EP0566537A1 - Procédé d'impression de matériau fibreux synthétique par impression par transfert - Google Patents

Procédé d'impression de matériau fibreux synthétique par impression par transfert Download PDF

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Publication number
EP0566537A1
EP0566537A1 EP93810251A EP93810251A EP0566537A1 EP 0566537 A1 EP0566537 A1 EP 0566537A1 EP 93810251 A EP93810251 A EP 93810251A EP 93810251 A EP93810251 A EP 93810251A EP 0566537 A1 EP0566537 A1 EP 0566537A1
Authority
EP
European Patent Office
Prior art keywords
component
weight
percent
printing paste
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
EP93810251A
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German (de)
English (en)
Other versions
EP0566537B1 (fr
Inventor
Paul Schafflützel
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0566537A1 publication Critical patent/EP0566537A1/fr
Application granted granted Critical
Publication of EP0566537B1 publication Critical patent/EP0566537B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5207Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257(Meth)acrylic acid
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/907Nonionic emulsifiers for dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/908Anionic emulsifiers for dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber

Definitions

  • the present invention relates to a method for printing synthetic fiber material in transfer printing and the printing paste used for this printing.
  • the transfer printing process has basically been around for a long time, e.g. from DE-OS-2,434,753 known.
  • sublimable disperse dyes are printed on carrier paper, so-called intermediate carriers, and transferred from there to the textile material by heat and pressure using transfer printing machines.
  • the printing pastes applied to the intermediate carriers are subject to high demands with regard to their viscosity behavior, fastness to rubbing and adhesive strength, etc.
  • printing pastes containing at least one thickener and one binder are used for transfer printing.
  • Known combinations represent e.g. Sodium alginate as a thickener and polyvinyl alcohol as a binder.
  • a printing paste containing these components however, has insufficient storage stability and homogeneity, which has a negative effect on the loss of pressure.
  • the present invention is therefore based on the object of providing a printing paste which is free of alginate compounds and at the same time insensitive to electrolytes, homogeneous and stable in storage. Surprisingly, it has now been found that the use of certain water-soluble polymers in printing pastes meet these conditions.
  • the printing pastes containing the components (a) and (b), (c) and / or (d) form a further subject of the invention.
  • a further advantage of the method according to the invention is the fact that component (a) acts simultaneously as a thickener and binder. As a result, the use of a further component acting as a binder becomes obsolete, which considerably simplifies the production and handling of the stock thickening or printing paste.
  • water-soluble polymers (a) there are e.g. Homo-co- or graft polymers containing 20 mol% units of a sulfo-containing monomer.
  • the polymeric compounds (a) are preferably homopolymers of sulfo-containing monomers or copolymers which contain more than 50 mol%, in particular more than 75 mol%, of sulfo-containing monomer units.
  • the polymers (a) can each be present as free acid or as ammonium, alkali metal (Na, K, Li) or alkaline earth metal salt (e.g. Ca); Mixtures of different cations are also possible.
  • alkali metal Na, K, Li
  • alkaline earth metal salt e.g. Ca
  • the polymer (a) is a copolymer
  • the following are used as sulfo-free comonomers, e.g. monomers containing carboxyl groups, monomers containing phosphoric acid groups or other comonomers.
  • Suitable comonomers with carboxyl function are, for example, (meth) acrylic acid, maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinyl acetic acid, vinyl oxyacetic acid, vinyl propionic acid, crotonic acid, aconitic acid, allyl acetic acid, allyloxyacetic acid, a, ß-dimethylacrylic acid, allylmalmalonic acid, allylmalmalonic acid (meth) acrylic acid, 2-Halogeno (meth) acrylic acid, ⁇ -ethyl acrylic acid, acrylamidoglycolic acid, glutaconic acid, ⁇ -carboxyethyl acrylate, allyloxy-3-hydroxybutanoic acid and allylsuccinic acid.
  • Suitable comonomers with a phosphoric acid group are e.g. Vinylphosphonic acid, (meth) allylphosphonic acid and acrylamidomethylpropanephosphonic acid.
  • the following monomers are also suitable as comonomers: N-vinylpyrrolidone, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methyl-acetamide, N-vinyl-N-ethyl acetamide, N-vinylimidazole, N-vinyl-N-methyl-imidazole, N-vinylimidazoline, N-vinyl-2-methylimidazoline, N-vinylcaprolactam, vinyl acetate, vinyl propionate, vinyl butyrate, C 1 -C 22 alkyl vinyl ketone, C 1 -C 22 -alkyl vinyl ether, olefins (ethylene, propylene, isobutene), 1,2-dimethoxyethylene, styrene derivatives, hydroxyethyl / propyl / butyl / - (meth) acrylate, (met h
  • the polymers or copolymers used and their preparation are known per se.
  • the water-soluble polymers used according to the invention are preferably prepared in aqueous solution.
  • Peroxidic compounds which are capable of forming free radicals are suitable as initiators, such as hydrogen peroxide, di-tertiary butyl oxide, benzoyl peroxide, lauryl peroxide or cumene hydroperoxide.
  • the polymerization can also be initiated with aliphatic azo compounds.
  • the usual redox catalyst systems such as hydrogen peroxide / iron (II) sulfate, are of course very suitable for initiating the polymerization.
  • the polymerization is usually carried out in the acid to new eel range.
  • the temperature during the polymerization is generally 20 to 100 ° C., preferably 40 to 80 ° C.
  • the polymer solutions obtained are e.g. 15 to 30% and have viscosities of e.g. 4,000 to 20,000 cP.
  • the viscosity which should preferably be above 9,000 cP, is a measure of the degree of polymerization.
  • deaerating agents can be used as component (b), provided that the rheological properties of the printing paste according to the invention are not adversely affected. Because of their good defoaming properties, low-silicone oil-free silicone oil-free deaerating agents are preferred, which generally contain 0 to about 10, in particular 2 to 8 percent by weight of a conventional silicone oil.
  • Preferred venting agents contain e.g. as active substance high-boiling hydrocarbons, hydrogenated naphthalenes, mineral oils, fatty oils or insoluble metal soaps or mixtures thereof and optionally have the silicone oil content indicated above.
  • they can also be present as aqueous solutions which, in addition to the active substances of the type mentioned, generally contain a nonionic surfactant, e.g. Include ethylene oxide adducts of an alkylphenol. Higher alcohols with boiling points above about 100 ° C., turpentine oils, mineral oils or mixtures thereof may be mentioned as preferred ingredients or active substances of the deaerating agents.
  • Hydrocarbon mixtures are preferably used which generally have a flash point above about 120 ° C., preferably from about 150 to 220 ° C. and a boiling range from about 250 to 500 ° C. under normal conditions.
  • deaerating agents which contain an octanol as active substance, e.g. Contain 2-ethyl-n-hexanol or its mixture with high-boiling hydrocarbon mixtures which have the above-mentioned content of silicone oils and are optionally present as an aqueous preparation, these preparations in addition to the active substances ethylene oxide adducts of an alkylphenol with 6 to 12 carbon atoms in the alkyl radical as a surfactant contain.
  • an octanol as active substance
  • these preparations in addition to the active substances ethylene oxide adducts of an alkylphenol with 6 to 12 carbon atoms in the alkyl radical as a surfactant contain.
  • the anionic or nonionic dispersant corresponding to component (c) serves as a protective colloid. This has the task of suppressing the undesired orthokinetic coagulation of the dye formulations used under the influence of high shear forces. It therefore has a stabilizing effect on the dye formulations used.
  • the addition of component (c) to the printing paste is advantageous, for example, if the dispersed dye formulation is present in the printing paste in amounts which are less than 12 percent by weight of the printing paste.
  • Suitable anionic dispersants are lignin sulfonates, polyphosphates or formaldehyde condensation products made from aromatic sulfonic acids and formaldehyde.
  • Usable nonionic dispersants are adducts of 15 to 100 moles of ethylene oxide or propylene oxide with polyhydric aliphatic C 2 -C s alcohols, such as ethylene glycol, glycerol or pentaerythritol.
  • Component (c) is preferably a polyvinyl acetate hydrolyzed to polyvinyl alcohol, which has a molecular weight of 12,000 to 30,000, preferably 15,000 to 25,000, and a degree of hydrolysis of 70 to 85 mole percent.
  • the printing paste contains a C 1 -C 3 alkanol as component (d), it is methanol, ethanol, n- or iso-propanol or a mixture of different C i -C 3 alkanols; the use of ethanol or mixtures of ethanol / methanol, ethanol / n-propanol or ethanol / iso-propanol is preferred. If a mixture of two alkanols is used as component (d), the mixing ratio can vary within wide limits.
  • component (a) a homo- or copolymer which has - 50 mol%, in particular - 75 mol% of 2-acrylamido-2-methylpropanesulfonic acid units, as component ( b) a deaerating agent which contains an octanol as active substance, and optionally as component (c) a polyvinyl acetate hydrolyzed to polyvinyl alcohol, which has a molecular weight of 12,000 to 30,000 and a degree of hydrolysis of 70 to 85 mol percent.
  • a preferred embodiment of the invention relates to the use of a printing paste which contains 1.5 to 6, preferably 2.5 to 5, and particularly preferably 3.2 to 4.4 percent by weight of component (a), 0.1 to 1.5 preferably 0.1 to 0.8 and particularly preferably 0.2 to 0.6 percent by weight of component (b), 0 to 1, preferably 0.3 to 0.5 percent by weight of component (c) and ad 100% by weight % Contains water.
  • a further preferred embodiment of the invention relates to the use of a printing paste which contains 0.5 to 2.5, preferably 1 to 2% by weight of component (a), 0.1 to 1.5, preferably 0.4 to 1, Contains 2% by weight of component (b), 1 to 6, preferably 2 to 4% by weight of component (c) and ad 100% by weight of water.
  • a printing paste which contains 0.5 to 2.5, preferably 1 to 2% by weight of component (a), 0 to 1.5, preferably 0.4 to 1.2% by weight of Component (b), 1 to 6, preferably 2 to 4 wt .-% of component (c), 5 to 45, preferably 20 to 40 wt .-% of component (d) and ad 100 wt .-% water.
  • Printing pastes according to the invention are irrimer-free from compounds containing alginate.
  • the amount of dye formulations present in the printing paste depends on the desired color strength and is generally 0.1 to 40 and preferably 0.1 to 30 percent by weight of the formulation, based on the weight of the printing paste.
  • a preferred embodiment of the present invention relates to the use of a printing paste consisting of 2.5 to 5% by weight of a homopolymer of alkali metal salts of 2-acrylamido-2-methylpropanesulfonic acid as component (a), 0.1 to 0.8% by weight. % of a deaerating agent which contains an octanol as active substance, as component (b), 0 to 1% by weight of a polyvinyl acetate partially hydrolyzed to polyvinyl alcohol, which has a molecular weight of 12,000 to 30,000 and a degree of hydrolysis of 70 to 85 mol percent, as Component (c), 0.1 to 30% by weight of a formulation of a sublimable disperse dye and ad 100% by weight of water.
  • the printing paste according to the invention is produced in a simple manner by mixing components (a) and (b), (c) and / or (d) with the desired dye formulation, with the amount of water required being added at the end, so that a sets a viscosity suitable for gravure printing, for example between 40 and 500, preferably between 100 to 300 and particularly preferably between 180 and 300 mPa.
  • Printing pastes for rotary screen printing advantageously have a higher viscosity, for example between 2000 and 5000 mPa.s.
  • the printing paste is applied over the entire surface, preferably in the form of a pattern, to the intermediate carrier, printing presses of conventional design, e.g. Rotary screen printing, flexographic and especially gravure printing machines can be used appropriately.
  • the intermediate carrier used in the transfer printing process is expediently a flexible, preferably spatially stable tape, a strip or a film with a smooth surface.
  • the intermediate carrier should be heat stable and inert, i.e. have no affinity for the various components of the printing paste. It can consist of different materials, e.g. made of metal, such as an aluminum or steel foil, made of plastic, paper or a textile fabric, which can optionally be coated with a film made of vinyl resin, ethyl cellulose or polyurethane resin. For cost reasons, primarily paper webs are used.
  • the printed fiber material is separated from the intermediate carrier.
  • no post-treatment is required, i.e. generally neither a steam treatment to fix the dye nor a washing process to improve the fastness properties.
  • the materials to be printed are e.g. around coated materials, synthetic or semi-synthetic foils, e.g. Films made of polyester, or in particular around textile materials, preferably around flat structures such as nonwovens, felts, especially carpets, knitted fabrics and in particular fabrics.
  • textile materials made from semi-synthetic and in particular fully synthetic fibers or their mixtures come into consideration.
  • the semi-synthetic fibers are mainly regenerated cellulose fibers, e.g. Triacetate and the fully synthetic fibers mainly around polyacrylonitrile, polyamide and especially polyester fibers. Mixed fabrics of triacetate and polyamide or polyester / cotton or polyester / wool are also suitable for the process according to the invention.
  • the printing pastes used according to the invention are new and form a further subject of the invention; they are characterized by good homogeneity, excellent storage stability and simple handling.
  • the printed intermediate carrier is dried at 100 ° C for 8 seconds. It is storable and rub-fast. Now, in the transfer printing process, the printed side of the intermediate carrier is brought into contact with a synthetic fiber material, for example a polyester fabric with a basis weight of 100 g / m 2 , then the intermediate carrier and the fiber material are pressed together in an ironing press for 30 seconds at 210 ° C, the Dye transferred from the intermediate carrier to the fabric.
  • a synthetic fiber material for example a polyester fabric with a basis weight of 100 g / m 2
  • a strong, red, pattern-like print on a white background with good levelness, good fastness properties and with sharp contours is obtained on the polyester fabric.
  • the printing paste has a pH of 7.8.
  • the viscosity is 130 mPas, measured on the Brookfleld RVT viscometer, spindle 2 (20 rpm) at 25 ° C.
  • the printing paste has a pH of 7.9.
  • the viscosity is 130 mPas, measured on the Brookfleld RVT viscometer, spindle 2 (20 rpm) at 25 ° C.
  • Example 13 If one proceeds as described in Example 13 and uses a printing paste which additionally has 5 g / kg of a deaerating agent based on 2-ethyl-n-hexanol and 295 g / kg instead of 300 g / kg of demineralized water, a printing paste is obtained, which has similarly good properties.
  • the viscosity is 220 mPa.s, measured on the Brookfield RVT viscometer, spindle 2 (20 rpm) at 25 ° C.
  • Example 15 The procedure described in Example 15 is followed and a printing paste is used which contains 10 g / kg of polyvinyl acetate partially hydrolyzed to polyvinyl alcohol (molecular weight 12000-30000, degree of hydrolysis 70-85%) as a 30% aqueous solution and 290 g / kg of demineralized water instead of 5 g / kg of deaerating agent based on 2-ethyl-n-hexanol and 295 g / kg of demineralized water, a printing paste is obtained which has similarly good properties.
  • Example 15 If one proceeds as described in Example 15 and uses a mixture of 200 g / kg ethanol and 200 g / kg isopropanol or n-propanol instead of 400 g / kg ethanol, printing pastes with similarly good properties are obtained.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP93810251A 1992-04-15 1993-04-05 Procédé d'impression de matériau fibreux synthétique par impression par transfert Expired - Lifetime EP0566537B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1246/92 1992-04-15
CH124692 1992-04-15

Publications (2)

Publication Number Publication Date
EP0566537A1 true EP0566537A1 (fr) 1993-10-20
EP0566537B1 EP0566537B1 (fr) 1996-09-18

Family

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EP93810251A Expired - Lifetime EP0566537B1 (fr) 1992-04-15 1993-04-05 Procédé d'impression de matériau fibreux synthétique par impression par transfert

Country Status (7)

Country Link
US (1) US5376148A (fr)
EP (1) EP0566537B1 (fr)
CZ (1) CZ63193A3 (fr)
DE (1) DE59303808D1 (fr)
DK (1) DK0566537T3 (fr)
SK (1) SK33893A3 (fr)
ZA (1) ZA932612B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1560858A1 (fr) * 2002-10-30 2005-08-10 The Lubrizol Corporation Promoteurs d'adherence pour systemes contenant du verre
CN102143941B (zh) * 2008-09-12 2014-02-12 株式会社日本触媒 带有磺酸基的醚化合物的制造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0100808A2 (fr) * 1982-08-06 1984-02-22 Ciba-Geigy Ag Epaississants et leur utilisation dans des pâtes d'impression pour imprimer des supports provisoires utilisés dans l'impression par transfert
EP0161038A1 (fr) * 1984-02-01 1985-11-13 Ciba Specialty Chemicals Water Treatments Limited Usage d'epaississants polymères dans l'impression
EP0190002A2 (fr) * 1985-01-30 1986-08-06 Ciba Specialty Chemicals Water Treatments Limited Compositions polymères, leur préparation et leurs utilisations dans des pâtes d'impression

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1595680A1 (de) * 1966-09-16 1970-04-23 Bayer Ag Sulfonsaeuregruppen enthaltende Polymerisate
DE2434753A1 (de) * 1974-07-19 1976-02-05 Henkel & Cie Gmbh Verfahren zum bedrucken von textilien aus synthetischen fasermaterialien

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0100808A2 (fr) * 1982-08-06 1984-02-22 Ciba-Geigy Ag Epaississants et leur utilisation dans des pâtes d'impression pour imprimer des supports provisoires utilisés dans l'impression par transfert
EP0161038A1 (fr) * 1984-02-01 1985-11-13 Ciba Specialty Chemicals Water Treatments Limited Usage d'epaississants polymères dans l'impression
EP0190002A2 (fr) * 1985-01-30 1986-08-06 Ciba Specialty Chemicals Water Treatments Limited Compositions polymères, leur préparation et leurs utilisations dans des pâtes d'impression

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 113 Columbus, Ohio, US; abstract no. 233284, JOZWIK, BOGUSLAW ET AL. 'Binding agent for finishing, printing, and dyeing of woven fabrics' *
CHEMICAL ABSTRACTS, vol. 93 Columbus, Ohio, US; abstract no. 73688, FUKUI, KIYOSHI 'Coloring assistants for dyeing or printing of textiles' *
DATABASE WPI Week 7535, Derwent Publications Ltd., London, GB; AN 75-57771W & JP-A-50 014 887 (SUMIMOTO CHEM IND KK) 17. Februar 1975 *

Also Published As

Publication number Publication date
DE59303808D1 (de) 1996-10-24
SK33893A3 (en) 1993-11-10
DK0566537T3 (da) 1996-10-07
US5376148A (en) 1994-12-27
ZA932612B (en) 1993-10-26
EP0566537B1 (fr) 1996-09-18
CZ63193A3 (en) 1993-12-15

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