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A class of silane coupling agent with ureido and imide structures, preparation method and application thereof

A silane coupling agent, alkyl technology, applied in the field of organosilicon compounds, can solve the problems of high price of phenylethynyl phthalic anhydride, unsuitable for large-scale industrial use and the like

Active Publication Date: 2020-10-27
POME TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, phenylethynyl phthalic anhydride is expensive and not suitable for large-scale industrial use

Method used

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  • A class of silane coupling agent with ureido and imide structures, preparation method and application thereof
  • A class of silane coupling agent with ureido and imide structures, preparation method and application thereof
  • A class of silane coupling agent with ureido and imide structures, preparation method and application thereof

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preparation example Construction

[0055] The preparation method of silane coupling agent of the present invention is as follows:

[0056] 1) The compound represented by formula (2) and the compound represented by formula (3) undergo condensation reaction;

[0057] 2) Imidization reaction is carried out after the condensation reaction to obtain the silane coupling agent represented by formula (1).

[0058]

[0059]

[0060] X, R in formula (2) and (3) 1 , R 2 , R 3 , R 4 The definitions are the same as those mentioned above.

[0061] Further, the condensation reaction is carried out in an aprotic polar solvent, and the effect of each aprotic polar solvent is equivalent. Considering the convenience of cost and acquisition method, preferably, the aprotic polar solvent is selected from N -Methylpyrrolidone, N,N -dimethylformamide, N,N -at least one of dimethylacetamide, dimethylsulfoxide and gamma-butyrolactone, preferably N -Methylpyrrolidone or / and N,N - Dimethylacetamide.

[0062] Further, the ...

Embodiment 1

[0070] Add 26.2 g (0.1 mol, X-12-967C, Shin-Etsu Chemical) of 3-(trimethoxysilyl)propyl succinic anhydride to a 500 mL three-necked flask equipped with a stirrer and a thermometer, and add the solvent N,N- Dimethylacetamide 150 mL, start stirring. At the same time, 7.4 g (0.1 mol, Tokyo Chemical Industry Co., Ltd.) of methylurea was weighed and dissolved in 100 mL N,N-in dimethylacetamide. Place the above-mentioned 500 mL three-necked flask in an ice-water bath, slowly add methylurea solution dropwise while stirring, and control the temperature of the reaction material below 10°C. After the dropwise addition was completed, the ice-water bath was removed to return to room temperature, and the reaction was continued at this temperature for 20 hr. After the reaction was completed, 15.8 g (0.2 mol) of pyridine was added to the reaction system, and after stirring evenly, 20.4 g (0.2 mol) of acetic anhydride was slowly added, and the reaction was carried out at room temperature ...

Embodiment 2

[0074] Add 26.2 g (0.1 mol, X-12-967C, Shin-Etsu Chemical) of 3-(trimethoxysilyl)propyl succinic anhydride to a 500 mL three-neck flask equipped with a stirrer and a thermometer, add the solvent N,N- Dimethylacetamide 150 mL, start stirring. At the same time, weigh 8.8 g (0.1 mol, Tokyo Chemical Industry Co., Ltd.) of ethyl urea and dissolve it in 100 mL N,N- in dimethylacetamide. Place the above-mentioned 500 mL three-neck flask in an ice-water bath, slowly add ethyl urea solution dropwise while stirring, and control the temperature of the reaction material below 10°C. After the dropwise addition was completed, the ice-water bath was removed to return to room temperature, and the reaction was continued at this temperature for 20 hr. After the reaction was completed, 15.8 g (0.2 mol) of pyridine was added to the reaction system, and after stirring evenly, 20.4 g (0.2 mol) of acetic anhydride was slowly added, and the reaction was carried out at room temperature for 20 hr. ...

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Abstract

The invention discloses a class of silane coupling agents with ureido and imide structures, a preparation method and application thereof, wherein the structural formula of the silane coupling agent isrepresented by a general formula (1), and the silane coupling agent is obtained by reacting substituted urea or thiourea with a butanedioic anhydride-terminated silane compound. According to the invention, the silane coupling agent not only has an imide structure similar to polyimide, but also has a ureido group or a thiourea group, and has a remarkable promoting effect on bonding of high-polarity heat-resistant organic materials such as polyimide resins, polyether sulfone resins or polybenzoxazole resins and the like and a base material.

Description

technical field [0001] The present invention relates to a kind of organosilicon compound, specifically relate to a kind of silane coupling agent with urea group and imide structure and its preparation method and application, this silane coupling agent can promote typical polyimide, polyethersulfone The combination of highly polar heat-resistant resin materials such as resin or polybenzoxazole resin and metal substrates is a good adhesion promoter for heat-resistant resins. Background technique [0002] Conventionally, polyimide resins, polybenzoxazole resins, and the like, which are excellent in heat resistance and mechanical properties, have been widely used in surface protective films and interlayer insulating films of semiconductor elements of electronic equipment. The heat-cured film exists in the device as a permanent film, so the physical properties of the cured film after heating are very important. In order to ensure the reliability of semiconductor packaging, the a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/5455C08K5/548C08L79/08C08L79/04C08J5/18C07F7/18
CPCC08K5/548C08J5/18C07F7/1892C08J2379/08C08J2379/04C08L79/08C08L79/04
Inventor 李铭新王华森公聪聪
Owner POME TECH CO LTD
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