CLEAR POLYAMIDE RESINS, ARTICLES, AND METHODS

• US 20200131312A1
• Filed: 10/31/2019
• Published: 04/30/2020
• Est. Priority Date: 10/31/2018
• Status: Active Grant

• Current Assignee: Shakespeare Company LLC (Newell Brands Inc.)
• Original Assignee: Shakespeare Company LLC (Newell Brands Inc.)
• Inventors: Wu, Yuhong, Parks, Keith D., Jessee, Alfred O., Bhargava, Saumitra
• Granted Patent: US 11,807,719 B2
• Time in Patent Office: Days
• CPC Class Codes: B29C 45/14 incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles B29C45/1671 takes precedence
• CPC Class Codes: B29C 45/14811 Multilayered articles B29C45/14827 takes precedence
• CPC Class Codes: B29D 12/02 Spectacle frames constructional form G02C
• CPC Class Codes: B29K 2075/00 Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2077/00 Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2995/0018 having particular optical properties, e.g. fluorescent or phosphorescent
• CPC Class Codes: B32B 2274/00 Thermoplastic elastomer material
• CPC Class Codes: B32B 25/08 of synthetic resin
• CPC Class Codes: B32B 27/08 of synthetic resin
• CPC Class Codes: B32B 27/285 comprising polyethers
• CPC Class Codes: B32B 27/34 comprising polyamides
• CPC Class Codes: B32B 27/36 comprising polyesters
• CPC Class Codes: B32B 27/40 comprising polyurethanes
• CPC Class Codes: C08G 69/265 from at least two different diamines or at least two different dicarboxylic acids
• CPC Class Codes: C08G 69/28 Preparatory processes
• CPC Class Codes: C08L 2201/10 Transparent films; Clear coatings; Transparent materials
• CPC Class Codes: C08L 2203/20 use in electrical or conductive gadgets
• CPC Class Codes: C08L 2203/30 used for thermoforming
• CPC Class Codes: C08L 75/06 from polyesters
• CPC Class Codes: C08L 75/08 from polyethers
• CPC Class Codes: C08L 77/06 : Polyamides derived from polyamines and polycarboxylic acids C08L77/10 takes precedence

Abstract

Polyamide resins including the reaction product of an intimate mixture of at least two monomers selected from HMDA and a diamine; and an organic diacid, wherein sebacic acid is present in the organic diacid in an amount of less than or equal to about 50 mol. %, and associated articles and methods are provided herein.

Claims

1. A polyamide resin comprising the reaction product of an intimate mixture of:

at least two monomers selected from HMDA and a diamine; and

an organic diacid,

wherein sebacic acid is present in the organic diacid in an amount of less than or equal to about 50 mol. %.

2. The polyamide resin of claim 1, wherein the diamine is a cycloaliphatic diamine selected from BAC, DMDC, MACM, IPDA, or any combination thereof.

3. The polyamide resin of claim 1, wherein the diamine is MPMD.

4. The polyamide resin of claim 1, wherein the organic diacid is substantially free of sebacic acid.

5. The polyamide resin of claim 1, wherein the at least two monomers are HMDA and DMDC.

6. The polyamide resin of claim 5, wherein the HMDA is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. %.

7. The polyamide resin of claim 1, wherein the at least two monomers are a cycloaliphatic diamine and DMDC.

8. The polyamide resin of claim 7, wherein the cycloaliphatic diamine is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. %.

9. The polyamide resin of claim 1, wherein the at least two monomers are DMDC and MPMD.

10. The polyamide resin of claim 9, wherein the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the MPMD is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. %.

11. The polyamide resin of claim 1, wherein the organic diacid comprises one or more C10-C18 aliphatic dicarboxylic acids.

12. The polyamide resin of claim 1, wherein the organic diacid comprises dodecanedioic acid, isophthalic acid, or any combinations thereof.

13. The polyamide resin of claim 1, wherein the organic diacid comprises from about 50 mol. % to about 100 mol. % C10-C18 aliphatic dicarboxylic acid and from about 0 mol. % to about 50 mol. % isophthalic acid.

14. The polyamide resin of claim 13, wherein the aliphatic dicarboxylic acid comprises dodecanedioic acid.

15. The polyamide resin of claim 1, wherein the resin comprises C10 and greater aliphatic chains.

16. The polyamide resin of claim 1, wherein the polyamide resin has a glass transition temperature of at least about 110°

C.

17. The polyamide resin of claim 1, wherein the polyamide resin is clear.

18. The polyamide resin of claim 17, wherein a 3 mm thick sample of the resin has a total transmittance of at least about 80% when measured by a spectrophotometer according to ASTM D1003.

19. The polyamide resin of claim 1, further comprising:

a pigment, a dye, a heat stabilizer, a UV stabilizer, a lubricant, an antistatic agent, an optical brightener, or any combinations thereof.

20. The polyamide resin of claim 1, wherein the resin has a surface energy of about 38 dyne/cm.

21. An article comprising the resin of claim 1.

22. The article of claim 21, wherein the article is an eyewear lens, an eyewear frame, an electronic device, a wearable device, or a container.

23. The article of claim 21, wherein the article further comprises an overmold layer which comprises a thermoplastic urethane (TPU) resin or a thermoplastic elastomer (TPE) resin.

24. The article of claim 23, wherein the TPU resin comprises a polyether, polyester, aliphatic TPU resin.

25. The article of claim 23, wherein the TPU resin comprises a polyether, polyester, or aliphatic polyol.

26. The article of claim 23, wherein the polyamide resin comprises an organic aliphatic diacid content in an amount of at least about 2 percent, by weight.

27. A method of making an article comprising:

injection molding, extruding, or continuously molding the resin of claim 1.

28. The method of claim 27, wherein the method comprises continuously molding the resin without the use of a mold-release spray.

29. The method of claim 27, wherein the method further comprises:

overmolding a thermoplastic urethane (TPU) resin or a thermoplastic elastomer (TPE) resin.

30. A method of making a polyamide resin comprising:

combining at least two monomers selected from HMDA, BAC, and DMDC and an organic diacid in a reaction vessel under pressure to form a polyamide resin,

wherein sebacic acid is present in the organic diacid in an amount of less than or equal to about 50 mol. %.

31. The method of claim 30, wherein the at least two monomers are HMDA and DMDC.

32. The method of claim 31, wherein the HMDA is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % of the at least two monomers.

33. The method of claim 30, wherein the at least two monomers are a cycloaliphatic diamine and DMDC.

34. The method of claim 33, wherein the cycloaliphatic diamine is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. %.

35. The method of claim 33, wherein the cycloaliphatic diamine is BAC.

36. The method of claim 33, wherein the cycloaliphatic diamine is IPDA.

37. The method of claim 30, wherein the at least two monomers are DMDC and MPMD.

38. The method of claim 37, wherein the DMDC is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. % and the MPMD is present in the at least two monomers in an amount of from about 25 mol. % to about 75 mol. %.

39. The method of claim 30, wherein the organic diacid comprises one or more C10-C18 aliphatic dicarboxylic acids.

40. The method of claim 30, wherein the organic diacid comprises dodecanedioic acid, isophthalic acid, or any combinations thereof.

41. The method of claim 30, wherein the organic diacid comprises from about 50 mol. % to about 100 mol. % C10-C18 aliphatic dicarboxylic acid and from about 0 mol. % to about 50 mol. % isophthalic acid.

42. The method of claim 41, wherein the aliphatic dicarboxylic acid comprises dodecanedioic acid.

43. The method of claim 30, wherein the resin comprises C10 and greater aliphatic chains.

44. The method of claim 30, wherein the polyamide resin has a glass transition temperature of at least about 110°

C.

45. The method of claim 30, wherein the polyamide resin is clear.

46. The method of claim 45, wherein a 3 mm thick sample of the resin has a total transmittance of at least about 80% when measured by a spectrophotometer according to ASTM D1003.

47. The method of claim 30, further comprising:

a pigment, a dye, a heat stabilizer, a UV stabilizer, a lubricant, an antistatic agent, an optical brightener, or any combinations thereof.

48. The method of claim 30, wherein the resin has a surface energy of about 38 dyne/cm.