Epoxy-functional amidoamine reacted with excess polyamine and monoepoxy as epoxy curative

• US 6,277,928 B1
• Filed: 06/10/1998
• Issued: 08/21/2001
• Est. Priority Date: 03/03/1998
• Status: Expired due to Term

• Current Assignee: Hexion Incorporated (Hexion Intermediate Holding 2, Inc.)
• Original Assignee: Resolution Performance Products LLC (Bakelite UK TopCo Ltd.)
• Inventors: Stark, Charles J., Stark, adminstrator, by Ann E., Ghosh, Kalyan, Dangayach, Kailash, Wang, Pen-Chung, Elmore, Jimmy D., Back, Gayle Edward
• Primary Examiner(s): SELLERS, ROBERT E
• Application Number:
  US09/095,079
• Time in Patent Office: 1,168 Days
• Field of Search: 525/438, 525/425, 523/417, 523/404, 523/414
• US Class Current: 525/423
• CPC Class Codes: C08G 59/184 with amines

Abstract

A water-dispersible curing agent for epoxy resins is prepared by the reaction of (a) an epoxy-functional compound obtained from the reaction of at least one epoxy resin and an amidoamine derived from the reaction of an acid-terminated polyalkylene glycol and a diamine in an active amine hydrogen:epoxy groups ratio of from 1:15 to 1:350, (b) at least one polyamine in an active amine hydrogen:epoxy groups ratio of from 2:1 to 30:1 which yields an amine-terminated product having an amine equivalent weight of at least 50, and, optionally, (c) a monoepoxy in a remaining active amine hydrogen:epoxy groups ratio of from 5:1 to 20:1.

Claims

1. A curing agent for epoxy resins comprising a reaction product having an amine equivalent weight of at least 50 prepared by the steps comprising reacting

(a) an epoxy-functional compound prepared by reacting an amidoamine having the formula:

wherein R¹ is an alkyl, aryl, or arylalkyl group having 1 to 15 carbon atoms, R² is aliphatic, cycloaphatic or aromatic group having 2 to 18 carbon atoms optionally containing non-reactive oxygen or at most an average of 4 secondary and/or tertiary nitrogen atoms per structure in the backbone, X and Y are independently a hydrogen, methyl or ethyl group with the provision that if X is methyl or ethyl, Y hydrogen or if Y is methyl or ethyl, X is hydrogen, and n+m+o is a real number from 65 to 200, and n, m, and o are each a real number such as to provide a number average molecular weight of the amidoamine from 3000 to 10,000, and n+o is within the range of from 80 percent to 100 percent of n+m+o, in a ratio of (I) to (II) by weight in the range of 100;

0 to 0;

100, in a ratio of (I) to (III) by weight in the range of 100;

0 to 0;

100, and in a ratio of (II) to (III) by weight in the range of 100;

0 to 0;

100, and at least one epoxy resin having a functionality of from 1.5 to 2.5 epoxide group per molecule in an active amine hydrogen atoms to epoxy groups ratio of from 1;

350 to 1;

15, said epoxy resin is a glycidyl ether containing aliphatic, cycloaliphatic, or aromatic moieties; and

(b) at least one polyamine in an active amine hydrogen atoms to epoxy groups ratio of 2;

1 to 30;

1 thereby producing an amine-terminated product having a amine equivalent weight of at least 50; and

(c) further reacting the amine terminated product with a monoepoxy in a remaining active amine hydrogen atoms to epoxy groups ratio of 5;

1 to 20;

1.

2. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structures (I) and (II) wherein the ratio of (I) to (II) by weight is in the range of 99:

1 to 1;

99 and the epoxy resin.

3. The curing agent of claim 2 wherein the ratio of (I) to (II) by weight is in the range of 20:

80 to 80;

20.

4. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structures (I) and (III) wherein the ratio of (I) to (III) by weight is in the range of 99:

1 to 1;

99 and the epoxy resin.

5. The curing agent of claim 4 wherein the ratio of (I) to (III) by weight is in the range of 20:

80 to 80;

20.

6. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structures (II) and (III) wherein the ratio of (II) to (III) by weight is in the range of 99:

1 to 1;

99, and the epoxy resin.

7. The curing agent of claim 6 wherein the ratio of (II) to (III) by weight is in the range of 20:

80 to 80;

20.

8. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structures (I), (II) and (III) in an amount of 4 to 98 percent by weight of (I), 1 to 95 percent by weight of (II), 1 to 95 percent by weight of (III) and the epoxy resin.

9. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structure (I) and the epoxy resin.

10. The curing agent of claim 9 wherein m is 0.

11. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structure (II) and the epoxy resin.

12. The curing agent of claim 11 wherein m is 0.

13. The curing agent of claim 1 wherein the epoxy-functional compound is prepared by reacting the amidoamine of structure (III) and the epoxy resin.

14. The curing agent of claim 13 wherein m is 0.

15. The curing agent of claim 1 wherein the polyamine in component (b) is present in an amount such that the active amine hydrogen atom to epoxy groups ratio is within the range of 5:

1 to 15;

1.

16. The curing agent of claim 1 wherein the amidoamine is prepared by reacting an acid-terminated polyalkyleneglycol alkylether having the formula

wherein R¹ is an alkyl, aryl, or arylalkyl group having 1 to 15 carbon atoms, o is a positive real number from about 100 to 200, and at least one diamine in an amine to acid equivalent ratio of 6: 1 to about 25;

1.

17. The curing agent of claim 1 wherein the monoepoxy is selected from the group consisting of glycidated C_8-20 aliphatic alcohol, C_1-18 alkylphenol glycidylether, glycidated versatic acid, and glycidoxyalkylalkoxysilanes.

18. A composition comprising (a) water, and (b) the curing agent of claim 1.