Hair dye compositions and new compounds useful therein

Claim 2

A dye composition for human hair comprising an aqueous or water-alcohol solution, having a pH between 3 and 11.5, of 0.001 to 5% by weight of at least one compound of the formula ##STR69## wherein Z is lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1-6 carbon atoms and R and R' are lower alkyl having 1-6 carbon atoms, each of R 1 and R 2 is H or lower alkyl having 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring.

Claim 3

The dye composition according to claim 1, wherein said pH is between 3 and 10.5.

Claim 4

The dye composition according to claim 1, wherein said compound is present in an amount ranging between 0.05 to 5% by weight of said composition.

Claim 5

The dye composition according to claim 1, which further includes at least one direct dye which is an azo dye, an anthraquinone dye, a nitro benzene dye, an indoaniline, an indophenol or an indamine.

Claim 6

The dye composition according to claim 1, wherein said alcohol is present in an amount of from 20 to 75% by weight of the composition and is a lower alcohol of from 1 to 4 carbon atoms.

Claim 7

The dye composition according to claim 5, wherein the alcohol is ethanol or isopropanol.

Claim 8

A dyeing composition of claim 5, and further including a cosmetic resin, which is present in an amount of between 1 to 3% by weight of said lotion, and is polyvinylpyrrolidone, a copolymer of crotonic acid and vinyl acetate, a copolymer of vinylpyrrolidone and vinyl acetate; a copolymer of methyl vinyl ether and maleic anhydride; a copolymer of the ethyl, isopropyl or butyl ester of maleic anhydride and methyl vinyl ether; or a copolymer of maleic anhydride-butyl vinyl ether.

Claim 9

The composition of claim 7, wherein said cosmetic resin is present in an amount ranging between 1 to 2% by weight of said lotion.

Claim 10

The composition of claim 5, wherein said alcohol is present in an amount ranging from between 25 to 50% by weight of the dye composition.

Claim 11

A process for dyeing human hair, comprising contacting the hair with an effective amount of a composition comprising an aqueous or water-alcohol solution, having a pH between 3 and 11.5, of 0.001 to 5% by weight of said composition, of at least one compound of the formula ##STR70## wherein Z is lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1-6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, each of R 1 and R 2 is H, lower alkyl having 1 to 6 carbon atoms the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring; for a period ranging between 5 and 25 minutes; rinsing the hair and drying said hair.

Claim 12

A process for dyeing human hair, comprising contacting the hair with an effective amount of a composition comprising an aqueous or water-alcohol solution, having a pH between 3 and 11.5, of 0.001 to 5% by weight of said composition, of at least one compound of the formula ##STR70## wherein Z is lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1-6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, each of R 1 and R 2 is H, lower alkyl having 1 to 6 carbon atoms the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring; for a period ranging between 5 and 25 minutes; rinsing the hair and drying said hair.

Claim 13

A process for dyeing human hair, comprising applying to washed and rinsed hair, an effective amount of a dyeing composition comprising a water-alcohol solution, having a pH between 3 and 11.5, of 0.001 to 5% by weight of at least one compound of the formula ##STR71## wherein Z is lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, each of R 1 and R 2 is H, lower alkyl having 1 to 6 carbon atoms, the --NO 2 substitutent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring; wherein said alcohol is present in an amount from 20 to 25% by weight of the composition and is a lower alcohol having from 1 to 4 carbon atoms; said water-alcohol solution containing 1 to 3% by weight of a cosmetic resin selected from polyvinylpyrrolidone, a copolymer of crotonic acid and vinyl acetate; a copolymer of vinylpyrrolidone and vinyl acetate; a copolymer of methyl vinyl ether and maleic anhydride; a copolymer of the ethyl, isopropyl or butyl ester of maleic anhydride with methyl vinyl ether; or a copolymer of maleic anhydride and butyl vinyl ether; setting the hair, and drying said hair.

Claim 14

A process for dyeing human hair, comprising applying to washed and rinsed hair, an effective amount of a dyeing composition comprising a water-alcohol solution, having a pH between 3 and 11.5, of 0.001 to 5% by weight of at least one compound of the formula ##STR71## wherein Z is lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, each of R 1 and R 2 is H, lower alkyl having 1 to 6 carbon atoms, the --NO 2 substitutent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring; wherein said alcohol is present in an amount from 20 to 25% by weight of the composition and is a lower alcohol having from 1 to 4 carbon atoms; said water-alcohol solution containing 1 to 3% by weight of a cosmetic resin selected from polyvinylpyrrolidone, a copolymer of crotonic acid and vinyl acetate; a copolymer of vinylpyrrolidone and vinyl acetate; a copolymer of methyl vinyl ether and maleic anhydride; a copolymer of the ethyl, isopropyl or butyl ester of maleic anhydride with methyl vinyl ether; or a copolymer of maleic anhydride and butyl vinyl ether; setting the hair, and drying said hair.

Claim 15

Dye composition for human hair which contains in aqueous or water-alcohol solution, with a pH between 3 and 11.5, 0.001 to 5% by weight of at least one compound of the formula ##STR72## wherein Z represents a substituted lower alkyl radical selected from the group consisting of carbalkoxyaminoalkyl, alkoxyalkyl, N,N-dialkylcarbamylalkyl, acylaminoalkyl, ureidoalkyl, mesylaminoalkyl and ##STR73## group, n being a whole number between 1 and 6 and X.sup.⊖ is an anionic residue, and each of R 1 and R 2 is hydrogen, lower alkyl having 1 to 6 carbon atoms or lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring.

Claim 16

Dye composition for human hair which contains in aqueous or water-alcohol solution, with a pH between 3 and 11.5, 0.001 to 5% by weight of at least one compound of the formula ##STR72## wherein Z represents a substituted lower alkyl radical selected from the group consisting of carbalkoxyaminoalkyl, alkoxyalkyl, N,N-dialkylcarbamylalkyl, acylaminoalkyl, ureidoalkyl, mesylaminoalkyl and ##STR73## group, n being a whole number between 1 and 6 and X.sup.⊖ is an anionic residue, and each of R 1 and R 2 is hydrogen, lower alkyl having 1 to 6 carbon atoms or lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring.

Claim 17

Dye composition according to claim 12, characterized by the fact that in the compounds of formula (I'), R 1 and R 2 , identical or different, are selected from the group consisting of hydroxyalkyl, aminoalkyl, carbamylalkyl and carboxyalkyl.

Claim 18

Composition according to claim 12, characterized by the fact that it contains other direct dyes.

Claim 19

Composition according to claim 14, characterized by the fact that it contains azo dyes, anthraquinone dyes, nitro dyes of the benzene series, indoanilines, indophenols or indamines.

Claim 20

Composition according to claim 12, characterized by the fact that it contains from 20 to 75% by weight of a lower aliphatic alcohol comprising 1 to 4 carbon atoms.

Claim 21

Composition according to claim 16, characterized by the fact that the alcohol is ethanol or isopropanol.

Claim 22

Composition according to claim 16 which also contains a cosmetic resin in a proportion of 1 to 3% by weight, and 20 to 75% by weight of a lower aliphatic alcohol having 1 to 4 carbon atoms.

Claim 23

Composition according to claim 18, characterized by the fact that the cosmetic resin which it contains is polyvinylpyrrolidone, a crotonic acid-vinyl acetate or vinylpyrrolidone-vinyl acetate copolymer, a methyl vinyl ether-maleic anhydride and its ethyl, isopropyl and butyl copolymer and maleic anhydride-butyl vinyl ether copolymer.

Claim 24

Composition according to claim 12, characterized by the fact that it also contains at least one or both of an oxidation base and a coupler.

Claim 25

Dye composition according to claim 20, characterized by the fact that the oxidation base is selected from the group consisting of a paraphenylene diamine, a para aminophenol and a pyridine derivative.

Claim 26

Dye composition according to claim 21, characterized by the fact that the paraphenylene diamine is a primary, secondary or tertiary amine of the formula ##STR74## wherein R 11 and R 12 can be identical or different and can signify hydrogen, a lower branched or straight line alkyl group, mono or polyhydroxyl alkylene, piperidinoalkyl, carbamylalkyl, morpholinoalkyl, acylaminoalkyl, mesyaminoalkyl, sulfoalkyl, sulfonamidoalkyl groups in which the alkyl radical comprises 1 to 4 carbon atoms, R 11 and R 12 also being able to form together a heterocyclic group with five or six groupings, R 13 , R 14 , R 15 and R 16 can signify independently of one another a a hydrogen atom or halogen atom, a lower alkyl or lower alkoxy group, comprising 1 to 4 carbon atoms.

Claim 27

Dye composition according to claim 21, characterized by the fact that the paraphenylene diamine is selected from the group consisting of paraphenylene diamine, paratoluylene diamine, methoxy paraphenylene diamine, chloroparaphenylene diamine, 2,6-dimethyl paraphenylene diamine, 2,5-dimethyl paraphenylene diamine, 2-methyl 5-methoxy paraphenylene diamine, 2,6-dimethyl 5-methoxy paraphenylene diamine, N,N-dimethyl paraphenylene diamine, 3-methyl 4-amino N,N-(diethyl) aniline, N,N-diβ-hydroxyethyl)paraphenylene diamine, 3-methyl 4-amino N,N-(diβ-hydroxyethyl) aniline, 3-chloro 4-amino N,N-(di-β-hydroxyethyl) aniline, 4-amino N,N-(ethyl, carbamylethyl) aniline, 3-methyl 4-amino N,N-(ethyl, carbamethyl) aniline, 4-amino N,N(ethyl, piperidinoethyl) aniline, 4-amino N,N-(ethyl, morpholinoethyl)aniline, 3-methyl 4-amino N,N-(ethyl, morpholinoethyl) aniline, 4-amino N,N-(ethyl, acetylaminoethyl) aniline, 3-methyl 4-amino N,N-(ethyl, acetylaminoethyl) aniline, 4-amino N,N-(ethyl, mesylaminoethyl) aniline, 2-methyl 4-amino N,N-(ethyl, mesylaminoethyl) aniline, 4-amino N,N-(ethyl, β-sulfoethyl) aniline, 3-methyl 4-amino N,N-(ethyl, β-sulfoethyl) aniline, N-[(4'-amino) phenyl]morpholine, N[(4'-amino) phenyl]piperidine, 3-methyl 4-amino N-methyl aniline, 2-chloro 4-amino N-(ethyl)aniline and 2-methyl 4-amino N-(β-hydroxyethyl)aniline.

Claim 28

Dye composition according to claim 21, characterized by the fact that the para aminophenol is selected from the group consisting of para aminophenol, 2-methyl 4-amino phenol, 3-methyl 4-amino phenol, 2-chloro 4-amino phenol, 3-chloro 4-amino phenol, 2,6-dimethyl 4-amino phenol, 3,5-dimethyl 4-amino phenol, 2,3-dimethyl 4-amino phenol and 2,5-dimethyl 4-amino phenol.

Claim 29

Dye composition according to claim 21, characterized by the fact that pyridine derivative is 2,6-diamino pyridine.

Claim 30

Dye composition according to claim 20 wherein said coupler has the formula ##STR75## wherein R 17 and R 18 , identical or different, represent hydroxy, --NHR wherein R is hydrogen, acyl, ureido, carbalkoxy, carbamylalkyl or alkyl or R 17 and R 18 can also represent hydrogen or alkyl, provided that at least one of R 17 and R 18 represents --OH, and R 19 and R 20 represent hydrogen, branched or chain alkyl, alkoxy, halogen, amino, amino substituted by alkyl, acylamino or ureido.

Claim 31

Dye composition according to claim 26, characterized by the fact that the coupler is resorcin, meta aminophenol, 2,4-diamino anisole, 2-methyl 5-ureido phenol, 2,6-dimethyl 5-amino phenol, 2-methyl 5-acetylamino phenol, 2,6-dimethyl 5-amino phenol, 2-methyl 5-acetylamino phenol, 2,6-dimethyl 5-acetylamino phenol or 3-amino 4-methoxy phenol.

Claim 32

Dye composition according to claim 20 wherein said coupler is 6-hydroxy phenomorpholine or α-naphthol.

Claim 33

Dye composition according to claim 20, characterized by the fact that it is used in a mixture with an oxidizing agent.

Claim 34

Dye composition according to claim 29, characterized by the fact that the oxidizing agent used is hydrogen peroxide or a peroxide or persalt.

Claim 35

Dye composition according to claim 20, characterized by the fact that the proportion of the oxidation base is between 0.03 and 2% and that of the coupler is between 0.015 and 2% by weight.

Claim 36

Process for dyeing human hair, characterized by the fact that there is applied to the hair a composition as defined in claim 12, the composition is left in contact with the hair for a period between 5 and 25 minutes after which the hair is rinsed, washed and thereafter dried.

Claim 37

Process for dyeing human hair, characterized by the fact that there is applied to hair previously washed and rinsed a dyeing composition as defined in claim 18, after which the hair is rolled up and dried.

Claim 38

Process for dyeing hair comprising impregnating the hair to be dyed with a composition as defined in claim 20, after having added to this composition hydrogen peroxide in a proportion of 100 to 300% by weight, and after a period varying from 10 to 40 minutes, rinsing the hair or washing the hair with shampoo followed by rinsing the hair and thereafter drying the hair.

Claim 39

A compound having the formula: ##STR76## wherein Z represents a substituted lower alkyl radical selected from the group consisting of carbalkoxyaminoalkyl, alkoxyalkyl, N,N-dialkylcarbamylalkyl, acylaminoalkyl, ureidoalkyl, mesylaminoalkyl and ##STR77## n being a whole number from 1 to 6 and X⊖ is an anionic residue, and each of R 1 and R 2 is hydrogen, lower alkyl having 1 to 6 carbon atoms or lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring.

Claim 40

A compound having the formula: ##STR76## wherein Z represents a substituted lower alkyl radical selected from the group consisting of carbalkoxyaminoalkyl, alkoxyalkyl, N,N-dialkylcarbamylalkyl, acylaminoalkyl, ureidoalkyl, mesylaminoalkyl and ##STR77## n being a whole number from 1 to 6 and X⊖ is an anionic residue, and each of R 1 and R 2 is hydrogen, lower alkyl having 1 to 6 carbon atoms or lower alkyl having 1 to 6 carbon atoms and substituted by a member selected from the group consisting of --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and --RCOOR', wherein R 3 is hydrogen or lower alkyl having 1 to 6 carbon atoms and R and R' are lower alkyl having 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring.

Claim 41

The compound according to claim 35 wherein R 1 and R 2 , identical or different, are selected from the group consisting of hydroxyalkyl, aminoalkyl, carbamylalkyl and carboxyalkyl.

Claim 42

The dye composition of claim 1 wherein said compound is (3-nitro-4-amino) phenoxyethanol.

Claim 43

A dye composition for human hair comprising an aqueous or water-alcohol solution having a pH between 3 and 11.5 of 0.001 to 5% by weight of a compound having the formula ##STR78## wherein Z is lower alkyl having 1-6 carbon atoms and substituted by --OH, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2,3,4,5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, with the proviso that when Z is said lower alkyl substituted by --OH and is β-hydroxy ethyl and --NO 2 is in the 4 position and --N(R 1 ) (R 2 ) is in the 2 position then either R 1 or R 2 is other than hydrogen.

Claim 44

A dye composition for human hair comprising an aqueous or water-alcohol solution having a pH between 3 and 11.5 of 0.001 to 5% by weight of a compound having the formula ##STR78## wherein Z is lower alkyl having 1-6 carbon atoms and substituted by --OH, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2,3,4,5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, with the proviso that when Z is said lower alkyl substituted by --OH and is β-hydroxy ethyl and --NO 2 is in the 4 position and --N(R 1 ) (R 2 ) is in the 2 position then either R 1 or R 2 is other than hydrogen.

Claim 45

A process for dyeing human hair comprising contacting the hair with an effective amount of a composition comprising an aqueous or water-alcohol solution, having a pH between 3 and 11.5 of 0.001 to 5% by weight of a compound having the formula ##STR79## wherein Z is lower alkyl having 1-6 carbon atoms and is substituted by --OH, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, for a period ranging between 5 and 25 minutes; rinsing the hair and drying said hair.

Claim 46

A process for dyeing human hair comprising contacting the hair with an effective amount of a composition comprising an aqueous or water-alcohol solution, having a pH between 3 and 11.5 of 0.001 to 5% by weight of a compound having the formula ##STR79## wherein Z is lower alkyl having 1-6 carbon atoms and is substituted by --OH, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, for a period ranging between 5 and 25 minutes; rinsing the hair and drying said hair.

Claim 47

The process of claim 39 wherein said compound is (3-nitro-4-amino) phenoxyethanol.

Claim 48

A compound of the formula ##STR80## wherein Z is lower alkyl having 1-6 carbon atoms and substituted by --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and 13 RCOOR', wherein R 3 is hydrogen or lower alkyl having 1-6 carbon atoms and R and R' are lower alkyl having 1-6 carbon atoms, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, with the proviso that when Z is said lower alkyl substituted by --OH and is β-hydroxy ethyl and --NO 2 is in the 4-position and --NR 1 R 2 is in the 2-position then either R 1 or R 2 is other than hydrogen.

Claim 49

A compound of the formula ##STR80## wherein Z is lower alkyl having 1-6 carbon atoms and substituted by --OH, --NH 2 , --N(R 3 ) 2 , --COOH, --CONH 2 and 13 RCOOR', wherein R 3 is hydrogen or lower alkyl having 1-6 carbon atoms and R and R' are lower alkyl having 1-6 carbon atoms, and each of R 1 and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms, the --NO 2 substituent is in the 2, 3, 4, 5 or 6 position on the ring and the --NR 1 R 2 substituent occupies any remaining position on the ring, with the proviso that when Z is said lower alkyl substituted by --OH and is β-hydroxy ethyl and --NO 2 is in the 4-position and --NR 1 R 2 is in the 2-position then either R 1 or R 2 is other than hydrogen.

Claim 50

The compound of claim 41 wherein Z is said lower alkyl substituted by --OH.

Claim 51

The compound of claim 41 which is (3-nitro-4-amino) phenoxyethanol.

Claim 52

A compound according to claim 41, wherein Z is β-hydroxyethyl, diethylaminoethyl, carbamylmethyl or carboxymethyl; and wherein each of R 1 and R 2 is hydrogen, methyl or ethyl.