Branched polymeric emulsifiers

Patent metadata

Field	Value
Publication number	US-9593204-B2
Application number	US-201314423151-A
Country	US
Kind code	B2
Filing date	Aug 8, 2013
Priority date	Aug 23, 2012
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The present invention relates to esterified glycerylated alkyl glycoside and to a process for making same. The esterified glycerylated alkyl glycoside have one or more polyglyceryl moieties and one or more acyl moieties, wherein all of the one or more acyl moieties are situated on the one or more polyglyceryl moieties via an ester linkage. These compounds have been found to be useful as emulsifiers and coemulsifiers in the formulation of a phase stable emulsions suitable for use in personal care, home care, industrial and institutional, and health care applications.

First claim

What is claimed is:

1. An esterified branched polyglyceryl ether of an alkyl glucoside having one or more polyglyceryl moieties and one or more acyl moieties, wherein all of said one or more acyl moieties are situated on said one or more polyglyceryl moieties via an ester linkage, wherein said alkyl glucoside is represented by the formula:

wherein R represents an alkyl group containing 1 to 22 carbon atoms; GLY is a substituted or unsubstituted glyceryl or polyglyceryl residue represented by the formulae:

and combinations thereof, wherein R 1 can be the same or different and is selected from hydrogen, an acyl group containing 8 to 54 carbon atoms, and GLY, wherein GLY is as defined above, the sum of v+w+x+y is an integer ranging from about 20 to about 150, subject to the proviso that a portion of R 1 represents said acyl group, and wherein the average degree of glyceryl substitution (DS g ) on the alkyl glucoside is about 4.

2. The esterified polyglyceryl alkyl glucoside of claim 1 wherein GLY contains a terminal glyceryl moiety represented by the formulae:

wherein R 1 is selected from hydrogen, an acyl group containing 8 to 54 carbon atoms, and combinations thereof, and wherein at least one of R 1 is said acyl group.

3. The esterified polyglyceryl alkyl glucoside of claim 1 wherein the total degree of acyl substitution (DS a ) ranges from about 1 to about 4.

4. The esterified polyglyceryl alkyl glucoside of claim 1 wherein the total degree of acyl substitution (DS a ) ranges from about 1 to about 3.

5. The esterified polyglyceryl alkyl glucoside of claim 1 wherein the total degree of acyl substitution (DS a ) is about 2.

6. The esterified polyglyceryl alkyl glucoside of claim 1 wherein the total degree of acyl substitution (DS a ) is about 1.

7. The esterified polyglyceryl alkyl glucoside of claim 1 wherein said acyl group contains unsaturation.

8. The esterified polyglyceryl alkyl glucoside of claim 1 wherein said acyl group is a residue of a fatty acid selected from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, vaccenic acid, linoleic acid, alpha-linolenic acid, gamma-linolenic acid, eicosanoic acid, 9-eicosenoic acid, 5,8,11,14-eicosatetraenoic acid, 5,8,11,14,17-eicosapentaenoic acid, behenic acid, erucic acid, 4,7,10,13,16,19-docosahexaenoic acid, lignoceric acid, triricinoleic acid, or combinations thereof.

9. The esterified polyglyceryl alkyl glucoside of claim 1 wherein said acyl group is a residue of oleic acid.

10. The esterified polyglyceryl alkyl glucoside of claim 1 wherein the sum of v+w+x+y is an integer ranging from about 40 to about 140.

11. The esterified polyglyceryl alkyl glucoside of claim 10 wherein the sum of v+w+x+y is an integer ranging from about 60 to about 120.

12. The esterified polyglyceryl alkyl glucoside of claim 11 wherein the sum of v+w+x+y ranges from about 65 to about 75.

13. An esterified branched polyglyceryl ether of an alkyl glucoside prepared by a process of:
(A) reacting an alkyl glucoside of the formula:

wherein R represents an alkyl group containing 1 to 10 carbon atoms with glycidol or glycerin carbonate to obtain a branched polyglyceryl alkyl glucoside of the formula:

wherein R is as defined as above; GLY is the same or different and is selected from hydrogen and a glyceryl or polyglyceryl residue represented by the formula:

wherein the sum of v+w+x+y is an integer ranging from about 20 to about 150 and the total degree of glyceryl substitution (DS g ) is about 4; and
(B) reacting the branched polyglyceryl alkyl glucoside obtained in step (A) with an acylating agent to obtain an acyl substituted polyglyceryl alkyl glucoside wherein a portion of the hydroxyl groups on said polyglyceryl alkyl glucoside are acylated.

14. The method of claim 13 wherein the total degree of acyl substitution (DS a ) on the glyceryl moieties ranges from about 1 to about 4.

15. The method of claim 14 wherein the total degree of acyl substitution (DS a ) on the glyceryl moieties ranges from about 1 to about 3.

16. The method of claim 15 wherein the total degree of acyl substitution (DS a ) on the glyceryl moieties ranges from about 1 to about 2.

17. The method of claim 13 wherein said acylating agent is selected from a fatty acid containing 8 to 54 carbon atoms.

18. The method of claim 17 wherein said acylating agent contains unsaturation.

19. The method of claim 17 wherein said acylating agent is selected from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, vaccenic acid, linoleic acid, alpha-linolenic acid, gamma-linolenic acid, eicosanoic acid, 9-eicosenoic acid, 5,8,11,14-eicosatetraenoic acid, 5,8,11,14,17-eicosapentaenoic acid, behenic acid, erucic acid, 4,7,10,13,16,19-docosahexaenoic acid, lignoceric acid, and combinations thereof.

20. The method of claim 18 wherein said acylating agent is oleic acid.

21. The method of claim 13 wherein the sum of v+w+x+y ranges from about 40 to about 140.

22. The method of claim 21 wherein the sum of v+w+x+y ranges from about 60 to about 120.

23. The method of claim 22 wherein the sum of v+w+x+y ranges from about 65 to about 100.

24. An O/W emulsion composition comprising:
(i) an effective stabilizing amount of a polyglyceryl alkyl glucoside of claim 1 ;
(ii) an oily phase;
(iii) an aqueous phase; and optionally
(iv) a coemulsifier.

25. The O/W emulsion of claim 24 wherein said oily phase component is selected from vegetable oils, animal oils, hydrocarbon oils, fatty alcohols, fatty acid esters, silicone oils, oily UV absorbers and sunscreens, fragrance oils, and mixtures thereof.

26. The O/W emulsion of claim 24 wherein said co-emulsifier is selected from low HLB emulsifier ranging from about 1 to about 7.

27. The O/W emulsion of claim 24 wherein said co-emulsifier is selected from sorbitan esters, glyceryl esters, polyglyceryl esters, glycol esters, sucrose esters, methyl glucose esters, ethoxylated methyl glucose esters, or mixtures thereof.

28. The O/W emulsion of claim 24 wherein said co-emulsifier is selected from sorbitan laurate, sorbitan palmitate, sorbitan sesquiisostearate, sorbitan sesquioleate, sorbitan sesquistearate, sorbitan stearate, sorbitan oleate, sorbitan monoisostearate, sorbitan trisostearate, sorbitan trioleate, sorbitan tristearate; glyceryl behenate, glyceryl caprate, glyceryl caprylate, glyceryl caprylate/caprate, glyceryl cocoate, glyceryl erucate, glyceryl hydroxystearate, glyceryl isostearate, glyceryl lanolate, glyceryl laurate, glyceryl linoleate, glyceryl myristate, glyceryl oleate, glyceryl palmitate lactate, glyceryl sesquioleate, glyceryl stearate

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Wu Anchuu
• Barr Douglas M
• Marchant Nancy S
• Sengupta Ashoke K
• Hsu Feng-Lung Gorden

Classifications

• A61K8/92

  Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof · CPC title

• C08G2650/54

  Polyglycerols · CPC title

• A61K8/608

  Derivatives containing from 2 to 10 oxyalkylene groups · CPC title

• C08G2650/26

  Sugars or saccharides used as initiators · CPC title

• C08G65/3322 Primary

  acyclic · CPC title