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Synthesis of a novel UV-curable prepolymer 1,3-bis[(3-ethyl-3-methoxyoxetane)propyl]tetramethyldisiloxane and study on its UV-curing properties

Cheng Chen
Cheng Chen
, 
Bi-Wu Huang
Bi-Wu Huang
, 
Zheng-Ting Lu
Zheng-Ting Lu
 et 
Yang Wu
Yang Wu
   | 13 déc. 2021
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Publié en ligne: 13 déc. 2021
Pages: 371 - 382
Reçu: 16 juil. 2021
Accepté: 17 oct. 2021
DOI: https://doi.org/10.2478/msp-2021-0030
Mots clés
© 2021 Cheng Chen 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 3-ethyl-3-hydroxymethyloxetane and 3-ethyl-3-allylmethoxyoxetane.
Synthesis route of 3-ethyl-3-hydroxymethyloxetane and 3-ethyl-3-allylmethoxyoxetane.

Fig. 2

Synthesis route of the prepolymer.
Synthesis route of the prepolymer.

Fig. 3

Dimensions of the designed samples.
Dimensions of the designed samples.

Fig. 4

(A) The infrared spectrum of 3-ethyl-3-hydroxymethyloxetane. (B) The infrared spectrum of 3-ethyl-3-allylmethoxyoxetane.
(A) The infrared spectrum of 3-ethyl-3-hydroxymethyloxetane. (B) The infrared spectrum of 3-ethyl-3-allylmethoxyoxetane.

Fig. 5

(B) The infrared spectrum curve of 3-ethyl-3-allylmethoxyoxetane. (C) The infrared spectrum curve of 1,1,3,3-tetramethyldisiloxane. (D) The infrared spectrum curve of the prepolymer.
(B) The infrared spectrum curve of 3-ethyl-3-allylmethoxyoxetane. (C) The infrared spectrum curve of 1,1,3,3-tetramethyldisiloxane. (D) The infrared spectrum curve of the prepolymer.

Fig. 6

1H-NMR spectrum of 3-ethyl-3-hydroxymethyloxetane.
1H-NMR spectrum of 3-ethyl-3-hydroxymethyloxetane.

Fig. 7

1H-NMR spectrum of 3-ethyl-3-allylmethoxyoxetane.
1H-NMR spectrum of 3-ethyl-3-allylmethoxyoxetane.

Fig. 8

1H-NMR spectrum of 1,1,3,3-tetramethyldisiloxane.
1H-NMR spectrum of 1,1,3,3-tetramethyldisiloxane.

Fig. 9

1H-NMR spectrum of the prepolymer.
1H-NMR spectrum of the prepolymer.

Fig. 10

TG (A) and DTG (B) curves of films cured with the prepolymer.
TG (A) and DTG (B) curves of films cured with the prepolymer.

Fig. 11

The viscosity of the prepolymer at different temperatures.
The viscosity of the prepolymer at different temperatures.

Fig. 12

Heat flow of prepolymer, E-51 and 2021p.
Heat flow of prepolymer, E-51 and 2021p.

Fig. 13

Total heat of prepolymer, E-51, and 2021p.
Total heat of prepolymer, E-51, and 2021p.

Fig. 14

Conversion of a prepolymer, E-51, and 2021p.
Conversion of a prepolymer, E-51, and 2021p.

Analytical table of the 1H-NMR spectrum for the 3-ethyl-3-allylmethoxyoxetane.

Location of H Chemical shift/(δ/ppm) Structural formula
1 0.86 3H, -CH3
2 1.73 2H, -CH2-
3 3.53 2H, -CH2-
4 3.97 2H, -CH2-
5 5.87 H, -CH=
6 5.24 2H, =CH2
7 4.36 2H, -CH2-
8 4.42 2H, -CH2-

Mechanical property test results of the prepolymer UV-cured samples.

Numbering Tensile strength /MPa Elastic modulus /MPa Elongation at break /%
1 26.28 3,028.72 4.13
2 23.99 2,831.19 3.89
3 22.97 2,730.26 4.23
4 27.90 3,195.19 3.96
5 28.62 2,890.40 4.26
Average value 25.95 2,935.15 4.09
Standard deviation 2.19 161.97 0.15

Mechanical property test results of the 2021p UV-cured samples.

Numbering Tensile strength/MPa Elastic modulus/MPa Elongation at break/%
1 32.11 3,165.01 2.63
2 24.17 3,454.75 2.58
3 34.87 2,719.27 2.13
4 26.26 3,012.03 2.67
5 25.76 2,855.39 2.08
Average value 28.63 3,041.29 2.42
Standard deviation 4.60 285.21 0.29

Materials and reagents.

Materials and reagents Purity (%) Manufacturer
Diethyl carbonate 99.7 Sinopharm Chemical Reagent Co., Ltd
Trihydroxypropane 99.7 Sinopharm Chemical Reagent Co., Ltd
Anhydrous magnesium sulfate (solid) Sinopharm Chemical Reagent Co., Ltd
Potassium hydroxide (solid) Tianjin Damao Chemical Reagent Factory
Allyl bromide 99.7 Tianjin Damao Chemical Reagent Factory
Toluene 99.9 Xilong Chemical Co., Ltd
Dichloromethane 99.7 Xilong Chemical Co., Ltd
Tetrabutylammonium bromide 99.7 Xilong Chemical Co., Ltd
Triarylsulfonium hexafluoroantimonate (UV-6976) 99.7 Dow Union Carbide
1,1,3,3-tetramethyldisiloxane 99 Shanghai Chuqing New Material Co., Ltd.
Karstedt catalyst 99.5 Shanghai Aladdin Technology Co., Ltd.
E-51 epoxy resin 98 Shanghai Resin Factory
2021p alicyclic epoxy resin 98 Daicel (China) Investment Co., Ltd

Analytical table of the 1H-NMR spectrum for the 3-ethyl-3-hydroxymethyloxetane.

Location of H Chemical shift /(δ/ppm) Structural formula
1 0.77 3H, -CH3
2 1.60 2H, -CH2-
3 3.58 2H, -CH2-
4 3.74 H, -OH
5 4.28 2H, -CH2-
6 4.33 2H, -CH2-

Mechanical property test results of the E-51 UV-cured samples.

Numbering Tensile strength/MPa Elastic modulus/MPa Elongation at break/%
1 20.75 2,224.11 5.83
2 19.60 1,912.03 6.12
3 21.03 2,329.58 4.76
4 20.57 2,168.32 4.92
5 18.44 1,895.36 5.43
Average value 20.08 2,105.88 5.41
Standard deviation 1.06 193.53 0.58

Analytical table of the 1H-NMR spectrum for the 1,1,3,3-tetramethyldisiloxane.

Location of H Chemical shift/(δ/ppm) Structural formula
1 0.17 12H, -CH3
2 4.66 2H, -Si-H

Analytical table of the 1H-NMR spectrum for the prepolymer.

Location of H Chemical shift/(δ/ppm) Structural formula
1 0.02 12H, -CH3
2 0.47 4H, -CH2-
3 1.55 4H, -CH2-
4 3.37 4H, -CH2-
5 3.49 4H, -CH2-
6 1.70 4H, -CH2-
7 0.85 6H, -CH3
8 4.35 4H, -CH2-
9 4.41 4H, -CH2-
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