DE19622610A1 - Carbodiimide group-containing, blocked di:isocyanate for stabiliser - Google Patents

Carbodiimide group-containing, blocked di:isocyanate for stabiliser

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Publication number
DE19622610A1
DE19622610A1 DE1996122610 DE19622610A DE19622610A1 DE 19622610 A1 DE19622610 A1 DE 19622610A1 DE 1996122610 DE1996122610 DE 1996122610 DE 19622610 A DE19622610 A DE 19622610A DE 19622610 A1 DE19622610 A1 DE 19622610A1
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DE
Germany
Prior art keywords
diisocyanate
cyclo
oxophospholine
blocked
stage
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.)
Withdrawn
Application number
DE1996122610
Other languages
German (de)
Inventor
Rainer Dr Gras
Elmar Dr Wolf
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.)
Huels AG
Original Assignee
Huels AG
Chemische Werke Huels AG
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Filing date
Publication date
Application filed by Huels AG, Chemische Werke Huels AG filed Critical Huels AG
Priority to DE1996122610 priority Critical patent/DE19622610A1/en
Publication of DE19622610A1 publication Critical patent/DE19622610A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Carbodiimide group-containing (cyclo)aliphatic diisocyanates which are blocked by sterically-hindered piperidine groups and which are of formula (I) are new: R = 4-16C (cyclo)alkylene optionally substituted by 1-4 Me groups; B = a 2,2,6,6-tetra-Me-piperidine group of formula (II); X = H, Me or -CO.Me; and Y =O or NH.

Description

Gegenstand der vorliegenden Erfindung sind mit sterisch gehinderten Piperidinverbindungen irreversibel blockierte Carbodiimidgruppen enthaltende (cyclo)aliphatische Diisocyanate, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung.The present invention relates to sterically hindered Piperidine compounds containing irreversibly blocked carbodiimide groups (Cyclo) aliphatic diisocyanates, a process for their preparation and their Use.

Solche Verbindungen würden eine Bereicherung bei der Stabilisierung von Polymeren darstellen, da sie neben der Schutzwirkung gegenüber UV-Licht auch Schutz gegenüber Einwirkungen von Wasser bieten würden.Such compounds would enrich the stabilization of polymers represent, because in addition to the protective effect against UV light also protection against the effects of water.

Aufgabe der Erfindung war somit die Bereitstellung dieser Verbindungen.The object of the invention was therefore to provide these compounds.

Überraschenderweise konnten Carbodiimidgruppen sowie sterisch gehinderte Aminogruppen enthaltende Verbindungen dadurch hergestellt werden, indem man mit 4-Hydroxy-2.2.6.6-tetramethylpiperidin (irreversibel) monoblockierte (cyclo)ali­ phatische Diisocyanate, die weitgehend frei von mit 4-Hydroxy-2.2.6.6- tetramethylpiperidin diblockierten Diisocyanaten und monomeren Diisocyanaten sind, katalytisch erhitzte.Surprisingly, carbodiimide groups as well as sterically hindered Compounds containing amino groups can be prepared by using 4-Hydroxy-2.2.6.6-tetramethylpiperidine (irreversible) monoblocked (cyclo) ali phatic diisocyanates that are largely free of with 4-hydroxy-2.2.6.6- tetramethylpiperidine are diblocked diisocyanates and monomeric diisocyanates, catalytically heated.

Gegenstand der vorliegenden Erfindung sind daher blockierte (cyclo)aliphatische Diisocyanate, dadurch gekennzeichnet, daß sie eine Carbodiimidgruppe enthalten und folgender Zusammensetzung entsprechen:The present invention therefore relates to blocked (cyclo) aliphatic Diisocyanates, characterized in that they contain a carbodiimide group and correspond to the following composition:

wobei R ein (Cyclo)alkylen-Rest mit 4-16 C-Atomen, der mit 1-4 CH₃-Gruppen substituiert sein kann, bedeutet und B die folgende Formel darstellt:where R is a (cyclo) alkylene radical with 4-16 carbon atoms, with 1-4 CH₃ groups may be substituted, and B represents the following formula:

Die erfindungsgemäßen Verbindungen enthalten im Durchschnitt 1 mol Carbodiimidgruppen (-N=C=N-) pro mol (A). Der irreversibel blockierte NCO-Gehalt liegt bei 10-20%. Weiterhin weisen die erfindungsgemäßen Verbindungen einen Schmelzbereich von 70-150°C auf, vorzugsweise 100-140°C.The compounds according to the invention contain an average of 1 mol Carbodiimide groups (-N = C = N-) per mol (A). The irreversibly blocked NCO content is 10-20%. Furthermore, the compounds according to the invention have one Melting range from 70-150 ° C, preferably 100-140 ° C.

Neben ihrer Schutzwirkung gegenüber Sonnenlichteinstrahlung weisen die erfindungsgemäßen Verbindungen zusätzlich einen hydrolysestabilisierenden Effekt auf.In addition to their protective effect against sunlight, the Compounds according to the invention additionally have a hydrolysis-stabilizing effect.

Für die erfindungsgemäßen Carbodiimidgruppen enthaltenden irreversibel blockierten (cyclo)aliphatischen Diisocyanate kommen alle Diisocyanate in Frage, die sich bei einer Temperatur destillieren lassen, die niedriger ist als die Deblockierungstemperatur des monoblockierten Diisocyanats. Als besonders geeignet haben sich folgende Diiso­ cyanate erwiesen: Hexamethylendiisocyanat (HDI), 2-Methyl-1.5-diiso-cyanatopentan (DI 51), 1.5-Diisocyanatohexan, 1.10-Diisocyanatodecan, 1.9-Diisocyanato-5- methylnonan, Dodecamethylendiisocyanat, Isophorondiisocyanat (IPDI), 2.2.4(2.4.4)- Trimethylhexamethylendiisocyanat (TMDI), Hexahydroxylylendiisocyanat-1.4 oder -1.3. Die Diisocyanate können allein oder auch als Mischungen in den erfindungsgemäßen Verbindungen enthalten sein.For the carbodiimide groups according to the invention containing irreversibly blocked (Cyclo) aliphatic diisocyanates are all diisocyanates that are in a Allow the temperature to distill lower than the deblocking temperature of the monoblocked diisocyanate. The following diiso have been found to be particularly suitable cyanates proven: hexamethylene diisocyanate (HDI), 2-methyl-1,5-diiso-cyanatopentane (DI 51), 1,5-diisocyanatohexane, 1.10-diisocyanatodecane, 1.9-diisocyanato-5- methylnonane, dodecamethylene diisocyanate, isophorone diisocyanate (IPDI), 2.2.4 (2.4.4) - Trimethylhexamethylene diisocyanate (TMDI), hexahydroxylylene diisocyanate-1.4 or -1.3. The diisocyanates can be used alone or as mixtures in the Compounds according to the invention may be included.

Als Reaktionskomponenten für die oben aufgeführten Diisocyanate werden 2.2.6.6- Tetramethylpiperidin-Derivate (TAA-Derivate), wie z. B. 4-Hydroxy-2.2.6.6- Tetramethylpiperidin, 4-Hydroxy-1.2.2.6.6-pentamethylpiperidin, 4-Amino-2.2.6.6- tetramethylpiperidin, 4-Amino-1.2.2.6.6-pentamethylpiperidin, eingesetzt. Die Blockierungsmittel können allein oder als Mischungen in den erfindungsgemäßen Verbindungen enthalten sein.2.2.6.6- are used as reaction components for the diisocyanates listed above. Tetramethylpiperidine derivatives (TAA derivatives), such as. B. 4-Hydroxy-2.2.6.6- Tetramethylpiperidine, 4-hydroxy-1.2.2.6.6-pentamethylpiperidine, 4-amino-2.2.6.6-  tetramethylpiperidine, 4-amino-1.2.2.6.6-pentamethylpiperidine. The Blocking agents can be used alone or as mixtures in the inventive Connections may be included.

Der Gehalt der irreversibel monoblockierten Diisocyanate, die nicht Gegenstand der Erfindung sind, sondern nur die Ausgangsverbindungen für die erfindungsgemäßen Verbindungen darstellen, beträgt - je nach Diisocyanat - 11-18 Gew.-%, an Gesamt- NCO 23-35 Gew.-%. Das Molverhältnis von Diisocyanat zum TAA-Derivat hängt davon ab, welcher Gehalt an diblockiertem Diisocyanat zugelassen werden kann. Je höher der Überschuß an Diisocyanat, desto niedriger ist der Gehalt an mit TAA-Derivaten diblockiertem Diisocyanat.The content of irreversibly monoblocked diisocyanates that are not the subject of Are invention, but only the starting compounds for the invention Represent compounds, is - depending on the diisocyanate - 11-18 wt .-%, in total NCO 23-35 wt%. The molar ratio of diisocyanate to TAA derivative depends depends on which content of diblocked diisocyanate can be permitted. Each the higher the excess of diisocyanate, the lower the content of with TAA derivatives diblocked diisocyanate.

Ein weiterer Gegenstand der vorliegenden Erfindung ist ein Verfahren zu ihrer Herstellung, dadurch gekennzeichnet, daß man in einer 1. Stufe 5-20 mol Diisocyanat und 1 mol TAA-Derivat bei 60-120°C umsetzt, und nach erfolgter Umsetzung das nicht umgesetzte Diisocyanat in einer 2. Stufe bei 90-140°C/0,1 mbar abtrennt, und anschließend das so erhaltene Zwischenprodukt bei 120-180°C mit 0,1-3 Gew.-% eines Carbodiimidisierungskatalysators so lange erhitzt, bis der NCO-Gehalt des Reaktionsprodukts (A) 0,1% beträgt.Another object of the present invention is a method for its Preparation, characterized in that in a 1st stage 5-20 mol of diisocyanate and 1 mol TAA derivative at 60-120 ° C, and after the reaction that unreacted diisocyanate in a second stage at 90-140 ° C / 0.1 mbar, and then the intermediate product thus obtained at 120-180 ° C with 0.1-3 wt .-% a carbodiimidization catalyst heated until the NCO content of the Reaction product (A) is 0.1%.

Bei der Umsetzung von überschüssigem Diisocyanat und dem TAA-Derivat geht man so vor, daß man zu 5-20 Molen Diisocyanat bei 60-120°C 1 Mol TAA-Derivat zudosiert und so lange weitererhitzt, bis ein 1 NCO-Äquivalent verbraucht ist. Der Reaktionsverlauf wird durch Bestimmung des NCO-Gehaltes verfolgt. Ist der erwartete NCO-Gehalt erreicht, wird das Reaktionsprodukt in einer 2. Stufe vom nicht umgesetzten Diisocyanat z. B. durch eine Dünnschichtdestillation bei ca. 0,1-0,2 mbar entfernt. Nach dem erfindungsgemäßen Verfahren wird nun das Reaktionsprodukt der 2. Stufe bei 120-180°C mit 0,1-3 Gew.-% eines Carbodiimidisierungskatalysators, wie z. B. Tributylphosphinoxid, oder Phospholinoxide, wie z. B. 1-Methyl-1- oxophospholin, 1-Ethyl-1-oxophospholin, 1-Phenyl-1-oxophospholin, 1.3-Dimethyl-1- oxophospholin, 1.3.4-Trimethyl-1-oxophospholin, so lange unter intensivem Rühren erhitzt, bis der NCO-Gehalt des Reaktionsprodukts (A) 0,1% beträgt. In the implementation of excess diisocyanate and the TAA derivative one goes so that 1 mol of TAA derivative is added to 5-20 moles of diisocyanate at 60-120 ° C metered in and continue to heat until a 1 NCO equivalent has been consumed. Of the The course of the reaction is followed by determining the NCO content. Is the expected NCO content reached, the reaction product in a second stage is not reacted diisocyanate z. B. by a thin film distillation at about 0.1-0.2 mbar away. The reaction product of the 2nd stage at 120-180 ° C with 0.1-3 wt .-% of a carbodiimidization catalyst, such as B. tributylphosphine oxide, or phospholine oxides, such as. B. 1-methyl-1- oxophospholine, 1-ethyl-1-oxophospholine, 1-phenyl-1-oxophospholine, 1,3-dimethyl-1- oxophospholine, 1.3.4-trimethyl-1-oxophospholine, so long with intensive stirring heated until the NCO content of the reaction product (A) is 0.1%.  

Die nach dem erfindungsgemäßen Verfahren hergestellten Verbindungen eignen sich besonders zur Stabilisierung von Polyestern und Polyamiden.The compounds produced by the process according to the invention are suitable especially for stabilizing polyesters and polyamides.

Experimenteller TeilExperimental part A) Herstellung der erfindungsgemäßen VerbindungenA) Preparation of the compounds according to the invention

10 mol Diisocyanat und 1 mol TAA-Derivat werden bei 60-120°C in gewohnter Weise (portionsweise Zudosierung des TAA-Derivats) umgesetzt und nach erfolgter Umsetzung das nicht umgesetzte Diisocyanat in einer 2. Stufe bei 90-140°C/0,1 mbar abgetrennt, und anschließend das so erhaltene Zwischenprodukt bei 120-180°C mit 0,3 Gew.-% 1-Methyl-1-oxophospholin so lange erhitzt (ca. 3 h), bis der NCO-Gehalt des Reaktionsproduktes 0,1 Gew.-% beträgt. Die in der Tabelle 1 angegebenen Verbindungen wurden nach diesem Verfahren hergestellt. 10 moles of diisocyanate and 1 mole of TAA derivative are used at 60-120 ° C in the usual way Way (portionwise addition of the TAA derivative) implemented and after Implementation of the unreacted diisocyanate in a second stage at 90-140 ° C / 0.1 mbar separated, and then the intermediate product thus obtained at 120-180 ° C. heated with 0.3% by weight of 1-methyl-1-oxophospholine (approx. 3 h) until the NCO content of the reaction product is 0.1% by weight. The in Table 1 specified compounds were prepared by this method.  

Tabelle 1 Table 1

Zusammensetzung der erfindungsgemäßen, eine Carbodiimidgruppe enthaltenden Verbindungen Composition of the compounds according to the invention containing a carbodiimide group

Claims (6)

1. Blockierte (cyclo)aliphatische Diisocyanate, dadurch gekennzeichnet, daß sie eine Carbodiimidgruppe enthalten und folgender Zusammensetzung entsprechen: wobei R ein (Cyclo)alkylen-Rest mit 4-16 C-Atomen, der mit 1-4 CH₃- Gruppen substituiert sein kann, bedeutet und B die folgende Formel darstellt: 1. Blocked (cyclo) aliphatic diisocyanates, characterized in that they contain a carbodiimide group and have the following composition: where R is a (cyclo) alkylene radical with 4-16 C atoms, which can be substituted with 1-4 CH₃ groups, and B represents the following formula: 2. Blockierte (cyclo)aliphatische Diisocyanate nach Anspruch 1, dadurch gekennzeichnet, daß R Reste von Hexamethylendiisocyanat (HDI), 2-Methyl-1.5-diiso­ cyanatopentan (DI 51), 1.5-Diisocyanatohexan, 1.10-Diisocyanatodecan, 1.9- Diisocyanato-5-methylnonan, Dodecamethylendiisocyanat, Isophorondiiso­ cyanat (IPDI), 2.2.4(2.4.4)-Trimethylhexamethylendiisocyanat (TMDI), Hexahydroxylylendiisocyanat-1.4 oder -1.3, und beliebige Mischungen dieser Reste bedeutet. 2. Blocked (cyclo) aliphatic diisocyanates according to claim 1, characterized in that that R residues of hexamethylene diisocyanate (HDI), 2-methyl-1.5-diiso cyanatopentane (DI 51), 1.5-diisocyanatohexane, 1.10-diisocyanatodecane, 1.9- Diisocyanato-5-methylnonane, dodecamethylene diisocyanate, isophorone diiso cyanate (IPDI), 2.2.4 (2.4.4) trimethylhexamethylene diisocyanate (TMDI), Hexahydroxylylenediisocyanat-1.4 or -1.3, and any mixtures of these Leftovers means.   3. Blockierte (cyclo)aliphatische Diisocyanate nach den Ansprüchen 1 bis 2, dadurch gekennzeichnet, daß B Reste von 4-Hydroxy-2.2.6.6-Tetramethylpiperidin, 4-Hydroxy- 1.2.2.6.6-pentamethylpiperidin, 4-Amino-2.2.6.6-tetramethylpiperidin, 4-Ami­ no-1.2.2.6.6-pentamethylpiperidin, bedeutet.3. Blocked (cyclo) aliphatic diisocyanates according to claims 1 to 2, characterized, that B residues of 4-hydroxy-2.2.6.6-tetramethylpiperidine, 4-hydroxy- 1.2.2.6.6-pentamethylpiperidine, 4-amino-2.2.6.6-tetramethylpiperidine, 4-amino no-1.2.2.6.6-pentamethylpiperidine means. 4. Verfahren zur Herstellung der Verbindungen gemäß den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß man in einer 1. Stufe 5-20 mol Diisocyanat (OCN-R-NCO) und 1 mol TAA-Derivat bei 60-120°C umsetzt und nach erfolgter Umsetzung das nicht umgesetzte Diisocyanat in einer 2. Stufe bei 90-140°C/0,1 mbar abtrennt, und anschließend das so erhaltene Zwischenprodukt bei 120-180°C mit 0,1-3 Gew.-% eines Carbodiimidisierungskatalysators so lange erhitzt, bis der NCO-Gehalt des Reaktionsprodukts A 0, 1 Gew.-% beträgt.4. A process for the preparation of the compounds according to claims 1 to 3, characterized, that in a 1st stage 5-20 mol of diisocyanate (OCN-R-NCO) and 1 mol TAA derivative implemented at 60-120 ° C and not after the implementation separated diisocyanate in a second stage at 90-140 ° C / 0.1 mbar, and then the intermediate product thus obtained at 120-180 ° C with 0.1-3 % By weight of a carbodiimidization catalyst is heated until the NCO content of the reaction product A is 0.1% by weight. 5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß als Katalysator Tributylphosphinoxid oder Phospholinoxide, wie z. B. 1-Methyl-1-oxophospholin, 1-Ethyl-1-oxophospholin, 1-Phenyl-1-oxophospho­ lin, 1.3-Diinethyl-1-oxophospholin, 1.3.4-Trimethyl-1-oxophospholin, einge­ setzt werden.5. The method according to claim 4, characterized, that as a catalyst tributylphosphine oxide or phospholine oxides, such as. B. 1-methyl-1-oxophospholine, 1-ethyl-1-oxophospholine, 1-phenyl-1-oxophospho lin, 1,3-diethyl-1-oxophospholine, 1,3,4-trimethyl-1-oxophospholine, inserted be set. 6. Verfahren nach den Ansprüchen 4 bis 5, dadurch gekennzeichnet, daß das nicht umgesetzte Diisocyanat der 2. Stufe durch eine Dünnschichtdestillation bei reduziertem Druck abgetrennt wird.6. The method according to claims 4 to 5, characterized, that the unreacted diisocyanate of the 2nd stage by a Thin-film distillation is separated off under reduced pressure.
DE1996122610 1996-06-05 1996-06-05 Carbodiimide group-containing, blocked di:isocyanate for stabiliser Withdrawn DE19622610A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7825276B2 (en) * 2006-01-05 2010-11-02 Bayer Materialscience Ag Process for the preparation of liquid, storage-stable organic isocyanates containing carbodiimide and/or uretoneimine groups
US20120238676A1 (en) * 2011-03-18 2012-09-20 Basf Se Use of oligomeric carbodiimides as stabilizers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7825276B2 (en) * 2006-01-05 2010-11-02 Bayer Materialscience Ag Process for the preparation of liquid, storage-stable organic isocyanates containing carbodiimide and/or uretoneimine groups
US20120238676A1 (en) * 2011-03-18 2012-09-20 Basf Se Use of oligomeric carbodiimides as stabilizers
US8623945B2 (en) * 2011-03-18 2014-01-07 Basf Se Use of oligomeric carbodiimides as stabilizers

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