WO2003030856A1 - Compositions d'ecran solaire au siloxane - Google Patents

Compositions d'ecran solaire au siloxane Download PDF

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Publication number
WO2003030856A1
WO2003030856A1 PCT/EP2002/010920 EP0210920W WO03030856A1 WO 2003030856 A1 WO2003030856 A1 WO 2003030856A1 EP 0210920 W EP0210920 W EP 0210920W WO 03030856 A1 WO03030856 A1 WO 03030856A1
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WO
WIPO (PCT)
Prior art keywords
sunscreen
water
soluble
salt
siloxane
Prior art date
Application number
PCT/EP2002/010920
Other languages
English (en)
Inventor
Katja Berg-Schultz
Horst Westenfelder
Original Assignee
Roche Vitamins 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 Roche Vitamins Ag filed Critical Roche Vitamins Ag
Publication of WO2003030856A1 publication Critical patent/WO2003030856A1/fr

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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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • 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
    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

  • the present invention relates to sunscreen compositions for protecting human skin from damaging effects of UN radiation.
  • the present invention relates to the use of a siloxane sunscreen in the manufacture of water-resistant sunscreen compositions which further contain a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen.
  • the present invention relates to novel water-resistant sunscreen compositions which contain a siloxane sunscreen, a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen.
  • the present invention relates to novel sunscreen compositions comprising certain siloxane sunscreens as defined below and certain water-soluble sunscreens as defined below and, optionally, further water-soluble, fat-soluble and/or pigment sunscreens.
  • Water-soluble sunscreen agents e.g., sunscreen agents which are acids or salts, or pigments used as sunscreens
  • sunscreen agents tend to be rinsed off from the skin, thus resulting in a reduced UV protection of the compositions on the skin after contact with water, e.g. in water sports.
  • siloxane sunscreens in sunscreen compositions containing a water-soluble sunscreen and/or a pigment sunscreen improves the fixation of those water-soluble sunscreen agents and/or sunscreen pigments on the skin that is exposed to water such as in water sport activities.
  • siloxane sunscreen denotes a siloxane, particularly a polysiloxane which carries at least one group which absorbs UV-A or UN-B radiation.
  • siloxane sunscreens are those of the general formula la or lb
  • Y is a group of the formula (a) or (b)
  • R 5 is hydrogen or C ⁇ - 6 alkyl
  • Z' and Z" are, independently, hydrogen, hydroxy, C ⁇ - 6 alkyl or C ⁇ - 6 alkoxy; and p is an integer from 1 to 6; or a group of the formula (c)
  • R is hydrogen or - 6 -alkyl.
  • Y is a group (a) or (b) and their preparation are disclosed, e.g., in EP 538,431 and EP 679,645.
  • the preferred siloxane sunscreens for use in the present invention are those of formula la above wherein Y is a group of the formulas (a) and/or (b), particularly those wherein R 1 and R 2 are ethyl, R 5 , Z' and Z" are hydrogen, and p is 1.
  • polysiloxane sunscreens of the formula la wherein s is an average number of 3 to 10 and r is an average number of 20 to 80. Most preferred are polysiloxane sunscreens of the formula la wherein s is ca. 4 and r is ca. 60, and wherein about 80 % of the groups Y are of the alkylidene structure (a) and about 20 % of the groups Y are of the alkylene structure (b), such as disclosed in EP 709,080 and referred to therein as "Polysiloxane A".
  • the water-soluble sunscreen which may be used in combination with the siloxane sunscreen according to the present invention can be any conventional water-soluble sunscreen.
  • Typical water-soluble sunscreens are UV- filtering agents which contain hydrophilic groups that promote the water-solubility of these compounds, such as sulfonic acid groups, as well as salts thereof.
  • Examples of such water-soluble sunscreens are phenylene-l,4-bis-benzimidazolsulfonic acids or salts thereof, particularly those of the general formula II
  • R 1 and R are sulfonic acid groups and salts thereof and R 2 and R 4 are, indepen- dently, hydrogen or a group R 1 or R 3 (see EP 669,323), preferably 2,2-(l,4-phenylene)bis- (lH-benzimidazol-4,6-disulfonic acid) mono sodium salt; 2-phenylbenzimidazol-5- sulfonic acid (PARSOL ® HS, see DE 4,203,072) and salts thereof, e.g.
  • compositions according to the present invention may contain one or more of such water-soluble sunscreens.
  • the present invention relates to novel sunscreen compositions which comprise a siloxane of the general formulas la or lb as defined earlier, and one or more water-soluble sunscreens selected from phenylene-l,4-bis-benzimidazolsulfonic acids or salts thereof of the formula II as defined above; 2-phenylbenzimidazol-5-sulfonic acid and salts thereof; benzophenone sulfonic acid derivatives and salts thereof; 3-benz- ylidenecamphor sulfonic acid derivatives and salts thereof; 2-methyl-5-(2-oxo-3-bornyl- idenemethyl) benzene sulfonic acid and salts thereof; and 3,3'-(l,4-phenylenedimethyl- ene)-bis-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-l-ylmethanesulfonic acid and salts thereof.
  • any sunscreen pigment conventionally used in sunscreen compositions maybe used in combination with the siloxane sunscreen according to the present invention.
  • Such pigment sunscreens are typically metal oxides, such as titanium, zinc, zirconium, or iron oxides, or mixtures thereof.
  • the pigments may be coated, e.g. by metal oxides such as e.g. aluminum or zirconium oxides or by organic coatings such as e.g. polyols, methicone, aluminum stearate, alkyl silane etc., and maybe of nanoparticle size, i.e. of an average particle diameter of less than about 200 nm, e.g. from about 15 to about 100 nm. Examples of such conventionally used sunscreen pigments are disclosed in WO 93/04,666.
  • the sunscreen compositions in accordance with the present invention may, besides the siloxane sunscreen, further contain one or more fat-soluble sunscreens which may be UN A screening agents i.e. substances having absorption maxima between about 320 and 400 nm; or UV B screening agents, i.e. substances having absorption maxima between about 290 and 320 nm.
  • UN A screening agents i.e. substances having absorption maxima between about 320 and 400 nm
  • UV B screening agents i.e. substances having absorption maxima between about 290 and 320 nm.
  • acrylates such as 2-efhylhexyl 2-cyano-3,3-diphenylacrylate (octocrylene, PARSOL 340), ethyl 2-cyano-3,3-diphenylacrylate, and the like
  • camphor derivatives such as 4-methyl benzylidene camphor (PARSOL 5000), 3-benzyl- idene camphor, polyacrylamidomethyl benzylidene camphor, and the like
  • cinnamate derivatives such as octyl methoxycinnamate (PARSOL MCX), ethoxyethyl methoxycinnamate, isoamyl methoxycinnamate and the like
  • p-aminobenzoic acid derivatives such as p-aminobenzoic acid, 2-ethylhexyl p-dimethyl- aminobenzoate, N-oxypropylenated ethyl p-aminobenz
  • benzophenone derivatives such as benzophenone-3, benzophenone-4, 2,2', 4, 4' tetra- hydroxy-benzophenone, 2,2'dihydroxy-4,4'dimethox benzophenone and the like
  • esters of benzalmalonic acid such as di (2-ethylhexyl) 4-methoxybenzalmalonate
  • benzotriazoles such as 2,2'-methylene-bis-(6(2H-benzotriazol-2-yl)4-(l,l,3,3-tetramethyl- butyl)phenol (Tinosorb M) and hydroxyphenyl-benzotriazole as disclosed in
  • compositions of the present invention may also contain stabilizing agents for any dibenzoylmethane derivatives present, such as PARSOL 1789, examples of which are 3,3-diphenylacrylate derivatives as described in EP 514,491 and EP 780,119 and benzylidene camphor derivatives as described in US 5,605,680.
  • PARSOL 1789 examples of which are 3,3-diphenylacrylate derivatives as described in EP 514,491 and EP 780,119 and benzylidene camphor derivatives as described in US 5,605,680.
  • the siloxane sunscreen is used preferably in an amount of from about 0.01 wt.-% to about 20.0. wt.-% based on the total weight of the composition.
  • the preparation of sunscreen compositions according to the present invention can be accomplished by conventional means, i.e. by incorporating the sunscreen agents in auxiliary agents, e.g. a cosmetic base, which are conventionally used for such formulations.
  • auxiliary agents e.g. a cosmetic base
  • the total amount of the sunscreen agents in the final composition is not critical and may range, e.g., from about 0.1 to about 20 % of active ingredient, i.e., screening agent(s).
  • cosmetic bases for sunscreen compositions of the present invention there can be used any conventional preparation which corresponds to the cosmetic requirements, e.g. creams, lotions, emulsions, salves, gels, solutions, sprays, sticks and milks; see also: Sunscreens, Development, Evaluation and Regulatory Aspects, ed. N.Y. Lowe, N.A. Shaath, Marcel Dekker, Inc. New York and Basel, 1990.
  • Titanium Dioxide 0,1 - 10
  • siloxane sunscreen in the manufacture of water-resistant sunscreen compositions which further contain a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen,
  • p is an integer from 1 to 6, preferably 1; more preferably the use of a siloxane sunscreen of the formula (la), wherein s is an average number 4 and r is an average number 60, and wherein about 80 % of the groups Y are of the alkylidene structure (a) and about 20 % of the groups Y are of the alkylene structure (b);
  • (Hi) preferably the use of a siloxane sunscreen of the formula la or lb wherein R and R" are C ⁇ - 10 alkyl or phenyl; X and X' are Q-ioalkyl, phenyl or a group Y wherein Y is a group of the formula (c) wherein R 3 , R 4 is hydrogen or - 6 -alkyl, preferably R 3 is methyl and R 4 is hydrogen or methyl.
  • a siloxane sunscreen in the manufacture of water-resistant sunscreen compositions which further contain a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen, wherein the pigment is a nanoparticle metal oxide, preferably a titanium dioxide having a mean particle size of about 15 to about 100 nm.
  • a siloxane sunscreen in the manufacture of water-resistant sunscreen compositions which further contain a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen, wherein the water-soluble sunscreen is a phenylen- 1,4-bis-benzimidazolsulfonic acid or salt thereof, 2-phenylbenzimidazol-5-sulf- onic acid or salt thereof, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid or salt thereof, 2,2-(l,4-phenylene)bis-(lH-benzimidazol-4,6-disulfonic acid) or salt thereof, 4(2-oxo- bornylidenemethyl)benzene sulfonic acid or salt thereof, 2-methyl-5-(2-oxo-3-bornyl- idenemethyl) benzene sulfonic acid or salt thereof, or 3,3'-(l,4-phenylenedimethylene)- bis-(7,7-di
  • a siloxane sunscreen in the manufacture of water-resistant sunscreen com- positions which further contain a water-soluble sunscreen and/or a pigment sunscreen and, optionally, a further fat-soluble sunscreen, wherein the water-resistant sunscreen composition is an oil-in-water or a water-in-oil emulsion, or a gel.
  • Water-resistant sunscreen compositions comprising a siloxane sunscreen, preferably as under (1), a water-soluble sunscreen, preferably as under (3), and/or a pigment sunscreen, preferably as under (2), and, optionally, a further fat-soluble sunscreen.
  • Sunscreen compositions comprising a siloxane sunscreen, preferably as under (1), a water-soluble sunscreen, preferably as under (3), and/or a pigment sunscreen, preferably as under (2), and, optionally, a further fat-soluble sunscreen.

Abstract

La présente invention concerne l'utilisation d'un écran solaire au siloxane pour préparer des compositions d'écran solaire résistantes à l'eau qui contiennent également un écran solaire soluble dans l'eau et/ou un écran solaire pigmentaire, et éventuellement un autre écran solaire soluble dans les graisses.
PCT/EP2002/010920 2001-10-08 2002-09-28 Compositions d'ecran solaire au siloxane WO2003030856A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01123967 2001-10-08
EP01123967.0 2001-10-08

Publications (1)

Publication Number Publication Date
WO2003030856A1 true WO2003030856A1 (fr) 2003-04-17

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2243465A1 (fr) * 2008-02-19 2010-10-27 Shiseido Company, Ltd. Produit cosmétique écran solaire du type émulsion eau-dans-huile

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350314A2 (fr) * 1988-07-08 1990-01-10 Shiseido Company Limited Dérivés de l'acide cinnamique du type silicone, méthode de préparation, absorbant pour rayons UV et agent de traitement externe de la peau
EP0478284A2 (fr) * 1990-09-25 1992-04-01 Shin-Etsu Chemical Co., Ltd. Composés organiques de silicium et compositions cosmétiques
WO1994006404A1 (fr) * 1992-09-17 1994-03-31 L'oreal Composition cosmetique filtrante photostable contenant un filtre uv-a et un polymere filtre du type silicone benzotriazole
EP0712856A1 (fr) * 1994-11-17 1996-05-22 L'oreal Nouveaux filtres solaires, compositions cosmétiques photoprotectrices les contenant et utilisations
WO1996035409A1 (fr) * 1995-05-12 1996-11-14 L'oreal Compositions cosmetiques pour la photoprotection de la peau et/ou des cheveux a base d'un melange synergique de filtres et utilisations
EP0860165A1 (fr) * 1997-02-24 1998-08-26 L'oreal Compositions cosmétiques pour la photoprotection de la peau et/ou des cheveux à base d'un mélange synergique de filtres
EP0979645A1 (fr) * 1998-07-16 2000-02-16 F. Hoffmann-La Roche Ag Composition de protection solaire contenant un agent anti UV-B de type polysiloxane et un agent anti UV-B de type benzimidazole
US6183728B1 (en) * 1991-08-29 2001-02-06 L'oreal Screening cosmetic composition comprising one nanopigment of metallic oxide and one fat-soluble screening polymer
EP1133980A2 (fr) * 2000-03-15 2001-09-19 Basf Aktiengesellschaft Utilisation d'une combinaison d'agents photoprotecteurs comprenant en tant que composé essentiel des hydroxybenzophénones aminosubstituées comme filtres UV photostables dans des préparations cosmétiques et pharmaceutiques
WO2002049594A2 (fr) * 2000-12-18 2002-06-27 L'oreal Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350314A2 (fr) * 1988-07-08 1990-01-10 Shiseido Company Limited Dérivés de l'acide cinnamique du type silicone, méthode de préparation, absorbant pour rayons UV et agent de traitement externe de la peau
EP0478284A2 (fr) * 1990-09-25 1992-04-01 Shin-Etsu Chemical Co., Ltd. Composés organiques de silicium et compositions cosmétiques
US6183728B1 (en) * 1991-08-29 2001-02-06 L'oreal Screening cosmetic composition comprising one nanopigment of metallic oxide and one fat-soluble screening polymer
WO1994006404A1 (fr) * 1992-09-17 1994-03-31 L'oreal Composition cosmetique filtrante photostable contenant un filtre uv-a et un polymere filtre du type silicone benzotriazole
EP0712856A1 (fr) * 1994-11-17 1996-05-22 L'oreal Nouveaux filtres solaires, compositions cosmétiques photoprotectrices les contenant et utilisations
WO1996035409A1 (fr) * 1995-05-12 1996-11-14 L'oreal Compositions cosmetiques pour la photoprotection de la peau et/ou des cheveux a base d'un melange synergique de filtres et utilisations
EP0860165A1 (fr) * 1997-02-24 1998-08-26 L'oreal Compositions cosmétiques pour la photoprotection de la peau et/ou des cheveux à base d'un mélange synergique de filtres
EP0979645A1 (fr) * 1998-07-16 2000-02-16 F. Hoffmann-La Roche Ag Composition de protection solaire contenant un agent anti UV-B de type polysiloxane et un agent anti UV-B de type benzimidazole
EP1133980A2 (fr) * 2000-03-15 2001-09-19 Basf Aktiengesellschaft Utilisation d'une combinaison d'agents photoprotecteurs comprenant en tant que composé essentiel des hydroxybenzophénones aminosubstituées comme filtres UV photostables dans des préparations cosmétiques et pharmaceutiques
WO2002049594A2 (fr) * 2000-12-18 2002-06-27 L'oreal Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2243465A1 (fr) * 2008-02-19 2010-10-27 Shiseido Company, Ltd. Produit cosmétique écran solaire du type émulsion eau-dans-huile
EP2243465A4 (fr) * 2008-02-19 2014-03-19 Shiseido Co Ltd Produit cosmétique écran solaire du type émulsion eau-dans-huile

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