EP-4734913-A1 - POLYGLYCEROL PARTIAL ESTER COMPRISING OLEIC ACID

Abstract

The invention relates to a polyglycerol partial ester obtainable by esterification of a) a polyglycerol mixture, b) at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and c) oleic acid, characterized in that oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.-%, more preferably at least 68 wt.-% of all monocarboxylic acids esterified into the polyglycerol partial ester.

Inventors

• VON HOF, JAN MARIAN
• TANTO, Tim
• BECKERS, Sebastian Johannes
• FRIEDRICH, ACHIM
• MEYER, JUERGEN
• ZIMMERMANN, SEBASTIAN

Assignees

• Evonik Operations GmbH

Dates

Publication Date

20260506

Application Date

20240627

Claims (15)

1. 1. Polyglycerol partial ester obtainable by esterification of a) a polyglycerol mixture, b) at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and c) oleic acid, characterized in that oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.-%, more preferably at least 68 wt.-% of all monocarboxylic acids esterified into the polyglycerol partial ester.
2. 2. Polyglycerol partial ester according to Claim 1 , characterized in that the polyglycerol esterified into the polyglycerol partial ester has a glycerin content of 0.05% by weight to 25.0% by weight, preferably of 0.1% by weight to 15.0% by weight, more preferably of 0.1% by weight to 10.0% by weight.
3. 3. Polyglycerol partial ester according to Claim 1 or 2, characterized in that the polyglycerol esterified into the polyglycerol partial ester has an average degree of condensation N of 2.4 to 6.0, preferably 2.6 to 4.5, especially 2.8 to 3.4.
4. 4. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that the polyglycerol esterified into the polyglycerol partial ester has a content of cyclic isomers of 1% by weight to 50% by weight, preferably of 2% by weight to 40% by weight, more preferably of 3% by weight to 30% by weight.
5. 5. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that the long-chain dicarboxylic acid is selected from those obtainable from the dimerization of oleic acid and/or linoleic acid.
6. 6. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that the dicarboxylic acid is provided in the form of a dimer acid with a functionality not exceeding, on molar average, a value of 2.4.
7. 7. Polyglycerol partial ester according to at least one of the preceding claims, in that the molar ratio of the oleic acid esterified into the polyglycerol partial ester and the at least one dicarboxylic acid esterified into the polyglycerol partial ester is in the range of 2.8 : 1.0 to 5.0 : 1.0, preferably 3.0 : 1.0 to 4.8 : 1.0, more preferably 3.2 : 1.0 to 4.5 : 1.0.
8. 8. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that it has a HLB value of from 2.0 to 7.0, preferably from 3.0 to 6.0 and more preferably from 4.0 to 5.0.
9. 9. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that it has an iodine value of 35.0 g 1/100 g to 70.0 g 1/100 g, preferably 40.0 g 1/100 g to 65.0 g 1/100 g, more preferably of 45.0 g 1/100 g to 60.0 g 1/100 g
10. 10. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that it a degree of esterification of 35% to 95%, preferably of 40% to 85%, more preferably of 45% to 75%, more preferably of 50% to 65%.
11. 11. Polyglycerol partial ester according to at least one of the preceding claims, characterized in that it has a viscosity at 25 °C of 1000 to 25000 mPas, preferably 5000 to 20000 mPas, more preferably 7500 to 15000 mPas.
12. 12. Method for preparing a polyglycerol partial ester, comprising the method steps of A) providing a polyglycerol, preferably having an average degree of condensation N of 2.4 to 6.0, preferably 2.6 to 4.5, especially 2.8 to 3.4, B) providing a carboxylic acid mixture comprising: at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and oleic acid, C) esterifying the polyglycerol with the carboxylic acid mixture, characterized in that said oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.- %, more preferably at least 68 wt.-% of all monocarboxylic acids present in said carboxylic acid mixture.
13. 13. Formulation, especially a cosmetic formulation, comprising 1) polyglycerol partial esters according to at least one of Claims 1 to 11 or obtainable according to the method of Claim 12, and optionally 2) at least one antioxidant.
14. 14. Formulation according to Claim 13, characterized in that component 2) is selected from the group of vitamin E, preferably in the form of a-tocopherol, p-tocopherol, y-tocopherol, 5-tocopherol and a-tocotrienol, p-tocotrienol, y-tocotrienol and/or 5-tocotrienol.
15. 15. Use of a polyglycerol partial ester according to at least one of Claims 1 to 11 or obtainable according to the method of Claim 12 as ingredient, especially as emulsifier and/or lubricity additive, in metalworking fluids.

Description

Polyglycerol partial ester comprising oleic acid Field of the invention The invention relates to a polyglycerol partial ester obtainable by esterification of a) a polyglycerol mixture, b) at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and c) oleic acid, characterized in that oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.-%, more preferably at least 68 wt.-% of all monocarboxylic acids esterified into the polyglycerol partial ester. Prior art EP0835862 discloses a polyglycerol partial ester of a saturated or unsaturated, linear or branched fatty acid and a polyfunctional carboxylic acid, obtainable by esterification of a polyglycerol mixture with saturated or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and dimer fatty acids obtained by catalytic dimerization of unsaturated fatty acids having 12 to 22 carbon atoms and have a mean functionality of from 2 to 2.4, the degree of esterification of the polyglycerol mixture being between 30 and 75%. It is an objective of the invention to improve the skin sensation of formulations even further. Description of the invention It was found that, surprisingly, that polyglycerol partial esters as described in claim 1 solve the problem underlying the instant invention. The present invention therefore provides a polyglycerol partial ester obtainable by esterification of a) a polyglycerol mixture, b) at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and c) oleic acid, characterized in that oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.-%, more preferably at least 68 wt.-% of all monocarboxylic acids esterified into the polyglycerol partial ester. The invention further provides a method for preparing a polyglycerol partial ester, comprising the method steps of A) providing a polyglycerol, preferably having an average degree of condensation N of 2.4 to 6.0, preferably 2.6 to 4.5, especially 2.8 to 3.4, B) providing a carboxylic acid mixture comprising: at least one dicarboxylic acid having 24 to 44, preferably 30 to 40, particularly preferably 34 to 38, carbon atoms, and oleic acid, C) esterifying the polyglycerol with the carboxylic acid mixture, characterized in that said oleic acid makes up for at least 50 wt.-%, preferably at least 60 wt.-%, more preferably at least 68 wt.-% of all monocarboxylic acids present in said carboxylic acid mixture. An advantage of the present invention is that the polyglycerol partial esters described herein may be prepared from exclusively renewable raw materials. A further advantage is that the polyglycerol partial esters described herein can be prepared on the basis of principles of green chemistry. Another advantage of the present invention is that formulations can be provided that are polyglycol ether-free. A further advantage is that the polyglycerol partial esters described herein are biodegradable. A further advantage is that the polyglycerol partial esters described herein have a good ecotoxicological profile. A further advantage of the polyglycerol partial esters described herein is that they are very mild on the skin, not irritating and non-toxic. Another advantage of the polyglycerol partial esters described herein is that they have improved sensory properties in formulations. The tackiness of sun protection formulations is reduced after application. The formulations undergo more rapid absorption into the skin since absorption is increased during application and for 5 min thereafter on the skin. Another advantage of the polyglycerol partial esters described herein is that they give rise to enhancement of “velvety-silkiness” in formulations. A further advantage is that the polyglycerol partial esters described herein have a good skinmoisturizing effect. Another advantage is that the polyglycerol partial esters described herein are very well suited to be used in sun protection formulations having very high concentrations of UV light protection filters. A further advantage of the polyglycerol partial esters described herein is that they impart very high water resistance to the formulations. In sun protection formulations this results in the formulations ensuring prolonged UV protection in the water or after bathing. Another advantage of the polyglycerol partial esters according to the invention is that they impart increased wear resistance to the colour pigments when used in make-up applications. In the context of pigment-containing formulations, a further advantage of the polyglycerol partial esters according to the invention is that they permit good dispersion of pigments in the formulations. A further advantage of the polyglycerol partial esters described herein is that they have good compatibility with formulations containing UV protection filters or pigments. In general, the polyglycerol partial esters described herein i