EP0066278B1 - Transferdruckträger, Verfahren zu seiner Herstellung und seine Verwendung - Google Patents

Transferdruckträger, Verfahren zu seiner Herstellung und seine Verwendung Download PDF

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Publication number
EP0066278B1
EP0066278B1 EP82104697A EP82104697A EP0066278B1 EP 0066278 B1 EP0066278 B1 EP 0066278B1 EP 82104697 A EP82104697 A EP 82104697A EP 82104697 A EP82104697 A EP 82104697A EP 0066278 B1 EP0066278 B1 EP 0066278B1
Authority
EP
European Patent Office
Prior art keywords
formula
dyestuffs
printing
dyes
printed
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
EP82104697A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0066278A1 (de
Inventor
Reinhard Dr. Hähnle
Manfred Schneider
Claus Schuster
Rudolf Dr. Schickfluss
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of EP0066278A1 publication Critical patent/EP0066278A1/de
Application granted granted Critical
Publication of EP0066278B1 publication Critical patent/EP0066278B1/de
Expired legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • D06P5/004—Transfer printing using subliming dyes
    • D06P5/006—Transfer printing using subliming dyes using specified dyes
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the invention relates to transfer printing media, which are characterized in that they are impregnated or printed with a preparation which contains a dye of the general formula I. in which R 1 is alkyl having 1 to 4 carbon atoms, R 2 is hydrogen or has the meaning of R 1 , R 3 is methyl, methoxy or ethoxy and R 4 is methyl, methoxy or ethoxy, or contain mixtures of such dyes.
  • Preferred transfer printing supports according to the invention are impregnated or printed with preparations which contain dyes of the formula I in which R 1 and R 2 are alkyl having 1 to 4 carbon atoms, and those in which R 3 is methyl, or mixtures of such dyes.
  • the invention further relates to a method for producing the carriers according to the invention, which is characterized in that the carrier material is impregnated or printed with preparations which contain a dye of the formula I or mixtures of such dyes.
  • the invention also relates to the use of the supports according to the invention for dyeing and printing sheet-like structures by the thermal transfer printing process.
  • These sheet-like structures preferably consist of synthetic or partially synthetic polymeric materials or of materials which have been prepared with such synthetic or partially synthetic polymeric materials.
  • the sheet-like structures can also consist of or contain natural fiber materials, but are then treated with preparations which give these natural materials an affinity for the dyes of the formula I.
  • the dyes of the formula I are known and can be obtained by the methods customary for this type of azo dyes.
  • the azo dyes of the formula I used here are prepared by azo dyes of the formula 11 in which R 1 , R 2 , R 3 and R 4 have the above meanings and Hal is chlorine or bromine, in a manner known per se, e.g. B. according to the details of DE-A-1 809 920 or 1 809 921 or GB-A-1 184 825, a nucleophilic exchange reaction, the cyanide ion being used as the nucleophilic agent.
  • Other processes for the preparation of the dyes of the formula I are known, for. B. in DE-A-2834386 and in US-A-4105655.
  • the dyes to be used in accordance with the invention not only show pronounced good transfer properties, but also provide color-deep prints with a point-sharp printed image. They are therefore also well suited in combination with other transfer printing dyes, for which it is known that it is assumed that all dyes show a largely similar transfer characteristic under the conditions used.
  • the dyes of the formula I have good lightfastness and have significantly higher color strengths than the blue anthraquinone dyes used in transfer printing.
  • the dyes of formula 1 also have the advantage that they can be used to produce easily pourable low-electrolyte and dispersant printing pastes with a high dye concentration, which are very sought after because of the small amount of printing pastes on paper.
  • Sheet structures which are inert to the dyes applied and which do not hinder sublimation are suitable as carrier material for the transfer printing supports according to the invention.
  • the preparations which contain the dyes of the formula I and with which the support materials are impregnated or printed can be aqueous printing pastes, as are customary in textile printing, or organic printing inks as used in graphic printing.
  • Aqueous printing inks contain the usual natural or synthetic thickeners, for example polyvinyl alcohols, methyl cellulose or polymerization products containing carboxy groups, for example polyacrylates.
  • composition of the organic printing inks depends on the type of substrate, the substrate, the printing process and the equipment available.
  • Such printing inks generally consist of one or more dyes of the formula I, a binder, a dispersant and, if appropriate, solvents, fillers and preservatives.
  • Suitable binders are natural, semi-synthetic and synthetic resins, i.e. H. Polymerization, polycondensation and polyaddition products.
  • suitable resins are: rosin and its derivatives, maleinate resins, oil-free alkyd resins, alkyd resins made from synthetic and natural fatty acids and arylated alkyd resins.
  • terpene resins Poiyvinylharze as polyvinyl acetate and polyvinyl chloride, copolymers and graft polymers with various vinyl monomers, acrylate resins, naphthalene-formaldehyde resins, ketone resins, silicone resins, and cellulose derivatives such as Celluloseester, for example nitrocellulose or cellulose acetates, and cellulose ethers such as methyl cellulose, and other derivatives of other polysaccharides.
  • terpene resins Poiyvinylharze as polyvinyl acetate and polyvinyl chloride, copolymers and graft polymers with various vinyl monomers, acrylate resins, naphthalene-formaldehyde resins, ketone resins, silicone resins, and cellulose derivatives such as Celluloseester, for example nitrocellulose or cellulose acetates, and cellulose ethers such as methyl cellulose, and other derivatives of other
  • Nonionic and anionogenic products are used as dispersants.
  • nonionic products are: addition products of about 5-100 mol of alkylene oxide to higher fatty acids, fatty alcohol polyglycol ethers, phenol and alkylphenol polyglycol ethers, but also oxalkylates of fatty acids esterified with polyhydric alcohols or of resin derivatives such as hydroabietyl alcohol.
  • Suitable anionic dispersants are: naphthalenesulfonic acid-formaldehyde condensates, ligninsulfonates and sulfite waste products.
  • esters, ketones or alcohols are particularly preferred, for example butyl acetate, acetone, methyl ethyl ketone, ethanol, isopropanol or butanol.
  • the printing inks can be printed using all common printing methods, such as letterpress, flat, gravure or screen printing.
  • Rotogravure and rotary film printing are particularly suitable printing processes for the production of printed paper auxiliary substrates.
  • Suitable substrates are sheet-like structures such as nonwovens, felts, furs, carpets, foils and, above all, woven and knitted fabrics made from synthetic or partially synthetic materials, in particular from aromatic polyesters such as polyethylene glycol terephthalate or cellulose acetates such as cellulose triacetate and cellulose 2 1/2 acetate or polyamides.
  • aromatic polyesters such as polyethylene glycol terephthalate or cellulose acetates such as cellulose triacetate and cellulose 2 1/2 acetate or polyamides.
  • These synthetic and semi-synthetic materials show an affinity for the dyes of the formula I.
  • Thermal transfer printing is generally known and is described in detail, for example, in FR-A-1 223330, 1 334829 and 1 585 119.
  • the auxiliary carriers which are impregnated or printed with the suitable preparations, are brought into close contact with the substrate to be colored or printed, whereupon the dye is transferred from the carrier to the substrate and fixed there under the action of heat and, if appropriate, pressure or vacuum .
  • the dyes of the formula I When used in accordance with the invention on the substrates, the dyes of the formula I give greenish-blue, strongly colored dyeings and prints with good fastness to use.
  • Dyes of similar structure are known from table examples a and e of EP-A1-0 025 903 and from table example 14 and from example 31 of DE-A-2 832 179 which do not have the properties “greenish-blue”, “brilliant and” well sublimable »combine and thus not optimally suitable dye mixtures in thermal transfer, especially for trichromatic.
  • the dried dye of the formula with 100 parts of a non-ionic dispersant (acetic acid ester of an ethoxylated nonylphenol, molecular weight 4700, ethylene oxide content 94%) and 26 parts of an anionic dispersant (neutralized dimethylnaphthalene methanesulfonate) as well as 180 parts of ethylene glycol, 300 parts of water and 5 parts of chloroacetamide as a preservative homogenized with vigorous stirring on a dissolver.
  • a non-ionic dispersant acetic acid ester of an ethoxylated nonylphenol, molecular weight 4700, ethylene oxide content 94
  • an anionic dispersant neutralized dimethylnaphthalene methanesulfonate
  • the approx. 36.4% dye mixture is placed in a pearl mill and ground with siliquartzite pearls with water cooling. After 5 hours, a dispersion is obtained whose particles are more than 90% smaller than 3 ⁇ m. The dispersion is made up to 1,000 parts with water and separated from the beads.
  • the 35% dye-containing preparation has good storage stability both at 50 ° C. and at room temperature. It can be stirred into and homogenized in a conventional pressure thickener based on alginate as well as in a synthetic one based on polyacrylic acid.
  • Transfer papers printed with the printing ink result in a strong, greenish-blue print after transfer to polyester (approx. 25 seconds at 200 ° C). You can also print polyester-cotton materials (80 20).

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Electronic Switches (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
EP82104697A 1981-06-03 1982-05-28 Transferdruckträger, Verfahren zu seiner Herstellung und seine Verwendung Expired EP0066278B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3121981 1981-06-03
DE19813121981 DE3121981A1 (de) 1981-06-03 1981-06-03 Transferdrucktraeger, verfahren zu seiner herstellungund seine verwendung

Publications (2)

Publication Number Publication Date
EP0066278A1 EP0066278A1 (de) 1982-12-08
EP0066278B1 true EP0066278B1 (de) 1985-10-30

Family

ID=6133794

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82104697A Expired EP0066278B1 (de) 1981-06-03 1982-05-28 Transferdruckträger, Verfahren zu seiner Herstellung und seine Verwendung

Country Status (4)

Country Link
US (1) US4422854A (enrdf_load_stackoverflow)
EP (1) EP0066278B1 (enrdf_load_stackoverflow)
JP (1) JPS57210082A (enrdf_load_stackoverflow)
DE (2) DE3121981A1 (enrdf_load_stackoverflow)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5232893A (en) * 1983-07-25 1993-08-03 Dai Nippon Insatsu Kabushiki Kaisha Heat transferable image-receiving sheet, heat transfer assembly and heat transfer process
US5095000A (en) * 1983-07-25 1992-03-10 Dai Nippon Insatsu Kabushiki Kaisha Image-receiving sheet
DE3347572C2 (de) * 1983-12-30 1987-03-19 Hoechst Ag, 6230 Frankfurt Färben von Synthesefasern mit Farbstoffpräparationen von Mischungen oder Mischkristallen blauer Dispersions-Azofarbstoffe
US4657590A (en) * 1984-10-22 1987-04-14 The First National Bank Of Cincinnati Basic dye ink formulations and methods
EP0217036B2 (en) * 1985-08-05 1994-11-30 Hitachi, Ltd. Color ink sheet for thermal transfer
DE3530339A1 (de) * 1985-08-24 1987-02-26 Hoechst Ag Verfahren zum faerben von polyesterfasern feinen titers
US5234887A (en) * 1986-02-28 1993-08-10 Imperial Chemical Industries Plc Thermal transfer printing
DE3819563A1 (de) * 1988-06-09 1989-12-14 Hoechst Ag Mehrkomponenten-mischungen blauer dispersions-azofarbstoffe fuer das faerben von synthetischen fasern
JPH03189192A (ja) * 1989-12-12 1991-08-19 Agfa Gevaert Nv 熱染料昇華転写に使用するための染料供与体材料
DE68922736T2 (de) * 1989-12-12 1996-01-18 Agfa Gevaert Nv Thermisches Farbstoffsublimations-Übertragungsverfahren.
US5640180A (en) * 1994-03-08 1997-06-17 Sawgrass Systems, Inc. Low energy heat activated transfer printing process
US6450098B1 (en) 1994-03-08 2002-09-17 Sawgrass Systems, Inc. Permanent heat activated ink jet printing process
USRE38952E1 (en) * 1994-03-08 2006-01-31 Hale Nathan S Heat activated ink jet ink
US5656379A (en) * 1994-03-10 1997-08-12 Canon Kabushiki Kaisha Paper for forming images and image forming process
GB9608489D0 (en) * 1996-04-25 1996-07-03 Zeneca Ltd Compositions, processes and uses
US6300279B1 (en) 2000-03-31 2001-10-09 Joseph Macedo Method for applying decorative designs to wood substrates
DE10252863B4 (de) 2002-11-12 2007-04-19 Kronotec Ag Holzfaserplatte, insbesondere Fussbodenpaneel
US9781307B2 (en) 2014-11-14 2017-10-03 Sawgrass Technologies, Inc. Networked digital imaging customization
US10419644B2 (en) 2014-11-14 2019-09-17 Sawgrass Technologies, Inc. Digital image processing network
US9302468B1 (en) 2014-11-14 2016-04-05 Ming Xu Digital customizer system and method
US10827098B2 (en) 2015-11-02 2020-11-03 Sawgrass Technologies, Inc. Custom product imaging method
US10827097B2 (en) 2015-11-02 2020-11-03 Sawgrass Technologies, Inc. Product imaging

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1809920U (de) 1960-01-12 1960-04-21 Wilhelm Fleissner Streichgeraet fuer lacke, farben u. dgl. anstrichmittel.
US4105655A (en) * 1966-02-17 1978-08-08 Bayer Aktiengesellschaft Phenyl-azo-anilino dyestuff
NL6706776A (enrdf_load_stackoverflow) 1966-05-26 1967-11-27
GB1385934A (en) * 1972-03-04 1975-03-05 Yorkshire Chemicals Ltd Monoazo disperse dyes
US4185957A (en) * 1976-12-17 1980-01-29 Crompton & Knowles Corporation Heat transfer black dyestuff B
CH617814B (de) * 1977-07-25 Ciba Geigy Ag Transferdruckverfahren.
DE2834386A1 (de) * 1978-08-05 1980-02-21 Bayer Ag Verfahren zur herstellung von azofarbstoffen
DE2937329A1 (de) * 1979-09-14 1981-04-02 Bayer Ag, 5090 Leverkusen Azofarbstoffe sowie deren herstellung und verwendung
DE3165218D1 (de) * 1980-07-04 1984-09-06 Ici Plc Disperse monoazo dyestuffs
DE3029475A1 (de) * 1980-08-02 1982-03-25 Hoechst Ag, 6000 Frankfurt Transferdrucktraeger, verfahren zu seiner herstellung und seine verwendung

Also Published As

Publication number Publication date
DE3267129D1 (en) 1985-12-05
DE3121981A1 (de) 1982-12-23
JPH0246714B2 (enrdf_load_stackoverflow) 1990-10-17
JPS57210082A (en) 1982-12-23
EP0066278A1 (de) 1982-12-08
US4422854A (en) 1983-12-27

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