EP0052730B1 - Matériaux pour l'enregistrement sensible à la pression - Google Patents

Matériaux pour l'enregistrement sensible à la pression Download PDF

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Publication number
EP0052730B1
EP0052730B1 EP81108067A EP81108067A EP0052730B1 EP 0052730 B1 EP0052730 B1 EP 0052730B1 EP 81108067 A EP81108067 A EP 81108067A EP 81108067 A EP81108067 A EP 81108067A EP 0052730 B1 EP0052730 B1 EP 0052730B1
Authority
EP
European Patent Office
Prior art keywords
acrylate
acid
recording material
alcohol
weight
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
Application number
EP81108067A
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German (de)
English (en)
Other versions
EP0052730A1 (fr
Inventor
Dietrich Hoffmann
Holger Dr. Schoepke
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0052730A1 publication Critical patent/EP0052730A1/fr
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Publication of EP0052730B1 publication Critical patent/EP0052730B1/fr
Expired legal-status Critical Current

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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
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132—Chemical colour-forming components; Additives or binders therefor
    • B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3331—Macromolecular compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component
    • Y10T428/249994—Composite having a component wherein a constituent is liquid or is contained within preformed walls [e.g., impregnant-filled, previously void containing component, etc.]
    • Y10T428/249995—Constituent is in liquid form
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component
    • Y10T428/249994—Composite having a component wherein a constituent is liquid or is contained within preformed walls [e.g., impregnant-filled, previously void containing component, etc.]
    • Y10T428/249995—Constituent is in liquid form
    • Y10T428/249997—Encapsulated liquid
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y10T428/254—Polymeric or resinous material

Definitions

  • the invention relates to pressure-sensitive recording material.
  • the carbon paper-free copy papers used today consist of a combination of sheets.
  • the cover sheet contains a coating with microcapsules on the back, the interleaves also have a microcapsule coating on the back (donor side: CB side) and on the front side an acidic compound (electron acceptor), on which the color formers react with color formation (recipient side: CF side).
  • CB side coated back
  • EXOR acidic compound
  • the color formers are known.
  • B. into consideration: crystal violet lactone, N-benzoyl leukomethylene blue, malachite green lactone, rhodamine lactones, spirodipyrans or fluoran derivatives (cf. DE-A 24 22 899, 20 25 171, 23 18 403, 23 23 803; DE-B 21 56 214; DE-A 22 43 483 and 2 230 225; GB-A 1417 695).
  • Activated clays attapulgite, aluminum oxide, bentonite, Silton-Clay, kaolin and other clays come into consideration as electron acceptors.
  • DE-C 2 252 901 and 2 303 405 describe the use of mixtures of clays and aromatic carboxylic acids and / or their metal salts as acceptors.
  • the receiving substances are first processed by grinding and mixing and optionally dispersing to form an aqueous dispersion which is then applied to the paper surface with the aid of doctor blades or by printing.
  • the polymers can be used as an organic solution, e.g. B. with the help of a flexographic printing unit.
  • DE-A 26 31 832 describes low molecular weight condensation products of hydroxybenzene or hydroxynaphthalenecarboxylic acids, phenols and formaldehyde as acceptors, which can be applied to the paper from organic solution. These agents are optionally used together with salts soluble in organic solvents.
  • DE-B 20 64 155 discloses the use of phenol-formaldehyde resins as the recipient, the resin being converted into an aqueous suspension / dispersion in the presence of anionic dispersants.
  • the dispersion can be prepared in a conventional manner by wet grinding the resin in an aqueous suspension.
  • the particle size should be 5 ⁇ m and below, preferably ⁇ 1 ⁇ m, so that an effective receiver layer is obtained (column 6, line 20/27).
  • the fine particles can also be obtained by dissolving the phenol / formaldehyde resin in alkali hydroxide solutions and precipitating the resin from the aqueous solution with acid (column 7, line 7/57; example 1).
  • the particle sizes in this case are between 3 and 80 ⁇ m.
  • These finely divided resin suspensions / dispersions can be dried by spray drying or in a drum dryer. According to the information in Example 1 of DE-B, the resin precipitated from the aqueous alkaline solution is distributed to a particle size of 1 ⁇ m using a high-speed disperser.
  • the inorganic or organic substances used as recipients may contain sharp-edged agglomerates which, when applied, e.g. B. cause printing, corrosion and abrasion.
  • the object is achieved according to the present invention in that secondary dispersion NEN of phenolic resins, which have spherical resin particles of ⁇ 5 microns in diameter, preferably from 0.5 to 2 microns in diameter, and aliphatic alcohols solid at room temperature used as a color-developing layer.
  • the recording material according to the present invention is obtained by applying an aqueous or aqueous-organic preparation which contains components (a), (b), (c) and optionally (d) to the support material.
  • the aqueous or aqueous-organic preparation is prepared by mixing the secondary dispersion containing (a) and (b) with the aliphatic alcohol which is solid at room temperature and, if appropriate, other auxiliaries usually present in such coatings.
  • the required aqueous or aqueous-organic secondary dispersion of (a) with (b) is carried out by introducing a solution of the phenolic resin (novolak) in a water-miscible solvent in water, which contains the copolymer (b) as a dispersing agent, suspended or suspended, with strong Get mixed.
  • the particle size of (a) can be determined by the temperature during the precipitation, the solvent used and by the stirrer used, e.g. B. propeller stirrer, siren or intensive stirrer can be influenced. Round particles of (a) in a size of 0.2 to 5 ⁇ m, preferably of 0.5 to 2 ⁇ m, are particularly suitable for the recording materials according to the invention. Smaller particles (a), in particular those ⁇ 0.2 11 m, disappear between the paper fibers when applied to paper and are therefore no longer or only partially available for color development.
  • water-miscible solvents for (a) are: ethanol, n- and i-propanol, methanol, butanol, tetrahydrofuran, acetone or mixtures thereof.
  • the organic solvent can be removed in whole or in part in a known manner from the dispersion obtained in the dispersion, for. B. by distillation.
  • radicals which are from C 8 - to C 20 -, in particular from C 10 - to C 20 -alkanols such as octyl, 2-ethylhexyl, nonyl, palmityl, stearyl, oleyl, lauryl, phenol or C Derive 1 - to C 2o -alkylphenols such as hexylphenol, dodecylphenol, hexadecylphenyl and octadecylphenol.
  • radicals are preferred which are derived from tallow fatty alcohol, coconut fatty alcohol or from C 5 to C 18 alkylphenols.
  • n is preferably from 10 to 100; m is preferably 0.
  • As comonomers (ß) are as C 3 - to C 5 carboxylic acids z.
  • acrylic acid methacrylic acid, crotonic acid, vinyl acetic acid and sulfoethyl (meth) acrylic acid, sulfopropyl (meth) acrylic acid, maleimide-N-ethanesulfonic acid, 2-acrylamido-2-methyl-propanesulfonic acid and vinylphosphonic acid.
  • Possible comonomers ( ⁇ ) to be used are: (meth) acrylamide, lauryl acrylate, styrene, vinyl acetate, methyl (meth) acrylate, tert.-, sec.- or n-butyl acrylate, hydroxypropyl acrylate, butanediol monoacrylate, vinyl propionate, 2-ethylhexyl acrylate , of which acrylamide, the butyl acrylates, 2-ethylhexyl acrylate, hydroxypropyl acrylate and lauryl acrylate are preferred.
  • copolymers of the acrylate of a reaction product of tallow fatty alcohol with 40 to 90 moles of ethylene oxide, acrylamide and 2-acrylamido-2-methylpropanesulfonic acid as well as copolymers of the modified tallow fatty alcohol acrylate with lauryl acrylate and methacrylic acid, or copolymers of the modified tallow fatty alcohol acrylate and approx. 30 wt % Methacrylic acid.
  • the amount of dispersant (b) is generally 1 to 10, preferably 2 to 8, in particular 3 to 8,% by weight, based on resin (a).
  • Suitable phenol resins (a) are those of the novolak type which are obtained by the condensation of phenol with formaldehyde or isobutyraldehyde in a molar ratio of 1: 0.5 to 1: 1. The production of these resins is known (see O. Nouvel, "The Industry of Phenol-Aldehyde Resins", Wilh. Knapp-Verlag, Halle (Saale) 1931; Robert W. Martin, "The Chemistry of Phenolic Resins", John Wiley and Sons, Inc. 1956; DE-A 28 05 763 and 2918593).
  • Aliphatic alcohols which are solid at room temperature are those having 12 to 18 carbon atoms, it being possible for the alkyl radicals to be linear or branched. Mixtures of these alcohols can also be used.
  • alcohols are z.
  • Cetyl alcohol and myristyl alcohol are preferably used.
  • binders such as starch, soluble cellulose derivatives, binder dispersions based on copolymers with acrylate or styrene-butadiene, white pigments and fillers such as insoluble starch, insoluble melamine-formaldehyde condensates, hollow microspheres, titanium dioxide, calcium carbonate and clay.
  • the coating of (a), (b), (c) and (d) can, for. B. in the form of the aqueous or aqueous-organic dispersion in a known manner on the carrier. If color formers still enclosed in microcapsules are added to the dispersion, so-called “self-contained” recording materials are obtained.
  • the cooled polymer solution had a solids content of 26%.
  • the polymer had a Fikentscher K value of 36 (measured on a 3% solution in dimethylformamide (DMF)).
  • the polymer solution obtained had a solids content of 25%; K value according to Fikentscher (3% in DMF) 32.
  • a disperser O Ultra-Turrax 000 rpm
  • a stable phenolic resin dispersion is obtained which is stable for weeks.
  • Solids content 36%; Particle diameter of the round particles m 1 ⁇ m.
  • the ink was removed with a doctor blade on paper (40 g / m 2 ) (application: 5.1 g / m 2 ).
  • Example 1a The procedure is as in Example 1a), but using a phenol-isobutyraldehyde novolak resin (molar ratio 1: 1; molecular weight 650; softening point 120 ° C. (ring ball according to DIN 52011; readily soluble in alkanols and ketones).
  • a phenol-isobutyraldehyde novolak resin molecular weight 650; softening point 120 ° C. (ring ball according to DIN 52011; readily soluble in alkanols and ketones).
  • the amount of cetyl alcohol dissolved with the resin is shown in the table below.
  • microcapsule dispersion was prepared by the process described in DE-OS 2940786, Example 1.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Color Printing (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Claims (8)

1. Matériau d'enregistrement sensible à la pression consistant en un support portant un revêtement développant une résine phénol/formaldéhyde en tant que chromogène, un agent dispersant pour la résine phénol/formaldéhyde et le cas échéant un ou plusieurs chromogènes réagissant avec le revêtement avec apparition de couleur, caractérisé en ce que le revêtement développant la couleur contient
a) une résine phénolique du type novolaque solide en fines particules de forme sphérique, à une dimension de particule inférieure ou égale à 5 microns,
b) en tant qu'agent dispersant un copolymère de
a) 5 à 95 % en poids d'un composé copolymérisable de formule
Figure imgb0009
dans laquelle
R1 représente un groupe alkyle en C 8-C 20 ou un groupe phényle éventuellement substitué par un groupe alkyle en C 1-C 20,
R2 représente l'hydrogène ou le groupe méthyle,
n = 2 à 100, et
m = 0 à 50,
ß) 5 à 95% en poids d'un acide carboxylique en C 3-C 5 à insaturation éthylénique copolymérisable, d'acide vinylsulfonique, d'acide sulfoéthylacrylique, d'acide sulfoéthylméthacrylique, d'acide sulfopropylacrylique, d'acide sulfopropylméthacrylique, d'acide maléimide-N-éthane-sulfonique, d'acide 2-acrylamido-2-méthylpropane-sulfonique ou d'acide vinylphosphonique,
γ) 0 à 50 % en poids d'acrylamide, de méthacrylamide, d'acrylate de lauryle, de styrène, d'acétate de vinyle, d'acrylate de méthyle, de méthacrylate de méthyle, d'acrylate de tert.-butyle, d'acrylate de sec.- butyle, d'acrylate de n-butyle, d'acrylate d'hydroxypropyle, de monoacrylate du butane-diol, de propionate de vinyle, d'acrylate de 2-éthylhexyle ou de mélanges de ces monomères,
c) au moins un alcool aliphatique solide à température ambiante et le cas échéant
d) d'autres produits auxiliaires usuels dans ces revêtements,

a) étant appliqué avec b) sous forme d'une dispersion secondaire aqueuse ou hydro-organique.
2. Matériau d'enregistrement selon la revendication 1, caractérisé en ce que la proportion de b) est de 1 à 10 % en poids par rapport à a).
3. Matériau d'enregistrement selon la revendication 1 ou 2, caractérisé en ce que la proportion de c) est de 10 à 100% en poids par rapport à a).
4. Matériau d'enregistrement selon la revendication 3, caractérisé en ce que la proportion de c) est de 25 à 50 % en poids par rapport à a).
5. Matériau d'enregistrement selon la revendication 1, 2, 3, ou 4, caractérisé en ce que le composant c) est l'alcool cétylique.
6. Matériau d'enregistrement selon la revendication 1, 2, 3, 4 ou 5, caractérisé en ce que a) a une dimension de particule de 0,5 à 2 microns.
7. Matériau d'enregistrement selon la revendication 1, 2, 3, 4, 5 ou 6, caractérisé en ce que b) est un copolymère de (a) au moins un (meth)acrylate d'un produit de réaction des alcools gras de suif, des alcools gras de coco ou d'alkylphénols en C 5-C 18 avec 10 à 100 moles d'oxyde d'éthylène par mole d'alcool ou de phénol, avec (ß) l'acide acrylique, l'acide méthacrylique, l'acide 2-acrylamido-2-méthylpro- pane-sulfonique ou un mélange de ces composés et le cas échéant (γ) l'acrylamide, des acrylates de butyle, l'acrylate de 2-éthylhexyle, l'acrylate d'hydroxypropyle, l'acrylate de lauryle ou des mélanges de ces composés.
8. Matériau d'enregistrement selon la revendication 7, caracérisé en ce que b) est un copolymère de (a) un acrylate d'un produit de réaction des alcools gras de suif avec 40 à 90 moles d'oxyde d'éthylène par mole d'alcool, avec (ß) l'acide 2-acryl-amido-2-méthylpropane-sulfonique, et (-y) l'acrylamide, ou avec (ß) l'acide méthacrylique et le cas échéant (γ) l'acrylate de lauryle.
EP81108067A 1980-11-24 1981-10-08 Matériaux pour l'enregistrement sensible à la pression Expired EP0052730B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803044120 DE3044120A1 (de) 1980-11-24 1980-11-24 Druck- und thermoempfindliches aufzeichnungsmaterial
DE3044120 1980-11-24

Publications (2)

Publication Number Publication Date
EP0052730A1 EP0052730A1 (fr) 1982-06-02
EP0052730B1 true EP0052730B1 (fr) 1985-03-13

Family

ID=6117382

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EP81108067A Expired EP0052730B1 (fr) 1980-11-24 1981-10-08 Matériaux pour l'enregistrement sensible à la pression

Country Status (4)

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US (1) US4407886A (fr)
EP (1) EP0052730B1 (fr)
JP (1) JPS57110493A (fr)
DE (2) DE3044120A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3539469A1 (de) * 1985-11-07 1987-05-14 Basf Ag Copolymerisate des ethylens mit polyalkylenglykol(meth)-acrylsaeureestern
US4762734A (en) * 1986-11-24 1988-08-09 Xerox Corporation Processes for thermal transfer ink donor films
US5397594A (en) * 1990-02-19 1995-03-14 New Oji Paper Co., Ltd. Process for producing heat-sensitive recording material
DE4227974C2 (de) * 1992-08-26 1996-04-18 Stockhausen Chem Fab Gmbh Alkoxygruppenhaltige Copolymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung zum Nachgerben von Leder
EP0671824B1 (fr) * 1994-03-07 2004-05-19 Siemens Aktiengesellschaft Procédé et dispositif de transmission d'informations codées par block sur plusieurs canaux dans un système radio numérique mobile
AU7387500A (en) * 1999-07-23 2001-02-13 Mead Corporation, The Copyable carbonless paper
JP6965400B1 (ja) 2020-06-02 2021-11-10 ぷらっとホーム株式会社 データ取引システム

Family Cites Families (24)

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US3322557A (en) * 1964-05-11 1967-05-30 Ncr Co Thermo-copy system
US3488207A (en) * 1965-10-22 1970-01-06 Us Plywood Champ Papers Inc Process of preparing a colored substance and transfer copy set
US3466184A (en) * 1967-02-14 1969-09-09 Ncr Co Record sheet sensitized with phenolic polymeric material
GB1277545A (en) * 1969-05-23 1972-06-14 Fuji Photo Film Co Ltd Fluoran compounds and pressure-sensitive copying paper
US3743619A (en) * 1969-12-29 1973-07-03 Mitsui Toatsu Chemicals Process for the production of suspensions of phenol-formaldehyde resins
US3934070A (en) * 1970-10-23 1976-01-20 Fuji Photo Film Co., Ltd. Recording sheet and color developer therefor
CA945371A (en) 1970-11-16 1974-04-16 Helmut Schwab Mixtures of two chromogenic compounds
BE790669A (fr) * 1971-10-28 1973-02-15 Fuji Photo Film Co Ltd Feuille d'enregistrement
GB1417695A (en) 1971-12-21 1975-12-17 Wiggins Teape Ltd Manifolding sheet material
BE794459A (fr) * 1972-01-24 1973-05-16 Fuji Photo Film Co Ltd Feuille d'enregistrement
DE2230225C2 (de) * 1972-06-21 1985-01-17 Basf Ag, 6700 Ludwigshafen Neue Chinoxalin-spiropyrane und deren Verwendung als Farbbildner für Kopierverfahren
DE2243483C2 (de) * 1972-09-05 1985-01-31 Basf Ag, 6700 Ludwigshafen Neue Diazaxanthenlactone, deren Herstellung und deren Verwendung als Farbbildner für Kopierverfahren
DE2323803C3 (de) * 1973-05-11 1983-12-01 Basf Ag, 6700 Ludwigshafen Spirodipyrane und deren Verwendung als Farbbildner für Kopierverfahren
GB1459417A (en) 1973-05-21 1976-12-22 Ciba Geigy Ag Diamino substituted fluoran compounds their manufacture and their use
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DE2758122A1 (de) * 1977-12-24 1979-07-05 Basf Ag Wasserloesliche copolymerisate auf der basis von hydrophilen aethylenisch ungesaettigten monomeren
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DE2918593A1 (de) 1979-05-09 1980-11-20 Basf Ag Verwendung von isobutyradehyd-formaldehyd-harzen als verlackungsmittel fuer basische farbstoffe
DE2940786A1 (de) 1979-10-08 1981-04-16 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von mikrokapseln
US4327148A (en) * 1979-11-28 1982-04-27 Mitsubishi Paper Mills, Ltd. Self-contained color forming pressure sensitive record paper of the single coating type

Also Published As

Publication number Publication date
EP0052730A1 (fr) 1982-06-02
DE3169276D1 (en) 1985-04-18
JPH021029B2 (fr) 1990-01-10
US4407886A (en) 1983-10-04
DE3044120A1 (de) 1982-07-15
JPS57110493A (en) 1982-07-09

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