EP0000798A1 - Vernis pulvérulents à base de polyuréthane - Google Patents

Vernis pulvérulents à base de polyuréthane Download PDF

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Publication number
EP0000798A1
EP0000798A1 EP78200117A EP78200117A EP0000798A1 EP 0000798 A1 EP0000798 A1 EP 0000798A1 EP 78200117 A EP78200117 A EP 78200117A EP 78200117 A EP78200117 A EP 78200117A EP 0000798 A1 EP0000798 A1 EP 0000798A1
Authority
EP
European Patent Office
Prior art keywords
isocyanate
isocyanatomethyl
isocyanurate
caprolactam
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
EP78200117A
Other languages
German (de)
English (en)
Other versions
EP0000798B1 (fr
Inventor
Rainer Dr. Gras
Felix Dr. Schmitt
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of EP0000798A1 publication Critical patent/EP0000798A1/fr
Application granted granted Critical
Publication of EP0000798B1 publication Critical patent/EP0000798B1/fr
Expired legal-status Critical Current

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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
    • C08G18/77—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
    • 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
    • C08G18/8074—Lactams
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/902—Particulate material prepared from an isocyanate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

Definitions

  • ⁇ -caprolactam has established itself as a blocking agent for the isocyanate groups with regard to the odor nuisance and blistering (DT-OS 19 57 483).
  • IPDI 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate
  • Polyurethane powder coatings based on IPDI blocked with C-caprolactam are particularly good compared to polyurethane powder coatings based on other polyisocyanates Weather stability, flow characteristics and thermal stability. However, they have the disadvantage - compared with, for example, epoxy resin powders - that the curing conditions, ie the curing temperature and the curing time, are relatively high.
  • powder coatings made of macromolecular compounds containing hydroxyl groups such as polyesters, polyacrylates and epoxy resins, and ⁇ -caprolactam-blocked polyisocyanates either do not have the abovementioned disadvantages, or do so in a very weakened form, when they are polyisocyanate, the trilsocyanato isocyanurate from 3-isocyanatomethyl -3,5,5-trimethylcyclohexyl isocyanate and optionally oligomers together with monomeric 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate.
  • the invention therefore relates to powdered polyurethane lacquers composed of hydroxyl-containing polyesters, polyacrylates or epoxy resins and ⁇ -caprolactam-blocked polyisocyanates as the curing component, characterized in that the polyisocyanate component is the triisocyanato isocyanurate of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate and optionally oligomers together with monomeric 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate is used.
  • This aliphatic triisocyanate isocyanurate can be prepared by the process of DT-OS 23 25 826.
  • a further suitable trimerization catalyst is also described in DT-OS 26 44 684.
  • the trimerization can be carried out in bulk or in inert solvents. To carry out the trimerization process, it is essential to test the reaction at a abort certain MCO content of the mixture, preferably when 30-60% of the NCO groups have reacted with trimerization.
  • the unreacted isocyanate is then separated from the friisocyanurate by thin-layer distillation.
  • the accessible triisocyanatoisocyanurate is used in a mixture with isocyanurate-free diisocyanate for blocking with ⁇ -caprolactam.
  • the addition of the isocyanurate-free diisocyanate allows the properties of the process products, in particular their melting point, to be varied in a desired manner in a simple manner.
  • a triisocyanato-isocyanurate mixture prepared in, among others can still contain other oligomers of diisocyanate, used directly with ⁇ -caprolactam in a mixture with the monomeric diisocyanate.
  • Triisocyanatoisocyanurate and diisocyanate are used in a weight ratio of approximately 80:20 to 30:70.
  • the isocyanurate groups which are not completely blocked with ⁇ -caprolactam are also suitable for the preparation of the powder-like crossover agents according to the invention, but not more than one isocyanate group per molecule must be free, since crosslinking occurs only when the components are mixed.
  • the polyesters can also contain monofunctional carboxylic acids, e.g. Benzoic acid and acyclic polycarboxylic acids, such as adipic acid, 2,4,4- (2,2,4) -trimethyladipic acid, sebacic acid, dodecanedicarboxylic acid.
  • the polyesters are prepared in a manner known per se by esterification or transesterification, if appropriate in the presence of customary catalysts, end products being obtained by suitable choice of the COOH / OH ratio, the hydroxyl number of which is between about 40 and 240, preferably between about 40 and about 150 , lies.
  • the softening temperatures of the polyesters must be so low that they can be processed at temperatures between about 70.degree. C. and 120.degree. C. with the additives necessary for the preparation of the coating compositions according to the invention.
  • the softening points must be so high that the coating compositions according to the invention obtained from the polyesters can be ground to form non-clumping, free-flowing powders with a particle size of approximately 20 to approximately 120 ⁇ m.
  • the coating agents according to the invention can be produced in suitable mixing units, for example in stirred tanks or mixing screws.
  • Conventional additives such as pigments, leveling agents, plasticizers, fillers and catalysts, can also be used in a simple manner without using solvents be added.
  • the powdery coating compositions can easily be processed in the usual way, for example in a fluidized bed or by electrostatic spraying; by heating to temperatures above about 150 ° C, preferably between about 160 and 200 ° C, coatings with excellent properties are obtained.
  • A-1 6.75 mol (1323 g) dimethyl terephthalate, 2.25 mol (373.5 g) terephthalic acid, 6 mol (624 g) 1,3-dimethylpropanediol, 1 mol (134 g) trimethylol propane and 3 , 0 moles (432 g) of 1,4-dimethylolcyclohexane were combined in a 5 1 glass flask and heated with the aid of an oil bath. After the majority of the substances had melted, 0.1% by weight at a temperature of 160 ° C. % Of dibutyltin oxide was added as the esterification catalyst, and the bottom temperature was slowly increased to 185 ° C.
  • A-2 9 moles (1746 g) of dimethyl terephthalate, 4 moles (416 g) of 1,3-dimethylpropanediol, 3.75 moles (540 g) of 1,4-dimethylolcyclohexane and 2.5 moles (335 g) of trimethylol propane were subjected to the esterification as described in A-1 under the catalytic action of 0.05% by weight of dibutyltin oxide.
  • the first elimination of methanol occurred at a bottom temperature of about 170 ° C.
  • the transesterification was completed after about 14 hours, with transesterification at a maximum temperature in the final phase of 220 ° C.
  • B-2 100 parts by weight of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate were mixed with 0.5 part by weight of a catalyst system composed of 2 parts by weight of 1,2-propylene oxide and 1 part by weight of 1 , 4-Diazabicyclooctan- (2,2,2) heated at 120 ° C for 3 h. During this time, the NCO content fell from 37.8% (100% IPDI) to 28.4% (50% IPDI sales). To deactivate the catalyst, 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%.
  • B-3 100 parts by weight of IPDI were mixed with 0.75 part by weight of a catalyst system composed of 2 parts by weight of propylene oxide and 1 part by weight of 1,4-diazabicyclooctane (2.2.2) for 2 hours at 120 ° C heated. During this time, the NCO content fell from 37.8% to 29.4%.
  • evacuation was carried out at 120 ° C. and 30 torr for 15 minutes. During this time the NCO content of the piaction mixture changed to 27%.
  • the powder coating was prepared in the manner corresponding to the prior art. It should therefore only be described briefly.
  • composition corresponded to the following recipe:
  • a masterbatch of the leveling agent was made in polyester. Masterbatch, polyester, hardener and pigment were intimately mixed in a solid mixer and then extruded at a melt temperature of 95 - 100 ° C. The solidified melt was ground to a grain size of ⁇ 100 ⁇ , and the powder coating was applied electrostatically to 1 mm steel test panels.
  • the paints were baked under various curing conditions and subjected to a paint test after 24 hours.
  • the elasticity which is measured by the Erichsen indentation, is a good parameter for assessing the degree of hardening.
  • Example 1 The technology described in Example 1 was used to produce a polyurethane powder coating of the formulation below, applied to 1 mm steel sheet and cured under various conditions.
  • polyester A-2 100 parts by weight of polyester A-2 were mixed with 46.8 parts by weight of the ⁇ -caprolactam blocked isocyanate-isocyanurate mixture of IPDI, prepared according to C-2.2, and 0.73 parts by weight of silicone oil in the Melt homogenized at temperatures of 120 - 140 ° C with an intensive stirrer. After cooling, the homogeneous melt was broken and then ground with a pin mill on a RorngrcSBe ⁇ 100 ⁇ . The clear lacquer powder produced in this way was applied with an electrical powder spraying system at 60 kV to iron plates primed with zinc phosphate and baked in a forced-air drying cabinet at temperatures between 180 and 200 ° C.
  • polyester A-2 was reacted with the hardener described in C-2.1 in an equivalent amount and prepared as described in Example 4.
  • the clearcoat was applied as described in Example 4 and baked in a forced-air drying cabinet between 180 and 200 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
EP78200117A 1977-08-06 1978-07-25 Vernis pulvérulents à base de polyuréthane Expired EP0000798B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2735497 1977-08-06
DE19772735497 DE2735497A1 (de) 1977-08-06 1977-08-06 Pulverfoermige polyurethanlacke

Publications (2)

Publication Number Publication Date
EP0000798A1 true EP0000798A1 (fr) 1979-02-21
EP0000798B1 EP0000798B1 (fr) 1981-09-02

Family

ID=6015781

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78200117A Expired EP0000798B1 (fr) 1977-08-06 1978-07-25 Vernis pulvérulents à base de polyuréthane

Country Status (9)

Country Link
US (1) US4246380A (fr)
EP (1) EP0000798B1 (fr)
JP (1) JPS5440832A (fr)
AT (1) AT376992B (fr)
DE (2) DE2735497A1 (fr)
DK (1) DK345478A (fr)
FI (1) FI63770C (fr)
IT (1) IT1097679B (fr)
ZA (1) ZA784439B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0023023A1 (fr) * 1979-07-19 1981-01-28 Chemische Werke Hüls Ag Masses de revêtement pulvérulentes de haute stabilité au stockage et leur préparation
EP0026448A1 (fr) * 1979-09-26 1981-04-08 Hüls Aktiengesellschaft Vernis au four à un composant
EP0075206A1 (fr) * 1981-09-18 1983-03-30 BASF Aktiengesellschaft Procédé de préparation de revêtements
EP0139830A2 (fr) * 1983-08-04 1985-05-08 Hüls Aktiengesellschaft Revêtements en poudre à base d'isocyanurates de diisocyanate d'isophorone partiellement bloqués et de polyesters contenant des groupes hydroxyles, procédé de préparation de revêtements mats
EP0023626B1 (fr) * 1979-07-19 1985-10-23 Hüls Aktiengesellschaft Préparation de produits d'addition d'isophorone-diisocyanate contenant des groupes NCO libres et bloqués par l'epsilon-caprolactame et produits d'addition ainsi fabriqués
GB2185988A (en) * 1986-01-31 1987-08-05 Inventa Ag Polyester melt-adhesive compositions
EP0538597A1 (fr) * 1991-10-15 1993-04-28 Hüls Aktiengesellschaft Produits d'addition de polyisocyanate bloqués ayant une fonctionnalité élevée, procédé pour sa préparation et son utilisation
EP0579042A2 (fr) * 1992-07-14 1994-01-19 Basf Corporation Composition de revêtement à composant unique résistant à la corrosion sans influence sur l'environnement, procédé de revêtement avec celle-ci et revêtement obtenu à partir de cell-ci

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US4293659A (en) * 1980-05-01 1981-10-06 Freeman Chemical Corporation Composition for coating molded articles
US4366109A (en) * 1980-05-01 1982-12-28 Freeman Chemical Corporation Method for making coated molded articles
DE3028496C2 (de) * 1980-07-26 1986-04-24 Preh, Elektrofeinmechanische Werke Jakob Preh Nachf. Gmbh & Co, 8740 Bad Neustadt Haftvermittler für ein Trägermaterial
DE3039824A1 (de) * 1980-10-22 1982-05-27 Bayer Ag, 5090 Leverkusen Neue lackpolyisocyanate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in hitzehaertbaren zweikomponenten-polyurethanlacken
US4395529A (en) * 1981-07-20 1983-07-26 Cargill, Incorporated Coating powders for protective films based on epsilon-caprolactam blocked isocyanates
US4375539A (en) * 1981-07-22 1983-03-01 Eastman Kodak Company Solid blocked crosslinking agents based on 1,4-cyclohexane bis(methylisocyanate)
DE3134640C1 (de) * 1981-09-02 1983-01-27 Dynamit Nobel Ag, 5210 Troisdorf Saeuresterilisationsfeste Polyesterlacke
DE3312028A1 (de) * 1983-04-02 1984-10-11 Chemische Werke Hüls AG, 4370 Marl Blockierte polysocyanate, ihre herstellung und verwendung
DE3434881A1 (de) * 1984-09-22 1986-04-03 Hüls AG, 4370 Marl Lagerstabile polyurethanharz-pulverlacke
JPS62282950A (ja) * 1986-06-02 1987-12-08 Hitachi Ltd 感熱記録ヘツド
DE3624775A1 (de) * 1986-07-22 1988-01-28 Bayer Ag Pulverlack und seine verwendung zur beschichtung von hitzeresistenten substraten
US5047439A (en) * 1987-12-03 1991-09-10 Somar Corporation Expandable powder coating composition, method of coating a substrate with heat-insulating foam and composite material obtained thereby
DE4204995C2 (de) * 1992-02-19 1994-11-03 Huels Chemische Werke Ag Mit 2,5-Diketopiperazinen blockierte Diisocyanate, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung in Polyurethan-Pulverlacken
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
DE4408230A1 (de) * 1994-03-11 1995-09-14 Bosch Gmbh Robert Transparente Abdeckscheibe aus Kunststoff für Kfz-Scheinwerfer u. dgl. und Verfahren zu ihrer Herstellung
US5795950A (en) * 1994-05-20 1998-08-18 Asahi Kasei Kogyo Kabushiki Kaisha Straight chain crystalline polyuretdione
DE9413475U1 (de) 1994-08-20 1994-10-13 Mannesmann Kienzle Gmbh, 78052 Villingen-Schwenningen Fahrtschreiber mit Mitteln zur geräteseitigen Befestigung eines den Geberleitungen zugeordneten Schutzrohres
DE19603389A1 (de) 1996-01-31 1997-08-07 Huels Chemische Werke Ag Blockierte aliphatische Diisocyanate oder Diisocyanat-Addukte
DE19604581A1 (de) 1996-02-08 1997-08-14 Bayer Ag Polyurethan-Pulvermattlacke
DE19754748B4 (de) * 1997-12-10 2004-04-29 Gras, Rainer, Dipl.-Chem. Dr. Verfahren zur Herstellung eines blockierten Lackpolyisocyanats und dessen Verwendung für PUR-Lacke
DE10015890A1 (de) 2000-03-30 2001-10-11 Degussa Isocyanuratgruppenhaltige Polyisocyanate aus 1,4-Diisocyanato-2,2,6-trimethylcyclohexan, ein Verfahren zur Herstellung und Verwendung
DE10033097A1 (de) 2000-07-07 2002-01-17 Degussa Verfahren zur Herstellung von hochreaktiven(semi)kristallinen und amorphen blockierten Polyisocyanaten
DE10159768A1 (de) * 2001-12-05 2003-06-26 Degussa Verwendung von Polyurethan-Pulverlacken
DE10163826A1 (de) 2001-12-22 2003-07-03 Degussa Strahlen härtbare Pulverlackzusammensetzungen und deren Verwendung
DE10320266A1 (de) 2003-05-03 2004-11-18 Degussa Ag Feste Uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen bei niedriger Temperatur härtbar
DE10346957A1 (de) 2003-10-09 2005-05-04 Degussa Hochreaktive, flüssige uretdiongruppenhaltige Polyurenthansysteme, die bei niedriger Temperatur härtbar sind
DE10347902A1 (de) * 2003-10-15 2005-05-19 Degussa Ag Feste uretdiongruppenhaltige Polyadditionsverbindungen
DE102004020429A1 (de) * 2004-04-27 2005-11-24 Degussa Ag Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten
DE102004020451A1 (de) * 2004-04-27 2005-12-01 Degussa Ag Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten
DE102007022789A1 (de) 2007-04-26 2008-10-30 Evonik Degussa Gmbh Bei niedriger Temperatur härtbare, Uretdiongruppen aufweisende Polyurethanzusammensetzungen enthaltend Polymere auf der Basis von sekundären OH-Gruppen tragenden Polyolen
DE102007038807A1 (de) 2007-08-16 2009-02-19 Evonik Degussa Gmbh Klebstoffe auf der Basis von Polyester-pfropf-Poly(meth)acrylat-Copolymeren
DE102007062316A1 (de) 2007-12-21 2009-06-25 Evonik Degussa Gmbh Reaktive Isocyanatzusammensetzungen
DE102008007386A1 (de) 2008-02-01 2009-08-06 Evonik Degussa Gmbh Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend
DE102008002703A1 (de) 2008-06-27 2009-12-31 Evonik Degussa Gmbh Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten
DE102008040464A1 (de) 2008-07-16 2010-01-21 Evonik Degussa Gmbh Gekoppelte Polyester-Acrylat-Pfropfpolymere
DE102010041239A1 (de) * 2010-09-23 2012-03-29 Evonik Degussa Gmbh Prepregs auf der Basis lagerstabiler reaktiven oder hochreaktiven Polyurethanzusammensetzung
DE102011006163A1 (de) * 2011-03-25 2012-09-27 Evonik Degussa Gmbh Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten
US10004292B2 (en) 2014-04-09 2018-06-26 Nike, Inc. Selectively applied adhesive particulate on nonmetallic substrates
US9707727B2 (en) * 2014-04-09 2017-07-18 Nike, Inc. Selectively applied adhesive particulate on nonmetallic substrates
DE102014214130A1 (de) 2014-07-21 2016-01-21 Evonik Degussa Gmbh Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten
MX2017014614A (es) * 2015-05-20 2018-03-01 Nike Innovate Cv Particulado adhesivo aplicado en forma selectiva en substratos no metalicos.
US9920219B2 (en) 2015-06-22 2018-03-20 Awi Licensing Llc Soil and dirt repellent powder coatings
US11130871B2 (en) 2016-06-29 2021-09-28 Awi Licensing Llc High performance coatings for building panels
EP3929233A1 (fr) 2020-06-25 2021-12-29 Evonik Operations GmbH Compositions de polyuréthane réactives
WO2023162870A1 (fr) 2022-02-28 2023-08-31 旭化成株式会社 Composition d'isocyanate séquencé, composition de matériau de revêtement et film de revêtement
EP4273176A1 (fr) 2022-05-06 2023-11-08 Röhm GmbH Production de copolymères de polyester alkyl(méth)acrylate par polymérisation en suspension

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DE2105777A1 (de) 1971-02-08 1972-08-24 Veba Chemie Ag Pulverförmige Überzugsmasse

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0023023A1 (fr) * 1979-07-19 1981-01-28 Chemische Werke Hüls Ag Masses de revêtement pulvérulentes de haute stabilité au stockage et leur préparation
EP0023626B1 (fr) * 1979-07-19 1985-10-23 Hüls Aktiengesellschaft Préparation de produits d'addition d'isophorone-diisocyanate contenant des groupes NCO libres et bloqués par l'epsilon-caprolactame et produits d'addition ainsi fabriqués
EP0026448A1 (fr) * 1979-09-26 1981-04-08 Hüls Aktiengesellschaft Vernis au four à un composant
EP0075206A1 (fr) * 1981-09-18 1983-03-30 BASF Aktiengesellschaft Procédé de préparation de revêtements
EP0139830A2 (fr) * 1983-08-04 1985-05-08 Hüls Aktiengesellschaft Revêtements en poudre à base d'isocyanurates de diisocyanate d'isophorone partiellement bloqués et de polyesters contenant des groupes hydroxyles, procédé de préparation de revêtements mats
EP0139830A3 (fr) * 1983-08-04 1986-01-29 Hüls Aktiengesellschaft Revêtements en poudre à base d'isocyanurates de diisocyanate d'isophorone partiellement bloqués et de polyesters contenant des groupes hydroxyles, procédé de préparation de revêtements mats
GB2185988A (en) * 1986-01-31 1987-08-05 Inventa Ag Polyester melt-adhesive compositions
EP0538597A1 (fr) * 1991-10-15 1993-04-28 Hüls Aktiengesellschaft Produits d'addition de polyisocyanate bloqués ayant une fonctionnalité élevée, procédé pour sa préparation et son utilisation
EP0579042A2 (fr) * 1992-07-14 1994-01-19 Basf Corporation Composition de revêtement à composant unique résistant à la corrosion sans influence sur l'environnement, procédé de revêtement avec celle-ci et revêtement obtenu à partir de cell-ci
EP0579042A3 (fr) * 1992-07-14 1994-03-16 Basf Corp

Also Published As

Publication number Publication date
AT376992B (de) 1985-01-25
JPS5440832A (en) 1979-03-31
FI63770B (fi) 1983-04-29
US4246380A (en) 1981-01-20
DE2735497A1 (de) 1979-02-15
DK345478A (da) 1979-02-07
IT7826477A0 (it) 1978-08-04
FI63770C (fi) 1983-08-10
FI782405A (fi) 1979-02-07
ZA784439B (en) 1979-10-31
DE2861007D1 (en) 1981-11-26
ATA568378A (de) 1984-06-15
EP0000798B1 (fr) 1981-09-02
IT1097679B (it) 1985-08-31
JPS6131744B2 (fr) 1986-07-22

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