EP1245401B1 - Tintenstrahlaufzeichnungselement und Druckverfahren - Google Patents

Tintenstrahlaufzeichnungselement und Druckverfahren Download PDF

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Publication number
EP1245401B1
EP1245401B1 EP20020076042 EP02076042A EP1245401B1 EP 1245401 B1 EP1245401 B1 EP 1245401B1 EP 20020076042 EP20020076042 EP 20020076042 EP 02076042 A EP02076042 A EP 02076042A EP 1245401 B1 EP1245401 B1 EP 1245401B1
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EP
European Patent Office
Prior art keywords
mole
ink jet
polymeric particles
porous polymeric
acrylic
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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
EP20020076042
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English (en)
French (fr)
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EP1245401A3 (de
EP1245401A2 (de
Inventor
Jeanne E. Kaeding
Richard J. Kapusniak
Dennis E. Smith
Gregory E. Missell
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority claimed from US09/822,730 external-priority patent/US6554419B2/en
Priority claimed from US09/822,731 external-priority patent/US6541103B2/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP1245401A2 publication Critical patent/EP1245401A2/de
Publication of EP1245401A3 publication Critical patent/EP1245401A3/de
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5254—Macromolecular coatings characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5218—Macromolecular coatings characterised by inorganic additives, e.g. pigments, clays

Definitions

  • This invention relates to an ink jet recording element. More particularly, this invention relates to an ink jet recording element containing porous polymeric particles and a printing method using the element.
  • ink droplets are ejected from a nozzle at high speed towards a recording element or medium to produce an image on the medium.
  • the ink droplets, or recording liquid generally comprise a recording agent, such as a dye or pigment, and a large amount of solvent.
  • the solvent, or carrier liquid typically is made up of water, an organic material such as a monohydric alcohol, a polyhydric alcohol or mixtures thereof.
  • an ink jet recording element must:
  • ink jet recording element that simultaneously provides an almost instantaneous ink dry time and good image quality is desirable.
  • these requirements of ink jet recording media are difficult to achieve simultaneously.
  • Ink jet recording elements are known that employ porous or non-porous single layer or multilayer coatings that act as suitable image-receiving layers on one or both sides of a porous or non-porous support. Recording elements that use non-porous coatings typically have good image quality but exhibit poor ink dry time. Recording elements that use porous coatings exhibit superior dry times, but typically have poorer image quality and are prone to cracking and flaking.
  • Japanese Kokai Hei 7[1995]-137433 relates to an ink jet recording paper containing polyester-based hollow porous resin particles containing cationic groups.
  • porous resin particles containing cationic groups which are not limited to polyester resins.
  • Japanese Kokai Hei 11 [1999]-8569 relates to an ink jet recording sheet comprising porous organic particles which may be made cationic by adsorbing a cationic surfactant.
  • porous organic particles which may be made cationic by adsorbing a cationic surfactant.
  • the cationic functionality is not part of the polymeric structure and is only adsorbed to the surface, not chemically bound, so that it could be desorbed from the particle surface during manufacture, storage or imaging.
  • an ink jet recording element comprising a support having thereon an image-receiving layer comprising porous polymeric particles in a polymeric binder, the porous polymeric particles having the formula: wherein:
  • an ink jet recording element which has better dry time, water fastness and coating quality (cracking and flaking) than prior art elements while providing good image quality.
  • x is from 55 to 99 mole %; y is from 0 to 44 mole %; and z is from 1 to 45 mole %.
  • the support used in the ink jet recording element of the invention may be opaque, translucent or transparent.
  • the support is paper or a voided plastic material.
  • the thickness of the support employed in the invention can be from 12 to 500 ⁇ m, preferably from 75 to 300 ⁇ m.
  • porous polymeric particles which are used in the invention are in the form of porous beads, porous irregularly shaped particles, or are aggregates of emulsion particles and contain an ionic functionality.
  • Suitable addition polymerizable monomers which can be used as Unit A above contain at least two ethylenically unsaturated groups, and may include, for example, the following monomers and their mixtures: esters of unsaturated monohydric alcohols with unsaturated monocarboxylic acids, such as allyl methacrylate, allyl acrylate, butenyl acrylate, undecenyl acrylate, undecenyl methacrylate, vinyl acrylate, and vinyl methacrylate; dienes such as butadiene and isoprene; esters of saturated glycols or diols with unsaturated monocarboxylic acids, such as, ethylene glycol diacrylate, ethylene glycol dimethacrylate, triethylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,3-butanediol dimethacrylate, pentaerythritol tetraacrylate, trimethylol propane trimethacrylate
  • A includes ethylene glycol dimethacrylate, ethylene glycol diacrylate, 1,4-butanediol dimethylacrylate or divinylbenzene. Most preferably, A is divinylbenzene or ethylene glycol dimethacrylate.
  • Copolymerizable monomers which can be used as Unit B above are the following monomers and their mixtures: acrylic monomers, such as acrylic acid, or methacrylic acid, and their alkyl esters such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, ethyl acrylate, butyl acrylate, hexyl acrylate, n-octyl acrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, nonyl acrylate, benzyl methacrylate; the hydroxyalkyl esters of the same acids, such as, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and 2-hydroxypropyl methacrylate; the nitriles and amides of the same acids, such as, acrylonitrile, methacrylonitrile, acrylamide, t-butylacrylamide and methacrylamide; vinyl compounds, such as,
  • B is styrene, vinyl toluene, ethylvinylbenzene, 2-hydroxyethyl methacrylate, chloromethylstyrene, methacrylic acid or methyl methacrylate.
  • the styrenic or acrylic repeating units of C above contain an ionic functionality which may be obtained using a preformed ionic monomer which carries a substantially permanent charge which survives the polymerization.
  • functionalities in a formed porous polymeric particle can be modified to make them ionic.
  • pyridine can be protonated with an acid to form a quaternary nitrogen
  • an amine group can be quaternized with a chloroalkane
  • a carboxylic acid group can be neutralized with an amine or an alkali metal hydroxide to form a carboxylic anion
  • a chloromethyl group can be reacted with an amine to form a quaternary ammonium group, etc.
  • Modifying functionalities in a formed porous polymeric particle is preferred.
  • Suitable copolymerizable, ⁇ , ⁇ -ethylenically unsaturated monomers containing a preformed ionic functionality which can be used as Unit C include, for example, the following monomers and their mixtures: cationic ethylenically unsaturated monomers, for example, vinylbenzyltrimethylammonium chloride, vinylbenzyldimethyl-dodecylammonium chloride, other vinylbenzylammonium salts in which the three other ligands on the nitrogen can be any alkyl or carbocyclic group including cyclic amines such as piperidine, the counter ions of which can be halides, sulfonates, phosphates, sulfates, etc.; [2-(methacryloyloxy)ethyl]trimethyl-ammonium chloride, [2-(acryloyloxy)ethyl]-trimethylammonium p-toluene-sulfonate, and other acrylate and
  • the cationic functionality is vinylbenzyltrimethylammonium chloride, vinylbenzyl-N-butylimidazolium chloride, vinylbenzyldimethyldodecylammonium chloride or vinylbenzyldimethyloctadecylammonium chloride.
  • Suitable copolymerizable, ⁇ , ⁇ -ethylenically unsaturated monomers containing a preformed ionic functionality which can be used as Unit C include, for example, the following monomers and their mixtures: anionic ethylenically unsaturated monomers such as 2-phosphatoethyl acrylate potassium salt, 3-phosphatopropyl methacrylate ammonium salt, and other acrylic and methacrylic esters of alkylphosphonates in which the alkyl group connecting the acrylic function to the phosphate function can be ⁇ 2 carbon atoms long, the counter ions of which can be alkali metal cations, quaternary ammonium cations, phosphonium cations, or the like; sodium methacrylate, potassium acrylate, and other salts of carboxylic acids; styrenesulfonic acid ammonium salt, methyltriphenylphosphonium styrenesulfonate, and other styrene sulfonic
  • repeating Unit C is to be formed after the porous polymeric particle is prepared, all or some of Units A or Units B in a porous polymeric particle can be modified to make them (or part of them) ionic. All of the cationic and anionic functionalities mentioned above can be incorporated by modifying a non-ionic porous polymeric particle.
  • the porous polymeric particles used in this invention can be prepared, for example, by pulverizing and classification of porous organic compounds, by emulsion, suspension, and dispersion polymerization of organic monomers, by spray drying of a solution containing organic compounds, or by a polymer suspension technique which consists of dissolving an organic material in a water immiscible solvent, dispersing the solution as fine liquid droplets in aqueous solution, and removing the solvent by evaporation or other suitable techniques.
  • the bulk, emulsion, dispersion, and suspension polymerization procedures are well known to those skilled in the polymer art and are taught in such textbooks as G. Odian in "Principles of Polymerization", 2nd Ed. Wiley (1981), and W.P. Sorenson and T.W. Campbell in “Preparation Method of Polymer Chemistry", 2nd Ed, Wiley (1968).
  • a preferred method of preparing the porous polymeric particles used in this invention includes forming a suspension or dispersion of ethylenically unsaturated monomer droplets containing the crosslinking monomer A, the monomer containing an ionic functionality or a monomer containing a group which will be converted to an ionic functionality, and a porogen in an aqueous medium, polymerizing the monomer to form porous polymeric particles, and optionally removing the porogen by vacuum stripping.
  • the particles thus prepared have a porosity as measured by a specific surface area of greater than 100 m 2 /g. The surface area is usually measured by B.E.T. nitrogen analysis known to those skilled in the art.
  • the porous polymeric particles used in the invention may be covered with a layer of colloidal inorganic particles as described in U.S. Patents 5,288,598 ; 5,378,577 ; 5,563,226 and 5,750,378 .
  • the porous polymeric particles may also be covered with a layer of colloidal polymer latex particles as described in U.S. Patent 5,279,934 .
  • the porous polymeric particles used in this invention generally have a median diameter of from 0.05 ⁇ m to 10 ⁇ m, preferably from 0.1 ⁇ m to 5 ⁇ m.
  • Median diameter is defined as the statistical average of the measured particle size distribution on a volume basis. For further details concerning median diameter measurement, see T. Allen, "Particle Size Measurement", 4th Ed., Chapman and Hall, (1990).
  • the polymeric particles used in the invention are porous.
  • porous is meant particles which either have voids or are permeable to liquids.
  • Preferred are particles which have voids. These particles can have either a smooth or a rough surface.
  • the image-receiving layer may also contain additives such as pH-modifiers like nitric acid, cross-linkers, rheology modifiers, surfactants, UV-absorbers, biocides, lubricants, water-dispersible latexes, mordants, dyes, optical brighteners etc.
  • pH-modifiers like nitric acid, cross-linkers, rheology modifiers, surfactants, UV-absorbers, biocides, lubricants, water-dispersible latexes, mordants, dyes, optical brighteners etc.
  • the image-receiving layer may be applied to one or both substrate surfaces through conventional pre-metered or post-metered coating methods such as blade, air knife, rod, roll, slot die, curtain, slide, etc.
  • coating process would be determined from the economics of the operation and in turn, would determine the formulation specifications such as coating solids, coating viscosity, and coating speed.
  • the ink jet inks used to image the recording elements of the present invention are well-known in the art.
  • the ink compositions used in ink jet printing typically are liquid compositions comprising a solvent or carrier liquid, dyes or pigments, humectants, organic solvents, detergents, thickeners, preservatives, and the like.
  • the solvent or carrier liquid can be solely water or can be water mixed with other water-miscible solvents such as polyhydric alcohols.
  • Inks in which organic materials such as polyhydric alcohols are the predominant carrier or solvent liquid may also be used. Particularly useful are mixed solvents of water and polyhydric alcohols.
  • the dyes used in such compositions are typically watersoluble direct or acid type dyes.
  • Such liquid compositions have been described extensively in the prior art including, for example, U.S. Patents 4,381,946 ; 4,239,543 and 4,781,758 .
  • the flask was placed in a 50°C constant temperature bath and the dispersion stirred at 130 rev./min. under positive pressure nitrogen for 16 hours to polymerize the monomer droplets into porous polymeric particles.
  • the product was filtered through a coarse filter to remove coagulum.
  • MAZU® antifoam agent BASF Corp.
  • the porous polymeric particles were measured by a particle size analyzer, Horiba LA-920®, and found to be 1.5 ⁇ m in median diameter.
  • the pH was measured and found to be 3.3.
  • a dried portion of the dispersion, analyzed by B.E.T. Multipoint using a Quantachrome Corp., NOVA® analyzer had a specific surface area of 21 m 2 /g.
  • the flask was placed in a 50° constant temperature bath and the dispersion stirred at 125 rev./min. under positive pressure nitrogen for 16 hours to polymerize the monomer droplets into porous polymeric particles.
  • the product was filtered through a coarse filter to remove coagulum.
  • toluene and some water were distilled off under vacuum at 60° to give 24.6% solids.
  • the porous polymeric particles were measured by a particle size analyzer, Horiba LA-920®, and found to be 1.3 ⁇ m in median diameter.
  • the pH was measured and found to be 4.3.
  • a dried portion of the dispersion, analyzed by B.E.T. Multipoint using a Quantachrome Corp. NOVA® analyzer had a specific surface area of 221.98 m 2 /g.
  • the flask was placed in a 50°C constant temperature bath and the dispersion stirred at 150 rev./min. under positive pressure nitrogen for 16 hours to polymerize the monomer droplets into porous polymeric particles.
  • Toluene and some water were distilled off under vacuum at 60°C.
  • the product was filtered through a coarse filter to remove coagulum to give a product of 22.7% solids.
  • the porous polymeric particles were measured by a particle size analyzer, Horiba LA-920®, and found to be 1.0 ⁇ m in median diameter.
  • porous polymeric particles were measured by a particle size analyzer, Horiba LA-920®, and found to be 1.2 ⁇ m in median diameter.
  • Propyl acetate and some water were distilled off under vacuum at 60°C.
  • the product was filtered through a coarse filter to remove coagulum.
  • the final product was 15.2 % solids.
  • the porous polymeric particles were measured by a particle size analyzer, Horiba LA-920®, and found to be 0.74 ⁇ m in median diameter.
  • a coating solution was prepared by mixing together the control porous polymeric particles of Preparation C1 with a binder of poly(vinyl alcohol) using Gohsenol GH 23® (Gohsen Nippon of Japan). The resulting coating solution was 15% solids and 85% water, with the solids being 85% porous polymeric particles and 15% poly(vinyl alcohol). The solution was stirred at 40°C for approximately 30 minutes before coating.
  • the solution was then coated on corona discharge-treated, photographic grade, polyethylene-coated paper using a wound wire metering rod, to a wet lay down of 120 ⁇ m, and oven dried for 30 minutes at 60°C. This element was coated to a dry thickness of 18 ⁇ m.
  • This element was prepared the same as Control Element C-1 except that the coating solution was made using Preparation C3.
  • Coating quality is a visual inspection of the above coated elements, looking at coating defects such as cracking, particle agglomeration, coating flaking off, coating uniformity or smoothness.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Ink Jet (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Claims (10)

  1. Tintenstrahl-Aufzeichnungselement mit einem Träger, auf dem sich eine Bildempfangsschicht befindet, die poröse polymere Teilchen in einem polymeren Bindemittel umfasst, wobei die porösen polymeren Teilchen folgende Formel haben:
    Figure imgb0004
     worin:
    A Einheiten eines durch Additionspolymerisation polymerisierbaren Monomers darstellt, das mindestens zwei olefinisch ungesättigte Gruppen enthält;
    B Einheiten von copolymerisierbaren Monomeren darstellt, die aus der aus Acrylmonomeren, Nitrilen und Amiden von Acrylsäure oder Methacrylsäure, Vinylverbindungen, aromatischen Vinylverbindungen, Dialkylestem bestehenden Gruppe und Gemischen davon ausgewählt wurden;
    C styrolische oder acrylische wiederkehrende Einheiten darstellt, die eine ionische Funktionalität aufweisen;
    x zwischen 27 und 99 Mol-%;
    y zwischen 0 und 72 Mol-%; und
    z zwischen 1 und 73 Mol-% liegt.
  2. Element nach Anspruch 1, worin die ionischen Funktionalität der wiederkehrenden styrolischen oder acrylischen Einheiten kationisch ist.
  3. Element nach Anspruch 2, worin es sich bei der kationischen Funktionalität um Vinylbenzyltrimethylammoniumchlorid, Vinylbenzyl-N-butylimidazoliumchlorid, Vinylbenzyldimethyldodecylammoniumchlorid oder Vinylbenzyldimethyloctadecylammoniumchlorid handelt.
  4. Element nach Anspruch 1, worin die ionische Funktionalität der wiederkehrenden styrolischen oder acrylischen Einheiten anionisch ist.
  5. Element nach Anspruch 4, worin es sich bei der anionischen Funktionalität um das Trimethylammoniumsalz der Methacrylsäure, das Dimethylbenzylammoniumsalz der Methacrylsäure, das Dimethyldodecylammoniumsalz der Methacrylsäure oder das Methyltrioctylammoniumsalz der Styrolsulfonsäure handelt.
  6. Element nach Anspruch 1, worin
    x zwischen 55 und 99 Mol-%;
    y zwischen 0 und 44 Mol-%; und
    z zwischen 1 und 45 Mol-% liegt.
  7. Element nach Anspruch 1, worin der Medianwert für den Durchmesser der porösen polymeren Teilchen zwischen 0,05 µm und 10 µm liegt.
  8. Element nach Anspruch 1, worin der Medianwert für den Durchmesser der porösen polymeren Teilchen zwischen 0,1 µm und 5 µm liegt.
  9. Element nach Anspruch 1, worin das polymere Bindemittel einen Polyvinylalkohol, eine Gelatine, einen Celluloseether, Polyvinylpyrrolidon oder Polyethylenoxid umfasst.
  10. Tintenstrahldruckverfahren mit folgenden Schritten:
    A) Bereitstellen eines Tintenstrahldruckers, der auf digitale Datensignale anspricht;
    B) Beladen des Druckers mit einem Tintenstrahl-Aufzeichnungselement mit einem Träger, auf dem sich eine Bildempfangsschicht befindet, die poröse polymere Teilchen in einem polymeren Bindemittel umfasst, wobei die porösen polymeren Teilchen folgende Formel haben:
    Figure imgb0005
     worin:
    A Einheiten eines durch Additionspolymerisation polymerisierbaren Monomers darstellt, das mindestens zwei olefinisch ungesättigte Gruppen enthält;
    B Einheiten von copolymerisierbaren Monomeren darstellt, die aus der aus Acrylmonomeren, Nitrilen und Amiden von Acrylsäure oder Methacrylsäure, Vinylverbindungen, aromatischen Verbindungen mit Vinylgruppen, Dialkylestem bestehenden Gruppe und Gemischen davon ausgewählt wurden;
    C styrolische oder acrylische wiederkehrende Einheiten darstellt, die eine ionische Funktionalität aufweisen;
    x zwischen etwa 27 und etwa 99 Mol-%;
    y zwischen 0 und etwa 72 Mol-%; und
    z zwischen etwa 1 und etwa 73 Mol-% liegt.
    C) Beladen des Druckers mit einer Tintenstrahl-Tintenkomposition; und
    D) Bedrucken der Bildempfangsschicht unter Verwendung der Tintenstrahl-Tintenkomposition entsprechend den digitalen Datensignalen.
EP20020076042 2001-03-30 2002-03-18 Tintenstrahlaufzeichnungselement und Druckverfahren Expired - Fee Related EP1245401B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US822730 1986-01-27
US09/822,730 US6554419B2 (en) 2001-03-30 2001-03-30 Ink jet printing method
US09/822,731 US6541103B2 (en) 2001-03-30 2001-03-30 Ink jet recording element
US822731 2001-03-30

Publications (3)

Publication Number Publication Date
EP1245401A2 EP1245401A2 (de) 2002-10-02
EP1245401A3 EP1245401A3 (de) 2005-01-05
EP1245401B1 true EP1245401B1 (de) 2007-11-28

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JP (1) JP4331436B2 (de)
DE (1) DE60223741T2 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
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WO2013006904A1 (en) * 2011-07-12 2013-01-17 University Of Tasmania Use of porous polymer materials for storage of biological samples

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Publication number Priority date Publication date Assignee Title
ATE470578T1 (de) * 2003-07-18 2010-06-15 Basf Se Tintenstrahlaufzeichnungsmedium
WO2011082449A1 (en) 2010-01-08 2011-07-14 University Of Tasmania Porous polymer monoliths, processes for preparation and use thereof

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US5840293A (en) 1988-11-16 1998-11-24 Advanced Polymer Systems, Inc. Ionic beads for controlled release and adsorption
CA2017570C (en) 1989-05-31 2000-12-19 James R. Gross Porous structure of an absorbent polymer
JP2999594B2 (ja) 1990-07-16 2000-01-17 三井化学株式会社 多層構造エマルション粒子
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Publication number Priority date Publication date Assignee Title
WO2013006904A1 (en) * 2011-07-12 2013-01-17 University Of Tasmania Use of porous polymer materials for storage of biological samples

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EP1245401A3 (de) 2005-01-05
JP2002362021A (ja) 2002-12-18
DE60223741D1 (de) 2008-01-10
EP1245401A2 (de) 2002-10-02
DE60223741T2 (de) 2008-10-30
JP4331436B2 (ja) 2009-09-16

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