GB773326A - Perfluoro quaternary nitrogen compounds - Google Patents

Perfluoro quaternary nitrogen compounds

Info

Publication number
GB773326A
GB773326A GB9937/55A GB993755A GB773326A GB 773326 A GB773326 A GB 773326A GB 9937/55 A GB9937/55 A GB 9937/55A GB 993755 A GB993755 A GB 993755A GB 773326 A GB773326 A GB 773326A
Authority
GB
United Kingdom
Prior art keywords
compounds
iodide
group
dimethyl
sulphate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB9937/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB773326A publication Critical patent/GB773326A/en
Expired legal-status Critical Current

Links

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises perfluoroalkyl carboxylic acid quaternary ammonium alkyl amides of the formula <FORM:0773326/IV(b)/1> where n is 3 to 11, m is 2 to 6, A is an anion and NQ is an oleophilic organic cationogenic group containing a quaternary nitrogen atom, the remaining co-valencies of which are satisfied by means of carbon-nitrogen bonds. Preferred products are compounds in which -NQ has the structure -N(R)(R1)R11, wherein R1 and R11\h are alkyl groups of 1 to 6 carbon atoms and R is an alkyl, cycloalkyl, alkaryl, aryl or aralkyl group of 1 to 17 carbon atoms, e.g. benzyl, a group (CH2)pCOOH, where p has a value of 1 to 4, or its esters and salts, or a group derived from a dicarboxylic acid such as -CH(COOH).CH2.-COOH or its esters and salts, and compounds wherein NQ is a pyridinium group or wherein the nitrogen atom forms part of a saturated heterocyclic ring such as a piperidine or morpholine ring. The compounds may be made by quaternizing the corresponding tertiary amines, for example by reaction with a halide or sulphate of the formula RA. Compounds wherein -NQ is a pyridinium group are made by reacting pyridine with a perfluoroalkyl-amido-polymethylene halide. The anion A is suitably a halide or sulphate. The corresponding hydroxides may be made by treating the halide salts with an aqueous suspension of silver oxide. The compounds are used as surface-active agents. In examples: (1) N:N-dimethyl-N1-perfluoroctanamidopropylamine is reacted with methyl iodide to give trimethyl gamma-(perfluoroctanamido)-propyl ammonium iodide; (2) beta-perfluoroctanamidoethyl chloride is reacted with pyridine to give beta-perfluoroctanamidoethyl pyridinium chloride; (3) N:N-diethyl-N1-perfluoroctanamidoethylamine is reacted with dimethyl sulphate to make methyldiethyl-gamma - (perfluoroctanamido) ethylammonium methyl sulphate and (4) N:N-diethyl-N1-perfluoroctanamidoethyl amine is quaternated with chloroacetic acid. Other specified products according to the invention include the perfluoro-hexanoyl derivative of 3-aminopropyldiethyl methyl ammonium iodide, the perfluorooctanoyl derivatives of 3-aminopropyl diethylmethylammonium iodide, 3-aminopropyl dimethyl decylammonium bromide, 3-aminopropyl dimethyl benzylammonium chloride and 2-aminoethyl diethyl methylammonium chloride and the perfluoro-decanoyl and dodecanoyl derivatives of 3-aminopropyl trimethylammonium iodide. Specification 773,327 is referred to.ALSO:Surface active agents useful as additives for oils and waxes comprise perfluoroalkyl compounds of the formula [CnF2n+1-CONH-(CH2)m-NQ]+A- wherein n has a value of 3 to 11, m has a value of 2 to 6, A is an anion and NQ is an oleophilic organic cationogenic group containing a quaternary nitrogen atom linked to the amide nitrogen atom through a polymethylene chain, the remaining covalencies of the group NQ being satisfied by carbon-nitrogen bonds. Concentrations of 0.1 per cent of the active compound are effective in reducing the surface tension of animal, vegetable and mineral oils and waxes such as petroleum solvents, petrol, paraffin, fuel oils, lubricating oils and paraffin waxes. The surface tensions of compositions of the active compounds with (a) linseed oil, (b) mineral oil and (c) paraffin wax are listed, the active compounds being perfluorohexanoylaminopropyl N : N - dimethyl - N - ethyl ammonium iodide (n=5, m=3, NQ= N(CH3)2C2H5); perfluorodecanoylaminopropyl trimethylammonium iodide (n=9, m=3, NQ=N(CH3)3); perfluorododecanoylaminopropyl trimethylammonium iodide (n=11, m=3, NQ=N(CH3)3) and corresponding perfluoro-octanoyl quaternary chlorides; bromides; idodides or methylsulphates in which m and NQ have the respective values; 2. N(C2H5)2CH3; 3, N(CH3)3; 3. N(C2H5)2CH3; 3N(CH3)2 C10H21; 3, N(CH3)2CH2C6H5; 2, NC5H4Cl (4-chloropyridinium and 2, N(C2H5)2CH2 COOH.
GB9937/55A 1954-04-21 1955-04-05 Perfluoro quaternary nitrogen compounds Expired GB773326A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US773326XA 1954-04-21 1954-04-21

Publications (1)

Publication Number Publication Date
GB773326A true GB773326A (en) 1957-04-24

Family

ID=22137444

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9937/55A Expired GB773326A (en) 1954-04-21 1955-04-05 Perfluoro quaternary nitrogen compounds

Country Status (1)

Country Link
GB (1) GB773326A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126633A (en) * 1973-09-12 1978-11-21 Pennwalt Corporation Fluorinated aliphatic sulfides
EP0311473A1 (en) * 1987-09-16 1989-04-12 Applications Et Transferts De Technologies Avancees Atta Fluorinated derivate of amino acids, useful as tensioactive or cotensioactive agents, and preparations for biomedical use containing these derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126633A (en) * 1973-09-12 1978-11-21 Pennwalt Corporation Fluorinated aliphatic sulfides
EP0311473A1 (en) * 1987-09-16 1989-04-12 Applications Et Transferts De Technologies Avancees Atta Fluorinated derivate of amino acids, useful as tensioactive or cotensioactive agents, and preparations for biomedical use containing these derivatives

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