EP0038527B1 - Supports provisoires, procédé pour leur préparation et leur utilisation - Google Patents

Supports provisoires, procédé pour leur préparation et leur utilisation Download PDF

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Publication number
EP0038527B1
EP0038527B1 EP81102902A EP81102902A EP0038527B1 EP 0038527 B1 EP0038527 B1 EP 0038527B1 EP 81102902 A EP81102902 A EP 81102902A EP 81102902 A EP81102902 A EP 81102902A EP 0038527 B1 EP0038527 B1 EP 0038527B1
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EP
European Patent Office
Prior art keywords
printing
dyes
preparation
formula
carrier sheet
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
EP81102902A
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German (de)
English (en)
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EP0038527A1 (fr
Inventor
Rudolf Dr. Schickfluss
Manfred Schneider
Claus Schuster
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Hoechst AG
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Hoechst AG
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Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0038527A1 publication Critical patent/EP0038527A1/fr
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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

Definitions

  • the invention relates to transfer printing media which are impregnated or printed with a preparation which contains a monoazo dye, characterized in that the preparation comprises a dye of the formula (1) in which X is hydrogen, chlorine or bromine, R 'is methoxy or ethoxy, or, if X is chlorine or bromine, also represents hydrogen or methyl, R 2 is alkyl having 1 to 4 carbon atoms, R 3 is hydrogen or the meaning of R 2 and R 4 is alkyl of 1 to 4 carbon atoms, or contains 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 X represents chlorine or bromine.
  • the invention further relates to a process for the preparation of the supports according to the invention, which is characterized in that the support 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.
  • the 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 as such and can be obtained by the preparation processes customary for azo dyes.
  • Dyes of the formula (I) and their use for dyeing polyethylene terephthalate from an aqueous dispersion with the addition of a carrier are known from US Pat. No. 4,076,498.
  • the dyeings produced with the dyes disclosed in Examples 1-3 there (these dyes fall under the formula (I) of the present invention) have very good or good fastness to sublimation on polyester yarn.
  • a sublimation-fast dyeing only with relatively poorly subliming i.e. H.
  • the disperse dyes of the general formula (I) used according to the invention can be used to achieve excellent transfer prints on sheetlike structures made of, for example, synthetic or partially synthetic polymeric materials.
  • DE-OS 2 655 882 relates to a non-textile transfer web with monoazo dyes of a certain structure and to a sublimation transfer printing process of textiles made of hydrophobic synthetic fibers by transferring such a dye.
  • the dyes used there contain the substituents on the benzene nucleus of the coupling component , in which R 2 is an alkyl C2-C4 radical which contains 1 or 2 chlorine or bromine atoms, while the coupling components of the dyes used according to the invention in principle contain no halogen atom.
  • DE-AS 2364475 describes a method for printing on hydrophobic fiber materials according to the transfer printing principle, wherein sulfo group-free monoazo dyes of a certain structure are used. These dyes differ from the monoazo dyes used according to the invention in that they necessarily contain 1-3 trifluoromethyl groups on the benzene nucleus of the diazo component and can contain one or more trifluoromethyl groups on the benzene nucleus of the coupling component.
  • the dyes used in accordance with the invention not only show extremely good transfer properties, but also provide color-deep prints with a dot-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 produce easily pourable low-electrolyte and dispersant printing pastes with a high concentration of dyes, which are very sought-after because of the small amount of printing paste on paper.
  • Sheet structures which are inert to the dyes applied 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 carrier 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.
  • Suitable binders are natural, semi-synthetic and synthetic resins, 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 acetate, and cellulose ethers and others, such as, for example, methyl cellulose acetate, such as methyl derivative polysaccharide.
  • 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 acetate, and cellulose ethers and others, such as, for example, methyl cellulose acetate, such
  • Nonionic and anionogenic products are used as dispersants.
  • nonionic products are: addition products of about 5-70 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 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, i.e. high, 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 acetate sheet-like structures such as nonwovens, felts, furs, carpets, films, and especially woven and knitted fabrics made of synthetic or semi-synthetic materials, in particular aromatic polyesters, such as polyethylene glycol terephthalate or cellulose acetates such as cellulose triacetate and cellulose 2 1/2, or polyamides .
  • 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 1223 330, 1 334829 and 1 585119.
  • 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 1 when used in accordance with the invention on the substrates, reddish-tinged to greenish-blue, strong colorations and prints with good fastness properties are obtained.
  • 300 parts of the dry dye of the following constitution are ground with 80 parts of a nonionic dispersant (reaction product of glycerol with castor oil fatty acid, reacted with 100 moles of ethylene oxide) and 25 parts of a lignin sulfonate as well as 150 parts of ethylene glycol, 200 parts of water and 5 parts of chloroacetamide as a preservative in a bead 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 filled with water to 1000 parts and separated from the beads.
  • a nonionic dispersant reaction product of glycerol with castor oil fatty acid, reacted with 100 moles of ethylene oxide
  • a lignin sulfonate as well as 150 parts of ethylene glycol, 200 parts of water and 5 parts of chloroacetamide as a preservative in a bead mill with silica quartz beads.
  • the preparation containing 30% of dye is stable in storage at room temperature and also at 50 ° C.
  • the preparation can be easily mixed into a conventional pressure thickener (alginate-based) as well as into a synthetic pressure thickener (acrylic-based) and can be printed using the usual printing methods without affecting the viscosity.
  • Transfer papers printed with the printing ink produce a greenish-blue, strong print after transfer to polyester (approx. 20s at 200 ° C).
  • the setting containing 25% of the dye is stable in storage. Transfer papers printed with an aqueous printing ink made therefrom result in a reddish-navy-blue, strong print after transfer to polyester (approx. 20 s at 200 ° C).
  • 150 parts of the dry dye of the following constitution and 150 parts of the dry dye of the following constitution are reacted with 85 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, as well as 160 parts of ethylene glycol, 200 parts of water and 5 parts of chloroacetamide as a preservative, ground in a bead mill with silica quartz beads.
  • a nonionic dispersant reaction product of glycerol with castor oil fatty acid, reacted with 100 mol Ethylene oxide
  • a lignin sulfonate as well as 160 parts of ethylene glycol, 200 parts of water and 5 parts of chloroacetamide as a preservative, ground in a bead mill with silica quartz beads.
  • a dispersion is obtained whose particles are more than 90% smaller than 3 11 m.
  • the setting is made up to 1000 parts with water and separated from the beads.
  • the preparation containing 30% dye has a good shelf life both at room temperature and at 50 ° C.
  • Transfer papers printed with an aqueous printing paste obtained therefrom result in a deep blue, strong print after transfer to polyester (approx. 20 s at 200 ° C.).
  • an anionic dispersant e.g. B. a ligninsulfonate or a condensation product of naphthalenesulfonic acid and formaldehyde, and 130 ml of water are mixed and converted into a dispersion in a ball mill by grinding for 12 hours.
  • the approx. 33% preparation thus obtained is stable on storage.
  • the above aqueous dispersion can be processed into a printing paste as follows: 300 g are pasted with 350 g of a 10% locust bean gum ether thickener and 350 ml of water.
  • This printing paste is used to print paper using the gravure printing process. If you press this paper for 20-60 s at 210 ° C with a textile made of polyester fibers, you get a bright blue print.
  • the following table shows other dyes and the shades obtainable by the process given in Example 1.
  • the dyes can be mixed with one another. blue green. blue blue green. blue blue blue blue blue blue blue blue blue blue blue blue blue blue blue blue blue blue blue

Claims (6)

1. Supports pour impression par report, supports qui sont imprégnés ou imprimés avec une composition contenant un colorant mono-azoïque et qui sont caractérisés en ce que ladite composition renferme un colorant répondant à la formule I:
Figure imgb0025
dans laquelle X représente l'hydrogène, le chlore ou le brome, R, représente un méthoxy ou un éthoxy ou encore, dans le cas où X désigne le chlore ou le brome, R, peut aussi représenter l'hydrogène ou un méthyle, R2 représente un alkyle contenant de 1 à 4 atomes de carbone, R3 représente l'hydrogène ou a la signification de R2, et R4 représente un alkyle contenant de 1 à 4 atomes de carbone, ou des mélanges de colorants de ce genre.
2. Supports selon la revendication 1 caractérisés en ce qu'ils ont été imprégnés ou imprimés avec des compositions contenant des colorants de formule dans lesquels X représente le chlore ou le brome.
3. Procédé de fabrication de supports selon l'une des revendications 1 et 2, caractérisé en ce qu'on imprègne ou imprime la matière support avec des compositions contenant un colorant de formule 1 ou des mélanges de tels colorants.
4. Application des supports selon l'une des revendications 1 et 2 à la teinture et à l'impression d'objets planiformes par le procédé de thermo- transfert.
5. Application des supports selon la revendication 4, caractérisée en ce que les objets planiformes sont constitués de matières polymères synthétiques ou partiellement synthétiques ou ont été traités par de telles matières.
6. Application des supports selon la revendication 4, caractérisée en ce que les objets planiformes sont constitués de matières fibreuses naturelles ou contiennent de telles matières, et ont été traités par des compositions leur conférant une affinité pour les colorants de formule I.
EP81102902A 1980-04-23 1981-04-15 Supports provisoires, procédé pour leur préparation et leur utilisation Expired EP0038527B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803015571 DE3015571A1 (de) 1980-04-23 1980-04-23 Transferdrucktraeger, verfahren zu seiner herstellung und seine verwendung
DE3015571 1980-04-23

Publications (2)

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EP0038527A1 EP0038527A1 (fr) 1981-10-28
EP0038527B1 true EP0038527B1 (fr) 1984-12-05

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EP81102902A Expired EP0038527B1 (fr) 1980-04-23 1981-04-15 Supports provisoires, procédé pour leur préparation et leur utilisation

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EP (1) EP0038527B1 (fr)
JP (1) JPS56165078A (fr)
DE (2) DE3015571A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19740325C5 (de) * 1997-09-13 2010-01-21 Siempelkamp Maschinen- Und Anlagenbau Gmbh & Co. Kg Kontinuierliche Presse zum Verpressen von Preßgutmatten zu Preßgutplatten

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3131849A1 (de) * 1981-08-12 1983-02-24 Hoechst Ag, 6000 Frankfurt Transferdrucktraeger, verfahren zu seiner herstellung und seine anwendung
DE3318451A1 (de) * 1983-05-20 1984-11-22 Basf Ag, 6700 Ludwigshafen Farbstoffmischungen

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076498A (en) * 1976-09-20 1978-02-28 Martin Marietta Corporation Dyed polyethylene terephthalate textile fibers with greenish blue shade

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH16372A4 (fr) * 1972-01-05 1974-05-15
FR2334721A1 (fr) * 1975-12-11 1977-07-08 Toms River Chemical Corp Colorants azoiques et leur application dans l'impression par transfert sublimation
DE2557002B1 (de) * 1975-12-18 1976-11-04 Hoechst Ag Verfahren zur herstellung von transferdrucken auf synthesefasern
GB1489016A (en) * 1976-04-02 1977-10-19 Yorkshire Chemicals Ltd Monoazo disperse dyes
JPS5845509B2 (ja) * 1976-05-12 1983-10-11 日本化薬株式会社 ポリエステル成型物の転写捺染法
JPS5358083A (en) * 1976-11-01 1978-05-25 Mitsubishi Chem Ind Process of transfer printing
CH617814B (de) * 1977-07-25 Ciba Geigy Ag Transferdruckverfahren.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076498A (en) * 1976-09-20 1978-02-28 Martin Marietta Corporation Dyed polyethylene terephthalate textile fibers with greenish blue shade

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19740325C5 (de) * 1997-09-13 2010-01-21 Siempelkamp Maschinen- Und Anlagenbau Gmbh & Co. Kg Kontinuierliche Presse zum Verpressen von Preßgutmatten zu Preßgutplatten

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EP0038527A1 (fr) 1981-10-28
DE3167551D1 (en) 1985-01-17
DE3015571A1 (de) 1981-10-29
JPS56165078A (en) 1981-12-18

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