Microcapsule toner compositions

Claim 2

A microcapsule toner, consisting essentially of a core comprising a colorant and a binder polymer; and a shell surrounding said core and comprising a shell polymer; wherein a part of said binder polymer is chemically grafted to said shell polymer via a spacer linkage which is a reaction product of a polyfunctional reagent with precursors of said binder polymer and said shell polymer.

Claim 3

A toner according to claim 1, wherein a layer of said binder polymer is chemically bonded to an inner surface of said shell.

Claim 4

A toner according to claim 1, wherein the binder polymer is selected from the group consisting of acrylate polymers, methacrylate polymers, styrene and styrene polymers; and the shell polymer is selected from the group consisting of polyureas, polyether-ureas, polyurethanes, polyamides, polyesters, and mixtures thereof.

Claim 5

A toner according to claim 3, wherein the binder polymer is an acrylate copolymer, a methacrylate copolymer, or a styrene copolymer.

Claim 6

A toner according to claim 1, wherein the polyfunctional reagent comprises at least one condensation functionality and at least one free radical polymerizable functionality.

Claim 7

A toner according to claim 5, wherein the condensation functionality is NCO, COCl, COBr, OCOCl, OH, or NH 2 ; and the free radical polymerizable functionality is a vinyl group.

Claim 8

A toner according to claim 1, wherein the shell polymer is a polyurea, and the binder polymer is an alkyl methacrylate polymer.

Claim 9

A toner according to claim 1, wherein the shell polymer is a polyurea, and the binder polymer is an alkyl acrylate polymer.

Claim 10

A toner according to claim 1, wherein the shell polymer is a polyurea, and the binder polymer is an acrylate or methacrylate copolymer.

Claim 11

A toner according to claim 1, wherein the toner contains surface additives.

Claim 12

A toner according to claim 10, wherein the surface additives are selected from the group consisting of conductive additives, flow aids and surface release agents.

Claim 13

A toner according to claim 10, wherein the surface additives are selected from the group consisting of carbon colloidal silica, and zinc stearate.

Claim 14

A toner according to claim 1, wherein said polyfunctional reagent is selected from the group consisting of isocyanato-ethyl methacrylate, 2-isocyanato-ethyl acrylate, 3-isocyanato-propyl methacrylate, 3-isocyanatopropyl acrylate, isocyanato-butyl methacrylate, isocyanato-butyl acrylate, isocyanato-pentyl methacrylate, isocyanato-pentyl acrylate, isocyanato-hexyl methacrylate, isocyanato-hexyl methacrylate, isocyanato-heptyl methacrylate, isocyanato-heptyl acrylate, isocyanato-octyl methacrylate, isocyanato-octyl acrylate, isocyanato-lauryl methacrylate, isocyanato-dodecane methacrylate, m-isocyanato-styrene, p-isocyanato-styrene, o-isocyanatostyrene, m-isocyanato-alpha-methyl styrene, o-isocyanato-alpha-methyl styrene, p-isocyanato-alpha-methyl styrene, (3-isocyanato-phenyl)-methacrylate, (2-isocyanato-phenyl)-methacrylate, (4-iso-cyanato-phenyl)-methacrylate, (3-isocyanato-phenyl)-acrylate, 2-amino-ethyl acrylate, 3-amino-propyl methacrylate, 3-amino-propyl acrylate, amino-butyl methacrylate, amino-butyl acrylate, amino-pentyl methacrylate, amino-pentyl acrylate, amino-hexyl methacrylate, amino-hexyl acrylate, amino-heptyl methacrylate, amino-heptyl acrylate, amino-octyl methacrylate, amino-octyl acrylate, amino-lauryl methacrylate, amino-dodecane methacrylate, 2-(2-amino-ethyl) acrylate, 3-amino-propyl methacrylate, 3-amino-propyl acrylate, amino-butyl methacrylate, amino-butyl acrylate, amino-pentyl methacrylate, amino-pentyl acrylate, amino-hexyl methacrylate, amino-hexyl methacrylate, amino-heptyl methacrylate, amino-heptyl acrylate, amino-octyl methacrylate, amino-octyl acrylate, amino-lauryl methacrylate, amino-dodecane methacrylate, and 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)-benzene.

Claim 15

A toner according to claim 1, wherein said polyfunctional reagent is selected from the group consisting of Bis-N,N'(2-hydroxyethyl) methacrylamide, Bis-N,N'(2-hydroxyethyl) acrylamide, Bis-N,N'(3-hydroxypropyl) methacrylamide, Bis-N,N'(3-hydroxypropyl) styrene, 2,3-diisocyanato-styrene, 2,5-diisocyanatostyrene, 3,5-diisocyanato-styrene, 2,3-diisocyanato-alpha-methylstyrene, 2,4-diisocyanato-alpha-methylstyrene, 2,5-diisocyanato-alpha-methylstyrene, 3,5-diisocyanato-alpha-methylstyrene, 3,5-diisocyanato-alpha-methylstyrene, Bis(N-ethyl-2-methacrylamido) amine, Bis(N-ethyl-2-acrylamido) amine, 2,4-diaminostyrene, 2,5-diaminostyrene, 3,5-diaminostyrene, 2,3-diaminostyrene, 2,4-diamino-alpha-methyl-styrene, 2,5-diamino-alpha-methyl-styrene, 3,5-diamino-alpha-methyl-styrene, 2,3-diamino-alpha-methyl-styrene, N-acryloyltris-(hydroxymethyl)-amino methane, 1,3-dimethacryloyl-4,6-diisocyanatobenzene, and 1,3-dimethaoryloyl-4,6-diamino-benzene.

Claim 16

A toner according to claim 1, wherein the polyfunctional reagent is represented by the formula Y-R-X wherein R is selected from the group consisting of polyalkylene, polysiloxane, polyether, and perfluorocarbon moieties; Y is methacryloxy, acryloxy, metharylamido, acrylamido or styryl; and X is --OH, --NH 2 , --NCO, --COCl, --OCOCl or epoxy.

Claim 17

A toner according to claim 1, wherein the polyfunctional reagent is ##STR4## wherein R is an alkyl group and n=10-1000.

Claim 18

A toner according to claim 1, wherein the toner comprises a volume particle size of from 7-19 microns.

Claim 19

The toner of claim 1, wherein the microcapsule toner is a dry toner.

Claim 20

The toner of claim 18, wherein the dry toner is a powder.

Claim 21

A process of preparing a microcapsule toner, comprising: forming a mixture comprising a core binder monomer, an oil soluble shell monomer, and a colorant; dispersing said mixture in an aqueous surfactant solution to form a homogeneous microdroplet suspension; subjecting said suspension to a shell forming interfacial polycondensation by adding to said suspension a water soluble shell monomer; and effecting a core binder forming polymerization, wherein binder is chemically grafted to the shell polymer via a spacer linkage which is a reaction product of a polyfunctional reagent with precursors of said core binder and said shell polymer.

Claim 22

A process of preparing a microcapsule toner, comprising: forming a mixture comprising a core binder monomer, an oil soluble shell monomer, and a colorant; dispersing said mixture in an aqueous surfactant solution to form a homogeneous microdroplet suspension; subjecting said suspension to a shell forming interfacial polycondensation by adding to said suspension a water soluble shell monomer; and effecting a core binder forming polymerization, wherein binder is chemically grafted to the shell polymer via a spacer linkage which is a reaction product of a polyfunctional reagent with precursors of said core binder and said shell polymer.

Claim 23

A process according to claim 20, wherein said core binder forming polymerization is a free radical polymerization.

Claim 24

A process according to claim 21, wherein the interfacial polycondensation is conducted at a temperature range of about room temperature to about 50° C., and wherein the free radical polymerization is conducted at a temperature range of about 30° C. to about 130° C.

Claim 25

A process according to claim 21, wherein the interfacial polycondensation is substantially completed before initiation of the free radical polymerization.

Claim 26

A process according to claim 20, wherein said polyfunctional reagent reacts with the oil soluble shell monomer during said dispersing step, and with the binder monomer during said core binder forming polymerization.

Claim 27

A process according to claim 20, wherein said polyfunctional reagent reacts with the water soluble shell monomer during the interfacial polycondensation, and reacts with the binder monomer during said core binder forming polymerization.

Claim 28

A process according to claim 20, wherein the polyfunctional reagent is represented by the formula Y-R-X wherein R is selected from the group consisting of polyalkylene, polysiloxane, polyether, and perfluorocarbon moieties; Y is methacryloxy, acryloxy, methacrylamido, acrylamido or styryl; and X is --OH, --NH 2 , --NCO, --COCl, --OCOCl or epoxy.

Claim 29

A process according to claim 20, wherein the polyfunctional reagent is ##STR5## wherein R is an alkyl group and n=10-1000.

Claim 30

A process according to claim 20, wherein said polyfunctional reagent is selected from the group consisting of isocyanato-ethyl methacrylate, 2-isocyanato-ethyl acrylate, 3-isocyanato-propyl methacrylate, 3-isocyanato-propyl acrylate, isocyanato-butyl methacrylate, isocyanato-butyl acrylate, isocyanato-pentyl methacrylate, isocyanato-pentyl acrylate, isocyanato-hexyl methacrylate, isocyanato-hexyl methacrylate, isocyanato-heptyl methacrylate, isocyanato-heptyl acrylate, isocyanato-octyl methacrylate, isocyanato-octyl acrylate, isocyanato-lauryl methacrylate, isocyanato-dodecane methacrylate, m-isocyanato-styrene, p-isocyanato-styrene, o-isocyanato-styrene, m-isocyanato-alpha-methyl styrene, o-isocyanato-alpha-methyl styrene, p-isocyanato-alpha-methyl styrene, (3-isocyanato-phenyl)-methacrylate, (2-isocyanato-phenyl)-methacrylate, (4-iso-cyanato-phenyl)-methacrylate, (3-isocyanato-phenyl)-acrylate, 2-amino-ethyl acrylate, 3-amino-propyl methacrylate, 3-amino-propyl acrylate, amino-butyl methacrylate, amino-butyl acrylate, amino-pentyl methacrylate, amino-pentyl acrylate, amino-hexyl methacrylate, amino-hexyl acrylate, amino-heptyl methacrylate, amino-heptyl acrylate, amino-octyl methacrylate, amino-octyl acrylate, amino-lauryl methacrylate, amino-dodecane methacrylate, 2-(2-amino-ethyl) acrylate, 3-amino-propyl methacrylate, 3-amino-propyl acrylate, amino-butyl methacrylate, amino-butyl acrylate, amino-pentyl methacrylate, amino-pentyl acrylate, amino-hexyl methacrylate, amino-hexyl methacrylate, amino-heptyl methacrylate, amino-heptyl acrylate, amino-octyl methacrylate, amino-octyl acrylate, amino-lauryl methacrylate, amino-dodecane methacrylate, 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)-benzene.

Claim 31

A process according to claim 20, wherein said polyfunctional reagent is selected from the group consisting of Bis-N,N'(2-hydroxyethyl) methacrylamide, Bis-N,N'(2-hydroxyethyl) acrylamide, Bis-N,N'(3-hydroxypropyl) methacrylamide, Bis-N,N'(3-hydroxy-propyl) acrylamide, 2,4-diisocyanato-styrene, 2,4-diiso-cyanato-styrene, 2,3-diisocyanato-styrene, 2,5-diiso-cyanato-styrene, 3,5-diisocyanato-styrene, 2,3-diiso-cyanato-alpha-methylstyrene, 2,4-diisocyanato-alpha-methylstyrene, 2,5-diisocyanato-alpha-methylstyrene, 3,5-diisocyanato-alpha-methylstyrene, 3,5-diisocyanato-alpha-methylstyrene, Bis(N-ethyl-2-methacrylamido) amine, Bis(N-ethyl-2-acrylamido) amine, 2,4-diaminostyrene, 2,5-diaminostyrene, 3,5-diaminostyrene, 2,3-diamino-styrene, 2,4-diamino-alpha-methyl-styrene, 2,5-diamino-alpha-methyl-styrene, 3,5-diamino-alpha-methyl-styrene, 2,3-diamino-alpha-methyl-styrene, N-acryloyltris-(hydroxy-methyl)-amino methane, 1,3-dimethacryloyl-4,6-diiso-cyanatobenzene, 1,3-dimethacryloyl-4,6-diamino-benzene.

Claim 32

A process according to claim 20, wherein the oil soluble shell monomer is a polyisocyanate or polyacyl halide, and the water soluble shell monomer is a polyamine, polyol or mixture thereof.

Claim 33

A process according to claim 20, wherein the binder monomer is an acrylate, methacrylate or styryl monomer.

Claim 34

A process according to claim 20, wherein said average diameter of said microcapsule is from about 3 to about 30 microns.

Claim 35

A process according to claim 20, wherein said mixture further comprises a preformed core binder.

Claim 36

A process according to claim 20, wherein said colorant comprises a color pigment, a dye or a mixture thereof.

Claim 37

A process according to claim 20, wherein said mixture further comprises an organic diluent.

Claim 38

A process according to claim 20, wherein said mixture is dispersed by high shear blending.

Claim 39

A process according to claim 20, wherein the toner comprises a volume particle size of from 7-19 microns.

Claim 40

The process of claim 20, wherein the microcapsule toner is a dry toner.

Claim 41

The process of claim 38, wherein the dry toner is a powder.