US3510494A - Certain perfluoro alkanamido-,perfluoro alkanoyloxy-,perfluoroalkyloxy and perfluoro mercapto - quaternary ammonium compounds,the corresponding pyridinium compounds and derivatives thereof - Google Patents

Certain perfluoro alkanamido-,perfluoro alkanoyloxy-,perfluoroalkyloxy and perfluoro mercapto - quaternary ammonium compounds,the corresponding pyridinium compounds and derivatives thereof Download PDF

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US3510494A
US3510494A US550646A US55064666A US3510494A US 3510494 A US3510494 A US 3510494A US 550646 A US550646 A US 550646A US 55064666 A US55064666 A US 55064666A US 3510494 A US3510494 A US 3510494A
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perfluoro
water
quaternary ammonium
oil
compounds
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Domenick Donald Gagliardi
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Colgate Palmolive Co
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Colgate Palmolive Co
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • D06M13/408—Acylated amines containing fluorine atoms; Amides of perfluoro carboxylic acids
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms

Definitions

  • the present invention is a continuation-in-part Ser. No. 301,628 now abandoned, filed Aug. 12, 1963, and relates to soil-proofing textiles and to the soil-proofing quaternary ammonium compounds used and, more'particularly to soil-proofing textiles with perfluoro quaternary ammonium compounds and to the perfluoro quaternary ammonium compounds per se.
  • thermosetting nor fiber reaction occurs when textiles are coated with such products, the treated textile is nondurable to washing and dry cleaning.
  • water repellency for rainwear fabrics such mixtures provide fabrics with a fair degree of spot and stain resistance to water-borne chromophoric materials.
  • chlorine resistant fluoroquaternary ammonium compounds having compositions corresponding to the following formula provide textiles with water-repellency, oil-repellency, resistance to staining by water-borne and oil-borne stains and the ability to shed dry soil:
  • R, R" and R' are alkyl groups having 1 to 6 carbon atoms of which two adjacent carbon atoms can form with the nitrogen a heterocyclic group having 5 or 6 carbon atoms or aromatic groups.
  • R, R" and R can be the same or different, e.g., two or R, R and R' can be alkyl or cyclo-alkyl groups and the other can be an aromatic group;
  • Q is an alkyl, aryl, alkyl-aryl or cyclo-alkyl radical having three to twenty-one carbon atoms and 7 to 43 hydrogen atoms of which hydrogen atoms 70 to percent are replaced by fluorine atoms and the terminal carbon group preferably has three fluorine atoms attached thereto; and
  • R is alkyl, hydroxyalkyl, aryl, haloalkyl, or haloaryl.
  • chlorine resistant refers to the ability of the compound on the fabric, after bleaching with chlorine, to resist yellowing and fabric damage which normally occurs when fabric treated with non-chlorine resistant fiuoro-quaternary compound is bleached during laundering and then is ironed.
  • textiles refers to fibers, yarns, woven fabrics, felted materials composed in part or in whole of cellulosic material such as cotton, synthetic cellulosic material such as regenerated cellulose, proteinaceous material such as wool or synthetic fibers such as nylon, fiberglass, acrylic, polyester fibers and non-woven fabrics.
  • cellulosic material such as cotton
  • synthetic cellulosic material such as regenerated cellulose
  • proteinaceous material such as wool
  • synthetic fibers such as wool
  • solid materials such aspaper, wood, leather and the like may also be treated where it is desired to impart oil, water or any soil repellency.
  • the quaternary ammonium compounds are made by the classical methods of organic chemistry. The methods of preparation of these quaternary ammonium compounds form no part of the present invention. Hence, the preparation of these quaternary ammonium compounds need not be described in detail. It suffices to describe the preparation of N-hydromethyl-perfluorooctanamidomethyl pyridinium acetate as illustrative of the preparation of these quaternary ammonium compounds corresponding to the formula:
  • Theperfluoroalkanoic acid amide can then be converted to N-alkyl, perfluorooctanamidomethyl pyridinium acetate by reaction with pyridine and paraformaldehyde in glacial acetic acid. This reaction can be considered to be represented by the Equation 2:
  • n has an integer value of 3 to 9 and the Rs are alkyl groups (which can be the same or different) that contain 1 to 5 carbon atoms.
  • X is chlorine or bromine
  • R is a divalent radical selected from the group consisting of 4 and m is an integerfrom l to 10; and Ii is an integer from 3 to 12.
  • n has an integer value of 3 to 21 even when R", R" and R' are the same as R, R and R in Formula C, and R, R", R, R and X having the meaning set forth in FormulaB.
  • the quaternarysammonium compounds of the present invention react with the active hydrogen in the surface of the substrate even at low temperatures, e.g., 300 F. and lower and are substrateor fiber-reactive.
  • the quaternary ammonium compounds of the present invention endow the substrates to which they are aflixed with water repellency when the number of carbon atoms in Q in the formula is at least three.
  • the quaternary ammonium compounds of the present invention have the highly desirable property of being chlorine resistant so that substrates to which they are afiixed, in addition to being provided with water, oil and soil repellency properties, and are highly resistant during and after laundering, bleaching and ironing to yellowing and fabric damage.
  • Equation 6 Equation 6:
  • the reaction is heated until the theoretical chloride content has formed and the Yet another product may be obtained by mixing one mole of pentadecafluorooctyl alcohol with one mole of p-hydroxy benzoic acid in toluene, sodium methoxide is added as a catalyst and the mixture is heated to reflux temperature. Reflux is continued using an azeotropic separator to remove water as it is formed during esterification:
  • the resulting product is filtered, 'washed with cold alcohol and dried. When applied to textiles at 0.5-3 .0% concentration it produces water, oil and soil repellency.
  • Still another product may be obtained by mixing one mole of perfluorobenzamide with one mole of paraformal- 4.5 dehyde and one mole of morpholine in xylol solution. The mixture is refluxed and water collected in an azeotropic separator. After 18 grams of water are collected, the solution is cooled to room temperature:
  • WATER REPELLENCY Resistance to wetting (spray test), AATCC standard test method 22-1952
  • This test is applicable to any textile fabric. It measures the resistance of fabrics to wetting by a water spray and the results depend primarily on the degree of hydrophobicity inherent in the fibers and yarns and subsequent treatments to which the fabric is subjected. Water is sprayed against the taut surface of a test specimen. Evaluation of the wetted pattern is readily brought about by comparing the wetted pattern with standard wetting pattern pictures:
  • test specimens of minimum size of 7" x 7" are conditioned at 70 F. and 65 percent relative humidity for a minimum of four hours before testing.
  • test specimen fastened securely and wrinkle-free in a metal hoop having a diameter of 6 inches, is placed and centered 6 inches under a standard spray nozzle at an angle of 45 to the horizontal.
  • Two hundred and fifty milliliters of water at 80i2 F. is poured into a funnel attached above the spray nozzle.
  • the spray lasts 25 to 30 seconds at the end of which time the loop is taken by one edge and the opposite edge tapped smartly once against a solid object with the wet side facing the solid; this procedure is repeated with the hoop reversed OIL REPELLENCY (3M Textile Chemicals" Appendix ATest Methods, page 1)
  • the Minnesota Mining oil repellency test is based on the different penetrating properties of the two hydrocarbon liquids, mineral oil (Nujol) and n-heptane.
  • Percent heptane (by volume) Percent Nujo I No hold out to Nujol. Percent The standard oil-heptane mixtures are contained in small stoppered medicine-dropper bottles. A drop of each mixture of Nujol and heptane is placed on the fabric. The appearance of the test oil is observed through the drop. Note is made whether wetting or penetration occurs.
  • the change in the optical refractivity of the drop is often an indication of wetting. In some cases wetting can be better determined by observing the other side of the fabric. In some cases reported hereinafter the term has been used to indicate a modicum of resistance to wetting by oil.
  • 80x 80 cotton including at least one untreated control, were tumbled for 30 minutes with 10% soil based on weight of the fabric.
  • the soil was prepared by the method described by Salisbury et al. in an article entitled Soil Resistant Treatment 8 of Fabrics, American Dyestuif Reporter, Mar. 26, 1956, page 199.
  • the soil had the following compostion:
  • the dry ingredients were blended thoroughly, dried in a forced draft convection oven for 8 hours at 50 C., then milled 25 hours with ceramic balls and stored in a polyethylene bag.
  • the tumbling was carried out in a 5 liter capacity Five Minute Homer Cleaner at 44 r.p.m.; six No. 8 neoprene rubber stoppers were distributed among the specimens to increase mechanical action. At the end of tumbling, the specimens were removed and each shaken up and down 15 times by hand to remove surface dirt.
  • the perfluoro-quaternary ammonium compounds of the present invention are soluble in water, it is preferred to alfix the compound to the substrate from an aqueous solution of the quaternary ammonium compound.
  • the substrate particularly a substrate having active hydrogen in the surface thereof, e.g., cellulose, wool, silk and in general natural or synthetic proteinaceous materials, nylon, etc.
  • the perfluoro quaternary ammonium compound present usually as a salt of acetic acid, hydrochloric acid, and the like, separated from the aqueous solution, wrung to to 100 percent wet pick-up, dried and preferably heat treated at an elevated temperature for a time inversely proportioned to temperature in the range of 250 to 350 F., e.g., for five to ten minutes at 300 F. In this manner about 0.15 to 3 percent of the perfluoro quaternary compound can be affixed to the textile substrate.
  • a solution containing 0.2 to 3 percent of the perfluoro quaternary ammonium compound present usually as a salt of acetic acid, hydrochloric acid, and the like
  • Illustrative of the reaction between a substrate having active hydrogen in the surface'and the present perfluoro quaternary compound is the reaction with the active hydrogen of a hydroxyl group of cellulose ZOH where Z is the cellulose radical and OH is a hydroxyl group.
  • Illustrative of the resistance to soiling by water, oil, water-borne, and oil-borne materials are the following data obtained when treating cotton with pentadecafluorooctanamidomethyl pyridinium acetate.
  • a B A vention provides novel perfiuoro quaternary ammonium compounds which are reactive with active hydrogen in the surface of a substrate having active hydrogen to produce a coated fiber or fabric or in general a coated textile in which at least a portion of the coating is attached to the substrate by chemical bonds. Consequently, these novel quaternary compounds provide substantive coatings for textiles having active hydrogen in the surfaces thereof. Such coatings moreover do not form chloramides when bleached with chlorine and do not yellow or degrade the fibers.
  • the compounds of the invention as previously stated can also be used to treat materials not having active hydrogen in the surface.
  • a water-soluble, chlorine-resistant fluoro-quaternary ammonium compound of the formula R [QXOH2NR" ]AN- 11 i X is -CN; S; or (JO 4 (2) R, R" and R are each alkyl radicals of 1 to 6 carbon atoms, or two of said radicals together with the nitrogen form morpholine with the proviso that when two of said terms R, R and R' represent morpholine the term X represents where:

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Pyridine Compounds (AREA)
US550646A 1963-08-12 1966-05-17 Certain perfluoro alkanamido-,perfluoro alkanoyloxy-,perfluoroalkyloxy and perfluoro mercapto - quaternary ammonium compounds,the corresponding pyridinium compounds and derivatives thereof Expired - Lifetime US3510494A (en)

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AT (1) AT289796B (enrdf_load_stackoverflow)
CH (1) CH432455A (enrdf_load_stackoverflow)
FR (1) FR1534666A (enrdf_load_stackoverflow)
GB (1) GB1059278A (enrdf_load_stackoverflow)
SE (1) SE316448B (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3759981A (en) * 1971-05-20 1973-09-18 Pennwalt Corp Esters of perfluoroalkyl terminated alkylene thioalkanoic acids
US4049668A (en) * 1975-03-21 1977-09-20 Diamond Shamrock Corporation Cationic fluorochemical surfactants
US4183367A (en) * 1976-06-17 1980-01-15 American Cyanamid Company Enhancing the drying of hair by the use of fluorinated catonic and amphoteric surfactants
JPS62181249A (ja) * 1986-01-07 1987-08-08 ソシエテ　アトケム ポリフルオロアルキルチオメチル化合物と、その製造方法と、その界面活性剤への応用またはその前駆体
US4859349A (en) * 1987-10-09 1989-08-22 Ciba-Geigy Corporation Polysaccharide/perfluoroalkyl complexes
FR2641781A1 (fr) * 1988-12-27 1990-07-20 Atochem Acetates, thioacetates et acetamides de polyfluoroalkyle substitues, leurs procedes de preparation et leur application
US5525261A (en) * 1994-10-18 1996-06-11 Henkel Corporation Anti-static composition and method of making the same
JP2009067788A (ja) * 2007-08-23 2009-04-02 Sumitomo Chemical Co Ltd 含フッ素有機硫黄化合物およびその有害節足動物防除剤
KR101621785B1 (ko) 2014-07-23 2016-05-19 한국화학연구원 하이브리드형 불소계 화합물 및 이의 제조방법
KR101621779B1 (ko) 2014-07-23 2016-05-19 한국화학연구원 사차 암모늄을 포함하는 하이브리드형 불소계 화합물 및 이의 제조방법
CN117486830A (zh) * 2023-12-29 2024-02-02 成都科宏达化学有限责任公司 一种氟碳烷基硫醚丙基甜菜碱及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3488358A (en) * 1967-03-06 1970-01-06 Minnesota Mining & Mfg Certain 1,1 - dihydroperfluoroalkylpyridinium trifluoromethane sulfonates
DE3347378A1 (de) * 1983-12-29 1985-07-11 Hoechst Ag, 6230 Frankfurt Fluorierte quaternaere ammonium-verbindungen, verfahren zu deren herstellung und deren verwendung als stroemungsbeschleuniger

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623902A (en) * 1950-03-15 1952-12-30 Sharp & Dohme Inc Bis-quaternary ammonium salts
US3147065A (en) * 1960-05-02 1964-09-01 Minnesota Mining & Mfg Quaternized halomethylamides
US3171861A (en) * 1957-06-11 1965-03-02 Minnesota Mining & Mfg Fluorinated aliphatic alcohols
US3420840A (en) * 1960-08-04 1969-01-07 Stevens & Co Inc J P Fluorinated compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623902A (en) * 1950-03-15 1952-12-30 Sharp & Dohme Inc Bis-quaternary ammonium salts
US3171861A (en) * 1957-06-11 1965-03-02 Minnesota Mining & Mfg Fluorinated aliphatic alcohols
US3147065A (en) * 1960-05-02 1964-09-01 Minnesota Mining & Mfg Quaternized halomethylamides
US3420840A (en) * 1960-08-04 1969-01-07 Stevens & Co Inc J P Fluorinated compounds

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3759981A (en) * 1971-05-20 1973-09-18 Pennwalt Corp Esters of perfluoroalkyl terminated alkylene thioalkanoic acids
US4049668A (en) * 1975-03-21 1977-09-20 Diamond Shamrock Corporation Cationic fluorochemical surfactants
US4183367A (en) * 1976-06-17 1980-01-15 American Cyanamid Company Enhancing the drying of hair by the use of fluorinated catonic and amphoteric surfactants
JPS62181249A (ja) * 1986-01-07 1987-08-08 ソシエテ　アトケム ポリフルオロアルキルチオメチル化合物と、その製造方法と、その界面活性剤への応用またはその前駆体
US4859349A (en) * 1987-10-09 1989-08-22 Ciba-Geigy Corporation Polysaccharide/perfluoroalkyl complexes
FR2641781A1 (fr) * 1988-12-27 1990-07-20 Atochem Acetates, thioacetates et acetamides de polyfluoroalkyle substitues, leurs procedes de preparation et leur application
JPH02225448A (ja) * 1988-12-27 1990-09-07 Soc Atochem 置換されたポリフルオロアルキル酢酸エステル、チオ酢酸エステル及びアセトアミド、その製造方法及び用途
EP0376801A3 (en) * 1988-12-27 1990-11-28 Atochem Polyfluoroalkyl-substituted acetates, thioacetates and acetamides, their preparation and uses
US5066672A (en) * 1988-12-27 1991-11-19 Societe Atochem Polyfluoroalkyl acetates, thioacetates and acetamides, and their applications
US5525261A (en) * 1994-10-18 1996-06-11 Henkel Corporation Anti-static composition and method of making the same
JP2009067788A (ja) * 2007-08-23 2009-04-02 Sumitomo Chemical Co Ltd 含フッ素有機硫黄化合物およびその有害節足動物防除剤
KR101621785B1 (ko) 2014-07-23 2016-05-19 한국화학연구원 하이브리드형 불소계 화합물 및 이의 제조방법
KR101621779B1 (ko) 2014-07-23 2016-05-19 한국화학연구원 사차 암모늄을 포함하는 하이브리드형 불소계 화합물 및 이의 제조방법
CN117486830A (zh) * 2023-12-29 2024-02-02 成都科宏达化学有限责任公司 一种氟碳烷基硫醚丙基甜菜碱及其制备方法和应用
CN117486830B (zh) * 2023-12-29 2024-03-22 成都科宏达化学有限责任公司 一种氟碳烷基硫醚丙基甜菜碱及其制备方法和应用

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AT289796B (de) 1971-05-10
CH1024164A4 (enrdf_load_stackoverflow) 1966-12-15
FR1534666A (fr) 1968-08-02
DE1469290A1 (de) 1969-04-30
SE316448B (enrdf_load_stackoverflow) 1969-10-27
GB1059278A (en) 1967-02-15
CH432455A (de) 1967-09-15

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