Spacer groups for functionalized resins in tires

Patent metadata

Field	Value
Publication number	US-9840569-B2
Application number	US-201515118701-A
Country	US
Kind code	B2
Filing date	Mar 6, 2015
Priority date	Mar 31, 2014
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

This invention relates to a functionalized resin composition having the formula P—S—X where S is a spacer selected from at least one of C 2 -C 40 straight chain and branched alkyl, C 6 -C 40 aromatics, butadiene, isoprene, and combinations thereof, P is a polymer backbone 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 X is a silane.

First claim

The invention claimed is:

1. A functionalized resin composition having the formula (I)
P—S—X  (I)

where S is a spacer selected from at least one of C 2 -C 40 straight chain and branched alkyl, C 6 -C 40 aromatics, butadiene, isoprene, and combinations thereof, P is a polymer backbone 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 X is a silane;
wherein P, S, and X are contacted in the presence of a metathesis catalyst to produce the functionalized resin composition,
wherein the metathesis catalyst comprises tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene][3-phenyl-1H-inden-1-ylidene]ruthenium(II) dichloride, tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene]ruthenium(II) dichloride, tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][(phenylthio)methylene]ruthenium(II) dichloride, bis(tricyclohexylphosphine)-3-phenyl-1H-inden-1-ylideneruthenium(II) dichloride, 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy) -5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride, [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(4-methylphenyl)imino]methyl]-4-nitrophenolyl]-[3-phenyl-1H-inden-1-ylidene]ruthenium(II) chloride, and fluoride and bromide derivatives thereof, or a mixture of any of the above.

2. The functionalized resin composition of claim 1 , wherein X is of the formulae

where each Y is independently a nitrogen, oxygen, or sulfur atom, each Z is independently a boron, nitrogen, oxygen, silicon, or sulfur atom, each R is independently a monovalent (for I) or a divalent (for II) substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms containing at least one olefinic group, each R 1 is independently a hydrogen atom, or a substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms, each R 2 is independently a divalent substituted or unsubstituted alkyl or aromatic group of from 1 to 20 carbon atoms, each R 3 is independently a hydrogen atom, a halogen atom, 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, where 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 where 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;
wherein each R is the spacer S.

3. The functionalized resin composition of claim 1 , wherein P comprises:
(i) within the range from 60-100 wt % cyclic components;
(ii) less than or equal to 15 wt % components derived from piperylene;
(iii) less than or equal to 15 wt % components derived from amylene;
(iv) less than or equal to 15 wt % components derived from isoprene;
(v) less than or equal to 20 wt % components derived from styrene; and
(vi) less than or equal to 20 wt % components derived from indene.

4. A tire tread composition comprising the functionalized resin composition of claim 1 .

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Blok Edward J
• Stewart Ian C
• Harris David T

Classifications

• C08L45/00

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• C08L9/06

  Copolymers with styrene · CPC title

• C08L9/00

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C08F2810/40

  taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains · CPC title

• C08F2810/30

  leading to the formation or introduction of aliphatic or alicyclic unsaturated groups · CPC title