DE1056368B - Use of stabilizing agents in foams made from polyoxy compounds and polyisocyanates - Google Patents
Use of stabilizing agents in foams made from polyoxy compounds and polyisocyanatesInfo
- Publication number
- DE1056368B DE1056368B DEF26169A DEF0026169A DE1056368B DE 1056368 B DE1056368 B DE 1056368B DE F26169 A DEF26169 A DE F26169A DE F0026169 A DEF0026169 A DE F0026169A DE 1056368 B DE1056368 B DE 1056368B
- Authority
- DE
- Germany
- Prior art keywords
- polyisocyanates
- stabilizing agents
- polyoxy compounds
- foams made
- foams
- 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
Links
- 239000006260 foam Substances 0.000 title claims description 13
- 239000003381 stabilizer Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title claims description 6
- 229920001228 polyisocyanate Polymers 0.000 title claims description 6
- 239000005056 polyisocyanate Substances 0.000 title claims description 6
- -1 polyoxy Polymers 0.000 title claims description 5
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002926 oxygen Chemical class 0.000 description 2
- 229960001147 triclofos Drugs 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- RZYMXMZJVMXDRP-UHFFFAOYSA-N 1-(2-hydroxyethoxy)ethanol Chemical compound CC(O)OCCO RZYMXMZJVMXDRP-UHFFFAOYSA-N 0.000 description 1
- YPFZMPJXTBJRCP-UHFFFAOYSA-N 6-[2-(diethylamino)ethoxy]-6-oxohexanoic acid Chemical compound CCN(CC)CCOC(=O)CCCCC(O)=O YPFZMPJXTBJRCP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HOKMYEORIPLLGI-KVVVOXFISA-N n-ethylethanamine;(z)-octadec-9-enoic acid Chemical compound CCNCC.CCCCCCCC\C=C/CCCCCCCC(O)=O HOKMYEORIPLLGI-KVVVOXFISA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0033—Use of organic additives containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Description
Verwendung von stabilisierenden Mitteln in aus Polyoxyverbindungen und Polyisocyanaten hergestellten Schaumstoffen Die Herstellung von Urethangruppen enthaltenden Schaumstoffen nach dem Polyisocyanat-Polyadditions.Use of stabilizing agents in polyoxy compounds and polyisocyanates made foams The manufacture of urethane groups containing foams after the polyisocyanate polyaddition.
Verfahren ist bekannt. Dabei werden Verbindungen mit mehreren reaktionsfähigen Wasserstoffatomen, insbesondere Polyoxyverbindungen, beispielsweise endständige Hydroxylgruppen enthaltende Polyester, Polyäther und Polythioäther, mit Polyisocyanaten zu hochmolekularen MateritaLien umgesetzt, wobei durch die gleichzeitig vorhandenen Carboxylgruppen oder durch den Zusatz von Wasser Kohlendioxyd entwickelt wird, welches die sich ausbildende hochmolekulare Struktur zu einem Schaumstoff auftreibt.Procedure is known. In doing so, compounds with several reactive Hydrogen atoms, especially polyoxy compounds, for example terminal ones Polyesters, polyethers and polythioethers containing hydroxyl groups, with polyisocyanates converted into high-molecular materitaLien, whereby by the simultaneously existing Carboxyl groups or carbon dioxide is developed through the addition of water, which the high-molecular structure that is formed expands into a foam.
Je nach Wahl der Ausgangskomponenten und deren Mengenverhältnis sowie der Reihenfolge ihrer Umsetzung und je nach Mitverwendung von Aktivatoren, Emulgatoren oder anderen Zusatzstoffen erhält man Schaumstoffe mit mit den verschiedenartigsten physikalischen Eigenschaften.Depending on the choice of the starting components and their proportions as well the order of their implementation and depending on the use of activators and emulsifiers or other additives, foams are obtained with a wide variety of materials physical properties.
Es ist ferner bekannt, daß man durch den Zusatz von Licht- und Alterungsschutzmitteln bei der Kautschukvulkanisation eine durch den Einfluß von Licht und Sauerstoff verursachte Minderung des Gebrauchswertes von Gummiartikeln weitgehend verhüten kann. Viele derartige Stabilisatoren enthalten OH- bzw. SH-Gruppen in aromatischer Bindung. It is also known that the addition of light and anti-aging agents in rubber vulcanization, one caused by the influence of light and oxygen Can largely prevent a reduction in the utility value of rubber articles. Many Such stabilizers contain OH or SH groups in aromatic bonds.
Ihre Wirkung wird dadurch erklärt, daß diese Gruppen den durch Licht aktivierten Sauerstoff und die durch Anlagerung des aktivierten Sauerstoffs an die im Gummi noch vorhandenen Doppelbindungen entstandenen Peroxyde inaktivieren.Their effect is explained by the fact that these groups use light activated oxygen and those caused by the addition of activated oxygen to the inactivate any peroxides that are still present in the rubber.
Gegenstand der Erfindung ist die Verwendung bestimmter Alterungsschutzmittel, welche die Licht echtheit und Alterungsbeständigkeit von Urethangruppen enthaltenden Schaumstoffen verbessern. Zu diesem Zweck wird 2-Mercaptovbenlzimidazol als stabilisierendes Mittel gegenüber dem Einfluß von Licht und Sauerstoff in im wesentlichen aus Polyoxyverbindungen und' Polyisocyanaten hergestellten Schaumstoffen verwendet. The invention relates to the use of certain anti-aging agents, which contain the light fastness and aging resistance of urethane groups Improve foams. For this purpose, 2-mercapto benzimidazole is used as a stabilizing agent Means against the influence of light and oxygen consisting essentially of polyoxy compounds and 'foams made from polyisocyanates are used.
Der Stabilisator wird in Mengen von 0,05 bis 10%, vorzugsweise 1 bis 20/o, zugesetzt. Dabei wird er entweder einer der Ausgangskomponenten für die Schaumstoffe vor der Umsetzung oder während deren Umsetzung in Substanz oder in Lösung zugegeben. wird der Stabilisator in Lösung zugesetzt, so hat sich insbesondere Trichloräthylphosphat als Lösungsmittel bewährt. Die Herstellung der Polyurethanschaumstoffe geschieht im übrigen ohne Abänderung nach den gebräuchlichen Verfahren. The stabilizer is used in amounts of 0.05 to 10%, preferably 1 up to 20 / o, added. It either becomes one of the starting components for the Foams before the implementation or during their implementation in bulk or in Solution added. if the stabilizer is added in solution, it has in particular been found Trichloroethyl phosphate has been tried and tested as a solvent. The manufacture of polyurethane foams otherwise takes place without modification according to the usual procedures.
Die Wirkung des erfindungsgemäß zu verwendenden 2-Mercapto-benzimidazols wird durch das nachfolgende Beispiel erläutert : Beispiel 100 Teile eines Polythioäthers aus 1 Mol Thiodiglykol und 1 Mol 1,4-Diäthylenglykoläther des Butandiols mit de OH-Zahl 60 werden mit einem Beschleunigergemisch folgender Zusammensetzung vermischt: 3 Gewichtsteile Adipinsäure-N,N-diäthylaminoäthylester, 2 Gewichtsteile ölsaures Diäthylamin, 1 Gewichtsteil sulfoniertes Rizinusöl mit 54% Wasser, 2 Gewichtsteile Wasser. The effect of the 2-mercapto-benzimidazole to be used according to the invention is explained by the following example: Example 100 parts of a polythioether from 1 mole of thiodiglycol and 1 mole of 1,4-diethylene glycol ether of butanediol with de OH number 60 are mixed with an accelerator mixture of the following composition: 3 parts by weight of adipic acid N, N-diethylaminoethyl ester, 2 parts by weight of oleic acid Diethylamine, 1 part by weight of sulfonated castor oil with 54% water, 2 parts by weight Water.
Nach gründlicher Vermischung werden 36 Gewichtsteile Toluylendiisocyanat zugesetzt, worauf das Gemisch zu einem Schaumstoff auftreibt. After thorough mixing, there are 36 parts by weight of tolylene diisocyanate added, whereupon the mixture expands to form a foam.
Nach dem Aushärten wird dieser Schaumstoff unter einer kohlenbogenlampe im Fade-o-meter bei 75°C belichtet. An den belichteten Stellen färbt sich der Schaumstoff stark braun unter gleichzeitiger Versprödung und' Abnahme seiner Festigkeit. After hardening, this foam is placed under a carbon arc lamp exposed in the fade-o-meter at 75 ° C. The foam changes color in the exposed areas strong brown with simultaneous embrittlement and decrease of its strength.
Werden dem vorgenannten Polythioäther indessen 2% 2-Mercapto-benzimidazol in Form einer 30%igen Lösung in Trichloräthylphosphat zugesetzt, so resultiert ein Schaumstoff, der an den wie vorhin belichteten Stellen nur noch eine leichte Gelbfärbung, aber keine Versprödung und keinen Festigkeitsabfall mehr aufweist. If the aforementioned polythioether, however, 2% 2-mercapto-benzimidazole added in the form of a 30% solution in trichloroethyl phosphate, the result is a Foam, which is only slightly yellow in the areas exposed as before, but no longer has any embrittlement or loss of strength.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26169A DE1056368B (en) | 1956-08-09 | 1956-08-09 | Use of stabilizing agents in foams made from polyoxy compounds and polyisocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26169A DE1056368B (en) | 1956-08-09 | 1956-08-09 | Use of stabilizing agents in foams made from polyoxy compounds and polyisocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1056368B true DE1056368B (en) | 1959-04-30 |
Family
ID=7091911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF26169A Pending DE1056368B (en) | 1956-08-09 | 1956-08-09 | Use of stabilizing agents in foams made from polyoxy compounds and polyisocyanates |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1056368B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106490B (en) | 1956-01-16 | 1961-05-10 | Du Pont | Molding and coating compound stabilized against light degradation based on chain-extended polyurethane resins |
| FR2196366A1 (en) * | 1972-08-15 | 1974-03-15 | Ici Ltd |
-
1956
- 1956-08-09 DE DEF26169A patent/DE1056368B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106490B (en) | 1956-01-16 | 1961-05-10 | Du Pont | Molding and coating compound stabilized against light degradation based on chain-extended polyurethane resins |
| FR2196366A1 (en) * | 1972-08-15 | 1974-03-15 | Ici Ltd |
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