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Details for Patent: 4,663,088

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Details for Patent: 4,663,088

Title: 3-benzylidene-camphors, process for their preparation and their use in protection against UV rays
Abstract:The invention relates to new 3-benzylidene-camphor derivatives of the formula: ##STR1## in which R.sub.1 denotes H or SO.sub.3.sup..crclbar. M.sup..sym., with M=H, an alkali metal or N.sup..sym. (R.sub.3).sub.4, with R.sub.3 =H or C.sub.1 -C.sub.4 alkyl or hydroxyalkyl; R.sub.2 denotes C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and n=0-4; and Z denotes ##STR2## in which R.sub.4 has the same meaning as R.sub.1 and can be identical or different, or alternatively ##STR3## in which R.sub.5 denotes H, optionally substituted aryl, C.sub.1 -C.sub.4 alkyl, --CN, --COOR7 or ##STR4## and R.sub.6 denotes --COOR.sub.8 or ##STR5## in which R.sub.7 and R.sub.8, which are identical or different, denote alkyl, alkenyl, cycloalkyl or aralkyl and R.sub.9 and R.sub.10, which are identical or different, denote H, alkyl, alkenyl or cycloalkyl; if R.sub.5 =H, alkyl or aryl, R.sub.6 can represent --COO.sup..crclbar. M.sup..sym. ; the methylidene-camphor radical, on the one hand, and the radical Z, on the other hand, are in the meta or para position. These derivatives act as sun filters.
Inventor(s): Lang; Gerard (Saint Gratien, FR), Leduc; Madeleine (Paris, FR), Malaval; Alain (Aulnay-sous-Bois, FR)
Assignee: L'Oreal (Paris, FR)
Filing Date:Feb 04, 1986
Application Number:06/825,933
Claims:1. 3-Benzylidene-camphor derivative having the general formula: ##STR43## in which R.sub.1 denotes a hydrogen atom; R.sub.2 denotes a linear or branched C.sub.1 to C.sub.4 alkyl radical or a C.sub.1 to C.sub.4 alkoxy radical, n being 0 or an integer from 1 to 4 such that when n is 2 or more the R.sub.2 radicals can be the same or different; and Z represents a group of the formula: ##STR44## in which R.sub.4 is a hydrogen atom or the radical SO.sub.3.sup..crclbar. M.sup..sym., in which M is hydrogen, an alkali metal or the group N.sup..sym. (R.sub.3).sub.4, each R.sub.3 independently denoting hydrogen or a C.sub.1 to C.sub.4 alkyl or hydroxyalkyl group with the proviso that the methylidene-camphor radical and the radical Z, which are attached to the aromatic nucleus A, are either in the meta position or in the para position relative to one another.

2. A derivative according to claim 1 which has the formula ##STR45## in which R.sub.1 denotes a hydrogen atom and Z represents a group of the formula ##STR46## in the form of the free acid or the triethanolamine salt or ##STR47##

3. A derivative according to claim 1 which has the formula: ##STR48##

4. A derivative according to claim 1 which has the formula: ##STR49## in which Z represents a group of the formula ##STR50## in which R.sub.4 denotes a hydrogen atom or a group --SO.sub.3 H.

5. Process for the preparation of a compound as claimed in claim 1 in which Z represents a group: ##STR51## which comprises reacting by heating under reflux a compound of the formula ##STR52## in which R.sub.2 is as defined in claim 1, with a compound of of the formula: ##STR53## in either anhydrous solvent, in the presence of an organic or inorganic base, the water formed being removed, or alternatively, in a water-immiscible solvent, in the presence of an aqueous solution of sodium hydroxide or potassium hydroxide.

6. Process for the preparation of a compound as claimed in claim 1 in which Z represents a group: ##STR54## wherein R.sub.4 is equal to R.sub.1 and which comprises reacting by heating under reflux one mole of a compound of the formula: ##STR55## in which R.sub.2 is as defined in claim 1, with two mols of a compound of the formula: ##STR56## in either an anhydrous solvent, in the presence of an organic or inorganic base, the water formed being removed, or, alternatively, in a water-immiscible solvent, in the presence of an aqueous solution of sodium hydroxide or potassium hydroxide.

7. A composition suitable for cosmetic use which contains at least one 3-benzylidene-camphor derivative as defined in claim 1.

8. A composition, which contains at least one derivative as claimed in claim 2.

9. A composition according to claim 7, in which the derivative is present in an amount from 0.5 to 15% by weight, relative to the total weight of the composition.

10. A composition according to claim 7, which contains at least one cosmetic adjuvant which is a thickener, softener, superfatting agent, emollient, humectant, wetting agent, surface-active agent, preservative, anti-foam agent, perfume, oil, wax, dyestuff or pigment.

11. A composition according to claim 7, which is in the form of an anti-sunburn composition and contains at least one derivative as claimed in claim 1 associated with another water-soluble or liposoluble sun filter having a filtering action with respect to UV-B rays, or with another sun filter which filters out the UV-A rays.

12. A composition according to claim 11 in which the said sun filter having a filtering action with respect to UV-B rays is a camphor derivative, coffee bean oil, salicylic acid derivative, cinnamic acid derivative, p-aminobenzoic acid derivative or benzophenone derivative.

13. A composition according to claim 11 in which the said sun filter which filters out UV-A rays is a dibenzoylmethane derivative.

14. A composition according to claim 7, which is in the form of a coloured or non-coloured cosmetic composition stabilised to light and is a hair lacquer, a setting lotion, a shampoo, a colouring shampoo or a hair dyeing composition, a nail varnish, a lipstick, an epidermis treatment cream or a make-up foundation.

15. Process for protecting the human epidermis against UV-A and/or UV-B rays, which comprises applying thereto at least one derivative as defined in claim 1.

16. Process for protecting a coloured cosmetic composition against UV radiation, which comprises incorporating therein at least one derivative as defined in claim 1.
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