Granted Patent B2

US 8,492,065 · App. 12/056,529 · Granted Jul 23, 2013

Abstract

Claims (31)

1. A process comprising:

providing at least one polyester resin possessing at least one acid group in at least one extruder by conducting a polycondensation reaction by contacting at least one diacid with at least one diol and with an optional seed resin and optional initiator to form the polyester resin;

wherein the polycondensation reaction occurs in the extruder at a temperature from about 200° C. to about 360° C.;

neutralizing the at least one acid group by contacting the resin with a base selected from the group consisting of ammonium hydroxide, potassium hydroxide, sodium hydroxide, sodium carbonate, sodium bicarbonate, lithium hydroxide, potassium carbonate, triethyl amine, triethanolamine, pyridine, diphenylamine, poly(ethylene amine), and combinations thereof;

emulsifying the neutralized resin by contacting the neutralized resin with an aqueous solution including at least one surfactant in the absence of a solvent to provide a latex emulsion containing latex particles; and

continuously recovering the latex particles.

2. A process as in claim 1 , wherein the at least one acid group is selected from the group consisting of carboxylic acids, carboxylic anhydrides, carboxylic acid salts, and combinations thereof.

3. A process as in claim 1 , wherein the surfactant is selected from the group consisting of anionic sulfate surfactants, anionic sulfonate surfactants, anionic acid surfactants, nonionic alcohol surfactants, nonionic acid surfactants, nonionic ether surfactants, cationic ammonium surfactants, cationic halide salts of quaternized polyoxyethylalkylamine surfactants, and combinations thereof.

4. A process as in claim 1 , wherein the surfactant is selected from the group consisting of sodium dodecylsulfates, sodium dodecylbenzene sulfonates, sodium dodecylnaphthalene sulfate, dialkyl benzenealkyl sulfates, dialkyl benzenealkyl sulfonates, abietic acid, alkyl diphenyloxide disulfonates, branched sodium dodecyl benzene sulfonates, polyvinyl alcohol, polyacrylic acid, methalose, methyl cellulose, ethyl cellulose, propyl cellulose, hydroxyl ethyl cellulose, carboxy methyl cellulose, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene octyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene sorbitan monolaurate, polyoxyethylene stearyl ether, polyoxyethylene nonylphenyl ether, dialkylphenoxy poly(ethyleneoxy) ethanol, alkylbenzyl dimethyl ammonium chloride, dialkyl benzenealkyl ammonium chloride, lauryl trimethyl ammonium chloride, alkylbenzyl methyl ammonium chloride, alkyl benzyl dimethyl ammonium bromide, benzalkonium chloride, C 12 trimethyl ammonium bromide, C 15 trimethyl ammonium bromide, C 17 trimethyl ammonium bromide, dodecylbenzyl triethyl ammonium chloride, cetyl pyridinium bromide, and combinations thereof.

5. A process as in claim 1 , wherein forming the neutralized resin occurs in the extruder at a pH of from about 8 to about 13 and emulsifying the neutralized resin occurs in the extruder at a temperature from about 80° C. to about 180° C.

6. A process as in claim 1 , wherein the at least one extruder spins at a rate of from about 50 rpm to about 1500 rpm.

7. A process as in claim 6 , wherein the at least one extruder comprises a single extruder comprising a polycondensation zone, a neutralization zone, and an emulsification zone.

8. A process as in claim 6 , wherein the at least one extruder comprises a first extruder comprising a polycondensation zone, and a second extruder comprising a neutralization zone and an emulsification zone.

9. A process as in claim 1 , further comprising subjecting the latex particles to sound waves at a frequency of from about 15 kHz to about 25 kHz, for a period of time from about 5 seconds to about 5 minutes, to obtain latex particles of a size of from about 30 nm to about 500 nm.

10. A process comprising:

preparing at least one polyester resin possessing acid groups by contacting at least one diacid with at least one diol, an optional seed resin and an optional initiator in at least one extruder which spins at a rate of from about 50 rpm to about 1500 rpm;

permitting the at least one diacid with at least one diol, optional seed resin and optional initiator to undergo a polycondensation reaction in the at least one extruder;

contacting the at least one polyester resin with a base in a neutralization reaction to form a neutralized resin;

emulsifying the neutralized resin by contacting the neutralized resin with an aqueous solution including at least one surfactant in the absence of a solvent to provide a latex emulsion containing latex particles; and

continuously recovering the latex particles from the at least one extruder.

11. A process as in claim 10 , wherein the at least one acid group comprises a carboxylic acid group, and wherein the polycondensation reaction occurs at a temperature of from about 200° C. to about 360° C.

12. A process as in claim 10 , wherein the surfactant is selected from the group consisting of sodium dodecylsulfates, sodium dodecylbenzene sulfonates, sodium dodecylnaphthalene sulfate, dialkyl benzenealkyl sulfates, dialkyl benzenealkyl sulfonates, abietic acid, alkyl diphenyloxide disulfonates, branched sodium dodecyl benzene sulfonates, polyvinyl alcohol, polyacrylic acid, methalose, methyl cellulose, ethyl cellulose, propyl cellulose, hydroxyl ethyl cellulose, carboxy methyl cellulose, polyoxyethylene cetyl ether, polyoxyethylene lauryl ether, polyoxyethylene octyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene sorbitan monolaurate, polyoxyethylene stearyl ether, polyoxyethylene nonylphenyl ether, dialkylphenoxy poly(ethyleneoxy) ethanol, alkylbenzyl dimethyl ammonium chloride, dialkyl benzenealkyl ammonium chloride, lauryl trimethyl ammonium chloride, alkylbenzyl methyl ammonium chloride, alkyl benzyl dimethyl ammonium bromide, benzalkonium chloride, C 12 trimethyl ammonium bromide, C 15 trimethyl ammonium bromide, C 17 trimethyl ammonium bromide, dodecylbenzyl triethyl ammonium chloride, cetyl pyridinium bromide, and optionally mixtures thereof.

13. A process as in claim 10 , further comprising subjecting the latex particles to sound waves at a frequency of from about 15 kHz to about 25 kHz, for a period of time from about 5 seconds to about 5 minutes, to obtain latex particles of a size of from about 30 nm to about 500 nm.

14. A process comprising:

preparing at least one polyester resin possessing acid groups by contacting at least one diacid with at least one diol, monomer, an optional seed resin and an optional initiator in an extruder and permitting the at least one diacid with at least one diol, optional seed resin and optional initiator to undergo a polycondensation reaction;

neutralizing the at least one polyester resin with a base to form a neutralized resin;

emulsifying the neutralized resin by contacting the neutralized resin with an aqueous solution including at least one surfactant in the absence of a solvent to provide a latex emulsion containing latex particles;

continuously recovering the latex particles;

subjecting the latex particles to sound waves at a frequency of from about 15 kHz to about 25 khz, for a period of time from about 5 seconds to about 5 minutes, to obtain latex particles of a size of from about 30 nm to about 500 nm; and

contacting the latex particles with a colorant and an optional wax to form toner particles.

15. A process as in claim 14 , wherein the colorant is selected from the group consisting of pigments, dyes, mixtures of pigments and dyes, mixtures of pigments, and mixtures of dyes, and the optional wax is selected from the group consisting of natural vegetable waxes, natural animal waxes, mineral waxes and synthetic waxes.

Assignments (10)