Colorant compounds containing copolymerizable vinyl groups
AssigneeEastman Chemical Company
InventorsMichael John Cyr, Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Phillip Michael Cook
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Abstract
Disclosed are novel colorant compounds which contain one or more ethylenically-unsaturated (vinyl), photopolymerizable radicals which may be copolymewrized (or cured) with ethylenically-unsaturated monomers to produce colored compositions such as colored acrylic coatings and polymers, e.g., coatings and polymers produced from acrylate and methacrylate esters, colored polystyrenes, and similar colored polymeric materials derived from other ethylenically-unsaturated monomers. The present invention also pertains to processes for the preparation of certain of the photopolymerizable colorant compounds.
Claims8
Photopolymerizable colorant compounds having Formula I:
- A—(—CO2—X)n I
- wherein
- A, is a mono-, di-, tri- or tetravalent anthrapyridone chromophore;
- X is —R1—O-Q or the phtopolymerizable group —CH2—C6H4-p-C(R2)═CH2;
- R1 is C2–C8 alkylene, —(—CH2CH2O—)m—CH2CH2- or 1,4-cyclohexylenedimethylene;
- R2 is hydrogen or C1–C6 alkyl;
- n is 1 to 4;
- m is 1–3;
- Q is a photopolymerizable group selected from an organic radical having the formula:
- —COC(R3)═CH—R4 Ia
- —CONHCOC(R3)═CH—R4 IIa
- —CONH—C1–C6-alkylene OCOC(R3)═CH—R4 IIIa
- —COCH═CH—CO2R7Va
- 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 and 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;
- or aryl;
- or R5 and R6 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;
- and
- R8 is hydrogen, C1–C6 alkyl or aryl.
A photopolymerizable anthrapyridone colorant having the formula
- wherein
- R28 is hydrogen, 4—C1–C6 alkoxy, 4-arylthio, 4-aryloxy, 4—C1–C6 alkylthio, 4—C1–C6 alkylsulfonyl, 4-arylsulfonyl, and 4-halogen;
- R30 is hydrogen, C1–C8 alkyl, substituted C1–C8 alkyl, or aryl;
- R31 is hydrogen, cyano, C1–C6 alkoxy, C1–C6 alkylthio, halogen, C1–C6 alkylsulfonyl, arylsulfonyl, aryl, arylthio, heteroaryl, heteroarylthio, C2–C6 alkoxycarbonyl, or aroyl;
- L4 is 6—NH—or 6—S—;
- and X is —CH2—C6H4-4—C(R2)═CH2, wherein R2 is hydrogen or methyl, or —R1—O-Q, wherein R1 is —(CH2)2-4—, —CH2CH(CH3)—, —CH2C(CH3)2CH2—, —(CH2CH2O—)1-2CH2CH2—, —CH2CH(OH)CH2—, or CH2—C6H10-4—CH2—, and Q is —COC(R3)═CH2, wherein R3 is hydrogen or methyl;
- or X is —CONHC(CH3)2—C6H4-4—C(CH3)═CH2.
A photopolymerizable anthrapyridone colorant compound having the formula
- wherein
- R28 is hydrogen, 4—C1–C6 alkoxy, 4-arylthio, 4-heteroarylthio, 4-aryloxy, 4—C1–C6 alkylthio, 4—C1–C6 alkylsulfonyl, 4-arylsulfonyl, or 4-halogen;
- R30 is hydrogen, C1–C8 alkyl, substituted C1–C8 alkyl, or aryl;
- R31 is hydrogen, cyano, C1–C6 alkoxy, C1–C6 alkylthio, halogen, C1–C6 alkylsulfonyl, arylsulfonyl, aryl, arylthio, heteroaryl, heteroarylthio, C2–C6 alkoxycarbonyl, or aroyl;
- L4 is 6—NH—or 6—S—;
- and X is —CH2—C6H4-4—C(R2)═CH2, wherein R2 is hydrogen or methyl, or —R1—O-Q, wherein R1 is —(CH2)2-4—, —CH2CH(CH3)—,—CH2C(CH3)2CH2, ——(CH2CH2O—) 1-2CHCH2—, —CH2CH(OH)CH2—, or CH2—C6H10—4—CH2—, and Q is —COC(R3)═CH2, wherein R3 hydrogen or methyl, or X is—CONHC(CH3)2—C6H4—4—C(CH3)═CH2.
Dependencies are inferred from the claim text.