Curable composition and process for the manufacture of an epoxy thermoset

• US 20160152764A1
• Filed: 07/03/2014
• Published: 06/02/2016
• Est. Priority Date: 07/03/2013
• Status: Active Grant

• Current Assignee: Specialty Operations France
• Original Assignee: Rhodia Operations (Solvac SA)
• Inventors: Jeol, Stephane
• Granted Patent: US 10,077,332 B2
• Time in Patent Office: Days
• CPC Class Codes: C08G 59/184 with amines
• CPC Class Codes: C08G 59/245 aromatic
• CPC Class Codes: C08G 59/5046 heterocyclic
• CPC Class Codes: C08K 5/1535 Five-membered rings
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C09J 163/00 Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• CPC Class Codes: C09J 2463/00 Presence of epoxy resin
• CPC Class Codes: C09J 5/00 Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers

Abstract

Curable composition comprising at least one epoxy resin and at least one curing agent selected from derivatives of 5-hydroxymethylfurfural. Curable dispersion, curable prepolymer composition and process for manufacturing it. Process for the manufacture of an epoxy thermoset, epoxy thermoset and method for adhering at least two substrates.

Claims

1. A curable composition comprising

(a) at least one curing agent, wherein said curing agent is a derivative of 5-hydroxymethylfurfural corresponding to formula I or to formula II

2. The curable composition according to claim 1, in which

(a) the curing agent is a derivative of 5-hydroxymethylfurfural selected from the group consisting of

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ and R₂ are both equal to —

(CH₂)_n—

NH₂;

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ and R₂ are both equal to —

COOH;

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ is equal to —

(CH₂)_n—

NH₂ and R₂ is equal to —

COOH;

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ is equal to —

(CH₂)_n—

NH₂ and R₂ is equal to

3. The curable composition according to claim 1, in which

(a) the curing agent is a derivative of 5-hydroxymethylfurfural selected from the group consisting of

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ and R₂ are both equal to —

(CH₂)_n—

NH₂;

derivatives of 5-hydroxymethylfurfural corresponding to formula I in which R₁ is equal to —

(CH₂)_n—

NH₂ and R₂ is equal to —

COOH;

derivatives of 5-hydroxymethylfurfural corresponding to formula II in which R₃ and R₄ are both equal to —

(CH₂)_n—

NH₂, and

derivatives of 5-hydroxymethylfurfural corresponding to formula II in which R₃ is equal to —

(CH₂)_n—

NH₂ and R₄ is equal to —

COOH.

4. The curable composition according to claim 1, in which

(a) the curing agent is a derivative of 5-hydroxymethylfurfural corresponding to formula I or to formula II in which n is equal to 1.

5. The curable composition according to claim 1, in which the curing agent is 2,5-bis(aminomethyl)furan.

6. The curable composition according to claim 1, in which the curing agent is 2,5-bis(aminomethyl)tetrahydrofuran.

7. The curable composition according to claim 1, in which curing agent (a) is the sole curing agent.

8. The curable composition according to claim 1, further comprising at least one dispersing agent.

13. A method for adhering at least two substrates comprising

applying the curable composition according to claim 1, to one or both of the substrates;

and

bringing the substrates into a contacting relationship.

14. The method according to claim 13, further comprising curing the epoxy resin.

15. The method according to claim 14, wherein the curing is made at a temperature comprised between −

25°

C. and 200°

C.

9. A curable prepolymer composition comprising a prepolymer which is the reaction product of at least one epoxy resin (b) with at least one curing agent (a),

wherein curing agent (a) is a derivative of 5-hydroxymethylfurfural corresponding to formula I or to formula II

10. A process for the manufacture of the curable prepolymer composition according to claim 9, the process comprising reacting at least one curing agent (a) with at least one epoxy resin (b),

wherein curing agent (a) is a derivative of 5-hydroxymethylfurfural corresponding to formula I or to formula II

16. A process for the manufacture of an epoxy thermoset comprising reacting at least one curable prepolymer composition according to claim 9 with at least one epoxy resin (b).

17. An epoxy thermoset obtained by the process according to claim 16.

18. A method for adhering at least two substrates comprising

applying the curable prepolymer composition according to claim 9 to one or both of the substrates;

and

bringing the substrates into a contacting relationship.

19. The method according to claim 18, further comprising curing the epoxy resin.

20. The method according to claim 19, wherein the curing is made at a temperature comprised between −

25°

C. and 200°

C.

11. A process for the manufacture of an epoxy thermoset comprising reacting at least one curing agent (a) with at least one epoxy resin (b),

wherein curing agent (a) is a derivative of 5-hydroxymethylfurfural corresponding to formula I or to formula II

12. An epoxy thermoset obtained by the process according to claim 11.