L'oreal

Societe Anonyme Dite: L'oreal

Charles Vayssie

Claude Bouillon

Francoise Richard

Alex M Junino

Gregoire Kalopissis

Daniel P Bauer

A process for dyeing keratinous fibers comprises a two-step operation in which in the first step the fibers are contacted with an indole dye in a medium suitable for dyeing the fibers, the medium being free from any oxidation catalyst and oxidation catalyst. Thereafter, in the second step the fibers are contacted with a para type oxidation dye precursor in a medium which is also suitable for dyeing the fibers and is free from any oxidation catalyst and oxidation agent. A multi-compartment kit housing the indole dye and para type oxidation dye precursor is also provided.

Dyeing process employing indole dyes and oxidation dye precursors and

The invention provides compounds which are particularly valuable for use as the active ingredient in sun tan lotions and creams and the like. These compounds have the general formula: ##STR1## in which Y denotes hydrogen or the radical SO.sub.3 H or a salt thereof with an organic or inorganic base, and Z denotes the radical --CH.sub.2 Br or --CHBrBr or a radical Z' which denotes the radical --CH.sub.2 I, --CH.sub.2 R, --CHR'R', --CHO or --COOR', in which R denotes --NR.sub.1 R.sub.2, --N.sup.+ R.sub.1 R.sub.2 R.sub.3, --OR.sub.4, --OCOR.sub.5, --SR.sub.6, --CN, -COOR' or --SSO.sub.3 Na, in which R.sub.1 and R.sub.2 independently denote hydrogen, C.sub.1-18 alkyl or hydroxyalkyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, denote a heterocyclic ring, R.sub.3 denotes C.sub.1-4 alkyl or hydroxyalkyl or sulphonatopropyl, R.sub.4 denotes hydrogen, alkyl, polyoxyethylene, aryl which is optionally substituted, menthyl or dialkylaminoalkyl, R.sub.5 denotes alkyl, alkenyl, aryl or a 5 or 6 membered heterocyclic ring which is optionally aromatic, and R.sub.6 denotes hydrogen, alkyl, carboxyalkyl, aminoalkyl, hydroxyalkyl, aryl or 3-alanyl, R' denotes --OR'.sub.4 or --SR'.sub.6, in which R'.sub.4 and R'.sub.6 are as defined under R.sub.4 and R.sub.6, respectively, except for hydrogen, polyoxyethylene, hydroxyalkyl, 3-alanyl and aryl, and R' denotes hydrogen or alkyl, such that when R denotes N.sup.+ R.sub.1 R.sub.2 R.sub.3, R.sub.1 and R.sub.2 are not hydrogen and either R.sub.3 denotes sulphonatopropyl, or the compound is in the form of a salt with an anion, which is SO.sub.4 alkyl, SO.sub.3 aryl, SO.sub.3 alkyl or halogen or an inorganic or organic acid addition salt thereof when R denotes --NR.sub.1 R.sub.2.

Benzylidene-camphors, processes for their preparation and cosmetic

The invention relates to oxybenzylidene-bornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical ##STR2## in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an amino-aliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.1 is a divalent radical, and, if R.sub.1 denotes hydrogen, R.sub.2 also denotes hydrogen. These compounds can be used in cosmetic compositions for providing protection against actinic rays.

Oxybenzylidene-bornanones, their preparation and their use in cosmetics

An anti-solar cosmetic composition contains as the anti-solar agent a compound of the formula ##STR1## wherein R represents a member selected from the group consisting of hydrogen, a halogen selected from the group consisting of chlorine and fluorine and alkyl containing 1-4 carbon atoms; R' and R' each independently represent a member selected from the group consisting of hydrogen and SO.sub.3 M wherein M represents a member selected from the group consisting of hydrogen, organic ammonium group and a metal, wherein at least one of R' and R' is other than hydrogen, and R' is a substituent at the para or meta position relative to the bornylidene ring. The anti-solar agent is present in amounts of 0.5-10 percent by weight of said composition.

Process of preparing 3-benzylidene-2-oxo-10-bomanesulfonic acid

Anti-solar cosmetic composition

4-(2-Oxo-3-bornylidene methyl) benzene sulfonic acid and salts thereof

The invention relates to oxybenzylidenebornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical --(CH.sub.2 CH.sub.2 O).sub.n H, ##STR2## --(CH.sub.2).sub.m CO.sub.2 R, in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an aminoaliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.1 is a divalent radical, and, if R.sub.1 denotes hydrogen, R.sub.2 also denotes hydrogen. These compounds can be used in cosmetic compositions for providing protection against actinic rays.

Process for preparing (2-oxo-3-bornylidene/methyl)-benzene sulfonic acids

(2-Oxo-3-bornylidene methyl)-benzene sulfonates and derivatives thereof

A method and composition for combatting the greasy and unaesthetic appearance of the hair and to improve the appearance of the skin comprises in a carrier at least one active component of the formula ##STR1## wherein R.sub.1 and R.sub.2 are methyl, ethyl, isopropyl, cyclohexyl, benzyl or .beta.-hydroxyethyl, or R.sub.1 and R.sub.2 taken together form --(CH.sub.2).sub.2 --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --CH.sub.2 --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --, ##STR2## and R is (i) linear or branched alkyl having 1-18 carbon atoms, (ii) alkenyl having 3-18 carbon atoms, (iii) alkyl having 2-3 carbon atoms and substituted by 1-2 alcohol functions, (iv) --(CH.sub.2).sub.m --CH(OR.sub.3).sub.2 wherein R.sub.3 is alkyl having 1-4 carbon atoms and m is 1-2, (v) --(CH.sub.2).sub.n R.sub.4 wherein n is 0, 1 or 2 and R.sub.4 is 2-pyridyl or phenyl, (vi) --(CH.sub.2).sub.q R'.sub.4 wherein q is 0 or 1 and R'.sub.4 is 1-naphthyl, 2-naphthyl ##STR3## WHEREIN P IS 1, 2 OR 3 IN WHICH INSTANCE R.sub.5 is F, Cl, Br, alkoxy having 1-5 carbon atoms or alkyl having 1-4 carbon atoms, or wherein p is 1 in which instance R.sub.5 is amino, dimethylamino and methylenedioxy, (vii) --CH(C.sub.6 H.sub.5).sub.2, (viii) --C(C.sub.6 H.sub.5).sub.3, (ix) --CH(C.sub.6 H.sub.4 p--OCH.sub.3).sub.2, ##STR4## (xi) --CH.sub.2 --CH.sub.2 --NH--Y wherein Y is hydrogen, nicotinyl or COR.sub.9 wherein R.sub.9 is hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 2-18 carbon atoms ##STR5## wherein R.sub.11 is H, F, Cl, Br or alkoxy having 1-4 carbon atoms, ##STR6## and (xiii) --(CH.sub.2).sub.s --COOH wherein s is 1-10.

Hydroxylated amine thioethers for improving the greasy and unaesthetic

An anti-solar cosmetic composition contains as the anti-solar agent a compound of the formula ##STR1## wherein R is hydrogen or alkyl containing 1-12 carbon atoms, Y is hydrogen, methyl or halogen and X is halide, arylsulfonate, alkylsulfonate, camphosulfonate or alkyl sulfate. The antisolar agent is present in amounts of 0.05-10 percent by weight of said composition.

Anti-solar agent and compositions containing the same

A method and composition for combatting the greasy and unaesthetic appearance of the hair and to improve the appearance of the skin comprises in a carrier at least one active component of the formula ##EQU1## wherein R.sub.1 and R.sub.2 are methyl, ethyl, isopropyl, cyclohexyl, benzyl or .beta.-hydroxyethyl, or R.sub.1 and R.sub.2 taken together form --(CH.sub.2).sub.2 --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --CH.sub.2 --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --, ##EQU2## or ##EQU3## ; and R is (1) linear or branched alkyl having 1-18 carbon atoms, (ii) alkenyl having 3-18 carbon atoms, (iii) alkyl having 2-3 carbon atoms and substituted by 1-2 alcohol functions, (iv) --(CH.sub.2).sub.m --CH(OR.sub.3).sub.2 wherein R.sub.3 is alkyl having 1-4 carbon atoms and m is 1-2, (v) --(CH.sub.2).sub.n R.sub.4 wherein n is 0, 1 or 2 and R.sub.4 is 2 -pyridyl or phenyl, (vi) --(CH.sub.2).sub.q R'.sub.4 wherein q is 0 or 1 and R'.sub.4 is 1-naphthyl, 2-naphthyl ##SPC1## Wherein p is 1, 2 or 3 in which instance R.sub.5 is F, Cl, Br, alkoxy having 1-5 carbon atoms or alkyl having 1-4 carbon atoms, or wherein p is 1 in which instance R.sub.5 is amino, dimethylamino and methylenedioxy, (vii) --CH(C.sub.6 H.sub.5).sub.2, (viii) --C(C.sub.6 H.sub.5).sub.3, (ix) --CH(C.sub.6 H.sub.4 p--OCH.sub.3).sub.2, (x) ##EQU4## (xi) --CH.sub.2 --CH.sub.2 --NH--Y wherein Y is hydrogen, nicotinyl or COR.sub.9 wherein R.sub.9 is hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 2-18 carbon atoms ##SPC2## Wherein R.sub.11 is H, F, Cl, Br or alkoxy having 1-4 carbon atoms, (xii) ##EQU5## and (xiii) --(CH.sub.2).sub.s --COOH wherein s is 1-10.

Growing community of inventors

Aulnay-sous-Bois, France

Charles Vayssie