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Fluorine-containing organosilicon compound, method for producing same, room temperature curable fluorine-containing rubber composition, cured product thereof, and article

A technology of organosilicon compound and fluorine-containing rubber, which is applied in the field of room temperature curing fluorine-containing rubber composition, can solve the problems of insufficient chemical resistance and durability, and achieve excellent water resistance and low moisture permeability, acid resistance and Excellent amine resistance and high fluorine content

Pending Publication Date: 2019-11-29
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

An organic fluorine compound and a composition containing the elastomer satisfying such characteristics have been reported in Patent Document 1 (Japanese Patent No. 3121245 ), but the composition has a silicon atom in the molecule The perfluoropolyether compound of the combined phenylene structure is used as the base polymer, so the chemical resistance of the cured product (fluoroelastomer) obtained from this composition, especially the long-term resistance to high-concentration acids and amine compounds The durability of time cannot be said enough

Method used

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  • Fluorine-containing organosilicon compound, method for producing same, room temperature curable fluorine-containing rubber composition, cured product thereof, and article
  • Fluorine-containing organosilicon compound, method for producing same, room temperature curable fluorine-containing rubber composition, cured product thereof, and article
  • Fluorine-containing organosilicon compound, method for producing same, room temperature curable fluorine-containing rubber composition, cured product thereof, and article

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0304] Drop into the following formula in the 300ml four-necked flask that possesses stirring rod, thermometer, serpentine condenser and dropping funnel:

[0305] 【Chemical 67】

[0306]

[0307] (In the formula, the average of p'+q' is 38.)

[0308] 189.2 g (0.030 mol, viscosity at 25°C: 430 mPa·s) of the indicated compound having acid fluoride groups at both terminals. Then, it was dripped from the dropping funnel while stirring at room temperature (25°C, the same below) by the following formula:

[0309] 【Chemical 68】

[0310]

[0311] A mixture of 15.8 g (0.072 mol) of the indicated compound and 6.5 g (0.064 mol) of triethylamine. After completion of the dropping, stirring was carried out at 60° C. for 2 hours. Next, the filtrate obtained by pressure-filtering the reaction mixture was stripped under reduced pressure at 120° C. / 3 mmHg to obtain 195.3 g of a pale yellow transparent liquid compound. This liquid compound was poured into the same flask as above, 50.0 ...

Embodiment 2

[0343] In Example 1, instead of 7.3 g of trimethoxysilane, the following formula (13) was used:

[0344] 【Chemical 74】

[0345]

[0346] Except for 7.9 g (0.050 mol) of the silane compound shown, the reaction and post-treatment were carried out in the same manner as in Example 1, and 279.3 g of a transparent oily compound tinged with pale yellow were obtained. The viscosity of the obtained oily compound was 34700 mPa·s (25°C), and the refractive index was 1.340 (25°C). the liquid compound 1 As a result of H-NMR measurement, the absorption shown below was observed.

[0347] 1 H-NMR (TMS standard)

[0348] δ=3.3~3.8ppm (m, N-C H 2 -,8H)

[0349] δ=4.1~4.2ppm (m, OC=C H 2 ,8H)

[0350] δ=6.9~7.4ppm (m, N- Ph , 20H)

[0351] In addition, this compound was hydrolyzed, and the amount of acetone desorbed was quantified. As a result, it was 0.028 mol / 100 g, which was confirmed by the following structural formula (14):

[0352] 【Chemical 75】

[0353]

[0354] (wher...

Embodiment 3

[0357] In Example 2, instead of 7.9 g of the silane compound represented by the above formula (13), the following formula (15) was used:

[0358] 【Chemical 76】

[0359]

[0360] Except for 8.1 g (0.050 mol) of the silane compound shown, the reaction and post-treatment were carried out in the same manner as in Example 2 to obtain 280.4 g of a transparent liquid compound tinged with light yellow. The obtained liquid compound had a viscosity of 35200 mPa·s (25°C) and a refractive index of 1.341 (25°C). the liquid compound 1 As a result of H-NMR measurement, the absorption shown below was observed.

[0361] 1 H-NMR (TMS standard)

[0362] δ=1.94ppm (s, SiOCC H 3 , 12H)

[0363] δ=3.3~3.8ppm (m, N-C H 2 -,8H)

[0364] δ=6.9~7.4ppm (m, N- Ph , 20H)

[0365] In addition, this compound was hydrolyzed, and the amount of acetic acid released was quantified, and the result was 0.028 mol / 100g, which was confirmed by the following structural formula (16):

[0366] 【Chemica...

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Abstract

The invention provides a new fluorine-containing organosilicon compound suitable for obtaining an elastomer excellent in mold releasability, water repellency and low moisture permeability and furtherenhanced in chemical resistance, especially acid resistance and amine resistance, a method for producing the same, and a room temperature curable fluorine-containing rubber composition containing thesame. The fluorine-containing organosilicon compound is represented by the following formula 1. [A is an unsubstituted or substituted aliphatic divalent hydrocarbon group, R2 and R1 are each an unsubstituted or substituted divalent hydrocarbon group, R3 is an unsubstituted or substituted saturated aliphatic divalent hydrocarbon group, Rf is a perfluoroalkylene group or a divalent perfluoropolyether group, X is a hydrolyzable group, Ph is a phenyl group, and Q is a group represented by the following formula (2) or (3). (R4 is at least one unsubstituted or substituted divalent hydrocarbon groupselected from O, N and Si, Ph is a phenyl group) (R5 and R6 are unsubstituted or substituted divalent hydrocarbon groups) a is 0 or more, b is 1, 2 or 3].

Description

technical field [0001] The present invention relates to a fluorine-containing organosilicon compound that can be suitably used as a base polymer of, for example, a fluorine-containing elastomer (cured fluorine-containing rubber) that is used in rubber materials and mold release agents and is excellent in acid resistance and amine resistance, and its production method , A room temperature curable fluorine-containing rubber composition containing the fluorine-containing organosilicon compound, a cured product thereof (cured fluorine-containing rubber product), and articles and applications using the same. Background technique [0002] Organic fluorine compounds have been used in various fields. For example, a fluorine-containing elastomer (cured fluorine-containing rubber) obtained by mixing an organic fluorine compound with a cross-linking agent and cross-linking at a high temperature of 150° C. or higher has been used as a rubber material or a mold release agent. However, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/336C08G77/46C08G65/333C08L83/12C08K3/04C08K5/57C08K5/5415
CPCC08G65/336C08G77/46C08G65/33317C08K3/04C08K5/57C08K5/5415C08L83/12
Inventor 林龙人
Owner SHIN ETSU CHEM IND CO LTD
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