Polyol partial esters of poly(polyhydroxy fatty acid)
Polyol partial esters of poly(polyhydroxy fatty acids, produced from renewable sources, address sustainability and compatibility issues of existing emulsifiers, offering improved sensory and stability properties in cosmetic and food formulations, as well as lubricant applications.
Patent Information
- Application Number
- PCT/EP2025/053056
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-02-12
- Filing Date
- 2025-02-06
- Publication Date
- 2025-08-21
AI Technical Summary
Existing emulsifiers based on castor plant seed oil-derived ricinoleic acid and hydroxystearic acid are unsustainable and have limitations in terms of raw material diversity, skin compatibility, and formulation stability, particularly in cosmetic and food applications.
The production of polyol partial esters of poly(polyhydroxy fatty acids using renewable raw materials through a process involving epoxidation and polymerization of unsaturated fatty acids, followed by esterification with polyols, to create emulsifiers that are biodegradable, ecotoxicologically friendly, and suitable for various formulations.
The resulting polyol partial esters provide improved sensory properties, increased absorption, enhanced UV protection, and stability in cosmetic formulations, while being tolerant to electrolytes and allowing for high gloss and wear resistance in make-up applications, with applications extending to metal working fluids and lubricants.
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Abstract
Description
Polyol partial esters of poly(polyhydroxy fatty acid)Field of the inventionThe invention provides polyol partial esters of poly(polyhydroxy fatty acid), their production and use, in particular in cosmetics.Prior artPrior art applicationsPoly(ricinoleic acid) and poly(hydroxystearic acid) are the homopolymers derived from the polymerization of the monohydroxy fatty acids ricinoleic acid and 12-hydroxystearic acid, respectively.Esters of poly (ricinoleic acid) and poly(hydroxystearic acid) are well known in cosmetic applications, for example under the following INCI names:Dimer Dilinoleyl Bis-Polyricinoleate, Ethylhexyl Polyricinoleate, Lauryl / Myristyl Polyricinoleate, Methyl Polyricinoleate, Polyglyceryl-4 Olivate / Polyricinoleate, Polyglyceryl-3 Polyricinoleate, Polyglyceryl-4 Polyricinoleate, Polyglyceryl-5 Polyricinoleate, Polyglyceryl-6 Polyricinoleate, Polyglyceryl-10 Polyricinoleate, Propanediol Dipolyricinoleate,Behenyl Polyhydroxystearate, Dipentaerythrityl Tetrabehenate / Polyhydroxystearate, Dipentaerythrityl Tri-Polyhydroxystearate, Ethylhexyl Polyhydroxystearate, Ethylhexyl Stearoyl Polyhydroxystearate Glycereth-18 Polyhydroxystearate, Isooctyl Polyhydroxystearate, PEG-30 Dipolyhydroxystearate, Pentaerythrityl Behenate / Polyhydroxystearate, Polyglyceryl-4Diisostearate / Polyhydroxystearate / Sebacate, Polyglyceryl-2 Dipolyhydroxystearate, Polyglyceryl-6 Polyhydroxystearate, Polyglyceryl-10 Polyhydroxystearate.In particular, esters obtainable by esterification of polyols and poly(ricinoleic acid) and / or poly(hydroxystearic acid) have proven to be highly versatile in terms of potential applications.For example, polyglycerol polyricinoleate (PGPR, E476) is an emulsifier which can be used to reduce viscosity in chocolate, compound chocolate and similar coatings, especially when being used in combination with other substances like lecithin. It can also be used as an emulsifier in salad dressings and spreads or to improve the texture of baked goods.EP1500427 discloses polyglycerol partial esters of polyhydroxystearic acid and polyfunctional carboxylic acids, obtainable by esterification of a a) polyglycerol mixture, with b) polyhydroxystearic acid and c) di-, tricarboxylic acids or mixtures thereof.These polyglycerol partial esters allow formulation of highly liquid emulsions which have a pleasant sensation on the skin and at the same time an improved resistance to low-temperature storage.EP1683781 discloses polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids prepared by esterification a) of a polyglycerol mixture with b) at least one certain polyricinoleic acid and, optionally polyhydroxystearic acid, and c) at least one di- and / or tricarboxylic acid and d) at least one fatty acid.These polyglycerol partial esters allow formulation of emulsions of low viscosity with a light skin feel as well as formulations of high stability at elevated temperatures which are also stable to cold.EP3500550 discloses polyglycerol partial esters obtained by esterification of a polyglycerol with a carboxylic acid mixture comprising: a) at least one polyhydroxycarboxylic acid of a hydroxycarboxylic acid having 8 to 32 b) at least one short-chain dicarboxylic acid having 2 to 16 carbon atoms, c) at least one long-chain dicarboxylic acid having 24 to 44 carbon atoms, and d) at least one fatty acid selected from linear, unsaturated and branched, saturated fatty acids having 14 to 24 carbon atoms.These polyglycerol partial esters can be used as W / O emulsifiers.The esters in the previously mentioned examples all suffer from the disadvantage of being based on castor plant seed oil, which is the source of ricinoleic acid (12-hydroxy-9-c / s-octadecenoic acid) and 12-hydroxystearic acid (which is hydrogenated ricinoleic acid).For sustainability reasons it is of great importance to diversify the basis of renewable feedstocks.Prior Art Epoxidation and PolymerizationThe epoxidation and dihydroxylation of unsaturated fatty acids and unsaturated vegetable oils is well- known. Also well-known is the condensation / polymerization of (polyhydroxy)monocarboxylic acids and epoxy-monocarboxylic acids.Aguilera et al. describe in Chemical Engineering & Processing: Process Intensification 174 (2022) 108882 the lipase catalyzed epoxidation of oleic acid. As a side reaction during the epoxidation, the formation of esters through ring-opening reactions with carboxylic acids groups as dominant nucleophiles is described, which is synonymous for the homopolymerization of 9,10-epoxystearic acid to give poly(9,10-dihydroxystearic acid).Miao et al. describe in Journal of Polymer Science, Part A: Polymer Chemistry (2008), 46 (12), 4243- 4248 the epoxidation of oleic acid (99% C18:1) using Candida antarctica lipase B enzyme and hydrogen peroxide (H2O2) in toluene as solvent to obtain what they call “oleic acid epoxide” (in fact, it is 9,10-epoxystearic acid). This intermediate epoxy fatty acid is then submitted to homopolymerization under solvent-free conditions to obtain what they call “poly(oleic acid)” (which is synonymous to poly (9, 10-dihydroxystearic acid)).In J. Polym. Sci. , Part A: Polym. Chem. 2016, 54, 3159-3170 Evans et al. describe the synthesis of 9,10-epoxystearic acid from oleic acid (90% C18:1) and its subsequent homopolymerization. Also, a schematic and representative presentation of the polymerization process is provided.In Angew. Chem. Int. Ed. 2003, 42, 5623-5625 Usui et al. describe the catalytic dihydroxylation of oleic acid to 9,10-dihydroxystearic acid using H2O2 and resin-supported sulfonic acid in an organic solvent- and metal-free system.DE2129994 A1 discloses the condensation of (polyhydroxy)monocarboxylic acids with 2 to 6 hydroxyl groups and a total of 3 to 22 carbon atoms (examples are glyceric acid, 9,10-dihydroxystearic acid or trihydroxystearic acid) for coating compositions. Co-condensation with other (mono-'hydroxy)mono- carboxylic acids such as 12-hydroxystearic and ricinoleic acid, oleic acid, lauric acid, etc. is also described. The obtained polymers are monofunctional with respect to the carboxyl group. Copolyesters of various dihydroxycarboxylic acids are also described. Example 2 describes the synthesis of poly(9,10-dihydoxystearic acid) in xylene starting from 9,10-dihydroxystearic acid. The resulting poly(9,10-dihydoxystearic acid) has an acid value of 22 mg KOH / g and a hydroxyl value of 166 mg KOH / g.Fehling describes in JAOCS 1995, 72, 355-359 that hydroxylated fatty acids (HOFAs) prepared from various plant oils contain considerable amounts of estolides which are formed by intermolecular esterification of the HOFA. These estolides contain predominantly saturated fatty acids which are esterified to threo-9,10-di hydroxy octadecanoic acid or dihydroxy tetra hydrofuran octadecanoic acids,e.g. 9,12-dihydroxy-10,13-epoxy octadecanoic acid and 10,13-dihydroxy-9,12-epoxy octadecanoic acid.Casali et al. describe in Green Chem 2022, 24, 2082-2093 that when linoleic acid is submitted to certain conditions of epoxidation and subsequent hydrolysis, dihydroxy tetrahydrofuran derivatives can be formed via an intramolecular dehydration of intermediate dihydroxy derivatives obtained by partial hydrolysis of the diepoxy stearic acid.DE4125031 discloses a process to produce hydroxylated fatty acid compounds by acid-catalyzed hydrolysis of epoxidized fatty acids, their esters and amides, characterized in that epoxidized fatty acid compounds with one or more central oxirane rings are reacted with water in the presence of acid- activated clays and / or silicates and / or activated carbons as a catalyst.JAOCS 1995, 72, 349 discloses a process for the industrial production of hydroxylated fatty acids by epoxidation of plant oils and their derivatives, followed by catalytic epoxy ring opening in the presence of water or other hydrogen donors, such as alcohols, diols, and amines.The object of the invention was to provide excellent emulsifiers, especially for use in cosmetic formulations and in food applications.Decription of the inventionSurprisingly, it was found that the polyol partial esters of poly(polyhydroxy fatty acid) obtainable by the process according to the instant invention described below are capable of solving the problem assigned to the invention.The subject matter of the instant invention is a process for production of a polyol partial ester of poly(polyhydroxy fatty acid) as described in claim 1 .A further subject of the instant invention is the polyol partial ester of poly(polyhydroxy fatty acid) obtainable by the process of the instant invention as well as formulations comprising them.Another subject of the instant invention is the use of polyol partial esters of poly(polyhydroxy fatty acid) according to the instant invention in various fields.An advantage of the present invention is that the polyol partial esters of poly(polyhydroxy fatty acid) described herein may be prepared from exclusively renewable raw materials.A further advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) 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 polyol partial esters of poly(polyhydroxy fatty acid) described herein are biodegradable.A further advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) described herein have a good ecotoxicological profile.A further advantage of the polyol partial esters of poly(polyhydroxy fatty acid) described herein is that they are very mild on the skin, not irritating and non-toxic.Another advantage of the polyol partial esters of poly(polyhydroxy fatty acid) 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 polyol partial esters of poly(polyhydroxy fatty acid) described herein is that they give rise to enhancement of “velvety-silkiness” in formulations.A further advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) described herein have a good skin-moisturizing effect.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) 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 polyol partial esters of poly(polyhydroxy fatty acid) 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 polyol partial esters of poly(polyhydroxy fatty acid) 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 polyol partial ester of poly(polyhydroxy fatty acid) according to the invention is that they permit good dispersion of pigments in the formulations.A further advantage of the polyol partial esters of poly(polyhydroxy fatty acid) described herein is that they have good compatibility with formulations containing UV protection filters or pigments.In general, the polyol partial esters of poly(polyhydroxy fatty acid) described herein impart good stability to the formulations.Another advantage of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention is that they are easily processable since they mix readily with typical cosmetic oils and can be rapidly incorporated into corresponding emulsions.A further advantage of the polyol partial esters of poly(polyhydroxy fatty acid) described herein is that they impart high gloss to solid or waxy formulations such as lipsticks.Yet another advantage of the polyglycerol partial esters according to the invention is that they are particularly tolerant to electrolytes, which means that, for example, formulations containing large amounts of salt remain stable.A further advantage of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention is that they have a structuring and viscosity-increasing effect in formulations having high oil contents or even pure oils.One advantage of the polyol partial ester of poly(polyhydroxy fatty acid) according to the invention is that formulations based on polyol partial esters of poly(polyhydroxy fatty acid) described herein can be prepared by a cold process without heating.Another advantage of the polyol partial ester of poly (poly hydroxy fatty acid) according to the invention is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention are very tolerant towards different oil phase contents in the emulsions.A further advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention are very tolerant towards different oil phase compositions in the emulsions.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention have a pleasant, less “technical” odor.Another advantage of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention is that even high proportions of natural oils such as almond oil are well stabilized in emulsions.Another advantage of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention is that emulsions can be stabilized over a wide viscosity range from sprays to lotions to creams.A further advantage of the present invention is that emulsions based on emulsifiers according to the invention have very good compatibility with propellants, such as mixtures of propane, n-butane and iso-butane, and thus simplify the production of aerosol systems.A further advantage of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention is that the skin feel of the emulsions stabilized with the described polyol partial esters of poly(polyhydroxy fatty acid) is at least as good as with the emulsifiers of the prior art.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention can be used as emulsifier and lubricity additive for metal working fluids (neat oils or water based fluids) where it provides excellent emulsion stabilizing properties, reduces oil droplet coalescence, increases lubricity properties e.g. of base oils especially at high frictions, is soluble even in GTL oils, gives best additional lubricity under stress, and reduces applied torque during tapping. Further, the polyol partial ester of poly(polyhydroxy fatty acid) according to the invention provides excellent stability of rolling oil emulsions with reduced coalescence, good lubricity and good surface quality.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention can be used as friction modifiers for lubricants.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention can reduce the friction coefficient.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention can lead to more efficient friction reduction due to a lower treat rate and / or a better combination of oil compatibility and friction reducing performance.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention can improve flow properties, reduce the Casson yield value in chocolates and compounds and provides excellent viscosity control.Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention works well in combination with ammonium phosphatide (AMP) and lecithin.Another advantage is that the polyol partial ester of poly(polyhydroxy fatty acid) according to the invention is tasteless and odourless, preventing off-flavour in the chocolate and bad castor oil odor. Another advantage is that the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention are pumpable at room temperature or can easily be blended with a (cosmetic) oil to facilitate handling.Another advantage is that the polyol partial ester of poly(polyhydroxy fatty acid) according to the invention allow for optimal moulding with an excellent distribution in the moulds with no air bubbles.The present invention therefore provides a process for production of a polyol partial ester of poly(polyhydroxy fatty acid) comprising the steps ofA) providing at least one poly(polyhydroxy fatty acid),B) providing at least one polyol, preferably a mixture of more than one polyol,C) esterification of said at least one poly(polyhydroxy fatty acid) and said at least one polyol.The term "polyhydroxy fatty acids " within the meaning of the present invention describes saturated or unsaturated, linear or branched, cyclic or acyclic carboxylic acids with 2 to 12, preferably 2 to 10, more preferably 2 to 6 hydroxyl groups and a total of 3 to 36, preferably 6 to 28, more preferably 8 to 22 carbon atoms.The term "epoxy fatty acids" within the meaning of the present invention describes saturated or unsaturated, linear or branched, cyclic or acyclic carboxylic acids with at least one epoxide functional group and a total of 3 to 36, preferably 6 to 28, more preferably 8 to 22 carbon atoms.The term "poly(polyhydroxy fatty acid)” within the meaning of the present invention describes the polyester polymer obtainable by the polymerization of at least one polyhydroxy fatty acid and / or at least one epoxy fatty acid.It is preferred that the poly(polyhydroxy fatty acid) within the meaning of the present invention is monofunctional with respect to the carboxyl group.It is further preferred that at least 2 of the 2 to 12, preferably 2 to 10, more preferably 2 to 6 hydroxyl groups in the polyhydroxy fatty acid building block of the poly(polyhydroxy fatty acid) form a vicinal diol, i.e. that at least 2 of the hydroxyl groups are attached to adjacent carbon atoms.Where average values are stated hereinbelow, then, unless stated otherwise, these are number- averaged average values.Unless stated otherwise, percentages are data in percent by weight. The same is true for parts per million (ppm).Wherever measurement values are stated hereinbelow, then, unless stated otherwise, these have been determined at a temperature of 25 °C and a pressure of 1013 mbar.A preferred process according to the instant invention is characterized in that step A) comprises the sub-steps ofA1) providing at least one unsaturated fatty acid,A2) epoxidation of at least one of the carbon-carbon double bonds of said at least one unsaturated fatty acid while obtaining an epoxy fatty acid,A3) opening of the epoxide group of said epoxy fatty acids while obtaining a polyhydroxy fatty acid, andA4) polymerizing said epoxy fatty acids and / or said polyhydroxy fatty acid while obtaining at least one poly(polyhydroxy fatty acid), wherein sub-step A3) is optional.A preferred process according to the instant invention is characterized in that said unsaturated fatty acid is selected from the group of arachidonic acid, calendic acid, catalpic acid, dihomo-y-linolenic acid, docosahexaenoic acid, docosapentaenoic acid, docosatetraenoic acid, eicosapentaenoic acid, eicosatetraenoic acid, eicosenoic acid, 11-eicosenoic acid, elaidic acid, a-eleostearic acid, p- eleostearic acid, erucic acid, gadoleic acid, linoleic acid, linolelaidic acid, linolenic acid, a-linolenic acid, gamma-linolenic acid, mead acid, myristoleic acid, nervonic acid, octadecatetraenoic acid, octadecatrienoic acid, oleic acid, omega-3 fatty acid, omega-6 fatty acid, omega-7 fatty acid, omega-9 fatty acid, palmitoleic acid, a-parinaric acid, paullinic acid, petroselinic acid, pinolenic acid, punicic acid, ricinoleic acid, rumenic acid, sapienic acid, stearidonic acid, tuataric acid, undecylenic acid, vaccenic acid and vernolic acid, preferably erucic acid, linoleic acid, oleic acid and palmitoleic acid.A preferred process according to the instant invention is characterized in that in sub-step A1) a mixture of at least two unsaturated fatty acids is provided, more preferably a mixture of at least two unsaturated fatty acid selected from erucic acid, linoleic acid, oleic acid and palmitoleic acid.An alternatively preferred process according to the instant invention is characterized in that in substep A1) a mixture of at least one unsaturated fatty acid and at least one saturated fatty acid is used. The saturated fatty acid is preferably selected from the group of caproic acid, enanthic acid (preferably obtained via pyrolysis of ricinoleic acid), caprylic acid, pelargonic acid (obtainable for example from the ozonolysis or oxidative cleavage of oleic acid), capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, arachidic acid, behenic acid, lignoceric acid and cerotic acid.A preferred process according to the instant invention is characterized in that the epoxidation in substep A2) is catalyzed by an enzyme, preferably selected from the group of cytochrome P450 enzymes, lipoxygenases, peroxidases, epoxide hydrolases and lipases, preferably lipases, more preferably in the presence of at least one peroxide, preferably hydrogen peroxide.Lipases used with preference in accordance with the invention in process step A2) are present immobilized on a solid support.Lipases used with preference in accordance with the invention in process step A2) are lipases 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, ABG73614 and ABG37906) and the lipase from Penicillium cyclopium (accession number P61869), particular preference being given to lipases A and B (accession number P41365) from Candida antarctica, and their respective at least 60%, with preference at least 80%, preferably at least 90% and especially preferably at least 95%, 98% or 99%, homologues at the amino acid level.The accession numbers listed in the context of the present invention correspond to the NCBI Protein Bank database entries with a date of 01 .01 .2017; the version number of the entry is in the present context generally identified by “.digit”, for example “.1”.Enzymes that are homologous at the amino acid level preferably exhibit, by comparison with the reference sequence, at least 50%, especially at least 90%, of the enzyme activity in propyl laurate units as defined in the context of the present invention.To determine the enzyme activity in PLU (propyl laurate units), 1-propanol and lauric acid are mixed homogeneously in an equimolar ratio at 60°C. The reaction is started with addition of enzyme and thereaction time is measured. Samples are taken from the reaction mixture at intervals and the content of converted lauric acid is determined by titration with potassium hydroxide solution. The enzyme activity in PLU results from the rate at which 1 g of the enzyme concerned synthesizes 1 pmol of propyl laurate per minute at 60°C; cf. in this regard also US20070087418, in particular
[0185] .Commercial examples, and lipases that are likewise used with preference in processes according to the invention, are the commercial products Lipozyme TL IM, Novozym 435, Lipozyme IM 20, Lipase SP382, Lipase SP525, Lipase SP523, (all commercial products from Novozymes A / S, Bagsvaerd, Denmark), Chirazyme L2, Chirazyme L5, Chirazyme L8, Chirazyme L9 (all commercial products from Roche Molecular Biochemicals, Mannheim, Germany), CALB Immo Plus TM from Purolite, and Lipase M “Amano”, Lipase F-AP 15 “Amano”, Lipase AY “Amano”, Lipase N “Amano”, Lipase R “Amano”, Lipase A “Amano”, Lipase D “Amano”, Lipase G “Amano” (all commercial products from Amano, Japan).“Homology at the amino acid level” is for the purposes of the present invention understood as meaning “amino acid identity”, which can be determined with the aid of known methods. In general, use is made of special computer programs with algorithms taking into account specific requirements. Preferred methods for determining the identity first generate the greatest alignment between the sequences to be compared. Computer programs for determining the identity include, but are not limited to, the GCG program package includingGAP (Deveroy, J. et al., Nucleic Acid Research 12 (1984), page 387, Genetics Computer Group University of Wisconsin, Medicine (Wl), andBLASTP, BLASTN and FASTA (Altschul, S. et al., Journal of Molecular Biology 215 (1990), pages 403-410. The BLAST program can be obtained from the National Center For Biotechnology Information (NCBI) and from other sources (BLAST Handbook, Altschul S. et al., NCBI NLM NIH Bethesda ND 22894; Altschul S. et al., above).Those skilled in the art are aware that various computer programs are available for the calculation of similarity or identity between two nucleotide or amino acid sequences. For instance, the percentage identity between two amino acid sequences can be determined for example by the algorithm developed by Needleman and Wunsch (J. Mol. Biol. (48): 444-453 (1970)), which has been integrated into the GAP program in the GCG software package (available at http: / / www.gcg.com), using either a Blossom 62 matrix or a PAM250 matrix, a gap weight of 16, 14, 12, 10, 8, 6 or 4 and a length weight of 1 , 2, 3, 4, 5 or 6. Those skilled in the art will recognize that the use of different parameters will lead to slightly different results, but that the percentage identity between two amino acid sequences overall will not be significantly different. The Blossom 62 matrix is typically employed, using the default settings (gap weight: 12, length weight: 1).In the context of the present invention, an identity of 60% according to the above algorithm means 60% homology. The same applies to higher identities.In process step A2), preference is given in accordance with the invention to using 1 PLU to 2000 PLU, preferably from 5 PLU to 1500 PLU, more preferably from 50 PLU to 1250 PLU of lipase per gram of unsaturated fatty acid to be converted.Process step A2) is according to the invention preferably carried out in the presence of a hydrogen peroxide solution in water with a concentration of 1% to 65%, preferably 5% to 60%, more preferably 15% to 55%.Process step A2) is according to the invention preferably carried out at a temperature of 20 °C to 95 °C, preferably 30 °C to 90 °C, more preferably 35 °C to 80 °C.Preferably, over the course of time of process step A2) the temperature is increased by a range from 10 K to 50 K. The temperature increase can be accomplished either stepwise or via temperature ramping.Process step A2) is according to the invention preferably carried out at a pressure of 1 mbar to 1013 mbar, preferably 5 mbar to 900 mbar, and more preferably 10 mbar to 500 mbar.Preferably, over the course of process step A2) the pressure is decreased by a range from 100 mbar to 1000 mbar. The pressure decrease can be accomplished either stepwise or via pressure ramping.A preferred process according to the instant invention is characterized in that in sub-step A4) at least one selected from 9,10-epoxy-18-hydroxyoctadecanoic acid and 9,10,18-Trihydroxyoctadecanoic acid is co-polymerized with said epoxy fatty acids and / or said polyhydroxy fatty acid.A preferred process according to the instant invention is characterized in that said poly(polyhydroxy fatty acid) provided in step A) of the process of the instant invention has an acid value (AV) of 10 to 200 mg KOH / g, preferably 35 to 120 mg KOH / g, especially preferably from 40 to 90 mg KOH / g. Suitable methods for determining the acid value are, in particular, those according to DGF C-V 2, DIN EN ISO 2114, Ph.Eur. 2.5.1 , ISO 3682 and ASTM D 974.A preferred process according to the instant invention is characterized in that said poly(polyhydroxy fatty acid) provided in step A) of the process of the instant invention has an epoxy-[O] content (oxirane oxygen content) of less than 10.0%, preferably 0.005% to 5.0% more preferably 0.05% to 1 .0%, wherein the percentages refer to all poly (poly hydroxy fatty acid) provided in step A).The determination of the epoxy-[O] content can be achieved as described below:The epoxy ring reacts with hydrochloric acid (HCI) in a strictly non-aqueous medium to form a C-CI and a C-OH group via ring opening. The excess of hydrochloric acid is re-titrated using potassium hydroxide (KOH) in ethanol considering a blank value titration which is done in parallel. Waterinterferes with the ring opening with hydrochloric acid. Basic compounds neutralize some of the hydrochloric acid necessary for ring splitting. Due to their basic property, amines neutralize part of the hydrochloric acid necessary for the ring opening. Acidic compounds cause incorrect consumption of KOH in the re-titration.Materials:■ 0.05 g cresol red in tetrahydrofuran (THF; 100 mL) as indicator solution■ A solution of 0.1 mol / l HCI in 1 ,4-dioxane / THF (2:1 v / v)■ KOH in ethanol (0.1 mol / l)■ Ethanol (technical grade)The needed sample quantity (SQ) is calculated according to the following formula and has to be weighed accurately to ±0.1 mg:3.2SQ (ing') = — A withSQ = needed sample quantity in gX = expected epoxy-[O] content (oxirane oxygen content) in %.The maximum deviation from the targeted sample quantity must not exceed 5%. To the calculated sample quantity, 40 ml of the solution of 0.1 mol / l HCI in 1 ,4-dioxane / THF (2:1 v / v) is added with a full pipette. The flask is closed with a suitable glass stopper. The mixture is gently swirled until the sample is completely dissolved. The mixture is now allowed to react at room temperature for 15 minutes. During the reaction time, the mixture should be gently swirled in between. Under no circumstances should the mixture be heated above 25 °C. Then, the mixture is filled with ethanol to a volume of 100 ml. After adding a few drops of the indicator solution, the mixture is titrated against 0.1 mol / l ethanolic potassium hydroxide solution. When the indicator is added, the solution turns brick red, and shortly before reaching the end point, it turns lemon yellow. The end point of titration is reached when a new color change to blue-violet occurs. Parallel to the titration of the sample, two blank values are collected in the same way as described above but without sample material. In addition, care must be taken to ensure that the ethanolic KOH does not come into contact with the air CO2. The use of a suitable absorption tube for CO2 is advisable, otherwise disturbances are to be expected. The consumption for the blank value determinations may only be between 38 and 42 ml and may not deviate from each other by more than 0.15 ml in the case of double determination. Otherwise, the blank value determination must be repeated. Taking into account the consumption of 0.1 mol / l ethanolic potassium hydroxide solution of the blank value titration and of the sample titration as well as the sample weight, the epoxy-[O] content is calculated as follows: epoxy — [0] content [inwithVbiind = consumption (in ml) of 0.1 mol / l KOH in ethanol during the blank value determinationV = consumption (in ml) of 0.1 mol / l KOH in ethanol during the sample titrationc = concentration of KOH in ethanol (here 0.1 mol / l)M = molecular weight of oxygen (here 16 g / mol) SQ = sample quantity (in g)A preferred process according to the instant invention is characterized in that said poly(polyhydroxy fatty acid) provided in step A) of the process of the instant invention has an hydroxyl value (OHV) of 10 to 400 mg KOH / g, preferably 50 to 300 mg KOH / g, especially preferably from 70 to 200 mg KOH / g.Suitable methods of determination for the determination of the hydroxyl value are, in particular, those according to DGF C-V 17 a (53), Ph. Eur. 2.5.3 Method A and DIN 53240.A preferred process according to the instant invention is characterized in that said poly(polyhydroxy fatty acid) provided in step A) of the process of the instant invention has an saponification value (SV) of from 140 to 500 mg KOH / g, preferably from 150 to 250 mg KOH / g.Suitable determination methods for determining the saponification value are, in particular, those according to DGF C-V 3, DIN EN ISO 3681 and Ph. Eur. 2.5.6.A preferred process according to the instant invention is characterized in that the poly(polyhydroxy fatty acid) provided in step A) comprises at least on dihydroxy tetra hydrofuran octadecanoic acids, either as free monomeric dihydroxy tetra hydrofuran octadecanoic acid or covalently incorporated in the poly(polyhydroxy fatty acid).Preferably said dihydroxy tetra hydrofuran octadecanoic acid is present in an amount of 0.0001% to 10%, wherein the percentages refer to the sum of the total poly(polyhydroxy fatty acid) provided in step A) and all the dihydroxy tetra hydrofuran octadecanoic acids.The term "dihydroxy tetrahydrofuran octadecanoic acid” within the meaning of the present invention is defined according to Fehling in JAOCS 1995, 72, 355-359 and Casali et al. in Green Chem 2022, 24, 2082-2093.A preferred process according to the instant invention is characterized in that said polyol provided in step B) has three or more, preferably four or more, in particular more than six, carbon atoms.In the case that several polyols are used, it is of course true that this mixture preferably has three or more, preferably four or more, in particular more than six, carbon atoms on average.A preferred process according to the instant invention is characterized in that said polyol provided in step B) is selected from the group of 11 ,10-decanediol, 1 ,12-dodecanediol, 1 ,2-hexanediol, 1 ,2- octanediol, 1 ,2-pentylene glycol, 1 ,4-bis(hydroxymethyl)cyclohexane, 1 ,5-pentanediol, 2,2,4-trimethyl- 1 ,3-pentanediol, 2,2-bis(4-hydroxycyclohexyl)propane, 2,2-dimethyl-1 ,3-propanediol (neopentylglycol), 2,4-diethyl-1 ,5-pentane, 2,5-dimethyl-3-hexine-2,5-diol, 2-butyl-2-ethy 1-1 ,3-propanediol, 2- buty l-2-ethy 1-1 ,3-propanediol, 2-ethy 1-1 ,3-hexanediol, 2-methyl-1 ,3-propanediol, 2-methyl-2-propyl-1 , 3-propanediol, 2-methyl-2-propyl-1 ,3-propanediol, 2-sec-butyl-2-methyl-1 ,3-propane, 3-hexine-2,5- diol, ditrimethylolpropane, isosorbide, pinacol, tricyclodecanediethanol, tripentaerythritol, 1 ,2-butylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, 1 ,3-propanediol, 1 ,4-butanediol, 1 ,4-sorbitan, 1 ,5- sorbitan, diglycerin, dipentaerythritol, erythritol, glycerin, isomalt, lactitol, maltitol, mannitol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, xylitan, xylitol and polyglycerol, preferably polyglycerol.The term "polyglycerol" within the meaning of the present invention is to be understood as a polyglycerol which may also contain glycerol. Thus, for the calculation of quantities, masses and the like, a glycerol content may have to be taken into account. Due to its polymeric properties, polyglycerol represents a statistical mixture of different compounds. Polyglycerol can have ether bonds between two primary, one primary, and one secondary, as well as two secondary positions of the glycerol monomers. For this reason, the polyglycerol backbone usually does not consist exclusively of linearly linked glycerol units but can also contain branched and cyclic structures. For details see e.g. "Original synthesis of linear, branched and cyclic oligoglycerol standards", Cassel et al., J. Org. Chem. 2001 , 875-896.A method preferred according to the invention is characterized by the fact that said polyol provided in step B) comprises polyglycerol, wherein the polyglycerol preferably accounts for at least 20% by weight, preferably at least 40% by weight, and even more preferably at least 60% by weight, in particular preferably at least 80% by weight, based on all polyols.More preferably the process according to the instant invention is characterized in that said polyglycerol provided in step B) has a mean degree of polymerization of from 2.0 to 20, preferably 2.5 to 16 and most preferably 3.0 to 12.For the calculation, the mean degree of polymerization of polyglycerol <n> is calculated via the hydroxyl value (OHV, in mg KOH / g) of the polyglycerol according to the formula = (112200 - 18*OHV) / (74*OHV - 56100).More preferably the process according to the instant invention is characterized in that said polyglycerol provided in step B) has a content of cyclic oligomers from 1 .0% by weight to 50% by weight, preferably from 2.0% by weight to 40% by weight, particularly preferably from 3.0% by weight to 30% by weight, wherein the weight percentages refer to all polyglycerols provided in step B).In case a mixture of polyols is provided in step B) that comprises polyglycerol, it is preferred, that at least one further polyol is selected from the group of 1 1 ,10-decanediol, 1 ,12-dodecanediol, 1 ,2- hexanediol, 1 ,2-octanediol, 1 ,2-pentylene glycol, 1 ,4-bis(hydroxymethyl)cyclohexane, 1 ,5-pentanediol,2.2.4-trimethy 1-1 ,3-pentanediol, 2,2-bis(4-hydroxycyclohexyl)propane, 2,2-dimethyl-1 ,3-propanediol (neopentyl glycol), 2,4-diethyl-1 ,5-pentane, 2,5-dimethyl-3-hexine-2,5-diol, 2-butyl-2-ethyl-1 ,3- propanediol, 2-butyl-2-ethyl-1 ,3-propanediol, 2-ethyl-1 ,3-hexanediol, 2-methyl-1 ,3-propanediol, 2- methyl-2-propyl-1 , 3-propanediol, 2-methyl-2-propyl-1 ,3-propanediol, 2-sec-butyl-2-methyl-1 ,3- propane, 3-hexine-2,5-diol, ditrimethylolpropane, isosorbide, pinacol, tricyclodecanediethanol, tripentaerythritol, 1 ,2-butylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, 1 ,3-propanediol, 1 ,4- butanediol, 1 ,4-sorbitan, 1 ,5-sorbitan, dipentaerythritol, erythritol, isomalt, lactitol, maltitol, mannitol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, xylitan and xylitol, preferably isosorbide, 1 ,2-butylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, 1 ,3-propanediol,1 .4-butanediol, 1 ,4-sorbitan, 1 ,5-sorbitan, dipentaerythritol, erythritol, isomalt, lactitol, maltitol, mannitol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, xylitan and xylitol.A preferred process according to the instant invention is characterized in that in said process step C) at least one selected from monocarboxylic acids and polycarboxylic acids, preferably dicarboxylic acids, are co-esterified into the polyol.However, it is preferred, that the total amount of all poly(polyhydroxy fatty acid) accounts for at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 20 wt.-%, of all carboxylic acids esterified into the polyol.Said monocarboxylic acid is preferably selected from the group of natural fatty acids. Natural fatty acids can be produced on the basis of naturally occurring vegetable or animal oils and have preferably 6 to 30 carbon atoms, especially 8 to 22 carbon atoms. Natural fatty acids are usually unbranched and usually consist of an even number of carbon atoms. Any double bonds have cis configuration. Even more preferred natural fatty acids present in process step C) of the instant invention are selected from caproic acid, enanthic acid (preferably obtained via pyrolysis of ricinoleic acid), caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, pelargonic acid (obtainable for example from the ozonolysis or oxidative cleavage of oleic acid), isostearic acid (for example a by-product of the dimer acid obtained in the process of catalytic dimerization of C18 unsaturated fatty acids), stearic acid, ricinoleic acid, 12-hydroxystearic acid, dihydroxystearic acid, undecylenic acid (obtainable from the pyrolysis of ricinoleic acid), oleic acid, linoleic acid, linolenic acid, petroselinic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid, 18-hydroxyoctadec-9-enoic acid, 20- hydroxyeicosanoic acid and 20-Hydroxyeicosanoic acid .Polycarboxylic acids, like for example aconitic acid, agaric acid, 1 ,2,3,4-butanetetracarboxylic acid, citric acid, ethene-1 ,1 ,2,2-tetracarboxylic acid, isocitric acid, propane-1 ,2, 3-tricarboxylic acid or trimesic acid, can be co-esterified into the polyol.Preferbaly said polycarboxylic acid is a dicarboxylic acid.Short-chain- and / or long chain dicarboxylic acids can be co-esterified into the polyol.The term “short-chain dicarboxylic acid” is in the context of the present invention to be understood as meaning dicarboxylic acids having 4 to 18, preferably 4 to 14, more preferably 6 to 10, carbon atoms, for example itaconic acid.The term “long-chain dicarboxylic acid” is in the context of the present invention to be understood as meaning dicarboxylic acids having 24 to 44, preferably 30 to 40, more preferably 34 to 38, carbon atoms.It is preferable in accordance with the invention when the short-chain dicarboxylic acid co-esterified into the polyol is selected from aliphatic, linear dicarboxylic acids, especially succinic acid, maleic acid, tartaric acid, malic acid, fumaric acid, sorbic acid, a-ketoglutaric acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid and brassylic acid, with particular preference given to adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid.It is preferable in accordance with the invention when the long-chain dicarboxylic acid co-esterified into the polyol is selected from the group comprising dimer fatty acids that are oligomeric forms of various unsaturated monomeric fatty acids. Dimer fatty acids are a mixture of acyclic and cyclic dicarboxylic acids obtained by catalytic dimerization of unsaturated fatty acids having 12 to 22 carbon atoms. For the preparation and use of dimer acids and the physical and chemical properties thereof, reference is made to the publication “The Dimer Acids: The chemical and physical properties, reactions and applications", ed. E.C. Leonard; Humko Sheffield Chemical, 1975, Memphis, Tenn..The dicarboxylic acids may also contain tri- and polyfunctional carboxylic acids to a minor extent. The functionality of the mixture should not exceed, on molar average, a value of 2.4. Particularly suitable as the long-chain dicarboxylic acid for the end use in accordance with the invention is dimer acid or a mixture of dimer and trimer acid (for example Radiacid 0977 from Oleon) obtained from vegetable oils having a high content of unsaturated C18 fatty acids (oleic acid, linoleic acid, linolenic acid).The present invention further provides a polyol partial ester of poly(polyhydroxy fatty acid) obtainable by a process according to the instant invention.The polyol partial ester of poly(polyhydroxy fatty acid) according to this invention preferably has an acid value of 0.005-50 mg KOH / g, preferably 0.01-25 mg KOH / g.Suitable methods for determining the acid value are in particular those according to DGF C-V 2, DIN EN ISO 2114, Ph. Eur. 2.5.1 , ISO 3682 and ASTM D 974.The polyol partial ester of poly(polyhydroxy fatty acid) according to this invention preferably has a hydroxyl value of 10-900 mg KOH / g, preferably 30-250 mg KOH / g.Suitable detection methods for determining the hydroxyl value are in particular those according to DGF C-V 17 a (53), Ph. Eur. 2.5.3 Method A and DIN 53240.The polyol partial ester of poly(polyhydroxy fatty acid) according to this invention preferably has a saponification value of 30-300 mg KOH / g, preferably 100-250 mg KOH / g.Suitable detection methods for determining the saponification value are in particular those according to DGF C-V 3, DIN EN ISO 3681 and Ph. Eur. 2.5.6.A further subject of the instant invention are mixtures comprising a polyol partial ester of poly(polyhydroxy fatty acid) obtainable by the process of the instant invention and at least one selected from cosmetic oils and emollients.To facilitate the handling of the polyol partial ester of poly(polyhydroxy fatty acid), said mixtures preferably comprise cosmetic oils and / or emollients, wherein the oils and / or emollients bear a viscosity in the range of 1-100 mPa s at 25 °C and a surface tension in the range of 25-34 mN / m.A suitable method for determining the viscosity is using a Brookfield RV viscometer (with spindle SC4- 21 , running at 20 RPM and displaying a % torque of 53.0; torque constant = 1 , spindle multiplier constant = 5, spindle shear rate constant = 0.93) and a Brookfield Thermosel.The surface tension is determined by the ring method in accordance with du Nouy at 20°C.The cosmetic oils and emollients which are compromised in said mixtures are preferably selected from the group of natural oils, isoamyl laurate, isoamyl cocoate, diethylhexyl carbonate, isopropyl myristate, isopropyl palmitate, decyl cocoate, ethylhexyl palmitate, phenoxyethyl caprylate, C12-15 alkyl benzoate, ethylhexyl stearate, cetyl ethylhexanoate, lauryl oleate, caprylic / capric triglyceride, tripelargonin, PPG-3 myristyl ether, oleyl erucate, adansonia, digitata seed oil, PPG -15, stearyl ether and PPG -14 butyl ether, preferably natural oils.Preferably, the ratio (w / w) of all polyol partial ester of poly(polyhydroxy fatty acid) to all cosmetic oil and emollient comprised in said mixture is from 30:70 to 99.5:0.5.Preferably, all polyol partial ester of poly(polyhydroxy fatty acid) and all cosmetic oil and emollient comprised in said mixture account for at least 50 wt.-%, preferably at least 70 wt.-%, more preferably at least 90 wt.-%, of the total mixture.Since the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention and the mixtures according to the instant invention have an excellent use profile in, especially cosmetic, formulations, the present invention further provides the use of a polyol partial ester of poly(polyhydroxy fatty acid) according to the instant invention for preparation of a formulation, preferably an aqueous formulation.The formulation prepared by the use according to the instant invention preferably is a cosmetic or pharmaceutical formulation, preferably for topical application.The formulation prepared by the use according to the instant invention preferably comprises at least one further additional component selected from the group comprising emollients, emulsifiers, co-emulsifiers, thickeners / viscosity regulators / stabilizers, antioxidants, hydrotropes (or polyols), solids and fillers, pearlescent additives and opacifiers, insect repellents, self-tanning agents, preservatives, conditioning agents, perfumes, colorants, cosmetic active substances, care additives, refatting agents, solvents.Substances that can be used as exemplary representatives of the individual groups are known to those skilled in the art and can for example be taken from German application DE102008001788.4. This patent application is hereby incorporated as reference and is thus considered to form part of the disclosure.As regards further optional components and also the amounts used of these components, reference is expressly made to the relevant handbooks known to those skilled in the art, for example K. Schrader, “Grundlagen und Rezepturen der Kosmetika” [Fundamentals and formulations of cosmetics], 2nd edition, pages 329 to 341 , Huthig Buch Verlag, Heidelberg.The amounts of the respective additives depend on the intended use.Typical guideline formulations for the relevant applications are known prior art and are contained for example in the brochures of the manufacturers of the relevant base materials and active substances. These existing formulations can generally be adopted unchanged. However, any desired modifications necessary for adjustment and optimization can be made in a straightforward manner through simple tests.The present invention further provides formulations comprising a polyol partial ester of poly(polyhydroxy fatty acid) according to the instant invention or a mixture of the instant invention,preferred formulations according to the instant invention are those preferably obtained in the above process according to the instant invention.The present invention further provides the use of a polyol partial ester of poly(polyhydroxy fatty acid) according to the instant invention or a mixture of the instant invention as emulsifier in aqueous formulations, preferably as W / O emulsifier.Brief description of the drawingsFigure 1 : Schematic drawing of the exemplary synthesis routes to obtain poly(9,10-dihydroxystearic acid) as precursor for the esterification with a polyol starting from oleic acid. The shown structure of poly(9,10-dihydroxystearic acid) is only a representative structure as the poly(polyhydroxy fatty acid) according to this invention can comprise mixtures of regioisomers as well as polyesters in which both of the vicinal hydroxyl groups of at least some of the monomers are esterified.The examples that follow describe the present invention by way of example without any intention to limit the invention, the scope of application of which is apparent from the entirety of the description and the claims, to the embodiments specified in the examples.ExamplesEpoxidationsExample 1: Enzymatic epoxidation of oleic acid to 9, 10-epoxyoctadecanoic acidA mixture of oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, iodine value (IV) = 92 g 1 / 100 g, 523.75 g, 1 .86 mol of carbon-carbon double bonds = 1 .00 equiv.) and immobilized Candida antarctica lipase B enzyme (15.7 g, Purolite D5619, corresponding to 136339 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 210.56 g, 1.85 mol, 1.00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 40 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a slightly yellow liquid which solidified upon storage to give a white solid with waxlike consistency and an epoxy-[O] content of 3.8%.Example 2: Enzymatic epoxidation of oleic acid to 9, 10-epoxyoctadecanoic acidA mixture of oleic acid (DakoLub MB 6098, AV = 198 mg KOH / g, IV = 87 g 1 / 100 g, 173.85 g, 0.62 mol of carbon-carbon double bonds = 1.00 equiv.) and immobilized Candida antarctica lipase B enzyme (5.4 g, Purolite D5619, corresponding to 46894 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 69.8 g, 0.62 mol, 1.00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 40 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a slightly yellow liquid which solidified upon storage to give a white solid with waxlike consistency with an epoxy-[O] content of 3.8%.Example 3: Enzymatic epoxidation of linoleic acid to 9, 10:12, 13-diepoxyoctadecanoic acidA mixture of linoleic acid (Caila & Pares Cypacid G-35, AV = 200 mg KOH / g, IV = 133 g 1 / 100 g, 246.4 g, 1.29 mol of carbon-carbon double bonds = 1.00 equiv.) and immobilized Candida antarctica lipase B enzyme (7.4 g, Purolite D5619, corresponding to 64261 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 146.3 g, 1 .29 mol, 1 .00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 40 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a yellow liquid which solidified upon storage to give a yellowish solid with waxlike consistency and an epoxy-[O] content of 3.4%.Example 4: Enzymatic epoxidation of erucic acid to 13, 14-epoxydocosanoic acidA mixture of erucic acid (Oleon Nouracid RE07, AV = 166 mg KOH / g, IV = 72 g 1 / 100 g, 292.1 g, 0.875 mol of carbon-carbon double bonds = 1.00 equiv.) and immobilized Candida antarctica lipase B enzyme (8.7 g, Purolite D5619, corresponding to 75550 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 99.2 g, 0.875 mol, 1 .00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 50 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a slightly yellow liquid which solidified upon storage to give a white solid with an epoxy-[O] content of 2.8%.Example 5: Enzymatic epoxidation ofricinoleic acid to 9, 10-epoxy-12-hydroxyoctadecanoic acidA mixture of ricinoleic acid (Oleon Nouracid CZ 80, AV = 183 mg KOH / g, IV = 90 g 1 / 100 g, 253.05 g, 0.789 mol of carbon-carbon double bonds = 1.00 equiv.) and immobilized Candida antarctica lipase Benzyme (7.5 g, Purolite D5619, corresponding to 64755 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 89.5 g, 0.790 mol, 1 .00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 40 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a colourless, clear liquid with an epoxy-[O] content of 1 .7%.Example 6: Enzymatic epoxidation of undecylenic acid to 10, 11-epoxy-undecanoic acidA mixture of undec-10-enic acid (TH. Geyer, 98%, 198.3 g, 1.076 mol of carbon-carbon double bonds = 1.00 equiv.) and immobilized Candida antarctica lipase B enzyme (6.0 g, Purolite D5619, corresponding to 52104 PLU) was heated to 40 °C with stirring and while N2 passing through. After reaching 40 °C, hydrogen peroxide (30% aq., 122.0 g, 1.076 mol, 1.00 equiv.) was added dropwise over the course of 2 h and then the mixture was stirred at 40 °C for 24 h. Afterwards the mixture was dried at 65 °C and 10 mbar for 2 h. The mixture was filtered through a Buchner funnel with black band filter to remove the enzyme. The obtained product was a colourless, clear liquid which partially solidified upon storage and had an epoxy-[O] content of 1 .2%.Conversion of epoxy-fatty acids to polyhydroxy fatty acidsExample 7: Conversion of 9, 10-epoxyoctadecanoic acid to 9, 10-dihydroxyoctadecanoic acidA mixture 9,10-epoxyoctadecanoic acid obtained according to Example 1 (90 g), water (8.23 g) and sulfuric acid (96%, 1 .79 g) was heated to reflux at 120 °C for 4 h with stirring. After cooling to room temperature, the mixture was washed with water (2 x 20 mL). The obtained product was a turbid, yellow liquid.Example 8: Conversion of 9, 10:12, 13-diepoxyoctadecanoic acid to 9, 10:12, 13- tetrahydroxyoctadecanoic acidA mixture of 9, 10: 12,13-diepoxyoctadecanoic acid obtained according to Example 3 (68.81 g), water (6.24 g) and sulfuric acid (96%, 1 .31 g) was heated to reflux at 120 °C with stirring for 4 h. After cooling to room temperature, the mixture was washed with water (2 x 20 mL). The obtained product was a turbid, amber liquid.Polymerization of Epoxy- or Polyhydroxy Fatty AcidsExample 9: Polymerization of 9, 10-epoxyoctadecanoic acid to poly(9, 1 O-dihydroxyoctadecanoic acid)9.10-epoxyoctadecanoic acid obtained according to Example 1 (196.0 g) was heated to 120 °C for 14 h with stirring and while N2 passing through. The obtained product was a viscous yellow liquid with an AV of 60 mg KOH / g, an SV of 202 mg KOH / g, an OHV of 135 mg KOH / g and an epoxy-[O] content of 0.3%.Example 10: Polymerization of 9, 10-dihydroxyoctadecanoic acid to poly(9, 10-dihydroxyoctadecanoic acid)9.10-dihydroxyoctadecanoic acid obtained according to Example 7 (155.3 g) was heated to 200 °C for 4.5 h with stirring and while N2 passing through. The obtained product was a viscous yellow liquid with an AV of 55 mg KOH / g, an SV of 202 mg KOH / g, and an OHV of 122 mg KOH / g.Example 11: Polymerization of 9, 10:12, 13-diepoxyoctadecanoic acid to poly(9, 10, 12, 13- tetrahydroxyoctadecanoic acid)9,10:12,13-diepoxyoctadecanoic acid obtained according to Example 3 (178.0 g) was heated to 120 °C for 14 h with stirring and while N2 passing through. The obtained product was a viscous yellow liquid with an AV of 58 mg KOH / g, an SV of 201 mg KOH / g, an OHV of 163 mg KOH / g and an epoxy- [O] content of 0.1 %.Example 12: Polymerization of 13, 14-epoxydocosanoic acid to poly( 13, 14-dihydroxydocosanoic acid)13,14-epoxydocosanoic acid obtained according to Example 4 (164.9 g) was heated to 120 °C for 16 h with stirring and while N2 passing through. The obtained product was a viscous yellow liquid with an AV of 54 mg KOH / g, an SV of 167 mg KOH / g, an OHV of 110 mg KOH / g and an epoxy-[O] content of 0.2%.Polyol partial esters of polvfpolvhydroxy fatty acid)Example 13: Polyglycerol partial esters with poly(9, 10-dihydroxyoctadecanoic acid) (inventive)A mixture of poly(9,10-dihydroxyoctadecanoic acid) obtained according to Example 9 (AV = 60 mg KOH / g, 27.1 g) and oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 69.7 g, 0.247 mol) was heated to 200 °C for 3 h. Then, polyglycerol (OHV = 1100 mg KOH / g, 35.2 g) was added, and the mixture was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 5 mg KOH / g was reached. The obtained product was two-phase mixture at the ratio top to bottom ~ 9:1 . The mixture was separated using a separatory funnel at 80 °C. The bottom phase consisted mainly of unreacted polyglycerol, the isolated upper / top phase of the mixture was a yellow, clear liquid (AV = 1 .2 mg KOH / g, OHV = 126 mg KOH / g, SV = 164 mg KOH / g).Example 14: Polyglycerol partial esters with poly(9, 10, 12, 13-tetrahydroxyoctadecanoic acid) (inventive)A Mixture of poly(9,10,12,13-tetrahydroxyoctadecanoic acid) obtained according to Example 11 (AV = 58 mg KOH / g, 29.8 g) and oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 77.0 g, 0.273 mol) was heated to 200 °C for 3 h with stirring and nitrogen passing through. Then, polyglycerol (OHV = 1100 mg KOH / g, 37.2 g) was added, and the mixture was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 5 mg KOH / g was reached. The obtained product was a two-phase mixture at the ratio top to bottom ~ 9:1 . The mixture was separated using a separatory funnel at 80 °C. The bottom phase consisted mainly of unreacted polyglycerol, the isolated upper / top phase of the mixture was a yellow, clear liquid (AV = 2.0 mg KOH / g, OHV = 109 mg KOH / g, SV = 175 mg KOH / g).Example 15: Polyglycerol partial esters with poly( 13, 14-dihydroxydocosanoic acid) (inventive)A mixture of poly(13,14-dihydroxydocosanoic acid) obtained according to Example 12 (AV = 54 mg KOH / g, 28.0 g) and oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 72.2 g, 0.257 mol) was heated to 200 °C with stirring and nitrogen passing through. Then, polyglycerol (OHV = 1100 mg KOH / g, 34.8 g) was added and the mixture was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 5 mg KOH / g was reached. The obtained product was a two-phase mixture at the ratio top to bottom ~ 9:1 . The mixture was separated using a separatory funnel at 80 °C. The bottom phase consisted mainly of unreacted polyglycerol, the isolated upper / top phase of the mixture was a yellow, clear liquid (AV = 1 .7 mg KOH / g, OHV = 96 mg KOH / g, SV = 170 mg KOH / g).Example 16: Polyglycerol partial esters with poly(9, 10-dihydroxyoctadecanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 33.6 g), poly(9,10-dihydroxyoctadecanoic acid) obtained according to Example 9 (AV = 60 mg KOH / g, 27.0 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 69.72 g, 0.247 mol) and sebacic acid (13.0 g, 0.064 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 2.0 mg KOH / g was reached. The obtained product was a yellow, clear liquid (AV = 0.4 mg KOH / g, OHV = 144 mg KOH / g, SV = 192 mg KOH / g).Example 17: Polyglycerol partial esters with poly(9, 10-dihydroxyoctadecanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 28.4 g), poly(9,10-dihydroxyoctadecanoic acid) obtained according to Example 9 (AV = 60 mg KOH / g, 45.6 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 58.9 g, 0.209 mol) and sebacic acid (11 .0 g, 0.054 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 3.0 mg KOH / g was reached. The obtained product was a yellow, clear liquid (AV = 0.5 mg KOH / g, OHV = 133 mg KOH / g, SV = 196 mg KOH / g).Example 18: Polyglycerol partial esters with poly(9, 10-dihydroxyoctadecanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 34.3 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 68 g, 0.241 mol) and sebacic acid (13.3 g, 0.066 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 7.0 mg KOH / g was reached. Then, a mixture of poly(9,10- dihydroxyoctadecanoic acid) obtained according to Example 9 (AV = 60 mg KOH / g, 26.7 g) and oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 2.8 g, 0.01 mol) which was preheated to 140 °C for 4 h was added, the combined mixtures were heated to 240 °C with stirring and nitrogen passing through and the resulting water was continuously distilled until an acid value of 2.0 mg KOH / g was reached. The product was a yellow, clear liquid with an AV = 0.6 mg KOH / g, an OHV = 137 and a SV = 196.Example 19: Polyglycerol partial esters with poly(9, 10-dihydroxyoctadecanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 33.6 g), poly(9,10-dihydroxyoctadecanoic acid) obtained according to Example 10 (AV = 55 mg KOH / g, 27.0 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 69.72 g, 0.247 mol) and sebacic acid (13.0g, 0.064 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 2.0 mg KOH / g was reached. The obtained product was a yellow, clear liquid (AV = 0.9 mg KOH / g, OHV = 128 mg KOH / g, SV = 194 mg KOH / g).Example 20: Polyglycerol partial esters with poly(9, 10, 12, 13-tetrahydroxyoctadecanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 33.7 g), poly(9,10,12,13-tetrahydroxyoctadecanoic acid) obtained according to Example 11 (AV = 58 mg KOH / g, 27.0 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 69.7 g, 0.248 mol) and sebacic acid (11 .0 g, 0.054 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 3.0 mg KOH / g was reached. The obtained product was a yellow, clear liquid (AV = 0.3 mg KOH / g, OHV = 150 mg KOH / g, SV = 200 mg KOH / g).Example 21: Polyglycerol partial esters with poly( 13, 14-dihydroxydocosanoic acid) (inventive)A mixture of polyglycerol (OHV = 1100 mg KOH / g, 33.6 g), poly(13,14-dihydroxydocosanoic acid) obtained according to Example 12 (AV = 54 mg KOH / g, 27.0 g), oleic acid (Palmera A1818 from KLK Emmerich GmbH, AV = 200 mg KOH / g, IV = 92 g 1 / 100 g, 69.72 g, 0.247 mol) and sebacic acid (13.0 g, 0.064 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 3.0 mg KOH / g was reached. The obtained product was a yellow, clear liquid (AV = 0.6 mg KOH / g, OHV = 145 mg KOH / g, SV = 196 mg KOH / g).Comparative Example 22: Polyglycerol partial esters according to Example 13 of EP 1500427 with poly( 12-hydroxystearic acid) (non-inventive)A mixture of polyglycerol (OHV = 1190 mg KOH / g, 63.0 g), isostearic acid (PRISORINE 3505-LQ- (GD) from CRODA GmbH, AV = 193 mg KOH / g, 91 .1 g, 0.313 mol) and sebacic acid (20.2 g, 0.100 mol) was heated to 240 °C with stirring and nitrogen passing through. The resulting water was continuously distilled until an acid value of 9.0 mg KOH / g was reached. Then, poly (12-hydroxystearic acid) (AV = 45 mg KOH / g, 141 .7 g, 0.114 mol) was added, the combined mixtures were heated to 240 °C with stirring and nitrogen passing through and the resulting water was continuously distilled until an acid value of 4.3 mg KOH / g was reached.Application ExamplesThe purpose of the following examples is to differentiate the emulsification performance of the polyol partial esters of poly(polyhydroxy fatty acid) according to the invention against the state of the art. Application Example 23:A comparison was performed against the poly(12-hydroxystearic acid) containing polyol partial esters of Comparative Example 22 according to Example 13 of EP1500427.For the preparation of the emulsions, homogenization techniques known to the skilled person were used. All concentrations are given in weight percent. The preparation was performed cold / cold. To analyse the emulsion stability, the emulsions were stored for one month at 25°C and three days at 50°C. The resistance of the emulsions to freeze-thawing was investigated by performing three consecutive freeze-thaw cycles (-15°C / 25°C).‘according to the inventionIn test formulation 1 , all inventive polyol partial esters showed a stabilization performance after storage for one month at 25 °C and for 3 days at 50 °C which was comparable to the one ofComparative Example 22. In addition, it was surprisingly found that all of the inventive polyol partial esters provided perfect stabilization over the course of three consecutive freeze-thaw cycles while covering a wide range of different viscosities and with Example 13 showing a viscosity nearly identical to the one of Comparative Example 22.It is to be noted, that Comparative Example 22, resembling an example of EP1500427, according to this writ, already bears outstanding resistance to freezing-thawing, which is outperformed by the polyol partial esters of poly(polyhydroxy fatty acid) of the instant invention.Application Example 23b:An even more challenging test was performed using formulations which were identical to formulations 1a-e but using only 1 .5% instead of 2.0% of polyol partial esters.When the formulations were submitted to storage testing at 50 °C for 48 h, also here the inventive polyol partial esters were able to perfectly stabilize these emulsions at almost identical viscosities.Application Example 24:The emulsions were prepared analogously to the formulations shown in Application Example 23.Formula 2a-e contain a less polar oil phase as compared to formula 1a-e.‘according to the inventionExactly as Comparative Example 22 which was used in formula 2a, the inventive polyol partial esters of poly(polyhydroxy fatty acid) gave emulsions that showed no instabilities upon storage at 50 °C for 3 days. Surprisingly it was found that inventive polyol partial ester Example 13 provided freeze-thaw resistance to the test formulation and outperformed Comparative Example 22 in formula 2a although both emulsions did not differ in their viscosity. It is to be noted, that Comparative Example 22, resembling an example of EP1500427, according to this writ, already bears outstanding resistance to freezing-thawing, which is outperformed by the polyol partial esters of poly(polyhydroxy fatty acid) of the instant invention.Formulation examplesThe following example emulsions are intended to explain the subject-matter of the invention in more detail without limiting it to these examples. The examples show that the inventive emulsifier can be used for the stabilization of versatile cosmetic formulations as well as for the dispersion of pigments and other solids. Furthermore, the examples show the compatibility with typical co-emulsifiers, cosmetic oils, emollients, waxes and stabilizers as well as the tolerance against emulsiondestabilizing components such as UV-filters, antimicrobials, electrolytes and active ingredients.The preparation was performed either hot / cold or cold / cold using homogenization techniques known to the skilled person. When using the hot / cold procedure, the oil phase was typically heated to 75 - 80°C. The water phase was then added within 2 min while stirring. Afterwards the mixture was homogenized shortly and cooled down. After reaching a temperature of < 30°C, the emulsion was homogenized again. In case of a cold / cold process the water phase was added to the oil phase within 2 min while stirring. Afterwards the emulsion was homogenized. Compounds like preservatives or active ingredients were preferably added below 40°C after homogenization. When using organic acid as preservative, the pH was adjusted in the water phase.The sample formulations listed below were prepared with each of the polyol partial esters of examples 13 to 21 according to the invention (hereinafter marked "Example X"). Therefore, 9 different formulations were prepared for each example formulation which is presented below.W / 0 creamCold processable lotionMoisturizing lotion with ureaW / O lotion with silky-velvety skin feelBaby careFoot careSun protection SPF 30 UVA with insect repellentSun protection SPF 30 UVA according to eco-criteriaSun protection spray SPF 30 UVASun protection spray SPF 50 UVASun protection lotion with SPF 50 according to FDA-criteriaFoundation 1Foundation 2:CC (Color Control) FluidAP / Deo spray or aerosol spraySun protection aerosol SPF 50 UVACooling Body Lotion
Claims
Claims1 . Process for production of a polyol partial ester of poly(polyhydroxy fatty acid) comprising the steps ofA) providing at least one poly(polyhydroxy fatty acid),B) providing at least one polyol, preferably a mixture of more than one polyol,C) esterification of said at least one poly(polyhydroxy fatty acid) and said at least one polyol.
2. Process according to claim 1 characterized in that step A) comprises the sub-steps of A1) providing at least one unsaturated fatty acid,A2) epoxidation of at least one of the carbon-carbon double bonds of said at least one unsaturated fatty acid while obtaining an epoxy fatty acid, optional A3) opening of the epoxide group of said epoxy fatty acids while obtaining a polyhydroxy fatty acid, andA4) polymerizing said epoxy fatty acids and / or said polyhydroxy fatty acid while obtaining at least one poly(polyhydroxy fatty acid).
3. Process according to claim 2 characterized in that said unsaturated fatty acid is selected from the group of arachidonic acid, calendic acid, catalpic acid, dihomo-y-linolenic acid, docosahexaenoic acid, docosapentaenoic acid, docosatetraenoic acid, eicosapentaenoic acid, eicosatetraenoic acid, eicosenoic acid, 11-eicosenoic acid, elaidic acid, a-eleostearic acid, p- eleostearic acid, erucic acid, gadoleic acid, linoleic acid, linolelaidic acid, linolenic acid, a- linolenic acid, gamma-linolenic acid, mead acid, myristoleic acid, nervonic acid, octadecatetraenoic acid, octadecatrienoic acid, oleic acid, omega-3 fatty acid, omega-6 fatty acid, omega-7 fatty acid, omega-9 fatty acid, palmitoleic acid, a-parinaric acid, paullinic acid, petroselinic acid, pinolenic acid, punicic acid, ricinoleic acid, rumenic acid, sapienic acid, stearidonic acid, tuataric acid, undecylenic acid, vaccenic acid and vernolic acid, preferably erucic acid, linoleic acid, oleic acid and palmitoleic acid.
4. Process according to claim 2 or 3 characterized in that the epoxidation in sub-step A2) is catalyzed by an enzyme, preferably selected from the group of cytochrome P450 enzymes, lipoxygenases, peroxidases, epoxide hydrolases and lipases, preferably lipases in the presence of at least one peroxide, preferably hydrogen peroxide.
5. Process according to any of the preceding claims characterized in that said poly(polyhydroxy fatty acid) provided in step A) has an acid value of 10 to 200 mg KOH / g, preferably 35 to 120 mg KOH / g, especially preferably from 40 to 90 mg KOH / g.
6. Process according to any of the preceding claims characterized in that said poly(polyhydroxy fatty acid) provided in step A) has an epoxy-[O] content of <10.0 %, preferably <5.0 % more preferably <1.0 %.
7. Process according to any of the preceding claims characterized in that said poly(polyhydroxy fatty acid) provided in step A) has an hydroxyl value of 10 to 400 mg KOH / g, preferably 50 to 300 mg KOH / g, especially preferably from 70 to 200 mg KOH / g.
8. Process according to any of the preceding claims characterized in that said polyol provided in step B) has three or more, preferably four or more, in particular more than six, carbon atoms.
9. Process according to any of the preceding claims characterized in that said polyol provided in step B) is selected from the group of 1 1 ,10-decanediol, 1 ,12-dodecanediol, 1 ,2-hexanediol, 1 ,2- octanediol, 1 ,2-pentylene glycol, 1 ,4-bis(hydroxymethyl)cyclohexane, 1 ,5-pentanediol, 2,2,4- trimethy 1-1 ,3-pentanediol, 2,2-bis(4-hydroxycyclohexyl)propane, 2,2-dimethyl-1 ,3-propanediol (neopentyl glycol), 2, 4-diethy 1-1 ,5-pentane, 2,5-dimethyl-3-hexine-2,5-diol, 2-buty l-2-ethy 1-1 ,3- propanediol, 2-butyl-2-ethyl-1 ,3-propanediol, 2-ethyl-1 ,3-hexanediol, 2-methyl-1 ,3-propanediol, 2-methyl-2-propyl-1 , 3-propanediol, 2-methyl-2-propyl-1 ,3-propanediol, 2-sec-butyl-2-methyl- 1 ,3-propane, 3-hexine-2,5-diol, ditrimethylolpropane, isosorbide, pinacol, tricyclodecanediethanol, tripentaerythritol, 1 ,2-butylene glycol, 1 ,2-propylene glycol, 1 ,3- butylene glycol, 1 ,3-propanediol, 1 ,4-butanediol, 1 ,4-sorbitan, 1 ,5-sorbitan, diglycerin, dipentaerythritol, erythritol, glycerin, isomalt, lactitol, maltitol, mannitol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, xylitan, xylitol and polyglycerol, preferably polyglycerol.
10. Process according to claim 9 characterized in that said polyglycerol provided in step B) has mean degree of polymerization of from 2.0 to 20, preferably 2.5 to 16 and most preferably 3.0 to 12.11 . Process according to claim 9 or 10 characterized in that said polyglycerol provided in step B) has a content of cyclic oligomers from 1 .0% by weight to 50% by weight, preferably from 2.0% by weight to 40% by weight, particularly preferably from 3.0% by weight to 30% by weight, wherein the weight percentages refer to all polyglycerols provided in step B).
12. Process according to any of the preceding claims characterized in that in process step C) at least one selected from monocarboxylic acids and polycarboxylic acids, preferably dicarboxylic acids, are co-esterified into the polyol.
13. Polyol partial ester of poly(polyhydroxy fatty acid) obtainable by a process according to any of the preceding claims.
14. Mixture comprising a polyol partial ester of poly(polyhydroxy fatty acid) of claim 13 and at least one selected from cosmetic oils and emollients.
15. Use of a polyol partial ester of poly(polyhydroxy fatty acid) according to claim 14 or a mixture of claim 14 for preparation of a formulation, preferably an aqueous formulation, and / or as emulsifier in an aqueous formulation, preferably as W / O emulsifier.
Citation Information
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