Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF7 Cites 1 Cited by
  • 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 polymer and the filler, the present invention provides a 2-thiothiazoline or 2-thioimidazoline-terminated Mercaptosilane coupling agent

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Embodiment 1

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

Embodiment 2

[0062] Under an inert gas argon atmosphere, in a 500mL Schlenk bottle, 11.92g (0.1mol) 2-mercaptothiazoline was dissolved in 250mL carbon tetrachloride to form 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), add 30.02g (0.11mol) triethoxysilylpropylsulfenyl chloride dropwise into the solution system, place it at room temperature after the dropwise addition, The molar ratio was 1.1:1, the magneton rotational speed was 500r / min, the reaction time was 10h, and the reaction progress was tracked by TLC detection. After the reaction was completed, the hydrochloride of triethylamine was removed by filtration, and the solvent was removed by a rotary evaporator, followed by column chromatography separation with 400 mesh silica gel powder, the eluent system was petroleum ether and ethyl acetate, and the gradient elution polarity The selection range is 8:1~5:1, and compound 23g is obtained. Characteri...

Embodiment 3

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com