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
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[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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