COMPOSITIONS COMPRISING METATHESIZED UNSATURATED POLYOL ESTERS

• US 20090220443A1
• Filed: 03/07/2007
• Published: 09/03/2009
• Est. Priority Date: 03/07/2006
• Status: Active Grant

• Current Assignee: Wilmar Trading Pte., Ltd. (Wilmar International Limited)
• Original Assignee: Elevance Renewable Sciences Incorporated
• Inventors: Russell, Stephen E., Walters, Scott A., Murphy, Timothy A., Braksmayer, Diza Pearl, Tupy, Michael John
• Granted Patent: US 8,815,257 B2
• Time in Patent Office: Days
• US Class Current: 424/64
• CPC Class Codes: A23D 7/0053 Compositions other than spreads
• CPC Class Codes: A61K 8/06 Emulsions
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/922 of vegetable origin
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C07C 69/34 Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C07C 69/52 Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C07C 69/593 Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C08K 5/103 with polyalcohols
• CPC Class Codes: C09D 11/0235 Duplicating inks, e.g. for stencil printing
• CPC Class Codes: C09D 5/022 Emulsions, e.g. oil in water
• CPC Class Codes: C09D 5/086 Organic or non-macromolecular compounds
• CPC Class Codes: C09G 1/18 on other substances
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/02 by esterification of fatty acids with glycerol
• CPC Class Codes: C11C 3/126 using catalysts based principally on other metals or derivates
• CPC Class Codes: Y10S 516/923 Emulsion

Abstract

Disclosed are petrolatum-like compositions that comprise metathesized unsaturated polyol esters. Also disclosed are emulsions comprising metathesized unsaturated polyol esters. The petrolatum-like compositions may be used as substitutes for petroleum-based petrolatum. The emulsions may be water-in-oil or oil-in-water emulsions and may be suitable for a variety of end uses.

Claims

1. A composition of matter comprising:

a petrolatum-like composition comprising a metathesized unsaturated polyol ester.

2. The composition of claim 1, wherein the metathesized unsaturated polyol ester is hydrogenated.

5. The composition of claim 1, wherein the petrolatum-like composition further comprises a polyol ester.

6. The composition of claim 5, wherein the polyol ester comprises a natural oil selected from the group of vegetable oil, algae oil, or an animal fat.

9. The composition of claim 6, wherein the natural oil comprises a vegetable oil selected from the group of canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, castor oils, and mixtures thereof.

13. The composition of claim 2, wherein the hydrogenated metathesized unsaturated polyol ester comprises hydrogenated metathesized vegetable oil selected from the group of hydrogenated metathesized soybean oil, hydrogenated metathesized canola oil, hydrogenated metathesized rapeseed oil, hydrogenated metathesized coconut oil, hydrogenated metathesized corn oil, hydrogenated metathesized cottonseed oil, hydrogenated metathesized olive oil, hydrogenated metathesized palm oil, hydrogenated metathesized peanut oil, hydrogenated metathesized safflower oil, hydrogenated metathesized sesame oil, hydrogenated metathesized sunflower oil, linseed oil, palm kernel oil, tung oil, castor oil, or a mixture thereof.

17. The composition of claim 5, wherein the composition comprises about 50% wt. or less hydrogenated metathesized unsaturated polyol ester.

18. The composition of claim 5, wherein the composition comprises about 5% wt. to about 25% wt. hydrogenated metathesized unsaturated polyol ester.

19. The composition of claim 5, wherein the composition comprises about 5% wt. to about 25% wt. hydrogenated metathesized unsaturated polyol ester and about 75% wt. to about 95% wt. polyol ester.

20. The composition of claim 2, wherein the hydrogenated metathesized unsaturated polyol ester has an iodine value of about 120 or less.

21. The composition of claim 5, wherein composition comprises a hydrogenated metathesized unsaturated polyol ester having an iodine value of about 100 or less;

and the composition comprises a polyol ester having an iodine value of about 80 to 120.

22. The composition of claim 1, wherein the composition has a congealing point of about 100°

F. to about 140°

F. (37.8°

C. to 60.0°

C.).

23. The composition of claim 1, wherein the composition has a cone penetration @ 77°

F. (25°

C.) of about 100 dmm to about 300 dmm.

24. The composition of claim 1, wherein the composition has a drop melt point of about 100°

F. to about 150°

F. (37.8°

C. to 65.6°

C.).

25. The composition of claim 1, wherein the composition has a viscosity at 210°

F. of about 100 SUS or less.

26. The composition of claim 1, wherein the composition has an iodine value (IV) that ranges from about 5 to about 100.

27. The composition of claim 1, wherein the composition comprises one or more internal olefin compounds.

28. The composition of claim 1, wherein the composition is hydrogenated;

and wherein the composition comprises one or more saturated hydrocarbon compounds.

59. The composition of claim 27, wherein the composition comprises one or more internal olefin compounds.

60. The composition of claim 27, wherein the metathesized unsaturated polyol ester is hydrogenated;

and wherein the composition comprises one or more saturated hydrocarbon compounds.

61. A personal care item comprising the petrolatum-like composition of claim 1, wherein the item is a cosmetic, lip balm, lipstick, hand cleaner, hair dressing, ointment, sun care product, moisturizer, fragrance stick, perfume carrier, or pharmaceutical ointment.

3. (canceled)

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12. The composition of claim 10, wherein at least a portion of the soybean oil is partially hydrogenated.

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29. A composition comprising:

an emulsion comprising a metathesized unsaturated polyol ester.

30. The composition of claim 29, wherein the composition is selected from an oil-in-water emulsion and a water-in-oil emulsion.

32. The composition of claim 29, wherein the composition is an oil-in-water emulsion comprising:

(a) a dispersed phase comprising a metathesized unsaturated polyol ester;

(b) a continuous phase comprising water; and

(c) an emulsifier.

33. The composition of claim 32, wherein the dispersed phase comprises a hydrogenated metathesized unsaturated polyol ester.

34. The composition of claim 33, wherein the dispersed phase further comprises a polyol ester.

35. The composition of claim 34, wherein the polyol ester comprises a natural oil selected from vegetable oil, algae oil, and animal fat.

38. The composition of claim 35, wherein the natural oil comprises a vegetable oil selected from canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, castor oil, and mixtures thereof.

42. The composition of claim 33, wherein the hydrogenated metathesized unsaturated polyol ester comprises hydrogenated metathesized vegetable oil selected from the group of hydrogenated metathesized soybean oil, hydrogenated metathesized canola oil, hydrogenated metathesized rapeseed oil, hydrogenated metathesized coconut oil, hydrogenated metathesized corn oil, hydrogenated metathesized cottonseed oil, hydrogenated metathesized olive oil, hydrogenated metathesized palm oil, hydrogenated metathesized peanut oil, hydrogenated metathesized safflower oil, hydrogenated metathesized sesame oil, hydrogenated metathesized sunflower oil, linseed oil, palm kernel oil, tung oil, castor oil, or a mixture thereof.

46. The composition of claim 33, wherein the dispersed phase comprises about 50% wt. or less hydrogenated metathesized unsaturated polyol ester.

47. The composition of claim 33, wherein the dispersed phase comprises about 5% wt. to about 25% wt. hydrogenated metathesized unsaturated polyol ester.

48. The composition of claim 33, wherein the dispersed phase comprises about 5% wt. to about 25% wt. hydrogenated metathesized unsaturated polyol ester and about 75% wt. to about 95% wt. polyol ester.

49. The composition of claim 33, wherein the hydrogenated metathesized unsaturated polyol ester has an iodine value of about 100 or less.

50. The composition of claim 34, wherein the hydrogenated metathesized unsaturated polyol ester has an iodine value of about 100 or less and the polyol ester has an iodine value of about 80 to 120.

51. The composition of claim 32, wherein the emulsion has a viscosity ranging from about 20,000 cps to 80,000 cps.

52. The composition of claim 32, wherein the dispersed phase has a congealing point of about 100°

F. to about 140°

F. (37.8°

C. to 60.0°

C.).

53. The composition of claim 32, wherein the dispersed phase has a cone penetration @ 77°

F. (25°

C.) of about 100 dmm to about 300 dmm.

54. The composition of claim 32, wherein the dispersed phase has a drop melt point of about 100°

F. to about 150°

F. (37.80°

C. to 65.60°

C.).

55. The composition of claim 32, wherein the dispersed phase has a viscosity at 210°

F. of about 100 SUS or less.

56. The composition of claim 32, wherein the dispersed phase has an iodine value (IV) that ranges from about 5 to about 100.

57. The composition of claim 32, wherein the dispersed phase comprises about 1% wt. to about 60% wt. and the continuous phase comprises about 40% wt. to about 99% wt. of the composition.

58. The composition of claim 32, wherein the emulsifier is selected from the group consisting of nonionic emulsifiers, anionic emulsifiers, cationic emulsifiers, amphoteric emulsifiers, and mixtures thereof.

83. A personal care item comprising the emulsion of claim 29.

31. (canceled)

36. (canceled)

37. (canceled)

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40. (canceled)

41. The composition of claim 40, wherein at least a portion of the soybean oil is partially hydrogenated.

43. (canceled)

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