Butylene glycol esters of c8-c10 fatty acids

Abstract

The invention relates to an enzymatic process of producing butylene glycol esters, the esters obtainable by the process and the use of said esters.

Description

Butylene glycol esters of C8-C10 fatty acidsField of the inventionThe invention relates to an enzymatic process of producing butylene glycol esters, the esters obtainable by the process and the use of said esters.Prior artIt is known that natural o / w-emulsions with a higher proportion of consistency enhancers and polymeric thickener tend to whiten and soap on the skin during application. The foam which leads to the white appearance on the skin can be reduced e.g. by the addition of a silicone oil to the formulation. In natural formulations silicone oils are not often used.The object of the present invention was therefore to provide an emollient that reduces whitening and soaping during the application of a formulation.Description of the inventionIt was found that, surprisingly, that the esters, enzymatically prepared by the process according to the instant invention help to solve the above problem and can reduce whitening of a cosmetic formulation significantly.The present invention therefore provides an enzymatic process of producing butylene glycol esters according to claim 1 .One advantage of the present invention is that the butylene glycol ester according to the instant invention have a superior colour.Another advantage of the present invention is that the butylene glycol ester according to the instant invention have a superior smell.A further advantage is that the butylene glycol esters according to the instant invention yield in a good spreadability of the formulation they are comprised in.Another advantage is that the butylene glycol ester according to the instant invention make formulations to be adsorbed by the skin in a better way.An additional advantage is that the butylene glycol ester according to the instant invention make formulations feel less waxy on the skin.Another advantage is that the butylene glycol ester according to the instant invention make formulations feel less sticky on the skin.A further advantage is that the butylene glycol ester according to the instant invention make formulations feel more slippery on the skin.A further advantage is that the butylene glycol ester according to the instant invention make pigment-containing formulations easier to distribute on the skin.A further advantage is that the butylene glycol ester according to the instant invention make pigment-containing formulations to distribute more homogeneously on the skin.A further advantage is that the butylene glycol ester according to the instant invention keeps the colour appearance of pigment-containing formulations more constant while distributing on the skin. A further advantage is that the butylene glycol ester according to the instant invention has excellent solvent properties for UV filters.The instant invention thus provides a process for the preparation of butylene glycol esters of at least one fatty acid with 8 to 10 carbon atoms comprising the stepsI) providing butylene glycol and at least one fatty acyl group donor providing at least one fatty acyl group comprising 8 to 10 carbon atoms,II) enzyme catalysed esterification of said butylene glycol and said at least one fatty acyl group, and optional III) packaging of said prepared butylene glycol esters in a closed container.Where average values are stated hereinbelow, then, unless stated otherwise, these are number- averaged average values.Unless stated otherwise, percentages are data in per cent 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.Any type of fatty acyl group donor can be provided in step I) of the process of the instant invention, as long as fatty acyl groups comprising 8 to 10 carbon atoms are provided.A preferred process according to the instant invention is characterised in that said acyl group donor is selected from fatty acids and fatty acid esters, preferably methyl-, ethyl- and glycerol esters, wherein the glycerol esters are preferably fatty acid triglycerides, more preferably natural oils.Most preferred fatty acyl group donor are fatty acids.Of course, said fatty acyl group donor provided in step I) of the process of the instant invention can also provide fatty acyl groups different from acyl groups comprising 8 to 10 carbon atoms. This is especially true for fatty acyl group donors of natural origin.However, it is preferred according to the instant invention, that at least 80 wt.%, preferably at least 95 wt.%, more preferably at least 98 wt.%, of all fatty acyl groups provided in the process of the instant invention are selected from said at least one fatty acyl group comprising 8 to 10 carbon atoms.A preferred process according to the instant invention is characterised in that said fatty acyl group is selected from caprylate, pelargonate and caprate, preferably a mixture of caprylate and caprate, most preferably pelargonate.If a mixture of caprylate and caprate is provided, it is preferred that they have a weight ratio of from 99 : 1 to 1 : 99, preferably from 65 : 40 to 55 : 40.A preferred process according to the instant invention is characterised in that the molar ratio of said butylene glycol to all fatty acyl groups provided by said fatty acyl group donor is in the range of from 1 : 1 .2 to 1 : 2.8, preferably from 1 : 1 .4 to 1 : 2.2, more preferably from 1 : 1 .51 to 1 : 1 :99.A preferred process according to the instant invention is characterised in that process step II) is catalysed by a lipase.Lipases preferably used in accordance with the invention in process step I) are present immobilized on a solid support.Preferably said lipase is selected from the group comprising, preferably consisting of, 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 ProteinBank 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 the reaction 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 thatthe 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 I), preference is given in accordance with the invention to using 500 PLU to 2000 PLU, preferably from 200 PLU to 1500 PLU, more preferably from 25 PLU to 1250 PLU, of lipase per gram of fatty acyl groups to be converted.A preferred process according to the instant invention is characterised in that process step II) is carried out in a temperature range of from 20 °C to 95 °C, preferably 30 °C bis 70 °C, more preferably 37 °C to 65 °C, even more preferably 45 °C to 60 °C.Preferably in the process according to the instant invention in process step II) reaction water is removed from the reaction, preferably under reduced pressure.Process step II) is according to the invention preferably carried out at a pressure of less than 0.8 bar, preferably less than 0.5 bar and more preferably less than 0.1 bar.The present invention further provides a butylene glycol ester of at least one fatty acid with 8 to 10 carbon atoms obtainable by a process according to the instant invention.A preferred butylene glycol ester according to the instant invention has a degree of esterification of from 90.0 % to 99.9 %, preferably from 95.0 % to 99.0 %.The degree of esterification can be determined by the hydroxyl value.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.Since the butylene glycol esters according to the invention have an excellent use profile in, especially cosmetic, formulations, the present invention further provides the use of a butylene glycol ester according to the invention for preparation of a formulation, preferably an aqueous formulation, even more preferably in form of an emulsion, preferably w / o- or o / w emulsion, most preferably o / w emulsion.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, film formers perfumes, colorants, cosmetic active substances, care additives, refatting agents, solvents andUV light protection filter substances.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 formulation prepared by the use according to the instant invention preferably comprises at least one natural thickener, preferably selected from the group of xanthan gum, guar gum, carrageenan, agar, gelatine, pectin, alginates, chitosan, konjac gum, cellulose gum, acacia gum, gellan gum, locust bean gum, arrowroot powder, corn-starch, rice starch, potato starch, tapioca starch, wheat starch, soybean flour, maltodextrin, inulin and squalene:The formulation prepared by the use according to the instant invention preferably comprises at least one substance selected from the group of UV light protection filter substances and pigments, especially UV light protection filter substances, which are preferably organic.The UV light protection filter substances present may for example be organic substances that are capable of absorbing ultraviolet rays and re-emitting the absorbed energy in the form of longer- wavelength radiation, for example heat.UVB filters can be oil-soluble or water-soluble. Examples of oil-soluble UVB light protection filters include:3-benzylidenecamphor derivatives, for example 3-(4-methylbenzylidene)camphor (INCI: 4- Methylbenzylidene Camphor), 4-aminobenzoic acid derivatives, for example 2-ethylhexyl 4- (dimethylamino)benzoate (INCI: Ethylhexyl Dimethyl PABA), 2-hydroxyethyl 4-{bis[2-(2- hydroxyethoxy)ethyl]amino}benzoate (INCI: PEG-25 PABA), cinnamic esters, for example 2- ethylhexyl 4-methoxycinnamate (INCI: Ethylhexyl Methoxycinnamate), isopentyl 4- methoxycinnamate (INCI: Isoamyl p-Methoxycinnamate), 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (INCI: Octocrylene), salicylic esters, for example 2-ethylhexyl salicylate (INCI: Ethylhexyl Salicylate), homomenthyl salicylate (INCI: Menthyl Salicylate), 3,3,5-trimethylcyclohexyl salicylate (INCI: Homosalate), 2-hydroxybenzoic acid - 2,2',2"-nitrilotriethanol (1 :1) (INCI: TEA-Salicylate), benzophenone derivatives, for example 2-hydroxy-4-methoxybenzophenone (INCI:Benzophenone-3), 2,2'-dihydroxy-4-methoxybenzophenone (INCI: Benzophenone-8), 2-hydroxy-4- methoxy-4‘-methylbenzophenone (INCI: Benzophenone-10), triazine derivatives, for example tris(2- ethylhexyl) 4,4',4"-(1 ,3,5-triazine-2,4,6-triyltriimino)tribenzoate (INCI: Ethylhexyl Triazone, obtainable for example under the trade name Uvinul T 150 from BASF), iscotrizinol (INCI: Diethylhexyl Butamido Triazone) and 2,4,6-tri(4-biphenylyl)-1 ,3,5-triazine (INCI: Tris-Biphenyl Triazine).An additional UVB filter is the (3-(4-(2,2- bis(ethoxycarbonyl)vinyl)phenoxy)propenyl)methoxysiloxane / dimethylsiloxane copolymer (INCI: Polysilicone-15) obtainable for example under the trade name Parsol SLX.Useful water-soluble UVB sun protection filters include for example: salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts, and also the sulfonic acid itself having the INCI name Phenylbenzimidazole Sulfonic Acid, sulfonic acid derivatives of benzophenone, for example 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid (INCI: Benzophenone-4) and salts thereof, benzenesulfonic acid derivatives of 3-benzylidenecamphor, for example 4-[(E)-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-ylidene)methyl]benzenesulfonic acid (INCI: Benzylidene Camphor Sulfonic Acid) and salts thereof.Examples of typical oil-soluble UVA / broadband light protection filters that may be used include derivatives of benzoylmethane, for example 1-(4-methoxyphenyl)-3-[4-(2-methyl-2- propanyl)phenyl]-1 ,3-propanedione (INCI: Butyl Methoxydibenzoylmethane) or 1-(4-isopropy lphenyl)-3-phenyl-1 ,3-propanedione (INCI: Isopropyl Dibenzoylmethane), triazine derivatives, for example 2,2'-[6-(4-methoxyphenyl)-1 ,3,5-triazine-2,4-diy I] bis{5-[(2- ethylhexyl)oxy]phenol} (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, obtainable for example under the trade name Tinosorb S from BASF), N,N'-bis[4-[5-(1 ,1-dimethylpropyl)-2- benzoxazolyl]phenyl]-N"-(2-ethylhexyl)-1 ,3,5-triazine-2,4,6-triamine (INCI: Ethylhexyl Bis- Isopentylbenzoxazolylphenyl Melamine, obtainable under the trade name Uvasorb K2A from 3V Sigma), and derivatives of benzophenone, for example hexyl 2-(4-diethylamino-2- hydroxybenzoyl)benzoate (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate).Useful water-soluble UVA / broadband light protection filters include, for example: 3 ,3'-(1 ,4- phenylenedimethylene)-bis(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-ylmethanesulfonic acid) and salts thereof, especially the corresponding sodium, potassium or triethanolammonium salt, which is also described as benzene-1 ,4-di(2-oxo-3-bornylidenemethyl-10-sulfonic acid) and has the INCI name Terephthalylidene Dicamphor Sulfonic Acid (obtainable under the trade name Mexoryl SX), 2,2'-(1 ,4-phenylene)-bis(6-sulfo-1 H-benzimidazole-4-sulfonic acid) and salts thereof, the corresponding sodium, potassium or triethanolammonium salts, for example disodium 2,2'-(1 ,4- phenylene)-bis(6-sulfo-1 H-benzimidazole-4-sulfonate) having the INCI name Disodium Phenyl Dibenzimidazole Tetrasulfonate, trade name for example Neo Heliopan AP.Examples of other UVA / broadband filters are 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(2,4,4- trimethyl-2-pentanyl)phenol] (INCI: Methylene Bis-Benzotriazoly I Tetramethylbutylphenol, obtainable for example under the trade name Tinosorb M from BASF), 2-(2H-benzotriazol-2-yl)-4- methyl-6-[2-methyl-3-[1 ,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]phenol (INCI: Drometrizole Trisiloxane, trade name: Mexoryl XL), (1 R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2- aminobenzoate (INCI: Menthyl Anthranilate) and 2-ethoxyethyl (2E)-3-(4-methoxyphenyl)acrylate (INCI: Cinoxate).The UV filters may of course also be present in mixtures in the formulations according to the invention.In addition to the soluble UV light protection filter substances mentioned, insoluble pigments may also be used for this purpose, namely finely dispersed metal oxides or salts, for example titanium dioxide, zinc oxide, iron oxide, aluminium oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate. The particles should here have an average diameter of less than 100 nm, for example of between 5 and 50 nm and especially between 15 and 30 nm. They may be spherical in shape, but it is also possible to use particles that are ellipsoidal in shape or have a shape that deviates in another way from spherical. Also possible however are micronized organic pigments, for example 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethyl-2- pentanyl)phenol] (INCI: Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, obtainable for example under the trade name Tinosorb M from BASF), having a particle size of < 200 nm, which is obtainable for example as a 50% aqueous dispersion.In addition, further suitable UV light protection filters are given in the review by P. Finkel in SOFW Journal, 122, 543 (1996) or in the chapter “The Chemistry of Ultraviolet Filters” by N.A. Shaath in “Principles and Practice of Photoprotection”, S.Q. Wang, H.W. Lim (eds.), Springer International Publishing, Switzerland, 2016.It is preferable in accordance with the invention that the formulation prepared by the use of the invention comprises at least two, preferably at least three, more preferably at least four, selected from the group of UV light protection filter substances.It is preferable in accordance with the invention that the formulation prepared by the use of the invention comprises at least one UV light protection filter substance selected from the group of triazine derivatives.The formulation prepared by the use according to the instant invention preferably comprises at least one pigment, preferably selected from unmodified or surface-modified, inorganic or organic pigments, preferably inorganic pigments such as activated carbon, talc, iron oxide pigments, titanium dioxide, zinc oxide, silica, cerium oxides, zirconium oxides, aluminium oxides, calcium carbonate, barium sulfate, chromium oxides, manganese oxides, bismuth oxychloride, ultramarine, calcium sulfate and alkali magnesium silicates.Examples of organic pigments may be: carotenoids, chlorophylls, xanthophylls, caramel and the salts of the recited examples and also dyes obtained from fruits of plants or other plant parts, for example from orange, cacao, turmeric, shea, sandalwood, onion, carob tree fruit, paprika, maize, tomato, beetroot, peanut, grape, red cabbage, red rice, radish, elderberry, lingonberry, blueberry, raspberry, blackberry, boysenberry, gooseberry, cranberry, saffron, strawberry, cherry, tea, hibiscus, plum, blueberry or mulberry. Also employable as dye pigments are the substances approved and suitable for cosmetic purposes, as listed for example in the publication “Kosmetische Farbemittel” [Cosmetic colorants] of the Dyes Committee of the Deutsche Forschungsgemeinschaft [German Research Foundation], Verlag Chemie, Weinheim, 1984, pages 81 to 106.It is in addition preferable in accordance with the invention that, when the formulation prepared by the use according to the invention comprises a component selected from the group of UV light protection filter substances, pigments selected from titanium dioxide and zinc oxide are additionally comprised in said formulation. In this connection too, the UV light protection filter substances that are preferably present correspond to the preferred UV light protection filter substances mentioned above.The present invention further provides the use of a butylene glycol esters according to the instant invention as anti-whitening-and-soaping agent in a formulation, preferably a cosmetic or pharmaceutical formulation for topical application. Preferred formulations in the context of saidinventive use are the formulations preferably prepared by the use the inventive use of a butylene glycol ester according to the invention for preparation of a formulation as described above.The present invention further provides a formulation comprising a butylene glycol ester according to the invention, preferred formulations according to the instant invention are those preferably obtained by the use the inventive use of a butylene glycol ester according to the invention for preparation of a formulation as described above.The examples adduced hereinafter describe the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, be restricted to the embodiments specified in the examples.Example 1: Synthesis example623.9 g of a mixture of caprylic and capric acid (60 : 40 molar ratio) (acid value = 361 mg KOH / g) was added alongside 180.0 g butylene glycol (hydroxy value = 1245 mg KOH Zg) into a stirring vessel. The mixture was heated to 80 °C under stirring. After adding immobilized enzyme Candida antarctica Lipase B (Fermenta TA10000; 8.00 g) the pressure was reduced to 20 mbar and the mixture stirred for 54 h. Water was continuously distilled from the reaction mixture. Finally, the immobilized enzyme was removed via filtration to yield the final product.Example 2: Synthesis example140.94 g of a mixture of caprylic and capric acid (60 : 40 molar ratio) (acid value = 361 mg KOH / g) was added alongside 41 .28 g butylene glycol (hydroxy value = 1245 mg KOH Zg) into bubble column. The mixture was heated to 80 °C under continuous nitrogen flow. After adding immobilized enzyme Candida antarctica Lipase B (Amano Lipase CL; 1 .82 g) the mixture was left for reaction for 25 h. Finally, the immobilized enzyme was removed via filtration to yield the final product.Example 3: Synthesis example, not according to the inventionA mixture of caprylic and capric acid (623.8 g; 60 : 40 molar ratio; acid value = 361 mg KOH / g) was added alongside butylene glycol (180.0 g; hydroxy value = 1245 mg KOH / g) into a stirring vessel, p-toluenesulfonic acid (1 .25 g; 0.2 %) was added and the mixture was heated to 200 °C under stirring and continuous nitrogen flow. After 8 h of stirring and continuous distillation of the occurring water the reaction was completed.Example 4: Whitening of a cosmetic formulations, given numbers are weight percentages:* according to the instant inventionThe natural o / w-emulsions which composition is shown in the table above was formulated according to the following procedure:1 . Heat phase A1 and phase B separately to 75°C2. Add Phase A2 to the heated phase A13. Add Phase B without stirring4. Homogenize5. Cool down to 30°C6. Add phase C and stir wellWhitening of the formulations was evaluated by a trained sensory panel. At least 5 persons are evaluating the whitening profile of the formulations without knowing the composition of the evaluated samples. The whitening was evaluated by a scoring from 0 (no whitening) to 10 (high whitening). Coming from the base system which is shown in formulation 1 whitening of the formulation can be reduced due to the addition of Example 1 and 2, shown in Formulation 2, 3 and 5 (according to the invention) but not by adding Example 3 as shown in Formulation 4 (not according to the invention).Example5: Skin feel of a formulation:The sensory of the creams of example 4 are evaluated by a trained sensory panel. At least 5 persons are evaluating the sensory profile of the formulations without knowing the composition of the evaluated samples. The properties the majority of the panelists have described is reported in the table below:* according to the instant inventionFormulation 4Formulation 5 ** according to the instant inventionExample formulations:The following examples demonstrate the applicability of the butylene glycol ester in different cosmetic formulations and their compatibility with various other ingredients such as emulsifiers, stabilizers, preservatives or active compounds like UV-filters or antimicrobial drugs which are usually challenging to formulate. The application of the invention is not limited to the formulations shown. The preparation of the examples has been done according to common standard methods.Natural body spray with moisturizing propertiesRegenerating anti-aging SerumBody cream 1Hydrating Body cream long-lasting moisturizing propertiesRich natural cream for enhanced elasticityDeep Comfort silky Body butter / W Sun Lotion with moisturizing effectUltra-comfortable waterproof Sun Spray SPF 30Revitalizing Cationic Hand Creme(PEG free) AP / Deo roll-onMilky Deo Roll-On for sensitive skinRenewal Body Oil Release LotionW / O-Make up foundationMake up with wrinkle filler effectW / 0 sun care - Sun Cream, SPF 50+All Day Sun Protection Lotion SPF 30High spreading Body sprayHydration & Wrinkle reduction O / W sunscreenW / 0 make-up FoundationDaily wear cationic lotion with UV protectionDaily Facial Cream, SPF 25Hydrating Foot Care CreamWater free Oil for Sun Care, SPF 50 1Water free Oil for Sun Care, SPF 50 2SPF 30 Sun Care Lotion 1SPF 30 Sun Care Lotion 2Natural Sun Care Formulation 1Natural Sun Care Formulation 2

Claims

Claims1 . Process for the preparation of butylene glycol esters of at least one fatty acid with 8 to 10 carbon atoms comprising the stepsI) providing butylene glycol and at least one fatty acyl group donor providing at least one fatty acyl group comprising 8 to 10 carbon atoms,II) enzyme catalysed esterification of said butylene glycol and said at least one fatty acyl group, and optional III) packaging of said prepared butylene glycol esters in a closed container.

2. Process according to claim 1 characterised in that said acyl group donor is selected from fatty acids and fatty acid esters, preferably fatty acids.

3. Process according to claim 1 or 2 characterised in that said fatty acyl group is selected from caprylate, pelargonate and caprate, preferably a mixture of caprylate and caprate, most preferably pelargonate.

4. Process according to any of the preceding claims characterized in that the molar ratio of said butylene glycol to all fatty acyl groups provided by said fatty acyl group donor is in the range of from 99 : 1 to 1 : 99, preferably from 65 : 40 to 55 : 40.

5. Process according to any of the preceding claims characterized in that process stop II) is catalysed by a lipase.6 Process according to claim 5 characterised in that said 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, 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.7 Process according to any of the preceding claims characterised in that in process step II) reaction water is removed from the reaction, preferably under reduced pressure.

8. Butylene glycol ester of at least one fatty acid with 8 to 10 carbon atoms obtainable by a process according to any of the preceding claims.

9. Butylene glycol ester according to claim 8 characterised in that it has a degree of esterification of from 90.0 % to 99.9 %, preferably from 95.0 % to 99.0 %.

10. Use of a butylene glycol ester according to claim 8 or 9 for preparation of a formulation.11 . Use according to claim 10 characterized in that said formulation comprises at least one natural thickener, preferably selected from the group of xanthan gum, guar gum, carrageenan, agar, gelatine, pectin, alginates, chitosan, konjac gum, cellulose gum, acacia gum, gellan gum, locust bean gum, arrowroot powder, corn-starch, rice starch, potato starch, tapioca starch, wheat starch, soybean flour, maltodextrin, inulin and squalene:

12. Use according to claim 10 or 11 characterized in that said formulation comprises at least one substance selected from the group of UV light protection filter substances and pigments, especially UV light protection filter substances, which are preferably organic.

13. Use according to any of claim 10 to 12 characterized in that said formulation comprises at least one pigment, preferably selected from unmodified or surface-modified, inorganic or organic pigments, preferably inorganic pigments14. Formulation, preferably an aqueous formulation, even more preferably in form of an emulsion, preferably w / o- or o / w emulsion, most preferably o / w emulsion, obtainable by the use according to any of claim 10 to 13.

15. Use of a butylene glycol ester according to claim 8 or 9 as anti-whitening-and-soaping agent in a formulation.

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