DE918983C - Process for the preparation of derivatives of the urethanes esterified with glycols and disubstituted on the nitrogen - Google Patents

Process for the preparation of derivatives of the urethanes esterified with glycols and disubstituted on the nitrogen

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Publication number
DE918983C
DE918983C DES33677A DES0033677A DE918983C DE 918983 C DE918983 C DE 918983C DE S33677 A DES33677 A DE S33677A DE S0033677 A DES0033677 A DE S0033677A DE 918983 C DE918983 C DE 918983C
Authority
DE
Germany
Prior art keywords
disubstituted
nitrogen
urethanes
esterified
glycols
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
DES33677A
Other languages
German (de)
Inventor
Marcel Jean Viard
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.)
Compagnie de Saint Gobain SA
Original Assignee
Compagnie de Saint Gobain SA
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 Compagnie de Saint Gobain SA filed Critical Compagnie de Saint Gobain SA
Application granted granted Critical
Publication of DE918983C publication Critical patent/DE918983C/en
Expired legal-status Critical Current

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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
    • 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
    • C08G12/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urethanes or thiourethanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

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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 Derivaten der mit Glykolen veresterten, am Stickstoff disubstituierten Urethane Die Erfindung betrifft die Herstellung von Derivaten der mit Glykolen veresterten, am Stickstoff disubstituierten Urethane, wobei man diese mit Aldehyden in Gegenwart eines sauren Katalysators umsetzt, in der Kälte arbeitet und auf i Mol Aldehyd i Mol Urethan anwendet. Der Aldehyd kann nur mit der OH-Gruppe des am Stickstoff disubstituierten Urethans reagieren unter Bildung einer Verbindung vom Halbacetaltyp folgender allgemeiner Formel in der die Substituenten folgende Bedeutung haben: R, R1 und R, sind einwertige aliphatische, arylaliphatische, aromatische oder alicyclische Radikale. R kann auch Wasserstoff sein, R3 ist ein Alkylenradikal. Die Verfahrensprodukte dienen als Ausgangsstoffe für die Herstellung von Kunststoffen.Process for the preparation of derivatives of the urethanes esterified with glycols, disubstituted on the nitrogen The invention relates to the preparation of derivatives of the urethanes esterified with glycols, disubstituted on the nitrogen Mole of aldehyde i mole of urethane applies. The aldehyde can only react with the OH group of the urethane disubstituted on the nitrogen to form a compound of the hemiacetal type with the following general formula in which the substituents have the following meanings: R, R1 and R are monovalent aliphatic, arylaliphatic, aromatic or alicyclic radicals. R can also be hydrogen, R3 is an alkylene radical. The process products serve as starting materials for the manufacture of plastics.

Beispiel 133 g (I Mol) N-Dimethylurethan des Glykols werden mit ioo cm3 wäßriger 3o°/oiger Formalinlösung (i Mol) unter Zusatz von 6 cm3 Salzsäure (22°B6) umgesetzt. Nach 8 Stunden ist die Reaktion beendet. Die Analyse ergibt nur noch o,2 g freien Formaldehyd.Example 133 g (I mol) of N-dimethyl urethane of glycol are with ioo cm3 aqueous 30% formalin solution (1 mol) with the addition of 6 cm3 hydrochloric acid (22 ° B6) implemented. The reaction has ended after 8 hours. The analysis only reveals 0.2 g of free formaldehyde.

Der erhaltene Stoff hat die folgende Formel Er kann nicht, auch nicht unter vermindertem Druck, destilliert werden, da sonst unter Abgabe von Formaldehyd Zersetzung eintritt.The obtained substance has the following formula It cannot be distilled, not even under reduced pressure, as otherwise decomposition occurs with the release of formaldehyde.

Werden i Mol Aldehyd mit 2 Molen Urethan umgesetzt, so werden acetalartige Verbindungen folgender Art erhalten In dieser Formel haben R, R1, R2 und R3 die oben angegebene Bedeutung.If 1 mole of aldehyde is reacted with 2 moles of urethane, acetal-like compounds of the following type are obtained In this formula, R, R1, R2 and R3 have the meaning given above.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung von Derivaten der mit Glykolen veresterten, am Stickstoff disubstituierten N-Urethane, dadurch gekennzeichnet, daß man diese mit Aldehyden in Gegenwart eines sauren Katalysators umsetzt, wobei in der Kälte gearbeitet und auf i Mol Aldehyd i Mol Urethan angewandt wird. PATENT CLAIMS: i. Process for the preparation of derivatives of the N-urethanes esterified with glycols and disubstituted on the nitrogen, characterized in that they are reacted with aldehydes in the presence of an acidic catalyst, working in the cold and using 1 mole of urethane for 1 mole of aldehyde. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß in wäßrigem Medium gearbeitet wird,2. The method according to claim i, characterized in that in an aqueous medium is being worked
DES33677A 1951-01-03 1951-12-30 Process for the preparation of derivatives of the urethanes esterified with glycols and disubstituted on the nitrogen Expired DE918983C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR918983X 1951-01-03

Publications (1)

Publication Number Publication Date
DE918983C true DE918983C (en) 1954-10-11

Family

ID=9424767

Family Applications (1)

Application Number Title Priority Date Filing Date
DES33677A Expired DE918983C (en) 1951-01-03 1951-12-30 Process for the preparation of derivatives of the urethanes esterified with glycols and disubstituted on the nitrogen

Country Status (1)

Country Link
DE (1) DE918983C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3142699A (en) * 1958-04-24 1964-07-28 Bayer Ag Urethane compounds and process therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3142699A (en) * 1958-04-24 1964-07-28 Bayer Ag Urethane compounds and process therefor

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