Colorants containing copolymerizable vinyl groups and sulfonamide linkages
AssigneeEastman Chemical Company
InventorsMichael John Cyr, Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Phillip Michael Cook, Jos Simon De Wit, Larry Keith Johnson
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Abstract
Disclosed are thermally-stable, colored, photopolymerizable compounds containing a vinyl group which are capable of being copolymerized with reactive vinyl monomers to produce colored compositions such as polyacrylates, polymethacrylates, polystyrene, etc. The compounds exhibit good thermal stability, fastness (stability) to UV-light, good solubility in the reactive monomers and good color strength.
Claims28
A photopolymerizable colorant compound having tie formula:
- wherein
- A is a mono-, di-, tri- or tetravalent chromophore;
- R1 is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, C3-C8 cycloalkyl, aryl or —R2—OQ;
- R2 is C2-C8 alkylene, arylene, C3-C8 cycloalkylene, arylene-C1-C6 alkylene, arylene-oxy-C1-C6 alkylene, arylenethio-C1-C6 alkylene, 1,4-cyclohexylenedimethylene or —(—CH2CH2O)m—CH2CH2—;
- m is 1-3;
- n is 1-4;
- Q is an ethylenically-unsaturated, photopolymerizable group selected from the following organic radicals:
- wherein
- R3 is hydrogen or C1-C6 alkyl;
- R4 is hydrogen, C1-C6 alkyl;
- phenyl;
- phenyl substituted with one or more groups selected from C1-C6 alkyl, C1-C6 alkoxy, —N(C1-C6 alkyl)2, nitro, cyano, C2-C6 alkoxycarbonyl, C2-C6 alkanoyloxy or halogen;
- 1- or 2-naphthyl;
- 1- or 2-naphthyl substituted with C1-C6 alkyl or C1-C6 alkoxy;
- 2- or 3-thienyl;
- 2- or 3-thienyl substituted with C1-C6 alkyl or halogen;
- 2- or 3-furyl;
- or 2- or 3-furyl substituted with C1-C6 alkyl;
- R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, aryl or may be combined to represent a —(—CH2—)—3-5 radical;
- R7 is hydrogen or C1-C6 alkyl, substituted C1-C6 alkyl, C3-C8 alkenyl, C3-C8 cycloalkyl or aryl;
- R8 is selected from hydrogen, C1-C6 alkyl or aryl;
- and
- A is a chromophore selected from residues of anthraquinone, anthrapyridone, anthrapyrimidine, anthrapyridine, anthrapyrazole, anthraisothiazole, 14H-naptho[2,3-a]-phenothiazine-8,13-dione, methine, bis-methine, perinone, coumarin, quinophthalone, 3-aryl-2,5-dioxypyrroline, or 3-aryl-5-dicyanomethylene-2-oxypyrroline.
A photopolymerizable colorant according to claim 4 having the formula:
A photopolymerizable colorant according to claim 7 wherein
- R1 is hydrogen, C1-C6 alkyl, or —R2—OQ;
- R2 is C2-C8 alkylene, arylene, C3-C8 cycloalkylene, arylene-C1-C6 alkylene, arylene-oxy-C1-C6 alkylene, arylenethio-C1-C6 alkylene, 1,4-cyclohexylenedimethylene or —(—CH2CH2O)m—CH2CH2—;
- m is 1-3;
- R17 is amino;
- C1-C8-alkylamino, substituted C1-C8-alkylamino as defined above, C3-C8-cycloalkylamino, C3-C8-alkenylamino, C3-C8-alkynylamino or arylamino;
- R18 is halogen, amino, C1-C8 alkylamino, substituted C1-C8-alkylamino, C3-C8-cycloalkylamino, C3-C8-alkenylamino, C3-C8-alkynylamino, arylamino, hydroxy, arylthio, heteroarylthio, C2-C6-alkanoylamino, aroylamino, C1-C6-alkylsulfonylamino, or arylsulfonylamino;
- and
- Q is —COC(R3)═CH2 wherein R3 is hydrogen or methyl.
A coating composition according to claim 15 comprising (i) one or more polymerizable vinyl compounds, (ii) one or more of the colorant compounds of claim 2 present in a concentration of about 0.05 to 15 weight percent based on the weight of component (i), and (iii) a photoinitiator present in a concentration of about 1 to 15 weight percent based on the weight of the polymerizable vinyl compound(s) present in the coating composition.
A coating composition according to claim 16 wherein the polymerizable vinyl compounds comprise a solution of a polymeric, polymerizable vinyl compound selected from acrylated or methacrylated polyesters, acrylated or methacrylated polyethers, acrylated or methacrylated epoxy polymers, acrylated or methacrylated urethanes, or mixtures thereof, in a diluent selected from monomeric acrylate or methacrylate esters.
A photopolymerizable colorant having the formula:
- wherein
- A is a residue of phthalocyanine or metal pthalocyanine;
- R1 is hydrogen, C1C6 alkyl, substituted C1-C6 alkyl, C3 -C8 cycloalkyl, aryl or —R2-OQ;
- R2 is C2-C8 alkylene, arylene, C3-C8 cycloalkylene, arylene —C1-C6 alkylene, arylene—oxy—C1-C6 alkylene, arylenethio —C1-C6 alkylene, 1,4-cyclohexylenedimethylene or —(—CH2CH2O)m—CH2CH2—;
- m is 1-3;
- n is 1-4;
- Q is —COC(R3)=CH-R4;
- R2 is C1-C6 alkyl;
- and
- R4 is hydrogen, C1-C6 alkyl;
- phenyl substituted with one or more groups selected from C1-C6 alkyl, C1-C6 alkoxy, —N(C1-C6 alkyl)2, nitro, cyano, C2-C6 alkoxycarbonyl, C2-C6 alkanoyloxy or halogen;
- 1- or 2-naphthyl;
- 1- or 2-naphthyl substituted with C1-C6 alkyl or C1-C6 alkoxy;
- 2- or 3-thienyl substituted with C1-C6 alkyl or halogen;
- 2- or 3- furyl;
- or 2- or 3-furyl substituted with C1-C6 alkyl.
A photopolymerizable colorant compound having the formula
- wherein
- A is a residue of phthalocyanine or metal phthalocyanine;
- R1 is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, C3-C8 cycloalkyl, aryl or —R2-OQ;
- R2 is C2-C8 alkylene, arylene, C3-C8 cycloalkylene, arylene —C1-C6 alkylene, arylene-oxy-C1-C6 alkylene, arylenethio —C1-C6 alyklene, 1,4-cyclohexylenedimethylene or —(—CH2CH2O)m—CH2CH2—;
- m is 1-3;
- n is 1-4;
- Q is an ethylenically-unsaturated, photopolymerizable group selected from the following organic radicals;
- wherein
- R3 is hydrogen or C1-C6 alkyl;
- R4 is hydrogen, C1-C6 alkyl;
- phenyl;
- phenyl substituted with one or more groups selected from C1-C6 alkyl, C1-C6 alkoxy, —N(C1-C6 alkyl)2, nitro, cyano, C2-C6 alkoxycarbonyl, C2-C6 alkanoyloxy or halogen;
- 1- or 2-naphthyl;
- 1- or 2-naphthyl substituted with C1-C6 alkyl or C1-C6 alkoxy;
- 2- or 3-thienyl;
- 2- or 3-thienyl substituted with C1-C6 alkyl or halogen;
- 2- or 3- furyl;
- or 2- or 3-furyl substituted with C1-C6 alkyl;
- R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, aryl or may be combined to represent a —(—CH2—)—3-5 radical;
- R7 is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, C3-C8 alkenyl, C3-C8 cycloalkyl or aryl;
- and
- R8 is hydrogen, C1-C6 alkyl or aryl.
Dependencies are inferred from the claim text.