Encapsulated toner compositions

Claim 2

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment, and a polymeric shell derived from the polycondensation of a glycidyl-functionalized reagent and a polyisocyanate with a polyamine.

Claim 3

A toner in accordance with claim 1 wherein the glycidyl functionalized reagent is a diglycidyl functionalized alkane, a triglycidyl functionalized alkane, a diglycidyl functionalized arene, or a triglycidyl functionalized arene.

Claim 4

A toner in accordance with claim 1 wherein the glycidylfunctionalized reagent is selected from the group consisting of ethanediol diglycidyl ether, propanediol diglycidyl ether, butanediol diglycidyl ether, pentanediol diglycidyl ether, hexanediol diglycidyl ether, 2-methylpropanediol diglycidyl ether, 2-methylbutanediol diglycidyl ether, 2,2-dimethylpropanediol diglycidyl ether, 1,4-dimethylenecylcohexanediol diglycidyl ether, 2,2-dimethylpentanediol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol Z diglycidyl ether, xylenediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, epichlorohydrinbutanediol epoxy resins, epichlorohydrin-2,2-dimethylpropanediol epoxy resins, epichlorohydrin-tetraphenylol ethane epoxy resins, epichlorohydrinresorcin epoxy resins, epichlorohydrin-bisphenol A epoxy resins, epichlorohydrin-bisphenol F epoxy resins, epichlorohydrin-bisphenol Z epoxy resins, epichlorohydrin-tetrahydroxyphenylmethane epoxy resins, epichlorohydrin-polyglycol epoxy resins, epichlorohydrin-glycerine triether epoxy resins, and epichlorohydrin-halogenated bisphenol epoxy resins.

Claim 5

A toner in accordance with claim 1 wherein the polyisocyanate is a diisocyanate, a triisocyanate, a polyether isocyanate prepolymer, or mixtures thereof.

Claim 6

A toner in accordance with claim 1 wherein the polyisocyanate is selected from the group consisting of benzene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocynate, and bis(4-isocyanatocyclohexyl)methane.

Claim 7

A toner in accordance with claim 1 wherein the polyamine is selected from the group consisting of ethylenediamine, trimethyelenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylelendiamine, octamethylenediamine, methylpentamethylenediamine, phenylenediamine, 2-hydroxy trimethylenediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, xylylenediamine, bis(hexamethylene)triamine, tris(aminoethyl)amine, 4,4'-methylene bis(cyclohexylamine), bis(aminopropyl)ethylenediamine, bis(aminomethyl)cyclohexane, 1,5-diamino-2-methylpentane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine, and 2,5-dimethylpentamethylene diamine.

Claim 8

A toner in accordance with claim 1 wherein the core resin binder is an acrylate, a methyacrylate, a styrene, or the copolymers thereof.

Claim 9

A toner in accordance with claim 1 wherein the core resin binder is obtained from the polymerization of a monomer or a plurality of monomers selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, pentyl acrylate, pentyl methacrylate, hexyl acrylate, hexyl methacrylate, heptyl acrylate, heptyl methacrylate, octyl acrylate, octyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, benzyl acrylate, benzyl methacrylate, ethoxypropyl acrylate, ethoxypropyl methacrylate, methylbutyl acrylate, methylbutyl methacrylate, ethylhexyl acrylate, ethylhexyl methacrylate, methoxybutyl acrylate, methoxybutyl methacrylate, cyanobutyl acrylate, cyanobutyl methacrylate, tolyl acrylate, tolyl methacrylate, styrene, dodecyl styrene, methylhexyl styrene, nonyl styrene, and tetradecyl styrene.

Claim 10

A toner in accordance with claim 1 wherein the core resin binder is poly(lauryl methacrylate).

Claim 11

A toner in accordance with claim 1 wherein the pigment is carbon black, magnetite, or mixtures thereof.

Claim 12

A toner in accordance with claim 10 wherein the magnetite selected is Mapico Black or surface treated magnetites.

Claim 13

A toner in accordance with claim 1 wherein the pigment is cyan, magenta, yellow, red, blue, green, brown, or mixtures thereof.

Claim 14

A toner in accordance with claim 1 wherein the pigment is Heliogen Blue, Pylam Oil Blue, Pylam Oil Yellow, Pigment Blue 1, Pigment Violet 1, Pigment Red, Lemon Chrome Yellow, E.D. Toluidine Red, Bon Red C, Novaperm Yellow FGL, Hostaperm Pink E, Cinquasia Magenta, Oil Red anthraquinone dye, Cl Dispersed Red 15, diazo dye, Cl Solvent Red 19, copper tetra-4-(octadecyl sulfonamido) phthalocyanine, X-copper phthalocyanine pigment, Cl Pigment Blue, Anthrathrene Blue, diarylide yellow 3,3-dichlorobenzidene acetoacetanilides, Cl Solvent Yellow, a nitrophenyl amine sulfonamide, Cl Dispersed Yellow 33, 2,5-dimethoxy-4-sulfonanilide phenylazo-4'-chloro-2,5-dimethoxy acetoacetanilide, or Permanent Yellow FGL.

Claim 15

A toner in accordance with claim 1 wherein the polymeric shell represents from 3 percent to 30 percent by weight of toner, the core resin binder represents from 15 percent to 95 percent by weight of toner, and the pigment or dye represents from 1 percent to 70 percent by weight of toner.

Claim 16

A toner in accordance with claim 1 containing surface additives.

Claim 17

A toner in accordance with claim 15 wherein the surface additives are carbon black, metal salts, metal salts of fatty acids, or colloidal silicas.

Claim 18

A toner in accordance with claim 16 wherein zinc stearate is selected.

Claim 19

A toner in accordance with claim 15 wherein the additives are present in an amount of from about 0.1 to about 5 weight percent.

Claim 20

A toner in accordance with claim 1 wherein the shell is prepared by interfacial polymerization.

Claim 21

A toner in accordance with claim 1 wherein the polymer shell is comprised of the interfacial polycondensation product of at least one polyisocyanate, one glycidyl functionalized reagent and one polyamine.

Claim 22

A toner in accordance with claim 20 wherein the mole fraction of the glycidyl functionalized reagent to polyisocyanate selected for the shell forming polycondensation with a polyamine is from about 0.1 to about 0.1, while the polyamine is employed in a slight molar excess of from about 0.1 to about 10 percent.

Claim 23

A toner in accordance with claim 21 wherein the mole fraction is from about 0.5 to about 0.9.

Claim 24

A toner in accordance with claim 20 wherein a plurality of glycidyl functionalized reagents is selected.

Claim 25

A toner in accordance with claim 20 wherein a plurality of polyisocyanates is selected.

Claim 26

A toner in accordance with claim 20 wherein a plurality of polyamines is selected.

Claim 27

A toner in accordance with claim 1 wherein the polyisocyanate is selected from the group consisting of benzene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, bis(4-isocyanatocyclohexyl)methane, the glycidyl functionalized reagent is selected from the group consisting of ethanediol diglycidyl ether, propanediol diglycidyl ether, butanediol diglycidyl ether, pentanediol diglycidyl ether, hexanediol diglycidyl ether, 2-methylpropanediol diglycidyl ether, 2-methylbutanediol diglycidyl ether, 2,2-dimethylpropanediol diglycidyl ether, 1,4-dimethylenecylcohexanediol diglycidyl ether, 2,2-dimethylpentanediol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol Z diglycidyl ether, xylenediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, epichlorohydrin-butanediol epoxy resins, epichlorohydrin-2,2-dimethylpropanediol epoxy resins, epichlorohydrin-tetraphenylol ethane epoxy resins, epichlorohydrin-resorcin epoxy resins, epichlorohydrin-bisphenol A epoxy resins, epichlorohydrin-bisphenol F epoxy resins, epichlorohydrin-bisphenol Z epoxy resins, epichlorohydrin-tetrahydroxyphenylmethane epoxy resins, epichlorohydrin-polyglycol epoxy resins, epichlorohydrin-glycerine triether epoxy resins, and epichlorohydrin-halogenated bisphenol epoxy resins; and the polyamine component is selected from the group consisting of ethylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethyelenediamine, octamethylenediamine, methylpentamethylenediamine, phenylenediamine, 2-hydroxy trimethylenediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, xylylenediamine, bis(hexamethylene)triamine, tris(aminoethyl)amine, 4,4'-methylene bis(cyclohexylamine), bis(aminopropyl)ethylenediamine, bis(aminomethyl)cyclohexane, 1,5-diamino-2-methylpentane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine, and 2,5-dimethylpentamethylene diamine.

Claim 28

A toner in accordance with claim 1 wherein the polymeric shell contains conductive components.

Claim 29

A toner in accordance with claim 27 wherein the conductive components are comprised of carbon black, graphite, or mixtures thereof.

Claim 30

A method of imaging which comprises forming by ion deposition on an electroreceptor a latent image, subsequently developing this image with the toner composition of claim 1, and thereafter transferring and fixing the image to a suitable substrate.

Claim 31

A method of imaging in accordance with claim 29 wherein there results images with excellent image fixing characteristics.

Claim 32

A pressure fixable toner composition comprised of a core comprised of a pigment or dye; and a polymer core resin component selected from the group consisting of acrylate polymers, methacrylate polymers, and styrene polymers, which core is encapsulated within a polymeric shell derived from the interfacial polycondensation of a polyisocyanate and a glycidyl functionalized reagent with a polyamine.

Claim 33

A pressure fixable toner composition comprised of a core comprised of a pigment or dye; and a polymer core resin component selected from the group consisting of acrylate polymers, methacrylate polymers, and styrene polymers, which core is encapsulated within a polymeric shell derived from the interfacial polycondensation of a polyisocyanate and a glycidyl functionalized reagent with a polyamine.

Claim 34

A toner composition in accordance with claim 31 wherein the polyisocyanate is selected from the group consisting of toluene diisocyanate, and polyether isocyanate prepolymers; the glycidyl functionalized reagent is selected from the group consisting of ethanediol diglycidyl ether, propanediol diglycidyl ether, butanediol diglycidyl ether, pentanediol diglycidyl ether, hexanediol diglycidyl ether, 2-methylpropanediol diglycidyl ether, 2-methylbutanediol diglycidyl ether, 2,2-dimethylpropanediol diglycidyl ether, 1,4-dimethylenecylcohexanediol diglycidyl ether, 2,2-dimethylpentanediol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol Z diglycidyl ether, xylenediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, epichlorohydrinbutanediol epoxy resins, epichlorohydrin-2,2-dimethylpropanediol epoxy resins, epichlorohydrin-tetraphenylol ethane epoxy resins, epichlorohydrinresorcine epoxy resins, epichlorohydrin-bisphenol A epoxy resins, epichlorohydrin-bisphenol F epoxy resins, epichlorohydrin-bisphenol Z epoxy resins, epichlorohydrin-tetrahydroxyphenylmethane epoxy resins, epichlorohydrin-polyglycol epoxy resins, epichlorohydrin-glycerine triether epoxy resins, and epichlorohydrin-halogenated bisphenol epoxy resins; and the polyamine is selected from the group consisting of ethylenediamine, trimethyelenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, methylpentamethylenediamine, phenylenediamine, 2-hydroxy trimethylenediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, xylylenediamine, bis(hexamethylene)triamine, tris(aminoethyl)amine, 4,4'-methylene bis(cyclohexylamine), bis(aminopropyl)ethylenediamine, bis(aminomethyl)cyclohexane, 1,5-diamino-2-methylpentane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine, and 2,5-dimethylpentamethylene diamine.

Claim 35

A toner in accordance with claim 31 wherein the pigment is carbon black, magnetites, or mixtures thereof.

Claim 36

A toner in accordance with claim 31 wherein the pigment is cyan, magenta, yellow, red, blue, green, brown pigments, or mixtures thereof.

Claim 37

A toner in accordance with claim 31 wherein the core resin binder is derived from the polymerization of an addition monomer or monomers selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, pentyl acrylate, pentyl methacrylate, hexyl acrylate, hexyl methacrylate, heptyl acrylate, heptyl methacrylate, octyl acrylate, octyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate, stearyl methacrylate, benzyl acrylate, benzyl methacrylate, ethoxypropyl acrylate, ethoxypropyl methacrylate, methylbutyl acrylate, methylbutyl methacrylate, ethylhexyl acrylate, ethylhexyl methacrylate, methoxybutyl acrylate, methoxybutyl methacrylate, cyanobutyl acrylate, cyanobutyl methacrylate, tolyl acrylate, tolyl methacrylate, styrene, dodecyl styrene, methylhexyl styrene, nonyl styrene, and tetradecyl styrene.

Claim 38

A method of imaging which comprises forming by ion deposition on an electroreceptor a latent image, subsequently developing this image with the toner composition of claim 31, and thereafter simultaneously transferring and fixing the image to a suitable substrate.

Claim 39

A method of imaging in accordance with claim 36 wherein there results images with excellent image fixing characteristics.

Claim 40

A method of imaging in accordance with claim 36 wherein fixing is accomplished at pressures of from about 500 psi to about 6,000 psi.

Claim 41

A toner composition in accordance with claim 31 wherein the resistivity thereof is from about 10 3 to about 10 8 ohm-cm.

Claim 42

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, dye particles, or mixtures thereof, and a polymeric shell derived from the polycondensation of a glycidyl functionalized component, a polyisocyanate and a polyamine.

Claim 43

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, dye particles, or mixtures thereof, and a polymeric shell derived from the polycondensation of a glycidyl functionalized component, a polyisocyanate and a polyamine.

Claim 44

Encapsulated toner compositions comprised of cores comprised of polymer binders, pigment particles, dye particles, and polymeric shells derived from the polycondensation of glycidyl functionalized components, polyisocyanates and polyamines.

Claim 45

Encapsulated toner compositions comprised of cores comprised of polymer binders, pigment particles, dye particles, and polymeric shells derived from the polycondensation of glycidyl functionalized components, polyisocyanates and polyamines.

Claim 46

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, and a polymeric shell derived from the polycondensation of a glycidyl functionalized component, a polyisocyanate and a polyamine.

Claim 47

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, and a polymeric shell derived from the polycondensation of a glycidyl functionalized component, a polyisocyanate and a polyamine.

Claim 48

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, dye particles, or mixtures thereof, and a polymeric shell derived from polycondensation of a glycidyl functionalized reagent and a polyisocyanate with a polyamine.

Claim 49

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment particles, dye particles, or mixtures thereof, and a polymeric shell derived from polycondensation of a glycidyl functionalized reagent and a polyisocyanate with a polyamine.

Claim 50

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment, and a polymeric shell derived from the polycondensation of a glycidyl-functionalized reagent and a polyisocyanate with a polyamine, and wherein the shell and the core are free of a curing component.

Claim 51

An encapsulated toner composition comprised of a core comprised of a polymer binder, pigment, and a polymeric shell derived from the polycondensation of a glycidyl-functionalized reagent and a polyisocyanate with a polyamine, and wherein the shell and the core are free of a curing component.