EP0429983A2 - Composition hydro- et oléophobante - Google Patents

Composition hydro- et oléophobante Download PDF

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Publication number
EP0429983A2
EP0429983A2 EP90121949A EP90121949A EP0429983A2 EP 0429983 A2 EP0429983 A2 EP 0429983A2 EP 90121949 A EP90121949 A EP 90121949A EP 90121949 A EP90121949 A EP 90121949A EP 0429983 A2 EP0429983 A2 EP 0429983A2
Authority
EP
European Patent Office
Prior art keywords
component
carbon atoms
agent according
hydrocarbon radical
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.)
Granted
Application number
EP90121949A
Other languages
German (de)
English (en)
Other versions
EP0429983B1 (fr
EP0429983A3 (en
Inventor
Wolfgang Dr. Henning
Walter Dr. Meckel
Thomas Dr. Münzmay
Wilfried Kortmann
Peter Selinger
Peter Nussbaum
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
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Filing date
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
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
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated 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
    • Y10T442/2164—Coating or impregnation specified as water repellent
    • Y10T442/2172—Also 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 based on methylol compounds are used to better fix the fluorine products and also to improve the dimensional stability of the textile substrates.
  • 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).
  • 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.
  • Suitable polyurethane components B) are known and are described, for example, in the following patents:
  • Such structural components are e.g. in the form of aliphatic dihydroxy compounds with aliphatic substituents which have at least 10 carbon atoms, described in DE-A 24 00 490.
  • 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 optionally 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 present as 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 covers, 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 mixture of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate is mixed with a solution of a mixture of 1-methyl-1-phospha-2-cyclopentene-1-oxide and 1-methyl-1-phospha-3-cyclopentene-1-oxide carbodiimidized in N-methylpyrrolidone.
  • NCO value 20.6%
  • 1,4-butanediol and acetone are added.
  • the NCO value has dropped to 0%.
  • stearic acid is added and the reaction is brought to an acid number of 0 for 40 minutes.
  • Phobianssflotten are made from these components, which contain different amounts of the components depending on the textile fiber substrate.
  • 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 equipped goods were checked using the following method:
  • the grade for oil repellency corresponds to the highest numbered test liquid that does not wet the fiber material within 30 seconds:
  • Component I claimed according to the invention gives this increase even when used, based on solid substance, of 1.5 g / l, while component III, which is not in accordance with the invention, is only effective at 10 g / l.
  • 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 claimed according to the invention improves the washing resistance of fluorine finishes in such a way that the phobia values are retained even after 5 machine washes, while the finishes without extender or with component III drop significantly.
  • a colored 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 claimed 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 at 140 ° C for 3 minutes:
  • component II While no hydrophobic values are achieved with fluorine component II, the addition of component I claimed according to the invention achieves very good irrigation values. Component III achieves only a slight improvement over the textile goods that are only equipped with component II.

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)
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
DE3939341A DE3939341A1 (de) 1989-11-29 1989-11-29 Hydrophobierungs- und oleophobierungsmittel
DE3939341 1989-11-29

Publications (3)

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

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0490150A2 (fr) * 1990-12-08 1992-06-17 Bayer Ag Ionomères de polyuréthane modifiés par des groupes polyétherester dispersables à l'eau et stables aux électrolytes
WO1992017636A1 (fr) * 1991-04-02 1992-10-15 Minnesota Mining And Manufacturing Company Compositions hydrophobes et oleophobes utilisant efficacement le fluor
EP0572269A1 (fr) * 1992-05-29 1993-12-01 Hoechst Gosei K.K. Composition aqueuse contenant du fluor, ayant des propriétés oléophobes et hydrophobes
US6309752B1 (en) 1991-04-02 2001-10-30 3M Innovative Properties Company Substrate having high initial water repellency and a laundry durable water repellency
WO2003078725A1 (fr) * 2002-03-15 2003-09-25 Rudolf Gmbh & Co. Kg Chemische Fabrik Preparations a base d'eau et/ou de solvants organiques et leur utilisation comme appret sur des produits plats
WO2004106623A1 (fr) * 2003-06-03 2004-12-09 Rudolf Gmbh & Co. Kg Preparations pour l'appret oleofuge et hydrofuge de structures et leur utilisation

Families Citing this family (17)

* 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
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
DE69424173T2 (de) * 1994-11-24 2000-09-28 Minnesota Mining & Mfg Carbodiimide-Verbindungen und dauerhafte wasserabweisende Zusammensetzungen, die diese Verbindungen enthalten
US6495624B1 (en) 1997-02-03 2002-12-17 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
US7268179B2 (en) 1997-02-03 2007-09-11 Cytonix Corporation Hydrophobic coating compositions, articles coated with said compositions, and processes for manufacturing same
US8653213B2 (en) 1997-02-03 2014-02-18 Cytonix, Llc Hydrophobic coating compositions and articles coated with said compositions
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
JP4656148B2 (ja) * 2005-09-21 2011-03-23 ダイキン工業株式会社 紙用処理剤および紙の処理方法
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

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2039746A5 (fr) * 1969-03-20 1971-01-15 Rimar Spa
US3763078A (en) * 1970-11-30 1973-10-02 Warnaco Inc Wear resistant garments and method and composition for production thereof
FR2277927A1 (fr) * 1974-07-12 1976-02-06 Martin Inc H C A Traitement de matieres textiles, notamment traitement antistatique
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
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2039746A5 (fr) * 1969-03-20 1971-01-15 Rimar Spa
US3763078A (en) * 1970-11-30 1973-10-02 Warnaco Inc Wear resistant garments and method and composition for production thereof
FR2277927A1 (fr) * 1974-07-12 1976-02-06 Martin Inc H C A Traitement de matieres textiles, notamment traitement antistatique
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
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 100, no. 24, 11 Juni 1984 Columbus, Ohio, USA "FINISHING OF FABRICS" & JP-A-58 214 586 (KANEBO)13-12-1983 ref. no. 193499J *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0490150A2 (fr) * 1990-12-08 1992-06-17 Bayer Ag Ionomères de polyuréthane modifiés par des groupes polyétherester dispersables à l'eau et stables aux électrolytes
EP0490150A3 (en) * 1990-12-08 1993-03-10 Bayer Ag Water-dispersible polyetherester-modified polyurethane ionomers having stability against electrolytes
WO1992017636A1 (fr) * 1991-04-02 1992-10-15 Minnesota Mining And Manufacturing Company Compositions hydrophobes et oleophobes utilisant efficacement le fluor
US6309752B1 (en) 1991-04-02 2001-10-30 3M Innovative Properties Company Substrate having high initial water repellency and a laundry durable water repellency
EP0572269A1 (fr) * 1992-05-29 1993-12-01 Hoechst Gosei K.K. Composition aqueuse contenant du fluor, ayant des propriétés oléophobes et hydrophobes
US5346949A (en) * 1992-05-29 1994-09-13 Hoechst Gosei K.K. Fluorine containing aqueous composition having water repellent and oil repellent properties
WO2003078725A1 (fr) * 2002-03-15 2003-09-25 Rudolf Gmbh & Co. Kg Chemische Fabrik Preparations a base d'eau et/ou de solvants organiques et leur utilisation comme appret sur des produits plats
US7354458B2 (en) 2002-03-15 2008-04-08 Rudolf Gmbh & Co., Kg, Chemische Fabrik Preparations based on water and/or organic solvents and their use as a finish on flat materials
WO2004106623A1 (fr) * 2003-06-03 2004-12-09 Rudolf Gmbh & Co. Kg Preparations pour l'appret oleofuge et hydrofuge de structures et leur utilisation
DE10325094A1 (de) * 2003-06-03 2004-12-30 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen für die öl- und wasserabweisende Ausrüstung von Flächengebilden und deren Anwendung
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
US8231802B2 (en) 2003-06-03 2012-07-31 Rudolf Gmbh Preparations for making planar structures oil-repellent and water-repellent, and use thereof

Also Published As

Publication number Publication date
JPH03172337A (ja) 1991-07-25
EP0429983B1 (fr) 1994-05-04
DE59005615D1 (de) 1994-06-09
DE3939341A1 (de) 1991-06-06
EP0429983A3 (en) 1991-10-23
US5164252A (en) 1992-11-17

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