EP1723190A1 - Procede de production de compositions de polyurethanne solides hautement reactives contenant des groupes uretdione - Google Patents

Procede de production de compositions de polyurethanne solides hautement reactives contenant des groupes uretdione

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Publication number
EP1723190A1
EP1723190A1 EP05716584A EP05716584A EP1723190A1 EP 1723190 A1 EP1723190 A1 EP 1723190A1 EP 05716584 A EP05716584 A EP 05716584A EP 05716584 A EP05716584 A EP 05716584A EP 1723190 A1 EP1723190 A1 EP 1723190A1
Authority
EP
European Patent Office
Prior art keywords
hydroxide
acid
alcoholate
atoms
radicals
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Withdrawn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
EP05716584A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Holger Loesch
Andreas Wenning
Thomas Weihrauch
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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 Degussa GmbH filed Critical Degussa GmbH
Publication of EP1723190A1 publication Critical patent/EP1723190A1/fr
Withdrawn legal-status Critical Current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
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • 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
    • C08G18/08—Processes
    • C08G18/0895—Manufacture of polymers by continuous processes
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
    • 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 invention relates to a process for the production of solid, highly reactive uretdione-containing polyurethane compositions which cure at low baking temperatures, such compositions and their use for the production of plastics, in particular powder coating coatings, which crosslink to give high-gloss or matt, light and weather-stable paint films.
  • Polyisocyanates which are solid at room temperature, blocked externally or internally, are valuable crosslinkers for thermally crosslinkable polyurethane (PUR) powder coating compositions.
  • B. DE-OS 27 35 497 PUR powder coatings with excellent weather and heat stability consist of isophorone diisocyanate containing ⁇ -caprolactam blocked isocyanurate groups.
  • Polyisocyanates containing urethane, biuret or urea groups are also known, the isocyanate groups of which are also blocked.
  • DE-OS 30 30 539 and DE-OS 30 30 572 describe processes for the preparation of uretdione group-containing polyaddition compounds whose terminal isocyanate groups are irreversibly blocked with monoalcohols or monoamines.
  • the chain-terminating constituents of the crosslinking agents which lead to low network densities of the PU powder coating and thus to moderate resistance to solvents, are particularly disadvantageous.
  • Hydroxyl group-terminated, polyaddition compounds containing uretdione groups are the subject of EP 0 669 353. Because of their functionality of two, they have improved resistance to solvents.
  • the powder coating compositions based on these uretdione group-containing polyisocyanates have in common that they do not emit any volatile compounds during the curing reaction. However, the baking temperatures are at a high level with at least 180 ° C.
  • amidines as catalysts in PU powder coating compositions. Although these catalysts lower the curing temperature, they show considerable yellowing, which is generally undesirable in the coating area. The cause of this yellowing is probably the reactive nitrogen atoms in the amidines. These can react with atmospheric oxygen to form N-oxides, which are responsible for the discoloration.
  • EP 0 803 524 also mentions other catalysts which have hitherto been used for this purpose, but without showing any particular effect on the curing temperature.
  • organometallic catalysts known from polyurethane chemistry, such as. B. Dibutylzujndilaurat (DBTL), or tertiary amines, such as. B. 1,4-diazabicylco [2.2.2] octane (DABCO).
  • catalysts based on metal acetylacetonates e.g. B. zinc acetylacetonate claimed.
  • Such catalysts are actually able to lower the curing temperature of uretdione group-containing polyureman powder coating compositions (M. Gedan-Smolka, F. Lehmarm, D. Lehmann "New catalysts for the low temperature curing of uretdione powder coatings" International Waterborne, High solids and powder coatings symposium, New Orleans, February 21-23, 2001).
  • Powder coating compositions are usually ground and sieved after production.
  • the resulting particles of the powder (usually 5 - 200 ⁇ m) must not cake together even during storage, as otherwise the spray application would be disrupted.
  • a glass transition point is therefore the Powder coating compositions of at least 40 - 50 ° C required.
  • powder coating compositions with such a glass transition point generally only melt at temperatures between 90 and 130 ° C.
  • the object of the present invention was therefore to find a process for the preparation of solid, highly reactive uretdione-containing polyurethane compositions which can be cured even at very low temperatures, but are particularly suitable for the production of plastics and of high-gloss or matt, light and weather-stable powder coating materials show no pronounced surface defects.
  • the present invention relates to a process for the preparation of a solid, highly reactive uretdione group-containing polyure composition, by mixing A) at least one uretdione-containing hardener, with a free NCO content of less than 5% by weight and a uretdione content of 1-30% by weight. -%, based on aromatic, aliphatic, (cyclo) aliphatic or cycloaliphatic polyisocyanates and compounds containing hydroxyl groups, with a melting point of 40 to 130 C, and B) optionally at least one polymer containing hydroxyl groups with a melting point of 40-130 ° C. and an OH number between 20 and 200 mg KOH / gram,
  • R 1 - R 4 simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R 1 - R 4 , with the formation of Cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1-18 carbon atoms and each radical R 1 - R 4 additionally also one or more alcohol, amino, ester, keto, thio, urethane -, Urea-, AUophanatg ⁇ ppen, double bonds, triple bonds or halogen atoms, and R 5 is either OH, F, or R 6 COO means with R 6 synonymous with alkyl, aryl, aralkyl, heteroaryl, AUcoxyalkyl residues, linear or branched , with 1 - 18 carbon atoms, which can
  • a mixing unit selected from an extruder, intensive kneader, intensive mixer or static mixer, component C) being the components A) and optionally B), D), E) and / or F) which have already been mixed partially or completely in the mixing unit , subsequently added in the mixing unit and mixed with the other components and subsequent isolation of the end product by cooling.
  • Essential to the invention is the introduction of a highly effective catalyst C) into a uretdione-containing polyurethane composition in a mixing unit, the addition a) in a certain range, preferably after 10, 20, 30 to 90%, 40-80%, 55-75%, of Total length of the mixing unit, preferably close to the outlet nozzle, particularly preferably in the last third of the mixing unit, b) in a specific temperature range from 70 to 170 ° C. of the melted polyurethane composition, preferably at temperatures from 70 to 130 ° C.
  • the invention also relates to solid, highly reactive polyurethane compositions containing uretdione groups, obtained by mixing
  • R 1 - R 4 simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or with other radicals R'- R 4 is bridged, with the exhaustion of cycles, bicycles or tricycles and the bridging atoms can also be heteroatoms in addition to carbon, with 1-18 carbon atoms and each radical R 1 - R 4 additionally also one or more alcohol, amino, ester, Keto, thio, urethane, urea, AUophanat phenomenon, double bonds, triple bonds or halogen atoms, and R 5 represents an alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radical, linear or branched, with 1 - 18 carbon atoms and additionally one or more alcohol, Amino, ester, keto, thio, acid, ure
  • a mixing unit selected from an extruder, intensive kneader, intensive mixer or static mixer, with component C) already partially or completely in the Mixing unit mixed components A) and optionally B), D), E) and / or F), subsequently added in the mixing unit and mixed with the other components and subsequent isolation of the end product by cooling, and the use in powder coatings.
  • Polyisocyanates containing uretdione groups are well known and are described for example in US 4,476,054, US 4,912,210, US 4,929,724 and EP 0 417 603.
  • a comprehensive overview of industrially relevant processes for the dimerization of isocyanates to uretdions Hefert the J. Prakt. Chem. 336 (1994) 185-200.
  • the conversion of isocyanates to uretdiones takes place in the presence of soluble dimerization catalysts such as.
  • the reaction - optionally carried out in solvents, but preferably in the absence of solvents - is stopped when a desired conversion is reached by adding catalyst poisons. Excess monomeric isocyanate is then separated off by short-path evaporation. If the catalyst is volatile enough, the reaction mixture can be freed from the catalyst in the course of the monomer separation. The addition of catalyst poisons is not required in this FaU.
  • a wide range of isocyanates is suitable for the production of polyisocyanates containing uretdione groups.
  • isophorone diisocyanate (TPDl), hexamethylene diisocyanate (HDI), 2-methylpentane diisocyanate (MPDI), 2,2,4-trimethylhexamethylene d ⁇ ocyana1, 2,4,4-trimethylhexamethylene ⁇ iüsc) cyanate (TMDI), norbornane diisocyanate (NBDI), methylene diphenyl diisocyanate (MDB and tetramethylxylylene diisocyanate (TMXDI) are preferably used. D? DI and HDI are particularly preferred.
  • the conversion of these polyisocyanates bearing uretdione groups to hardeners A) containing uretdione groups involves the reaction of the free NCO groups with hydroxyl-containing monomers or polymers, such as, for. B. polyesters, polythioethers, polyethers, polycaprolactams, polyepoxides, polyesteramides, polyurethanes or low molecular weight di-, tri- and / or tetraalcohols as chain extenders and optionally monoamines and or monoalcohols as chain terminators and has already been described frequently (EP 0 669 353, EP 0 669 354, DE 30 30 572, EP 0 639 598 or EP 0 803 524).
  • hydroxyl-containing monomers or polymers such as, for. B. polyesters, polythioethers, polyethers, polycaprolactams, polyepoxides, polyesteramides, polyurethanes or low molecular weight di-, tri- and / or
  • Preferred hardener A) containing uretdione groups have a free NCO content of less than 5% by weight and a uretdione group content of 6 to 30% by weight (calculated as C 2 N 2 O 2 , molecular weight 84). Polyesters and monomeric dialcohols are preferred. In addition to the uretdione groups, the hardeners can also have isocyanurate, biuret, AUophanat, urethane and / or urea structures.
  • polyesters, polyethers, polyacrylates, polyurethanes and / or polycarbonates with an OH number of 20-200 (in mg KOH / gram).
  • Polyesters with an OH number of 30-150, an average molecular weight of 500-6000 g / mol and a melting point between 40 and 130 ° C. are particularly preferably used.
  • Such binders have been described, for example, in EP 669 354 and EP 254 152. Of course, mixtures of such polymers can also be used.
  • the amount of component B, based on the total formulation can be between 0 and 80% by weight.
  • Examples of the catalysts C1) are lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, beiühumium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, aluminum hydroxide, zinc hydroxide, lithium methanolate, sodium methoxide, potassium methoxide, magnesium ethanolate, sodium ethanolate, sodium methoxide, sodium methoxide, sodium methoxide, calcium methoxide, calcium methoxide, magnesium ethanolate, Calziumethanolat, Bariumethanolat, Lithiumpropylalkoholat, Natriumpropylalkoholat, Kaliumpropylalkoholat, Magnesiumpropylalkoholat, Calziumpropyl- alcoholate, Bariumpropylalkoholat, LithiumisopropylaUcoholat, Natriumisopropylalkoholat, KaUumisopropylaU
  • catalysts C2 are methyltributylammonium hydroxide, methyltriethylammonium hydroxide, tetramernylammordium hydroxide, tetiaethylammonium hydroxide, tetiapropylan ammonium hydroxide, telrabutylammonium hydroxide, tetiapentylammonium hydroxide, Tetiaoclylammonium hydroxide, Tetradecylammoniumhydroxy4 Tet ⁇ ecyltnhexylarrjmomumhydroxid, Tetiaoctadecylammonium hydroxide Berizyltrimethylammoniumhydroxid, Benzyltriethylammoniumhydroxid, Trimethyl- phenyimmor umhydroxid, Triethylmidiummylammonium hydroxide, tetamethylanunonium fluoride, tettaethyl
  • catalysts C3 are tetiamemylammonium formate, tetramethylammonium acetate, tetramethylammonium propionate, tetiamethylammonium butyrate, tetramethylammonium benzate, tetiaelethylammonium ammonium formate, tetraethylammonium acetate, tetrahydronammonium benzionate, tammethylammonium tammonium tammate, tammethylammonium tammate,
  • Examples of catalysts C4) are zinc acetylacetonate and lithium acetylacetonate.
  • catalysts C5) are teträbutylphosphonium acetate, tetrabutylphosphorus benzotriazolate, tetabutylphosphonium hydroxide, ethylthenylphosphonium acetate,
  • Tetraphenylphosphonium phenolate, trihexyltetradecylphosphonium decanoate and / or tetiabutylphosphonium fluoride Mixtures of such catalysts can of course also be used. They are contained in the polyLirethane composition in an amount of 0.001-5% by weight, preferably 0.01-3% by weight, based on components A) and possibly B).
  • the catalysts can contain water of crystallization, which is not taken into account when calculating the amount of catalyst used, ie the amount of water is eliminated.
  • a variant according to the invention includes the polymeric attachment of such catalysts C) to hardener A) or hydroxyl group-containing polymers B).
  • So z. B. free alcohol, thio or amino groups of the catalysts with acid, isocyanate, or glycidyl groups of the hardener A) or hydroxyl group-containing polymers B) are implemented in order to integrate the catalysts C) into the polymeric composite.
  • Reactive acid-trapping compounds D) are, for example, epoxy compounds, carbodiimides, hykoxyalkylamides or 2-oxazolines, but also inorganic salts such as hydroxides, hydrogen carbonates or carbonates. Possible z. B.
  • triglycidyl ether isocyanurate TGIC
  • EPIKOTE ® 828 diglycidyl ether based on bisphenol A, ScheU
  • versatic acid glycidyl ester ethylhexylglycidyl ether, butylglycidyl ether
  • POLYPOX ® R 16 penentaerythritol tetraglycidyl ether, Epox ® EPON type, UPPC AG type
  • UPPC AG type VESTX type AGEST EPPC type AGEST, with UPPC AG type, as well as UPPC AG type, EPPC type AGEST, as well as UPPX type AGEST with AGP type AGP, AGP type AG) Hydroxyallcylamide, Degussa AG), but also phenylenebisoxazoline, 2-methyl-2-oxazoline, 2-hydroxyethyl-2-oxazoline, 2-hydroxypropyl-2-oxazoline, 5-hydroxy
  • Acids mentioned under E) are all substances, solid or liquid, organic or inorganic, monomeric or polymer, which have the properties of a Brönstedt or a Lewis acid. Examples include: sulfuric acid, acetic acid, benzoic acid, malonic acid, terephthalic acid, but also copolyesters or copolyamides with an acid number of at least 20.
  • the hoof and additives F) common in powder coating technology such as leveling agents, e.g. B. PolysiUcone or acrylates, light stabilizers such. B. sterically hindered amines, or other auxiliary agents such as z. B. have been described in EP 669 353, are added in a total amount of 0.05 to 5 wt .-%. Fuels and pigments such as B. Titanium dioxide can be added in an amount of up to 50% by weight of the total composition.
  • Additional catalysts can optionally be included. These are mainly meta-organic catalysts, such as. B. dibutyltin dilaurate, or tertiary amines, such as. B. 1,4-diazabicylco [2,2,2] octane, in amounts of 0.001-1% by weight.
  • suitable mixing units such as. B. heatable kneaders, in particular intensive kneaders, or intensive mixers, static mixers, but preferably in extruders, with temperature limits of 170 ° C. should not be exceeded.
  • suitable mixing units such as. B. heatable kneaders, in particular intensive kneaders, or intensive mixers, static mixers, but preferably in extruders, with temperature limits of 170 ° C.
  • the fact that short-term, as small as possible, is of a fundamental nature thermal stress in combination with the effect of the aggregates is sufficient to homogeneously mix the components and the catalyst without reaction or decomposition.
  • the residence time of the starting materials in the above-mentioned units is usually 3 seconds to 15 minutes, preferably 3 seconds to 5 minutes, particularly preferably 5 to 180 seconds.
  • Extruders such as single-screw or multi-screw extruders, in particular twin-screw extruders,
  • Planetary roller extruders or ring extruders are particularly suitable for the process according to the invention and are preferably used.
  • the introduction of a highly effective catalyst C) into a polyurethane composition containing uretdione groups in a mixing unit is essential to the invention, the addition a) in a certain range preferably after 10, 20, 30 to 90%, 40-80%, 55-75 % of the total length of the mixing unit, preferably close to the outlet nozzle, particularly preferably approximately in the last third of the mixing unit, b) in a specific temperature range from 70 to 170 ° C of the applied polyurel harmony, preferably at the lowest possible temperatures of 70 to 130 ° C.
  • Cooling downstream of the mixture can be integrated in the same reaction part, in the form of a multi-housing design as in extruders or Conterna machines. Pipe bundles, coils, chill rolls, air conveyors and conveyor belts made of MetaU can also be used.
  • the process is carried out in an extruder
  • the mixing in of the catalyst during the extrusion can be varied as follows:
  • the polyurethane composition is metered as a solid into one of the first housings of a co-rotating twin-screw extruder.
  • the catalyst is fed in solid or liquid into one of the rear housings.
  • the extruder has separately temperature-controlled housings (heatable and coolable).
  • the housing into which the polyurethane composition is dosed is cooled (typically 20 to 90 ° C).
  • the following housing is tempered just above the melting point of the mixture. All The following housings are kept at a slightly higher temperature (40 to 150 ° C).
  • the outlet temperature is just above the temperature of the last housing (40 to 170 ° C).
  • the catalyst is metered into a housing close to the extruder outlet (this corresponds to approximately 70% of the extruder length) via a pipe or a nozzle.
  • the extruder speed is 100 to 400 rpm.
  • the emerging product is quickly cooled down (e.g. using a cooling roller mill or a
  • Cooling belt and collected.
  • the screw design is selected in such a way that a fast, homogeneous increase in the cost of the catalyst is made possible.
  • different elements can be combined in the screw elements (e.g.
  • the assembly is first brought to a suitable temperature by further cooling using the aforementioned devices, then the pasting or comminution into a desired particle size is carried out using a roller crusher, pin mill, hammer mill, classifier mill, flaking rollers or similar.
  • the extruded mass After cooling to room temperature and after suitable comminution, the extruded mass is ground to a ready-to-spray powder.
  • the application of the ready-to-spray powder to suitable substrates can be carried out by the known methods, such as. B. by electrostatic powder spraying, fluidized bed sintering, or electrostatic fluidized bed sintering.
  • the coated workpieces After powder application, the coated workpieces are cured to a temperature of 120 to 220 ° C. for 4 to 60 minutes, preferably 120 to 180 ° C. for 6 to 30 minutes
  • OH number consumption mg KOH / g polymer
  • SZ acid number, consumption mg KOH / g polymer mp: melting point
  • T G glass transition point
  • WG water content in% by weight
  • the finished mixture is fed in powder form via a solid dosing weigher continuously into a co-rotating twin-screw extruder.
  • the throughput is 2.0 kg / h (DSK 25).
  • the extruder has separately temperature-controlled housings (heatable and coolable). Housing 1 is heated to room temperature, housing 2 is heated to 95 to 115 ° C, the following housings are heated to 120 to 130 ° C.
  • the catalyst is metered in liquid, at room temperature, into a housing after 70% of the extruder length.
  • the outlet temperature of the product is 121 to 135 ° C.
  • the extruder speed is around 200 rpm
  • the emerging white melt is cooled on a kuHwalzenstuhl and then collected.
  • Production of a powder coating After cooling, the extrudate is broken and ground with a pencil mill to a grain size ⁇ 100 ⁇ m.
  • the powder produced in this way is applied to degreased iron sheets using an electrostatic powder spraying system at 60 KV and baked in an odorless drying cabinet.
  • Powder coating compositions (figures in% by weight, except for OH / UD):
  • OH / UD Ratio of OH groups to uretdione groups (MoLMol) 40.0% by weight of KRONOS 2160, 1.0% by weight of RESIFLOW PV 88 and 1.5% by weight of Araldit PT 810 were added to each of the formulations used. Curing results after 30 min at 160 ° C:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un procédé de production de compositions de polyuréthanne solides hautement réactives contenant des groupes urétdione qui durcissent à des températures de cuisson basses, des compositions de ce type ainsi que l'utilisation de ces compositions pour la fabrication de plastiques, en particulier de revêtements à base de peinture en poudre qui réticulent pour former des films de peinture très brillants ou mats et stables à la lumière et aux intempéries.
EP05716584A 2004-03-06 2005-01-13 Procede de production de compositions de polyurethanne solides hautement reactives contenant des groupes uretdione Withdrawn EP1723190A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004011004A DE102004011004A1 (de) 2004-03-06 2004-03-06 Verfahren zur Herstellung fester, hochreaktiver Uretdiongruppen haltiger Polyurethanzusammensetzungen
PCT/EP2005/050120 WO2005085314A1 (fr) 2004-03-06 2005-01-13 Procede de production de compositions de polyurethanne solides hautement reactives contenant des groupes uretdione

Publications (1)

Publication Number Publication Date
EP1723190A1 true EP1723190A1 (fr) 2006-11-22

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EP05716584A Withdrawn EP1723190A1 (fr) 2004-03-06 2005-01-13 Procede de production de compositions de polyurethanne solides hautement reactives contenant des groupes uretdione

Country Status (5)

Country Link
US (1) US20070282089A1 (fr)
EP (1) EP1723190A1 (fr)
CN (1) CN1930205A (fr)
DE (1) DE102004011004A1 (fr)
WO (1) WO2005085314A1 (fr)

Families Citing this family (20)

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DE102005013401A1 (de) * 2005-03-23 2006-09-28 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
DE102005013329A1 (de) * 2005-03-23 2006-11-16 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
US20080265201A1 (en) * 2007-04-26 2008-10-30 Degussa Gmbh Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups
WO2008138855A1 (fr) * 2007-05-11 2008-11-20 Evonik Degussa Gmbh Compositions à base de polyuréthane, durcissables à basse température et comportant des groupes uretdione, qui contiennent des polymères formés à partir de polyols portant des groupes oh secondaires
JP5925405B2 (ja) * 2007-10-17 2016-05-25 日立化成株式会社 熱硬化性樹脂組成物
DE102007057057A1 (de) * 2007-11-27 2009-05-28 Evonik Degussa Gmbh Uretdiongruppen haltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und haftungsverbessernde Harze enthalten
US20100227942A1 (en) * 2007-12-18 2010-09-09 Emmanouil Spyrou Dual-cure formulations with components containing uretdione groups
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
US8476376B2 (en) 2010-03-11 2013-07-02 Evonik Degussa Gmbh Heat-curing powder-lacquer compositions yielding a matte surface after curing of the coating, as well as a simple method for production of same
DE102010041247A1 (de) 2010-09-23 2012-03-29 Evonik Degussa Gmbh Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung
DE102011006163A1 (de) 2011-03-25 2012-09-27 Evonik Degussa Gmbh Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten
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US20070282089A1 (en) 2007-12-06
WO2005085314A1 (fr) 2005-09-15
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