US3147064A - Fluorinated ethers and derivatives - Google Patents
Fluorinated ethers and derivatives Download PDFInfo
- Publication number
- US3147064A US3147064A US79033459A US3147064A US 3147064 A US3147064 A US 3147064A US 79033459 A US79033459 A US 79033459A US 3147064 A US3147064 A US 3147064A
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- US
- United States
- Prior art keywords
- carbon atoms
- cloth
- methyl
- treated
- oil
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- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
- B23Q3/00—Devices holding, supporting, or positioning work or tools, of a kind normally removable from the machine
- B23Q3/02—Devices holding, supporting, or positioning work or tools, of a kind normally removable from the machine for mounting on a work-table, tool-slide, or analogous part
- B23Q3/06—Work-clamping means
- B23Q3/08—Work-clamping means other than mechanically-actuated
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/438—Sulfonamides ; Sulfamic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
- B23Q2703/00—Work clamping
- B23Q2703/02—Work clamping means
- B23Q2703/04—Work clamping means using fluid means or a vacuum
-
- 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
-
- 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
- Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
- Y10T442/2287—Fluorocarbon containing
Definitions
- This invention relates to halomethylethers and more particularly to certain new N-perfiuoroalkylsulfonamidoalkyl halomethylethers and quaternized derivatives thereof, and to a process for rendering textiles soil-resistant as well as oil and water repellent.
- novel halomethylethers of the invention conta n a halogen atom attached to a perfiuoroalkylsulfonamidoalkyl group through a labile oxymethylene radical.
- These halomethylethers are found to react w1th tertiary organic bases to form quaternary ammonium derivatives.
- the perfluoroalkyl group contains from about 6 to about 12 fully fluorinated carbon atoms, it has been found that these compounds can be employed as textile finishes, and particularly to treat cellulosic materials such as cotton to produce a chemically bonded water and 011 repellent finish material for such cellulosic materials.
- Another object of this invention is to provide agents by means of which cellulosic materials and particularly cotton fibers can be rendered lastingly oil and water repellent.
- a further object of this invention is to provide oil and water repellent cellulosic materials such as cotton cloth.
- Still another object of the invention is to provide a process for rendering cellulosic materials soilresistant.
- R,- is a perfluoroalkyl group containing 4 to 12 carbon atoms (providing the perfluorocarbon tail which has certain useful characteristics as set forth in US. Patent 2,803,656, R is an alkylene bridging group containing l to 12 carbon atoms, R is hydrogen or an alkyl group containing 1 to 6 carbon atoms and X is chlorine or bromine.
- Q represents a nitrogenous organic residue having the free valence attached to the nitrogen atom and three other valences attached to at least two carbon atoms, and bearing a positive charge.
- quaternary salt derivatives of the compounds of the invention can be applied to woven and non-woven fabrics as more fully described hereinafter to provide oil and water repellency with improved resistance to laundering.
- R R and R have the significance set forth above, and which are described and claimed in US. Patent No. 2,803,656, with formaldehyde and anhydrous hydrogen chloride or anhydrous hydrogen bromide.
- the resulting perfiuoroalkanesulfonamidoalkyl halomethyl ethers are waxy solids having softening points of from about 25 to about C.; that is, they vary in consistency from that of hard butter to that of beeswax or carnauba wax. When sufiiciently pure they are white, but as commonly obtained they are slightly yellowish in color. This does not affect their utility for quaternization, and special purification prior to quaternization is not necessary.
- the process for preparation of the halomethyl ethers is conveniently carried out by passing the selected anhydrous hydrogen halide in gaseous form into a solution of the alkanol and paraformaldehyde in an inert solvent such as toluene, benzene and the like, until there is substantially no further absorption of the hydrogen halide.
- Quaternization is conveniently eifected by dissolving the selected halomethyl compound in anhydrous ether or other solvert (such as toluene, benzene or dioxane) in which the quaternary salt is insoluble and adding the desired tertiary organic base, while heating at a temperature in the range of about 25 C. to 100 C.
- tertiary amines including trialkyl amines such as trimethylamine, tributylamine and tridodecylamine; alkarylamines such as dimethylaniline; and heterocyclic amines such as pyridine, picoline, lutidine, quinoline and the like are suitable.
- Pyridine is particularly preferred for convenience and economy in the formation of clothtreating agents as shown above.
- the quaternary derivatives of the compounds of the invention are employed for treating woven or non-woven fibrous materials including wool, cotton, rayon, acetate, nylon and the like textiles, or paper, leather, wood, felt and similar organic fibrous constructions, and particularly cellulosic materials, by applying the selected quaternary derivatives, in aqueous medium buffered to about pH 6, to the cloth, removing any excess, drying at a temperature in the range of about 40 to 100 C., and heating the dried material to about 100 to 140 C. for a period of the order of about 5 to 30 minutes to fix the finish. Thereafter the material is desirably treated with a mildly alkaline washing to remove any residual acidic material, and dried.
- the treatment may be followed by a simple aqueous wash before drying, if desired, although this may be omitted since subsequent laundering of the treated fabric accomplishes the same purpose.
- the treatment may be termed a finishing treatment, since it is most usefully applied after weaving, forming, dyeing, weighting, filling or the like have been carried out.
- the cloth so treated appears to contain residual combined fluorine, indicating that at least a portion of the treating agent has reacted in some fashion, probably through the hydroxyl groups present in the fiber, although this theory is not to be construed as limiting the invention.
- finishing treatment of the invention can be applied to resin-treated, wrinkle-resistant fabrics without adversely affecting the desirable non-wrinkling feature of such fabrics.
- compositions have furthermore been found to con fer oil and water-repellency on vitreous surfaces and the like, such as glass, including glass fibers.
- EXAMPLE 1 Anhydrous hydrogen chloride is passed through a solution of 155 parts of N-methyl-perfluorooctanesulfonamidohendecanol (prepared as described in Example 6 of US. Patent 2,803,656) in 320 parts of toluene containing 6.9 parts of paraformaldehyde, until no further absorption occurs and the reaction is complete. The solution is evaporated under reduced presure to remove toluene leaving the chloromethyl ether as a residue.
- N-methyl-ll-perfluorooctanesulfonamidohendecanoxymethyl chloride is a hard waxy solid which melts at about 50 C.
- the corresponding pyridinium salt is prepared therefrom by dissolving the above chloromethyl ether in about 300 parts of ether, adding 17.9 parts of pyridine and refluxing the solution for 1 hour. A precipitate of the quaternary salt forms and is collected, washed with ether and dried. N-rnethyl-l1-(perfiuorooctanesulfonamido)hendecanoxy 4 methyl pyridinium chloride thus prepared melts at about 93-108" C.
- the treating solution is prepared by warming sodium acetate trihydrate and the selected treating agent in water at the desired concentrations, which can range from about 0.1 to about 5 percent, at about 30 to 40 C. until solution is effected. It is to be noted that at higher concentration the solution tends to become mucilaginous and diffitficult to handle, resembling a colloidal dispersion.
- the cloth to be treated is soaked in the solution for 1 minute, removed and squeezed so that a weight of solution approximately equal to 75 to 125 percent of the weight of the cloth is retained. Under these conditions, the preferred concentration of treating solution ranges from about 0.5 to about 2 percent.
- the cloth is then dried for about 10 to 30 minutes at 40 to 100 C.
- alkaline agents such as dilute alkali metal hydroxides, bicarbonates, ammonium hydroxide and the like can be used instead of alkali metal carbonates.
- the effectiveness of the treatments is determined by means of tests for spray rating, oil repellency rating and visual estimation of soil repellency both before further treatment and after one or more cycles of laundering.
- laundering is accomplished by washing in a 1957 model automatic washing machine of the stationary tub type using a detergent under normal household procedures or by means of a standard 60 minute cycle in a Launder-O-Meter, using chip soap as specified in ASTM D-496.
- Oil repellency of the treated cloth is measured by a severe test in which its resistance to penetration by solutions of mineral oil in heptane is determined. (Higher proportions of heptane bring about quicker penetration.) A material wet by mineral oil alone in less than 3 minutes rates zero, if it is only wet after 3 minutes it rates fifty, while resistance to penetration by a mixture of equal volumes of heptane and mineral oil rates 100. The ratings for resistance for 3 minutes are as follows.
- Percent heptane Rating 0 50 drying, it is subjected to tests to determine oil and water repellency with the following results:
- Table II containing 1 percent of sodium acetate trihydrate by w./v. together with N-methyl-perfluorooctanesulfonamidohendecanoxymethyl pyridinium chloride in the concentrations indicated in Table III, and dried and cured under the conditions there set forth. After washing with a detergent (sodium lauryl sulfate), rinsing and drying, they are rated for oil and water repellency as well as dry soil resistance. Small portions of the fabric are removed and analyzed to determine the percentage of fluorine present.
- a detergent sodium lauryl sulfate
- Dry soil resistance simulates soil repellency of a material under especially exaggerated conditions.
- a control sample of untreated cloth and the treated sample to be tested are shaken together in a paper bag with about 2 ounces of a standard synthetic soil mixture having the composition described in the report of Salisbury et al., American Dyestuff Reporter, March 26, 1956, p. 199, then removed and sharply struck against a solid object to remove loosely adherent soil and compared visually with a similarly soiled untreated sample.
- the ratings are from to 3.
- Treating agent 1 Values low due to inhomogenolty 0f analytncal samples. 3 Not determined.
- the solution used for treating fabric as set forth above can also be applied to paper with slight modifications in procedure to avoid damaging the structure of the paper, which, as is well known, is weakened by treatment with water.
- the excess of treating solution is removed by permitting the paper to drip dry or by running the web between rolls, while drying and fixing are accomplished by heating the individual sheets or by hot-rollcalendering long strips or continuous rolls.
- the treated paper is oiland water-repellent.
- EXAMPLE 3 This example further illustrates the effectiveness of the process of this invention and variations within the scope of the process.
- Samples of kier-boiled standard cotton EXAMPLE 4 N methyl 5 perfluorooctanesulfonamidopentanoxymethyl pyridinium chloride is prepared as follows, using the general procedure described above. A mixture of 198 parts of the dry sodium salt of N-methyl perfluorooctanesulfonamide and 61.5 parts of 5-chloropentyl ace jeanss cloth are treated as described above with solutions 75 tate is stirred at about 120 to C. for 15 hours and then cooled.
- N-methyl-S-perfluorooctanesulfonamidopentyl acetate boils at about 140 C. to 145 C. under 0.4 mm. Hg pressure and melts at about 40 C.
- a mixture of 35 parts of the above N-methyl-S-perfluorooctanesulfonamidopentanol and 2 parts of paraformaldehyde in about 120 parts of toluene is treated with hydrogen chloride gas as described hereinabove until absorption ceases and the solution has become clear and homegeneous.
- the toluene is then removed under reduced pressure and the N-methyl-5-perfiuorooctanesulfonamidopentanoxymethyl chloride is obtained as a waxy residue.
- N methyl 5 perfluorooctanesulfonamidopentanoxymethyl pyridinium chloride is employed for treating kierboiled cotton jeans cloth as described above, using a 2 percent aqueous solution containing 1 percent of sodium acetate.
- the soaked cloth is dried for 30 minutes at 100 C. and then cured for 5 minutes at 135 C.
- the treated fabric has an oil rating of 100+ and a spray rating of 80; and contains 0.5 percent F. After laundering in the Launder-O-Meter, the oil rating is 100+, spray rating 70+ and there is still 0.48 percent F in the cloth.
- the dry soil rating both before and after laundering is +3, that is, visually estimated, the treated cloth is less than about one-half as readily soiled as an untreated sample of the cloth.
- N-butyl-8-perfluorododecanesulfonamidooctanol and N-hexyl-12-perfluorohexanesulfonamidododecanol there are produced N-butyl-S-perfiuorododecanesulfonamidooctanoxymethyl chloride and N-hexyl-12-perfluorohexanesulfonamidododecanoxymethyl chloride, from which are prepared, using tri-n-hexylamine in ether solution, the corresponding N-butyl-8-perfluorododecanesulfonamidooctanoxymethyl tri n hexylammonium chloride and N-hexyl-IZ-perfiuorohexanesulfonamidododecanoxymethyl tri n heXyl-ammonium chloride.
- R is perfluoroalkyl having 4 to 12 carbon atoms
- R is alkylene having 1 to 12 carbon atoms
- R is a member of the group consisting of hydrogen and alkyl having from 1 to 6 carbon atoms
- X is a halogen of the group consisting of chlorine and bromine.
- R is perfluoroalkyl having 4 to 12 carbon atoms
- R is alkylene having 1 to 12 carbon atoms
- R is a member of the group consisting of hydrogen and alkyl having from 1 to 6 carbon atoms
- Q is a nitrogenous organic residue selected from the group consisting of trialkylamino having up to 36 carbon atoms, alkaryl amino having up to 8 carbon atoms, pyridino, picolino, lutidino and quinolino
- X is a holgen of the group consisting of chlorine and bromine.
- Rf is a perfluoroalkyl group containing 4 to 12 carbon atoms
- R is an alkylene bridging radical containing 1 to 12 carbon atoms
- R is a member of the group consisting of hydrogen and alkyl radicals having from 1 to 6 carbon atoms; with formaldehyde and a member of the group consisting of anhydrous hydrogen chloride and anhydrous hydrogen bromide while maintaining the temperature in the range of from about 25 to C.
- a cellulosic fabric having oiland water-repellent properties finished with N-rnethyl-S-perfiuorooctanesulfonamidopentanoxymethyl pyridinium chloride.
- R is perfluoroalkyl having 4 to 12 carbon atoms
- R is alkylene having 1 to 12 carbon atoms
- R is a member of the group consisting of hydrogen and alkyl having from 1 to 6 carbon atoms
- X is a halogen of the group consisting of chlorine and bromine, in aqueous medium buffered to about pH 5.5 to 6.5, drying the treated fibrous material and heating the dried, treated material to about 9 100 to 140 C. for a period of the order of 5 to 30 minutes.
- Bi Rr-S 0zN-ROH,O omx wherein R, is perfluoroalkyl having 4 to 12 carbon atoms, R is alkylene having 1 to 12 carbon atoms, R is a member of the group consisting of hydrogen and alkyl having from 1 to 6 carbon atoms, and X is a halogen of the group consisting of chlorine and bromine; whereby the fabric contains residual combined fluorine and has oiland water-repellent properties.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US79033459 US3147064A (en) | 1959-02-02 | 1959-02-02 | Fluorinated ethers and derivatives |
GB281960A GB933056A (en) | 1959-02-02 | 1960-01-26 | Improvements in fluorinated ethers |
DEM44189A DE1150383B (de) | 1959-02-02 | 1960-02-01 | Verfahren zur Herstellung von quaternaeren Verbindungen von Perfluor-alkylsulfonamidoalkanohlalogen-methylaethern |
US180274A US3147004A (en) | 1959-02-02 | 1962-03-16 | Work securing clamp |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US79033459 US3147064A (en) | 1959-02-02 | 1959-02-02 | Fluorinated ethers and derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
US3147064A true US3147064A (en) | 1964-09-01 |
Family
ID=25150356
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US79033459 Expired - Lifetime US3147064A (en) | 1959-02-02 | 1959-02-02 | Fluorinated ethers and derivatives |
Country Status (3)
Country | Link |
---|---|
US (1) | US3147064A (de) |
DE (1) | DE1150383B (de) |
GB (1) | GB933056A (de) |
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3622590A (en) * | 1969-04-04 | 1971-11-23 | Fmc Corp | Certain perfluoroalkyl polyoxyalkylene quaternary ammonium salts and derivatives thereof |
US3734687A (en) * | 1969-04-04 | 1973-05-22 | Fmc Corp | A fabric finished with a fluorinated quarternized halomethyl ether |
USB378621I5 (de) * | 1971-06-07 | 1975-01-28 | ||
US3993745A (en) * | 1974-05-31 | 1976-11-23 | Alberto Culver Company | Perfluorinated compounds in hair treatment compositions |
US3993744A (en) * | 1974-05-31 | 1976-11-23 | Alberto Culver Company | Live human hair treatment compositions containing perfluorinated compounds |
US4013786A (en) * | 1974-05-31 | 1977-03-22 | Alberto Culver Company | Hair creme rinses and hair conditioners containing hydrophobic-lipophobic perfluorinated compounds |
US4176176A (en) * | 1974-05-31 | 1979-11-27 | Alberto-Culver Company | Hair shampoo and cleanser compositions |
US4362527A (en) * | 1982-01-04 | 1982-12-07 | The United States Of America As Represented By The Secretary Of Agriculture | Radiation-resistant fluoroaromatic cellulosic ethers |
US4484990A (en) * | 1980-06-16 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Mist suppressant for solvent extraction metal electrowinning |
US4873020A (en) * | 1988-10-04 | 1989-10-10 | Minnesota Mining And Manufacturing Company | Fluorochemical surfactants and process for preparing same |
US5821195A (en) * | 1996-08-16 | 1998-10-13 | Monsanto Company | Sequential application method for enhancing glyphosate herbicidal effectiveness with reduced antagonism |
US5985793A (en) * | 1996-08-16 | 1999-11-16 | Monsanto Company | Sequential application method for treating plants with exogenous chemicals |
US20060019830A1 (en) * | 2000-05-19 | 2006-01-26 | Monsanto Technology Llc | Pesticide compositions containing oxalic acid |
US7008904B2 (en) | 2000-09-13 | 2006-03-07 | Monsanto Technology, Llc | Herbicidal compositions containing glyphosate and bipyridilium |
US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
EP1820553A2 (de) | 2000-09-05 | 2007-08-22 | Donaldson Company, Inc. | Polymer, Polymermikrofaser, Polymernanofaser und Anwendungen mit Filterstrukturen |
US7309372B2 (en) | 2004-11-05 | 2007-12-18 | Donaldson Company, Inc. | Filter medium and structure |
EP1894609A1 (de) | 2004-11-05 | 2008-03-05 | Donaldson Company, Inc. | Filtermedium und -struktur |
US7985344B2 (en) | 2004-11-05 | 2011-07-26 | Donaldson Company, Inc. | High strength, high capacity filter media and structure |
US8021455B2 (en) | 2007-02-22 | 2011-09-20 | Donaldson Company, Inc. | Filter element and method |
US8057567B2 (en) | 2004-11-05 | 2011-11-15 | Donaldson Company, Inc. | Filter medium and breather filter structure |
US8177875B2 (en) | 2005-02-04 | 2012-05-15 | Donaldson Company, Inc. | Aerosol separator; and method |
US8267681B2 (en) | 2009-01-28 | 2012-09-18 | Donaldson Company, Inc. | Method and apparatus for forming a fibrous media |
WO2012129094A1 (en) | 2011-03-18 | 2012-09-27 | Donaldson Company, Inc. | High temperature treated media |
US8404014B2 (en) | 2005-02-22 | 2013-03-26 | Donaldson Company, Inc. | Aerosol separator |
US8512431B2 (en) | 2000-09-05 | 2013-08-20 | Donaldson Company, Inc. | Fine fiber media layer |
US9114339B2 (en) | 2007-02-23 | 2015-08-25 | Donaldson Company, Inc. | Formed filter element |
US9317068B2 (en) | 2012-09-24 | 2016-04-19 | Donaldson Company, Inc. | Venting assembly and microporous membrane composite |
EP3238807A1 (de) | 2000-09-05 | 2017-11-01 | Donaldson Company, Inc. | Filtrationsanordnung mit gefalteter konstruktion und verfahren |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2639473C2 (de) * | 1976-09-02 | 1986-03-27 | Bayer Ag, 5090 Leverkusen | Alkoxylierte Perfluoralkansulfonamide und deren Quaternierungsprodukte, Verfahren zu deren Herstellung und deren Verwendung |
Citations (10)
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US2146392A (en) * | 1939-02-07 | Quaternary ammonium salts | ||
US2204653A (en) * | 1938-12-06 | 1940-06-18 | Rohm & Haas | Aliphatic di-oxymethylene quaternary ammonium halides and process for producing them |
US2212654A (en) * | 1938-12-17 | 1940-08-27 | Du Pont | Process for preparing quaternary ammonium compounds and intermediates therefor |
US2314277A (en) * | 1939-05-23 | 1943-03-16 | Rohm & Haas | Process for glazing fabric |
US2567011A (en) * | 1949-01-10 | 1951-09-04 | Minnesota Mining & Mfg | Fluorocarbon acids and derivatives |
US2609270A (en) * | 1949-11-15 | 1952-09-02 | Inst Textile Tech | Mildewproof cellulose produced by reaction with chlord-benzyl quaternary ammonium salts |
US2732398A (en) * | 1953-01-29 | 1956-01-24 | cafiicfzsojk | |
US2759019A (en) * | 1954-08-09 | 1956-08-14 | Minnesota Mining & Mfg | Perfluoro amine compounds and quaternary derivatives |
US2793929A (en) * | 1953-12-04 | 1957-05-28 | Onyx Oil And Chemical Company | Process of shrinkproofing regenerated cellulose fabric with alkoxymethylene quaternary ammonium compositions and product produced therefrom |
US2803656A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbonsulfonamidoalkanols and sulfates thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE710965C (de) * | 1937-12-25 | 1941-09-24 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Halogen enthaltenden Formaldehydkondensationserzeugnissen aus Sulfonamiden |
DE729892C (de) * | 1937-12-25 | 1943-01-04 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Kondensationsprodukten von Sulfonsaeureamiden |
-
1959
- 1959-02-02 US US79033459 patent/US3147064A/en not_active Expired - Lifetime
-
1960
- 1960-01-26 GB GB281960A patent/GB933056A/en not_active Expired
- 1960-02-01 DE DEM44189A patent/DE1150383B/de active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2146392A (en) * | 1939-02-07 | Quaternary ammonium salts | ||
US2204653A (en) * | 1938-12-06 | 1940-06-18 | Rohm & Haas | Aliphatic di-oxymethylene quaternary ammonium halides and process for producing them |
US2212654A (en) * | 1938-12-17 | 1940-08-27 | Du Pont | Process for preparing quaternary ammonium compounds and intermediates therefor |
US2314277A (en) * | 1939-05-23 | 1943-03-16 | Rohm & Haas | Process for glazing fabric |
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US2609270A (en) * | 1949-11-15 | 1952-09-02 | Inst Textile Tech | Mildewproof cellulose produced by reaction with chlord-benzyl quaternary ammonium salts |
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US2793929A (en) * | 1953-12-04 | 1957-05-28 | Onyx Oil And Chemical Company | Process of shrinkproofing regenerated cellulose fabric with alkoxymethylene quaternary ammonium compositions and product produced therefrom |
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US2803656A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbonsulfonamidoalkanols and sulfates thereof |
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Also Published As
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GB933056A (en) | 1963-07-31 |
DE1150383B (de) | 1963-06-20 |
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