DE2214261B2 - Amino- oder ammoniumgruppen enthaltende amide der acryl- bzw. methacrylsaeure, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polymerisaten - Google Patents

Amino- oder ammoniumgruppen enthaltende amide der acryl- bzw. methacrylsaeure, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polymerisaten

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Publication number
DE2214261B2
DE2214261B2 DE19722214261 DE2214261A DE2214261B2 DE 2214261 B2 DE2214261 B2 DE 2214261B2 DE 19722214261 DE19722214261 DE 19722214261 DE 2214261 A DE2214261 A DE 2214261A DE 2214261 B2 DE2214261 B2 DE 2214261B2
Authority
DE
Germany
Prior art keywords
production
amides
ammonium
acrylic
methacrylic acid
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.)
Granted
Application number
DE19722214261
Other languages
English (en)
Other versions
DE2214261A1 (de
DE2214261C3 (de
Inventor
Donald Irvin Chagrin Falls; Surbey Donald Lee Lyndhurst; Ohio Hoke (V.St.A.)
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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
Priority to US832412A priority Critical patent/US3666810A/en
Priority to US203853A priority patent/US3883491A/en
Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Priority claimed from DE19722214261 external-priority patent/DE2214261C3/de
Priority to DE19722214261 priority patent/DE2214261C3/de
Priority to DE2233337*A priority patent/DE2233337A1/de
Priority to US00237871A priority patent/US3856689A/en
Priority to US00292697A priority patent/US3761407A/en
Publication of DE2214261A1 publication Critical patent/DE2214261A1/de
Priority to US05/455,162 priority patent/US3979441A/en
Publication of DE2214261B2 publication Critical patent/DE2214261B2/de
Publication of DE2214261C3 publication Critical patent/DE2214261C3/de
Application granted granted Critical
Expired legal-status Critical Current

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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D21/00—Separation of suspended solid particles from liquids by sedimentation
    • B01D21/01—Separation of suspended solid particles from liquids by sedimentation using flocculating agents
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    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
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    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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    • 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
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    • 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
    • C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
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    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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Description

in der R1, R2 und R3 jeweils ein Wasserstoffatom oder einen Alkylrest mit 1 bis 10 Kohlenstoffatomen und R4 und R5 jeweils einen Alkylrest mit 1 bis 10 Kohlenstoffatomen bedeuten, R* ein Wasserstoff- «tonrt oder eine Methylgruppe darstellt, Y die Gruppe
■ von Schwefelsäure umsetzt oder
b) eine Verbindung der Formel
Z1 Z2
N R2 R4 O (IV)
R^CH-C-C-N-C-CHCH1OR7
III I "
R3 Rs H R6
in der R7 einen Kohlenwasserstoffrest darstellt und R», R2, R3, R4, R5, R6, Z1 und Z2 die vorstehende Bedeutung haben, der Pyrolyse in Gegenwart einer Base bei Temperaturen von 70 bis 150° C unterwirft.
3. Verwendung der Verbindungen nach Anspruch
zur Herstellung von Polymerisaten
Z1
— N
\
Z2
Z1
— N — Z2 X
bedeutet, X ein salzbildendes Anion ist, Z1 und Z2 jeweils ein Wasserstoffatom, einen Alkylrest mit 1 bis 10 Kohlenstoffatomen oder einen Cycloalkylrest mit 3 bis 8 Kohlenstoffatomen darstellen und Z3 ein Wasserstoffatom oder einen Alkylrest mit 1 bis 10 Kohlenstoffatomen bedeutet.
2. Verfahren zur Herstellung der Aminogruppen enthaltenden Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise
a) ein ungesättigtes Nitril der Formel
CH7 = C-CN (II)
R6
in der R6 die in Anspruch 1 angegebene Bedeutung hat, mit einem ungesättigten Amin der Formel
Z1 Z2
N R2 R4 ho
I /
R1—CH- C=CX (III)
R3 R5
in der R1, R2, R4, R5, Z1 und Z2 die in Anspruch 1 angegebene Bedeutung haben, in Gegenwart Die Erfindung betrifft den in den Atisprüchen gekennzeichneten Gegenstand
In den bevorzugten Verbindungen der Erfindung ist X ein typisches salzbildendes Anion, wie das Chlorid. Bromid, Jodid, Sulfat, Bisulfat, Acetat, Carbonat oder Bicarbonat. Besonders bevorzugt sind Verbindungen, in denen die Reste R1, R2 und R3 Wasserstoffatome oder Alkylreste mit 1 bis 10 Kohlenstoffatomen, R4 und R5 Alkylreste mit 1 bis 10 Kohlenstoffatomen, Rb ein Wasserstoffatom, Z1 und Z2 Alkylreste mit 1 bis 10 Kohlenstoffatomen und 7J (sofern anwesend) eine Methylgruppe bedeutet.
In der US-PS 25 95 907 sind Acrylnitrii-Dialkyiaminopropylacrylamid-Copolymerisate beschrieben, die sich mit sauren Farbstoffen leichter färben lassen als bis dahin bekannte Acrylnitril-Polymerisate. Aus der GB-PS 7 85 992 sind Acrylamido- bzw. Methacrylamidogruppen enthaltende quartäre Ammoniumsalze bekannt, die sich zur Herstellung von Textilhilfsmitteln eignen. In der US-PS 32 77 056 sind N-3-OxoaIkylacrylamide und die entsprechenden Polymerisate beschrieben, die zur Herstellung von Kunststoffen, Harzen, synthetischen Schmiermitteln, Fasern und Zusätzen für Kohlenwasserstofföle verwendet werden. In der GB-PS 12 50 987 sind Hydroxyalkylreste enthaltende N-3-Oxoalkylacrylamide und die entsprechenden Polymerisate beschrieben, die zur Herstellung von Korrosionsschutzanstrichen, Textilklebstoffen und abziehbaren Beschichtungen geeignet sind. Schließlich sind aus der GB-PS 12 54 763 N-3-Hydroxyalkylacrylamide und entsprechende Polymerisate bekannt, für die folgende Anwendungsgebiete genannt sind: Herstellung von Tinten, Anstrichfarben, Verdickungsmitteln, Klebstoffen, Pulvern zur Überführung in Formkörper oder Beschichtungen, Zusätzen zur Verbesserung der Viskositätseigenschaften von Schmierstoffen, Fasern, Schutzbeschichtungen für Fotografien, Konservierungsmitteln für Pflanzen, Verfestigungsmitteln für Flugzeuglandebahnen, Leimungsmitteln für Glaslasergelege, wasserabstoßenden Materialien für Bekleidung und Polsterwaren, halbdurchlässigen Nahrungsmittelverpackungen, Lederpflegt mitteln, Tonbändern und halbdurchlässigen Membranen zur Hyperfiltration.
Die Aminogruppen enthaltende ! Amide der Erfin-
dung, die nachstehend auch als »Acrylamidoverbiiidungen« bezeichnet werden, können aus den Oxyverbindungen der Formel IV durch Abspaltung eines Alkohols der Formel R7OH nach an sich bekannten Methoden hergestellt werden. Typische Methoden sind von P. F. ßutskus et al.. Russian Chemical Reviews, Bd. 35 (1966), S. 39, beschrieben. Die bevorzugte Methode besteht in der Pyrolyse in Gegenwart einer Base, gewöhnlich einer starken Base, wie festem Natriumhydroxid, bei Temperaturen von 70 bis 1100C. Diese Umsetzung wird vorzugsweise unter vermindertem Druck durchgeführt.
Bei der Umsetzung des ungesättigten Amins der Formel III mit dem ungesättigten Nitril der Formel 11 werden vorzugsweise mindestens etwa 1,5 Mol, im allgemeinen etwa 1,9 bis 3,0 Mol des Nitrils je Mol des ungesättigten Amins verwendet. Die Konzentration der Schwefelsäure soll mindestens etwa 90 Prozent, vorzugsweise etwa 96 bis 98 Prozent, betragen. Das Jvlolverhältnis von Schwefelsäure zu Amin soll mindestens etwa 1:1, vorzugsweise von etwa 1.1 : 1 bis 2:1, betragen. Lösungsmittel sind gewöhnlich nicht erforderlich, es kann jedoch vorteilhaft sein, eine geringe Menge eines Polymerisationsinhibitors, wie Hydrochinon oder ein sterisch gehindertes Phenol, zuzusetzen. Nach beendeter Umsetzung kann das Produkt durch Verdünnen und Neutralisation des Gemisches und Abtrennen des ungesättigten Amids nach üblichen Methoden isoliert werden.
Die erfindungsgemäß eingesetzten ii'-gesattigien Amine der Formel III können durch Umsetzung eines Amins der Formel
HN
mit einem 1,3-Dien, gewöhnlich in Gegenwart eines stark alkalischen Katalysators, wie Natriummetall, hergestellt werden. Diese Umsetzung ist eine typische 1,4-Additionsreaktion.
Die erfindungsgemäßen Amide der Formel I weisen gegenüber bekannten Amiden eine bessere Hydrolyse beständigkeit auf. Zur Erläuterung ist in der Zeichnung die Hydrolysegeschwindigkeit bei Rückflußtemperatur von N-il.l-Dimethyl-S-dimethylaminopropylJ-acrylarnid (Verbindungl) und N-(3-Dimethylaminopropyl)-acrylamid (Verbindung II) in lOprozentiger wäßriger Lösung zugegeben. Aus der Zeichnung ist zu ersehen, daß die erfindungsgemäße Verbindung I aer bekannten Verbindung Il deutlich überlegen ist.
Die Herstellung der Acrylamidoverbindungen der Erfindung wird durch die folgenden Beispiele erläutert. 5s Teile und Prozentangaben beziehen sich auf das Gewicht, sofern nichts anderes angegeben ist.
Beispiel 1
Ein Gemisch aus 144,7 Teilen (0,63 Mo!) N-(I1I-Di- (.0 rnethyl-3-dimethylaminobutyl)-3-methoxypropionamiu, 1 Teil festem Natriumhydroxid und 1 Teil Hydrochinon wird in einen Reaktionsbehälter gegeben, der mit einem Kühler mit einer durch Trockeneis gekühlten Vorlage, einem Rührwerk und einer Einrichtung zur Steuerung (15 der Temperatur ausgerüstet ist. Der Druck in de»n Behälter wird auf weniger als 5 Torr vermindert, und der Behälter wird auf 8O0C erhitzt. Es setzt eine heftige Reaktion ein, und In der Vorlage kondensiert sich eine Flüssigkeit. Nach etwa 30 Minuten wird die Temperatur auf 9O0C erhöht und 3 Stunden bei diesem Wert gehalten. Das gebildete N-(l,l-Dimethyl-3-dimethylaminobuty!)-acrylamid siedet bei 80 bis 9i°C/0,3 bis 0,4 Torr. Ausbeute 109,1 Teile (87,4 Prozent der Theorie). Die Verbindung enthält 14,1 Prozent Stickstoff.
Beispiel 2
Ein Gemisch aus 273 Teilen (4 Mol) isopren und 2 Teilen (0,087 Mol) Natriummetall wird bei 00C innerhalb einer Stunde mit 180 Teilen (4 Mol) Dimethylamin versetzt. Die Temperatur wird durch Kühlung mit einer mit Trockeneis und Isopropanol gefüllten Kühlschlange unter 12C gehalten. Nach beendeter Zugabe des Dimethylamins wird das Gemisch weitere 3'/2 Stunden gerührt und gekühlt. Dann werden 6 Teile Methanol zugegeben, um das Natrium aufzulösen, und das Gemisch wird destilliert. Die bei 117,5 bis 119,5 C siedende Fraktion ist das l-Dimethylamino-3-methv1 2 kiten.
Ein Behälter aus einem Kunst^'Oi'r wird auf 0 C abgekühlt und mit 450 g (8.5 MoH Acrylnitril. 1020 g (10 Mol) Schwefelsäure und 37 g Wasser beschickt. Dann w iid dieses Gemisch mit 47 5 g (4.2 Mol) des erhaltenen l-Dimeih_\liimino-3-methyl-2-buiens sowie 8,5 g 2,6-Ditert.-butyl-p-kresol versetzt. Das Gemisch wird etwa i Stunde bei 68C C gerührt und danach mit etwa 30prozentiger Natronlauge neutralisiert. Die organische .Schicht wird abgetrennt, mit 2050 ml Methanol verdünnt und mit Ammoniak neutralisiert. Danach werden 1000 mi Methanol zugegeben, und die Lösung wird filtriert. Aus dem Filtrat wird das Methanol abdestilliert und der Rückstand unter vermindertem Druck destilliert. Es werden 400g (64,5% der Theorie) N-(IJ-Dinieth\l-3-dimethylaminopropyl)-acrylamid vom Siedepunkt 75 bis 92 C bei 0.25 bis 0,9 Torr erhalten. Das Produkt enthält 15,4% Stickstoff, der theoretische Wert beträgt 15,2υ/ο.
Die auf die vorstehend beschriebene Weise hergestellten Aminoverbindungen können durch Umsetzung mit einer geeigneten Säure in ein Aminsalz oder durch Umsetzung z. B. mit einem Alkylhalogenid oder -sulfat in die quartären Ammoniumsalze übergeführt werden. Dies wird in dem folgenden Beispiel erläutert.
Beispiel 3
2,8 g (0,197 Mol) Methyljodid werden zu einer Lösung von 3,6g (0,0182 Mol) N-(i,l-Dimethyl-3-dimethylaminobutyl)-acrylamid in 10 ml Benzol gegeben. Es setzt eine exotherme Reaktion ein, wobei die Temperatur des Gemisches durch äußere Kühlung bei 25 bis 300C gehalten wird. Nach 16- bis 18stündigem Rühren scheidet sich ein schmieriger Feststoff aus. Dieser Feststoff wird abgetrennt und aus einer Mischung von Methanol und Benzol umkristallisiert. Ausbeute 4,7 g Trimethyl-3-(l -acrylamido-1,1 -dimethylbutyl)-ammoniumjodid. Die Verbindung enthält 12,2% Stickstoff.
Die A.crylamidoverbindungen der Erfindung lassen sich entweder allein oder mit anderen polymerisierbaren Monomeren unter Bildung von Homopolymerisa ten, Copolymerisaten, Terpolymerisaten und anderen Unterpolymerisaten polymerisieren.
Durch Einbau der Acrylamidoverbindunger. der Erfindung in Acrylnitril-Polymerisate wild deren Anfärbbarkeit verbessert. Auch die Anfärbbarkeit von Polypropylen wird durch Behandlung mit den Polymerisaten der Erfindung verbessert.
Die aus den Acrylamidoverbindungen der Erfindung erhaltenen Polymerisate sind auch wertvoll zur Verbesserung der Trockenfestigkeit und Naßfestigkeit von Papier.
Die unter Verwendung erfindungsgemäßer Amide hergestellten Polymerisate mit quartären Ammoniumgruppen eignen sich auch als Ausflockungsmittel für rohes Abwasser.
Da die Acrylamidverbindungen der Erfindung durch Photopolymerisation polymerisiert werden können, eignen sie sich auch für Lichtdruckformen (Photogravüren) und photographische Methoden.
Sie können auch mit Vernetzern, wie Divinylbenzol, in Gegenwart von Suspendiermitteln, wie Benionit, unter Bildung von Anionenharzaustauschern copolymerisiert werden.
Hierzu 1 Blatt Zeichnungen

Claims (1)

Patentansprüche:
1. Amino- oder Ammoniumgruppen enthaltende Amide der Acryl- bzw. Methacrylsäure der Formel
Y R2 R4 O
IiI Ii
R1—CH-C—C—N—C-C-CH2 (1) R3 R5 H R6
DE19722214261 1969-06-11 1972-03-23 Amino- oder Ammoniumgruppen enthaltende Amide der Acryl- bzw. Methacrylsäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Polymerisaten Expired DE2214261C3 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US832412A US3666810A (en) 1969-06-11 1969-06-11 Novel n-3-aminoalkyl amides, polymers thereof, and method for their preparation
US203853A US3883491A (en) 1969-06-11 1971-12-01 Novel N-3-aminoalkyl amides, polymers thereof, and method for their preparation
DE19722214261 DE2214261C3 (de) 1972-03-23 Amino- oder Ammoniumgruppen enthaltende Amide der Acryl- bzw. Methacrylsäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Polymerisaten
DE2233337*A DE2233337A1 (de) 1969-06-11 1972-03-23 Polymerisate von amiden und ihre verwendung als flockungsmittel
US00237871A US3856689A (en) 1969-06-11 1972-03-24 Oil-soluble polymers of n-3-aminoalkyl acrylamides, and lubricants containing them
US00292697A US3761407A (en) 1969-06-11 1972-09-27 Quaternized n aminoalkyl acrylamide polymers in flocculation of suspended solids from water
US05/455,162 US3979441A (en) 1969-06-11 1974-03-27 Oil-soluble polymers of N-3-aminoalkyl acrylamides, and lubricants containing them

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83241269A 1969-06-11 1969-06-11
DE19722214261 DE2214261C3 (de) 1972-03-23 Amino- oder Ammoniumgruppen enthaltende Amide der Acryl- bzw. Methacrylsäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Polymerisaten

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DE2214261A1 DE2214261A1 (de) 1973-10-04
DE2214261B2 true DE2214261B2 (de) 1976-12-02
DE2214261C3 DE2214261C3 (de) 1977-07-21

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