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Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof

A benzothiazole mercaptosilane and low-volatility technology, which is applied in the field of low-volatility benzothiazole-mercaptosilane and its preparation, can solve the physical damage of workers, pollute the processing workshop environment, and cannot remove methoxy and ethoxy groups and other problems, to achieve the effect of fast vulcanization speed, long scorch time, improved mechanical properties and dynamic mechanical properties

Active Publication Date: 2012-02-08
JIANGSU QIXIANG HIGH NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This multifunctional additive integrates multiple functions such as plasticizing, dispersing, promoting, and reinforcing, but because the silicon atom of the additive has three alkoxy substituents, it will release a large amount of alcohol during or after mixing with fillers, polluting The environment of the processing workshop has a certain degree of damage to the body of the workers; among them, the commonly used trimethoxysilane and triethoxysilane will release a considerable amount of corresponding alcohols - methanol and ethanol
[0007] In addition, methoxy-substituted silanes and ethoxy-substituted silanes are more reactive than the corresponding long-chain alkoxy-substituted silanes and react with fillers more quickly while completely removing the methoxy and ethoxy groups

Method used

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  • Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof
  • Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof
  • Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047] A kind of low volatility benzothiazole mercaptosilane, wherein, the molecular structural formula of silane is:

[0048]

[0049] The preparation method of above-mentioned silane is:

[0050] Step a: Weigh 0.1mol (28.86g) of γ-chloropropyltriethoxysilane and 0.2mol (54.8g) of polyether HO-(C 2 h 4 -O) 2 -C 12 h 25 Place in a three-necked flask, add 0.5g of zinc naphthenate, react at 70°C for 2 hours, and remove ethanol in a vacuum for one hour to obtain polyether-modified chloropropylsilane (ie, semi-finished silane);

[0051] Step b: Weigh 0.1mol (16.7g) of 2-mercaptobenzothiazole and 250g of toluene, place them in a round-bottomed three-neck flask, add 0.1mol (5.4g) of sodium methoxide, stir well, and heat the mixture to 120°C, and from one side of the three-necked flask at a distance of 0.1m 3 Nitrogen was introduced at a speed of 1 / h, and then 75.3g of polyether modified chloropropylsilane was added to the above solution, and then reacted at 120°C for 10 hou...

Embodiment 2

[0066] A kind of low volatility benzothiazole mercaptosilane, wherein, the molecular structural formula of silane is:

[0067]

[0068] The preparation method of above-mentioned silane is:

[0069] Step a: Weigh 0.1mol (17.1g) γ-chloromethyltrimethoxysilane and 0.2mol (81.2g) polyether HO-(C 2 h 4 -O) 5 -C 12 h 25 Place in a three-necked flask, add 0.5g of sodium ethoxide, react at 165°C for 7 hours, and remove methanol in a vacuum for one hour to obtain polyether-modified chloropropylsilane (ie semi-finished silane);

[0070] Step b: Weigh 0.1mol (16.7g) of 2-mercaptobenzothiazole and 250g of toluene, place them in a round-bottomed three-neck flask, add 0.1mol (5.4g) of sodium methoxide, stir well, and heat the mixture to 120°C, then add 81.4g of the above-mentioned polyether-modified chloropropylsilane to the above-mentioned solution, and then react at 50°C for 24 hours under the protection of nitrogen, filter the obtained product, wash, and remove the low-boiling fr...

Embodiment 3

[0085] A kind of low volatility benzothiazole mercaptosilane, wherein, the molecular structural formula of silane is:

[0086]

[0087] The preparation method of above-mentioned silane is:

[0088] Step a: Weigh 5mol (862.5) γ-chloropropyltrimethoxysilane and 10mol (508g) polyether HO-(C 2 h 4 -O) 7 -C 13 h 27 Put it in a reaction kettle, add 50g of butyl aluminate, and react under 0.09Mpa vacuum at 180°C for 10 hours to obtain polyether-modified chloropropylsilane (ie, semi-finished silane);

[0089] Step b: Weigh 5mol (835g) of 2-mercaptobenzothiazole and 10kg of acetone, place in a stainless steel container, add 7.5mol (300g) of sodium hydroxide, heat to 80°C, stir evenly, and blow in nitrogen , and then added to the above solution, and then reacted at 80°C for 6 hours under the protection of nitrogen, the obtained product, the sediment was filtered, and the low boiling point fraction was removed by vacuum distillation to obtain a brownish red liquid with a yield of...

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Abstract

The invention discloses a low-volatility benzothiazolyl mercaptosilane and a preparation method thereof. A molecular structural formula of the low-volatility benzothiazolyl mercaptosilane is shown in the patent specification. The preparation method of the low-volatility benzothiazolyl mercaptosilane comprises the following steps that 1, a polyether and a chloroalkyl silane undergo a reaction at a temperature of 30 to 180 DEG C in the presence of one or more catalysts; and R3-H is separated from the reaction products so that a silane semi-finished product is obtained; and 2, 2-mercaptobenzothiazole is added into an organic solvent; and one or more alkalis and semi-finished silane are added into the 2-mercaptobenzothiazole solution to undergo a reaction with stirring at a temperature of 20 to 120 DEG C in a nitrogen atmosphere for 0.5 to 24 hours; the reaction products are subjected to filtration, washing and reduced pressure distillation to produce a brown-red liquid desired product. The low-volatility benzothiazolyl mercaptosilane can release a small quantity of alcohols, can improve reinforcing effects, mechanical properties and dynamic mechanical properties of vulcanized rubbers, and rolling resistance and wet skid resistance of tread rubber, has long scorch time and fast sulfuration speed, and can improve greatly sulfuration performances of rubber materials.

Description

technical field [0001] The invention relates to the technical field of rubber additives, in particular to a low-volatility benzothiazole-mercaptosilane and a preparation method thereof. Background technique [0002] Various fillers such as carbon black, white carbon black, clay, calcium carbonate, talcum powder, halloysite, magnesium hydroxide, aluminum hydroxide, etc. are widely used in rubber formulations, among which carbon black, white carbon black, etc. are reinforcing fillers , Clay, calcium carbonate, talc, halloysite, magnesium hydroxide, aluminum hydroxide, etc. are non-reinforcing fillers. Studies have shown that the interaction between the reinforcing filler and the rubber cross-linked network can effectively improve the reinforcing effect of the filler. Even non-reinforcing fillers can produce different degrees of reinforcement after proper surface modification to form a strong bond with the rubber network. Silanes such as bis[3-(triethoxysilyl)propyl]tetrasulf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C08L7/00C08L21/00C08K5/548
Inventor 彭华龙
Owner JIANGSU QIXIANG HIGH NEW MATERIAL
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