US 11,866,578 B2
Rubber composition based on epoxy resin, an amine hardener and an imidazole
Emmanuel Landreau, Clermont-Ferrand (FR); and Etienne Fleury, Clermont-Ferrand (FR)
Assigned to COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN, Clermont-Ferrand (FR)
Appl. No. 17/276,637
Filed by COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN, Clermont-Ferrand (FR)
PCT Filed Sep. 12, 2019, PCT No. PCT/FR2019/052117
§ 371(c)(1), (2) Date Mar. 16, 2021,
PCT Pub. No. WO2020/058604, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 1858347 (FR), filed on Sep. 17, 2018.
Prior Publication US 2022/0041843 A1, Feb. 10, 2022
Int. Cl. C08L 7/00 (2006.01); B60C 1/00 (2006.01)
CPC C08L 7/00 (2013.01) [B60C 1/0016 (2013.01); C08L 2312/00 (2013.01)] 15 Claims
 
1. A rubber composition based on at least:
a diene elastomer;
a reinforcing filler;
a crosslinking system;
from 1 to 30 parts by weight, per hundred parts by weight of elastomer, phr, of an epoxy resin;
between 1 and 15 phr of an amine hardener comprising at least two primary amine functions, located on at least one six-membered aromatic ring, the at least one six-membered aromatic ring comprising:
at least one primary amine function, and
at least two Ri radicals, which are identical or different, selected from the group consisting of linear or branched C1-C6 alkyl radicals, halogens, ethers, tertiary amines, thioethers, ketones, esters, and amides, any of which can be substituted by linear or branched C1-C6 alkyl radicals,
so that the at least one six-membered aromatic ring does not comprise a hydrogen atom located in the ortho position with respect to the primary amine functions; and
an imidazole of general formula (A)

OG Complex Work Unit Chemistry
in which:
Ra represents a naphthylalkyl group, optionally interrupted by one or more heteroatoms, optionally substituted, or both optionally interrupted by one or more heteroatoms and optionally substituted,
Rb represents a hydrocarbon group,
Rc and Rd represent, independently of one another, a hydrogen atom or a hydrocarbon group, optionally interrupted by one or more heteroatoms, optionally substituted, or both optionally interrupted by one or more heteroatoms and optionally substituted,
or else Rc and Rd form, together with the carbon atoms of the imidazole ring to which they are attached, a ring optionally interrupted by one or more heteroatoms, optionally substituted, or both optionally interrupted by one or more heteroatoms and optionally substituted.