EP0000963B1 - Isocyanuratgruppen und endständig-blockierte Isocyanatgruppen-enthaltende Verbindungen und Verfahren zu ihrer Herstellung - Google Patents

Isocyanuratgruppen und endständig-blockierte Isocyanatgruppen-enthaltende Verbindungen und Verfahren zu ihrer Herstellung Download PDF

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Publication number
EP0000963B1
EP0000963B1 EP78200106A EP78200106A EP0000963B1 EP 0000963 B1 EP0000963 B1 EP 0000963B1 EP 78200106 A EP78200106 A EP 78200106A EP 78200106 A EP78200106 A EP 78200106A EP 0000963 B1 EP0000963 B1 EP 0000963B1
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EP
European Patent Office
Prior art keywords
isocyanurate
dimethylketoxime
groups
weight
group
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
EP78200106A
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German (de)
English (en)
French (fr)
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EP0000963A1 (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
Chemische Werke Huels AG
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Filing date
Publication date
Application filed by Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of EP0000963A1 publication Critical patent/EP0000963A1/de
Application granted granted Critical
Publication of EP0000963B1 publication Critical patent/EP0000963B1/de
Expired legal-status Critical Current

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    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • 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
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8077—Oximes
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings

Definitions

  • the present invention relates to a process for the preparation of new compounds with an adjusted isocyanurate group content, and to the compounds obtainable by this process.
  • masked isocyanates also called isocyanate releasers
  • isocyanate releasers Tertiary alcohols, phenols, acetoacetic esters, malonic esters, actylacetone, phthalimide, imidazole, hydrogen chloride, hydrogen cyanide and e-caprolactam are known as blocking agents.
  • blocked isocyanates have the property of reacting like isocyanates at elevated temperature. The more acidic the H atom of the masking group is, the easier it is to split off. Such blocked isocyanates are described in DT-A-21 66 423. Terminal-blocked isocyanates which additionally contain uretdione groups have also been described in DE-A 25 02 934, they are dimerizates, not trimerizates, only the latter catalyzing the subsequent deblocking.
  • NL-A 7 403 748 relates to the production of isocyanate trimers, but IPDI is not mentioned as the diisocyanate.
  • the invention relates to a process for the preparation of blocked isocyanate groups and isocyanurate group-containing compounds from polyisocyanates and monofunctional, acidic hydrogen-containing blocking agents, characterized in that first 3 - isocyanatomethyl - 3,5,5 - trimethyl-cyclohexyl isocyanate in a known manner an isocyanurate mixture containing more than 2 free isocyanate groups is transferred and this intermediate is then reacted with dimethyl ketoxime as a monofunctional, acidic hydrogen-containing blocking agent at 50-120 ° C., the dimethyl ketoxime being used in amounts such that an NCO group equivalent is used Equivalent dimethyl ketoxime is coming.
  • One variant is that the intermediate product obtained is first freed of the monomeric polyisocyanate and then the practically monomer-free polyisocyanate is then blocked in the manner described.
  • the invention further relates to a mixture containing blocked isocyanate groups and isocyanurate groups, consisting of at least 10% by weight of an isocyanurate containing 3-isocyanatomethyl-3,3,3-trimethyl and containing more than 2 isocyanate group-containing blocks prior to blocking cyclohexyl isocyanate and, if appropriate, an amount of the monomeric 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexyl isocyanate blocked with dimethyl ketoxime and adding to 100% by weight, the total content of unblocked NCO groups being ⁇ 0.6% by weight lies.
  • the monomeric polyisocyanate is therefore identical to that which was used to prepare the isocyanurate.
  • the isocyanurate can also be a mixture of the trimeric and higher addition product of the monomeric polyisocyanate.
  • the isocyanurate group content in the compounds produced according to the invention is 2-8% by weight.
  • trimerization of the cycloaliphatic isocyanate is a catalytic reaction.
  • Metal compounds from the group consisting of salts and bases and homeopolar metal compounds wide metal naphthenates, sodium benzoate in DMF, alkaline earth metal acetates, formates and carbonates, metal alkoxides, AICI 3 and Fe acetylacetonate can be used as catalysts.
  • the proposed catalyst system composed of N, N'-endoethylene piperazine and propylene oxide is particularly suitable for trimerization.
  • the trimerization can be carried out in bulk or in inert organic solvents. To carry out the trimerization process, it is essential to terminate the reaction at a certain isocyanate content of the mixture, preferably when 30-50% of the NCO groups have reacted with trimerization. The unreacted isocyanate then becomes thin Layer distillation separated from the isocyanurate formed.
  • the isocyanurate isocyanates thus accessible can be used either as the exclusive isocyanate component or else in a mixture with isocyanurate-free polyisocyanate.
  • the addition of isocyanurate-free polyisocyanate allows the properties of the process products, in particular their melting point, to be varied in a desired manner in a simple manner.
  • the isocyanurate group-containing polyisocyanate thus obtained, the triisocyanate, or deodorant mixtures with isocyanurate group-free polyisocyanate is the precursor to the process products according to the invention referred to above as an intermediate.
  • this intermediate stage is then converted into the process product according to the invention and terminally blocked isocyanate groups as described below without further modification.
  • Dimethyl ketoxime has proven to be particularly suitable since it easily undergoes an addition reaction with the compounds containing isocyanate groups at temperatures above 50 ° C., preferably between 80-120 ° C.
  • the addition products thus obtained in a mixture with non-volatile primary hydroxyl-containing polyols react at temperatures between 100 and 200 ° C. with the liberation of dimethyl ketoxime with the non-volatile polyols with formation of urethane.
  • the isocyanate component is generally introduced and the blocking agent is added.
  • the reaction can be carried out in bulk or in the presence of suitable (inert) solvents.
  • the blocking reaction is generally carried out at 80-120 ° C.
  • the dimethyl ketoxime is used in such amounts that there is one equivalent of blocking agent per NCO group equivalent.
  • the customary isocyanate polyaddition reaction accelerating catalysts such as tin (11) octoate, can also be used.
  • the catalysts are generally used in an amount between 0.001 and 1% by weight, based on the amount of compounds having hydrogen atoms which are reactive toward isocyanates.
  • the process products according to the invention are generally compounds of the molecular weight range 300-3000, preferably 400-2000.
  • the process products have melting points or ranges from 30-200 ° C, preferably 60-170 ° C.
  • the preferred polyisocyanates containing isocyanurate groups according to the invention are moreover characterized by a content of isocyanurate groups (calculated as (CO-N-) 3) of 2% by weight to 14% by weight, preferably 3-10% by weight and a content of terminally in blocked form present isocyanate groups (calculated as NCO) of 2-18, preferably 10-17% by weight.
  • the compounds of the invention described above are particularly suitable because of their low melting points and at the same time higher molecular weights than cocatalysts for the anionic polymerization of E- caprolactam.
  • the process products are also suitable as hardeners for higher functional thermoplastic compounds containing Zerewittinoff active hydrogen atoms.
  • the process products form above 120 ° C., preferably at 160-200 ° C., systems curable to high-quality plastics.
  • the most important field of application for such systems is their use as binders for (PUR) powder coatings.
  • the process products according to the invention are also well suited for the production of storage-stable one-component stoving enamels (especially for coil coating).
  • IPDI Isophorone diisocyanate
  • the catalyst system from 1,4 - -diazobicyclooctane [2,2,2] (also Dabco @ gennant) and propylene oxide heated at 120 ° C for 3 h. During this time, the NCO content fell from 37.8% (corresponding to 100% IPDI) to 28.4% (50% IPDI sales).
  • the reaction mixture was cooled to 40 ° C. and stripped with nitrogen at this temperature for 1/2 h. The NCO content of the reaction mixture changed slightly to 28.2%.
  • this isocyanato-isocyanurate mixture was 49 parts by weight at 100 ° C.
  • Dimethylketoxime added in portions so that the reaction temperature did not rise above 120 ° C.
  • the reaction mixture was kept at 120 ° C. for a further 2 hours.
  • Fig. 1 shows the IR spectrum of the reaction product.
  • this isocyanato-isocyanurate mixture was 46.9 parts by weight at 100 ° C.
  • Dimethylketoxime added in portions so that the reaction temperature did not rise above 120 ° C.
  • the reaction mixture is kept at 120 ° C. for a further 2 hours.
  • Fig. 2 shows the IR spectrum of the reaction product.
  • This isocyanato-isocyanurate mixture was 43.4 parts by weight at 120 ° C.
  • Dimethylketoxim slowly metered in with good stirring. After the addition of dimethyl ketoxin, the reaction mixture was heated at 130 ° C. for a further hour.
  • Fig. 3 shows the IR spectrum of the reaction product.
  • An isocyanato-isocyanurate mixture (with deactivated cat. 1), the NCO content of which was 20.9%, was prepared from IPDI by the process described in 1a-3a.
  • Fig. 4 shows the IR spectrum of the reaction product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyamides (AREA)
EP78200106A 1977-07-20 1978-07-17 Isocyanuratgruppen und endständig-blockierte Isocyanatgruppen-enthaltende Verbindungen und Verfahren zu ihrer Herstellung Expired EP0000963B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2732662 1977-07-20
DE19772732662 DE2732662A1 (de) 1977-07-20 1977-07-20 Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen-enthaltende verbindungen

Publications (2)

Publication Number Publication Date
EP0000963A1 EP0000963A1 (de) 1979-03-07
EP0000963B1 true EP0000963B1 (de) 1982-06-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78200106A Expired EP0000963B1 (de) 1977-07-20 1978-07-17 Isocyanuratgruppen und endständig-blockierte Isocyanatgruppen-enthaltende Verbindungen und Verfahren zu ihrer Herstellung

Country Status (6)

Country Link
US (2) US4246132A (da)
EP (1) EP0000963B1 (da)
JP (1) JPS5448777A (da)
DE (2) DE2732662A1 (da)
DK (1) DK323578A (da)
IT (1) IT1097038B (da)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2842641A1 (de) * 1978-09-29 1980-04-10 Bayer Ag Lackpolyisocyanat auf basis von modifiziertem 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexan, ein verfahren zu seiner herstellung und seine verwendung in zweikomponenten-polyurethan-pulverlacken
DE3001060A1 (de) * 1980-01-12 1981-07-16 Chemische Werke Hüls AG, 4370 Marl Blockierte polyisocyanato-isocyanurate und ihre herstellung und verwendung
DE3033860A1 (de) * 1980-09-09 1982-04-15 Bayer Ag, 5090 Leverkusen Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethanlacken
DE3041732A1 (de) * 1980-11-05 1982-06-09 Bayer Ag, 5090 Leverkusen Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid
DE3226131A1 (de) * 1982-07-13 1984-01-19 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von ueberzuegen
DE3303221A1 (de) * 1983-02-01 1984-08-02 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung zur herstellung von polyurethanen
DE3318147A1 (de) * 1983-05-18 1984-11-22 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von, isocyanuratgruppen und olefinische doppelbindungen aufweisenden verbindungen, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung als bindemittel bzw. bindemittelkomponente in ueberzugsmitteln
DE3322719A1 (de) * 1983-06-24 1985-01-03 Chemische Werke Hüls AG, 4370 Marl Pulverfoermige ueberzugsmittel
DE3322829A1 (de) * 1983-06-24 1985-01-03 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von ueberzuegen
DE3322721A1 (de) * 1983-06-24 1985-01-03 Chemische Werke Hüls AG, 4370 Marl Einkomponenten-einbrennlacke
DE3322830A1 (de) * 1983-06-24 1985-01-03 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von ueberzuegen
DE3337395A1 (de) * 1983-10-14 1985-05-02 Herberts Gmbh, 5600 Wuppertal Nichtwaessriger lack mit hohem steinschlagschutz, verfahren zu seiner herstellung und dessen verwendung
DE3337394A1 (de) * 1983-10-14 1985-05-02 Herberts Gmbh, 5600 Wuppertal Steinschlagschutzschicht-lack, verfahren zu seiner herstellung und dessen verwendung
DE3339579A1 (de) * 1983-11-02 1985-05-09 Bayer Ag, 5090 Leverkusen Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung sowie ihre verwendung als isocyanat-komponente in polyurethanlacken
US4547410A (en) * 1983-12-21 1985-10-15 Inmont Corporation Process for applying a multi-layer paint containing mica pigment
US4607103A (en) * 1985-08-13 1986-08-19 General Electric Company, Silicone Products Division Methods for making blocked isocyanurates
DE3735198A1 (de) * 1987-10-17 1989-05-03 Bayer Ag In wasser loesliche oder dispergierbare, blockierte polyisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung
US4868298A (en) * 1988-06-22 1989-09-19 Cargill, Incorporated Continuous process for the production of blocked isocyanate containing polyisocyanurates
US5095087A (en) * 1989-07-03 1992-03-10 Eastman Kodak Company Oxime-blocked polyisocyanates and polyester and powder coating compositions containing such oxime-blocked polyisocyanates
US5028682A (en) * 1989-07-03 1991-07-02 Eastman Kodak Company Oxime-blocked polysicyanates and polyester and powder coating compositions containing such oxide-blocked polyisocyanates
US5296160A (en) * 1991-07-23 1994-03-22 Miles Inc. Aqueous dispersions of blocked polyisocyanates
US5238999A (en) * 1991-08-29 1993-08-24 Basf Corporation Environmental etch resistant, one-component, coating composition, method of coating therewith, and coating obtained therefrom
DE4130336A1 (de) * 1991-09-12 1993-03-18 Bayer Ag Verfahren zur herstellung von pulverlacken und ihre verwendung
US5232988A (en) * 1992-02-25 1993-08-03 Miles Inc. Blocked polyisocyanates prepared from partially trimerized cyclic organic diisocyanates having (cyclo)aliphatically bound isocyanate groups and their use for the production of coatings
DE4419216C1 (de) * 1994-06-01 1995-08-31 Bollig & Kemper Wäßrige Überzugsmittel und deren Verwendung
DE10159768A1 (de) * 2001-12-05 2003-06-26 Degussa Verwendung von Polyurethan-Pulverlacken
EP2625215B1 (de) * 2010-10-07 2019-02-13 Basf Se Verfahren zur herstellung von monomer-zusammensetzungen und deren verwendung zur herstellung eines polyamid-formteils
EP2760906B1 (de) * 2011-09-28 2017-03-01 Basf Se Verfahren zur herstellung von polyamiden durch anionische polymerisation
JP7334875B1 (ja) 2023-03-10 2023-08-29 東ソー株式会社 ブロックイソシアネート組成物及びその製造方法、塗料用硬化剤、塗料組成物、並びに、塗膜

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US2952665A (en) * 1955-12-08 1960-09-13 Mobay Chemical Corp High molecular weight cyclic trimers containing blocked isocyanate groups
GB1032059A (en) * 1963-10-29 1966-06-08 Takeda Chemical Industries Ltd Blocked isocyanate compositions
US3625986A (en) * 1967-12-28 1971-12-07 Nat Distillers Chem Corp Bis 1, 1 isocyanatoalkyl cycloalkanes
NL6808140A (da) * 1968-06-10 1969-12-12
US3577391A (en) * 1968-10-08 1971-05-04 Marathon Oil Co Alcohol-blocker isocyanate compositions and derivatives
US3799854A (en) * 1970-06-19 1974-03-26 Ppg Industries Inc Method of electrodepositing cationic compositions
DE2105777C3 (de) * 1971-02-08 1976-02-05 Veba Chemie Ag Pulverförmige Überzugsmasse
DE2225958C3 (de) * 1972-05-27 1980-08-21 Bayer Ag, 5090 Leverkusen Bindemittel für das elektrostatische Pulverspriihverfahren
DE2325826C3 (de) * 1973-05-22 1981-01-29 Chemische Werke Huels Ag, 4370 Marl Isocyanato-isocyanurate und Herstellung lagerstabiler Lösungen hiervon
FI62677C (fi) * 1974-06-21 1983-02-10 Grow Group Inc Belaeggningskomposition omfattande ett polymeriserat harts medisocyanatreaktiva grupper och ett tvaerbindningsmedel med bockerade isocyanatgrupper
DE2456469C2 (de) * 1974-11-29 1983-01-13 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel
DE2502934A1 (de) * 1975-01-24 1976-07-29 Bayer Ag Uretdiongruppen und endstaendige blockierte isocyanatgruppen aufweisende organische verbindungen
DE2606976A1 (de) * 1975-02-24 1976-09-09 Du Pont Stoffgemische aus blockierten isocyanattrimeren
DE2542706C3 (de) * 1975-09-25 1981-04-09 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Imidgruppen enthaltenden Polykondensaten
DE2644684C2 (de) * 1976-10-02 1983-01-13 Chemische Werke Huels Ag, 4370 Marl Verfahren zur Herstellung von 2,4,6-Triketohexahydrotriazinen
US4055551A (en) * 1976-12-08 1977-10-25 Cargill, Incorporated Continuous process for the production of blocked isocyanates

Also Published As

Publication number Publication date
JPS5448777A (en) 1979-04-17
DE2861909D1 (en) 1982-08-12
DK323578A (da) 1979-01-21
DE2732662A1 (de) 1979-02-01
IT7825905A0 (it) 1978-07-20
US4246132A (en) 1981-01-20
EP0000963A1 (de) 1979-03-07
IT1097038B (it) 1985-08-26
US4306051A (en) 1981-12-15

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