Method of coloring hair with direct dye compounds

Abstract

Described herein is a method of dyeing the hair. The method includes applying to the hair a hair color composition including one or more direct dye compounds and rinsing the hair with water. The one or more direct dye compounds each include a chromophore, one or two permanent cations, one to four incipient cations, and one or more hydrophobic moieties. The incipient cations are pendant to the core structure and are neutral. The one or more direct dye compounds enter the hair shaft after the hair color composition is applied to the hair. The hair color composition has a pH of from about 7 to about 11. The pH of the hair after rinsing is from about 3.5 to about 6. The rinsing of the hair causes one or more of the one to four incipient cations to change from neutral to positively charged inside of the hair shaft.

1 . A method of dyeing the hair, the method comprising:
 a. applying to the hair a hair color composition comprising one or more direct dye compounds, the one or more direct dye compounds each comprising:   i. a chromophore;   ii. one or two permanent cations, wherein the permanent cations are pendant to the chromophore or part of the chromophore, and wherein the chromophore and the permanent cations form a core structure;   iii. one to four incipient cations, wherein each of the incipient cations is pendant via a linker group to the core structure, and wherein the incipient cations are neutral; and   iv. one or more C5-C9 hydrophobic moieties, wherein the one or more C5-C9 hydrophobes are pendant to the core structure;   wherein the one or more direct dye compounds enter the hair shaft after the hair color composition is applied to the hair; and   wherein the hair color composition has a pH of from about 7 to about 11;   b. rinsing the hair with water;   wherein the pH of the hair after rinsing is from, about 3.5 to about 6; and   wherein the rinsing of the hair causes one or more of the one to four incipient cations to change from neutral to positively charged inside of the hair shaft,   wherein the chromophore has a structure according to Formula (XIXa), Formula (XIXc), Formula (XIXd), Formula (XIXf), Formula (XIXg), Formula (XIXi), Formula (XIXj), Formula (XIXo), homologs thereof, the partially or fully protonated forms thereof, cosmetically acceptable salts thereof, and any combination thereof wherein these Formulas and homologs thereof have the following structures:   
       
         
           
           
               
               
           
         
         wherein 
         R 1b , R 1c , R 1e , R 1f , R 1i , R 1j  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group; and 
         R 1h  and R 1g  are each independently hydrogen, C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         R 1a  and R 1d  are each independently C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary ammo group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXa); and 
         the total number of amino groups attached to R 1a , R 1d , R 1g  and R 1h  is 1-4; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 3b , R 3c , R 3d , R 3e , R 3h , R 3i  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, and, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an ammo group on the other end of the linker; and 
         R 3f  and R 3 g are each independently hydrogen, C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         R 3a  is C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXc); and 
         the total number of amino groups attached to R 3a , R 3f , and R 3g  is 1-3; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 4b , R 4c , R 4d , R 4e , R 4g , R 4h  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group on the other end of the linker; and 
         R 4f  is hydrogen, C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         R 4a  is C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXd); and 
         the total number of amino groups attached to R 4a  and R 4f  is 1 or 2; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 6c , R 6d , R 6e , R 6g , R 6h , R 6i , and R 6j  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group on the other end of the linker; and 
         R 6a  and R 6e  are each independently a linker group with a cationic moiety attached, the cationic group is quaternary ammonium, imidazolium, pyridinium, oxazolium, or thiazoliumis, and wherein R 6a  and R 6e  can also each independently take on the form of L 1 −Q*(−L 2 A) n , where L 1  and L 2  can be the same or different linkers, Q* is the cationic moiety, A is an amino group and n is either 1 or 2; and 
         R 6b  and R 6f  are each independently a hydrogen, alkyl or linker group L with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXf); and 
         the total number of ammo groups attached to R 6a , R 6b , R 6e  and R 6f  is 1, 2, 3 or 4 and the total number of cationic moiety attached to R 6a  and R 6e  is 1 or 2; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 7b , R 7c , R 7d , R 7f , R 7g , R 7h , R 7i , R 7j , R 7k  and R 7m  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, and, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group on the other end of the linker; and 
         R 7a  and R 7e  are each independently C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary ammo group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXg); and 
         the total number of amino groups attached to R 7a  and R 7e  is 1 or 2; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 9b , R 9c , R 9g , R 9h , and R 9i  each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group on the other end of the linker; and 
         R 9d  and R 9e  are each independently hydrogen, C 5 -C 9  alkyl, hydroxyl alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         R 9a  and R 9f  are each independently C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XLXi); and 
         the total number of amino groups attached to R 9a , R 9d , R 9e  and R 9f  is 1-4; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 10b , R 10c , R 10d , R 10e , and R 10i  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, aryl, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an ammo group on the other end of the linker; and 
         R 10f  and R 10g  are each independently hydrogen, C 5 -C 9  alkyl, hydroxyl alkyl or a linker group with a primary, secondary or tertiary ammo group attached; and 
         R 10a  and R 10h  are each independently C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXj); and 
         the total number of amino groups attached to R 10a , R 10f , R 10g  and R 10h  is 1-4; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 15b , R 15e , R 15d , R 15e , R 15g , R 15h , R 15k  and R 15i  are each independently hydrogen, alkyl, halogen substituted alkyl, alkenyl, alkynyl, and, hydroxyl alkyl, alkoxy, aryloxy, acyl, halogen, nitro, nitroso, cyano, a heterocyclic moiety, thioether or are attached to a linker with or without an amino group on the other end of the linker; and 
         R 15i  and R 15j  are each independently hydrogen, C 5 -C 9  alkyl, hydroxyl alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         R 15a  and R 15f  are each independently C 5 -C 9  alkyl or a linker group with a primary, secondary or tertiary amino group attached; and 
         there is minimally one C 5 -C 9  alkyl group attached to the chromophore of Formula (XIXo); and 
         the total number of amino groups attached to R 15a , R 15f , R 15i  and R 15j  is 1-4. 
       
     
     
         2 . The method of  claim 1 , wherein the one or more C 5 -C 9  hydrophobic moieties are C 5 -C 6  hydrophobic moieties. 
     
     
         3 . The method of  claim 1 , wherein the one or more direct dye compounds each comprise two incipient cations. 
     
     
         4 . The method of  claim 1 , wherein the one or more direct dye compounds each has a molecular weight of less than about 1,000 g/mol. 
     
     
         5 . The method of  claim 1 , wherein the hair color composition has a pH of from about 9 to about 11. 
     
     
         6 . The method of  claim 1 , wherein the hair color composition has a pH of from about 7 to about 9. 
     
     
         7 . The method of  claim 1 , wherein an oxidizing agent is applied before or during the application of the hair color composition. 
     
     
         8 . The method of  claim 7 , wherein the oxidizing agent is selected from the group consisting of peroxides, perborates, percarbonates, persulfates, oxidant generating enzymes, oxidant generating substrates, and combinations thereof. 
     
     
         9 . The method of  claim 1 , wherein the hair color composition further comprises one or more oxidation dyes. 
     
     
         10 . The method of  claim 1 , wherein the chromophore has a structure according to Formula (XIXa), Formula (XIXf), or Formula (XIXg). 
     
     
         11 . The method of  claim 10 , wherein the one or more C 5 -C 9  hydrophobic moieties are C 5 -C 6  hydrophobic moieties. 
     
     
         12 . The method of  claim 10 , wherein the one or more direct dye compounds each comprise two incipient cations. 
     
     
         13 . The method of  claim 10 , wherein the one or more direct dye compounds each has a molecular weight of less than about 1,000 g/mol. 
     
     
         14 . The method of  claim 10 , wherein the hair color composition has a pH of from about 7 to about 9. 
     
     
         15 . The method of  claim 1 , wherein the chromophore has a structure according to Formula (XIXo). 
     
     
         16 . The method of  claim 15 , wherein the one or more C 5 -C 9  hydrophobic moieties are C 3  -C 6  hydrophobic moieties. 
     
     
         17 . The method of  claim 15 , wherein the one or more direct dye compounds each comprise two incipient cations. 
     
     
         18 . The method of  claim 15 , wherein the one or more direct dye compounds each has a molecular weight of less than about 1,000 g/mol. 
     
     
         19 . The method of  claim 15 , wherein the hair color composition has a pH of from about 7 to about 9. 
     
     
         20 . The method of  claim 15 , wherein the hair color composition further comprises one or more oxidation dyes.