Classifications

• • 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
  • C07D251/24—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 three ring carbon atoms
• • 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
• • 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
  • 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
• • 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

Definitions

• the present invention relates to the use of specific symmetrical triazine derivatives for the protection of human and animal hair and skin against the damaging effect of UV radiation, cosmetic compositions comprising these triazine derivatives and process for preparation of these compounds.
• Triazines which are symmetrically substituted by biphenyl or naphthyl are known, for example from US-A-6,225,467. They are used as for electroluminescent devices.
• the present invention refers to the non-therapeutic use of the compounds of formula
• A is a radical of formula (1a) ⁇ — ; or (1b)
• Ri and R 5 independently from each other are hydrogen; C ⁇ -C 18 alkyl; or C ⁇ -C ⁇ 2 aryl; R 2 , R 3 and R independently from each other are hydrogen; or a radical of formula
• y is a number from 2 to 10; for the protection of human and animal hair and skin against the damaging effect of UV radiation.
• CrC ⁇ ⁇ alkyl according to the definition for the radicals of the compound of formula (1) are straight-chain or branched alkyl radicals like methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.butyl, tert.butyl, amyi, isoamyl ⁇ rtert.amyl, hexyl, 2-ethylhexyl, heptyl, octyl, isooc yl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl.
• C ⁇ -C ⁇ salkyl according to the definition for the radicals of the compound of formula (1) may be substituted by methoxyethyl, ethoxypropyl, 2-ethylhexyl, hydroxyethyl, chloropropyl, N,N-di- ethylaminopropyl, cyanoethyl, phenethyl, benzyl, p-tert-butylphenethyi, p-tert-octylphenoxy- ethyl, 3-(2,4-di-tert-amylphenoxy)-propyI, ethoxycarbonylmethyl-2-(2-hydroxyethoxy)ethyl, or 2-furylethyl.
• Cieaikyl according to the definition for the radicals of the compound of formula (1) are for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec.butoxy, tert.butoxy, amyloxy, isoamyloxy or tert.amyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy or octa- decyloxy.
• radicals of the compound of formula (1) is for example naphthyl und preferably phenyl.
• Ri, R5, e, R7 und R 8 are defined as in formula (1).
• Riand R 5 are preferably hydrogen.
• R 7 is hydrogen; hydroxy; C C 5 alkyl; C ⁇ -C 5 alkoxy; -COOM; -COOH; or COOR 10 ;
• M is an alkali metal ion
• R 10 is d-Csalkyl.
• R11 R2, R3, Rg and R i0 are defined as in formula (1).
• compounds of formula (3) are used, wherein
• Ri, R ⁇ , Re, R9 and R10 are hydrogen; or, independently from each other, C C ⁇ alkyl.
• triazine derivatives which are preferably used in the present invention, are the compounds of formula
• the compounds of the formula (1) according to the present invention are particularly suitable as UV filters, i.e. for protecting ultraviolet-sensitive organic materials, in particular the skin and hair of humans and animals, from the harmful effects of UV radiation. These compounds are therefore suitable as sunscreens in cosmetic, pharmaceutical and veterinary medical preparations. These compounds can be used both in dissolved form and in the micronized state.
• the UV absorbers according to the present invention can be used either in the dissolved state (soluble organic filters, soiubelized organic filters) or in the micronised state (nanoscalar organic filters, particulate organic filters, UV-absorber pigments).
• the triazine derivatives of formula (1) which have no alkyl substituents or only lower-alkyl substituents are characterized by a poor oil-solubility and a high melting point. They are therefore suitable in particular as UV absorbers in the micronized state.
• the micronised UV absorbers so obtained usually have an average particle size from 0.02 to 2, preferably from 0.03 to 1.5, and more especially from 0.05 to 1.0 micrometer.
• UV absorbers according to the present invention can also be used as dry substrates in powder form.
• the UV absorbers according to the present invention can also be used in specific carriers for cosmetics, for example in solid lipid nanoparticles (SLN) or in inert sol-gel microcapsules wherein the UV absorbers are encapsulated (Pharmazie, 2001 (56), p. 783-786).
• the cosmetic formulations or pharmaceutical compositions according to the present invention may additionally contain one or more than one further UV filter as listed in tables 1-3.
• the cosmetic or pharmaceutical 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, like octyl methoxy cinnamate, salicylic acid isooctyl ester, etc.
• the UV absorber can be used, for example, without further treatment, or in the micronised state, or in the form of a powder.
• Cosmetic or pharmaceutical preparations contain from 0.05-40% by weight, based on the total weight of the composition, of one UV absorber or UV absorber mixtures.
• UV absorbers of formula (1 ) according to the present invention or combinations of UV filters are useful to protect skin, hair and/or natural or artificial hair color.
• Suitable UV filter substances which can be additionally used with the UV absorbers according to the present invention p-aminobenzoic acid derivatives, for example 4-dimethylaminobenzoic acid 2-ethylhexyl ester; salicylic acid derivatives, for example salicylic acid 2-ethylhexyl ester; benzophenone derivatives, for example 2-hydroxy-4-methoxybenzophenone and its 5-sulfonic acid derivative; 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-(benzofura- nyl) 2-cyanoacrylate;
• p-aminobenzoic acid derivatives for example 4-dimethylaminobenzoic acid 2-ethylhexyl ester
• 3-imidazol-4-ylacrylic acid and esters 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-613893; polymeric UV absorbers, for example the benzylidene malonate derivatives described in EP-A-709080; cinnamic acid derivatives, for example the 4-methoxycinnamic acid 2-ethylhexyl ester and isoamyl ester or cinnamic acid derivatives described in US-A-5 601 811 and WO 97/00851 ; camphor derivatives, for example 3-(4'-methyl)be ⁇ zylidene-boman-2-one, 3-benzylidene- bornan-2-one, N-[2(and 4)-2-oxyborn-3-ylidene-methyl)-benzyl]acrylamide polymer, 3-(4
• the primary particle size is an average of 15nm-35nm and the particle size in dispersion is in the range of 100nm - 300nm.
• 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.
• UV filter combinations are of special interest:
• Ri and R 2 independently from each other are; Ci-Czoalkyl; C 2 -C2oalkenyl; C 3 -
• Ciocycloalkyl; C -C 10 cycloalkenyl; or Ri and R 2 together with the linking nitrogen atom form a 5- or 6-membered heterocyclic ring; ni is a number from 1 to 4; when n ! 1 ,
• R 3 is a saturated or unsaturated heterocyclic radical; hydroxy-d-C ⁇ alkyl; cyclohexyl, M optionally substituted with one or more d-Csalkyl; phenyl optionally substituted with a heterocyclic radical, amin ⁇ carb ⁇ nyl or d-Csalkylcarboxy;
• R 3 is an alkylene-, cycloalkylene, alkenylene or phenylene radical which is optionally substituted by a carbonyl- or carboxy group; a radical of formula — CH J -C ⁇ C-CHJ— « or R 3 together with A forms a bivalent radical of the
• n 2 is a number from 1 to 3;
• R 3 is an alkanetriyl radical;fect n ⁇ is 4,
• R 3 is an alkanetetrayl radical
• A is -0-; or-N(R 5 )-;
• R 5 is hydrogen; d-Csalkyl; or hydroxy-Ci-Csalkyl.
• UV-filter combinations (A1) comprising (a 3 ) at least one compound of formula (6) and/or (9);
• R 1 and R 2 independently from each other is hydrogen, d-doalkyl; C 2 -C 20 alkenyl; C 3 -
• Ciocycloalkenyl wherein R and R 2 may form a five- or six-membered ring; R 3 and R 4 independently from each other is d-doalkyl; C 2 -C 20 alkenyl; C 3 -
• X is hydrogen; COOR 5 ; or CONR e R 7:
• R 6 , R ⁇ , R 7 independently from each other are hydrogen, C ⁇ -C 20 alkyl; C 2 -C 20 alkenyl; C 3 -
• UV-filter combinations (B1) comprising (b 3 ) the compound of formula (6) and/or (9);
• T 2 is C ⁇ -C ⁇ oalkyl or phenyl-substituted d-dalkyl
• UV-filter combinations (C1) comprising (c 3 ) the compound of formula (6) and/or (9);
• Ri and R 2 independently of one another, are C 3 -C 18 alkyl; C 2 -C 18 alkenyl; a radical of the formula -CH 2 -CH(-OH)-CH 2 -0-T 1 ; or
• Ri and R 2 are a radical of the formula (4a) — ijj-Si— o- -Si-R,
• R ⁇ 2 is a direct bond; a straight-chain or branched C ⁇ -C 4 alkylene radical or a radical of the formula -C H- or -c m H— o- ;
• Ri3, Ri4 and R15 independently of one another, are d-C ⁇ 8 alkyl; C ⁇ -C ⁇ 8 alkoxy or a radical
• R 1 ⁇ is d-C 6 alkyl; mi and m 3 , independently of one another, are 1 to 4;
• Pi is 0; or a number from 1 to 5;
• Ai is a radical of the formula
• R 3 is hydrogen; d-d 0 alkyl, -(CH 2 CHR 5 - ⁇ ) -R 4 ; or a radical of the formula n 1
• Rt is hydrogen; M; d-Csalkyl; or a radical of the formula -(CH 2 ) m -0-T 1 ;
• R 5 is hydrogen; or methyl
• T1 is hydrogen; or d-C 8 alkyl
• M is a metal cation
• m 2 is 1 to 4.
• UV-filter combinations (D1) comprising (d 3 ) the compound of formula (6) and/or (9); and (d 4 ) the compound of
• R-i, R 2 and R 3 are each independently of the others C ⁇ -C ⁇ 8 alkyl; d-doalkenyl; or phenyl- C ⁇ -C 4 alkyl; and R 4 is hydrogen; or d-Csalkyl.
• UV-filter combinations (E1) comprising (e 3 ) the compound of formula (6) and/or (9);
• UV-filter combinations (F1) comprising
• UV-filter combinations comprising (hi) at least one symmetrical triazine derivatives of formula (1); and (h 2 ) benzoxazole-substituted triazines of formula
• Ri, R 2 and R 3 independently from each other are branched or unbranched d-Csalkyl.
• UV-filter combinations comprising (h 3 ) the compound of formula (6) and/or (9);
• UV filter combination (H2) comprising (h 5 ) the compound of formula (6) or (9); and (h ⁇ ) at least one of the compound of formula (h 2 1), wherein (h ⁇ 1 ) Ri and R 2 are tertamyl; and R 3 is tert.butyl; or wherein (h ⁇ ) Ri and R 2 are tert.butyl and R 3 is tert.octyl; or wherein (he 3 ) Ri and R 2 are tert.butyl; and R 3 is 2-ethylhexyl; or wherein (h M ) Ri and R 2 are tert.amyl; and R 3 is 2-ethylhexyl; are of preferred interest.
• (ki) at least one symmetrical triazine derivatives of formula (1), preferably the compound of formula (6) and/or (9); and (k 2 ) siloxanes and silicones, di-Me, 1-[[4-[3-ethoxy-2-(ethoxycarbonyl)-3-oxo-1-propenyl]p- henoxy]methyl]ethenyl Me, 3-[4-[3-ethoxy-2-(ethoxycarbonyl)-3-oxo-1 -propenyl]-
• (I-i) at least one symmetrical triazine derivatives of formula (1), preferably the compound of formula (6) and/or (9); and (l 2 ) (+/-)-1 ,7,7-trimethyl-3-[(4-methylphenyl)methylene]bicyclo[2.2.1 ]heptan-2-one; p-methyl benzylidene camphor;
• (ni) at least one symmetrical triazine derivatives of formula (1), preferably the compound of formula (6) and/or (9); and (n 2 ) methyl N,N,N-trimethyl-4-[(4,7,7-trimethyl-3-oxobicyclo[2,2,1]hept-2-ylidene)methyl]- anilinium sulphate (Mexoryl SO);
• compositions (A) - (S) the compound of formula (1), (6) and (9) respectively are preferably present in the composition in micronized form.
• the compounds of formula (1) may also be used as as an anti-wrinkle perception modifier (see Example 29). This is a futher object of the present invention.
• the compounds of formula (1) can be prepared according to known methods as described for example in US-A-6,225,467.
• the compounds of formula (1) may be obtained in a Grignard reaction starting from the corresponding halogen aromatic compounds and a trihalogen triazine.
• R 1 -R 10 are defined as in formula (1)
• Cyanu ⁇ c chloride is preferably used as tr ⁇ halogen-1 ,3,5-t ⁇ az ⁇ ne
• the reaction temperature is from -10 to 250°C, preferably from 5-150°C, most preferably from 70-130°C
• Preferred catalysts are (as single compounds or in combination AICI 3 , AIBr 3 , BF 3 , BCl 3 , BBr 3 , BeCI 2 , CdCI 2 , ZnCI 2 , GaCI 3 , GaBr 3 , FeCI 3 , SbCI 3 , B ⁇ CI 3 , T ⁇ CI 4 , ZrCI 4 , SnCI 4 , UCI 4 and SbCI 5
• alcohols water, HCl, HF, H 2 S0 4 , H 3 P0 4 , RCOOH (organic acids), sulfonic acids like for example p-toluene sulfonic acid.
• co-catalysts can also be used in stoichiometric amounts or in excess.
• gaseus HCl is used as co-catalyst.
• co-catalysts or promotors compounds or classes of compounds are used: Cations forming compounds: preferred are alkyl- and acyl-halogenides as well as compounds comprising oxygen-, sulfur-, or halogen-donor atoms.
• Suitable solvents are: aliphatic hydrocarbons, aromatic hydrocarbons, sulfur-hydrocarbons, halogenaromatic compounds, halogenaliphatic compounds, alyl-aryl ethers, alkyl-alkyl ethers, sulfolane, nitroaromatic compounds and nitroaliphatic compounds.
• chlorbenzene 1 ,2-dichlorbenzene, 1 ,4-dichlorbenzene, nitrobenzene, nitromethane, tetrachlormethane.
• reaction can be carried out in ionic fluids like for example 1-butylpyri- diniume chloride - aluminum(lll) chloride and 1 -butyl-3-methylimidazolium chloride - alu- minum(lll) chloride (s. 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene. Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry 1999 (1), 63).
• ionic fluids like for example 1-butylpyri- diniume chloride - aluminum(lll) chloride and 1 -butyl-3-methylimidazolium chloride - alu- minum(lll) chloride (s. 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene. Journal of the Chemical Society
• the cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments.
• the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.
• 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 50
• the cosmetic or pharmaceutical compositions/preparations according to the invention may also contain one or one more additional compounds like fatty alcohols esters of fatty acids, natural or synthetic triglycerides including glyceryl esters and derivatives, pearlescent waxes: hydrocarbon oils, silicones or siloxanes (organosubstituted polysiloxanes) fluorinated or per- fluorinated oilsemuisifiers, super-fatting agents, surfactants, consistency regulators/thickeners and rheology modifiers, polymers, biogenic active ingredients, deodorising active ingredients anti-dandruff agents, antioxidants, hydrotropic agents, preservatives and bacteria-inhibiting agents, perfume oils, colourants, polymeric beads or hollow spheres as SPF enhancers.
• additional compounds like fatty alcohols esters of fatty acids, natural or synthetic triglycerides including glyceryl esters and derivatives, pearlescent waxes: hydrocarbon oils, silicones or siloxanes (organosubstitute
• Cosmetic or pharmaceutical formulations are contained in a wide variety of cosmetic preparations. There come into consideration, for ⁇ ssample, especially the following preparations like skin-care preparations, bath preparations, cosmetic personal care preparations, foot-care preparations,; light-protective preparations, skin-tanning preparations, depigmenting preparations, insect-repellents, deodorants, antiperspirants, preparations for cleansing and caring for blemished skin, hair-removal preparations in chemical form (depilation), shaving preparations, fragrance preparations or cosmetic hair-treatment preparations.
• the final formulations listed may exist in a wide variety of presentation forms, for example: in the form of liquid preparations as a W/O, O/W, O/W/O, W/O W or PIT emulsion and all kinds of microemulsions, in the form of a gel, an oil, a cream, milk or lotion, a powder, a lacquer, a tablet or make-up, a stick, a spray or an aerosol, a foam, or a paste.
• 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 milk and sun protection preparations in the form of a spray are particularly interested.
• 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.
• the cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight. Examples
• Cyanuric chloride (36.9 g, 0.20 mol) is dissolved in 1 ,2-dichlorobenzene (500 ml).
• Aluminum chloride (96.0 g, 0.72 mol) is added and the reaction mixture is heated up to 140°C.
• Biphenyl (111.0 g, 0.72 mol), dissolved in 200 ml 1 ,2-dichlorobenzene, is added slowly dropwise and the temperature is maintained at 140-145°C for 1 to 4 hours.
• the reaction mixture is cooled down to about 60°C and added to a mixture of 150ml cone. HCl and 350g ice. After phase separation at about 110°C the dichloro benzene phase is removed, stirred with Na 2 C0 3 and filtered hot at 100 - 110°C. The desired compound recrystallizes from the filtrate.
• Biphenyl (200.0 g, 1.28 mol) is submitted and melted at 70-75°C.
• Cyanuric chloride (9.2 g, 0.05 mol) is added and hydrogen chloride is discharged for 10 minutes.
• Aluminum chloride (20.0 g, 0.15 mol) is added within 40 minutes in 5 equal portions, whereby hydrogen chloride is discharged again after the first two additions.
• 95 per cent ethanol 200 ml is added dropwise slowly. The reaction mixture is heated up for 1h under reflux. Finally, acetone (400 ml) is added and agitated for 1h, cooled down to room temperature and the failed product is filterd under suction.
• the bromide also the chloride, iodide or tosylate might be used as starting material. Bromide is preferred.
• the compound of formula (103) can be synthesized alternatively via the following pathway:
• Part A and part B are heated separately to 75°C. Part A is poured into part B under continuous stirring. Immediately after the emulsification, cyclopentasiloxane and PEG-12 Di-
• methicone from part D are incorporated into the mixture. Afterwards the mixture is homogenized with an Ultra Turrax at 11 000 rpm for 30 sec. After cooling down to 65°C Sodium Acrylates Copolymer (and) Paraffinium Liquidum (and) PPG-1 Trideceth-6 are incorporated. Part C is added at a temperature ⁇ 50°C. At a temperature ⁇ 35°C Tocopheryl Acetate is incorporated and subsequently the pH is adjusted with Water (and) Citric Acid. At room temperature part E is added.
• Part A by is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75"C.
• Part B s prepared and heated to 75°C. At this temperature part B is poured into part A under progressive stirring speed. Then the mixture is homogenized (30sec, 15000 rpm ) . At a temperature ⁇ 55°C the ingredients of part C are incorporated. The mixture is cooled down under moderate stirring, then the pH is checked and adjusted with triethanolamine.
• Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75°C.
• Part B is prepared and heated to 75°C. At this temperature, part B is poured into part A under progressive stirring speed. Below 65°C the ingredients of part D are added separately. After cooling down under moderate stirring to 55°C part C is added. The pH is then checked and adjusted with sodium hydroxide. The mixture is homogenized for 30 sec at
• Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75°C.
• Part C is prepared and heated to 75°C.
• Part C is poured into the part A under moderate stirring.
• emulsification part B is added, then neutralized with a part of the triethanolamine.
• the mixture is homogenized for 30 sec.
• Cyclopentasiloxane (and) Dimethiconol are added. Below 35°C the pH is checked and adjusted with triethanolamine.
• Part A and part B are heated up to 80°C.
• Part A is blended into part B under stirring and homogenized with an UltraTurrax at 11 000 rpm for 30 sec.
• Part C is heated to 60°C and added slowly to the emulsion. After cooling down to 40°C part D is incorporated at room temperature and part E is added.
• Part A and B are heated to 75°C. Part A is added into part B under continuous stirring and homogenized with 11000 rpm for 1 minute. After cooling down to 50°C part C is added under continuous stirring. After cooling further down to 30°C part D is added. Afterwards the pH is adjusted between 6.00 - 6.50.
• Part A and B are heated separately to 75°C. After adding part B into part A the mixture is homogenized with Ultra Turrax for one minute at 11000 rpm. After cooling down to 50°C part C is added. Afterwards the mixture is homogenized for one minute at 16000 rpm. At a temperature ⁇ 40°C part D is added. At room temperature the pH-value is adjusted with part E between 6.00 and 6.50.
• Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
• Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
• Part A and part B are heated separately to 75°C.
• Part B is added into part A under continuous stirring and afterwards homogenized with Ultra Turrax for 30sec at 11000 rpm .
• After cooling down to 60°C part C is added.
• At 40°C part C is added and homogenized for 15sec at 11000 rpm.
• the pH-value is adjusted with part E.
• Example 18 UVA/UVB Daily Care Lotion, type O/W
• Part A and B are heated separately to 75°C; part C to 60°C.
• Part B is poured into part A under stirring. After one-minute of homogenization at 11000 rpm part C is added to the mixture of A/B. After cooling down to 40°C part D is incorporated. At room temperature the pH value is adjusted with part E between 6.3 and 7.0. Finally part F is added.
• Part A and part B are heated separately to 75°C.
• Part A is poured into part B under stirring.
• part C is added to the mixture and homogenized with an Ultra Turrax at 11000 rpm for 30 sec. After cooling down to 65°C Sodium Acrylates Copolymer (and) Mineral Oil (and) PPG-1 Trideceth-6 At 50°C is added slowly to the UV absorber dispersion. At about 35-30°C part F is incorporated. The pH is adjusted with part G between 5.5 and 6.5.
• Part A and part B are heated separately up to 80°C.
• Part A is poured into part B while stirring and homogenized with an Ultra Turrax by 11000 rpm for 30 sec. After cooling down to 60°C part C is incorporated.
• At40°C part D is added slowly under continuous stirring. The pH is adjusted with part E between 6.50 - 7.00.
• Part A and part B are heated separately up to 80°C, part C is heated to 50°C.
• Part B is poured into part A and homogenized with an Ultra Turrax for 1 minute at 11000 rpm. After cooling down to 50°C part C is added under continuous stirring. At 40°C part D is incorporated and homogenized again for 10 sec. at 11000 rpm. The pH is adjusted with part E.
• Part A and part B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
• Part A and part B are heated separately to 80°C.
• Part A is poured into part B under continuous stirring. Afterwards the mixture is homogenized with an Ultra Turrax at 11 000 rpm for 1 min. After cooling down to 60°C part C is incorporated. At 40°C part D is added and the mixture homogenized for a short time again. At 35°C part E is added and at room temperature Fragrance is added. Finally the pH is adjusted with Sodium Hydroxide.
• Part A and part B are heated separately up to 80°C.
• Part B is poured into part A under moderate stirring.
• the mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 minute.
• After cooling down to 70°C part C is added under stirring.
• After cooling further down to 50°C part D is incorporated very slowly.
• At 40°C part E is added.
• At room temperature the pH adjusted with part F to 7.00 and part G is added.
• Example 25 UVA/UVB Sun Protection Lotion, O/W type
• Part A and part B are heated separately up to 80°C.
• Part B is poured into part A under moderate stirring.
• the mixture is homogenized with an Ultra Turrax at 11000 rpm for
• Part A and part B are heated separately up to 75°C.
• Part B is poured into part A under progressive stirring speed.
• the ingredients of part D are added separately.
• After cooling down to 55°C under moderate stirring part C is added.
• At a temperature ⁇ 35°C the pH is checked and adjusted with Sodium Hydroxide and homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm.
• At room temperature part F is added.
• Example 27 W/O Sunscreen Lotion
• Part A is heated to 80°C whilst stirring.
• Part B is added into part A and homogenized with an
• Part A is heated separately to 80°C under gentle stirring.
• Part B is added to part A and homogenized for one minute at 11000 rpm. After cooling down to 30°C part C is added under continuous stirring.
• This Sunscreen may also be used as an anti-wrinkle perception modifier.

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