DE1545748A1 - Process for the production of aziridinylaethers - Google Patents
Process for the production of aziridinylaethersInfo
- Publication number
- DE1545748A1 DE1545748A1 DE19651545748 DE1545748A DE1545748A1 DE 1545748 A1 DE1545748 A1 DE 1545748A1 DE 19651545748 DE19651545748 DE 19651545748 DE 1545748 A DE1545748 A DE 1545748A DE 1545748 A1 DE1545748 A1 DE 1545748A1
- Authority
- DE
- Germany
- Prior art keywords
- aziridine
- diglycidyl ether
- moles
- aziridinyl
- formula
- 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.)
- Pending
Links
Classifications
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/64—Amino alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/10—Radicals substituted by singly bound oxygen atoms
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/506—Amines heterocyclic containing only nitrogen as a heteroatom having one nitrogen atom in the ring
- C08G59/5066—Aziridines or their derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Description
Dipl.-Ing.F.Weickmann, Dr. Ing. A/Weickmann, Dipl-iwi». Ai. ,,...Jmann Dipl.-Phys. Dr. K. Fincke Patentanwälte λ r / ir η ro Dipl.-Ing.F.Weickmann, Dr. Ing. A / Weickmann, Dipl-iwi ». Ai . ,, ... Jmann Dipl.-Phys. Dr. K. Fincke Patent Attorneys λ r / ir η ro
CIlB 8 MÜNCHEN 27, MCIHLSTRASSE 22, RUFNUMMER 483921/22 I ' CIlB 8 MÜNCHEN 27, MCIHLSTRASSE 22, CALL NUMBER 483921/22 I '
HE DOW- CHEKICAl COMPAlIY, MIDLAND, MICHIGM -HE DOW- CHEKICAl COMPAlIY, MIDLAND, MICHIGM -
Verfahren zur Herstellung von AziridinyläthernProcess for the preparation of aziridinyl ethers
Die Erfindung betrifft ein Verfahren zur Herstellung von Aziridinyläthern, nämlich Bis-(3-aziridinyl-2-hydroxypropyl)äthern der allgemeinen FormelThe invention relates to a method for producing Aziridinyl ethers, namely bis (3-aziridinyl-2-hydroxypropyl) ethers the general formula
NCH2CHOHCH2O ('11O)3nCH2CHOHC HNCH 2 CHOHCH 2 O ('11O) 3n CH 2 CHOHC H
v/orin R ein zweiwertiger Kohlenwasserstoffrest mit 2 Ms 15 kohlenstoffatomen, η eine ganze Zahl von 0 bis 4 und π eine ^anze Zahl von 0 bis 10 sind.v / orin R is a divalent hydrocarbon radical with 2 Ms 15 carbon atoms, η is an integer from 0 to 4 and π is a number from 0 to 10.
BAD OBiGlNALBAD OBiGlNAL
909831 /1516909831/1516
Bevorzugte Verbindungen, die unter diese Charakterisierung fallen, sind diejenigen, in denen R durch die 'Jegnahme der zwei OH-(Jruppen des Bisphenols darstellbar ist, in denen m 0 oder 1 ist und in denen RO der Rest -CgEL-C(CH^)o-C6H4-O-CH2CHOHCH2-O-ist. Insbesondere betrifft die Erfindung die Herstellung der Verbindungen Bis-/~3- (1 -aziridinyl) -2-hydroxypropyl_J7äther und 2,2,-Bis/~p- 3-(1 -aziridinyl)^-hyaroxypropoxyphenylj/ propan.Preferred compounds that fall under this characterization are those in which R can be represented by the removal of the two OH- (J groups of bisphenol, in which m is 0 or 1 and in which RO is the radical -CgEL-C (CH ^ ) oC 6 H 4 -O-CH 2 CHOHCH 2 -O-. In particular, the invention relates to the preparation of the compounds of bis / ~ 3- (1 -aziridinyl) -2-hydroxypropyl_J7äther and 2,2-bis / ~ p - 3- (1 -aziridinyl) ^ - hyaroxypropoxyphenylj / propane.
Die erfindungsgemäß herzustellenden Äther können auf verschiedene Weise gewonnen v/erden.The ethers to be produced according to the invention can be different Way won v / earth.
Eine Art der Synthetisierung besteht darin, do λ das Aziridin mit dem jeweiligen Di0 -IyOidylather umgesetzt wird. Diese Synthese wird a im folgenden noch ni-.her erläutert. One type of synthesis is to do λ the aziridine is reacted with the respective Di 0 - IyOidylather. This synthesis is explained in more detail below.
Nach einem anderen Verfahren wird das Aziridin mit einem entsprechenden Bis(halogenhydrin)äther in aeger.w^rt eines Säurealczeptors durchgeführt.Another method is the aziridine with a corresponding bis (halohydrin) ether in aeger.w ^ rt an acid acceptor carried out.
Wieder eine andere Ϊ-Iethode besteht d;..rin, daß -^zi mit Epichlorhydrin umzusetzen und dieaes letztere :;o mit dem Diol HO(RO) H in Gegenwart von Alkali umr.nz^ Yet another Ϊ-Iethode is d; .. rin that - ^ zi react with epichlorohydrin and dieaes latter: o umr.nz with the diol HO (RO) H in the presence of alkali ^
909831/1516909831/1516
Die "bevorzugte Synthese "besteht darin, daß man einen Diglycidyläther mit zwei Hol Aziridin umsetzt und zwar einen Diglycidyläther der FormelThe "preferred synthesis" is that one Diglycidyl ether reacts with two Hol aziridine, namely a diglycidyl ether of the formula
■ CH2-CII2CH2O (RO ^CH2CHC2
/ " \/■ CH 2 -CII 2 CH 2 O (RO ^ CH 2 CHC 2
/ "\ /
o o ■o o ■
in der m und H die ölen angegebenen Bedeutungen haben.in which m and H have the meanings given for oils.
Geeignete Äther sind der eigentliche Diglycidyläther selbst und die Diglycidyläther von Diolen, wie z.B. von A'thylenglycol, von Diilthylenglycol, von Polyäthylenglycolen nit "bis zu 10 und mehr O:r;öthylengruppen, von 1,2- und 1,3-Propylenglycolen und den entsprechenden ■Toiypropyler.glycolen mit bis zu 10 und mehr Oxypropylengrurpen, von ',■■-- und 2,3-!3utylenglycolen, von Polybutylenglycolen mit bis zu 10 und mehr Oxybutylengruppen, von den höheren All-rylenglycolen rr.it "his zu 15 und mehr kohlenstoffatomen, von Arylendiolen, wie z.B. von o-, m- und c-Dih;;äroxybenzol, von -^isphenolen, wie z.B. vor. 0::yl ic phenol, von Thiobisphenol, von ^iphenol, von Alkylenbisrhennlen, insbesondere von Iletliylenbisj'heziole?:, vor: Z30,:r^ "Ii li::;i;: ;;l:pi:.ol^n, von Zyklo::e;:ylidinbisr-i:i-2^olen uii-i von ähnlichen. Die ■;.roir.iitiache Ringe entiiuli,ei:u.ei: A't-hcr können im allgemeinen in o-, m- oder r-Stellun^ substituiert sein, ohne daiS dies einen jro^eii Einfluß hätte.Suitable ethers are the actual diglycidyl ether itself and the diglycidyl ethers of diols, such as, for example, of ethylene glycol, of ethylene glycol, of polyethylene glycols with up to 10 and more O: r; ethylene groups, of 1,2- and 1,3-propylene glycols and the corresponding Toiypropyl glycols with up to 10 and more oxypropylene groups, of ', ■■ - and 2,3-! 3utylene glycols, of polybutylene glycols with up to 10 and more oxybutylene groups, of the higher all-rylene glycols rr.it "his to 15 or more carbon atoms, of arylene diols, such as o-, m- and c-Dih ;; aroxybenzene, of - ^ isphenols, such as before. 0 :: yl ic phenol, from Thiobisphenol, from ^ iphenol, from Alkylenbisrhennlen, especially from Iletliylenbisj'heziole?:, Before: Z30,: r ^ "Ii li :: ; i ;: ;; l: pi: .ol ^ n, from cyclo :: e;: ylidinbisr-i: i-2 ^ olen uii-i of similar -, m- or r-position, without this having a jro ^ eii influence.
909831/1516909831/1516
BADBATH
Als Aziridinreaktionsteilnehmer wird entweder - bevorzugt · Aziridin selbst oder ein C-alkylaziridin verwendet. Wenn auch das substituierte Aziridin den Vorzug verdient, so können doch auch Alkylaziridine verwendet werden, z.B. 2-methylaziridin, 2-äthylaziridin und die Isomeren von 2-butylaziridin.Either - preferably aziridine itself or a C-alkylaziridine is used as the aziridine reactant. if the substituted aziridine also deserves preference, but alkylaziridines can also be used, e.g. 2-methylaziridine, 2-äthylaziridine and the isomers of 2-butylaziridine.
Die Reaktion zwischen dem Diglycidyläther und dem Aziridin kann leicht dadurch ausgelöst werden, daß man die Reaktionsteilnehmer miteinander vermischt und erhitzt. Mindestens zwei Mol Aziridin sollten, pro Mol Diglycidyläther verwendet werden; gewöhnlich arbeitet man mit erheblichem Aziridinüberschußj man beschleunigt dadurch die Reaktion und erreicht mit Sicherheit vollständige Umsetzung des Diglycidyläthers. Da es leicht zu verflüchtigen ist, läßt sich das überschüssige Aziridin ohne weiteres abtrennen und wiedergewinnen. Grundsätzlich ist kein Katalysator erforderlich; es kann aber ein alkalischer Katalysator, z.B. ein tertiäres Amin oder ein Alkali verwendet werden. Bei Temperaturen von 50 bis 100 G ergeben sich auch in Abwesenheit eines Katalysators brauchbare Reaktionsgeschwindigkeiten,The reaction between the diglycidyl ether and the aziridine can easily be initiated by one of the reactants mixed together and heated. At least two moles of aziridine should be used per mole of diglycidyl ether be used; Usually one works with a considerable excess of aziridine, which speeds up the process the reaction and achieved with certainty complete implementation of the diglycidyl ether. Because it is easy to volatilize is, the excess aziridine can be easily separated and recovered. Basically no catalyst is required; but it can be an alkaline catalyst, for example a tertiary amine or an alkali can be used. At temperatures of 50 to 100 G, even in the absence of one Catalyst usable reaction rates,
Die folgenden Beispiele erläutern die Srfijdung.The following examples explain the concept.
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BAD ORIGINALBATH ORIGINAL
Beispiel 1 Bis-/~3-(1-aziridinyl)-2-hydroxypropyl_7äther Ein Gemisch von 370,9 g Aziridin (Äthylenimin) und 50,5 g Diglycidyläther wurden vier Stunden lang bei 6O0C und Atmosphärendruck in einer Stickstoffatmosphäre im Rückfluß umgewälzt. Die Temperatur wurde dann auf 5O0C abgesenkt und auf diesem Wert gehalten, während das nicht zur Reaktion gekommene Aziridin durch Druckminderung abdestilliert wurde. Das dabei in quantitativer Ausbeute erhaltene Produkt Example 1 Bis- / ~ 3- (1-aziridinyl) -2-hydroxypropyl_7äther A mixture of 370.9 g of aziridine (ethyleneimine) and 50.5 g diglycidyl ether were tumbled for four hours at 6O 0 C and atmospheric pressure in a nitrogen atmosphere at reflux . The temperature was then lowered to 5O 0 C and maintained at that value, while the non-reaction has come to the aziridine was distilled off by pressure reduction. The product obtained in quantitative yield
20 war eine Flüssigkeit mit einem Brechungsindex η von 1,4732 und einem Analysenwert von 37,7 fo Aziridinylgruppen (GpH JT); demgegenüber beträgt der theoretische viert ^8,9 a>. Das Infrarotspektrum bestätigte die vermutete Struktur.20 was a liquid with a refractive index η of 1.4732 and an analytical value of 37.7 fo aziridinyl groups (GpH JT); In contrast, the theoretical fourth is ^ 8.9 a>. The infrared spectrum confirmed the suspected structure.
Beispiel 2 2,2-Bis-/~p- 3(1-aziridinyl)-2-hydroxypropyoxyphenyl_ypr ο pan Example 2 2,2-bis - / ~ p- 3 (1-aziridinyl) -2-hydroxypropyoxyphenyl_ypr ο pan
Ein Gemisch von 102 g des Diglycidyläthers von Bisphenol A und 200 ml Aziridin wurde gemäß Beispiel 1 umgesetzt. Man erhielt einen weißen Feststoff mit einem Schmelzpunkt bei 113 bis 115°0 und mit einem Gehalt -von 19,2 fo Aziridinylgruppen. Demgegenüber beträgt der theoretische Wert 20,2 %. A mixture of 102 g of the diglycidyl ether of bisphenol A and 200 ml of aziridine was reacted according to Example 1. A white solid was obtained having a melting point at 113 to 115 ° 0, and with a content -from 19.2 fo aziridinyl. In contrast, the theoretical value is 20.2 %.
Der verwendete Diglycidyläther hatte die Formel CH2-CHCH2O-^-C (CH5 )2-j2i-OCH2CHThe diglycidyl ether used had the formula CH 2 -CHCH 2 O - ^ - C (CH 5 ) 2 -j2i-OCH 2 CH
in der 0 einen p-Phenylenreat bedeutet. An seiner Stelle können auch Epoxyharze (Diglycidyläther), die vonin which 0 means a p-Phenylenreat. Epoxy resins (diglycidyl ether) produced by
909831/1516
BAD GRtGtNAt 909831/1516
BAD GRtGtNAt
Bisphenol A abgeleitet sind und typischerweise das BindegliedBisphenol A are derived and typically the link
enthalten, mit χ in der Bedeutung einer ganzen Zahl von 1 bis 10 und darüber, verwendet werden. Diese Harze sind im Handel erhältlich und können leicht gewonnen werden durch Umsetzen des Diglycidyläthers von Bisphenol A mit der richtigen Menge von Bisphenol A. Analoge und ebenfalls geeignete Diglycidylüther können aus anderen Bisphenolen gewonnen werden.included, with χ meaning an integer from 1 to 10 and above can be used. These resins are commercially available and can be easily are obtained by reacting the diglycidyl ether of bisphenol A with the correct amount of bisphenol A. Analogous and likewise suitable diglycidyl ethers can can be obtained from other bisphenols.
Die erfindungsgemäß gewonnenen Verbindungen sind als Bakterizide und Desinfektionsmittel geeignet. Sie sind in hohem Maße toxisch gegenüber vielen pathogenen Bakterien. Dies wurde wie folgt nachgewiesen: Eine mit einem liähragar beschichtete Platte wurde streifenförmig mit der nach Beispiel 1 gewonnenen Verbindung behandelt und dann quer zu diesen Streifen mit einer Kultur von E. CoIi. Diese Platte wurde anschließend 72 Stunden lang einer Temperatur von 250C ausgesetzt. In den infizierten Streifen trat ein üppiges Bakterienwachstum ein mit Ausnahme derjenigen Stellen, in denen die infizierten Streifen sieh mit dem chemisch behandelten Streifen kreuzten. Dort zeigte sich kein Bakterienwachstum. Ähnliche Resultate erhielt man, wenn man andere Bakterien mit den erfindungsgemäß hergestellten Verbindungen bekämpfte.The compounds obtained according to the invention are suitable as bactericides and disinfectants. They are highly toxic to many pathogenic bacteria. This was demonstrated as follows: A plate coated with a liquid agar was treated in strips with the compound obtained according to Example 1 and then across these strips with a culture of E. Coli. This plate was then exposed to a temperature of 25 ° C. for 72 hours. Bacterial growth was abundant in the infected strips, with the exception of those locations where the infected strips intersected with the chemically treated strip. There was no bacterial growth there. Similar results were obtained when controlling other bacteria with the compounds prepared according to the invention.
909831/1516909831/1516
BAD ORiGlNAtBAD ORiGlNAt
Infolge des Vorhandenseins der beiden Aziridingruppen können die erfindungsgemäß hergestellten Verbindungen
allein oder in Gemisch mit anderen Polymeren polymerisiert werden unter Bildung von festen Harzen* Auch
sind die erfindungsgemäß hergestellten Verbindungen
als Katalysatoren von Polyurethan und Epoxyharze
verwendbar.As a result of the presence of the two aziridine groups, the compounds prepared according to the invention can be polymerized alone or in a mixture with other polymers with the formation of solid resins * Also
are the compounds prepared according to the invention
as catalysts of polyurethane and epoxy resins
usable.
909831/1516
BAD ORIGINAL909831/1516
BATH ORIGINAL
Claims (4)
daß man die Reaktion in Gegenwart eines Säureakzeptors durchführt.2. The method according to claim 1, characterized in that
that the reaction is carried out in the presence of an acid acceptor.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40022764A | 1964-09-29 | 1964-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1545748A1 true DE1545748A1 (en) | 1969-07-31 |
Family
ID=23582733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545748 Pending DE1545748A1 (en) | 1964-09-29 | 1965-08-20 | Process for the production of aziridinylaethers |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE670264A (en) |
| DE (1) | DE1545748A1 (en) |
| GB (1) | GB1117780A (en) |
| NL (1) | NL6512597A (en) |
-
1965
- 1965-08-20 DE DE19651545748 patent/DE1545748A1/en active Pending
- 1965-09-27 GB GB4103265A patent/GB1117780A/en not_active Expired
- 1965-09-29 NL NL6512597A patent/NL6512597A/xx unknown
- 1965-09-29 BE BE670264D patent/BE670264A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1117780A (en) | 1968-06-26 |
| BE670264A (en) | 1966-03-29 |
| NL6512597A (en) | 1966-03-30 |
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