IP Library › Granted Patent US 10,059,825
Granted Patent B2
US 10,059,825 · App. 15/118,660 · Granted Aug 28, 2018

Silica treating of functionalized resins in tires

Inventors: David T. Harris (Houston, TX); Ian C. Stewart (Houston, TX); Olivier J. Georjon (Uccle, BE); Edward J. Blok (Huffman, TX)
Assignee: ExxonMobil Chemical Patents Inc.
C08K3/36B60C1/0016C08F8/42C08G61/02C08G83/001C08K9/06C08K9/08C08K9/10C08L9/06C09C1/309C09C1/3072C09C1/3081C08F2810/40C08G2261/3325C08G2261/726C08K2003/2296Y02T10/862
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Quick Facts
Patent No.
US 10,059,825
App. No.
15/118,660
Granted
Aug 28, 2018
Kind
B2
Abstract

This invention relates to a process for the preparation of a silica-treated functionalized resin composition comprising the steps of reacting a polymer backbone with a hydrosilylation agent to produce a silane-functionalized resin composition, wherein the polymer backbone is selected from at least one of dicyclopentadiene (DCPD)-based polymers, cyclopentadiene (CPD)-based polymers, DCPD-styrene copolymers, C 5 homopolymers and copolymer resins, C 5 -styrene copolymer resins, terpene homopolymer or copolymer resins, pinene homopolymer or copolymer resins, C 9 homopolymers and copolymer resins, C 5 /C 9 copolymer resins, alpha-methylstyrene homopolymer or copolymer resins, and combinations thereof; and mixing the silane-functionalized resin composition with a silica to produce a silica-treated functionalized resin composition.

Claims (34)

1. A process for the preparation of a silica-treated functionalized resin composition comprising the steps of:

(A) reacting a polymer backbone with a hydrosilylation agent to produce a silane-functionalized resin composition,

wherein the polymer backbone is selected from at least one of dicyclopentadiene (DCPD)-based polymer, a cyclopentadiene (CPD)-based polymer, a DCPD-styrene copolymer, a C 5 copolymer resin, a C 5 -styrene copolymer resin, a terpene copolymer resin, a pinene copolymer resin, a C 9 copolymer resin, a C 5 /C 9 copolymer resin, an alpha-methylstyrene copolymer resin, and combinations thereof;

wherein the polymer backbone comprises:

within the range from 60 to 100 wt % cyclic components;

(i) less than or equal to 15 wt % components derived from piperylene;

(ii) from 0.1 to 10 wt % components derived from amylene;

(iii) less than or equal to 15 wt % components derived from isoprene;

(iv) from 0.1 to 20 wt % components derived from styrene; and

(v) from 5 to 15 wt % components derived from indene; and

(B) mixing the silane-functionalized resin composition with silica to produce a silica-treated functionalized resin composition;

wherein the hydrosilylation agent is selected from at least one of those represented by formulas (I), (II), or (III):

where “a” is an integer from 1 to about 1000, and R″ is an alkyl or an aryl group;

where x is from about 2 to about 40 SiO-groups/moieties, and R is an alkyl or an aryl group;

where Y is independently a nitrogen, oxygen, or sulfur atom, Z is independently a boron, nitrogen, oxygen, silicon or sulfur atom, R 1 is independently a hydrogen atom, or a substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms, R 2 is independently a divalent substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms, R 3 is independently a hydrogen atom, a halogen atom, a sulfonate group, a substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms, R 1 , R 2 , and R 3 may form single or multinuclear rings with each other, a-f are independently integers of 1, 2, or 3, with the proviso that a+b+c and d+e+f are both equal to 3, and independently for each Y and Z, if Z is a boron atom, then x=2, if Y or Z is a nitrogen atom, then x=2, if Y or Z is an oxygen atom or sulfur atom, then x=1, if Z is a silicon atom, then x=3.

2. The process of claim 1 wherein the ratio of the wt % of the silane-functionalized resin composition to the wt % of the silica is about 1:3.

3. The process of claim 1 , wherein the hydrosilylation agent and the polymer backbone are contacted in the presence of a hydrosilylation catalyst to produce a catalyzed reaction product.

4. The process of claim 3 , wherein the hydrosilylation agent and the polymer backbone are contacted in the presence of a metathesis catalyst, wherein the metathesis catalyst is a ruthenium catalyst.

5. A silica-treated functionalized resin composition of claim 1 prepared by the method of

(A) reacting the polymer backbone with the hydrosilylation agent to produce a silane-functionalized resin composition; and

(B) mixing the silane-functionalized resin composition with silica to produce a silica-treated functionalized resin composition.

6. The composition of claim 5 , wherein the ratio of the wt % of the silane-functionalized resin composition to the wt % of the silica is about 1:3.

7. A tire tread composition comprising the silica-treated functionalized resin composition made by the process of claim 1 .

8. The tire tread composition of claim 7 , comprising:

(i) the silica-treated functionalized resin composition within the range from 5 to 100 phr;

(ii) 100 phr of a diene elastomer; and

(iii) an inorganic filler within the range from 50 to 150 phr.

9. The tire tread composition of claim 8 , wherein the silica-treated functionalized resin composition is present within the range from 20 to 50 phr.

10. The tire tread composition of claim 8 , wherein the inorganic filler comprises silica.

11. The tire tread composition of claim 8 , wherein the diene elastomer is selected from at least one of natural rubber, polybutadiene rubber, polyisoprene rubber, styrene-butadiene rubber, isoprene-butadiene rubber, high cis-polybutadiene, ethylene-propylene rubber, ethylene-propylene-diene rubber, nitrile rubber, butyl rubber, halogenated butyl rubber, branched (“star-branched”) butyl rubber, halogenated star-branched butyl rubber, poly(isobutylene-co-p-methylstyrene), brominated butyl rubber, chlorinated butyl rubber, star-branched polyisobutylene rubber, and mixtures thereof.

12. The tire tread composition of claim 11 , wherein the diene elastomer comprises a mixture of polybutadiene rubber and styrene-butadiene rubber.

13. The tire tread composition of claim 8 , further comprising a coupling agent.

14. The tire tread composition of claim 8 , wherein the composition is cured.

15. A tire comprising the tire tread composition of claim 8 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2016
From: HARRIS, DAVID T.; STEWART, IAN C.; GEORJON, OLIVIER J.; BLOK, EDWARD J.
To: EXXONMOBIL CHEMICAL PATENTS INC.
Reel/Frame 040186/0689 →
Continuity (2)
Provisional Application 61972964 · Mar 31, 2014
Related Publication 20170066898A1 · Mar 9, 2017
Cited By (1)
US 12,729,288