IP Library Granted Patent US 9,658,545
Granted Patent B2
US 9,658,545 · App. 14/867,062 · Granted May 23, 2017

Polymeric composite materials, manufacture, and uses

Inventors: Mridula Nair (Penfield, NY); Joseph Salvatore Sedita (Albion, NY); Peter David Rollinson (Rochester, NY)
Assignee: EASTMAN KODAK COMPANY
G03G9/081C08J3/20C09D11/54G03G9/08G03G9/087G03G9/0819G03G9/0821G03G9/0825G03G9/08711G03G9/08755G03G9/08766G03G9/08777G03G9/08795G03G9/08797G03G9/093G03G9/09385G03G13/013G03G15/08
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Quick Facts
Patent No.
US 9,658,545
App. No.
14/867,062
Granted
May 23, 2017
Kind
B2
Abstract

Composite materials such as composite particles have a solid non-elastomeric continuous phase made of an organic polymer having a glass transition temperature of at least 25° C. Dispersed within this solid non-elastomeric continuous phase are many multi-compartment porous chemically crosslinked elastomeric particles that have a mode particle size of at least 1 μm and up to and including 10 μm. The composite particles can be used as toner particles in electrophotographic imaging methods to provide fused toner images and especially stacked fused toner images.

Claims (25)

1. A method for preparing composite particles, the method comprising:

melt blending one or more non-elastomeric organic polymers, each having a glass transition temperature of at least 40° C. and up to and including 120° C. as measured using differential scanning calorimetry at a scanning rate of 20° C./minute, with a plurality of multi-compartment porous chemically crosslinked elastomeric particles that have a mode particle size of at least 1 μm to and including 10 μm, wherein the non-elastomeric organic polymer comprises a polyester, styrene-acrylic copolymer, cellulosic polymer, polyamide, polyimide, vinyl ester polymer, mono-olefin polymer, vinyl ether polymer, vinyl ketone polymer, or a polymer formed from one or more α-methylene aliphatic mono-carboxylic acid esters, to form a composite blend, and

grinding the composite blend to form composite particles,

each composite particle comprising a solid non-elastomeric continuous phase comprising the non-elastomeric organic polymer and an external particle surface, the composite particle having a mode particle size of at least 10 μm to and including 100 μm, and having dispersed within the solid non-elastomeric continuous phase, a plurality of the multi-compartment porous chemically crosslinked elastomeric particles that have a mode particle size of at least 1 μm to and including 10 μm.

2. A method for forming an electrophotographic toner image, comprising:

applying a layer of composite particles to a substrate in an imagewise fashion to form a non-fused toner image on the substrate,

applying the same composite particles one or more times on the non-fused toner image to form a multi-dimensional toner image of the composite particles, and

fusing the multi-dimensional toner image of composite particles to form a fused multi-dimensional toner image on the substrate,

wherein each composite particle comprises a solid non-elastomeric continuous phase comprising an organic polymer having a glass transition temperature of at least 40° C. and up to and including 120° C. as measured using differential scanning calorimetry at a scanning rate of 20° C./minute, and an external particle surface, the composite particle having a mode particle size of at least 10 μm to and including 100 and having dispersed within the solid continuous phase, a plurality of multi-compartment porous chemically crosslinked elastomeric particles that have a mode particle size of at least 1 μm to and including 10 μm, wherein the organic polymer comprises a polyester, styrene-acrylic copolymer, cellulosic polymer, polyamide, polyimide, vinyl ester polymer, mono-olefin polymer, vinyl ether polymer, vinyl ketone polymer, or a polymer formed from one or more α-methylene aliphatic mono-carboxylic acid esters.

3. The method of claim 2 , wherein the fracture resistance of each composite particle at 20° C. is at least 10% greater than the fracture resistance of the organic polymer that contains none of the multi-compartment porous chemically crosslinked elastomeric particles.

4. The method of claim 2 , wherein the multi-compartment porous chemically crosslinked elastomeric particles are present in an amount of at least 3 weight % and up to and including 25 weight % of the total composite material weight.

5. The method of claim 2 , wherein the organic polymer comprises a polyester, styrene-acrylic copolymer, cellulosic polymer, polyamide, or polyimide.

6. The method of claim 2 , wherein the multi-compartment porous chemically crosslinked elastomeric particles have a mode particle size of at least 2 μm and up to and including 8 μm, and comprise a plurality of discrete compartments that are isolated from each other and dispersed within a chemically-crosslinked organic solid phase, and the plurality of discrete compartments have an average size greater than or equal to 100 nm.

7. The method of claim 2 , wherein each composite particle further comprises a colorant.

8. The method of claim 7 , wherein the colorant is present only in the solid non-elastomeric continuous phase.

9. The method of claim 2 , wherein each composite particle further comprises a colorant in at least some of the multi-compartment porous chemically crosslinked elastomeric particles.

10. The method of claim 2 , wherein each composite particle further comprises a colorant in at least some compartments of the multi-compartment porous chemically crosslinked elastomeric particles.

11. The method of claim 2 , wherein the organic polymer comprises a polyester.

12. A method for forming a toner image, comprising:

applying a layer of composite particles to an electrostatic image on a primary toner receiver to form a non-fused toner image on the primary toner receiver,

transferring the composite particles in the non-fused toner image from the primary toner receiver to a final receiver material,

fusing the composite particles on the final receiver material,

repeating the foregoing applying, transferring, and fusing features using the same composite particles one or more times to form a fused multi-dimensional toner image on the final receiver material,

wherein each composite particle comprises a solid non-elastomeric continuous phase comprising an organic polymer having a glass transition temperature of at least 40° C. and up to and including 120° C. as measured using differential scanning calorimetry at a scanning rate of 20° C./minute, and an external particle surface, the composite particle having a mode particle size of at least 10 μm to and including 100 μm, and having dispersed within the solid continuous phase, a plurality of multi-compartment porous chemically crosslinked elastomeric particles that have a mode particle size of at least 1 μm to and including 10 μm,

wherein the organic polymer comprises a polyester, styrene-acrylic copolymer, cellulosic polymer, polyamide, polyimide, vinyl ester polymer, mono-olefin polymer, vinyl ether polymer, vinyl ketone polymer, or a polymer formed from one or more α-methylene aliphatic mono-carboxylic acid esters.

Assignments (11)
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 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 036912/0560 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 036912/0553 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER SPECIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA N.A.
Reel/Frame 036912/0167 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2015
From: NAIR, MRIDULA; SEDITA, JOSEPH SALVATORE; ROLLINSON, PETER DAVID
To: EASTMAN KODAK COMPANY
Reel/Frame 036665/0265 →
Continuity (2)
Division 14057251 · Oct 18, 2013
Related Publication 20160018749A1 · Jan 21, 2016