EP0429983A2 - Composition hydro- et oléophobante - Google Patents
Composition hydro- et oléophobante Download PDFInfo
- 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
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
- D06M15/564—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)
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992017636A1 (fr) * | 1991-04-02 | 1992-10-15 | Minnesota Mining And Manufacturing Company | Compositions hydrophobes et oleophobes utilisant efficacement le fluor |
| EP0490150A3 (en) * | 1990-12-08 | 1993-03-10 | Bayer Ag | Water-dispersible polyetherester-modified polyurethane ionomers having stability against electrolytes |
| 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)
| 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 |
| EP0713863B1 (fr) * | 1994-11-24 | 2000-04-26 | Minnesota Mining And Manufacturing Company | Dérivés de carbodiimide et compositions hydrofuges durables qui les contiennent |
| 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 |
| US6495624B1 (en) | 1997-02-03 | 2002-12-17 | 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 |
| 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 |
| US10683606B2 (en) * | 2015-05-18 | 2020-06-16 | Teijin Aramid Gmbh | Textile fabric having a water-repellent finish and method for producing the same |
Family Cites Families (6)
| 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 |
| 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 DE DE59005615T patent/DE59005615D1/de not_active Expired - Fee Related
- 1990-11-16 EP EP90121949A patent/EP0429983B1/fr not_active Expired - Lifetime
- 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
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5164252A (en) | 1992-11-17 |
| EP0429983B1 (fr) | 1994-05-04 |
| EP0429983A3 (en) | 1991-10-23 |
| DE59005615D1 (de) | 1994-06-09 |
| DE3939341A1 (de) | 1991-06-06 |
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