US20230055814A1 - Process for enzymatically preparing sugar esters and/or sugar alcohol esters - Google Patents

Process for enzymatically preparing sugar esters and/or sugar alcohol esters Download PDF

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US20230055814A1
US20230055814A1 US17/757,576 US202017757576A US2023055814A1 US 20230055814 A1 US20230055814 A1 US 20230055814A1 US 202017757576 A US202017757576 A US 202017757576A US 2023055814 A1 US2023055814 A1 US 2023055814A1
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acid
residue
evonik
gmbh
mixture
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Jan Marian von Hof
Stefan Julian Liebig
Hans Henning Wenk
Marrit Friederike Eckstein
Sunay Karacocuk
Maxim Yavorsky
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Evonik Operations GmbH
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • C12N9/20—Triglyceride splitting, e.g. by means of lipase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6454—Glycerides by esterification
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the invention provides a process for the enzymatic preparation of sugar esters and/or sugar alcohol esters and also provides mixture compositions containing sugar esters and/or sugar alcohol esters.
  • Fatty acid esters of sugars and sugar alcohols have surfactant properties and due to their natural raw material basis and sustainability are in particular suitable for applications in the food sector and in the cosmetics industry.
  • Fatty acid esters of sugars or sugar alcohols are conventionally synthesized by reaction of the sugars or sugar alcohols with fatty acid chlorides in the presence of pyridine (Surfactants, K. Kosswig in Ullmann's Encyclopedia of Industrial Chemistry, Online, Wiley-VCH, Weinheim, 2000, https://doi.org/10.1002/14356007.a25_747).
  • a disadvantage of this process described in the prior art is that the use of such solvents for applications in the food or cosmetics sector is not acceptable and in addition a corresponding removal of the solvents requires additional process steps such as crystallization, filtration or distillation.
  • a further disadvantage of this process described in the prior art is the quantitative release of HCl when using fatty acid chlorides, since HCl can lead to corrosion of the metallic surfaces of the reactors.
  • a disadvantage of this process described in the prior art is that, during the reaction for example of sorbitol under the conditions mentioned, dehydration of the sugars or sugar alcohols occurs as a side reaction.
  • This side reaction occurs in the presence of acidic catalysts even from temperatures as low as approx. 140° C.
  • sorbitol is dehydrated first to sorbitan (by the loss of a molecule of water) and further to isosorbide (by the loss of a further molecule of water).
  • the sugars or sugar alcohols used thus lose hydrophilicity and are thus increasingly less suitable as hydrophilic head groups for surfactants.
  • a further disadvantage of this process described in the prior art is that the side reactions occurring lead to a dark colouration of the products obtained, which possibly requires a further treatment, for example with bleaching agents such as hydrogen peroxide or activated carbon, in order to be able to use the products obtained in cosmetic formulations, for example.
  • This process described in the prior art has the further disadvantage that the side reactions occurring lead to an unpleasant odour in the products obtained, which can interact undesirably with the perfume used in cosmetic formulations.
  • a further disadvantage of these processes described in the prior art is that the ionic liquids are produced from petrochemical raw materials and hence their use is undesirable for natural and sustainable applications in the food sector or in the cosmetics industry.
  • a further disadvantage of the processes described in the prior art is the use of fatty acid vinyl esters as acyl donor, since these release toxicologically hazardous acetaldehyde during the reaction, which complicates handling on an industrial scale and in addition is undesirable for applications in the food sector or in the cosmetics industry.
  • the fatty acid vinyl esters are prepared from petrochemical raw materials such as acetylene or ethylene in the presence of toxicologically hazardous metal catalysts such as mercury, cadmium, palladium or silver salts (G.
  • choline chloride or other ammonium or phosphonium salts as a result of their salt character can negatively affect the use profiles of fatty acid esters of sugars or sugar alcohols, if they remain in the product.
  • a further disadvantage of this process described in the prior art is that the industrially available quality of choline chloride is a petrochemical raw material, the presence of which in the product is therefore undesirable for natural and sustainable applications in the food sector or in the cosmetics industry. It is thus a further disadvantage of this process described in the prior art that at least one additional process step such as crystallization, filtration or distillation is necessary for removing the choline chloride or other ammonium or phosphonium salts.
  • fatty acid vinyl esters as acyl donor, since these release toxicologically hazardous acetaldehyde during the reaction, which complicates handling on an industrial scale and in addition is undesirable for applications in the food sector or in the cosmetics industry.
  • the fatty acid vinyl esters are prepared from petrochemical raw materials such as acetylene or ethylene in the presence of toxicologically hazardous metal catalysts such as mercury, cadmium, palladium or silver salts (G.
  • a further disadvantage of this process described in the prior art is the use of at most only 0.066 equivalents of the acyl donor based on the total amount of sugars and sugar alcohols.
  • a further disadvantage of this process described in the prior art is that the large excess of the sugars and sugar alcohols used necessitates at least one further additional process step such as extraction, crystallization, filtration or distillation for isolation of the fatty acid esters of the sugars and sugar alcohols.
  • a further disadvantage of this process described in the prior art is that the large excess of the sugars and sugar alcohols used is uneconomical on an industrial scale and in addition necessitates complex recycling of the sugars and sugar alcohols used.
  • a further disadvantage of this process described in the prior art is that, in the case of honey as substrate, only glucose esters are detected and, in the case of agave syrup as substrate, only fructose esters are detected, that is to say in each case only one of the sugar components present in the honey or agave syrup is actually esterified.
  • JPS58116688 discloses the enzymatically catalyzed esterification of mixtures of polysaccharides and/or monosaccharides and oligosaccharides: oligosaccharides and/or polysaccharides are thus always present.
  • the reactions are carried out in water or hexane as solvent; the comparative examples show that, without solvent or with only small quantities of solvent, barely any conversion can be achieved.
  • KR20180007129 discloses a process for preparing mixtures of sucrose esters, fructose esters and glucose esters by enzymatic esterification of sucrose.
  • the process is carried out in solutions which have been diluted with water to such an extent that lauric acid employed is present in dissolved form. Owing to the aqueous, acidic conditions, sucrose is split into the corresponding monosaccharides and esterified during the course of the reaction.
  • the acyl groups are always employed in deficiency, in relation to esterified saccharides obtained, so that the product always contains unreacted saccharides.
  • the sucrose esters always make up the majority of esters obtained.
  • a further disadvantage of this prior art process is that the ratio of the different saccharide esters obtained cannot be predicted or controlled.
  • the object of the invention was to provide a process for preparing sugar esters and/or sugar alcohol esters which contain in particular 4 to 12, preferably 4 to 6, carbon atoms in the sugar moiety or sugar alcohol moiety, which is able to overcome at least one disadvantage of the processes of the prior art.
  • the sugar esters and/or sugar alcohol esters are to be represented by the readily available sugars or sugar alcohols having 4 to 12, preferably 4 to 6, carbon atoms.
  • the present invention provides a process for the enzymatic preparation of a mixture composition comprising at least two selected from sugar esters and/or sugar alcohol esters which contain 4 to 12, preferably 4 to 6, carbon atoms in the sugar moiety or sugar alcohol moiety, comprising the process step
  • acyl group donor preferably fatty acid acyl group donor, especially selected from fatty acid esters and fatty acids, particularly preferably fatty acids,
  • the invention further provides mixture compositions containing particular sugar esters and/or sugar alcohol esters which contain in particular 4 to 12, preferably 4 to 6, carbon atoms in the sugar moiety or sugar alcohol moiety.
  • An advantage of the present invention is that the process according to the invention can be carried out in the absence of a solvent.
  • Another advantage of the present invention is that the process according to the invention can be carried out using natural and sustainable synthesis components.
  • a further advantage of the present invention is that the sugar esters and/or sugar alcohol esters according to the invention are obtained in homogeneous reaction mixtures, and this property can be achieved even at low degrees of esterification.
  • a further advantage of the present invention is that the sugar esters and/or sugar alcohol esters according to the invention have outstanding colour properties.
  • a further advantage of the present invention is that the sugar esters and/or sugar alcohol esters according to the invention have low odour, in particular a caramel-typical odour is barely perceptible.
  • An advantage of the present invention is that substrates in a mixture can be successfully converted, whereas their conversion alone in the absence of a solvent is not successful.
  • a further advantage of the present invention is that no undesired byproducts are formed from the employed sugars/sugar alcohols by elimination of water, such as sorbitans from sorbitol.
  • a further advantage of the present invention is that the sugar esters and/or sugar alcohol esters obtained can be incorporated very readily into formulations, especially into cosmetic formulations.
  • a further advantage of the present invention is that gentle formulations can be prepared using the sugar esters and/or sugar alcohol esters obtained.
  • a further advantage of the present invention is that formulations having a particularly good skin feel can be prepared using the sugar esters and/or sugar alcohol esters obtained.
  • a further advantage of the present invention is that sustainable formulations without petrochemical components can be prepared using the sugar esters and/or sugar alcohol esters obtained.
  • a further advantage of the present invention is that the sugar esters and/or sugar alcohol esters obtained can be prepared without the quantitative release of HCl or acetaldehyde.
  • a further advantage of the present invention is that the reaction can be effected in a bubble column on account of the good miscibility of the reaction mixture, as a result of which relatively long catalyst lifetimes can be achieved.
  • a further advantage of the present invention is that a large amount of acyl donors can be used, based on the total molar amount of sugars and/or sugar alcohols.
  • a further advantage of the present invention is that the esters of the sugars and sugar alcohols used are obtained in a homogeneous reaction mixture, so that no additional process steps such as extraction, crystallization, filtration or distillation are required.
  • a further advantage of the present invention is that during the reaction more than just one of the sugar and sugar alcohol components used is esterified.
  • a further advantage of the present invention is that homogeneous melts are obtained when reacting at relatively low degrees of esterification.
  • the present invention provides a process for the enzymatic preparation of a mixture composition comprising at least two selected from sugar esters and/or sugar alcohol esters which contain in particular 4 to 12, preferably 4 to 6, carbon atoms in the sugar moiety or sugar alcohol moiety, comprising the process step
  • two selected from sugar esters and/or sugar alcohol esters in the context of the present invention should be understood to mean that the two esters differ in terms of their sugars and/or in terms of their sugar alcohols. Esters must therefore be present which have two different residues in terms of sugar and/or sugar alcohol residue.
  • all of the sugars and sugar alcohols such as for example agarose, amylopectin, amylose, cellulose, chitin, cyclodextrins, dextrans, fructans, glycogen, hyaluronic acid, inulin, isomelizitose, maltohexose, maltopentose, maltotetrose, maltotriose, melizitose, pectins, raffinose, stachyose, starch, starch hydrolysate, umbelliferose, cellobiose, isomalt, isomaltulose, lactitol, lactose, lactulose, maltitol, maltose, maltulose, sucrose, trehalose, trehalulose,
  • the sugars and sugar alcohols are selected from the group of sugars and sugar alcohols containing 4 to 12, preferably 4 to 6, carbon atoms.
  • the sugars and sugar alcohols from the group of sugars and sugar alcohols containing 4 to 12 carbon atoms are selected from
  • allitol allulose, altritol, arabinitol, arabinose, deoxyribose, erythritol, fructose, fucose, galactitol, galactose, glucose, iditol, mannitol, mannose, rhamnose, ribitol, ribose, sorbitol, sorbose, threitol, xylitol and xylose,
  • allitol, allulose, altritol, arabinitol, arabinose, cellobiose, deoxyribose, erythritol, fructose, fucose, galactitol, galactose, glucose, iditol, isomalt, isomaltulose, lactitol, lactose, lactulose, maltitol, maltose, maltulose, mannitol, mannose, rhamnose, ribitol, ribose, sorbitol, sorbose, threitol, trehalulose, xylitol and xylose are particularly preferred and
  • erythritol fructose, glucose, isomalt, isomaltulose, lactitol, lactose, maltitol, maltose, maltulose, mannitol, sorbitol, sorbose, xylitol and xylose are very particularly preferred.
  • the sugars and sugar alcohols from the group of sugars and sugar alcohols containing 4 to 6 carbon atoms are selected from
  • the sugars and sugar alcohols are selected from the group.
  • a process which is preferred according to the invention is characterized in that in process step B), as mixture containing at least two selected from sugars and sugar alcohols, mixtures containing glucose, fructose and maltose with, in each case based on all sugars and sugar alcohols present in the mixture, a glucose content of 40% by weight to 50% by weight and a fructose content of 47% by weight to 57% by weight, and
  • glucose, fructose and sucrose with, in each case based on all sugars and sugar alcohols present in the mixture, a glucose content of 5% by weight to 24% by weight and a fructose content of 75% by weight to 94% by weight
  • acyl group donors may be used according to the invention. These are, for example, carboxylic esters or carboxylic acids themselves and mixtures thereof.
  • carboxylic esters used as acyl group donor are selected from esters based on alkanols and polyols having up to 6 carbon atoms, particularly preferably having up to 3 carbon atoms, very preferably glycerol esters.
  • carboxylic esters used as acyl group donor are selected from triglycerides, especially natural fats and oils, particularly preferably selected from the group comprising, preferably consisting of, coconut fat, palm kernel oil, olive oil, palm oil, argan oil, castor oil, linseed oil, babassu oil, rapeseed oil, algal oils, sesame oil, soya oil, avocado oil, jojoba oil, safflower oil, almond oil, cottonseed oil, shea butter, sunflower oil, cupuaçu butter and oils having a high proportion of polyunsaturated fatty acids (PUFAs).
  • Sorbitan esters, monoglycerides and diglycerides, in particular containing the acyl groups described hereinafter, may likewise preferably be used.
  • the acyl group donor is selected from fatty acid acyl group donors which in particular provide an acyl group selected from the group of acyl groups of natural fatty acids.
  • Natural fatty acids can be produced on the basis of naturally occurring vegetable or animal oils and have preferably 6-30 carbon atoms, especially 8-22 carbon atoms. Natural fatty acids are generally unbranched and usually consist of an even number of carbon atoms. Any double bonds have cis configuration.
  • caproic acid caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, pelargonic acid (obtainable from the ozonolysis of oleic acid), isostearic acid, stearic 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, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid.
  • acyl group donors used are carboxylic acids, especially fatty acids, with particular preference being given to using the fatty acids specifically mentioned hereinabove.
  • the fatty acid vinyl esters are prepared from petrochemical raw materials such as acetylene or ethylene in the presence of toxicologically hazardous metal catalysts such as mercury, cadmium, palladium or silver salts (G.
  • the sugars and sugar alcohols prefferably be selected from erythritol, fructose, glucose, sorbitol, xylitol and xylose and for the acyl group donor to be selected from at least one from the group of caproic acid, caprylic acid, pelargonic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, petroselinic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid.
  • a process which is preferred in accordance with the invention is characterized in that the mixture used in process step B) and containing at least two selected from sugars and sugar alcohols comprises substances selected from the group consisting of choline salts, ammonium salts and phosphonium salts in an amount of less than 2% by weight, preferably less than 1% by weight, particularly preferably less than 0.1% by weight, especially does not comprise any of these substances, where the weight percentages relate to all sugar and sugar alcohols in process step B) in the mixture containing at least two selected from sugars and sugar alcohols.
  • a process which is preferred in accordance with the invention is characterized in that in process step B) the molar ratio of all sugars and sugar alcohols to acyl groups present in all acyl group donors is in a range from 1.00:0.08 to 1.00:10.00, preferably from 1.00:0.50 to 1.00:7.00, particularly preferably from 1.00:1.25 to 1.00:2.25, alternatively particularly preferably from 1.00:2.00 to 1.00:4.50.
  • a process which is preferred in accordance with the invention is characterized in that in process step B) the molar ratio of all primary hydroxyl groups in all sugars and sugar alcohols to acyl groups present in all acyl group donors is in a range from 1.00:0.10 to 1.00:3.00, particularly preferably from 1.00:1.25 to 1.00:2.25.
  • a process which is preferred in accordance with the invention is characterized in that in process step B) a mixture containing sugars and/or sugar alcohols having 4 to 6 carbon atoms is employed and the molar ratio of all primary hydroxyl groups in all sugars and sugar alcohols having 4 to 6 carbon atoms to acyl groups present in all acyl group donors is in a range from 1.00:0.20 to 1.00:1.5.
  • Lipases used with preference in accordance with the invention are present immobilized on a solid support.
  • Lipases used with preference in accordance with the invention in process step B) are lipases selected from the group comprising the lipase from Thermomyces lanuginosus (accession number O59952), lipases A and B (accession number P41365) from Candida antarctica and the lipase from Mucor miehei (accession number P19515), the lipase from Humicola sp.
  • the enzymes that are homologous at the amino acid level, by comparison with the reference sequence, preferably have at least 50%, especially at least 90%, enzyme activity in propyl laurate units as defined in the context of the present invention.
  • carboxylic ester hydrolases 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” in the context of the present invention is understood to mean “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 initially 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 including
  • the person skilled in the art is 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.
  • Blossom 62 matrix is typically used applying the default settings (gap weight: 12, length weight: 1).
  • an identity of 60% means 60% homology. The same applies to higher identities.
  • process step B) is conducted at reaction temperatures in the range between 20° C. and 160° C., preferably 35° C. and 130° C., in particular between 50° C. and 110° C.
  • process step B) is conducted at a pressure of less than 1 bar, preferably less than 0.5 bar and particularly preferably less than 0.05 bar.
  • process step B) is conducted in a bubble column reactor, with at least one inert gas being passed through the reaction mixture; this gas is preferably selected from the group comprising, preferably consisting of, nitrogen and argon.
  • the gas stream it is preferable in accordance with the invention for the gas stream to be 1 to 60 kg/h, preferably 5 to 25 kg/h, yet more preferably 10 to 14 kg/h.
  • a process which is preferred in accordance with the invention is characterized in that in process step B) the mixture containing at least two selected from sugars and sugar alcohols and the acyl group donor make up in total at least 10% by weight, preferably at least 86% by weight, particularly preferably at least 90% by weight, of the overall reaction mixture.
  • a process which is preferred in accordance with the invention is characterized in that, in the process, solvent, in particular water or hexane, is added in an amount of at most 5% by weight, preferably at most 2% by weight, particularly preferably is not added at all, where the weight percentages relate to the overall reaction mixture.
  • solvent in particular water or hexane
  • a process which is preferred in accordance with the invention is characterized in that byproducts forming in process step B), for example water in the case where the acyl group donor used is an acid, the corresponding alcohol in the case where the acyl group donor used is an ester, are removed.
  • the process according to the invention comprises process step A) providing the at least two selected from sugars and sugar alcohols spatially separately from each other in solid form or in a form dissolved in water and mixing them to give the mixture used in process step B) and containing at least two selected from sugars and sugar alcohols. It may be especially preferable here to concentrate the mixture containing at least two selected from sugars and sugar alcohols and the acyl group donor by means of removing water, in order for the abovementioned mixture and acyl group donor to reach in total at least 10% by weight, preferably at least 86% by weight, particularly preferably at least 90% by weight, of the overall reaction mixture.
  • process step A) comprises a reduction of the water content of the mixture used in process step B) and containing at least two selected from sugars and sugar alcohols to less than 17% by weight, preferably less than 14% by weight, particularly preferably less than 10% by weight, where the weight percentages relate to the total mixture used in process step B) and containing at least two selected from sugars and sugar alcohols.
  • the process according to the invention comprises process step C) removing the lipase.
  • the process according to the invention comprises process step D) filtering the mixture composition comprising at least two selected from sugar esters and/or sugar alcohol esters through a filter, especially a bag filter, having a fineness of 0.1 ⁇ to 1250 ⁇ , preferably from 0.5 ⁇ to 100 ⁇ .
  • process step D) is conducted in a temperature range of from 20° C. to 150° C., especially 40° C. to 120° C.
  • process step D) is conducted in a pressure range of from 1 bar to 25 bar, especially of from 1.5 bar to 10 bar.
  • the process according to the invention does not comprise any further purification step besides process steps C) and D), if these are present.
  • the present invention further provides a mixture composition
  • a mixture composition comprising at least two selected from sugar esters and sugar alcohol esters obtainable by the process according to the invention which contain in particular 4 to 12, preferably 4 to 6, carbon atoms in the sugar moiety or sugar alcohol moiety.
  • the present invention also provides a mixture composition containing sugar esters and/or sugar alcohol esters, characterized in that the sugar and/or sugar alcohol residue of the sugar ester and/or of the sugar alcohol ester is selected from at least two sugar and/or sugar alcohol residues selected from the group of the residues of allitol, allulose, altritol, arabinitol, arabinose, cellobiose, deoxyribose, erythritol, fructose, fucose, galactitol, galactose, glucose, iditol, iditol, isomalt, isomaltulose, lactitol, lactose, lactulose, maltitol, maltose, maltulose, mannitol, mannose, rhamnose, ribitol, ribose, sucrose, sorbitol, sorbose, threitol, trehalose, trehal
  • erythritol preferably from erythritol, fructose, glucose, isomalt, isomaltulose, lactitol, lactose, maltitol, maltose, maltulose, mannitol, sucrose, sorbitol, sorbose, xylitol and xylose, especially preferably from erythritol, fructose, glucose, sorbitol, xylitol and xylose, and
  • ester residue is selected from at least one acyl group of the group of acid residues of the fatty acids
  • caproic acid preferably of caproic acid, caprylic acid, pelargonic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, 12-hydroxystearic acid, dihydroxystearic acid, oleic acid, linoleic acid, linolenic acid, petroselinic acid, elaidic acid, arachic acid, behenic acid, erucic acid, gadoleic acid, linolenic acid, eicosapentaenoic acid, docosahexaenoic acid and arachidonic acid.
  • Mixture compositions that are preferred in accordance with the invention contain preferably 4 to 6 carbon atoms in the sugar moiety or sugar alcohol moiety.
  • Mixture compositions that are preferred in accordance with the invention contain the sugar ester and/or the sugar alcohol ester in an amount of at least 50% by weight, preferably at least 80% by weight, particularly preferably at least 95% by weight, where the percentages by weight relate to the overall mixture composition.
  • sugar esters and/or sugar alcohol esters present have a degree of esterification of 1.00 and above, in particular of 1.00 to 7.00, particularly preferably of 1.25 to 2.25, alternatively particularly preferably of 2.00 to 4.50.
  • Suitable methods for determining the acid number are particularly those according to DGF C-V 2, DIN EN ISO 2114, Ph. Eur. 2.5.1, ISO 3682 and ASTM D 974.
  • the mixture was stirred at 80° C. and 15 mbar for 24 h, during which time the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, colourless and had an acid number of 1.8 mg KOH/g.
  • the product obtained was inhomogeneous in the melt, reddish coloured and had an acid number of approx. 140.5 mg KOH/g (due to the inhomogeneity the acid number could not be determined unambiguously).
  • Example 3 Physical Mixture of Example 1 and Example 2 (Not in Accordance with the Invention)
  • Example 2 A mixture of an ester obtained as described in Example 1 (42.00 g) and an ester as described in Example 2 (18.00 g) was heated to 80° C. for 1 h with stirring and while passing N 2 through.
  • the product obtained was inhomogeneous in the melt, cloudy, orange and had an acid number of approx. 40 mg KOH/g (due to the inhomogeneity the acid number could not be determined unambiguously).
  • the mixture was stirred at 80° C. and 20 mbar for 24 h, during which time the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, clear and colourless and had an acid number of 1.3 mg KOH/g.
  • Example 7 Physical Mixture of Example 5 and Example 6
  • Example 8 Enzymatic Esterification of a Mixture of Xylitol and Sorbitol (70:30) with 1.50 eq. of Caprylic Acid (According to the Invention)
  • Example 9 Enzymatic Esterification of a Mixture of Xylitol and Sorbitol (66:34) with 2.00 eq. of Technical-Grade Oleic Acid (According to the Invention)
  • the mixture was subsequently stirred at 80° C. and 10 mbar for 24 h, during which time the water formed was continuously distilled off. Subsequently, the mixture was filtered at 80° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, slightly cloudy and pale yellow and had an acid number of 2.0 mg KOH/g.
  • Example 10 Enzymatic Esterification of a Mixture of Xylitol and Sorbitol (70:30) with 2.00 eq. of Technical-Grade Oleic Acid (According to the Invention)
  • Example 13 Physical Mixture of Example 11 and Example 12
  • Example 11 A mixture of an ester obtained as described in Example 11 (42.00 g) and an ester as described in Example 12 (18.00 g) was heated to 80° C. for 1 h with stirring and while passing N 2 through.
  • the product obtained was homogeneous in the melt, clear, orange and had an acid number of 5.1 mg KOH/g.
  • Example 14 Enzymatic Esterification of a Mixture of Xylitol and Fructose (70:30) with 2.00 eq. of Stearic Acid (According to the Invention)
  • the mixture was subsequently filtered at 80′C and 2 bar N 2 pressure through a filter press with a Seitz T-750 depth filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, clear and had an acid number of 3.2 mg KOH/g.
  • Example 15 Enzymatic Esterification of a Mixture of Xylitol, Sorbitol and Fructose (50:25:25) with 1.91 eq. of Caprylic Acid (According to the Invention)
  • a mixture of xylitol (39.59 g, 0.260 mol), sorbitol (19.80 g, 0.109 mol), fructose (19.80 g, 0.110 mol) and caprylic acid (acid number 389 mg KOH/g, >98%, 138.05 g, 0.957 mol, 1.91 eq. based on the total initial weight of xylitol, sorbitol and fructose) was heated to 100° C. with stirring and while passing N 2 through and stirred for 1 h.
  • Candida antarctica lipase B enzyme (5.92 g; Purolite D5619, corresponding to 51257 PLU) was added and the mixture was stirred further at 80° C. and 20 mbar for 24 h, during which time the water formed was continuously distilled off, Subsequently, the mixture was filtered at 90° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, clear and yellow and had an acid number of 3.1 mg KOH/g.
  • Example 16 Enzymatic Esterification of a Mixture of Xylitol, Sorbitol and Glucose (65:25:10) with 1.91 eq. of Caprylic Acid (According to the Invention)
  • a mixture of xylitol (52.12 g, 0.342 mol), sorbitol (20.05 g, 0.110 mol), glucose (8.02 g, 0.045 mol) and caprylic acid (acid number 389 mg KOH/g, >98%, 136.91 g, 0.949 mol, 1.91 eq, based on the total initial weight of xylitol, sorbitol and glucose) was heated to 100° C. with stirring and while passing N 2 through and stirred for 1 h.
  • Candida antarctica lipase B enzyme (5.91 g; Purolite D5619, corresponding to 51170 PLU) was added and the mixture was stirred further at 80° C. and 20 mbar for 24 h, during which time the water formed was continuously distilled off, Subsequently, the mixture was filtered at 90° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme. The product obtained was homogeneous in the melt, clear and pale yellow and had an acid number of 10.0 mg KOH/g.
  • Example 17 Enzymatic Esterification of a Mixture of Xylitol and Sorbitol (70:30) with 1.50 eq. of Lauric Acid (According to the Invention)
  • a mixture of xylitol (51.7 g, 0.340 mol), sorbitol (22.16 g, 0.122 mol) and lauric acid (acid number 280 mg KOH/g, >99%, 138.60 g, 0.692 mol, 1.50 eq. based on the total initial weight of xylitol and sorbitol) was heated to 100° C. with stirring and while passing N 2 through, and after 60 min immobilized Candida antarctica lipase B enzyme (6.02 g; Purolite D5619, corresponding to 52122 PLU) was added. The mixture was subsequently stirred at 95° C. and 50 mbar for 24 h, during which time the water formed was continuously distilled off.
  • the mixture was filtered at 90° C. through a Büchner funnel with black ribbon filter in order to remove the enzyme.
  • the product obtained was homogeneous in the melt, slightly cloudy and pale yellow to virtually colourless and had an acid number of 0.8 mg KOH/g.
  • Table 1 compares Example 4 according to the invention with Examples 1, 2 and 3 not in accordance with the invention in terms of reaction course, homogeneity and odour.
  • Example 1 Example 2
  • Example 3 Example 4 not in not in not in not in according to accordance with accordance with the invention the invention the invention the invention Sugar/sugar alcohol xylitol fructose xylitol/fructose xylitol/fructose (70:30)
  • Fatty acid caprylic acid caprylic acid caprylic acid caprylic acid Sugar/fatty acid 1:2 1:2 1:2 1:2 molar ratio Appearance in the homogeneous inhomogeneous/ inhomogeneous/ homogeneous melt after 2 phases 2 phases filtration/after mixing Acid number AN ⁇ 1.3 after AN 140.5 after AN approx.
  • Example 2 not in accordance with the invention after 24 h reaction time is inhomogeneous, still has a high residual acid number of approx. 140.5 mg KOH/g and in addition still has a pronounced odour of fatty acid, which is perceived as unpleasant in the case of the short-chain fatty acids such as caprylic acid.
  • Example 1 not in accordance with the invention after 24 h reaction time is homogeneous and has a residual acid number of just ⁇ 1.3 mg KOH/g, a pronounced odour of fatty acid can also be detected for this example.
  • Example 3 Only in Example 4 according to the invention are a low residual acid number (i.e. a high conversion of the fatty acid), a homogeneous product and a pleasant odour (popcorn-like) achieved after 24 h reaction time.
  • Table 2 compares Example 8 according to the invention with Examples 5 and 6 not in accordance with the invention in terms of reaction course and homogeneity.
  • Example 5 Example 6
  • Example 7 Example 8 not in not in not in not in according to accordance with accordance with the invention the invention the invention the invention the invention Sugar/sugar alcohol xylitol sorbitol xylitol/sorbitol xylitol/sorbitol (70:30)
  • Fatty acid caprylic acid caprylic acid caprylic acid caprylic acid Sugar/fatty acid 1:1.5 1:1.5 1:1.5 1:1.5 molar ratio Appearance in the approx. 2.5% approx. 30% approx.
  • Example 5 not in accordance with the invention at 80° C. exhibits phase separation in the melt in the form of a sediment. This phenomenon is even more pronounced in Example 6 not in accordance with the invention and also occurs in the physical mixture of Example 5 and Example 6 (Example 7). Only Example 8 according to the invention at 80° C. is homogeneous in the melt and exhibits no phase separation, despite the comparatively low degree of esterification of 1:1.5 (sugar/fatty acid molar ratio).
  • Table 3 compares Example 14 according to the invention with Example 13 not in accordance with the invention in terms of reaction course and colour.
  • Example 14 not in according to accordance with the invention the invention
  • Example 13 the physical mixture (Example 13) exhibits a much poorer colour than a process product according to the invention (Example 14).
  • compositions according to the invention can be used in a large number of cosmetic formulations.
  • Formulations 1a, 1b and 1c Aluminium Salt-Containing Antiperspirant/Deodorant Formulations
  • Formulation 1a 1b 1c Composition from Example 14 3.2% 3.2% 3.2% C18-C22 Hydroxyalkyl Hydroxypropyl Guar 0.2% (ESAFLOR HM 22, Lamberti S.p.A.) Hydroxypropyl Guar (ESAFLOR HDR, Lamberti 0.2% 0.2% S.p.A.) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik 5.4% 5.4% 5.4% Operations GmbH) Water to 100% to 100% to 100% Aluminum Chlorohydrate (50% aq.; Locron LIC, 20.0% 20.0% 20.0% Clariant AG) Methylisothiazolinone, Methylparaben, Ethylparaben; 0.8% 0.8% Dipropylene Glycol (Microcare MEM, Thor) Undecylenamidopropyltrimonium methosulfate; Aqua; 1.0% Propylene Glycol (dermosoft ® UTM, Evonik Dr. Straetmans GmbH)
  • Formulations 2a, 2b and 2c Aluminium-Free Deodorant Formulation without Antiperspirant Active Ingredients
  • Formulation 2a 2b 2c Composition from Example 14 3.2% 3.2% 3.2% Hydroxypropyl Guar (ESAFLOR HDR, Lamberti S.p.A.) 0.15% C18-22 Hydroxyalkyl Hydroxypropyl Guar (ESAFLOR HM 0.15% 0.15% 22, Lamberti S.p.A.) Polyglyceryl-3 Caprylate (TEGO ® Cosmo P 813, Evonik 0.5% 0.5% 0.5% Operations GmbH) Zinc Ricinoleate (TEGODEO ® PY 88 G, Evonik Operations 1.0% 1.0% 1.0% GmbH) Caprylic/Capric Triglyceride (TEGOSOFT ® CT, Evonik 5.65% 5.65% 5.65% Operations GmbH) Water to 100% to 100% to 100% to 100% Glycerin 3.0% 3.0% 3.0% Benzyl Alcohol, Benzoic Acid, Sorbic Acid (Rokonsal BSB- 1.0% 1.0% 1.0% N, Ashland Specialty Ingredients) Citric acid (50% aq.) q.s
  • Formulations 3a, 3b and 3c O/W Deodorant Emulsion Containing Potassium Alum
  • Formulation 3a 3b 3c Composition from Example 14 4.8% 4.8% 4.8% C18-C22 Hydroxyalkyl Hydroxypropyl Guar (ESAFLOR 0.25% HDR, Lamberti S.p.A.) Hydroxypropyl Guar (ESAFLOR HDR, Lamberti S.p.A.) 0.25% 0.25% Isopropyl Palmitate (TEGOSOFT ® P, Evonik Operations 5.0% 5.0% 5.0% GmbH) Water to 100% to 100% to 100% to 100% Glycerin 3.0% 3.0% 3.0% Potassium alum 5.0% 5.0% 5.0% 5.0% Methylisothiazolinone, Methylparaben, Ethylparaben; 0.8% 0.8% Dipropylene Glycol (Microcare MEM, Thor) Pentylene Glycol (dermosoft ® Pentiol eco, Evonik Dr. 3.5% Straetmans GmbH)
  • Formulation 4a and 4b Antiperspirant/Deodorant Lotion
  • Formulation 4a 4b Composition from Example 14 3.0% 3.0% Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik Operations 3.0% 3.0% GmbH) PPG-14 Butyl Ether (TEGOSOFT ® PBE, Evonik Operations GmbH) 3.0% 3.0% Polyglyceryl-3 Caprylate (TEGO ® Cosmo P813, Evonik Operations 0.5% 0.5% GmbH) Demineralized Water to 100% to 100% Hydroxyethylcellulose (Natrosol 250 HHR, Ashland Specialty 1.0% 1.0% Chemicals) Aluminum Chlorohydrate (50%) (Reach 501L, Reheis) 15.0% 15.0% Methylisothiazolinone, Methylparaben, Ethylparaben; Dipropylene 0.8% 3.0% Glycol (Microcare MEM, Thor) 1,2-Hexanediol (dermosoft ® Hexiol, Evonik Dr. Straetmans GmbH) 2.8%
  • Formulations 5a, 5b and 5c Antiperspirant/Deodorant Creams
  • Formulation 5a 5b 5c Composition from Example 14 3.0% 2.5% 2.5% Sodium Cetearyl Sulfate (Lanette E, BASF SE) 0.5% 0.5% Glyceryl Stearate 1.0% 1.0% 1.0% Stearyl Alcohol 1.0% 1.0% 1.0% PPG-15 Stearyl Ether 5.0% 5.0% 5.0% Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations 5.0% 5.0% 5.0% GmbH) Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik 5.0% 5.0% 5.0% Operations GmbH) Persea Gratissima (Avocado) Oil 2.0% 2.0% 2.0% Polyglyceryl-3 Caprylate (TEGO ® Cosmo P813, Evonik 0.5% 0.5% 0.5% Operations GmbH) Zinc Ricinoleate (TEGODEO ® PY88 G, Evonik Operations 1.0% 1.0% 1.0% GmbH) Demineralized Water to 100% to 100% to 100% Hydroxyethylcellulose (Natrosol 250 HHR (A
  • Formulation 6a 6b Composition from Example 14 4.0% 4.0% Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik Operations GmbH) 3.2% 3.2% Isopropyl Palmitate (TEGOSOFT ® P, Evonik Operations GmbH) 2.0% 2.0% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb S, BASF 3.0% 3.0% SE) Butyl Methoxydibenzoylmethane 2.0% 2.0% EHC 2.0% 2.0% Ethylhexyl salicylate 4.0% 4.0% Octocrylene 4.0% 4.0% Glycerin 3.0% 3.0% Water to 100% to 100% Carbomer suspension 1 (Acrylates/C10-30 Alkyl Acrylate Crosspolymer, 1.0% 1.0% TEGO ® Carbomer 341ER, Evonik Operations GmbH, 20% in Phenoxyethyl Caprylate) Tris(hydroxymethyl)aminomethane (30% aq.) 0.6%
  • Formulations 7a, 7b and 7c Sunscreen Spray
  • Formulation 7a 7b 7c Composition from Example 14 3.0% 2.5% 2.5% Glyceryl Stearate Citrate (AXOL ® C 62, Evonik 0.5% 0.5% Operations GmbH) Glyceryl Stearate 0.5% 0.5% 0.5% 0.5% Stearyl Alcohol 0.5% 0.5% 0.5% 0.5% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 3.0% 3.0% 3.0% (Tinosorb S, BASF SE) Butyl Methoxydibenzoylmethane 2.0% 2.0% 2.0% Ethylhexyl Methoxycinnamate 2.0% 2.0% 2.0% Ethylhexyl salicylate 4.0% 4.0% 4.0% Octocrylene 4.0% 4.0% 4.0% Isopropyl Palmitate 2.0% 2.0% 2.0% Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 3.2% 3.2% 3.2% Operations GmbH) Glycerin 3.0% 3.0% 3.0% Demineralized Water to 100% to 100% to 100% Carb
  • Formulations 8a, 8b and 8c Sunscreen Lotion, SPF 30
  • Formulation 8a 8b 8c Composition from Example 14 3.00% 2.00% 2.00% Cetearyl Glucoside (TEGO ® Care CG 90, Evonik 0.50% 0.50% Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 8.00% 8.00% 8.00% Operations GmbH) Diethylamino Hydroxybenzoyl Hexyl Benzoate (Uvinul A 6.00% 6.00% 6.00% Plus, BASF SE) Ethylhexyl Methoxycinnamate 8.00% 8.00% 8.00% Stearyl Alcohol 1.00% 1.00% 1.00% Glyceryl Stearate 1.00% 1.00% 1.00% 1.00% Tocopheryl Acetate 0.50% 0.50% 0.50% Glycerin 2.00% 2.00% 2.00% Demineralized Water to 100% to 100% to 100% Tromethamine 0.90% 0.90% 0.90% Phenylbenzimidazole Sulfonic Acid 2.00% 2.00% 2.00% Acrylates
  • Formulations 9a, 9b and 9c Sunscreen Lotion SPF 30, High UVA Protection
  • Formulation 9a 9b 9c Composition from Example 14 3.00% 2.50% 2.50% Sodium Cetearyl Sulfate (Lanette E, BASF SE) 0.50% 0.50% Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 7.30% 7.30% 7.30% Operations GmbH) Butyl Methoxydibenzoylmethane 5.00% 5.00% Diethylhexyl Butamido Triazone (UVAsorb HEB, 3V 1.00% 1.00% 1.00% Sigma) Ethylhexyl Salicylate 1.50% 1.50% 1.50% Octocrylene 3.50% 3.50% 3.50% 3.50% Titanium Dioxide; Diethylhexyl Carbonate; Polyglyceryl-6 2.20% 2.20% 2.20% Polyhydroxystearate (TEGO ® Sun TDEC 45, Evonik Operations GmbH) Stearyl Alcohol 1.00% 1.00% 1.00% Nylon-10/10 (TEGOLON ® ECO 10-10
  • Formulations 10a, 10b and 10c Sunscreen Lotion, SPF 30
  • Formulation 10a 10b 10c Composition from Example 14 3.00% 2.00% 2.00% Methylglucose Sesquistearate (TEGO ® Care PS, 1.00% 1.00% Evonik Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 1.50% 1.50% 1.50% Operations GmbH) Octocrylene 10.00% 10.00% 10.00% Butyl Methoxydibenzoylmethane 3.50% 3.50% 3.50% Titanium Dioxide; Diethylhexyl Carbonate; 14.50% 14.50% 14.50% Polyglyceryl-6 Polyhydroxystearate (TEGO ® Sun TDEC 45, Evonik Operations GmbH) Stearyl Alcohol 0.20% 0.20% 0.20% Glyceryl Stearate 0.20% 0.20% 0.20% Tocopheryl Acetate 0.50% 0.50% 0.50% Glycerin 2.00% 2.00% 2.00% Demineralized Water to 100% to 100% to 100% Acrylates/C10-30 Alkyl
  • Formulations 11a, 11b and 11c Sunscreen Lotion SPF 50, High UVA Protection
  • Formulation 11a 11b 11c Composition from Example 14 3.00% 2.50% 2.50% Polyglyceryl-3 Methylglucose Distearate (TEGO ® Care 450, 0.50% 0.50% Evonik Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik Operations 2.00% 2.00% 2.00% GmbH) Nylon-10/10 (TEGOLON ® ECO 10-10, Evonik Operations 0.50% 0.50% 0.50% GmbH) Butyl Methoxydibenzoylmethane 5.00% 5.00% 5.00% Diethylhexyl Butamido Triazone (UVAsorb HEB, 3V Sigma) 1.00% 1.00% 1.00% 1.00% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb S, 3.00% 3.00% 3.00% BASF SE) Ethylhexyl Salicylate 1.00% 1.00% 1.00% 1.00% Octocry
  • Formulations 12a, 12b and 12c Sunscreen Lotion, SPF 50
  • Formulation 12a 12b 12c Composition from Example 14 3.50% 3.00% 3.00% Glyceryl Stearate Citrate (AXOL ® C 62, Evonik 1.00% 1.00% Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 2.50% 2.50% 2.50% Operations GmbH) Diethylamino Hydroxybenzoyl Hexyl Benzoate 10.00% 10.00% 10.00% Ethylhexyl Methoxycinnamate 10.00% 10.00% 10.00% 10.00% Stearyl Alcohol 1.00% 1.00% 1.00% Glyceryl Stearate 1.00% 1.00% 1.00% 1.00% Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.50% 0.50% 0.50% 0.50% Tocopheryl Acetate 0.50% 0.50% 0.50% Glycerin 2.00% 2.00% Demineralized Water to 100% to 100% to 100% Phenylbenzimidazole Sul
  • Formulations 13a, 13b and 13c Sunscreen Lotion SPF 50+
  • Formulation 13a 13b 13c Composition from Example 14 3.00% 2.5% 2.5% Potassium Cetyl Phosphate 1.0% 1.0% Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik 3.00% 3.00% 3.00% Operations GmbH) Butyl Methoxydibenzoylmethane 5.00% 5.00% Octocrylene 4.90% 4.90% 4.90% Ethylhexyl Methoxycinnamate 0.10% 0.10% 0.10% 0.10% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 4.70% 4.70% 4.70% (Tinosorb S, BASF SE) Diethylhexyl Butamido Triazone (UVAsorb HEB, 3V 3.70% 3.70% 3.70% Sigma) Titanium Dioxide; Diethylhexyl Carbonate; 11.00% 11.00% 11.00% Polyglyceryl-6 Polyhydroxystearate (TEGO ® Sun
  • Formulation 14a 14b Composition from Example 14 4.0% 4.0% Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations GmbH) 2.5% 2.5% Caprylic/Capric Triglyceride (TEGOSOFT ® CT, Evonik Operations 3.5% 3.5% GmbH) Water to 100% to 100% Creatine (TEGO ® Cosmo C 100, Evonik Operations GmbH) 0.5% 0.5% Carbomer suspension 2 (Carbomer, TEGO ® Carbomer 141, Evonik 1.0% 1.0% Operations GmbH, 20% in Ethylhexyl Stearate) Sodium hydroxide (10% aq.) 0.6% 0.6% Phenoxyethanol, Ethylhexylglycerin (Euxyl PE 9010, Schülke & Mayr 0.7% GmbH) Aqua; Sodium Levulinate; Sodium Benzoate (Versatil ® BL; Evonik Dr. 1.5% Straetmans GmbH) Glyceryl Caprylate (dermosoft ® GMCY
  • Formulation 15a 15b Composition from Example 14 6.0% 6.0% Caprylic/Capric Triglyceride (TEGOSOFT ® CT, Evonik Operations 8.0% 8.0% GmbH) Isopropyl Palmitate (TEGOSOFT ® P, Evonik Operations GmbH) 11.0% 11.0% Prunus Amygdalus Dulcis (Sweet Almond) Oil 10.0% 10.0% Water to 100% to 100% Glycerin 3.0% 3.0% Sodium hydroxide (10% aq.) 0.2% 0.2% Benzyl Alcohol, Benzoic Acid, Sorbic Acid (Rokonsal BSB-N, Ashland 0.8% Specialty Ingredients) Glycerin; Aqua; Sodium Levulinate; Sodium Anisate (dermosoft ® 1388 3% eco; Evonik Dr. Straetmans GmbH) Glyceryl Caprylate (dermosoft ® GMCY MB; Evonik Dr. Straetmans 0.2% GmbH)
  • Formulation 16a and 16b Anti-Aging Cream
  • Formulation 16a 16b Composition from Example 14 6.0% 6.0% Caprylic/Capric Triglyceride (TEGOSOFT ® CT, Evonik Operations 9.5% 9.5% GmbH) C12-15 Alkyl Benzoate (TEGOSOFT ® TN, Evonik Operations GmbH) 9.5% 9.5% Water to 100% to 100% Glycerin 3.0% 3.0% Tetrapeptide-21; Glycerin; Butylene Glycol; Aqua (TEGO ® PEP 4-17, 4.0% 4.0% Evonik industries) Sodium Hyaluronate (HyaCare ®, Evonik Operations GmbH) 0.1% 0.1% Hydrolyzed Hyaluronic Acid (HyaCare ® 50, Evonik Operations GmbH) 0.1% 0.1% Aqua; Ethylhexyl Stearate; Sodium Hyaluronate Crosspolymer; 5.0% 5.0% Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate; Sodium Isostearate (HyaCare ® Filler CL,
  • Formulation 17a 17b Composition from Example 14 6.0% 6.0% Myristyl Myristate (TEGOSOFT ® MM, Evonik Operations GmbH) 2.0% 2.0% Isopropyl Myristate (TEGOSOFT ® M, Evonik Operations GmbH) 6.0% 6.0% Decyl Cocoate (TEGOSOFT ® DC, Evonik Operations GmbH) 6.0% 6.0% Cetyl Ricinoleate (TEGOSOFT ® CR, Evonik Operations GmbH) 1.0% 1.0% Water to 100% to 100% Glycerin 1.0% 1.0% Titanium Dioxide (Hombitan AC 360, Sachtleben) 8.0% 8.0% Iron Oxides (Sicovit Yellow 10 E 172, Rockwood Pigments) 0.9% 0.9% Iron Oxides (Sicovit Red 30 E 172, Rockwood Pigments) 0.2% 0.2% Iron Oxides (Sicovit Brown 70 E 172, Rockwood Pigments) 0.4% 0.4% Iron Oxides (Sicovit Black 80 E 172, Rockwood Pigments) 0.1% 0.1% Cellulose (TEGO ®
  • Formulations 18a, 18b, 18c and 18d Lotions with Cosmetic Active Ingredients
  • Formulation 18a 18b 18c 18d Composition from Example 14 3.5% 3.5% 3.0% 3.0% Stearic Acid 0.5% 0.5% Glyceryl Stearate 0.5% 0.6% 0.6% 0.6% Cetearyl Alcohol 0.5% 0.6% 0.6% 0.6% 0.6% Caprylic/Capric Triglyceride 8.5% 8.5% 8.5% 8.5% Evonik Operations GmbH) Demineralized Water to 100% to 100% to 100% Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.8% 0.8% 0.8% 0.8% 0.8% Terminalia Arjuna Bark Extract; Pentylene 2.0% 2.0% 2.0% Glycol (proposed; TEGO ® Arjuna S, Evonik Operations GmbH) Betaine; Urea; Potassium Lactate; Sodium 5.0% Polyglutamate (proposed); Hydrolyzed Sclerotium Gum (TEGO ® Smooth; Evonik Operations GmbH) Phenoxyethanol, Methylpara
  • Formulations 19a, 19b and 19c Lotion with Low Oil Phase Content
  • Formulation 19a 19b 19c Composition from Example 14 3.0% 2.0% 2.0% Polyglyceryl-3 Dicitrate/Stearate (TEGO ® Care PSC 3, 1.0% 1.0% Evonik Operations GmbH) Cetearyl Alcohol 0.5% 0.5% 0.5% Caprylic/Capric Triglyceride 6.5% 6.5% 6.5% Demineralized Water to 100% to 100% to 100% Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% Methylisothiazolinone, Methylparaben, Ethylparaben; 0.8% 0.8% Dipropylene Glycol (Microcare MEM, Thor) Glycerin; Aqua; Sodium Levulinate; Sodium Anisate 3.0% (dermosoft ® 1388; Evonik Dr. Straetmans GmbH)
  • Formulations 20a, 20b, 20c and 20d O/W Serums 1
  • Formulation 20a 20b 20c 20d Composition from Example 14 2.5% 2.5% 4.0% 4.0% Sodium Stearoyl Glutamate (Eumulgin SG, BASF 1.0% SE) Glyceryl Stearate 0.75% 0.75% Stearyl Alcohol 0.75% 0.75% Caprylic/Capric Triglyceride 2.0% 2.0% 2.0% 2.0% Oleyl Erucate (TEGOSOFT ® OER, Evonik 2.0% 2.0% 2.0% 2.0% Operations GmbH) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik 3.0% 3.0% Operations GmbH) Persea Gratissima (Avocado) Oil 1.0% 1.0% 1.0% 1.0% 1.0% Aqua; Ethylhexyl Stearate; Sodium Hyaluronate 3.0% 3.0% Crosspolymer; Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate; Sodium Isostearate (HyaCare ® Filler CL, Evonik Industries) Deminer
  • Formulations 20e 20f, 20g and 20h O/W Serums 2
  • Formulation 20e 20f 20g 20h Composition from Example 14 3.0% 3.0% 2.0% 2.0% Cetearyl Glucoside (TEGO ® Care CG 90, Evonik Operations 0.5% GmbH) Polyglyceryl-3 Dicitrate/Stearate (TEGO ® Care PSC 3, 1.5% 1.5% Evonik Operations GmbH) Glyceryl Stearate 0.75% 0.5% 0.5% 0.5% 0.5% Stearyl Alcohol 0.75% 0.5% 0.5% 0.5% 0.5% Caprylic/Capric Triglyceride 2.0% 2.0% 2.0% 2.0% Oleyl Erucate (TEGOSOFT ® OER, Evonik Operations 2.0% 2.0% 2.0% 2.0% GmbH) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations 3.0% GmbH) Persea Gratissima (Avocado) Oil 1.0% 1.0% 1.0% 1.0% Aqua; Ethylhexyl Stearate; Sodium Hyaluronate 3.0% 3.0% 3.0% Crosspolymer; Polyglyceryl-4 Di
  • Formulations 21a, 21b and 21c O/W Blemish Balm Lotion
  • Formulation 21a 21b 21c Composition from Example 14 4.00% 3.00% 3.00% Polyglyceryl-3 Methylglucose Distearate (TEGO ® Care 450, 1.00% 1.00% Evonik Operations GmbH) Glyceryl Stearate 0.75% 0.75% 0.75% Stearyl Alcohol 0.75% 0.75% 0.75% 0.75% Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik Operations 7.40% 7.40% 7.40% GmbH) Aqua; Ethylhexyl Stearate; Sodium Hyaluronate Crosspolymer; 2.00% 2.00% 2.00% Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate; Sodium Isostearate (HyaCare ® Filler CL, Evonik Industries) Ethylhexyl Methoxycinnamate 5.00% 5.00% Diethylamino Hydroxybenzoyl Hexyl Benzoate (Uvinul A
  • Formulations 22a, 22b, 22c and 22d Lotion for Sensitive Skin
  • Formulation 22a 22b 22c 22d Composition from Example 14 3.0% 3.0% 3.0% 3.0% Glyceryl Stearate 0.5% 1.0% 0.5% 0.5% Cetearyl Alcohol 1.0% 1.0% 1.0% 1.0% Butyrospermum Parkii (Shea) Butter 3.0% 3.0% 3.0% Caprylic/Capric Triglyceride 5.0% 5.0% 5.0% 5.0% Isopropyl Palmitate (TEGOSOFT ® P, Evonik 5.0% 5.0% 5.0% 5.0% Operations GmbH) Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.2% 0.2% 0.2% 0.2% 0.2% Glycerin 5.0% 5.0% 5.0% 5.0% 5.0% 5.0% 5.0% Urea 10.0% 15.0% 20.0% 20.0% Demineralized Water to 100% to 100% to 100% to 100% Phenoxyethanol, Ethylhexylglycerin (Euxyl PE 0.7% 9010, Schülke & Mayr GmbH) Sodium Hydroxide (10% aq.)(pH adjustment to q.
  • Formulations 23a, 23b, 23c and 23d Care Lotion for Dry Skin 1
  • Formulation 23a 23b 23c 23d Composition from Example 14 3.0% 2.5% 3.0% 3.0% Sodium Stearoyl Glutamate (Eumulgin SG, 1.0% BASF SE) Glyceryl Stearate 1.0% 1.0% 1.5% 1.5% Cetearyl Alcohol 1.0% 1.0% 1.5% 1.5% Cetyl Ricinoleate 2.0% 2.0% 2.0% 2.0% Oleyl Erucate (TEGOSOFT ® OER, Evonik 5.0% 5.0% 5.0% 5.0% Operations GmbH) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik 8.0% 8.0% 8.0% Operations GmbH) Decyl Cocoate (TEGOSOFT ® DC, Evonik 3.0% 3.0% 3.0% 3.0% Operations GmbH) Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.2% 0.2% 0.2% 0.2% 0.2% Glycerin 5.0% 5.0% 5.0% 5.0% 5.0% 5.0% 5.0% Urea 10.0% 10.0% 15.0% 15.0% Demineralized Water to 100% to 100% to 100% to 100% Methy
  • Formulations 23e, 23f, 23g and 23h Care Lotion for Dry Skin 2
  • Formulation 23e 23f 23g 23h Composition from Example 14 2.5% 3.0% 3.0% 3.0% Polyglyceryl-6 Distearate 0.5% Stearic Acid 0.5% 0.5% Glyceryl Stearate 1.5% 1.5% 1.5% Cetearyl Alcohol 1.5% 1.5% 1.5% 1.5% Cetyl Ricinoleate 2.0% 2.0% 2.0% Oleyl Erucate (TEGOSOFT ® OER, Evonik 5.0% 5.0% 5.0% Operations GmbH) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik 8.0% 8.0% 8.0% Operations GmbH) Decyl Cocoate (TEGOSOFT ® DC, Evonik 3.0% 3.0% 3.0% 3.0% Operations GmbH) Xanthan Gum (Keltrol CG-SFT, CP Kelco) 0.2% 0.2% 0.2% 0.2% 0.2% 0.2% Glycerin 5.0% 5.0% 5.0% 5.0% 5.0% 5.0% Urea 15.0% 20.0% 20.0% 20.0% Demineralized Water to 100% to 100% to 100% to 100% Methylisothiazolin
  • Formulations 24a, 24b and 24c Preservative-Free Lotions 1
  • Formulation 24a 24b 24c Composition from Example 14 3.0% 2.0% 3.0% (AXOL ® C 62, Evonik Operations GmbH) 1.0% Glyceryl Stearate 0.2% 0.2% 0.5% Stearyl Alcohol 0.2% 0.2% 0.5% Prunus Amygdalus Dulcis (Sweet Almond) Oil 10.0% 10.0% 10.0% 10.0% Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations 6.6% 6.6% 6.0% GmbH) Glycerin 4.0% 4.0% 4.0% Demineralized Water to 100.0% to 100.0% to 100.0% Caprylyl Glycol, Glycerin, Glyceryl Caprylate, Phenylpropanol 1.0% 1.0% (Dermosoft ® LP, Evonik Dr.
  • Formulations 24d, 24e and 24f Preservative-Free Lotions 2
  • Formulation 24d 24e 24f Composition from Example 14 3.0% 3.0% 1.5% Glyceryl Stearate SE 0.5% Polyglyceryl-3 Dicitrate/Stearate (TEGO ® Care PSC 3, Evonik 1.5% Operations GmbH) Glyceryl Stearate 0.5% 0.5% 0.5% Stearyl Alcohol 0.5% 0.5% 0.5% Prunus Amygdalus Dulcis (Sweet Almond) Oil 10.0% 10.0% 10.0% 10.0% Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations GmbH) 6.0% 6.0% 6.0% Glycerin 4.0% 4.0% 4.0% Demineralized Water to 100.0% to 100.0% to 100.0% Methylpropanediol, Caprylyl Glycol, Phenylpropanol 4.0% (Dermosoft ® OMP, Evonik Dr.
  • Formulation 25a 25b Composition from Example 9 or 10 2.0% 2.0% Beeswax 0.5% 0.5% Castor wax 0.5% 0.5% Paraffinum Perliquidum 10.5% 10.5% Decyl Cocoate (TEGOSOFT ® DC, Evonik 8.0% 8.0% Operations GmbH) Tocopheryl acetate 0.5% 0.5% Cyclopentasiloxane 6.0% 6.0% Sodium chloride 0.5% 0.5% Water to 100% to 100% Glycerin 3.0% 3.0% Phenoxyethanol; Ethylhexylglycerin (Euxyl 0.7% PE 9010, Schülke & Mayr GmbH) Ethanol 5.0% 5.0% Glyceryl Caprylate (dermosoft ® GMC; 0.4% Evonik Dr. Straetmans GmbH) Zinc Sulfate 1.0%
  • Formulation 26a 26b Composition from Example 9 or 10 2.0% 2.0% Mineral oil 17.0% 17.0% Castor wax 0.4% 0.4% Microcrystalline wax 0.6% 0.6% Water to 100% to 100% Sodium chloride 0.5% 0.5% Urea 10.0% 10.0% Phenoxyethanol; Ethylhexylglycerin (Euxyl PE 9010, 0.7% Schülke & Mayr GmbH) Glyceryl Caprylate (dermosoft ® GMC; Evonik Dr. 0.35% Straetmans GmbH) Pentylene Glycol (dermosoft ® Pentiol eco; Evonik 2.0% Dr. Straetmans GmbH)
  • Formulation 27a 27b Composition from Example 9 or 10 0.8% 0.8% Cetyl Dimethicone (ABIL ® Wax 9801, Evonik 1.6% 1.6% Operations GmbH) Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik 4.0% 4.0% Operations GmbH) Dimethicone (ABIL ® 350, Evonik Operations 1.0% 1.0% GmbH) Cyclopentasiloxane 4.0% 4.0% Magnesium stearate 0.3% 0.3% Water to 100% to 100% Propylene glycol 5.0% 5.0% Sodium chloride 1.0% 1.0% Methylisothiazolinone, Methylparaben, Ethylparaben; 0.8% Dipropylene Glycol (Microcare MEM, Thor) Glyceryl Caprylate (dermosoft ® GMC; Evonik Dr. 0.25% Straetmans GmbH) Phenylpropanol (dermosoft ® 250 eco; Evonik Dr. 0.35% Straet
  • Formulation 28a 28b 28c Composition from Example 9 or 10 2.0% 1.5% 1.5% Polyglyceryl-4 Diisostearate/ 0.5% 0.5% Polyhydroxystearate/Sebacate (ISOLAN ® GPS, Evonik Operations GmbH) Castor wax 0.5% 0.5% 0.5% Beeswax 0.5% 0.5% 0.5% 0.5% Ethylhexyl Stearate (TEGOSOFT ® 10.0% 10.0% 10.0% OS, Evonik Operations GmbH) Diethylhexyl Carbonate (TEGOSOFT ® 8.5% 8.5% 8.5% DEC, Evonik Operations GmbH) Dimethicone (Belsil DM 5, Wacker 6.0% 6.0% 6.0% Chemical Corp.) Tocopheryl acetate 0.5% 0.5% 0.5% Glycerin 3.0% 3.0% 3.0% Water to 100% to 100% to 100% Sodium chloride 1.0% 1.0% 1.0% Ethanol 20.0% 20.0% 20.0% 0.5%
  • Formulations 29a, 29b and 29c W/O Cream Based on Natural Ingredients
  • Formulation 29a 29b 29c Composition from Example 9 or 10 3.0% 2.5% 2.5% Diisostearyl Polyglyceryl-3 Dimer 0.5% 0.5% Dilinoleate (ISOLAN ® PDI, Evonik Operations GmbH) Diethylhexyl Carbonate (TEGOSOFT ® 7.0% 7.0% 7.0% DEC, Evonik Operations GmbH) Oleyl Erucate (TEGOSOFT ® OER, Evonik 3.0% 3.0% 3.0% Operations GmbH) Almond oil 7.0% 7.0% 7.0% Shea butter 2.0% 2.0% 2.0% Cetyl Ricinoleate (TEGOSOFT ® CR, 1.0% 1.0% 1.0% Evonik Operations GmbH) Beeswax 0.6% 0.6% 0.6% Castor wax 0.4% 0.4% 0.4% Glycerin 5.0% 5.0% 5.0% 5.0% Water to 100% to 100% to 100% Magnesium sulfate heptahydrate 1.5% 1.5% 1.5% Sodium Benzoate, Potassium Sorbate (Euxyl 0.5% 0.5% K 712,
  • Formulation 30a 30b 30c Composition from Example 9 or 10 3.0% 2.5% 2.5% Polyglyceryl-3 Oleate (ISOLAN ® 0.5% 0.5% GO 33, Evonik Operations GmbH) Isoamyl Cocoate (TEGOSOFT ® AC, 5.0% 5.0% 5.0% Evonik Operations GmbH) Diethylhexyl Carbonate (TEGOSOFT ® 12.0% 12.0% 12.0% DEC, Evonik Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® 4.0% 4.0% 4.0% 4.0% XC, Evonik Operations GmbH) Zinc stearate 0.5% 0.5% 0.5% Water to 100% to 100% to 100% Glycerin 3.0% 3.0% 3.0% Sodium chloride 1.5% 1.5% 1.5% Phenoxyethanol; Ethylhexylglycerin (Euxyl 0.7% 0.7% PE 9010, Schülke & Mayr GmbH) Benzyl Alcohol; Caprylyl Glycol; Benzoic 1.5% Acid (Verstatil ® BOB;
  • Formulations 31a, 31b and 31c Moisturizing Lotion Containing Urea
  • Formulation 31a 31b 31c Composition from Example 9 or 10 2.0% 1.5% 1.5% Cetyl PEG/PPG-10/1 Dimethicone (ABIL ® 0.5% 0.5% EM 180, Evonik Operations GmbH) Microcrystalline wax 0.5% 0.5% 0.5% Castor wax 0.5% 0.5% 0.5% C12-15 Alkyl Benzoate 7.5% 7.5% 7.5% Oleyl Erucate (TEGOSOFT ® OER, Evonik 5.0% 5.0% 5.0% Operations GmbH) Ethylhexyl Palmitate (TEGOSOFT ® OP, 5.0% 5.0% Evonik Operations GmbH) Caprylic/Capric Triglyceride 5.0% 5.0% 5.0% Glycerin 3.0% 3.0% 3.0% Urea 20.0% 20.0% 20.0% Magnesium sulfate heptahydrate 1.0% 1.0% 1.0% Water to 100% to 100% to 100% Phenoxyethanol; Ethylhexylglycerin (Euxyl 0.70% 0.70% PE 9010, Schülke & Mayr GmbH)
  • Formulations 32a, 32b, 32c and 32d W/O Lotion with Light-as-Silk Skin Feel
  • Formulation 32a 32b 32c 32d Composition from Example 9 or 10 2.5% 2.0% 2.0% 2.0% Cetyl PEG/PPG-10/1 Dimethicone (ABIL ® EM — 0.5% — — 90, Evonik Operations GmbH) Bis-PEG/PPG-14/14 Dimethicone; Dimethicone — — 1.0% 1.0% (ABIL ® EM 97 S, Evonik Operations GmbH) Microcrystalline wax 0.1% 0.1% 0.1% 0.1% Castor wax 0.1% 0.1% 0.1% 0.1% 0.1% 0.1% Diethylhexyl Carbonate (TEGOSOFT ® DEC, 11.8% 11.8% 11.8% 11.8% Evonik Operations GmbH) Myristyl Myristate (TEGOSOFT ® MM, Evonik 1.0% 1.0% 1.0% 1.0% 1.0% Operations GmbH) Dimethicone (Belsil DM 5, Wacker Chemical Corp.) 8.0% 8.0% 8.0% 8.0% Dimethicone (ABIL ® 350, Evonik Operations GmbH) 0.5% 0.5% 0.5%
  • Formulations 33a, 33b and 33c Baby-Care Product
  • Formulation 33a 33b 33c Composition from Example 9 or 10 3.0% 2.0% 2.0% Paraffinum Liquidum; Petrolatum; Ozokerite; Glyceryl Oleate; 1.0% 1.0% Lanolin Alcohol (PROTEGIN ® XN, Evonik Operations GmbH) Castor wax 0.1% 0.1% 0.1% Microcrystalline wax 0.1% 0.1% 0.1% 0.1% Oleyl Erucate (TEGOSOFT ® OER, Evonik Operations GmbH) 1.0% 1.0% 1.0% 1.0% 1.0% Isoamyl Cocoate (TEGOSOFT ® AC, Evonik Operations GmbH) 3.8% 3.8% 3.8% Ethylhexyl Palmitate (TEGOSOFT ® OP, Evonik Operations GmbH) 1.0% 1.0% 1.0% 1.0% Almond oil 1.0% 1.0% 1.0% 1.0% Zinc oxide 20.0% 20.0% 20.0% Glycerin 3.0% 3.0% 3.0% Magnesium sulfate heptahydrate 1.0% 1.0% 1.0% Sodium Lactate; Sodium PCA; Glycine; Fruc
  • Formulation 34a 34b 34c Composition from Example 9 or 10 3.0% 2.5% 2.5% Petrolatum; Ozokerite; Hydrogenated Castor Oil; Glyceryl isostearate; 0.5% 0.5% Polyglyceryl-3 Oleate (PROTEGIN ® W, Evonik Operations GmbH) Castor wax 0.1% 0.1% 0.1% Microcrystalline wax 0.1% 0.1% 0.1% 0.1% Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik Operations GmbH) 9.0% 9.0% 9.0% 9.0% Ethylhexyl Palmitate (TEGOSOFT ® OP, Evonik Operations GmbH) 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% 9.0% Stearyl Heptanoate (TEGOSOFT ® SH, Evonik Operations GmbH) 8.8% 8.8% 8.8% Glycerin 3.0% 3.0% 3.0% 3.0% Magnesium sulfate
  • Formulations 35a and 35b Sunscreen Lotion SPF 30 UVA with Insect Repellent
  • Formulations 36a and 36b Sunscreen Lotion SPF 30 UVA in Accordance with Exocet Criteria
  • Formulation 36a 36b Composition from Example 9 or 10 3.0% 2.0% Polyglyceryl-3 Polyricinoleate (Cithrol — 1.0% PG3PR, Croda Int. PLC) Isoamyl Cocoate (TEGOSOFT ® AC, Evonik 2.0% 2.0% Operations GmbH) Decyl Cocoate (TEGOSOFT ® DC, Evonik 10.0% 10.0% Operations GmbH) Isopropyl Palmitate (TEGOSOFT ® P, 10.0% 10.0% Evonik Operations GmbH) Zinc Oxide (Zinc Oxide PI, Symrise) 16.0% 16.0% Titanium Dioxide [nano]; Alumina; 9.0% 9.0% Stearic Acid (Eusolex T-S, Merck KGaA) Water to 100% to 100% Glycerin 3.0% 3.0% Magnesium sulfate heptahydrate 1.0% 1.0% Sodium Benzoate, Potassium Sorbate 0.5% 0.5% (Euxyl K 712, Schülke & Mayr
  • Formulations 37a, 37b, 37c and 37d Sunscreen Spray SPF 30 UVA
  • Formulation 37a 37b 37c 37d Composition from Example 9 or 10 3.0% 2.0% 3.0% 2.0% Cetyl PEG/PPG-10/1 Dimethicone (ABIL ® EM 90, — 1.0% — — Evonik Operations GmbH) Polyglyceryl-4 Diisostearate/Polyhydroxystearate/ — — — 1.0% Sebacate (ISOLAN ® GPS, Evonik Operations GmbH) Diethyihexyl Carbonate (TEGOSOFT ® DEC, Evonik 13.0% 13.0% 11.3% 11.3% Operations GmbH) C12-15 Alkyl Benzoate 13.0% 13.0% 11.3% 11.3% Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 1.0% 1.0% 1.5% 1.5% (Tinosorb S, BASF SE) Butyl Methoxydibenzoylmethane — — 3.0% 3.0% Ethylhexyl Methoxycinnamate 5.0% 5.0% — — Octocrylene —
  • Formulations 38a, 38b, 38c and 38d Sunscreen Lotion SPF 50 UVA
  • Formulation 38a 38b 38c 38d Composition from Example 9 or 10 3.0% 2.5% 3.0% 2.5% Cetyl PEG/PPG-10/1 Dimethicone (ABIL ® EM 90, Evonik — 1.0% — 1.0% Operations GmbH) Microcrystalline wax 0.3% 0.3% 0.3% 0.3% Castor wax 0.3% 0.3% 0.3% 0.3% 0.3% Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik 2.4% 2.4% — — Operations GmbH) Phenoxyethyl Caprylate (TEGOSOFT ® XC, Evonik — — 3.9% 3.9% Operations GmbH) Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb 6.0% 6.0% — — S, BASF SE) Diethylamino Hydroxybenzoyl Hexyl Benzoate (Uvinul A 7.0% 7.0% 5.0% 5.0% Plus, BASF SE) Butyl Methoxydibenzoylmethane —
  • Formulations 39a, 39b and 39c Sunscreen Lotion SPF 50 in Accordance with FDA Criteria
  • Formulation 39a 39b 39c Composition from Example 9 or 10 2.0% 1.5% 1.5% Lauryl PEG-10 Tris(Trimethylsiloxy)silylethyl Dimethicone (ES- — 0.5% 0.5% 5300 Formulation Aid, Dow Corning Corp.) Ethylhexyl Methoxycinnamate; Diethylamino Hydroxybenzoyl 7.5% 7.5% 7.5% Hexyl Benzoate (Uvinul A + B, BASF SE) Ethylhexyl Salicylate 5.0% 5.0% 5.0% Homosalate 15.0% 15.0% 15.0% 15.0% Butyl Methoxydibenzoylmethane 3.0% 3.0% 3.0% Benzophenone-3 6.0% 6.0% 6.0% Octocrylene 10.0% 10.0% 10.0% Triisostearin 2.0% 2.0% 2.0% Microcrystalline wax 1.2% 1.2% 1.2% Castor wax 0.8% 0.8% 0.8% Cetyl Dimethicone (ABIL ® Wax 9801, Evonik Operations 2.0% 2.0% 2.0% GmbH)
  • Formulation 40a 40b 40c 40d 40e 40f Composition from Example 9 4.5% 2.5% 3.0% 2.5% 2.0% 2.0% or 10 Bis-(Glyceryl/Lauryl) Glyceryl — 2.0% — — — — Lauryl Dimethicone; Caprylic/Capric Triglyceride (ABIL ® EM 120, Evonik Operations GmbH) Polyglyceryl-4 Isostearate — — 1.0% — — — (ISOLAN ® GI 34, Evonik Operations GmbH) Cetyl Diglyceryl — — 1.0% — — Tris(Trimethylsiloxy)silylethyl Dimethicone (DC-5600, Dow Corning Corp.) Lauryl Polyglyceryl-3 — — — — 1.0% — Polydimethylsiloxyethyl Dimethicone (KF-6105, Shin- Etsu Chemical Co.) Polyglyceryl-4 Isostearate; — — — —
  • Formulations 41a, 41b, 41c, 41d, 41e, 41f and 41g CC (Colour Control) Fluid
  • Formulation 41a 41b 41c 41d 41e 41f 41g Composition from Example 9 3.0% 2.0% 2.5% 3.0% 2.5% 2.0% 1.0% or 10
  • Formulations 42a, 42b, 42c, 42d and 42e Antiperspirant/Deodorant Spray or Aerosol Spray
  • Formulation 42a 42b 42c 42d 42e Composition from Example 9 or 10 3.0% 2.0% 3.0% 2.0% 2.0% Polyglyceryl-4 — 1.0% — 1.0% 1.0% Diisostearate/Polyhydroxystearate/ Sebacate (ISOLAN ® GPS, Evonik Operations GmbH) Isopropyl Palmitate (TEGOSOFT ® 20.0% 20.0% 20.0% 20.0% 20.0% P, Evonik Operations GmbH) Diethylhexyl Carbonate 7.0% 7.0% 7.0% 7.0% 7.0% 7.0% 7.0% 7.0% 7.0% (TEGOSOFT ® DEC, Evonik Operations GmbH) Triethyl Citrate (dermofeel ® TEC 5.0% eco; Evonik Dr.
  • Formulations 43a, 43b, 43c and 43d Sunscreen Aerosol SPF 50 UVA
  • Formulation 43a 43b 43c 43d Composition from Example 9 or 10 4.0% 4.0% 4.0% 4.0% Cetyl PEG/PPG-10/1 Dimethicone (ABIL ® EM 90, Evonik — — 1.0% 1.0% Operations GmbH) C12-15 Alkyl Benzoate 10.0% 8.0% 10.0% 8.0% Diethylhexyl Carbonate (TEGOSOFT ® DEC, Evonik 13.0% 10.0% 13.0% 10.0% Operations GmbH) Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb 4.0% 4.0% 4.0% 4.0% S, BASF SE) Diethylamino Hydroxybenzoyl Hexyl Benzoate (Uvinul A 5.0% 5.0% 5.0% 5.0% Plus, BASF SE) Ethylhexyl Salicylate 5.0% 5.0% 5.0% 5.0% 5.0% Ethylhexyl Methoxycinnamate 4.0% 4.0% 4.0% 4.0% Water to 100% to 100% to 100% to 100% to 100% Glycerin
  • Formulations 47a 47b Water to 100.0% to 100.0% Composition from Example 4, 8, 15 or 16 2.5% 2.5% Composition from Example 14 1.5% 1.5% Cocamidopropyl Betaine (TEGO ® Betain F 50, Evonik 22.0% 22.0% Operations GmbH, 38%) Lauryl Glucoside (Plantacare 1200 UP, BASF, 50%) 6.0% 6.0% Sodium Cocoyl Glutamate (Plantapon ACG HC, BASF) 1.5% 1.5% Sodium Cocoyl Glycinate (Hostapon SG, Clariant) 0.8% 0.8% Zinc Pyrithione (Microcare ZP, Thor) 0.1% 0.1% PEG-120 Methyl Glucose Dioleate (ANTIL ® 120 Plus, Evonik) 0.4% 0.4% Sodium Chloride 0.5% 0.5% Isostearamide MIPA; Glyceryl Laurate (ANTIL ® SPA 80, Evonik) 0.5% 0.5% Xanthan Gum (Keltrol CG-SFT,
  • Formulation 49 Cream Soap
  • Formulation 51 Micellar Water for Make-Up Removal
  • Formulation 52a 52b Composition from Example 4, 8, 15 or 16 3.5% 3.5% Aloe Barbadensis Leaf Extract (Aloe-Con UP 40, Florida Food 0.2% 0.2% Products Inc.) Isopropyl Myristate (TEGOSOFT ® M, Evonik) 0.2% 0.2% Disodium Cocoamphodiacetate (REWOTERIC ® AM 2 C NM, 1.5% 1.5% Evonik Operations GmbH, 39%) Perfume 0.2% 0.2% Propylene Glycol (Euxyl K 320, Schülke & Mayr GmbH) 2.5% 2.5% Hydrolyzed Silk (Crosilk 10000, Croda Inc.) 0.2% 0.2% Caprylyl/Capryl Glucoside (Plantacare 810 UP, BASF) 1.0% 1.0% Water to 100.0% to 100.0% Citric Acid to pH 5.0 to pH 5.0 Phenoxyethanol (S&M Phenoxyethanol, Schülke & Mayr GmbH) 0.5% 0.5% Dehydroacetic Acid (Unisept DHA

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US17/757,576 2019-12-20 2020-12-17 Process for enzymatically preparing sugar esters and/or sugar alcohol esters Pending US20230055814A1 (en)

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EP19218421.6 2019-12-20
EP19218421.6A EP3839052A1 (fr) 2019-12-20 2019-12-20 Procédé de fabrication enzymatique d'esters de sucre et/ou d'esters d'alcool de sucre
PCT/EP2020/086736 WO2021122971A1 (fr) 2019-12-20 2020-12-17 Procédé de préparation enzymatique d'esters de sucre et/ou d'esters d'alcool de sucre

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US17/757,528 Pending US20230023141A1 (en) 2019-12-20 2020-12-17 Sorbitan esters and process for enzymatically preparing same
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GB947830A (en) * 1961-06-20 1964-01-29 Ledoga Spa Esters of fatty acids with xylite
GB1016885A (en) * 1962-10-16 1966-01-12 Ledoga Spa Xylitol esters
BE623684A (fr) * 1962-10-19
GB1025028A (en) * 1962-12-28 1966-04-06 Ledoga Spa Xylitol esters
JPS58116688A (ja) * 1981-12-28 1983-07-11 Asahi Denka Kogyo Kk 油脂類のエステル基交換反応方法
US4614718A (en) 1983-08-23 1986-09-30 Dai-Ichio Kogyo Seiyaku Co., Ltd. Synthesis of sugar or sugar-alcohol fatty acid esters
JPH0665309B2 (ja) 1986-11-26 1994-08-24 花王株式会社 エステル化方法
EP0413307A1 (fr) * 1989-08-15 1991-02-20 Lion Corporation Procédé de fabrication de saccharides mono-estérifiés par des acides gras
DK144292D0 (da) 1992-12-01 1992-12-01 Novo Nordisk As Forbedret fremgangsmaade
US5635614A (en) * 1995-06-09 1997-06-03 National Research Council Of Canada Sugar/sugar alcohol esters
GB0409066D0 (en) 2004-04-23 2004-05-26 Ici Plc Surfactant composition
DK1934342T3 (en) 2005-09-30 2015-03-23 Novozymes As Immobilization of enzymes
DE102009001748A1 (de) 2009-03-23 2010-09-30 Evonik Goldschmidt Gmbh Formulierungen enthaltend Sorbitancarbonsäureester
KR101452769B1 (ko) * 2012-09-25 2014-10-21 지준홍 지속성 냉감 효과를 갖는 자일리톨 지방산 에스테르를 유효성분으로 함유하는 화장료 조성물
KR101939851B1 (ko) 2013-10-01 2019-01-17 켐유니온 키미카 엘티디에이 화장품, 약제학 및 수의학 적용분야를 위한 항미생물, 공-유화제 및 증점제 특성을 가지는 자일리틸 에스테르 함유 조성물
KR20150057589A (ko) * 2013-11-20 2015-05-28 지준홍 자일리톨 지방산 에스테르를 유효성분으로 포함하는 방부제 조성물
CN105754982B (zh) * 2014-12-15 2021-12-07 丰益(上海)生物技术研发中心有限公司 固定化脂肪酶以及固定化脂肪酶的制备方法
KR101823324B1 (ko) * 2016-07-12 2018-03-14 주식회사 일신웰스 당 지방산 에스테르 제조방법

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JP2023507446A (ja) 2023-02-22
BR112022011453A2 (pt) 2022-08-23
CN114787118A (zh) 2022-07-22
EP4077696A1 (fr) 2022-10-26
EP3839052A1 (fr) 2021-06-23
US20230023141A1 (en) 2023-01-26
BR112022011457A2 (pt) 2022-08-23
CN114829617A (zh) 2022-07-29
JP2023507448A (ja) 2023-02-22
WO2021122972A1 (fr) 2021-06-24
WO2021122971A1 (fr) 2021-06-24
JP2023507450A (ja) 2023-02-22
EP4077697A1 (fr) 2022-10-26
BR112022011988A2 (pt) 2022-08-30
US20230033620A1 (en) 2023-02-02
CN114787368A (zh) 2022-07-22
EP4077698A1 (fr) 2022-10-26

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