Epoxidized esters of vegetable oil fatty acids as reactive diluents

• US 20060020062A1
• Filed: 07/08/2005
• Published: 01/26/2006
• Est. Priority Date: 07/08/2004
• Status: Abandoned Application

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: Bloom, Paul D.
• Application Number:
  US11/176,633
• Publication Number:
  US 20060020062A1
• Time in Patent Office: Days
• US Class Current: 524/114
• CPC Class Codes: C07D 303/42 Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
• CPC Class Codes: C07D 407/14 containing three or more hetero rings
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08K 5/15 Heterocyclic compounds having oxygen in the ring
• CPC Class Codes: C08K 5/1515 Three-membered rings
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C09D 133/06 of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical

Abstract

The present invention is directed to compositions containing epoxidized esters of vegetable oil fatty acids, and to methods of making such compositions. The esters are C_1-6 alkyl or C_2-6 alkenyl, monoglycerol or diglycerol, C_4-6 polyol or glycol esters of a vegetable oil fatty acid. The compositions include latex coating compositions comprising the epoxidized esters; epoxy resin compositions comprising the epoxidized esters; thermoset plastic compositions comprising the epoxidized esters; and PVC compositions comprising the epoxidized esters. The invention is also directed to epoxidized monoglycerides or diglycerides, and expoxidized C_4-6 polyol esters of vegetable oil fatty acids.

Claims

1. A coating composition comprising, a latex resin and a C_1-6 alkyl, C_2-6 alkenyl, epoxidized C_2-6 alkenyl, monoglycerol, diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid.

2. The coating composition of claim 1, wherein said ester is present in an amount between about 1 percent and about 70 percent by weight of said latex resin.

3. The coating composition of claim 2, wherein said ester is present in an amount between about 5 percent and about 40 percent by weight of said latex resin.

4. The coating composition of claim 3, wherein said ester is present in an amount between about 10 percent and about 20 percent by weight of said latex resin.

5. The coating composition of claim 1, wherein said ester is a glycol monoester.

6. The coating composition of claim 5, wherein said ester is a propylene glycol monoester, dipropylene glycol monoester, ethylene glycol monoester or diethylene glycol monoester.

7. The coating composition of claim 1, wherein said ester is a propylene glycol monoester.

8. The coating composition of claim 1, wherein said ester is a C_1-6 alkyl ester.

9. The coating composition of claim 1, wherein said ester is a methyl ester.

10. The coating composition of claim 1, wherein said ester is an allyl ester.

11. The coating composition of claim 1, wherein said ester is derived from an unsaturated vegetable oil fatty acid.

12. The coating composition of claim 11, wherein said unsaturated vegetable oil fatty acid is derived from an unsaturated vegetable oil selected from the group consisting of soybean oil, linseed oil, sunflower oil, castor oil, corn oil, canola oil, rapeseed oil, palm kernel oil, cottonseed oil, peanut oil, coconut oil, palm oil, tung oil, safflower oil and derivatives, conjugated derivatives, genetically-modified derivatives, and mixtures thereof.

13. The coating composition of claim 12, wherein said unsaturated vegetable oil is soy, sunflower corn or linseed oil.

14. The coating composition of claim 13, wherein said unsaturated vegetable oil is soy oil.

15. The coating composition of claim 1, wherein said glycol or C_4-6 polyol ester has the following structure:

16. A method of preparing the coating composition of claim 1 comprising, combining a latex resin and a C_1-6 alkyl, epoxidized C_2-6 alkenyl, C_2-6 alkenyl, monoglycerol or diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid, wherein a coating composition is prepared.

17. The method of claim 16, wherein said ester is a glycol monoester, C_1-6 alkyl ester, sorbitol ester, sorbitan ester, isosorbide ester, furfural alcohol ester or allyl ester.

18. The method of claim 16, wherein said ester is a propylene glycol monoester.

19. The method of claim 16, wherein said ester is derived from an unsaturated vegetable oil fatty acid.

20. The method of claim 16, wherein said ester is a propylene glycol monoester of an unsaturated vegetable oil fatty acid.

21. The method of claim 20, wherein said unsaturated vegetable oil fatty acid is derived from unsaturated soy oil.

22. An epoxy resin composition comprising an epoxy resin and a C_1-6 alkyl, C_2-6 alkenyl, epoxidized C_2-6 alkenyl, monoglycerol, diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid.

23. The epoxy resin composition of claim 22, wherein said ester is present in an amount between about 1 percent and about 70 percent by weight of said epoxy resin.

24. The epoxy resin composition of claim 23, wherein said ester is present in an amount between about 5 percent and about 40 percent by weight of said epoxy resin.

25. The epoxy resin composition of claim 24, wherein said ester is present in an amount between about 10 percent and about 20 percent by weight of said epoxy resin.

26. The epoxy resin composition of claim 22, wherein said ester is a glycol monoester.

27. The epoxy resin composition of claim 26, wherein said ester is a propylene glycol monoester, dipropylene glycol monoester, ethylene glycol monoester or diethylene glycol monoester.

28. The epoxy resin composition of claim 27, wherein said ester is a propylene glycol monoester.

29. The epoxy resin composition of claim 22, wherein said ester is a C_1-6 alkyl ester.

30. The epoxy resin composition of claim 22, wherein said ester is a methyl ester.

31. The epoxy resin composition of claim 22, wherein said ester is an allyl ester.

32. The epoxy resin composition of claim 22, wherein said glycol or C_4-6 polyol ester has the following structure:

33. The epoxy resin composition of claim 22, wherein said ester is derived from an unsaturated vegetable oil fatty acid.

34. The epoxy resin composition of claim 33, wherein said unsaturated vegetable oil fatty acid is derived from an unsaturated vegetable oil selected from the group consisting of soybean oil, linseed oil, sunflower oil, castor oil, corn oil, canola oil, rapeseed oil, palm kernel oil, cottonseed oil, peanut oil, coconut oil, palm oil, tung oil, safflower oil and derivatives, conjugated derivatives, genetically-modified derivatives, and mixtures thereof.

35. The epoxy resin composition of claim 34, wherein said unsaturated vegetable oil is soy or linseed oil.

36. The epoxy resin composition of claim 35, wherein said unsaturated vegetable oil is linseed oil.

37. The epoxy resin composition of claim 22, wherein said ester is a propylene glycol monoester derived from a fatty acid of linseed oil.

38. The epoxy resin composition of claim 22, wherein said ester is an allyl ester of oleic acid.

39. A method of preparing the epoxy resin composition of claim 22 comprising, combining an epoxy resin and a C_1-6 alkyl, C_2-6 alkenyl, epoxidized C_2-6 alkenyl, monoglycerol, diglycerol, C_4-6 polyol or glycol ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid, wherein an epoxy resin composition is prepared.

40. The method of claim 39, wherein said ester is an allyl or propylene glycol mono-ester of a vegetable oil fatty acid.

41. The method of claim 39, wherein said ester is an allyl ester of oleic acid.

42. The method of claim 39, wherein said ester is a propylene glycol monoester of a fatty acid derived from linseed oil.

43. A thermoset plastic composition comprising the epoxy resin composition of claim 22, and an amine.

44. The thermoset plastic composition of claim 43, wherein said amine is selected from the group consisting of aromatic amines, ethylene diamine, methylene dianiline diethylene triamine, polyamides, imidazoles and amine anhydrides.

45. The thermoset plastic composition of claim 43, wherein said amine is diethylene triamine.

46. A method of preparing a thermoset plastic comprising, combining the epoxy resin composition of claim 22, and an amine, wherein a thermoset plastic composition is prepared.

47. A polymer composition comprising polyvinylchloride and a C_2-6 alkenyl, epoxidized C_2-6 alkenyl, C_4-6 polyol, or glycol mono-ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid, and wherein said C_4-6 polyol ester has the following structure:

48. The polymer composition of claim 47, wherein said ester is present in an amount between about 1 percent and about 70 percent by weight of said polyvinylchloride.

49. The polymer composition of claim 47, wherein said ester is present in an amount between about 5 percent and about 40 percent by weight of said polyvinylchloride.

50. The polymer composition of claim 47, wherein said ester is present in an amount between about 10 percent and about 20 percent by weight of said polyvinyl chloride.

51. The polymer composition of claim 47, wherein said ester is a glycol monoester.

52. The polymer composition of claim 47, wherein said ester is a propylene glycol monoester, dipropylene glycol monoester, ethylene glycol monoester or diethylene glycol monoester.

53. The polymer composition of claim 47, wherein said ester is a propylene glycol monoester.

54. The polymer composition of claim 47, wherein said ester is an allyl ester.

55. The polymer composition of claim 47, wherein said ester is derived from an unsaturated vegetable oil fatty acid.

56. The polymer composition of claim 47, wherein said unsaturated vegetable oil fatty acid is derived from an unsaturated vegetable oil selected from the group consisting of soybean oil, linseed oil, sunflower oil, castor oil, corn oil, canola oil, rapeseed oil, palm kernel oil, cottonseed oil, peanut oil, coconut oil, palm oil, tung oil, safflower oil and derivatives, genetically-modified derivatives, and mixtures thereof.

57. The polymer composition of claim 47, wherein said unsaturated vegetable oil is soy, corn, sunflower or linseed oil.

58. The polymer composition of claim 57, wherein said unsaturated vegetable oil is soy oil.

59. The polymer composition of claim 47, wherein said ester is a propylene glycol monoester of a fatty acid derived from soy oil.

60. A method of preparing the polymer composition of claim 47 comprising combining polyvinylchloride and said ester of a vegetable oil fatty acid, wherein a polymer composition is prepared.

61. An ester of an epoxidized vegetable oil fatty acid comprising a C_2-6 alkenyl, epoxidized C_2-6 alkenyl or C_4-6 polyol ester of a vegetable oil fatty acid, wherein said ester has at least one oxirane ring formed between two adjacent carbons in the carbon chain of said fatty acid, and wherein said C_4-6 polyol ester has the following structure:

62. The ester of claim 61, wherein said C_4-6 polyol ester is derived from a monosaccharide.

63. The ester of claim 61, wherein said C_4-6 polyol ester is derived from sorbitol, sorbitan or isosorbide.

64. The ester of claim 61, wherein said C_4-6 polyol is derived from hydroxymethyl furfural.

65. The ester of claim 61, wherein said vegetable oil fatty acid is derived from soy, corn, sunflower or linseed oil.

66. The ester of claim 61, wherein

R in each instance is independently hydrogen, hydroxy(C_1-10)alkyl,

or amino(C_1-10)alkyl, and

R′

is hydrogen.

67. The ester of claim 61, wherein

m is an integer between about 2 and about 5, and

n is an integer between about 4 and about 7.

68. A method of lowering the glass transition temperature, T_g, of a composition comprising a polymer having a first T_g, said method comprising:

combining said composition comprising a polymer and the ester of claim 61, wherein said first T_g is lowered by not less than about 2°

C.