 6 DSC under nitrogen atmosphere
Copyright © 2011 SciRes. OJPChem
Copyright © 2011 SciRes. OJPChem
(20 cm3/min) at a heating rate of 20˚C /min. (1N) with various aromatic diamines (a-c).
As shown in Scheme 1, bis(imide-carboxylic acid)
monomers, 1 were converted to bis(imide-carbonyl azide)
components, 2 using DPAP in DMSO as the reaction
solvent. The thermal decomposition of the in situ ob-
tained bis(imide-carbonyl azide) 2 via Curtius rearran-
gement gave the corresponding diisocyanates 3. In con-
tinuation of this reaction, compounds 3 have been re-
acted with various aromatic diamines (a-c) to prepare the
final benzazole-based poly(imide-urea)s (PIUs).
3. Result and Discussion
3.1. Synthesis and Characterization
Bis(imide-carboxylic acid) monomers such as 1O, 1S, and
1N were synthesized by the condensation reaction be-
tween the appropriate aromatic diamine, 5-(2-benzoxa-
zole)-1,3-phenylenediamine, and 5-(2-benzothiazole)
-1,3-phenylenediamine, 5-(2-benzimidazole)-1,3-pheny-
lenediamine, and two mole equivalents of trimellitic an-
hydride in glacial acetic acid, respectively. The details of
this synthesis route and the characterization data were
reported in our previous works [22,23].
The reactions including diisocyanate formation and
polyaddition readily proceeded in a dark yellow to brown
homogeneous solution for all polymers preparation. The
poly(imide-urea)s were prepared in total yields of about
60% starting from bis(imide-carboxylic acid)s 1. These
low yields are reasonable because the yields of the Cur-
tius rearrangement reactions are known generally not to
be very high [24]. Moreover, some impurities containing
unfunctionalized or monofunctionalized species are gen-
erated in these reactions, which their presence in the po-
lymerization flask causes a significant decrease in mo-
lecular weight of the final products. The details about
various aspects of this one-pot polyaddition were
Three series of aromatic poly(imide-urea)s (PIUs)
having benzoxazole, benzothiazole, and benzimidazole
pendent group were prepared by the diphenyl azido-
phosphate (DPAP) activated one-pot polycondensation
reaction of three bis(imide-carboxylic acid) monomers,
2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzoxazole (1O),
2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzothiazole (1S),
and 2-[3,5-bis(N-trimellitimidoyl)-phenyl]benzimidazole
Scheme 1. One-pot synthetic route to pre par e new poly(imide-urea)s.
reported in literature [25]. As listed in Table 1, the re-
sulting dark yellow to brown poly(imide-urea)s pos-
sessed inherent viscosities ranging between 0.10 dL/g
and 0.22 dL/g, measured in DMAc at a concentration of
0.5 g/dL at 30˚C.
Because, the inherent viscosity is a criterion for the es-
timation of molecular weight [23] the prepared PIUs
showed reasonable molecular weights.
Also, structural features of these poly(imide-urea)s
were verified by IR and proton NMR spectroscopy.
Representative FT-IR spectrum of PIUSb is shown in
Figure 1. It displays characteristic absorption bands for
Table 1. Some characterization data of the resulting poly(urea-imide)s.
Polymer code bis(imide-carboxylic acid)s Diamine structure Yield (%) ηinha (dL/g) Color and appearance
51 0.22 dark brown powder
56 0.17 peal brown powder
50 0.15 brown powder
61 0.19 greenish powder
54 0.20 brown powder
63 0.17 greenish powder
57 0.15 black powder
43 0.10 peal brown powder
54 0.13 black powder
aMeasured at a polymer concentration of 0.5 g/dL in DMAc at 30 °C.
Figure 1. FTIR spectrum of PIUSb.
Copyright © 2011 SciRes. OJPChem
the imide ring at around 1779 and 1725 cm–1 (imide-I),
which is indicative of the asymmetrical and symmetrical
C=O stretching vibration, and at 1351 (imide-II), 1078
(imide-III) and 728 cm–1 (imide-IV) whereas the imide-I,
-III, -IV bands were assigned to axial, transverse, and
out-of-plane vibrations of the cyclic imide structure, re-
spectively [22,28]. The N–H stretching band of the urea
could be observed around 3200 - 3350 cm–1, and the
C=O stretching band of urea groups at 1676 cm–1, the
C=N stretching band benzothiazole groups at 1619 cm–1
and the N-H bending and C-N stretching bands at 1557
cm–1 could also be observed. Other PIUs had similar
functional groups.
In general, the 1H-NMR spectra of the resulting
poly(imide-urea)s are divided two parts, with the first
showing the urea-group protons in the most downfield
region (around 8.60 - 9.05 ppm), and the second, reso-
nance signals of aromatic protons in the region of
about 7.25 - 8.53 ppm. On the basis of the description
above, we can conclude that the PIUs have the expected
structures. For example, the 1H-NMR spectrum of PIUOa
is presented in Figure 2. The 1H-NMR spectrum of
PIUOa shows four protons at 8.81 δ that are assigned to
hydrogen atoms of ureylene linkages, aromatic protons at
7.44 - 8.46 δ with expected multiples and integration is
consistent with the expected structure of the compound.
3.2. Properties of the Poly(Imide-Urea)s
The solubility of all poly(imide-urea)s was tested quali-
tatively in various organic solvents, with the results
summarized in Table 2. One of the aims of the present
investigation was the enhancement of the polymer solu-
bility by introducing voluminous pendent groups
Figure 2. 1H-NMR spectrum of PIUOa (500 MHz, DMSO-d6).
Table 2 Solubility of the poly(imide-urea)s.
Polymer code DMAc DMSO DMF NMP m-cresol THF Py CF
PIUOa + + + + +h – +h –
PIUOb + + + + + +h +h –
PIUOc + + + + + +h + +h
PIUSa + + + + + – – –
PIUSb + + + + + +h + +h
PIUSc + + + + + +h + +h
PIUNa + + + + +h – +h –
PIUNb + + + + +h – +h –
PIUNc + + + + + +h –
a Qualitative solubility was determined by dissolving 10 mg of poly(imide-urea)s in 1 ml of solvent at room temperature or upon heating; + : soluble at room
temperature; +h : soluble on heating; and –: insoluble even on heating; DMAc: N,N-dimethylacetamide; DMSO: dimethyl sulfoxide; DMF: N,N-dimethylfor-
mamide; NMP: N-methyl pyrrolidone; THF: tetrahydrofuran; Py: pyridine; CF: Chloroform.
Copyright © 2011 SciRes. OJPChem
along the polymer backbone.
The poly(imide-urea)s, PIUOa-c were readily soluble
in polar aprotic solvents (DMF, NMP, DMAc, DMSO).
They also dissolved in m-cresol and pyridine, while they
were partially soluble in chloroform and tetrahydrofuran
upon heating at about 70˚C. Poly(imide-urea)s, PIUSa-c,
compared to PIUOa-c displayed almost the same solubil-
ity in these solvents. In general, the flexible amide, ether,
and urea linkages affect the solubility of a copolyimide
to a great extent due to a salvation effect. Besides the
solvation effects related to enthalpy factor, the good
solubility of these polymers is also caused, mainly by the
entropy advantage which resulted from bulky pendant
groups in the polymer structures that lead to expansion of
the macromolecular chains in their solution state. Fur-
thermore, this block of copolyimides showed somewhat
further solubility toward the above solvents compared
with that of the other copolyimides with analogous struc-
ture [22,23,28,29]. The better solubility of poly(imide-urea)s,
should be attributed to the interchain steric repulsion
caused by the bulky benzoxazole, benzothiazole or ben-
zimidazole side groups. The chain separation effect ac-
counts for a weakening of the strong interactions through
hydrogen bonding and the steric factor must be dominant
because the other effects, such as dipole attraction or
chain rigidity enhancement, should work against good
The thermal properties of the resulting poly(im-
ide-urea)s were determined by means of differential
scanning calorimetry (DSC) and thermogravimetric
analysis (TGA). The thermal behavior data of the poly-
mers are summarized in Table 3. The DSC profiles were
achieved at a heating rate of 20˚C/min in a nitrogen at-
mosphere in the temperature range from 100˚C to 300˚C.
The DSC thermograms of the poly(imide-urea)s showed
glass-transition temperatures (Tg’s) in the range between
192˚C and 236˚C. The nature of the diamine moiety
played a significant role on the Tg values. These went
down in the series as follows b > c > a (Table 3). This
could be attributed to the incorporation of rigid ben-
zoxazole or benzothiazole ring in diamine segments,
which restricted the free rotation of the macromolecular
chains leading to an enhanced Tg value. Upon comparing
the chemical structures of the pendent groups, it is seen
that benzoxazole was somewhat more Tg than benzothi-
azole [20,22]. Figure 3 shows DSC curves of the poly-
mers PIUOb, PIUSb, and PIUNb.
In order to compare the thermal properties, some ho-
mo and copolymers, including polyimide, polyurea, poly
(imide-amide), poly(imide-ether), and poly(imide-amide-
ether) with the structures shown in Scheme 2 were con-
Table 3. Thermal properties of the poly(imide-urea)s.
Polymer code Tg a (°C ) T10 b (°C ) Char yield c (wt%)
PIUOa 209 408 38
PIUOb 236 441 47
PIUOc 216 412 44
PIUSa 194 390 30
PIUSb 223 417 41
PIUSc 219 394 38
PIUNa 192 397 36
PIUNb 201 437 42
PIUNc 197 415 39
a Form the second heating traces of DSC measurements with a heating rate
of 20°C.min-1 in nitrogen.b Temperature at which 10% weight loss was
recorded by TGA at a heating rate of 20°C.min-1 in nitrogen.c Char yield at
Figure 3. DSC thermograms of PIUOb, PIUSb, and PIUNb.
The thermal properties of these reference polymers are
also listed in Table 4. All the poly(imide-urea)s exhib-
ited lower Tg’s than the fully aromatic homopolyimide
R1, the poly(imide-amide) R4, the poly(imide-ether) R5,
and the poly(imide-amide-ether) R6 due to higher flexi-
bility of the urea linkages than those of imide, amide and
ether bonds.
Thermal stability of the polymers was evaluated by
TGA in nitrogen at a heating rate of 20˚C/min. The
poly(imide-urea)s obtained were stable up to 400˚C and
lost 10% of their total weight between 390˚C and 441˚C,
which showed a remarkably improvement of decomposi-
tion temperature in comparison with common ho-
mopolyurea R3. There are similarities in the thermal sta-
bilities of all PIUs. In fact, all of them showed two step
thermal decomposition pattern in their thermograms. The
temperature maximum decomposition of the first stage is
Copyright © 2011 SciRes. OJPChem
Scheme 2. The chemical structure of some reference polymers.
Table 4. Thermal properties of some reference polymers.
Polymer code Polymer class Tg (°C ) T10 (°C ) Char yield (wt%)a Ref.
R1 Polyimide 412 551c 57 20, 26
R2 Polyimide —b 616c 62 20
R3 Polyurea —b 300 —b 27
R4 Poly(imide-amide) —d 561 60 22
R5 Poly(imide-ether) 279 543 59 28
R6 Poly(imide-amide-ether) 263 513 52 29
a Residual wt% at 800°C in nitrogen. b Was not reported. c Maximum polymer decomposition temperature. d No discernible transition was observed on the DSC
at around 360˚C - 385˚C, which corresponds to the de-
composition of the urea groups. The second-stage de-
decomposition of the imide linkages. Therefore, the 10%
weight loss temperatures are mainly caused by the de-
composition, started around 540˚C - 570˚C, is due to the composition of ureylene linkages. As shown in Table 4,
Copyright © 2011 SciRes. OJPChem
lation reactions of bis(imide-carboxylic
cid)s, namely, 1, 1, and 1with a number of aromatic
D. Stenzenberger and P. M. Hergenrother,
Polyimides. New York: Chapman & Hall, 1990, pp.
the poly(imide-urea)s exhibited less thermal stability
than those of the homopolyimide R1 and R2, the
poly(imide-amide) R4, the poly(imide-ether) R5, and the
poly(imide-amide-ether) R6. However, they showed
higher T10% values than the homopolyurea R3. These obs-
ervations might be attributed to the early degradation of
the urea linkages than those of the imide, amide and even
ether groups against high temperatures. Furthermore,
when the heat-resistant benzoxazole or benzothiazole
ring incorporated as pendent group to the diamines c and
b, an obvious increase was observed for decomposition
profiles aromatic PIU than unsubstituted diamine a in
each series. Upon comparing the chemical structures of
the pendent groups, it is seen that benzoxazole was some-
what more thermally stable than benzothiazole (Table 3 ).
4. Conclusions
The one-pot polyurey
diamines (a-c) resulted in preparation of aromatic
poly(imide-urea)s (PIUOa-c, PIUSa-c, and PIUNa-c). The
main objectives of this study were to improve the solu-
bility of homopolyimides as well as the thermal stability
of homopolyurea by the introduction of both imide and
urea linkages into the macromolecular chains. Most of
the poly(imide-urea)s presented an excellent solubility in
polar aprotic solvents such as, NMP, DMF, DMAc, and
DMSO, while they were partially soluble in m-cresol and
pyridine and also they were not soluble in less polar sol-
vents such as chloroform and tetrahydrofuran at room
temperature. The resulting poly(imide-urea)s showed a
better solubility in common organic solvents than the
polyimides, poly(imide-amide)s, and even poly(ether-imide)s
with the same aromatic structure. Furthermore, the
amorphous polymers obtained exhibited a desirable heat
resistance in comparison with aromatic polyureas due to
the presence of thermally stable imide groups as well as
heat-resistant benzoxazole and benzothiazole rings into
the fully aromatic structures.
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