DE519049C - Process for the preparation of condensation products from urea or its derivatives - Google Patents

Process for the preparation of condensation products from urea or its derivatives

Info

Publication number
DE519049C
DE519049C DE1930I0010230 DEI0010230D DE519049C DE 519049 C DE519049 C DE 519049C DE 1930I0010230 DE1930I0010230 DE 1930I0010230 DE I0010230 D DEI0010230 D DE I0010230D DE 519049 C DE519049 C DE 519049C
Authority
DE
Germany
Prior art keywords
urea
derivatives
condensation products
preparation
condensation
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
DE1930I0010230
Other languages
German (de)
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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
Priority to DEI29210D priority Critical patent/DE506963C/en
Priority claimed from DEI29210D external-priority patent/DE506963C/en
Priority to DEI29471D priority patent/DE508795C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DE1930I0010230 priority patent/DE519049C/en
Application granted granted Critical
Publication of DE519049C publication Critical patent/DE519049C/en
Expired legal-status Critical Current

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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Description

Verfahren zur Herstellung von Kondensationsprodukten aus Harnstoff oder seinen Derivaten Das Patent 5o6 963 beschreibt ein Verfahren, Kondensationsprodukte durch Kondensation von Harnstoff oder seinen Derivaten mit Alkoholen oder Ketonen zu gewinnen.Process for the production of condensation products from urea or its derivatives The patent 5o6 963 describes a process, condensation products by condensation of urea or its derivatives with alcohols or ketones to win.

Es wurde nun gefunden, daß bei Verwendung von hochpolymeren Alkoholen, z. B. Polyvinylalköhol, nicht ölige oder harzartige, sondern kautschukartige Kondensationsprodukte entstehen, die ganz anderen Verwendungszwecken zugeführt werden können.It has now been found that when using high polymer alcohols, z. B. polyvinyl alcohol, not oily or resinous, but rubber-like condensation products arise that can be used for completely different purposes.

Man kondensiert zweckmäßig bei Gegenwart von \\,asser oder Lösungsmitteln, welche einen besseren Kontakt der Komponenten gewährleisten. Es können auch solche Lösungsmittel oder solche nicht flüchtige Substanzen Verwendung finden, die wie z. B. Glykol, Glycerin, Sorbit entsprechend dem Patent 506963 mit Harnstoff reagieren. 111 diesem halle muß die Harnstoffmenge entsprechend erhöht werden. Nenn die Kondensation beendet ist, was an dein Nachlassen der Ainmoniakentwicklung festzustellen ist, kann unter Rühren das noch überschüssige: Lösungsmittel verdampft werden. Es hinterbleibt eine kautschukartige. äußerst elastische \Iasse, welche sich, wenn die Kondensation in Gegenwart von Wasser oder den obenerwähnten wasserlöslichen Zusatzstoffen vorgenommen wurde, in Wasser leicht löst. Die gewonnenen neurar Produkte können vielfache Verwendung finden: als elastisch machende Zusätze für Eiweißstoffe oder Celluloseester und -iither sowie als Fiirlicr"ihilfsprodukte, z. B. für Kunstseidenschlichte. Textildruckerei o. dgl.It is advisable to condense in the presence of water or solvents which ensure better contact between the components. It can also be found such solvents or such non-volatile substances use such. B. glycol, glycerin, sorbitol according to the patent 506963 react with urea. In this hall, the amount of urea must be increased accordingly. If the condensation has ended, which can be seen from the decrease in the development of ammonia, the excess solvent can be evaporated with stirring. What remains is a rubbery one. extremely elastic mass, which, if the condensation has been carried out in the presence of water or the above-mentioned water-soluble additives, easily dissolves in water. The neurar products obtained can be used in many ways: as elastic additives for protein substances or cellulose esters and cellulose ethers and as auxiliary products, e.g. for rayon sizing, textile printing or the like.

Beispiel i a7o Gewichtsteile Polyvinylalkoliol werden mit 360 Gewichtsteilen Harnstoff und goo Gewichtsteilen Wasser im ölbade bei i 2o ain Rückflußkühler gerührt. Die Masse schmilzt homogen zusammen und entwickelt Ammoniak. Sie wird immer mehr kautschukartig und fadenziehend, besonders am Schlusse der Kondensation. Nach 6 Stuilden ist die Ammoniakentwlcklung beendet. Der Kühler wird entfernt und das Wasser bei einer Badtcinperatur von i4o" abgedampft. Das Kondensationsprodukt ist dickflüssig zäh. läßt sich aber bis zuletzt gut rühren. In kaltem Zustande hat es Eigenschaften, die denen des Kautschuks sehr ähneln mit dem Unterschied, daß es in Wasser leicht löslich ist. Beispiel z 270 Gewichtsteile Polvvinylalkohol werden. mit .16o Gewichtsteilen I-Iartistolf und .15o Gewiclitsteilen Glykol tuiter Rühren am Rückflußkühler im Ölbade bei 145' kondensiert. Die Umsetzung der sehr zähen homogenen Masse ist nach 312 Stunden beendet. Bei 155' wird nach dem Entfernen des Kühlers das nicht umgesetzte Glykol abgedampft. Die entstandene klare, kautschukartige Masse verhält sich ebenso wie die nach Beispiel i erhaltene.EXAMPLE 100 parts by weight of polyvinyl alcohol are stirred with 360 parts by weight of urea and 100 parts by weight of water in an oil bath at a reflux condenser. The mass melts together homogeneously and develops ammonia. It becomes more and more rubbery and stringy, especially at the end of the condensation. The evolution of ammonia is over after 6 hours. The cooler is removed and the water evaporated at a bath temperature of 140 ". The condensation product is viscous. But can be stirred well until the end. When cold, it has properties which are very similar to those of rubber, with the difference that it is in water slightly soluble. for example, for 270 parts by weight Polvvinylalkohol be. with .16o parts by weight of I-Iartistolf and .15o Gewiclitsteilen glycol tuiter stirring under a reflux condenser in an oil bath at 145 'condensed. the reaction of the very viscous homogeneous mass is complete after 312 hours. at 155' the unreacted glycol is evaporated after removing the cooler The resulting clear, rubber-like mass behaves in the same way as that obtained according to Example i.

Beispiel 3 27o Gewichtsteile Polyvinylalkohol werden mit q.6o Gewichtsteilen Harnstoff, ioo Gewichtsteilen Sorbit und 25o Gewichtsteilen Wasser im Ölbade bei i 2o° am Rückflußkühler gerührt. Nach 3 Stunden ist die Kondensation beendet, und man erhält nach Verdampfen des Wassers Produkte von ähnlichen Eigenschaften wie die im Beispiel i und 2 beschriebenen Produkte.Example 3 27o parts by weight of polyvinyl alcohol are q.6o parts by weight Urea, 100 parts by weight of sorbitol and 250 parts by weight of water in the oil bath i 20 ° stirred on the reflux condenser. After 3 hours, the condensation has ended, and after evaporation of the water, products with properties similar to those obtained the products described in example i and 2.

Claims (1)

PATENTANSPRUCH: Ausführungsform des Verfahrens nach Patent 5o6963 zur Herstellung von Kondensationsprodukten aus Harnstoff oder seinen Derivaten mit Alkoholen, Ketonen oder ihren Derivaten, dadurch gekennzeichnet, daß, hier hochpolymere Alkohole verwendet werden.PATENT CLAIM: Embodiment of the method according to patent 5o6963 for the production of condensation products from urea or its derivatives with Alcohols, ketones or their derivatives, characterized in that, here highly polymeric Alcohols are used.
DE1930I0010230 1926-10-04 1930-02-07 Process for the preparation of condensation products from urea or its derivatives Expired DE519049C (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEI29210D DE506963C (en) 1926-10-04 1926-10-04 Process for the production of condensation products from urea and alcohols or ketones
DEI29471D DE508795C (en) 1926-10-04 1926-11-06 Process for the production of condensation products from urea and alcohols or ketones
DE1930I0010230 DE519049C (en) 1926-10-04 1930-02-07 Process for the preparation of condensation products from urea or its derivatives

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEI29210D DE506963C (en) 1926-10-04 1926-10-04 Process for the production of condensation products from urea and alcohols or ketones
DEI29471D DE508795C (en) 1926-10-04 1926-11-06 Process for the production of condensation products from urea and alcohols or ketones
DE1930I0010230 DE519049C (en) 1926-10-04 1930-02-07 Process for the preparation of condensation products from urea or its derivatives

Publications (1)

Publication Number Publication Date
DE519049C true DE519049C (en) 1931-02-28

Family

ID=42103020

Family Applications (2)

Application Number Title Priority Date Filing Date
DEI29471D Expired DE508795C (en) 1926-10-04 1926-11-06 Process for the production of condensation products from urea and alcohols or ketones
DE1930I0010230 Expired DE519049C (en) 1926-10-04 1930-02-07 Process for the preparation of condensation products from urea or its derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DEI29471D Expired DE508795C (en) 1926-10-04 1926-11-06 Process for the production of condensation products from urea and alcohols or ketones

Country Status (1)

Country Link
DE (2) DE508795C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2466404A (en) * 1944-03-08 1949-04-05 Eastman Kodak Co Polyvinyl carbamates
US3193534A (en) * 1961-02-02 1965-07-06 Kurashiki Rayon Co Production of nitrogenous polyvinyl alcohol derivatives
US3250748A (en) * 1960-12-08 1966-05-10 Kurashiki Rayon Co Production of water-soluble polyvinyl alcohol-urea derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1196507A (en) * 1957-06-13 1959-11-24 Nopco Chem Co Process and condensation product of ethylene urea oxide with a glycol

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2466404A (en) * 1944-03-08 1949-04-05 Eastman Kodak Co Polyvinyl carbamates
US3250748A (en) * 1960-12-08 1966-05-10 Kurashiki Rayon Co Production of water-soluble polyvinyl alcohol-urea derivatives
US3193534A (en) * 1961-02-02 1965-07-06 Kurashiki Rayon Co Production of nitrogenous polyvinyl alcohol derivatives

Also Published As

Publication number Publication date
DE508795C (en) 1930-10-02

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