EP0000963A1 - Isocyanurates contenant des groupes isocyanates bloqués et leur procédé de préparation - Google Patents

Isocyanurates contenant des groupes isocyanates bloqués et leur procédé de préparation Download PDF

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Publication number
EP0000963A1
EP0000963A1 EP78200106A EP78200106A EP0000963A1 EP 0000963 A1 EP0000963 A1 EP 0000963A1 EP 78200106 A EP78200106 A EP 78200106A EP 78200106 A EP78200106 A EP 78200106A EP 0000963 A1 EP0000963 A1 EP 0000963A1
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EP
European Patent Office
Prior art keywords
isocyanurate
groups
blocked
isocyanate
weight
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.)
Granted
Application number
EP78200106A
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German (de)
English (en)
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EP0000963B1 (fr
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
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Chemische Werke Huels AG
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Publication date
Application filed by Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of EP0000963A1 publication Critical patent/EP0000963A1/fr
Application granted granted Critical
Publication of EP0000963B1 publication Critical patent/EP0000963B1/fr
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, acetylacetone, phthalimide, imidazole, hydrogen chloride, hydrogen cyanide and ⁇ -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-OS 21 66 423. Terminally blocked isocyanates are also the in addition, uretdione groups have been described in DT-OS 25 02 934.
  • the invention relates to a process for the preparation of blocked isocyanate group and isocyanurate group-containing compounds from aliphatic and / or cycloaliphatic polyisocyanates and monofunctional acidic hydrogen-containing blocking agents, which is characterized in that first the aliphatic and / or cycloaliphatic polyisocyanates transferred in a known manner into a mixture comprising at least 2 free isocyanate group-containing isocyanurate and then reacting this intermediate with dimethyl ketoxime as a monofunctional, acidic hydrogen-containing blocking agent at 50-120 ° C., the dimethyl ketoxime being used in amounts such that a NCO group equivalent comes one equivalent of dimethyl ketoxime.
  • 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 blocked isocyanate group and isocyanurate group-containing compounds consisting of at least 10% by weight of an isocyanurate containing dimethyl ketoxime and at least 2 isocyanate groups before blocking and optionally an amount of a monomeric polyisocyanate blocked with dimethylketoxime and 100% by weight, and an unblocked NCO group content of ⁇ 0.5% by weight.
  • the monomeric polyisocyanate is expediently identical to that which was used to prepare the isocyanurate. Because of the good optical properties, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate is particularly preferred because of the good optical properties and the addition products derived therefrom as isocyanurates.
  • 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.
  • Polyisocyanates in particular diisocyanates, such as aliphatic, cycloaliphatic and / or araliphatic, ie aryl-substituted aliphatic diisocyanates, as described, for example, in the article by W.
  • diisocyanates such as aliphatic, cycloaliphatic and / or araliphatic, ie aryl-substituted aliphatic diisocyanates, as described, for example, in the article by W.
  • isocyanurate isocyanates ie for trimerization - 136
  • isocyanurate isocyanates such as 1,2-ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexaethylene diisocyanate, 2,2,4- or 2,4,4-trimethyl-1, 6-hexamethylene diisocyanate (TMDI), 1,12-Dodscan diisocyanate, ⁇ , ⁇ '-diisocyanatodipropyl ether, cyclobutane-1,3-diisocyanate, cyclohexane-1,3 and 1,4-diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate, which is also known as Isophorone diisocyanate and is abbreviated IPDI, hexahydro-1,3- or -1
  • aliphatic or cycloaliphatic diisocyanates such as 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexyl isocyanate, 2,4- and 3,6-hexahydrotoluenediisocyanate, perhydro-2,4'-and / or -4,4'-diphenylmethane diisocyanate and 1,6-hexamethylene diisocyanate and their isomeric mixtures.
  • aliphatic and / or cycloaliphatic monoisocyanates comparable to the above polyisocyanates can also be used to a limited extent, provided that the isocyanurate isocyanate formed contains on average at least 2 free isocyanate groups.
  • trimerization in a known manner, as described for example in GB-PS 1 391 066 and DT-OS 23 25 826.
  • the trimerization of the aliphatic or cycloaliphatic isocyanates described is a catalytic reaction.
  • Metal compounds from the group consisting of salts and bases and homeopolar metal compounds such as metal naphthenates, sodium benzoate in DMF, alkaline earth metal acetates, formates and carbonates, metal alkoxides, AlCl 3 and Fe acetylacetonate can be used as catalysts.
  • the proposed catalyst system composed of N, N'-3ndoethylene piperazine and propylene oxide is particularly suitable for the trimerization of aliphatic isocyanates.
  • the trimerization can be carried out in bulk or in inert organic solvents.
  • 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 is then separated from the isocyanurate formed by thin-layer distillation.
  • the isocyanurate isocyanates thus accessible can be used either as the exclusive isocyanate component or as a mixture with isocyanurate-free poly Isocyanates are used.
  • the addition of isocyanurate group-free polyisocyanates 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 polyisocyanates preferably triisocyanates, or mixtures thereof with isocyanurate group-free polyisocyanates, preferably diisocyanates, are the precursors to the process products according to the invention, which are referred to above as intermediates.
  • this intermediate stage is now described below without further modification in the present invention e isocyanurate and transferred terminally blocked isocyanate groups product of the process.
  • 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 polyols containing primary hydroxyl groups react at temperatures between 100 and 200 ° C. with the release of dimethylketoxime with the non-volatile polyols with urethane formation.
  • the isocyanate component is generally initially introduced and the blocking agent is added.
  • the reaction can be in substance or in counter suitable (inert) solvents had to be carried out.
  • 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 (II) 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 terminated 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 terminal Isocyanate groups present in blocked form (calculated as NCO) of 2-18, preferably 10-17,% by weight are characterized.
  • 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 Zerewitinoff active hydrogen atoms. In combination with such compounds having Zerewitinoff-active hydrogen atoms, the process products form above 120 ° C. Systems that can be hardened to high-quality plastics, preferably at 160 - 200 ° C. 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).
  • Fig. 1 shows the IR spectrum of the reaction product.
  • Fig. 2 shows the IR spectrum of the reaction product.
  • Fig. 3 shows the IR spectrum of the reaction product.
  • 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)
  • Polyamides (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP78200106A 1977-07-20 1978-07-17 Isocyanurates contenant des groupes isocyanates bloqués et leur procédé de préparation Expired EP0000963B1 (fr)

Applications Claiming Priority (2)

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

Publications (2)

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

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78200106A Expired EP0000963B1 (fr) 1977-07-20 1978-07-17 Isocyanurates contenant des groupes isocyanates bloqués et leur procédé de préparation

Country Status (6)

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

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132515A1 (fr) * 1983-06-24 1985-02-13 Hüls Aktiengesellschaft Revêtements en poudre
EP0132513A1 (fr) * 1983-06-24 1985-02-13 Hüls Aktiengesellschaft Vernis au four à composant unique
US4547410A (en) * 1983-12-21 1985-10-15 Inmont Corporation Process for applying a multi-layer paint containing mica pigment
EP0312836A3 (en) * 1987-10-17 1990-10-03 Bayer Ag Water-soluble or -dispersable, blocked polyisocyanates, a method for their preparation and their use
WO1991000267A1 (fr) * 1989-07-03 1991-01-10 Eastman Kodak Company Polyisocyanates bloques par l'oxime et compositions polyester et a couche de poudre contenant de telles polyisocyanates bloquees par l'oxime
EP0531862A1 (fr) * 1991-09-12 1993-03-17 Bayer Ag Procédé de préparation de vernis en poudre et leur utilisation
EP0557822A3 (en) * 1992-02-25 1993-12-22 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
EP0579042A3 (fr) * 1992-07-14 1994-03-16 Basf Corp

Families Citing this family (21)

* 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
DE3322829A1 (de) * 1983-06-24 1985-01-03 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von ueberzuegen
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
US4607103A (en) * 1985-08-13 1986-08-19 General Electric Company, Silicone Products Division Methods for making blocked isocyanurates
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
US5296160A (en) * 1991-07-23 1994-03-22 Miles Inc. Aqueous dispersions of blocked polyisocyanates
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
WO2012045806A1 (fr) * 2010-10-07 2012-04-12 Basf Se Procédé de production de compositions monomériques et utilisation desdites compositions monomériques pour fabriquer un article façonné en polyamide
CN103842400B (zh) * 2011-09-28 2015-04-22 巴斯夫欧洲公司 通过阴离子聚合制备聚酰胺的方法
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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7403748A (en) * 1968-06-10 1974-06-25 Two-component catalyst system for trimerisation of
FR2292724A1 (fr) * 1974-11-29 1976-06-25 Bayer Ag Procede de preparation de polyisocyanates bloques solubles ou dispersables dans l'eau
DE2502934A1 (de) * 1975-01-24 1976-07-29 Bayer Ag Uretdiongruppen und endstaendige blockierte isocyanatgruppen aufweisende organische verbindungen
FR2299354A1 (fr) * 1974-06-21 1976-08-27 Grow Chemical Corp Polyisocyanate bloque et son obtention
US4031050A (en) * 1970-06-19 1977-06-21 Ppg Industries, Inc. Cationic electrodepositable compositions of blocked NCO and acid salt of adduct of amine and polyepoxide
US4055551A (en) * 1976-12-08 1977-10-25 Cargill, Incorporated Continuous process for the production of blocked isocyanates
DE2644684A1 (de) * 1976-10-02 1978-04-06 Veba Chemie Ag Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen

Family Cites Families (9)

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US2952665A (en) * 1955-12-08 1960-09-13 Mobay Chemical Corp High molecular weight cyclic trimers containing blocked isocyanate groups
BE654888A (fr) * 1963-10-29 1965-02-15
US3625986A (en) * 1967-12-28 1971-12-07 Nat Distillers Chem Corp Bis 1, 1 isocyanatoalkyl cycloalkanes
US3577391A (en) * 1968-10-08 1971-05-04 Marathon Oil Co Alcohol-blocker isocyanate compositions and derivatives
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
JPS51108080A (fr) * 1975-02-24 1976-09-25 Du Pont
DE2542706C3 (de) * 1975-09-25 1981-04-09 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Imidgruppen enthaltenden Polykondensaten

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7403748A (en) * 1968-06-10 1974-06-25 Two-component catalyst system for trimerisation of
US4031050A (en) * 1970-06-19 1977-06-21 Ppg Industries, Inc. Cationic electrodepositable compositions of blocked NCO and acid salt of adduct of amine and polyepoxide
FR2299354A1 (fr) * 1974-06-21 1976-08-27 Grow Chemical Corp Polyisocyanate bloque et son obtention
FR2292724A1 (fr) * 1974-11-29 1976-06-25 Bayer Ag Procede de preparation de polyisocyanates bloques solubles ou dispersables dans l'eau
DE2502934A1 (de) * 1975-01-24 1976-07-29 Bayer Ag Uretdiongruppen und endstaendige blockierte isocyanatgruppen aufweisende organische verbindungen
DE2644684A1 (de) * 1976-10-02 1978-04-06 Veba Chemie Ag 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

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132515A1 (fr) * 1983-06-24 1985-02-13 Hüls Aktiengesellschaft Revêtements en poudre
EP0132513A1 (fr) * 1983-06-24 1985-02-13 Hüls Aktiengesellschaft Vernis au four à composant unique
US4547410A (en) * 1983-12-21 1985-10-15 Inmont Corporation Process for applying a multi-layer paint containing mica pigment
EP0312836A3 (en) * 1987-10-17 1990-10-03 Bayer Ag Water-soluble or -dispersable, blocked polyisocyanates, a method for their preparation and their use
WO1991000267A1 (fr) * 1989-07-03 1991-01-10 Eastman Kodak Company Polyisocyanates bloques par l'oxime et compositions polyester et a couche de poudre contenant de telles polyisocyanates bloquees par l'oxime
EP0409745A1 (fr) * 1989-07-03 1991-01-23 Eastman Kodak Company Polyisocyantes bloqués par une oxime et compositions à base de polyesters ou compositions de revêtement en poudre à base de polyesters les contenant
EP0531862A1 (fr) * 1991-09-12 1993-03-17 Bayer Ag Procédé de préparation de vernis en poudre et leur utilisation
EP0557822A3 (en) * 1992-02-25 1993-12-22 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
EP0579042A3 (fr) * 1992-07-14 1994-03-16 Basf Corp

Also Published As

Publication number Publication date
EP0000963B1 (fr) 1982-06-23
US4246132A (en) 1981-01-20
JPS5448777A (en) 1979-04-17
DE2732662A1 (de) 1979-02-01
US4306051A (en) 1981-12-15
DE2861909D1 (en) 1982-08-12
DK323578A (da) 1979-01-21
IT1097038B (it) 1985-08-26
IT7825905A0 (it) 1978-07-20

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