DE904591C - Process for the preparation of quaternary ammonium compounds - Google Patents

Process for the preparation of quaternary ammonium compounds

Info

Publication number
DE904591C
DE904591C DEC2390D DEC0002390D DE904591C DE 904591 C DE904591 C DE 904591C DE C2390 D DEC2390 D DE C2390D DE C0002390 D DEC0002390 D DE C0002390D DE 904591 C DE904591 C DE 904591C
Authority
DE
Germany
Prior art keywords
quaternary ammonium
ammonium compounds
preparation
unsaturated
compounds
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
DEC2390D
Other languages
German (de)
Inventor
Dr Oscar Leupin
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC2390D priority Critical patent/DE904591C/en
Application granted granted Critical
Publication of DE904591C publication Critical patent/DE904591C/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
    • 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
    • C08F18/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F18/02—Esters of monocarboxylic acids
    • C08F18/04—Vinyl esters
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/56—Acrylamide; Methacrylamide
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von quaternären Ammoniumverbindungen Es wurde gefunden, diaB mart wertvolle quaternäre Ammoniumverbindungen erhält, wenn, man ungesättigte niedrigmolekulare organische Verbindu,ngen, die außer einer polynterisationsTähigen Doppelbindung mindestens eitle mit Formaldehyd zu einer Methylolgruppe untsetzungsfäh-iglei Gruppe -enthalten, nach. alt sich bekannten: Methoden in, ungesättigte quatertläre Ammoniuntverbindung-en umwandelt. Die, Erzeugnisse lassen, sich gewünschtenr falls für sich oder zusammen mit anderen polymerisationsfähigen Verbindungen. polymerisieren.Process for the preparation of quaternary ammonium compounds Es it was found that diaB mart receives valuable quaternary ammonium compounds if, one unsaturated, low molecular weight organic compounds, which apart from one polyinterization-capable Double bond at least void with formaldehyde to form a methylol group Group -contained, according to. old known: methods in, unsaturated quatertiary Converts ammonia compounds. The, products, can, if desired alone or together with other polymerizable compounds. polymerize.

Geeignete! Ausgangsetoffe sind z. B, Acr-yls,äureodeir Met#.hacryl,säurcami,d, Malein,s,5,u,red#iamid! oder -imid', Crotyliden.dihar-n;stoff, Acryl,id.endiharn,stoff oder Allyl-chlo.rrnethylätheir, Die Umwandlung in ungesiLütigte quaternäre Meithyleniammon-i#timverb#indungen erfolgt z. B. in der Weise, daß man, die Ausgangsstoff#, zusammen; mit Formaldehyd oder Fo-nnalde,Iivd bildendem, Verbindungen mit mine,ra,1-sauren Saiz-ein tertiäreir Amine, zweckmäß,ig in Gegenwart des betreffenden freien Amins, unter Erwärmen umsetzt. Geeignete Vertiäre Amine sind z. B. Pvridin, Chinolin, Trimethyl- und Tr.iäthylamin#, I#inteithylbenzylamin und D,iäthylam.inoosis#igsäure.Suitable! Starting materials are z. B, acr-yls, aureodeir Met # .hacryl, säurcami, d, Malein, s, 5, u, red # iamid! or -imid ', Crotyliden.dihar-n; stoff, Acryl, id.endiharn, stoff or allyl chloromethyl ether, the conversion into unsaturated quaternary methylene ammonium compounds takes place z. B. in such a way that one, the starting material #, together; with formaldehyde or Fo-nnalde, Iivd forming, compounds with mine, ra, 1-acidic Saiz-a tertiaryir Amines, expediently, reacted in the presence of the free amine in question with heating. Suitable vertical amines are e.g. B. Pvridine, quinoline, trimethyl- and diethylamine #, I # inteithylbenzylamine and D, iäthylam.inoosis # igsäure.

Die, Polymerisation der so, erhaltenen ungesättigten quaternüren, Methylenammoniumverbindungen erfolgt z. B. mit Hilfe von anorganischen oder organischen Peroxydlen oder Persalzen, die man, in Wasser oder in, organischen Lösungsmitteln gelöst oder suspendiert verwenden kann. Andere pely merisa,tio,ii(sifähi,ge Verbindungen, die man, zu- #;ammen. mit den in Rede stehenden ungesät#tigten Ammoniumvierbindunglen. zu Mischpolymerisaten polymerisieren kann, sind z. B. Vinylester und -ät#er, Butadien, Acry1säureester oder Styrol. je nach den verNvendeten: Mengenverhältnisisren erhält man in Wass-er mehr oder weniger lösliche oder leicht verteilbare Erzeugnisse.The, polymerization of the unsaturated quaternures thus obtained, Methylenammoniumverbindungen takes place z. B. with the help of inorganic or organic Peroxydlene or persalts, which one, in water or in, organic solvents can use dissolved or suspended. Other pely merisa, tio, ii (sifähi, ge connections, which one, too- #; nurses. with the unsaturated ammonium bonds in question. Can polymerize to form copolymers, are z. B. vinyl esters and ethers, butadiene, Acrylic acid ester or styrene. depending on the used: quantitative proportions obtained one in water more or less soluble or easily distributable products.

Die erhaltenen Produkte sind wertvolle Hilfsmittel für die Faser- und Kunfststoffveredelung. Die in dem folgenden Beispiel vomrendeten Teile sind Gewichtsteile.The products obtained are valuable aids for fiber and plastic finishing. The parts dated in the following example are Parts by weight.

Beispi#el Eine Lösung von, 71 Teilen Acrylsätireamid, 115 Teilen. Pyridiniumchlorid und 3o Teilen ParaJorm-9,ld'ehvd in 2oo Teilen Pyridin, wird, 3 Stunden am Rückilußkühler zum Sieden erhitzt. Dann, destilliert man, das! überschüssige! Pyridin bei vermindertem Druck ab, löst dlen:Rückstand in 5oo Teilen, WasseT, versetzt die Lösung mit io Teilen Ammoniumpersulfat und erhitzt einigie Zeit auf dem Wasserhad.Example A solution of, 71 parts of acrylic acid amide, 1 15 parts. Pyridinium chloride and 30 parts of ParaJorm-9, Id'ehvd in 2oo parts of pyridine, is heated to boiling for 3 hours on a reflux condenser. Then, you distill that! excess! Pyridine is removed under reduced pressure, dissolves the residue in 500 parts of water, the solution is treated with 10 parts of ammonium persulfate and heated for some time on the water bath.

Man erhält einie viskose Lösung, die sich z. B. zum Veredeln, von Leder, Papier oder Textilfasern eignet.A viscous solution is obtained, which z. B. for refining, of Leather, paper or textile fibers are suitable.

Claims (1)

PATENTANSPRUCII: Verfahren, zur Herstellung von qtiaternären Ammoniumverbindungen, däclurch gekennzeichnet, daß man ungesättigte nied-rigmolekulare orgamische Verbindungen, die außer einer polymeri#s,a,tio,ns,fähigen Doppelbindung mindlestens eine miti Formaldehyd zu einer Methylolgruppe umsetzungsfähige Gruppe eiühalten, nach an sich bekannten Methoden in ungesättigte quaternär-- Ammoniumvorbindungen umwandelt und letzMr.c gewünschtenfallisi für sich ader zusammen mit anderen polymerisatiions-fähigen Verbindungen polymer-is-iort.PATENT CLAIM: Process for the production of qtiaternary ammonium compounds, characterized by the fact that unsaturated low molecular weight organic compounds, the double bond capable of polymeri # s, a, tio, ns, at least one miti Keep formaldehyde in a group capable of reacting with a methylol group known methods into unsaturated quaternary ammonium precursors and LastMr.c desired case for himself or together with other polymerisatiions-capable Connections polymer-is-iort.
DEC2390D 1944-01-04 1944-01-04 Process for the preparation of quaternary ammonium compounds Expired DE904591C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC2390D DE904591C (en) 1944-01-04 1944-01-04 Process for the preparation of quaternary ammonium compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC2390D DE904591C (en) 1944-01-04 1944-01-04 Process for the preparation of quaternary ammonium compounds

Publications (1)

Publication Number Publication Date
DE904591C true DE904591C (en) 1954-02-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEC2390D Expired DE904591C (en) 1944-01-04 1944-01-04 Process for the preparation of quaternary ammonium compounds

Country Status (1)

Country Link
DE (1) DE904591C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1009809B (en) * 1954-11-10 1957-06-06 Basf Ag Process for the production of polyvinyl betaines
DE1021824B (en) * 1954-02-12 1958-01-02 Ici Ltd Process for modifying the properties of synthetic fibers
DE1123468B (en) * 1955-01-22 1962-02-08 Hermann Leinfelder Process for the production of water-soluble, poly-N-quaternary substances that increase diffusion in tissues
DE1131406B (en) * 1954-10-11 1962-06-14 Ciba Geigy Process for the production of copolymers in stable, fine aqueous dispersion

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1021824B (en) * 1954-02-12 1958-01-02 Ici Ltd Process for modifying the properties of synthetic fibers
DE1131406B (en) * 1954-10-11 1962-06-14 Ciba Geigy Process for the production of copolymers in stable, fine aqueous dispersion
DE1009809B (en) * 1954-11-10 1957-06-06 Basf Ag Process for the production of polyvinyl betaines
DE1123468B (en) * 1955-01-22 1962-02-08 Hermann Leinfelder Process for the production of water-soluble, poly-N-quaternary substances that increase diffusion in tissues

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