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Alkoxysilyl group-containing azo compound and rubber composition using the same

a technology of alkoxysilyl group and rubber composition, which is applied in the field of alkoxysilyl group containing azo compound and rubber composition using the same, can solve the problems of low productivity and strict synthesis conditions in any of the production methods, and achieve the effect of improving the less heat build-up characteristic, and reducing the heat build-up of rubber

Active Publication Date: 2014-06-19
TOYO TIRE & RUBBER CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The resulting azo compound effectively reduces heat build-up in rubber compositions by generating carbon radicals that form strong bonds, improving the thermal stability and performance of rubber materials, such as in pneumatic tires, compared to conventional polysulfide silane coupling agents.

Problems solved by technology

However, an isocyanate group and a metal alkoxide used in a production method of the above-described conventional technique have high reactivity with water, and therefore have the problem that synthesis conditions are strictly restricted in any of the production methods, and productivity is low.
From the above facts, an alkoxysilyl group-containing azo compound does not yet result in practical use as a silane coupling agent.

Method used

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  • Alkoxysilyl group-containing azo compound and rubber composition using the same
  • Alkoxysilyl group-containing azo compound and rubber composition using the same
  • Alkoxysilyl group-containing azo compound and rubber composition using the same

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis 2,2′-azobis[2-methyl-N-(3- (3- (triethoxysilyl)propilthio)propyl)propionamide]

[0044]20 g of 2,2′-azobis[N-(2-propenyl)-2-methylpropionamide; (VF-096, 10 hour half-life temperature: 96° C., manufactured by Wako Pure Chemical Industries, Ltd.), 34.5 g of 3-mercaptopropyl triethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.66 g of 2,2′-azobis(4-methoxy-2,4-dimethyl-valeronitrile) (V-70, 10 hour half-life temperature: 30° C., manufactured by Wako Pure Chemical Industries, Ltd.) and 55 g of toluene were placed in an eggplant flask. The flask was purged with nitrogen for 20 minutes while stirring with a magnetic stirrer, and then capped tightly. The flask containing a reaction solution was placed in a water bath maintained at 35° C., and reaction was conducted for 2 hours while stirring. The reaction product obtained was concentrated by an evaporator, and then purified by column chromatography.

[0045]The reaction product after purification was subjected to 1H-N...

synthesis example 2

Synthesis of 2,2′-azobis[2-methyl-N-(3-(3-(trimethoxysilyl)propylthio)propyl)propionamide]

[0048]20 g of 2,2′-azobis[N-(2-propenyl)-2-methylpropionamide] (VF-096, manufactured by Wako Pure Chemical Industries, Ltd.), 33.5 g of 3-mercaptopropyl trimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.66 of 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (V-70, manufactured by Wako Pure Chemical Industries, Ltd.) and 55 of toluene were placed in an eggplant flask. The flask was purged with nitrogen for 20 minutes while stirring with a magnetic stirrer, and then capped tightly. The flask containing a reaction solution was placed in a water bath maintained at 35° C., and reaction was conducted for 2 hours while stirring. The reaction product obtained was concentrated by an evaporator, and then purified by column chromatography.

[0049]The reaction product after purification was subjected to 1H-NMR and 13C-NMR analyses, and it was conformed that the reaction product is 2,2′-...

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Abstract

An alkoxysilyl group-containing azo compound represented by the following formula (I), a method for easily obtaining the alkoxysilyl group-containing azo compound, and a rubber composition having improved heat build-up characteristic and the like obtained using the azo compound are provided. The alkoxysilyl group-containing azo compound is preferably obtained by reacting a compound represented by the following formula (2) and a compound represented by the following formula (3);wherein R1 and R2 represent an alkyl group having from 1 to 3 carbon atoms, R3 and R8 represent an alkylene group having from 1 to 3 carbon atoms, R4, R5, R6 and R7 represent hydrogen or an alkyl group having from 1 to 3 carbon atoms, n is an integer of from 1 to 3, and m is an integer of from 1 to 5.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The present invention relates to a novel alkoxysilyl group-containing azo compound usable as a radical generator having reactivity with silica and a metal oxide, a method for producing the azo compound, a rubber composition using the azo compound, and a pneumatic tire using the rubber composition.[0003]2. Background Art[0004]When silica is used in a rubber composition, various sulfur-containing silane coupling agents are used for the purpose of improving dispersion of silica. Performance of a rubber is influenced by a silane coupling agent added. Therefore, for example, a silane coupling agent capable of improving performance such as less heat build-up required in a tire is demanded.[0005]A polymer having a functional group introduced in a molecular terminal is useful because the functional group can be used for a crosslinking reaction of the polymer and stabilization of dispersion of a filler such as silica particles. ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08K5/548
CPCB60C1/0016B60C1/0025C08K5/548C08L21/00
Inventor HISHIKAWA, YASUHIRO
Owner TOYO TIRE & RUBBER CO LTD