DE60016758D1 - Phosphorylierte polymerdispergiermittel für tinten - Google Patents

Phosphorylierte polymerdispergiermittel für tinten

Info

Publication number
DE60016758D1
DE60016758D1 DE60016758T DE60016758T DE60016758D1 DE 60016758 D1 DE60016758 D1 DE 60016758D1 DE 60016758 T DE60016758 T DE 60016758T DE 60016758 T DE60016758 T DE 60016758T DE 60016758 D1 DE60016758 D1 DE 60016758D1
Authority
DE
Germany
Prior art keywords
inks
dispersing agents
polymer dispersing
phosphorylated polymer
phosphorylated
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.)
Expired - Fee Related
Application number
DE60016758T
Other languages
English (en)
Other versions
DE60016758T2 (de
Inventor
Sheau-Hwa Ma
Francis Mcbride
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Application granted granted Critical
Publication of DE60016758D1 publication Critical patent/DE60016758D1/de
Publication of DE60016758T2 publication Critical patent/DE60016758T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/12Polymerisation in non-solvents
    • C08F2/16Aqueous medium
    • C08F2/22Emulsion polymerisation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/06Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
    • C08F299/065Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes from polyurethanes with side or terminal unsaturations
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/30Inkjet printing inks
    • C09D11/32Inkjet printing inks characterised by colouring agents
    • C09D11/324Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
DE60016758T 1999-08-04 2000-08-03 Phosphorylierte polymerdispergiermittel für tinten Expired - Fee Related DE60016758T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/366,573 US6433117B1 (en) 1999-08-04 1999-08-04 Phosphorylated polymer dispersants for inks
US366573 1999-08-04
PCT/US2000/021155 WO2001010918A1 (en) 1999-08-04 2000-08-03 Phosphorylated polymer dispersants for inks

Publications (2)

Publication Number Publication Date
DE60016758D1 true DE60016758D1 (de) 2005-01-20
DE60016758T2 DE60016758T2 (de) 2005-12-08

Family

ID=23443590

Family Applications (1)

Application Number Title Priority Date Filing Date
DE60016758T Expired - Fee Related DE60016758T2 (de) 1999-08-04 2000-08-03 Phosphorylierte polymerdispergiermittel für tinten

Country Status (8)

Country Link
US (1) US6433117B1 (de)
EP (1) EP1200492B1 (de)
JP (1) JP2003506536A (de)
AT (1) ATE284906T1 (de)
AU (1) AU6398300A (de)
CA (1) CA2378837A1 (de)
DE (1) DE60016758T2 (de)
WO (1) WO2001010918A1 (de)

Families Citing this family (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2371553A (en) * 2000-12-23 2002-07-31 Ilford Imaging Uk Ltd Inks for Ink Jet Printers
EP1302515B1 (de) 2001-10-01 2008-08-06 Rohm And Haas Company Beschichtungszusammensetzung auf Basis eines bimodalen Emulsionscopolymeren, Verfahren zur Fleckenbeseitigung, Deckkraftverbesserung, Blockneigungsreduzierung und Verbesserung der Scherstabilität
CN100334171C (zh) 2001-12-28 2007-08-29 花王株式会社 水性油墨
US6582510B1 (en) 2002-04-16 2003-06-24 Arco Chemical Technology, L.P. Use of comb-branched copolymers as pigment dispersants
DE10242106A1 (de) * 2002-09-11 2004-04-15 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Phosphorgruppenhaltige Carbonsäurederivate mit organisch polymerisierbaren Gruppen
BR0315345A (pt) * 2002-10-17 2005-08-23 Ciba Sc Holding Ag Composição aquosa de tinta, processo para impressão de substrato planar, partìcula de alumìnio, processo para produzir flocos de alumìnio e os referidos flocos
US7045002B2 (en) * 2002-11-15 2006-05-16 E. I. Du Pont De Nemours And Company Interactive ink set for inkjet printing
US20050215663A1 (en) * 2004-01-21 2005-09-29 Berge Charles T Inkjet inks containing crosslinked polyurethanes
US20050282928A1 (en) * 2004-06-21 2005-12-22 Tyau-Jeen Lin Ink jet ink
JP4087822B2 (ja) * 2004-07-22 2008-05-21 東芝テック株式会社 インクジェットプリンタヘッド用洗浄液、およびそれを用いた洗浄方法
WO2006105322A2 (en) * 2005-03-31 2006-10-05 Rhodia Inc. Mineral particle dispersions stabilized with a poly (oxyalkene) phosphonate
JP2007070567A (ja) * 2005-09-09 2007-03-22 Dainippon Ink & Chem Inc 水性顔料分散体及びインクジェット記録用水性インク
WO2007035505A1 (en) * 2005-09-15 2007-03-29 E. I. Du Pont De Nemours And Company Aqueous inkjet ink
BRPI0618109A2 (pt) * 2005-10-31 2011-08-16 Cabot Corp colorantes modificados e composições de tinta de impressora a jato de tinta compreendendo colorantes modificados
JP4835132B2 (ja) * 2005-12-02 2011-12-14 Dic株式会社 水性顔料分散体及びインクジェット記録用水性インク
WO2007119836A1 (ja) * 2006-04-13 2007-10-25 Toyo Ink Mfg. Co., Ltd. 着色樹脂組成物およびそれを用いたインクジェットインキ
JP5239208B2 (ja) * 2006-05-12 2013-07-17 東洋インキScホールディングス株式会社 インクジェットインキおよび該インキを用いた印刷物
DE102006049381A1 (de) * 2006-10-19 2008-04-24 Süd-Chemie AG Amphiphile Pfropfpolymere
DE102006062441A1 (de) 2006-12-27 2008-07-03 Byk-Chemie Gmbh Modifizierte Kammcopolymere
DE102007021867A1 (de) * 2007-05-10 2008-11-20 Clariant International Limited Pigmentpräparationen auf Wasserbasis
DE102007021869A1 (de) * 2007-05-10 2008-11-13 Clariant International Limited Anionische wasserlösliche Additive
DE102007039784A1 (de) * 2007-08-23 2009-02-26 Clariant International Limited Anionische wasserlösliche Additive auf Allyl- und Vinyletherbasis
US8186822B2 (en) * 2008-05-08 2012-05-29 E I Du Pont De Nemours And Company Inkjet inks containing crosslinked polyurethanes
JP2011521085A (ja) * 2008-05-22 2011-07-21 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー インクジェットインクと共に用いられる定着インク
WO2011014615A1 (en) 2009-07-30 2011-02-03 E. I. Du Pont De Nemours And Company Method of preparing dispersions
KR20120112481A (ko) 2009-11-23 2012-10-11 이 아이 듀폰 디 네모아 앤드 캄파니 가교결합된 착색제 분산물의 제조 방법
WO2011150301A1 (en) 2010-05-27 2011-12-01 E. I. Du Pont De Nemours And Company Fixer inks for use with ink jet inks
US8859644B2 (en) 2010-12-15 2014-10-14 E I Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions with monomers which have a lower critical solution temperature
US20130225739A1 (en) 2010-12-15 2013-08-29 Harry Joseph Spinelli Ink-jet ink comprising encapsulated cross-linked pigment dispersions
WO2012082965A1 (en) 2010-12-15 2012-06-21 E. I. Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions
WO2012082991A2 (en) 2010-12-15 2012-06-21 E. I. Du Pont De Nemours And Company Method of preparing pigment dispersions
WO2012083013A2 (en) 2010-12-15 2012-06-21 E. I. Du Pont De Nemours And Company Encapsulated cross-linked pigment dispersions
WO2012148476A2 (en) 2011-04-25 2012-11-01 E. I. Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions which include polyurethane dispersions
US20140045975A1 (en) 2011-04-29 2014-02-13 E I Du Pont De Nemours And Company Method of preparing cross-linked colorant dispersions
US20140026784A1 (en) 2011-05-27 2014-01-30 E I Du Pont De Nemours And Company Pigmented inkjet ink comprising hydrophilic polymer as a bleed control agent
US8957134B2 (en) 2011-07-14 2015-02-17 E I Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions with minimal free polymer
WO2013009343A1 (en) 2011-07-14 2013-01-17 E. I. Du Pont De Nemours And Company Ink jet ink comprising encapsulated pigment dispersions with minimal free polymer
US9371459B2 (en) 2011-07-20 2016-06-21 E I Du Pont De Nemours And Company Inkjet inks and ink sets
US20140249248A1 (en) 2011-10-27 2014-09-04 E I Du Pont De Nemours And Company Inkjet ink comprising encapsulated pigment dispersions with two encapsulation steps
WO2013062600A1 (en) 2011-10-27 2013-05-02 E. I. Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions with two encapsulation steps
US20140296395A1 (en) 2011-12-15 2014-10-02 Ei Du Pont De Nemours And Company Method of preparing encapsulated pigment dispersions with continuous additon of encapsulating monomer
WO2013101856A1 (en) 2011-12-30 2013-07-04 E. I. Du Pont De Nemours And Company Aqueous pigment dispersions with components to interact with cellulose
US9062228B2 (en) 2011-12-30 2015-06-23 E I Du Pont De Nemours And Company Aqueous inkjet inks containing polyurethane binders with components to interact with cellulose
JP2015528838A (ja) 2012-06-29 2015-10-01 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company 顔料プレスケーキの製造方法およびその使用
US9085707B2 (en) 2012-08-31 2015-07-21 E I Du Pont De Nemours And Company Aqueous pigment dispersions and inkjet inks
JP6020177B2 (ja) * 2013-01-07 2016-11-02 株式会社リコー インクジェットインク
WO2014142013A1 (en) 2013-03-15 2014-09-18 Ricoh Company, Ltd. Inkjet recording ink, ink cartridge, inkjet recording method, inkjet recording device and ink recorded matter
WO2015038254A2 (en) 2013-08-06 2015-03-19 E. I. Du Pont De Nemours And Company Aqueous inkjet inks containing polymeric binders with components to interact with cellulose
JP2016527379A (ja) 2013-08-06 2016-09-08 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company セルロースと相互作用する成分を有する水性顔料分散体
JP6224990B2 (ja) * 2013-10-31 2017-11-01 株式会社リコー インクジェット記録用インク、並びに該インクを用いたインクカートリッジ、インクジェット記録物の製造方法、インクジェット記録装置、およびインク記録物
JP2017508030A (ja) 2013-12-30 2017-03-23 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company 分散されたポリウレタンおよびオレフィンイオン性コポリマーを含んでなる顔料系インクジェットインク
JP6279344B2 (ja) * 2014-02-24 2018-02-14 株式会社リコー インクジェット記録用インク、インクカートリッジ、インクジェット記録物の製造方法、インクジェット記録装置、及びインク記録物
JP2016094498A (ja) 2014-11-12 2016-05-26 株式会社リコー インク、インクカートリッジ、インクジェット記録装置及び共重合体
WO2016100009A1 (en) 2014-12-19 2016-06-23 E. I. Du Pont De Nemours And Company Carbon black pigment for improved durability
EP3234040A1 (de) 2014-12-19 2017-10-25 E. I. du Pont de Nemours and Company Wässrige tintenstrahltinte mit polymerbindemitteln
JP2018505257A (ja) 2014-12-19 2018-02-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company オフセット媒体に印刷するためのインクジェットインクセット
US10280321B2 (en) * 2015-01-29 2019-05-07 Ricoh Company, Ltd. Ink, ink container, inkjet recording device, and recorded matter
JP2018536736A (ja) 2015-11-02 2018-12-13 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company 低沸点溶剤を含有する水性インクジェットインク
JP2019524916A (ja) 2016-06-24 2019-09-05 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company 非水溶性添加剤を含有する水性インクジェットインク
US11389867B2 (en) * 2017-02-24 2022-07-19 Hewlett-Packard Development Company, L.P. Three-dimensional (3D) printing
WO2018156933A1 (en) * 2017-02-24 2018-08-30 Hewlett-Packard Development Company, L.P. Three-dimensional printing
US11597850B2 (en) 2017-12-18 2023-03-07 Dupont Electronics, Inc. Ink fluid set for printing on offset media
US20220064473A1 (en) 2018-12-19 2022-03-03 Dupont Electronics, Inc. A textile printing fluid set containing a pretreatment and a mixture of pigment and disperse dye
EP4077556B1 (de) 2019-12-18 2023-11-29 DuPont Electronics, Inc. Tintenstrahltinte und primerflüssigkeitsset
US20230023036A1 (en) 2019-12-18 2023-01-26 Dupont Electronics, Inc. Inkjet ink and primer fluid set
WO2021126611A1 (en) 2019-12-18 2021-06-24 Dupont Electronics, Inc. Inkjet ink and primer fluid set
WO2023114574A1 (en) 2021-12-14 2023-06-22 Dupont Electronics, Inc. Inkjet ink and primer fluid set
WO2023114575A1 (en) 2021-12-14 2023-06-22 Dupont Electronics, Inc. Aqueous inkjet inks containing a polyurethane polymer
US20240124731A1 (en) 2022-09-26 2024-04-18 Dupont Electronics, Inc. Aqueous inkjet inks containing silanized silica particles

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3728992A1 (de) * 1987-08-29 1989-03-09 Basf Ag Phosphatgruppen enthaltende waessrige sekundaerdispersionen fuer anstrichmittel
EP0449456A1 (de) 1990-03-16 1991-10-02 Three Bond Co., Ltd. Klebstoffzusammensetzung
JPH0822991B2 (ja) 1990-05-21 1996-03-06 日本ペイント株式会社 水性塗料組成物
WO1993011181A1 (en) 1991-12-03 1993-06-10 Emmons William D Process for preparing an aqueous dispersion including polymeric latex and titanium dioxide pigment
US5231131A (en) 1991-12-24 1993-07-27 E. I. Du Pont De Nemours And Company Aqueous graft copolymer pigment dispersants
US5640180A (en) * 1994-03-08 1997-06-17 Sawgrass Systems, Inc. Low energy heat activated transfer printing process
US5502113A (en) 1994-08-22 1996-03-26 E. I. Du Pont De Nemours And Company Stable aqueous metallic flake dispersion using phosphated acrylic polymer dispersant
US5589522A (en) 1994-12-21 1996-12-31 Lexmark International, Inc. Ink composition
US5708066A (en) 1995-03-01 1998-01-13 E. I. Du Pont De Nemours And Company Reaction curable composition and solid surface material
US6248438B1 (en) 1995-10-25 2001-06-19 Rohm And Haas Company Method for preparing a paper label
US5746816A (en) * 1996-08-01 1998-05-05 Sawgrass Systems, Inc. Liquid ink process and printing method
US5708095A (en) 1996-08-30 1998-01-13 E. I. Du Pont De Nemours And Company Graft copolymers containing sulfonate and phosphonate groups having particular utility as pigmented ink dispersants

Also Published As

Publication number Publication date
ATE284906T1 (de) 2005-01-15
DE60016758T2 (de) 2005-12-08
AU6398300A (en) 2001-03-05
WO2001010918A1 (en) 2001-02-15
JP2003506536A (ja) 2003-02-18
US6433117B1 (en) 2002-08-13
EP1200492B1 (de) 2004-12-15
EP1200492A1 (de) 2002-05-02
CA2378837A1 (en) 2001-02-15

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