WO1997003643A1 - Sunscreen compositions - Google Patents

Sunscreen compositions Download PDF

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Publication number
WO1997003643A1
WO1997003643A1 PCT/EP1996/003044 EP9603044W WO9703643A1 WO 1997003643 A1 WO1997003643 A1 WO 1997003643A1 EP 9603044 W EP9603044 W EP 9603044W WO 9703643 A1 WO9703643 A1 WO 9703643A1
Authority
WO
WIPO (PCT)
Prior art keywords
absorber
alkyl
formula
insoluble organic
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1996/003044
Other languages
English (en)
French (fr)
Inventor
Helmut Luther
Albert Stehlein
Marina Minklei
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG, Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Geigy AG
Priority to AT96924893T priority Critical patent/ATE196730T1/de
Priority to US09/000,026 priority patent/US5980872A/en
Priority to AU65199/96A priority patent/AU699875B2/en
Priority to DK96924893T priority patent/DK0840595T3/da
Priority to EP96924893A priority patent/EP0840595B1/en
Priority to DE69610559T priority patent/DE69610559T2/de
Priority to NZ313189A priority patent/NZ313189A/xx
Priority to JP50625697A priority patent/JP3960625B2/ja
Priority to CA002227004A priority patent/CA2227004C/en
Priority to BR9609538A priority patent/BR9609538A/pt
Priority to IL12278896A priority patent/IL122788A/xx
Publication of WO1997003643A1 publication Critical patent/WO1997003643A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • the present invention relates to a method for producing new formulations of UV absorbers and to their use in sunscreen compositions which, in turn, are useful, in particular, for the protection of human skin.
  • sunscreen formulations which include a material which is intended to counteract UV radiation, thereby inhibiting the said undesired effects on the skin.
  • UV protectants in sunscreen formulations, especially soluble organic UV absorbers and insoluble micronised inorganic compounds, in particular zinc oxide and titanium dioxide.
  • SPF Sun Protection Factor
  • insoluble inorganic compounds such as zinc oxide and titanium dioxide leads to a reduced stability of formulations containing them.
  • inorganic compounds have been claimed to generate toxic radicals under the influence of light ("Redox Mechanisms in Heterogeneous Photocatalysis", Serpone et al, Electrochemistry in Colloids and Dispersions, Editors Mackay and Texter, VCH Publishers Inc., NewYork 1992).
  • formulations provide excellent UV protection and have at least as high an SPF rating as corresponding sunscreen formulations containing a known inorganic UV absorber. Unlike the latter UV absorbers, micronised, insoluble organic UV absorbers show no tendency, under the influence of light, to generate radicals which could damage or sensitise human skin.
  • the present invention provides, as a first aspect, a method of producing a composition , which is especially suitable for use in pharmaceutical or cosmetic applications, comprising a micronised insoluble organic UV absorber, which method comprises grinding the insoluble organic UV absorber, in coarse particle form, in a grinding apparatus, in the presence of 1 to 50%, preferably 5 to 40% by weight, based on the micronised insoluble organic UV absorber, of an alkyl polyglucoside having the formula C n H 2n+1 O(C 6 H 10 O 5 ) x H, in which n is an integer ranging from 8 to 16 and x is the mean polymerisation level of the glucoside moiety (C 6 H 10 O 5 ) and ranges from 1.4 to 1.6, or an ester thereof.
  • the insoluble organic UV absorber may be, e.g., an oxanilide, a triazine, a triazole, a vinyl group-containing amide, a cinnamic acid amide or a sulfonated benzimidazole UV absorber.
  • One preferred class of oxanilide UV absorbers is that having the formula:
  • R 1 and R 2 independently, are C 1 -C 18 alkyl or C 1 -C 18 alkoxy.
  • a preferred compound of formula (1 ) is N-(2-ethoxyphenyl)-N'-(2-ethylphenyl)-ethanediamide.
  • a preferred class of triazine compounds is that having the formula: in which R 3 , R 4 and R 5 , independently, are H, OH, C 1 -C 18 alkoxy, NH 2 , NH-R 6 or N(R 6 ) 2 in which R 6 is C 1 -C 18 alkyl, OR 6 in which R 6 has its previous significance, phenyl, phenoxy or anilino, or pyrrolo, in which the respective phenyl, phenoxy or anilino, or pyrrolo moieties are optionally substituted by one, two or three substitutents selected from OH, carboxy, CO-NH 2 , C 1 -C 18 alkyl or -alkoxy, C 1 -C 18 carboxyalkyl, C 5 -C 8 cycloalkyl, a methylidenecamphor group, a group
  • ammonium mono-, di- or tri-C 1 -C 4 alkylammonium, mono-, di- or tri- C 2 -C 4 alkanolammonium salts, or the C 1 -C 18 alkyl esters thereof.
  • Preferred compounds of formula (2) are those having one of the formulae:
  • Particularly preferred compounds of formula (2) are those having the formula:
  • R 7 are the same or different and each is hydrogen; an alkali metal; an ammonium group N(R 8 ) 4 in which R 8 is hydrogen or an organic radical; C 1 -C 20 alkyl; or a polyoxyethylene radical which contains from 1 to 10 ethylene oxide units and the terminal OH group of which may be etherified by a C 1 -C 3 alcohol.
  • R 7 when R 7 is an alkali metal it is preferably potassium or, especially sodium; when R 7 is a group N(R 8 ) 4 in which R 8 has its previous significance, it is preferably a mono-, di- or tri-C 1 -C 4 alkylammonium salt, a mono-, di- or tri-C 2 -C 4 alkanolammonium salt or a C 1 -C 20 alkyl ester thereof; when R 8 is a C 1 -C 20 alkyl group, it is preferably a C 6 -C 12 alkyl group, more preferably a C 8 -C 9 alkyl group, especially the 3,5,5-trimethylpentyl group or, most particularly, the 2-ethylhexyl group; and when R 8 is polyoxyethylene group, this preferably contains from 2-6 ethylene oxide units.
  • triazole insoluble organic UV absorbers having the formula:
  • T 1 is C 1 -C 18 alkyl or, preferably, hydrogen; and T 2 is C 1 -C 18 alkyl, optionally substituted by phenyl, preferably ⁇ , ⁇ -dimethylbenzyl.
  • a further preferred class of triazole insoluble organic UV absorbers is that having the formula:
  • a still further preferred class of triazole insoluble organic UV absorbers is that having the formula:
  • T 2 has its previous significance and is preferably t-butyl.
  • a preferred class of vinyl group-containing amide insoluble organic UV absorbers is that having the formula:
  • R 9 -(Y) m -CO-C(R 10 ) C(R 11 )-N(R 12 )(R 13 ) (34) in which R 9 is C 1 -C 18 alkyl, preferably C 1 -C 5 alkyl, or phenyl optionally substituted by one, two or three substituents selected from OH, C 1 -C 18 alkyl, C 1 -C 18 alkoxy or CO-OR 6 in which R 6 has its previous significance; R 10 , R 11 , R 12 and R 13 are the same or different and each is C 1 -C 18 alkyl, preferably C 1 -C 5 alkyl, or hydrogen; Y is N or O; and m has its previous
  • Preferred compounds of formula (34) are 4-octyl-3-penten-2-one, ethyl-3-octylamino-2-butenoate, 3-octylamino-1-phenyl-2-buten-1-one and 3-dodecylamino-1-phenyl-2-buten-1-one.
  • a preferred class of cinnamic acid amide insoluble organic UV absorbers is that having the formula: in which R 14 is hydroxy or C 1 -C 4 alkoxy, preferably methoxy or ethoxy; R 15 is hydrogen or C 1 - dalkyl, preferably methyl or ethyl; and R 16 is -(CONH) m -phenyl in which m has its previous significance and the phenyl group is optionally substituted by one, two or three substituents selected from OH, C 1 -C 18 alkyl, C 1 -C 18 alkoxy or CO-OR 6 in which R 6 has its previous significance.
  • R 16 is phenyl, 4-methoxyphenyl or the phenylaminocarbonyl group.
  • a preferred class of sulfonated benzimidazole insoluble organic UV absorbers is that having the formula:
  • d-d 8 alkyl groups may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.-butyl, n-amyl, n-hexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, tetradecyl, hexydecyl or
  • C 1 -C 18 alkoxy groups include methoxy, ethoxy, propoxy, butoxy, n-hexoxy, n-heptoxy, n-octoxy, isooctoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, tetradecoxy, hexadecoxy or octadecoxy, methoxy and ethoxy being preferred.
  • C 1 -C 18 carboxyalkyl includes carboxymethyl, carboxyethyl, carboxypropyl,
  • carboxy isopropyl, carboxybutyl, carboxyisobutyl, carboxybutyl, carboxyamyl, carboxyhexyl, carboxyheptyl, carboxyoctyl, carboxyisooctyl, carboxynonyl, carboxydecyl, carboxyundecyl, carboxydodecyl, carboxytetradecyl,
  • C 5 -C 8 cycloalkyl includes cyclopentyl, cyclohexyl and cyclooctyl.
  • the compounds of formula (1) to (35) are known.
  • the compounds of formula (30) are described, together with their production, in US-A-4617390.
  • polyglucoside provide high SPF values. Moreover, such formulations do not agglomerate and they remain in a dispersed form and do not readily settle.
  • the micronised insoluble organic UV absorber produced according to the method of the present invention, has a mean particle size in the range of from 0.01 to 2, more preferably from 0.02 to 1.5, especially from 0.05 to 1.0 ⁇ .
  • the grinding apparatus used to conduct the method of the present invention may be, e.g., a jet, ball, vibration or hammer mill, preferably a high speed stirring mill or impact mill, especially a rotating ball mill, vibrating mill, tube mill or rod mill.
  • the alkyl polyglucoside may consist of a C 1 -C 12 ester of the compound of formula C n H 2n+1 O(C 6 H 10 O 5 ) x H, namely an ester formed by reacting a C 1 -C 12 acid, such formic, acetic, propionic, butyric, sulfosuccinic, citric or tartaric acid, with one or more free OH groups on the glucoside moiety (C 6 H 10 O 5 ).
  • a C 1 -C 12 acid such formic, acetic, propionic, butyric, sulfosuccinic, citric or tartaric acid
  • the micronised formulation of a insoluble organic UV absorber produced according to the method of the present invention may be used together with one or more further UV absorbers, such as soluble organic UV absorbers, insoluble inorganic UV absorbers and/or melanine, which are conventionally used in cosmetic compositions for the protection of human skin against UV radiation.
  • further UV absorbers such as soluble organic UV absorbers, insoluble inorganic UV absorbers and/or melanine, which are conventionally used in cosmetic compositions for the protection of human skin against UV radiation.
  • the use of such combinations of active ingredients may lead to synergistic effects.
  • composition produced according to the method of the present invention is particularly suitable for use in a sunscreen formulation.
  • the present invention also provides a sunscreen composition
  • a sunscreen composition comprising a) 0.1 to 15%, preferably 0.5 to 10% by weight, based on the total composition of a micronised formulation of an insoluble organic UV absorber, produced according to the method of the present invention; and optionally b) a cosmetically acceptable carrier.
  • the sunscreen composition of the present invention may be produced by physically blending the micronised formulation of an insoluble organic UV absorber and carrier components by any conventional method, e.g. by simply stirring the two materials together.
  • a mixture of the coarse, insoluble organic UV absorber, the alkyl polyglucoside grinding aid, and the milling bodies are ground until the coarse, insoluble organic UV absorber has been converted into micronised form, as described earlier in relation to the production of the micronised insoluble organic UV absorber.
  • the filtrate consisting of the micronised insoluble organic UV absorber and grinding aid components, may be blended with a cosmetically compatible carrier.
  • the sunscreen composition of the invention may be formulated as a water-in oil or an oil-in-water dispersion, an oil or oil-alcohol lotion, a vesicular dispersion of an ionic or nonionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation.
  • the optional cosmetically acceptable carrier When formulated as a water-in oil or an oil-in-water dispersion, the optional cosmetically acceptable carrier preferably comprises 5 to 50% of an oil phase, 5 to 20% of an emulsifier and 30 to 90% of water, each by weight based on the total weight of the carrier.
  • the oil phase may comprise any oil conventionally used in cosmetic formulations, e.g., one or more of a hydrocarbon oil, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol.
  • a hydrocarbon oil e.g., one or more of a hydrocarbon oil, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol.
  • Preferred mono- or polyols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerine and sorbitol.
  • the emulsifier also may comprise any emulsifier conventionally used in cosmetic formulations, e.g., one or more of an ethoxylated ester of a natural oil derivative such as a polyethoxylated ester of hydrogenated castor oil; a silicone oil emulsifier such as a silicone polyol; an optionally ethoxylated fatty acid soap; an ethoxylated fatty alcohol; an optionally ethoxylated sorbitan ester; an ethoxylated fatty acid; or an ethoxylated glyceride.
  • an ethoxylated ester of a natural oil derivative such as a polyethoxylated ester of hydrogenated castor oil
  • silicone oil emulsifier such as a silicone polyol
  • an optionally ethoxylated fatty acid soap an ethoxylated fatty alcohol
  • an optionally ethoxylated sorbitan ester an ethoxylated fatty
  • the sunscreen composition of the invention may also comprise further components which are known to perform a useful function in a sunscreen composition.
  • further components include, e.g., emollients, skin moisturisers, skin tanning accelerators, antioxidants, emulsion stabilisers, thickening agents such as xanthan, moisture-retention agents such as glycerine, film formers, preservatives, perfumes and colourants.
  • the sunscreen composition of the invention provides excellent protection of the human against the damaging effects of sunlight, while permitting safe tanning of the skin. Moreover, the sunscreen composition of the invention has a skin waterproofing effect.
  • Example 1 30g of 2,4,6-trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)-1 ,3,5-triazine having the formula:
  • 5 g of the resulting dispersion are then formulated with 0.25 g NaCl, 0.25 g of a polydimethylsiloxane de-foamer, 13.25 g of water and 6.25 g of a thickener which contains, per litre, 16 g imidazolidinyl urea, 24 g of a mixture of methyl-, ethyl-, i-butyl- and n-butyl esters of 4-hydroxybenzoic acid in phenoxyethanol, 40 g xanthan gum and 940 g water.
  • the resulting lotion formulation is composed of:
  • the lotion has an average SPF (measured on an SPF analyzer/Optometrics according to DIN 67501) of 13.2.
  • Example 2 Using an analogous procedure to that described in Example 1 but applying a grinding time of 30 minutes, a formulation is obtained having a mean particle size of 0.9 ⁇ (measured on a Malvern Mastersizer) and an average SPF of 19.5.
  • Example 2 Using an analogous procedure to that described in Example 1 but applying a grinding time of 45 minutes, a formulation is obtained having a mean particle size of 0.88 ⁇ (measured on a Malvern Mastersizer) and an average SPF of 22.8.
  • Example 2 Using an analogous procedure to that described in Example 1 but applying a grinding time of 80 minutes, a formulation is obtained having a mean particle size of 0.73 ⁇ (measured on a Malvern Mastersizer) and an average SPF of 33.7.
  • the lotion has an average SPF (measured on an SPF analyzer/Optometrics according to DIN 67501) of 18.7 at a particle size of 0.22 ⁇ .
  • Example 5 Using the procedure described in Example 5, but replacing the compound of formula (102) used therein by the compound having the formula: there is obtained a lotion formulation which has an average SPF (measured on an SPF analyzer/Optometrics according to DIN 67501) of 17.5 at a particle size of 0.44 ⁇ .
  • Example 5 Using the procedure described in Example 5, but replacing the compound of formula (102) used therein by the compound having the formula: there is obtained a lotion formulation which has an average SPF (measured on an SPF analyzer/Optometrics according to DIN 67501) of 23.3 at a particle size of 0.43 ⁇ .
  • Example 5 Using the procedure described in Example 5, but replacing the compound of formula (102) used therein by the compound having the formula: there is obtained a lotion formulation which has an average SPF (measured on an SPF analyzer/Optometrics according to DIN 67501) of 17.0 at a particle size of 0.3 ⁇ .

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
PCT/EP1996/003044 1995-07-22 1996-07-11 Sunscreen compositions Ceased WO1997003643A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
AT96924893T ATE196730T1 (de) 1995-07-22 1996-07-11 Sonnenschutzmittel
US09/000,026 US5980872A (en) 1995-07-22 1996-07-11 Sunscreen compositions
AU65199/96A AU699875B2 (en) 1995-07-22 1996-07-11 Sunscreen compositions
DK96924893T DK0840595T3 (da) 1995-07-22 1996-07-11 Solbeskyttelsesmiddel
EP96924893A EP0840595B1 (en) 1995-07-22 1996-07-11 Sunscreen compositions
DE69610559T DE69610559T2 (de) 1995-07-22 1996-07-11 Sonnenschutzmittel
NZ313189A NZ313189A (en) 1995-07-22 1996-07-11 Sunscreen compositions
JP50625697A JP3960625B2 (ja) 1995-07-22 1996-07-11 サンスクリーン組成物
CA002227004A CA2227004C (en) 1995-07-22 1996-07-11 Sunscreen compositions
BR9609538A BR9609538A (pt) 1995-07-22 1996-07-11 Composições de filtro solar
IL12278896A IL122788A (en) 1995-07-22 1996-07-11 Method for producing new formulations of uv absorbers and their use in sunscreen compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9515048.8 1995-07-22
GBGB9515048.8A GB9515048D0 (en) 1995-07-22 1995-07-22 Sunscreen compositions

Publications (1)

Publication Number Publication Date
WO1997003643A1 true WO1997003643A1 (en) 1997-02-06

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Application Number Title Priority Date Filing Date
PCT/EP1996/003044 Ceased WO1997003643A1 (en) 1995-07-22 1996-07-11 Sunscreen compositions

Country Status (17)

Country Link
US (1) US5980872A (cg-RX-API-DMAC7.html)
EP (1) EP0840595B1 (cg-RX-API-DMAC7.html)
JP (1) JP3960625B2 (cg-RX-API-DMAC7.html)
KR (1) KR100444100B1 (cg-RX-API-DMAC7.html)
AR (1) AR003464A1 (cg-RX-API-DMAC7.html)
AT (1) ATE196730T1 (cg-RX-API-DMAC7.html)
AU (1) AU699875B2 (cg-RX-API-DMAC7.html)
BR (1) BR9609538A (cg-RX-API-DMAC7.html)
CA (1) CA2227004C (cg-RX-API-DMAC7.html)
DE (1) DE69610559T2 (cg-RX-API-DMAC7.html)
DK (1) DK0840595T3 (cg-RX-API-DMAC7.html)
ES (1) ES2151670T3 (cg-RX-API-DMAC7.html)
GB (2) GB9515048D0 (cg-RX-API-DMAC7.html)
IL (1) IL122788A (cg-RX-API-DMAC7.html)
NZ (1) NZ313189A (cg-RX-API-DMAC7.html)
PT (1) PT840595E (cg-RX-API-DMAC7.html)
WO (1) WO1997003643A1 (cg-RX-API-DMAC7.html)

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2755966A1 (fr) * 1996-11-20 1998-05-22 Ciba Geigy Ag Composes, compositions les contenant, et leur utilisation pour stabiliser une matiere organique
WO1998022447A1 (en) * 1996-11-20 1998-05-28 Ciba Specialty Chemicals Holding Inc. Symmetrical triazine derivatives
EP0878469A1 (de) * 1997-05-16 1998-11-18 Ciba SC Holding AG Resorcinyl-Triazine
DE19726189A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen mit einem Gehalt an in gelöster Form vorliegenden s-Triazinderivaten
DE19726121A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an Bis-Resorcinyltriazinderivaten
DE19726184A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an lichtschutzwirksamen Benzotriazolderivaten
DE19726172A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an s-Triazinderivaten
DE19726132A1 (de) * 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen mit einem Gehalt an in gelöster Form vorliegenden Bis-Resorcinyltriazinderivaten
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FR3163267A1 (fr) 2024-06-14 2025-12-19 L'oreal Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé polysaccharide silicié à fonctions acétoacétates
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WO2025242884A1 (en) 2024-05-24 2025-11-27 Basf Se Substituted cinnamic acid derivatives as uv absorbers and uses thereof

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DK0840595T3 (da) 2001-01-08
NZ313189A (en) 1999-07-29
PT840595E (pt) 2001-03-30
DE69610559D1 (de) 2000-11-09
EP0840595A1 (en) 1998-05-13
GB2303549A (en) 1997-02-26
US5980872A (en) 1999-11-09
AU6519996A (en) 1997-02-18
DE69610559T2 (de) 2001-05-31
BR9609538A (pt) 1999-02-23
IL122788A0 (en) 1998-08-16
JP3960625B2 (ja) 2007-08-15
ATE196730T1 (de) 2000-10-15
KR19990035753A (ko) 1999-05-25
GB9515048D0 (en) 1995-09-20
GB9614912D0 (en) 1996-09-04
CA2227004C (en) 2008-06-03
EP0840595B1 (en) 2000-10-04
AR003464A1 (es) 1998-08-05
ES2151670T3 (es) 2001-01-01
IL122788A (en) 2001-03-19
JP2000501064A (ja) 2000-02-02
KR100444100B1 (ko) 2004-11-06
CA2227004A1 (en) 1997-02-06
AU699875B2 (en) 1998-12-17

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