EP0066278A1 - Support de transfert par impression, procédé pour sa fabrication et son utilisation - Google Patents

Support de transfert par impression, procédé pour sa fabrication et son utilisation Download PDF

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Publication number
EP0066278A1
EP0066278A1 EP82104697A EP82104697A EP0066278A1 EP 0066278 A1 EP0066278 A1 EP 0066278A1 EP 82104697 A EP82104697 A EP 82104697A EP 82104697 A EP82104697 A EP 82104697A EP 0066278 A1 EP0066278 A1 EP 0066278A1
Authority
EP
European Patent Office
Prior art keywords
dyes
formula
contain
printed
printing
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.)
Granted
Application number
EP82104697A
Other languages
German (de)
English (en)
Other versions
EP0066278B1 (fr
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/fr
Application granted granted Critical
Publication of EP0066278B1 publication Critical patent/EP0066278B1/fr
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, R2 is hydrogen or has the meaning of R 1 , R 3 is methyl, methoxy or ethoxy and R 4 is hydrogen, 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 and R 2 are alkyl having 1 to 4 carbon atoms, as well as those in which R 3 is methyl and those in which R 4 is hydrogen means 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 after thermal transfer printing drive.
  • 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 II 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, for example according to the specifications of DE-OS 1 809 920 or 1 809 921 or GB-PS 1 184 825, is subjected to a nucleophilic exchange reaction, the cyanide ion being used as the nucleophilic agent. Further processes for the preparation of the dyes of the formula I are described, for example, in DE-OS 2,834,386 and in US Pat. No. 4,105,655.
  • 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 the formula I also have the advantage that they can be used to prepare easily pourable low-electrolyte and dispersant printing pastes with a high dye concentration, which are very sought after due to the low printing paste application on paper.
  • Sheet structures which are inert to the applied dyes and which do not hinder sublimation are suitable as the carrier material for the transfer printing supports according to the invention.
  • the formulations 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 are 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.
  • Natural, semi-synthetic and synthetic resins are suitable as binders, i.e. 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 polyvinyl resins such 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 cellulose esters, for example nitrocellulose or cellulose acetates, and cellulose ethers and others, such as methyl derivative cellulose ethers, such as, for example, methyl cellulose ethers, such as methyl derivative cellulose.
  • Nonionic and anionogenic products are used as dispersants.
  • Suitable nonionic products are for example: addition products of about 5 to 100 moles alkylene oxide to higher fatty acids, fatty alcohol polyglycol ethers, phenolic and Alkylphenolpolygkolether, but also oxalkylates of esterified fatty acids with polyhydric alcohols or resin derivatives such as H y DRO abietyl.
  • Suitable anionic dispersants are: naphthalenesulfonic acid-formaldehyde condensates, ligninsulfonates and sulfite waste products.
  • esters, ketones or alcohols for example butyl acetate, acetone, methyl ethyl ketone, ethanol, isopropanol or butanol, are particularly preferred.
  • 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 . 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-PSS 1 223 330, 1 334 829 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.
  • a nonionic dispersant diacetic acid ester of a propylene-ethylene oxide block polymer with an average
  • the preparation containing 30% dye 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. The viscosity of the synthetic pressure thickening is only slightly influenced by the preparation, so that printing can be done with shallow engravings using the usual printing methods. Transfer papers printed with the printing ink produce a strong, blue print after transfer to polyester (approx. 25 seconds at 200 ° C). Similarly good results are obtained when transferring to polyester / cotton (80:20).
  • the dried dye 350 parts of the dried dye of the following constitution 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 intensive 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 you get one Dispersion, the particles of which are more than 90% smaller than 3 ⁇ m.
  • the dispersion is made up to 1000 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 and homogenized just as easily in a conventional alginate-based pressure thickener as in a synthetic one based on polyacrylic acid.
  • Transfer papers printed with the printing ink produce a strong, greenish-blue print after transfer to polyester (approx. 25 seconds at 200 ° C). You can also print polyester-cotton materials (80:20).
  • each of the dried dyes mentioned in Examples 1 and 2 are mixed with 80 parts of a nonionic dispersant (reaction product of glycerol with castor oil fatty acid, reacted with 100 mol ethylene oxide) and 25 parts of a lignin sulfonate and 150 parts of ethylene glycol, 200 parts of water and 5 parts Chloroacetamide as a preservative ground in a pearl mill with silica quartz beads. After seven hours, a dispersion is obtained whose particles are more than 90% smaller than 3 ⁇ m. The setting is made up to 1000 parts with water and separated from the beads.
  • a nonionic dispersant reaction product of glycerol with castor oil fatty acid, reacted with 100 mol ethylene oxide
  • the preparation containing 30% of dye is stable in storage at room temperature and also at 50 ° C.
  • the preparation can be stirred into a conventional pressure thickener (alginate base) as well as into a synthetic pressure thickener (polyacrylic acid base) and can be printed using the usual printing methods. Transfer papers printed with this printing ink produce one after transfer to polyester (approx. 25 seconds at 200 ° C) blue, strong print. A strong blue print is also obtained on polyester / cotton (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 Support de transfert par impression, procédé pour sa fabrication et son utilisation Expired EP0066278B1 (fr)

Applications Claiming Priority (2)

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

Publications (2)

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

Family

ID=6133794

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82104697A Expired EP0066278B1 (fr) 1981-06-03 1982-05-28 Support de transfert par impression, procédé pour sa fabrication et son utilisation

Country Status (4)

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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147783A2 (fr) * 1983-12-30 1985-07-10 Hoechst Aktiengesellschaft Mélanges de colorants azoiques dispersés bleus pour la teinture de fibres synthétiques
US5234887A (en) * 1986-02-28 1993-08-10 Imperial Chemical Industries Plc Thermal transfer printing

Families Citing this family (20)

* 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
US4657590A (en) * 1984-10-22 1987-04-14 The First National Bank Of Cincinnati Basic dye ink formulations and methods
EP0217036B2 (fr) * 1985-08-05 1994-11-30 Hitachi, Ltd. Feuille avec couche d'encre colorée pour transfert thermique
DE3530339A1 (de) * 1985-08-24 1987-02-26 Hoechst Ag Verfahren zum faerben von polyesterfasern feinen titers
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.
US6450098B1 (en) 1994-03-08 2002-09-17 Sawgrass Systems, Inc. Permanent heat activated ink jet printing process
US5640180A (en) * 1994-03-08 1997-06-17 Sawgrass Systems, Inc. Low energy heat activated transfer 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
US9302468B1 (en) 2014-11-14 2016-04-05 Ming Xu Digital customizer system and method
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
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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1385934A (en) * 1972-03-04 1975-03-05 Yorkshire Chemicals Ltd Monoazo disperse dyes
DE2832179A1 (de) * 1977-07-25 1979-02-01 Ciba Geigy Ag Transferdruckfarbstoffe
US4185957A (en) * 1976-12-17 1980-01-29 Crompton & Knowles Corporation Heat transfer black dyestuff B
DE2834386A1 (de) * 1978-08-05 1980-02-21 Bayer Ag Verfahren zur herstellung von azofarbstoffen
EP0025903A1 (fr) * 1979-09-14 1981-04-01 Bayer Ag Colorants monoazoiques ainsi que leur préparation et leur utilisation pour la teinture et l'impression de matières fibreuses selon des méthodes classiques et selon le procédé d'impression par transfert, ainsi que les encres et les substrats porteurs pour le procédé d'impression par transfert
EP0044131A1 (fr) * 1980-07-04 1982-01-20 Imperial Chemical Industries Plc Colorants azoiques dispersés
EP0045479A1 (fr) * 1980-08-02 1982-02-10 Hoechst Aktiengesellschaft Support provisoire, procédé pour sa préparation et son utilisation

Family Cites Families (3)

* 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 (fr) 1966-05-26 1967-11-27

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
DE2832179A1 (de) * 1977-07-25 1979-02-01 Ciba Geigy Ag Transferdruckfarbstoffe
DE2834386A1 (de) * 1978-08-05 1980-02-21 Bayer Ag Verfahren zur herstellung von azofarbstoffen
EP0025903A1 (fr) * 1979-09-14 1981-04-01 Bayer Ag Colorants monoazoiques ainsi que leur préparation et leur utilisation pour la teinture et l'impression de matières fibreuses selon des méthodes classiques et selon le procédé d'impression par transfert, ainsi que les encres et les substrats porteurs pour le procédé d'impression par transfert
EP0044131A1 (fr) * 1980-07-04 1982-01-20 Imperial Chemical Industries Plc Colorants azoiques dispersés
EP0045479A1 (fr) * 1980-08-02 1982-02-10 Hoechst Aktiengesellschaft Support provisoire, procédé pour sa préparation et son utilisation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147783A2 (fr) * 1983-12-30 1985-07-10 Hoechst Aktiengesellschaft Mélanges de colorants azoiques dispersés bleus pour la teinture de fibres synthétiques
EP0147783A3 (fr) * 1983-12-30 1985-12-27 Hoechst Aktiengesellschaft Mélanges de colorants azoiques dispersés bleus pour la teinture de fibres synthétiques
US5234887A (en) * 1986-02-28 1993-08-10 Imperial Chemical Industries Plc Thermal transfer printing

Also Published As

Publication number Publication date
JPH0246714B2 (fr) 1990-10-17
EP0066278B1 (fr) 1985-10-30
US4422854A (en) 1983-12-27
DE3121981A1 (de) 1982-12-23
DE3267129D1 (en) 1985-12-05
JPS57210082A (en) 1982-12-23

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