Structural adhesive compositions

Patent metadata

Field	Value
Publication number	US-11242427-B2
Application number	US-201514887353-A
Country	US
Kind code	B2
Filing date	Oct 20, 2015
Priority date	Oct 20, 2015
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

An adhesive composition is disclosed. The adhesive composition comprises an epoxy-containing component; rubber particles having a core-shell structure; and a curing component comprising a mixture of an amine-containing compound substantially free of hydroxyl functional groups and a polymeric phenol-containing compound, wherein the amine-containing compound comprises primary and/or secondary amino groups, and wherein the curing component chemically reacts with the epoxy-containing component upon activation from an external energy source. Also disclosed are methods of preparing the adhesive composition and for forming a bonded substrate with the adhesive composition. Further disclosed are curing components for an adhesive composition and methods of making the curing components.

First claim

We claim:

1. A curing component comprising a mixture of an amine-containing compound having a structure of formula (I):

wherein each R 1 is independently H or a C 1 -C 18 alkyl group; R 2 is oxygen; each R 3 is independently absent or C 1 -C 4 divalent alkyl or divalent cycloaliphatic, wherein the amine-containing compound comprises primary and/or secondary amino groups and tertiary amines in an amount of less than 2% by weight based on total weight of the amine-containing compound and is substantially free of hydroxyl functional groups, and a polymeric phenol-containing compound; wherein the curing component is ground to a D97 of no more than 500 μm using an air classifying mill; and wherein the amine-containing compound is blocked by the polymeric phenol-containing compound in the absence of activation from an external energy source.

2. The curing component of claim 1 , wherein the amine-containing compound has an amine equivalent weight of at least 30.

3. The curing component of claim 1 , wherein the amine-containing compound further comprises dipropylenetriamine.

4. The curing component of claim 1 , wherein the polymeric phenol-containing compound has a phenol equivalent weight of at least 62.

5. The curing component of claim 1 , wherein the polymeric phenol-containing compound comprises a phenol formaldehyde resin.

6. The curing component of claim 1 , wherein the mixture is substantially free of solvent.

7. An adhesive composition comprising:
an epoxy-containing component;
rubber particles having a core-shell structure; and
the curing component of claim 1 .

8. The adhesive composition of claim 7 , wherein the epoxy-containing component is present in an amount of from 50% to 90% by weight based on total composition weight.

9. The adhesive composition of claim 7 , wherein the curing component is present in an amount of from 0.2% to 15% by weight based on total composition weight.

10. The adhesive composition of claim 7 , further comprising a secondary latent curing catalyst.

11. The adhesive composition of claim 7 , wherein the adhesive composition is substantially free of solvent.

12. The adhesive composition of claim 7 , wherein the polymeric phenol-containing compound blocks the amine-containing compound from reacting with the epoxy-containing component in the absence of activation from the external energy source.

13. A method for forming a bond between two substrates comprising:
applying the adhesive composition of claim 7 to a first substrate;
contacting a second substrate to the adhesive composition such that the adhesive composition is located between the first substrate and the second substrate; and
applying an external energy source to cure the adhesive composition.

14. The curing component of claim 1 , wherein the amine-containing compound and the polymeric phenol-containing compound are present in a molar ratio of from 1.5:1 to 1:3.

15. The method of claim 13 , wherein the external energy source comprises thermal heating to a temperature of at least 100° C.

16. A curing component comprising a mixture of an amine-containing compound comprising an alkyl polyetheramine and/or a cycloaliphatic polyetheramine, wherein the amine-containing compound comprises primary and/or secondary amino groups and tertiary amines in an amount of less than 2% by weight based on total weight of the amine-containing compound and is substantially free of hydroxyl functional groups, and a polymeric phenol-containing compound comprising a phenol-equivalent weight of at least 124; wherein the curing component is ground to a D97 of no more than 500 μm using an air classifying mill; and wherein the amine-containing compound is blocked by the polymeric phenol-containing compound in the absence of activation from an external energy source.

17. The curing component of claim 16 , wherein the amine-containing compound has an amine equivalent weight of at least 30.

18. The curing component of claim 16 , wherein the amine-containing compound further comprises dipropylenetriamine.

19. The curing component of claim 16 , wherein the polymeric phenol-containing compound comprises a phenol formaldehyde resin.

20. The curing component of claim 16 , wherein the mixture is substantially free of solvent.

21. An adhesive composition comprising:
an epoxy-containing component;
rubber particles having a core-shell structure; and
the curing component of claim 16 .

22. The adhesive composition of claim 21 , wherein the epoxy-containing component is present in an amount of from 50% to 90% by weight based on total composition weight.

23. The adhesive composition of claim 21 , wherein the curing component is present in an amount of from 0.2% to 15% by weight based on total composition weight.

24. A method for forming a bond between two substrates comprising:
applying the adhesive composition of claim 21 to a first substrate;
contacting a second substrate to the adhesive composition such that the adhesive composition is located between the first substrate and the second substrate; and
applying an external energy source to cure the adhesive composition.

25. A curing component comprising a mixture of an amine-containing compound having a structure of formula (I):

wherein each R 1 is independently H or a C 1 -C 18 alkyl group; R 2 is oxygen; each R 3 is independently absent or C 1 -C 4 divalent alkyl or divalent cycloaliphatic, wherein the amine-containing compound comprises primary and/or secondary amino groups and tertiary amines in an amount of less than 2% by weight based on total weight of the amine-containing compound and is substantially free of hydroxyl functional groups, and a polymeric phenol-containing compound; wherein the curing component is a powder having a D97 particle size of no more than 500 μm; and wherein the amine-containing compound is blocked by the polymeric phenol-containing compound in the absence of activation from an external energy source.

26. The curing component of claim 25 , wherein the amine-containing compound has an amine equivalent weight of at least 30 and/or the polymeric phenol-containing compound has a phenol equivalent weight of at least 62.

27. The curing component of claim 25 , wherein the amine-containing compound further comprises dipropylenetriamine and/or the polymeric phenol-containing compound comprises a phenol formaldehyde resin.

28. The curing component of claim 25 , wherein the amine-containing compound and the polymeric phenol-containing compound are present in a molar ratio of from 1.5:1 to 1:3.

29. An adhesive composition comprising:
an epoxy-containing component;
rubber particles having a core-shell structure; and
the curing component of claim 25 .

30. The adhesive composition of claim 29 , wherein the epoxy-containing component is present in an amount of from 50% to 90% by weight based on total composition weight and/or wherein the curing component is present in an amount of from 0.2% to 15% by weight based on total composition weight.

31. A method for forming a bond between two substrates comprising:
applying the adhesive composition of c

Assignees

• Ppg Ind Ohio Inc

Inventors

• Nakajima Masayuki
• Zhou Hongying
• Chao Tien-Chieh
• Swarup Shanti

Classifications

• C09J163/00

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

• C09J5/06

  involving heating of the applied adhesive · CPC title

• C08G59/5006 Primary

  aliphatic · CPC title

• C08L63/00

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

• C09J161/06

  of aldehydes with phenols · CPC title