2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent as well as synthesis method and application thereof

A mercapto-terminated silane coupling agent and thioimidazoline group-capped technology, which is applied in the field of silane coupling agents, can solve the problem that silane coupling agents cannot improve the interaction between polymers and fillers, and shorten the vulcanization time , Promote vulcanization, reduce fuel consumption and carbon dioxide emissions

Active Publication Date: 2020-04-24
EVE RUBBER RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problem that the silane coupling agent in the prior art cannot well improve the interaction between the p

Method used

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  • 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent as well as synthesis method and application thereof
  • 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent as well as synthesis method and application thereof
  • 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0028] Example 1

[0029] Under inert gas nitrogen atmosphere, in a 1LSchlenk bottle, dissolve 23.84g (0.2mol) 2-mercaptothiazoline in 400mL toluene, make a solution with a concentration of 0.5mol / L, add 41.70mL (0.3mol) triethyl Amine, then place the solution in an ice water bath (0°C), and add 65.50g (0.24mol) of triethoxysilylpropylsulfenyl chloride dropwise to the solution system. After the dropwise addition, place it at room temperature, the molar ratio is 1.2 :1, the magnetron rotation speed is 800r / min, the reaction time is 12h, and the TLC detection tracks the reaction process. After the reaction is completed, the hydrochloride of triethylamine is removed by filtration, and the solvent is removed with a rotary evaporator, and then separated by column chromatography with 400 mesh silica gel powder. The eluent system is petroleum ether and ethyl acetate, with gradient elution polarity The selection range is 8:1~5:1 to obtain 48g of the new compound. It was characterized a...

Example Embodiment

[0061] Example 2

[0062] Under an inert gas argon atmosphere, in a 500mL Schlenk flask, 11.92g (0.1mol) 2-mercaptothiazoline was dissolved in 250mL carbon tetrachloride to prepare a solution with a concentration of 0.4mol / L, and 20.85mL (0.15 mol) triethylamine, then place the solution in an ice-water bath (0°C), and add 30.02g (0.11mol) triethoxysilylpropylsulfenyl chloride dropwise to the solution system. After the addition is complete, place it at room temperature. The molar ratio is 1.1:1, the magnetron rotation speed is 500r / min, the reaction time is 10h, and the reaction process is tracked by TLC detection. After the reaction is completed, the hydrochloride of triethylamine is removed by filtration, and the solvent is removed with a rotary evaporator, and then separated by column chromatography with 400 mesh silica gel powder. The eluent system is petroleum ether and ethyl acetate, with gradient elution polarity The selection range is 8:1~5:1 to obtain 23g of compound. C...

Example Embodiment

[0064] Example 3

[0065] Under inert gas nitrogen atmosphere, in a 250mL Schlenk bottle, 11.72g (0.1mol) 2-mercaptothiazole was dissolved in 150mL dichloromethane to prepare a solution with a concentration of 0.67mol / L, and 20.85mL (0.15mol) was added. Ethylamine, then place the solution in an ice-water bath (0°C), 32.75g (0.12mol) triethoxysilylpropylsulfenyl chloride is added dropwise to the solution system, and after the addition is complete, it is placed at room temperature. The molar ratio is 1.2:1, the magnetron rotation speed is 600r / min, the reaction time is 10h, and the TLC detection tracks the reaction process. After the reaction is completed, the hydrochloride of triethylamine is removed by filtration, and the solvent is removed with a rotary evaporator, and then separated by column chromatography with 400 mesh silica gel powder. The eluent system is petroleum ether and ethyl acetate, with gradient elution polarity The selection range is 10:1~5:1 to obtain 21g of the...

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Abstract

The invention belongs to a silane coupling agent, and particularly relates to a 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent as well as a synthesis method and application thereof. The 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent has a structure represented by a formula (I) or a formula (II). According to the 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent represented by the formula (I) or the formula (II), the interaction between a polymer and a filler can be significantly enhanced, the hysteresis lossof a rubber material can be reduced, the heat generation can be reduced, the Payne effect of the rubber material can be reduced, and the dispersibility of white carbon black can be improved so as toreduce the oil consumption and the carbon dioxide emission during the tire driving process and enhance the wear resistance of a tire; meanwhile, the 2-thiothiazolyl or 2-thioimidazolyl terminated mercaptosilane coupling agent provided by the invention has the effect of promoting vulcanization, so that the energy loss in a vulcanization process can be reduced.

Description

technical field [0001] The invention relates to a silane coupling agent, in particular to a 2-thiothiazolinyl or 2-thioimidazolinyl-terminated mercaptosilane coupling agent and its synthesis method and application. Background technique [0002] As an inorganic filler, white carbon black has become the most important inorganic reinforcing filler after carbon black because of its excellent reinforcing properties. Because its surface is covered with a large number of silanol groups, it exhibits strong polarity and high surface energy. . The rubber molecule is non-polar as an alkyl chain. When the two are blended, phase interface separation is easy to occur due to thermodynamic incompatibility. [0003] Silane coupling agent is a silane containing two groups with different chemical properties, including organic functional groups and hydrolyzable silicon functional groups. Its general formula can be expressed as Y-R-SiX 3 . Since there are two kinds of functional groups, organ...

Claims

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Application Information

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IPC IPC(8): C08K5/548C08L9/06C08L9/00C07F7/18
CPCC07F7/1804C07F7/1892C08L9/06C08L2205/02C08K5/5477C08L9/00
Inventor 王滨贾维杰柳海江王祥飞
Owner EVE RUBBER RES INST
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