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Multi-functional silane coupling agent as well as preparation method and application thereof

A silane coupling agent, multi-functional technology, applied in the field of silane coupling agent synthesis, can solve the problems of carbon black, silica and rubber modification, single functional group, etc.

Active Publication Date: 2019-05-14
ZHUZHOU TIMES NEW MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such sulfur-containing silane coupling agents or amino silane coupling agents have a relatively single type of functional group. For the compound filled with carbon black and silica, it is impossible to modify carbon black, silica and rubber at the same time. properties, the effect of carbon black and white carbon black mixed filling reinforcement needs to be further improved

Method used

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  • Multi-functional silane coupling agent as well as preparation method and application thereof
  • Multi-functional silane coupling agent as well as preparation method and application thereof
  • Multi-functional silane coupling agent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of multifunctional silane coupling agent of the present invention, comprises the following steps:

[0033] (1) to [HCl] NH 2 (CH 2 ) 2 S 2 (CH 2 ) 2 NH 2 ·[HCl] dehydrochlorination: prepare 20% ammonia solution, then add [HCl]·NH 2 (CH 2 ) 2 S 2 (CH 2 ) 2 NH 2 [HCl], stirred in ice-water bath for 2.5h; then added diethyl ether to extract 5 times, combined the organic layer; washed the organic layer 3 times with saturated aqueous sodium chloride solution, added anhydrous magnesium sulfate, stirred and dried for a day and night, filtered, and the filtrate was rotary evaporated The organic solvent was removed, and dried in vacuum at 20 °C to constant weight to obtain NH 2 (CH 2 ) 2 S 2 (CH 2 ) 2 NH 2 ;

[0034] (2) take by weighing 24g gamma-chloropropyltriethoxysilane ((C 2 h 5 O) 3 Si(CH 2 ) 3 Cl), 20g NH 2 (CH 2 ) 2 S 2 (CH 2 ) 2 NH 2 Add 80g of dimethylformamide into a three-necked round-bottomed flask under nitrogen...

Embodiment 2

[0036] A preparation method of multifunctional silane coupling agent of the present invention, comprises the following steps:

[0037] (1) NH 2 (CH 2 ) 2 SH·[HCl] dehydrochlorination: prepare 15% NaOH aqueous solution, add NH 2 (CH 2 ) 2 SH·[HCl], stirred in an ice-water bath for 2 h; added dichloromethane to extract 4 times, combined the organic layer; then washed the organic layer 4 times with saturated aqueous sodium chloride solution, added anhydrous magnesium sulfate, stirred and dried for a day and night, filtered, and the filtrate The organic solvent was removed by rotary evaporation, and dried in vacuum at 25 °C to constant weight to obtain NH 2 (CH 2 ) 2 sh.

[0038] (2) Weigh 20g gamma-chloropropyltrimethoxysilane ((CH 3 O) 3 Si(CH 2 ) 3 Cl), 15g NH 2 (CH 2 ) 2 SH and 110g toluene were added into a three-necked round-bottomed flask under the protection of nitrogen, stirred, slowly heated up, and reacted at 110°C for 24h; solvent, vacuum-dried to const...

Embodiment 3

[0040] A preparation method of multifunctional silane coupling agent of the present invention, comprises the following steps:

[0041] (1) NH 2 (CH 2 ) 4 SH·[HCl] dehydrochlorination: prepare 10% KOH solution, add NH 2 (CH 2 ) 4 SH·[HCl], stirred in an ice-water bath for 1 h; added ethyl acetate to extract 3 times, combined the organic layer; washed the organic layer 5 times with saturated aqueous sodium chloride solution, added anhydrous magnesium sulfate, stirred and dried for a day and night, filtered, and the filtrate was rotary evaporated The organic solvent was removed, and dried in vacuum at 30 °C to constant weight to obtain NH 2 (CH 2 ) 4 sh.

[0042] (2) Weigh 20g gamma-chloropropyltrimethoxysilane ((CH 3 O) 3 Si(CH 2 ) 3 Cl), 31gNH 2 (CH 2 ) 4 SH and 110g DMSO were added into a three-necked round-bottomed flask under nitrogen protection, stirred, and the temperature was raised slowly, and reacted at 120°C for 24h. After the reaction is over, let it s...

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Abstract

The invention relates to a multi-functional silane coupling agent. The molecular structure of the silane coupling agent simultaneously contains an amino group, an alkoxysilyl group and a sulfur-containing functional group; the amino functional group comprises one or more of an amino group, a secondary amino group and a tertiary amino group; the sulfur-containing functional group comprises one or several of sulfydryl, a mono-sulfide bond, a dis-ulfide bond, a tri-sulfide bond and a tetra-sulfide bond. The multi-functional silane coupling agent provided by the invention contains the amino group,the alkoxysilyl group and the sulfur-containing functional group and can simultaneously modify carbon black, white carbon black and rubber, fully realize the effect of carbon black and / or white carbon black mixed filling and reinforcing rubber, effectively improve the tensile strength, the elongation at break and the constant tensile stress of the rubber, significantly reduce the permanen compression deformation and significantly improve the heat generation performance.

Description

technical field [0001] The invention belongs to the technical field of silane coupling agent synthesis, and in particular relates to a multifunctional silane coupling agent and its preparation method and application. Background technique [0002] Silane coupling agent is a kind of low-molecular organosilane with organic functional groups that can combine with organic materials such as rubber and hydrolyzable functional groups that can combine with inorganic materials such as fillers. It can interact with each other through chemical reactions or physical actions. The inert organic material and the inorganic material form a "bridge bond" to combine the two, thereby enhancing the bonding force between the inorganic material and the organic material interface and improving the performance of the composite material. [0003] At present, when producing carbon black or silica-filled rubber compounds in the rubber industry, sulfur-containing silane coupling agents (such as Si69) or ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/548C08K3/36C08K3/04C08L7/00C07F7/18
Inventor 王雪飞吴玲玲余海文黎华明杨军
Owner ZHUZHOU TIMES NEW MATERIALS TECH
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