Abstract:
Disclosed are styryl sulfide dyes of formula (1), wherein R 1 , R' 1 , R 2 , R' 2 , R 3 and R' 3 , independently from each other are hydrogen; C 1 -C 20 alkyl or C 1 - C 20 alkoxy, which may be substituted by one or more C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 or hydroxy; C 3 -C 6 cycloalkyl; -C(O)H; -C(O)-C 1 -C 5 alkyl; halogen; NO 2 ; OH; phenyl, which may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 or hydroxy; or a radical of formula -NR 4 R 5 , wherein R 4 and R 5 independently from each other are hydrogen; C 1 -C 12 alkyl, which may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 -alkoxy, hydroxy or -(CO)-H; -(CO)-C 1 -C 5 alkyl; phenyl or phenyl-C 1 -C 4 alkyl, wherein the phenyl moiety may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 , carboxy or hydroxy; W 1 , W' 1 , W 2 , W' 2 , W 3 , W' 3 , W 4 or W' 4 , independently from each other are -CH- or -N + -; wherein only one of W 1 /W' 1 , W 2 /W' 2 , W 3 /W' 3 , W 4 /W 4 ' is -N + ; and the bivalent radical -Q-Z-Y-S-S-Y'-Z'-Q'- is bonded to W 1 or W 2 and W' 1 or W' 2 respectively; Y 1 and Y 2 independently from each other are C 1 -C 10 alkylene; C 5 -C 10 cycloalkylene; C 5 -C 12 arylene; or C 5 -C 12 arylene-(C 1 -C 10 alkylene); Q and Q' independently from each other are the direct bond; or -C(O)-; -C(O)O-; -OCO-; -N(R 6 )-; formula (AA); -C(O)N(R 6 )-; -(R 6 )NC(O)-; -O-; -S-; -S(O)-; or -S(O) 2 -; and R 6 and R 7 independently from each other are hydrogen; C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 - C 12 aryl; C 6 -C 12 aryl-C 1 -C 10 alkyl; or C 1 -C 10 alkyl(C 5 -C 12 aryl). Further, the present invention relates to novel styryl sulfide compounds, compositions thereof, especially comprising other dyes, and to processes for their preparation.
Abstract:
Disclosed are thiol dyes of formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 independently from each other are hydrogen; unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 -C 10 aryl; C 6 -C 10 aryl-C 1 -C 10 alkyl; or C 5 -C 10 alkyl(C 5 -C 10 aryl); A is a residue of an organic dye; and Y 1 is the direct bond; C 1 C 10 alkylene; C 5 -C 10 cycloalkylene; C 5 -C 12 arylene; or C 5 -C 12 arylene- (C1-C 10 alkylene). The compounds are used to dye hair with or without reducing agents. Furthermore, the present invention relates to compositions comprising thiol dyes of formula (I) and to process for the preparation of theses compounds.
Abstract:
Disclosed is a method of dyeing keratin-containing fibers comprising treating the fiber with at least one compound of formula (1), wherein R 1 , R 2 , R 3 , R 4 independently from each other are hydrogen; hydroxy; -S-H; -S-C 1 -C 12 alkyl; halogen; C 1 -C 12 alkyl or C 1 -C 12 alkoxy, which may be substituted by one or more C 1 - C 5 alkyl, C 1 -C 5 -alkoxy, hydroxy, -(CO)-H or -(CO)-C 1 -C5alkyl; -NR 5 R 6 ; -NO 2 ; -(CO)H or (CO)-C 1 -C 5 alkyl; C 6 -C 12 aryl, C 6 -C 12 aryl-C 1 -C 4 alkyl or C 6 -C 12 aryl-C 1 -C 4 alkoxy, wherein the aryl moiety may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, -(CO)-H or -(CO)-C 1 -C 5 alkyl; R 5 and R 6 independently from each other are hydrogen; hydroxy; C 1 -C 12 alkyl; hydroxy-C 1 - C 12 alkyl; -(CO)-H; -(CO)-C 1 -C 5 alkyl; phenyl or phenyl-C 1 -C 5 alkyl, wherein the phenyl moiety may be substituted by one or more C1-C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH2, mono-C 1 -C 5 alkylamino, di-C 1 -C5alkylamino, -NO 2 , carboxy or hydroxy; and An is an anion. Furthermore, the present invention relates to novel heterocyclic compounds, compositions thereof, especially comprising other dyes, and to processes for their preparation and application to hair dying.
Abstract:
Disclosed are styryl sulfide dyes of formula (1), wherein R 1 , R' 1 , R 2 , R' 2 , R 3 and R' 3 , independently from each other are hydrogen; C 1 -C 20 alkyl or C 1 - C 20 alkoxy, which may be substituted by one or more C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 or hydroxy; C 3 -C 6 cycloalkyl; -C(O)H; -C(O)-C 1 -C 5 alkyl; halogen; NO 2 ; OH; phenyl, which may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 or hydroxy; or a radical of formula -NR 4 R 5 , wherein R 4 and R 5 independently from each other are hydrogen; C 1 -C 12 alkyl, which may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 -alkoxy, hydroxy or -(CO)-H; -(CO)-C 1 -C 5 alkyl; phenyl or phenyl-C 1 -C 4 alkyl, wherein the phenyl moiety may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 , carboxy or hydroxy; W 1 , W' 1 , W 2 , W' 2 , W 3 , W' 3 , W 4 or W' 4 , independently from each other are -CH- or -N + -; wherein only one of W 1 /W' 1 , W 2 /W' 2 , W 3 /W' 3 , W 4 /W 4 ' is -N + ; and the bivalent radical -Q-Z-Y-S-S-Y'-Z'-Q'- is bonded to W 1 or W 2 and W' 1 or W' 2 respectively; Y 1 and Y 2 independently from each other are C 1 -C 10 alkylene; C 5 -C 10 cycloalkylene; C 5 -C 12 arylene; or C 5 -C 12 arylene-(C 1 -C 10 alkylene); Q and Q' independently from each other are the direct bond; or -C(O)-; -C(O)O-; -OCO-; -N(R 6 )-; formula (AA); -C(O)N(R 6 )-; -(R 6 )NC(O)-; -O-; -S-; -S(O)-; or -S(O) 2 -; and R 6 and R 7 independently from each other are hydrogen; C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 - C 12 aryl; C 6 -C 12 aryl-C 1 -C 10 alkyl; or C 1 -C 10 alkyl(C 5 -C 12 aryl). Further, the present invention relates to novel styryl sulfide compounds, compositions thereof, especially comprising other dyes, and to processes for their preparation.
Abstract:
Disclosed are azo dyes of formula (1) , wherein R1 is hydrogen; C1-C14alkyl; hydroxy- C1-C14alkyl; C2-C14alkenyl; a radical of formula (1a) -(CH2)n1-O-(CH2)n2-CH3; a radical of formula (1b) C10aryl; or C6-C10aryl-C1-C6alkyl; R3 is hydrogen; C1-C14alkyl; C2-C14alkenyl; C6-C10aryl; C6-C10aryl-C1-C6alkyl; or CO-R6; R4 is CO-R6; R5 is C1-C14alkyl; C2-C14alkenyl; C6-C10aryl; or C6-C10aryl-C1-C6alkyl; R6 is hydrogen; C1-C14alkyl; C2-C14alkenyl; or C6-C10aryl; R7, R8, R9 and R10, independently from each other are hydrogen; or C1-C5alkyl; m is 1; or 2; An is an anion; If m = 1, R2 is hydrogen; C1-C14alkyl; C2-C14alkenyl; a radical of formula (1a); a radical of formula (1b) ; C6-C10aryl; or C6-C10aryl-C1-C6alkyl; If m = 2, R2 is the direct bond; or C1-C14alkylene, which is optionally substituted by one or more C1-C4alkyl, or which is optionally interrupted by C5-C10arylene, -O- or -NR9R10-; R9 and R10, independently from each other are hydrogen; or C1-C5alkyl; and n1, n2, n3 and n4, independently from each other are a number from 0 to 5. The compounds are useful for the dyeing of organic material, preferably human hair.
Abstract:
Disclosed are thiol dyes of formula (1 ) wherein L1 is hydrogen; C 1 -C 12 alkyl; or phenyl-C 1 -C4alkyl; X is C 1 -C 12 alkylene, C 2 -C 12 alkenylene, C 5 -C 10 cycloalkylene, C 5 -C 10 arylene, or C 5 -C 10 arylene-C 1 -C 10 alkylene, which may by interrupted by -O-, -NH-, -S-, -CO-, o -SO 2 -; Y is the residue of an organic dye Z is a group of formula (1b) or -C?N; wherein A is O; S; or N-L 2 ; B is L 3 ; -OL 3 ; -NL 3 L 4; or -SL 3 ; and L 2 , L 3 and L 4 , indepently from other are are hydrogen; C 1 -C 12 alkyl; C 5 -C 12 aryl-C 1 -C 12 alkyl. The compounds are useful for the dyeing of organic materials, such as keratin fibers, preferably human hair.
Abstract:
Disclosed are azo dyes of formula (1) , wherein R 1 is hydrogen; C 1 -C 14 alkyl; hydroxy- C 1 -C 14 alkyl; C 2 -C 14 alkenyl; a radical of formula (1a) -(CH 2 ) n1 -O-(CH 2 ) n2 -CH 3 ; a radical of formula (1b) C 10 aryl; or C 6 -C 10 aryl-C 1 -C 6 alkyl; R3 is hydrogen; C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 -C 10 aryl; C 6 -C 1 0aryl-C 1 -C 6 alkyl; or CO-R 6 ; R 4 is CO-R 6 ; R 5 is C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 -C 10 aryl; or C 6 -C 10 aryl-C 1 -C 6 alkyl; R 6 is hydrogen; C 1 -C 14 alkyl; C 2 -C 14 alkenyl; or C 6 -C 10 aryl; R 7 , R 8 , R 9 and R 10 , independently from each other are hydrogen; or C 1 -C 5 alkyl; m is 1; or 2; An - is an anion; If m = 1, R 2 is hydrogen; C 1 -C 14 alkyl; C 2 -C 14 alkenyl; a radical of formula (1a); a radical of formula (1b) ; C 6 -C 10 aryl; or C 6 -C 10 aryl-C 1 -C 6 alkyl; If m = 2, R 2 is the direct bond; or C 1 -C 14 alkylene, which is optionally substituted by one or more C 1 -C 4 alkyl, or which is optionally interrupted by C 5 -C 10 arylene, -O- or -NR 9 R 10 -; R 9 and R 10 , independently from each other are hydrogen; or C 1 -C 5 alkyl; and n1, n2, n3 and n4, independently from each other are a number from 0 to 5. The compounds are useful for the dyeing of organic material, preferably human hair.
Abstract:
Disclosed are dyes of Formula (I) wherein D is the radical of anthraquinone, acridine, azo, azomethine, hydrazomethine, benzodifuranone, coumarine, diketopyrrolopyrrol, dioxaxine, diphenylmethane, formazane, indigoid, indophenol, naphtalimide, naphthaquinone, nitroaryl, merocyanine, methine, oxazine,perinone, perylene, pyrenequinone, phtalocyanine, phenazine, quinoneimine, quinacridone, quinophtalone, stilbene, styryl, triphenylmethane, xanthene, thiazine dye and thioxanthene dye; Q is C 1 -C 30 alkylene, -C 2 -C 12 alkenylene, C 5 -C 10 arylene-, C 5 -C 10 cycloalkylene-or -C 1 - C 10 alkylene(C 5 -C 10 arylene)-which may be interrupted and/or terminated at one or both ends by one or more than one -O-, -S-, -N=, -N(R 1 )-, SO 2, -(CH 2 CH 2-O) 1-5-, -(CH 2 CH 2 CH 2 -O) 1-5-, -C(O)-, -C(O)-C 1 -C 12 alkenylene, -C(O)O-, -OCO-, A N+ R 1 R 2, -CON(R 1 )-, -C(NR 1 R 2 ) 2 -, -(R 1 )NC(O)-, -CSR 1 -or an optionally substituted, saturated or unsaturated, fused or non-fused aromatic or nonaromatic (hetero)cyclic) bivalent radical optionally comprising at least one heteroatom; -O-; -S-; -N(R 1 )-; SO 2 ; -(CH 2 CH 2 -O) 1-5 -; -C(O)-; -C(O)-C 1 -C 12 alkenylene; -C(O)O-, -OCO-; B N+ R 1 R 2; -CON(R 1 )-; -C(NR 1 R 2 ) 2 -; -(R 1 )NC(O)-; CSR 1 ; saturated or unsaturated, fused or non-fused aromatic or nonaro- matic bivalent radical optionally comprising at least one heteroatom; which is optionally substituted by C 1 -C 30 alkyl, C 1 -C 30 alkoxy, -C 2 -C 12 alkenyl, C 5 -C 10 aryl, C 5 -C 10 cycloalkyl, C 1 - C 10 alkyl(C 5 -C 10 arylene), hydroxy or D+; R 1 and R 2 independently from each other are hydrogen; or unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C 1 - C 14 alkyl; C 1 -C 14 hydroxyalkyl; C 1 -C 14 aminoalkyl; C 2 -C 14 alkenyl; C 6 -C 10 aryl; C 6 -C 10 aryl-C 1 - C 10 alkyl; or C 5 -C 10 alkyl(C 5 -C 10 aryl).
Abstract:
Disclosed are thiol dyes of formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 independently from each other are hydrogen; unsubstituted or substituted, straight-chain or branched, monocyclic or polycyclic, interrupted or uninterrupted C 1 -C 14 alkyl; C 2 -C 14 alkenyl; C 6 -C 10 aryl; C 6 -C 10 aryl-C 1 -C 10 alkyl; or C 5 -C 10 alkyl(C 5 -C 10 aryl); A is a residue of an organic dye; and Y 1 is the direct bond; C 1 C 10 alkylene; C 5 -C 10 cycloalkylene; C 5 -C 12 arylene; or C 5 -C 12 arylene- (C1-C 10 alkylene). The compounds are used to dye hair with or without reducing agents. Furthermore, the present invention relates to compositions comprising thiol dyes of formula (I) and to process for the preparation of theses compounds.
Abstract:
Disclosed are oligomeric cationic azo dyes of formula (I), wherein their salts, isomers, hydrates and other solvates, wherein R 1 is hydrogen; C 1 -C 12 alkyl, which may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 -alkoxy, hydroxy or -(CO)-H; -(CO)-C 1 -C 5 alkyl; phenyl or phenyl-C 1 -C 4 alkyl, wherein the phenyl moiety may be substituted by one or more C 1 -C 5 alkyl, C 1 -C 5 alkoxy, halogen, -NH 2 , mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -NO 2 , carboxy or hydroxy; R 2 is hydrogen; or C 1 -C 5 alkyl; X is C 1 -C 10 alkylene, which may be substituted by one or more C 1 -C 5 alkyl, hydroxy, C 1 -C 5 -alkoxy, amino, mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -SH, and/or interrupted by one or more -O- or -S-S-; C 5 -C 10 cycloalkylene; C 5 -C 12 arylene; C 5 -C 12 arylene-(C 1 -C 10 alkylene); biphenylene, which may be substituted by one or more C 1 -C 5 alkyl, hydroxy, C 1 -C 5 -alkoxy, amino, mono-C 1 -C 5 alkylamino, di-C 1 -C 5 alkylamino, -SH, and/or interrupted by one or more -O-, C 1 -C 4 -alkylene, -NR 3 -, -S- or -S-S-; R 3 is hydrogen; C 1 -C 12 alkyl; C 2 -C 14 alkenyl; C 6 -C 12 aryl; C 6 -C 12 aryl-C 1 -C 12 alkyl; or C 1 -C 12 alkyl-C 6 -C 12 aryl; Y is an anion; Z is 1,3-thiazolyl; 1,2-thiazolyl; 1,3-benzothiazolyl; 2,3-benzothiazolyl; imidazolyl; 1,3,4-thiadiazolyl; 1,3,5-thiadiazolyl; 1,3,4-triazolyl; pyrazolyl; benzimidazolyl; benzopyrazolyl; pyridinyl; quinolinyl; pyrimidinyl; or isoxazolyl; and n is a number from 2-100. Furthermore, the present invention relates to novel cationic oligomeric azo dyes, compositions thereof, especially comprising other dyes, and to application for hair dying.