Syntheses and polymerization of epoxy monomers consisting of carbosilane segments and properties of the networked polymers

Article abstract of DOI:10.1016/j.polymer.2016.09.043

Two diglycidyl ethers which consist of a flexible carbosilane segments and of rigid phenylene moieties (1 and 2) were synthesized and investigated in order to evaluate their heat-curing behavior (epoxy homopolymerization) as well as thermal and mechanical properties of the networked polymers. Differential scanning calorimetry (DSC) analysis revealed that melting points of both diepoxides were??73.9 and??50.7?°C, respectively. Networked polymers of 1 and 2 showed glass transition temperature (T_g)s below ambient temperature of 2.2 and 18.7?°C, respectively. High thermal stability of cured 1 and 2 were confirmed by thermogravimetric analysis (TGA) (5% weight loss temperature (T_d5)?=?369?°C for 1 and 351?°C for 2). Tensile tests of cured 1 and 2 clarified that their Young's moduli were (9.76?±?0.135)^?2 and (1.29?±?0.114) ^?1?MPa, respectively.

Full text of DOI:10.1016/j.polymer.2016.09.043

Polymer 103 (2016) 140e145
Contents lists available at ScienceDirect
Polymer
journal homepage: www.elsevier.com/locate/polymer
Short communication
Syntheses and polymerization of epoxy monomers consisting of
carbosilane segments and properties of the networked polymers
,
, *
Ayumu Karimata a, Kozo Matsumoto a b, Takeshi Endo a
a Molecular Engineering Institute, Kindai University, 11-6 Kayanomori, Iizuka, Fukuoka, 820-8555, Japan
b Department of Biological & Environmental Chemistry, Kindai University, 11-6 Kayanomori, Iizuka, Fukuoka, 820-8555, Japan
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 5 July 2016
Received in revised form
8 September 2016
Accepted 15 September 2016
Available online 15 September 2016
Two diglycidyl ethers which consist of a flexible carbosilane segments and of rigid phenylene moieties (1
and 2) were synthesized and investigated in order to evaluate their heat-curing behavior (epoxy
homopolymerization) as well as thermal and mechanical properties of the networked polymers. Dif-
ferential scanning calorimetry (DSC) analysis revealed that melting points of both diepoxides were ꢀ73.9
and ꢀ50.7 ꢁC, respectively. Networked polymers of 1 and 2 showed glass transition temperature (Tg)s
below ambient temperature of 2.2 and 18.7 ꢁC, respectively. High thermal stability of cured 1 and 2 were
confirmed by thermogravimetric analysis (TGA) (5% weight loss temperature (Td5) ¼ 369 ꢁC for 1 and
Keywords:
Carbosilane
Silicon
351 ꢁC for 2). Tensile tests of cured 1 and 2 clarified that their Young's moduli were (9.76 0.135)ꢀ2 and
ꢀ1
(1.29 0.114)
MPa, respectively.
© 2016 Elsevier Ltd. All rights reserved.
Epoxy resin
1. Introduction
to provide networked polymers with good thermal stability (Td5 of
>380 ꢁC) [13], which suggested a large potential of carbosilane-
based network polymers.
Epoxy resins are one of the most important thermoset materials
in the industrial applications such as coatings, adhesives, electrical
insulations, and composites [1e5]. Epoxy resins require high
chemical and thermal stabilities, high durability, good adhesion
and mechanical properties as well as good reactivities. In addition,
fine-tuning of these properties are of the necessary for particular
applications. To control the characteristics of epoxy resins, intro-
ducing a heteroatom component is considered great effective. Thus,
we focused on introducing carbosilane as a component for epoxy
resins. Polycarbosilanes, consisting of whole backbone CeSieC,
generally show high thermal stabilities with low glass transition
temperature (Tg) [6e11]. Although polysiloxanes exhibit low Tg, the
chemical stability of carbosilanes are higher than those of siloxanes
in general. Because SieC bond is less polarized than SieO bond,
SieC bonds are less prone to be hydrolysed or attacked by nucle-
ophiles [17]. A great number of researches on development of
siloxane-based epoxy resins have been reported [12], while studies
about carbosilane-based epoxy resins have been limited so far. Poly
[1,1-diethylsilabutane-co-1-(3,4-epoxybutyl)-1-methylsilabutane]
has been reported from our laboratory. It can be cationically cured
In this study, we synthesized carbosilane-based epoxy mono-
mers 1 and 2, which consist of not only flexible CeSieC bonds and
alkyl chains but also rigid phenylene units, and compared their
reactivity for cationic polymerization and the properties of their
cured resins with the representative epoxy monomer bisphenol A
diglycidyl ether (BADGE). We expected that the epoxy resins
bearing a carbosilane segment would show lower Tg and Young's
moduli as well as high thermal properties, which will be a useful
information in the development of new epoxy resins for the elas-
tomer applications.
2. Experimental
2.1. Analyses and measurements
1H (400 MHz) and 13C (100 MHz) NMR spectra were recorded on
JEOL JME-ECS 400 NMR spectrometer in CDCl3. Chemical shifts
were determined relative to internal TMS (1H,
CDCl3 ( d 77.16). Attenuated total reflection fourier transform
d
0.00) or internal
13C,
infrared spectroscopy (ATR-FTIR) analyses were recorded by using a
Thermo Scientific Nicolet iS10 spectrometer equipped with a Smart
iTR diamond ATR sampling accessory. Differential scanning calo-
rimetry (DSC) analyses were carried out using Seiko Instrument
* Corresponding author.
E-mail address: tendo@moleng.fuk.kindai.ac.jp (T. Endo).
http://dx.doi.org/10.1016/j.polymer.2016.09.043
0032-3861/© 2016 Elsevier Ltd. All rights reserved.

A. Karimata et al. / Polymer 103 (2016) 140e145
141
DSC-6200R in an aluminum pan under
a
nitrogen flow of
2.3. Preparation of cured resins of 1 and 2
50 mL minꢀ1. Thermogravimetric analysis (TGA) were performed
on a Seiko Instrument TG-DTA 6200 using an aluminum pan under
nitrogen atmosphere (flow rate 100 mL minꢀ1) at a heating rate of
10 ꢁC minꢀ1. Tensile testing was conducted and recorded on tensile
testing machine (EZ-LX, SHIMADZU) using dumbbell-shaped films
(ca. 0.3 mm (T) ꢂ 2 mm (W) ꢂ 12 mm (L)) with speed of 500 mm/
min. Reported values of Ultimate strength, Strain at break and
Young's modulus (E) are average and standard deviations of three
samples.
Monomer 1 or 2 (4 mmol) and 2-methylbenzylmethyl-p-
hydroxyphenylsulfonium hexafluoroantimonate (SAN-AID SI-80)
(0.2 mmol) were dissolved in a solution of chloroformemethanol
(8:1/v:v). The solution was casted into Petri dish made from poly-
tetrafluoroethylene and the solvents were evaporated at room
temperature for 15 h. The sample was further dried under vacuum
at room temperature for 24 h. The sample was heated at 100 ꢁC for
2 h, then 130 ꢁC for 1 h under a N2 atmosphere.
2.2. Materials
3. Results and discussion
1,4-bis(dimethylsilyl)benzene and platinum(0)-1,3-divinyl-
1,1,3,3-tetramethyl disiloxane complex in xylene [2 wt%] were
purchased form Aldrich. Bisphenol A diglycidyl ether (BADGE, 99%
purity) was purchased from ADEKA corporation. Methanol and
chloroform were purchased from Wako Pure Chemical Industry
(Osaka, Japan). 2-methylbenzylmethyl-p-hydroxyphenylsulfonium
hexafluoroantimonate (SAN-AID SI-80) was purchased from San-
shin Chemical Industry co., ltd. 4-vinylbenzyl glycidylehter was
purchased from AGC Seimi Chemical (Kanagawa, Japan). All the
reagents were used without further purification. Silica gel 60
(70e230 mesh ASTM) for column chromatography was purchased
from Merck (Japan).
3.1. Syntheses of epoxy monomers 1 and 2
Syntheses of carbosilane-containing diepoxy monomers 1 and 2
were outlined in Scheme 1. Hydrosylilation of allylglycidylether or
4-vinylbenzylglycidylether with 1,4-bis(dimethylsilyl)benzene
were carried out using Karsted's catalyst to obtain diepoxy mono-
mers 1 and 2 in 97 and 90% yields, respectively. Compound 1 has
been already reported [14], but curing properties of monomer 1 has
not been studied. Nuclear magnetic resonance (NMR) spectroscopy
confirmed the chemical structures of 1 and 2. 1H NMR spectra of 1
and 2 in CDCl3 are shown in Fig. 1. A 12H singlet signal corre-
sponding to SieCH3 protons (b) was observed in upfield region
(0.265 ppm for 1 and 0.290 ppm for 2). Ten protons on diglycidyl
ether moieties (f, g, h, i, j for 1 and h, i, j, k, l for 2) around 2.5e4 ppm
and 4H singlet signals on bis(dimethylsilyl)phenylene at 7.48 ppm
for 1 and 7.53 ppm for 2 were also observed, which confirmed the
corresponding chemical structures of 1 and 2.
2.2.1. Synthesis of 1,4-bis(dimethyl(3-(oxiran-2-ylmethoxy)propyl)
silyl)benzene (1)
Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyl disiloxane complex
in xylene [2 wt%] (0.02 mL, 0.9 mmol) was added to a mixture of 1,4-
bis(dimethylsilyl)benzene (975 mg, 5.01 mmol) and allyl glycidyl
ehter (1.19 g, 10.4 mmol) at 0 ꢁC under a N2 atmosphere. After
stirring for 10 min, the reaction mixture was allowed to warm to
room temperature and stirred for 1 h. The reaction mixture was
purified by silica column chropatography using hexaneeether (2:1)
as an eluent to give a colorless oil (2.05 g, 97%). 1H NMR (400 MHz,
3.2. Curing behavior of 1 and 2
Differential scanning calorimetry (DSC) scans of monomers 1
and 2 are shown in Fig. 2a. The melting points of 1 and 2 are
determined to be ꢀ73.9 and ꢀ50.3 ꢁC from the peak top of heating
cycle of DSC scans. These low melting points might be due to the
CeSieC bonds and flexible alkyl chains.
CDCl3,
d
, ppm): 7.48 (s, 4H), 3.68 (dd, J ¼ 8.7 and 2.4 Hz, 2 H), 3.42
(m, 4H), 3.36, (m, 2H), 3.13 (m, 2H), 2.79, (t, J ¼ 3.9 Hz, 2H), 2.60 (m,
2H), 1.62 (m, 4H), 0.74 (m, 4H), 0.27 (s, 12H). 13C NMR (100 MHz,
To gain insight into the thermal cationic polymerization, DSC
analyses of 1 and 2 were performed with mixing 5 mol% of the
thermally-latent cationic initiator: 2-methylbenzylmethyl-p-
hydroxyphenylsulfonium hexafluoroantimonate (The chemical
structure is shown in supporting information). DSC analysis of
BADGE was also performed under the same condition as reference
experiment. With the addition of the thermally-latent initiator, DSC
CDCl3,
d, ppm): 139.88, 133.00, 74.47, 71.59, 51.00, 4452, 24.23,
11.76, e3.07. 29Si NMR (400 MHz, CDCl3,
d
, ppm): 2.73. ATR-FTIR (y,
cmꢀ1): 2930, 2866, 1380, 1337, 1248, 1133, 1105, 1057, 909, 833, 797,
764, 735. HRMS [FAB] m/z Calcd. for C22H38O4Si2: 422.2309, Found
[M þ Hþ] 423.2384.
2.2.2. Synthesis of 1,4-bis(dimethyl(4-((oxiran-2-ylmethoxy)
methyl)phenethyl)silyl)benzene (2)
Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyl disiloxane complex
in xylene [2 wt%] (0.02 mL, 0.9 mmol) was added to a mixture of 1,4-
bis(dimethylsilyl)benzene (978 mg, 5.03 mmol) and 4-vinylbenzyl
glycidylehter (1.90 g, 9.99 mmol) at 0 ꢁC under a N2 atmosphere.
After stirring for 10 min, the reaction mixture was allowed to warm
to room temperature and stirred for 3 h. The reaction mixture was
purified by silica column chropatography using hexaneeether (2:1)
as an eluent to give a colorless oil (2.57 g, 90%). 1H NMR (400 MHz,
curve (heating scan) of
1 showed exothermic peak around
70e160 ꢁC, which can be attributed to the exotherm by ring-
opening polymerization of the epoxy moieties (Fig. 2b). Similar
tendencies were also observed for 2 and BADGE (see supporting
information). Further experimental information about the cationic
ring-opening reactions of these glycidyl ethers 1 and 2 were ob-
tained by DSC analyses conducted at different heating rate. The
samples containing 5 mol% of 2-methylbenzylmethyl-p-hydrox-
yphenylsulfonium hexafluoroantimonate were scanned at heating
rates of 5, 10, 15, and 20 ꢁC/min. The DSC curves of 1 and 2 are
shown in Fig. 3a and b along with the peak top temperature (Tp). As
increasing the heating rate, the Tps were shifted to higher tem-
perature. From these results, activation energies (Ea)s of 1, 2 and
BADGE were estimated using both Ozawa's method (eq (1)) and
Kissinger's method (eq (2)) [15,16], as follows:
CDCl3,
d, ppm): 7.53 (s, 4H), 7.24 (d, J ¼ 6.3 Hz, 4 H), 7.16 (d,
J ¼ 6.3 Hz, 4 H), 4.54 (quart., J ¼ 8.4 Hz, 4 H), 3.73 (dd, J ¼ 8.7 and
2.4 Hz, 2 H), 3.41 (m, 2H), 3.18 (m, 2H), 2.79 (t, J ¼ 3.9 Hz, 2H),
2.66e2.61 (m, 6H) 1.11, (m, 4H), 0.29 (s, 12H). 13C NMR (100 MHz,
CDCl3,
51.02, 44.47, 29.79, 17.76, e3.02. 29Si NMR (400 MHz, CDCl3,
ppm): 3.02. ATR-FTIR (
, cmꢀ1): 2951, 1513, 1417, 1380, 1248, 1133,
1090, 1019, 902, 834, 811, 767, 691. HRMS [FAB] m/z Calcd. for
34H46O4Si2: 574.2935, Found: [Mþ]574.2925.
d, ppm): 144.80, 139.84, 133.05, 128.08, 127.96, 73.33, 70.75,
d
,
ꢀ
y
ln q ¼ e1:052 ꢂ Ea RTp þ lnðAEa=RÞ ꢀ ln FðxÞe5:331
(1)
C

142
A. Karimata et al. / Polymer 103 (2016) 140e145
Scheme 1. Syntheses of 1 and 2.
Fig. 1. 1H NMR spectra of 1 (a) and 2 (b) in CDCl3.
We also attempted anionic polymerization of 1 and 2 using 2-
ethyl-4-methylimidazole (see supporting information). However,
significant exothermic curves were not observed.
ꢁ .
ꢂ
ꢀ
ꢀln q Tp2 ¼ Ea RTp ꢀ ln ðAR=EaÞ
(2)
where q is heating rate, Tp is the absolute temperature of
exothermic peak, A is the frequency factor, R is the gas constant,
F(x) is conversion dependent term. Ea can be provided from the
slope of the plot of ln (q) against 1/Tp using Ozawa's method
(Fig. 3c). As for the Kissinger's method, the plot of eln (q/Tp [2])
versus 1/Tp gave the straight line, whose slope can be used to give
Ea (Fig. 3d). The Ea obtained from both Ozawa's and Kissinger's
3.3. Preparation of cured epoxy resin of 1 and 2 by cationic
polymerization
A solution of 1 or 2 with 5 mol% of thermally-latent cationic
polymerization
initiator:
2-methylbenzylmethyl-p-hydrox-
yphenylsulfonium hexafluoroantimonate in chloroformemethanol
(8:1) was casted on Petri dish that made of polytetrafluoroethylene.
After removing solvents, the mixture was heated at 100 ꢁC for 2 h,
then 130 ꢁC for 1 h. Photographs of the obtained resins of 1 and 2
are provided in supporting information.
Attenuated total reflection fourier transform infrared (ATR-FTIR)
spectra of 1 and 2 were measured before and after curing procedure
(Fig. 4). In the spectra of 1 and 2 after curing, absorption at
methods are summarized in Table 1. In comparison of Ea estimated
by Ozawa's method, 1, 2 and BADGE showed Ea of 230, 100 and
128 kJ/mol, respectively. In the case of Ea of Kissinger's method,
similar results were obtained. The lower Ea of 2 might be due to the
electron withdrawing effect of benzyl alcoxy groups that activate
epoxy rings on 2. It is noteworthy that the Ea of 2 is comparable for
that of BADGE.

A. Karimata et al. / Polymer 103 (2016) 140e145
143
Fig. 2. (a) DSC scans of 1 (solid line) and 2 (dashed line). (b) DSC scans of 1 (black solid line) and 2 (gray solid line) including cationic initiator (5 mol%) and 1 (black dashed line) and
2 (gray dashed line) without cationic initiator.
Fig. 3. DSC scans of 1 (a) and 2 (b) containing 5 mol% of thermal cationic initiator at different heating rate. (c) plot of ln(q) versus 1000/Tp using Ozawa's method (d) plot of ln(q/Tp)
versus 1000/Tp using Kissinger's method.
epoxy groups in these networked polymers do not undergo further
polymerization (discussed below), which might be due to the steric
hinderance around the epoxy rings in the networked polymers.
Table 1
Curing behaviors of 1 and 2.
Compound
Ea (kJ/mol)
Ea (kJ/mol)
Ozawa method
Kissinger method
1
2
230
100
128
220
84.7
106
3.4. Thermal properties of cured resins
BADGE
DSC scans of cured 1, 2 and BADGE are shown in Fig. 5a. In
heating cycles of 1 and 2, exothermic peaks that can be attributed to
ring-opening polymerization were not observed, indicating that
the epoxy groups in the cured resins of 1 and 2 do not undergo
further reaction, due to the steric hinderance. Tgs of cured 1 and 2
903 cmꢀ1 and 1248 cmꢀ1 that can be assigned to epoxy groups
decreased, indicating that the epoxy moieties reacted. Remained

144
A. Karimata et al. / Polymer 103 (2016) 140e145
Fig. 4. IR spectra of 1 (a) and 2 (b) before and after curing.
Fig. 5. (a) DSC scans of cured 1 (solid line) and cured 2 (dashed line). (b) TGA profiles of cured 1 (solid line), 2 (dashed line) and BADGE (gray line).
were determined to be 2.2 and 18.7 ꢁC, respectively. As expected,
Tgs of both cured 1 and 2 were below ambient temperature because
of flexible SieC bonds and alkyl chains, which lower than that of
BADGE (Tg ¼ 147 ꢁC).
Table 2
Thermal properties of cured 1 and 2.
Compound
Tg (ꢁC)
Td5 (ꢁC)
Td10 (ꢁC)
Cured-1
Cured-2
BADGE
2.2
18.7
147
369
351
382
356
342
399
Thermal stability of 1 and 2 were examined by thermogravi-
metric analysis (TGA) and compared with BADGE. The TGA profiles
are shown in Fig. 5b. Thermal properties of cured resins of 1 and 2
including The 5% weight loss temperatures (Td5) and the 10%
weight loss temperature (Td10) are provided in Table 2. Td5 of 1 and
2 are estimated to be 369 and 351 ꢁC. Although these values are
lower than that of BADGE (Td5 ¼ 382), a CeSieC backbone in epoxy
resin showed good thermal stability. We assume that the remained
initiator and terminal hydroxyl groups could react with carbosilane
at higher temperature because the SieC bond is weaker than the
CeC bond, which lead to lower thermal stability of cured 1 and 2
than cured BADGE.

A. Karimata et al. / Polymer 103 (2016) 140e145
145
good thermal stability (Td5 > 350 ꢁC). Moreover, films of cured 1 and
2 showed Young's moduli in the range of 9.76ꢀ2e1.29ꢀ1 MPa. These
results indicate that 1 and 2 can be promising monomers for the
applications of epoxy resin-based network polymers.
Acknowledgements
This work was financially supported by JSR Co., Ltd.
Appendix A. Supplementary data
Supplementary data related to this article can be found at http://
dx.doi.org/10.1016/j.polymer.2016.09.043.
Fig. 6. Representative strainestress curves of 1 (solid line) and 2 (dashed line).
References
Table 3
[1] R. Auvergne, S. Caillol, G. David, B. Boutevin, J.P. Pascault, Chem. Rev. 114
(2014) 1082e1115.
Mechanical properties of 1 and 2.
[2] R. Bagheri, B.T. Marouf, R.A. Pearson, Polym. Rev. 49 (2009) 201e225.
[3] R.S. Drake, D.R. Egan, W.T. Murphy, Epoxy Resin Chemistry II, American
Chemical Society, Washington, D.C, 1983, p. 221 (Chapter 1).
[4] L.T. Manzione, Plastic Packaging of Microelectronic Devices, Van Nostrand
Reinhold, New York, 1990.
Sample Ultimate strength (MPa) Strain at break (%) Young's modulus (GPa)
1
2
5.42 0.37
12.2 1.39
45.0 1.52
61.7 3.42
(9.76 0.135)ꢀ3
(1.29 0.114) ꢀ2
[5] N. Kinjo, M. Ogata, K. Nishi, A. Kaneda, K. Dusek, Epoxy molding compounds as
encapsulation materials for microelectronic devices, Adv. Polym. Sci. 88
(1989) 1e48.
[6] R.G. Jones, A. Wataru, C. Julian, Silicon-containing Polymers, Kluwer Academic
Publishers, The Netherlands, 2000, pp. 247e321 (Chapter 10).
[7] M. Birot, J.-P. Pillot, J. Dunogues, Chem. Rev. 95 (1995) 1443e1477.
[8] S. Putzien, O. Nuyken, F.E. Kühn, Prog. Polym. Sci. 35 (2010) 687e713.
[9] L.V. Interrante, J.S. Rathore, Dalton Trans. 39 (2010) 9193e9202.
[10] (a) D. Kim, S. Joung, J. Kim, S. Chang, Angew. Chem. Int. Ed. 54 (2015)
14805e14809;
(b) V. Rittscher, M. Gallei, Polym. Chem. 6 (2015) 5653e5662.
[11] (a) K. Matsumoto, H. Shimazu, M. Deguchi, H. Yamaoka, J. Polym. Sci. Part A
Polym. Chem. 35 (1997) 3207e3216;
(b) K. Matsumoto, M. Deguchi, M. Nakano, H. Yamaoka, J. Polym. Sci. Part A
Polym. Chem. 36 (1998) 2699e2706.
[12] (a) M. Jang, J. Crivello, J. Polym. Sci. Part Polym. Chem. 41 (2003) 3056e3073;
(b) Z. Tao, S. Yang, J. Chen, L. Fan, Eur. Polym. J. 43 (2007) 1470e1479;
(c) S.-S. Hou, Y.-P. Chung, C.-K. Chan, P.-L. Kuo, Polymer 41 (2000)
3263e3272;
3.5. Mechanical properties of cured resins
Tensile test of cured 1 and 2 were performed to examine their
mechanical properties. The dumbbell shaped mold of BADGE for
the tensile test could not be prepared in our methods because the
cured BADGE provided too brittle film. Fig. 6 shows representative
strainestress curves of cured 1 and 2. The curves of 1 and 2 were
almost straight line and showed some stretchability. Mechanical
properties including ultimate strength, strain at break, and Young's
modulus are provided in Table 3. Cured 1 and 2 exhibited moderate
ultimate strength of 5.42 0.37 and 12.2 1.39 MPa and elongation
of 45.0
1.52 and 61.7 3.42%, respectively. These mechanical
characters can be mainly attributed to these rubber state due to the
(d) P. Murias, H. Maciejewski, H. Galina, Eur. Polym. J. 48 (2012) 769e773;
(e) C. Hamciuc, D. Serbezeanu, I.-D. Carja, T. Vlad-Bubulac, V.-E. Musteata,
lower Tg below room temperature. Young's moduli of 1 and 2 were
ꢀ2
estimated to be (9.76
0.135)ꢀ3 and (1.29
0.114)
GPa,
ꢀ
ꢀ
V. Perez, C. Lopez, A. Buendia, J. Mater Sci. (2013) 7670e7675;
(f) S. Kandpal, A.K. Saxena, Eur. Polym. J. 58 (2014) 115e124.
[13] K. Matsumoto, Y. Goto, N. Nagao, T. Endo, J. Polym. Sci. Part A Polym. Chem. 52
(2014) 3400e3405.
respectively. From these results, 1 and 2 are expected to be useful in
the development of new elastic materials.
[14] (a) D.A. Girgvliani, L.M. Khananashvill, S.P. Davtian, A.R. Khachatrian,
N.I. Tsomala, A.O. Tonolan, Int. J. Polym. Mater. 25 (1994) 65e76;
(b) H. Schweikl, G. Schmalz, W. Weinmann, Mutat. Res. 521 (2002) 19e27.
[15] T. Ozawa, J. Therm. Anal. Calor. 3 (1970) 301e324, 2.
4. Conclusion
In this study, we synthesized diglycidyl ethers (1 and 2) which
possess not only flexible carbosilane segments but also rigid phe-
nylene moieties. We have also studied their potential curing be-
haviors and thermal and mechanical properties. Cured resins of 1
and 2 exhibited Tg below room temperature (Tg < 19 ꢁC) along with
[16] H.E. Kissinger, J. Res. Natl. Bur. Stand 57 (1956) 217e221.
[17] (a) M. Roth, A. Oesterreicher, F.H. Mostegel, A. Moser, G. Pinter, M. Edler,
R. Piock, T. Griesser, J. Polym. Sci. Part A Polym. Chem. 54 (2016) 418e424;
ꢀ
(b) P. Ortega, J.F. Bermejo, L. Chonco, E. De Jesus, F.J. De La Mata, G. Fernandez,
ꢀ
~
J.C. Flores, R. Gomez, M.J. Serramía, M. Angeles Munoz-Fernandez, Eur. J. Inorg.
Chem. (2006) 1388e1396.