Amidopolyamines with enhanced gel-time for elevated temperature applications

Patent metadata

Field	Value
Publication number	US-10174154-B2
Application number	US-201514932095-A
Country	US
Kind code	B2
Filing date	Nov 4, 2015
Priority date	Nov 4, 2014
Publication date	Jan 8, 2019
Grant date	Jan 8, 2019

Abstract

An epoxy curing agent is disclosed that can be obtained by reacting at least one carboxylic acid with at least one polyamine. The disclosed curing agent can be obtained by preparing an amidoamine with about 0.15 to about 0.30 molar excess of carboxylic acid.

First claim

The invention claimed is:

1. An epoxide-based composition, comprising
(A) an epoxide component comprising at least one phenyl glycidyl ether polyepoxide having at least two epoxide group of oxirane structure in the molecule;
(B) a curing agent component comprising an amidoamine of a polyamine with tall oil fatty acid which is obtained by reacting one molar equivalent of the polyamine with about 1.30 molar equivalent of tall oil fatty acid, wherein the polyamine is selected from the group consisting of diethylenetriamine, triethylenetetramine, and tetraethylenepentamine;
wherein the composition has an imidazoline to amide ratio of about 0.8, and wherein the composition has a viscosity of less than about 20,000 cP within about 24 hours to about 30 hours of combining the epoxide component and the curing agent component.

2. The composition of claim 1 wherein the composition has a curing temperature of about 65° C.

3. The composition of claim 1 prepared by a process comprising the steps of reacting at least one carboxylic acid with at least one polyamine.

4. The composition of claim 1 wherein the curing time is about 5 hours.

5. The composition of claim 4 wherein the cured composition has a viscosity of at least 20,000 cP.

6. A method for producing a curing agent comprising reacting at least one carboxylic acid with at least one polyamine selected from the group consisting of diethylenetriamine, triethylenetetramine, and tetraethylenepentamine;
wherein about 0.30 molar excess of carboxylic acid to polyamines is reacted at a temperature above 190° C., and wherein the curing agent has an imidazoline to amide ratio of about 0.8.

7. The method of claim 6 wherein the carboxylic acid comprise at least one member selected from the group consisting of octanoic acid, 2-ethylhexanoic acid, decanoic acid, dodecanoic acid, tall oil fatty acid and dimer fatty acid.

8. The method of claim 6 wherein the polyamine further comprises at least one member selected from the group consisting of dipropylenetriamine, polypropyleneamines, N-3-aminopropyl ethylenediamine, aminopropylated ethylenediamines, aminopropylated propylenediamines, 1,6-hexanediamine, 3,3,5-trimethyl-1,6-hexanediamine, tripropylenetetramine, N-3-aminopropyl-1,3-diaminopropane, N,N′-bis(3-aminopropyl)-1,3-diaminopropane, N,N,N′-5 tris(3-aminopropyl)-1,3-diaminopropane, 2-methyl-1,5-pentanediamine, N,N′-bis(3-aminopropyl) ethylenediamine (N4), N,N,N′-tris(3-aminopropyl) ethylenediamine (N5), and any combination thereof.

9. The method of claim 6 wherein the curing agent has a structure of:

R=alkyl chain of 8-20 carbon atoms, n=2-3, R′=polyalkylamine chain with or without an imidazoline ring.

Assignees

• Evonik Degussa Gmbh

Inventors

• Lal Gauri Sankar
• Ananthachar Sudhir
• Boyce Stephen Michael

Classifications

• C08G59/54 Primary

  Amino amides> · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C07C233/38

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C08G59/22

  Di-epoxy compounds · CPC title