EP0196309B1 - Procede d'obtention d'un appret textile resistant au lavage et au nettoyage compose d'au moins (co)polymeres et/ou des precondensats reactifs contenant des radicaux perfluoriques - Google Patents

Procede d'obtention d'un appret textile resistant au lavage et au nettoyage compose d'au moins (co)polymeres et/ou des precondensats reactifs contenant des radicaux perfluoriques Download PDF

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Publication number
EP0196309B1
EP0196309B1 EP85904458A EP85904458A EP0196309B1 EP 0196309 B1 EP0196309 B1 EP 0196309B1 EP 85904458 A EP85904458 A EP 85904458A EP 85904458 A EP85904458 A EP 85904458A EP 0196309 B1 EP0196309 B1 EP 0196309B1
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EP
European Patent Office
Prior art keywords
groups
blocked
process according
compounds containing
nco
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
Application number
EP85904458A
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German (de)
English (en)
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EP0196309A1 (fr
Inventor
Hans Deiner
Bernhard Sandner
Franz Mosch
Willy Bernheim
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Chemische Fabrik Pfersee GmbH
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Chemische Fabrik Pfersee GmbH
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Publication date
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Priority to AT85904458T priority Critical patent/ATE33048T1/de
Publication of EP0196309A1 publication Critical patent/EP0196309A1/fr
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Publication of EP0196309B1 publication Critical patent/EP0196309B1/fr
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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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/437—Amino-aldehyde resins containing fluorine
    • 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
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D06M15/295—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing fluorine
    • 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
    • D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine

Definitions

  • the present invention describes a process for achieving washable and cleaning-resistant textile finishes by impregnation with conventional reactive (co) polymers containing perfluoroalkyl radicals and / or precondensates which contain OH or OR groups as reactive groups, where R is an alkyl radical with 1 to 3 carbon atoms, in aqueous dispersion and final heating, the dispersions containing NCO groups (low molecular weight polyurethanes with isocyanate groups and / or polyisocyanates) which have a molecular weight of at least 450 and / or a polyisocyanate mixture based on diphenylmethane in blocked Form included.
  • NCO groups low molecular weight polyurethanes with isocyanate groups and / or polyisocyanates
  • R f perfluoroalkyl radical with at least 4, in particular 6 to 14, C. Atoms.
  • These finishes can be used in combination with known finishing agents, methylolated compounds in particular, but also diisocyanates, being mentioned.
  • the disadvantage here is that the diisocyanates have to be prepared from solvents (aqueous emulsions are not stable) and the improvement in cleaning resistance achieved is insufficient.
  • washing and cleaning-resistant textile finishes with reactive, perfluoroalkyl group-containing (co) polymers and / or precondensates are obtained from aqueous dispersion when selected compounds containing NCO groups are used in blocked form.
  • the present invention thus relates to the method described in claim 1 and embodiments of this method specified in the subclaims.
  • the reactive, perfluoroalkyl groups contain the (co) polymers which contain OH or OR groups as reactive groups, in which R denotes an alkyl radical having 1 to 3 C atoms, are sufficiently known to the person skilled in the art (see, for example, DE -AS 1 419 505).
  • copolymers based on vinyl esters, in particular vinyl acetate and acrylic acid esters, in particular butyl acrylate.
  • Comonomers come from a wide variety of compounds, such as other acrylates, e.g. As ethyl, methyl or 2-ethylhexyl acrylate, ethylene, styrene, acrylamide and acrylonitrile into consideration, which also contain small amounts of carboxyl-containing monomers, for. B. itaconic acid and (meth) acrylic acid, or monomers with several double bonds, e.g. B. butanediol diacrylate, copolymerized.
  • These (co) polymers contain customary monomers containing perfluoroalkyl groups, which may also be the main component.
  • the perfluoroalkyl group-containing (co) polymers containing N-methylol or N-methylol (C 1 to C 3 alkyl) ether groups used as reactive groups are those which are obtained by using methylolated and optionally etherified (meth) acrylamides or allyl carbamates be built into the copolymer.
  • OH group-containing comonomers e.g. B. hydroxyalkyl (meth) acrylates, such as 2-hydroxyethyl or 2-hydroxypropyl acrylate, very suitable.
  • the monomers with the reactive groups are generally polymerized in amounts of 2 to 20, in particular 2.5 to 12,% by weight, based on the total polymer. These copolymers are prepared in a known manner by emulsion copolymerization in an aqueous medium.
  • Pre-condensates containing reactive perfluoroalkyl groups are used as reactive compounds instead of or together with the (co) polymeric.
  • these are the customary methylolmelamines or methylolureas, which are optionally etherified with C 1 to C 3 alcohols and are present in a form modified with perfluoroalkyl groups.
  • a typical representative of this group of compounds is described in EP-OS 073 364.
  • R f polyurethanes containing free OH groups may be mentioned as examples.
  • reactive (co) polymers containing R f groups should therefore be interpreted broadly.
  • Low molecular weight polyurethanes are suitable as compounds containing NCO groups. These polyurethanes are - and this is well known to the person skilled in the art - by reacting polyvalent, aliphatic, cycloaliphatic, araliphatic and aromatic polyisocyanates, such as, for example, hexamethylene-1,6-diisocyanate, the various isomers of tolylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate and the like with low molecular weight compounds with at least 2, preferably at least 3 OH groups.
  • low molecular weight polyols are trimethylolpropane, 1,3,5-hexanetriol, glycerin, pentaerythritol, but also propylene glycol, hexylene glycol or diethylene glycol.
  • Other low molecular weight polyhydroxy compounds such as triethanolamine, are also suitable.
  • the molecular weight of the polyhydroxy compounds which can be used is in the range from 62 to about 400, in particular up to about 250.
  • the production of the low molecular weight polyurethanes which have a molecular weight of at least 450, in particular at least 600, is known per se.
  • the polyhydroxy compounds mentioned are reacted with an excess of polyisocyanates.
  • the equivalent ratio of OH to NCO groups is at least 1: 1.3, in particular 1: 1.5 to 2.5.
  • the upper limit is variable, but connections with a ratio of 1: over 6.0 are no longer particularly important.
  • polyisocyanates with a molecular weight of at least 450, in particular at least 600, are also included as compounds containing NCO groups
  • the method according to the invention can be used after the blocking described below.
  • Such polyisocyanates are known. Examples include: trimeric isophorone diisocyanate or trimeric hexamethylene-1, 6-diisocyanate or DESMODUR RF (Bayer AG, Leverkusen).
  • a polyisocyanate mixture based on diphenylmethane is also suitable.
  • the selected compounds containing NCO groups described are not used as such, but rather in blocked form.
  • the blocking takes place by reacting these compounds with approximately stoichiometric amounts of blocking agent. After the reaction, the free NCO groups have practically completely disappeared.
  • Suitable blocking agents are phenols, malonic esters, acetoacetic esters and other known substances, but preferably C 2 -C 8 -alkanone oximes, in particular butanone oxime (see, for example, EP-OS 107 838).
  • the compounds containing blocked NCO groups can be broken down in the heat, so that again ready-to-react compounds are present.
  • the compounds blocked with C 2- to C 8-alkanone oximes, in particular butanone oxime, can be broken down again at relatively low temperatures, which is why these blocking agents are preferred.
  • the cleavage by adding catalysts, for. B. Sn alkyl compounds are accelerated.
  • the blocked low molecular weight polyurethane or the blocked polyisocyanate are used to achieve the washing and (chemical) cleaning-resistant textile equipment as so-called extenders, i.e. substances that improve oil and water repellency and thereby reduce the amount of compounds containing fluoroalkyl residues.
  • extenders i.e. substances that improve oil and water repellency and thereby reduce the amount of compounds containing fluoroalkyl residues.
  • Amounts of 3 to 25% by weight, in particular 7 to 17% by weight, based on 100% reactive perfluoroalkyl group-containing (co) polymer and / or precondensate, are completely sufficient, so that higher amounts are sufficient Cost reasons are out of the question.
  • the compounds containing blocked NCO groups are added to the finishing liquor in emulsified form.
  • These emulsions are prepared in a known manner using known emulsifiers and are ultimately in solvent-free form. These production processes are known to the person skilled in the art and it is not necessary to go into them in more detail.
  • the blocked NCO group-containing compounds must not be dissolved in the solvent alone, but only together with another known water-insoluble textile auxiliary, if appropriate at a slightly elevated temperature, in order to achieve fleets which are stable for several hours, only then, as is known, this solution stirred into an emulsifier / water mixture (commercially available products can be used as emulsifiers) and then subjected to high-pressure homogenization, and the mixture obtained is then subjected to high-pressure homogenization. Finally, as usual, the solvent is distilled off under reduced pressure at a slightly elevated temperature and the emulsion is adjusted to the desired dry substance content with water.
  • Such additives include customary crease and softening agents, flame retardants, oleophobicizing agents, water repellents, finishing agents and others. Of course, it is also appropriate, if necessary, to use known hardening agents.
  • the method according to the invention is used to impregnate all types of textiles from an aqueous medium.
  • the water is of course used in different quantities, depending on whether impregnation, i.e. impregnation of the material, is carried out by padding, spraying, splashing or the like.
  • impregnation is a very common finishing method, which the skilled worker is familiar with. These methods therefore require no special explanation and reference can be made to the known literature. Further details can be found in the examples. It should be noted, however, that the use of organic solvents is not necessary in the process according to the invention, but is carried out without solvents.
  • the method according to the invention is suitable for impregnating textiles of all kinds, be it in the form of woven, knitted or non-woven fabrics. These can be made both from natural fibers, such as cellulose or keratin fibers, and from synthetic fibers, such as polyacrylonitrile, polyamide, polyvinyl alcohol or polyester. Of course, textile materials that consist of mixtures of natural and synthetic fibers are also suitable. It should be emphasized that even slightly adjusted fabrics, such as taffeta or slightly adjusted poplin fabrics, can be finished using the method according to the invention. This is important, for example, for rain protective clothing such as anoraks and the like.
  • the oil repellency is tested using the method as specified in AATCC 118-1972.
  • the dry cleaning is carried out in a liquor ratio of 1:10 (sample weight to liquor volume) for 15 minutes, the tetrachlorethylene used being renewed for each cleaning. The samples are washed in the manner specified in each case.
  • the fleet intake is 78%.
  • the fabric treated in this way is then dried at 110 ° C. for 10 minutes and then condensed at 150 ° C. for 5 minutes (equipment A).
  • equipment B is carried out in the same way, but the emulsion is produced in the absence of the blocked low-molecular-weight polyurethane, but with the liquor batch 20 g / 1 of a commercially available extender based on fat-modified synthetic resin (see, for example, DE-PS 12 33 874, Examples 1 and 4) can also be used.
  • a commercially available extender based on fat-modified synthetic resin see, for example, DE-PS 12 33 874, Examples 1 and 4
  • Example 1 is repeated using the perfluoroalkyl-modified methylol melamine ether according to Example 2 B of EP-OS 073 364, with comparable results.
  • polyisocyanates are blocked in succession with butanone oxime in the manner described in Example 1: trimeric isophorone diisocyanate (A), DESMODUR RF from Bayer (B), trimeric hexamethylene-1,6-diisocyanate (C), hexamethylene-1,6-diisocyanate (D) and naphthylene-1,5-diisocyanate (E).
  • A trimeric isophorone diisocyanate
  • DESMODUR RF from Bayer
  • C trimeric hexamethylene-1,6-diisocyanate
  • D hexamethylene-1,6-diisocyanate
  • E naphthylene-1,5-diisocyanate
  • methyl ethyl ketone 100 g of the blocked polyurethane prepared as described below are added at about 60 ° C. and heated to 60 ° C.
  • the liquid consists of two immiscible layers. It is turbinated in a solution of 10 g of the emulsifier described in Example 1 in 290 g of water at a temperature of 60 ° C. and then homogenized on a high-pressure homogenizing machine, likewise at a temperature of 60 ° C.
  • the solvent is then distilled off in vacuo at 30 to 40 ° C. with stirring and the emulsion is adjusted to 25% by weight dry matter content with water.

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

Abstract

Un procédé d'obtention d'un revêtement pour textiles résistant au lavage et au nettoyage consiste à imprégner les textiles avec des (co)polymères réactifs conventionnels, contenant des radicaux perfluoriques, et/ou des précondensats dans une dispersion aqueuse suivie de réchauffement. La dispersion comprend des liaisons contenant des groupes NCO ayant un poids moléculaire d'au moins 450, et un mélange de polyisocyanates à base de diphénylmethane sous forme bloquée. Ce procédé permet de protéger des textiles avec un revêtement imperméable à l'eau et à l'huile, et ayant une très bonne résistance au lavage et au nettoyage.

Claims (11)

1. Procédé pour l'obtention d'apprêts pour textiles résistant au lavage et au nettoyage par imprégnation, en dispersion aqueuse, à l'aide de (co)polymères et/ou de précondensats réactifs classiques renfermant des restes perfluoroalkyles avec au moins 4 atomes de C, qui contiennent respectivement des groupes OH, ou OR en tant que groupes réactifs, R représentant un reste alkyle avec 1 à 3 atomes de carbone et par chauffage final, caractérisé en ce que les dispersions contiennent des composés porteurs de groupes NCO possédant une masse moléculaire d'au moins 450 et/ou un mélange polyisocyanate à base de diphénylméthane, entièrement sous forme bloquée.
2. Procédé selon la revendication 1, caractérisé en ce que les dispersions contiennent, en tant que composés porteurs de groupes NCO, ceux des composés sous forme bloquée possédant une masse moléculaire d'au moins 600.
3. Procédé selon les revendications 1 à 2, caractérisé en ce que les composés bloqués contenant des groupes NCO sont mis en oeuvre en des quantités de 3 à 25 % en poids par rapport au (co)polymère et/ou au précondensat réactif contenant des groupes perfluoroalkyles à 100 %.
4. Procédé selon les revendications 1 à 3, caractérisé en ce que les composés bloqués contenant des groupes NCO sont mis en oeuvre en des quantités de 7 à 17 % en poids, par rapport au (co)polymère et/ou au précondensat réactif contenant des groupes perfluoroalkyles à 100 %.
5. Procédé selon les revendications 1 à 4, caractérisé en ce que les composés bloqués contenant des groupes NCO sont mis en oeuvre sous forme émulsionnée, exempte de solvent.
6. Procédé selon la revendication 5, caractérisé en ce que les composés bloqués contenant des groupes NCO sont émulsionnés conjointement avec un adjuvant pour textiles insoluble dans l'eau connu et mis en oeuvre sous cette forme avec des précondensats de mélamine-Rf, Rf représentant un reste perfluoroalkyle avec 6 à 14 atomes de C.
7. Procédé selon les revendications 1 à 6, caractérisé en ce que des polyuréthanes bloqués de bas poids moléculaire sont utilisés en tant que composés bloqués contenant des groupes NCO.
8. Procédé selon la revendication 7, caractérisé en ce que les polyuréthanes bloqués de bas poids moléculaire ont été obtenus par réaction de composés polyols de bas poids moléculaire et de polyisocyanates dans un rapport d'équivalents d'au moins 1 : 1,3 groupes OH à groupes isocyanates et que les groupes NCO ont été ultérieurement bloqués.
9. Procédé selon la revendication 8, caractérisé en ce que le rapport des équivalents de groupes OH aux groupes isocyanates s'élève à 1 : 1,5 à 2,5.
10. Procédé selon les revendications 1 à 6, caractérisé en ce que des polyisocyanates bloqués sont utilisés en tant que composés bloqués contenant des groupes NCO.
11. Procédé selon les revendications 1 à 10, caractérisé en ce qu'on utilise simultanément des adjuvants pour textiles courants.
EP85904458A 1984-09-28 1985-09-17 Procede d'obtention d'un appret textile resistant au lavage et au nettoyage compose d'au moins (co)polymeres et/ou des precondensats reactifs contenant des radicaux perfluoriques Expired EP0196309B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85904458T ATE33048T1 (de) 1984-09-28 1985-09-17 Verfahren zur erzielung wasch- und reinigungsbestaendiger textilausruestungen mit reaktiven, perfluoralkylreste enthaltenden (co)polymeren und bzw. oder vorkondensaten.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3435618 1984-09-28
DE19843435618 DE3435618A1 (de) 1984-09-28 1984-09-28 Verfahren zur erzielung wasch- und reinigungsbestaendiger textilausruestungen mit reaktiven (co)polymeren bzw. vorkondensaten

Publications (2)

Publication Number Publication Date
EP0196309A1 EP0196309A1 (fr) 1986-10-08
EP0196309B1 true EP0196309B1 (fr) 1988-03-16

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EP85904458A Expired EP0196309B1 (fr) 1984-09-28 1985-09-17 Procede d'obtention d'un appret textile resistant au lavage et au nettoyage compose d'au moins (co)polymeres et/ou des precondensats reactifs contenant des radicaux perfluoriques

Country Status (7)

Country Link
US (1) US4834764A (fr)
EP (1) EP0196309B1 (fr)
JP (1) JPS62500311A (fr)
KR (1) KR920009256B1 (fr)
DE (2) DE3435618A1 (fr)
ES (1) ES8801006A1 (fr)
WO (1) WO1986002115A1 (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3737753A1 (de) * 1987-11-06 1989-06-15 Pfersee Chem Fab Waessriges ausruestungsmittel und verfahren zur weichen hydrophob/oleophob-behandlung von fasermaterialien
DE3831452A1 (de) * 1988-01-29 1990-03-22 Pfersee Chem Fab Verwendung von modifizierten, perfluoraliphatische gruppen enthaltenden polyurethanen zusammen mit textilhilfsmitteln zur oel- und wasserabweisenden ausruestung von textilmaterialien
US5258458A (en) * 1991-02-28 1993-11-02 Minnesota Mining And Manufacturing Company Composition for providing oil and water repellency
US6309752B1 (en) 1991-04-02 2001-10-30 3M Innovative Properties Company Substrate having high initial water repellency and a laundry durable water repellency
US5508370A (en) * 1991-10-17 1996-04-16 Bayer Aktiengesellschaft Water-dispersible blocked isocyanates, method of manufacture, and use thereof
DE4207851A1 (de) * 1992-03-12 1993-09-16 Bayer Ag Mittel und verfahren zur ausruestung von textilien
US5753568A (en) * 1993-04-28 1998-05-19 Komatsu Seiren Co., Ltd. Moisture-permeable, waterproof fabric and its production process
EP0648889B1 (fr) * 1993-04-28 1998-08-19 Komatsu Seiren Co., Ltd. Tissu etanche permeable a l'humidite et son procede de production
US5466770A (en) * 1994-05-26 1995-11-14 Minnesota Mining And Manufacturing Company Fluorine-efficient oil- and water-repellent compositions
DE69424173T2 (de) * 1994-11-24 2000-09-28 Minnesota Mining & Mfg Carbodiimide-Verbindungen und dauerhafte wasserabweisende Zusammensetzungen, die diese Verbindungen enthalten
US5768761A (en) * 1997-02-13 1998-06-23 Milliken Research Corporation Chair seat frame system
DE19715416A1 (de) * 1997-04-14 1998-10-15 Ciba Sc Pfersee Gmbh Umsetzungsprodukte von Isocyanaten mit Hydroxyverbindungen für die Textilveredelung
JPH11279527A (ja) * 1997-06-30 1999-10-12 Asahi Glass Co Ltd 防汚加工剤組成物、その製造方法およびそれを用いた被処理物
ATE293135T1 (de) 1998-12-22 2005-04-15 Ciba Sc Pfersee Gmbh Wässrige dispersionen für die textilveredlung
CA2331755C (fr) * 1999-03-29 2009-06-09 Asahi Glass Company, Limited Compose d'eau et d'oleophobe hydrofuge
ITMI991303A1 (it) * 1999-06-11 2000-12-11 Ausimont Spa Oligouretani fluorurati
EP1088867A1 (fr) 1999-09-30 2001-04-04 Ciba Spezialitätenchemie Pfersee GmbH Compositions pour le finissage oléo-et hydrorépulisif de matériaux textiles
US6451717B1 (en) 1999-12-14 2002-09-17 E. I. Du Pont De Nemours And Company Highly durable oil/water repellents for textiles
DE10016610A1 (de) 2000-04-04 2001-10-11 Ciba Sc Pfersee Gmbh Silikonhaltige Zusammensetzung für die Behandlung von Wollematerialien
CN1296403C (zh) * 2001-05-07 2007-01-24 陶氏环球技术公司 包含氟基团的可能量固化加合物和由此得到的涂料
EP1264863A1 (fr) * 2001-06-08 2002-12-11 Ciba Spezialitätenchemie Pfersee GmbH Compositions contenant des polysiloxanes et d'autres polymères
DE10139126A1 (de) 2001-08-09 2003-02-20 Ciba Sc Pfersee Gmbh Zusammensetzungen aus Polysiloxanen, Fluorpolymeren und Extendern
AU2002231369A1 (en) * 2001-12-19 2004-07-22 3M Innovative Properties Company Aqueous composition for rendering fibrous substrates water repellent
EP1496073A1 (fr) 2003-07-08 2005-01-12 Ciba Spezialitätenchemie Pfersee GmbH Extenseurs pour le traitement de matériaux fibreux
US20050215145A1 (en) * 2004-03-25 2005-09-29 Guerrero Cesar H Liquid resistant articles and method of producing the same
US20070265412A1 (en) * 2006-05-09 2007-11-15 3M Innovative Properties Company Extenders for fluorochemical treatment of fibrous substrates
US8828098B2 (en) * 2006-12-18 2014-09-09 3M Innovative Properties Company Extenders for fluorochemical treatment of fibrous substrates
EP2177550B1 (fr) * 2007-07-20 2014-11-05 Daikin Industries, Ltd. Agent de traitement de fibres contenant du fluor présentant des propriétés de résistance à l'alcool et de libération des salissures
DE102013224140A1 (de) * 2013-11-26 2015-05-28 Rudolf Gmbh Ausrüstungsmittel mit blockierten Polyisocyanaten
DE102017202827A1 (de) 2017-02-22 2018-08-23 Cht R. Beitlich Gmbh Wässrige Formulierung zur Verbesserung der Abriebbeständigkeit

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1468295A1 (de) * 1960-09-02 1969-05-29 Minnesota Mining & Mfg Perfluoralkylgruppen enthaltende Urethane und Verfahren zu deren Herstellung
FR1316488A (fr) * 1961-09-01 1963-02-01 Minnesota Mining & Mfg Compositions fluorocarburées
FR1383076A (fr) * 1963-11-12 1964-12-24 Pechiney Saint Gobain Alumine active de grande porosité
US3356628A (en) * 1964-12-01 1967-12-05 Minnesota Mining & Mfg Copolymers of perfluoro acrylates and hydroxy alkyl acrylates
US3503915A (en) * 1966-08-29 1970-03-31 Minnesota Mining & Mfg Fabric treating composition and treated fabric
US3506661A (en) * 1966-09-20 1970-04-14 Pfersee Chem Fab Manufacture of melamine derivatives and products resulting therefrom
GB1157796A (en) * 1966-10-12 1969-07-09 Pfersee Chem Fab The Preparation of Melamine Derivatives Modified by Fatty Acid Groups
US3528849A (en) * 1967-05-22 1970-09-15 Hooker Chemical Corp Method for imparting oil and water repellency to textile materials
BE757123A (fr) * 1969-10-07 1971-03-16 Soltex Soc Civ Nouvelles compositions antistatiques pour matieres fibreuses ettextile
US3968066A (en) * 1974-04-18 1976-07-06 Ciba-Geigy Corporation Oil and water repellent textile composition containing a fluorochemical polyurethane resin and a quaternary ammonium salt
US4124553A (en) * 1975-12-05 1978-11-07 Commonwealth Scientific And Industrial Research Organization Method for the preparation of a composition containing polycarbamoyl sulphonates from polyisocyanates
JPS5335098A (en) * 1976-09-09 1978-04-01 Toyo Boseki Treatment of fiber article
JPS5333251A (en) * 1976-09-09 1978-03-29 Nippon Synthetic Chem Ind Co Ltd:The Crosslinkable composition
JPS5365492A (en) * 1976-11-17 1978-06-10 Dainichiseika Color Chem Fiber treating agent
JPS5386899A (en) * 1976-12-29 1978-07-31 Toyo Boseki Treating of fiber article
US4240943A (en) * 1978-02-27 1980-12-23 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Textile finishing composition
JPS54139641A (en) * 1978-04-21 1979-10-30 Asahi Glass Co Ltd Water and oil repellent treatment
DE3133303A1 (de) * 1981-08-22 1983-03-03 Chemische Fabrik Pfersee Gmbh, 8900 Augsburg Verfahren zur herstellung von perfluoralkylreste enthaltenden kondensationsprodukten, die so hergestellten kondensationsprodukte und deren verwendung
JPS5834866A (ja) * 1981-08-27 1983-03-01 Dainippon Ink & Chem Inc ウレタン塗料用組成物
DE3239900A1 (de) * 1982-10-28 1984-05-03 Bayer Ag, 5090 Leverkusen Verlaufmittelhaltige polyurethan-high-solid-reaktivbeschichtungssysteme und ihre verwendung zur reaktivbeschichtung
DE3307420A1 (de) * 1983-03-03 1984-09-13 Bayer Ag, 5090 Leverkusen Textilausruestungsmittel
JPS60151378A (ja) * 1984-01-17 1985-08-09 大日本インキ化学工業株式会社 繊維織物素材用撥水撥油処理剤及び処理方法

Also Published As

Publication number Publication date
ES547313A0 (es) 1987-12-01
WO1986002115A1 (fr) 1986-04-10
EP0196309A1 (fr) 1986-10-08
KR920009256B1 (ko) 1992-10-15
ES8801006A1 (es) 1987-12-01
DE3561895D1 (en) 1988-04-21
DE3435618A1 (de) 1986-04-10
KR880700124A (ko) 1988-02-15
JPS62500311A (ja) 1987-02-05
US4834764A (en) 1989-05-30

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