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Functionalized organosulfur compound for reducing hysteresis in rubber article

A rubber composition and compound technology, applied in organic chemistry, transportation and packaging, special tires, etc., can solve problems such as hysteresis increase

Inactive Publication Date: 2020-12-18
SI GROUP INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a common undesired side effect of using these resins in rubber compounds is increased hysteresis, heat build-up under dynamic stress of the rubber product

Method used

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  • Functionalized organosulfur compound for reducing hysteresis in rubber article
  • Functionalized organosulfur compound for reducing hysteresis in rubber article
  • Functionalized organosulfur compound for reducing hysteresis in rubber article

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1A

[0269] Example 1A: Synthesis of an Exemplary Functionalized Organosulfur Compound—2,2'-[Dithiobis(2,1-Ethylenenitriloethylidene)]bisphenol

[0270]

[0271] Cystamine dihydrochloride (90.1 g) and 2'-hydroxyacetophenone (108.9 g) were added to a round bottom flask along with 1-butanol (600.1 g). The contents form a suspension with stirring. The reaction was heated to 120°C and refluxed for a total of 10 hours. The reaction mixture was cooled to 40°C and sodium hydroxide (32 g) was added. The reaction mixture was stirred for a total of 1 hour during which time the temperature increased from about 40°C to about 73.4°C over a period of 30 minutes. The reaction mixture was cooled to room temperature and vacuum filtered through a sintered Buchner funnel. The product was washed with additional 1-butanol (100 g) and the product isolated on the filter was dried overnight. The solid product was dissolved in dichloromethane (703.7 g) and transferred to a separatory funnel. All pr...

Embodiment 1B

[0275] Example 1B: Synthesis of Modified Phenol Novolac Resin

[0276]

[0277] Phenol novolak resin (SI Group HRJ-12952, 400.0g) and 40.0g 2,2'-[dithiobis(2,1-ethylenediylnitriloethylidene)]bisphenol (10% by weight Resin) and the functionalized organosulfur compound prepared in Example 1A (or 1A') were charged together into a round bottom flask. The contents of the flask were mixed using a mechanical stirrer fitted with a metal stirring paddle. The reaction mixture was then heated to 160°C. After about 1 hour, the temperature reached 160°C and the temperature set point was lowered to 120°C. After a total of 2 hours of heating, the reaction mixture was poured into a pot and allowed to cool to form a solid. The final weight of the recovered product was 438.5 g, the yield was 99.6%.

Embodiment 2A

[0278] Example 2A: Synthesis of an Exemplary Functionalized Organosulfur Compound—Diphenyl 3,3'-dithiodipropionate (DPE)

[0279]

[0280] Dithiodipropionic acid (80.2 g) and pyridine (0.1 g) were charged via syringe into a 500 mL round bottom flask equipped with thermocouple, addition funnel, drying tube, septum and nitrogen blanket. Thionyl chloride (92.3 g) was added to the addition funnel and charged to the reaction flask dropwise at room temperature (24° C.) over about 30 minutes. During this addition and over the next 2 hours, the batch endothermed to a temperature of about 8°C and then slowly returned to room temperature. During the reaction time of approximately 18 hours, the batch was stirred and gassed, as indicated by bubbles forming in the solution. Once gas evolution ceased, the yellow solution was heated to 60-85°C and vacuum was applied to 55-60 mmHg to remove excess thionyl chloride. The total amount of overhead collected was 14.8 g. The solution was then...

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Abstract

This invention relates to a process of mixing a phenolic resin and one or more functionalized organosulfur compounds into a rubber composition comprising a rubber component. The interaction between the phenolic resin component and the functionalized organosulfur compound component with the rubber component reduces the hysteresis increase compared to a rubber composition without the functionalizedorganosulfur compound component, upon curing the rubber composition. The invention also relates to a rubber composition prepared according to this process and a rubber product formed from the rubber composition.

Description

[0001] related application [0002] This application claims U.S. Provisional Application No. 62 / 643,611, filed March 15, 2018, U.S. Provisional Application No. 62 / 644,160, filed March 16, 2018, and 62 Priority of U.S. Provisional Application No. 749,996; all of these applications are hereby incorporated by reference in their entirety. [0003] field of invention [0004] The present invention generally relates to the use of functionalized organosulfur compounds in rubber compositions. [0005] Background of the invention [0006] The rolling resistance of a tire on the road accounts for most of the energy wasted by a car propelling itself forward. The improvement (lowering) of rolling resistance is important as the automotive industry strives for better fuel economy. Rolling resistance is affected by external factors such as aerodynamic drag and road friction, but also by the properties of the tire material itself. It is estimated that the tire's internal friction and hyste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B60C1/00C08K5/37C07C323/25C08G8/28C08L7/00
CPCB60C1/00C08K5/37C08L7/00C08K5/3725C08L61/06C08L61/14C08L2310/00C08J3/226
Inventor D·C·希尔Q·麦格林J·M·惠特尼A·克拉维兹T·E·巴纳赫
Owner SI GROUP INC
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