Epoxy systems for composites

Patent metadata

Field	Value
Publication number	US-9751973-B2
Application number	US-201615060411-A
Country	US
Kind code	B2
Filing date	Mar 3, 2016
Priority date	Jun 24, 2010
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Compositions and methods for forming epoxy resin systems are provided. In one embodiment, a composition is provided for an epoxy resin system including a reaction product of an epoxy resin component and a curing agent component comprising a first amine compound having the formula R1R2R3N, wherein R1 and R2 are independently an aliphatic or alicyclic organic functional group and R3 is an alkyl group, having a backbone of 2-18 carbon atoms, and a second amine compound having one or more primary or secondary amine groups, with the stoichiometic ratio of —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component being from 1:20 to about 21:20. The composition may be used to form composites, such as used in commercial wind turbine blade manufacturing.

First claim

What is claimed is:

1. A method for preparing an epoxy resin product, comprising:
providing an epoxy resin component to a mixing device;
providing a curing agent component to the mixing device, and the curing agent component comprising:
a first amine compound represented by the formula:

 wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an aralkyl group; and
a second amine compound having one or more primary amine groups, one or more secondary amine groups, or combinations thereof, wherein the stoichiometric ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from 3:10 to 19:20 and the molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1; and

reacting the epoxy resin component and curing agent.

2. The method of claim 1 , wherein the reaction of the epoxy resin component and the curing agent exhibits a maximum exothermic temperature of 230° C. or lower for a 100 gram mass in a water bath at 70° C.

3. The method of claim 1 , wherein the second amine compound comprises one or more amine compounds selected from the group consisting of a polyether diamine, a saturated aliphatic ring diamine, and combinations thereof.

4. The method of claim 1 , wherein the R3 further comprises a functional group selected from the group consisting of a primary amine group, a secondary amine group, a tertiary amine group, and combinations thereof.

5. The method of claim 1 , wherein R1 and R2 each comprise a functional group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a C5-C6 carbocyclic aliphatic ring, a C5-C6 heterocyclic aliphatic ring, a C5-C6 saturated aliphatic ring, a C5-C6 unsaturated aliphatic ring, and combinations thereof.

6. The method of claim 1 , wherein the R3 group comprises a benzyl group.

7. The method of claim 1 , wherein the polyether diamine has the formula: H 2 NCH(CH 3 )CH 2 [OCH 2 CH(CH 3 )] X NH 2 , and x is from 2 to 70.

8. The method of claim 1 , wherein the epoxy resin component further comprises:
a polyglycidyl ether of a compound selected from the group consisting of an aliphatic glycol, a cycloaliphatic glycol, a triol, a polyol, a polyglycol, and combinations thereof,
a polyacrylate or polymethacrylate ester of a polyol, or
a combination thereof.

9. The method of claim 1 , wherein the composition of the epoxy resin component and the curing agent exhibits a T g of 75° C. at a cure time of less than 3 hours as measured by Differential Scanning Calorimetry.

10. The method of claim 1 , further comprising
providing a reinforcing fiber substrate; and
contacting the reinforcing fiber substrate with the epoxy resin system.

11. The method of claim 10 , wherein the reinforced fiber substrate comprises one or more layers of fiberglass material.

12. The method of claim 10 , wherein the contacting the reinforcing fiber substrate with the epoxy resin system comprises an application process selected from the group consisting of an infusion process, a molding process, a layering process, and combinations thereof.

13. A composition comprising an epoxy resin system, the epoxy resin system comprising a reaction product of:
an epoxy resin component; and
a curing agent component comprising:
a first amine compound represented by the formula:

 wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an aralkyl group;
a second amine compound having one or more primary amine groups, one or more secondary amine groups, or combinations thereof, wherein the stoichiometric ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 19:20 and the molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1.

14. The composition of claim 13 , wherein the second amine compound comprises one or more amine compounds selected from the group consisting of a polyether diamine, a saturated aliphatic ring diamine, a linear aliphatic amine, and combinations thereof.

15. The composition of claim 13 , wherein the R3 group further comprises a functional group selected from the group consisting of a primary amine group, a secondary amine group, a tertiary amine group, and combinations thereof.

16. The composition of claim 13 , wherein R1 and R2 each comprise a functional group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a C5-C6 carbocyclic aliphatic ring, a C5-C6 heterocyclic aliphatic ring, a C5-C6 saturated aliphatic ring, a C5-C6 unsaturated aliphatic ring, and combinations thereof.

17. The composition of claim 13 , wherein the R3 group comprises a benzyl group.

18. The composition of claim 14 , wherein the polyether diamine has the formula: H 2 NCH(CH 3 )CH 2 [OCH 2 CH(CH 3 )] X NH 2 , and x is from 2 to 70.

19. The composition of claim 13 , wherein the epoxy resin component further comprises:
a polyglycidyl ether of a compound selected from the group consisting of an aliphatic glycol, a cycloaliphatic glycol, a triol, a polyol, a polyglycol, and combinations thereof,
a polyacrylate or polymethacrylate ester of a polyol, or
a combination thereof.

20. The composition of claim 13 , wherein, when cured, the reaction product of the epoxy resin component and the curing agent exhibits a T g of 75° C. or higher at a cure time of three hours or less as measured by Differential Scanning Calorimetry.

21. The composition of claim 13 , wherein, when curing, the reaction product of the epoxy resin component and the curing agent exhibits a maximum exothermic temperature of 230° C. or lower for a 100 gram mass in a water bath at 70° C.

22. The composition of claim 13 , wherein the curing agent further comprises a modified amine compound selected from the group consisting of a secondary amine, a Mannich base, an amine-epoxy adduct, and combinations thereof.

23. The composition of claim 13 , wherein R1 and R2 are both methyl functional groups.

24. The composition of claim 13 , wherein the composition further comprises a mineral material selected from the group consisting of clay, boehmite, calcium carbonates, aluminosilicates, silica, and combinations thereof.

Assignees

• Corley Larry Steven
• Farris Robert D
• Ash Carlton E
• Hexion Inc

Inventors

• Corley Larry Steven
• Farris Robert D
• Ash Carlton E

Classifications

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C08J5/043

  with glass fibres · CPC title

• C08G59/56

  together with other curing agents · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G59/5033

  aromatic · CPC title