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Influence of chemical structure on glass transition temperature of polyimides

Article  in  Structural Chemistry · October 2010

DOI: 10.1007/s11224-010-9639-1

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Struct Chem (2010) 21:1013–1020
DOI 10.1007/s11224-010-9639-1
ORIGINAL RESEARCH
Influence of chemical structure on glass transition temperature
of polyimides
Inga A. Ronova • Maria Bruma
Received: 30 April 2010 / Accepted: 11 June 2010 / Published online: 25 June 2010
Ó Springer Science+Business Media, LLC 2010
Abstract A study of the relationship between glass
transition temperature of various polyimides and their
conformational parameters is presented. The dependence of
glass transition temperature on the rigidity of either dia-
mine or dianhydride component is discussed by selecting
groups of polymers based each on one diamine and dif-
ferent dianhydrides. The solubility of such polymers is also
discussed in connection with the rigidity of their chains.
Keywords Polyimides  Conformational rigidity 
Glass transition temperature  Solubility
Introduction
Aromatic polyimides belong to the class of high perfor-
mance polymers due to their excellent thermal and chem-
ical stability, good mechanical resistance and low dielectric
constant. Such polymers are appropriate for use in micro-
electronics, aerospace, and other industries, as films and
coatings, adhesives, membranes for separation of gases or
liquids, impregnating resins in high temperature compos-
ites [1–3]. But, wholly aromatic polyimides have a major
drawback related with their insolubility in organic solvents
and lack of glass transition, or too high glass transition
temperature, practically in the same domain with their
I. A. Ronova
A. N. Nesmeyanov Institute of Organoelement Compounds,
Russian Academy of Sciences, Vavilov st. 28, Moscow
119991, Russia
M. Bruma (&)
Petru Poni’’ Institute of Macromolecular Chemistry,
Aleea Grigore Ghica Voda 41A, 700487 Iasi, Romania
e-mail: mbruma@icmpp.ro
decomposition, which makes their processing very diffi-
cult. The two-step process in which the intermediate
soluble polyamic acid resulting form the polycondensation
reaction of an aromatic dianhydride with an aromatic
diamine is processed into thin films or other thin layer
articles that are afterwards converted into the final insolu-
ble and infusible polyimide structure still has some disad-
vantages: water evolved during cyclization would produce
voids in the final article and thus deteriorate its physical
properties; also, the cyclization of polyamic acid to poly-
imide structure is never complete and the remaining
non-cyclized groups would cause the degradation in time
of the macromolecular chain. Therefore, much research is
carried out on new polyimides which should be soluble in
certain solvents and should have a reasonable high glass
transition temperature so that they could be processed by
casting the solutions or by thermoforming of the already
cyclized polyimides. Such polymers can be mainly
obtained by the introduction of flexible bridges into the
macromolecular chain [4–11]. The flexible bridges can
come either from the starting dianhydride or diamine
monomer. The solubility and glass transition temperature
of polymers depends very much on their conformational
rigidity: with increasing rigidity, the solubility decreases
and glass transition temperature increases [12]. Therefore,
it is very useful to find out in what way the glass transition
is influenced by the presence of various connecting bridges
in the macromolecular chain.
Here, we present a study of the relationship between
glass transition temperature of various polyimides taken
from published literature, including our own publications,
and their conformational parameters which were calculated
by using our own method. The solubility of these polymers
is also examined in dependence on their conformational
rigidity.
123
1014
Method of calculation
As conformational parameter, we have taken the statistical
Kuhn segment Afr, which was calculated under the
assumption of free rotation with the Eq. 1 [13, 14]:
 2 
hR i
Afr ¼ lim ð1Þ
n!1 nlo
where R2 is mean square distance between the ends of the
chain calculated for all possible conformations, n is the
number of repeating units, lo is the contour length of a
repeating unit, and L = nlo is the contour length of the
chain, a parameter which does not depend on the chain
conformation. All the values of Kuhn segment were cal-
culated with Monte Carlo method and geometry of
repeating unit was assigned by using quantum-chemical
method AM1 [15]. For some of the studied polymers, we
also calculated the Kuhn segment values taking into con-
sideration the hindrance of rotation, according to the
method previously described [16]. Some of these polymers
did not have any hindrance of rotation, or their hindrance
was too low, and it was neglected (Table 1).
Results and discussion
Table 1 shows the chemical structure of the repeating unit,
conformational parameters and glass transition temperature
of a series of 26 polyimides. These polyimides were
synthesized by polycondensation reaction of an aromatic
diamine with an aromatic dianhydride, each of them con-
taining various bridges between the aromatic rings [17–28].
We divided these polymers in to five groups, each of them
being based on one diamine (or two very similar diamines)
and various dianhydrides. The first group contains polymers
1–5 based on hexafluoroisopropylidene-bis(aniline) (poly-
mers 1, 2, 4, 5) or isopropylidene-bis(aniline) (polymer 3);
the second group contains polyimides 6–10 based on the
diamine having cyano-substituted meta-phenylene ring,
namely 2,5-bis(aminophenoxy)-benzonitril; the third group
contains polyimides 11–16 based on bis(aminophenoxy-
phenyl)-isopropane (polymers 11, 13) or bis(aminophenoxy-
phenyl)-hexafluoroisopropane (polymers 12, 14, 15, 16); the
fourth group contains polymers 17–20 based on bis(4-ami-
nophenyl)-oxadiazole, and the fifth group contains polymers
21–26 based on bis(aminophenoxy-phenyl)-oxadiazole.
Now, we examine how the glass transition temperature
is influenced by the connecting bridge between two imide
rings in polyimides based on one diamine monomer (or two
very similar diamines). Table 2 contains the parameters of
equation y = A ? Bx. The coefficient B in this equation
shows how much the bridge between two imide rings
influences the rigidity of polymer and consequently its
123
Struct Chem (2010) 21:1013–1020
glass transition temperature. Higher the coefficient B,
higher this influence. The values of B in Table 2 are not
very high, and therefore they are statistically independent.
Figure 1 shows the dependence of glass transition tem-
perature on Kuhn segment for the first group of polymers,
1–5. It can be seen that with increasing of conformational
rigidity (from 19.25 to 37 Å), glass transition temperature
increases (from 188 to 329 °C). This dependence is linear,
with a high correlation coefficient (R = 99.13%) and big
slope of the line (coefficient B in equation y = A ? Bx is
equal to 9.20). It means that in this group of polymers,
containing hexafluoroisopropylidene-diphenyl (polymers 1,
2, 4, 5) or isopropylidene-diphenyl (polymer 3) in diamine
component, the glass transition temperature depends very
much on the connecting bridge between imide rings coming
from dianhydride component; it does not depend signifi-
cantly on what bridges, isopropylidene or hexafluoroiso-
propylidene, are present in the diamine component.
Therefore, the conformational rigidity of these polymers is
determined by the dianhydride component.
In the second group of polymers (6–10) (Fig. 2), the
diamine component has flexible ether linkages and phe-
nylene rings meta-substituted, and therefore the rigidity of
this fragment is weak (Afr in the range of 14.54–19.38 Å)
and it determines the rigidity of the whole polymer, and
its glass transition temperature. The influence of the
dianhydride component on the rigidity of polymer is also
weak (coefficient B is equal to 2.07). However, the
polymers 9 and 10, containing silicon bridge between
imide rings, are out of the general dependence. Two
reasons could determine this behavior of polymers 9 and
10: low molecular weight or significant decrease of
polymer rigidity. In the first case, the macromolecular coil
(ball) could not form, the chains are short and confor-
mational transitions take place easier than in the other
polymers in this group, and consequently the glass tran-
sition temperature decreases significantly. In the second
case, the rigidity of polymers 9 and 10 is substantially
lower because the silicon bridge is composed of two
Si(CH3)2 groups which change clearly the orientation of
chains and leads to a decrease of polymer rigidity com-
pared with the other polymers studied here.
In the third group of polymers (11–16) (Fig. 3), the
situation is similar to the second group: the slope of line is
small (coefficient B is equal to 1.89), therefore the influ-
ence of dianhydride component on glass transition tem-
perature is weak. Here, the polymer 16 is out of the general
dependence, possibly due to the same reasons shown in
case of polymers 9 and 10 belonging to the second group.
In the fourth group (17–20) (Fig. 4), the diphenyl-oxa-
diazole fragment of diamine component is quite rigid and
its influence on the whole rigidity of polymer is high:
coefficient B is equal to 4.68. For the polymer 18, we did
Struct Chem (2010) 21:1013–1020 1015

Table 1 Chemical structure of the repeating unit, glass transition temperature and conformational rigidity parameters of the studied polyimides
Polymer Repeating unit Tg ( C) lo (Å) Afr, Ah (Å) Solubility Ref.

The first group of polymers (1–5): polyimides based on isopropylidene-bis(aniline) or hexafluoroisopropylidene-bis(aniline)

1 O O
CF3
329 21.16 37.00 Soluble in NMP, DMA, DMF [17]
N N C
CF3
40.70
O O

O O O
2 CF 3 260 22.47 28.82 Soluble in NMP, DMA, DMF [17]
N N C
CF 3 31.59
O O

O O
3 CF3
CH3 310 22.40 24.21 Soluble in NMP, DMA, DMF, CHCl3 [18]
N N C
CF3
CH3 38.18
O O

O O
4 CF3
CF3 320 22.40 24.21 Soluble in NMP, DMA, DMF, CHCl3 [19]
N N C
CF3
CF3 39.27
O O

O
5 CH3
Si
CH3 O
CF3 188 26.08 19.25 Soluble in NMP, DMA, DMF, CHCl3 [20]
O Si
N N C
CH3 CH3
CF3 25.62
O O

The second group of polymers (6–10): polyimides based on 2,5-bis(aminophenoxy)-benzonitril

6 O O CN
232 25.66 19.38 Soluble in NMP, DMA, DMF [21]
N N O O

O O

7 O O O CN 226 26.96 16.68 Soluble in NMP, DMA, DMF [21]

C
N N O O

O O

8 O CF3 O CN 235 26.92 16.16 Soluble in NMP, DMA, DMF, CHCl3 [21]
C
N N O O

O
CF3
O
21.07

9 O CH3 CH3 O CN 153 30.65 14.54 Soluble in NMP, DMA, DMF, CHCl3 [20]
Si O Si
N N O O

O
CH3 CH3

O
17.59

10 O CH3 CH3 O CN 152 31.47 18.55 Soluble in NMP, DMA, DMF, CHCl3 [20]
Si O Si
N N O O

O
CH3 CH3
22.44

The third group of polymers (11–16): polyimides based on bis(aminophenoxy-phenyl)-isopropane or bis(aminophenoxy-phenyl)-

hexafluoroisopropane

11 O O
CH3 249 30.97 35.89 Soluble in NMP, DMA, DMF, CHCl3 [17]
N N O C O
CH3
O O

O O
12 N N O
CF3
C O
250 30.97 36.97 Soluble in NMP, DMA, DMF, CHCl3 [22]
CF3
O O

O O
13 N
O
C
N O
CH3
C O
234 32.05 27.51 Soluble in NMP, DMA, DMF [23]
CH3
O O

O O O
14 N
C
N O
CF3

C O
232 32.05 27.51 Soluble in NMP, DMA, DMF [23]
CF3
O O

O
15 N
O
O

N O
CF3

C
233 32.07 27.06 Soluble in NMP, DMA, DMF [24]
O

O O
CF3
28.4

16 N
O CH3
Si O
CH3
Si
O

N O
CF3

C O
162 35.80 20.41 Soluble in NMP, DMA, DMF, CHCl3 [20]
CH3 CH3
CF3
O O

123
1016 Struct Chem (2010) 21:1013–1020

Table 1 continued
Polymer Repeating unit Tg ( C) lo (Å) Afr, Ah (Å) Solubility Ref.

The fourth group of polymers (17–20): polyimides based on bis(4-aminophenyl)-oxadiazole

O
17 O
N N
297 25.31 47.52 Insoluble in organic solvents [25]
O
N N
O

O O

O O
18 N N 434* 24.21 78.11
N N
O

O O

O CF3 O
19 C
N N 300 25.44 35.94 Soluble in NMP, DMA, DMF [26]
N N
CF3 O

O O
50.68
O
20 CH3
Si O
CH3

Si
O
N N 187 29.04 25.55 Soluble in NMP, DMA, DMF, CHCl3 [20]
N N
CH3 CH3 O

O O

The fifth group of polymers (21–26): polyimides based on bis(aminophenoxy-phenyl)oxadiazole

21 O O
N N
235 35.30 36.16 Soluble in NMP, DMF, DMA [27]
O
N N O O
O

O O

22 O O
N N
272 34.20 45.18 Insoluble in organic solvents [28]
N N O O
O

O O

23 O O O
N N
250 35.47 32.32 Soluble in NMP, DMF, DMA [26]
C
N N O O
O

O O

24 O CF3 O
N N
282 35.43 30.92 Soluble in NMP, DMF, DMA [26]
C
N N O O

O
CF3
O
O
31.85

25 O CH3 CH3 O
N N
183 39.03 25.38 Soluble in NMP, DMA, DMF, CHCl3 [20]
Si O Si
N N O O
CH3 CH3 O

O O

26 O CH3 CH3 O
N N
165 38.80 19.01 Soluble in NMP, DMA, DMF, CHCl3 [20]
Si O Si
N N O O
CH3 CH3 O

O O

Tg glass transition temperature, lo contour length of a repeating unit, Afr Kuhn segment calculated under the assumption of free rotation, Ah Kuhn
segment calculated under the assumption of hindered rotation, Ref reference

not find any data regarding its synthesis and glass transition The fifth group of polymers (21–26) (Fig. 5) similarly to
temperature. The dependence of glass transition tempera- the fourth one, contains a quite rigid diamine component and
ture on conformational rigidity for the other three polymers the overall conformational rigidity of the polymer is deter-
in this group is linear with a high correlation coefficient mined by the bridge connecting two imide rings. This is
(R = 95.57%). On the basis of equation describing this confirmed by parameter B equal to 4.20, which is lower than
dependence, we calculated the Tg value (which should be that (9.20) of the first group, but significantly higher than that
found experimentally) of polymer 18: 434 °C. This value is (1.89) of the third group of polymers. In the diagram
close to the decomposition temperature of the polymers describing the dependence of glass transition temperature on
belonging to this group. As a consequence, the Tg of Kuhn segment of this group, the points corresponding to
polymer 18 is difficult to be measured experimentally. polymers 23 and 24 are out. The synthesis of these two
Besides, the conformational rigidity of polymer 18 is the polymers was performed in N-methyl-pyrrolidinone (NMP)
highest (Afr = 78.11 Å) compared with all the polymers as solvent at high temperature [26]. In reference [30, 31], on
studied here. It influences the solubility of this polymer and the basis of IR spectra recorded at high temperature, it was
with increasing the length of the macromolecular chain shown that in case of polycondensation in NMP at high
during synthesis it will not dissolve any longer and it will temperature, crosslinking may take place, as represented in
precipitate out of solution; thus the polymer will not reach scheme below, which leads to the increase of polymer
a high molecular weight [29]. rigidity and of glass transition temperature:

123
Struct Chem (2010) 21:1013–1020 1017

O O
C NH C NH
O
O
C OH -H2O C
O O
OH
C
C
O
C NH
C NH
O
O

Table 2 Parameters of equation y = A ? Bx for all five groups of

polymers
Group of polymers A B Correlation
coefficient R (%)
Fig. 2 Dependence of glass transition temperature on Kuhn segment
The first group: 1–5 41.36 9.20 ± 1.22 99.13 for the second group of polymers (6–10)
The second group: 6–10 191.65 2.07 ± 0.12 99.83
The third group: 11–16 180.34 1.89 ± 0.13 99.32
The fourth group: 17–20 68.11 4.68 ± 0.43 99.57
The fifth group: 21–26 81.47 4.20 ± 0.23 99.70

Fig. 3 Dependence of glass transition temperature on Kuhn segment

for the third group of polymers (11–16)

Fig. 1 Dependence of glass transition temperature on Kuhn segment

for the first group of polymers (1–5)

Now, we examine how the diamine component influences

the Tg of the corresponding polyimides containing identical
bridge between the imide rings coming from dianhydride
component. Fig. 6 shows the dependence of glass transition
temperature on conformational rigidity of polyimides 1, 6,
11, 12 and 22, in which two imide rings are directly con-
nected, without any bridge. This dependence is linear, with a
high correlation coefficient (R = 95.17%) and a weak slope
of the line towards abscise (B is equal to 1.44, Table 3). It
means that in this group of polymers, the glass transition
temperature changes only very little when changing the
rigidity of the diamine component. An exception is made by
the point belonging to polymer 1: this is out of that depen- Fig. 4 Dependence of glass transition temperature on Kuhn segment
dence. The rigid connection between two imide rings, and for the fourth group of polymers (17–20)

123
1018 Struct Chem (2010) 21:1013–1020

flexibility of polymers, the change of diamine component has

a significant influence (Table 3; Figs. 7, 8, 9): higher the
rigidity of the diamine component, higher the overall rigidity
of the polymers having identical dianhydride component.
The polymers containing carbonyl bridge are more sensitive
to the change of rigidity of diamine component (B = 6.97).
Now, we examine how the structure of diamine and
dianhydride components influences the solubility of poly-
mers in organic solvents. The presence of hexafluoroiso-
propylidene bridge in diamine component, independent of
the bridge between two imide rings coming from dianhy-
dride component, leads to good solubility in organic sol-
vents. The same behavior was found in case of polymers
containing meta-phenylene rings having cyano substituents
and in those containing 2,2-bis(4-aminophenoxy-phenyl)-
Fig. 5 Dependence of glass transition temperature on Kuhn segment
propane fragment in diamine component.
for the fifth group of polymers (21–26)

Fig. 6 Influence of diamine component on glass transition temper- Fig. 7 Influence of diamine component on glass transition temper-
ature of polyimides based on 3,30 ,4,40 -diphenyltetracarboxylic ature of polyimides based on 3,30 ,4,40 -benzophenonetetracarboxylic
dianhydride dianhydride

Table 3 Parameters of equation y = A ? Bx for polymers having

identical bridge between two imide rings
Structure of the bridge between A B Correlation
imide rings coefficient R
(%)

– 201.15 1.44 ± 0.33 95.17

–C(CF3)2– 132.04 4.48 ± 0.33 99.89
–CO– 40.00 6.97 ± 0.44 99.60
–Si(CH3)2–Si(CH3)2– 102.56 3.23 ± 0.38 97.24

the structure of the diamine component determine a high

conformational rigidity (Afr = 37 Å) of this polymer and,
consequently, a high glass transition temperature.
In the last three groups of polymers containing various
Fig. 8 Influence of diamine component on glass transition temper-
bridges between imide rings, such as carbonyl, hexafluoro- ature of polyimides based on 3,30 ,4,40 -diphenylhexafluoroisopropyli-
isopropylidene or tetramethylsiloxane, which increase the dene-tetracarboxylic dianhydride

123
Struct Chem (2010) 21:1013–1020
Fig. 9 Influence of diamine component on glass transition temper-
ature of polyimides based on 3,30 ,4,40 -diphenyltetramethylsiloxane-
tetracarboxylic dianhydride
The introduction of diamine components containing
diphenyl-oxadiazole segment leads to insolubility only in
case of polymer having just one ether bridge between imide
rings (17), in the fourth group of polymers, while in case of
polymers containing diphenoxy-phenyl-oxadiazole seg-
ment, in the fifth group of polymers, only the polyimide
containing imide rings directly connected (22) is insoluble;
these two polymers are the most rigid in these two groups
(Afr of polymer 17 is 47.52 A, and Afr of polymer 22 is
45.18 Å). All the other polymers in these two groups are
soluble in organic solvents.
Thus, when studying the data in Tables 2 and 3, it can
be seen that higher the coefficient B, higher the influence of
the bridge between two imide rings, coming from dian-
hydride component, on the rigidity of polymer. By com-
paring these five groups of polymers, it can be seen that the
highest influence of the rigidity of dianhydride component
exists when the rigidity of the diamine component is high
(the first group of polymers, where B = 9). Consequently,
in a group based on the same diamine component, the
rigidity of polymer is very sensitive to the rigidity of dia-
mine. Higher the rigidity of the diamine, higher the influ-
ence of the rigidity of dianhydride. At the same time, by
comparing the polymers having the same bridge between
two imide rings, it can be seen that higher the rigidity of
this bridge, lower the influence of diamine component on
the rigidity of polymer (in the case of direct connection
between two imide rings, the coefficient B is the lowest).
Conclusions
In the case of a rigid diamine component, the change of
connecting bridge in the dianhydride component influences
significantly the rigidity of the whole polymer chain, and
1019
consequently the glass transition temperature. In the case of
a flexible diamine component, this influence is weak.
In the case of a rigid dianhydride component, when the
resulting imide rings are directly connected, the change of
rigidity of the diamine component has a weak influence on
the whole conformational rigidity and, as a consequence, a
weak influence on glass transition temperature. By con-
trary, in the case of flexible bridges between imide rings,
such as ether, carbonyl, isopropylidene or silicon, the
change of rigidity of diamine component influences sig-
nificantly the rigidity of the respective polymer and its
glass transition temperature.
This study is useful for future work on new soluble and
easy processable polyimides: the appropriate selection of
the monomers – diamines and dianhydrides, more specifi-
cally of the flexible bridges inside them, may be very
beneficial for advanced applications of such polymers.
Acknowledgments The financial support provided through the
Project no. 11008/2007 from the Romanian Program PNCD-2 and
through the Grant P-7 from the Presidium of Russian Academy of
Sciences is warmly acknowledged.
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