Monoazo metal complex compound containing composition and production method thereof

Molded resin product made of a colored thermoplastic molding resin composition in molded form, consisting essentially of a purified monoazo metal complex compound containing colorant composition and a thermoplastic resin, the monoazo metal complex compound containing colorant being formed by the steps of providing a non-purified monoazo metal complex compound and purifying the non-purified monoazo metal complex compound to provide a purified monoazo metal complex compound containing colorant composition with the incidence of skin sensitization in a skin sensitization potential test, based on the maximization method, of said purified monoazo metal complex compound containing colorant composition being not more than 20%, the purity of said purified monoazo metal complex compound containing colorant composition being not less than 90% as determined by separation of the colorant composition by high performance liquid chromatography, wherein the purity corresponds to the peak area percent of the monoazo metal complex peak using detection at 313 nm, said purified monoazo metal complex compound containing colorant composition containing less than 10% of impurity substances of said non-purified monoazo metal complex compound associated with monoazo dyes and byproducts and impurity substances associated with metallization of monoazo dyes as determined by high performance liquid chromatography, said monoazo metal complex compound being a compound of the following formula (1):

• wherein each of R1 through R4 and R6 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—R7;
• R7 represents a normal or branched alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms;
• R5 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—R8 or
• R8 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+, NH4+, 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.

Method of providing a colored thermoplastic molding resin composition, the method comprising;

• providing a thermoplastic resin;
• providing a non-purified monoazo metal complex compound;
• purifying the non-purified monoazo metal complex compound to provide a purified monoazo metal complex compound containing colorant composition, the incidence of skin sensitization in a skin sensitization potential test, based on the maximization method, of said purified monoazo metal complex compound containing colorant composition being not more than 20%, the purity of said purified monoazo metal complex compound being not less than 90% as determined by separation of the colorant composition by high performance liquid chromatography, wherein the purity corresponds to the peak area percent of the monoazo metal complex peak using detection at 313 nm, said purified monoazo metal complex compound containing colorant composition containing less than 10% of impurity substances of said non-purified monoazo metal complex compound as determined by high performance liquid chromatography;
• mixing the purified monoazo metal complex compound containing colorant composition with said thermoplastic resin, said purified monoazo metal complex compound being a compound of the following formula (1):
• wherein each of R1 through R4 and R6 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—R7;
• R7 represents a normal or branched alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms;
• R5 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—R8 or
• R8 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+, NH4+, 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.

Method of providing a molded resin product, the method comprising:

• providing a colored thermoplastic molding resin composition in molded form, the resin composition consisting essentially of a thermoplastic resin and a monoazo metal complex compound containing colorant composition, the incidence of skin sensitization in a skin sensitization potential test, based on the maximization method, of said colorant composition being not more than 20%, the purity of said monoazo metal complex compound being not less than 90% as determined by separation of the colorant composition by high performance liquid chromatography, wherein the purity corresponds to the peak area percent of the monoazo metal complex peak using detection at 313 nm, said colorant composition containing less than 10% of remaining starting materials and impurity substances associated with monoazo dyes and byproducts and impurity substances associated with metallization of monoazo dyes relative to said colorant composition as determined by high performance liquid chromatography;
• and
• molding the resulting resin composition including the monoazo metal complex compound containing colorant composition to form a molded resin product, said monoazo metal complex compound being a compound of the following formula (1):
• wherein each of R1 through R4 and R6 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—R7;
• R7 represents a normal or branched alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms;
• R5 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—R8 or
• R8 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+, NH4+, 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.