IP Library Granted Patent US 8,207,246
Granted Patent B2
US 8,207,246 · App. 12/512,398 · Granted Jun 26, 2012

Processes for producing polyester latexes via solvent-free emulsification

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Quick Facts
Patent No.
US 8,207,246
App. No.
12/512,398
Granted
Jun 26, 2012
Kind
B2
Abstract

A process for making a latex emulsion suitable for use in a toner composition includes contacting a resin with a solid neutralizing agent in the absence of an organic solvent to form a mixture either via a co-feeding process or a pre-blend mixture, and adding a solid or aqueous surfactant to the pre-blend mixture or prior to melt mixing the mixture.

Claims (35)

1. A process comprising:

contacting at least one polyester resin with a solid neutralizing agent selected from the group consisting of ammonium hydroxide flakes, potassium hydroxide flakes, sodium hydroxide flakes, sodium carbonate flakes, sodium bicarbonate flakes, lithium hydroxide flakes, potassium carbonate flakes, organoamines, and combinations thereof, in the absence of an organic solvent to form a pre-blend mixture;

contacting the pre-blend mixture with a surfactant;

melt mixing the mixture;

contacting the melt mixed mixture with de-ionized water to form an oil in water emulsion; and

continuously recovering latex particles.

2. A process according to claim 1 , wherein the polyester resin is selected from the group consisting of amorphous resins, crystalline resins, and combinations thereof.

3. A process according to claim 1 , wherein the surfactant is selected from the group consisting of sodium dodecylsulfates, sodium dodecylbenzene sulfonates, sodium dodecyinaphthalene sulfate, dialkyl benzenealkyl sulfates, dialkyl benzenealkyl sulfonates, abitic 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, and wherein the surfactant is an aqueous solution.

4. A process according to claim 1 , wherein the surfactant is a solid and is pre-blended with the at least one polyester resin prior to melt mixing.

5. A process according to claim 1 , wherein the de-ionized water is added at a rate of from about 40 g/min to about 400 g/min.

6. A process according to claim 1 , wherein the latex particles have a low coarse content of from about 0.01% to about 1%, and a particle size from about 30 nm to about 1000 nm.

7. A process according to claim 1 , wherein the latex particles have a solids content of from about 30% to about 45%, and a particle size of from about 60 nm to about 300 nm.

8. A process comprising:

contacting at least one polyester resin and a solid neutralizing agent selected from the group consisting of ammonium hydroxide flakes, potassium hydroxide flakes, sodium hydroxide flakes, sodium carbonate flakes, sodium bicarbonate flakes, lithium hydroxide flakes, potassium carbonate flakes, organoamines, and combinations thereof, in the absence of an organic solvent to form a mixture;

contacting the mixture with a surfactant;

melt mixing the mixture;

contacting the melt mixed mixture with de-ionized water to form an oil in water emulsion; and

continuously recovering latex particles having a coarse content of from about 0.01% to about 1%.

9. A process according to claim 8 , wherein the polyester resin is selected from the group consisting of amorphous resins, crystalline resins, and combinations thereof.

10. A process according to claim 8 , wherein the surfactant is selected from the group consisting of sodium dodecylsulfates, sodium dodecylbenzene sulfonates, sodium dodecyinaphthalene sulfate, dialkyl benzenealkyl sulfates, dialkyl benzenealkyl sulfonates, abitic 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; and wherein the surfactant is an aqueous solution.

11. A process according to claim 8 , wherein the surfactant is a solid and is pre-blended with the at least one polyester resin and neutralizing agent prior to melt mixing.

12. A process according to claim 8 , wherein the de-ionized water is added at a rate of from about 40 g/min to about 400 g/min.

13. A process according to claim 8 , wherein the latex particles have a solids content of from about 30% to about 45%.

14. A process according to claim 8 , wherein the latex particles have a particle size of from about 60 nm to about 300 nm.

15. A process comprising:

contacting at least one polyester resin and sodium hydroxide flakes in the absence of an organic solvent to form a mixture;

contacting the mixture with a solid surfactant;

melt mixing the mixture;

contacting the melt mixed mixture with de-ionized water to form an oil in water emulsion; and

continuously recovering latex particles having a coarse content of from about 0.01% to about 1%.

16. A process according to claim 15 , wherein the polyester resin is selected from the group consisting of amorphous resins, crystalline resins, and combinations thereof.

17. A process according to claim 15 , wherein the surfactant is selected from the group consisting of sodium dodecylsulfates, sodium dodecylbenzene sulfonates, sodium dodecyinaphthalene sulfate, dialkyl benzenealkyl sulfates, dialkyl benzenealkyl sulfonates, abitic 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, C12 trimethyl ammonium bromide, C 15 trimethyl ammonium bromide, C 17 trimethyl ammonium bromide, dodecylbenzyl triethyl ammonium chloride, cetyl pyridinium bromide, and combinations thereof, and wherein the surfactant is an aqueous solution.

18. A process according to claim 15 , wherein the surfactant is a solid and is pre-blended with the at least one polyester resin and neutralizing agent.

19. A process according to claim 15 , wherein the de-ionized water is added at a rate of from about 40 g/min to about 400 g/min.

20. A process according to claim 15 , wherein the latex particles have a solids content of from about 30% to about 45% and a particle size of from about 60 nm to about 300 nm.

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 30, 2009
From: FAUCHER, SANTIAGO; CHUNG, JOO T.; HIGUCHI, FUMII; QIU, SHIGANG; LEONARDO, JOSEPH L.; ANDAYA, BRIAN J.
To: XEROX CORPORATION
Reel/Frame 023027/0565 →