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Synthesis of [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane and study on its amine curing properties

Yanling Yu

Yanling Yu

School of Physics and Materials, Nanchang UniversityNanchang, China
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Yu, Yanling
, 
Biwu Huang

Biwu Huang

School of Physics and Materials, Nanchang UniversityNanchang, China
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Huang, Biwu
, 
Yafen Qu

Yafen Qu

School of Physics and Materials, Nanchang UniversityNanchang, China
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Qu, Yafen
, 
Junshan Qiu

Junshan Qiu

School of Physics and Materials, Nanchang UniversityNanchang, China
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Qiu, Junshan
 e 
Yong Lai

Yong Lai

School of Physics and Materials, Nanchang UniversityNanchang, China
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Lai, Yong
  
05 ago 2024
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Pubblicato online: 05 ago 2024
Pagine: 70 - 80
Ricevuto: 15 apr 2024
Accettato: 20 giu 2024
DOI: https://doi.org/10.2478/msp-2024-0020
Parole chiave
© 2024 Yanling Yu et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Fig. 1.

Synthesis route of [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane
Synthesis route of [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane

Fig. 2.

Effect of different catalysts and their contents on the yield of ECETPS
Effect of different catalysts and their contents on the yield of ECETPS

Fig. 3.

Effect of different reaction times and temperatures on the yield of ECETPS
Effect of different reaction times and temperatures on the yield of ECETPS

Fig. 4.

FTIR spectra of triphenylsilane, 1,2-epoxy-4-vinylcyclohexane, [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane
FTIR spectra of triphenylsilane, 1,2-epoxy-4-vinylcyclohexane, [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane

Fig. 5.

1H -NMR hydrogen spectra of TPS, ECV, [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane
1H -NMR hydrogen spectra of TPS, ECV, [2-(3,4-epoxycyclohexyl) ethyl] triphenylsilane

Fig. 6.

1H-NMR pattern of [2-(3,4-epoxycyclohexyl)ethyl] triphenylsilane
1H-NMR pattern of [2-(3,4-epoxycyclohexyl)ethyl] triphenylsilane

Fig. 7.

Amine curing process diagram. (In the ball-and-stick model: red spheres represent oxygen atoms, gray spheres represent carbon atoms, black spheres represent hydrogen atoms, blue spheres represent nitrogen atoms, and purple spheres represent silicon atoms.)
Amine curing process diagram. (In the ball-and-stick model: red spheres represent oxygen atoms, gray spheres represent carbon atoms, black spheres represent hydrogen atoms, blue spheres represent nitrogen atoms, and purple spheres represent silicon atoms.)

Fig. 8.

Chemical equations involved in amine curing
Chemical equations involved in amine curing

Fig. 9.

Effect of different reaction temperatures and reaction times on tensile strength
Effect of different reaction temperatures and reaction times on tensile strength

Fig. 10.

The effect of adding different concentrations of ECETPS on mechanical properties. (left: force and displacement curves for bending properties, right: stress and strain curves for tensile properties).
The effect of adding different concentrations of ECETPS on mechanical properties. (left: force and displacement curves for bending properties, right: stress and strain curves for tensile properties).

Fig. 11.

TG analysis vs. DTG analysis. (The left graph shows TG vs. DTG without added synthetics, right graph shows TG vs. DTG with added synthetics).
TG analysis vs. DTG analysis. (The left graph shows TG vs. DTG without added synthetics, right graph shows TG vs. DTG with added synthetics).

ECETPS yields based on different ratios

Numbering TPS:ECV ECETPS
1 1:1.10 81.58%
2 1:1.15 83.70%
3 1:1.20 92.24%
4 1:1.25 92.34%
5 1:1.30 92.61%

Bending mechanical property data for cured samples

Numbering Elastic modulus (MPa) Bending strength (MPa) Elongation at break (%)
ETE-0 1136.65 25.38 8.31
ETE-1 1847.91 39.10 9.73
ETE-2 1342.19 20.24 8.93
ETE-3 573.75 8.71 8.25
ETE-4 239.12 3.06 7.74

Tensile mechanical property data for cured samples

Numbering Elastic modulus (MPa) Tensile strength (MPa) Elongation at break (%)
ETE-0 505.65 14.53 2.33
ETE-1 581.22 37.95 4.00
ETE-2 443.08 22.78 12.42
ETE-3 384.06 20.60 19.36
ETE-4 290.10 16.08 26.59

1H-NMR spectral analysis of ECETPS

Location of H Chemical shift/ (δ/ppm) Integral ratio Structural formula
1 3.15 2.00 2H -O-CH-
2 1.40~1.70 5.90 6H-CH-CH2-CH-
3 1.72 1.17 1H -CH-
4 1.17 1.98 2H C-CH2-CH2-
5 2.24 2.37 2H Si-CH2-CH2-
6 7.57 6.21 6H Si-C-CH-
7 7.41 9.22 9H -CH-CH-CH-

Amine curing ratios

Numbering ECETPS:E-51:593 amine
ETE-0 0.0:8.0:2.0
ETE-1 0.8:7.2:2.0
ETE-2 1.6:6.4:2.0
ETE-3 2.4:5.6:2.0
ETE-4 3.2:4.8:2.0
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