Method for preparation of an anthraquinone colorant composition

Abstract

Disclosed herein is a method for producing a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition where the method comprises: reacting 4-halobenzoic acid with about 1 mole to about 4 moles of a halogenating agent per mole of said 4-halobenzoic acid to form a 4-halobenzoyl halide composition; reacting in the presence of a first catalyst composition, said 4-halobenzoyl halide composition with biphenyl, in a solvent, to form a 1-[4-(biphenyl-4-carbonyl)]halobenzene composition; and reacting in the presence of a second catalyst composition and an acid scavenger, said 1-[4-(4-phenylbenzoyl)]halobenzene composition with a 1-aminoanthraquinone, in a reaction medium comprising a dipolar aprotic solvent, to form said 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition.

1 . A method for producing a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition, said method comprising: 
 reacting a 4-halobenzoic acid with about 1 mole to about 4 moles of a halogenating agent per mole of said 4-halobenzoic acid to form a 4-halobenzoyl halide composition;    reacting in the presence of a first catalyst composition, said 4-halobenzoyl halide composition with biphenyl, in a solvent to form a 1-[4-(biphenyl-4-carbonyl)]halobenzene composition; and    reacting in the presence of a second catalyst composition and an acid scavenger, said 1-[4-(4-phenylbenzoyl)]halobenzene composition with a 1-aminoanthraquinone, in a reaction medium comprising a dipolar aprotic solvent, to form said 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition.    
     
     
         2 . The method of  claim 1 , wherein said reacting 4-halobenzoic acid with a halogenating agent to form a 4-halobenzoyl halide composition further is conducted in a solvent comprising aromatic compounds having from about 6 to about 9 carbon atoms, and aliphatic and alicyclic compounds having from about 1 to about 6 carbon atoms.  
     
     
         3 . The method of  claim 1 , wherein said 4-halobenzoic acid is at least one selected from the group consisting of 4-chlorobenzoic acid, 4-bromobenzoic acid, 4-iodobenzoic acid, and mixtures thereof.  
     
     
         4 . The method of  claim 1 , wherein said halogenating agent comprises a halogen-containing phosphorus compound, a halogen-containing sulfur compound, and a carbonyl halide.  
     
     
         5 . The method of  claim 1 , wherein said halogenating agent is selected from the group consisting of PCl 3 , PCl 5 , PBr 3 , POCl 3 , POBr 3 , carbonyl chloride, carbonyl bromide, thionyl chloride, thionyl bromide, sulfuryl chloride, and mixtures thereof.  
     
     
         6 . The method of  claim 1 , wherein said reacting 4-halobenzoic acid with a halogenating agent further is conducted in the presence of from about 0.1 parts to about 5 parts per 100 parts by weight of said 4-halobenzoic acid, of a catalyst comprising an amide compound or a urea compound.  
     
     
         7 . The method of  claim 1 , wherein said solvent comprises nitroaromatic compounds, nitroaliphatic compounds, and halogen-containing C 1 -C 4  aliphatic compounds,  
     
     
         8 . The method of  claim 1 , wherein reacting said 4-halobenzoyl halide composition with biphenyl is carried out at from about an ambient temperature to about 200° C.  
     
     
         9 . The method of  claim 1 , wherein reacting said 4-halobenzoyl halide composition with biphenyl is carried out at from about 50° C. to about 200° C.  
     
     
         10 . The method of  claim 1 , wherein reacting said 4-halobenzoyl halide composition with biphenyl is carried out for a duration from about 1 hours to about 10 hours.  
     
     
         11 . The method of  claim 1 , wherein reacting said 4-halobenzoyl halide composition with biphenyl is carried out for a duration from about 2 hours to about 8 hours.  
     
     
         12 . The method of  claim 1 , wherein said first catalyst composition comprises an inorganic halide having the formula M 1 X m , wherein “M 1 ” is at least one element selected from groups 3 to 15 of the Periodic Table; and “m” is an integer having a value from about 2 to about 5.  
     
     
         13 . The method of  claim 1 , wherein said first catalyst composition comprises at least one of zinc(II) chloride, aluminum(III) chloride, boron(III) fluoride etherate, and iron(III) chloride.  
     
     
         14 . The method of  claim 1 , wherein said first catalyst composition comprises from about 90 moles to about 100 moles per 100 moles of said 4-halobenzoyl chloride.  
     
     
         15 . The method of  claim 1 , wherein said dipolar aprotic solvent is selected from the group consisting of N,N-dimethylformamide, N-methyl-3-pyrrolidinone, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, and sulfolane, and mixtures comprising any of the foregoing solvents.  
     
     
         16 . The method of  claim 1 , wherein reacting said 1-[4-(4-phenylbenzoyl)]halobenzene composition with said 1-aminoanthraquinone is carried out at a temperature of from about 50° C. to about 200° C.  
     
     
         17 . The method of  claim 1 , wherein reacting said 1-[4-(4-phenylbenzoyl)]halobenzene composition with said 1-aminoanthraquinone is carried out at a temperature of from about 100° C. to about 170° C.  
     
     
         18 . The method of  claim 1 , wherein reacting said 1-[4-(4-phenylbenzoyl)]halobenzene composition with said 1-aminoanthraquinone is carried out for a period from about 12 hours to about 30 hours.  
     
     
         19 . The method of  claim 1 , wherein reacting said 1-[4-(4-phenylbenzoyl)]halobenzene composition with said 1-aminoanthraquinone is carried out for a period from about 18 hours to about 24 hours.  
     
     
         20 . The method of  claim 1 , wherein said second catalyst composition comprises of copper, CuX, and CuX 2 , wherein “X” is selected from chloride, bromide, iodide, and a mixture thereof.  
     
     
         21 . The method of  claim 1 , wherein said second catalyst composition comprises copper and CuI.  
     
     
         22 . The method of  claim 1 , wherein said second catalyst composition comprises about 0.05 parts to about 25 parts per 100 parts by weight of 1-aminoanthraquinone.  
     
     
         23 . The method of  claim 1 , wherein said acid scavenger comprises alkali metal carbonates, alkaline earth metal carbonates, alkali metal bicarbonates; alkaline earth metal bicarbonates, and alkali metal carboxylates and alkaline earth metal carboxylates having the general formula M(COOR 1 ) n , wherein “M” is an alkali metal or an alkaline earth metal, R 1  is a monovalent alkyl group having from about 1 to about 6 carbons, and “n” is selected from 1 and 2.  
     
     
         24 . A thermoplastic resin composition comprising a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition prepared according to the method of  claim 1 .  
     
     
         25 . The method of  claim 24 , wherein said thermoplastic resin is selected from the group consisting of polyesters, polycarbonates, bisphenol A polycarbonate, polyamides, polyimides, polyamideimides, polystyrenes, rubber-modified polystyrenes, acrylonitrile-containing polymers, polyarylene ethers, poly(2,6-dimethyl-1,4-phenylene ether) and any combination thereof.  
     
     
         26 . A method for producing a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition, said method comprising: 
 reacting one mole of a 4-bromobenzoic acid with about 1.1 moles to about 4 moles of thionyl chloride per mole of 4-bromobenzoic acid to form a 4-bromobenzoyl chloride composition;    reacting in the presence of aluminum chloride, said 4-bromobenzoyl chloride composition with biphenyl in a solvent comprising nitrobenzene, to form a 1-[4(biphenyl-4-carbonyl)]bromobenzene composition; and    reacting in the presence of an acid scavenger comprising potassium carbonate and sodium acetate, and a second catalyst composition comprising about 1 part of copper per part by weight of copper(I) iodide, said 1-[4-(4-phenylbenzoyl)]bromobenzene composition with a 1-aminoanthraquinone in a solvent comprising N,N-dimethylformamide, to form said 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition.    
     
     
         27 . A thermoplastic resin composition comprising a 1-[4-(biphenyl-4-carbonyl)]phenylaminoanthraquinone colorant composition prepared according to the method of  claim 26 .  
     
     
         28 . The method of  claim 27 , wherein said thermoplastic resin is selected from the group consisting of polyesters, polycarbonates, bisphenol A polycarbonate, polyamides, polyimides, polyamideimides, polystyrenes, rubber-modified polystyrenes, acrylonitrile-containing polymers, polyarylene ethers, poly(2,6-dimethyl1,4-phenylene ether) and any combination thereof.