EP0429983B1 - Composition hydro- et oléophobante - Google Patents

Composition hydro- et oléophobante Download PDF

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Publication number
EP0429983B1
EP0429983B1 EP90121949A EP90121949A EP0429983B1 EP 0429983 B1 EP0429983 B1 EP 0429983B1 EP 90121949 A EP90121949 A EP 90121949A EP 90121949 A EP90121949 A EP 90121949A EP 0429983 B1 EP0429983 B1 EP 0429983B1
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EP
European Patent Office
Prior art keywords
carbon atoms
compositions
component
polyurethane
groups
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.)
Expired - Lifetime
Application number
EP90121949A
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German (de)
English (en)
Other versions
EP0429983A3 (en
EP0429983A2 (fr
Inventor
Wolfgang Dr. Henning
Walter Dr. Meckel
Thomas Dr. Münzmay
Wilfried Kortmann
Peter Selinger
Peter Nussbaum
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Bayer AG
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Bayer AG
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Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0429983A2 publication Critical patent/EP0429983A2/fr
Publication of EP0429983A3 publication Critical patent/EP0429983A3/de
Application granted granted Critical
Publication of EP0429983B1 publication Critical patent/EP0429983B1/fr
Anticipated expiration legal-status Critical
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2164Coating or impregnation specified as water repellent
    • Y10T442/2172Also specified as oil repellent

Definitions

  • the present invention relates to water repellents and oil repellents based on perfluoroalkyl group-containing polymers.
  • fluorine compounds are rarely used alone in equipment formulations.
  • urea resins, melamine resins or other resins mostly based on methylol compounds.
  • fluorine compounds are combined with extenders, e.g. with paraffin fractions or paraffin waxes and / or fatty acid esters and melamine resins (cf. Chwala / Anger: "Handbuch der Textilosstoff", Verlag Chemie-Weinheim-New York 1977, pages 745 to 747, 721).
  • Suitable components A) are commercially available perfluoroalkyl polymers from the series of perfluofalkyl group-containing vinyl, styryl, vinylidene, acrylic, methacrylic and ⁇ -chloroacrylic polymers with 4 to 20 carbon atoms in the perfluoroalkyl radical.
  • Preferred compounds are acrylate (co) polymers with a fluorine content of 20 to 45, in particular 35 to 45% by weight.
  • Such compounds were preferably used in the form of their aqueous emulsions or dispersions.
  • the cationically modified polyurethanes are very particularly preferably used in the form of their aqueous solutions or dispersions and contain a content of incorporated ternary or quaternary ammonium groups which ensures their solubility or dispersibility in water, and, if appropriate, of built-in ethylene oxide units present within a polyether chain, the content of ternaries or quaternary ammonium compounds at 2 to 300 milliequivalents per 100 g of solid and the content of the ethylene oxide units mentioned is from 0 to 25% by weight, based on the solid.
  • the agents according to the invention serve in particular as textile finishing agents for the phobing of textiles. They are in the form of aqueous dispersions with a solids content of 10 to 50%, preferably 15 to 40%. With a solids content of 15% this is Mixing ratio of perfluoro compound A) to cationically modified polyurethanes B) in the finishing liquor, for example at 0.5: 1 to 10: 1, in particular at 1: 1 to 5: 1, based on the solids content.
  • aqueous dispersions according to the invention can contain further components such as other textile auxiliaries, e.g. Synthetic resins.
  • These further constituents are preferably nonionic or cationic in nature.
  • the aqueous dispersions are diluted with water before use on the textile materials.
  • the application amounts are chosen so that a coating amount of 0.5 to 15 g, preferably 0.5 to 5 g and in particular 0.5 to 1.5 g of solids of the substance according to the invention per kg of textile material is obtained.
  • natural and synthetic materials such as fibers, filaments, yarns, nonwovens, fabrics, knitted fabrics and knitted fabrics made in particular of cellulose and its derivatives but also of polyester, polyamide and polyacrylonitrile materials, wool or silk can be successfully finished.
  • hydrophobized or oleophobicized textile structures such as nonwovens or, in particular, fabrics are used, for example, for the production of umbrella coverings, tents, water-repellent clothing or covers, balloon envelopes, awnings, textile floor coverings, packaging materials or footwear,
  • the finishing is carried out by known methods, preferably by the pull-out or padding method, for example between room temperature and 40 ° C., but also by splashing or spraying with a subsequent temperature treatment at 80 to 180, preferably 120 to 150 ° C.
  • a cotton gabardine fabric with a m2 weight of approx. 240 g was equipped with the following formulations:
  • the cotton fabric was soaked in a chassis with the liquors and squeezed between 2 rubber rollers (foulard).
  • the liquor absorption was 70% based on the textile weight.
  • the samples were dried at 100 ° C and condensed at 150 ° C for 5 minutes.
  • the grade for oil repellency corresponds to the highest numbered test liquid that does not wet the fiber material within 30 seconds: Grade 1 lowest value Grade 8 highest value.
  • Component I added according to the invention already gives this increase with use, based on solid substance, of 1.5 g / l, while component III, which is not in accordance with the invention, is effective only when 10 g / l is used.
  • the cotton swatches finished in Example 1 were washed 5 times at 40 ° C. on a Miele washing machine type W 763 washed with an easy care program with the addition of a household detergent and dried at 80 ° C in a Miele household dryer.
  • Component I added in accordance with the invention improves the wash resistance of fluorine finishes in such a way that even after 5 machine washes, the phobia values are retained, while the finishes without extender or with component III drop significantly.
  • a dyed polyester / cotton poplin fabric (67% PES / 33% cotton) with a weight of approx. 160 g m2 was equipped with the following formulations on the foulard:
  • Component I added according to the invention improves the wash resistance in such a way that even after 5 machine washes, the phobic values are almost completely retained,
  • a wool fabric with a weight of 280 g / m2 is padded as follows:
  • the fleet uptake was 80%. After treatment at 100 ° C, the tissues are treated for 3 minutes at 140 ° C:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Claims (7)

  1. Composition conférant le caractère hydrophobe et oléophobe, contenant
    A) un polymère porteur de groupes perfluoralkyle et
    B) un polyuréthanne, caractérisée en ce que le polyuréthanne a subi une modification cationique et contient des composants structuraux contenant des groupes acylurée de formule
    Figure imgb0016
    dont la quantité est calculée de manière qu'il y ait dans le produit d'addition polyisocyanate 0,1 à 20 % en poids, par rapport à la fraction de matière solide, du motif structural formant les groupes acylurée mentionnés, de formule
    Figure imgb0017
    et
    R   représente un reste d'hydrocarbure aliphatique saturé ou non saturé ayant jusqu'à 35 atomes de carbone, de préférence 9 à 22 atomes de carbone ou un reste d'hydrocarbure aromatique ayant 6 à 10 atomes de carbone ou un reste d'hydrocarbure araliphatique ayant 7 à 10 atomes de carbone.
  2. Composition suivant la revendication 1, caractérisée en ce qu'on utilise comme composant A) des polymères portant un groupe perfluoralkyle ayant 4 à 20 atomes de carbone, qui peut être interrompu par de l'oxygène.
  3. Composition suivant la revendication 1 ou 2, caractérisée en ce que le composant A) est un polymère d'acrylate ayant une teneur en fluor de 20 à 45 % en poids.
  4. Composition suivant les revendications 1 à 3, caractérisée en ce qu'on utilise le composant polyuréthanne B) sous forme de solutions ou de dispersions aqueuses.
  5. Procédé d'apprêtage de matières textiles, caractérisé en ce qu'on utilise des compositions suivant les revendications 1 à 4.
  6. Procédé d'apprêtage de matières textiles, avec des compositions conférant le caractère hydrophobe et/ou le caractère oléophobe, à base de polymères contenant des groupes perfluoralkyle, caractérisé en ce qu'on utilise comme diluant un polyuréthanne modifié par voie cationique.
  7. Corps textiles apprêtés avec des compositions suivant les revendications 1 à 4.
EP90121949A 1989-11-29 1990-11-16 Composition hydro- et oléophobante Expired - Lifetime EP0429983B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3939341 1989-11-29
DE3939341A DE3939341A1 (de) 1989-11-29 1989-11-29 Hydrophobierungs- und oleophobierungsmittel

Publications (3)

Publication Number Publication Date
EP0429983A2 EP0429983A2 (fr) 1991-06-05
EP0429983A3 EP0429983A3 (en) 1991-10-23
EP0429983B1 true EP0429983B1 (fr) 1994-05-04

Family

ID=6394353

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90121949A Expired - Lifetime EP0429983B1 (fr) 1989-11-29 1990-11-16 Composition hydro- et oléophobante

Country Status (4)

Country Link
US (1) US5164252A (fr)
EP (1) EP0429983B1 (fr)
JP (1) JPH03172337A (fr)
DE (2) DE3939341A1 (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5509939A (en) * 1989-12-29 1996-04-23 E. I. Du Pont De Nemours And Company Soil-release process
DE4039193A1 (de) * 1990-12-08 1992-06-11 Bayer Ag In wasser dispergierbare, elektrolytstabile polyetherester-modifizierte polyurethanionomere
US6309752B1 (en) 1991-04-02 2001-10-30 3M Innovative Properties Company Substrate having high initial water repellency and a laundry durable water repellency
KR100214319B1 (ko) * 1991-04-02 1999-08-02 스프레이그 로버트 월터 불소-효율이 우수한 발유 및 발수 조성물
JP2608195B2 (ja) * 1991-06-24 1997-05-07 セントラル硝子株式会社 熱可塑性ウレタン樹脂組成物
US5403514A (en) * 1991-10-07 1995-04-04 Canon Kabushiki Kaisha Solvent composition and water-repellent/oil-repellent composition using the same
JP2660312B2 (ja) * 1992-05-29 1997-10-08 ヘキスト合成株式会社 含フッ素系水性撥水撥油組成物
DE69424173T2 (de) * 1994-11-24 2000-09-28 Minnesota Mining & Mfg Carbodiimide-Verbindungen und dauerhafte wasserabweisende Zusammensetzungen, die diese Verbindungen enthalten
US7268179B2 (en) * 1997-02-03 2007-09-11 Cytonix Corporation Hydrophobic coating compositions, articles coated with said compositions, and processes for manufacturing same
US5853894A (en) * 1997-02-03 1998-12-29 Cytonix Corporation Laboratory vessel having hydrophobic coating and process for manufacturing same
US8653213B2 (en) 1997-02-03 2014-02-18 Cytonix, Llc Hydrophobic coating compositions and articles coated with said compositions
US6495624B1 (en) * 1997-02-03 2002-12-17 Cytonix Corporation Hydrophobic coating compositions, articles coated with said compositions, and processes for manufacturing same
EP0985741A1 (fr) * 1998-09-07 2000-03-15 The Procter & Gamble Company Traitements par plasma de décharge luminescente pour la fabrication de substrats super-hydrophobiques
DE19857106C2 (de) * 1998-12-10 2000-10-26 Heinz Neubaur Badebekleidung aus einem wasserabweisenden Stoff und Verfahren zu ihrer Herstellung
US6353051B1 (en) * 1999-03-10 2002-03-05 E. I. Du Pont De Nemours And Company Top coating for synthetic leathers
ITVA20000017A1 (it) * 2000-06-08 2001-12-08 Lamberti Spa Dispersioni acquose di copolimeri uretano-acrilici e loro impiego come agenti di finissaggio.
DE10120989A1 (de) * 2001-04-25 2002-11-07 Inst Polymerforschung Dresden Hydrophobe permanente Beschichtungen auf Substraten und Verfahren zu ihrer Herstellung
US6479605B1 (en) 2001-05-15 2002-11-12 E. I. Du Pont De Nemours And Company High-durability, low-yellowing repellent for textiles
DE10211549B9 (de) * 2002-03-15 2004-11-25 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen auf Basis von Wasser und/oder organischen Lösemitteln und deren Anwendung als Appretur auf Flächengebilden
DE10325094B4 (de) * 2003-06-03 2006-02-16 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen für die öl- und wasserabweisende Ausrüstung von Flächengebilden und deren Anwendung
US20090155600A1 (en) * 2005-09-21 2009-06-18 Daikin Industries, Ltd. Treatment for paper and method for treatment of paper
US8202579B2 (en) * 2008-03-31 2012-06-19 Cooley Group Holdings, Inc. Water-resistant fabrics and methods of preparation thereof
WO2016184877A1 (fr) * 2015-05-18 2016-11-24 Teijin Aramid Gmbh Surface textile à apprêt hydrophobe et son procédé de production

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CH416670D (fr) * 1969-03-20
US3763078A (en) * 1970-11-30 1973-10-02 Warnaco Inc Wear resistant garments and method and composition for production thereof
US3949124A (en) * 1974-07-12 1976-04-06 Hca-Martin, Inc. Method for treating textile materials and textile materials treated in such a way, and textile treating compositions
JPS58214586A (ja) * 1983-05-09 1983-12-13 カネボウ株式会社 繊維構造物の加工方法
DE3407362A1 (de) * 1984-02-29 1985-08-29 Bayer Ag, 5090 Leverkusen Waessrige dispersionen von pfropfpolymerisaten oder -copolymerisaten, ein verfahren zu ihrer herstellung und ihre verwendung als hydrophobierungs- und oleophobierungsmittel fuer textilien
DE3438563A1 (de) * 1984-10-20 1986-04-24 Bayer Ag, 5090 Leverkusen Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier
DE3523856A1 (de) * 1985-07-04 1987-01-08 Bayer Ag Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier

Also Published As

Publication number Publication date
EP0429983A3 (en) 1991-10-23
DE59005615D1 (de) 1994-06-09
US5164252A (en) 1992-11-17
DE3939341A1 (de) 1991-06-06
EP0429983A2 (fr) 1991-06-05
JPH03172337A (ja) 1991-07-25

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