EP2084202A1 - Epoxydes d'uréthanne pour le durcissement à faible température de revêtements, son procédé de fabrication et son utilisation - Google Patents

Epoxydes d'uréthanne pour le durcissement à faible température de revêtements, son procédé de fabrication et son utilisation

Info

Publication number
EP2084202A1
EP2084202A1 EP07819864A EP07819864A EP2084202A1 EP 2084202 A1 EP2084202 A1 EP 2084202A1 EP 07819864 A EP07819864 A EP 07819864A EP 07819864 A EP07819864 A EP 07819864A EP 2084202 A1 EP2084202 A1 EP 2084202A1
Authority
EP
European Patent Office
Prior art keywords
coating composition
composition according
powdery coating
powdery
diisocyanate
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Withdrawn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
EP07819864A
Other languages
German (de)
English (en)
Inventor
Michael Kraus
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.)
EMS Patent AG
Original Assignee
EMS Patent 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 EMS Patent AG filed Critical EMS Patent AG
Publication of EP2084202A1 publication Critical patent/EP2084202A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a novel coating system based on epoxy-functional urethanes (urethane epoxides) for thermosetting compositions. Moreover, the present invention relates to the preparation and application of paint systems, consisting of the urethane epoxides and a Koreaktan- den, and other, known for the production of paints fillers and additives.
  • urethane epoxides epoxy-functional urethanes
  • Patent EP 0 228 935 mentions urethane epoxides in connection with the preparation of oxazolidines.
  • Patent GB 1,072,716 describes a process of preparing urethane epoxides by the reaction of epoxy alcohols (eg 3,4-epoxy-4-methylpentanol-2) and isocyanates (eg 2-naphthyl isocyanate, TDI). Also mentioned is the use as a crosslinker in paints.
  • US Pat. No. 4,020,034 describes weathering-resistant coatings obtained from the crosslinking reaction of a urethane epoxide with an aliphatic or cycloaliphatic acid or its anhydride (for example tetrahydrophthalic acid). The coatings were applied from a solvent.
  • Patent DE 31 38 196 describes powdery coating compositions and their use.
  • binder there are mentioned both resins obtained by olefin polymerization and condensation reactions.
  • hardener Urethanepoxide, obtained by reaction egg nes (poly) isocyanate with glycidol (such as TDI) and have a melting point of 30 to 100 0 C.
  • Patent RU 2 230 088 describes urethane epoxides obtained by reaction of polyisocyanates (eg TDI), a Spacer (eg polytetrahydrofuran) and glycidol were prepared. From the present invention, this technique differs by the crosslinking by means of polyamines (eg, organosilicone diamines) and the use of an organic solvent.
  • polyisocyanates eg TDI
  • Spacer eg polytetrahydrofuran
  • glycidol glycidol
  • Patent JP 5295079 describes thermosetting coatings in which the urethane epoxide component is represented as follows. Monosubstitution of TDI with glycidol and subsequent reaction with an alcohol or thiol having a functionality ⁇ 1. The resulting liquid resins are mixed with a diamine (eg, 1,3-bis (aminomethyl) cyclohexane) and at 80 0 C for one hour hardened.
  • a diamine eg, 1,3-bis (aminomethyl) cyclohexane
  • Patents DE 103 20 431 and DE 103 20 432 describe urethane-epoxide-functional silanes, a process for their preparation and their use. This mentions both the thermal hardening and the hardening by blasting. In particular, they differ from the present invention in that the coatings are so-called sol-gel coatings.
  • Edwards et al. the synthesis of urethane epoxides and their use as a thermosetting coating material (Edwards PA, Erickson J., Webster D.C., Polymer Preprints 2003, 44 (1), 54; Edwards PA, Erickson J., Webster D.C. Polymer Preprints 2003, 45 (1), 935; Edwards PA, Erickson J., Webster D.C., ICT Research 2005, 2 (7), 517).
  • the application of the coating material takes place from solution.
  • the curing takes place by reaction with added amines or from temperatures of 150 0 C intermolecular with others
  • Curing the coatings to ensure curing temperatures of 150 to 200 0 C are necessary. In addition to the high energy costs for the curing process, this type of coating is limited to thermoresistant materials. Objects made of wood or plastic can not be coated.
  • thermosetting powdery coating composition comprising (A) 5 to 100 wt .-% of a 2 or more epoxy groups per molecule containing reaction product of a di- and / or polyisocyanate with a di- and / or polyol, and / or a di- and / or polyamine, and a glycidyl alcohol and / or glycidophenol, wherein the reaction product has a Tg between 30 and 120 0 C, as measured by DSC.
  • Polymer has a Tg in the range of 30 0 C to 80 0 C, as measured by DSC, and an acid number of 20 to 200 mgKOH / g, and / or
  • the solution according to the invention consists in the use of condensates of polyisocyanates and alcohols and / or amines, as well as glycidyl alcohols. Characterized powder coatings can be prepared which cure in a temperature range tem- from 90 to 150 0 C. In view of the prior art, it was surprising and unforeseeable for the skilled worker that the object on which the present invention was based can be achieved with the aid of the system according to the invention and the method according to the invention.
  • the curing agents of the present invention can be readily modified to provide thermally cured coatings and coatings that are weather resistant, flexible, clear, scratch resistant, and resistant to chemicals.
  • the present invention thus relates to a powdered coating agent based on a solid urethane epoxide. It is preferable to use one or more of the co-reactants selected from the group consisting of alcohols, carboxylic acids and their anhydrides, and oligomers and curing polymers prepared by addition or condensation reactions.
  • the present invention also relates to the use of the urethane epoxy system of the invention for electrostatic powder coating and the fluidized bed sintering process.
  • thermosetting powder coatings have.
  • both aromatic and aliphatic or heterocyclic di- or poly-isocyanate can be used, for example, 4,4 x - methylene-bis- (benzyl), 4, 4 v methylene-bis- ( cyclohexyl isocyanate), 1,5-naphthylene diisocyanate, 2,4- and 2,5-toluene diisocyanate, tetramethylxylylene-1,4-diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, trimethylhexamethylene diisocyanate and isocyanurated diisocyanates, such as isocyanurated isophorone diiso
  • Suitable glycidyl alcohols are compounds of the formula
  • Ri is an alkylene or arylene radical having 1 to 10 carbon atoms
  • R 2 , R 3 , R 4 are hydrogen, a methyl or ethyl group, for example glycidol.
  • Suitable alcohol components include aliphatic diols, such as, for example Ethylene glycol, 1, 3-propanediol, 1, 2-butanediol, 1,3-butanediol, 1, 4-butanediol, 2, 2-dimethylpropanediol-l, 3 (neopentyl glycol), 2, 5-hexanediol, 1, 6-hexanediol , 2,2- [bis (4-hydroxycyclohexal)] -propane, 1, 4-dimethylol-cyclohexane, diethylene glycol, dipropylene glycol and
  • 2, 2-bis [4- (2-hydroxy)] phenylpropane or also polyols, such as, for example, neopentyl glycol, glycerol, hexanetriol, pentaerytlitol, sorbitol, trimethylolethane, trimethylolpropane, and tris (2 -hydroxy) -isocyanurate, or else oligomers, polymers, and copolymers of ethylene oxide, propylene oxide, tetrahydrofuran, lactones and lactams.
  • polyols such as, for example, neopentyl glycol, glycerol, hexanetriol, pentaerytlitol, sorbitol, trimethylolethane, trimethylolpropane, and tris (2 -hydroxy) -isocyanurate, or else oligomers, polymers, and copolymers of ethylene oxide, propylene oxide, tetrahydr
  • amine components and aromatic may be mentioned aliphatic, such as ethylenediamine, isophoronediamine, 3, 4 nylamin ⁇ -Methylendiphe-, 4, 4 ⁇ -Methylendiphenylamin, methylenediamine Trimethylhexa-, m-xylylenediamine, 1, 2-Diaminocyclo- hexane. Also suitable are diethanolamine, N-methylethanolamine and diisopropylamine.
  • the urethane epoxides are preferably prepared in an organic polar aprotic solvent, such as ethyl acetate, and can be freed from the original solvent after the reaction by vacuum distillation, spray drying or precipitation in a solvent of other polarity.
  • organic polar aprotic solvent such as ethyl acetate
  • the component serving as the reactant may be a polycarboxylic acid, an anhydride, a polyestercarboxylic acid, a polyacrylate carboxylic acid, a polyol, or mixtures thereof.
  • Suitable coreactants are aliphatic and / or cycloaliphatic carboxylic acids, such as, for example, 1,4-cyclohexadicarboxylic acid, tetrahydrophthalic acid, hexachlorophthalic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, adipic acid, dodecanedicarboxylic acid, succinic acid, maleic acid or dimecane.
  • fatty acids and, where available, their anhydrides, hydroxycarboxylic acids, such as 12-hydroxystearic acid, and / or aromatic polybasic carboxylic acids, such as terephthalic acid, isophthalic acid, phthalic acid, pyromellitic acid, trimellitic acid, 3,6-dichlorophthalic acid, tetrachlorophthalic acid, and, where available, their anhydride.
  • Monocarboxylic acids such as, for example, benzoic acid, tert-butylbenzoic acid, hexahydrobenzoic acid and saturated aliphatic monocarboxylic acids are also used in small amounts.
  • the content of reactive groups of the co-reactants is generally 0.1 to 3 times, preferably 0.5 to 1.5 times, the stoichiometric amount based on the epoxide content of the urethane epoxide.
  • the powder coatings according to the invention preferably contain a catalyst for the accelerated reaction of the epoxide groups.
  • Suitable catalysts are, for example, quaternary ammonium and phosphonium salts, metal salts or metal compounds, such as, for example
  • the catalyst or Katalysatormi- research is preferably added in an amount such that the gelling time of the mixture at 130 0 C to 400 seconds preferably about 70, is 90 to 200 seconds.
  • compositions comprising:
  • compositions comprising:
  • the coating composition is preferably in the form of a pulverulent ground extrudate, it being advantageous if the mean particle size of the powder-ground extrudate is ⁇ 100 ⁇ m.
  • thermosetting powdery coating composition as mentioned above, in which the formulation constituents are extruded at from 60 to 140 ° C. and then cooled and granulated.
  • the pulverulent ground extrudate is screened to a particle size ⁇ 100 microns.
  • formulation constituents are subjected to granulation by means of high-pressure spraying (PGSS, RESS or GAS processes), by extrusion under addition of gas, the VEDOC Advanced Manufacturing Process (VAMP), the Continuos Powder
  • CPCSP Coating Spraying Process
  • the present invention likewise relates to the use of the pulverulent coating compositions according to the invention, if appropriate in combination with Pigments, flow control agents, antistatic agents, catalysts and other auxiliaries and the electrostatic powder coating, for example by the triboelectric or corona powder spraying process or the fluidized bed process or by the fluidized-sintering process.
  • Suitable application methods for the powder coatings according to the invention are, for example, flame spraying, charge-free scattering onto the materials to be coated, vortex sintering and, preferably, electrostatic powder spraying.
  • the applied powder coatings of this invention are generally between 50 to 200 0 C, preferably 70 to 150 0 C, particularly preferably 80 to 130 0 C, for 5 to 60 minutes cured.
  • the powdery coating compositions according to the invention are suitable, e.g. for coating metal parts such as car bodies, window parts, facade cladding and the like, and for coating non-metallic surfaces such as glass, ceramics, plastics and wood. In the unpigmented state they are also to be used as topcoat for metallic paints. Furthermore, they are suitable for the coating of household appliances, pipes and equipment of agriculture and forestry.
  • the application of the coating compositions according to the invention from aqueous or nonaqueous solvents is also conceivable.
  • coreactant also aliphatic and aromatic di- and / or polyamines, such as ethylenediamine min, isophoronediamine, 3, 4 ⁇ -Methylendiphenylamin, 4, 4 x -Methylendiphenylamin, Trimethylhexamethylendia- min, m-xylylenediamine, 1 2 are, -diaminocyclohexane.
  • diethanolamine N-methylethanol amine and diisopropylamine.
  • the resulting reaction mixture was stirred under nitrogen for 14 hours at room temperature and 10 hours at 60 0 C, after which the reaction was complete (detected by the disappearance of the isocyanate in the IR spectrum of the reaction mixture).
  • the reaction product was separated by precipitation in petroleum ether.
  • T 3 65 ° C.
  • the powder coatings are electrostatically applied (Corona or Tribo) both on aluminum sheets (Q- panel AL-36 5005 H 14/08 (0.8mm)), as well as on steel sheets (Q-panel R-36 (0.8 mm)) and in a Burning temperature of 130 0 C and a baking time of 15 min in the electric oven UT6060 the
  • Heraeus (D) company cured.
  • the layer thickness is about 80 microns.
  • the film properties are shown in the table.
  • Resiflow PV88 leveling agent on polyacrylate basis
  • benzoin 10.0 g Resiflow PV88 (leveling agent on polyacrylate basis) and 2.0 g benzoin are mixed dry in a Henschelmi- sec shear at 700 U / min for 30 and then on a Thysson-co-kneader (TSK 20) at a jacket temperature of 80 0 C and a worm ckenumwindung 500 U / min extruded. The extrudate is cooled, ground and sieved to ⁇ 90 ⁇ m.
  • TSK 20 Thysson-co-kneader
  • the powder coatings are applied electrostatically (corona or tri-boule) both on aluminum sheets (Q-panel AL-36 5005 H 14/08 (0.8 mm)) and on steel sheets (Q-panel R-36 (0.8 mm)) and cured at a stoving temperature of 130 0 C and a baking time of 15 min in the electric furnace UT6060 Heraeus (D).
  • the layer thickness is about 80 microns. The film properties can be found in the table.
  • TSK 20 Thysson-Co Kneader
  • Powder coatings are applied electrostatically (corona or tri-bo) to aluminum sheets (Q-panel AL-36 5005 H 14/08 (0.8 mm)) as well as to steel sheets (Q-panel R-36 (0.8 mm)) Einbrenntempe- a temperature of 130 0 C and a baking time of 15 min in
  • 657.5 g Crylcoat 2630-2 having an acid value of 33 mgKOH / g and a Tg of about 60 0 C, 32.5 g Primid XL-552, 300.0 g Kronos Titan 2160 8.0 g Resiflow PV88 and 2.0 g benzoin are in a Henschelmi- shear dry mixed at 700 U / min for 30 sec and then extruded on a Thysson co-kneader (TSK 20) at a jacket temperature of 110 0 C and a screw revolution of 500 rev / min.
  • TSK 20 Thysson co-kneader
  • Extrudate is cooled, ground and screened to ⁇ 90 microns.
  • the powder coatings are electrostatically applied (Corona or Tribo) both on aluminum sheets (Q-panel AL-36 5005 H 14/08 (0.8 mm)), and on steel sheets (Q-panel R-36 (0.8 mm)) and at a Burning temperature of 180 0 C and a baking time of 15 min in the electric oven UT6060 Heraeus (D) hardened.
  • the layer thickness is about 80 microns.
  • the film properties are shown in the table.
  • the powder coatings are electrostatically (corona or
  • Tribo on both aluminum sheets (Q-panel AL-36 5005 H 14/08 (0.8 mm)), as well as on steel sheets (Q-panel R-36 (0.8 mm)) applied and at a baking temperature of 180 0 C and a baking time of 15 min in the electric oven UT6060 from Heraeus (D) hardened.
  • the layer thickness is about 80 microns.
  • the film properties are shown in the table.
  • Test The tests are carried out 1 h after the coating of the sheets.
  • the coated sheet is clamped in the test apparatus (see attachment).
  • the bend in the middle of the sheet is 2 mm.
  • the sheet thus exposed to mechanical stress is immersed in absolute ethanol (98%) for 30 seconds and visually inspected for stress cracks. If no cracks are visible, the bend is increased by 2 mm and rechecked. This is repeated until first cracks occur.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne un nouveau système de revêtement à base d'uréthannes à fonction époxy (époxydes d'uréthanne) pour matériaux durcissant thermiquement. La présente invention concerne également la fabrication et l'application de systèmes de revêtement, contenant des époxydes d'uréthanne et un coréactif, ainsi qu'également des charges et additifs connus pour la fabrication de revêtements.
EP07819864A 2006-11-22 2007-11-19 Epoxydes d'uréthanne pour le durcissement à faible température de revêtements, son procédé de fabrication et son utilisation Withdrawn EP2084202A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610055081 DE102006055081A1 (de) 2006-11-22 2006-11-22 Urethanepoxide für die Tieftemperaturhärtung von Beschichtungen, Verfahren zur Herstellung sowie Verwendung
PCT/EP2007/009991 WO2008061687A1 (fr) 2006-11-22 2007-11-19 Epoxydes d'uréthanne pour le durcissement à faible température de revêtements, son procédé de fabrication et son utilisation

Publications (1)

Publication Number Publication Date
EP2084202A1 true EP2084202A1 (fr) 2009-08-05

Family

ID=39091743

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07819864A Withdrawn EP2084202A1 (fr) 2006-11-22 2007-11-19 Epoxydes d'uréthanne pour le durcissement à faible température de revêtements, son procédé de fabrication et son utilisation

Country Status (3)

Country Link
EP (1) EP2084202A1 (fr)
DE (1) DE102006055081A1 (fr)
WO (1) WO2008061687A1 (fr)

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Publication number Priority date Publication date Assignee Title
US8722154B2 (en) 2008-09-22 2014-05-13 Commonwealth Scientific And Industrial Research Organisation Composition and method for preparation of electro-conductive polymer surfaces
US20140364540A1 (en) 2009-02-26 2014-12-11 Jotun Powder Coatings (N) As Powder coating
CN105764950B (zh) 2013-09-25 2020-04-21 巴斯夫欧洲公司 用于涂料化合物的新交联剂
CN111040103B (zh) * 2019-12-27 2021-08-24 福建华夏蓝新材料科技有限公司 一种可再分散的水性聚氨酯粉末的制备方法
US20250243381A1 (en) * 2022-03-22 2025-07-31 Jotun A/S Composition
EP4265690A1 (fr) * 2022-04-22 2023-10-25 Jotun A/S Composition

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
US4069208A (en) * 1975-10-14 1978-01-17 E. I. Du Pont De Nemours And Company Heat-activatable polyurethane powder coatings
DE3138196A1 (de) * 1981-09-25 1983-04-14 Basf Farben + Fasern Ag, 2000 Hamburg Pulverfoermiges ueberzugsmittel und seine verwendung
DE10348966A1 (de) * 2003-10-22 2005-06-02 Degussa Ag Hochreaktive Polyurethan-Pulverlackzusammensetzungen auf Basis epoxidgruppenterminierter, uretdiongruppenhaltiger Polyadditionsverbindungen
EP1994104B1 (fr) * 2006-02-14 2010-03-31 E.I. Du Pont De Nemours And Company Compositions de revetement liquides, non aqueuses

Non-Patent Citations (1)

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Title
See references of WO2008061687A1 *

Also Published As

Publication number Publication date
DE102006055081A1 (de) 2008-05-29
WO2008061687A1 (fr) 2008-05-29

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