Monoazo metal complex compound containing composition and production method thereof

Abstract

Monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test based on the maximization method of said composition being not more than 20% and method for producing said composition which comprises a step for removing impurity substances using an alcoholic organic solvent; charge control agent comprising said composition and toner containing said charge control agent; coloring agent containing said composition and colored thermoplastic resin composition containing said coloring agent.

What is claimed is:  
     
         1 . Monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         2 . Monoazo metal complex compound containing composition of  claim 1  wherein said skin sensitization potential test is a skin sensitization potential test based on the maximization method.  
     
     
         3 . Monoazo metal complex compound containing composition of  claim 1  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         4 . Monoazo metal complex compound containing composition of  claim 2  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         5 . Monoazo metal complex compound containing composition of any of claims  1 ,  2 ,  3  or  4  wherein said monoazo metal complex compound is a compound of the following formula (1):  
       
         
           
           
               
               
           
         
       
       wherein each of R 1  through R 4  and R 6  independently represents a hydrogen atom, a normal or branched alkyl group having 1 to 18 carbon atoms, a normal or branched alkenyl group having 2 to 18 carbon atoms, a sulfonamide group, a mesyl group, a sulfonic acid group, a hydroxy group, an alkoxy group having 1 to 18 carbon atoms, an acetylamino group, a benzoylamino group, a halogen atom, or —COO—R 7 ;  
       R 7  represents a normal or branched alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms;  
       R 5  represents a hydrogen atom, a halogen atom, a nitro group, a carboxyl group, a normal or branched alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, —COO—R 8  or  
       
         
           
           
               
               
           
         
       
       R 8  represents a normal or branched alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms;  
       Y represents a hydrogen atom, a normal or branched alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a nitro group, or a halogen atom;  
       m represents an integer from 1 to 3;  
       M represents a divalent or trivalent metal;  
       p represents 1 or 2;  
       (A) q+  represents H + , NH 4   + , a cation based on an alkali metal, a cation based on an organic amine, or a quaternary organic ammonium ion;  
       q represents 1 or 2; and  
       X represents 1 or 2.  
     
     
         6 . Monoazo metal complex compound containing composition of  claim 5  wherein R 2  in Formula (1) above is Cl;  
       each of R 1  and R 3  through R 5  is a hydrogen atom;  
       R 6  is a hydrogen atom or a normal or branched alkyl group having 1 to 18 carbon atoms;  
       M is Cr, Fe, or Cu; and  
       (A) q+  is H + .  
     
     
         7 . Method for producing a monoazo metal complex compound containing composition which comprises a step for removing impurity substances using an alcoholic organic solvent, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         8 . Method for producing the monoazo metal complex compound containing composition of  claim 7  wherein said skin sensitization potential test is a skin sensitization potential test based on the maximization method.  
     
     
         9 . Method for producing the monoazo metal complex compound containing composition of  claim 7  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         10 . Method for producing the monoazo metal complex compound containing composition of  claim 8  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         11 . Method for producing the monoazo metal complex compound containing composition of  claim 7 ,  8 ,  9  or  10  wherein said alcoholic organic solvent is one member or a mixture of two or more members selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, n-butanol, ethylene glycol, propylene glycol monomethyl ether and ethylene glycol monoethyl ether.  
     
     
         12 . Method for producing a monoazo metal complex compound containing composition which comprises a step for synthesizing a monoazo metal complex compound in an alcoholic organic solvent, and a step for removing impurity substances from the product of the synthetic step using an alcoholic organic solvent, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         13 . Method for producing the monoazo metal complex compound containing composition of claims  12  wherein said skin sensitization potential test is a skin sensitization potential test based on the maximization method.  
     
     
         14 . Method for producing the monoazo metal complex compound containing composition of claims  12  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         15 . Method for producing the monoazo metal complex compound containing composition of claims  13  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         16 . Method for producing the monoazo metal complex compound containing composition of  claim 12 ,  13 ,  14  or  15  wherein said alcoholic organic solvent is one member or a mixture of two or more members selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, n-butanol, ethylene glycol, propylene glycol monomethyl ether and ethylene glycol monoethyl ether.  
     
     
         17 . Method for producing a monoazo metal complex compound containing composition which comprises a step for synthesizing a monoazo metal complex compound in an alcoholic organic solvent, and a step for removing impurity substances by directly filtering a reaction mixture containing the product obtained by the synthetic step, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         18 . Method for producing the monoazo metal complex compound containing composition of claims  17  wherein said skin sensitization potential test is a skin sensitization potential test based on the maximization method.  
     
     
         19 . Method for producing the monoazo metal complex compound containing composition of claims  18  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         20 . Method for producing the monoazo metal complex compound containing composition of claims  19  wherein the purity of said monoazo metal complex compound is not less than 90% as determined by high performance liquid chromatography.  
     
     
         21 . Method for producing the monoazo metal complex compound containing composition of  claim 17 ,  18 ,  19  or  20  wherein said alcoholic organic solvent is one member or a mixture of two or more members selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, n-butanol, ethylene glycol, propylene glycol monomethyl ether and ethylene glycol monoethyl ether.  
     
     
         22 . Charge control agent comprising a monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         23 . Toner for developing electrostatic images which contains a charge control agent comprising a monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         24 . Coloring agent containing the monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.  
     
     
         25 . Colored thermoplastic resin composition containing the monoazo metal complex compound containing composition as a coloring agent, the incidence of skin sensitization in a skin sensitization potential test of said composition being not more than 20%.