EP0769083A1 - Procede de fabrication de substrats naturels ou synthetiques colores - Google Patents

Procede de fabrication de substrats naturels ou synthetiques colores

Info

Publication number
EP0769083A1
EP0769083A1 EP95924910A EP95924910A EP0769083A1 EP 0769083 A1 EP0769083 A1 EP 0769083A1 EP 95924910 A EP95924910 A EP 95924910A EP 95924910 A EP95924910 A EP 95924910A EP 0769083 A1 EP0769083 A1 EP 0769083A1
Authority
EP
European Patent Office
Prior art keywords
fluoro
pyrimidinyl
substrate
reactive
coupling component
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.)
Withdrawn
Application number
EP95924910A
Other languages
German (de)
English (en)
Inventor
Joachim GRÜTZE
Hermann Henk
Konrad Bootz
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of EP0769083A1 publication Critical patent/EP0769083A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • D06P1/02—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 azo dyes
    • D06P1/12—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 azo dyes prepared in situ
    • D06P1/125—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 azo dyes prepared in situ one or both of the components having fibre-reactive groups
    • 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
    • D06P3/68—Preparing azo dyes on the material
    • D06P3/685—Preparing azo dyes on the material one or both components having fibre-reactive group

Definitions

  • the invention relates to an improved method for producing colored native or synthetic substrates with covalently bound azo dyes produced on the substrate.
  • Reactive dyes containing azo groups can be reacted with reactive enolic ones
  • Coupling components are made with diazomum compounds.
  • the diazonium or the coupling component contains one or more, identical or different reactive molecular building blocks, which are usually called reactive groups.
  • the reactive groups are only synthetically inserted into the "color base" after the coupling step. After synthesis has been completed, these reactive dyes are reacted under customary dyeing conditions with the material to be dyed in printing or in various dyeing processes with the substrate.
  • the hydrolyzate has a characteristic substantivity that leads to intense dye-fiber Interaction leads and thus the washability of the dye necessary after the dyeing process significantly more difficult.
  • a water-insoluble naphthol compound in the form of its water-soluble naphtholate is applied to the material to be printed or dyed, and the material thus impregnated is then reacted with sulfo-free diazonium salts to give the water-insoluble, pigment-like dye.
  • a disadvantage of this process is the formation of considerable amounts of unpigmented dyes, so-called colored lacquers, which can form on the fiber and in the dyeing liquors. Because of their inadequate pigment-like character, they have little washability and therefore poor wet rub fastness. They have to be rinsed out after the coupling. This significantly extends the overall dyeing time.
  • the coupling component can contain a fiber-reactive group.
  • the primer is first primed, an intermediate fixation may be carried out in a sodium chloride bath or by rinsing in sodium chloride solution. In none of the examples is the excess coupling component removed by rinsing before reaction with the diazo component.
  • DE-A 2 603 445 and GB-A 1 568 172 it is known to block textile material with water-soluble coupling components, which contain a group which is fiber-reactive in the alkaline medium, from aqueous alkaline liquors, and then by treatment with a diazocom components and acid to bring about the dye formation. Again, there is no indication of rinsing off excess coupling component prior to reaction with the diazo component.
  • 1,576,061 relates to a process for dyeing or printing fiber materials, the fiber materials being dissolved with the coupling component treated with a diazotizable amine and sodium nitrite or first primed with a coupling component in the customary manner, if necessary rinsing and then allowing a diazotizable amine to act in the presence of nitrite, or by adding a diazotizable fiber-reactive amine to an intermediate rinse bath.
  • cotton jersey is primed with a coupling component, followed by an intermediate rinse and then sodium nitrite and a diazotizable amine are added to the same bath with diazotization and coupling.
  • the coupling component obviously does not have a fiber-reactive group.
  • DE-A 2 712 088 relates to a further embodiment of DE-A 2 603 446, which consists in using as coupling components those which likewise have at least one fiber-reactive group.
  • DE-A 2 712 106 relates to a further embodiment of DE-A 2 603 445, according to which the fiber-reactive coupling component is fixed by heat treatment or lingering in the dyeing of mixed fabrics of polyester and cellulose fibers.
  • the invention has for its object to provide an improved dyeing process based on reactive dyes, but which has improved application and ecological properties.
  • the invention relates to a process for the production of colored native or synthetic substrates with covalently bonded azo color substances produced on the substrate, characterized in that the hydrolyzate of the dye remains in the process in amounts of at most 1% by weight, based on the dye .
  • steps la) and lb) are carried out at 0 to 102 ° C. and a pH of 5 to 12, in particular 8 to 11.
  • Cross-wound washing machines cross-wound dyeing machines and flake dyeing machines.
  • wash liquor temperatures for washing out excess coupling components or hydrolyzed coupling components are 20 to 100 ° C., preferably 20 to 60 ° C. They are preferably aqueous washing liquors.
  • step ld) is carried out at pH 7 to 11.
  • step ld) is carried out at pH 3 to 7.
  • At least one sulfo group-containing and / or sulfo group-free reactive coupling component is chemically fixed as weak color or colored dye intermediate product on fibers, fabrics and knitted fabrics to be dyed or printed with OH, NH or SH groups. After an intermediate cleaning of the impregnated in this way. Materials are synthesized in a subsequent chromogenic coupling step with one or more diazonium compounds on the fiber, so that real, strongly colored dyeings or prints with the same or different nuances result in a short time and the final and wash liquors are carried out in comparison to conventional ones
  • Reactive stains are only slightly stained.
  • the materials to be dyed or printed are preferably native or synthetic OH, nitrogen and sulfur-containing fibers, knitted fabrics, fabrics, foils or films, in particular based on cotton.
  • the reactive coupling component is a phenol, naphthol, pyridone, acetoacetic anilide, pyrimidine or barbiturate.
  • the reactive coupling component corresponds to one of the following formulas
  • R j , R 2 independently of one another hydrogen, C j -C 4 alkyl, aryl, in particular phenyl, alkoxy, in particular C j -C 4 alkoxy, aryloxy, in particular phenyloxy,
  • R 3 K ⁇ R 2 , C ; S NR ;
  • R 4 R ⁇ ; R 2 ; R 3 ; -CN; -OH 2 -SO 3 H; -SO 3 H,
  • B bridge member in particular alkylene with 1 to 4 carbon atoms, arylene or bisarylene, carbonyl or a heterocyclic radical, in particular a triazinyl radical, where combinations of these constituents can occur and the bridge member can be interrupted by
  • X fiber-reactive radical in particular a) a nitrogen-containing 5- or 6-membered heterocycle with at least one halogen atom is substituted, or b) acryloyl, or c) vinylsulfonyl or d) SO 2 -C 2 H 4 Z, where Z is a removable group, in particular -O-SO 3 H, -S-SO 3 H, -O-PO 2 H 2 or -O-acyl, especially acetyl;
  • Amino-8-hydroxynaphthalene-6-sulfonic acid l-amino-8-hydroxynaphthalene-2,4-disulfonic acid, 2-hydroxy-3-aminonaphthalene-5,7-disulfonic acid, 1-amino-8-hydroxy-naphthalene 2,4,6-trisulfonic acid, l-hydroxy-8-acetylaminonapthalene-3-sulfonic acid, 2-amino-5-hydroxynaphthalene-7-sulfonic acid, 2-methyl- or 2-ethylamino-5-hydroxynaphthalene-7- sulfonic acid, 2- (N-acetyl-N-methylamino) -5-hydroxynaphthalene-7-sulfonic acid, 2-acetylamino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-5-hydroxynaphthalene-l, 7-disulfonic acid, 2-amino-8-hydroxynaphthalene-6
  • 6- or 4,6-disulfonic acid 6- or 4,6-disulfonic acid, l- (4'-nitro-benzoylamino) -8-hydroxynaphthalene-3.6- or 4,6-disulfonic acid, l- (3'-amino-benzoylamino) -8-hydroxynaphthalene 3.6- or 4,6-disulfonic acid, l- (3'-nitrobenzoylamino) -8-hydroxynaphthalene-3.6- or 4,6-disulfonic acid, l-amino-8-hydroxynaphthalene-4-sulfonic acid.
  • the diazotization of the diazo components or the intermediates containing a diazotizable amino group is generally carried out by the action of nitrous oxide
  • Particularly suitable reactive radicals are those which contain at least one reactive substituent bound to a 5- or 6-membered aromatic-heterocyclic ring, for example to a monoazine, diazine or triazine ring, in particular a pyridine, pyrimidine, pyridazine, Pyrazine, thiazine, oxazine or asymmetrical or symmetrical triazine ring, or to such a ring system which has one or more fused aromatic-carbocyclic rings, for example a quinoline, phthalazine, quinazoline, quinoxaline, acridine or phenazine - and phenanthridine ring system.
  • reactive substituents on the heterocycle are, for example, halogen (Cl, Br or F), ammonium including hydrazinium, sulfonium, sulfonyl, azido (N 3 ), rhodanido, thio, thiol ether, oxyether, sulfinic acid and sulfonic acid.
  • halogen Cl, Br or F
  • ammonium including hydrazinium, sulfonium, sulfonyl, azido (N 3 ), rhodanido, thio, thiol ether, oxyether, sulfinic acid and sulfonic acid.
  • alkyl is preferably optionally substituted C j -C 4 - alkyl, aralkyl, preferably optionally substituted phenyl-C j -C 4 alkyl and aryl, preferably optionally substituted phenyl or naphthyl, and preferred substituents for alkyl, hydroxy , Cyan, C 1 -C 4 alkoxy, sulfo or sulfato and for phenyl and naphthyl,
  • 2-amino-4-fluorotriazinyl-6 2-methylamino-4-fluorotriazinyl-6, 2-ethylamino-4-fluorotriazinyl-6, 2-isopropylamino-4-fluorotriazinyl-6, 2-dimethylamino-4- fluorotriazinyl-6, 2-diethylamino-4-fluorotriazinyl-6, 2-ß-methoxy-ethylamino-4-fluoro-triazinyl-6, 2-ß-hydroxyethylamino-4-fluorotriazinyl-6, 2-di- (ß-hydroxyethylamino) -4-fluoro-triazinyl-6, 2-ß-sulfoethylamino-4-fluoro-triazinyl-6, 2-ß-sulfoethyl-methylamino-4-fluoro-triazinyl-6, 2- Carboxymethylamino-4-fluoro
  • halotriazinyl radicals can also be linked to a second halotriazinyl radical or a halodiazinyl radical or a vinylsulfone or sulfatoethylsulfonyl radicals, for example via a bridge member or in the case of sulfatoethylsulfonyl or vinylsulfonyl group
  • alkylene in particular C j -C 6 alkylene
  • Mono-, di- or trihalopyrimidinyl radicals such as 2,4-dichloropyrimidinyl-6, 2,4,5-trichloropyrimidinyl-6-, 2,4-dichloro-5-nitro- or -5-methyl- or -5-carboxy - methyl- or -5-carboxy- or -5-cyano- or -5-vinyl- or -5-sulfo- or -5-mono-, -di or -trichloromethyl- or -5-carbalkoxy-pyrimidinyl-6 -, 2,6-dichloropyrimidine-4-carbonyl-, 2,4-dichloro yrimidine-5-carbonyl-, 2-chloro-4-methyl-pyrimidine-5-carbonyl-, 2-methyl-4-chloropyrimidine-5- carbonyl-, 2-methylthio-4-fluoropyrimidine-5-carbonyl-, 6-methyl-2,4-dichloropyrimidine-5-carbonyl
  • Ammonium especially -N ⁇ (C 1 -C 4 alkyl) 3 An e ,
  • An ⁇ anion for example -OSO 3 H, -OPO 3 H 2 , -Cl, -Br, -F, -SCN, -OCN, -OSO 2 CH 3 , -OSO 2 C 6 H 5 , OCOCH 3 .
  • the reactive coupling components can be prepared by reacting the coupling components, which are known per se, with the corresponding reactive radicals mentioned above, in particular by condensation in water at pH values from 1 to 14, preferably 2 to 12 and temperatures from 0 to 100 ° C. , preferably from 0 to 80 ° C, wherein the acid formed during the reaction by simultaneous neutralization with suitable bases or buffer mixtures is bound.
  • Suitable diazonium compounds to be used according to the invention are all those substances mentioned by K.Unger, Ulimann, Encyclopedia of Industrial Chemistry, Chapter 6, Development Dyes, as are also customary in naphthol dyeing, for example.
  • Sulfo ⁇ group-containing diazonium salts in dissolved, suspended, solid or encapsulated form are also suitable.
  • diazo components for this are 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-diamino-4-methylbenzene, 1,3-diamino-4-ethylbenzene, 1,3-diamino-4-methoxybenzene , l, 3-diamino-4-ethoxybenzene, l, 4-diamino-2-methylbenzene, l, 4-diamino-2-methoxybenzene, l, 4-diamino-2-ethoxybenzene, 1,4-diamino-
  • the reactive coupling component or differently concentrated mixtures of 2 or more different coupling components are fixed under acidic, neutral or alkaline conditions of the reactive dyeing, under fixing conditions of the reactive printer or the padding impregnation / fixing method with formation of covalent conditions between the reactive group and the material to be colored.
  • one or more coupling components can be separated or mixed with one another from sprayers, such as those e.g. in carpet dyeing or so-called ink printing (ink jet process) for cellulose and paper are known, applied to the material to be dyed and then fixed.
  • sprayers such as those e.g. in carpet dyeing or so-called ink printing (ink jet process) for cellulose and paper are known, applied to the material to be dyed and then fixed.
  • the application temperatures are preferably between 15 ° C and 180 ° C, in particular 15-110 ° C, the pH values between pH 4 and pH 13 depending on the task.
  • the chemically derivatized material is possibly neutralized or acidified and washed or rinsed and with or without intermediate drying in a further reaction step in the printing, padding impregnation or exhaust process, by knife coating, printing or spraying, with the diazonium salt in acidic, neutral or alkaline pH Area with the already fixed dye intermediate product developed chromatogenically (synthesized).
  • reactive coupling components can be fixed on paper, leather, films and foils, which, after implementation, are matched with the corresponding ones
  • Diazonium salts also give real, brilliant, strong colorations.
  • OH, NH, NH 2 and SH group-containing materials for.
  • different reactive couplers can be successfully converted into mixed dyes after rinsing with a diazonium salt. It is surprising that the reactive couplers are similar
  • the development conditions used here result in very short process times. In view of the short dyeing time, a surprisingly high coloration of the material and a surprisingly uniform product appearance are achieved.
  • the application according to the invention of reactive development dyes containing sulfo groups mentioned here can preferably be used for dyeing and printing cellulose, regenerated cellulose, wool, silk, paper and leather.
  • the application of reactive coupling components to the materials mentioned above can be carried out from a long or short liquor in the exhaust process, moreover in practical impregnation processes by means of padding and gusset rollers and by spraying.
  • the reactive coupling components can be applied to the materials mentioned in the customary processes of reactive textile printing.
  • the coupling components can be incorporated into film and foil-like materials by extruders.
  • the desired covalent bond between the coupling components and the material to be colored is formed in the presence of inorganic, organic or inorganic / organic buffer mixtures, organic or inorganic acids or alkalis in the pH range between 2 and 12.
  • fixing temperatures are between 15 ° C and 105 ° C.
  • the chromogenic development of the coupling components covalently fixed on the material to be colored with the corresponding diazonium salt is carried out from a long liquor in the exhaust process, using a padding or spraying process at temperatures between 15 ° C and 90 ° C in the neutral, acidic or alkaline pH range.
  • the dye formation is complete within a few minutes, even with great depths of color.
  • the dye liquors only have the intrinsic color of the diazonium salt or diazonium salts used during and after the chromogenic coupling. This also applies to the following washing liquors.
  • the wet fastness and rub fastness of the dyeings produced in this way correspond to the usual level of reactive dyes, but are achieved after a significantly shorter dyeing time and after a few, minimally colored rinsing baths.
  • monofluorotriazine-morpholine-H-acid of the formula (I) is used as the reactive coupling component used.
  • the preparation of this compound is described in detail in DE-A-3 723 474 and DE-A-3 733 571.
  • This reactive coupling component is e.g. chemically fixed to cellulose in a foulard impregnation process under alkaline conditions by forming covalent bonds. Excess I or hydrolyzate of I is washed out, excess alkali is neutralized if necessary.
  • the material treated in this way is mixed with an aqueous dye liquor which contains the dissolved diazonium salt which is free of sulfo groups or contains sulfo groups.
  • the desired shade develops in a short time. Any irregularities that arise at the beginning are completely compensated for.
  • Cell means cellulose. Furthermore, sulfo-containing diazonium salts such as
  • 1000 g of cotton knitwear are padded in a padding process using a mixture consisting of 15 g / 1 of the product of the formula (I) and 29 g / 1 of sodium carbonate (Na 2 CO 3 ) at 22 ° C. in the impregnation process, and wound up for 24 hours 22 ° C lingers.
  • the derivatized material is then washed twice in a 1:10 liquor ratio with water at 40 ° C. and neutralized by adding 0.5 g / 1 acetic acid (pH ⁇ 7).
  • the cotton which has been covalently impregnated with the product of the formula (I) as described above, undergoes a second process step in the exhaust process in a liquor ratio 1: 8 at 40 ° C. and pH 3.5 with a 5% solution of the diazonium salt of 2 , 5-dichloroaniline with formation of the dye of the following formula
  • the hydrolyzate of this dye is less than 0.8%, based on the dye.
  • the hydrolyzate of this dye is less than 0.9%, based on the dye.
  • the derivatized material is subjected to percolation washing at 40 ° C on the perforated tree. Then the derivatized material with the
  • Diazionium salt of o-amino-benzenesulfonic acid (VI) implemented to:
  • the counter ion is a common anion for diazonium salts, in particular Cl ⁇ ,
  • Table 3b List of the chromogenic couplings currently carried out on the fiber

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne un procédé perfectionné de fabrication de substrats naturels ou synthétiques colorés, procédé caractérisé en ce qu'on effectue les opérations ci-après: (a) on met en contact le substrat avec un composé de copulation capable de réagir, (b) on fixe le composé de copulation sur le substrat par formation d'une liaison chimique, (c) on élimine le composé de copulation non fixé et hydrolysé, (d) on fait réagir le produit réactionnel fixé avec un sel de diazonium approprié pour la formation d'un colorant azoïque, (e) on élimine le composé diazonium en excès.
EP95924910A 1994-07-05 1995-06-22 Procede de fabrication de substrats naturels ou synthetiques colores Withdrawn EP0769083A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19944423444 DE4423444A1 (de) 1994-07-05 1994-07-05 Verfahren zur Herstellung von farbigen nativen oder synthetischen Substraten
DE4423444 1994-07-05
PCT/EP1995/002432 WO1996001338A1 (fr) 1994-07-05 1995-06-22 Procede de fabrication de substrats naturels ou synthetiques colores

Publications (1)

Publication Number Publication Date
EP0769083A1 true EP0769083A1 (fr) 1997-04-23

Family

ID=6522239

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95924910A Withdrawn EP0769083A1 (fr) 1994-07-05 1995-06-22 Procede de fabrication de substrats naturels ou synthetiques colores

Country Status (5)

Country Link
EP (1) EP0769083A1 (fr)
AU (1) AU2923695A (fr)
DE (1) DE4423444A1 (fr)
FI (1) FI970045A (fr)
WO (1) WO1996001338A1 (fr)

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DE19600633A1 (de) * 1996-01-10 1997-07-17 Dystar Textilfarben Gmbh & Co Verfahren zur Herstellung von farbigen nativen oder synthetischen Substraten
DE19600634A1 (de) * 1996-01-10 1997-07-17 Dystar Textilfarben Gmbh & Co Verfahren zur Herstellung von farbigen nativen oder synthetischen Substraten und deren Nachbehandlung
US6262047B1 (en) 1996-10-11 2001-07-17 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6369080B2 (en) 1996-10-11 2002-04-09 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6194435B1 (en) 1996-10-11 2001-02-27 Cor Therapeutics, Inc. Lactams as selective factor Xa inhibitors
US6063794A (en) 1996-10-11 2000-05-16 Cor Therapeutics Inc. Selective factor Xa inhibitors
CA2285685A1 (fr) 1997-04-14 1998-10-22 Cor Therapeutics, Inc. Inhibiteurs selectifs du facteur xa
NZ500351A (en) * 1997-04-14 2001-10-26 Cor Therapeutics Inc Cyclic diaza compounds as selective factor Xa inhibitors
JP2002514214A (ja) 1997-04-14 2002-05-14 シーオーアール セラピューティクス インコーポレイテッド 選択的Ｘａ因子阻害剤
US6218382B1 (en) 1997-08-11 2001-04-17 Cor Therapeutics, Inc Selective factor Xa inhibitors
US6228854B1 (en) 1997-08-11 2001-05-08 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6333321B1 (en) 1997-08-11 2001-12-25 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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FR1225332A (fr) * 1958-05-24 1960-06-30 Basf Ag Procédé pour la teinture de produits en cellulose
FR1247796A (fr) * 1960-02-11 1960-12-02 Sandoz Sa Procédé pour la teinture, le foulardage et l'impression de fibres cellulosiques aumoyen de colorants azoïques créés sur la fibre
DE1253227B (de) * 1961-01-18 1967-11-02 Basf Ag Verfahren zum Faerben und bzw. oder Bedrucken von Textilgut
FR81432E (fr) * 1962-03-22 1963-09-20 Ciba Geigy Procédé de teinture de matières polyhydroxylées de structure fibreuse
FR1356513A (fr) * 1963-03-25 1964-03-27 Ciba Geigy Procédé de teinture de fibres azotées à l'aide des composants de colorants réactifs
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Also Published As

Publication number Publication date
WO1996001338A1 (fr) 1996-01-18
FI970045A0 (fi) 1997-01-03
FI970045A (fi) 1997-01-03
DE4423444A1 (de) 1996-01-11
AU2923695A (en) 1996-01-25

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