# US 9,040,613 B2 · Plasticizing system and rubber composition for tire containing said system > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,613 B2 - Document ID: US9040613B2 - Status: Granted - Kind: B2 - Application number: 12/521,463 - Filed: 2007-12-19 - Published: 2011-02-17 - Granted: 2015-05-26 - Earliest claimed: 2006-12-27 - Assignees: Michelin Recherche et Technique S.A. - Applicants: Garance Lopitaux; Didier Vasseur - Inventors: Garance Lopitaux; Didier Vasseur - Web page: https://patentgrep.com/patent/US9040613B2 ## CPC - C08K 5/12: of cyclic polycarboxylic acids - B60C 1/0016: {Compositions of the tread} - C08K 5/0016: {Plasticisers} - C08L 21/00: Compositions of unspecified rubbers - C08K 3/013: Fillers, pigments or reinforcing additives - C08L 47/00: 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Plasticizing system which can be used in particular for the plasticizing of a tire diene elastomer composition containing, in combination: a plasticizing hydrocarbon resin, the glass transition temperature of which is greater than 0° C.; and a tri- or pyromellitate ester corresponding to the formula (I): in which the R radicals, which are identical or different, represent a hydrocarbon radical and the R′ radical represents hydrogen or COOR group. Also, a rubber composition incorporating the plasticizing system and the use of such a composition for the manufacture of a tire or tire semi-finished product made of rubber, in particular of a tire tread, exhibiting an improved wear resistance without having a detrimental affect on its wet grip. ## Claims ### Claim 1 A rubber composition comprising at least one diene elastomer, one reinforcing filler and one plasticizing system, wherein the plasticizing system comprises: a plasticizing hydrocarbon resin, the glass transition temperature (Tg) of which is greater than 0° C.; and a tri- or pyromellitate ester corresponding to the formula (I): wherein the R radicals, which are identical or different, represent a hydrocarbon radical and the R′ radical represents hydrogen or COOR group. ### Claim 2 (depends on 1) The rubber composition according to claim 1, wherein the R radicals, which are identical or different, are selected from the group consisting of linear alkyls comprising from 1 to 30 carbon atoms, branched alkyls comprising from 1 to 30 carbon atoms, cyclic alkyls comprising from 1 to 30 carbon atoms, aryls comprising from 6 to 30 carbon atoms, aralkyls comprising from 6 to 30 carbon atoms, and alkaryls comprising from 6 to 30 carbon atoms. ### Claim 3 (depends on 2) The rubber composition according to claim 2, wherein the R radicals represent a linear, branched or cyclic alkyl group comprising from 1 to 20 carbon atoms. ### Claim 4 (depends on 3) The rubber composition according to claim 3, wherein the ester is a trimellitate of formula (II): ### Claim 5 (depends on 4) The rubber composition according to claim 4, wherein the trimellitate is selected from the group consisting of trioctyl trimellitate (TOTM), triisooctyl trimellitate (TIOTM), and mixtures thereof. ### Claim 6 (depends on 1) The rubber composition according to claim 1, wherein the tri or pyromellitate ester is present at a level of between 5 and 60 pce. ### Claim 7 (depends on 1) The rubber composition according to claim 1, wherein the Tg of the plasticizing hydrocarbon resin is greater than +20° C. ### Claim 8 (depends on 1) The rubber composition according to claim 1, wherein the plasticizing hydrocarbon resin has a number-average molecular weight of between 400 and 2000 g/mol. ### Claim 9 (depends on 1) The rubber composition according to claim 1, wherein the plasticizing hydrocarbon resin has a polydispersity index of less than 3. ### Claim 10 (depends on 1) The rubber composition according to claim 1, wherein the plasticizing hydrocarbon resin is selected from the group consisting of cyclopentadiene (abbreviated to CPD) homopolymer resin, CPD copolymer resin, dicyclopentadiene (abbreviated to DCPD) homopolymer resin, DCPD copolymer resin, terpene homopolymer resin, terpene copolymer resin, C5 fraction homopolymer resin, C5 fraction copolymer resin, and blends thereof. ### Claim 11 (depends on 10) The rubber composition according to claim 10, wherein the plasticizing hydrocarbon resin is selected from the group consisting of CPD homopolymer resin, DCPD homopolymer resin, CPD/styrene copolymer resin, DCPD/styrene copolymer resin, polylimonene resin, limonene/styrene copolymer resin, limonene/CPD copolymer resin, limonene/DCPD copolymer resin, C5 fraction/styrene copolymer resin, C5 fraction/C9 fraction copolymer resin, and blends thereof. ### Claim 12 (depends on 1) The rubber composition according to claim 1, wherein the plasticizing hydrocarbon resin is present in a level of between 5 and 60 pce. ### Claim 13 (depends on 1) The rubber composition according to claim 1, wherein the at least one diene elastomer is selected from the group consisting of polybutadienes, synthetic polyisoprenes, natural rubber, butadiene copolymers, isoprene copolymers, and blends thereof. ### Claim 14 (depends on 1) The rubber composition according to claim 1, wherein the tri- or pyromellitate ester is trioctyl trimellitate. ### Claim 15 (depends on 14) The rubber composition according to claim 14, wherein the tri- or pyromellitate ester is present in an amount between 5 and 40 pce. ### Claim 16 (depends on 15) The rubber composition according to claim 15, wherein the amount of the tri- or pyromellitate ester is between 10 and 30 pce. ### Claim 17 (depends on 1) The rubber composition according to claim 1, wherein the tri- or pyromellitate ester is present in an amount between 5 and 40 pce. ### Claim 18 (depends on 17) The rubber composition according to claim 17, wherein the amount of the tri- or pyromellitate ester is between 10 and 30 pce. ### Claim 19 (depends on 5) The rubber composition according to claim 5, wherein the tri- or pyromellitate ester is present in an amount between 5 and 40 pce. ### Claim 20 (depends on 19) The rubber composition according to claim 19, wherein the amount of the tri- or pyromellitate ester is between 10 and 30 pce. ### Claim 21 (depends on 1) A tire tread comprising the rubber composition according to claim 1. ### Claim 22 (depends on 21) A tire comprising the tread according to claim 21. ### Claim 23 A process for preparing a rubber composition comprising at least one diene elastomer, one reinforcing filler and one plasticizing system, the process comprising the following stages: incorporating in the at least one diene elastomer, in a mixer: the reinforcing filler; the plasticizing system; kneading everything thermomechanically, in one or more goes, until a maximum temperature of between 110° C. and 190° C. is reached; cooling the combined mixture to a temperature of less than 100° C.; subsequently incorporating: a crosslinking system; kneading everything up to a maximum temperature of less than 110° C.; and extruding or calendering the rubber composition thus obtained; and wherein the plasticizing system comprises at least: one plasticizing hydrocarbon resin, the glass transition temperature (Tg) of which is greater than 0° C.; and a tri- or pyromellitate ester corresponding to the formula (I): wherein the R radicals, which are identical or different, represent a hydrocarbon radical and the R′ radical represents hydrogen or COOR group.