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Ureido silane compound and room temperature curable organopolysiloxane composition

A technology of ureidosilane and compound, which is applied in the field of new ureidosilane compounds, can solve the problems of reduced storage stability, catalyst deactivation, and poor curability over time, and achieves improved storage stability, excellent adhesion, and stable storage excellent effect

Inactive Publication Date: 2012-01-25
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the conventional RTV silicone rubber composition containing various silane coupling agents such as 3-aminopropyltriethoxysilane and ureidopropyltriethoxysilane has excellent adhesiveness, but the silane coupling agent The coupling agent exhibits basicity, therefore, problems such as catalyst deactivation in RTV silicone rubber compositions may arise
This leads to poor curability over time, which causes a decrease in storage stability.

Method used

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  • Ureido silane compound and room temperature curable organopolysiloxane composition
  • Ureido silane compound and room temperature curable organopolysiloxane composition
  • Ureido silane compound and room temperature curable organopolysiloxane composition

Examples

Experimental program
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Effect test

Embodiment 1

[0179] 24.7 g (0.1 mol) of 3-isocyanatopropyltriethoxysilane and 50 mL (2 M) of dichloromethane were added to a 200 mL two-necked eggplant-shaped flask equipped with a stirring element and a dropping funnel, and the mixture was kept at 0°C. In this state, 18.7 g (0.105 mol, 1.05 equivalent) of 3-aminopropyltrimethoxysilane was dripped and reacted. During the dropwise addition, heat generation was confirmed, and when the dropwise addition was terminated, the heat generation ceased, and the system was returned to room temperature. After returning to room temperature, it was further stirred for 10 minutes, dichloromethane as a solvent was distilled off, and the following target compound - formula (9) was obtained.

[0180] For the target compound-formula (9), by 1 H-NMR, 13 C-NMR, 29 Si-NMR analysis confirms that purity and yield are both 99% ( 1 H-NMR is figure 1 , 13 C-NMR is figure 2 , 29 Si-NMR is image 3 ).

[0181] 【Chemical 25】

[0182]

Embodiment 2

[0184] 24.7 g (0.1 mol) of 3-isocyanatopropyltriethoxysilane and 50 mL (2 M) of dichloromethane were added to a 200 mL two-necked eggplant-shaped flask equipped with a stirring element and a dropping funnel, and the mixture was kept at 0°C. In this state, 6.8 g (0.05 mol, 0.5 equivalent) of m-xylylenediamine was dropped and reacted. During the dropwise addition, heat generation was confirmed, and when the dropwise addition was terminated, the heat generation ceased, and the system was returned to room temperature. After returning to room temperature, it was further stirred for 10 minutes, dichloromethane as a solvent was distilled off, and the following target compound - formula (10) was obtained.

[0185] For the target compound-formula (10), by 1 H-NMR, 13 C-NMR, 29 Si-NMR analysis confirms that purity and yield are both 99% ( 1 H-NMR is Figure 4 , 13 C-NMR is Figure 5 , 29 Si-NMR is Figure 6 ).

[0186] 【Chemical 26】

[0187]

Embodiment 3

[0189] 24.7 g (0.1 mol) of 3-isocyanatopropyltriethoxysilane and 50 mL (2 M) of dichloromethane were added to a 200 mL two-necked eggplant-shaped flask equipped with a stirring element and a dropping funnel, and the mixture was kept at 0°C. In this state, bis[3-trimethoxysilylpropyl]amine (KBM-666P, manufactured by Shin-Etsu Chemical Co., Ltd.) was dropped and reacted. During the dropwise addition, heat generation was confirmed, and when the dropwise addition was terminated, the heat generation ceased, and the system was returned to room temperature. After returning to room temperature, it was further stirred for 10 minutes, dichloromethane as a solvent was distilled off, and the following target compound - formula (11) was obtained.

[0190] With regard to the target compound-formula (11), by 1 H-NMR, 13 C-NMR, 29 Si-NMR analysis confirms that purity and yield are both 99% ( 1 H-NMR is Figure 7 , 13 C-NMR is Figure 8 , 29 Si-NMR is Figure 9 ).

[0191] 【Chemical ...

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Abstract

The invention provides an ureido silane compound, which is expressed by the following formula (1). Acording to the invention, the ureido silane compound can be applied as a bonding adjuvant, and is specially effective as the bonding adjuvant of a room temperature solidified organic silicon rubber (RTV) compound, the ureido silane compound possesses an urea-bond, which has chemical interactive effect with the polar functional groups of the object to be bonded to display effective bonding performance.

Description

technical field [0001] The present invention relates to a novel ureidosilane compound not described in the literature. The ureidosilane compound of the present invention is approximately neutral and has excellent storage stability. At the same time, it can be used as an adhesion promoter with various resins and various inorganic materials, a modifier for composite materials, and a surface modification agent for inorganic materials. Agents etc. are useful. In particular, it is useful as an adhesion aid for room temperature curing silicone rubber (RTV) compositions. [0002] In addition, the present invention relates to a room temperature curable (RTV) organopolysiloxane composition used for bonding, fixing, and the like of electric and electronic components. Background technique [0003] It is known that the ureidosilane compound is a coupling agent on the glass surface listed in Japanese PCT Publication No. 2002-526615 (Patent Document 1) or as an example in Japanese PCT P...

Claims

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Application Information

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IPC IPC(8): C07F7/18C08K5/5455C08L83/06
CPCC07F7/081C08K5/5455C08L83/04C09J183/04
Inventor 藤原晃嗣坂本隆文
Owner SHIN ETSU CHEM IND CO LTD
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