Silane-functionalized hydrocarbon polymer modifiers for elastomeric compositions

Patent metadata

Field	Value
Publication number	US-9376566-B2
Application number	US-201113822103-A
Country	US
Kind code	B2
Filing date	Aug 25, 2011
Priority date	Jan 18, 2008
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

An elastomeric composition and method incorporating a hydrocarbon polymer modifier with improved permanence. The composition comprises elastomer, filler and silane-functionalized hydrocarbon polymer modifier (Si-HPM) adapted to couple the Si-HPM to the elastomer, filler or both, wherein the Si-HPM comprises an interpolymer of monomers chosen from piperylenes, cyclic pentadienes, aromatics, limonenes, pinenes, amylenes, and combinations thereof. The method comprises melt processing a mixture to form the elastomeric composition in the shape of an article, wherein the mixture comprises elastomer, Si-HPM, silica, bifunctional organosilane crosslinking agent; and curing the elastomeric composition to form the article. Also disclosed are a silylated hydrocarbon polymer modifier coupled with a bifunctional organosilane crosslinking agent, and a silica-coupled hydrocarbon polymer modifier coupled to the silica via the bifunctional organosilane crosslinking agent.

First claim

We claim:

1. An elastomeric composition comprising (i) at least one elastomer; (ii) at least one filler; and (iii) at least one silane-functionalized hydrocarbon polymer modifier (Si-HPM) wherein the Si-HPM comprises an interpolymer comprising at least one piperylene component, at least one cyclic pentadiene component, at least one aromatic component, and optionally at least one monomer chosen from limonenes, pinenes, and amylenes, the Si-HPM further comprising at least one functional group comprising a silane structure; wherein the modifier has a glass transition temperature of from about 60° C. to about 100° C., and wherein the interpolymer, prior to functionalization, has a weight average molecular weight of 2500 to 25,000 g/mole, a number average molecular weight of 900 to 3,000 g/mole, and a softening point from 40° C. to 160° C.

2. The elastomeric composition of claim 1 , wherein the one or more functional groups further comprise olefinic unsaturation, wherein the interpolymer comprises at least 1 mole percent olefinic hydrogen, based on the total moles of hydrogen in the interpolymer.

3. The elastomeric composition of claim 1 or claim 2 , wherein the Si-HPM comprises the reaction product of the interpolymer and a bifunctional organosilane crosslinking agent of the formula:
X 3 Si—R—F—[R—Si—X 3 ] p

wherein each X is independently a silicon functional group, each R is independently a divalent substituted or unsubstituted hydrocarbon group of from 1 to 20 carbon atoms, F is a monovalent or multivalent organo-functional group, p is 0 when F is monovalent and p is at least 1 when F is multivalent.

4. The elastomeric composition of claim 3 , wherein X is hydroxy or R 1 —O— wherein R 1 is an alkyl, alkoxyalkyl, aryl, aralkyl or cycloalkyl group of up to 20 carbon atoms, R is alkylene, wherein p is 0 or 1, and when p is 0, F is selected from amino, amido, hydroxy, alkoxy, halo, mercapto, hydrosilyl, carboxy, acyl, vinyl, allyl, styryl, ureido, epoxy, isocyanato, glycidoxy, and acryloxy groups, and when p is 1, F is divalent polysulfide of from 2 to 20 sulfur atoms.

5. The elastomeric composition of claim 1 , wherein the at least one filler comprises silica.

6. The elastomeric composition of claim 1 , wherein the interpolymer is coupled via at least one of the one or more functional groups to the at least one elastomer.

7. The elastomeric composition of claim 1 , wherein the interpolymer is coupled via at least one of the one or more functional groups to the at least one filler.

8. The elastomeric composition of claim 1 , wherein the interpolymer is coupled to a combination of the at least one elastomer and the at least one filler.

9. The elastomeric composition of claim 1 , wherein the at least one elastomer is coupled to the at least one filler.

10. The elastomeric composition of claim 1 , wherein the interpolymer is immiscible with the at least one elastomer.

11. A tire or tire component comprising the elastomeric composition of claim 1 .

12. A method of forming an article, comprising:
(a) melt processing an elastomeric mixture to form an elastomeric composition in the shape of an article, wherein the elastomeric mixture comprises (i) at least one elastomer;
(ii) at least one hydrocarbon polymer modifier wherein the hydrocarbon polymer modifier comprises an interpolymer comprising at least one functional group, at least one piperylene component, at least one cyclic pentadiene component, at least one aromatic component, and optionally at least one monomer chosen from limonenes, pinenes, and amylenes, and wherein the one or more functional groups comprise a bifunctional organosilane crosslinking agent, and wherein the interpolymer, prior to functionalization, has a weight average molecular weight of 2500 to 25,000 g/mole, a number average molecular weight of 900 to 3,000 g/mole, and a softening point from 40° C. to 160° C.; and (iii) a filler comprising silica; and
(b) curing the elastomeric composition to form the article.

13. The method of claim 12 , comprising coupling the interpolymer to one or both of the elastomer and the filler, coupling the elastomer to one or both of the interpolymer and the filler, and coupling the filler to one or both of the interpolymer and the elastomer.

14. The method of claim 12 , comprising coupling the filler to a silane functional group of the bifunctional organosilane crosslinking agent and coupling the interpolymer to an organofunctional group of the bifunctional organosilane crosslinking agent.

15. The method of claim 12 , comprising pre-reacting the interpolymer and the bifunctional organosilane crosslinking agent to provide the interpolymer with the silane functionality.

16. The method of claim 15 , wherein the pre-reaction comprises contacting the interpolymer and the bifunctional organosilane crosslinking agent in the presence of a catalyst.

17. The method of claim 15 , wherein the pre-reaction comprises incorporating the bifunctional organosilane crosslinking agent in a mixture of the monomers in a feed to a polymerization reactor.

18. The method of claim 15 , comprising coupling the pre-reacted interpolymer-bifunctional organosilane crosslinking agent to the filler.

19. The method of claim 12 , wherein the bifunctional organosilane crosslinking agent is a silane having the formula:
X 3 Si—R—F—[R—Si—X 3 ] p

wherein each X is independently a silicon functional group, each R is independently a divalent hydrocarbon group of from 1 to 20 carbon atoms, F is a monovalent or bivalent organo-functional group, p is 0, when F is monovalent and p is 1, when F is divalent.

20. The method of claim 12 , wherein the interpolymer comprises at least 1 mol % olefinic hydrogen, based on the total moles of hydrogen in the interpolymer.

21. The method of claim 12 , further comprising adhering a build component to a surface of the elastomeric composition and co-curing the build component with the article to form a construct.

22. The method of claim 21 , wherein the construct comprises a tire and the article comprises a tire tread, a tire innerliner or a tire carcass.

Assignees

• Blok Edward J
• Dias Anthony J
• Claassen Ii Robert J
• Uhl Eugene Ronald
• Exxonmobil Chem Patents Inc

Inventors

• Blok Edward J
• Dias Anthony J
• Claassen Ii Robert J
• Uhl Eugene Ronald

Classifications

• B29D30/06

  Pneumatic tyres or parts thereof {(e.g. produced by casting, moulding, compression moulding, injection moulding, centrifugal casting)} · CPC title

• C08L47/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers (C08L45/00 takes precedence; of conjugated diene rubbers C08L9/00 - C08L21/00) · CPC title

• C08J2351/00

  Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers · CPC title

• C08C19/25

  Incorporating silicon atoms into the molecule · CPC title

• C08L23/22

  Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins · CPC title