EP0155232A1 - Procédé de teinture de matières textiles cellulosiques - Google Patents

Procédé de teinture de matières textiles cellulosiques Download PDF

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Publication number
EP0155232A1
EP0155232A1 EP85810091A EP85810091A EP0155232A1 EP 0155232 A1 EP0155232 A1 EP 0155232A1 EP 85810091 A EP85810091 A EP 85810091A EP 85810091 A EP85810091 A EP 85810091A EP 0155232 A1 EP0155232 A1 EP 0155232A1
Authority
EP
European Patent Office
Prior art keywords
dyes
acrylamide
adduct
graft polymer
methacrylamide
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
EP85810091A
Other languages
German (de)
English (en)
Other versions
EP0155232B1 (fr
Inventor
Carl Alfred Jaeger
Hans-Ulrich Berendt
Paul Dr. Schäfer
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 EP0155232A1 publication Critical patent/EP0155232A1/fr
Application granted granted Critical
Publication of EP0155232B1 publication Critical patent/EP0155232B1/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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • 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
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/60—General 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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
    • 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
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/52—General 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
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257—(Meth)acrylic acid
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to a process for the block-free dyeing of textile materials which consist entirely or partly of cellulose fibers with substantive dyes or preferably with reactive dyes.
  • the present invention therefore relates to a process for dyeing cellulose-containing textile material with substantive dyes or reactive dyes by block-free impregnation of the textile material with an aqueous dye liquor and fixation of the dyes by the action of heat or by the cold dwell method, the dye liquor containing dyes and optionally other auxiliaries, such as wetting agents or fixing alkalis, characterized in that the dye liquor is a homopolymer or copolymer of acrylamide or methacrylamide or a graft polymer which consists of an adduct of an alkylene oxide of an at least trihydric aliphatic alcohol having 3 to 10 carbon atoms and acrylamide or methacrylamide is available.
  • the dye liquor can also contain mixtures of the polymers mentioned.
  • the polymers based on acrylamide or methacrylamide used according to the invention are preferably the graft polymers according to the definition.
  • graft polymers which can be obtained by graft polymerization of methacrylamide or, in particular, acrylamide onto an adduct of 4 to 100 mol, preferably 40 to 80 mol, of propylene oxide with 3 to 6 carbon atoms having trivalent to hexavalent alkanols.
  • alkanols can be straight-chain or branched. Examples include glycerol, trimethylolethane, trimethylolpropane, erythritol, pentaerythritol, mannitol or sorbitol.
  • graft polymers are those which are prepared by grafting methacrylamide or acrylamide onto addition products of mixtures of ethylene oxide and propylene oxide or else of ethylene oxide alone with the polyhydric alcohols mentioned.
  • Graft polymers of acrylamide and addition products of 40 to 80 moles of propylene oxide with 1 mole of glycerol have proven to be particularly suitable.
  • the graft polymers used according to the invention contain in some cases 2.5 to 50% by weight of the defined adduct as a parent chain and 50 to 97.5% by weight of grafted methacrylamide or preferably acrylamide as side chains.
  • the graft polymers preferably have 2.5 to 30% by weight of the alkylene oxide adduct by definition and 70 to 97.5% by weight of grafted methacrylamide or, in particular, acrylamide. Still before-.
  • the amide content is 80 to 97.5% by weight, based on the graft polymer.
  • the graft polymers used according to the invention are prepared by methods known per se, expediently in such a way that (1) an adduct of an alkylene oxide with an at least trihydric aliphatic alcohol of 3 to 10 carbon atoms with (2) acrylamide or methacrylamide and in the presence of Catalysts, advantageously polymerized at a temperature of 40 to 100 ° C.
  • Free radical-forming organic or preferably inorganic initiators are expediently used as catalysts.
  • Suitable organic initiators to carry out the radical Polymerization are, for example, symmetrical peroxidicarbonates, butyl peroctoates, butyl perbenzoates, peracetates or peroxidicarbamates.
  • Suitable inorganic initiators are hydrogen superoxide, perborates, persulfates or peroxidisulfates.
  • the preferred initiator or activator is potassium peroxydisulfate.
  • These catalysts can be used in amounts of 0.05 to 5 percent by weight, advantageously 0.05 to 2 percent by weight and preferably 0.1 to 1 percent by weight, based on the starting products.
  • the graft polymerization is advantageously carried out in an inert atmosphere, e.g. carried out in a nitrogen atmosphere.
  • the graft polymers are obtained as a very viscous mass.
  • gel-like products with a dry content of e.g. Produce 0.5 to 20 wt .-%, preferably 2 to 20 wt .-%.
  • preservatives such as e.g. Chloroacetamide, N-hydroxymethylchloroacetamide, pentachlorophenolates, alkali metal nitrites, triethanolamine or preferably hydroquinone monomethyl ether or also antibacterial agents, such as e.g. Sodium azide or surface-active quaternary ammonium compounds which have one or two fatty alkyl radicals can be added. Mixtures of these preservatives and germicidal compounds can also advantageously be used.
  • the particularly preferred 2 to 5% solutions of the graft polymers obtained have a viscosity of 3,000 to 150,000, preferably 15,000 to 120,000 and in particular 40,000 to 80,000 mPas (milli Pascal second at 25 ° C. ).
  • the polyalkylene oxide adducts used to prepare the graft polymers have in the Usually have a molecular weight of 400 to 6000, preferably 3000 to 4500.
  • linear or branched polymers of acrylic acid amide or methacrylic acid amide as well as copolymers of acrylic acid amide or methacrylic acid amide and other ethylenically unsaturated monomers, such as e.g.
  • Acrylic acid methacrylic acid, a-haloacrylic acid, 2-hydroxyethylacrylic acid, a-cyanoacrylic acid, crotonic acid, vinyl acetic acid, maleic acid, acrylonitrile, methacrylonitrile, vinyl alkyl ether, (methyl vinyl ether, isopropyl vinyl ether), vinyl ester (vinyl acetate), styrene, vinyl toluene, vinyl sulfido acid, 2-acrylamido acid, 2-acrylamido acid -methylpropane sulfonic acid or esters of the said a, ⁇ -unsaturated carboxylic acids and especially half-esters of maleic acid with adducts of 2 to 15 moles of ethylene oxide with monoalcohols with 8 to 22 carbon atoms.
  • the weight ratio of the acrylic acid amide to the other monomers is preferably from 9: 1 to 1: 1.
  • the amount in which the acrylic acid amide polymers are used alone or as a mixture in the dyeing liquors can vary within wide limits. Quantities of 0.1 to 20 g, preferably 0.5 to 10 g and in particular 1 to 5 g in the form of 2 to 10% aqueous solutions per liter of dye liquor have proven to be advantageous.
  • the dyes used in the process according to the invention are the substantive dyes usually used for dyeing cellulose textile materials or, above all, reactive dyes.
  • direct dyes are suitable as noun dyes, for example those in Color Index, 3rd edition (1971) Volume 2 on pages 2005 - 2478 "Direct Dyes".
  • Reactive dyes are understood to be the usual dyes that form a chemical bond with the cellulose, e.g. the "Reactive Dyes” listed in Color Index, Volume 3 (3rd Edition, 1971) on pages 3391-3560 and Volume 6 (Revised 3rd Edition, 1975) on Pages 6268-6345.
  • the amount of the dyes is generally based on the desired color strength and is advantageously 0.1 to 80 g per liter of liquor, preferably 2 to 50 g / 1 liquor.
  • the preparations When using reactive dyes, the preparations usually contain fixing alkalis.
  • alkaline compounds for fixing the reactive dyes are sodium carbonate, sodium bicarbonate, sodium hydroxide, disodium phosphate, trisodium phosphate, borax, aqueous ammonia or alkali donors, such as e.g. Sodium trichloroacetate used.
  • alkali donors such as e.g. Sodium trichloroacetate used.
  • a mixture of water glass and a 30% aqueous sodium hydroxide solution has proven particularly useful as an alkali.
  • the pH of the dye liquors containing alkali is usually 7.5 to 13.2, preferably 8.5 to 11.5.
  • the dyeing liquors are expediently prepared by dissolving the dye and by adding the acrylamide polymer and alkali.
  • the dye liquors can contain other conventional additives, for example electrolytes, such as sodium chloride or sodium sulfate, and also sequestering agents, reducing agents, such as sodium nitrobenzenesulfonic acid, and also urea, glycerol and / or sodium formate.
  • electrolytes such as sodium chloride or sodium sulfate
  • sequestering agents such as sodium nitrobenzenesulfonic acid
  • reducing agents such as sodium nitrobenzenesulfonic acid
  • urea glycerol and / or sodium formate.
  • thickeners such as alginates, cellulose derivatives, Starch ether or core meal ether such as locust bean meal ether may be contained therein.
  • alkali-resistant wetting agents e.g. Sulfonates of polycarboxylic acid esters such as dihexyl sulfosuccinates or dioctyl sulfosuccinates; Straight chain or branched chain alkylarylsulfonates with at least 6 carbon atoms, e.g. Dodecylbenzenesulfonates or preferably alkylsulfonates whose alkyl chain contains 8 to 20 carbon atoms, e.g. Add dodecyl sulfonates or pentadecyl sulfonates.
  • Sulfonates of polycarboxylic acid esters such as dihexyl sulfosuccinates or dioctyl sulfosuccinates
  • Straight chain or branched chain alkylarylsulfonates with at least 6 carbon atoms e.g. Dodecylbenzenesulfonates or
  • the sulfonates mentioned as wetting agents are generally present as alkali metal salts, but in particular as sodium salts or ammonium salts.
  • the amounts used in which the wetting agents are added to the dye liquor are advantageously between 1 to 20 g, preferably 2 to 10 g, per liter of liquor.
  • An advantageous embodiment of the invention consists in impregnating the cellulose material with a dyeing liquor which contains the graft polymer according to the definition in combination with a wetting agent which consists of (A) an alkyl sulfonate whose alkyl radical has 8 to 20 carbon atoms and (B) an adduct from 2 to 40 moles of ethylene oxide to 1 mole of fatty alcohol or fatty acid each having 8 to 22 carbon atoms or to 1 mole of alkylphenol with a total of 4 to 12 carbon atoms in the alkyl part.
  • Components (A) and (B) are generally present in a weight ratio of 5: 1 to 1: 1, preferably 5: 1 to 2: 1 and in particular 4: 1 to 3: 1.
  • Preferred ethylene oxide adducts (B) are those obtained by adding 2 to 10 moles of ethylene oxide to 1 mole of fatty alcohol having 8 to 12 carbon atoms.
  • the process according to the invention is suitable for dyeing textiles which consist of or contain cellulose.
  • Suitable cellulose material is regenerated or, in particular, natural cellulose, such as Cellulose, viscose silk, hemp, linen, jute or preferably cotton, as well as fiber blends e.g. those made of polyamide / cotton or in particular polyester / cotton, the polyester content being able to be pre-, simultaneously or post-dyed with disperse dyes.
  • fiber blends e.g. those made of polyamide / cotton or in particular polyester / cotton, the polyester content being able to be pre-, simultaneously or post-dyed with disperse dyes.
  • acid or dispersion dyes can also be sprayed.
  • the textile can be used in any form, e.g. Yarns, skeins of yarn, woven fabrics, knitted fabrics, felts, preferably in the form of textile fabrics, such as woven fabrics, knitted fabrics or carpets, which consist entirely or partially of native, regenerated or modified cellulose. Both raw and pretreated goods can be used.
  • Raw cotton e.g. used in cable or hose form.
  • the cellulose-containing textile material can be impregnated by application or, preferably, by spraying the dye liquor.
  • the fiber material is advantageously sprayed on at room temperature through a nozzle with a fine distribution, the flow rate being set such that a liquor absorption of 20 to 150% and particularly 80 to 150% can be achieved.
  • the textile material is subjected to a heat treatment process in order to fix the applied dyes.
  • the dyes are preferably fixed by the cold residence method.
  • the heat setting step can be carried out by a steaming process, a heat retention process, a thermal insulation process or by a microwave treatment.
  • the textile materials impregnated with the dye liquor for fixing the dyes are subjected to a treatment in a steamer with possibly superheated steam, advantageously at a temperature of 98 to 210 ° C., advantageously 100 to 180 ° C. and preferably 102 to 120 ° C.
  • the impregnated goods are left moist, e.g. Linger for 5 to 120 minutes, advantageously at temperatures of 85 to 102 ° C.
  • the wetted goods can be preheated to 85 to 102 ° C by infrared treatment.
  • the residence temperature is preferably 95 to 100.degree.
  • the fixation of the dyes by the so-called thermal insulation process can be done after or without intermediate drying e.g. at a temperature of 100 to 210 ° C.
  • the thermal insulation is preferably carried out at a temperature of 120 to 210 ° C., preferably 140 to 180 ° C. and after intermediate drying at 80 to 120 ° C. of the impregnated goods.
  • the thermal insulation can take 20 seconds to 5 minutes, preferably 30 to 60 seconds.
  • the heat setting of the dyes can be carried out using microwaves. After impregnation with the dye liquor, the goods are expediently rolled up and treated in a chamber by means of microwaves.
  • the microwave treatment can take 2 to 120 minutes. Preferably 2 to 15 minutes will suffice.
  • Microwaves are electromagnetic waves (radio waves) in the frequency range from 300 to 100,000 MHz, preferably 1000 to 30,000 MHz.
  • the dyes are fixed in accordance with the cold residence process expediently by storing the impregnated and preferably paneled or rolled goods at room temperature (15 to 30 ° C.), for example for 3 to 24 hours, the cold residence time being known to depend on the dye. If necessary, it can also be stored at a slightly elevated temperature (30 to 80 ° C).
  • the dyed cellulose material can be washed out in the usual way to remove unfixed dye.
  • the substrate is treated, for example, at from 40 ° C. to cooking temperature in a solution which contains soap or synthetic detergent. Treatment with a fixative can then be carried out to improve wet fastness.
  • level and vivid colorations are obtained which are characterized by a calm product appearance. Furthermore, the fastness to use of the colored goods, such as Light fastness, rub fastness and wet fastness are not negatively affected by the use of the defined acrylic acid amide polymer.
  • Example 1 A raw knitted cotton fabric (basis weight 165 g / m 2 ) is mixed with a liquor containing 5 g of the dye of the formula in liters
  • the knitted fabric is then rinsed and washed for 20 minutes at boiling temperature with a nonionic detergent (0.5 g / 1 of the addition product of 9 mol of ethylene oxide with 1 mol of nonylphenol) in a liquor ratio of 1:40.
  • a nonionic detergent 0.5 g / 1 of the addition product of 9 mol of ethylene oxide with 1 mol of nonylphenol
  • the substrate is then rinsed again and dried. You get a level and strong blue color, which is well colored, is characterized by a very calm appearance and shows no edge marking.
  • the dye solution is applied where it is needed, thus avoiding a complete penetration of the entire tissue.
  • Spraying can be carried out directly after dyeing the polyacrylonitrile fiber without intermediate drying (wet-on-wet).
  • the plush fabric is then placed in a container, sealed airtight and stored at 25 ° C. for 6 hours.
  • the knitted fabric is then rinsed and washed for 20 minutes at boiling temperature with a nonionic detergent (0.5 g / 1 of the addition product of 9 mol of ethylene oxide and 1 mol of nonylphenol) in a liquor ratio of 1:40.
  • a nonionic detergent 0.5 g / 1 of the addition product of 9 mol of ethylene oxide and 1 mol of nonylphenol
  • a uniformly colored, deeply colored, level red coloration is obtained on both sides. Similar effects are obtained if, instead of the graft polymer prepared according to regulation 2, the same amount of the graft polymers prepared according to regulations 1 and 4 are used.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP85810091A 1984-03-08 1985-03-04 Procédé de teinture de matières textiles cellulosiques Expired EP0155232B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1148/84 1984-03-08
CH114884 1984-03-08

Publications (2)

Publication Number Publication Date
EP0155232A1 true EP0155232A1 (fr) 1985-09-18
EP0155232B1 EP0155232B1 (fr) 1988-06-08

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP85810091A Expired EP0155232B1 (fr) 1984-03-08 1985-03-04 Procédé de teinture de matières textiles cellulosiques

Country Status (7)

Country Link
US (1) US4612016A (fr)
EP (1) EP0155232B1 (fr)
JP (1) JPS60209082A (fr)
KR (1) KR850006566A (fr)
CA (1) CA1241804A (fr)
DE (1) DE3563228D1 (fr)
ZA (1) ZA851716B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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FR2616164A1 (fr) * 1987-06-05 1988-12-09 Ciba Geigy Ag Procede de teinture ou appret par foulardage avec fixation a la continue de matieres textiles

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US7014665B2 (en) * 2003-01-13 2006-03-21 Milliken & Company Selective application of chemical agents in the pattern dyeing of textiles
US7799097B2 (en) * 2003-06-23 2010-09-21 Hbi Branded Apparel Enterprises, Llc Processes for spray dyeing fabrics
US8814953B1 (en) 2003-06-23 2014-08-26 Hbi Branded Apparel Enterprises, Llc System and method for spray dyeing fabrics
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US20090147905A1 (en) * 2007-12-05 2009-06-11 Kimberly-Clark Worldwide, Inc. Ultrasonic treatment chamber for initiating thermonuclear fusion
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CN115012234B (zh) * 2022-07-18 2023-08-04 苏州联胜化学有限公司 一种用于回用水活性染色的抗絮凝匀染剂及其制备方法

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US4397650A (en) * 1978-09-19 1983-08-09 United Merchants & Manufacturers, Inc. Textile dyeing process
EP0098803A1 (fr) * 1982-07-06 1984-01-18 Ciba-Geigy Ag Polymères greffés solubles ou dispersables dans l'eau, leur fabrication et utilisation
EP0111454A1 (fr) * 1982-12-14 1984-06-20 Ciba-Geigy Ag Procédé de teinture par foulardage de matières textiles cellulosiques

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH5206A (de) * 1892-04-12 1892-10-31 Blickensderfer George Canfield Schreibmaschine
US4323363A (en) * 1975-09-18 1982-04-06 Cassella Aktiengesellschaft Dyeing of mixed fibers
US4397650A (en) * 1978-09-19 1983-08-09 United Merchants & Manufacturers, Inc. Textile dyeing process
EP0019188A1 (fr) * 1979-05-09 1980-11-26 Hoechst Aktiengesellschaft Procédé de teinture par foulardage de matières textiles cellulosiques en forme de bandes
DE2932124A1 (de) * 1979-08-08 1981-02-26 Hoechst Ag Verfahren und vorrichtung zum auftragen von praeparationen auf warenbahnen
DE3202548A1 (de) * 1982-01-27 1983-08-04 Bayer Ag, 5090 Leverkusen Faerbeverfahren unter verwendung salzhaltiger schaeume
EP0098803A1 (fr) * 1982-07-06 1984-01-18 Ciba-Geigy Ag Polymères greffés solubles ou dispersables dans l'eau, leur fabrication et utilisation
EP0111454A1 (fr) * 1982-12-14 1984-06-20 Ciba-Geigy Ag Procédé de teinture par foulardage de matières textiles cellulosiques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2616164A1 (fr) * 1987-06-05 1988-12-09 Ciba Geigy Ag Procede de teinture ou appret par foulardage avec fixation a la continue de matieres textiles
EP0295205A1 (fr) * 1987-06-05 1988-12-14 Ciba-Geigy Ag Procédé de teinture ou apprêt par foulardage avec fixation à la continue de matières textiles

Also Published As

Publication number Publication date
CA1241804A (fr) 1988-09-13
ZA851716B (en) 1985-10-30
DE3563228D1 (en) 1988-07-14
KR850006566A (ko) 1985-10-14
US4612016A (en) 1986-09-16
EP0155232B1 (fr) 1988-06-08
JPS60209082A (ja) 1985-10-21

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