CROSSLINKABLE COMPOSITION, CROSSLINKED PRODUCT AND METHOD FOR PRODUCTION THEREOF, MULTILAYERED STRUCTURE, CROSSLINKING AGENT, AND COMPOUND AND METHOD FOR PRODUCTION THEREOF

• US 20130029070A1
• Filed: 03/10/2011
• Published: 01/31/2013
• Est. Priority Date: 03/11/2010
• Status: Active Grant

• Current Assignee: Kuraray Company Limited
• Original Assignee: Kuraray Company Limited
• Inventors: Ikeda, Kaoru, Kurosaki, Kazuhiro
• Granted Patent: US 8,617,678 B2
• Time in Patent Office: Days
• US Class Current: 428/35.7
• CPC Class Codes: C07C 233/38 having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• CPC Class Codes: C08F 261/04 on to polymers of vinyl alcohol
• CPC Class Codes: C09J 151/003 grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds C09J151/04, C09J151/06 take precedence
• CPC Class Codes: Y10T 428/1352 Polymer or resin containing [i.e., natural or synthetic]
• CPC Class Codes: Y10T 428/31725 Of polyamide
• CPC Class Codes: Y10T 428/31728 Next to second layer of polyamide

Abstract

Providing a crosslinkable composition and a crosslinking agent is objected to, which are capable forming a crosslinked product that is superior in retort resistance, with suppressed bleeding out from the crosslinked product, and that has favorable interlayer adhesiveness when formed into a multilayered structure crosslinked product. The present invention provides a crosslinkable composition containing (A) a polymer having an SP value of no less than 9.5 (cal/cm³)^1/2 and no greater than 16.5 (cal/cm³)^1/2, and (B) a crosslinking agent having one or more polar groups that include an oxygen atom and a nitrogen atom not constituting an aromatic ring, and two or more polymerizable groups. The difference between the SP value of the polymer (A) and the SP value of the crosslinking agent (B) is preferably no greater than 2 (cal/cm³)^1/2, and more preferably no greater than 1 (cal/cm³)^1/2. A decomposition temperature of the crosslinking agent (B) is preferably no less than 240° C., and a melting point of the crosslinking agent (B) is preferably no greater than 220° C.

Claims

1. A crosslinkable composition comprising:

(A) a polymer having an SP value of no less than 9.5 (cal/cm³)^1/2 and no greater than 16.5 (cal/cm³)^1/2; and

(B) a crosslinking agent having one or more polar groups and two or more polymerizable groups wherein the polar groups comprise an oxygen atom and a nitrogen atom that are not part of an aromatic ring.

2. The crosslinkable composition of claim 1, wherein a difference between the SP value of the polymer (A) and an SP value of the crosslinking agent (B) is no greater than 2 (cal/cm³)^1/2.

3. The crosslinkable composition of claim 2, wherein the difference between the SP value of the polymer (A) and the SP value of the crosslinking agent (B) is no greater than 1 (cal/cm³)^1/2.

4. The crosslinkable composition of claim 1, wherein a decomposition temperature of the crosslinking agent (B) is no less than 240°

C.

5. The crosslinkable composition of claim 1, wherein a melting point of the crosslinking agent (B) is no greater than 220°

C.

6. The crosslinkable composition of claim 1, wherein the polar group of the crosslinking agent (B) is an amide group, and the polymerizable groups are each independently an unsaturated hydrocarbon group having 2 to 12 carbon atoms.

7. The crosslinkable composition of claim 6, wherein the crosslinking agent (B) comprises 2 or 3 amide groups, and 2 or 3 unsaturated hydrocarbon groups having 2 to 12 carbon atoms.

8. The crosslinkable composition of claim 6, wherein the unsaturated hydrocarbon group is a vinyl group, or an alkenyl group or an alkadienyl group having 3 to 12 carbon atoms.

9. The crosslinkable composition of claim 1, wherein the crosslinking agent (B) is represented by formula (1):

10. The crosslinkable composition of claim 9, wherein R¹, R² and R³ each independently represent a vinyl group or an alkenyl group having 3 to 6 carbon atoms;

R⁴ and R⁵ represent a hydrogen atom;

X¹ and X² each independently represent an alkanediyl group having 1 to 3 carbon atoms; and

n is 0 or 1.

11. The crosslinkable composition of claim 1, wherein the polymer (A) is a polyvinyl alcohol type polymer.

12. The crosslinkable composition of claim 11, wherein the polyvinyl alcohol type polymer is an ethylene-vinyl alcohol copolymer.

13. The crosslinkable composition of claim 1, which is crosslinkable by an activated energy ray.

14. The crosslinkable composition of claim 13, wherein the activated energy ray is an electron beam.

15. A crosslinked product comprising, in reacted form, the crosslinkable composition of claim 1.

16. The crosslinked product of claim 15, which is in the form of a film.

17. A multilayered structure comprising layers comprising the crosslinked product of claim 15.

18. The multilayered structure of claim 17, which is a retort container.

19. A method for producing a crosslinked product, the method comprising irradiating the crosslinkable composition of claim 13 with an activated energy ray.

20. The method of claim 19, wherein the activated energy ray is an electron beam.

31. The crosslinkable composition of claim 9, wherein the polymer (A) is a polyvinyl alcohol type polymer.

32. The crosslinkable composition of claim 31, wherein the polyvinyl alcohol type polymer is an ethylene-vinyl alcohol copolymer.

21. A crosslinking agent represented by formula (2):

22. The crosslinking agent of claim 21, wherein R¹¹, R¹² and R¹³ each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms;

R¹⁴ and R¹⁵ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;

X¹¹ and X¹² each independently represent an alkanediyl group having 1 to 6 carbon atoms; and

m is an integer of 0 to 4.

23. The crosslinking agent of claim 21, wherein R¹¹, R¹² and R¹³ represent an alkyl group having 1 to 4 carbon atoms;

R¹⁴ and R¹⁵ represent a hydrogen atom;

X¹¹ and X¹² each independently represent an alkanediyl group having 1 to 3 carbon atoms; and

m is 0 or 1.

24. The crosslinking agent of claim 21, which has a decomposition temperature of no less than 240°

C.

25. The crosslinking agent of claim 21, which has a melting point of no greater than 220°

C.

26. The crosslinking agent of claim 21, which has an SP value of no less than 11.0 (cal/cm³)^1/2 and no greater than 14.5 (cal/cm³)^1/2.

27. A composition comprising a polyvinyl alcohol type polymer crosslinked by the crosslinking agent of claim 21.

28. The composition of claim 27, wherein the polyvinyl alcohol type polymer is an ethylene-vinyl alcohol copolymer.

29. A compound represented by formula (2′

);

30. A method for producing the compound of claim 29, the method comprising reacting an unsaturated carboxylic acid derivative with a compound having at least two amino groups.