Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4966—Triazines or their condensed derivatives
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
  • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
  • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/54—Three nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/54—Three nitrogen atoms
  • C07D251/70—Other substituted melamines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

• the present invention relates to novel triazine derivatives, to a process for the preparation of such compounds and to the use of such compounds for cosmetic preparations.
• novel triazine derivatives correspond to the formula
• R is a -C ⁇ alkyl, C 2 -C 18 alkenyl, C 6 -C 10 aryl or C 6 -C 10 heteroaryl radical each unsubstituted or mono- or poly-substituted by hydroxy, C,-C 18 alkyl, C,-C 18 alkoxy, amino, C,-C 5 mono- alkylamino or by di-C C 5 alkylamino; C 5 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl each unsubstituted or substituted by C,-C 5 alkyl; -OR'; or -NR'R";
• R 2 is hydrogen; a C,-C 18 alkyl, C 2 -C 18 alkenyl; C 3 -C 10 aryl or C 6 -C 10 heteroaryl radical each unsubstituted or mono- or poly-substituted by hydroxy, C,-C 18 alkyl, C,-C 18 alkoxy, cyano, amino, C,-C 5 monoalkylamino or by di-C,-C 5 alkylamino; -OR'; or -NR'R"; or
• R, and R 2 together form a 5- to 7-membered carbocyclic or heterocyclic ring;
• A is C,-C 5 alkyl; an unsubstituted or hydroxy-, C,-C 18 alkyl- or C,-C 18 alkoxy-substituted
• R' and R" are each independently of the other hydrogen; unsubstituted or mono- or poly- hydroxy-, halo-, C ⁇ C ⁇ alkyl-, C,-C 18 alkoxy-, amino- or quaternary ammonium group- substituted C,-C 18 alkyl, C 5 -C 7 cycloalkyl or phenyl;
• R 3 is hydrogen; or C,-C 6 alkyl; and n is 0 or 1.
• C,-C 18 Alkyl denotes straight-chain or branched hydrocarbon radicals, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1 -methylpentyl, 1 ,3-dimethylbutyl, n-hexyl, 1 -methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetra-methylbutyl, 1 -methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3- trimethylhexyl, 1,1 ,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1 -methylundecyl, dodecyl, tri
• C,-C 18 Alkoxy denotes straight-chain or branched radicals, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert- amyloxy, n-hexyloxy, 1 -methylhexyloxy, n-heptyloxy, isoheptyloxy, 1,1 ,3,3-tetramethyl- butoxy, 1 -methylheptyloxy, 3-methylheptyloxy, n-octyloxy, 2-ethylhexyloxy, 1,1,3-tri- methylhexyloxy, 1 ,1 ,3,3-tetramethylpentyloxy, nonyloxy, decyloxy, undecyloxy, 1 -methyl- undecyloxy, dodecyloxy, tridecyloxy, tetradecyl
• C 2 -C 18 AIkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n- dodec-2-enyl or n-octadec-4-enyl.
• C 6 -C 10 Aryl is, for example, phenyl or naphthyl.
• a heterocyclic ring is a heteroaromatic system containing at least one oxygen, sulfur and/or nitrogen hetero atom in the ring structure.
• Preferred heteroaryl groups preferably contain from 2 to 15 carbon atoms.
• Examples of mono- or di-C,-C 3 alkylamino are methylamino, ethylamino, propylamino, n- butylamino, sec-butylamino, tert-butylamino, pentylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino and methyl-ethylamino.
• R, and R 2 are each independently of the other C,-C, ⁇ alkyl or phenyl each unsubstituted or substituted by C 1 -C 5 alkyl, hydroxy or by C,-C 5 alkoxy; -OR'; or -NR'R"; or R, and R 2 together form a 5- to 7-membered carbocyclic or heterocyclic ring.
• R is C,-C 3 alkyl; C,-C 5 alkoxy; or unsubstituted or C,-C 5 alkyl-, hydroxy- or C,-C 5 alkoxy- substituted phenyl.
• R 2 is hydrogen; C,-C 5 alkyl; C,-C 3 alkoxy; unsubstituted or hydroxy-, C C 5 alkyl- or C,-C 5 - alkoxy-substituted phenyl; and n is 1.
• R, and R 2 together are a -(CH 2 ) 2J - radical that is not further substituted or is substituted by one or more C,-C 3 alkyl and is uninterrupted or interrupted by one or two -O- and/or -
• R, and R 2 together are a or ,N .
• R 5 is hydrogen; or C,-C 3 alkyl.
• a in formula (1 ) is especially amino; phenyl; or C,-C 5 alkoxyphenyl.
• R 3 in formula (1) is especially hydrogen. Special preference is given to compounds of formula (1) wherein R, and R 2 are C,-C 5 alkyl.
• the triazine derivatives of formula (1) according to the invention are prepared in a manner known perse by reacting a diaminotriazine compound of formula
• R 4 is C,-C 5 alkyl and R perpetrator R 2 , R 3 , A and n are as defined for formula (1), to form a compound of formula (1).
• the reaction is carried out in the presence of an acid, with or without the addition of one or more solvents at a reaction temperature of from 0 to 200°C.
• the reaction is preferably carried out in DMSO, N-methylpyrroIidone, DMF or DMA. It is also possible, however, to use protic solvents, such as ethanol, methanol, isobutanol or iso- propanol.
• the reaction can also be carried out in an aliphatic or aromatic solvent, such as hexane, toluene or xylene. It is also possible to use ethers, such as diethyl ether and tetrahy- drofuran, or halogenated solvents, such as chloroform or dichloromethane.
• the reaction is preferably carried out as a one-pot reaction.
• the individual reactants may, however, be added in any desired order.
• the catalyst may be present from the beginning or may be introduced only later. It is also possible first to start the reaction between (1 b) and (1 c) in the presence of the catalyst and only later to add the triazine compound of formula (1 a). It is equally possible first to react the compound of formula (1 a) with the compound of formula (1 b) in the presence of a catalyst and to add (1 c) later.
• the reaction can be carried out at a temperature of from 0 to 200°C, preferably at from 20 to 100°C and especially from 50 to 80°C.
• reaction times are dependent upon the reaction temperature. Within the preferred temperature range, the reactions are generally completed within from 1 to 6 hours. At low temperatures, the reaction time increases considerably and may be 48 hours or more.
• catalysts there are used organic and inorganic Br ⁇ nstedt or Lewis acids or mixtures thereof.
• typical acids are phosphoric acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, toluenesulfonic acid, phenylsulfonic acid and trifluoromethanesulfonic acid.
• acid anhydrides for example trifluoromethanesulfonic anhydride, methanesulfonic anhydride and acetic anhydride.
• Lewis acids such as phosphorus oxychloride, copper chlorides, zinc chloride, lanthanum chloride, chromium chlorides, iron chlorides, aluminium chloride, titanium chlorides, germanium chloride, and hydrates thereof. It is also possible to use acidic ion exchangers.
• the product is isolated according to conventional techniques, such as filtration, centrifuga- tion, phase separation and liquid extraction.
• the products are purified, inter alia, by recrys- tallisation from a solvent or from a solvent mixture, preference being given to solvents or solvent mixtures containing alcohols. Purification can also be carried out by chroma- tographic methods and by distillation.
• the compounds of formula (1) according to the invention are suitable especially as UV filters, that is to say to protect organic materials that are sensitive to ultraviolet light, especially human and animal skin and hair, against the damaging effect of UV radiation.
• the compounds are accordingly suitable as light-protective agents in cosmetic, pharmaceutical and veterinary medicine preparations.
• the compounds can be used either in the dissolved state or in the micronised state.
• the invention accordingly relates also to a cosmetic preparation comprising at least one compound of formula (1 ), and to cosmetically tolerable carriers or adjuvants.
• the cosmetic preparation may also comprise one or more further UV protective substances of the following substance classes:
• p-aminobenzoic acid derivatives for example 4-dimethylaminobenzoic acid 2- ethylhexyl ester;
• salicylic acid derivatives for example salicylic acid 2-ethylhexyl ester
• dibenzoylmethane derivatives for example 1 -(4-tert-butylphenyl)-3-(4-methoxyphenyl)- propane-1 ,3-dione;
• diphenylacrylates for example 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, and 3- (benzofuranyl) 2-cyanoacrylate;
• benzofuran derivatives especially 2-(p-aminophenyl)benzofuran derivatives, described in EP-A-582 189, US-A-5 338 539, US-A-5 518 713 and EP-A-61 3 893;
• polymeric UV absorbers for example the benzylidene malonate derivatives described in EP-A-709 080;
• cinnamic acid derivatives for example the 4-methoxycinnamic acid 2-ethylhexyl ester and isoamyl ester or cinnamic acid derivatives disclosed in US-A-5 601 81 1 and
• camphor derivatives for example 3-(4'-methyl)benzylidene-boman-2-one, 3-benzyl- ideneboman-2-one, N-[2(and 4)-2-oxyborn-3-ylidene-methyl)-benzyl]acrylamide polymer, 3-(4'-trimethylammonium)-benzylidene-bornan-2-one methyl sulfate, 3,3'-(1 ,4- phenylenedimethine)-bis(7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1 -methanesulfonic acid) and salts, 3-(4'-sulfo)benzylidene-boman-2-one and salts; camphorbenzalkonium methosulfate;
• hydroxyphenyltriazine compounds for example 2-(4'-methoxyphenyl)-4,6-bis(2'- hydroxy-4'-n-octyloxyphenyl)-1,3,5-triazine; 2,4-bis ⁇ [4-(3-(2-propyloxy)-2-hydroxy- propyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1 ,3,5-triazine; 2,4-bis ⁇ [4-(2-ethyl- hexyloxy)-2-hydroxyJ-phenyl ⁇ -6-[4-(2-methoxyethyl-carboxyl)-phenylamino]-1 ,3,5- triazine; 2,4-bis ⁇ [4-(tris(trimethylsilyloxy-silylpropyloxy)-2-hydroxy]-phenyl ⁇ -6-(4- methoxyphenyl)-1 ,3,5-triazine; 2,4-bis ⁇ [4
• UV absorbers described in "Sunscreens”, Eds. N.j. Lowe, N.A.Shaath, Marcel Dekker, Inc. , New York and Basle or in Cosmetics & Toiletries (107), 50ff (1992) also can be used as additional UV protective substances.
• ETHYLHEXYL TRIAZONE benzoic acid 4,4',4"-(1,3,5-triazine-2,4,6- 88122-99-0 triyltriimino)tris-, tris(2-ethylhexyl) ester; 2,4,6-trianilino-(p-carbo-2'-ethylhexyl-1 '-oxy)- 1 ,3,5-triazine
• PEG-25 PABA benzoic acid 4-amino-, ethyl ester, 113010-52-9 polymer with oxirane
• DIETHYLHEXYL BUTAMIDO benzoic acid 4,4'-[[6-[[4-[[(1,1 -dimethyl- 154702-15-5 TRIAZONE ethyl)amino]carbonyl]phenyl]amino]-1 ,3,5- triazine-2,4-diyl]diimino]bis-, bis(2-ethyl- hexyl) ester
• each of the above-mentioned light-protective agents can be used in admixture with the UV absorbers according to the invention. It will be understood in that connection that, in addition to the UV absorbers according to the invention, it is also possible for more than one of the additional light-protective agents to be used, for example, two, three, four, five or six further light- protective agents.
• mixing ratios of UV absorbers according to the invention/further light-protective agents of from 1 :99 to 99:1, especially from 1 :95 to 95:1 and preferably from 10:90 to 90:10, based on weight.
• mixing ratios of from 20:80 to 80:20, especially from 40:60 to 60:40 and preferably of approximately 50:50.
• Such mixtures can be used, inter alia, to improve solubility or increase UV absorption.
• the cosmetic preparations are suitable especially as UV filters, that is to say for the protection of organic materials that are sensitive to ultraviolet light, especially skin and hair, against the damaging effect of UV radiation.
• the UV absorbers can be used either in the dissolved state or in the micronised state.
• any known process suitable for the preparation of microparticles can be used for the preparation of the micronised UV absorbers, for example:
• a hard grinding medium for example zirconium silicate and a protective surfactant or a protective polymer in water or in a suitable organic solvent;
• a suitable solvent for example aqueous suspensions or suspensions containing organic solvents, or true solutions in water, ethanol, dichloroethane, toluene, N-methylpyrrolidone inter alia;
• grinding apparatus for the preparation of the micronised organic UV absorbers there may be used, for example, a jet mill, ball mill, vibratory mill or hammer mill, preferably a highspeed mixing mill.
• the grinding is preferably carried out with a grinding aid, for example an alkylated vinylpyrrolidone polymer, a vinylpyrrolidone/vinyl acetate copolymer, an acyl glu- tamate, an alkyl polyglucoside, ceteareth-25 or a phospholipid.
• a grinding aid for example an alkylated vinylpyrrolidone polymer, a vinylpyrrolidone/vinyl acetate copolymer, an acyl glu- tamate, an alkyl polyglucoside, ceteareth-25 or a phospholipid.
• the micronised UV absorbers so obtained usually have an average particle size that is from 0.02 to 2, preferably from 0.05 to 1.5, and more especially from 0.1 to 1.0, nm.
• the UV absorbers can also be used dry in powder form.
• the UV absorbers are subjected to known grinding methods, such as vacuum atomization, countercurrent spray-drying etc.. Such powders have a particle size of from 0.1 nm to 2 ⁇ m.
• the UV absorbers can be coated with a surface-active compound prior to the pulverisation process, for example with an anionic, non-ionic or ampho- teric surfactant, e.g. a phospholipid or a known polymer, such as PVP, an acrylate etc.
• the cosmetic preparations contain, for example, from 0.1 to 30 % by weight, preferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers and at least one cosmetically tolerable adjuvant.
• the cosmetic preparations can be prepared by physically mixing the UV absorber(s) with the adjuvant using customary methods, for example by simply stirring together the individual components, especially by making use of the dissolution properties of already known cosmetic UV absorbers, for example OMC, salicylic acid isooctyl ester, inter alia.
• the UV absorber can be used, for example, without further treatment, or in the micronised state, or in the form of a powder.
• the cosmetic preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments.
• the preparations contain, for example, from 0.1 to 30 % by weight, preferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, especially from 30 to 90 % by weight, based on the total weight of the composition, of water, and from 0 to 88.9 % by weight, especially from 1 to
• oil components of oil-containing compositions e.g. oils, W/O, O/W, O/W/O and W/O/W emulsions or microemulsions
• Guerbet alcohols based on fatty alcohols having from 6 to 18, preferably from 8 to 10, carbon atoms, esters of linear C 6 -C 24 fatty acids with linear C 3 -C 24 alcohols, esters of branched C 6 -C 13 carboxylic acids with linear C 6 -C 24 fatty alcohols, esters of linear C 6 -C 24 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols, especially dioctyl malates, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol) and/or Guerbet alcohols,
• polyhydric alcohols
• Finsolv ® TN linear or branched, symmetric or asymmetric dialkyl ethers having a total of from 12 to 36 carbon atoms, especially from 12 to 24 carbon atoms, for example di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n-undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n- decyl ether, n-decyl n-undecyl ether, n-undecyl n-dodecyl ether, n-hexyl n-undecyl ether, di-tert-butyl ether, diisopentyl ether, di-3-ethyldecyI ether, tert-butyl n-octyl ether, is
• That group of substances comprises the esterification products of fatty acids having from 8 to 24 carbon atoms, for example caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and technical- grade mixtures thereof (obtained, for example, in the pressure removal of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or in the dimerisation of un- saturated fatty acids) with alcohols, for example, is
• isopropyl myristate isononanoic acid C l6 -C 18 alkyl esters
• stearic acid 2- ethylhexyl ester cetyl oleate
• glycerol tricaprylate coconut fatty alcohol caprinate/caprylate
• n-butyl stearate isopropyl myristate, isononanoic acid C l6 -C 18 alkyl esters, stearic acid 2- ethylhexyl ester, cetyl oleate, glycerol tricaprylate, coconut fatty alcohol caprinate/caprylate and n-butyl stearate.
• dicarboxylic acid esters such as di-n-butyl adipate, di(2-ethylhexyl) adipate, di(2-ethylhexyl) succinate and diiso- tridecyl acetate
• diol esters such as ethylene glycol dioleate, ethylene glycol diiso- tridecanoate, propylene glycol di(2-ethylhexanoate), propylene glycol diisostearate, propylene glycol dipelargonate, butanediol diisostearate and neopentyl glycol dicaprylate.
• Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol. It is also possible to use di- and/or tri-valent metal salts (alkaline earth metal, Al 3+ inter alia) of one or more alkylcarboxylic acids.
• the oil components can be used in an amount of, for example, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition.
• any conventionally usable emulsifier can be used for the compositions.
• non-ionic surfactants from the following groups:
• polyol esters and especially polyglycerol esters for example diisostearoyl polyglyceryl-3- diisostearates, polyglyceryl-3-diisostearates, triglyceryl diisostearates, polyglyceryl-2- sesquiisostearates or polyglyceryl dimerates.
• polyglycerol esters for example diisostearoyl polyglyceryl-3- diisostearates, polyglyceryl-3-diisostearates, triglyceryl diisostearates, polyglyceryl-2- sesquiisostearates or polyglyceryl dimerates.
• esters based on linear, branched, unsaturated or saturated C 6 -C 22 fatty acids, rici- noleic acid and also 12-hydroxystearic acid and on glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and also polyglucosides (e.g. cellulose), for example po- lyglyceryl-2-dihydroxystea rates or polygIyceryl-2-diricinoIeates;
• ethoxylated esters of natural derivatives for example polyethoxylated esters of hydrogenated castor oil
• silicone oil emulsifiers for example silicone polyol
• DE-A-1 1 65 574 and/or mixed esters of fatty acids having from 6 to 22 carbon atoms, methylglucose and polyols, preferably glycerol or polyglycerol, for example polyglyceryl- 3-glucose distearates, polyglyceryl-3-glucose dioleates, methyl glucose dioleates or dico- coyl pentaerythryl distearyl citrates and also
• the addition products of ethylene oxide and/or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and di-esters and also sorbitan mono- and di-esters of fatty acids, or with castor oil, are known, commercially available products. They are usually homologue mixtures, the average degree of alkoxylation of which corresponds to the ratio of the amounts of ethylene oxide and/or propylene oxide and substrate with which the ad- dition reaction is carried out.
• C, 2 -C, s fatty acid mono- and di-esters of addition products of ethylene oxide with glycerol are known, for example, from DE-A-2 024 051 as fat-restoring substances for cosmetic preparations.
• C 8 -C 18 Alkyl-mono- and -oligo-glycosides their preparation and their use are known from the prior art. They are prepared especially by reacting glucose or oligosaccharides with primary alcohols having from 8 to 18 carbon atoms.
• Suitable glycoside radicals include mono- glycosides in which a cyclic sugar radical is glycosidically bonded to the fatty alcohol and also oligomeric glycosides having a degree of oligomerisation of up to preferably about 8. The degree of oligomerisation is a statistical average value based on a homologue distribution customary for such technical-grade products.
• zwitterionic surfactants denotes especially surface-active compounds that carry at least one quaternary ammonium group and at least one carboxylate and/or sulfonate group in the molecule.
• Zwitterionic surfactants that are especially suitable are the so-called betaines, such as N-alkyl- N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyl- dimethylammonium glycinate, and 2-a!kyl-3-carboxymethyl-3-hydroxyethylimidazolines each having from 8 to 18 carbon atoms in the alkyl or acyl group and also cocoacylamino- ethylhydroxyethylcarboxymethylglycinate.
• betaines such as N-alkyl- N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for
• ampholytic surfactants are to be understood as meaning especially those which, in addition to containing a C 8 -C 18 -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group in the molecule and are capable of forming internal salts.
• ampholytic surfactants include N- alkylglycines, N-alkylpropionic acids, N-aikylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each having approximately from 8 to 18 carbon atoms in the alkyl group.
• Ampholytic surfactants to which special preference is given are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C, 8 - acylsarcosine.
• ampholytic emulsifiers there also come into consideration quaternary emulsifiers, special preference being given to those of the esterquat type, preferably methyl-quaternised di-fatty acid triethanolamine ester salts.
• Non-ionic emulsifiers are preferred. Of the non-ionic emulsifiers mentioned, special preference is given to ethoxylated fatty alcohols having from 8 to 22 carbon atoms and from 4 to 30 EO units.
• the emulsifiers may be used in an amount of, for example, from 1 to 30 % by weight, especially from 4 to 20 % by weight and preferably from 5 to 10 % by weight, based on the total weight of the composition. It is, however, also possible in principle to dispense with the use of emulsifiers.
• the preparations according to the invention may in addition contain, as further adjuvants and additives, mild surfactants, super-fatting agents, pearlescent waxes, consistency regulators, thickeners, polymers, silicone compounds, fats, waxes, stabilisers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, film formers, swelling agents, further UV light-protective factors, antioxidants, hydrotropic agents, preservatives, insect repellents, self-tanning agents, solubilisers, perfume oils, colourants, bacteria-inhibiting agents and the like.
• mild surfactants super-fatting agents
• pearlescent waxes consistency regulators, thickeners, polymers, silicone compounds, fats, waxes, stabilisers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, film formers, swelling agents, further UV light-protective factors, antioxidants, hydrotropic agents, preservatives, insect repellents, self-tanning agents, solubilisers, perfume oils,
• Substances suitable for use as super-fatting agents are, for example, lanolin and lecithin and also polyethoxylated or acrylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter simultaneously acting as foam stabilisers.
• Suitable mild surfactants include fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and/or di-alkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ⁇ -olefin sulfonates, ether carboxylic acids, alkyl oligogluco- sides, fatty acid glucamides, alkylamidobetaines and/or protein fatty acid condensation products, the latter preferably being based on wheat proteins.
• alkylene glycol esters especially ethylene glycol distearate
• fatty acid alkanolamides especially coco fatty acid di- ethanolamide
• partial glycerides especially stearic acid monoglyceride
• fatty substances for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which in total have at least 24 carbon atoms, especially laurone and distearyl ether
• fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring-opening products of olefin epoxides having from 12 to 22 carbon atoms with fatty alcohols having from 12 to 22 carbon atoms and/or polyo
• fatty alcohols or hydroxy fatty alcohols having from 12 to 22 carbon atoms and preferably from 16 to 18 carbon atoms, and in addition partial glycerides, fatty acids and hydroxy fatty acids.
• Suitable thickeners include, for example, Aerosil types (hydrophilic silicic acids), polysaccha- rides, especially xanthan gum, guar-guar, agar-agar, alginates and Tyloses, carboxymethyl cellulose and hydroxymethyl cellulose, also relatively high molecular weight polyethylene glycol mono- and di-esters of fatty acids, polyacrylates (e.g.
• surfactants for example ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane
• fatty alcohol ethoxylates with restricted homologue distribution and alkyl-oligoglucosides as well as electrolytes, such as sodium chloride or ammonium chloride.
• Suitable cationic polymers are, for example, cationic cellulose derivatives, for example a qua- temised hydroxymethyl cellulose obtainable under the name Polymer JR 400 ® from Amer- chol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternised vi- nylpyrrolidone/vinyl imidazole polymers, for example Luviquat ® (BASF), condensation products of polyglycols and amines, quaternised collagen polypeptides, for example lauryldimo- nium hydroxypropyl hydrolyzed collagen (Lamequat ® L/Gr ⁇ nau), quaternised wheat polypeptides, polyethyleneimine, cationic silicone polymers, for example amidomethicones, co- polymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Car- taretin ® /Sandoz), copolymers of
• anionic, zwitterionic, amphoteric and non-ionic polymers there come into consideration, for example, vinyl acetate/crotonic acid copolymers, vinylpyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobomyl acrylate copolymers, methyl vinyl ether/maleic anhydride copolymers and esters thereof, uncrosslinked polyacrylic acids and polyacrylic acids crosslinked with polyols, acrylamidopropyltrimethylammonium chloride/acrylate copolymers, octyl acrylamide/methyl methacrylate/tert-butylaminoethyl methacrylate/2- hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone/vinyl acetate copolymers, vinylpyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam
• Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenyl- polysiloxanes, cyclic silicones, and also amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and/or alkyl-modified silicone compounds, which at room temperature may be in either liquid or resinous form.
• simethicones which are mixtures of dimethicones having an average chain length of from 200 to 300 dimethylsiloxane units with hydrogenated silicates.
• Typical examples of fats are glycerides, and as waxes there come into consideration, inter alia, beeswax, camauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils and fatty acid esters or microwaxes solid at room temperature optionally in combination with hydrophilic waxes, e.g. cetylstearyl alcohol or partial glycerides.
• Hydrophilic waxes e.g. cetylstearyl alcohol or partial glycerides.
• Metal salts of fatty acids for example magnesium, aluminium and/or zinc stearate or ricinoleate, may be used as stabilisers.
• Biogenic active ingredients are to be understood as meaning, for example, tocopherol, to- copherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bis- abolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudocera- mides, essential oils, plant extracts and vitamin complexes.
• deodorising active ingredients there come into consideration, for example, anti- perspirants, for example aluminium chloro hydrates (see J. Soc. Cosm. Chem. 24, 281 (1973)). Under the trade mark Locron ® of Hoechst AG, Frankfurt (FRG), there is available commercially, for example, an aluminium chlorohydrate corresponding to formula AI 2 (OH) 5 CI x 2.5 H 2 0, the use of which is especially preferred (see J. Pharm. Pharmacol. 26, 531 (1975)). Besides the chlorohydrates, it is also possible to use aluminium hydroxy- acetates and acidic aluminium/zirconium salts. Esterase inhibitors may be added as further deodorising active ingredients.
• Such inhibitors are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen ® CAT, Henkel KGaA, D ⁇ sseldorf/FRG), which inhibit enzyme activity and hence reduce odour formation.
• trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen ® CAT, Henkel KGaA, D ⁇ sseldorf/FRG), which inhibit enzyme activity and hence reduce odour formation.
• esterase inhibitors are sterol sulfates or phosphates, for example lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester and hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tar- taric acid or tartaric acid diethyl ester.
• dicarboxylic acids and esters thereof for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid
• Antibacterial active ingredients that influence the mi- crobial flora and kill or inhibit the growth of sweat-decomposing bacteria can likewise be present in the preparations (especially in stick preparations). Examples include chitosan, phenoxyethanol and chlorhexidine gluconate. 5-Chloro-2-(2,4-dichlorophenoxy)-phenol (Ir- gasan ® , Ciba Specialty Chemicals Inc.) has also proved especially effective.
• Customary film formers include, for example, chitosan, microcrystalline chitosan, quaternised chitosan, polyvinylpyrrolidone, vinylpyrrolidone/vinyl acetate copolymers, polymers of quaternary cellulose derivatives containing a high proportion of acrylic acid, collagen, hyaluronic acid and salts thereof and similar compounds.
• swelling agents for aqueous phases there may be used montmorillonites, clay mineral substances, Pemulen and also alkyl-modified types of Carbopol (Goodrich). Further suitable polymers and swelling agents can be found in the review by R. Lochhead in Cosm. Toil. 108, 95 (1993).
• antioxidants are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) and derivatives thereof, peptides, such as D,L- carnosine, D-carnosine, L-carnosine and derivatives thereof (e.g. anserine), carotinoids, carotenes (e.g.
• thioredoxin glutathione, cysteine, cystine, cys- tamine and the glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters thereof) and also salts thereof, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and also sulfoximine compounds (e.g.
• buthionine sulfoximines homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, hepta-thionine sulfoximine
• very small tolerable amounts e.g. from pmol to ⁇ mol/kg
• metal chelating agents e.g. ⁇ -hydroxy fatty acids, palmitic acid phytic acid, lactofer- rin
• ⁇ -hydroxy acids e.g.
• citric acid citric acid, lactic acid, malic acid
• humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof
• unsaturated fatty acids and derivatives thereof e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
• folic acid and derivatives thereof ubiquinone and ubiquinol and derivatives thereof
• vitamin C and derivatives e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate
• tocopherols and derivatives e.g. vitamin E acetate
• vitamin A and derivatives e.g.
• vitamin A palmitate and also coniferyl benzoate of benzoin resin, rutinic acid and derivatives thereof, ⁇ -glycosylrutin, ferulic acid, furfurylidene glucitol, camosine, butyl hydroxytoluene, butyl hydroxyanisole, resinous nordihydroguaiaretic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, N- [3-(3,5-di-tert-butyI-4-hydroxyphenyl)propionyl]sulfaniIic acid (and salts thereof, for example the disodium salts), zinc and derivatives thereof (e.g.
• ZnO, ZnSO selenium and derivatives thereof (e.g. selenium methionine), stilbene and derivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of those mentioned active ingredients.
• HALS "Hindered Amine Light Stabilizers" compounds may also be mentioned.
• the amount of antioxidants present is usually from 0.001 to 30 % by weight, preferably from 0.01 to 3 % by weight, based on the weight of the UV absorber(s).
• hydrotropic agents for example ethanol, isopropyl alcohol or polyols.
• the polyols that come into consideration for that purpose have preferably from 2 to 15 carbon atoms and at least two hydroxy groups.
• the polyols may also contain further functional groups, especially amino groups, and/or may be modified with nitrogen. Typical examples are as follows:
• alkylene glycols for example ethylene glycol, diethylene glycol, propylene glycol, buty- lene glycol, hexylene glycol and also polyethylene glycols having an average molecular weight of from 100 to 1000 dalton;
• - technical oligoglycerol mixtures having an intrinsic degree of condensation of from 1 .5 to 10, for example technical diglycerol mixtures having a diglycerol content of from 40 to 50 % by weight;
• - methylol compounds such as, especially, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
• alkyl-glucosides especially those having from 1 to 8 carbon atoms in the alkyl radical, for example methyl and butyl glucoside;
• - sugar alcohols having from 5 to 12 carbon atoms, for example sorbitol or mannitol;
• sugars having from 5 to 12 carbon atoms, for example glucose or saccharose;
• dialcohol amines such as diethanolamine or 2-amino-1 ,3-propanediol.
• Suitable preservatives include, for example, phenoxyethanol, formaldehyde solution, Para- bens, pentanediol or sorbic acid and the further substance classes listed in Schedule 6, Parts A and B of the Cosmetics Regulations.
• Natural aromatic substances are, for example, extracts from blossom (lilies, lavender, roses, jasmine, neroli, ylang-ylang), from stems and leaves (geranium, patchouli, petit- grain), from fruit (aniseed, coriander, carraway, juniper), from fruit peel (bergamot, lemons, oranges), from roots (mace, angelica, celery, cardamom, costus, iris, calmus), from wood (pinewood, sandalwood, guaiacum wood, cedarwood, rosewood), from herbs and grasses (tarragon, lemon grass, sage, thyme), from needles and twigs (spruce, pine, Scots pine, mountain pine), from resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
• Animal raw materials also come into consideration, for example c
• Aromatic substance compounds of the ester type are, for example, benzyl acetate, phe- noxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethyl- benzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl- phenyl glycinate, allylcyclohexyl propionate, styrallyl propionate and benzyl salicylate.
• the ethers include, for example, benzyl ethyl ether;
• the aldehydes include, for example, the linear alkanals having from 8 to 18 hydrocarbon atoms, citral, citronellal, citronellyl oxyacetal- dehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal;
• the ketones include, for example, the ionones, ⁇ -isomethylionone and methyl cedryl ketone;
• the alcohols include, for example, anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenyl ethyl alcohol and terpinol; and
• the hydrocarbons include mainly the terpenes and balsams.
• Ethereal oils of relatively low volatility which are chiefly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, clove oil, melissa oil, oil of cinnamon leaves, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, gal- banum oil, labolanum oil and lavandin oil.
• bacteria-inhibiting agents are preservatives that have a specific action against gram-positive bacteria, such as 2,4,4'-trichIoro-2'-hydroxydiphenyl ether, chlor- hexidine (1,6-di(4-chlorophenyl-biguanido)hexane) or TCC (3,4,4'-trichlorocarbanilide).
• gram-positive bacteria such as 2,4,4'-trichIoro-2'-hydroxydiphenyl ether, chlor- hexidine (1,6-di(4-chlorophenyl-biguanido)hexane) or TCC (3,4,4'-trichlorocarbanilide).
• TCC 3,4,4'-trichlorocarbanilide
• a large number of aromatic substances and ethereal oils also have antimicrobial properties.
• Typical examples are the active ingredients eugenol, menthol and thymol in clove oil, mint oil and thyme oil.
• a natural deodorising agent of interest is the terpene alcohol farnesol (3,7,1 1 -trimethyl-2,6,10-dodecatrien-1 -ol), which is present in lime blossom oil.
• Glycerol monolaurate has also proved to be a bacteriostatic agent.
• the amount of the additional bacteria-inhibiting agents present is usually from 0.1 to 2 % by weight, based on the solids content of the preparations.
• the cosmetic preparations may contain, as adjuvants, anti-foams, such as silicones, structurants, such as maleic acid, solubilisers, such as ethylene glycol, propylene glycol, glycerol or diethylene glycol, opacifiers, such as latex, styrene/PVP or sty- rene/acrylamide copolymers, complexing agents, such as EDTA, NTA, ⁇ -alaninediacetic acid or phosphonic acids, propellants, such as propane/butane mixtures, N 2 0, dimethyl ether, CO 2 , N 2 or air, so-called coupler and developer components as oxidation dye precursors, reducing agents, such as thioglycolic acid and derivatives thereof, thiolactic acid, cysteamine, thiomalic acid or ⁇ -mercaptoethanesulfonic acid, or oxidising agents, such as hydrogen peroxide, potassium bromate or sodium bro
• insect repellents for example, N,N-diethyl-m-toluamide, 1 ,2-pentanediol or insect repellent 3535;
• suitable self-tanning agents are, for example, di- hydroxyacetone, erythrulose or mixtures of dihydroxyacetone and erythrulose.
• Cosmetic formulations according to the invention are contained in a wide variety of cosmetic preparations. There come into consideration, for example, especially the following preparations: skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes, bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts; skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils; cosmetic personal care preparations, e.g.
• skin-care preparations e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes
• bath preparations e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts
• skin-care preparations e.g. skin emul
• eye-care preparations e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix creams
• lip-care preparations e.g. lipsticks, lip gloss, lip contour pencils
• nail-care preparations such as nail varnish, nail varnish removers, nail hardeners or cuticle removers
• foot-care preparations e.g.
• foot baths foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations
• light-protective preparations such as sun milks, lotions, creams or oils, sunblocks or tropicals, pre-tanning preparations or after-sun preparations
• skin-tanning preparations e.g. self-tanning creams
• depigmenting preparations e.g. preparations for bleaching the skin or skin-lightening preparations
• insect-repellents e.g.
• insect-repellent oils lotions, sprays or sticks
• deodorants such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons
• antiperspirants e.g. antiperspirant sticks, creams or roll-ons
• preparations for cleansing and caring for blemished skin e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks
• shaving preparations e.g.
• fragrance preparations e.g. fragrances (eau de Cologne, eau de toilette, eau de perfume, perfume de toilette, perfume), perfume oils or perfume creams
• cosmetic hair-treatment preparations e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g.
• hair-waving preparations for permanent waves hot wave, mild wave, cold wave
• hair-straightening preparations liquid hair- setting preparations
• hair foams hairsprays
• bleaching preparations e.g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colourants, preparations containing self-oxidising dyes, or natural hair colourants, such as henna or camomile.
• liquid preparations as a W/O, O/W, O/W/O, W/O/W or PIT emulsion and all kinds of microemulsions,
• cosmetic preparations for the skin are light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or tropicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams.
• light-protective preparations such as sun milks, lotions, creams, oils, sunblocks or tropicals
• pretanning preparations or after-sun preparations also skin-tanning preparations, for example self-tanning creams.
• sun protection creams, sun protection lotions, sun protection oils, sun protection milk and sun protection preparations in the form of a spray are particularly useful for sun protection cream.
• hair-washing preparations in the form of shampoos, hair conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair- straightening preparations, liquid hair-setting preparations, hair foams and hairsprays.
• hair-washing preparations in the form of shampoos.
• a shampoo has, for example, the following composition: from 0.01 to 5 % by weight of a UV absorber according to the invention, 12.0 % by weight of sodium laureth-2-sulfate, 4.0 % by weight of cocamidopropyl betaine, 3.0 % by weight of sodium chloride, and water ad 100%.
• hair-cosmetic formulations may be used: a,) spontaneously emulsifying stock formulation, consisting of the UV absorber according to the invention, PEG-6-C 10 oxoalcohol and sorbitan sesquioleate, to which water and any desired quaternary ammonium compound, for example 4 % minkamidopropyl dimethyl-2-hydroxyethylammonium chloride or Quaternium 80 is added; a 2 ) spontaneously emulsifying stock formulation consisting of the UV absorber according to the invention, tributyl citrate and PEG-20-sorbitan monooleate, to which water and any desired quaternary ammonium compound, for example 4 % minkamidopropyl dimethyl-2-hydroxyethylammonium chloride or Quaternium 80 is added; b) Quat-doped solutions of the UV absorber according to the invention in butyl triglycol and tributyl citrate; c) mixtures or
• the cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight.
• percentages relate to weight.
• the amounts of the triazine derivatives used relate to the pure substance.
• 0.1 ml of trifluoromethanesulfonic anhydride is added, at 90°C , to a solution of 7.5 g (0.05 mol) of orthoformic acid triethyl ester in 50 ml of isobutanol.
• 2.3 g (0.0125 mol) of 2,2-diamino-6-phenyl-1 ,3,5-triazine are then introduced in portions in the course of 1.5 hours.
• the resulting solution is stirred for 30 minutes at 100 °C.
• the reaction mixture is maintained at reflux for 4 hours. After cooling to room temperature, the suspension is filtered.
• 2,4-Diamino-6-phenyl-1 ,3,5-triazine (0.0013 mol, 0.24 g) is dissolved in N-methylpyrroIidone (1.15 ml).
• Orthoformic acid trimethyl ester (0.0038 mol, 0.42 ml)
• copper chloride dihydrate solution (0.001 3 mol, 0.22 g in 0.5 ml of NMP)
• the appropriate ketone (0.0038 mol dissolved in 2 ml of NMP) are added to the solution.
• the reaction mixture is shaken for 4 hours at 70°C.
• the crude product is precipitated by the addition of 10 ml of 10 % aqueous sodium sulfate solution, and the precipitate is then filtered off and washed with copious amounts of ethanol. Subsequent column chromatography (Nucleosil 5C18) using a mixture of acetonitrile and water yields the pure product.
• the crude product is precipitated by the addition of 10 ml of 10 % aqueous sodium sulfate solution, and the precipitate is then filtered off and washed with copious amounts of ethanol. Subsequent column chromatography (Nucleosil 5C18)) using a mixture of acetonitrile and water yields the pure product.
• Example 1 Sprayable Sunscreen Lotion
• This emulsion contains a combination of insoluble UV-absorber.
• the choice of emollients provides quick absorption and smooth after skin feeling.
• Example 14 O/W emulsion water resistant
• This emulsion is smooth and spreads easily.

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