Solubilization of triazine UV-screening agents with arylalkyl benzoate compounds/amide-based oils and photoprotective compositions comprised thereof

• US 20060002872A1
• Filed: 07/05/2005
• Published: 01/05/2006
• Est. Priority Date: 07/02/2004
• Status: Active Grant

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Candau, Didier, Fiandino, Cecile
• Granted Patent: US 9,717,931 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/44 Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• CPC Class Codes: A61K 8/4966 Triazines or their condensed derivatives
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Abstract

Topcially applicable photoprotective compositions having improved sun protection factor, cosmetic properties and/or stability contain: (a) at least one 1,3,5-triazine UV-screening agent, (b) at least one mixture including: (i) at least one arylalkyl benzoate compound, and (ii) at least one oil containing in its structure at least one amide unit.

Claims

1. A topically applicable cosmetic/dermatological photoprotective composition, comprising an effective UV-photoprotecting amount of at least one 1,3,5-triazine UV-screening agent and, as a solubilizing admixture therefor, a thus effective amount of at least one arylalkyl benzoate compound and at least one amide-based oil, formulated into a topically applicable, cosmetically/dermatologically acceptable medium.

2. The cosmetic/dermatological composition as defined by claim 1, said at least one amide-based oil having the formula (1) below:

3. The cosmetic/dermatological composition as defined by claim 2, wherein formula (1):

R¹ is a linear or branched C₁-C₂₂ alkyl radical, a linear or branched C₂-C₂₂ alkenyl radical, or an aryl radical;

R² is a hydrogen atom or a linear or branched C₁-C₆ alkyl radical;

R³ is a hydrogen atom or a linear or branched C₁-C₆ alkyl radical;

R⁴ is a linear or branched C₁-C₁₀ alkyl radical or a linear or branched C₂-C₁₀ alkenyl radical, or a sterol residue.

4. The cosmetic/dermatological composition as defined by claim 3, said at least one amide-based oil of formula (1) comprising ethyl N-acetyl-N-butylaminopropionate, having the following formula:

5. The cosmetic/dermatological composition as defined by claim 1, said at least one amide-based oil comprising from 0.1% to 40% by weight thereof.

6. The cosmetic/dermatological composition as defined by claim 1, said at least one arylalkyl benzoate compound being selected from among those of formula (2) or (3) below:

7. The cosmetic/dermatological composition as defined by claim 6, said at least one arylalkyl benzoate compound comprising 2-phenylethyl benzoate of formula:

8. The cosmetic/dermatological composition as defined by claim 1, said at least one arylalkyl benzoate compound comprising from 0.1% to 40% by weight thereof.

9. The cosmetic/dermatological composition as defined by claim 1, said at least one 1,3,5-triazine UV-screening agent having the formula (I) below:

10. The cosmetic/dermatological composition as defined by claim 9, in which the at least one 1,3,5-triazine UV-screening agent of formula (I), A₁, A₂ and A₃ are of formula (II) and have all of the following definitions:

one of the groups X_a-R_a is a radical —

NH—

R_a wherein R_a is a C₅-C₁₂ cycloalkyl radical optionally substituted with one or more C₁-C₄ alkyl radicals, or a radical of formula (X), (XI) or (XII) above in which;

B is a C₁-C₄ alkyl radical;

R₉ is a methyl radical;

the other two groups X_a-R_a is a radical —

O—

R_a wherein the radicals R_a, which may be identical or different, are each hydrogen, an alkali metal, an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals, a linear or branched C₁-C₁₈ alkyl radical, a C₅-C₁₂ cycloalkyl radical optionally substituted with one or more C₁-C₄ alkyl radicals, or a radical of formula (X), (XI) or (XII) above in which;

B is a C₁-C₄ alkyl radical;

R₉ is a methyl radical.

11. The cosmetic/dermatological composition as defined by claim 9, in which the at least one 1,3,5-triazine UV-screening agent of formula (I), A₁, A₂ and A₃ are of formula (II) and have all of the following definitions:

one or two groups X_a-R_a is a radical —

NH—

R_a, wherein R_a is a linear or branched C₁-C₁₈ alkyl radical, a C₅-C₁₂ cycloalkyl radical optionally substituted with one or more C₁-C₄ alkyl radicals, or a radical of formula (X), (XI) or (XII) above in which;

B is a C₁-C₄ alkyl radical;

R₉ is a methyl radical;

the other or the other two group(s) X_a-R_a being a radical —

O—

R_a wherein R_a, which may be identical or different, are each hydrogen, an alkali metal, an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals, a linear or branched C₁-C₁₈ alkyl radical, a C₅-C₁₂ cycloalkyl radical optionally substituted with one or more C₁-C₄ alkyl radicals, or a radical of formula (X), (XI) or (XII) above in which;

B is a C₁-C₄ alkyl radical;

R₉ is a methyl radical.

12. The cosmetic/dermatological composition as defined by claim 11, said at least one 1,3,5-triazine UV-screening agent comprising 2-[(p-(tert-butylamido)anilino]4,6-bis[(p-(2′

-ethylhexyl-1′

-oxycarbonyl)anilino]-1,3,5-triazine having the following formula;

13. The cosmetic/dermatological composition as defined by claim 9, said at least one 1,3,5-triazine UV-screening agent having the formula (I) in which A₁, A₂ and A₃ are of formula (II) and have all of the following definitions:

X_a are identical and represent oxygen;

R_a, which may be identical or different, are each a C₆-C₁₂ alkyl radical or a polyoxyethylenated radical having from 1 to 6 ethylene oxide units, the terminal OH group of which is methylated.

14. The cosmetic/dermatological composition as defined by claim 13, said at least one 1,3,5-triazine UV-screening agent comprising 2,4,6-tris[p(2′

-ethylhexyl-1′

-oxycarbonyl)anilino]-1,3,5-triazine of the following formula;

15. The cosmetic/dermatological composition as defined by claim 9, said at least one 1,3,5-triazine UV-screening agent having formula (I) in which A₁ and A₂ are of formula (III) and A₃ is of formula (IX) and have all of the following definitions:

R₁, which may be identical or different, are each a C₃-C₁₈ alkyl radical, a C₂-C₁₈ alkenyl radical or a residue of formula —

CH₂—

CH(OH)—

CH₂—

OT₁ in which T₁ is a hydrogen atom or a C₁-C₈ alkyl radical; and

R₇ is a hydrogen atom or a C₁-C₁₀ alkyl radical.

16. The cosmetic/dermatological composition as defined by claim 15, said at least one 1,3,5-triazine UV-screening agent comprising 2,4-bis{[4-2-ethylhexyloxy)]-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine of the following formula:

17. The cosmetic/dermatological composition as defined by claim 9, said at least one 1,3,5-triazine UV-screening agent having formula (I) in which A₁, A₂ and A₃ are of formulae (VII) to (XI).

18. The cosmetic/dermatological composition as defined by claim 1, said at least one 1,3,5-triazine UV-screening agent being selected from the group consisting of:

2,4,6-tris(diisobutyl 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(bis(2-ethylhexyl) 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(bis(2-ethylhexyl) 4′

-aminobenzalmalonate)-6-chloro-s-triazine,

2,4,6-tris(bis(2-ethylhexyl) 4′

-aminobenzalmalonate)-6-(2-ethylhexyl 4′

-aminobenzoate)-s-triazine,

2,4,6-tris(diisobutyl 4′

-aminobenzalmalonate)-6-butoxy-s-triazine,

2,4,6-tris(diisobutyl 4′

-aminobenzalmalonate)-6-(2-ethylhexylamino)-s-triazine,

2,4-bis(4′

-aminobenzylidenecamphor)-6-(2-ethylhexylamino)-s-triazine,

2,4-bis(4′

-aminobenzylidenecamphor)-6-(diisobutyl 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(diethyl 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(diisopropyl 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(dimethyl 4′

-aminobenzalmalonate)-s-triazine,

2,4,6-tris(ethyl α

-cyano-4-aminocinnamate)-s-triazine,

2,4,6-tris[(3′

-benzotriazol-2-yl-2′

-hydroxy-5′

-methyl)phenylamino]-s-triazine, and

2,4,6-tris[(3′

-benzotriazol-2-yl-2′

-hydroxy-5-tert-octyl)phenylamino]-s-triazine.

19. The cosmetic/dermatological composition as defined by claim 1, said at least one 1,3,5-triazine UV-screening agent comprising from 0.05% to 15% by weight thereof.

20. The cosmetic/dermatological composition as defined by claim 1, further comprising at least one additional organic photoprotective agent and/or at least one additional mineral photoprotective agent, which is/are water-soluble, liposoluble or insoluble in the cosmetic solvents commonly employed.

21. The cosmetic/dermatological composition as defined by claim 20, comprising at least one additional organic photoprotective agent selected from among anthranilates;

cinnamic derivatives;

salicylic derivatives;

camphor derivatives;

benzophenone derivatives;

β

,β

′

-diphenylacrylate derivatives;

benzotriazole derivatives;

benzalmalonate derivatives;

benzimidazole derivatives;

imidazolines;

bis-benzazolyl derivatives;

p-aminobenzoic acid (PABA) derivatives;

methylenebis(hydroxyphenylbenzotriazole) derivatives;

benzoxazole derivatives;

screening polymers and screening silicones;

dimers derived from α

-alkylstyrene;

4,4-diarylbutadienes, and mixtures thereof.

22. The cosmetic/dermatological composition as defined by claim 21, comprising at least one additional organic photoprotective agent selected from among:

Homosalate,

Ethylhexyl salicylate,

Ethylhexyl methoxycinnamate,

Octocrylene,

Phenylbenzimidazolesulfonic acid,

Benzophenone-3,

Benzophenone-4,

Benzophenone-5,

n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate,

4-Methylbenzylidenecamphor,

Terephthalylidenedicamphorsulfonic acid,

Disodium phenyldibenzimidazoletetrasulfonate,

Methylenebis(benzotriazolyl)tetramethylbutylphenol,

Drometrizole trisiloxane,

Polysilicone-15,

1,1-Dicarboxy(2,2′

-dimethylpropyl)4,4-diphenylbutadiene,

2,4-Bis[5-1(dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine,

and mixtures thereof.

23. The cosmetic/dermatological composition as defined by claim 20, comprising at least one additional mineral photoprotective agent selected from among coated or uncoated metal oxide pigments or nanopigments.

24. The cosmetic/dermatological composition as defined by claim 20, comprising at least one additional mineral screening agent selected from among nanopigments of titanium oxide, which is amorphous or crystallized in rutile and/or anatase form, or of iron oxide, zinc oxide, zirconium oxide or cerium oxide.

25. The cosmetic/dermatological composition as defined by claim 1, further comprising at least one agent for artificially tanning and/or browning the skin.

26. The cosmetic/dermatological composition as defined by claim 1, further comprising at least one adjuvant selected from among fatty substances, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants and acidifying or basifying agents.

27. The cosmetic/dermatological composition as defined by claim 1, said amide-based oil/arylalkyl benzoate compound admixture being present in an amount that itself is sufficient for dissolving all of the triazine screening agent present in the composition.

28. A regime or regimen for cosmetically treating or caring for the skin, lips, nails, hair, eyelashes, eyebrows and/or scalp of an individual in need of such treatment, comprising topically applying thereon, a thus effective amount of the cosmetic/dermatological composition as defined by claim 1.

29. A regime or regimen for photoprotecting the skin, hair, lips and/or scalp against the damaging effects of UV-irradiation, comprising topically applying thereon, a thus effective amount of the cosmetic/dermatological composition as defined by claim 1.

31. The cosmetic/dermatological composition as defined by claim 1, formulated as an emulsion, a milk, a gel, a cream, a lotion, a powder, a stick, a mousse, or a spray.

30. A process for enhancing the sun protection factor, cosmetic properties and/or stability of at least one 1,3,5-triazine UV-screening agent, comprising formulating therewith a thus effective amount of at least one arylalkyl benzoate compound and at least one amide-based oil.