Silane disulfide vegetable oils, method of making and use in rubber compositions and tires

Patent metadata

Field	Value
Publication number	US-11440877-B2
Application number	US-201916671271-A
Country	US
Kind code	B2
Filing date	Nov 1, 2019
Priority date	Nov 1, 2019
Publication date	Sep 13, 2022
Grant date	Sep 13, 2022

Abstract

The present invention is directed to novel silane disulfide vegetable oils, a method of making the oils, their use in rubber compositions, and their use in tires.

First claim

What is claimed is:

1. A vegetable oil derivative comprising the structure

where R 1 , R 2 , and R 3 are independently C15-C20 alkenyl, C15-C20 alkyl, and optionally containing aromatic groups; R 4 is —S—S—R 7 — or R 4 is —S—X—S—S—R 7 — where X is unsubstituted C1 to C10 alkane diyl; R 5 , R 6 are independently C1 to C10 alkyl, R 7 is C1 to C10 alkane diyl, j=0 to 2, k=1 to 3, and j+k=3; wherein each R 4 is attached via a carbon-sulfur linkage to one of R 1 , R 2 or R 3 ; and m is the number of the carbon-sulfur linkages based on olefinic unsaturation of R 1 , R 2 and R 3 .

2. The vegetable oil derivative of claim 1 comprising the structure

where m″ is the number of the carbon-sulfur linkages based on olefinic unsaturation of R 1 , R 2 and R 3 .

3. The vegetable oil derivative of claim 1 comprising the structure

where m′ is the number of the carbon-sulfur linkages based on olefinic unsaturation of R 1 , R 2 and R 3 and n is 1 to 6.

4. The vegetable oil derivative of claim 1 wherein the vegetable oil is selected from the group consisting of soybean oils, canola oils, castor oils, palm oils, coconut oil, and corn oils.

5. The vegetable oil derivative of claim 1 wherein the vegetable oil is a high oleic soybean oil comprising about 75 percent by weight oleic acid residues.

6. The vegetable oil derivative of claim 4 wherein R 1 , R 2 , and R 3 together comprise about 75 weight percent oleyl groups.

7. A vulcanizable rubber composition comprising the vegetable oil derivative of claim 1 .

8. A vulcanizable rubber composition comprising the vegetable oil derivative of claim 4 .

9. A pneumatic tire comprising the vulcanizable rubber composition of claim 7 .

10. A manufactured item comprising the vulcanizable rubber composition of claim 7
wherein the manufactured item is selected from the group consisting of tire treads, shoes, shoe soles, transmission belts, hoses, airsprings, conveyor belts, track belts, and vibration isolators.

11. A method of making a vegetable oil derivative comprising the steps of:
obtaining a thiolized triglyceride; and
reacting the thiolized triglyceride with a silane disulfide comprising a silyl group at one terminus and a leaving group at the other terminus, to produce the vegetable oil derivative.

12. The method of claim 11 wherein the thiolized triglyceride is of the formula

where R 1 , R 2 , and R 3 are independently C15-C20 alkenyl, C15-C20 alkyl, and optionally containing aromatic groups; n is from 1 to 6; each S—(CH 2 ) n —SH or —SH is covalently bonded to a carbon atom of one of R 1 , R 2 or R 3 ; and m is the number of —S—(CH 2 ) n —SH or —SH groups based on olefinic unsaturation of R 1 , R 2 and R 3 .

13. The method of claim 11 wherein the silane disulfide is of formula

where R 5 , R 6 are independently C1 to C10 alkyl, R 7 is C1 to C10 alkane diyl, j=0 to 2, k=1 to 3, and j+k=3, and R 8 is an organic leaving group.

14. The method of claim 13 wherein R 8 is a benzothiazolyl group.

15. The method of claim 11 wherein the silane disulfide is 2-[[3-triethoxysilyl)propyl]dithio]benzothiazole.

16. The method of claim 11 wherein the triglyceride is a vegetable oil selected from the group consisting of soybean oils, canola oils, castor oils, palm oils, coconut oil, and corn oils.

17. The method of claim 11 wherein the triglyceride is a high oleic soybean oil comprising about 75 percent by weight of oleic acid residues.

Assignees

• Goodyear Tire & Rubber

Inventors

• Kulig Joseph John
• Cantwell Kelsey Elizabeth
• Feher Frank James
• Spilker Thomas Franklin
• Papakonstantopoulos George Jim

Classifications

• C11B1/108

  after-treatment, e.g. of miscellae · CPC title

• B60C1/00

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title

• C08L9/06

  Copolymers with styrene · CPC title

• C07C321/12 Primary

  Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms · CPC title

• C11B3/02

  by chemical reaction {(C11B3/003 takes precedence)} · CPC title