|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)|
1. 3-Benzylidene-camphor derivative having the general formula: ##STR38## in which R.sub.1 denotes 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; 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 O 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: ##STR39## in which R.sub.4 is as defined under R.sub.1, 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 ##STR40## in which R.sub.1 denotes a group--SO.sub.3 H and Z denotes a group ##STR41## in the form of the free diacid or the sodium or triethanolamine disulphonate.
3. Process for the preparation of a compound as claimed in claim 1 in which Z represents a group: ##STR42## which comprises reacting by heating under reflux a compound of the formula ##STR43## in which R.sub.2 is as defined in claim 1, with a compound of the formula: ##STR44## 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.
4. Process for the preparation of a compound as claimed in claim 1 in which Z represents a group: ##STR45## which comprises reacting by heating under reflux one mol of a compound of the formula: ##STR46## in which R.sub.2 is as defined in claim 1, with two mols of a compound of the formula: ##STR47## 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.
5. A composition suitable for cosmetic use which contains at least one 3-benzylidene-camphor derivative as defined in claim 1.
6. A composition which contains at least one derivative as claimed in claim 2.
7. A composition according to claim 5, in which the derivative is present in an amount from 0.5 to 15% by weight, relative to the total weight of the composition.
8. A composition according to claim 5, 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.
9. A composition according to claim 5, 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.
10. A composition according to claim 9 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.
11. A composition according to claim 9 in which the said sun filter which filters out UV-A rays is a dibenzoylmethane derivative.
12. A composition according to claim 5, 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.
13. 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.
14. Process for protecting a coloured cosmetic composition against UV radiation, which comprises incorporating therein at least one derivative as defined in claim 1.
Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.