EP0196309A1 - Verfahren zur erzielung wasch- und reinigungsbeständiger textilausrüstungen mit reaktiven, perfluoralkylreste enthaltenden (co)polymeren und bzw. oder vorkondensaten. - Google Patents
Verfahren zur erzielung wasch- und reinigungsbeständiger textilausrüstungen mit reaktiven, perfluoralkylreste enthaltenden (co)polymeren und bzw. oder vorkondensaten.Info
- Publication number
- EP0196309A1 EP0196309A1 EP85904458A EP85904458A EP0196309A1 EP 0196309 A1 EP0196309 A1 EP 0196309A1 EP 85904458 A EP85904458 A EP 85904458A EP 85904458 A EP85904458 A EP 85904458A EP 0196309 A1 EP0196309 A1 EP 0196309A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- blocked
- groups
- compounds
- molecular weight
- nco 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
Links
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 the production of washable and cleaning-resistant textile finishes by impregnation with conventional reactive (per) fluoroalkyl radical-containing (co) polymers and / or precondensates which contain OH or OR groups as reactive groups , where R is an alkyl radical having 1 to 3 carbon atoms, in aqueous dispersion and final heating, the dispersions containing compounds containing NCO groups (low molecular weight polyurethane with isocyanate groups and / or polyisocyanates) and having a molecular weight of at least 450 have, and / or contain a polyisocyanate mixture based on diphenylmethane in blocked form.
- NCO groups low molecular weight polyurethane with isocyanate groups and / or polyisocyanates
- These finishes can be carried out in combination with known finishing agents, ethylolated compounds being mentioned above all, but also diisocyanates. Disadvantageous 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, co-polymers containing perfluoroalkyl groups 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 the embodiments of this method specified in the subclaims.
- the reactive, perfluoroalkyl group-containing (co) polymers which contain OH or OR groups as reactive groups, in which R is an alkyl radical having 1 to 3 C atoms, are well known to the person skilled in the art (see, for example, DE-AS 1 419 505) o
- copolymers based on vinyl esters, in particular vinyl acetate and acrylic acid esters, in particular butyl acrylate.
- Comonomers which can be used are a wide variety of compounds, such as other acrylates, for example ethyl, methyl or 2-ethylhexyl acrylate, ethylene, styrene, acrylic id and acrylonitrile, which also contain small amounts of monomers containing carboxyl groups, for example itaconic acid and (meth) Acrylic acid, or monomers with several double bonds, for example butanediol diacrylate, can be copolymerized.
- These (co) polymers contain monomers containing customary perfluoroalkyl groups, these monomers also being the main component.
- the perfluoroalkyl group-containing (co) polymeric 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 are incorporated into the copolymer.
- comonomers containing OH groups for example hydroxyalkyl (meth) acrylates, such as 2-hydroxyethyl or 2-hydroxypropyl acrylate, are also 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 polymer as a whole. 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) polymers.
- these are the customary methylolmelamines or methylolureas which are optionally etherified with C 1 to C 3 alcohols and which 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 examples which may be mentioned are free OH groups containing R f polyurethanes.
- the term reactive (R) group-containing (co) polymers should therefore be interpreted broadly. Low molecular weight polyurethanes are suitable as compounds containing NCO groups.
- 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.
- 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 there are suitable, in particular, trimethylolpropane, '1, 3,5-hexanetriol, glycerol, Pentaaerythrit, but also P opylenglykol, hexylene glycol, or D-Lethylenglykol into consideration.
- 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 of no particular importance.
- the compounds containing NCO groups are also polyisocyanates with a molecular weight of at least 450, in particular at least 600, within the scope of the process according to the invention Blocking described below can be used.
- polyisocyanates are known. Examples include: trimeric isophorone diisocyanate or trimeric hexamethylene-1, 6-diisocyanate or DESMODUR RF (Bayer AG, Leverkusen).
- the selected compounds containing selected NCO groups 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, acetic acetic esters and other known substances, but preferably C 2 to C 8 alkanone oximes, in particular butanone oxime (see e.g. EP-OS 107 838).
- the blocked compounds containing NCO groups can be split up in the heat, so that in turn there are ready-to-react compounds.
- 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. If necessary, the cleavage can be reduced by adding catalysts, e.g. Sn alkyl compounds are accelerated.
- the blocked low molecular weight polyurethane or the blocked polyisocyanate are used to achieve the wash and (chemical) cleaning-resistant textile equipment as so-called extenders, substances that improve oil and water repellency and allow a reduction in the amount of the compounds containing fluoroalkyl radicals. 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 not considered for cost reasons.
- 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.
- a special embodiment of the emulsion preparation is required when using melamine precondensates as reactive R f precondensates. If such are used, the compounds containing blocked NCO groups must not be used alone in order to obtain liquors which are stable for several hours, but only together with a further known water-insoluble textile auxiliary in the solvent, if appropriate with slightly increased Temperature, dissolved, then, as is known, this solution is stirred into an emulsifier / water mixture (the commercially available products can be used as emulsifiers) and then turbinated in and then the mixture obtained is subjected to high-pressure homogenization.
- an emulsifier / water mixture the commercially available products can be used as emulsifiers
- 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.
- other conventional textile auxiliaries can also be used in the process according to the invention, the addition of which can take place already during the production of compounds (see above), but of course also only subsequently , can also be used.
- 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 is familiar to the person skilled in the art. 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 nonwoven 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, come too Textile materials are considered, which consist of mixtures of natural with synthetic fibers. 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 patterns are washed in the manner indicated. example 1
- a blue cotton twill (222 g / m) is padded with the following fleet:
- the fleet intake is 78%.
- the fabric treated in this way is then dried at 110 ° C. for 10 minutes and then condensed after 5 minutes at 150 ° C. (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.
- 20 g / l of a commercial extender based on fat-modified synthetic resin are also used in the liquor formulation.
- Example 1 is repeated using the perfluoroalkyl-modified methylolmelamine ether corresponding to Example 2 B of EP-OS 073 364, with comparable results. - 1 2 -
- 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 di-isocyanate (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 di-isocyanate
- 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. Then the solution medium distilled off in vacuo at 30 to 40 ° C. with stirring and the emulsion was adjusted to 25% by weight dry matter content with water.
- Oil repellent Water repellent oil repellent a) b) a) b)
- a cotton / polyester jacketed poplin (35/65; 200 g / m) is treated in the manner given in Example 1 (fleet absorption approx. 65%):
- Example 3 25 g / 1 of the emulsion of Example 1 of EP-OS 073 364, 6 g / 1 of the emulsion of the blocked polyurethane described in Example 3, which additionally contains 50 g of paraffin (melting point 52-54 ° 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)
- Polyurethanes Or Polyureas (AREA)
Description
Claims
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 |
---|---|---|---|
DE19843435618 DE3435618A1 (de) | 1984-09-28 | 1984-09-28 | Verfahren zur erzielung wasch- und reinigungsbestaendiger textilausruestungen mit reaktiven (co)polymeren bzw. vorkondensaten |
DE3435618 | 1984-09-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0196309A1 true EP0196309A1 (de) | 1986-10-08 |
EP0196309B1 EP0196309B1 (de) | 1988-03-16 |
Family
ID=6246589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85904458A Expired EP0196309B1 (de) | 1984-09-28 | 1985-09-17 | Verfahren zur erzielung wasch- und reinigungsbeständiger textilausrüstungen mit reaktiven, perfluoralkylreste enthaltenden (co)polymeren und bzw. oder vorkondensaten |
Country Status (7)
Country | Link |
---|---|
US (1) | US4834764A (de) |
EP (1) | EP0196309B1 (de) |
JP (1) | JPS62500311A (de) |
KR (1) | KR920009256B1 (de) |
DE (2) | DE3435618A1 (de) |
ES (1) | ES8801006A1 (de) |
WO (1) | WO1986002115A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5372731A (en) * | 1992-03-12 | 1994-12-13 | Bayer Aktiengesellschaft | Composition and process for the finishing of textiles |
Families Citing this family (29)
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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 |
US5753568A (en) * | 1993-04-28 | 1998-05-19 | Komatsu Seiren Co., Ltd. | Moisture-permeable, waterproof fabric and its production process |
WO1994025663A1 (en) * | 1993-04-28 | 1994-11-10 | Komatsu Seiren Co., Ltd. | Moisture-permeable waterproof fabric and process for producing the same |
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 |
DE59812738D1 (de) | 1998-12-22 | 2005-05-19 | Ciba Sc Pfersee Gmbh | Wässrige Dispersionen für die Textilveredlung |
JP4613420B2 (ja) | 1999-03-29 | 2011-01-19 | 旭硝子株式会社 | 水分散型撥水撥油剤組成物 |
ITMI991303A1 (it) * | 1999-06-11 | 2000-12-11 | Ausimont Spa | Oligouretani fluorurati |
EP1088867A1 (de) | 1999-09-30 | 2001-04-04 | Ciba Spezialitätenchemie Pfersee GmbH | Zusammensetzungen für die öl- und wasserabweisende Ausrüstung von Fasermaterialien |
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 |
EP1387858A1 (de) * | 2001-05-07 | 2004-02-11 | Dow Global Technologies Inc. | Energiehärtbares addukt enthaltend eine fluorgruppe und daraus hergestellte beschichtungen |
EP1264863A1 (de) * | 2001-06-08 | 2002-12-11 | Ciba Spezialitätenchemie Pfersee GmbH | Zusammensetzungen mit Polysiloxanen und weiteren Polymeren |
DE10139126A1 (de) | 2001-08-09 | 2003-02-20 | Ciba Sc Pfersee Gmbh | Zusammensetzungen aus Polysiloxanen, Fluorpolymeren und Extendern |
CN1315903C (zh) * | 2001-12-19 | 2007-05-16 | 3M创新有限公司 | 给纤维质基材提供斥水性的含水组合物 |
EP1496073A1 (de) | 2003-07-08 | 2005-01-12 | Ciba Spezialitätenchemie Pfersee GmbH | Extender für die Behandlung von Fasermaterialien |
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 |
JP5392081B2 (ja) * | 2007-07-20 | 2014-01-22 | ダイキン工業株式会社 | 撥アルコール性および汚れ脱離性を有する含フッ素繊維加工剤 |
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 |
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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 |
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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 |
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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 |
-
1984
- 1984-09-28 DE DE19843435618 patent/DE3435618A1/de not_active Withdrawn
-
1985
- 1985-09-17 WO PCT/EP1985/000478 patent/WO1986002115A1/de active IP Right Grant
- 1985-09-17 EP EP85904458A patent/EP0196309B1/de not_active Expired
- 1985-09-17 DE DE8585904458T patent/DE3561895D1/de not_active Expired
- 1985-09-17 JP JP60504048A patent/JPS62500311A/ja active Pending
- 1985-09-17 KR KR1019860700310A patent/KR920009256B1/ko not_active IP Right Cessation
- 1985-09-26 ES ES547313A patent/ES8801006A1/es not_active Expired
-
1987
- 1987-11-20 US US07/124,339 patent/US4834764A/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO8602115A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5372731A (en) * | 1992-03-12 | 1994-12-13 | Bayer Aktiengesellschaft | Composition and process for the finishing of textiles |
Also Published As
Publication number | Publication date |
---|---|
US4834764A (en) | 1989-05-30 |
EP0196309B1 (de) | 1988-03-16 |
JPS62500311A (ja) | 1987-02-05 |
ES547313A0 (es) | 1987-12-01 |
KR880700124A (ko) | 1988-02-15 |
WO1986002115A1 (en) | 1986-04-10 |
DE3435618A1 (de) | 1986-04-10 |
KR920009256B1 (ko) | 1992-10-15 |
DE3561895D1 (en) | 1988-04-21 |
ES8801006A1 (es) | 1987-12-01 |
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