CA2628425A1 - Chemical toner with covalently bonded release agent - Google Patents

Chemical toner with covalently bonded release agent Download PDF

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Publication number
CA2628425A1
CA2628425A1 CA002628425A CA2628425A CA2628425A1 CA 2628425 A1 CA2628425 A1 CA 2628425A1 CA 002628425 A CA002628425 A CA 002628425A CA 2628425 A CA2628425 A CA 2628425A CA 2628425 A1 CA2628425 A1 CA 2628425A1
Authority
CA
Canada
Prior art keywords
group
toner composition
hydrogen
monomer
release agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002628425A
Other languages
French (fr)
Other versions
CA2628425C (en
Inventor
Daryl W. Vanbesien
Edward G. Zwartz
Cuong Vong
Maria N.V. Mcdougall
Timothy P. Bender
Jennifer L. Belelie
Tyler Norsten
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xerox Corp
Original Assignee
Xerox Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of CA2628425A1 publication Critical patent/CA2628425A1/en
Application granted granted Critical
Publication of CA2628425C publication Critical patent/CA2628425C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726—Polymers of unsaturated acids or derivatives thereof
    • G03G9/08728—Polymers of esters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/0802—Preparation methods
    • G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
    • G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08706—Polymers of alkenyl-aromatic compounds
    • G03G9/08708—Copolymers of styrene
    • G03G9/08711—Copolymers of styrene with esters of acrylic or methacrylic acid
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726—Polymers of unsaturated acids or derivatives thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726—Polymers of unsaturated acids or derivatives thereof
    • G03G9/08733—Polymers of unsaturated polycarboxylic acids

Abstract

A chemical toner composition including a polymer polymerized from starting ingredients comprising a resin monomer and a release agent monomer.

Claims (20)

1. A chemical toner composition comprising a polymer polymerized from starting ingredients comprising a resin monomer and a release agent monomer.
2. The chemical toner composition of claim 1, wherein the release agent monomer is selected from at least one of the following:

(a) an acrylic monomer having the formula:

wherein R1 is hydrogen or carboxylic acid or a salt thereof, R2 is hydrogen, or methyl, or ethyl, R3 is a methylene group wherein n is from about 15 to about 200, or R3 is an ethoxy, propoxy or butoxy group, or a propylene group, wherein n is from about 10 to about 100, R4 is a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof; and (b) a styrenic monomer having the following formula:

wherein R1 is a hydrogen or a methyl group, R2 is a hydrogen or a methyl group, R3 is a methylene group, an oxygen, or a carbonyl group, R4 is a methylene group or an oxygen, R5 is a methylene group, n is from about 15 to about 200, or R5 is an ethoxy, propoxy or butoxy group or a propylene group wherein n is from about 10 to about 100, R6 is a hydrogen, a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof.
3. The chemical toner composition of claim 1, wherein the chemical toner composition is substantially free of a non-covalently bonded release agent.
4. The chemical toner composition of claim 1, wherein the chemical toner composition comprises particles have a circularity ranging from about 0.930 to 1.000.
5. The chemical toner composition of claim 1, wherein the chemical toner composition comprises particles having a volume average particle size distribution index of about 1.30 or less.
6. The chemical toner composition of claim 1, wherein the resin monomer comprises a styrene and an acrylate.
7. The chemical toner composition of claim 1, wherein the release agent monomer comprises an octadecylacrylate.
8. An emulsion aggregation toner composition comprising a polymer polymerized from starting ingredients comprising a resin monomer and a release agent monomer.
9. The emulsion aggregation toner composition of claim 8, wherein the release agent monomer is selected from at least one of the following:

(a) an acrylic monomer having the formula:

wherein R1 is hydrogen or carboxylic acid or a salt thereof, R2 is hydrogen, or methyl, or ethyl, R3 is a methylene group wherein n is from about 15 to about 200, or R3 is an ethoxy, propoxy or butoxy group, or a propylene group, wherein n is from about 10 to about 100, R4 is a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof; and (b) a styrenic monomer having the following formula:

wherein R1 is a hydrogen or a methyl group, R2 is a hydrogen or a methyl group, R3 is a methylene group, an oxygen, or a carbonyl group, R4 is a methylene group or an oxygen, R5 is a methylene group, n is from about 15 to about 200, or R5 is an ethoxy, propoxy or butoxy group or a propylene group wherein n is from about 10 to about 100, R6 is a hydrogen, a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof.
10. The emulsion aggregation toner composition of claim 8, wherein the emulsion aggregation toner composition is substantially free of a non-covalently bonded release agent.
11. The emulsion aggregation toner composition of claim 8, wherein the emulsion aggregation toner composition comprises particles have a circularity ranging from about 0.930 to 1.000.
12. The emulsion aggregation toner composition of claim 8, wherein the emulsion aggregation toner composition comprises particles having a volume average particle size distribution index of about 1.30 or less.
13. The emulsion aggregation toner composition of claim 8, wherein the resin monomer comprises a styrene and an acrylate.
14. The emulsion aggregation toner composition of claim 8, wherein the release agent monomer comprises an octadecylacrylate.
15. A process comprising:

(a) forming a dispersion comprising (i) a disperse phase including starting ingredients comprising a resin monomer and a release agent monomer; and (ii) a continuous phase including starting ingredients comprising water and a phase transport catalyst;

(b) polymerizing the resin monomer and the release agent monomer to result in a polymer;

(c) aggregating toner precursor materials comprising the polymer and a colorant to result in aggregated toner precursor materials; and (d) coalescing the aggregated toner precursor materials to result in an emulsion aggregation toner composition comprising the colorant and the polymer.
16. The process of claim 15, wherein the phase transport catalyst is a cyclodextrin, a cyclodextrin derivative, or a mixture thereof.
17. The process of claim 15, wherein the release agent monomer is selected from at least one of the following:

(a) an acrylic monomer having the formula:

wherein R1 is hydrogen or carboxylic acid or a salt thereof, R2 is hydrogen, or methyl, or ethyl, R3 is a methylene group wherein n is from about 15 to about 200, or R3 is an ethoxy, propoxy or butoxy group, or a propylene group, wherein n is from about 10 to about 100, R4 is a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof; and (b) a styrenic monomer having the following formula:

wherein R1 is a hydrogen or a methyl group, R2 is a hydrogen or a methyl group, R3 is a methylene group, an oxygen, or a carbonyl group, R4 is a methylene group or an oxygen, R5 is a methylene group, n is from about 15 to about 200, or R5 is an ethoxy, propoxy or butoxy group or a propylene group wherein n is from about 10 to about 100, R6 is a hydrogen, a methyl group, a hydroxyl group, or a carboxylic acid group or a salt thereof.
18. The process of claim 15, wherein the emulsion aggregation toner composition comprises particles having a volume average particle size distribution index of about 1.30 or less.
19. The process of claim 15, wherein the resin monomer comprises a styrene and an acrylate.
20. The process of claim 15, wherein the release agent monomer comprises an octadecylacrylate.
CA2628425A 2007-04-10 2008-04-03 Chemical toner with covalently bonded release agent Active CA2628425C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/733,367 US7901859B2 (en) 2007-04-10 2007-04-10 Chemical toner with covalently bonded release agent
US11/733,367 2007-04-10

Publications (2)

Publication Number Publication Date
CA2628425A1 true CA2628425A1 (en) 2008-10-10
CA2628425C CA2628425C (en) 2012-02-14

Family

ID=39539565

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2628425A Active CA2628425C (en) 2007-04-10 2008-04-03 Chemical toner with covalently bonded release agent

Country Status (8)

Country Link
US (1) US7901859B2 (en)
EP (1) EP1980914B1 (en)
JP (1) JP5596274B2 (en)
KR (1) KR101459349B1 (en)
CN (2) CN101286020A (en)
BR (1) BRPI0800962B1 (en)
CA (1) CA2628425C (en)
MX (1) MX2008004557A (en)

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US9213248B2 (en) * 2013-07-23 2015-12-15 Xerox Corporation Latex comprising colorant and methods of making the same

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Also Published As

Publication number Publication date
KR101459349B1 (en) 2014-11-07
KR20080092287A (en) 2008-10-15
EP1980914B1 (en) 2015-09-23
US7901859B2 (en) 2011-03-08
MX2008004557A (en) 2009-02-27
CA2628425C (en) 2012-02-14
CN101286020A (en) 2008-10-15
BRPI0800962A2 (en) 2008-11-25
JP5596274B2 (en) 2014-09-24
CN105068390A (en) 2015-11-18
BRPI0800962B1 (en) 2018-12-04
EP1980914A1 (en) 2008-10-15
US20080254381A1 (en) 2008-10-16
JP2008262200A (en) 2008-10-30
CN105068390B (en) 2020-01-10

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