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EP-4734930-A1 - MIXED COMPOSITIONS COMPRISING 1,3-PROPANEDIOL ESTERS FOR COSMETIC FORMULATIONS IN PARTICULAR

EP4734930A1EP 4734930 A1EP4734930 A1EP 4734930A1EP-4734930-A1

Abstract

The present invention relates to mixed compositions of 1,3-propanediol esters which have thickening and/or antimicrobial properties in cosmetic formulations in particular, and to the preparation and use thereof.

Inventors

  • SCHUCH, Dominik
  • Brandt, Kathrin Daniela
  • LIEBIG, Stefan Julian
  • HÜBNER, Marlene
  • KONIETZNY, Agnes
  • STEINMETZER, Sabine

Assignees

  • Evonik Operations GmbH

Dates

Publication Date
20260506
Application Date
20240626

Claims (16)

  1. 1. Mixed composition comprising A) 1,3-propanediol, B) 1,3-propanediol monocarboxylic acid esters, and C) 1,3-propanediol dicarboxylic acid esters, characterized in that, based on all acyl groups present in components B) and C), at least 80 mol% are selected from acyl groups of carboxylic acids comprising 7 to 12 carbon atoms.
  2. 2. Mixed composition according to Claim 1, characterized in that, based on all acyl groups present in components B) and C), at least 60 mol% are selected from acyl groups of carboxylic acids comprising 8 to 10 carbon atoms.
  3. 3. Mixed composition according to Claim 1 or 2, characterized in that, based on all the acyl groups present in components B) and C), at least 35 mol% are selected from capryloyl groups and at least 30 mol% are selected from caproyl groups.
  4. 4. Mixed composition according to at least one of the preceding claims, characterized in that A) from 0.1% to weight to 40.0% by weight, B) from 10.0% by weight to 65.0% by weight, and C) from 15.0% by weight to 75.0% by weight, are present in the mixed composition, wherein the percentages by weight refer to the total mixed composition.
  5. 5. Mixed composition according to at least one of the preceding claims, characterized in that said composition has a saponification number of 150 mg KOH/g to 400 mg KOH/g, preferably 175 mg KOH/g to 375 mg KOH/g, particularly preferably 200 mg KOH/g to 350 mg KOH/g.
  6. 6. Mixed composition according to at least one of the preceding claims, characterized in that said composition has an acid number of less than 80 mg KOH/g, preferably less than 50 mg KOH/g, particularly preferably from 0.1 mg KOH/g to 20 mg KOH/g.
  7. 7. Mixed composition according to at least one of the preceding claims, characterized in that said composition has a hydroxyl number of 50 mg KOH/g to 1000 mg KOH/g, preferably from 75 mg KOH/g to 500 mg KOH/g, particularly preferably 100 mg KOH/g to 400 mg KOH/g.
  8. 8. Enzyme-catalysed process for preparing a mixed composition comprising 1 ,3-propanediol, 1,3-propanediol monocarboxylic acid esters and 1,3-propanediol dicarboxylic acid esters comprising the process step of I) reacting 1 ,3-propanediol with at least one acyl group donor, preferably a fatty acid acyl group donor, selected in particular from fatty acid esters and fatty acids, particularly preferably fatty acids, to obtain the mixed composition, in the presence of a lipase.
  9. 9. Process according to Claim 8, characterized in that the acyl group donor is selected from fatty acid acyl group donors which in particular provide an acyl group selected from the group of the acyl groups of caproic acid, caprylic acid, pelargonic acid, capric acid, undecylenoic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, petroselic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid, particularly preferably caprylic acid, pelargonic acid, capric acid and undecylenoic acid.
  10. 10. Process according to claim 8 or 9, characterized in that in process step I) the molar ratio of 1,3-propanediol to acyl groups present in all acyl group donors is within a range from 1.0:0.7 to 1.0:1.6, preferably from 1.0:0.75 to 1.0:1.5, particularly preferably from 1.0:0.8 to 1.0:1.4.
  11. 11 . Process according to at least one of Claims 8 to 10, characterized in that the lipase is selected from the group comprising the lipase from Thermomyces lanuginosus (accession number 059952), lipases A and B (accession number P41365) from Candida antarctica and the lipase from Mucor miehei (accession number P19515), the lipase from Humicola sp. (accession number 059952), the lipase from Rhizomucorjavanicus (accession number S32492), the lipase from Rhizopus oryzae (accession number P61872), the lipases from Candida rugosa (accession number P20261, P32946, P32947, P3294 and P32949), the lipase from Rhizopus niveus (accession number P61871), the lipase from Penicillium camemberti (accession number P25234), the lipases from Aspergillus niger (ABG73613, ABG7361 and ABG37906) and the lipase from Penicillium cyclopium (accession number P61869), and their respective at least 60% homologues at the amino acid level.
  12. 12. Process according to at least one of Claims 8 to 11 , characterized in that process step I) is conducted at reaction temperatures in the range between 20°C and 100°C, preferably 30°C and 80°C, in particular between 35°C and 70°C.
  13. 13. Process according to at least one of Claims 8 to 12, characterized in that in process step I) the 1 ,3-propanediol and the acyl group donor make up in total at least 10% by weight, preferably at least 80% by weight, particularly preferably at least 90% by weight, of the overall reaction mixture.
  14. 14. Mixed composition comprising 1,3-propanediol, 1 ,3-propanediol monocarboxylic acid esters and 1,3-propanediol dicarboxylic acid esters obtainable by the process according to at least one of Claims 8 to 13.
  15. 15. Formulation, in particular a cosmetic, pharmaceutical or dermatological formulation, comprising a mixed composition according to at least one of Claims 1 to 7 or 14.
  16. 16. Use of a mixed composition according to at least one of Claims 1 to 7 or 14 as an antimicrobial active ingredient and/or thickener.

Description

Mixed compositions comprising 1,3-propanediol esters for cosmetic formulations in particular Field of the invention The present invention relates to a mixed composition of 1 ,3-propanediol esters which, in particular, have thickening and/or antimicrobial properties in cosmetic formulations, and to the preparation and use thereof. Prior art Many of the thickeners and preservatives for cosmetic formulations that are widely used on the market no longer meet the demands of industry and consumers in terms of sustainability. The trend is towards toxicologically safe, readily biodegradable and completely naturally based products. Such thickeners include glyceryl and sorbitan fatty acid esters. With regard to antimicrobial additives, glyceryl caprylate, p-anisic acid and levulinic acid are among those that meet the requirements. In addition, a completely natural-based 1 ,3-propanediol caprylate (Crinipan PMC green, Symrise) as a pure monoester is also available as an antimicrobial active ingredient. GB2597354A discloses that, in addition to antimicrobial properties, this substance also has viscosity-increasing and hence thickening properties. However, this 1 ,3-propanediol caprylate has the disadvantage that it is not suitable for a use as thickening agent in low- to medium-priced cosmetic surfactant formulations for the mass market due to an inadequate cost/performance ratio. WO2012080231 A1 discloses the use of 1 ,3-propanediol dicaprylate in a process for permanently modifying the shape of keratinic fibers. WO2008123845A2 discloses compositions comprising esters of 1 ,3-propanediol, wherein the 1,3- propanediol has a biological origin. The disadvantage of the disclosed production processes is the use of problematic catalysts. In formulation, the esters result in insufficiently thickened formulations and require the addition of polymer thickeners to increase viscosity. WO 2007095262 discloses compositions comprising esters of 1 ,3-propanediol and an extraction product. WO 20201 7934 discloses diesters of 1,3-propanediol with linear fatty acids having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, with the proviso that both the 1 ,3-propanediol and the fatty acids originate exclusively from plant sources. WO 2010100887 discloses cosmetic preparations comprising an emulsifier, 1 ,3-propanediol and a 1,3-propanediol difatty acid ester, wherein the fatty acids constituting the 1 ,3-propanediol difatty acid ester are selected from isostearic acid, n-octanoic acid and n-decanoic acid. WO 2020160743 discloses the use of a fatty acid ester or a mixture of two or more fatty acid esters, wherein the fatty acid ester or one, two, three or more, preferably all, of the fatty acid esters are selected from the group consisting of 3-hydroxypropyl caprylate, glyceryl monocaprylate, 3- hydroxypropyl undecylenate and glyceryl monoundecylenate, to modify the physicochemical properties of a skincare product. WO 2020160905 discloses the use of a fatty acid ester or a mixture comprising or consisting of two or more fatty acid esters in a cosmetic product for (i) and/or (ii): (I) inhibition of the growth of microorganisms on the skin or mucous membrane of a mammal; (II) preserving the cosmetic product against microbial growth; wherein the fatty acid ester or at least one of the two or more fatty acid esters in the mixture is selected from the group consisting of: 3-hydroxypropyl caprylate, 3-hydroxypropyl undecylenate and glyceryl monoundecylenate. WO 2020160904 discloses the use of a fatty acid ester or a mixture of two or more fatty acid esters or a mixture of one or more fatty acid esters, wherein the fatty acid ester or one, two or more of the fatty acid esters is/are selected from the group consisting of 3-hydroxypropyl caprylate, 3- hydroxypropyl undecylenate and glyceryl monoundecylenate for modifying the physicochemical properties of a skincare product. W020160742 discloses the use of a fatty acid ester or a mixture of two or more fatty acid esters or a mixture of one or more fatty acid esters, wherein the fatty acid ester or one, two, three or more of the fatty acid esters is/are selected from the group consisting of 3-hydroxypropyl caprylate, glyceryl monocaprylate, 3-hydroxypropyl undecylenate and glyceryl monoundecylenate, to modify the sensory properties of a skincare product. W020160741 discloses fatty acid esters or mixtures of two or more fatty acid esters or mixtures comprising one or more fatty acid esters, wherein the fatty acid ester or one, two, three or more of the fatty acid esters is/are selected from the group consisting of 3-hydroxypropyl caprylate, glyceryl monocaprylate, 3-hydroxypropyl undecylenate and glyceryl monoundecylenate for use in the treatment of an excess of Malassezia on the surface of the skin of mammals. of the invention It was therefore an object of the present invention to provide 1,3-propanediol carboxylic acid esters which can be prepared by a simple process, ideally without a disti