EP0447352B1 - Procédé pour améliorer le rendement et la solidité au mouillé de la teinture ou de l'impression avec des colorants anioniques de matériau fibreux cellulosique - Google Patents

Procédé pour améliorer le rendement et la solidité au mouillé de la teinture ou de l'impression avec des colorants anioniques de matériau fibreux cellulosique Download PDF

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Publication number
EP0447352B1
EP0447352B1 EP91810016A EP91810016A EP0447352B1 EP 0447352 B1 EP0447352 B1 EP 0447352B1 EP 91810016 A EP91810016 A EP 91810016A EP 91810016 A EP91810016 A EP 91810016A EP 0447352 B1 EP0447352 B1 EP 0447352B1
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formula
process according
dyeing
carried out
methyl
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EP0447352A1 (fr
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Rosemarie Töpfl
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Novartis AG
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Ciba Geigy AG
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    • 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
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5242—Polymers of unsaturated N-containing compounds
    • 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
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5278—Polyamides; Polyimides; Polylactames; Polyalkyleneimines
    • 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
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium 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
    • D06P3/62—Natural or regenerated cellulose using direct dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to a process for improving the yield and the wet fastness properties of dyeings or prints produced with anionic dyes on cellulose fiber material. From DE-A-3 626 410 it is known that monomeric cationic compounds, such as imidazolium salts, can be used to improve the coloration of cellulose fibers.
  • the process according to the invention is characterized in that cellulose fiber material is dyed with a quaternary ammonium salt of the formula before dyeing or during dyeing wherein R C1-C3-alkyl, X the group Hal is a halogen atom and Q ⁇ the anion of an aromatic sulfonic acid or especially a C1-C3 alkyl sulfate ion, such as, for example, benzenesulfonate, p-toluenesulfonate, chlorobenzenesulfonate, ethyl sulfate (CH3CH2SO4) or especially methyl sulfate (CH3SO4), mean treated.
  • a quaternary ammonium salt of the formula before dyeing or during dyeing wherein R C1-C3-alkyl, X the group Hal is a halogen atom and Q ⁇ the anion of an aromatic sulfonic acid or especially a C1-C3 alkyl
  • Suitable alkyl groups for R are methyl, ethyl, propyl, isopropyl. Ethyl and especially methyl are preferred.
  • Halogen means, for example, bromine, fluorine, iodine or preferably chlorine.
  • Specific ammonium salts of formula (1) that can be used in the present invention are N-epoxy-2,3-propyl-N-methyl-N, N-diallylammonium methyl sulfate, N- (3-chloro-2-hydroxypropyl) -N-methyl-N, N-diallylammonium methyl sulfate, N- (3-chloro-2-hydroxypropyl) -N-ethyl-N, N-diallylammonium ethyl sulfate, N- (3-chloro-2-hydroxypropyl) -N-methyl-N, N-diallylammonium p-toluenesulfonate, N-epoxy-2,3-propyl-N-ethyl-N, N-diallylammonium ethyl sulfate and N-epoxy-2,3-propyl-N-methyl-N, N-diallylammonium p-toluen
  • the first two representatives are particularly preferred.
  • the quaternary ammonium salts of the formula (1) are prepared by adding a tertiary diallylamine of the formula wherein X has the meaning given, with a sulfonic acid alkyl ester of the formula (3) Z-SO2-OR wherein Z represents an aryl radical or -OR and R has the meaning given.
  • the quaternary ammonium salt thus produced contains practically no dihalopropanol like dichloropropanol.
  • sulfonic acid esters are e.g. Benzenesulfonates, p-toluenesulfonates, p-bromobenzenesulfonates, p-chlorobenzenesulfonates, p-nitrobenzenesulfonates and especially dialkyl sulfates such as diethyl sulfate and especially dimethyl sulfate.
  • reaction is conveniently carried out at 30-90 ° C, preferably at 30-60 ° C.
  • the quaternization can be carried out in a non-polar or polar solvent, such as water, dimethylformamide or ethanol.
  • the quaternized product is isolated in the usual way.
  • the diallylamine compound of the formula (2) is prepared in a manner known per se by reacting diallylamine with an ⁇ -epihalohydrin, whereupon the halohydrin compound obtained is isolated. If one sets the reaction product e.g. an alkali metal hydroxide such as sodium hydroxide, the 1-diallylamino-2,3-epoxypropane is formed.
  • an alkali metal hydroxide such as sodium hydroxide
  • the epihalohydrin which is reacted with diallylamine can be any ⁇ -epihalohydrin, e.g. Epibromohydrin, Epifluorhydrin, Epijodhydrin, ß-Methylepichlorhydrin or preferably epichlorohydrin.
  • Quaternary ammonium salts which can be used according to the invention are particularly suitable for improving the color yield and the wet fastness of dyeings or prints which are based on cellulose fiber materials with anionic dyes, such as e.g. Reactive or direct dyes are generated.
  • the treatment of the cellulose material is preferably carried out semi-continuously by the cold residence method.
  • the cellulose material is impregnated with the treatment agent (fixative) e.g. subjected to a fixing process by printing or preferably padding and then by storage.
  • This application can be carried out before dyeing or during dyeing.
  • the treatment is preferably carried out by the block-cold dwell process and in particular during the dyeing.
  • the impregnation can be carried out at 20 to 50 ° C, but preferably at room temperature.
  • the fixing process is carried out by storing the impregnated goods for 4 to 48 hours, preferably 10 to 25 hours at room temperature.
  • the preparations advantageously contain the quaternary ammonium salt of the formula (1) in an amount of 10 to 70 g / l, preferably 25 to 50 g / l, of active ingredient.
  • the squeezing effect is expediently 60 to 120% by weight.
  • these preparations expediently also contain alkaline compounds, such as, for example, potassium hydroxide or preferably sodium hydroxide.
  • alkaline compounds such as, for example, potassium hydroxide or preferably sodium hydroxide.
  • a 30% aqueous sodium hydroxide solution is preferred, which is added to the preparation in an amount of 20 to 50 ml / l, preferably 25 to 40 ml / l.
  • the pH of the preparations can therefore generally be 8 to 13.5, preferably 10 to 12.
  • the preparations can also contain other conventional additives e.g. Electrolytes, e.g. Sodium chloride or sodium sulfate, urea, glycerin, thickeners such as e.g. Alginates, starch ethers or polyacrylates, reducing agents, dispersants and wetting agents, homopolymers or copolymers of acrylamide or methacrylamide or graft polymers, as described in EP-A-111 454 and EP-A-363 319, and also contain defoamers and other cationic fixing agents , which the latter can also be fiber-reactive.
  • Electrolytes e.g. Sodium chloride or sodium sulfate, urea, glycerin
  • thickeners such as e.g. Alginates, starch ethers or polyacrylates, reducing agents, dispersants and wetting agents, homopolymers or copolymers of acrylamide or methacrylamide or graft polymers, as described in EP-A
  • Regenerated or in particular natural cellulose can be considered as fiber material, such as e.g. Cellulose, viscose silk, hemp, linen, jute or preferably cotton, as well as fiber blends with synthetic fibers e.g. those made of polyamide / cotton or in particular polyester / cotton.
  • 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.
  • the pretreatment of the cellulose fiber material with the cationic compounds of the formula (1) can be coupled with other pretreatment operations.
  • the treatment of the cellulose fiber material is preferably carried out simultaneously with the dyeing.
  • the dyeings are carried out with reactive dyes or preferably with substantive dyes by the cold residence process, it being possible for the impregnation to be carried out both by printing and by padding.
  • the amount of the dyes generally depends on the desired color strength and is expediently 0.1 to 100 g per liter of liquor, preferably 5 to 40 g / l of liquor.
  • the dyeing can be carried out by the exhaust process or by two-stage processes, e.g. the padding process or printing can be produced, the padding process, in particular the so-called pad-steam process, pad-fix process or the pad-cold retention process being possible.
  • the usual direct dyes are suitable as noun dyes, for example the "Direct Dyes” mentioned in Color Index, 3rd edition (1971) Volume 2 on pages 2005-2478.
  • Reactive dyes are understood to be the usual dyes which 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 process according to the invention gives uniform and vivid colorations both in the pretreatment with subsequent dyeing and in the simultaneous application of the cationic fixative and dye, which are distinguished from known dyeing options by an improved color yield.
  • dyeings on cellulose fiber material with substantive dyes are produced, which show a considerable improvement in wet fastness properties.
  • the shade and lightfastness of the dyeings are not adversely affected.
  • the process is particularly environmentally friendly, since the cationic, fiber-reactive fixing agent does not contain a disruptive by-product like the dichloropropanol.
  • the percentages relate to the weight, unless stated otherwise.
  • the quantities relate to commercially available, that is to say coupe goods for the dyes and to the pure substance for the auxiliaries.
  • the five-digit Color Index numbers (CI) refer to the 3rd edition of the Color Index.
  • Example 1 247.6 g of dimethyl sulfate are added to 360 g of 1-diallylamino-3-chloro-2-hydroxypropane with stirring in 60 minutes at 20-40 ° C. and the mixture is stirred for 3 1/2 hours at room temperature.
  • the reaction product of the formula is viscous, clear and soluble in water.
  • the N, N-diallyl-N- (3-chloro-2-hydroxypropyl) amine used in Example 1 is produced as follows.
  • the reaction product of the formula is viscous, clear and soluble in water. Amine number: 0.012, epoxy number: 3.52.
  • the 1-diallylamino-2,3-epoxypropane used in Example 2 is produced as follows.
  • diallylamine 230 g are heated to 28 ° C. together with 222 g of ⁇ -epichlorohydrin and 7 g of water.
  • the reaction mixture is stirred at 28-30 ° C. for 7 hours.
  • a solution of 112 g of sodium hydroxide in 182 g of water is then added at 20 ° C.
  • the mixture is stirred at 22-25 ° C for 16 hours.
  • the mixture is then diluted with 400 g of water and the organic phase is separated off. The latter is dried over potassium carbonate and at Distilled at 40-42 ° C.
  • the 1-diallylamino-2,3-epoxypropane obtained has an amine number of 6.48 and an epoxy number of 6.23.
  • Example 3 108.9 g of diethyl sulfate are added to 108.8 g of 1-diallylamino-2,3-epoxypropane with stirring in 70 minutes at 60-85 ° C. and the mixture is stirred at 75 ° C. for 1 1/2 hours.
  • the product of the formula is viscous, clear and soluble in water.
  • Example 4 189.5 g of 1-diallylamino-3-chloro-2-hydroxypropane are dissolved in 126 g of acetone, 186 g of methyl p-toluenesulfonic acid are added at 30-40 ° C. in 2 hours and the mixture is stirred for 1 1/2 hours this temperature. The solvent is then removed.
  • reaction product of the formula is viscous, clear and soluble in water. Amine number: 0.014.
  • Table 1 The authenticity assessments are listed in Table 1 below.
  • Table 1 Coloring g / l dye Fastness to wet ironing ISO C2S wash Change the nuance Bleeding on cotton (1) without 45 3-4 4th 2nd With 20th 5 5 3-4 (2) without 16 2nd 4th 2nd With 12th 5 5 5 (3) without 25th 2-3 4-5 4th With 12th 4-5 5 5 (4) without 35 4-5 4-5 3-4 With 20th 5 5 5
  • the goods are then rinsed cold and hot and dried.
  • Example 3 20 g of cotton tricot, bleached and mercerized, are padded with a preparation in a liter of 90% with a liquor absorption 35 g of the quaternary ammonium salt of the formula (4) 30 ml sodium hydroxide solution (30%) contains. After padding, the tricot is rolled up wet and stored in a plastic bag for 18 hours at room temperature. The goods are then rinsed cold and hot.
  • the pretreated tricot is wetted together with 20 g of untreated tricot in an aqueous dye liquor at 50 ° C., which, at a liquor ratio of 1:40, 1% of the dye Direct Blue 71 C.I. 43140 contains.
  • the temperature is raised to 98 ° C. within 30 minutes and dyeing is carried out at this temperature for 45 minutes.
  • Example 4 The tricot pretreated according to example 3 is wetted together with 20 g of untreated tricot at 98 ° C. in an aqueous liquor which has a liquor ratio of 1:30 1% of the dye of the formula contains. The temperature is then reduced to 85 ° C. within 30 minutes, adds 5 g / l sodium carbonate calc. 2 ml / l sodium hydroxide solution (30%) and treat the material for a further 45 minutes at 85 ° C. The dyeings are then rinsed in boiling water for 5 minutes.
  • Example 5 The tricot pretreated according to example 3 is wetted together with 20 g of non-pretreated tricot and 20 g of tricot treated in the same way, but only with 30 ml / l sodium hydroxide solution (30%) in an aqueous liquor at 50.degree a liquor ratio of 1:40, 1% of a dye of the formula contains. The material is then dyed for 40 minutes at 50 ° C and then rinsed warm for 5 minutes.

Claims (10)

  1. Procédé pour améliorer le rendement tinctorial et les solidités au mouillé de teintures ou impressions produites par des colorants anioniques sur des matières fibreuses cellulosiques, caractérisé en ce que l'on traite la matière fibreuse, avant la teinture ou pendant la teinture, avec un sel d'ammonium quaternaire de formule :
    Figure imgb0026
     dans laquelle R représente un groupe alkyle en C₁-C₃, X représente le groupe
    Figure imgb0027
     Hal représente un atome d'halogène et Q- représente l'anion d'un acide sulfonique aromatique ou un ion alkyl(C₁-C₃)sulfate.
  2. Procédé selon la revendication 1, caractérisé en ce que R représente un groupe méthyle ou éthyle dans la formule (1).
  3. Procédé selon la revendication 1 ou 2, caractérisé en ce que X représente, dans la formule (1), le groupe chlorhydrine
    Figure imgb0028
  4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé en ce que Q- représente, dans la formule (1), l'ion méthylsulfate ou l'ion éthylsulfate.
  5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que, dans la formule (1), R représente le groupe méthyle, X représente le groupe
    Figure imgb0029
     et Q- représente l'ion méthylsulfate.
  6. Procédé selon l'une quelconque des revendications 1 à 5, caractérisé en ce que le traitement est réalisé de manière semi-continue, selon le procédé de séjour à froid.
  7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé en ce que le traitement est réalisé selon le procédé de séjour à froid avec foulardage et pendant la teinture.
  8. Procédé selon l'une quelconque des revendications 1 à 7, caractérisé en ce que le traitement a lieu en milieu alcalin.
  9. Procédé selon l'une quelconque des revendications 1 à 8, caractérisé en ce que le traitement est réalisé pour l'amélioration du rendement tinctorial et des solidités au mouillé des teintures produites par des colorants substantifs.
  10. Procédé selon l'une quelconque des revendications 1 à 9, caractérisé en ce que l'on obtient le sel d'ammonium quaternaire de formule (1) en faisant réagir une diallylamine tertiaire de formule :
    Figure imgb0030
     dans laquelle X a les significations indiquées dans les revendications 1 à 9, avec un ester d'alkyle d'acide sulfonique de formule :



            Z-SO₂-OR   (3)



    dans laquelle Z représente un groupe aryle ou OR, et R a les significations indiquées dans les revendications 1 à 9.
EP91810016A 1990-03-15 1991-01-10 Procédé pour améliorer le rendement et la solidité au mouillé de la teinture ou de l'impression avec des colorants anioniques de matériau fibreux cellulosique Expired - Lifetime EP0447352B1 (fr)

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CH84890 1990-03-15
CH848/90 1990-03-15

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EP0447352A1 EP0447352A1 (fr) 1991-09-18
EP0447352B1 true EP0447352B1 (fr) 1994-12-21

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US (1) US5147411A (fr)
EP (1) EP0447352B1 (fr)
JP (1) JPH04214479A (fr)
DE (1) DE59103947D1 (fr)
PT (1) PT96523B (fr)
ZA (1) ZA91377B (fr)

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GB9120227D0 (en) * 1991-09-23 1991-11-06 Ici Plc Printing process and pretreatment composition
ES2091611T3 (es) * 1992-06-04 1996-11-01 Ciba Geigy Ag Proceso para la fijacion de colorantes, que contienen como minimo un doble enlace polimerizable, por medio de radiacion ionizante.
ES2088654T3 (es) * 1992-10-01 1996-08-16 Ciba Geigy Ag Procedimiento para teñir materiales de fibra de lana.
US5725604A (en) * 1993-09-16 1998-03-10 Ciba Specialty Chemicals Corporation Thermofixing of dyes in presence of polymerizable compound and an initiator
US5698476A (en) * 1995-03-01 1997-12-16 The Clorox Company Laundry article for preventing dye carry-over and indicator therefor
DE19509982A1 (de) * 1995-03-18 1996-09-19 Sandoz Ag Textilnachbehandlungsmittel
US5667533A (en) * 1996-02-07 1997-09-16 The Virkler Company Heather dyed fabric and method of producing same
US5833720A (en) * 1996-04-29 1998-11-10 Kent; Johnny Joe Energy efficient dyeing method
GB9703813D0 (en) * 1997-02-24 1997-04-16 Ici Plc Dyeing of textiles
US6323306B1 (en) 1998-09-08 2001-11-27 Ciba Specialty Chemicals Water Treatments Ltd. Preparation of water-soluble cross-linked cationic polymers
CN1823042B (zh) * 2003-07-14 2010-06-23 西巴特殊化学品控股有限公司 制备位阻n-烃氧基胺类化合物的过氧化氢催化的方法
WO2005123581A1 (fr) * 2004-06-09 2005-12-29 University Of Florida Research Interfaces ultralyophobes
EP1948700A2 (fr) * 2005-11-14 2008-07-30 Ciba Holding Inc. Preparation de polymeres cationiques fonctionnalises et preparation et application de ceux-ci dans les soins personnels
JP5642554B2 (ja) * 2007-12-20 2014-12-17 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ カチオン性三元共重合体およびパーソナルケア組成物の調製
US9745694B2 (en) 2013-01-25 2017-08-29 Colorzen, Llc Treatment of fibers for improved dyeability
WO2018190328A1 (fr) * 2017-04-14 2018-10-18 日東紡績株式会社 Améliorant de solidité au frottement humide pour fibres à base de cellulose, procédé de production de fibre de cellulose colorée l'utilisant et son utilisation

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JPS6071786A (ja) * 1983-09-28 1985-04-23 第一工業製薬株式会社 染色堅牢度向上方法
JPS60110987A (ja) * 1983-11-15 1985-06-17 日東紡績株式会社 染色堅牢度向上法
JPS61133213A (ja) * 1984-11-30 1986-06-20 Sumitomo Chem Co Ltd ジアリルアミン系共重合体、その製法およびそれを含有する染色堅牢度向上剤
JPS61231283A (ja) * 1985-04-01 1986-10-15 日東紡績株式会社 染色堅牢度向上法
DE3626410A1 (de) * 1985-08-08 1987-02-19 Ciba Geigy Ag Verfahren zum klotzfaerben von cellulose-textilmaterialien
CH677857B5 (fr) * 1986-07-02 1992-01-15 Sandoz Ag
DE3720508A1 (de) * 1986-07-02 1988-01-07 Sandoz Ag Wasserloesliche polymer von diallylamin
DE3706176A1 (de) * 1987-02-26 1988-09-08 Sandoz Ag Mischung mit synergistischen eigenschaften

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PT96523B (pt) 1998-06-30
US5147411A (en) 1992-09-15
ZA91377B (en) 1991-08-28
JPH04214479A (ja) 1992-08-05
PT96523A (pt) 1991-10-15
DE59103947D1 (de) 1995-02-02
EP0447352A1 (fr) 1991-09-18

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