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 groupsInfo
- 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
Links
- 238000006243 chemical reaction Methods 0.000 title claims description 7
- 239000012948 isocyanate Substances 0.000 title claims description 6
- 150000002513 isocyanates Chemical class 0.000 title claims description 6
- -1 polyoxy Polymers 0.000 title claims description 5
- 239000000126 substance Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- BBYSGWAYRRMWOW-UHFFFAOYSA-N 1-hexylpiperidine Chemical compound CCCCCCN1CCCCC1 BBYSGWAYRRMWOW-UHFFFAOYSA-N 0.000 description 1
- QKVUSSUOYHTOFQ-UHFFFAOYSA-N 3-methyl-n,n-bis(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCN(CCC(C)C)CCC(C)C QKVUSSUOYHTOFQ-UHFFFAOYSA-N 0.000 description 1
- TXCNLGPPSXYYHY-UHFFFAOYSA-N C(C)P(CC)CC.P Chemical group C(C)P(CC)CC.P TXCNLGPPSXYYHY-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical group CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
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:
Claims (1)
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)
| 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 |
-
1944
- 1944-06-13 DE DED5932D patent/DE919072C/en not_active Expired
Cited By (4)
| 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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