EP0429983B1 - Composition hydro- et oléophobante - Google Patents
Composition hydro- et oléophobante Download PDFInfo
- 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
- Authority
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 11
- 239000004753 textile Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000006185 dispersion Substances 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 6
- 150000007945 N-acyl ureas Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- -1 methylol compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000005871 repellent Substances 0.000 description 6
- 206010034912 Phobia Diseases 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 208000019899 phobic disease Diseases 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 230000002262 irrigation Effects 0.000 description 3
- 238000003973 irrigation Methods 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 2
- MQLQAXIVFGHSDE-UHFFFAOYSA-N 1-methyl-2,5-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CC=CC1 MQLQAXIVFGHSDE-UHFFFAOYSA-N 0.000 description 2
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 2
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- JQALNNOQTGZTJZ-UHFFFAOYSA-N [[4,6-bis[bis(methoxymethyl)amino]-1,3,5-triazin-2-yl]-(methoxymethyl)amino]methanol Chemical compound COCN(CO)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 JQALNNOQTGZTJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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 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)
- Composition conférant le caractère hydrophobe et oléophobe, contenantA) un polymère porteur de groupes perfluoralkyle etB) un polyuréthanne, caractérisée en ce que le polyuréthanne a subi une modification cationique et contient des composants structuraux contenant des groupes acylurée de formuleR 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.
- 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.
- 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.
- 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.
- Procédé d'apprêtage de matières textiles, caractérisé en ce qu'on utilise des compositions suivant les revendications 1 à 4.
- 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.
- Corps textiles apprêtés avec des compositions suivant les revendications 1 à 4.
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)
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 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
1989
- 1989-11-29 DE DE3939341A patent/DE3939341A1/de not_active Withdrawn
-
1990
- 1990-11-16 EP EP90121949A patent/EP0429983B1/fr not_active Expired - Lifetime
- 1990-11-16 DE DE59005615T patent/DE59005615D1/de not_active Expired - Fee Related
- 1990-11-21 US US07/616,554 patent/US5164252A/en not_active Expired - Fee Related
- 1990-11-27 JP JP2321383A patent/JPH03172337A/ja active Pending
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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