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Diacylthioxo silane coupling agent and preparation method thereof

A technology of bisacylthiosilane coupling agent and mercaptopropyltrialkoxysilane, applied in the field of bisacylthiosilane coupling agent and its preparation, achieving the effects of low equipment requirements, reasonable design, and reasonable synthesis route

Inactive Publication Date: 2013-11-20
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problem of premature vulcanization of rubber, the present invention proposes a bisacylthiosilane coupling agent and a preparation method thereof in combination with various existing sulfur-containing silane coupling agents

Method used

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  • Diacylthioxo silane coupling agent and preparation method thereof
  • Diacylthioxo silane coupling agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] This embodiment is implemented according to route one.

[0026] In a dry 2L flask, add 476g (2mol) 3-mercaptopropyltriethoxysilane, add 252.5g (2.5mol) anhydrous triethylamine, add 200mL anhydrous toluene to dilute, start mechanical stirring, after mixing evenly, 127 g (1 mol) of oxalyl chloride was slowly added dropwise from the constant pressure dropping funnel, and a large amount of white insoluble precipitate was formed immediately. After 30 minutes, the dropwise addition was completed. After stirring for 2 hours, the precipitate was removed by filtration, and triethylamine and toluene were removed by distillation under reduced pressure. , obtain a light yellow viscous liquid, slightly turbid, after filtering once, remove low boiling under reduced pressure, obtain 659g light yellow transparent viscous liquid, namely the product oxalyl-bis-[triethoxysilylpropyl sulfur ], the yield is 98%. Through gas chromatography analysis, the content of the two raw materials has ...

Embodiment 2

[0028] This embodiment is implemented according to the second route.

[0029] 1) Prepare an aqueous solution of sodium dithioadipate. In a 2L three-necked flask, add 240g (1mol) of solid sodium sulfide nonahydrate, add 150g of water, and dissolve to obtain a sodium sulfide solution with a concentration of 20%. Press the dropping funnel and drop it in about 20 minutes. With the dropping of adipoyl chloride, the temperature in the bottle will rise to about 70 °C, keep stirring, and cool the system to room temperature naturally to obtain a slightly viscous transparent Aqueous sodium dithioadipate solution.

[0030] 2) Preparation of adipyl-bis-[triethoxysilylpropyl sulfide]. Add 3g saturated tetrahexylammonium chloride solution to the solution prepared in step 1), under mechanical stirring, drop 240g (1mol) 3-chloropropyltriethoxysilane from the constant pressure dropping funnel, within 15 minutes The dropwise addition was completed, after completion, the temperature was raise...

Embodiment 3

[0032] This embodiment is implemented according to route one.

[0033] Add 238 g (1 mol) of 3-mercaptopropyl triethoxysilane to a dry 2 L flask, add 50 mL of anhydrous tetrahydrofuran to dilute, take 101.5 g (0.5 mol) of terephthaloyl chloride and dissolve it in 200 mL of anhydrous tetrahydrofuran. The constant pressure dropping funnel was slowly added dropwise. Under mechanical stirring, the generated hydrogen chloride was discharged with nitrogen. After 30 minutes, the dropwise addition was completed. The stirring was maintained for 2 hours, and the toluene was distilled off under reduced pressure. At this time, the pH value of the system was about 4. Add 5 g After neutralization with sodium ethoxide, filter to obtain light yellow viscous liquid, remove low boiling under reduced pressure to obtain 294g light yellow transparent viscous liquid, which is the product phthaloyl-bis-[triethoxysilylpropyl sulfide] ], the yield is 97%. Gas chromatography analysis showed that the co...

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Abstract

The invention discloses a diacylthioxo silane coupling agent and a preparation method thereof. A structural general formula of the silane coupling agent is shown in the specification, wherein in the formula, R1 is methyl or ethyl, and the X group is oxalyl group, phthaloyl / m-benezene diformyl / terephthaloyl, malonyl, succinyl, adipoyl, fumaryl, isodivaleryl, 2-methyladipyl, octanedioyl, decanedioyl and other dicapryloyl. The diacylthioxo silane coupling agent is accessible in raw materials and low in equipment requirements, can be produced in most plants or laboratories, can be widely used in rubber chemicals and effectively improves rubber properties.

Description

technical field [0001] The invention relates to a bisacylthio silane coupling agent and a preparation method thereof. Background technique [0002] Sulfur-containing silane coupling agent is an important auxiliary agent in the rubber industry. It can enhance the adhesion between rubber and fillers, and has significant effects on the tensile strength, wear resistance, wet slip resistance and other properties of rubber products. optimization effect. Sulfur-containing silane coupling agents, such as bis-[3-(triethoxysilyl)propyl]-tetrasulfide (trade name Si-69), have become indispensable in the rubber industry, especially in tire manufacturing The product. At present, the most commonly used sulfur-containing silane coupling agent in the rubber industry is polysulfide silane, of which Si-69 is used in the largest amount. Polysulfide silane usually contains polysulfide bonds connected with multiple sulfur atoms. At high temperature, polysulfide bonds can be cleavage, thereby p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C08K5/548C08L21/00
Inventor 唐红定熊英梁秋鸿
Owner WUHAN UNIV
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