DE1932306A1 - N-glycidyl glycolurils from clycolurils and epichlorohy - drin - Google Patents

N-glycidyl glycolurils from clycolurils and epichlorohy - drin

Info

Publication number
DE1932306A1
DE1932306A1 DE19691932306 DE1932306A DE1932306A1 DE 1932306 A1 DE1932306 A1 DE 1932306A1 DE 19691932306 DE19691932306 DE 19691932306 DE 1932306 A DE1932306 A DE 1932306A DE 1932306 A1 DE1932306 A1 DE 1932306A1
Authority
DE
Germany
Prior art keywords
glycolurils
aralkyl
aryl
glycidyl
alkyl
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
Application number
DE19691932306
Other languages
German (de)
Inventor
Raubach Dipl-Chem Dr Heinz
Fedtke Dipl-Chem Dr Manfred
Teige Dipl-Chem Wolfgang
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.)
Akademie der Wissenschaften der DDR
Original Assignee
Akademie der Wissenschaften der DDR
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 Akademie der Wissenschaften der DDR filed Critical Akademie der Wissenschaften der DDR
Publication of DE1932306A1 publication Critical patent/DE1932306A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Abstract

N-glycidyl-glycolurils of formula I. (where R is N-substituted (cyclo)alkyl, aryl, aralkyl or H, m is zero, 1, 2 or 3, and R' is (cyclo)alkyl, aryl, aralkyl, furyl or H) are prepared by glycoluril/epichlorohydrin condensation, for example with NaOH at 100-115 C, and separated in the usual manner.

Description

Verfahren zur Herstellung von N-Glykoluril-Derivaten Die Erfindung betrifft ein Verfahren zur Herstellung von neuen N-Glykoluril-Derivaten.Process for the preparation of N-glycoluril derivatives The invention relates to a process for the production of new N-glycoluril derivatives.

N-Glykoluril-Derivate, denen das bicyclische Clykoluril-System, worin R' Wasserstoff, Alkyl, Cycloalkyl1 Aryl, Aralkyl oder Puryl bedeuten kann, zugrunde liegt, sind bekannt.N-Glykoluril-Derivate, which the bicyclic Clykoluril-System, in which R 'is based on hydrogen, alkyl, cycloalkyl1 aryl, aralkyl or puryl are known.

Als Ausgangsstoffe zur Herstellung der N-substituierten Derivate dienen die durch Umsetzung von Harnstoff bzw. substituierten Harnstoffen mit Glyoxal bzw. substituierten Glyoxalen auf direictem Wege oder Uber die entsprechenden Dihydroxyimidazolidinone leicht zugänglichen Glykolurile.Serve as starting materials for the production of the N-substituted derivatives the reaction of urea or substituted ureas with glyoxal or substituted glyoxals directly or via the corresponding dihydroxyimidazolidinones easily accessible glycolurils.

Bekannt sind beispielsweise N-Tetramethylol-glykolurile und N-Halogenderivate des Glykolurils sowie deren Verwendung als Textilhilfs-, Bleich- und Schädlingsbekärnpfungsmittel.For example, N-tetramethylol-glycolurils and N-halogen derivatives are known of glycoluril and its use as Textile auxiliaries, bleach and pesticides.

Auf Grund der technisch wertvollen Eigenschaften der bekannten N-Glykoluril-Derivate erscheint die Herstellung weiterer N-Glykoluril-Derivate wUnschenswert.Due to the technically valuable properties of the well-known N-glycoluril derivatives the production of further N-glycoluril derivatives appears to be desirable.

Der Erfindung liegt deshalb die Aufgabe zugrunde, ein Verfahren zur Herstellung von neuen N-Glykoluril-Derivaten zu entwickeln.The invention is therefore based on the object of providing a method for To develop production of new N-glycoluril derivatives.

Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß Glykolurile mit Epichlorhydrin umgesetzt und aus dem Reaktionsgemisch N-Glycidyl-glykolurile der allgemeinen Formel, worin R N-substituiertes Alkyl, Cycloalkyl, Aryl, Aralkyl oder Wasserstoff, m ganze Zahlen von 0 bis 3 R' Alkyl, Cycloalkyl, Aryl, Aralkyl, Puryl oder Wasserstoff bedeziten, in üblicher Weise isoliert werden.According to the invention, the object is achieved in that glycolurils are reacted with epichlorohydrin and N-glycidyl glycolurils of the general formula where R is N-substituted alkyl, cycloalkyl, aryl, aralkyl or hydrogen, m integers from 0 to 3 R 'alkyl, cycloalkyl, aryl, aralkyl, puryl or hydrogen denote, can be isolated in a customary manner.

N-Glycidylderivate von Glykolurilen sind neue Verbindungen, wobei sich durch die Variationsmöglichkeiten der Substituenten R und R' ein weiter Bereich von noch nicht völlig zu übersehenden Verwendungsmöglichkeiten erschließt.N-glycidyl derivatives of glycolurils are new compounds, whereby A wide range is possible due to the possible variations of the substituents R and R ' of not yet completely overlooked Uses opens up.

Das folgende Beispiel. erläutert die Erfindung anhand der Herstellung von 1.3-Di-n-propyl-5.7-diglycidyl-glykoluril. Die Herstellung anderer Derivate kann in sinngemäß gleicher Weise erfolgen.The following example. explains the invention on the basis of production of 1,3-di-n-propyl-5.7-diglycidyl-glycoluril. The manufacture of other derivatives can be done in the same way.

Beispiel 1.3-Di-n-propyl-5.7-diglycidyl-glykoluril 453 Gewichtsteile 1.3-Di-n-propyl-glykoluril werden in 3700 Gewichtsteilen Epichlorhydrin unter RUhren bei 100 bis 1150C gel8st. Zu der Lösung gibt man portionsweise 160 Gewichtsteile Natriumhydroxyd. Das bei der Jetzt einsetzenden Reaktion freiwerdende Wasser wird aseotrop abdestilliert. Nach Beendigung der Reaktion wird das gebildete Natriumchlorid abfiltriert und aus dem Filtrat nicht ungesetXes Epichlorhydrin abdestilliert.Example 1.3-Di-n-propyl-5.7-diglycidyl-glycoluril 453 parts by weight of 1,3-di-n-propyl-glycoluril are dissolved in 3700 parts by weight of epichlorohydrin with stirring at 100 to 1150C. 160 parts by weight of sodium hydroxide are added in portions to the solution. The water released during the reaction that now begins is distilled off aseotropically. After the reaction has ended, the sodium chloride formed is filtered off and non-unset epichlorohydrin is distilled off from the filtrate.

Der Rückstand beträgt 610 Gewichtsteile und ist eine hellgelbe viskose Flüssigkeit, die ein Epoxydäquivalentgewicht von 217 aufweise. Die Flüssigkeit läßt sich im Hochvakuum destillieren; sie geht in der Kurzwegdistillation bei Kp. 0,006 210° fast unzersetzt als wasserklare farblose Substanz mit folgenden Kenndaten über: D420 1,1979 nD25 1,5082, EAG 185The residue is 610 parts by weight and is a light yellow viscous one Liquid that has an epoxy equivalent weight of 217. The liquid leaves distill themselves in a high vacuum; it goes in the short-path distillation at bp 0.006 210 ° almost undecomposed as a clear, colorless substance with the following characteristics: D420 1.1979 nD25 1.5082, EAG 185

Claims (2)

PatentansprUche: 1. Verfahren zur Herstellung von N"Glykoluril-Derivaten, dadurch gekennzeichnet, daß Glykolurile mit Epichlorhydrin umgesetzt und aus dem Reaktionsgemisch N-Glycidyl-glykolurile der allgemeinen Formel, worin R N-substituiertes Alkyl, Cycloalkyl, Aryl, Aralkyl oder Wasserstoff, m ganze Zahlen von 0 bis 3 und R' Alkyl, Cycloalkyl, Aryl, Aralkyl, Furyl oder Wasserstoff bedeuten, in üblicher Weise isoliert werden.Claims: 1. Process for the preparation of N "glycoluril derivatives, characterized in that glycolurils are reacted with epichlorohydrin and N-glycidyl-glycolurils of the general formula in which R is N-substituted alkyl, cycloalkyl, aryl, aralkyl or hydrogen, m is integers from 0 to 3 and R 'is alkyl, cycloalkyl, aryl, aralkyl, furyl or hydrogen, are isolated in the customary manner. 2. N-Glycidyl-glykolurile der allgemeinen Formel, worin R N-substituiertes Alkyl, Cycloalkyl, Aryl, Aralkyl oder Wasserstoff, m ganze Zahlen von 0 bis 3 und R' Alkyl, Cycloalkyl, Aryl, Aralkyl, Furyl oder Wasserstoff bedeuten.2. N-glycidyl glycolurils of the general formula, where R is N-substituted alkyl, cycloalkyl, aryl, aralkyl or hydrogen, m is integers from 0 to 3 and R 'is alkyl, cycloalkyl, aryl, aralkyl, furyl or hydrogen.
DE19691932306 1968-09-13 1969-06-26 N-glycidyl glycolurils from clycolurils and epichlorohy - drin Pending DE1932306A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DD13471968 1968-09-13

Publications (1)

Publication Number Publication Date
DE1932306A1 true DE1932306A1 (en) 1970-03-19

Family

ID=5480386

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19691932306 Pending DE1932306A1 (en) 1968-09-13 1969-06-26 N-glycidyl glycolurils from clycolurils and epichlorohy - drin

Country Status (3)

Country Link
AT (1) AT293417B (en)
CH (1) CH517112A (en)
DE (1) DE1932306A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2217914A1 (en) * 1971-04-14 1972-11-09 Ciba-Geigy Ag, Basel (Schweiz) New heterocyclic triglycidyl compounds
JP2015120885A (en) * 2013-11-19 2015-07-02 四国化成工業株式会社 Epoxy resin composition for semiconductor encapsulation and semiconductor device
JP2015120889A (en) * 2013-11-20 2015-07-02 四国化成工業株式会社 Epoxy resin composition and optical semiconductor device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2217914A1 (en) * 1971-04-14 1972-11-09 Ciba-Geigy Ag, Basel (Schweiz) New heterocyclic triglycidyl compounds
JP2015120885A (en) * 2013-11-19 2015-07-02 四国化成工業株式会社 Epoxy resin composition for semiconductor encapsulation and semiconductor device
JP2015120889A (en) * 2013-11-20 2015-07-02 四国化成工業株式会社 Epoxy resin composition and optical semiconductor device

Also Published As

Publication number Publication date
CH517112A (en) 1971-12-31
AT293417B (en) 1971-09-15

Similar Documents

Publication Publication Date Title
DE1932306A1 (en) N-glycidyl glycolurils from clycolurils and epichlorohy - drin
DE3225818A1 (en) Process for the preparation of spiroorthocarbonates
DE1720124C3 (en) Metal complexes as IR absorbers
DE1468842C3 (en) Phenylenediamines
DE1156809B (en) Process for the preparation of cyanoalkylfluorosilanes
DE2152686A1 (en) New derivatives of diaethanolamine and morpholine and processes for their preparation
DE1444866A1 (en) Improvements in and related to functional fluids
DE2521347B2 (en) Hydroxyl-substituted 2-chloro-a - (tert-butylaminomethyl-benzyl alcohols, manufacturing processes and pharmaceuticals
DE2064956B2 (en) N-heterocyclic mono- or dialcohols and processes for their preparation
DE1643784C (en) Biologically active isothiocyanates and processes for their preparation
CH500221A (en) N-disubstd-3-amino-1 2-benzisothiazole derivs antimycotic
DE3220712C2 (en)
DE1470102A1 (en) 2-Hydroxymethyl-5-nitroimidazoles and process for their preparation
DE708678C (en) Process for the production of carboduemides
DE1643797A1 (en) New thionocarbamic acid esters and processes for their preparation
DE1158973B (en) Process for the preparation of di-silyl-substituted alkali amides
EP0006102A1 (en) 1-Hydroxymethylimidazoles, their preparation and use as chemical intermediates
AT242138B (en) Process for the preparation of new esters of quaternary ammonium compounds
AT220152B (en) Process for the preparation of new azetidines
DE1154107B (en) Process for the production of organomercury compounds
DE1249864B (en) Process for the production of cyclic organosilicon compounds
DE1695770A1 (en) Piperidine-N-oxyl-spiro-hydantoin derivatives and process for the preparation thereof
AT282594B (en) PROCESS FOR THE PREPARATION OF NEW RACEMIC OR OPTICALLY ACTIVE (1-2'-NITRILOPHENOXY) -2-HYDROXY-3-ISOPROPYLAMINOPROPANE AND ITS SALTS
DE952802C (en) Process for the production of vinyl compounds
DE2360679A1 (en) METHOD OF MANUFACTURING DIKETONS