US3864396A - Acylated perfluoroalkanesulphonamides - Google Patents

Acylated perfluoroalkanesulphonamides Download PDF

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Publication number
US3864396A
US3864396A US313276A US31327672A US3864396A US 3864396 A US3864396 A US 3864396A US 313276 A US313276 A US 313276A US 31327672 A US31327672 A US 31327672A US 3864396 A US3864396 A US 3864396A
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US
United States
Prior art keywords
formula
perfluoroalkanesulphonamides
acid
polyamines
acylated
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Expired - Lifetime
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US313276A
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English (en)
Inventor
Adolf Staffe
Klaus Gerlach
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Bayer AG
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Bayer AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • D06M13/405—Acylated polyalkylene polyamines
    • 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
    • D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • 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
    • D06M13/418—Cyclic amides, e.g. lactams; Amides of oxalic acid
    • 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
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/09—Sulfur-containing compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/11—Halides

Definitions

  • the perfluoroalkanesulfonamides are excellent oleophobic agents.
  • the invention relates to perfluoroalkanesulphonamides; more particularly it concerns perfluoroalkanesulphonamides of the formula with the proviso that R and R only represents an optionally substituted alkyl group if the nitrogen atom to which the two radicals are bonded is an amine nitrogen atom or a sulphonamide nitrogen atom; the invention further relates to a process for the manufacture of the perfluoroalkanesulphonamides of the formula (I) and to their use as oleophobic agents.
  • Possible alkylene groups A are above all alkylene radicals with 2 to ID, preferably with 2 or 3, C atoms, for example the ethylene, ethylidene, propylene-(1,3), butylene-( 1,4), hexylene-( 1,6) and 4-oxaheptylene- (1,7) group. 7
  • R and R examples which may be mentioned of optionally substituted alkyl groups which R and R can be are: lower alkyl radicals, for example C,C,-alkyl radicals, such as the methyl, ethyl, n-propyl, n-butyl and sec.-butyl radical, and lower alkyl radicals substituted by nitrile or lower alkoxy groups, such as the Z-methoxyethyl, 3- methoxypropyl, Z-ethoxyethyl, 3-ethoxypropyl and 2- cyanoethyl radical. 7
  • lower alkyl radicals for example C,C,-alkyl radicals, such as the methyl, ethyl, n-propyl, n-butyl and sec.-butyl radical
  • lower alkyl radicals substituted by nitrile or lower alkoxy groups such as the Z-methoxyethyl, 3- methoxypropyl, Z-ethoxyethy
  • carboxylic acids from which R, is derived as an acyl radical are both aromatic and saturated or unsaturated aliphatic monocarboxylic or dicarboxylic acids.
  • aromatic carboxylic acids benzoic acid.
  • lower monocarboxylic acids may above all be mentioned, such as acetic acid, propionic acid, butyric acid, acrylic acid and methacrylic acid and also lower dicarboxylic acids, such as succinic acid, adipic acid and maleic acid.
  • perfluoroalkanesulphonamides of the formula (I), according to the invention are obtainable in various ways; preferably, they are obtained by reacting polyamines of the formula in which A and n have the meaning indicated under the formula (l) with perfluoroalkanesulphonyl halides of the formula (Ill) in which R, and m have the meaning indicated under the formula (l) and in which X represents chlorine or preferably fluorine, and optionally acylating the resulting polyperfluoroalkane-sulphonyl-polyamines in a manner which is in itself known and/or alkylating them in a manner which is in itself known.
  • Another possible method of manufacture consits of first acylating the polyamines of the formula (H) in a manner which is in itself known and to react the acylated polyamines of the formula l flf tAtw -t t l (41 (Iv) in which n and y have the meaning indicated under the formula (l) with perfluoroalkanesulphonyl halides of the formula (III), in the manner described for the polyamines.
  • the reaction of the polyamines (II) with the perfluoroalkanesulphonyl halides (lll) is carried out at temperatures of to 150C, preferably 40 to 90C, in the presence of acid-binding agents, such as inorganic bases, for example potassium carbonate, or organic bases, for example tertiary amines, such as triethylam-
  • acid-binding agents such as inorganic bases, for example potassium carbonate, or organic bases, for example tertiary amines, such as triethylam-
  • the poly-perfluoroalkanesulphonyl-polyamines are reacted in a manner which is in itself known,at temperatures of 0 to l00C, preferably at 30 to 60C, optionally in solvents which are inert under the reaction conditions, such as pyridine.
  • acyl halides for example benzoyl chloride, acetyl chloride, propionyl chloride, butyryl chloride, acrylic acid chloride, methacrylic acid chloride, choroformic acid methyl ester or chloroformic acid ethyl ester; acid anhydrides, for example acetic anhydride, succinic anhydride and maleic anhyd'ride; carboxylic acid esters, for example acetic acid methyl ester, propionic acid methyl ester and benzoic acid methyl ester; isocyanates, for example methylisocyanate, methoxymethylisocyanate, ethylisocyanate, cyclohexylisocyanate, phenylisocyanate and tolyisocyanate; and inorganic cyanates, for example potassium cyanate.
  • acyl halides for example benzoyl chloride, acetyl chloride, propionyl chloride, butyryl chloride,
  • the optionally acyl' ated poly-perfluoroalkanesulphonyl-polyamines are converted, in a manner which is in itself known, into the alkali compounds of the sulphonamides, for example by reaction of the sulphonamides with sodium methylate in absolute methanol, and the alkali compounds are reacted, optionally in a solvent which is inert under the reaction conditions, with alkyl halides of the fomula RX, and/or RX
  • alkyl halides of the fomula RX, and/or RX instead of starting from polyamines of the formula (ll) it is also possible, in manufacturing the compounds of the formula (I) according to the invention, to start from diamines containing cyanoalkyl groups, for example N-cyanoethylethylenediamine, to react these with perfluoroalkanesulphonyl halides in the manner described above for the polyamines (ll), and to reduce the resulting bis-perfluor
  • the compounds according to the invention, of the formula (I) are valuable agents for the oleophobic finishing of materials made of paper, wood, textiles and yarns.
  • EXAMPLE l 604 g (2 mols) of perfluoro-n-butanesulphonic acid fluoride are added dropwise, at a temperature of 89C, to a mixture of 103 g (1 mol) of diethylenetriamine, 505 g (5 mols) of triethylamine and 67.5 g (0.5 mol) of N-dimethylbenzylamine at such speed that the temperature of the reaction mixture does not drop below C.
  • the reaction mixture is stirred for 5 hours at 80C. After distilling off the triethylamine, the residue is dissolved in 550 ml of pyridine.
  • N,N-Bis-( 2-perfluorobutanesulphonylaminoethylJ-methaerylic acid amide I CH -C 3 n (molecular weight 735) precipitates in the form of a yellowish brown amorphous powder in a yield of 647 I5 g 88% of theory).
  • N,N-bis-( 2-perfluorobutanesulphonylaminoethyl)-N,N'-bis-methacryloyl-ethylenediamine on -c on -c 5" 5" CH CH CH -NHSO C F (molecular weight 846) is obtained in the form of a brownish amorphous powder in a yield of 778 g 92% of theory).
  • Cotton fabric was impregnated with a 1% strength solution of the N,N-bis-(2- in which R is carbonyl, oxalyl, succinyl, adipyl, or maleoyl;
  • R and R independently of one another are hydrogen; C -C alkyl; or C,C, alkyl substituted by nitrile or lower alkoxy;
  • A is Crcw-alkylene or C -C alkylene interrupted by oxygen
  • R is perf'luorinated butyl; and m is 1 or 0.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Paper (AREA)
US313276A 1971-12-10 1972-12-08 Acylated perfluoroalkanesulphonamides Expired - Lifetime US3864396A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2161341A DE2161341A1 (de) 1971-12-10 1971-12-10 Acylierte perfluoralkansulfonamide

Publications (1)

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US3864396A true US3864396A (en) 1975-02-04

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Country Status (9)

Country Link
US (1) US3864396A (cg-RX-API-DMAC7.html)
JP (1) JPS4864024A (cg-RX-API-DMAC7.html)
BE (1) BE792563A (cg-RX-API-DMAC7.html)
CH (1) CH570369A5 (cg-RX-API-DMAC7.html)
DE (1) DE2161341A1 (cg-RX-API-DMAC7.html)
FR (1) FR2162627B1 (cg-RX-API-DMAC7.html)
GB (1) GB1371160A (cg-RX-API-DMAC7.html)
IT (1) IT973945B (cg-RX-API-DMAC7.html)
NL (1) NL7216732A (cg-RX-API-DMAC7.html)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917691A (en) * 1972-08-09 1975-11-04 Nat Starch Chem Corp Perfluoro alkyl sulfonamides useful as water and oil repellency agents
US4149979A (en) * 1977-07-02 1979-04-17 Cassella Aktiengesellschaft Conditioning and water-repellent agents for cellulose-containing textiles and leather
US4163754A (en) * 1977-02-28 1979-08-07 Ici Americas Inc. Fluorinated sulfonamides
US4175096A (en) * 1976-09-02 1979-11-20 Bayer Aktiengesellschaft Alkoxylated perfluoroalkanesulphonamides
US20070049646A1 (en) * 2005-08-30 2007-03-01 Moore George G I Compositions of fluorochemical surfactants
CN106905197A (zh) * 2017-03-08 2017-06-30 江苏理文化工有限公司 一种含氟丙烯酰胺及其合成方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2921142A1 (de) * 1979-05-25 1980-12-11 Bayer Ag Verwendung von perfluoralkansulfonamid- salzen als tenside
EP3187516B1 (en) * 2014-08-28 2018-10-10 Fujifilm Corporation Curable composition, cured product of functional polymer, stack or device provided with functional polymer film, amide compound and method for producing same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2759019A (en) * 1954-08-09 1956-08-14 Minnesota Mining & Mfg Perfluoro amine compounds and quaternary derivatives
US2803656A (en) * 1956-01-23 1957-08-20 Minnesota Mining & Mfg Fluorocarbonsulfonamidoalkanols and sulfates thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2759019A (en) * 1954-08-09 1956-08-14 Minnesota Mining & Mfg Perfluoro amine compounds and quaternary derivatives
US2803656A (en) * 1956-01-23 1957-08-20 Minnesota Mining & Mfg Fluorocarbonsulfonamidoalkanols and sulfates thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917691A (en) * 1972-08-09 1975-11-04 Nat Starch Chem Corp Perfluoro alkyl sulfonamides useful as water and oil repellency agents
US4175096A (en) * 1976-09-02 1979-11-20 Bayer Aktiengesellschaft Alkoxylated perfluoroalkanesulphonamides
US4163754A (en) * 1977-02-28 1979-08-07 Ici Americas Inc. Fluorinated sulfonamides
US4149979A (en) * 1977-07-02 1979-04-17 Cassella Aktiengesellschaft Conditioning and water-repellent agents for cellulose-containing textiles and leather
US20070049646A1 (en) * 2005-08-30 2007-03-01 Moore George G I Compositions of fluorochemical surfactants
US7547732B2 (en) * 2005-08-30 2009-06-16 3M Innovative Properties Company Compositions of fluorochemical surfactants
CN106905197A (zh) * 2017-03-08 2017-06-30 江苏理文化工有限公司 一种含氟丙烯酰胺及其合成方法

Also Published As

Publication number Publication date
IT973945B (it) 1974-06-10
JPS4864024A (cg-RX-API-DMAC7.html) 1973-09-05
FR2162627A1 (cg-RX-API-DMAC7.html) 1973-07-20
BE792563A (fr) 1973-06-12
FR2162627B1 (cg-RX-API-DMAC7.html) 1974-08-02
CH570369A5 (cg-RX-API-DMAC7.html) 1975-12-15
NL7216732A (cg-RX-API-DMAC7.html) 1973-06-13
GB1371160A (en) 1974-10-23
DE2161341A1 (de) 1973-06-14

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