In this paper, a series of bio-based epoxy resins containing organic silicone were prepared from eugenol through a mild synthetic route. Then, 4,4′-diaminophenyl methane (DDM) was applied to cure these epoxy resins, and bisphenol A epoxy resin (DGEBA) was used as a control. The chemical structures of the synthesized resins were characterized by nuclear magnetic resonance (1H-NMR). Properties of the cured epoxy resins were investigated by dielectric test, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA), and scanning electron microscopy (SEM). Compared with DGEBA, the bio-based epoxy resin containing cyclic organic silicon structure exhibited a dramatically lower dielectric constant at both low and high frequencies (3.46, 1 kHz, room temperature). Moreover, the silicone-modified bio-based epoxy resins demonstrated no weight loss below 325 °C and higher residues at 800 °C than that of DGEBA.

References

References
1.
Auvergne
,
R.
,
Caillol
,
S.
,
David
,
G.
,
Boutevin
,
B.
, and
Pascault
,
J. P.
,
2014
, “
Biobased Thermosetting Epoxy: Present and Future
,”
Chem. Rev.
,
114
(
2
), pp.
1082
1115
.
2.
Jin
,
F. L.
,
Li
,
X.
, and
Park
,
S. J.
,
2015
, “
Synthesis and Application of Epoxy Resins: A Review
,”
J. Ind. Eng. Chem.
,
29
, pp.
1
11
.
3.
Li
,
H. Y.
,
Wang
,
L. J.
,
Jacob
,
K.
, and
Wong
,
C. P.
,
2002
, “
Syntheses and Characterizations of Thermally Degradable Epoxy Resins—III
,”
J. Polym. Sci. Pol. Chem.
,
40
(
11
), pp.
1796
1807
.
4.
Li
,
J. H.
,
Zhang
,
G. P.
,
Deng
,
L. B.
,
Jiang
,
K.
,
Zhao
,
S. F.
,
Gao
,
Y. J.
,
Sun
,
R.
, and
Wong
,
C. P.
,
2015
, “
Thermally Reversible and Self-Healing Novolac Epoxy Resins Based on Diels–Alder Chemistry
,”
J. Appl. Polym. Sci.
,
132
(
26
), p.
42167
.
5.
Liu
,
W. S.
,
Wang
,
Z. G.
,
Chen
,
Z.
, and
Zhao
,
L. N.
,
2012
, “
Thermo-Initiated Cationic Polymerization of Phosphorus-Containing Cycloaliphatic Epoxides With Tunable Degradable Temperature
,”
Polym. Degrad. Stab.
,
97
(
5
), pp.
810
815
.
6.
Wang
,
X.
, and
Chung
,
D. D. L.
,
1998
, “
Short Carbon Fiber Reinforced Epoxy Coating as a Piezoresistive Strain Sensor for Cement Mortar
,”
Sens. Actuators, A
,
71
(
3
), pp.
208
212
.
7.
Ashrafi
,
B.
,
Guan
,
J.
,
Mirjalili
,
V.
,
Zhang
,
Y.
,
Chun
,
L.
,
Hubert
,
P.
,
Simard
,
B.
,
Kingston
,
C. T.
,
Bourne
,
O.
, and
Johnston
,
A.
,
2011
, “
Enhancement of Mechanical Performance of Epoxy/Carbon Fiber Laminate Composites Using Single-Walled Carbon Nanotubes
,”
Compos. Sci. Technol.
,
71
(
13
), pp.
1569
1578
.
8.
Ratna
,
D.
, and
Banthia
,
A. K.
,
2000
, “
Epoxidized Soybean Oil Toughened Epoxy Adhesive
,”
J. Adhes. Sci. Technol.
,
14
(
1
), pp.
15
25
.
9.
Ratna
,
D.
, and
Banthia
,
A. K.
,
2000
, “
Toughened Epoxy Adhesive Modified With Acrylate Based Liquid Rubber
,”
Polym. Int.
,
49
(
3
), pp.
281
287
.
10.
Agrawal
,
A.
, and
Satapathy
,
A.
,
2015
, “
Epoxy Composites Filled With Micro-Sized AlN Particles for Microelectronic Applications
,”
Part. Sci. Technol.
,
33
(
1
), pp.
2
7
.
11.
Liu
,
W. S.
,
Wang
,
Z. G.
,
Chen
,
Z.
,
Li
,
J. F.
, and
Zhao
,
L. N.
,
2012
, “
Synthesis and Properties of Two Novel Silicon-Containing Cycloaliphatic Epoxy Resins for Electronic Packaging Application
,”
Polym. Adv. Technol.
,
23
(
3
), pp.
367
374
.
12.
Liu
,
W. S.
,
Wang
,
Z. G.
,
Xiong
,
L.
, and
Zhao
,
L. N.
,
2010
, “
Phosphorus-Containing Liquid Cycloaliphatic Epoxy Resins for Reworkable Environment-Friendly Electronic Packaging Materials
,”
Polymer
,
51
(
21
), pp.
4776
4783
.
13.
Rashid
,
E. S. A.
,
Ariffin
,
K.
,
Kooi
,
C. C.
, and
Akil
,
H. M.
,
2009
, “
Preparation and Properties of POSS/Epoxy Composites for Electronic Packaging Applications
,”
Mater. Des.
,
30
(
1
), pp.
1
8
.
14.
Saidina
,
D. S.
,
Mariatti
,
M.
, and
Julie
,
M. J.
,
2015
, “
Dielectric Properties and Thermal Properties of Calcium Copper Titanate and Barium Titanate Hybrid Fillers Filled Epoxy Thin Film Composites for Electronic Packaging Applications
,”
J. Mater. Sci. Mater. Electron.
,
26
(
8
), pp.
6245
6251
.
15.
Sancaktar
,
E.
, and
Bai
,
L.
,
2011
, “
Electrically Conductive Epoxy Adhesives
,”
Polymers
,
3
(
1
), pp.
427
466
.
16.
Sham
,
M. L.
, and
Kim
,
J. K.
,
2005
, “
Curing Behavior and Residual Stresses in Polymeric Resins Used for Encapsulanting Electronic Packages
,”
J. Appl. Polym. Sci.
,
96
(
1
), pp.
175
182
.
17.
Sun
,
X. B.
,
Yu
,
A. P.
,
Ramesh
,
P.
,
Bekyarova
,
E.
,
Itkis
,
M. E.
, and
Haddon
,
R.
,
2011
, “
Oxidized Graphite Nanoplatelets as an Improved Filler for Thermally Conducting Epoxy-Matrix Composites
,”
ASME J. Electron. Packag.
,
133
(
2
), p. 020905.
18.
Wan
,
W. T.
,
Yu
,
D. M.
,
He
,
J.
,
Xie
,
Y. C.
,
Huang
,
L. B.
, and
Gu
,
X. S.
,
2008
, “
Simultaneously Improved Toughness and Dielectric Proverties of Epoxy/Core-Shell Particle Blends
,”
J. Appl. Polym. Sci.
,
107
(
2
), pp.
1020
1028
.
19.
Wang
,
Z.
,
Zhou
,
W.
,
Dong
,
L.
,
Sui
,
X.
,
Cai
,
H.
,
Zuo
,
J.
, and
Chen
,
Q.
,
2016
, “
Dielectric Spectroscopy Characterization of Relaxation Process in Ni/Epoxy Composites
,”
J. Alloys Compd.
,
682
, pp.
738
745
.
20.
Zeng
,
X. L.
,
Ye
,
L.
,
Guo
,
K.
,
Sun
,
R.
,
Xu
,
J. B.
, and
Wong
,
C. P.
,
2016
, “
Fibrous Epoxy Substrate With High Thermal Conductivity and Low Dielectric Property for Flexible Electronics
,”
Adv. Electron. Mater.
,
2
(
5
), p.
1500485
.
21.
Agrawal
,
A.
, and
Satapathy
,
A.
,
2014
, “
Thermal and Dielectric Behavior of Epoxy Composites Filled With Ceramic Micro Particulates
,”
J. Compos. Mater.
,
48
(
30
), pp.
3755
3769
.
22.
Singha
,
S.
, and
Thomas
,
M. J.
,
2010
, “
Dielectric Properties of Epoxy-Al2O3 Nanocomposite System for Packaging Applications
,”
IEEE Trans. Compon. Packag. Technol.
,
33
(
2
), pp.
373
385
.
23.
Chen
,
C.
,
Tang
,
Y. J.
,
Ye
,
Y. S.
,
Xue
,
Z. G.
,
Xue
,
Y.
,
Xie
,
X. L.
, and
Mai
,
Y. W.
,
2014
, “
High-Performance Epoxy/Silica Coated Silver Nanowire Composites as Underfill Material for Electronic Packaging
,”
Compos. Sci. Technol.
,
105
, pp.
80
85
.
24.
Du
,
F. P.
,
Yang
,
W.
,
Zhang
,
F.
,
Tang
,
C. Y.
,
Liu
,
S. P.
,
Yin
,
L.
, and
Law
,
W. C.
,
2015
, “
Enhancing the Heat Transfer Efficiency in Graphene-Epoxy Nanocomposites Using a Magnesium Oxide-Graphene Hybrid Structure
,”
ACS Appl. Mater. Interfaces
,
7
(
26
), pp.
14397
14403
.
25.
Gonon
,
P.
,
Sylvestre
,
A.
,
Teysseyre
,
J.
, and
Prior
,
C.
,
2001
, “
Dielectric Properties of Epoxy/Silica Composites Used for Microlectronic Packaging, and Their Dependence on Post-Curing
,”
J. Mater. Sci.: Mater. Electron.
,
12
(
2
), pp.
81
86
.
26.
Ho
,
T. H.
, and
Wang
,
C. S.
,
2001
, “
Modification of Epoxy Resin With Siloxane Containing Phenol Aralkyl Epoxy Resin for Electronic Encapsulation Application
,”
Eur. Polym. J.
,
37
(
2
), pp.
267
274
.
27.
Jubsilp
,
C.
,
Takeichi
,
T.
,
Hiziroglu
,
S.
, and
Rimdusit
,
S.
,
2009
, “
Effect of Resin Compositions on Microwave Processing and Thermophysical Properties of Benzoxazine-Epoxy-Phenolic Ternary Systems Filled With Silicon Carbide (SiC) Whisker
,”
Polym. Eng. Sci.
,
49
(
5
), pp.
1022
1029
.
28.
Khanam
,
P. N.
,
Al-Maadeed
,
M. A.
, and
Mrlik
,
M.
,
2016
, “
Improved Flexible, Controlled Dielectric Constant Material From Recycled LDPE Polymer Composites
,”
J. Mater. Sci.: Mater. Electron.
,
27
(
8
), pp.
8848
8855
.
29.
Kim
,
Y. H.
,
Lim
,
Y. W.
,
Kim
,
Y. H.
, and
Bae
,
B. S.
,
2016
, “
Thermally Stable Siloxane Hybrid Matrix With Low Dielectric Loss for Copper-Clad Laminates for High-Frequency Applications
,”
ACS Appl. Mater. Interfaces
,
8
(
13
), pp.
8335
8340
.
30.
Kong
,
L. Q.
,
Cheng
,
Y. R.
,
Jin
,
Y. X.
,
Qi
,
T. K.
, and
Xiao
,
F.
,
2016
, “
Low k Epoxy Resin Containing Cycloaliphatic Hydrocarbon With High Crosslinking Density
,”
J. Appl. Polym. Sci.
,
133
(
21
), pp. 3456–3465.
31.
Lee
,
L. H.
, and
Chen
,
W. C.
,
2005
, “
Organic-Inorganic Hybrid Materials From a New Octa(2,3-Epoxypropyl)Silsesquioxane With Diamines
,”
Polymer
,
46
(
7
), pp.
2163
2174
.
32.
Li
,
L.
, and
Zheng
,
S. X.
,
2016
, “
Enhancement of Dielectric Constants of Epoxy Thermosets Via a Fine Dispersion of Barium Titanate Nanoparticles
,”
J. Appl. Polym. Sci.
,
133
(
16
), pp. 1322–1328.
33.
Miao
,
X.
,
Gui
,
D. Y.
,
Zeng
,
G. F.
, and
Liu
,
J. H.
,
2010
, “
Study on Preparation and Properties of Epoxy Resin Modified by Amine-Terminated Polyimide as Electronic Packaging Materials
,”
11th International Conference on Electronic Packaging Technology and High Density Packaging
(
ICEPT-HDP
), Xi'an, China, Aug.16–19, pp. 160–164.
34.
Albarran-Preza
,
E.
,
Corona-Becerril
,
D.
,
Vigueras-Santiago
,
E.
, and
Hernandez-Lopez
,
S.
,
2016
, “
Sweet Polymers: Synthesis and Characterization of Xylitol-Based Epoxidized Linseed Oil Resins
,”
Eur. Polym. J.
,
75
, pp.
539
551
.
35.
Chatterjee
,
S.
, and
Saito
,
T.
,
2015
, “
Lignin-Derived Advanced Carbon Materials
,”
Chemsuschem
,
8
(
23
), pp.
3941
3958
.
36.
Duval
,
A.
, and
Lawoko
,
M.
,
2014
, “
A Review on Lignin-Based Polymeric, Micro- and Nano-Structured Materials
,”
React. Funct. Polym.
,
85
, pp.
78
96
.
37.
Desroches
,
M.
,
Escouvois
,
M.
,
Auvergne
,
R.
,
Caillol
,
S.
, and
Boutevin
,
B.
,
2012
, “
From Vegetable Oils to Polyurethanes: Synthetic Routes to Polyols and Main Industrial Products
,”
Polym. Rev.
,
52
(
1
), pp.
38
79
.
38.
Diaz
,
A.
,
Katsarava
,
R.
, and
Puiggali
,
J.
,
2014
, “
Synthesis, Properties and Applications of Biodegradable Polymers Derived From Diols and Dicarboxylic Acids: From Polyesters to Poly(Ester Amide)s
,”
Int. J. Mol. Sci.
,
15
(
5
), pp.
7064
7123
.
39.
Li
,
C.
,
Fan
,
H.
,
Wang
,
D.-Y.
,
Hu
,
J.
,
Wan
,
J.
, and
Li
,
B.
,
2013
, “
Novel Silicon-Modified Phenolic Novolacs and Their Biofiber-Reinforced Composites: Preparation, Characterization and Performance
,”
Compos. Sci. Technol.
,
87
, pp.
189
195
.
40.
Oliveira
,
A.
,
Becker
,
C. M.
, and
Amico
,
S. C.
,
2015
, “
Evaluation of the Characteristics of an Epoxy Resin With Different Degassing Agents
,”
Polimeros
,
25
(
2
), pp.
186
191
.
41.
Lora
,
J. H.
, and
Glasser
,
W. G.
,
2002
, “
Recent Industrial Applications of Lignin: A Sustainable Alternative to Nonrenewable Materials
,”
J. Polym. Environ.
,
10
(
1
), pp.
39
48
.
42.
Sasaki
,
C.
,
Wanaka
,
M.
,
Takagi
,
H.
,
Tamura
,
S.
, and
Asada
,
C.
,
2013
, “
Evaluation of Epoxy Resins Synthesized From Steam-Exploded Bamboo Lignin
,”
Ind. Crops Prod.
,
43
, pp.
757
761
.
43.
Sun
,
G.
,
Sun
,
H.
,
Liu
,
Y.
,
Zhao
,
B.
,
Zhu
,
N.
, and
Hu
,
K.
,
2007
, “
Comparative Study on the Curing Kinetics and Mechanism of a Lignin-Based-Epoxy/Anhydride Resin System
,”
Polymer
,
48
(
1
), pp.
330
337
.
44.
Li
,
C.
,
Dai
,
J. Y.
,
Liu
,
X. Q.
,
Jiang
,
Y. H.
,
Ma
,
S. Q.
, and
Zhu
,
J.
,
2016
, “
Green Synthesis of a Bio-Based Epoxy Curing Agent From Isosorbide in Aqueous Condition and Shape Memory Properties Investigation of the Cured Resin
,”
Macromol. Chem. Phys.
,
217
(
13
), pp.
1439
1447
.
45.
Dai
,
J. Y.
,
Ma
,
S. Q.
,
Zhu
,
L. X.
,
Wang
,
S.
,
Yang
,
L. J.
,
Song
,
Z. L.
,
Liu
,
X. Q.
, and
Zhu
,
J.
,
2016
, “
UV-Thermal Dual Cured Anti-Bacterial Thiolene Networks With Superior Performance From Renewable Resources
,”
Polymer
,
108
, pp.
215
222
.
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