# US 10,767,086 B2 · Aqueous adhesive composition based on polyaldehyde and polyphenol > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,086 B2 - Document ID: US10767086B2 - Status: Granted - Kind: B2 - Application number: 15/805,824 - Filed: 2017-11-07 - Published: 2018-05-03 - Granted: 2020-09-08 - Earliest claimed: 2011-08-04 - Assignees: Compagnie Generale Des Establissements Michelin - Applicants: Compagnie Generale Des Etablissements Michelin; Michelin Recherche et Technique S.A. - Inventors: David Doisneau; Hélène Decorps - Web page: https://patentgrep.com/patent/US10767086B2 ## CPC - C09J 109/08: Latex - C08L 21/02: Latex - C09J 7/21: Paper; Textile fabrics - C09J 7/30: characterised by the adhesive composition - C09J 107/02: Latex - C09J 121/02: Latex - C09J 161/12: with polyhydric phenols - C08L 61/06: of aldehydes with phenols - Y10T 428/249921: Web or sheet containing structurally defined element or component - Y10T 442/2738: Coating or impregnation intended to function as an adhesive to solid surfaces subsequently associated therewith - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract An aqueous adhesive composition includes: a phenol/aldehyde resin and an unsaturated elastomer latex. The phenol/aldehyde resin is based on: an aromatic polyaldehyde bearing at least two aldehyde functional groups and including at least one aromatic nucleus; and a polyphenol including at least one aromatic nucleus. If there is just one aromatic nucleus, the nucleus bears two or three hydroxyl functional groups in a meta position with respect to each other or with respect to one another, with a remainder of the nucleus being unsubstituted. If there are plural aromatic nuclei, at least two of the nuclei each bear two or three hydroxyl functional groups in the meta position with respect to each other or with respect to one another, with two positions ortho to at least one of these hydroxyl functional groups being unsubstituted. The adhesive composition is useable to adhere a textile material to a crosslinkable rubber composition. ## Claims ### Claim 1 An aqueous adhesive composition comprising: an unsaturated elastomer latex; and a phenol/aldehyde resin, wherein the phenol/aldehyde resin is based on at least: an aromatic polyaldehyde including at least one aromatic nucleus bearing at least two aldehyde functional groups, and a flavonoid. ### Claim 2 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the at least one aromatic nucleus of the aromatic polyaldehyde is a benzene nucleus. ### Claim 3 (depends on 2) The aqueous adhesive composition according to claim 2, wherein the at least two aldehyde functional groups are in the ortho, meta or para position. ### Claim 4 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde bears only two aldehyde functional groups. ### Claim 5 (depends on 4) The aqueous adhesive composition according to claim 4, wherein the two aldehyde functional groups are in the ortho position. ### Claim 6 (depends on 4) The aqueous adhesive composition according to claim 4, wherein the two aldehyde functional groups are in the meta position. ### Claim 7 (depends on 4) The aqueous adhesive composition according to claim 4, wherein the two aldehyde functional groups are in the para position. ### Claim 8 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde is selected from the group consisting of 1,2-benzenedicarboxaldehyde, 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde, 2-hydroxybenzene-1,3,5-tricarbaldehyde, and mixtures thereof. ### Claim 9 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde is 1,2-benzenedicarboxaldehyde. ### Claim 10 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde is 1,3-benzenedicarboxaldehyde. ### Claim 11 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde is 1,4-benzenedicarboxaldehyde. ### Claim 12 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the aromatic polyaldehyde is 2-hydroxybenzene-1,3,5-tricarbaldehyde. ### Claim 13 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the phenol/aldehyde resin includes a basic solvent. ### Claim 14 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the basic solvent is an aqueous solution having a pH between 9 and 13. ### Claim 15 (depends on 1) The aqueous adhesive composition according to claim 1, wherein an unsaturated elastomer of the unsaturated elastomer latex is a diene elastomer selected from the group consisting of polybutadienes, butadiene copolymers, polyisoprenes, isoprene copolymers, vinylpyridine/styrene/butadiene terpolymers, and mixtures thereof. ### Claim 16 (depends on 1) The aqueous adhesive composition according to claim 1, wherein a ratio by weight of the flavonoid to the aromatic polyaldehyde is between 0.1 and 3.0. ### Claim 17 (depends on 1) The aqueous adhesive composition according to claim 1, wherein a content of the phenol/aldehyde resin as dry matter of the adhesive composition is between 5% and 60% by weight of the dry matter of the adhesive composition. ### Claim 18 (depends on 1) The aqueous adhesive composition according to claim 1, wherein a content of unsaturated elastomer as dry matter of the adhesive composition is between 40% and 95% by weight of the dry matter of the adhesive composition. ### Claim 19 (depends on 1) The aqueous adhesive composition according to claim 1, wherein a ratio by weight of dry matter corresponding to the phenol/aldehyde resin to dry matter corresponding to the unsaturated elastomer latex is between 0.1 and 2.0. ### Claim 20 (depends on 1) The aqueous adhesive composition according to claim 1, wherein a water content of the adhesive composition is between 60% and 90% by weight of the aqueous adhesive composition. ### Claim 21 A textile material coated at least partially with an adhesive layer, the adhesive layer including an adhesive composition comprising: an unsaturated elastomer latex; and a phenol/aldehyde resin, wherein the phenol/aldehyde resin is based on at least: an aromatic polyaldehyde including at least one aromatic nucleus bearing at least two aldehyde functional groups, and a flavonoid. ### Claim 22 (depends on 21) The textile material according to claim 21, wherein the adhesive composition is an aqueous adhesive composition. ### Claim 23 (depends on 21) The textile material according to claim 21, wherein the textile material has been dried. ### Claim 24 (depends on 21) The textile material according to claim 21, wherein the textile material is a material selected from the group consisting of films, monofilaments, multifilament fibres, assemblies of monofilaments or multifilament fibres, and mixtures thereof. ### Claim 25 (depends on 21) The textile material according to claim 21, wherein the textile material is formed of a substance that includes a thermoplastic polymer. ### Claim 26 (depends on 25) The textile material according to claim 25, wherein the thermoplastic polymer is an aliphatic polyamide or a polyester. ### Claim 27 A rubber composite reinforced with a textile material coated at least partially with an adhesive layer, the adhesive layer including an adhesive composition comprising: an unsaturated elastomer latex; and a phenol/aldehyde resin, wherein the phenol/aldehyde resin is based on at least: an aromatic polyaldehyde including at least one aromatic nucleus bearing at least two aldehyde functional groups, and a flavonoid. ### Claim 28 (depends on 3) The rubber composite according to claim 3, wherein the rubber composite is incorporated in a tire. ### Claim 29 An adhesive composition comprising: an unsaturated elastomer latex; and a phenol/aldehyde resin, wherein the phenol/aldehyde resin is based on at least: an aromatic polyaldehyde including at least one aromatic nucleus bearing at least two aldehyde functional groups, and a flavonoid. ### Claim 30 (depends on 29) The adhesive composition according to claim 29, wherein the adhesive composition is in an uncured state. ### Claim 31 (depends on 29) The adhesive composition according to claim 29, wherein the adhesive composition is in a cured state. ### Claim 32 (depends on 1) The aqueous adhesive composition according to claim 1, wherein the flavonoid is 2′,4′,3,5,7-pentahydroxyflavone. ### Claim 33 (depends on 21) The textile material according to claim 21, wherein the flavonoid is 2′,4′,3,5,7-pentahydroxyflavone. ### Claim 34 (depends on 27) The rubber composite according to claim 27, wherein the flavonoid is 2′,4′,3,5,7-pentahydroxyflavone. ### Claim 35 (depends on 29) The adhesive composition according to claim 29, wherein the flavonoid is 2′,4′,3,5,7-pentahydroxyflavone.