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Acryl multi-arm silane coupling agent and preparation method thereof

A silane coupling agent and aryl technology, which is applied in the field of aryl multi-arm silane coupling agent and its preparation, can solve the problems of weak binding force and few cross-linking points of the coupling agent, and achieve enhanced affinity. , Improve the bonding force, the effect of strong adhesion

Active Publication Date: 2014-10-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the coupling agent disclosed in the above-mentioned documents has few cross-linking points, and the matrix resin, especially, has a weak binding force with the aromatic group-containing resin.

Method used

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  • Acryl multi-arm silane coupling agent and preparation method thereof
  • Acryl multi-arm silane coupling agent and preparation method thereof
  • Acryl multi-arm silane coupling agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Add 0.1mol (12.32g) of 1,3,5-triaminobenzene and 200ml of dichloromethane into a four-neck round-bottomed flask equipped with a dropping funnel, a stirrer and a thermometer, blow nitrogen, stir, and add dropwise 0.3mol (61.58g) of isocyanate propyltrimethoxysilane, keep the reaction temperature at 10°C for 2h, then raise the temperature to 35°C for 2h, distill off dichloromethane to get the target compound - (I-1), yield was 98.7%.

[0067] For target compound-(I-1), by 1 H-NMR and 13 Confirmed by C-NMR analysis. 1 H-NMR (CDCl 3 ,ppm):δ7.87(s,C 6 h 3 ); δ6.0(s, NH), δ3.38(t, CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ1.6(m,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ0.58(t,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ3.55(s,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ); 13 C-NMR (CDCl 3 ,ppm): δ108.9(C 6 h 3 ), δ136.3(C 6 h 3 (substitution)), δ154.3 (C=O), δ45.6 (CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ24.8 (CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ12.5(CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ50.2(CH 2...

Embodiment 2

[0070] Add 0.1mol (21.43g) of 3,3',4,4'-biphenyltetramine and 200ml of dichloromethane into a four-neck round-bottomed flask equipped with a dropping funnel, a stirrer and a thermometer, blow nitrogen, and stir , add 0.3mol (61.58g) isocyanate propyltrimethoxysilane dropwise, keep the reaction temperature at 10°C for 2h, then raise the temperature to 40°C and continue the reaction for 3h, distill off the solvent dichloromethane to obtain the target compound -(II- 1), the yield is 95.6%.

[0071] For target compound-(II-1), by 1 H-NMR and 13 Confirmed by C-NMR analysis. 1 H-NMR (CDCl 3 ,ppm):δ6.87-8.05(m,C 12 h 6 ), δ6.08(s, NH), δ6.27(s, NH 2 ),δ3.42(t,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ1.58(m,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ0.61(t,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ3.58(s, CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ); 13 C-NMR (CDCl 3 ,ppm): δ114.8-142.3(C 12 h6 ), δ155.6 (C=O), δ46.8 (CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ25.9(CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ11.4 (C...

Embodiment 3

[0074] Add 0.1mol (21.43g) of 3,3',4,4'-biphenyltetramine and 300ml of dichloromethane into a four-necked round-bottomed flask equipped with a dropping funnel, a stirrer and a thermometer, blow nitrogen, and stir , add 0.4mol (82.11g) isocyanate propyltrimethoxysilane dropwise, keep the reaction temperature at 10°C for 2h, then raise the temperature to 45°C to continue the reaction for 3h, distill off the solvent dichloromethane to obtain the target compound -(III- 1), the yield is 96.7%.

[0075] For target compound-(III-1), by 1 H-NMR and 13 Confirmed by C-NMR analysis. 1 H-NMR (CDCl 3 ,ppm):δ7.51-8.05(m,C 12 h 6 ), δ6.05(s, NH), δ3.43(t, CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ1.63(m,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ0.55(t,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ),δ3.59(s,CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ); 13 C-NMR (CDCl 3 ,ppm): δ116.5-135.2(C 12 h 6 ), δ153.2 (C=O), δ46.2 (CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ24.1(CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ), δ13.2 (CH 2 CH 2 C...

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Abstract

The invention relates to an acryl multi-arm silane coupling agent and a preparation method thereof. The coupling agent comprises a compound with a structure as shown in formula (I) in the specification, wherein in the formula (I), R<1> represents straight-chain type, branch-chain type or cyclic alkylene with carbon number of 1-15, enylene, arylidene or a combination thereof; R<2> represents alkyl with carbon number of 1-18, alkenyl, aryl, halogenated alkyl, halogenated aryl, or an organic group with epoxy, acryloyl, methacryloyl, sulfydryl, amino or cyan; R<3> represents alkoxy, acyloxy or halogen atom; n is 0, 1 or 2. The acryl multi-arm silane coupling agent provided by the invention is good in compatibility with acryl-rich resin materials. While being applied as a coupling agent to treat the surface of an inorganic material, the acryl multi-arm silane coupling agent generates more chemical cross-linking points, so that adhesive force between the inorganic material and the matrix resin is stronger.

Description

technical field [0001] The invention relates to an aryl multi-arm silane coupling agent and a preparation method thereof, belonging to the field of material chemistry. Background technique [0002] The coupling agent is a functional compound that can enhance the bonding performance between inorganic substances and organic substances. The coupling agent molecule contains two groups with different properties, one is an inorganic-philic group, usually a hydroxyl group, which can chemically react with the surface of inorganic materials; the other is an organophilic organic group, which can interact with organic The polymer undergoes physical action or chemical reaction. Therefore, coupling agents are often used to improve the interfacial interaction between inorganic substances and organic substances, and to improve the bonding performance of the interface between organic components and inorganic materials. [0003] Silane coupling agent is the most important type of coupling ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 朱庆增赵冰洁冯圣玉
Owner SHANDONG UNIV
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