Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/01—Hydrocarbons
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/04—Dispersions; Emulsions
  • A61K8/06—Emulsions
  • A61K8/068—Microemulsions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
  • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
  • A61K8/731—Cellulose; Quaternized cellulose derivatives
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/12—Preparations containing hair conditioners
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/54—Polymers characterized by specific structures/properties
  • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
  • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic

Definitions

• the invention is in the field of cosmetic agents which are in the form of finely divided emulsions and further relates to a process for the preparation of such emulsions.
• the object of the present invention has thus been to provide aqueous finely divided emulsions which are easier to prepare.
• a first object of the invention relates to the preparation of aqueous emulsions having an average particle size of less than 1 micron by first preparing in a first step a microemulsion containing at least 10-20 wt.% Of an alkyl (oligo) glycoside of the general formula R.
• R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
• G is a sugar radical having 5 or 6 carbon atoms
• p is a number from 1 to 10 and 4-10% by weight an ester of glycerol with a fatty acid of chain length C12-C22 and 5-30% by weight of an oil body and the balance to 100% by weight of water and optionally further ingredients, and then in a second step this microemulsion with the 5 to 20 times the volume of the microemulsion at temperatures of 10 to 45 ° C, preferably from 15 to 35 ° C diluted with water.
• the method according to the invention is therefore a two-stage process in which a microemulsion is prepared in a known manner in the first step.
• Microemulsions are understood to mean initially all macroscopically homogeneous, optically transparent, low-viscosity and in particular thermodynamically stable mixtures of two immiscible liquids and at least one nonionic or ionic surfactant.
• the average particle sizes of the microemulsions are usually below 100 nm, they have a high transparency and are stable on centrifugation at 2000 rpm for at least 30 minutes against a visible phase separation.
• step 1 The preparation of the microemulsions in step 1 is preferably carried out simply by mixing the oil phase with the further oil-soluble ingredients, heating the O phase over the melting point of all constituents and then adding the aqueous surfactant-containing phase.
• the thermodynamically stable microemulsion then forms spontaneously, if necessary, a little more stirring is required.
• the microemulsion contains as compulsory constituents a sugar surfactant, specifically an acyl (oligo) glycoside (also referred to below as "APG").
• a sugar surfactant specifically an acyl (oligo) glycoside (also referred to below as "APG").
• Alkyl and / or alkenyl oligoglucosides in the context of the present teaching follow the formula R' ⁇ - [cf. G] P in which R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10.
• the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketones having 5 or 6 carbon atoms, preferably glucose,
• the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides
• Index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
• the value p for a given alkyloligoglycoside is an analytically determined arithmetic quantity, which usually represents a fractional number. Preference is given to using alkyl and / or alkenyl oligoglycosides having an average degree of oligomerization p of from 1.1 to 3.0. From an application point of view, those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4 are preferred.
• APGs are present in amounts of between 10 and 20% by weight, based in each case on the total amount of microemulsions. emulsion included. Amounts in the range of 14 to 19 wt .-% are particularly preferred.
• esters of fatty acids of chain length C12-C22 with glycerol are contained in the emulsions according to the invention.
• Monoesters of glycerol are preferably used in this case, with monoesters of glycerol in particular being suitable with unsaturated linear fatty acids.
• Glycerol mono-oleate is particularly preferred for the purposes of the invention.
• These glycerol esters are contained in the microemulsions in amounts of from 4 to 10% by weight, preferably from 5 to 9% by weight, based in each case on the total weight of the microemulsion.
• the microemulsions of the present invention still contain an oil body, ie a non-water-soluble organic phase in amounts of 5 to 30 wt .-%.
• Particularly preferred oil phases are selected from the group of Guerbet alcohols based on fatty alcohols having 6 to 18 C atoms, esters of linear C 6 -C 22 fatty acids with linear or branched C 6 -C 22 fatty alcohols or esters of branched C ⁇ -C ⁇ carboxylic acids with linear or branched C 6 -C 22 fatty alcohols, esters of linear C 6 -C 22 fatty acids with branched alcohols, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, triglycerides based on C 6 - Cio fatty acids, liquid mono- / di- / Triglyceridmischept based on C 6 -C] 8 fatty acids, esters of C 2 -Cj 2 dicarbox
• hydrocarbon mixture mixtures of hydrocarbons containing up to 10% by weight of substances other than hydrocarbons.
• the percentages by weight of the linear C11 and linear C13 hydrocarbons relate in each case to the sum of the hydrocarbons present in the mixture.
• the non-hydrocarbons present up to 10% by weight are not taken into account for this calculation.
• the substances which do not belong to the hydrocarbons and which may contain up to 10% by weight, in particular up to 8% by weight, preferably up to 5% by weight, in the hydrocarbon mixture are, for example, fatty alcohols , which remain as unreacted starting materials in the hydrocarbon mixture.
• CX hydrocarbon includes hydrocarbons having a C number of X, for example, the term Cl 1 hydrocarbon includes all hydrocarbons having a C number of 11.
• hydrocarbon mixture which contains at least 2 different hydrocarbons whose carbon number differs by more than 1, wherein these 2 mutually different hydrocarbons at least 60 wt .-%, preferably at least 70 wt .-% - based on the Make up the sum of hydrocarbons.
• n is an odd number, in particular 7, 9, 11, 13, 15, 17, 19, 21 and / or 23.
• hydrocarbon a hydrocarbon mixture can be used which contains 14 C isotopes and wherein the hydrocarbon mixture contains at least 2 different hydrocarbons whose C number differs by more than 1.
• solid fats and / or waxes can also be used as the oil component. These may also be in mixture with the oils mentioned in the previous section.
• Typical examples of fats are glycerides, i. solid or liquid vegetable or animal products consisting essentially of mixed glycerol esters of higher fatty acids. Particular mention should be made of solid mono- and diglycerides, e.g. Glycerol monooleate or glycerol monostearate.
• waxes come u.a. natural waxes, e.g.
• microemulsions Another essential component of the microemulsions, as used in the process according to the invention is water.
• the water should preferably be demineralized.
• the microemulsions used in the first step of the process preferably contain up to 81% by weight of water. Preferred ranges are amounts of 30 to 80 wt .-% and in particular from 45 to 65 wt .-% water.
• the microemulsions may contain, as an additional constituent, also fatty alcohols of the general formula R -OH, where R is a saturated or unsaturated, branched or unbranched alkyl or Alkenyl radical having 6 to 22 carbon atoms, may contain.
• Typical examples are caprol alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol , Behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures which are obtained, for example, in the high-pressure hydrogenation of industrial methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as monomer fraction in the dimerization of unsaturated fatty alcohols.
• fatty alcohols having 12 to 18 carbon atoms such as coconut, palm, palm kernel or Taigfettalkohol. Particularly preferred is the concomitant use of cetyl alcohol, stearyl alcohol, arachyl alcohol and behenyl alcohol and mixtures thereof.
• fatty alcohols are included, they are preferably used in amounts of up to 15% by weight, based on the total microemulsion, with the range from 1 to 10% by weight and preferably from 2 to 8% by weight being particularly preferred.
• These fatty alcohols, which are water-insoluble organic constituents also do not fall under the definition of the oil body according to the invention.
• the microemulsion which is prepared in the first step of the process according to the invention may also contain anionic surfactants.
• anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, alkyl ether sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, monoglyceride sulfates, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates , Fatty acid sarcosinates, fatty acid taurides, N-acyl amino acids such as acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl
• fatty alcohol ether sulfates are preferred, especially those of the general formula R 3 O- (CH 2 CH 2 O) 1n SOsX in which R 3 is a linear or branched alkyl and / or alkenyl group containing 6 to 22 carbon atoms n is a number from 1 to 10 and X is an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
• ether sulfates are known anionic surfactants which are industrially produced by SO 3 or chlorosulfonic acid (CSA) sulfation of fatty alcohol or oxoalcohol polyglycol ethers and subsequent neutralization.
• Typical examples are the sulfates of addition products of on average 1 to 10 and especially 2 to 5 moles of ethylene oxide, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol, and technical mixtures thereof Form of their sodium and / or magnesium salts.
• the ether sulfates can aur rub both a conventional and a narrow homolog distribution.
• ether sulfates based on adducts of an average of 2 to 3 moles of ethylene oxide to technical C 12 / H - or C ⁇ / JS - Kokosfettalkoholfr hopeen in the form of their sodium and / or magnesium salts.
• microemulsions used in the process according to the invention may contain further nonionic, amphoteric and / or cationic surfactants, preferably in amounts of from 1 to 25% by weight, based on the total weight of the emulsion.
• Typical examples of other nonionic surfactants are, for example, fatty acid N-alkylglucamides, polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates, alcohol ethoxylates and amine oxides.
• Alcohol ethoxylates are referred to as fatty alcohol or Oxoalkoholethoxylate production and preferably follow the formula R 4 O (CH 2 CH 2 O) n HR 4 for a linear or branched alkyl and / or alkenyl radical having 6 to 22 carbon atoms and n for numbers of 1 to 50 stands.
• Typical examples are the adducts of an average of 1 to 50, preferably 5 to 40 and especially 10 to 25 moles of caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, Petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures, for example, in the high pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from the Roelen 1 - rule oxo synthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
• Preferred are adducts of 10 to 40 moles of ethylene oxide with technical fatty alcohols having 12
• amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
• suitable alkylbetaines are the carboxyalkylation products of secondary and in particular tertiary amines. Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, dodecylethylamine.
• methylamine Ci 2 / i 4 -Kokosalkyldimethylamin, myristyldimethylamine, cetyldimethylamine, Stearyldimethyl-amine, stearyl, oleyldimethylamine, C16 / 18 tallow alkyl dimethyl amine and technical mixtures thereof.
• carboxyalkylation products of amidoamines are also suitable.
• Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely capronic, caprylic, capric, lauric, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic and behenic acids and erucic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, which are condensed with sodium chloroacetate.
• condensation product of C 8 / i 8 coconut fatty acid-N, N-dimethylaminopropylamidamide with sodium chloroacetate Preference is given to the use of a condensation product of C 8 / i 8 coconut fatty acid-N, N-dimethylaminopropylamidamide with sodium chloroacetate.
• imidazolinium betaines are also suitable. These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyfunctional amines, such as, for example, aminoethylethanolamine (AEEA) or diethylenetriamine.
• AEEA aminoethylethanolamine
• the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
• Typical examples are condensation products of the above mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or turn Ci 2/14 coconut oil fatty acid, which are subsequently betainized with sodium chloroacetate.
• Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, especially quaternized fatty acid trialkanolamine ester salts.
• microemulsions for step 1 are composed as follows:
• microemulsions prepared in the first step of the process according to the invention in accordance with the above general description are diluted with water in a separate step and then spontaneously form the finely divided emulsion according to the invention having an average particle size of less than 1 ⁇ m.
• 4 to 9 parts of water are added to a portion of the microemulsion.
• the dilution step can be carried out immediately upon the completion of the microemulsion in step 1 - but it is also possible and preferred in practice that the dilution be done later.
• the microemulsions of step 1 are likewise storage-stable, so that no disadvantages with regard to the stability or constitution of the emulsion produced later in the second step occur even after prolonged storage of this intermediate.
• the emulsion which are obtained by the final dilution step, have an average particle size of less than 1 micron, preferably less than 0.8 microns.
• the proportion of particles with a diameter or a size of ⁇ 1 ⁇ m is preferably at least 70%, preferably at least 80% and particularly preferably at least 90% of all particles.
• the finely divided emulsions thus prepared are themselves an object of the present application.
• the finely divided emulsions according to the invention can be used for the preparation of cosmetic preparations, such as hair shampoos, hair lotions, bubble baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat compounds, stick preparations, powders or ointments ,
• These cosmetic agents may also contain, as further auxiliaries and additives, mild surfactants, oil bodies, emulsifiers, pearlescent waxes, bodying agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic agents, UV sun protection factors, antioxidants , Deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanner, tyrosine inhibitors (depigmentation agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the
• microemulsion of the following composition was prepared by mixing the ingredients:
• the particle size of the emulsions was measured with a Horiba LB500 meter.
• the resulting emulsions are storage stable, i. when stored at 40 ° C for 4 weeks no visible oil separation occurs.

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• 2008
  • 2008-06-14 WO PCT/EP2008/004802 patent/WO2008155074A2/de active Application Filing
  • 2008-06-14 CN CN200880020996A patent/CN101835451A/zh active Pending
  • 2008-06-14 US US12/665,494 patent/US20100247588A1/en not_active Abandoned
  • 2008-06-14 EP EP08773439A patent/EP2162112A2/de not_active Ceased
  • 2008-06-14 JP JP2010512581A patent/JP5690138B2/ja not_active Expired - Fee Related
• 2013
  • 2013-06-12 JP JP2013123436A patent/JP2013237672A/ja active Pending

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