Non-aqueous dispersing agent and liquid developing agent for electrostatic photography

Claim 2

A liquid developing agent for electrostatic photography, which contains one or more of a pigment or dye, a resin insoluble in or swellable with a carrier liquid and a pigment or dye as coated with the resin, and a dispersing agent and a charge-adjusting agent in a non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, wherein the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerizable functional group, wherein the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at least one mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (2) at least one monomer represented by formula (III), said monofunctional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR115## wherein V is ##STR116## (wherein Z 1 is hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which may be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted: ##STR117## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 22 carbon atoms or an aromatic group having from 6 to 12 carbon atoms; Q is ##STR118## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and B 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR119## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macrometer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms.

Claim 3

A liquid developing agent for electrostatic photography, which contains one or more of a pigment or dye, a resin insoluble in or swellable with a carrier liquid and a pigment or dye as coated with the resin, and a dispersing agent and a charge-adjusting agent in a non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, wherein the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerizable functional group, wherein the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at least a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (2) at least one monomer represented by formula (III), said monofunctional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR120## wherein V is ##STR121## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which may be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted: ##STR122## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 22 carbon atoms or an aromatic group having from 6 to 12 carbon atoms; Q is ##STR123## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR124## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms, and wherein said graft copolymer is a copolymer having a polar group selected from --PO 3 H 2 , --SO 3 H, --COOH, --OH, ##STR125## --P--Z 0 (wherein Z 0 is --Z 10 or --OZ 10 (wherein Z 10 is a hydrocarbon group)), a formyl group, and an amino group at one terminal of a polymer main chain.

Claim 4

A liquid developing agent for electrostatic photography, which contains one or more of a pigment or dye, a resin insoluble in or swellable with a carrier liquid and a pigment or dye as coated with the resin, and a dispersing agent and a charge-adjusting agent in a non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, wherein the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerizable functional group, wherein the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at least a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (2) at least one monomer represented by formula (III), said monofunctional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR120## wherein V is ##STR121## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which may be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted: ##STR122## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 22 carbon atoms or an aromatic group having from 6 to 12 carbon atoms; Q is ##STR123## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR124## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms, and wherein said graft copolymer is a copolymer having a polar group selected from --PO 3 H 2 , --SO 3 H, --COOH, --OH, ##STR125## --P--Z 0 (wherein Z 0 is --Z 10 or --OZ 10 (wherein Z 10 is a hydrocarbon group)), a formyl group, and an amino group at one terminal of a polymer main chain.

Claim 5

A liquid developing agent to be employed in a method of forming printing plates where an electrostatic latent image as formed on the surface of a printing plate precursor comprising an electroconductive support and an electrophotographic light-sensitive layer as provided on the support is developed with a liquid developing agent and thereafter the non-image portions are dissolved to give a printing plate, the liquid developing agent containing at least a resin insoluble in or swellable with a carrier liquid and/or a dye or pigment as coated with the resin, and a dispersing agent and a charge-adjusting agent in a high electric-resistance non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, in which the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerization functional group, wherein the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at least a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (2) at least one monomer represented by formula (III), said mono-functional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR126## wherein V is ##STR127## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which may be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted: ##STR128## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 12 carbon atoms or an aromatic group having from 6 to 12 carbon atoms, Q is ##STR129## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR130## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms.

Claim 6

A liquid developing agent to be employed in a method of forming printing plates where an electrostatic latent image as formed on the surface of a printing plate precursor comprising an electroconductive support and an electrophotographic light-sensitive layer as provided on the support is developed with a liquid developing agent and thereafter the non-image portions are dissolved to give a printing plate, the liquid developing agent containing at least a resin insoluble in or swellable with a carrier liquid and/or a dye or pigment as coated with the resin, and a dispersing agent and a charge-adjusting agent in a high electric-resistance non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, in which the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerization functional group, wherein the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at least a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (2) at least one monomer represented by formula (III), said mono-functional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR126## wherein V is ##STR127## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which may be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted: ##STR128## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 12 carbon atoms or an aromatic group having from 6 to 12 carbon atoms, Q is ##STR129## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR130## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms.

Claim 7

A liquid developing agent to be employed in a method of forming printing plates where an electrostatic latent image as formed on the surface of a printing plate precursor comprising an electroconductive support and an electrophotographic light-sensitive layer as provided on the support is developed with a liquid developing agent and thereafter the non-image portions are dissolved to give a printing plate, the liquid developing agent containing at least a resin insoluble in or swellable with a carrier liquid and/or a dye or pigment as coated with the resin, and a dispersing agent and a charge-adjusting agent in a high electric-resistance non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, in which the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerizable functional group and that the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at lest a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (20 at least one monomer represented by formula (III), said mono-functional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR131## wherein V is ##STR132## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which ma be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted): ##STR133## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 22 carbon atoms or an aromatic group having from 6 to 12 carbon atoms; Q is ##STR134## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR135## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms and wherein said graft copolymer is a copolymer having a polar group selected from --PO 3 H 2 , --SO 3 H, --COOH, --OH, ##STR136## --P--Z 0 (wherein Z 0 is --Z 10 or --OZ 10 (wherein Z 10 is a hydrocarbon group)), a formyl group, and an amino group at one terminal of a polymer main chain.

Claim 8

A liquid developing agent to be employed in a method of forming printing plates where an electrostatic latent image as formed on the surface of a printing plate precursor comprising an electroconductive support and an electrophotographic light-sensitive layer as provided on the support is developed with a liquid developing agent and thereafter the non-image portions are dissolved to give a printing plate, the liquid developing agent containing at least a resin insoluble in or swellable with a carrier liquid and/or a dye or pigment as coated with the resin, and a dispersing agent and a charge-adjusting agent in a high electric-resistance non-aqueous solvent carrier liquid having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, in which the dispersing agent comprises a graft copolymer, wherein monomer(s) to constitute the graft portion(s) of the graft copolymer is(are) at least one or more macromonomers each having a terminal polymerizable functional group and that the graft copolymer is substantially soluble in a non-aqueous solvent having a dielectric constant of 3 or less and a volume specific resistance of 10 9 Ωcm or more, and wherein said graft copolymer is a copolymer comprising (1) at lest a mono-functional macromonomer (M) having a weight average molecular weight of from 1×10 3 to 4×10 4 , and (20 at least one monomer represented by formula (III), said mono-functional macromonomer (M) having a polymerizable double bond group represented by formula (I) bonded to only one terminal of a polymer main chain containing at least one kind of a polymer component represented by formula (IIa) or (IIb): ##STR131## wherein V is ##STR132## (wherein Z 1 is a hydrogen atom or a hydrocarbon group and l represents an integer of from 1 to 3); a 1 and a 2 , which ma be the same or different, each is a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COO--Z 2 , or --COO--Z 2 bonded via a hydrocarbon group (wherein Z 2 is a hydrogen atom or a hydrocarbon group which may be substituted): ##STR133## wherein X 0 has the same meaning as V in formula (I); Q 0 is an aliphatic group having from 1 to 22 carbon atoms or an aromatic group having from 6 to 12 carbon atoms; Q is ##STR134## wherein Y is a hydrogen atom, a halogen atom, an alkoxy group, or --COOZ 3 (wherein Z 3 is an alkyl group, an aralkyl group, or an aryl group); and b 1 and b 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I): ##STR135## wherein X 1 has the same meaning as X 0 in formula (IIa); Q 1 has the same meaning as Q 0 in formula (IIa); and d 1 and d 2 , which may be the same or different, have the same meanings as a 1 and a 2 in formula (I); with the proviso that, in the component of the macromonomer (M) represented by formula (IIa) and in the component of the monomer represented by formula (III), at least one of Q 0 and Q 1 is an aliphatic group having from 8 to 22 carbon atoms and wherein said graft copolymer is a copolymer having a polar group selected from --PO 3 H 2 , --SO 3 H, --COOH, --OH, ##STR136## --P--Z 0 (wherein Z 0 is --Z 10 or --OZ 10 (wherein Z 10 is a hydrocarbon group)), a formyl group, and an amino group at one terminal of a polymer main chain.