USE OF HIGHLY-BRANCHED POLYESTERS IN COSMETIC AND DERMATOLOGICAL FORMULATIONS

Abstract

The present invention relates to compositions which comprise highly branched polyesters, to the use of these highly branched polyesters in cosmetics and dermatology and to substituted highly branched polyesters.

Claims

1.-8. (canceled)

9. A method for thickening a cosmetic or dermatologic formulation, the method comprising: providing a functionalized, highly branched polyester having linear or branched C.sub.4-C.sub.40 alkyl radicals or C.sub.4-C.sub.40 alkenyl radicals, wherein the functionalized, highly branched polyester is a reaction product of at least one aliphatic, cycloaliphatic, araliphatic, or aromatic dicarboxylic acid (A.sub.2), optionally, a dihydric, aliphatic, cycloaliphatic, araliphatic, or aromatic alcohol (B.sub.2), having two OH groups, and at least one x-hydric aliphatic, cycloaliphatic, araliphatic, or aromatic alcohol (C.sub.x), having x OH groups, wherein x is an integer 3 to 6, to provide a highly branched polyester, and reacting the highly branched polyester with a monoisocyanate functionalization reagent, the reaction conducted with a molar ratio of functionalization reagent to reactive groups of the highly branched polyester is from 1:5 to 1:1.1; providing an oil component selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, butylene glycol dicaprylate/dicaprate, 2-ethylhexyl cocoate, C.sub.12-15-alkyl benzoate, caprylic-capric triglyceride, dicaprylyl ether, any one mixture of octyldodecanol, caprylic-capric triglyceride, dicaprylyl ether, dicaprylyl carbonate, cocoglycerides or mixtures of C.sub.12-15-alkyl benzoate and 2-ethylhexyl isostearate, a mixture of C.sub.12-15-alkyl benzoate and butylene glycol dicaprylate/dicaprate, a mixture of C.sub.12-15-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate, paraffin oil, cycloparaffin, squalane, squalene, hydrogenated polyisobutene, polydecene, phospholipid, and a fatty acid triglyceride; combining the functionalized, highly branched polyester and the oil component; and adding the combined functionalized polyester/oil component to the cosmetic or the dermatologic formulation.

10. The method of claim 9, wherein the monoisocyanate functionalization reagent is a linear C.sub.4-C.sub.40 alkyl isocyanate or a linear C.sub.4-C.sub.40-alkenyl isocyanate.

11. The method of claim 9, wherein the monoisocyanate functionalization reagent is selected from the group consisting of octyl (capryl) isocyanate, nonyl isocyanate, decyl (caprinyl) isocyanate, undecyl isocyanate, dodecyl (laurinyl) isocyanate, tetradecyl isocyanate, hexadecyl (palmityl) isocyanate, heptadecyl isocyanate, and octadecyl (stearyl) isocyanate.

12. The method of claim 9, wherein the monoisocyanate functionalization reagent is selected from the group consisting of dodecenyl, hexadienyl (sorbinyl), octadecenyl (oleyl), linolyl and linolenyl isocyanate.

13. The method of claim 11, wherein the monoisocyanate functionalization reagent is stearyl isocyanate.

14. The method of claim 9, wherein x is 3.

15. The method of claim 14, wherein the C.sub.x is trimethylolpropane.

16. The method of claim 9, wherein the at least one x-hydric alcohol (C.sub.x) is selected from the group consisting of glycerol, diglycerol, triglycerol, trimethylolethane, trimethylolpropane, 1,2,4-butanetriol, pentaerythritol, tris(hydroxyethyl) isocyanurate, and ethylene oxide and/or propylene oxide derivatives of each thereof.

17. The method of claim 9, wherein the fatty acid triglyceride is a natural oil selected from the group consisting of olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, castor oil, wheatgerm oil, grapeseed oil, thistle oil, evening primrose oil, and macadamia nut oil.

18. The method of claim 9, wherein the combined functionalized polyester/oil component is added to a dermatologic formulation selected from the group consisting of day and night creams, eye creams, face creams, antiwrinkle creams, mimic creams, moisturizing creams, bleaching creams, vitamin creams, skin lotions, care lotions and moisturizing lotions.

19. The method of claim 9, wherein the combined functionalized polyester/oil component is added to a cosmetic formulation selected from the group consisting of face toners, face masks, deodorants and other cosmetic lotions and preparations for decorative cosmetics, for example concealing sticks, stage make-up, mascara, eyeshadows, lipsticks, kohl pencils, eyeliners, make-ups, foundations, blushers, powders and eyebrow pencils.

20. A method for thickening a cosmetic or dermatologic formulation, the method comprising: providing a functionalized, highly branched polyester having linear or branched C.sub.4-C.sub.40 alkyl radicals or C.sub.4-C.sub.40 alkenyl radicals, wherein the functionalized, highly branched polyester is a reaction product of at least one aliphatic, cycloaliphatic, araliphatic, or aromatic dicarboxylic acid (A.sub.2), optionally, a dihydric, aliphatic, cycloaliphatic, araliphatic, or aromatic alcohol (B.sub.2), having two OH groups, and at least one x-hydric alcohol (C.sub.x) selected from the group consisting of glycerol, diglycerol, triglycerol, trimethylolethane, trimethylolpropane, 1,2,4-butanetriol, pentaerythritol, tris(hydroxyethyl) isocyanurate, and ethylene oxide and/or propylene oxide derivatives of each thereof, to provide a highly branched polyester, and reacting the highly branched polyester with a monoisocyanate functionalization reagent selected from the group consisting of octyl (capryl) isocyanate, nonyl isocyanate, decyl (caprinyl) isocyanate, undecyl isocyanate, dodecyl (laurinyl) isocyanate, tetradecyl isocyanate, hexadecyl (palmityl) isocyanate, heptadecyl isocyanate, octadecyl (stearyl) isocyanate, dodecenyl, hexadienyl (sorbinyl), octadecenyl (oleyl), linolyl and linolenyl isocyanate, wherein the reaction is conducted with a molar ratio of functionalization reagent to reactive groups of the highly branched polyester of from 1:5 to 1:1.1; providing an oil component; combining the functionalized, highly branched polyester and the oil component; and adding the combined functionalized polyester/oil component to the cosmetic or the dermatologic formulation.

21. The method of claim 20, wherein the oil component is selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, butylene glycol dicaprylate/dicaprate, 2-ethylhexyl cocoate, C.sub.12-15-alkyl benzoate, caprylic-capric triglyceride, dicaprylyl ether, any one mixture of octyldodecanol, caprylic-capric triglyceride, dicaprylyl ether, dicaprylyl carbonate, cocoglycerides or mixtures of C.sub.12-15-alkyl benzoate and 2-ethylhexyl isostearate, a mixture of C.sub.12-15-alkyl benzoate and butylene glycol dicaprylate/dicaprate, a mixture of C.sub.12-15-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate, paraffin oil, cycloparaffin, squalane, squalene, hydrogenated polyisobutene, polydecene, phospholipid, and a fatty acid triglyceride.

Description

EXAMPLES

Measurement Methods

[0182] The IR measurements were carried out using a Nicolet 210 instrument.

[0183] The acid number and the hydroxyl number were determined in accordance with DIN 53240, part 2.

[0184] The molecular weight was determined with the help of gel permeation chromatography using a refractometer as detector. The mobile phase used was dimethylacetamide, and the standard used for determining the molecular weight was polymethyl methacrylate (PMMA).

Feed Materials

[0185] DBTL: Dibutyltin dilaurate, manufacturer Sigma-Aldrich

[0186] Paraffin oil: Nujol, Fluka AG

Example 1: Preparation of a Highly-Branched Polyester

[0187] 233.2 g of adipic acid (1.6 mol) and 266.0 g (1.33 mol) of a triol based on trimethylolpropane which has been etherifled in a random manner with 1,2-propylene oxide units were initially introduced into a 1000 ml glass reactor fitted with stirrer, reflux condenser, gas inlet, attached thereto a vacuum system with interconnected cold trap and internal thermometer. After adding 200 ppm of DBTL, the mixture was heated to 150 C. During this, the internal pressure was reduced to a final value of ca. 10 mbar in such a way that the water that formed was removed in a controlled manner. Stirring was carried out for 5.5 hours at this temperature. The acid number was 68 mg KOH/g. 97 g of the aforementioned trial (0.8 equivalents per acid group) were added to the reaction mixture. The reaction mixture was stirred for a further 5 hours at an Internal pressure of ca. 10 mbar and then cooled to ambient temperature at this pressure.

[0188] The end product was obtained as viscous, clear liquid which has the following properties: acid number=26 mg KOH/g; hydroxyl number=204 mg KOH/g; viscosity: 6800 mPas (75 C.)

Examples 2-8: Modification of the Highly-Branched Polyester with Stearyl Isocyanate

[0189] Highly-branched polyester from example 1 was initially introduced into a 250 ml glass reactor equipped with stirrer, reflux condenser, gas inlet, internal thermometer and dropping funnel, which comprised the required amount of stearyl isocyanate. The amounts of highly-branched polyester and stearyl isocyanate used are given in the table below.

[0190] The reactor was heated to 80 C. and the isocyanate was added dropwise over the course of 15 minutes. The reaction mixture was then stirred for a further 2 hours at 120 C. and the reaction progress was monitored via the disappearance of the isocyanate groups with the help of IR spectroscopy (disappearance of the isocyanate band at 2270 cm.sup.1).

TABLE-US-00001 Example 2 3 4 5 6 7 8 Highly-branched 50 50 51.2 76.6 50 50 50 polyester (example 1) [g] Mol % NCO 40 50 60 70 80 90 100 Amount of stearyl 21.5 26.9 33.1 58 43.04 48.4 53.8 isocyanate [g]

Example 9: Gel Formation by Adding the Stearyl-Modified Highly-Branched Polyester to Paraffin Oil

[0191] Various amounts (0.5 to 20% by weight) of the polymers in examples 3 to 8 were dissolved in paraffin oil. The concentration at which visible gel formation occurred is given in the table below.

TABLE-US-00002 Polymer from example . . . 3 4 5 6 7 8 NCO/OH ratio [%] 50 60 70 80 90 100 Gel formation concentration (%) 10 10 7 6 4 4