IP Library › Granted Patent US 12,291,626
Granted Patent B2
US 12,291,626 · App. 17/414,204 · Granted May 6, 2025

Rubber composition based on at least one functionalized elastomer comprising polar functional groups and a specific phenolic compound

Inventors: Odile Gavard-Lonchay (Clermont-Ferrand, FR); Anne-Lise Thuilliez (Clermont-Ferrand, FR)
Assignee: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
C08L15/00B60C1/0016B60C1/0041C08J5/041C08K13/02B60C2001/0066C08J2315/00C08K3/04C08K5/07C08K5/13C08K5/134C08K5/18
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 12,291,626
App. No.
17/414,204
Granted
May 6, 2025
Kind
B2
Abstract

The invention relates to a rubber composition based on at least one functionalized elastomer comprising polar functional groups, a reinforcing filler and a specific phenolic compound.

Claims (25)

1. A rubber composition based on at least one functionalized elastomer comprising polar functional groups, a reinforcing filler and 2-30 phr of a phenolic compound of general formula (I)

in which:

G 1 is a hydroxyl, carboxyl or alkoxy group or a hydrogen atom;

G 2 is a hydroxyl group or a hydrogen atom;

G 3 is a hydrogen atom or a group selected from the group consisting of hydroxyl, carboxyl, hydrogenocarbonyl, alkyl, carboxylalkyl, carboxylalkenyl, carbonylalkyl, aryl, aryloxy, arylthioxy, arylcarbonyl, amino, and aminoalkyl; and

at least one of the substituents G 1 to G 3 comprises an oxygen atom,

wherein the polar functional groups of the at least one functionalized elastomer comprise at least one group selected from the group consisting of hydroxyl, carbonyl, imine and epoxide groups,

wherein the rubber composition does not comprise molecular sulfur,

wherein the rubber composition does not comprise zinc oxide, and

wherein the rubber composition does not simultaneously comprise an alkyl-imidazole and a polycarboxylic acid of general formula (P1):

in which A is a covalent bond or a hydrocarbon-based group including at least 1 carbon atom, which is optionally substituted and optionally interrupted with one or more heteroatoms.

2. The rubber composition according to claim 1 , wherein G 3 is a hydrogen atom or a group selected from the group consisting of hydroxyl, carboxyl, carboxylalkyl, aryl, aryloxy, arylthioxy, and arylcarbonyl.

3. The rubber composition according to claim 1 , wherein the phenolic compound of general formula (I) comprises at least one aromatic nucleus bearing at least two hydroxyl functions in the meta position relative to each other, the two positions ortho to at least one of the hydroxyl functions being unsubstituted.

4. The rubber composition according to claim 1 , wherein the phenolic compound of general formula (I) bears at least three hydroxyl functions.

5. The rubber composition according to claim 4 , wherein two positions ortho to hydroxyl functions of the phenolic compound of general formula (I) are unsubstituted.

6. The rubber composition according to claim 1 , wherein G 3 is a group selected from the group consisting of aryl, aryloxy, arylthioxy, and arylcarbonyl.

7. The rubber composition according to claim 6 , wherein at least two aromatic nuclei of the phenolic compound of general formula (I) bear at least two hydroxyl functions in the meta position relative to each other, the two positions ortho to at least one of the hydroxyl functions of at least one aromatic nucleus being unsubstituted.

8. The rubber composition according to claim 7 , wherein the two positions ortho to at least one hydroxyl function of each aromatic nucleus of the phenolic compound of general formula (I) are unsubstituted.

9. The rubber composition according to claim 1 , wherein the phenolic compound of general formula (I) is selected from the group consisting of resorcinol, phloroglucinol, 2,2′,4,4′-tetrahydroxydiphenyl sulfide, 2,2′,4,4′-tetrahydroxybenzophenone and mixtures thereof.

10. A composite based on at least one reinforcing element and on the rubber composition according to claim 1 .

11. The composite according to claim 10 , wherein the reinforcing element comprises a metallic surface.

12. A finished or semi-finished article comprising the rubber composition according to claim 1 .

13. A finished or semi-finished article comprising the composite according to claim 10 .

14. A tire comprising the rubber composition according to claim 1 .

15. A tire comprising the composite according to claim 10 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2021
From: GAVARD-LONCHAY, ODILE; THUILLIEZ, ANNE-LISE
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 057586/0333 →
Priority Claims (2)
FR 1873024 · Dec 17, 2018 · national
FR 1900923 · Jan 31, 2019 · national
Continuity (1)
Related Publication 20220025163A1 · Jan 27, 2022
References Cited (69)
US 5576080A · Sugimoto et al. · 1996 [cited by applicant]
US 6387524B1 · Finefrock · 2002 [cited by applicant]
US 6903165B2 · Yabui et al. · 2005 [cited by applicant]
US 7199175B2 · Vasseur · 2007 [cited by applicant]
US 7250463B2 · Durel et al. · 2007 [cited by applicant]
US 7900667B2 · Vasseur · 2011 [cited by applicant]
US 10544298B2 · Doisneau et al. · 2020 [cited by applicant]
US 10604613B2 · Doisneau et al. · 2020 [cited by applicant]
US 10647848B2 · Thuilliez et al. · 2020 [cited by applicant]
US 11091580B2 · Doisneau et al. · 2021 [cited by applicant]
US 20030212185A1 · Vasseur · 2003 [cited by applicant]
US 20050004297A1 · Durel et al. · 2005 [cited by applicant]
US 20060151084A1 · Serra · 2006 [cited by applicant]
US 20070112120A1 · Vasseur · 2007 [cited by applicant]
US 20110098404A1 · Kwag et al. · 2011 [cited by applicant]
US 20120103487A1 · Majumdar · 2012 [cited by applicant]
US 20130068336A1 · Kanbe et al. · 2013 [cited by applicant]
US 20150114539A1 · Fudemoto · 2015 [cited by examiner]
US 20150368444A1 · Fleury et al. · 2015 [cited by applicant]
US 20160121654A1 · Shibata · 2016 [cited by applicant]
US 20170073509A1 · Koda · 2017 [cited by examiner]
US 20170362370A1 · Doisneau et al. · 2017 [cited by applicant]
US 20180326786A1 · Thuilliez et al. · 2018 [cited by applicant]
US 20180362754A1 · Thuilliez et al. · 2018 [cited by applicant]
US 20180371141A1 · Thuilliez et al. · 2018 [cited by applicant]
US 20200031980A1 · Doisneau et al. · 2020 [cited by applicant]
US 20210087366A1 · Thuilliez et al. · 2021 [cited by applicant]
US 20210347966A1 · Gavard-Lonchay et al. · 2021 [cited by applicant]
US 20210380784A1 · Thuilliez et al. · 2021 [cited by applicant]
US 20220064415A1 · Gavard-Lonchay et al. · 2022 [cited by applicant]
US 20230077022A1 · Thuilliez et al. · 2023 [cited by applicant]
CN 102463846A · 2012 [cited by applicant]
CN 104356457A · 2015 [cited by applicant]
EP 0247580A2 · 1987 [cited by applicant]
EP 0763564A2 · 1997 [cited by applicant]
EP 1403287A1 · 2004 [cited by applicant]
EP 2639055A1 · 2013 [cited by applicant]
EP 3006206A1 · 2016 [cited by applicant]
JP 11220258A · 1999 [cited by applicant]
JP 2000160479A · 2000 [cited by applicant]
JP 2004525022A · 2004 [cited by applicant]
JP 2005002182A · 2005 [cited by examiner]
JP 2010084112A · 2010 [cited by examiner]
JP 201257104A · 2012 [cited by applicant]
JP 2012207088A · 2012 [cited by applicant]
JP 2012229282A · 2012 [cited by applicant]
JP 2014129509A · 2014 [cited by applicant]
JP 20172141A · 2017 [cited by applicant]
JP 2017179118A · 2017 [cited by applicant]
KR 1020140126489A · 2014 [cited by applicant]
WO 9736724A2 · 1997 [cited by applicant]
WO 9916600A1 · 1999 [cited by applicant]
WO 0210269A2 · 2002 [cited by applicant]
WO 02078983A1 · 2002 [cited by applicant]
WO 0316387A1 · 2003 [cited by applicant]
WO 2014095586A1 · 2014 [cited by applicant]
WO 2016116468A1 · 2016 [cited by applicant]
WO 2017081387A1 · 2017 [cited by applicant]
WO 2017081388A1 · 2017 [cited by applicant]
WO 2017103403A1 · 2017 [cited by applicant]
WO 2017103404A1 · 2017 [cited by applicant]
WO 2017103406A1 · 2017 [cited by applicant]
English Machine Translation of JP 2005-002182. (Year: 2005). [cited by examiner]
English Machine Translation of JP 2010-084112. (Year: 2010). [cited by examiner]
International Search Report dated Feb. 20, 2020, in corresponding PCT/FR2019/053019 (6 pages). [cited by applicant]
Thomson Scientific, London GB; vol. 2015, No. 33, AN 2015-22497F, retrieved from: Database WPI (online) XP 002796186, 4 pages. [cited by applicant]
M.M. Jacobi, et al., “Study of the Epoxidation of Polydiene Rubbers II.”, KGK Kautschuk Gummi Kunststoffe 57, Jahrgang, Nr. Mar. 2004. [cited by applicant]
J.J. Yu, et al., “Ultraviolet-Initiated Photografting of Glycidyl Methacrylate onto Styrene-Butadiene Rubber”, J. Appl. Polymer Sci., vol. 73, 1733-1739 (1999). [cited by applicant]
N.M. Ahmad, et al., “Chain Transfer to Polymer in Free-Radical Solution Polymerization of n-Butyl Acrylate Studied by NMR Spectroscopy”, Macromolecules 1998, 31, 2822-2827. [cited by applicant]