EP0957197A1 - Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique - Google Patents

Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique Download PDF

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Publication number
EP0957197A1
EP0957197A1 EP99810385A EP99810385A EP0957197A1 EP 0957197 A1 EP0957197 A1 EP 0957197A1 EP 99810385 A EP99810385 A EP 99810385A EP 99810385 A EP99810385 A EP 99810385A EP 0957197 A1 EP0957197 A1 EP 0957197A1
Authority
EP
European Patent Office
Prior art keywords
acid
homo
parts
dyes
fiber material
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
EP99810385A
Other languages
German (de)
English (en)
Other versions
EP0957197B1 (fr
Inventor
Philippe Ouziel
Jean-Marie Adam
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding 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 Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP99810385A priority Critical patent/EP0957197B1/fr
Publication of EP0957197A1 publication Critical patent/EP0957197A1/fr
Application granted granted Critical
Publication of EP0957197B1 publication Critical patent/EP0957197B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/08—After-treatment with organic compounds macromolecular
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • 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
    • Y10S8/93—Pretreatment before dyeing

Definitions

  • the present invention relates to a method for the treatment of natural or synthetic polyamide fiber materials to improve the durability of the dyes against exposure to ozone.
  • Dyes and prints with dyes often show a high sensitivity to Ozone.
  • anthraquinone dyes are easily oxidatively degraded by ozone and in this way change their absorption behavior and thus the color. This Behavior is particularly observed with blue anthraquinone dyes.
  • the nuance a trichromatic stain based on blue anthraquinone dyes, for example one Polyamide carpet fabric, is easily changed by exposure to ozone. You meet this deficiency in general by resinating the dyed polyamide fiber material treated on the basis of phenol-formaldehyde condensates.
  • improvements in ozone resistance have disadvantages, e.g.
  • the present invention therefore relates to a process for improving the resistance of dyes on natural or synthetic polyamide fiber materials to the effects of ozone, characterized in that the fiber material is treated with a liquor containing a homo- or copolymer with recurring structural units before, during or after dyeing of the formula (1) wherein R 1 is optionally substituted C 1 -C 4 alkyl.
  • Suitable C 1 -C 4 alkyl for R 1 are, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, these alkyl radicals being unsubstituted or substituted, for example by halogen, such as fluorine, chlorine or bromine, hydroxy or sulfo.
  • R 1 is preferably C 1 -C 4 alkyl and especially methyl.
  • They preferably contain according to the invention as agents for improving the Homo- or copolymers used 50 to 100 mol% and ozone resistance in particular 80 to 100 mol% of repeating structural units of the formula (1).
  • polymers used according to the invention are copolymers, then come as copolymerizable monomers e.g. anionic or non-ionic groups containing compounds in question.
  • the following unsaturated compounds may be mentioned as examples of monomers containing anionic groups: 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, allylacetic acid, allyloxyacetic acid, ⁇ , ⁇ -dimethylacrylic acid, allylmalonic acid, allyloxymaloxy, allylacrylic acid, carboxylate, methacryloyloxyacyl, methacrylate, carboxylate Allyl succinic acid, acrylamidoglycolic acid, vinylsulfonic acid, (meth) allylsulfonic acid, (meth) acrylamidomethylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, (meth) acrylamidoethanesulfonic acid, (meth) acrylamidomethanes
  • unsaturated compounds may be mentioned as examples of monomers containing nonionic groups: Maleic anhydride, vinylcaprolactam, diallylamine, N-methyldiallylamine, N-ethyldiallylamine, N-vinylpyrrolidone, N-vinylformamide, N-vinyl acetamide, N-vinyl-N-methylformamide, 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 such as ethylene, propylene, isobutene, styrene
  • Copolymerizable monomers in the polymers used according to the invention Acrylic acid, maleic acid, vinyl acetic acid, acrylamidoglycolic acid, (meth) acrylamidomethanesulfonic acid, vinylsulfonic acid, (meth) allylsulfonic acid, (meth) acrylamidomethylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, (meth) acrylamidoethanesulfonic acid, (meth) acrylamidomethanesulfonic acid, sulfopropyl (st) sulfatonic acid, sulfopropyl (meth) acrylate sulfate, Maleic anhydride, N-vinylpyrrolidone, vinylcaprolactam, N-vinylformamide, N-vinyl-N-methylformamide, N-vinyl acetamide, N-vinyl-N-methyl-acetamide
  • Very particularly preferred as copolymerizable monomers in the polymers used according to the invention are: Vinylsulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 3- (meth) acrylamidopropanesulfonic acid, maleic anhydride, N-vinylpyrrolidone, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methyl-acetamide, N -Vinylimidazole, vinyl acetate, styrene, hydroxyethyl / propyl- (meth) acrylate, (meth) acrylic acid-C 1 -C 6 alkyl ester, (meth) acrylonitrile, (meth) acrylamide, N-mono / N, N-di -C 1 -C 6 alkyl- (meth) acrylamide or 2-methoxy-3,4-dihydro-2H-pyran.
  • Particularly important as copolymerizable monomers in the polymers used according to the invention are: Vinylsulfonic acid, 3- (meth) acrylamidopropanesulfonic acid or 2-methoxy-3,4-dihydro-2H-pyran.
  • the homopolymers or copolymers used in the process according to the invention have average molecular weight of 1,000 to 1,000,000, preferably 1,000 to 500,000 and in particular 5,000 to 200,000.
  • the homopolymers or copolymers containing recurring structural units of the above formula (1) used according to the invention as agents for improving the ozone resistance are prepared in a manner known per se, for example by polymerization of the monomers of the formula (2) initiated ionically or preferably by free radicals.
  • R 1 has the meanings and preferences given above, for example in solution, suspension or emulsion, optionally in the presence of the unsaturated compounds mentioned above as examples of copolymerizable monomers.
  • the polymerization is preferably carried out in solution with a peroxide, persulfate or an azo compound, for example with sodium persulfate or azo-bis- (2-amidinopropane) hydrochloride, as a free-radical initiator, for example in an amount of 0.005 to 10% by weight, based on the monomers used, is present.
  • a peroxide, persulfate or an azo compound for example with sodium persulfate or azo-bis- (2-amidinopropane) hydrochloride, as a free-radical initiator, for example in an amount of 0.005 to 10% by weight, based on the monomers used, is present.
  • the homo- or copolymers used in the process according to the invention are regardless of the fleet ratio e.g. in an amount of 0.05 to 10% by weight, preferably 0.1 to 6% by weight and particularly preferably 0.5 to 4% by weight, based on the weight of the polyamide fiber material used.
  • Treatment of the polyamide fiber material with the homo- or copolymers can be before, during or after dyeing and preferably during or after dyeing.
  • the polyamide fiber material is treated with those used according to the invention Homopolymers or copolymers during the dyeing process, that's how it is done Process according to the invention advantageously such that the polymers of Dyeing liquor is added in the amount specified above and the fiber material in the usual way Way colors.
  • the polyamide fiber material is treated with those used according to the invention Homopolymers or copolymers after dyeing, this is done according to the invention Process advantageously such that the polyamide fiber material is first in usually colors and then an aftertreatment with a polymer in the connects the previously specified amount containing fresh aqueous liquor. After that the dyed polyamide fiber material can be dewatered and opened without further rinsing can be dried in the usual way.
  • the after-treatment is usually carried out in a fresh one Fleet. However, it can also be carried out directly in the dye bath, provided that the dye bath is at the end largely stripped and is still sufficiently acidic. After the treatment is usually rinsed briefly with water.
  • Natural polyamide fiber material such as e.g. Wool or Silk, or synthetic polyamide fiber material, e.g. Polyamide 6 or polyamide 6.6, or fiber mixtures such as Wool / cellulose or polyamide / cellulose mixed fibers or Polyamide / wool mixed fibers into consideration.
  • the fiber material is preferred around synthetic polyamide fiber material.
  • the textile can be used in any form, e.g. as fiber, yarn, woven or knitted fabric.
  • the dyeings are carried out, for example, with anionic dyes, all of the usual anionic dyes, e.g. as in Color Index, 3rd edition (1971) and the Addenda to this are described under the heading "Acid Dyes”.
  • Examples are sulfo group-containing monoazo, polyazo, metal complex azo, anthraquinone, Phthalocyanine or formazan dyes.
  • the dyeings are preferably carried out using anthraquinone dyes and in particular blue ones Anthraquinone dyes.
  • the anionic dyes used to dye the polyamide fiber material lie either in the form of their free sulfonic acid or preferably as their salts.
  • the salts include, for example, the alkali, alkaline earth or ammonium salts or the salts an organic amine.
  • Examples include sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
  • the anionic dyes used to dye the polyamide fiber material can other additives, e.g. Cooking salt or dextrin.
  • the dyeing of the polyamide fiber material with anionic dyes can be carried out according to the these dyes usual dyeing or printing processes, for example according to Pull-out procedure.
  • the dyeing liquors or printing pastes can also Water and the dyes further additives, for example wetting agents, anti-foaming agents, Leveling agents or agents influencing the property of the textile material, e.g. Plasticizers, additives for flame retardant or dirt, water and oil repellent Agents and water softening agents and natural or synthetic Thickeners, e.g. Alginates and cellulose ethers.
  • the amounts of anionic dyes in the dye baths or printing pastes can be used within wide limits depending on the desired depth of color fluctuate, in general amounts have from 0.01 to 15% by weight, in particular 0.01 up to 10% by weight, based on the dye material or the printing paste, has proven to be advantageous.
  • the dyeing is preferably carried out with anionic dyes at a pH of 3 to 7, in particular 4 to 7, one used in the presence of those according to the invention Homo- or copolymers preferably at a pH of 2 to 7 and especially 4 to 7 colors.
  • the liquor ratio can be chosen within a wide range, e.g. from 1: 5 to 1:50, preferably 1: 5 to 1:30. It is preferred to dye at a temperature from 70 to 110 ° C, in particular 80 to 105 ° C, wherein in the presence of the invention homo- or copolymers used preferably at 50 to 100 ° C and in particular is dyed at 80 to 100 ° C.
  • the aftertreatment with the homo- or copolymers used according to the invention preferably takes place using the pull-out method.
  • the fleet ratio can be within a wide range can be selected and is e.g. 1: 4 to 1: 100, preferably 1:10 to 1:40 and especially 1: 5 to 1:40.
  • Dyeing machines e.g. open baths, reel runners, jigger or paddle, jet or Circulators can be used.
  • the treatment time can e.g. 10 to 60 minutes and preferably 15 to 40 minutes.
  • the pH of the fleet is usually included 2 to 7, preferably 4 to 7 and in particular 4 to 6.
  • the liquor can contain other conventional additives, e.g. Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
  • Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
  • the process according to the invention gives dyeings or prints of Dyes, e.g. anionic dyes, on polyamide fiber material, which a have significant improvement in ozone fastness, without the color yield, nuance or the light fastness can be negatively affected.
  • Dyes e.g. anionic dyes
  • a dye bath containing 600 parts of water, 0.0108 parts of a dye of the formula 0.0135 parts of a dye of the formula and 0.033 parts of a dye of the formula is adjusted to a pH of 6.5 with 0.72 parts of sodium dihydrogenphosphate monohydrate and 0.6 part of disodium hydrogenphosphate dodecahydrate.
  • This dye bath is mixed with 30 parts of polyamide carpet fabric (polyamide 6) at 30 ° C. The temperature is raised uniformly to the boiling point within 45 minutes and dyeing is then carried out for a further 30 minutes at this temperature. The gray colored carpet is then rinsed.
  • the dyed carpet fabric is in a fresh bath from 600 parts of water, 1.5 parts of the polymer solution according to Example 1 (amount of 2 wt .-% polymer based on the carpet fabric), 0.6 parts of sodium acetate and 0.7 parts of acetic acid at a pH of 4.5 and a temperature of 75 ° C for 15 minutes.
  • the carpet fabric is then rinsed and dried.
  • the ozone fastness of the dyeing obtained is carried out in accordance with the test specification ISO 105-G03. The comparison of the after-treated carpet fabric with a carpet fabric that was not after-treated shows a significant increase in the ozone resistance of the after-treated carpet fabric.
  • Example 5 The procedure is as described in Example 5, but instead of 2% by weight, based on the carpet fabric, the polymer according to Example 1, the equivalent amount one of the polymers according to one of Examples 2 to 4, is also a Obtain polyamide carpet fabric with a gray, ozone-resistant color.
  • a dye bath containing 600 parts of water, 0.0108 parts of a dye of the formula 0.0135 parts of a dye of the formula and 0.033 parts of a dye of the formula and 1.5 parts of the polymer solution from Example 1 (amount used 2% by weight) is adjusted to a pH of 6.5 using 0.72 part of sodium dihydrogenphosphate monohydrate and 0.6 part of disodium hydrogenphosphate dodecahydrate.
  • This dye bath is mixed with 30 parts of polyamide carpet fabric (polyamide 6) at 30 ° C. The temperature is raised uniformly to the boiling point within 45 minutes and dyeing is then carried out for a further 30 minutes at this temperature. The gray colored carpet is then rinsed briefly with cold water and dried.
  • the ozone fastness of the dyeing obtained is carried out in accordance with the test specification ISO 105-G03.
  • the comparison of the dyed carpet fabric with a carpet fabric which was not dyed in the presence of the polymer solution from Example 1 shows a significant increase in the resistance to ozone.
  • Example 6 The procedure is as described in Example 6, but instead of 2% by weight, based on the carpet fabric, the polymer according to Example 1, the equivalent amount one of the polymers according to one of Examples 2 to 4, is also a Obtain polyamide carpet fabric with a gray, ozone-resistant color.

Landscapes

  • 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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP99810385A 1998-05-13 1999-05-04 Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique Expired - Lifetime EP0957197B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99810385A EP0957197B1 (fr) 1998-05-13 1999-05-04 Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP98810433 1998-05-13
EP98810433 1998-05-13
EP99810385A EP0957197B1 (fr) 1998-05-13 1999-05-04 Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique

Publications (2)

Publication Number Publication Date
EP0957197A1 true EP0957197A1 (fr) 1999-11-17
EP0957197B1 EP0957197B1 (fr) 2006-06-21

Family

ID=8236082

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99810385A Expired - Lifetime EP0957197B1 (fr) 1998-05-13 1999-05-04 Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique

Country Status (8)

Country Link
US (1) US6280482B1 (fr)
EP (1) EP0957197B1 (fr)
JP (1) JP4443669B2 (fr)
AU (1) AU751951B2 (fr)
CA (1) CA2271873A1 (fr)
DE (1) DE59913578D1 (fr)
DK (1) DK0957197T3 (fr)
ZA (1) ZA993274B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003041639A2 (fr) * 2001-10-30 2003-05-22 Microbiotix, Inc. Methodes et preparations pour le traitement de maladies a rotavirus

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0957197B1 (fr) * 1998-05-13 2006-06-21 Ciba SC Holding AG Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique
US20030165404A1 (en) * 2000-06-05 2003-09-04 Takeshi Omatsu Ozone indicator and method of measuring ozone concentration
JP2005511909A (ja) * 2001-12-05 2005-04-28 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 天然または合成のポリアミド繊維材料の処理方法
JP2007321247A (ja) * 2006-05-30 2007-12-13 Seiren Co Ltd ポリアミド系繊維構造物
CN110882680A (zh) * 2019-12-05 2020-03-17 广东海纳新材料科技有限公司 一种疏水矿化废弃纤维吸附材料的制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1254743A (en) * 1969-06-16 1971-11-24 Textilmaschb Zittau Veb Application of dyestuffs to napped and pile textiles
US3984202A (en) * 1972-02-14 1976-10-05 Allied Chemical Corporation Alkanolamines to reduce ozone attack on dyes in polyamide fibers
US4097546A (en) * 1976-03-30 1978-06-27 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene copolymers
GB2024874A (en) * 1978-07-07 1980-01-16 Sandoz Ltd After treatment of cellulosic fibres dyed with reactive dyes
WO1989007519A1 (fr) * 1988-02-17 1989-08-24 The Dow Chemical Company Complexe de polymeres et de sels servant au traitement de fibres ou de tissus
US5464452A (en) * 1994-05-10 1995-11-07 Henkel Corporation Process for fixing dyes in textile materials
EP0824155A1 (fr) * 1996-08-15 1998-02-18 Clariant Finance (BVI) Limited Solutions aqueuses concentrées de sels de sodium d'acides polycarboxyliques, leur préparation et leur utilisation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822373A (en) 1988-03-11 1989-04-18 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance with sulfonated novolak resin and polymethacrylic acd
US4937123A (en) 1988-03-11 1990-06-26 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance
EP0812949A3 (fr) 1996-06-11 1998-07-22 Ciba SC Holding AG Procédé pour traiter des matériaux fibreux cellulosiques teints
JPH1096180A (ja) 1996-08-15 1998-04-14 Clariant Internatl Ltd ポリカルボン酸ナトリウム塩の濃厚な水溶液及びその使用方法
US5948125A (en) 1997-05-20 1999-09-07 Ciba Specialty Chemicals Corporation Method of treating dyed, natural or synthetic polyamide fibre materials
EP0957197B1 (fr) * 1998-05-13 2006-06-21 Ciba SC Holding AG Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1254743A (en) * 1969-06-16 1971-11-24 Textilmaschb Zittau Veb Application of dyestuffs to napped and pile textiles
US3984202A (en) * 1972-02-14 1976-10-05 Allied Chemical Corporation Alkanolamines to reduce ozone attack on dyes in polyamide fibers
US4097546A (en) * 1976-03-30 1978-06-27 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene copolymers
GB2024874A (en) * 1978-07-07 1980-01-16 Sandoz Ltd After treatment of cellulosic fibres dyed with reactive dyes
WO1989007519A1 (fr) * 1988-02-17 1989-08-24 The Dow Chemical Company Complexe de polymeres et de sels servant au traitement de fibres ou de tissus
US5464452A (en) * 1994-05-10 1995-11-07 Henkel Corporation Process for fixing dyes in textile materials
EP0824155A1 (fr) * 1996-08-15 1998-02-18 Clariant Finance (BVI) Limited Solutions aqueuses concentrées de sels de sodium d'acides polycarboxyliques, leur préparation et leur utilisation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003041639A2 (fr) * 2001-10-30 2003-05-22 Microbiotix, Inc. Methodes et preparations pour le traitement de maladies a rotavirus
WO2003041639A3 (fr) * 2001-10-30 2003-07-24 Microbiotix Inc Methodes et preparations pour le traitement de maladies a rotavirus

Also Published As

Publication number Publication date
DE59913578D1 (de) 2006-08-03
EP0957197B1 (fr) 2006-06-21
CA2271873A1 (fr) 1999-11-13
DK0957197T3 (da) 2006-10-09
JPH11350354A (ja) 1999-12-21
AU2810299A (en) 1999-11-25
US6280482B1 (en) 2001-08-28
AU751951B2 (en) 2002-09-05
ZA993274B (en) 1999-11-15
JP4443669B2 (ja) 2010-03-31

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