Modified amine curing agents and epoxy resins cured therewith

• US 4,514,530 A
• Filed: 07/05/1983
• Issued: 04/30/1985
• Est. Priority Date: 07/05/1983
• Status: Expired due to Fees

• Current Assignee: Huntsman Petrochemical LLC (Huntsman Corporation)
• Original Assignee: Texaco Incorporated (Chevron Corp.)
• Inventors: Speranza, George P., Sellstrom, Kathy B.
• Primary Examiner(s): Pertilla, Theodore
• Application Number:
  US06/510,695
• Time in Patent Office: 665 Days
• Field of Search: 525/454, 524/108, 524/590, 523/456
• US Class Current: 523/456
• CPC Class Codes: C08G 59/50 Amines
• CPC Class Codes: C08G 59/504 containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 75/04 Polyurethanes

Abstract

In accordance with the present invention an epoxy resin is cured with an amine curative comprising an alkylene carbonate solution of a solid elastomeric polyurethane in admixture with an amine-type curing agent.

Claims

1. A composition for use in the curing of a 1,2-epoxy resin comprising an alkylene carbonate solution of a normally solid cured elastomeric polyurethane in admixture with a primary amine curing agent.

2. A composition as in claim 1 wherein the elastomeric polyurethane is an elastomeric polyurethane formed by reaction injection molding and wherein the amine has the formula:

space="preserve" listing-type="equation">H.sub.2 NC.sub.2 H.sub.4 (HNC.sub.2 H.sub.4).sub.n NH.sub.2

wherein n is a number having a value of 0 to 5.

3. A composition as in claim 2 wherein the amine is diethylenetriamine.

4. A composition as in claim 3 wherein the alkylene carbonate is ethylene carbonate.

5. A composition as in claim 3 wherein the alkylene carbonate is propylene carbonate.

6. A method for the preparation of a composition useful in the curing of a 1,2-epoxy resin which comprises the steps of:

a. heating an alkylene carbonate to a temperature of 100 to about 200 degrees C. and dissolving therein a soluble amount of a cured solid elastomeric polyurethane, and

b. adding the resultant solution to a primary amine curing agent.

7. A method as in claim 6 wherein the polyurethane is a polyurethane prepared by reaction injection molding and wherein the amine is an amine having the formula:

space="preserve" listing-type="equation">H.sub.2 NC.sub.2 H.sub.4 (HNC.sub.2 H.sub.4).sub.n NH.sub.2

wherein n is a number having a value of about 0 to 5.

8. A method as in claim 7 wherein the amine is diethylenetriamine.

9. A method as in claim 8 wherein the alkylene carbonate is ethylene carbonate.

10. A method as in claim 8 wherein the alkylene carbonate is propylene carbonate.

11. A method for curing a 1,2-epoxy resin which comprises intimately mixing said epoxy resin with an effective amount of a primary amine curing agent comprising an alkylene carbonate solution of a normally cured solid polyurethane elastomer and a primary amine curing agent, whereby reaction of amino hydrogens of said amine with epoxy groups in said epoxy resin composition will result in the curing of said epoxy resin.

12. A method as in claim 11 wherein the said polyurethane is a polyurethane prepared by reaction injection molding and wherein the amine has the formula:

space="preserve" listing-type="equation">H.sub.2 NC.sub.2 H.sub.4 (HNC.sub.2 H.sub.4).sub.n X

wherein n is a number having a value of 0 to 5.

13. A method as in claim 12 wherein the amine is diethylenetriamine.

14. A method as in claim 13 wherein the alkylene carbonate is ethylene carbonate.

15. A method as in claim 13 wherein the alkylene carbonate is propylene carbonate.

16. An epoxide resin composition prepared by curing a 1,2-epoxy resin with an epoxy curative comprising a primary amine curing agent admixed with an alkylene carbonate solution of a cured solid elastomeric polyurethane.

17. A composition as in claim 16 wherein the polyurethane is a polyurethane prepared by reaction injection molding, and wherein the amine is an amine having the formula:

space="preserve" listing-type="equation">H.sub.2 NC.sub.2 H.sub.4 (HNC.sub.2 H.sub.4).sub.n X

wherein n has a value of 0 to 5.

18. A composition as in claim 17 wherein the amine is diethylene triamine.

19. A composition as in claim 18 wherein the alkylene carbonate is ethylene carbonate.

20. A composition as in claim 18 wherein the alkylene carbonate is propylene carbonate.

21. A method for preparing an epoxide resin composition which comprises the steps of:

(a) heating an alkylene carbonate to a temperature of about 100°

to 200°

C.,

(b) dissolving a primary amine curing agent and a soluble amount of a cured solid elastomeric polyurethane in said thus-heated alkylene carbonate,

(c) to thereby provide an epoxy resin curing composition comprising a solution of said solid elastomeric polyurethane and said amine curing agent in said alkylene carbonate, and

(d) mixing a 1,2-epoxy resin with an effective amount of said epoxy resin curing composition whereby reaction of amino hydrogens in said amine with epoxy groups in said epoxy resins will result in the curing of said epoxy resin.

22. An epoxide resin composition formed by curing a 1,2-epoxy resin with an epoxy resin curing composition comprising an alkylene carbonate having a primary amine curing agent and a cured solid elastomeric polyurethane dissolved therein, said epoxy resin curing composition having been prepared by heating said alkylene carbonate at a temperature of about 100°

to about 200°

C. and dissolving said amine curing agent and a soluble amount of said solid elastomeric polyurethane therein.