IP Library Granted Patent US 8,546,057
Granted Patent B2
US 8,546,057 · App. 13/017,384 · Granted Oct 1, 2013

Carbon based black toners prepared via limited coalescence process

Inventors: Dinesh Tyagi (Fairport, NY); Louise Granica (Victor, NY)
Assignee: Eastman Kodak Company
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Quick Facts
Patent No.
US 8,546,057
App. No.
13/017,384
Granted
Oct 1, 2013
Kind
B2
Abstract

A black toner composition comprising toner particles prepared by a chemical process of manufacture comprising carbon black pigment, a first addition polymer comprising carboxylic acid groups along the polymer backbone, and a thermoplastic second polymer binder distinct from the first polymer, wherein the first polymer has an Acid Value of from 30 to 220 and is present at a weight ratio of greater than 1:2 relative to the amount of carbon, and at a relatively lower weight percent than the second polymer. A process for preparation of such toner particles comprising: preparing a masterbatch comprising a carbon black and a first addition polymer comprising carboxylic acid groups along the polymer backbone and having an Acid Value of from 30 to 220, where the first polymer is present at a weight ratio of greater than 1:2 relative to the amount of carbon; dissolving a thermoplastic second polymer binder in an organic solvent; adding the masterbatch to the solution of second polymer binder to form an organic phase, wherein the first polymer is present at a lower weight percent than the second polymer; dispersing the organic phase in an aqueous phase comprising a particulate stabilizer to form a dispersion; and removing the solvent from the organic phase to form toner particles comprising the first polymer, the second polymer binder and carbon black.

Claims (20)

1. A process for preparation of toner particles comprising carbon black and polymeric binder, comprising:

preparing a masterbatch comprising carbon black particles and a first addition polymer comprising carboxylic acid groups along the polymer backbone and having an Acid Value of from 50-200, where the first addition polymer is present at a weight ratio of greater than 1:2 relative to the amount of carbon;

dissolving a thermoplastic second polymer binder in an organic solvent;

adding the masterbatch to the solution of second polymer binder to form an organic phase, wherein the first addition polymer is present at a lower weight percent than the second polymer;

dispersing the organic phase in an aqueous phase comprising a particulate stabilizer to form a dispersion; and

removing the solvent from the organic phase to form toner particles comprising the first addition polymer, the second polymer binder, and carbon black.

2. A process according to claim 1 , wherein the first addition polymer is present at a weight ratio of up to 4:1 relative to the amount of carbon.

3. A process according to claim 1 , wherein the first addition polymer is present at a weight ratio of from 1:1 to 3:1 relative to the amount of carbon.

4. A process according to claim 1 , wherein the first addition polymer is present at a weight ratio of from 1:1 to 2:1 relative to the amount of carbon.

5. A process according to claim 1 , wherein the first addition polymer has a weight average molecular weight Mw of from 3,000-20,000.

6. A process according to claim 1 , wherein the first addition polymer has a weight average molecular weight Mw of from 4,000-10,000.

7. A process according to claim 1 , wherein the formed toner particles have a mean volume-average diameter of less than about 8 μm, and include 1 wt. % to 20 wt. % carbon pigment.

8. A process according to claim 1 , wherein the formed toner particles have a mean volume-average diameter of from 3 μm to 7 μm, and include 3 wt. % to 10 wt. % of carbon pigment.

9. A process according to claim 1 , wherein the second polymer binder comprises a polyester.

10. A process for preparation of toner particles comprising carbon black and polymeric binder, comprising:

preparing a masterbatch comprising carbon black particles and a first addition polymer comprising carboxylic acid groups along the polymer backbone and having an Acid Value of from 50-150, where the first addition polymer is present at a weight ratio of greater than 1:2 relative to the amount of carbon;

dissolving a thermoplastic second polymer binder in an organic solvent;

adding the masterbatch to the solution of second polymer binder to form an organic phase, wherein the first addition polymer is present at a lower weight percent than the second polymer;

dispersing the organic phase in an aqueous phase comprising a particulate stabilizer to form a dispersion; and

removing the solvent from the organic phase to form toner particles comprising the first addition polymer, the second polymer binder, and carbon black.

Assignments (14)
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST) INC.; KODAK AMERICAS LTD.; KODAK REALTY INC.; LASER PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES LTD.; NPEC INC.
Reel/Frame 052773/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (ABL) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 031162/0117 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (SECOND LIEN) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 031159/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (FIRST LIEN) Recorded Sep 5, 2013
From: QUALEX INC.; EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC; KODAK AMERICAS, LTD.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE
Reel/Frame 031158/0001 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 5, 2013
From: CITICORP NORTH AMERICA, INC., AS SENIOR DIP AGENT; WILMINGTON TRUST, NATIONAL ASSOCIATION, AS JUNIOR DIP AGENT
To: EASTMAN KODAK COMPANY; PAKON, INC.
Reel/Frame 031157/0451 →
PATENT SECURITY AGREEMENT Recorded Apr 1, 2013
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 030122/0235 →
SECURITY INTEREST Recorded Feb 21, 2012
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: CITICORP NORTH AMERICA, INC., AS AGENT
Reel/Frame 028201/0420 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2011
From: TYAGI, DINESH; GRANICA, LOUISE
To: EASTMAN KODAK COMPANY
Reel/Frame 025768/0605 →
Continuity (1)
Related Publication 20120196221A1 · Aug 2, 2012