Photostable cosmetic screening composition containing a UV-A screening agent and an alkyl .beta., .beta.-diphenylacrylate or .alpha.-cyano-.beta. , .beta.-diphenylacrylate

• US 5,587,150 A
• Filed: 06/05/1995
• Issued: 12/24/1996
• Est. Priority Date: 02/14/1990
• Status: Expired due to Term

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Dubois, Michel, Richard, Herve, Forestier, Serge, Deflandre, Andre
• Primary Examiner(s): Dodson, Shelley A.
• Application Number:
  US08/461,842
• Time in Patent Office: 568 Days
• Field of Search: 424/59, 514/685, 558/400, 560/57, 560/101, 568/304
• US Class Current: 424/59
• CPC Class Codes: A61K 2800/52 Stabilizers
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/40 containing nitrogen quinones containing nitrogen A61K8/355
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Abstract

A photostable cosmetic screening composition and process for protection of the human epidermis against UV rays of wavelengths between 280 and 380 nm, the composition having, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative and at least 1% by weight of an alkyl β-β-diphenylacrylate or α-cyano-β-β-diphenylacrylate of formula (I), the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

Claims

1. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative and at least 1% by weight of an alkyl β

, β

-diphenylacrylate or a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR2## in which R₁ and R'"'"'₁, which may be identical or different, represent a hydrogen atom, a straight- or branched-chain C₁ -C₈ alkoxy radical or a straight- or branched-chain C₁ -C₄ alkyl radical, R₁ and R'"'"'₁ being in the para or meta position;

R₂ represents a straight- or branched-chain C₁ -C₁₂ alkyl radical; and

R₃ represents hydrogen atom or a --CN radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

2. Cosmetic screening composition according to claim 1, wherein the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative is not more than 8.

3. Cosmetic screening composition according to claim 1, wherein the dibenzoylmethane derivative is selected from the group consisting of 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'"'"'-diisopropyldibenzoylmethane, 4-tert-butyl-4'"'"'-methoxydibenzoyl-methane, 2-methyl-5-isopropyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'"'"'-methoxydibenzoylmethane,2,4-dimethyl-4'"'"'-methoxy-dibenzoylmethane, and 2,6-dimethyl-4-tert-butyl-4'"'"'-methoxydi-benzoylmethane.

4. Cosmetic screening composition according to claim 1, wherein the dibenzoylmethane derivative is selected from the group consisting of 4-tert-butyl-4'"'"'methoxydibenzoylmethane and 4-isopropyldibenzoylmethane.

5. Cosmetic screening composition according to claim 1, wherein the alkyl β

,β

-diphenylacrylate or α

-cyano-β

,β

-diphenylacrylate is selected form the group consisting of ethyl α

cyano-β

,β

-diphenylacrylate, 2-ethylhexyl β

,β

-diphenylacrylate and ethyl β

,β

-bis(4-methoxyphenyl)acrylate.

6. Cosmetic screening composition according to claim 1, wherein the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative is between 1.2 and 8.

7. Cosmetic screening composition according to claim 1, which is in the form selected from the group consisting of oily and oleoalcoholic lotions, fatty and oleoalcoholic gels, solid sticks, emulsions, a vesicular dispersion of ionic or nonionic amphiphilic lipids, and aerosols.

8. Cosmetic screening composition according to claim 1, which contains, in addition, at least one cosmetic adjuvant selected from the group consisting of thickeners, emollients, humectants, surfactants, preservatives, antifoaming agents, fragrances, oils, waxes, lower monoalcohols, lower polyols, propellants, colorants and pigments.

9. Cosmetic screening composition according to claim 1, which constitutes an emulsion in the form of a cream or milk comprising, as a cosmetic vehicle, fatty alcohols, fatty acid, esters, and in particular fatty acid triglycerides, fatty acids, lanolin, natural or synthetic oils and waxes and emulsifiers, in the presence of water.

10. Cosmetic screening composition according to claim 1, in the form of an emulsion or a vesicular dispersion, which contains, in addition, water-soluble UV screening agents.

11. Cosmetic screening composition according to claim 1, which constitutes an oily lotion comprising, as a cosmetic vehicle, fatty acid esters, oils and natural or synthetic waxes.

12. Cosmetic screening composition according to claim 1, which constitutes an oleoalcoholic lotion comprising, as a cosmetic vehicle, oils, waxes or fatty acid esters, and in particular fatty acid triglycerides, and lower polyols, alcohols and/or glycols.

13. Cosmetic screening composition according to claim 1, which constitutes an oleoalcoholic gel comprising, as a cosmetic vehicle, a natural or synthetic oil or wax, a lower polyol or alcohol and a thickener.

14. Cosmetic screening composition according to claim 1, wherein the composition consists essentially of the cosmetically acceptable vehicle, the dibenzoylmethane derivative and the alkyl β

,β

-diphenylacrylate or α

-cyano-β

,β

-diphenylacrylate.

15. Process for protecting the human epidermis against UV radiation of wavelengths between 280 and 380 nm, which consists in applying to the skin an effective quantity of a cosmetic screening composition as defined in claim 1.

16. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative selected from the group consisting of 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyl-dibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'"'"'-diisopropyldibenzoylmethane, 2-methyl-5-isopropyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2,4-dimethyl-4'"'"'-methoxydibenzoylmethane and 2,6-dimethyl-4-tert-butyl-4'"'"'-methoxydibenzoylmethane and at least 1% by weight of an alkyl β

,β

-diphenylacrylate or a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR3## in which R₁ and R'"'"'₁, which may be identical or different, represent a hydrogen atom, a straight- or branched-chain C₁ -C₈ alkyl radical or a straight- or branched-chain C₁ -C₄ alkyl radical, R₁ and R'"'"'₁ being in the para or meta position;

R₂ represents a straight- or branched-chain C₁ -C₁₂ alkyl radical; and

R₃ represents a hydrogen atom or a --CN radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

17. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative selected from the group consisting of 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyl-dibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldi-benzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'"'"'-diisopropyldi-benzoylmethane, 4-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5isopropyl-4'"'"'-methoxydibenzoylmethane-2-methyl-5-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2,4-diemthyl-4'"'"'-methoxydibenzoylmethane and 2,6-dimethyl-4-tert-butyl-4'"'"'-methoxydibenzoylmethane and at least 1% by weight of an alkyl β

,β

-diphenylacrylate or a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR4## in which R₁ and R'"'"'₁, which may be identical or different, represent a hydrogen atom, a straight- or branched-chain C₁ -C₈ alkoxy radical or a straight- or branched-chain C₁ -C₄ alkyl radical, R₁ and R'"'"'₁ being in the para or meta position;

R₂ represents a straight- or branched-chain C₁ -C₁₂ alkyl radical; and

R₃ represents a hydrogen atom or a --CN radical, with the proviso that R₃ represents a hydrogen atom when R₁ and R'"'"'₁ represents a hydrogen atom and R₂ represents a 2-ethylhexyl radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

18. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative, said dibenzoylmethane derivative being selected from the group consisting of 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'"'"'-diisopropyldibenzoylmethane, 2-methyl-5-isopropyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2,4-diemthyl-4'"'"'-methoxydibenzoylmethane and 2,6-dimethyl-4-tert-butyl-4'"'"'-methoxydibenzoylmethane and at least 1% by weight of an acrylate selected from the group consisting of 2-ethylhexyl-α

-cyano-β

,β

-diphenylacrylate, ethyl α

-cyano-β

,β

-diphenylacrylate, 2-ethylhexyl β

,β

-diphenylacrylate and ethyl β

,β

-bis(4-methoxyphenyl)acrylate, the mole ratio of the acrylate to the dibenzoylmethane derivative being not less than 0.8.

19. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which consists essentially of a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative, said dibenzoylmethane derivative being selected from the group consisting of 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5-diemthyldibenzoylmethane, 4,4'"'"'-diisopropyldibenzoylmethane, 4-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5-isopropyl-4'"'"'-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'"'"'-methoxydibenzoylmethane, 2,4-dimethyl-4'"'"'-methoxydibenzoylmethane and 2,6-diemthyl-4-tert-butyl-4'"'"'-methoxydibenzoylmethane and at least 1% by weight of an acrylate selected from the group consisting of ethyl α

-cyano-β

,β

-diphenylacrylate, 2-ethylhexyl β

,β

-diphenylacrylate and ethyl β

,β

-bis(4-methoxyphenyl)acrylate, the mole ratio of the acrylate to the dibenzoylmethane derivative being not less than 0.8.

20. In an improved photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, a dibenzoylmethane derivative, wherein the improvement consists essentially of adding at least 1% by weight of an alkyl β

,β

-diphenylacrylate or a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR5## in which R₁ and R'"'"'₁ which may be identical or different, represent a hydrogen atom, a straight- or branched-chain C₁ -C₈ alkoxy radical or a straight- or branched-chain C₁ -C₄ alkyl radical, R₁ and R'"'"'₁ being in the para or meta position;

R₂ represents a straight- or branched-chain C₁ -C₁₂ alkyl radical; and

R₃ represents hydrogen atom or a --CN radical, to said cosmetically acceptable vehicle consisting essentially of 1 to 5% by weight of dibenzoylmethane derivative, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8, whereby the dibenzoylmethane derivative is stabilized against ultraviolet rays.

21. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which comprises, in a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative, said dibenzoylmethane derivative being 4-tert-butyl-4'"'"'-methoxydibenzoylmethane, and at least 1% by weight of a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR6## in which R₁ and R'"'"'₁ represent a hydrogen atom;

R₂ represents a 2-ethylhexyl radical; and

R₃ represents a --CN radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

22. Cosmetic screening composition according to claim 21, wherein the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative is not more than 8.

23. Cosmetic screening composition according to claim 21, wherein the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative is between 1.2 and 8.

24. Cosmetic screening composition according to claim 21, which is in the form of an oily or oleoalcoholic lotion or the form of a fatty or oleoalcoholic gel, of a solid stick, of an emulsion or of a vesicular dispersion of ionic or non-ionic amphiphilic lipids, or is packaged as an aerosol.

25. Cosmetic screening composition according to claim 21, which contains, in addition, cosmetic adjuvants selected from the group consisting of thickeners, emollients, humectants, sufactants, preservatives, antifoams, fragrances, oils, waxes, lower polyols and monohydric alcohols, propellants, colorings and pigments.

26. Cosmetic screening composition according to claim 21, which constitutes an emulsion in the form of a cream or milk comprising, as a cosmetic vehicle, fatty alcohols, fatty acid esters, and in particular fatty acid triglycerides, fatty acids, lanolin, natural or synthetic oils and waxes and emulsifiers, in the presence of water.

27. Cosmetic screening composition in the form of an emulsion or of a vesicular dispersion according to claim 21, which contains, in addition, water-soluble UV screening agents.

28. Cosmetic screening composition according to claim 21, which constitutes an oily lotion comprising, as a cosmetic vehicle, fatty acid esters, oils and natural or synthetic waxes.

29. Cosmetic screening composition according to claim 21, which constitutes an oleoalcoholic lotion comprising, as a cosmetic vehicle, oils, waxes or fatty acid esters, and in particular fatty acid triglycerides, and lower polyols, alcohols and/or glycols.

30. Cosmetic screening composition according to claim 21, which constitutes an oleoalcoholic gel comprising, as a cosmetic vehicle, a natural or synthetic oil or wax, a lower polyol or alcohol and a thickener.

31. Process for protecting the human epidermis against UV radiation of wavelengths between 280 and 380 nm, which consists in applying to the skin an effective quantity of a cosmetic screening composition as defined in claim 21.

32. A photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm, which consists essentially of a cosmetically acceptable vehicle containing at least one fatty phase, 1 to 5% by weight of a dibenzoylmethane derivative, said dibenzoylmethane derivative being 4-tert-butyl-4'"'"'-methoxydibenzoylmethane, and at least 1% by weight of a α

-cyano-β

,β

-diphenylacrylate of formula;

##STR7## in which R₁ and R'"'"'₁ represents a hydrogen atom;

R₂ represents a 2-ethylhexyl radical; and

R₃ represents a --CN radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.

33. In a photostable cosmetic screening composition for protection of the human epidermis against ultraviolet rays of wavelengths between 280 and 380 nm which consists essentially of a dibenzoylmethane derivative as a UV-A screen in combination with a UV-B screen in a cosmetically acceptable vehicle containing at least one fatty phase, wherein the improvement comprises increasing the protection of the skin against UV rays of wavelengths between 280 and 380 nm by using 1 to 5% by weight of a dibenzoylmethane derivative, said dibenzoylmethane derivative being 4-tert-butyl-4'"'"'-methoxydibenzoylmethane, and an effective amount of at least 1% by weight of a α

-cyano-β

,β

-diphenyl-acrylate of formula;

##STR8## in which R₁ and R'"'"'₁ represent a hydrogen atom;

R₂ represents a 2-ethylhexyl radical; and

R₃ represents a --CN radical, the mole ratio of the compound of formula (I) to the dibenzoylmethane derivative being not less than 0.8.