Curing agent composition for epoxy resins and epoxy resin composition

• US 20070142572A1
• Filed: 12/12/2006
• Published: 06/21/2007
• Est. Priority Date: 12/16/2005
• Status: Active Grant

• Current Assignee: Mitsubishi Gas Chemical Company Incorporated (Mitsubishi Electric Corporation)
• Original Assignee: Mitsubishi Gas Chemical Company Incorporated (Mitsubishi Electric Corporation)
• Inventors: Kuwahara, Hisayuki, Ogawa, Shun
• Granted Patent: US 8,431,653 B2
• Time in Patent Office: Days
• US Class Current: 525/476
• CPC Class Codes: C08G 59/184 with amines
• CPC Class Codes: C08G 59/50 Amines
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Abstract

The present invention relates to a curing agent composition for epoxy resins comprising (A) a polyamine compound which is a reaction product of a compound having at least one glycidyl group in a molecule with a diamine having a specific structure, (B) a polyether-modified polysiloxane having a surface tension in the range of 19 dyne/cm to 25 dyne/cm and (C) an amino group-modified polysiloxane having a total amine value in the range of 150 mgKOH/g to 650 mgKOH/g which can provide excellent curing performances, excellent performances of epoxy resin cured coating films and excellent physical properties of epoxy resin cured products, an epoxy resin composition comprising said curing agent composition for epoxy resins and an epoxy resin cured product obtained by curing said epoxy resin composition.

Claims

1. A curing agent composition for epoxy resins comprising the following components (A), (B) and (C):

(A) a polyamine compound which is a reaction product of a compound having at least one glycidyl group in a molecule with a diamine represented by the formula (I);

H₂N—

H₂C-A-CH₂—

NH₂ 

 

(1)

wherein A is a phenylene group or a cyclohexylene group

(B) a polyether-modified polysiloxane having a surface tension in the range of 19.0 dyne/cm to 25.0 dyne/cm

(C) an amino group-modified polysiloxane having a total amine value in the range of 150 mgKOH/g to 650 mgKOH/g.

2. The curing agent composition for epoxy resins according to claim 1, wherein said polyether-modified polysiloxane (B) has a surface tension in the range of 22.5 dyne/cm to 24.0 dyne/cm.

3. The curing agent composition for epoxy resins according to claim 1, wherein said amino group-modified polysiloxane (C) has a total amine value in the range of 300 mgKOH/g to 550 mgKOH/g.

4. The curing agent composition for epoxy resins according to claim 2, wherein said amino group-modified polysiloxane (C) has a total amine value in the range of 300 mgKOH/g to 550 mgKOH/g.

5. The curing agent composition for epoxy resins according to claim 1, wherein the content of said polyether-modified polysiloxane (B) is in the range of 0.025 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

6. The curing agent composition for epoxy resins according to claim 2, wherein the content of said polyether-modified polysiloxane (B) is in the range of 0.025 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

7. The curing agent composition for epoxy resins according to claim 3, wherein the content of said polyether-modified polysiloxane (B) is in the range of 0.025 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

8. The curing agent composition for epoxy resins according to claim 1, the content of said amino group-modified polysiloxane (C) is in the range of 0.05 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

9. The curing agent composition for epoxy resins according to claim 2, the content of said amino group-modified polysiloxane (C) is in the range of 0.05 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

10. The curing agent composition for epoxy resins according to claim 3, the content of said amino group-modified polysiloxane (C) is in the range of 0.05 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

11. The curing agent composition for epoxy resins according to claim 5, the content of said amino group-modified polysiloxane (C) is in the range of 0.05 to 4.0% by weight based upon the total amount of said components (A), (B) and (C).

12. An epoxy resin composition comprising at least the following components (A), (B) and (C):

(A) a polyamine compound which is a reaction product of a compound having at least one glycidyl group in a molecule with a diamine represented by the formula (I);

H₂N—

H₂C-A-CH₂—

NH₂ 

 

(1)

wherein A is a phenylene group or a cyclohexylene group

(B) a polyether-modified polysiloxane having a surface tension in the range of 19.0 dyne/cm to 25.0 dyne/cm

(C) an amino group-modified polysiloxane having a total amine value in the range of 150 mgKOH/g to 650 mgKOH/g.

13. The epoxy resin composition according to claim 12, wherein the content of said polyamine compound (A) is in the range of 0.7 to 1.2 in terms of a proportion of the number of active hydrogen atoms of said polyamine compound (A) to the number of epoxy groups of the epoxy resin.

14. The epoxy resin composition according to claim 12, wherein the content of said polyether-modified polysiloxane (B) is in the range of 0.005 to 1.5% by weight based upon the total amount of said epoxy resin composition.

15. The epoxy resin composition according to claim 13, wherein the content of said polyether-modified polysiloxane (B) is in the range of 0.005 to 1.5% by weight based upon the total amount of said epoxy resin composition.

16. The epoxy resin composition according to claim 12, wherein the content of said amino group-modified polysiloxane (C) is in the range of 0.01 to 1.5% by weight based upon the total amount of said epoxy resin composition.

17. The epoxy resin composition according to claim 13, wherein the content of said amino group-modified polysiloxane (C) is in the range of 0.01 to 1.5% by weight based upon the total amount of said epoxy resin composition.

18. The epoxy resin composition according to claim 14, wherein the content of said amino group-modified polysiloxane (C) is in the range of 0.01 to 1.5% by weight based upon the total amount of said epoxy resin composition.

19. An epoxy resin cured product obtained by curing the epoxy resin composition according to claim 12.

20. An epoxy resin cured product obtained by curing the epoxy resin composition according to claim 13.

21. An epoxy resin cured product obtained by curing the epoxy resin composition according to claim 14.

22. An epoxy resin cured product obtained by curing the epoxy resin composition according to claim 16.