WO2001044386A1 - Ink compositions - Google Patents

Ink compositions Download PDF

Info

Publication number
WO2001044386A1
WO2001044386A1 PCT/US2000/033409 US0033409W WO0144386A1 WO 2001044386 A1 WO2001044386 A1 WO 2001044386A1 US 0033409 W US0033409 W US 0033409W WO 0144386 A1 WO0144386 A1 WO 0144386A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
binder
weight
colorant
ranges
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.)
Ceased
Application number
PCT/US2000/033409
Other languages
English (en)
French (fr)
Inventor
Bradley Leonard Beach
Ann P. Holloway
Ajay Kanubhai Suthar
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.)
Lexmark International Inc
Original Assignee
Lexmark International Inc
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 Lexmark International Inc filed Critical Lexmark International Inc
Priority to AU20788/01A priority Critical patent/AU2078801A/en
Priority to JP2001544866A priority patent/JP2004530732A/ja
Priority to EP00984110A priority patent/EP1268688B1/en
Priority to DE60014179T priority patent/DE60014179T2/de
Publication of WO2001044386A1 publication Critical patent/WO2001044386A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks

Definitions

  • This invention relates to the field of ink compositions for ink jet printers.
  • the present invention relates to ink compositions for ink jet printers. More particularly, the present invention relates to ink compositions comprising a colorant and a
  • Ink jet printing is a conventional technique by which printing is normally
  • piezo-electric elements and/or heaters for vapor phase bubble formation are piezo-electric elements and/or heaters for vapor phase bubble formation.
  • the ink compositions used in ink jet printing typically employ an aqueous carrier, usually water, colorants and low molecular weight water miscible materials.
  • an aqueous carrier usually water, colorants and low molecular weight water miscible materials.
  • colorants which may be employed include dyes and pigments. Pigments provide improved
  • pigment based ink compositions have a tendency to dry smear, have low resistance to wet-
  • dry smear means
  • wet-rub means applying a drop of water to the printed substrate followed by applying abrasive pressure across the printed substrate using
  • wet-rub differs from waterfastness because abrasion is used.
  • highlighter resistance means applying abrasive pressure across the
  • an ink composition comprising a colorant and a polymeric binder that improves
  • the present invention has
  • Polymers have been added to ink jet ink compositions to improve durability, to improve print quality and to reduce color bleeding and feathering.
  • the inclusion of polymers has resulted in increased printhead maintenance problems, including clogging
  • the resin is a polymeric core/shell material with a
  • Tg glass transition temperature of the core in the range of from -100°C to 40°C, and a
  • the colorants and form a film on the substrate when the ink is jetted.
  • Sacripante discloses a Tg range of 10°C - 100°C, preferably 35°C
  • Anton discloses an ink composition utilizing a core/shell emulsion
  • Anton illustrates a core/shell emulsion polymer containing two distinct phases having different Tj take-up i.e. one phase has a Tg above ambient temperature
  • thermoplastic resin and water. Fujisawa teaches that the thermoplastic resin has a Tg of
  • thermoplastic resin 50° - 150°C. Fujisawa further teaches that the particle diameter of the thermoplastic resin
  • Kubota discloses an ink composition which comprises a colorant, an
  • Nichols discloses an inkjet ink formulation with colorant
  • Nichols has 1 to 40 wt.% "carboxylic acid groups", and Tg of 0°C to 120°C; exemplified
  • embodiments of the resin include copolymers of butyl acrylate, methyl methacrylate and
  • (meth)acrylic acid with 3 to 20 wt.% acid, Tg of 53°C to 95°C and particle size of 63 nm
  • binder particles generally less than about 200nm average diameter
  • the apparent Tg of the binder should be significantly above ambient temperature (i.e., above about 25°C) to avoid maintenance problems such as kogation.
  • rub may be incorporated into inks by utilizing polymer resins or core/shell polymer
  • an ink composition comprising a colorant and a polymeric binder wherein the polymeric
  • binder has an average particle diameter of greater than about 200nm, a below ambient Tg
  • the present invention provides improved resistance to dry smear, improved resistance to wet-rub, and improved highlighter resistance without creating the printhead maintenance problems of kogation and clogging.
  • the present invention is an aqueous ink. More specifically, this invention relates
  • inks comprising a colorant and a polymeric binder wherein the binder has suitable glass
  • Tg transition temperature
  • present invention includes a colorant and a polymeric binder with the extraordinary and
  • An ink composition utilizing a polymeric binder with a below ambient Tg is an ink composition utilizing a polymeric binder with a below ambient Tg.
  • a polymeric binder with a below ambient Tg removes the
  • a polymeric binder with a below ambient Tg generally causes increased
  • the ink composition according to the present invention contains a colorant, a
  • the colorant of the present invention may be a dye or a pigment, and preferably is
  • the colorant is a water insoluble pigment.
  • the colorant may be a
  • sclf-disperscd pigment a pigment mixed with a dispersant, or a combination of these.
  • the colorant is selected from the group consisting of the following compounds:
  • the colorant is present at from about 1 % to about 5% by weight of
  • the colorant is present al from about 2% to about 4% by weight of the final ink composition.
  • organic or inorganic pigments may be used.
  • pigments which may be employed in this invention includes azo pigments such as condensed
  • polycyclic pigments such as phthalocyanines, anthraquinones,
  • quinacridones thioindigoids, isoindolinones, quinophthalones.
  • Still other pigments which may be employed include, for example, nitro pigments, daylight fluorescent pigments,
  • pigments may be prepared via conventional techniques and many are commercially available.
  • the pigment particle size ranges from about lOnm to about 250nm, and in one
  • it is about 130nm.
  • pigment for inks including preparation of self-dispersed pigment and preparation of
  • a process for preparing pigment dispersions used in inks is
  • pigments which may be used in the present invention are carbon black, such as Monarch
  • Raven 1 170 and Raven 2500 (from Columbian Chemicals Company); yellow pigment, such as pigment yellow 74 and pigment yellow 13 (from Sun Chemical Corporation), pigment yellow 138 (from Toyo Manufacturing); cyan pigment, such as pigment blue
  • magenta pigment such as pigment red 122, pigment red 57 and
  • pigment red 81 (from Sun Chemical Corporation), pigment red 122 (from Toyo
  • the polymeric binder of the present invention comprises a polymer or copolymer
  • acrylate esters methacrylate
  • esters styrenes, substituted styrenes, vinyl acrylates, vinyl acetates, fluoromethacrylates,
  • acrylamides substituted acrylamides, methacrylamides, substituted methacrylamides, and combinations thereof.
  • esters of acrylic acid and methacrylic acid preferred
  • monomers include methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, lauryl
  • the binder comprises copolymer of butyl acrylate and methyl methacrylate.
  • the polymeric binder comprises a co-polymer ranging
  • the polymeric binder may comprise a copolymer
  • the polymeric binder in another embodiment, is not limited to 72% by weight of butyl acrylate.
  • the polymeric binder in another embodiment, is not limited to 72% by weight of butyl acrylate.
  • polymeric binder for example 14.5% by weight methyl methacrylate, 80.5% by weight
  • polymeric binder compositions examples include polymer or copolymers with from 1 to 10% by weight acid
  • the polymeric binder is present at about 0.5% and at about 3% by
  • the polymeric binder further comprises an acid component.
  • the acid component is an acid component.
  • acrylic acid methacrylic acid, itaconic acid, vinyl sulfonic acid, maleic
  • acids or combinations thereof may be derived from salts or anhydrides of such acids,
  • the acid component is methacrylic acid.
  • the acid component is methacrylic acid in combination with another acid.
  • the acid component of the polymeric binder ranges from about 1% to about 10% by weight of the total weight of the polymeric binder. In one embodiment, when the acid
  • the acid component is methacrylic acid, the acid component is about 1.1% to about 1.5% by
  • the acid component is methacrylic acid, the acid component is about 1.3% by weight of the total
  • compositions shown below do not represent the only possible formulations encompassed
  • the present invention includes ink compositions when
  • the acid component of the polymeric binder ranges from about 1% to about 10% by
  • the optimal Tg range of the polymeric binder is from about -20°C to about 70°C.
  • the optimal preferable Tg range is from about - 12°C to about 25°C.
  • polymeric binder of the present invention is suitable for use in conventional (i.e., thermal
  • Lexmark 5700 Lexmark Z51 and Lexmark 2050 printers.
  • binder may range from about -I 0°C to about 25°C, or from about -10°C to about 0°C.
  • the polymeric binder has a Tg of about -10°C. At these glass transition
  • the binder is believed to form an adhesive film, continuous or otherwise,
  • the adhesive effect may be achieved through
  • spot welds in which sufficient polymer is present to adhere one or more colorant particles to the substrate.
  • the polymer particles comprising the polymeric binder have an average diameter
  • average diameter less than 200nm are less likely to cause printhead maintenance
  • the particle size distribution of the polymeric binder may be unimodal, bimodal or
  • the polymeric binder has a bimodal particle size
  • the small size particles have an average diameter in the
  • the large size particles have an average diameter in the
  • the average particle size is within the range from about 250
  • the polymeric binder has a unimodal
  • the polymeric binder has a unimodal particle size distribution
  • the average particle size and particle size distribution may be determined by the capillary hydrodynamic fractionation (CHDF) technique.
  • CHDF capillary hydrodynamic fractionation
  • the molecular weight of the polymeric binder is not critical. However, it has been
  • the polymeric binder preferably has a molecular weight in the range from about
  • molecular weight as used herein, is defined as the weight average molecular weight
  • polymeric binder of the present invention may further comprise additional components
  • sufactants include sodium lauryl
  • the polymeric binder may be prepared by a conventional persulfate-initiated
  • thermal process known in the art such as batch, semi-batch, gradual addition or
  • the monomers are polymerized to preferably greater than 99% conversion
  • pH 8-9 preferably between pH 8-9; with neutralizer such as, for example, ammonia,
  • potassium hydroxide is used as neutralizer.
  • the preparation process used has
  • present invention allows for controlled particle size and particle size distribution at the
  • the polymeric binder may be illustrated, in certain embodiments, through the
  • SLS sodium lauryl sulfate
  • NaPS sodium persulfate
  • the filtered product was neutralized by combining 865 g of unneutralized
  • the average particle size was 280 nm with a particle size distribution ranging
  • BA butyl acrylate
  • MMA methyl methacrylate
  • MAA MAA
  • polymer had an average particle sized of 286 nm with a particle size distribution ranging
  • Example 3 A sample of butyl acrylate (BA), methyl methacrylate (MMA), and acrylic acid
  • monomer mixture consisted of 23.5 g AA, 667.7 g MMA, 1468.8 g BA and 10.5 g SLS.
  • reaction vessel containing 1 130 g deionized, buffered water and 3.0 g SLS
  • the resultant polymer had an average particle size of 348 nm with a particle
  • MAA acid
  • the resultant polymer had an average particle size of 301 nm
  • MAA acid
  • reaction vessel containing 1 130 g deionized, buffered water and 5.0
  • the resultant polymer had an average particle size of 254 nm with a particle
  • MAA amino acid
  • reaction vessel containing 1 130 g deionized, buffered water and 5.0
  • the resultant polymer had an average particle size of 238 nm with a particle size distribution ranging from 133 nm to 340 nm.
  • the calculated Tg of this polymer was
  • the aqueous carrier of the present invention is water (preferably deionized water).
  • the aqueous carrier is present at from about 40% to about 95%, may be present at from
  • the ink composition of the present invention may also include water miscible
  • humectants such as humectants, dispersants, penetrants, chelating agents, buffers, biocides,
  • fungicides fungicides, bacteriocides, surfactants, anti-curling agents, anti-bleed agents and surface
  • the amount of humectant used is determined by the desired properties of the ink
  • humectants include ethylene glycol, 1 ,3 propanediol, 1 ,4 butanediol, 1 ,4
  • tetraethylene glycol polyethylene glycol with average molecular weight of 200, 300, 400,
  • Preferred humectants are polyethylene glycol with
  • the amount of penetrant used is determined by the desired properties of the ink
  • penetrants are 1 ,2 alkyl diols of from 4 to 10 carbon atoms forming the alkyl such as 1 ,2-
  • Useful penetrants include N-propanol, isopropyl alcohol, 1 ,2 hexanediol, and
  • the amount of dispersant used is determined by the properties of the colorant when the colorant is a pigment.
  • Useful dispersants are graft copolymers compromising a
  • hydrophilic polymeric segment a hydrophobic polymeric segment incorporating a
  • hydrolytically-stable siloxyl substituent hydrolytically-stable siloxyl substituent, and a stabilizing segment.
  • a preferred dispersant hydrolytically-stable siloxyl substituent, and a stabilizing segment.
  • composition is not critical as long as its use results in a stable and printable ink.
  • the ink composition of the present invention may be prepared by any method
  • the ink composition of the present invention would include any one of
  • additives include chelating agents, buffers, biocides, fungicides,
  • ink composition examples include the following
  • humectant 5% polyethylene glycol 1000, 5% 2,2-thiodiethanol and 5% 2-
  • humectant (10% polyethylene glycol 400 and 10% 2,2-thiodiethanol)
  • humectant 10% polyethylene glycol 400 and 10%> 2,2 thiodiethanol
  • humectant 10% polyethylene glycol 400 and 10%. 2,2-thiodiethanol
  • the pigment particles together to form a film successfully adhering the pigment particles together and to the substrate. It is believed that the polymeric binder encapsulates the
  • polymeric binder forms a film on the substrate, holding the pigment particles in place
  • the polymeric binder of the present invention is a polymeric binder of the present invention
  • the printhead apparatus eg. nozzle openings, nozzle

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Ink Jet (AREA)
PCT/US2000/033409 1999-12-14 2000-12-08 Ink compositions Ceased WO2001044386A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU20788/01A AU2078801A (en) 1999-12-14 2000-12-08 Ink compositions
JP2001544866A JP2004530732A (ja) 1999-12-14 2000-12-08 インク組成物
EP00984110A EP1268688B1 (en) 1999-12-14 2000-12-08 Ink compositions
DE60014179T DE60014179T2 (de) 1999-12-14 2000-12-08 Tintenzusammensetzungen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/460,959 1999-12-14
US09/460,959 US6646024B2 (en) 1999-12-14 1999-12-14 Ink compositions

Publications (1)

Publication Number Publication Date
WO2001044386A1 true WO2001044386A1 (en) 2001-06-21

Family

ID=23830707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/033409 Ceased WO2001044386A1 (en) 1999-12-14 2000-12-08 Ink compositions

Country Status (7)

Country Link
US (1) US6646024B2 (enExample)
EP (1) EP1268688B1 (enExample)
JP (1) JP2004530732A (enExample)
AU (1) AU2078801A (enExample)
DE (1) DE60014179T2 (enExample)
TW (1) TWI228529B (enExample)
WO (1) WO2001044386A1 (enExample)

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EP1245653A3 (en) * 2001-03-30 2002-11-06 Eastman Kodak Company Ink jet ink composition and printing method
US6716912B2 (en) * 1999-12-14 2004-04-06 Rohm And Haas Company Polymeric binders for water-resistant ink jet inks
US7479183B2 (en) 2001-03-30 2009-01-20 Eastman Kodak Company Ink jet ink composition
EP2213707A4 (en) * 2007-11-15 2014-03-05 Seiko Epson Corp Ink Composition
US9382438B2 (en) 2012-03-12 2016-07-05 Seiko Epson Corporation Ink composition for ink jet recording, penetrant for ink jet recording, and recording apparatus

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EP1333072A3 (en) * 2002-01-30 2003-11-12 Rohm And Haas Company Ink composition
US8363299B2 (en) 2002-06-10 2013-01-29 E Ink Corporation Electro-optic displays, and processes for the production thereof
US9470950B2 (en) 2002-06-10 2016-10-18 E Ink Corporation Electro-optic displays, and processes for the production thereof
US7110164B2 (en) 2002-06-10 2006-09-19 E Ink Corporation Electro-optic displays, and processes for the production thereof
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EP1418209A3 (en) * 2002-11-08 2005-03-16 Rohm And Haas Company Method for forming an aqueous carbon black dispersion
US20050032930A1 (en) * 2003-07-02 2005-02-10 Christian Jackson Inkjet ink
CN101382719B (zh) * 2003-10-24 2012-04-04 伊英克公司 电光显示器
EP1676165B1 (en) * 2003-10-24 2017-12-13 E Ink Corporation Film for use in manufacturing electro-optic displays
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US7156514B2 (en) * 2004-04-30 2007-01-02 Lexmark International, Inc. Inks and printheads with internal clog prevention
WO2006006994A2 (en) * 2004-06-22 2006-01-19 Lexmark International, Inc. Inkjet ink composition
US7381753B2 (en) * 2004-06-29 2008-06-03 Lexmark International, Inc. Inkjet ink composition
US20060065138A1 (en) * 2004-09-30 2006-03-30 Tucker Robert C Pad printing method for making colored contact lenses
US7677714B2 (en) * 2004-10-01 2010-03-16 Hewlett-Packard Development Company, L.P. Inkjet inks providing improved wet smudge on porous print media
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JP2006225637A (ja) * 2005-01-18 2006-08-31 Canon Inc インク、インクセット、インクジェット記録方法、インクカートリッジ及びインクジェット記録装置
US20060167135A1 (en) * 2005-01-25 2006-07-27 Lexmark International, Inc. Inkjet ink binder and inkjet ink composition
US7842347B2 (en) * 2005-06-09 2010-11-30 Lexmark International, Inc. Inkjet printing of layers
KR100750129B1 (ko) * 2005-09-06 2007-08-21 삼성전자주식회사 잉크 조성물, 이를 포함한 잉크 카트리지 및 잉크젯 기록장치
US7655707B2 (en) * 2005-12-02 2010-02-02 Hewlett-Packard Development Company, L.P. Pigmented ink-jet inks with improved image quality on glossy media
US8659158B2 (en) * 2006-08-16 2014-02-25 Funai Electric Co., Ltd. Thermally inkjettable acrylic dielectric ink formulation and process
US8226222B2 (en) * 2008-03-28 2012-07-24 Nippon Kayaku Kabushiki Kaisha Ink set, recording method, and colored object
US7841687B2 (en) 2008-08-06 2010-11-30 Lexmark International, Inc. System and method for identifying a prescribed inkjet ink
JP2010260956A (ja) * 2009-05-07 2010-11-18 Seiko Epson Corp インクジェット記録用インク組成物
EP2295509B1 (en) * 2009-09-10 2013-01-09 Canon Kabushiki Kaisha Liquid composition, set, liquid cartridge, inkjet recording method, and inkjet recording apparatus
US8282202B2 (en) * 2010-10-29 2012-10-09 Eastman Kodak Company Aqueous inkjet printing fluid compositions
US20120162332A1 (en) * 2010-12-22 2012-06-28 Hong Kong Applied Science and Technology Research Institute Company Limited Sublimation inks for thermal inkjet printers using thermally stable dye particles
US20120172490A1 (en) * 2010-12-31 2012-07-05 Xiaorong Cai Carbon black pigmented inkjet ink to reduce kogation and improve text quality
DE102012208512A1 (de) * 2012-05-22 2013-11-28 Océ Printing Systems GmbH & Co. KG Verfahren und Reinigungsflüssigkeit zur Reinigung von Inkjet-Druckköpfen, Verwendung einer solchen Reinigungsflüssigkeit
US9570751B2 (en) * 2013-02-26 2017-02-14 Samsung Sdi Co., Ltd. Binder composition for secondary battery, anode including the binder composition, and lithium battery including the anode
JP2015044405A (ja) * 2013-08-02 2015-03-12 株式会社リコー インクジェット記録方法及びインクジェット記録装置
GB201610925D0 (en) * 2016-06-22 2016-08-03 Imp Innovations Ltd Aqueous ink compositions
FI127636B (en) * 2017-04-13 2018-11-15 Tikkurila Oyj An aqueous universal colourant composition and a method for tinting a base paint
CN110540776B (zh) * 2019-10-12 2022-04-19 深圳市墨库图文技术有限公司 一种应用于数码印花颜料的分散液

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Publication number Publication date
DE60014179D1 (de) 2004-10-28
TWI228529B (en) 2005-03-01
EP1268688A1 (en) 2003-01-02
AU2078801A (en) 2001-06-25
DE60014179T2 (de) 2006-02-16
US20020147250A1 (en) 2002-10-10
EP1268688A4 (en) 2003-06-25
US6646024B2 (en) 2003-11-11
JP2004530732A (ja) 2004-10-07
EP1268688B1 (en) 2004-09-22

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