IP Library Granted Patent US 12,486,385
Granted Patent B2
US 12,486,385 · App. 17/629,668 · Granted Dec 2, 2025

Tire incorporating a rubber composition including a specific hydrocarbon resin

Inventors: Fabien Bonnette (Clermont-Ferrand, FR); Laurent Copey (Clermont-Ferrand, FR); Benoit De Gaudemaris (Clermont-Ferrand, FR); Olivier J. F. Georjon (Uccle, BE); Derek W. Thurman (Friendswood, TX); Ranjan Tripathy (Sugar Land, TX); Alain Hut (Clermont-Ferrand, FR)
Assignee: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
C08L9/06B60C1/0016
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,486,385
App. No.
17/629,668
Granted
Dec 2, 2025
Kind
B2
Abstract

Described herein are tires comprising a rubber composition based on at least an elastomer matrix comprising from 50 to 100 phr of one or more copolymers of butadiene and of vinylaromatic monomer, having a content of vinylaromatic units of between 0 and 5% by weight and a Tg within a range extending from −110° C. to −70° C.; and a hydrocarbon resin, wherein the hydrocarbon resin is based on a cyclic monomer selected from the group consisting of a distillation cut from a petroleum refinery stream, and/or C 4 , C 5 or C 6 cyclic olefins and mixtures thereof, and wherein the hydrocarbon resin has a content of aromatic protons (H Ar, expressed in mol %), a glass transition temperature (Tg, expressed in ° C.), and a number average molecular weight (Mn, expressed in g/mol) that are represented by (1) H Ar>6 mol %, (2) Tg≥95−2.2*(H Ar), and (3) Tg≥−53+(0.265*Mn).

Claims (32)

1 . A tire comprising a rubber composition based on at least:

an elastomer matrix comprising from 50 to 100 phr of one or more copolymers of butadiene and of vinylaromatic monomer, having a content of vinylaromatic units of between 0 and 5% by weight and a Tg within a range extending from −110° C. to −70° C.; and

a hydrocarbon resin,

wherein the hydrocarbon resin is based on a cyclic monomer selected from the group consisting of a distillation cut from a petroleum refinery stream, C 4 , C 5 or C 6 cyclic olefins and mixtures thereof,

wherein the hydrocarbon resin has a content of aromatic protons (H Ar, expressed in mol %), a glass transition temperature (Tg, expressed in ° C.), and a number average molecular weight (Mn, expressed in g/mol) that are represented by:

HAr>6 mol %,  (1)

Tg≥95−2.2*(HAr),  (2)

and

Tg≥−53+(0.265*Mn),  (3)

wherein a content of the hydrocarbon resin is within a range extending from 65 to 110 phr.

2 . The tire according to claim 1 , wherein the hydrocarbon resin comprises methylcyclopentadiene in an amount between 0.1 wt. % and 15 wt. %.

3 . The tire according to claim 1 , wherein the hydrocarbon resin has at least one of the following additional features:

a MMAP cloud point of between 10° C. and 60° C.;

a number average molecular weight (Mn) of between 150 and 800 g/mol;

a glass transition temperature (Tg) represented by Tg≥100−2.2*(H Ar);

a glass transition temperature (Tg) represented by Tg≥−32+(0.265*Mn); and

an aromatic proton content (H Ar) of greater than 6 mol % and less than 25 mol %.

4 . The tire according to claim 1 , wherein a content of the hydrocarbon resin is within a range extending from 15 to 150 phr.

5 . The tire according to claim 1 , wherein each copolymer of butadiene and of vinylaromatic monomer has a Tg within a range extending from −110° C. to −80° C.

6 . The tire according to claim 1 , wherein each copolymer of butadiene and of vinylaromatic monomer has a content of vinylaromatic units of 1 to 4% by weight relative to the total weight of the copolymer, and also a content of vinylaromatic units, relative to the diene portion, ranging from 8 to 15% by weight.

7 . The tire according to claim 1 , wherein the rubber composition further comprises a reinforcing filler.

8 . The tire according to claim 1 , wherein the hydrocarbon resin comprises the cyclic monomer in an amount between 10 wt. % and 90 wt. %.

9 . The tire according to claim 8 , wherein the cyclic monomer is selected from the group consisting of cyclopentene, cyclopentadiene, dicyclopentadiene, cyclohexene, 1,3-cyclohexadiene, 1,4-cyclohexadiene, methylcyclopentadiene, di(methylcyclopentadiene) and mixtures thereof.

10 . The tire according to claim 1 , wherein at least 70% by weight of the one or more copolymers of butadiene and of vinylaromatic monomer is functionalized.

11 . The tire according to claim 10 , wherein each copolymer of butadiene and of vinylaromatic monomer comprises more than 0 and up to 30% by weight, relative to a total weight of the copolymer of butadiene and of vinylaromatic monomer, of a star-branched copolymer of butadiene and of vinylaromatic monomer.

12 . The tire according to claim 1 , wherein the hydrocarbon resin is further based on an aromatic monomer.

13 . The tire according to claim 12 , wherein the aromatic monomer is selected from the group consisting of olefin-aromatic compounds, aromatic distillation cuts and mixtures thereof.

14 . The tire according to claim 13 , wherein the aromatic monomer is an aromatic distillation cut or an olefin-aromatic compound selected from the group consisting of indene derivatives, vinylaromatic compounds and mixtures thereof.

15 . The tire according to claim 14 , wherein the aromatic monomer comprises an indene derivative of Formula (I)

wherein R 1 and R 2 represent, independently of one another, a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group or an arylalkyl group,

or a vinylaromatic compound of Formula (II)

wherein R 3 and R 4 represent, independently of one another, a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group or an arylalkyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2023
From: BONNETTE, FABIEN; COPEY, LAURENT; DE GAUDEMARIS, BENOIT; GEORJON, OLIVIER J.F.; HUT, ALAIN; THURMAN, DEREK W.; TRIPATHY, RANJAN
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 063807/0268 →
Priority Claims (1)
FR 1908541 · Jul 26, 2019 · national
Continuity (1)
Related Publication 20220259415A1 · Aug 18, 2022
References Cited (115)
US 4398582A · Yuto et al. · 1983 [cited by applicant]
US 5171793A · Johnson et al. · 1992 [cited by applicant]
US 5227425A · Rauline · 1993 [cited by applicant]
US 5552489A · Merrill et al. · 1996 [cited by applicant]
US 5852099A · Vanel · 1998 [cited by applicant]
US 5900449A · Custodero et al. · 1999 [cited by applicant]
US 5977238A · Labauze · 1999 [cited by applicant]
US 6013718A · Cabioch et al. · 2000 [cited by applicant]
US 6218588B1 · Dommisse et al. · 2001 [cited by applicant]
US 6420488B1 · Penot · 2002 [cited by applicant]
US 6433104B1 · Macedo et al. · 2002 [cited by applicant]
US 6503973B2 · Robert et al. · 2003 [cited by applicant]
US 6536492B2 · Vasseur · 2003 [cited by applicant]
US 6774255B1 · Tardivat et al. · 2004 [cited by applicant]
US 6815473B2 · Robert et al. · 2004 [cited by applicant]
US 6825291B2 · Klosiewicz et al. · 2004 [cited by applicant]
US 7217751B2 · Durel et al. · 2007 [cited by applicant]
US 7250463B2 · Durel et al. · 2007 [cited by applicant]
US 7300970B2 · Durel et al. · 2007 [cited by applicant]
US 7488768B2 · Tardivat et al. · 2009 [cited by applicant]
US 7491767B2 · Durel et al. · 2009 [cited by applicant]
US 8492475B2 · Araujo Da Silva et al. · 2013 [cited by applicant]
US 8735500B2 · Barbee et al. · 2014 [cited by applicant]
US 9010393B2 · Araujo Da Silva et al. · 2015 [cited by applicant]
US 9856368B2 · Herzog et al. · 2018 [cited by applicant]
US 9909004B2 · Blok et al. · 2018 [cited by applicant]
US 10689507B2 · Abad · 2020 [cited by applicant]
US 10889147B2 · Chatard et al. · 2021 [cited by applicant]
US 11203680B2 · DeGaudemaris et al. · 2021 [cited by applicant]
US 11220591B2 · DeGaudemaris et al. · 2022 [cited by applicant]
US 11225567B2 · Cabioch et al. · 2022 [cited by applicant]
US 11352484B2 · Copey et al. · 2022 [cited by applicant]
US 11365308B2 · DeGaudemaris et al. · 2022 [cited by applicant]
US 11492465B2 · DeGaudemaris et al. · 2022 [cited by applicant]
US 20010034389A1 · Vasseur · 2001 [cited by applicant]
US 20040051210A1 · Tardivat et al. · 2004 [cited by applicant]
US 20040132880A1 · Durel et al. · 2004 [cited by applicant]
US 20050004297A1 · Durel et al. · 2005 [cited by applicant]
US 20050016650A1 · Durel et al. · 2005 [cited by applicant]
US 20050016651A1 · Durel et al. · 2005 [cited by applicant]
US 20050148718A1 · Ishida et al. · 2005 [cited by applicant]
US 20060089445A1 · Gandon-pain · 2006 [cited by applicant]
US 20090186961A1 · Araujo Da Silva et al. · 2009 [cited by applicant]
US 20090209709A1 · Araujo Da Silva et al. · 2009 [cited by applicant]
US 20090234066A1 · Araujo Da Silva et al. · 2009 [cited by applicant]
US 20100204359A1 · Robert et al. · 2010 [cited by applicant]
US 20100216939A1 · Zhao et al. · 2010 [cited by applicant]
US 20110152458A1 · Araujo Da Silva et al. · 2011 [cited by applicant]
US 20130087953A1 · Rodgers et al. · 2013 [cited by applicant]
US 20130196085A1 · Voge et al. · 2013 [cited by applicant]
US 20150065655A1 · Blok et al. · 2015 [cited by applicant]
US 20150283854A1 · Saintigny et al. · 2015 [cited by applicant]
US 20160194485A1 · Herzog et al. · 2016 [cited by applicant]
US 20170198122A1 · Rodgers et al. · 2017 [cited by applicant]
US 20180171124A1 · Ingratta et al. · 2018 [cited by applicant]
US 20180186978A1 · Abad · 2018 [cited by applicant]
US 20180284085A1 · Arigo et al. · 2018 [cited by applicant]
US 20180340055A1 · DeGaudemaris et al. · 2018 [cited by applicant]
US 20190077887A1 · Dire et al. · 2019 [cited by applicant]
US 20190367707A1 · De Gaudemaris · 2019 [cited by examiner]
US 20200131347A1 · Cabioch et al. · 2020 [cited by applicant]
US 20200223259A1 · Hellot et al. · 2020 [cited by applicant]
US 20200325312A1 · Abrunie et al. · 2020 [cited by applicant]
US 20200385550A1 · Cabioch et al. · 2020 [cited by applicant]
US 20200392314A1 · DeGaudemaris et al. · 2020 [cited by applicant]
US 20220227975A1 · Bonnette et al. · 2022 [cited by applicant]
US 20220251349A1 · Bonnette et al. · 2022 [cited by applicant]
US 20220251350A1 · Bonnette et al. · 2022 [cited by applicant]
US 20220363875A1 · DeGaudemaris et al. · 2022 [cited by applicant]
EP 0501227A1 · 1992 [cited by applicant]
EP 0735088A1 · 1996 [cited by applicant]
EP 0810258A1 · 1997 [cited by applicant]
EP 0890607B1 · 2003 [cited by applicant]
EP 1127909B1 · 2005 [cited by applicant]
FR 2740778A1 · 1997 [cited by applicant]
FR 2765882A1 · 1999 [cited by applicant]
WO 9113106A1 · 1991 [cited by applicant]
WO 19736724A2 · 1997 [cited by applicant]
WO 9916600A1 · 1999 [cited by applicant]
WO 0005300A1 · 2000 [cited by applicant]
WO 0005301A1 · 2000 [cited by applicant]
WO 0192402A1 · 2001 [cited by applicant]
WO 0230939A1 · 2002 [cited by applicant]
WO p231041A1 · 2002 [cited by applicant]
WO 02083782A1 · 2002 [cited by applicant]
WO 03002648A1 · 2003 [cited by applicant]
WO 03002649A1 · 2003 [cited by applicant]
WO 03016387A1 · 2003 [cited by applicant]
WO 2004096865A2 · 2004 [cited by applicant]
WO 2006069792A1 · 2006 [cited by applicant]
WO 2006069793A1 · 2006 [cited by applicant]
WO 2006125532A1 · 2006 [cited by applicant]
WO 2006125533A1 · 2006 [cited by applicant]
WO 2006125534A1 · 2006 [cited by applicant]
WO 2008003434A1 · 2008 [cited by applicant]
WO 2008003435A1 · 2008 [cited by applicant]
WO 2008141702A1 · 2008 [cited by applicant]
WO 2009000750A1 · 2008 [cited by applicant]
WO 2009000752A1 · 2008 [cited by applicant]
WO 2012050658A1 · 2012 [cited by applicant]
WO 2013176712A1 · 2013 [cited by applicant]
WO 2015043902A1 · 2015 [cited by applicant]
WO WO2016043851A1 · 2016 [cited by examiner]
WO 2016202968A1 · 2016 [cited by applicant]
WO 2017060395A1 · 2017 [cited by applicant]
WO 2017064235A1 · 2017 [cited by applicant]
WO 2017168099A1 · 2017 [cited by applicant]
WO WO2018115621A1 · 2018 [cited by examiner]
WO 2019002764A1 · 2019 [cited by applicant]
WO 2019002766A1 · 2019 [cited by applicant]
WO 2019115954A1 · 2019 [cited by applicant]
WO 2019115955A1 · 2019 [cited by applicant]
International Search Report dated Oct. 6, 2020, in corresponding PCT/EP2020/069497 (2 pages). [cited by applicant]
T. Sun, et al., “Effect of Short Chain Branching on the Coil Dimensions of Polyolefins in Dilute Solution”, Macromolecules 2001, 34, 6812-6820. [cited by applicant]
Kirk-Othmer Encyclopedia of Chemical Terminology, 4th ed., Wiley-Interscience, vol. 13, pp. 717-744 (1995). [cited by applicant]