IP Library Granted Patent US 10,005,929
Granted Patent B2
US 10,005,929 · App. 14/235,521 · Granted Jun 26, 2018

Aqueous adhesive composition based on polyaldehyde and 2,2′,4,4′-tetrahydroxydiphenyl sulphide

Inventors: David Doisneau (Clermont-Ferrand, FR); Hélène Decorps (Clermont-Ferrand, FR)
Assignee: Compagnie Generale Des Etablissements Michelin
C09J109/08C08L7/02C09J7/21C09J7/30C09J107/02C09J121/02C09J161/12C08L21/02Y10T428/249921Y10T442/2738
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Quick Facts
Patent No.
US 10,005,929
App. No.
14/235,521
Granted
Jun 26, 2018
Kind
B2
Abstract

An aqueous adhesive composition includes: a phenol/aldehyde resin; and an unsaturated elastomer latex. The phenol/aldehyde resin is based on at least: an aromatic polyaldehyde bearing at least two aldehyde functional groups and including at least one aromatic nucleus; and 2,2′,4,4′-tetrahydroxydiphenyl sulphide. The adhesive composition is useable to make a textile material adhere to a crosslinkable rubber composition, and may be used as an advantageous alternative to a formaldehyde-based RFL adhesive.

Claims (44)

1. An aqueous adhesive composition comprising:

a phenol/aldehyde resin; and

an unsaturated elastomer latex,

wherein the phenol/aldehyde resin is based on:

2,2′,4,4′-tetrahydroxydiphenyl sulphide, and

wherein the aldehyde in the phenol/aldehyde resin is an aromatic polyaldehyde bearing at least two aldehyde functional groups, the aromatic polyaldehyde including at least one aromatic nucleus.

2. The aqueous adhesive composition according to claim 1 , wherein the at least one aromatic nucleus of the aromatic polyaldehyde is a benzene nucleus.

3. The aqueous adhesive composition according to claim 1 , wherein the at least two aldehyde functional groups are borne by the at least one aromatic nucleus.

4. The aqueous adhesive composition according to claim 3 , wherein the aromatic polyaldehyde is selected from a group consisting of 1,2-benzenedicarboxaldehyde, 1,3-benzenedicarboxaldehyde, 1,4-benzenedicarboxaldehyde, 2-hydroxybenzene-1,3,5-tricarbaldehyde, and mixtures thereof.

5. The aqueous adhesive composition according to claim 4 , wherein the aromatic polyaldehyde is 1,4-benzenedicarboxaldehyde.

6. The aqueous adhesive composition according to claim 1 , wherein the phenol/aldehyde resin includes a basic solvent.

7. The aqueous adhesive composition according to claim 6 , wherein the basic solvent is an aqueous solution having a pH between 9 and 13.

8. The aqueous adhesive composition according to claim 1 , wherein an unsaturated elastomer of the unsaturated elastomer latex is a diene elastomer selected from a group consisting of polybutadienes, butadiene copolymers, polyisoprenes, isoprene copolymers, vinylpyridine/styrene/butadiene terpolymers, and mixtures thereof.

9. The aqueous adhesive composition according to claim 1 , wherein a ratio by weight of the 2,2′,4,4′-tetrahydroxydiphenyl sulphide to the aromatic polyaldehyde is between 0.1 and 3.0.

10. 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.

11. 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.

12. 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.

13. 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.

14. A textile material coated at least partially with an adhesive layer, the adhesive layer including an adhesive composition comprising:

a phenol/aldehyde resin; and

an unsaturated elastomer latex,

wherein the phenol/aldehyde resin is based on:

2,2′,4,4′-tetrahydroxydiphenyl sulphide, and

wherein the aldehyde in the phenol/aldehyde resin is an aromatic polyaldehyde bearing at least two aldehyde functional groups, the aromatic polyaldehyde including at least one aromatic nucleus.

15. The textile material according to claim 14 , wherein the adhesive composition is an aqueous adhesive composition.

16. The textile material according to claim 14 , wherein the textile material has been dried.

17. The textile material according to claim 14 , wherein the textile material is a material selected from a group consisting of films, monofilaments, multifilament fibres, assemblies of monofilaments or multifilament fibres, and mixtures thereof.

18. The textile material according to claim 14 , wherein the textile material is formed of a substance that includes a thermoplastic polymer.

19. The textile material according to claim 18 , wherein the thermoplastic polymer is an aliphatic polyamide or a polyester.

20. A rubber composite reinforced with a textile material coated at least partially with an adhesive layer, the adhesive layer including an adhesive composition comprising:

a phenol/aldehyde resin; and

an unsaturated elastomer latex,

wherein the phenol/aldehyde resin is based on:

2,2′,4,4′-tetrahydroxydiphenyl sulphide, and

wherein the aldehyde in the phenol/aldehyde resin is an aromatic polyaldehyde bearing at least two aldehyde functional groups, the aromatic polyaldehyde including at least one aromatic nucleus.

21. The rubber composite according to claim 20 , wherein the rubber composite is incorporated in a tire.

22. An adhesive composition comprising:

a phenol/aldehyde resin; and

an unsaturated elastomer latex,

wherein the phenol/aldehyde resin is based on:

2,2′,4,4′-tetrahydroxydiphenyl sulphide, and

wherein the aldehyde in the phenol/aldehyde resin is an aromatic polyaldehyde bearing at least two aldehyde functional groups, the aromatic polyaldehyde including at least one aromatic nucleus.

23. The adhesive composition according to claim 22 , wherein the adhesive composition is in an uncured state.

24. The adhesive composition according to claim 22 , wherein the adhesive composition is in a cured state.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2017
From: MICHELIN RECHERCHE ET TECHNIQUE S.A.
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 044069/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2014
From: DOISNEAU, DAVID; DECORPS, HELENE
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
Reel/Frame 032779/0244 →
Priority Claims (1)
FR 11 57158 · Aug 4, 2011 · national
Continuity (1)
Related Publication 20140308864A1 · Oct 16, 2014
Cited By (2)
US 12,202,966 US 12,252,559