Low emission epoxy curing agents

Patent metadata

Field	Value
Publication number	US-9469721-B2
Application number	US-201314439594-A
Country	US
Kind code	B2
Filing date	Dec 11, 2013
Priority date	Dec 20, 2012
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

A hardener composition comprising: a) an amine component; and b) a glycol ether component comprising i) from 10 weight percent to 70 weight percent alkylene glycol phenyl ether; ii) from 25 weight percent to 80 weight percent dialkylene glycol phenyl ether; iii) from 5 weight percent to 20 weight percent trialkylene glycol phenyl ether, is disclosed. The hardener composition can be used in epoxy thermoset formulations.

First claim

The invention claimed is:

1. A hardener composition comprising:
a) an amine component; and
b) a glycol ether component comprising
i) from 10 weight percent to 70 weight percent alkylene glycol phenyl ether;
ii) from 25 weight percent to 80 weight percent dialkylene glycol phenyl ether; and
iii) from 5 weight percent to 20 weight percent trialkylene glycol phenyl ether, based on the total weight of the glycol ether component.

2. A hardener composition in accordance with claim 1 wherein said alkylene glycol phenyl ether is selected from the group consisting of ethylene glycol phenyl ether and propylene glycol phenyl ether, said dialkylene glycol phenyl ether is selected from diethylene glycol phenyl ether and dipropylene glycol phenyl ether, and said trialkylene glycol phenyl ether is selected from the group consisting of triethylene glycol phenyl ether and tripropylene glycol phenyl ether.

3. A hardener composition in accordance with claim 1 wherein said glycol ether component has a vapor pressure of less than 0.004 mm Hg at 20° C.

4. A hardener composition in accordance with claim 1 wherein said glycol ether component comprises i) 70 weight percent ethylene glycol phenyl ether; ii) from 25 weight percent to 27 weight percent diethylene glycol phenyl ether; and iii) from 3 weight percent to 5 weight percent triethylene glycol phenyl ether, based on the total weight of said glycol ether component.

5. A hardener composition in accordance with claim 1 wherein said glycol ether component comprises i) from 15 weight percent to 25 weight percent ethylene glycol phenyl ether; ii) from 60 weight percent to 75 weight percent diethylene glycol phenyl ether; and iii) from 5 weight percent to 20 weight percent triethylene glycol phenyl ether, based on the total weight of said glycol ether component.

6. A hardener composition in accordance with claim 1 wherein the glycol ether component comprises a polyalkylene glycol phenyl ether with a number average molecular weight of from 300 daltons to 400 daltons.

7. A hardener composition in accordance with claim 1 wherein said amine component is selected from the group consisting of isophorone diamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, poly(oxypropylene diamine), meta-xylene diamine, and combinations thereof.

8. A hardener composition in accordance with claim 1 wherein said amine component is present in an amount in the range of from 25 weight percent to 90 weight percent and said glycol ether component is present in an amount in the range of from 10 weight percent to 75 weight percent, based on the total weight of the hardener composition.

9. A thermoset composition comprising:
a) an epoxy resin;
b) an amine component;
c) a glycol ether component comprising
i) from 10 weight percent to 70 weight percent alkylene glycol phenyl ether;
ii) from 25 weight percent to 80 weight percent dialkylene glycol phenyl ether; and
iii) from 5 weight percent to 20 weight percent trialkylene glycol phenyl ether, based on the total weight of the glycol ether component; and

d) a catalyst.

10. A thermoset composition in accordance with claim 9 wherein the thermoset composition has an epoxide to amine hydrogen equivalent ratio in the range of from 0.5 to 1.5.

11. A thermoset composition in accordance to claim 9 wherein the catalyst is present in an amount in the range of from 0.2 weight percent to 12 weight percent, based on the total weight of the composition.

12. A thermoset composition in accordance with claim 9 wherein said alkylene glycol phenyl ether is selected from the group consisting of ethylene glycol phenyl ether and propylene glycol phenyl ether, said dialkylene glycol phenyl ether is selected from diethylene glycol phenyl ether and dipropylene glycol phenyl ether, and said trialkylene glycol phenyl ether is selected from the group consisting of triethylene glycol phenyl ether and tripropylene glycol phenyl ether.

13. A thermoset composition in accordance with claim 9 wherein said glycol ether component has a vapor pressure of less than 0.004 mm Hg at 20° C.

14. A thermoset composition in accordance with claim 9 wherein said glycol ether component comprises i) 70 weight percent ethylene glycol phenyl ether; ii) from 25 weight percent to 27 weight percent diethylene glycol phenyl ether; and iii) from 3 weight percent to 5 weight percent triethylene glycol phenyl ether, based on the total weight of said glycol ether component.

15. A thermoset composition in accordance with claim 9 wherein said glycol ether component comprises i) from 15 weight percent to 25 weight percent ethylene glycol phenyl ether; ii) from 60 weight percent to 75 weight percent diethylene glycol phenyl ether; iii) from 5 weight percent to 20 weight percent triethylene glycol phenyl ether, based on the total weight of said glycol ether component.

16. A thermoset composition in accordance with claim 9 wherein said amine component is selected from the group consisting of isophorone diamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, poly(oxypropylene diamine), meta-xylene diamine, and combinations thereof.

17. A thermoset composition in accordance with claim 9 wherein said catalyst is salicylic acid.

18. A thermoset composition in accordance with claim 9 further comprising e) a toughening agent.

19. An article prepared from the thermoset composition of claim 9 , wherein said article is selected from the group consisting of a composite, a coating, an adhesive, and a mortar.

Assignees

• Blue Cube Ip Llc

Inventors

• Turakhia Rajesh H
• Falsarella Larissa
• Michalski Eva-Maria
• Pfarherr Marcus
• Marshall Jr Carl J
• Dellinger Bill Z
• Donate Felipe A

Classifications

• C04B26/14

  Polyepoxides · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G59/50 Primary

  Amines · CPC title

• C08K5/0016

  Plasticisers · CPC title

• C08G59/502

  Polyalkylene polyamines · CPC title