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Sulfur-containing silane coupling agent and preparation method thereof

A technology of sulfur silane coupling agent and alkyl, which is applied in the field of sulfur-containing silane coupling agent compounds and their preparation, can solve the problems of reducing rubber porosity, increasing product porosity, increasing organic matter emissions, etc., to achieve the reduction of volatile organic compounds Emissions, avoiding premature scorch, and reducing the effect of organic matter emissions

Inactive Publication Date: 2013-10-16
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since these coupling agents usually have multiple alkoxy groups, when they are used in rubber additives, they will increase the emission of organic matter and increase the porosity of the product. Long-chain polysulfide silane coupling agents such as Si-69, Since the polysulfide bond is easy to decompose, it is easy to cause premature scorch of the rubber during the rubber mixing process
In order to improve these shortcomings, the present invention designs a silane coupling agent containing long-chain hydrocarbon-based polyether. Since the long-chain hydrocarbon-based polyether does not produce volatile organic compounds, it can reduce the emission of organic matter in the rubber production process, and can also reduce rubber pores. At the same time, the shielding effect of long-chain hydrocarbon-based polyether can overcome the problem of premature scorch of polysulfide silane coupling agent

Method used

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  • Sulfur-containing silane coupling agent and preparation method thereof
  • Sulfur-containing silane coupling agent and preparation method thereof

Examples

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Embodiment 1

[0029] Example 1 [x=2, y=5, m=1]

[0030] In this embodiment, Route 1 is adopted.

[0031] 1) Preparation of γ-chloropropylethoxypropyl polyether-based silane

[0032] In a 2L dry three-necked flask, under the protection of nitrogen, add 212g (1mol) γ-chloropropyltrichlorosilane, 46g (1mol) ethanol and 560g (2mol) polyethylene glycol monopropyl ether. The molecular formula can be expressed as CH 3 CH 2 CH 2 (OCH 2 CH 2 ) 5 After the OH is mixed evenly, drop it from the constant pressure dropping funnel, discharge the generated hydrogen chloride with nitrogen, and remove it through tail gas absorption treatment. After 30 minutes, the dropwise addition is completed, and the reaction is continued at 90-120°C. After 2 hours, no Then there is ethanol reflux, gas chromatography detects that γ-chloropropyltrichlorosilane and ethanol have completely reacted, stop heating, and after cooling down to below 60°C, reduce the pressure to -0.08Mpa, keep the reduced pressure for 15 minu...

Embodiment 2

[0037] Example 2 [x=2, y≈12, m=1]

[0038] This embodiment adopts route two.

[0039] 1) Preparation of γ-chloropropylethoxybis(polyethylene glycol monomethyl ether) silane

[0040] Add 240g (1mol) γ-chloropropyltriethoxysilane to a dry 2L three-necked flask, add 1100g (2mol) polyethylene glycol with an average molecular weight of 550 (mPEG-550, the average y value is about 12, Aldrich reagent) Alcohol monomethyl ether, under the protection of nitrogen, add 5g of sodium ethylate as a catalyst, start stirring, heat to 90-110°C, distill out the ethanol produced after transesterification, stop the reaction until the ethanol is no longer distilled out, and cool down to After 50°C, start to reduce the pressure to -0.8Mpa to remove the low boiling point. After reducing the pressure for 15 minutes, cool and filter to obtain γ-chloropropylethoxybis(polyethylene glycol monomethyl ether) silane.

[0041] 2) An aqueous solution of sodium polysulfide was prepared in the same manner as i...

Embodiment 3

[0042] Example 3 [x=2, y=5, m=2]

[0043] This embodiment adopts route three.

[0044] Add 530g (1.0mol) bis-[3-(triethoxysilyl)propyl]-tetrasulfide (Si-69) with an average sulfur chain length of 3.75 into a 2L dry three-necked flask, add 840g (2mol) molecular weight 420 polyethylene glycol monotridecyl ether (molecular formula can be expressed as: C 13 h 27 (OCH 2 CH 2 ) 5 OH), add 3g of sodium ethylate as a catalyst, heat to 90-110°C, continue to distill ethanol, react until no ethanol is distilled out, stop the reaction, add a little hydrogen chloride ethanol solution to neutralize to neutral, nitrogen protection to lower the temperature When the temperature is below 50°C, start to decompress and remove the low boiling point. After completion, cool and filter to obtain bis-[3-(diethoxy(polyethylene glycol monotridecyl ether) silicon)propyl]-tetrasulfide . The product is identified by proton nuclear magnetic resonance spectrum, and the result is 1 H-NMR (CDCl 3 , δ,...

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Abstract

The invention discloses a sulfur-containing silane coupling agent and a preparation method thereof. The structural general formula of the sulfur-containing silane coupling agent is as follows (see the specification), wherein n=2-10, Z is perssad (R1O) m (G) 3-mSi, m is 1 or 2, R1 is methyl or ethyl, G is (R2) (O (CR' R'') x) yO, x=2-10, y=1-20, R2 is alkyl, R' is hydrogen, alkyl or phenyl, and R'' is hydrogen or alkyl. The preparation method is simple and reliable, and the prepared sulfur-containing silane coupling agent can be widely used in rubber chemicals to effectively improve the rubber performance.

Description

technical field [0001] The invention relates to a sulfur-containing silane coupling agent compound and a preparation method thereof. Background technique [0002] Sulfur-containing silane coupling agent is a commonly used additive in the rubber industry, which can improve the compatibility between rubber and fillers, such as carbon black and silica, and improve the properties of rubber products. Taking automobile tires as an example, the addition of sulfur-containing silane coupling agents can significantly improve the tire's wet skid resistance, wear resistance, heat generation and other properties. At present, in the automobile tire industry, bis-[3-(triethoxysilyl)propyl]-tetrasulfide is the most widely used. This silane coupling agent is also called Si-69, and the polysulfide bond can participate in When the rubber is vulcanized, the siloxy group can react with the surface of the filler to bond, which acts as a "molecular bridge" between the filler and the rubber. Anot...

Claims

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Application Information

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IPC IPC(8): C07F7/18C08K5/548C08L21/00
Inventor 唐红定熊英梁秋鸿
Owner WUHAN UNIV
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