Cross-linked polyglycerol esters

Patent metadata

Field	Value
Publication number	US-11807603-B2
Application number	US-201716322566-A
Country	US
Kind code	B2
Filing date	May 15, 2017
Priority date	Aug 18, 2016
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

The invention relates to a polyglycerol partial ester obtainable by esterification of a polyglycerol with a carboxylic acid mixture comprising at least one polyhydroxycarboxylic acid of a hydroxycarboxylic acid having 8 to 32 carbon atoms, at least one short-chain dicarboxylic acid having 2 to 16, preferably 6 to 14, particularly preferably 8 to 12, carbon atoms, at least one long-chain dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and at least one fatty acid selected from linear, unsaturated and branched, saturated fatty acids having 14 to 24 carbon atoms, to a method for preparing polyglycerol partial esters, and to the use of corresponding polyglycerol partial esters as W/O emulsifier.

First claim

The invention claimed is:

1. A quick-break emulsion comprising
a polyglycerol partial ester obtained by esterification of a polyglycerol with a carboxylic acid mixture comprising:
a) a polyhydroxycarboxylic acid of a hydroxycarboxylic acid having from 14 to 18 carbon atoms,
b) at least one short-chain dicarboxylic acid having from 2 to 16 carbon atoms,
c) at least one long-chain dicarboxylic acid having from 34 to 38 carbon atoms, and
d) at least one fatty acid selected from linear, unsaturated and branched, saturated fatty acids having from 14 to 24 carbon atoms;
wherein the polyglycerol comprises
i. from 0 to 15% by weight of glycerol,
ii. from 10 to 40% by weight of diglycerol,
iii. from 10 to 50% by weight of triglycerol,
iv. from 5 to 25% by weight of tetraglycerol, and
v. from 0 to 55% by weight of pentaglycerol and higher glycerols;

wherein the polyglycerol has a hydroxyl number of from 1520 to 845 and wherein the carboxylic acid mixture of a), b), c) and d) make up at least 80% by weight based on the total carboxylic acid mixture; and

wherein, in the esterification, the molar ratio of b) to c) is from 0.5:1.0 to 1.0:0.5, and wherein the quick-break emulsion contains an internal aqueous phase of from 83% by weight to 94.5% by weight and an external oil phase in an amount of from 5% by weight to 17% by weight, and from 0.5% by weight to 2.0% by weight of the polyglycerol partial ester, wherein the % by weight is based on the total emulsion.

2. The quick-break emulsion according to claim 1 , wherein the polyglycerol has an average degree of condensation of from 1.5 to 8, and wherein the polyglycerol has a hydroxyl number of from 1350 to 970, and wherein the carboxylic acid mixture of a), b), c) and d) make up at least 90% by weight based on the total carboxylic acid mixture.

3. The quick-break emulsion according to claim 1 , wherein the polyhydroxycarboxylic acid is selected from the group consisting of polyhydroxystearic acid and polyricinoleic acid, and wherein the carboxylic acid mixture of a), b), c) and d) make up at least 95% by weight based on the total carboxylic acid mixture.

4. The quick-break emulsion according to claim 1 , wherein the polyhydroxycarboxylic acid has an average degree of condensation of from 1.5 to 9, and wherein the polyglycerol has a hydroxyl number of from 1170 to 1010.

5. The quick-break emulsion according to claim 1 , wherein the short-chain dicarboxylic acid is selected from the group consisting of aliphatic, linear dicarboxylic acids, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecanedioic acid.

6. The quick-break emulsion according to claim 1 , wherein the long-chain dicarboxylic acid is selected from the long-chain dicarboxylic acid obtainable from the dimerization of oleic acid and/or linoleic acid.

7. The quick-break emulsion according to claim 1 , wherein the at least one fatty acid selected from linear, unsaturated and branched, saturated fatty acid is selected from the group consisting of isostearic acid, undecylenic acid, myristoleic acid, palmitoleic acid, petroselinic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, icosenoic acid, cetoleic acid, erucic acid, nervonic acid, linoleic acid, alpha-linolenic acid, gamma-linolenic acid, calendulic acid, punicic acid, alpha-elaeostearic acid, beta-elaeostearic acid, arachidonic acid, timnodonic acid, clupanodonic acid, and cervonic acid.

8. The quick-break emulsion according to claim 1 , wherein the degree of esterification is from 35 to 95% of all OH groups present in the polyglycerol partial ester, including the ones present in the polyhydroxycarboxylic acid.

9. The quick-break emulsion according to claim 1 , wherein, in the esterification,
from 0.1 to 2 mol of a),
from 0.1 to 2 mol of b),
from 0.1 to 2 mol of c), and
from 0.5 to 4 mol of d)
are used per mole of polyglycerol.

10. The quick-break emulsion according to claim 1 , wherein, in the esterification, the molar ratio of b) to c) is from 0.7:1.0 to 1.0:0.7.

11. A method for preparing a quick-break emulsion with a polyglycerol partial ester, comprising the esterification of a polyglycerol with a carboxylic acid mixture comprising:
a) a polyhydroxycarboxylic acid of a hydroxycarboxylic acid having from 14 to 18 carbon atoms,
b) a short-chain dicarboxylic acid having from 2 to 16 carbon atoms,
c) a long-chain dicarboxylic acid having from 34 to 38 carbon atoms, and
d) a fatty acid selected from linear, unsaturated and branched, saturated fatty acids having from 14 to 24 carbon atoms;
wherein the polyglycerol comprises
i. from 0 to 15% by weight of glycerol,
ii. from 10 to 40% by weight of diglycerol,
iii. from 10 to 50% by weight of triglycerol,
iv. from 5 to 25% by weight of tetraglycerol, and
v. from 0 to 55% by weight of pentaglycerol and higher glycerols;
wherein the polyglycerol has a hydroxyl number of from 1520 to 845 and wherein the carboxylic acid mixture of a), b), c) and d) make up at least 80% by weight based on the total carboxylic acid mixture, and
wherein, in the esterification, the molar ratio of b) to c) is from 0.5:1.0 to 1.0:0.5, and further comprising homogenizing an aqueous phase, an oil phase and said polyglycerol partial ester to form the quick-break emulsion, wherein the quick-break emulsion comprises the polyglycerol partial ester, and the quick-break emulsion contains an internal aqueous phase of from 83% by weight to 94.5% by weight and an external oil phase in an amount of from 5% by weight to 17% by weight, and from 0.5% by weight to 2.0% by weight of the polyglycerol partial ester, wherein the % by weight are based on the total emulsion.

12. A cosmetic or pharmaceutical preparation comprising from 0.5% by weight to 20% by weight of the quick-break emulsion according to claim 1 .

13. The cosmetic or pharmaceutical preparation according to claim 12 , wherein the quick-break emulsions comprises
an internal aqueous phase in an amount from 83% by weight to 92% by weight,
an external oil phase in an amount from 8% by weight to 17% by weight, and
the polyglycerol partial ester in an amount from 0.5% by weight to 2.0% by weight.

14. A pharmaceutical preparation comprising the quick-break emulsion according to claim 1 .

15. The quick-break emulsion according to claim 1 , wherein the quick-break emulsion contains an internal aqueous phase of from 83% by weight to 92% by weight and an external oil phase in an amount of from 8% by weight to 17% by weight, and wherein the amount of polyglycerol partial ester is from 0.5% by weight to 1.5% by weight wherein the % by weight are based on the total emulsion.

16. The quick-break emulsion according to claim 1 , wherein the carboxylic acid mixture consists of:
a) the polyhydroxycarboxylic acid of a hydroxycarboxylic acid having from 14 to 18 carbon atoms,
b) at least one short-chain dicarboxylic acid having from 8 to 12 carbon atoms,
c) at least one long-chain dicarboxylic acid having from 34 to 38 carbon atoms, and
d) at least one fatty acid selected from linear, unsaturated and branched, saturated fatty acids having from 16 to 20 carbon atoms, and wherein the polyglycerol has an average degree of condensation of from 3 to 5.

17. The quick-break emulsion according to claim 1 , wherein the polyhydroxycarboxylic acid has an average degree of condensation of 3 to 5.

18. The quick-break emulsion according to claim 1 , wherein the short-chain dicarboxylic acid is sebacic acid.

19. T

Assignees

• Evonik Operations Gmbh

Inventors

• Von Hof Jan Marian
• Friedrich Achim
• Berkels Wolfgang
• Hohenberg Barbara
• Springer Oliver
• Meyer Juergen

Classifications

• C07C69/675 Primary

  of saturated hydroxy-carboxylic acids · CPC title

• A61K8/064

  Water-in-oil emulsions, e.g. Water-in-silicone emulsions · CPC title

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• A61K8/39

  Derivatives containing from 2 to 10 oxyalkylene groups · CPC title

• A61K47/14

  Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters · CPC title