2-(Amino or Substituted Amino)-5, 6-Substituted Phenol Compounds, Dyeing Compositions Containing Them, and Use Thereof

Abstract

The present invention relates to 2-(amino or substituted amino)-5,6-substituted phenol compounds according to the Formula (I), as defined herein and compositions for the oxidative dyeing of keratin fibres, comprising a medium suitable for dyeing and a compound of the Formula (I).

1 . A compound of the formula (I), or its salts with an inorganic or organic acid,  
       
         
           
           
               
               
           
         
       
       wherein both R 5  and R 6  are substituted and R 5  is selected from: 
 (a) the group of C-linked monovalent substituents consisting of: (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and (iii) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (i), (ii) and (iii) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms independently selected from O, S and Si;  
 (b) the group of O-linked monovalent substituents consisting of OA 9 , OCN and ONA 6 A 7 ;  
 (c) the group of N-linked monovalent substituents consisting of NA 6 A 10 , (NA 6 A 7 A 8 ) + , NA 6 OA 7 , NA 6 SA 7 , NCO, NCS, N═NA 6 , N═NOA 6 , NA 6 CN, and NA 6 NA 7 A 8 ;  
 (d) the group of monovalent substituents consisting of CON 3 , CONA 6 COA 7 , C(═NA 6 )NA 6 A 7 , CHO, and CHS; and  
 (e) the group of fluoroalkyl monovalent substituents consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and about 0 to about 4 heteroatoms, 
 wherein for the groups (b) to (e), A 6 , A 7 , and A 8  are monovalent and are independently selected from:  
 (1) H,  
 (2) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (3) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (4) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (2), (3) and (4) comprising from about 1 to about 10 carbon atoms and about 0 to about 5 heteroatoms selected from O, S, N, P, and Si;  
 wherein A 9  is monovalent and is independently selected from:  
 (1) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (2) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (3) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (1), (2) and (3) comprising independently from about 2 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si, and  
 wherein A 10  is monovalent and is independently selected from:  
 (1) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (2) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (3) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (1), (2) and (3) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si; and wherein X is a halogen selected from the group consisting of F, Cl, Br, and I, and  
 wherein the substituent R 6  is selected from:  
 
 (a) the group of C-linked monovalent substituents consisting of: (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and (iii) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (i), (ii) and (iii) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms independently selected from O, S, N, P, and Si;  
 (b) the group of O-linked monovalent substituents consisting of OA 14 , OCN and ONA 11 A 12 ;  
 (c) the group of N-linked monovalent substituents consisting of NA 11 A 15 , (NA 11 A 12 A 13 ) + , NA 11 OA 12 , NA 11 SA 12 , NCO, NCS, NO 2 , N═NA 11 , N═NOA 11 , NA 11 CN, and NA 11 NA 12 A 13 ;  
 (d) the group of monovalent substituents consisting of CON 3 , CONA 11 COA 12 , C(═NA 11 )NA 11 A 12 , CHO, and CHS and  
 (e) the group of fluoroalkyl monovalent substituents consisting of mono-, poly-, or per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and from about 0 to about 4 heteroatoms, 
 wherein for the groups (b) to (e), A 11 , A 12 , and A 13  are monovalent and are independently selected from:  
 (1) H,  
 (2) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (3) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (4) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (2), (3) and (4) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si and wherein A 14  is monovalent and is independently selected from:  
 (1) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (2) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (3) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (1), (2) and (3) comprising independently from about 2 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si, and wherein A 15  is monovalent and is independently selected from:  
 (1) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (2) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (3) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (1), (2) and (3) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si; and wherein X is a halogen selected from the group consisting of F, Cl, Br, and I and  
 wherein R 5  and R 6  are not both methyl and wherein R 2  is selected from H and any of the groups defined for R 5  and R 6 .  
 
 
     
     
         2 . A compound according to  claim 1 , wherein R 5  is selected from:—
 (a) the group of C-linked monovalent substituents consisting of: (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and (iii) substituted or unsubstituted mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected independently from O, S and N;    (b) the group of monovalent substituents consisting of CON 3 , CONA 6 COA 7 , C(═NA 6 )NA 6 A 7 , CHO, and CHS; and    (c) the group of fluoroalkyl monovalent substituents consisting of mono-, poly-, and per-fluoro alkyl systems comprising from about 1 to about 8 carbon atoms and from about 0 to about 3 heteroatoms, 
 wherein for the groups (b) to (c), A 6  and A 7  are monovalent and are independently selected from:  
 (1) H,  
 (2) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (3) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (4) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (2), (3) and (4) comprising from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si and  
 wherein R 6  is selected from:— 
   (a) the group of C-linked monovalent substituents consisting of: (i) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and (iii) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; said systems of (i), (ii) and (iii) independently comprising from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms independently selected from O, S and N.    (b) the group of monovalent substituents consisting of CON 3 , CONA 11 COA 12 , C(═NA 11 )NA 11 A 12 , CHO, and CHS; and    (c) the group of fluoroalkyl monovalent substituents consisting of mono-, poly-, or per-fluoro alkyl systems comprising from about 1 to about 12 carbon atoms and about 0 to about 4 heteroatoms, 
 wherein for the groups (b) and (c), A 11  and A 12  are monovalent and are independently selected from:  
 (1) H,  
 (2) substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems,  
 (3) substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclic systems, and  
 (4) substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein said systems of (2), (3) and (4) comprising independently from about 1 to about 10 carbon atoms and from about 0 to about 5 heteroatoms selected from O, S, N, P, and Si, and wherein R 5  and R 6  are not both methyl.  
   
     
     
         3 . A compound according to  claim 1 , wherein R 5  is selected from:—
 the group of C-linked monovalent substituents consisting of substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, wherein said systems comprising independently from about 1 to about 6 carbon atoms and from about 0 to about 2 heteroatoms selected from O, S and N, and wherein,    R 6  is selected from:—
 the group of C-linked monovalent substituents consisting of substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, wherein said systems comprising independently from about 1 to about 6 carbon atoms and from about 0 to about 2 heteroatoms selected from O, S and N and wherein R 5  and R 6  are not both methyl and wherein R 2  is H.  
   
     
     
         4 . A composition for the oxidative dyeing of keratin fibres, comprising a medium suitable for dyeing and from about 0.001% to about 10%, by weight, of the composition, of a compound according to  claim 1 .  
     
     
         5 . A composition according to  claim 4 , further comprising a primary intermediate selected from p-phenylenediamine, p-aminophenol, o-phenylenediamine, o-aminophenol, heterocyclics, derivatives thereof, and mixtures thereof.  
     
     
         6 . A composition according to  claim 4 , further comprising a coupler selected from phenol, resorcinol, naphthol, m-phenylenediamine, m-aminophenol, heterocyclics, derivatives thereof, and mixtures thereof.  
     
     
         7 . A composition according to  claim 4 , further comprising a primary intermediate and coupler combination selected from the group consisting of: (a) resorcinol, 4-amino-m-cresol, 2-methylresorcinol, 4-amino-2-hydroxytoluene, m-aminophenol and 2-amino-4-hydroxyethyl anisole sulphate; (b) resorcinol, 4-amino-m-cresol, 2-methylresorcinol, 4-amino-2-hydroxytoluene, m-aminophenol, 2-amino-4-hydroxyethyl anisole sulphate, 1-napthol and toluene-2,5-diamine; (c) 2-methyl-5-hydroxyethylaminophenol, resorcinol, toluene-2,5-diamine, m-aminophenol, p-aminophenol and p-methylaminophenol; (d) 2-methyl-5-hydroxyethylaminophenol, m-aminophenol, p-aminophenol, p-methylaminophenol and p-phenylenediamine; (e) 1-hydroxyethyl-4,5-diamino pyrazole sulphate and m-aminophenol; and (f) 2-methylresorcinol, p-aminophenol, 4-amino-2-hydroxytoluene, p-phenylenediamine and N,N-Bis(2-hydroxyethyl)-p-phenylenediamine.  
     
     
         8 . A composition according to  claim 4 , further comprising an oxidizing agent selected from the group consisting of: hydrogen peroxide; inorganic alkali metal peroxides; organic peroxides; inorganic perhydrate salt bleaching compounds; alkali metal bromates; enzymes; and mixtures thereof.  
     
     
         9 . A composition according to  claim 4 , further comprising a thickener selected from salt tolerant thickeners selected from the group consisting of: xanthan, guar, hydroxypropyl guar, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, N-vinylpyrollidone, Acrylates/Ceteth-20 Itaconate copolymer, PEG-150/Decyl/SMDI copolymer, PEG-150/Stearyl/SMDI copolymer, trihydroxystearin, Acrylates/Steareth-20 Methacrylate copolymer, blended Ceteth-10 phosphate/Di-cetyl phosphate/Cetearyl alcohol, and mixtures thereof.  
     
     
         10 . A composition according to  claim 4 , further comprising a chelant.  
     
     
         11 . A composition according to  claim 4 , wherein said medium comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, glycerol, 1,2-propylene glycol, hexylene glycol, ethoxy diglycol, and mixtures thereof.  
     
     
         12 . A method for oxidative dyeing of keratin fibres, said method comprising the step of applying a composition according to  claim 4  to keratin fibres in the presence of an oxidizing agent.  
     
     
         13 . A multi-compartment device for the oxidative dyeing of keratin fibres or a multi-compartment kit for the oxidative dyeing of keratin fibres, comprising at least a first compartment containing a composition according to  claim 4 , and at least a second compartment containing an oxidizing composition.  
     
     
         14 . A composition for the oxidative dyeing of keratin fibres, comprising a medium suitable for dyeing and from about 0.001% to about 10%, by weight, of the composition, of a compound according to formula (I)  
       
         
           
           
               
               
           
         
         wherein R 2  is selected from H and the group of C-linked monovalent substituents consisting of substituted or unsubstituted, straight or branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, wherein said systems comprising independently from about 1 to about 6 carbon atoms and from about 0 to about 2 heteroatoms selected from O, S and N.  
       
     
     
         15 . A composition according to  claim 14 , further comprising a primary intermediate selected from p-phenylenediamine, p-aminophenol, o-phenylenediamine, o-aminophenol, heterocyclics, derivatives thereof, and mixtures thereof.  
     
     
         16 . A composition according to  claim 14 , further comprising a coupler selected from phenol, resorcinol, naphthol, m-phenylenediamine, m-aminophenol, heterocyclics, derivatives thereof, and mixtures thereof.  
     
     
         17 . A composition according to  claim 14 , further comprising a primary intermediate and coupler combination selected from the group consisting of: (a) resorcinol, 4-amino-m-cresol, 2-methylresorcinol, 4-amino-2-hydroxytoluene, m-aminophenol and 2-amino-4-hydroxyethyl anisole sulphate; (b) resorcinol, 4-amino-m-cresol, 2-methylresorcinol, 4-amino-2-hydroxytoluene, m-aminophenol, 2-amino-4-hydroxyethyl anisole sulphate, 1-napthol and toluene-2,5-diamine; (c) 2-methyl-5-hydroxyethylaminophenol, resorcinol, toluene-2,5-diamine, m-aminophenol, p-aminophenol and p-methylaminophenol; (d) 2-methyl-5-hydroxyethylaminophenol, m-aminophenol, p-aminophenol, p-methylaminophenol and p-phenylenediamine; (e) 1-hydroxyethyl-4,5-diamino pyrazole sulphate and m-aminophenol; and (f) 2-methylresorcinol, p-aminophenol, 4-amino-2-hydroxytoluene, p-phenylenediamine and N,N-Bis(2-hydroxyethyl)-p-phenylenediamine.  
     
     
         18 . A composition according to  claim 14 , further comprising an oxidizing agent selected from the group consisting of: hydrogen peroxide; inorganic alkali metal peroxides; organic peroxides; inorganic perhydrate salt bleaching compounds; alkali metal bromates; enzymes; and mixtures thereof.  
     
     
         19 . A composition according to  claim 14 , further comprising a thickener selected from salt tolerant thickeners selected from the group consisting of: xanthan, guar, hydroxypropyl guar, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, N-vinylpyrollidone, Acrylates/Ceteth-20 Itaconate copolymer, PEG-150/Decyl/SMDI copolymer, PEG-150/Stearyl/SMDI copolymer, trihydroxystearin, Acrylates/Steareth-20 Methacrylate copolymer, blended Ceteth-10 phosphate/Di-cetyl phosphate/Cetearyl alcohol, and mixtures thereof.  
     
     
         20 . A composition according to  claim 14 , further comprising a chelant.  
     
     
         21 . A composition according to  claim 14 , wherein said medium comprises a solvent selected from the group consisting of water, ethanol, propanol, isopropanol, glycerol, 1,2-propylene glycol, hexylene glycol, ethoxy diglycol, and mixtures thereof.  
     
     
         22 . A method for oxidative dyeing of keratin fibres, said method comprising the step of applying a composition according to  claim 4  to keratin fibres in the presence of an oxidizing agent.  
     
     
         23 . A multi-compartment device for the oxidative dyeing of keratin fibres or a multi-compartment kit for the oxidative dyeing of keratin fibres, comprising at least a first compartment containing a composition according to  claim 4 , and at least a second compartment containing an oxidizing composition.