DE1220383B - Verfahren zum UEberziehen oder Schlichten von Fasermaterialien - Google Patents
Verfahren zum UEberziehen oder Schlichten von FasermaterialienInfo
- Publication number
- DE1220383B DE1220383B DEM44876A DEM0044876A DE1220383B DE 1220383 B DE1220383 B DE 1220383B DE M44876 A DEM44876 A DE M44876A DE M0044876 A DEM0044876 A DE M0044876A DE 1220383 B DE1220383 B DE 1220383B
- Authority
- DE
- Germany
- Prior art keywords
- coating
- fiber materials
- fabric
- oil
- water
- 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.)
- Pending
Links
- 238000000576 coating method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 239000011248 coating agent Substances 0.000 title claims description 6
- 239000002657 fibrous material Substances 0.000 title claims description 4
- 238000004513 sizing Methods 0.000 title claims description 3
- 239000006185 dispersion Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 229920005570 flexible polymer Polymers 0.000 claims 2
- RRRXPPIDPYTNJG-UHFFFAOYSA-N perfluorooctanesulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RRRXPPIDPYTNJG-UHFFFAOYSA-N 0.000 claims 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 239000000835 fiber Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- MRPUVAKBXDBGJQ-UHFFFAOYSA-N methyl 2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)F MRPUVAKBXDBGJQ-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- -1 yarns Substances 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
- D06M15/21—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- 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
- Y10T442/2189—Fluorocarbon containing
Description
BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. Cl.:
D06m
Deutsche 10.: 8 k - 3
Nummer: 1220 383
Aktenzeichen: M 44876IV c/8 k
Anmeldetag: 22. Januar 1957
Auslegetag: 7. Juli 1966
Die Erfindung betrifft ein Verfahren zum Überziehen und Schlichten von Fasermaterialien mit einem
nach Patent 1106 960 hergestellten Polymerisat von Fluorkohlenstoffestern, nach dem Gewebe sowohl
wasserabstoßend als auch widerstandsfähig gegen Absorption und Verschmutzen durch ölige und fettige
Substanzen gemacht werden können. Die Erfindung umfaßt Gewebe und andere Gegenstände, die mit
diesen Polymerisaten zugerichtet worden sind.
Die Herstellung der verwendeten Polymerisate ist in dem Patent 1106 960 beschrieben und beansprucht.
Es ist nun gefunden worden, Gegenstände, insbesondere Gewebe, mit biegsamen Homopolymerisaten
von Fluorkohlenstoffestern nach Patent 1106960 hergestellt, zu überziehen bzw. zu schlichten, so daß sie
sowohl wasser- als auch ölabstoßend gemacht werden.
Überzüge aus den genannten Polymerisaten können aus einer Lösung oder einer Emulsion aufgebracht
werden, um so fest gebundene Oberflächenüberzüge oder -appreturen auf natürlichen oder synthetischen ao
Geweben, Fasern, Garnen, Tuch, Papier, Cellulosefilmen, Leder, Gesteinsmaterial, Glas und auf keramischen
Gegenständen und Metallen herzustellen. Wegen der Orientierung der Polymermoleküle liefern
die Fluorkohlenstoffketten eine inerte fluorkohlenstoffartige äußere Oberfläche, die sowohl hydrophob
als auch oleophob ist. Auf der Oberfläche abgelagerte Wasser- oder Öltropfen bleiben dort oder laufen eher
ab, als daß sie sich auf der Oberfläche ausbreiten oder diese benetzen.
Die Behandlung von Textilgeweben z. B. kann so durchgeführt werden, daß das behandelte Gewebe
einen nicht wahrnehmbaren Überzug auf den Fasern trägt, der die Durchlässigkeit, Biegsamkeit, den Griff,
die Festigkeit, das Aussehen oder die Farbe nicht wesentlich beeinflußt. Der Überzug ist fest an die
Fasern gebunden. Das Gewebe kann wiederholt gewaschen oder chemisch gereinigt werden, ohne daß
es seine Wasser- oder Ölfestigkeit verliert. Dies ermöglicht die Herstellung von Geweben, die gegen
Absorption und Verschmutzung nicht nur durch Wasser und wäßrige Substanzen, sondern auch durch
ölige und fettige Stoffe widerstandsfähig sind. Derartige Substanzen werden nicht absorbiert und lassen
sich leicht durch Waschen oder Trockenreinigen entfernen. Es können z. B. Gewebe behandelt werden, die
als Polster für Kraftwagen, als Arbeitskleidung, Sportkleidung, Mäntel, Jacken und Decken und
Teppiche verwendet werden sollen und die besonders der Verschmutzung durch ölige oder fettige Substanzen
ausgesetzt sind.
Verschmutzende Stoffe auf Wasser- und Ölgrund-Verfahren zum Überziehen oder Schlichten von
Fasermaterialien
Anmelder:
Minnesota Mining and Manufacturing Company, St. Paul, Minn. (V. St. A.)
Vertreter:
Dr.-Ing. H. Ruschke, Patentanwalt, Berlin 33, Auguste-Viktoria-Str. 65
Als Erfinder benannt:
Arthur Harold Ahlbrecht,
Harvey Allem Brown, Washington, Minn.; Samuel Smith, Ramsey, Minn. (V. St. A.)
Beanspruchte Priorität:
V. St. ν. Amerika vom 23. Januar 1956 (560 900)
V. St. ν. Amerika vom 23. Januar 1956 (560 900)
lage (wie Tinte, süße Getränke, Kaffee, Salatöl, Bratenfett und Haaröl) können von dem behandelten
Gewebe durch Ablöschen und Reiben ohne Hinterbleiben eines Flecks entfernt werden. Die erfindungsgemäße
Ausrüstung beeinträchtigt nicht den Griff, das Aussehen, die Festigkeit oder die Durchlässigkeit
des Gewebes, macht es aber hydrophob und oleophob zugleich.
Wegen der Unlöslichkeit der Polymerisate in Wasser, Kohlenwasserstoffen und gewöhnlichen organischen
Lösungsmitteln ist die Gewebeappretur mit derartigen Substanzen nur schwer zu entfernen, und das appretierte
Gewebe kann daher gewaschen und gereinigt werden, ohne daß die Wirksamkeit der Appretur
nachläßt.
Geeignete Lösungsmittel für das Polymerisat sind fluorhaltige Lösungsmittel, wie Xylolhexafluorid,
Benzotrifluorid, Methylperfluorbutyrat, Trichlorfluormethan und l,l,2-TricUor-l,2,2-trifluoräthan.
Verschiedenartige durchlässige Papiere, die in die Behandlungslösung getaucht und getrocknet worden
waren, wurden in hohem Maße wasser- und ölabstoßend.
Das Polymerisat kann aber auch aus flüchtigen Lösungen mittels einer Aerosolbombe oder -spritzkanne
aufgebracht werden.
Das folgende Beispiel erläutert die Ausführung des erfindungsgemäßen Verfahrens.
609 588/374
Eine Latex-Appretierlösung wird durch Verdünnen der gemäß Beispiel 1 des Patents 1106 960 erhaltenen
wäßrigen Latexdispersipn des Acrylatpolymerisats mit Was.ser auf einen .Gehalt an Latexfestsubstanz von
1 Gewichtsprozent hergestellt. Proben verschiedenartiger Gewebe werden in die Lösung eingetaucht,
durch Quetschwalzen geschickt, um überschüssige Lösung zu entfernen, und 10 Minuten lang durch
Erwärmen auf 14O0C getrocknet. Auf die Oberfläche
der behandelten Gewebe gebrachte Wasser- und Öltropfen bleiben in allen Fällen unverändert, ohne sich
auf der Oberfläche auszubreiten oder diese zu benetzen, woraus die hydrophoben und oleophoben Eigenschaften
des Polymerisats auf den Faseroberfiächen und die Ausschaltung der Kapillarwirkung deutlich
wird. Die untersuchten Gewebe sind: köperartiger Baumwollstoff, Wollstoff, Stoff aus Polyamidfasern
und ein Gewebe aus einer Mischung von 55% Polyesterfasern und 45% Kammgarnfasern.
Das hohe Wasserabstoßungsvermögen, das dem Polyester-Kammgarn-Gewebe verliehen wurde, ging
aus einer »Sprühprobe« hervor (Standard Untersuchungsverfahren Nr. 22 bis 52, veröffentlicht 1952
im Technical Manual und Yearbook of the American Association of Textile Chemists and Colorists,
Bd. XXViri, S. 136), bei der der Wert 100 ermittelt wurde, der bei einer Abstufung von 0 bis 100 der
größtmögliche Wert ist. Es wurde gefunden, daß das energischste. Verfahren zur Untersuchung der Ölabstoßung
darin besteht, die Widerstandsfähigkeit gegenüber der Durchdringung mit Lösungen von
Mineralöl in Heptan festzustellen, da diese das Gewebe besser durchdringen können als Mineralöl allein.
Je größer der Mengenanteil an Heptan ist, um so schneller erfolgt die Durchdringung. Bei diesen
behandelten Geweben wurde gefunden, daß die Wider
standsfähigkeit gegenüber Durchdringung bei Verwendung einer Lösung von weißem Mineralöl, die
Volumprozent Heptan enthielt, mindestens 3 Minuten betrug, woraus die ausgezeichnete Ölfestigkeit
hervorgeht.
Die Behandlung verschiedenartiger Gewebe und Papiere mit Polymerisaten, die gemäß anderen Beispielen
des Patents 1106 960 hergestellt wurden, liefert Ergebm'sse, die denen im zuvor angegebenen
ίο Beispiel beschriebenen entsprechen, wobei ein hohes
Maß an Widerstandfähigkeit gegenüber Wasser und Öl und eine stark hydrophobe und oleophobe Oberfläche
erhalten wurde.
Claims (2)
1. Verfahren zum Überziehen oder Schlichten von Fasermaterialien, dadurch gekennzeichnet,
daß die Materialien mit Lösungen zo oder wäßrigen Dispersionen eines biegsamen Polymerisats mit wiederkehrenden Einheiten
CH8
das nach Patent 1106 960 hergestellt worden ist, in an sich bekannter Weise behandelt werden.
2. Verfahren nach Anspruch 1 dadurch gekennzeichnet, daß man als biegsame Polymerisate
solche der Acrylsäureester von N-Propyl-N-äthanolperfluoroctansulfonamid
oder von N-Butyl-N-äthanolperfluoroctansulfonamid
mit anderen Monomeren verwendet.
In Betracht gezogene ältere Patente:
Deutsches Patent Nr. 1106 960.
Deutsches Patent Nr. 1106 960.
609 588/374 6.66 ® Bundesdruckerei Berlin
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US560900A US2803615A (en) | 1956-01-23 | 1956-01-23 | Fluorocarbon acrylate and methacrylate esters and polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1220383B true DE1220383B (de) | 1966-07-07 |
Family
ID=24239820
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM32991A Pending DE1106960B (de) | 1956-01-23 | 1957-01-22 | Verfahren zur Herstellung von Polymerisaten |
| DEM44876A Pending DE1220383B (de) | 1956-01-23 | 1957-01-22 | Verfahren zum UEberziehen oder Schlichten von Fasermaterialien |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM32991A Pending DE1106960B (de) | 1956-01-23 | 1957-01-22 | Verfahren zur Herstellung von Polymerisaten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2803615A (de) |
| CH (1) | CH357872A (de) |
| DE (2) | DE1106960B (de) |
| FR (1) | FR1172081A (de) |
| GB (1) | GB857689A (de) |
| SE (2) | SE300310B (de) |
Families Citing this family (251)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995542A (en) * | 1957-05-20 | 1961-08-08 | Minnesota Mining & Mfg | Fluorocarbon acrylic-type amides and polymers |
| DE1794282A1 (de) * | 1957-06-11 | 1971-11-25 | Minnesota Mining & Mfg | Verwendung von hoehermolekularen Kondensationsprodukten als Oberflaechenbehandlungsmittel |
| US3011950A (en) * | 1959-05-19 | 1961-12-05 | Colgate Palmolive Co | Liquid composition containing discrete gaseous bodies |
| US3016318A (en) * | 1959-07-15 | 1962-01-09 | Goodyear Tire & Rubber | Fabric covered cellular cushioning article and manufacture thereof |
| DE1102406B (de) * | 1959-08-01 | 1961-03-16 | Bayer Ag | Verfahren zur Herstellung von Polymerisaten mit sauren Eigenschaften |
| NL254721A (de) * | 1959-08-10 | |||
| US3087905A (en) * | 1960-05-03 | 1963-04-30 | American Cyanamid Co | Durable fluorochemical-melamine resin textile finish |
| US3061473A (en) * | 1960-06-23 | 1962-10-30 | Stevens & Co Inc J P | Process of and composition for producing improved textile materials having oil and water repellent and antistatic properties |
| US3100180A (en) * | 1960-12-19 | 1963-08-06 | Minnesota Mining & Mfg | Dermal protective compositions |
| US3034925A (en) * | 1961-02-02 | 1962-05-15 | Marco Carlo G De | Water-resistant and oil-resistant fibrous substances, and processes therefor |
| BE635437A (de) * | 1961-05-03 | |||
| US3256231A (en) * | 1961-05-03 | 1966-06-14 | Du Pont | Polymeric water and oil repellents |
| US3255131A (en) * | 1961-05-10 | 1966-06-07 | Minnesota Mining & Mfg | Fluorochemical-containing varnishes |
| US3108015A (en) * | 1961-06-15 | 1963-10-22 | Lever Brothers Ltd | Anti-stick pan coating |
| US3150000A (en) * | 1961-06-24 | 1964-09-22 | Pfersee Chem Fab | Method and means for treating textiles |
| DE1272298B (de) * | 1962-02-14 | 1968-07-11 | Pfersee Chem Fab | Verfahren zur Herstellung von N-Fluoralkyl-N'-aethylenharnstoffen |
| US3377198A (en) * | 1962-08-28 | 1968-04-09 | Pfersee Chem Fab | Oil and water repellent surfaces containing fluorinated metal chelates |
| US3227073A (en) * | 1962-11-19 | 1966-01-04 | John J Reich | Ink repellent inking pad and cover for stencil printing devices |
| US3304198A (en) * | 1963-10-28 | 1967-02-14 | Allied Chem | Process for preparing oleophobic and hydrophobic fiber and fiber prepared therewith |
| US3326713A (en) * | 1964-01-29 | 1967-06-20 | Burlington Industries Inc | Breathable and waterproof coated fabric and process of making same |
| US3293767A (en) * | 1964-03-24 | 1966-12-27 | Time Inc | Felt driers for paper-making machinery |
| US3330812A (en) * | 1964-04-27 | 1967-07-11 | Minnesota Mining & Mfg | Vinyl polymers containing perfluorocarbon groups and acyl halide groups |
| US3365329A (en) * | 1964-06-30 | 1968-01-23 | Du Pont | Process of treating fabrics to render them oil- and water-repellent |
| US3384628A (en) * | 1964-09-21 | 1968-05-21 | Agriculture Usa | Fluorinated ester compounds and use thereof |
| US3356628A (en) * | 1964-12-01 | 1967-12-05 | Minnesota Mining & Mfg | Copolymers of perfluoro acrylates and hydroxy alkyl acrylates |
| GB1123829A (en) * | 1964-12-01 | 1968-08-14 | Minnesota Mining & Mfg | Fluorine containing copolymers |
| US3318852A (en) * | 1965-04-05 | 1967-05-09 | Minnesota Mining & Mfg | Fluorine-containing polymers |
| US3385812A (en) * | 1965-06-25 | 1968-05-28 | Du Pont | Finishing composition comprising a fluorochemical and a polyorganosiloxane |
| US3407183A (en) * | 1965-09-07 | 1968-10-22 | Allied Chem | Acrylate and methacrylate esters and polymers thereof |
| US3341497A (en) * | 1966-01-21 | 1967-09-12 | Minnesota Mining & Mfg | Organic solvent soluble perfluorocarbon copolymers |
| US3468697A (en) * | 1966-03-02 | 1969-09-23 | Colgate Palmolive Co | Method of treating textile articles which are usually laundered |
| US3458348A (en) * | 1966-05-31 | 1969-07-29 | Minnesota Mining & Mfg | Transparent coated optical element |
| US3480664A (en) * | 1966-06-07 | 1969-11-25 | Us Agriculture | 2,3-bis(heptafluoroisopropoxy)-r-propyl acrylate |
| GB1175420A (en) * | 1967-02-15 | 1969-12-23 | Minnesota Mining & Mfg | Fluorine-Containing Polymers |
| US3528849A (en) * | 1967-05-22 | 1970-09-15 | Hooker Chemical Corp | Method for imparting oil and water repellency to textile materials |
| US3486911A (en) * | 1967-08-21 | 1969-12-30 | Sun Chemical Corp | Textile treating compositions and textiles treated therewith |
| US3476583A (en) * | 1967-10-30 | 1969-11-04 | Colgate Palmolive Co | Method for rendering fibrous material oil and water repellent |
| US3628997A (en) * | 1967-10-30 | 1971-12-21 | Colgate Palmolive Co | Method and means for treating fibrous materials and articles produced thereby |
| US3525634A (en) * | 1967-11-28 | 1970-08-25 | Colgate Palmolive Co | Method for treating fibrous substrates |
| US3540923A (en) * | 1967-12-15 | 1970-11-17 | Dow Chemical Co | Method for treating textile materials with a fluorocarbon resin |
| US3540924A (en) * | 1967-12-15 | 1970-11-17 | Dow Chemical Co | Method for treating textile materials with a fluorocarbon resin |
| US4066746A (en) * | 1968-05-01 | 1978-01-03 | Lever Brothers Company | Reducing the drying time of hair with fluorine-containing vinyl polymers |
| US3816229A (en) * | 1972-01-14 | 1974-06-11 | Minnesota Mining & Mfg | Plural coated pile fabric |
| CH587381B5 (de) * | 1972-03-06 | 1977-04-29 | Minnesota Mining & Mfg | |
| US4032495A (en) * | 1972-03-10 | 1977-06-28 | Produits Chimiques Ugine Kuhlmann | Water-repellent and oil-repellent compositions based on fluorine compound |
| US3997500A (en) * | 1972-04-10 | 1976-12-14 | The Dow Chemical Company | Process and composition for water- and oil-proofing textiles |
| US3923715A (en) * | 1973-07-26 | 1975-12-02 | Du Pont | Aqueous dispersions of perfluoroalkyl esters and vinyl polymers for treating textiles |
| US3976588A (en) * | 1975-01-14 | 1976-08-24 | Center For New Product Development | Detergents providing faster drying of cleansed substrates |
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-
1956
- 1956-01-23 US US560900A patent/US2803615A/en not_active Expired - Lifetime
-
1957
- 1957-01-22 DE DEM32991A patent/DE1106960B/de active Pending
- 1957-01-22 SE SE619/57A patent/SE300310B/xx unknown
- 1957-01-22 DE DEM44876A patent/DE1220383B/de active Pending
- 1957-01-22 FR FR1172081D patent/FR1172081A/fr not_active Expired
- 1957-01-23 CH CH357872D patent/CH357872A/de unknown
- 1957-01-23 GB GB2464/57A patent/GB857689A/en not_active Expired
-
1965
- 1965-11-26 SE SE15306/65A patent/SE310162B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1172081A (fr) | 1959-02-05 |
| SE300310B (de) | 1968-04-22 |
| GB857689A (en) | 1961-01-04 |
| SE310162B (de) | 1969-04-21 |
| CH357872A (de) | 1961-10-31 |
| DE1106960B (de) | 1961-05-18 |
| US2803615A (en) | 1957-08-20 |
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