WO2000036026A1 - Composition de liant pour peinture en poudre - Google Patents

Composition de liant pour peinture en poudre Download PDF

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Publication number
WO2000036026A1
WO2000036026A1 PCT/NL1999/000765 NL9900765W WO0036026A1 WO 2000036026 A1 WO2000036026 A1 WO 2000036026A1 NL 9900765 W NL9900765 W NL 9900765W WO 0036026 A1 WO0036026 A1 WO 0036026A1
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WO
WIPO (PCT)
Prior art keywords
polymer
unsaturated
crosslinker
acid
instance
Prior art date
Application number
PCT/NL1999/000765
Other languages
English (en)
Inventor
Aylvin Jorge Angelo Athanasius Dias
Johan Franz Gradus Antonius Jansen
Saskia Udding-Louwrier
Original Assignee
Dsm N.V.
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 Dsm N.V. filed Critical Dsm N.V.
Priority to AU16977/00A priority Critical patent/AU1697700A/en
Publication of WO2000036026A1 publication Critical patent/WO2000036026A1/fr

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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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation

Definitions

  • the invention relates to a powder paint binder composition and to a radiation curable powder paint formulation comprising this binder composition.
  • a radiation-curable powder paint binder composition which comprises a polymer and optionally a crosslinker, that results in a powder coating with good properties, such as for instance a good storage stability and a viscosity at a relatively low curing temperature that is low enough to obtain a good flow, and that also results in a powder paint binder formulation that can be cured on metal, wood and plastic.
  • the powder paint binder composition comprises: a) a polymer with an amount of unsaturation such that the ratio (polymer weight) / (number of mol of unsaturated groups) is between 300 and 1800 g per mole of unsaturated group (WPU) and with a molecular weight (Mn) of between 800 and 5000 g per mole and b) a crosslinker comprising units of N-vinyl amide or N-propenyl amide.
  • the number of polymerizable N-vinyl amide or N-propenyl amide unsaturations of the crosslinker is higher than or equal to 2.
  • the crosslinker comprises N- vinyl amide units.
  • the powder paint binder composition according to the invention results due to the presence of a crosslinker comprising N-vmylamide units m a powder paint having an excellent hydrolytic stability and further having sufficient adhesion and flexibility for application on metal substrates and exhibits very good storage or powder stability, processing properties and good flow properties.
  • a powder paint formulation comprising the binder composition according to the invention can be applied on substrates such as for instance wood, metal, chipboard, MDF (medium density fibre board) , paper and plastic .
  • a manor practical advantage of the binder composition according to the invention is the combination of fast curing and the absence of emissions of volatile organic compounds.
  • Another advantage is the relative high cure speed due to the crosslinker according to the invention compared to, for example, vmylether based crosslmkers .
  • the N-vmylamide or propenylam de crosslinker is a difunctional urethane N- vmylamide or a difunctional propenylamide.
  • the crosslinker b) comprising units of N- vinylamide has the general structure
  • Polymer P can for example, be a polyester, a polyacrylate, a polyamide, a polyolefine, a polyurethane or a epoxy resin.
  • the polymer is a saturated polyester and/or unsaturated polyester and/or polyacrylate .
  • R H
  • R 2 - C - C - C -Y - R 3 or - C - Y - R 3
  • R 2 - C" - Y - R1
  • X 0.
  • Y O or N
  • R , R , R and R are hydrogen or R , R and R are hydrogen and R is methyl.
  • the crosslinker b) can comprise units of a polymer having a molecular weight (Mn) higher than 400 and units of a N-vinyl amide or a N-propenylamide .
  • the polymer of crosslinker b) is a linear polymer.
  • crosslinker b) can be either saturated or unsaturated.
  • the polymer of crosslinker b) can be a hydroxyl functional polymer, an acetoacetate functional polymer, an epoxy functional polymer, an acid functional polymer, an isocyanate functional polymer or an ester functional polymer.
  • the crosslinker can be obtained, for instance, by reaction of the components in the presence of a catalyst such as, for instance, dibutyl tin laurate.
  • a catalyst such as, for instance, dibutyl tin laurate.
  • the reaction can optionally take place in bulk or in a suitable solvent such as, for instance, chloroform, ethyl acetate, butyl acetate, toluene, xylene or benzene at temperatures ranging from 70 °C to 150 °C.
  • a suitable solvent such as, for instance, chloroform, ethyl acetate, butyl acetate, toluene, xylene or benzene at temperatures ranging from 70 °C to 150 °C.
  • the order of addition can be varied depending on the end product that is desired.
  • the number of polymerizable unsaturations of the crosslinker is higher than or equal to 2 , is generally between 2 and 10, and is preferably 2-4.
  • the crosslinker can be either linear or branched.
  • the WPU of the crosslinker generally ranges between about 200 to about 1500.
  • the molecular weight (Mn) of the hydroxyl - functional polymer generally ranges from about 200 to about 2500.
  • the polyesters can be prepared using a customary process by esterification or trans- esterification of the customary polyalcohols and polycarboxylic acids, optionally in the presence of customary esterification catalysts such as, for instance, dibutyl tin oxide or tetratbutyl titanate.
  • customary esterification catalysts such as, for instance, dibutyl tin oxide or tetratbutyl titanate.
  • the preparation conditions and the COOH/OH ratio are preferably chosen so that the end products have a hydroxyl number ranging from 25 to 150 mg KOH/gram of resin .
  • a preferred crosslinker is the reaction product of a hydroxyl -functional polymer, a (poly) isocyanate and a functional N-vmyl amide.
  • suitable (poly) isocyanates include isophorone diisocyanate (IPDI) , toluene diisocyanate, p- and m-phenylene diisocyanate, 1,4- tetramethylene diisocyanate, 1 , 6-hexamethylene diisocyanate (HDI), 2 , 2 , 4-tr ⁇ methyl hexamethylene diisocyanate, 1 , 4-cyclohexane diisocyanate, , ' dicyclohexyl methane diisocyanate, 4,4'- diphenylmethane diisocyanate, 1 , 5-tetrahydronaphthalene diisocyanate, naphthalene-1 , 5 ' -diisocyanate, 5-b ⁇ s(2- methyl-3
  • the isocyanate is IMCI, IPDI or HDI .
  • N-vmyl amides are for instance N-vmyl formamides .
  • Suitable N-vmylformamides are, for example, the Michael adducts 3 -N-vmyl formamido-propionates and 2 -methyl -3 - (N-vmyl formamido) propionates or the corresponding propionamides .
  • the crosslinker comprises units of a hydroxyfunctional polymer, a (poly) isocyanate and a N-vmylamide .
  • the selected ratio between a) and b) in the binder composition depends m part on the choice of b) .
  • the unsaturation a) : unsaturation b) equivalent ratio generally ranges from about 1:5 to about 5:1.
  • crosslinker b) m It is also possible to use crosslinker b) m combination with a crosslinker c) .
  • the crosslinker c) comprises ethylenically unsaturated units.
  • Suitable units include, for example, vmylether, allylether, allylurethane, or fumarate, maleate, itaconate and their Diels-Alder adducts or unsaturated (meth) acrylate units.
  • Suitable unsaturated (meth) acrylates are, for example, unsaturated urethane (meth) acrylates , unsaturated polyester (meth) acrylates, unsaturated epoxy (meth) acrylates and unsaturated polyether (meth) acrylates .
  • the crossl k g agent c) can be a liquid or a solid. Solid crosslmkmg agents are preferred because a good powder stability and processability is more easily achieved.
  • the ratio between the crosslmkers can be selected depending on the desired application, especially with regard to flexibility and hardness.
  • the weight ratio of crosslmkers b) : c) can range between 99 : 1 and 1 : 99.
  • EP-A-632111 and EP-A-559135 disclose compositions comprising pure N-vmylformamide as the crosslinker and an oligomer. These compositions cannot be applied m the technical field of powder paints.
  • N- vinylformamide is a liquid which cannot be used because it results in powder coatings which are not powder stable.
  • the powder paint binder composition according to the present application comprises a preferably solid crosslinker comprising units of N-vinylamide which results in a stable powder paint composition.
  • the degree of polymerizable unsaturation in the polymer a) - expressed as WPU - ranges from about 145 to about 3000 grams per mole of unsaturated group (WPU) , and preferably from about 300 to about 1800 grams of polymer per mole of unsaturated group.
  • the unsaturated groups may be positioned both within the chain and at the end of the chain.
  • the molecular weight (Mn) generally ranges from 800 to 5000 and preferably from 2000 to 4500. Mn is determined by means of gel permeation chromatography (GPC) using a polystyrene standard.
  • the polymer (a) is an unsaturated polyester and/or an unsaturated polyacrylate.
  • the amount of unsaturation is preferably between 300 and 1800 grams per mole of unsaturated group (WPU) and the molecular weight (Mn) is preferably between 800 and 5000 grams per mole.
  • the polymer a) and the crosslinker b) can be either (semi) crystalline or amorphous. Depending on the required application, a mixture of crystalline and amorphous compounds can be selected in which the optimum balance of flow and processing properties can be obtained through the choice of the weight ratio.
  • the glass transition temperature (Tg) of an amorphous polyester generally ranges between 25 °C and 100 °C, and preferably between about 30 °C and about 80°C.
  • the melting point of a crystalline unsaturated polyester and of a crystalline crosslinker generally lies between 35 °C and 180 °C, preferably between 50 °C and 120 °C.
  • the preparation of the unsaturated polyester can for instance take place m one step, with (un) saturated acids and glycols being heated at, for instance, between about 180 °C and about 230 °C for, between about, 6 and about 15 hours.
  • the unsaturated polyester is generally composed of one or more aliphatic and/or cycloaliphatic , mono-, di- and/or polyhyd ⁇ c alcohols and one or more aliphatic, cycloaliphatic and/or aromatic di- or polycarboxylic acids and, if desirable, monocarboxylic acids and/or esters derived therefrom.
  • suitable alcohols are benzyl alcohol, ethylene glycol, 1 , 2 -propylene glycol, 1,3- propylene glycol, neopentyl glycol, butane diol, hexane diol, dimethylol cyclohexane, diethylene glycol, glycerol, trimethylol propane, pentaerythritol and/or dipentaerythritol .
  • one or several epoxy compounds such as, for instance, ethylene oxide, propylene oxide, epoxides (for instance Cardura TM), triglycidyl isocyanurate, carbonates such as, for instance, ethylene carbonate and propylene carbonate and/or allyl glycidyl ether can be used.
  • epoxy compounds such as, for instance, ethylene oxide, propylene oxide, epoxides (for instance Cardura TM), triglycidyl isocyanurate
  • carbonates such as, for instance, ethylene carbonate and propylene carbonate and/or allyl glycidyl ether can be used.
  • Suitable di- or polycarboxylic acids are maleic acid, fumaric acid, itaconic acid, citraconic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, 1 , 4-cyclohexane dicarboxylic acid, hexahydrophthalic acid, hexachloroendomethylene tetrahydrophthalic acid, dichlorophthalic acid, isophthalic acid, terephthalic acid and/or trimellitic acid.
  • the carboxylic acid can also be used in the form of an anhydride, for instance tetrahydrophthalic anhydride, maleic anhydride or phthalic anhydride.
  • the unsaturated polyester may also contain saturated or unsaturated monocarboxylic acids, such as synthetic and/or natural fatty acids with 2 to 36 carbon acids or esters prepared from these carboxylic acids and polyhydric alcohols such as glycerol.
  • suitable monocarboxylic acids are lauric acid, stearic acid, oleic acid, linolic acid, benzoic acid, acrylic acid and/or methacrylic acid.
  • the unsaturated polyester may also contain dicyclopentadiene .
  • unsaturated carboxylic acid use is preferably made of fumaric acid and/or maleic acid.
  • the monomers for the synthesis of (semi) crystalline polyesters preferably comprise diols and diacids with an even number of carbon atoms, such as, for instance, terephthalic acid, isophthalic acid, adipic acid and cyclohexane dicarboxylic acid, hexane diol, butane diol, ester diol and dimethylol cyclohexane .
  • Hydroxyl -functional unsaturated polyesters usually have a hydroxyl number between 5 mg KOH/gram of resin and 75 mg KOH/gram of resin and preferably a hydroxyl number of between 25 mg KOH/gram of resin and 60 mg KOH/gram of resin.
  • the acid number is as a rule lower than 10 mg KOH/gram of resin and is preferably chosen as low as possible.
  • Acid-functional unsaturated polyesters usually have an acid number of between 15 mg KOH/gram of resm and 75 mg KOH/gram of resm, and preferably an acid number of between 25 mg KOH/gram of resm and 45 mg KOH/gram of resm.
  • Suitable acrylate polymers are acrylate polymers containing several side chains with unsaturated groups . These polymers can be obtained by means of a two-step process. In a first step an acrylate polymer is prepared using the customary polymerization process, with also a certain proportion of functional monomer being copolymerized. This functional monomer, which is usually present amounts ranging from 3 to 60 wt.%, may for instance be epoxy functional, acid functional or isocyanate functional.
  • an addition reaction is carried out between the functional groups of the acrylate polymer from the first step and a compound containing a group capable of reacting with the functional groups and also containing an unsaturated group the side chain.
  • the functional acrylate resm can be dissolved m a solvent such as, for instance, toluene, xylene or butyl acetate.
  • a solvent such as, for instance, toluene, xylene or butyl acetate.
  • the compound containing an unsaturated group capable of reacting with the functional polymer is added at temperatures of between, for instance, 50 °C and 150 °C. Stirring is then continued for some hours.
  • the progress of the reaction can be monitored by means of titrations of, for instance, acid groups or isocyanate groups.
  • Possible addition reactions m the second step are, for instance, reactions between an acid group and an epoxy-functional acrylate polymer, a hydroxyl group and an isocyanate-functional acrylate polymer, an isocyanate group and a hydroxy- functional acrylate polymer, an anhydride group and a hydroxyl -functional acrylate polymer or an epoxy group and an acid- functional acrylate polymer.
  • an epoxy- functional acrylate polymer and (meth) acrylic acid is used.
  • the side chain with unsaturated groups can thus be formed by, for instance, anhydrides containing unsaturated groups, (meth) acrylate groups, allyl groups, vinyl groups and vmylether groups.
  • Suitable examples of compounds with unsaturated groups are (meth) acrylic acid, glycidyl (meth) acrylate, TMI , allyl glycidyl ether, hydroxybutyl vinyl ether and maleic anhydride.
  • the acrylate polymers can also be obtained by a multistep process.
  • one of the isocyanate groups of a diisocyanate compound for instance isophorone diisocyanate, hexane diisocyanate or methylene biscyclohexylisocyanate
  • a diisocyanate compound for instance isophorone diisocyanate, hexane diisocyanate or methylene biscyclohexylisocyanate
  • a hydroxy- functional (meth) acrylate monomer for instance, be reacted with a hydroxy-functional (meth) acrylate monomer.
  • the resulting compound which contains an isocyanate group and a (meth) acrylate group, can then be reacted with a hydroxy-functional polymer such as, for instance, an acrylate polymer which contains hydroxyethyl methacrylate as functional monomer .
  • a radiation-curable system can comprise a resm, a crosslinker, a photomitiator, a flow agent and pigments.
  • Radiation curing of the binder composition according to the invention preferably takes place through UV and EB curing.
  • composition according to the invention is cured by radical polymerization. Compared with cationic UV polymerization this has the advantage that curing is not affected by moisture and proceeds completely almost at once (no dark reaction needed) .
  • a photomitiator can, at a temperature ranging from, for instance, 40 °C to 120 °C, be mixed with a binder composition according to the invention. Mixing can take place both m a solvent and m the melt, for instance m an extruder or m a static mixer. Further, pigments and the desired auxiliary materials such as, for instance, flow agents can be added. The paint can subsequently be applied to the substrate or be sprayed electrostatically.
  • the powder paint is molten at temperatures ranging from, for instance, 40 °C to 170 °C by being placed m an oven, exposure to infra-red radiation, or a combination of both, so that a closed, smooth coating film is formed with a layer thickness ranging from, for instance, 20 to 200 ⁇ m, after which the still warm panel is cured under a UV light source. Afterwards post-heating may take place.
  • Photoinitiators initiate curing of the compositions according to the invention upon exposure to light.
  • Suitable initiators for radical polymerizations are ketonic and may be aromatic such as, for instance, benzophenone .
  • Irgacure 184 ® (Ciba) is an aryl ketone with hydroxycyclohexyl-phenyl-ketone as active component and is, like Irgacure 369 ® (active component 2 -benzyl-2 -dimethylamino-1- (4- morpholinophenyl) -butanone-1) , a suitable photoinitiator .
  • Acryl phosphine such as 2,4,6- trimethyl benzoyl diphenyl phosphine oxide (Lucerine TPO ® , BASF) can also be used. Chemical derivatives of this photoinitiator are also suitable, as are combinations of these initiators.
  • a suitable combination of photoinitiators is formed by Irgacure 1800 ® (Ciba), which consists of 75 wt . % Irgacure 184 ® and 25 wt . % (bis (2 , 6-dimethoxy benzoyl) -2 , 4 , 4 - trimethylpentyl phosphine oxide) .
  • the binder composition according to the invention can also yield a good coating after thermal curing under the influence of a latent catalyst such as, for instance, a peroxide.
  • Thermal curing can take place at temperatures ranging from, for instance, about 80°C to about 200°C, depending on the selected polymers .
  • customary additives in the paint formulations are pigments, emulsifiers, preservatives, light stabilizers, UV absorption agents, flow agents, degassing agents, fillers, stabilizers and/or catalysts.
  • saturated and unsaturated acrylates are polyurethane (meth) acrylates , polyester (meth) acrylates, polyether (meth) acrylates and/or polyepoxy (meth) acrylates .
  • a 4-litre round-bottom flask provided with a thermometer, stirrer and distillation head was filled with 98.6 g of trimethylol propane, 1,014 g of neopentyl glycol and 1.1 g of butylchlorotin dihydroxide . While a constant nitrogen flow was supplied, the temperature was raised to 175 °C, after which 1,204 g of terephthalic acid was added. The temperature was then raised to 220 °C in 2 hours, with water being distilled off. After an acid number lower than 100 mg KOH/g of resin had been reached, the reaction mixture was cooled to 140 °C.
  • the resulting polyester had an Mn (theor.) of 3000, a WPU of 1000 g resm/mole of unsaturated group, a hydroxy number of 62 mg KOH/g of resm, a Tg of 49°C (Mettler, TA 3.000 at 10 °C/mm.) and a viscosity of 110 dPas (Emila, 165°C) .
  • the resulting coating had a good flow (visually determined) , a good acetone resistance (no damage after 100 acetone double rubs) and a pendulum hardness (ISO 1522/DIN 53157) of 162 seconds.

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

Abstract

L'invention concerne une composition de liant durcissable par rayonnement et destinée aux formulations de peinture en poudre. La composition de liant pour peinture en poudre comprend: a) un polymère avec un certain degré d'insaturation, par exemple, avec un taux (poids du polymère) / (nombre de moles de groupes insaturés) compris entre 300 et 1800 g par mole de groupe insaturé (WPU) et avec un poids molaire (Mn) entre 800 et 5000 g par mole; et b) un agent de réticulation comprenant des unités de formamide de N-vinyle ou d'amide de N-propényle.
PCT/NL1999/000765 1998-12-14 1999-12-13 Composition de liant pour peinture en poudre WO2000036026A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16977/00A AU1697700A (en) 1998-12-14 1999-12-13 Powder paint binder composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98204222 1998-12-14
EP98204222.8 1998-12-14

Publications (1)

Publication Number Publication Date
WO2000036026A1 true WO2000036026A1 (fr) 2000-06-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1999/000765 WO2000036026A1 (fr) 1998-12-14 1999-12-13 Composition de liant pour peinture en poudre

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AU (1) AU1697700A (fr)
WO (1) WO2000036026A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4424314A (en) * 1974-08-28 1984-01-03 Basf Aktiengesellschaft Curable coating composition
EP0559135A1 (fr) * 1992-03-03 1993-09-08 Air Products And Chemicals, Inc. Compositions durcissables par radiation et méthode d'utilisation
EP0632111A1 (fr) * 1993-07-01 1995-01-04 Air Products And Chemicals, Inc. Procédé de revêtement utilisant des compositions durcissables par radiations
EP0636669A2 (fr) * 1993-07-30 1995-02-01 Dsm N.V. Composition de liant pour peintures en poudre, durcissable par irradiation
WO1998055550A1 (fr) * 1997-06-06 1998-12-10 Dsm N.V. Composition liante de peinture en poudre

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4424314A (en) * 1974-08-28 1984-01-03 Basf Aktiengesellschaft Curable coating composition
EP0559135A1 (fr) * 1992-03-03 1993-09-08 Air Products And Chemicals, Inc. Compositions durcissables par radiation et méthode d'utilisation
EP0632111A1 (fr) * 1993-07-01 1995-01-04 Air Products And Chemicals, Inc. Procédé de revêtement utilisant des compositions durcissables par radiations
EP0636669A2 (fr) * 1993-07-30 1995-02-01 Dsm N.V. Composition de liant pour peintures en poudre, durcissable par irradiation
WO1998055550A1 (fr) * 1997-06-06 1998-12-10 Dsm N.V. Composition liante de peinture en poudre

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