DE953012C - Process for the production of soluble, preferably higher molecular weight, polyisocyanates capable of further conversion - Google Patents
Process for the production of soluble, preferably higher molecular weight, polyisocyanates capable of further conversionInfo
- Publication number
- DE953012C DE953012C DEF9416A DEF0009416A DE953012C DE 953012 C DE953012 C DE 953012C DE F9416 A DEF9416 A DE F9416A DE F0009416 A DEF0009416 A DE F0009416A DE 953012 C DE953012 C DE 953012C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- molecular weight
- soluble
- polyisocyanates
- 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
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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
Description
Verfahren zur Herstellung von löslichen, vorzugsweise höhenmolekularen und zur weiteren Umsetzung befähigten Polyisocyanaten Organische Polyisocyanate, insbesondere Tri-und Polyisocyanate,finden bereits weitgehende technische Verwendung für Lacke, Kunststoffe und Verklebungen.Process for the production of soluble, preferably high molecular weight and polyisocyanates capable of further conversion Organic polyisocyanates, in particular tri- and polyisocyanates are already widely used industrially for paints, plastics and bonds.
Sie ermöglichen die Herstellung von hochmolekularen unlöslichen Körpern, indem man sie beispielsweise mit Polyoxyverbindungen, Polyaminen, Wasser oder einem Gemisch derselben reagieren läßt.They enable the production of high molecular weight insoluble bodies, by for example with polyoxy compounds, polyamines, water or a Can react mixture of the same.
Es ist gemäß Patent 87040o bereits vorgeschlagen worden, Polyisocyanate aus Diisocyanaten durchUmsetzung mit 3- oder q.wertigenAlkoholen; gegebenenfalls im Gemisch mit 2wertigen Alkoholen, herzustellen, wobei pro Hydroxylgruppe des Polyalkohols mindestens r Diisocyanatmolekül zur Anwendung gelangt. Hierbei entsteht im Fall eines Trialkohols, wie Trimethylolpropan oder Glycerin, im wesentlichen ein niedermolekulares, klar lösliches und lagerbeständiges Urethan mit drei Isocyanatgruppen. Da hierbei im Verlaufe der Reaktion dieses drei Isocyanatgruppen enthaltende Produkt zum Teil mit dem noch vorhandenen Triol in Reaktion tritt, entstehen nebenher höhenmolekulare, jedoch lösliche Polyisocyanate. Diese Nebenreaktion hat zur Folge, daß ein Teil des eingesetzten Diisocyanates unverändert erhalten bleibt.It has already been proposed according to patent 87040o, polyisocyanates from diisocyanates by reaction with trivalent or equivalent alcohols; possibly as a mixture with dihydric alcohols, with per hydroxyl group of the polyalcohol at least r diisocyanate molecule is used. This arises in the case of a trial alcohol, such as trimethylolpropane or glycerine, essentially a low molecular weight, Clearly soluble and storage-stable urethane with three isocyanate groups. Since here in the course of the reaction of this product containing three isocyanate groups in part reacts with the triol that is still present, high molecular but soluble polyisocyanates. This side reaction has the consequence that a part of the diisocyanate used remains unchanged.
Im Fall physiologisch wirksamer Diisocyanate - also leichtflüchtiger Produkte - würde die beim Arbeiten in geschlossenen Räumen zumal bei empfindlichen Personen auftretende' Belästigung im Vergleich zu freien Diisocyanaten zwar wesentlich abgeschwächt, aber nicht aufgehoben sein.In the case of physiologically active diisocyanates - that is, more volatile Products - would be used when working in enclosed spaces, especially with sensitive ones Nuisance occurring to people compared to free diisocyanates be significantly weakened, but not abolished.
Es wurde nun gefunden, daB ohne Beeinträchtigung der Löslichkeit und der Lagerbeständigkeit aus Diisocyanaten und niedermolekularen Polyalkoholen Produkte aufgebaut werden können, die diesen Nachteil kaum oder überhaupt nicht mehr zeigen. Werden die Mengenverhältnisse nämlich so gewählt, daß mehr als eine und weniger als zwei Isocyanatgruppen pro Hydroxylgruppe des Polyalkohols zum Einsatz gelangen; so werden die höhermolekularen Polyisocyanate bevorzugt entstehen und das eingesetzte Diisocyanat je nach dem Einsatzverhältnis weitgehend oder sogar völlig in das gewünschte, nicht flüchtige Polyisocyanat verwandelt werden.It has now been found that without impairing the solubility and the shelf life of diisocyanates and low molecular weight polyalcohols products can be built that show this disadvantage hardly or not at all. If the proportions are chosen so that more than one and less as two isocyanate groups per hydroxyl group of the polyalcohol are used; so the higher molecular weight polyisocyanates are preferentially formed and the used Depending on the use ratio, diisocyanate largely or even completely in the desired, non-volatile polyisocyanate can be converted.
Die maximalen Mengenverhältnisse richten sich nach der Natur des verwendeten Polyalkohols, wobei im Fall eines Diols gegenüber Triolen zur Erzielung noch löslich bleibender Produkte naturgemäß ein höherer Einsatz an Polyalkoholen möglich ist.The maximum proportions depend on the nature of the one used Polyalcohol, although still soluble in the case of a diol compared to triols to achieve this In the case of permanent products, a higher use of polyalcohols is naturally possible.
Selbstverständlich können auch Gemische von Polyalkoholen zur Erzielung besonderer Effekte verwendet werden, wie auch Aminopolyalkohole mit tertiär gebundenem Stickstoff für sich allein oder im Gemisch mit mehrwertigen Alkoholen geeignet sind.Mixtures of polyalcohols can of course also be used to achieve this special effects are used, as well as aminopolyalcohols with tertiary bonded Nitrogen on its own or in a mixture with polyhydric alcohols are suitable.
Der Grenzwert der Polyalkoholmenge, der den Übergang zum vernetzten Produkt angibt, wird zweckmäßig von Fall zu Fall ermittelt.The limit of the amount of polyalcohol that makes the transition to the crosslinked Product is determined on a case-by-case basis.
.Beispiele für geeignete Polyalkohole sind Äthylenglykol, Butylenglykol, Hexandiol, Methylhexandiol, Diäthylenglykol, Glycerin, Trimethyloläthan, Trimethylolpropan, 1, 2, 4-Trioxybutan, Pentaerythrit, Triäthanolamin. Geeignete Diisocyanate sind beispielsweise Tetramethylendiisocyanat, Hexamethylendiisocyanat, Toluylendiisocyanat, 4, 4'-Diphenylmethandiisocyanat..Examples of suitable polyalcohols are ethylene glycol, butylene glycol, Hexanediol, methylhexanediol, diethylene glycol, glycerine, trimethylolethane, trimethylolpropane, 1, 2, 4-trioxybutane, pentaerythritol, triethanolamine. Suitable diisocyanates are for example tetramethylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate.
Zweckmäßig erfolgt die Herstellung der Polyisocyanate in der Weise, daß man das Diisocyanat in Form seiner Lösung im indifferenten Lösungsmittel, wie Essigsäureester, vorlegt und den Polyalkohol bei etwas erhöhter Temperatur allmählich zugibt.The polyisocyanates are expediently prepared in such a way that that the diisocyanate in the form of its solution in the inert solvent, such as Acetic acid ester, and the polyalcohol gradually at a slightly elevated temperature admits.
Der besondere Wert der neuen Polyisocyanate besteht darin, daß sie infolge ihres erhöhten Molekulargewichtes praktisch keinen Dampfdruck mehr zeigen und daher vom physiologischen Standpunkt aus harmlos sind. Darüber hinaus 'verleihen sie z. B. den Lacklösungen, die unter Mitverwendung von oxygruppenhaltigen Polyestern gebildet werden, einen wesentlich verbesserten Verlauf bei sonst gleichbleibenden Eigenschaften. Die erwähnten Polyisocyanate lassen sich selbstverständlich auch in die in der Hitze spaltbaren Addukte mit Phenol oder Malonester überführen. Beispiel i iooo Gewichtsteile Toluylendiisocyanat werden in Form der 5o%igen Essigesterlösung in einer sauerstofffreien Atmosphäre unter Rühren bei 70° nach und nach mit der -5o%igen Essigesterlösung des Gemisches aus 85 Gewichtsteilen Trimethylolpropan und 34o Gewichtsteilen 1, 3-Butylenglykol versetzt (Umsetzungsverhältnis O H zu N C O wie 1: z,22). Nach erfolgtem Zulauf und einem iostündigen Weitenerhitzen auf 70° hinterbleibt eine ölige, hellgelbe Lösung mit 2,9 % N CO. Für die reine Substanz errechnet sich hieraus ein Gehalt von 5,6 0% N C O. Ungebundenes Tolnylendiisocyanat ließ sich analytisch nicht nachweisen. Die Lösung ist monatelang ohne Beeinträchtigung des Reaktionsvermögens lagerfähig und liefert in der Kombination mit Oxygruppen enthaltenden Polyestern, wie sie durch Veresterung von mehrbasischen» Carbonsäuren mit Überschuß Polyalkoholen erhältlich sind, wertvolle physiologisch einwandfreie Lacklösungen. Beispiel e iooo Gewichtsteile Toluylendiisocyanat werden in 333 G'ewichtstei.len Essigsäureäthylester gelöst, und diese Lösung wird bei 70°, wie im Beispiel i beschrieben, mit dem Alkoholgemisch aus 24o Gewichtsteilen Trimethylolpropan und 103 Gewichtsteilen i, 3-Butylenglykol, gelöst in 114 Gewichtsteilen Äthylacetat, versetzt (Umsetzungsverhältnis O H zu N C O wie i: 1,5). Nach erfolgtem Zulauf werden 447 Gewichtsteile Toluol nachgegeben, so daß eine 6o%ige Lösung des Reaktionsproduktes hinterbleibt, die 7,2% N C O enthält. Hieraus errechnet sich ein Gehalt von i2 % N C O für das lösungsmittelfreie Produkt. Nach 4 Monaten Lagerung konnte kein Abfall im Wirkungsgrad analytisch festgestellt werden. Sie liefert mit oxygruppenhaltigen Polyestern hervorragende Filme und Überzüge. Werden iooo Gewichtsteile dieser 6oo/oigen Lösung mit 161 Gewichtsteilen Phenol bei 70° umgesetzt, so entsteht eine Abspalterlösung, die erst bei erhöhtenTemperaturen wie eine Polyisocyanatlösung reagiert. Beispiel 3 17q. Gewichtsteile Toluylendiisocyanat werden in 58 Gewichtsteilen Äthylacetat gelöst und unter Rühren bei 5o° allmählich mit 7g Gewichtsteilen i, 3-Butylernglykol, gelöst in 26 Gewichtsteilen Äthylacetat, versetzt (Umsebzungsverhültnis O H zu NCO wie 1:1,Z4). Der Zulauf wird so geregelt, daß die Innentemperatur von 5o° erhalten bleibt. Die 75%igeLösung wird noch etwa io Stunden bei dieser Temperatur belassen. Es hinfierbleibt eine bei Raumtemperatur dickflüssige, hellgelbe Lösung mit 4,2'/o N C O, bezogen auf lösungsmittelfreies Produkt, in der kein ungebundenes Toluylendiisocyanat mehr nachgewiesen werden konnte. In Verbindung mit einem Oxygruppen enthaltenden Polyester entstehen für Luft- _ und Ofentrocknung geeignete Lacklösungen. Beispiel 4 6oo Gewichtsteile Hexamethylendiisocyanat werden in Zoo Gewichtsteilen Äthylacetat gelöst und gemäß Beispiel i bei 70° mit der Lösung von 136 Gewichtsteilen Trimethylolpropan und 58 Gewichtsteilen 1, 3-Butylenglykol in 65 Gewichtsteilen Athyla£etat umgesetzt (Umsetzungsrvenhältnis O H zu N C O wie r : 1,66). Es entsteht eine nahezu farblose Lösung mit einem Gehalt von r5,2°% N C O, bezogen auf lösungsmittelfreies Produkt, die für die üblichen Umsetzungen mit Polyoxyverbindungen herangezogen werden kann und auch für sich allein angewandt einen hervorragenden Klebstoff darstellt. Beispiel s 8oo Gewichtsteile einer 75%igen Äthylacetat-Lösung von Toluylendiisocyanat werden, wie im Beispiel 1 beschrieben, mit dem Alkoholgemisch aus j3 Gewichtsteilen Triäthanolamin und 85 Gewichtsteilen 1, 3-Butylenglykol gelöst, in 59 Gewichtsteilen Äthylacetat bei 50° umgesetzt (Umsetzungsverhältnis O H zu N C O wie 1:1,83). Die 12,7% N C O, bezogen auf lösungsmittelfreies Produkt, besitzende beständige Lösung liefert, im stöchiometrischen Verhältnis mit Polyoxyverbindungen kombiniert, schnell trocknende, gegen chemische Einflüsse sehr gut beständige Überzüge. Werden 622 g dieser Lösung mit 188 g Phenol zur Reaktion gebracht, so entsteht ein bei Raumtemperatur indifferentes Produkt, das erst nach dem Erhitzen zusammen mit oxygruppenhaltigen Reaktionspartnern wie ein Polyisocyanat reagiert. Beispiel"6 Werden 6oo Gewichtsteile Toluylendi.isocyanat, gelöst in 258 Gewichtsteilen Äthylacetat, wie im Beispiel 1 beschrieben, mit xlem Gemindh aus 59 Gewichtsteilen Trimethylolpropan, 65 Gewichtsteilen Triäthanolamin und 5o Gewichtsteilen 1, 3-Butylenglykol (Umsetzungsverhältnis O H zu N C O wie 1:i,78) umgesetzt, so entsteht eine etwa z2,7°/0 N C O, bezogen auf lösungsmittelfreies Produkt, enthaltende Lösung eines Polyisocyanates, die direkt oder in Form ihres Phenol- oder Malonesteradduktes den bekannten Isocyanaturnsetzungsreaktionen zugeführt werden kann.The particular value of the new polyisocyanates is that they due to their increased molecular weight practically no longer show any vapor pressure and are therefore harmless from a physiological point of view. In addition, 'lend she z. B. the paint solutions with the use of polyesters containing oxy groups are formed, a significantly improved course while otherwise remaining the same Properties. The polyisocyanates mentioned can of course also be used convert into the hot-fissile adducts with phenol or malonic ester. example 100 parts by weight of tolylene diisocyanate are in the form of the 50% ethyl acetate solution in an oxygen-free atmosphere with stirring at 70 ° gradually with the -5o% ethyl acetate solution of the mixture of 85 parts by weight of trimethylolpropane and 34o parts by weight of 1,3-butylene glycol are added (conversion ratio O H to N C O as 1: z, 22). After the addition and heating for another 10 hours 70 ° an oily, light yellow solution with 2.9% N CO remains. For the pure substance A content of 5.6% N CO is calculated from this. Unbound tolnylene diisocyanate could not be proven analytically. The solution is unimpaired for months of reactivity and delivers in combination with oxy groups containing polyesters, such as those produced by the esterification of polybasic »carboxylic acids are obtainable with excess polyalcohols, valuable physiologically flawless Paint solutions. EXAMPLE 100 parts by weight of toluene diisocyanate are used in 333 parts by weight Dissolved ethyl acetate, and this solution is at 70 °, as described in Example i, with the alcohol mixture of 240 parts by weight of trimethylolpropane and 103 parts by weight i, 3-Butylene glycol, dissolved in 114 parts by weight of ethyl acetate, added (conversion ratio O H to N C O as i: 1.5). After the addition has taken place, 447 parts by weight of toluene are added given in, so that a 6o% solution of the reaction product remains, the Contains 7.2% N C O. From this a content of i2% N C O is calculated for the solvent-free Product. After 4 months of storage, no decrease in the degree of efficiency could be determined analytically will. It provides excellent films and coatings with polyesters containing oxy groups. Become 100 parts by weight of this 600% solution with 161 parts by weight of phenol reacted at 70 °, a cleavage solution is formed, which only occurs at elevated temperatures how a polyisocyanate solution reacts. Example 3 17q. Parts by weight of tolylene diisocyanate are dissolved in 58 parts by weight of ethyl acetate and gradually stirred at 5o ° with 7g parts by weight of i, 3-butylene glycol, dissolved in 26 parts by weight of ethyl acetate, added (conversion ratio O H to NCO such as 1: 1, Z4). The inflow is regulated in such a way that that the internal temperature of 5o ° is maintained. The 75% solution will still be around Leave at this temperature for 10 hours. It remains at room temperature viscous, light yellow solution with 4.2% N C O, based on solvent-free Product in which no more unbound toluene diisocyanate could be detected. In connection with a polyester containing oxy groups, air _ and oven drying suitable paint solutions. Example 4 600 parts by weight of hexamethylene diisocyanate are dissolved in zoo parts by weight of ethyl acetate and according to Example i at 70 ° with the solution of 136 parts by weight of trimethylolpropane and 58 parts by weight 1, 3-butylene glycol in 65 parts by weight of Athyla £ etat implemented (conversion ratio O H to N C O like r: 1.66). An almost colorless solution with a content is formed of r5.2 °% N C O, based on solvent-free product, which is necessary for the usual Reactions with polyoxy compounds can be used and also on their own when applied is an excellent adhesive. Example s 8oo parts by weight a 75% ethyl acetate solution of toluene diisocyanate, as in the example 1 described, with the alcohol mixture of j3 parts by weight of triethanolamine and 85 Parts by weight of 1,3-butylene glycol dissolved in 59 parts by weight of ethyl acetate at 50 ° implemented (conversion ratio O H to N C O such as 1: 1.83). The 12.7% N CO, based on solvent-free product, possessing stable solution supplies, in the stoichiometric Ratio combined with polyoxy compounds, quick drying, against chemical Coatings very resistant to influences. Become 622 g of this solution with 188 g of phenol brought to reaction, the result is an indifferent product at room temperature, that only after heating together with oxy group-containing reactants such as a polyisocyanate reacts. Example "6 If 600 parts by weight of toluene diisocyanate, dissolved in 258 parts by weight of ethyl acetate, as described in Example 1, with xlem Gemindh from 59 parts by weight of trimethylolpropane, 65 parts by weight of triethanolamine and 5o parts by weight of 1,3-butylene glycol (conversion ratio of O H to N C O such as 1: i, 78) reacted, the result is an approximately z2.7 ° / 0 N C O, based on solvent-free Product, containing solution of a polyisocyanate, directly or in the form of their Phenol or malonic ester adducts fed to the known isocyanate addition reactions can be.
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DEF9416A DE953012C (en) | 1952-07-04 | 1952-07-04 | Process for the production of soluble, preferably higher molecular weight, polyisocyanates capable of further conversion |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DEF9416A DE953012C (en) | 1952-07-04 | 1952-07-04 | Process for the production of soluble, preferably higher molecular weight, polyisocyanates capable of further conversion |
Publications (1)
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DE953012C true DE953012C (en) | 1956-11-22 |
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DEF9416A Expired DE953012C (en) | 1952-07-04 | 1952-07-04 | Process for the production of soluble, preferably higher molecular weight, polyisocyanates capable of further conversion |
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Cited By (44)
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---|---|---|---|---|
DE1079625B (en) * | 1957-04-29 | 1960-04-14 | Mobay Chemical Corp | Process for the production of practically diisocyanate-free polyisocyanates |
DE2400490A1 (en) * | 1974-01-05 | 1975-07-17 | Akzo Gmbh | METHOD FOR MANUFACTURING CATIONIC POLYURETHANES |
US5747628A (en) * | 1991-12-10 | 1998-05-05 | Bayer Aktiengesellschaft | Polyisocyanates containing ether and urethane groups, a process for their preparation and their use in the production of polyurethane lacquers |
DE19957351A1 (en) * | 1999-11-29 | 2001-10-31 | Henkel Kgaa | Monomer-free reactive polyurethane adhesive or sealant composition, e.g. for use as a hot melt, obtained by reacting polyol with high-mol. wt. di-isocyanate with a low monomer content |
US6903167B2 (en) | 2000-12-15 | 2005-06-07 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Polyurethane prepolymers comprising NCO groups and a low content of monomeric polyisocyanate |
WO2008157013A1 (en) | 2007-06-13 | 2008-12-24 | Hontek Corporation | Method and coating for protecting and repairing an airfoil surface using molded boots, sheet or tape |
WO2011068855A1 (en) | 2009-12-04 | 2011-06-09 | Basf Coatings Gmbh | Method and composition for refinish coatings |
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WO2014139873A1 (en) | 2013-03-12 | 2014-09-18 | Bayer Materialscience Ag | Method for producing light-coloured tdi-polyisocantes |
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WO2018210592A1 (en) | 2017-05-17 | 2018-11-22 | Basf Se | Polyisocyanate (p) and method for the production thereof |
EP3424910A1 (en) | 2017-07-05 | 2019-01-09 | Covestro Deutschland AG | Continuous dilution of polyisocyanates |
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WO2019211127A1 (en) | 2018-04-30 | 2019-11-07 | Evonik Degussa Gmbh | Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters |
WO2020016116A1 (en) | 2018-07-20 | 2020-01-23 | Covestro Deutschland Ag | Ionically hydrophilized polyisocyanates with improved drying |
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EP4105251A1 (en) | 2021-06-18 | 2022-12-21 | Covestro Deutschland AG | Crosslinkable compositions containing imine and / or aminal-forming components |
WO2022263306A1 (en) | 2021-06-18 | 2022-12-22 | Covestro Deutschland Ag | Aldehyde-blocked organic polyisocyanates |
EP4108695A1 (en) | 2021-06-21 | 2022-12-28 | Covestro Deutschland AG | Coating agent and coatings produced therefrom having improved soiling resistances and (self) cleaning properties |
EP4108694A1 (en) | 2021-06-21 | 2022-12-28 | Covestro Deutschland AG | Coating agent and coatings produced therefrom having improved soiling resistances and (self) cleaning properties |
WO2023020755A1 (en) | 2021-08-17 | 2023-02-23 | Evonik Operations Gmbh | Polyurea compositions from polyaspartic esters and 2-substituted butanedioic acid esters |
EP4198094A1 (en) | 2021-12-20 | 2023-06-21 | Covestro Deutschland AG | Multilayer structure on metal substrates based on polyaspartate coatings |
EP4265663A1 (en) | 2022-04-21 | 2023-10-25 | Covestro Deutschland AG | Polyaspartate-based two-component coating compositions for the production of coatings having improved self-heating properties and low adhesion |
EP4279522A1 (en) | 2022-05-17 | 2023-11-22 | Covestro Deutschland AG | Water-dispersible polyisocyanates with aldehyde blocking and aqueous compositions obtainable therefrom |
Citations (1)
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DE838826C (en) * | 1949-02-23 | 1952-05-12 | Bayer Ag | Process for the production of molded articles |
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1952
- 1952-07-04 DE DEF9416A patent/DE953012C/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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DE838826C (en) * | 1949-02-23 | 1952-05-12 | Bayer Ag | Process for the production of molded articles |
Cited By (58)
Publication number | Priority date | Publication date | Assignee | Title |
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