DE919072C - Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups - Google Patents

Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups

Info

Publication number
DE919072C
DE919072C DED5932D DED0005932D DE919072C DE 919072 C DE919072 C DE 919072C DE D5932 D DED5932 D DE D5932D DE D0005932 D DED0005932 D DE D0005932D DE 919072 C DE919072 C DE 919072C
Authority
DE
Germany
Prior art keywords
accelerating
reaction
compounds containing
polyfunctional isocyanates
similar substances
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
DED5932D
Other languages
German (de)
Inventor
Dr Eugen Kuhr
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.)
Dynamit Nobel AG
Original Assignee
Dynamit Nobel 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
Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG
Priority to DED5932D priority Critical patent/DE919072C/en
Application granted granted Critical
Publication of DE919072C publication Critical patent/DE919072C/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
    • 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
    • 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
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C08G18/168—Organic compounds
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7692—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing at least one isocyanate or isothiocyanate group linked to an aromatic ring by means of an aliphatic group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Description

Verfahren zur Beschleunigung der Umsetzung von polyfunktionellen Isocyanaten oder ähnlich wirkenden Stoffen mit polyoxy- oder polycarboxylgruppenhaltiqen Verbindungen Es wurde gefunden, daß durch den Zusatz geringer Mengen tertiärer Amine oder Phosphine aliphatischer Natur die Umsetzung von polyfunktionellen Isocyanaten oder ähnlich wirkenden, d. h. Isocyanate abspaltenden Stoffen, mit polyoxy- oder polycarboxylgruppenhaltigen Verbindungen wesentlich beschleunigt wird. Von besonderem Interesse ist die Umsetzung von zwei- oder höherwertigen Isocyanaten mit Polyestern, Celluloseabkömmlingen oder anderen Polymeren mit reaktionsfähigen H-Atomen.Process for accelerating the conversion of polyfunctional isocyanates or similarly acting substances with compounds containing polyoxy or polycarboxyl groups It has been found that by adding small amounts of tertiary amines or phosphines aliphatic nature, the conversion of polyfunctional isocyanates or similar acting, d. H. Substances that split off isocyanates with polyoxy or polycarboxyl groups Connections is accelerated significantly. The implementation is of particular interest of di- or higher-valent isocyanates with polyesters, cellulose derivatives or other polymers with reactive hydrogen atoms.

Als tertiäre Amine aliphatischer Natur seien beispielsweise genannt Triäthylamin, Triisopentylamin, Diäthylbenzylamin, N-Hexylpiperidin, als tertiäre PhosphineTriäthylphosphin,Triisobutylphosphin.Tertiary amines of an aliphatic nature may be mentioned as examples Triethylamine, triisopentylamine, diethylbenzylamine, N-hexylpiperidine, as tertiary Phosphine Triethylphosphine, Triisobutylphosphine.

Im allgemeinen genügt ein Zusatz von 0,5 bis 5°/o der tertiären Amine oder Phosphine, um eine deutliche Beschleunigung der Umsetzung zu erzielen.In general, an addition of 0.5 to 5% of the tertiary amines or phosphines is sufficient in order to achieve a marked acceleration of the reaction.

Natriumphenolat wirkt auch beschleunigend auf die genannten Umsetzungen, doch läßt es sich nur schlecht einarbeiten, wirkt unregelmäßig und liefert in den meisten Fällen weniger brauchbare Produkte als die genannten Amine. Tertiäre aromatische Amine, wie Dimethylanilin, Pyridin, Chinolin, wirken wesentlich weniger beschleunigend als die gemäß der Erfindung beanspruchten Amine. Von besonderer technischer Bedeutung ist die Tatsache, daß die erfindungsgemäß beanspruchten Amine und Phosphine schon bei gewöhnlicher Temperatur ihre beschleunigende Wirkung entfalten, so daß es mit ihrer Hilfe möglich ist, kalt härtende Harzmischungen zu bereiten. Ferner ist es von besonderer Bedeutung, daß die so gewonnenen Harze von gleichmäßiger Beschaffenheit sind. Beispiel 50 g eines dickflüssigen Polyesters aus 3 Mol Adipinsäure und 4 Mol Trimethylolpropan werden mit 55 g p, p'-Di-p-xylylmethandiisocyanat vermischt. Der Mischung werden noch 4 g Diäthylbenzylamin als Beschleuniger zugefügt. Die Härtezeiten im Vergleich mit einer nicht mit Beschleuniger versetzten Probe sind wie folgt: Temperatur ohne Amin mit Amin 20° noch nach mehreren Tagen weich 2 Tage 6o° 15 Stunden 2 Stunden 95° 3 - 2o Minuten 12o° z Stunde 8 - Sodium phenolate also has an accelerating effect on the reactions mentioned, but it is difficult to incorporate, has an irregular effect and in most cases gives less useful products than the amines mentioned. Tertiary aromatic amines, such as dimethylaniline, pyridine, quinoline, have a significantly less accelerating effect than the amines claimed according to the invention. Of particular technical importance is the fact that the amines and phosphines claimed according to the invention develop their accelerating effect even at ordinary temperature, so that with their help it is possible to prepare cold-curing resin mixtures. It is also of particular importance that the resins so obtained are of uniform consistency. Example 50 g of a viscous polyester made from 3 mol of adipic acid and 4 mol of trimethylolpropane are mixed with 55 g of p'-di-p-xylylmethane diisocyanate. Another 4 g of diethylbenzylamine are added to the mixture as an accelerator. The hardening times in comparison with a sample not mixed with accelerator are as follows: Temperature without amine with amine 20 ° after several Days soft 2 days 60 ° 15 hours 2 hours 95 ° 3 - 20 minutes 12o ° z hour 8 -

Claims (1)

PATENTANSPRUCH: Verfahren zur Beschleunigung der Umsetzung von polyfunktionellen Isocyanaten oder ähnlich wirkenden Stoffen mit polyoxy- oder polycarboxylgruppenhaltigen Verbindungen, dadurch gekennzeichnet, daß die Umsetzung in Gegenwart geringer Mengen tertiärer, aliphatischer Amine oder Phosphine erfolgt. PATENT CLAIM: Process for accelerating the reaction of polyfunctional isocyanates or similarly acting substances with compounds containing polyoxy or polycarboxyl groups, characterized in that the reaction takes place in the presence of small amounts of tertiary, aliphatic amines or phosphines.
DED5932D 1944-06-13 1944-06-13 Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups Expired DE919072C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED5932D DE919072C (en) 1944-06-13 1944-06-13 Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED5932D DE919072C (en) 1944-06-13 1944-06-13 Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups

Publications (1)

Publication Number Publication Date
DE919072C true DE919072C (en) 1954-10-11

Family

ID=7031631

Family Applications (1)

Application Number Title Priority Date Filing Date
DED5932D Expired DE919072C (en) 1944-06-13 1944-06-13 Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups

Country Status (1)

Country Link
DE (1) DE919072C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1040233B (en) * 1955-11-18 1958-10-02 Hudson Foam Plastics Corp Process for the production of an elastic foam with essentially open cells based on polyester isocyanate
DE1048020B (en) * 1955-07-18 1958-12-31 Lemfoerder Metallwarengesellsc Process for producing highly elastic polyurethanes
DE1056820B (en) * 1955-03-04 1959-05-06 Ici Ltd Process for the production of polyurethane foams
DE1127075B (en) * 1959-02-27 1962-04-05 Ici Ltd Process for the production of polyurethane plastics

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1056820B (en) * 1955-03-04 1959-05-06 Ici Ltd Process for the production of polyurethane foams
DE1048020B (en) * 1955-07-18 1958-12-31 Lemfoerder Metallwarengesellsc Process for producing highly elastic polyurethanes
DE1040233B (en) * 1955-11-18 1958-10-02 Hudson Foam Plastics Corp Process for the production of an elastic foam with essentially open cells based on polyester isocyanate
DE1127075B (en) * 1959-02-27 1962-04-05 Ici Ltd Process for the production of polyurethane plastics

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