EP1171501A1 - Materiau de revetement aqueux durcissable par rayonnement thermique et/ou actinique et son utilisation - Google Patents

Materiau de revetement aqueux durcissable par rayonnement thermique et/ou actinique et son utilisation

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Publication number
EP1171501A1
EP1171501A1 EP00916960A EP00916960A EP1171501A1 EP 1171501 A1 EP1171501 A1 EP 1171501A1 EP 00916960 A EP00916960 A EP 00916960A EP 00916960 A EP00916960 A EP 00916960A EP 1171501 A1 EP1171501 A1 EP 1171501A1
Authority
EP
European Patent Office
Prior art keywords
layer
coating material
groups
aqueous coating
acid
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Withdrawn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
EP00916960A
Other languages
German (de)
English (en)
Inventor
Karl Haeberle
Heinz-Peter Rink
Bernhard Lettmann
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.)
BASF Coatings GmbH
Original Assignee
BASF Coatings 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 BASF Coatings GmbH filed Critical BASF Coatings GmbH
Publication of EP1171501A1 publication Critical patent/EP1171501A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50—Multilayers
    • B05D7/52—Two layers
    • B05D7/53—Base coat plus clear coat type
    • B05D7/534—Base coat plus clear coat type the first layer being let to dry at least partially before applying the second layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50—Multilayers
    • B05D7/56—Three layers or more
    • B05D7/57—Three layers or more the last layer being a clear coat
    • B05D7/574—Three layers or more the last layer being a clear coat at least some layers being let to dry at least partially before applying the next layer
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin 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
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • 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

Definitions

  • the present invention relates to a new aqueous coating material based on polyurethane, its production and its use in automotive refinishing, industrial painting, including coil coating and container coating, plastic painting and furniture painting.
  • aqueous coating materials which contain at least one ionically and / or nonionically stabilized polyurethane based on bis (4-isocyanatocyclohexyl) methane with a trans / trans content of up to 18 mol%, based on the diisocyanate, in an aqueous phase contain dispersed are known from the German patent DE-A-44 14 032. They have very good film-forming properties and provide clear, transparent coatings. The patent also states that these known coating materials can also contain pigments.
  • Aqueous coating materials which are curable thermally and / or with actinic radiation and a saturated, unsaturated and / or grafted with olefinically unsaturated compounds, ionically and / or nonionically stabilized polyurethane based on bis (4-isocyanatocyclohexyl) methane of a trans / trans Contents of up to 18 mol%, based on the diisocyanate, and contain a crosslinking agent are not apparent from the patent.
  • Thermally curable aqueous coating materials which contain a crosslinking agent and a saturated, unsaturated and / or grafted with olefinically unsaturated, ionically and / or nonionically stabilized polyurethane based on aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic, aliphatic-aromatic and / or cycloaliphatic Contain polyisocanates, and the corresponding coatings, for example, from the patents EP-A-0 089 497, EP-A- 0 256 540, EP-A-0 260 447, EP-A-0 297 576, WO 96/12747, EP-A-0 523 610, EP-A-0228 003, EP-A-0397 806, EP-A -0 574417, EP-A-0531 510, EP-A-0 581 211, EP-A-0708788, EP-A-0 593 454,
  • the object of the present invention is to provide a new thermally and / or actinic radiation curable coating material which contains at least one saturated, unsaturated and / or grafted with olefinically unsaturated compounds, ionically and / or nonionically stabilized polyurethane dispersed in an aqueous phase and which with an application-related property profile that corresponds to or even exceeds that of the prior art, has no or only a very slight tendency to form coagulates.
  • coating material curable thermally and / or with actinic radiation
  • the new process for producing a single-layer or multi-layer clear or color and / or effect coating by applying at least one layer of the coating material of the invention to a primed or unprimed substrate and thermal curing and / or curing with actinic radiation of the resulting wet layer found.
  • This new method is referred to below as the “first method according to the invention”.
  • aqueous coating material which contains at least one saturated, unsaturated and / or grafted with olefinically unsaturated compounds, ionically and / or nonionically stabilized polyurethane (A) based on bis (4-isocyanatocyclohexyl) methane of a trans / trans content of up to 30% by weight .-%, based on the diisocyanate, contains.
  • A polyurethane
  • a variant of the second method according to the invention was also found, which comprises at least the following method steps:
  • aqueous coating material which contains at least one saturated, unsaturated and / or grafted with olefinically unsaturated compounds, contains ionically and / or nonionically stabilized polyurethane (A) based on bis (4-isocyanatocyclohexyl) rnethan with a trans / trans content of up to 30% by weight, based on the diisocyanate.
  • A polyurethane
  • second process the new processes for producing a multi-layer coloring and / or effect coating according to the wet-on-wet process are collectively referred to as “second process according to the invention”.
  • the term “physical hardening” means the hardening of a layer made of a coating material
  • the coating material according to the invention is thermal and / or actinic
  • thermal curing means the heat-initiated curing of a layer of a coating material, in which a crosslinking agent that is usually present is used. Usually this is referred to by experts as external crosslinking.
  • the crosslinking agents are already in the binder built-in, one speaks of self-crosslinking, according to the invention the external crosslinking is advantageous and is therefore preferred.
  • actinic radiation is understood to mean electron radiation or preferably UV radiation. Curing by UV radiation is usually initiated by radical or cationic photoinitiators. If thermal and curing with actinic light are used together in one coating material, this is also referred to as "dual cure”.
  • the coating material of the invention can be a one-component (IC) system.
  • a one-component (IC) system is to be understood as a thermally curing coating material in which the binder and the crosslinking agent coexist, i.e. in one component.
  • the prerequisite for this is that the two components only crosslink with one another at higher temperatures and / or when irradiated with actinic radiation.
  • the coating material of the invention can also be a two-component (2K) or multi-component (3K, 4K) system.
  • this is to be understood as a coating material in which, in particular, the binder and the crosslinking agent are present separately from one another in at least two components, which are only combined shortly before application. This form is selected when the binder and crosslinking agent react with one another at room temperature. Coating materials of this type are used primarily for coating thermally sensitive substrates, in particular in automotive refinishing.
  • the coating material of the invention is used to produce transparent clear lacquer layers and / or to produce color and / or effect water-based lacquer layers. It is particularly preferably used for the production of water-based lacquer layers.
  • the first essential component of the coating material of the invention is its binder (A).
  • this is at least one saturated, unsaturated and / or grafted with olefinically unsaturated compounds, ionically and / or nonionically stabilized polyurethane based on bis (4-isocyanatocyclohexyl) methane with a trans / trans content of up to 30% by weight. -%, based on the diisocyanate, which for the sake of brevity is referred to as "polyurethane (A) to be used according to the invention".
  • the polyurethane (A) to be used according to the invention advantageously has an acid number or amine number of 10 to 250 mg KOH / g (ionic stabilization or nonionic plus ionic stabilization) or from 0 to 10 mg KOH / g (nonionic stabilization), an OH number of 30 to 350 mg KOH / g and a number average molecular weight of 1,500 to 55,000 daltons.
  • the essential starting product of the polyurethane to be used according to the invention is liquid bis (4-isocyanatocyclohexyl) methane with a trans / trans content of up to 30% by weight, preferably up to 25% by weight and in particular up to 20% by weight.
  • trans / trans contents of over 30% by weight, the advantages achieved by the present invention are no longer reliable and safe.
  • the liquid bis (4-isocyanatocyclohexyl) methane having a trans / trans content of up to 30% by weight, preferably up to 25% by weight and in particular up to 20% by weight, and its preparation by phosgenation of isomer mixtures of bis ( 4- aminocyclohexyl) methane or by fractional crystallization of commercially available bis (4-isocyanatocyclohexyl) rnethan is from the patents DE-A-44 14 032, GB-A-1220717, DE-A-16 18 795 or DE-A-17 93 785 known.
  • liquid bis (4-isocyanatocyclohexyl) methane in addition to the liquid bis (4-isocyanatocyclohexyl) methane, other aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic, aliphatic-aromatic and / or cycloaüphatic-aromatic polyisocanates can be used in minor amounts for the production of the polyurethanes to be used according to the invention.
  • “minor amounts” are to be understood as meaning a proportion of other polyisocyanates which does not reduce the profile of application properties achieved according to the invention, but varies in an advantageous manner.
  • the proportion of other polyisocyanates should be 40 mol%, preferably 30 mol% and in particular 20 mol%, in each case based on the total amount of the polyisocanates used for the production, do not exceed.
  • Suitable polyols are saturated or olefinically unsaturated polyester polyols which are obtained by reacting
  • Polycarboxylic acids or their esterifiable derivatives optionally together with monocarboxylic acids, and
  • suitable polycarboxylic acids are aromatic, aliphatic and cycloaliphatic polycarboxylic acids. Aromatic and / or aliphatic polycarboxylic acids are preferably used.
  • aromatic polycarboxylic acids examples include phthalic acid, isophthalic acid, terephthalic acid, phthalic acid, isophthalic acid or terephthalic acid monosulfonate, or halophthalic acids, such as tetrachloro- or tetrabromophthalic acid, of which isophthalic acid is advantageous and is therefore used with preference.
  • Suitable acyclic aliphatic or unsaturated polycarboxylic acids are oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, dodecanedicarboxylic acid or dimer fatty acid or maleic acid, fumaric acid, sebacic acid, of which adacidic acid, of which Dimer fatty acids and maleic acid are advantageous and are therefore used with preference.
  • Suitable cycloaliphatic and cyclic unsaturated polycarboxylic acids are 1,2-cyclobutanedicarboxylic acid, 1,3-
  • Cyclopentanedicarboxylic acid hexahydrophthalic acid, 1, 3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 4-methylhexahydrophthalic acid, tricyclodecanedicarboxylic acid, tetrahydrophthalic acid or 4-methyltetrahydrophthalic acid.
  • dicarboxylic acids can be used both in their ice and in their trans form and as a mixture of both forms.
  • esterifiable derivatives of the abovementioned polycarboxylic acids are also suitable Alcohols with 1 to 4 carbon atoms or hydroxy alcohols with 1 to 4 carbon atoms.
  • anhydrides of the above-mentioned polycarboxylic acids can also be used if they exist.
  • monocarboxylic acids can also be used together with the polycarboxylic acids, such as, for example, benzoic acid, tert-butylbenzoic acid, lauric acid, isononanoic acid, fatty acids of naturally occurring oils, acrylic acid, methacrylic acid, ethacrylic acid or crotonic acid.
  • Isononanoic acid is preferably used as the monocarboxylic acid.
  • Suitable polyols are diols and triols, especially diols.
  • triols are usually used in minor amounts in order to introduce branches into the polyester polyols.
  • Suitable diols are ethylene glycol, 1,2- or 1,3-propanediol, 1,2-, 1,3- or 1,4-butanediol, 1,2-, 1,3-, 1,4- or 1.5 Pentanediol, 1,2-, 1,3-, 1,4-, 1,5- or 1,6-hexanediol, hydroxypivalic acid neopentyl ester, neopentyl glycol,
  • diols can also be used as such for the production of the polyurethanes (A) to be used according to the invention.
  • diols of the formula I or II are diols of the formula I or II:
  • R 1 and R 2 each represent the same or different radical and represent an alkyl radical having 1 to 18 carbon atoms, an aryl radical or a cycloaliphatic radical, with the proviso that R 1 and / or R 2 must not be methyl ;
  • R 3 , R 4 , R 6 and R 7 each represent the same or different radicals and represent an alkyl radical with 1 to 6 C atoms, a cycloalkyl radical or an aryl radical and R 5 is an alkyl radical with 1 to 6 C atoms, represents an aryl radical or an unsaturated alkyl radical having 1 to 6 C atoms, and n is either 0 or 1.
  • Suitable diols I of the general formula I are all propanediols of the formula in which either R 1 or R 2 or R 1 and R 2 is not methyl, such as 2-butyl-2-ethylpropanediol-1,3,2-butyl -2-methylpropanediol-1,3,2-phenyl-2-methylpropane-diol-3,2-propyl-2-ethylpropanediol-1,3
  • diols ⁇ of the general formula II for example, 2,5-dimethyl-hexanediol-2,5, 2,5-diethylhexanediol-2,5, 2-ethyl-5-methylhexanediol-2,5, 2,4-dimethylpentanediol-2 , 4, 2,3-dimethylbutanediol-2,3,1,4- (2'-hydroxypropyl) benzene and 1,3- (2'-hydroxypropyl) benzene can be used.
  • hexanediol and neopentyl glycol are particularly advantageous and are therefore used with particular preference.
  • the diols mentioned above can also be used as such for the preparation of the polyurethanes (A) to be used according to the invention.
  • suitable triols are trimethylolethane, trimethylolpropane or glycerol, in particular trimethylolpropane.
  • triols mentioned above can also be used as such for the production of the polyurethanes (A) to be used according to the invention (cf. patent EP-A-0 339433).
  • monools can also be used.
  • suitable monools are alcohols or phenols such as ethanol, propanol, n-butanol, sec-butanol, tert-butanol, amyl alcohols, hexanols, fatty alcohols, allyl alcohol or phenol.
  • the polyester polyols can be prepared in the presence of small amounts of a suitable solvent as an entrainer.
  • a suitable solvent as an entrainer z.
  • polyester diols which are obtained by reacting a lactone with a diol. They are characterized by the presence of hydroxyl groups and recurring
  • No substituent contains more than 12 carbon atoms. The total number of carbon atoms in the substituent does not exceed 12 per lactone ring. Examples include hydroxycaproic acid, hydroxybutyric acid, hydroxydecanoic acid and / or hydroxystearic acid.
  • the unsubstituted ⁇ -caprolactone in which m has the value 4 and all R ⁇ substituents are hydrogen, is preferred.
  • the reaction with lactone is started by low molecular weight polyols such as ethylene glycol, 1,3-propanediol, 1,4-butanediol or dimethylolcyclohexane.
  • polyols such as ethylene glycol, 1,3-propanediol, 1,4-butanediol or dimethylolcyclohexane.
  • other reaction components such as ethylenediamine, alkyldialkanolamines or even urea, can also be reacted with caprolactone.
  • polylactam diols which are prepared by reacting, for example, ⁇ -caprolactam with low molecular weight diols.
  • suitable polyols are polyethene polyols, in particular with a number average molecular weight from 400 to 5000, in particular from 400 to 3000.
  • suitable polyether diols are e.g. General polyether diols
  • the polyether diols should not introduce excessive amounts of ether groups, because otherwise the polyurethanes (A) to be used according to the invention swell in water. On the other hand, they can be used in amounts which ensure the nonionic stabilization of the polyurethanes (A). They then serve as the functional nonionic groups (a3) described below.
  • suitable polyols are poly (meth) acrylate diols, polycarbonatediols or polyolefin polyols such as POLYTAIL® from Mitsubishi Chemical Group.
  • the polyurethane (A) to be used according to the invention contains either (al) functional groups which can be converted into cations by neutralizing agents and / or quaternizing agents and / or cationic groups, in particular ammonium groups,
  • Suitable functional groups (a1) to be used according to the invention which can be converted into cations by neutralizing agents and / or quaternizing agents, are primary, secondary or tertiary amino groups, secondary sulfide groups or tertiary phosphine groups, in particular tertiary amino groups or secondary sulfide groups.
  • Suitable cationic groups (a1) to be used according to the invention are primary, secondary, tertiary or quaternary ammonium groups, tertiary sulfonium groups or quaternary phosphomium groups, preferably quaternary ammonium groups or quaternary ammonium groups, tertiary sulfonium groups, but especially tertiary sulfonium groups.
  • Suitable functional groups (a2) to be used according to the invention which can be converted into anions by neutralizing agents Carboxylic acid, sulfonic acid or phosphonic acid groups, especially carboxylic acid groups.
  • Suitable anionic groups (a2) to be used according to the invention are carboxylate, sulfonate or phosphonate groups, in particular carboxylate groups.
  • Suitable neutralizing agents for functional grappa (al) which can be converted into cations are inorganic and organic acids such as sulfuric acid, hydrochloric acid, phosphoric acid, formic acid, acetic acid, lactic acid, dimethylolpropionic acid or citric acid.
  • Suitable neutralizing agents for functional groups (a2) which can be converted into anions are ammonia, ammonium salts, such as, for example, ammonium carbonate or ammonium bicarbonate, and amines, such as, for example, Triethylamine, triethylamine, tributylamine, dimethylaniline, diethylaniline, triphenylamine, dimethylethanolamine, diethyletbanolamine, methyldiethanolamine, triethanolamine and the like.
  • the neutralization can take place in the organic phase or in the aqueous phase. Dimethylethanolamine is preferably used as the neutralizing agent.
  • the total amount of neutralizing agent used in the coating composition according to the invention is selected so that 1 to 100 equivalents, preferably 50 to 90 equivalents, of the functional groups (a1) or (a2) of the polyurethane (A) to be used according to the invention are neutralized.
  • the (potentially) anionic groups (a2) are advantageous and are therefore used with particular preference.
  • the introduction of (potentially) anionic groups (a2) into the polyurethane molecules takes place via the incorporation of compounds which contain at least one group which is reactive towards isocyanate groups and one which is capable of forming anions in the molecule; the amount to be used can be calculated from the target acid number.
  • suitable compounds of this type are those which contain two groups which are reactive toward isocyanate groups in the molecule.
  • Suitable groups which are reactive toward isocyanate groups are, in particular, hydroxyl groups and primary and / or secondary amino groups.
  • alkanoic acids with two substituents on the ⁇ -carbon atom can be used.
  • the substituent can be a hydroxyl group, an alkyl group or preferably an alkylol group.
  • These alkanoic acids have at least one, generally 1 to 3 carboxyl groups in the molecule. They have 2 to about 25, preferably 3 to 10, carbon atoms.
  • suitable alkanoic acids are dihydroxypropionic acid, dihydroxysuccinic acid and dihydroxybenzoic acid.
  • a particularly preferred group of alkanoic acids are the ⁇ , ⁇
  • RIO represents a hydrogen atom or an alkyl group with up to about 20 carbon atoms.
  • alkanoic acids are 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-
  • Dimethylolbutyric acid and 2,2-dimenthylolpentanoic acid Dimethylolbutyric acid and 2,2-dimenthylolpentanoic acid.
  • the preferred dihydroxyalkanoic acid is 2,2-dimethylolpropionic acid.
  • Compounds containing amino groups are, for example, ⁇ , ⁇ -diaminovaleric acid, 3,4-diaminobenzoic acid, 2,4-diaminotoluenesulfonic acid and 2,4-diamino-diphenyl ether sulfonic acid.
  • Nonionic stabilizing poly (oxyalkylene) groups (a3) can be introduced into the polyurethane molecules as lateral or terminal groups.
  • R 12 is a hydrogen atom or an alkyl radical having 1 to 6 carbon atoms and the index r is a number between 20 and 75, (see. The patents EP-A-0 354 261 or EP-A-0 424 705).
  • polyols, polyamines and amino alcohols leads to an increase in the molecular weight of the polyurethanes (A).
  • Suitable polyols for chain extension are polyols with up to 36 carbon atoms per molecule, such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,2-butylene glycol, 1,6-hexanediol , Trimethylolpropane, castor oil or hydrogenated castor oil, di-trimethylolpropane ether, pentaerythritol, 1,2-cyclohexanediol, 1,4-cyclohexanedimethanol, bisphenol A, bisphenol F, neopentyl glycol, hydroxypivalic acid-neopentyl glycol ester, hydroxyethylated or hydroxypropylated bisphenol A, mixtures of these (see patent specifications EP-A-0339 433, EP-A-0436 941, EP-A-0517 707).
  • polyamines have at least two primary and / or secondary amino groups.
  • Polyamines are essentially alkylene polyamines having 1 to 40 carbon atoms, preferably about 2 to 15 carbon atoms. They can carry substituents that have no hydrogen atoms that are reactive with isocyanate grapples. Examples are polyamines with a linear or branched aliphatic, cycloahphatic or aromatic structure and at least two primary amino groups.
  • Diamines are hydrazine, alkyl or cycloalkyl diamines such as propylenediamine and 1-amino-3-aminomethyl-3, 5, 5-trimethylcyclohexane.
  • polyamines which contain more than two amino groups in the molecule. In these cases, however - e.g. by using monoamines - make sure that no cross-linked polyurethane resins are obtained.
  • useful polyamines are diethylenetriamine, triethylenetetramine, dipropylenediamine and dibutylenetriamine.
  • An example of a monoamine is ethylhexylamine (cf. patent EP-A-0 089 497).
  • Suitable amino alcohols are ethanolamine or diethanolamine.
  • the polyurethanes (A) to be used according to the invention can contain terminal and / or lateral olefinically unsaturated grapples. Grapples of this type can be introduced, for example, with the aid of compounds which have at least one isocyanate-reactive group, in particular hydroxyl group, and at least one vinyl group. Examples of suitable compounds of this type are trimethylolpropane monoallyl ether or trimethylolpropane mono (meth) acrylate.
  • polyurethanes (A) to be used according to the invention can be grafted with ethylenically unsaturated compounds.
  • suitable polyurethanes (A) to be used according to the invention which are present as graft copolymers, are known from the patents EP-A-0 521 928, EP-A-0 522420, EP-A-0 522419 or EP-A-0730 613.
  • the production of the polyurethanes (A) to be used according to the invention has no special features in terms of method, but is carried out by the customary and known methods as described in the prior art cited at the beginning.
  • the second essential component of the coating material of the invention is at least one crosslinking agent (B).
  • crosslinking agents (B) for the one-component (IC) systems are amino resins, compounds or resins containing anhydride groups, compounds or resins containing epoxy groups, tris (alkoxycarbonylamino) triazines, compounds or resins containing carbonate groups, blocked and / or unblocked polyisocyanates, beta - Hydroxyalkylamides and compounds with an average of at least two grappes capable of transesterification, for example reaction products of diesters of malonic acid and polyisocyanates or of esters and parts of polyesters of malonic acid with monoisocyanates, as described in European patent EP-A-0596460.
  • crosslinking agents are well known to the person skilled in the art and are offered by numerous companies as sales products.
  • any aminoplast resin or a mixture of such aminoplast resins suitable for topcoats or transparent clearcoats can be used here.
  • the customary and known amino resins come into consideration, the methylol and / or methoxymethyl groups z. T. are defunctionalized by means of carbamate or allophanate groups.
  • Crosslinking agents of this type are described in the patents US-A-4 710 542 and EP-B-0 245 700 and in the article by B. Singh and co-workers "Carbamylmethylated Melamines, Novel Crosslinkers for the Coatings Industry" in Advanced Organic Coatings Science and Technology Series, 1991, Volume 13, pages 193 to 207.
  • polyepoxides examples include all known aliphatic and / or cycloaliphatic and / or aromatic polyepoxides, for example based on bisphenol-A or bisphenol-F.
  • polyepoxides commercially available under the names Epikote® from Shell, Denacol® from Nagase Chemicals Ltd., Japan, such as Denacol EX-411 (pentaerythritol polyglycidyl ether), Denacol EX-321
  • methyl-butyl mixed esters, the butyl-2-ethylhexyl mixed esters and the butyl esters are advantageous. Compared to the pure methyl ester, these have the advantage of better solubility in polymer melts and also have less tendency to crystallize out.
  • An example of a suitable polyanhydride is polysuccinic anhydride.
  • beta-hydroxyalkylamides are N, N, N ', N'-tetrakis (2-hydroxyethyl) adipamide or N, N, N', N'-tetrakis (2-hydroxypropyl) adipamide.
  • the blocked polyisocyanates are further examples of suitable crosslinking agents.
  • blocking agents are the blocking agents known from US Pat. No. 4,444,954:
  • phenols such as phenol, cresol, xylenol, nitrophenol, chlorophenol, ethylphenol, t-butylphenol, hydroxybenzoic acid, esters of this acid or 2,5-di-tert-butyl-4-hydroxytoluene;
  • lactams such as ⁇ -caprolactam, ⁇ -valerolactam, ⁇ -butyrolactam or ß-propiolactam
  • active methylenic compounds such as diethyl malonate, dimethyl malonate, ethyl or methyl acetoacetate or
  • alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-amyl alcohol, t-amyl alcohol, lauryl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,
  • mercaptans such as butyl mercaptan, hexyl mercaptan, t-butyl mercaptan, t-dodecyl mercaptan, 2-mercaptobenzothiazole, thiophenol,
  • acid amides such as acetoanilide, acetoanisidinamide, acrylamide, methacrylamide, acetic acid amide, stearic acid amide or benzamide;
  • imides such as succinimide, phthalimide or maleimide
  • amines such as diphenylamine, phenylnaphthylamine, xylidine, N-phenylxyüdin, carbazole, anion, naphthylamine, butylamine, dibutylamine or butylphenylamine;
  • imidazoles such as imidazole or 2-ethyumidazole
  • ureas such as urea, thiourea, ethylene urea, ethylene thiourea or 1,3-diphenyl urea;
  • xi) carbamates such as phenyl N-phenylcarbamate or 2-oxazolidone
  • xii) ixnines such as ethyleneimine
  • oximes such as acetone oxime, formal doxime, acetaldoxime, acetoxime, methyl ethyl ketoxime, diisobutyl ketoxime, diacetyl monoxime,
  • xiv) salts of sulfurous acid such as sodium bisulfite or potassium bisulfite
  • hydroxamic acid esters such as benzyl methacrylohydroxamate (BMH) or allyl methacrylohydroxamate; or xvi) substituted pyrazoles, ketoximes, hnidazoles or triazoles; such as
  • suitable organic polyisocyanates to be blocked are in particular the so-called lacquer polyisocyanates with aliphatic, cycloaliphatic, araliphatic and / or aromatically bound isocyanate groups.
  • the polyisocyanates can be modified in a customary and known manner to be hydrophilic or hydrophobic.
  • Polyurethane prepolymers which can be prepared by reacting polyols with an excess of polyisocyanates and which are preferably of low viscosity.
  • polyisocyanates to be blocked are polyisocyanates containing isocyanurate, biuret, allophanate, iminooxadiazindone, urethane, urea and / or uretdione groups.
  • Polyisocyanates containing urethane groups are obtained, for example, by reacting some of the isocyanate groups with polyols, such as, for example, trimethylolpropane and glycerol.
  • Ahphatic or cyclophilic polyisocyanates, in particular hexamethylene diisocyanate are preferably dimerized and trimerized hexamethylene diisocyanate, isophorone diisocyanate,
  • Diisocyanates derived from dimer fatty acids such as those sold by Henkel under the trade name DDI 1410 and described in patents DO 97/49745 and WO 97/49747, in particular 2-heptyl-3,4-bis (9-isocyanatononyl) -l pentyl cyclohexane; or 1,2-, 1,4- or 1,3-bis (isocyanatomethyl) cyclohexane, 1,2-, 1,4- or 1,3-bis (2-isocyanatoeth-l-yl) cyclohexane, 1,3 -Bis (3-isocyanatoprop-l-yl) cyclohexane or 1,2-, 1,4- or 1,3-bis (4-isocyanatobut-l-yi) cyclohexane, 1,8-diisocyanato-4-isocyanatomethyl-octane , l, 7-diisocyanato-4-isocyan
  • crosslinking agents for the two-component (2K) or multicomponent (3K, 4K) systems are the unblocked polyisocyanates mentioned above.
  • the coating material of the invention may contain additives (D) in effective amounts.
  • the type and amount of the additives (D) depend primarily on the intended use of the coating material of the invention. It is essential that these additives (D) should not be volatile under the processing and application conditions of the coating material of the invention.
  • the coating materials according to the invention are used as a topcoat or waterborne basecoat, they contain coloring and / or effect pigments (D) in usual and known amounts.
  • the pigments (D) can consist of inorganic or organic compounds and can give effect and / or color. Because of this large number of suitable pigments (D), the coating material according to the invention therefore ensures a universal range of use for the coating materials and enables a multitude of color tones and optical effects to be achieved.
  • Metal pigments such as commercially available aluminum bronzes, aluminum bronzes chromated according to DE-A-36 36 183, and commercially available stainless steel bronzes as well as non-metallic effect pigments such as pearlescent or interference pigments can be used as effect pigments (D).
  • suitable inorganic color pigments (D) are titanium dioxide, iron oxides, Sicotrans yellow and carbon black.
  • suitable organic coloring pigments are indanthrene blue, cromophthal red, ixgazin orange and heliogen green.
  • the coating material of the invention can contain organic and inorganic fillers (D) in customary and known, effective amounts.
  • suitable fillers are chalk, calcium sulfates, barium sulfate, silicates such as talc or Kaohn, silicas, oxides such as aluminum hydroxide or magnesium hydroxide, nanoparticles or organic fillers such as textile fibers, cellulose fibers, polyethylene fibers or wood flour.
  • additives (D) are omitted if the coating materials of the invention are used as clear lacquers.
  • Emulsifiers in particular non-ionic emulsifiers such as alkoxy-etherified alkanols and polyols, phenols and alkylphenols or anionic emulsifiers such as alkali metal salts or ammonium salts of alkane carboxylic acids, alkane sulfonic acids, and sulfonic acids of alkoxy etherified alkanols and polyols, phenols and alkylphenols;
  • non-ionic emulsifiers such as alkoxy-etherified alkanols and polyols, phenols and alkylphenols
  • anionic emulsifiers such as alkali metal salts or ammonium salts of alkane carboxylic acids, alkane sulfonic acids, and sulfonic acids of alkoxy etherified alkanols and polyols, phenols and alkylphenols;
  • wetting agents such as siloxanes, fluorine-containing compounds,
  • - film-forming aids such as cellulose derivatives
  • rheology-controlling additives such as those known from the patent specifications WO 94/22968, EP-A-0 276 501, EP-A-0 249 201 or WO 97/12945; crosslinked polymeric microparticles, as described, for example, in EP-A-0 008 127; inorganic layered silicates such as aluminum-magnesium silicates, sodium-magnesium and
  • Photoinitiators such as photoinitiators of the Norrish LT type, whose mechanism of action is based on an intramolecular variant of the hydrogen abstraction reactions, as they occur in diverse ways in photochemical reactions; for example here on Römpp Chemie Lexikon, 9th extended and revised edition, Georg
  • the coating material of the invention may further contain reactive diluents (E) for thermal curing or for curing with actinic radiation.
  • Suitable reactive diluents (E) for thermal curing are oligomeric polyols which are obtained from oligomeric intermediates
  • Metathesis reactions of acyclic monoolefins and cyclic monoolefins are obtained by hydroformylation and subsequent hydrogenation;
  • suitable cyclic monoolefins are cyclobutene, cyclopentene, cyclohexene, cyclooctene, cycloheptene, norbornene or 7- Oxanorbones;
  • suitable acycüsche mono-olefms are contained in hydrocarbon mixtures which are obtained in petroleum processing by cracking (C 5 cut );
  • Examples of suitable ougomeric polyols to be used according to the invention have a hydroxyl number from 200 to 450, a number average molecular weight Mn from 400 to 1000 and a mass average molecular weight Mw from 600 to 1100;
  • suitable polyols are branched, cyclic and / or acyclic Cg-Ciö-alkanes which are functionalized with at least two hydroxyl groups, in particular diethyloctanediols.
  • polyols to be used are hyperbranched compounds with a tetrafunctional central group, derived from ditrimethylolpropane, diglycerol, ditrimethylolethane, penteerythritol, tetrakis (2-hydroxyethyl) methane, tetrakis (3-hydroxypropyl) methane or 2,2-bis-hydroxymethyl-butanediol- ( 1,4) (homopentaerythritol).
  • These reactive diluents can be prepared by the customary and known methods of producing hyperbranched and dendrimeric compounds.
  • Suitable synthesis methods are described, for example, in the patent specifications WO 93/17060 or WO 96/12754 or in the book by GR Newkome, CN Moorefield and F. Vögtie, "Dendritic Molecules, Concepts, Syntheses, Perspectives", VCH, Weinheim, New York, 1996 , described.
  • Low-molecular polyfunctional ethylenically unsaturated compounds are suitable as radiation-curable reactive diluents (E).
  • suitable compounds of this type are esters of acrylic acid with polyols, such as neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate or pentaerythritol tetraacrylate; or reaction products of hydroxyalkyl acrylates with polyisocyanates, especially aliphatic polyisocyanates.
  • the coating materials according to the invention can also contain up to 50% by weight, based on the total amount of binders, of one or more binders (F) different from (A), such as non-linear and / or branched and / or block-like, comb-like and / or randomly constructed poly (meth) acrylates, polyesters, polyurethanes, acrylated polyurethanes, acrylic polyesters, polylactones, polycarbonates, polyethers, (meth) acrylate diols or polyureas.
  • binders (F) different from (A) such as non-linear and / or branched and / or block-like, comb-like and / or randomly constructed poly (meth) acrylates, polyesters, polyurethanes, acrylated polyurethanes, acrylic polyesters, polylactones, polycarbonates, polyethers, (meth) acrylate diols or polyureas.
  • the coating material of the invention can contain the constituents described above dispersed in aqueous phase (C) and / or dissolved in a molecular dispersion.
  • the constituents are advantageously dispersed in the aqueous phase (C) because this generally does not require the addition of organic cosolvents.
  • the constituents and thus the coating material of the invention can be present in the dispersion in finely divided liquid or solid form. If they are in finely divided solid form, the coating material of the invention is a powder coating slurry.
  • the aqueous phase (C) essentially contains water.
  • the aqueous medium (C) can contain minor amounts of other solid, liquid or gaseous organic and / or inorganic, low and / or high molecular weight substances in a molecularly dispersed solution.
  • the term “minor amount” is understood to mean an amount which does not cancel out the aqueous character of the aqueous medium (C).
  • the aqueous phase (C) can also be pure water.
  • the production of the coating material according to the invention has no peculiarities, but was carried out by dispersing its constituents in the aqueous medium (C), it being possible to use primary or secondary dispersion processes.
  • C aqueous medium
  • the coating material of the invention is outstandingly suitable for the production of single- or multi-layer clear or coloring and / or effect-imparting varnishes.
  • the single-coat and multi-coat paint bars according to the invention can be produced by the most varied of processes. It is advantageous to manufacture them using the method according to the invention.
  • the method according to the invention is based on the substrate to be coated.
  • the substrate can consist of metal, wood, plastic, glass or paper or contain these substances as composites. It is preferably car body parts or industrial components, including containers, made of MetaU.
  • the substrate can be provided with a primer, hu in the case of plastics it is a so-called hydro-primer which is cured before the application of the coating material of the invention, in particular the water-based lacquer or the clear lacquer, in the case of metals, in particular automobile body parts around customary and well-known hardened electro-dipping paints onto which a filler is applied and baked.
  • a primer hu in the case of plastics it is a so-called hydro-primer which is cured before the application of the coating material of the invention, in particular the water-based lacquer or the clear lacquer, in the case of metals, in particular automobile body parts around customary and well-known hardened electro-dipping paints onto which a filler is applied and baked.
  • the coating material of the invention is cured thermally and / or with actinic radiation in a customary and known manner.
  • the first method according to the invention is particularly suitable for the production of single-layer clear lacquer or color and / or effect lacquer layers (top lacquer layers) on said substrates.
  • the second method according to the invention is particularly suitable for the production of a multi-layer coloring and / or effect coating by the wet-on-wet method.
  • the wet-on-wet process for the production of multilayer topcoat coats is described, for example, in US Pat. DE-A-39 03 804, EP-A-0 320 552, DE-A-36 28 124, US-A-4,719,132, EP-A-0 297 576, EP-A-0 069 936, EP-A- 0 089 497, EP-A-0 195 931, EP-A-0228 003, EP-A-0 038 127 and DE-A-28 18 100.
  • a waterborne basecoat is applied in a process step (1) to the surface of one of the substrates described above and flashed off and dried (process step LT), but is not cured.
  • a clear lacquer layer is applied to the surface of the water-based lacquer layer.
  • the water-based lacquer layer and the clear lacquer layer are cured physically or thermally and optionally with actinic light (wet-on-wet method).
  • the physically curing coating materials of DE-A-44 14 032, which contain no crosslinking agents (B) can also be used in the context of the second method according to the invention. This is a particular advantage of the second method according to the invention, since it can be used in particular for the gentle coating of thermally sensitive substrates such as plastics.
  • the stoving temperature depends primarily on whether the coating materials used in each case are one-component (1K) or two-component (2K) or multi-component (3K, 4K) systems.
  • the baking temperatures are generally above 120 ° C.
  • the baking temperatures are usually below 100 ° C, especially below 80 ° C .
  • a further clear lacquer layer can be applied to the surface of the clear lacquer layer, which differs materially from the first clear lacquer layer. This is then cured in a process step (VI).
  • the methods described above are used for curing. This variant of the method according to the invention is particularly useful in automotive refinishing.
  • the clear lacquer layer applied in process step (LTI) can only be dried in process step (IV).
  • the further clear lacquer layer is then applied wet-on-wet in process step (V), after which the lacquer layers are cured together (extended wet-on-wet method).
  • At least one of the lacquer layers described above is manufactured from a coating material according to the invention.
  • the water-based lacquer layer and / or the clear lacquer layer or at least one of the clear lacquer layers is or are produced from a coating material according to the invention.
  • a further particular advantage of the coating material according to the invention and of the method according to the invention is that all conventional and known clear lacquers can be combined with the water-based lacquer layer according to the invention in the context of the second method according to the invention.
  • Suitable known one-component (IC), two-component (2-component) or multi-component (3-component, 4-component) clearcoats are from the patents DE-A-42 04 518, US-A-5,474,811, US-A-5,356,669, US-A-5,605,965, WO 94/10211, WO 94/10212, WO 94/10213, EP-A-0 594 068, EP-A-0 594 071, EP-A-0 594 142, EP-A-0 604992, WO 94/22969, EP-A-0 596460 or WO 92/22615.
  • One-component (IC) clearcoats are known to contain binders and crosslinking agents containing hydroxyl groups, such as blocked polyisocyanates, tris (alkoxycarbonylamino) triazines and / or aminoplast resins.
  • binders and crosslinking agents containing hydroxyl groups such as blocked polyisocyanates, tris (alkoxycarbonylamino) triazines and / or aminoplast resins.
  • they contain, as binders, polymers with pendant carbamate and / or AUophanatrappen and carbamate and / or ⁇ Uophanat modified aminoplast resins as crosslinking agents (cf.
  • Two-component (2K) or multicomponent (3K, 4K) clearcoats contain, as is known, essential components of hydroxyl group-containing binders and polyisocyanates as crosslinking agents, which are stored separately until they are used.
  • powder clearcoats are known, for example, from German patent specification DE-A-42 22 194 or the product information from BASF Lacke + Weg AG, "Powder coatings", 1990.
  • Powder clear lacquers contain, as is known, essential components of binders containing epoxy groups and polycarboxylic acids as crosslinking agents.
  • powder slurry clearcoats are known, for example, from US Pat. No. 4,268,542 and German patent applications DE-A-195 18 392.4 and DE-A-196 13 547 or are described in the unpublished German patent application DE-A-198 14471.7.
  • Powder slurry clearcoats are known to contain powder clearcoats dispersed in an aqueous medium.
  • UV-curable clearcoats are known, for example, from the patents EP-A-0 540 884, EP-A-0 568 967 or US-A-4,675, 234.
  • the coating materials can be applied by customary application methods, such as e.g. Spraying, knife coating, brushing, pouring, dipping or rolling can be applied to the substrates.
  • spraying knife coating, brushing, pouring, dipping or rolling
  • the usual and known methods such as heating in a forced air oven, irradiation with IR lamps and, if appropriate, with UV lamps can be used for curing.
  • the thickness of the individual layers can vary widely within the multi-layer coating system according to the invention. According to the invention, however, it is advantageous if the basecoat layer has a thickness of 5 to 25 ⁇ m, in particular 7 to 15 ⁇ m, and the one- or two-layer clearcoat layer has a total thickness of 15 to
  • the ratio of the layer thicknesses can vary widely, but it is also advantageous for economic reasons if the first clear lacquer layer is the thicker of the two layers. This clear coat can then, so to speak
  • the second clear lacquer layer with its other, optionally specially selected composition provides particularly desirable application properties.
  • the single-coat and multi-coat paint bars according to the invention have excellent optical, mechanical and chemical properties. So they are free from any surface defects such as shrinkage. As clear lacquer layers, they are of excellent transparency and scratch resistance. The etch resistance is excellent.
  • water-based lacquer layers As water-based lacquer layers, they have a particularly high covering power and excellent optical effects, in particular MetaUic effects.
  • the very special advantage of the multi-layer coating line according to the invention is that the profile of properties of its surface varies in a particularly ready manner and can therefore be easily and precisely adapted to the most varied of requirements.
  • the coating materials according to the invention and the methods according to the invention are therefore outstandingly suitable for the production of single-layer or multi-layer clear or pigmented coating compositions for automotive repair painting, industrial coating, including coil coating and container coating, plastic coating and furniture coating.
  • the resulting dispersion had a solids content of 27.8% by weight and a pH of 7.82. It was homogeneous and free of specks and threads.
  • the methyl ethyl ketone was removed to a residual content of less than 0.5% by weight by vacuum distillation.
  • the resulting dispersion was adjusted to a solids content of 30.3% by weight with deionized water.
  • the pH was 7.73. Even after long storage, it was free of specks and threads.
  • the dispersion was used in place of the polyurethane dispersions of Examples 1.1, 1.2 and 1.3 of EP-A-0 574 417 for the production of water-based paints and multi-layer paint coats according to Examples 2, 3 and 4 of EP-A-0 574417.
  • the resulting waterborne basecoats proved to be extraordinarily stable in storage and easy to apply.
  • the corresponding multi-layer painting rods had a high brilliance combined with an excellent MetaUic effect.
  • Example 1 was repeated, except that instead of bis (4-isocyanatocyclohexyl) methane having a trans / trans content of 17% by weight, based on the diisocyanate, one of bis (4-isocyanatocyclohexyl) methane having a trans / trans content of 32 wt .-%, based on the diisocyanate, was used.
  • the resulting dispersion had specks and threads, especially after prolonged storage.
  • the waterborne basecoats produced with it were found to be less stable in storage and less easy to apply than the waterborne basecoats of Example 1. Accordingly, the multicoat paint systems produced with them were also inferior to those of Example 1.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Manufacturing & Machinery (AREA)
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Abstract

L'invention concerne un matériau de revêtement aqueux durcissable par rayonnement thermique et/ou actinique, qui contient : A) comme liant, au moins un polyuréthane saturé, insaturé et/ou greffé avec des composés insaturé par oléfine, stabilisé par voie ionique et/ou non ionique, à base de bis(4-isocyanatocyclohéxyle)méthane à teneur trans/trans allant jusqu'à 30 % en poids par rapport au diisocyanate, et B) au moins un agent de réticulation.
EP00916960A 1999-04-01 2000-03-16 Materiau de revetement aqueux durcissable par rayonnement thermique et/ou actinique et son utilisation Withdrawn EP1171501A1 (fr)

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DE19914896 1999-04-01
DE19914896A DE19914896A1 (de) 1999-04-01 1999-04-01 Thermisch und/oder mit aktinischer Strahlung härtbarer wäßriger Beschichtungsstoff und seine Verwendung
PCT/EP2000/002340 WO2000059978A1 (fr) 1999-04-01 2000-03-16 Materiau de revetement aqueux durcissable par rayonnement thermique et/ou actinique et son utilisation

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