WO2000073395A1 - Thermisch und mit aktinischer strahlung härtbarer beschichtungsstoff und seine verwendung - Google Patents
Thermisch und mit aktinischer strahlung härtbarer beschichtungsstoff und seine verwendung Download PDFInfo
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- WO2000073395A1 WO2000073395A1 PCT/EP2000/004807 EP0004807W WO0073395A1 WO 2000073395 A1 WO2000073395 A1 WO 2000073395A1 EP 0004807 W EP0004807 W EP 0004807W WO 0073395 A1 WO0073395 A1 WO 0073395A1
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- coating material
- material according
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- actinic radiation
- thermally
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Classifications
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- 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
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31533—Of polythioether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
- Y10T428/31794—Of cross-linked polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
Definitions
- the present invention relates to a new coating material which is curable thermally and with actinic radiation.
- the present invention relates to the use of the new coating material for the production of new clearcoat and coloring and / or effect-giving multi-layer coatings for automotive initial and refinishing, industrial painting, including coil coating and container coating, plastic coating and furniture coating.
- the clear coat can be used as the sole coat of paint or form the top layer of a multi-layer top coat.
- IC One-component
- 2K two-component
- 3K, 4K multicomponent clearcoats
- Powder clearcoats are known, for example, from German patent DE 4222 194 AI or the product information from the company BASF Lacke + Wegner AG, "Powder Coatings", 1990.
- a powder coating which is curable thermally and with actinic radiation is known from the European patent EP 0 844 286 AI. It contains an unsaturated binder and a second resin that can be copolymerized with it, as well as a photoinitiator and a thermal initiator, and is thus curable thermally and with actinic radiation.
- this dual-cure powder coating is used as a pigmented topcoat, which is thermally cured on the surface with UV light and in the areas close to the substrate. It is not clear from the patent whether this known powder coating is also suitable for the production of clear coating layers, particularly in multi-layer coatings.
- Powder slurry coatings are powder coatings in the form of aqueous dispersions. Such slurries are described, for example, in US Pat. No. 4,268,542 and German patent applications DE 195 18 392.4 AI and DE 196 13 547 AI and the unpublished German patent application DE 198 14 471.7 AI.
- UV-curable clearcoats are known, for example, from the patents EP 0 540 884 AI, EP 0 568 967 AI or US 4,675,234.
- EP 0 568 967 A1 discloses a process for the production of multi-layer coatings, in which a thermally curable clear coat is applied to a pigmented base coat by the wet-on-wet process, after which the two layers are cured together in the heat. Then at least one further clear lacquer layer based on coating materials curable with actinic radiation is applied to the hardened clear lacquer layer and thermally hardened with actinic radiation or with actinic radiation.
- This process provides clear lacquer coatings of high chemical resistance and optical quality. However, the scratch resistance is not satisfactory.
- EP 0 568 967 A1 also discloses a process in which a coating material curable with actinic radiation is applied to the pigmented basecoat layer and cured. Another layer of the same coating material is then applied and hardened with actinic radiation. The result is a high-gloss surface without any noticeable structure, but the clear coat in question yellows. The scratch resistance also leaves something to be desired.
- (al2) at least one functional group which can undergo thermal crosslinking reactions with the hydroxyl and / or thiol groups (a21) in component (a2),
- (a2) at least one branched, cyclic and / or acyclic C 9 -C 16 alkane which is functionalized with at least two hydroxyl or thiol groups or at least one hydroxyl and at least one thiol group (a21).
- coating material curable thermally and with actinic radiation
- the branched, cyclic and / or acyclic C -Ci6 alkanes (a2) to be used according to the invention which are functionalized with at least two hydroxyl or thiol groups or at least one hydroxyl and at least one thiol group, for the sake of brevity as functionalized alkanes (a2) ".
- the new clearcoats and color and / or effect multi-layer coatings were found, which can be produced with the aid of the coating material of the invention.
- thermal hardening means the heat-initiated hardening of a lacquer layer made 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. Are the crosslinking agents already in the binders 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 free-radical or cationic photoinitiators and, according to its mechanism, is free-radical or cationic photopolymerization.
- the use of the coating material of the invention results in clear coats and multi-coat coats according to the invention which, when baked, show no decomposition of constituents and which are not only scratch-resistant, weather-resistant, resistant to yellowing, hard, flexible and free from surface defects, are high on all substrates Have adhesion and can be produced in the high layer thickness necessary for an excellent overall optical impression, but also have an extraordinarily high reflow.
- the coating material of the invention contains at least one component (al) with at least two functional groups (al l), which are used for crosslinking with actinic radiation.
- suitable functional groups (A1) are epoxy groups or olefinically unsaturated double bonds, as are present in vinyl, allyl, cinnamoyl, methacrylic or acrylic groups, in particular methacrylic or acrylic groups.
- the epoxy groups are used for cationic photopolymerization, whereas the olefinically unsaturated double bonds are mainly used for radical photopolymerization.
- the constituent (a1) can contain epoxy groups and olefinic double bonds, so that it can be subjected to crosslinking with actinic radiation by both mechanisms. However, it is advantageous to use only olefinically unsaturated double bonds of the type mentioned as functional groups (al 1).
- constituent (al) to be used according to the invention contains at least one, preferably at least two functional groups (al2) which correspond to the hydroxyl and / or thiol groups (a21) below Component (a2) described can undergo thermal crosslinking reactions.
- radicals R mean aliphatic, cycloaliphatic, aromatic, aliphatic-cycloaliphatic, aliphatic-aromatic or cycloaliphatic-aromatic organic groups which are optionally substituted and / or contain heteroatoms such as oxygen, nitrogen and / or sulfur.
- groups (a21) is based on the one hand on the fact that they do not undergo any undesirable reactions initiated by actinic radiation or on the other hand they must not interfere with or inhibit curing with actinic radiation, and on the other hand in which temperature range the thermal curing should take place.
- a temperature range which does not exceed 100 ° C., in particular 80 ° C.
- isocyanate groups (al2) have proven to be advantageous, which is why they are preferably used according to the invention.
- the particularly advantageous constituent (al) is an oligomeric or polymeric compound curable with actinic radiation or thermally curable, which has at least one, preferably at least two and in particular at least three isocyanate group (s) (al2) and at least two and in particular at least three Contains (meth) acrylic groups (al 1).
- an oligomeric compound is understood to mean a compound which generally has an average of 2 to 15 repeating basic structures or monomer units.
- a polymeric compound is understood to mean a compound which generally has on average at least 10 repeating basic structures or monomer units. Compounds of this type are also referred to by experts as binders or resins.
- a low-molecular compound is understood to mean a compound which is essentially derived only from a basic structure or a monomer unit.
- Compounds of this type are generally referred to by the experts as reactive thinners.
- the polymers or oligomers used as component (a1) usually have a number average molecular weight of 500 to 50,000, preferably 1,000 to 5,000. They preferably have a double bond equivalent weight of 400 to 2,000, particularly preferably 500 to 900. In addition, they preferably have a viscosity of 250 to 11,000 mPas at 23 ° C. They are preferably used in an amount of 5 to 90% by weight, particularly preferably 10 to 80% by weight and in particular 15 to 70% by weight, in each case based on the total amount of the coating material.
- suitable constituents (al) come from the oligomer and / or polymer classes of the linear or branched, in particular the branched (mem) acyl-functional (meth) acrylic copolymers, polyether acrylates,
- Polyester acrylates unsaturated polyesters, epoxy acrylates, urethane acrylates, amino acrylates, melamine acrylates, silicone acrylates and the corresponding methacrylates. It is preferred to use binders (A1) which are free from aromatic structural units.
- Urethane (meth) acrylates are preferred and / or polyester (meth) acrylates, particularly preferably urethane (meth) acrylates, very particularly preferably aliphatic urethane (meth) acrylates and in particular urethane acrylates.
- the urethane (meth) acrylates (al) are obtained by reacting a diisocyanate and or polyisocyanate, in particular a polyisocyanate, with a chain extender from the group of the diols / polyols and / or diamines / polyamines and or dithiols / polythiols and / or alkanolamines and subsequent Reaction of part of the free isocyanate groups with at least one hydroxyalkyl (meth) acrylate, especially a hydroxyalkyl acrylate.
- hydroxyalkyl esters of other ethylenically unsaturated carboxylic acids such as ethacrylic acid or itaconic acid can also be used.
- chain extender di- and / or polyisocyanate and hydroxyalkyl ester are preferably chosen so that
- the equivalent ratio of the NCO groups to the reactive groups of the chain extender is between 20: 1 and 2: 1, preferably between 15: 1 and 5: 1, and
- the OH groups of the hydroxyalkyl esters of the ethylenically unsaturated carboxylic acids are present in substoichiometric amounts with respect to the free isocyanate groups of the prepolymer of isocyanate and chain extender.
- the urethane (meth) acrylates (al) by first reacting some of the isocyanate groups of a polyisocyanate with at least one hydroxyalkyl ester and then reacting some of the remaining isocyanate groups with a chain extender.
- the amounts of chain extender, isocyanate and hydroxyalkyl ester are chosen so that the equivalent ratio of the NCO groups to the reactive groups of the chain extender is between 20: 1 and 2: 1, preferably between 15: 1 and 5: 1 and the equivalent ratio of the remaining NCO groups to the OH groups of the hydroxyalkyl ester is more than 1.
- the urethane (meth) acrylate (al) contains on average at least one, preferably at least two, isocyanate group (s) (al2). Particular advantages result if an average of more than two, very particularly preferably more than three, isocyanate groups (al2) are present.
- the number of isocyanate groups (al2) per need not exceed six on average in order to achieve the advantages according to the invention. In special cases, however, more than six isocyanate groups (al2) per urethane (meth) acrylate (al) have proven to be advantageous.
- component (al) in particular urethane (meth) acrylate (al), has an isocyanate group (al2) content of 7 to 20% by weight, particularly preferably 8 to 18% by weight and in particular 9 up to 16% by weight, based in each case on the component (al).
- Suitable di- and / or polyisocyanates are the following in the
- Crosslinking agent (a7) described.
- component (al) in particular urethane (meth) acrylate (al)
- polyisocyanurates containing isocyanurate groups are particularly advantageous and are therefore used with particular preference.
- the coating material of the invention further contains the functionalized alkanes (a2).
- the functionalized alkanes (a2) are derived from branched, cyclic or acyclic alkanes with 9 to 16 carbon atoms, which each form the basic structure.
- alkanes of this type with 9 carbon atoms examples include 2-methyloctane, 4-methyloctane, 2,3-dimethyl-heptane, 3,4-dimethyl-heptane, 2,6-dimethyl-heptane, 3,5-dimethyl-heptane, 2 -Methyl-4-ethylhexane or isopropylcyclohexane.
- alkanes of this type with 10 carbon atoms are 4-ethyloctane, 2,3,4,5-tetramethyl-hexane, 2,3-diethyl-hexane or l-methyl-2-n-propyl-cyclohexane.
- alkanes of this type with 11 carbon atoms examples include 2,4,5,6-tetramethyl-heptane or 3-methyl-6-ethyl-octane.
- alkanes of this type with 12 carbon atoms are 4-methyl-7-ethyl-nonane, 4,5-diethyl-octane, l'-ethyl-butyl-cyclohexane, 3,5-diethyl-octane or 2,4-diethyl- octane.
- alkanes of this type with 13 carbon atoms are 3,4-dimethyl-5-ethyl-nonane or 4,6-dimethyl-5-ethyl-nonane.
- An example of a suitable alkane of this type with 14 carbon atoms is 3,4-dimethyl-7-ethyl-decane.
- Examples of suitable alkanes of this type with 15 carbon atoms are 3,6-diethyl-undecane or 3,6-dimethyl-9-ethyl-undecane.
- alkanes of this type with 16 carbon atoms are 3,7-diethyl-dodecane or 4-ethyl-6-isopropyl-undecane.
- alkanes with 10 to 14 and in particular 12 carbon atoms are particularly advantageous and are therefore used with preference.
- the octane derivatives are particularly advantageous.
- the functionalized alkanes (a2) which are derived from these branched, cyclic or acyclic alkanes as basic structures, are liquid at room temperature. Either individual liquid .functionalized alkanes (a2) or liquid mixtures of these compounds can thus be used. This is particularly the case when functionalized alkanes (a2) are used which are solid as individual compounds due to their high number of carbon atoms in the alkane backbone. The person skilled in the art can therefore select the corresponding functionalized alkanes (a2) in a simple manner.
- the functionalized alkanes (a2) have a boiling point above 200, preferably 220 and in particular 240 ° C. In addition, they are said to have a low evaporation rate.
- the functionalized alkanes (a2) are acycic.
- the functionalized alkanes (a2) have primary and / or secondary hydroxyl and / or thiol groups.
- the coating materials of the invention it is advantageous if there are primary and secondary groups of this type in a connection.
- the functionalized alkanes (a2) are therefore polyols, polythiols or polyol-polythiols (a2), but in particular polyols (a2). These compounds can be used individually or together as mixtures. There are particular advantages if the polyols (a2) are diols and / or triols, but in particular diols. They are therefore used with particular preference.
- the functionalized alkanes (a2) described above are compounds known per se and can be prepared using customary and known synthetic methods of organic chemistry, such as base-catalyzed aldol condensation, or they are obtained as by-products of large-scale chemical syntheses, such as the preparation of 2-ethylhexanol.
- the functionalized alkanes (a2) are generally present in the coating materials of the invention in an amount of 5 to 60% by weight, based on the total amount of the coating material in question. Although they can be contained here in larger amounts, this is an advantageous range within which the advantages according to the invention are achieved safely and reliably. Within this range, that of 10 to 50% by weight is particularly advantageous because the coating materials according to the invention, which contain this amount of functionalized alkanes (a2), have a particularly advantageous profile of properties. All However, particular advantages result from the use of 15 to 40% by weight of functionalized alkanes (a2).
- the ratio of isocyanate groups (al2) to the isocyanate-reactive groups (a21) can vary widely in the coating material of the invention. It depends in particular on which technical effects are to be achieved with regard to the clear coating and multi-layer coating according to the invention. According to the invention, it is advantageous if the ratio (al2) / (a21) is between 2: 1 and 1: 2, particularly preferably 1.5: 1 and 1: 1.5.
- the coating material to be used according to the invention can contain at least one photoinitiator (a3). If the coating material or the clear lacquer layer is to be crosslinked with UV radiation, the use of a photoinitiator (a3) is generally necessary. If they are also used, they are preferably present in the coating material in proportions of 0.1 to 10% by weight, 1 to 8% by weight and in particular 2 to 6% by weight, in each case based on the total amount of the coating material .
- Suitable photoinitiators (a3) are those of the Norrish II type whose mechanism of action is based on an intramolecular variant of the hydrogen
- Benzoin ether or phosphine oxides There can also be, for example, those commercially available under the names Irgacure® 184, Irgacure® 1800 and Irgacure® 500 from the company
- Ciba Geigy Grenocure® MBF from Rann and Lucirin® TPO from BASF AG can be used.
- conventional sensitizers (a3) such as anthracene can be used in effective amounts.
- the coating material can contain at least one initiator of the thermal crosslinking (a4). From 80 to 120 ° C, these form radicals that start the crosslinking reaction. Examples of thermolabile radicals
- Initiators are organic peroxides, organic azo compounds or C-C-cleaving initiators such as dialkyl peroxides, peroxocarboxylic acids,
- C-C-cleaving initiators are particularly preferred, since during their thermal cleavage no gaseous decomposition products are formed which could lead to defects in the lacquer layer. If they are used, their amounts are generally between 0.1 and 10% by weight.
- % preferably 0.5 to 8% by weight and in particular 1 to 5% by weight, in each case based on the total amount of the coating material.
- the coating material can contain at least one reactive diluent (a5) curable with actinic radiation and / or thermally.
- thermally crosslinkable reactive diluents (a5) are oligomeric polyols which can be obtained from oligomeric intermediates which are obtained by metathesis reactions of acyclic monoolefins and cyclic monoolefins by hydroformylation and subsequent hydrogenation;
- suitable cyclic monoolefins are cyclobutene, cyclopentene, cyclohexene, cyclooctene, cycloheptene, norbones or 7-oxanorbones;
- suitable acyclic monoolefins are contained in hydrocarbon mixtures which are obtained by cracking in petroleum processing (C 5 cut );
- suitable oligomeric polyols to be used according to the invention have a hydroxyl number (OHZ) 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;
- 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. Vögtle, "Dendritic Molecules, Concepts, Syntheses, Perspectives", VCH, Weinheim, New York, 1996 , described.
- Suitable reactive diluents (a5) are polycarbonate diols, polyester polyols, poly (meth) acrylate diols or polyadducts containing hydroxyl groups.
- Suitable reactive solvents which can be used as reactive diluents (a5) are butyl glycol, 2-methoxypropanol, n-butanol, methoxybutanol, n-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol
- Trimethylolpropane, 2-hydroxypropionic acid ethyl ester or 3-methyl-3-methoxybutanol as well as derivatives based on propylene glycol, e.g. Called ethoxyethyl propionate, isopropoxypropanol or methoxypropylacetate.
- the reactive diluents (a5) which can be crosslinked with actinic radiation are, for example, (meth) acrylic acid and its esters, maleic acid and its esters or half esters, vinyl acetate, vinyl ether, vinyl ureas and the like. used.
- examples include alkylene glycol di (meth) acrylate, Polyethylene glycol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate,
- the two acrylate groups can be separated by a polyoxibutylene structure.
- Preferred reactive diluents (a5) are mono- and or diacrylates, such as e.g. Isobomylacrylate, hexanediol diacrylate, tripropylene glycol diacrylate, Laromer® 8887 from BASF AG xmd Actilane® 423 from Akcros Chemicals Ltd., GB. Isobomylacrylate, hexanediol diacrylate and tripropylene glycol diacrylate are particularly preferably used.
- the reactive diluents (a5) are used in an amount of preferably 2 to 70% by weight, particularly preferably 10 to 65% by weight and in particular 15 to 50% by weight, in each case based on the total amount of Coating material applied.
- the coating material can contain at least one customary and known paint additive (a6) in effective amounts, ie in amounts preferably up to 40% by weight, particularly preferably up to 30% by weight and in particular up to 20 wt .-%, each based on the total amount of the coating material.
- a6 customary and known paint additive
- UV absorber
- Light stabilizers such as HALS compounds, benzotriazoles or oxalanilides
- Crosslinking catalysts such as dibutyltin dilaurate or lithium decanoate
- Emulsifiers in particular nonionic emulsifiers such as alkoxylated 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 alkoxylated alkanols and polyols, phenols and alkylphenols;
- nonionic emulsifiers such as alkoxylated 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 alkoxylated alkanols and polyols, phenols and alkylphenols;
- wetting agents such as siloxanes, fluorine-containing compounds,
- - film-forming aids such as cellulose derivatives
- the coating material can contain at least one thermally curable component (a7) in minor amounts.
- “minor amounts” are to be understood as amounts which do not adversely affect the dual cure properties of the coating material, but rather vary and supplement in an advantageous manner. If they are used, their proportions of the coating material should generally be 40 % By weight, preferably 35% by weight and in particular 30% by weight.
- suitable constituents (a7) are the binders and crosslinking agents known from the thermally curable coating materials.
- suitable binders (a7) are linear and or branched and / or block-like, comb-like and / or randomly constructed poly (meth) acrylates or acrylate copolymers, polyesters, alkyds, aminoplast resins, polyurethanes, polylactones, polycarbonates, polyethers, epoxy-hare-amine adducts, (Meth) acrylate diols, partially saponified polyvinyl esters or polyureas, of which the acrylate copolymers, the polyesters, the polyurethanes, the polyethers and the epoxy-hara-amine adducts are advantageous.
- Suitable binders (a7) are, for example, under the trade names Desmophen® 650, 2089, 1100, 670, 1200 or 2017 from Bayer, under the trade names Priplas or Pripol® from Uniqema, under the trade names Cempol® polyester or polyacrylate-polyol distributed by the CCP, under the trade names Crodapol® 0-85 or 0-86 by the company Croda or under the trade name Formrez® ER417 by the company Witco.
- Suitable crosslinking agents (a7) are blocked di- and or polyisocyanates.
- Suitable di- and / or polyisocyanates for the preparation of the blocked derivatives (a7) are organic polyisocyanates, in particular so-called lacquer polyisocyanates, with aliphatic, cycloaliphatic, araliphatic and / or aromatically bound, free isocyanate groups. To be favoured
- Polyisocyanates with 2 to 5 isocyanate groups per molecule and with viscosities of 100 to 10,000, preferably 100 to 5000 and in particular 1000 to 2000 mPas (at 23 ° C.) are used.
- small amounts of organic solvent, preferably 1 to 25% by weight, based on pure polyisocyanate, can also be added to the polyisocyanates in order to improve the incorporability of the isocyanate and, if appropriate, the viscosity of the polyisocyanate to one
- Solvents suitable as additives are the polyisocyanates, for example
- Polyisocyanates can be modified hydrophilically or hydrophobically in the usual and known manner.
- polystyrene foams examples include polyurethane prepolymers containing isocyanate groups, which can be prepared by reacting polyols with an excess of polyisocyanates and which are preferably low-viscosity.
- polyisocyanates are polyisocyanates containing isocyanurate, biuret, allophanate, iminooxadiazindone, urethane, urea and / or uretdione groups.
- Polyisocyanates containing urethane groups are obtained, for example, by reacting part of the isocyanate groups with polyols, e.g. Trimethylolpropane xmd glycerin, obtained.
- Aliphatic or cycloaliphatic polyisocyanates, in particular hexamethylene diisocyanate are preferably dimerized and trimerized
- Hexamethylene diisocyanate isophorone diisocyanate, 2-isocyanatopropylcyclohexyl isocyanate, dicyclohexyl methane-2,4'-diisocyanate,
- the polyisocyanate component can also consist of any mixtures of the free polyisocyanates mentioned by way of example.
- blocking agents examples include the blocking agents known from US Pat. No. 4,444,954, such as
- phenols such as phenol, cresol, xylenol, nitrophenol, chlorophenol,
- lactams such as ⁇ -caprolactam, ⁇ -valerolactam, ⁇ -butyrolactam or ß-propiolactam
- active methylenic compounds such as diethyl malonate, dimethyl malonate, ethyl or methyl acetoacetate or acetylacetone;
- alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-amyl alcohol, t-amyl alcohol, laxyl alcohol,
- mercaptans such as butyl mercaptan, hexyl mercaptan, t-butyl mercaptan, t-dodecyl mercaptan, 2-mercaptobenzothiazole, thiophenol,
- Methylthiophenol or ethylthiophenol vi) 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-phenylxylidine, carbazole, aniline, naphthylamine, butylamine, dibutylamine or butylphenylamine;
- imidazoles such as imidazole or 2-ethylimidazole
- ureas such as urea, thiourea, ethylene urea, ethylene thiourea or 1,3-diphenyl urea
- carbamates such as phenyl N-phenylcarbamate or 2-oxazolidone
- 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
- 5 xv) hydroxamic acid esters such as benzyl methacrylohydroxamate (BMH) or allyl methacrylohydroxamate
- BMH benzyl methacrylohydroxamate
- allyl methacrylohydroxamate or
- Tris (alkoxycarbonylamino) triazines of the general formula 5 can also be used as crosslinking agents (a7)
- tris (alkoxycarbonylammo) triazines (a7) are described in the patents US 4,939,213, US 5,084,541 or EP 0 624 577 AI.
- the tris (methoxy-, tris (butoxy- and / or tris (2-ethy_hexoxycarbonylar ___ ino) triazines are used.
- methyl-butyl mixed esters the butyl-2-ethylhexyl mixed esters xmd 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.
- aminoplast resins for example melamine resins
- Crosslinking agent (a7) can be used. Anything can be done for transparent
- Topcoats or clearcoats suitable aminoplast resin or a mixture of such aminoplast resins can be used.
- the usual ones come xmd known aminoplast resins 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 4,710,542 and EP 0 245 700 B1 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 Seiles, 1991, Volume 13, Pages 193 to 207.
- the aminoplast resins can also be used as binders (A1) in the base color (AI).
- crosslinking agents (a7) are beta-hydroxyalkylamides such as N, N, N ', N'-tetrakis (2-hydroxyethyl) adipamide or N, N, N, N'-tetrakis (2-hydroxypropyl) adipamide.
- suitable crosslinking agents (a7) are siloxanes, in particular siloxanes with at least one trialkoxy or dialkoxysilane group.
- crosslinking agents (a7) are polyanhydrides, in particular polysuccinic anhydride.
- the coating material of the invention may contain organic solvents (a8) which do not react with isocyanate groups.
- organic solvents of this type are esters, ketones, keto esters, glycol ethers such as ethylene, propylene or butylene glycol ethers, glycol esters such as ethylene, propylene or butylene glycol esters or glycol ether esters such as ethoxyethyl propionate and isopropoxypropanol.
- aliphatic and aromatic solvents such as dipentene, xylene or Shellsol R.
- the coating material to be used according to the invention can be in various forms. Thus, with a corresponding choice of its constituents described above, it can be in the form of a liquid coating substance which is essentially free of organic solvents. However, the coating material can be a solution or dispersion of the components described above in organic solvents (a8). It is a further advantage of the coating material according to the invention that solids contents of up to more than 80% by weight, based on the coating material, can be adjusted.
- the coating material can be a powder clearcoat if the components described above are selected accordingly.
- the component (a1) is advantageously microencapsulated. This powder clearcoat can then optionally be dispersed in water, resulting in a powder slurry clearcoat.
- the coating material according to the invention is advantageously a two- or multi-component system, in which at least the component (a1) is stored separately from the other components and is added to them only shortly before use.
- the coating substance according to the invention can also be aqueous, the constituent (a1) preferably being present in a component containing a solvent (a8).
- the coating material of the invention is used to produce the clearcoats and multi-layer coatings of the invention on primed or unprimed substrates.
- Suitable substrates here are all surfaces to be painted, which are accessible for a combined hardening using heat xmd actinic jet xmg.
- the coating material of the invention is also for applications Suitable outside of automotive painting, especially for painting furniture and industrial painting, including coil coating and container coating. As part of industrial painting, it is suitable for painting practically all parts for private or industrial use, such as radiators, household appliances, small parts made of metal, hubcaps or rims.
- plastics such as ABS, AMMA, ASA, CA, CAB, EP, UF, CF, MF, MPF, PF, PAN, PA, PE, HDPE, LDPE, LLDPE, UHMWPE, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (short names according to DIN 7728T1) can be painted.
- the plastics to be painted can of course also be polymer blends, modified plastics or fiber-reinforced plastics.
- plastics typically used in vehicle construction in particular motor vehicle construction.
- these can be subjected to a pretreatment, such as with a plasma or with flame treatment, in a known manner before the coating.
- one or more clear lacquer layer (s) can be applied as part of the painting method according to the invention. Become several
- Applied clear lacquer layers coating materials of different material composition according to the invention can be used. In the vast majority of cases, however, the desired property profile of the clearcoats and multi-coat coatings according to the invention is achieved with a clearcoat layer.
- the clear lacquer layer was applied in a wet layer thickness that after the
- Curing in the finished clearcoats and multi-layer coatings according to the invention a dry layer thickness of the seal of 10 to 100, preferably 15 to 75, particularly preferably 20 to 55 ⁇ md, in particular 20 to 35 ⁇ m, results.
- the application of the coating material according to the invention for the purpose of producing the clear lacquer layer can be carried out by all customary application methods, such as e.g. Spraying, knife coating, painting, pouring, dipping or rolling.
- Spray application methods are preferably used, such as, for example, compressed air spraying, airless spraying, high rotation, electrostatic spray application (ESTA), optionally combined with hot spray application such as, for example, hot-air spraying.
- the application can be carried out at temperatures of max. 70 to 80.degree. C. are carried out so that suitable application viscosities are achieved without the change in or damage to the coating material and its overspray, which may need to be reprocessed, occurring under the briefly acting thermal load.
- hot spraying can be designed in such a way that the coating material is heated only very briefly in or shortly before the spray nozzle.
- the spray booth used for the application can be operated, for example, with a circulation that can be tempered, if necessary, which is equipped with a suitable absorption medium for the overspray, e.g. B. the coating material according to the invention itself is operated.
- the application is preferably carried out when illuminated with visible light of a wavelength of more than 550 ⁇ m or in the absence of light. This avoids material changes or damage to the coating material and the overspray.
- the application methods described above can also be used in the production of the basecoat of the multi-layer coatings according to the invention in the context of the painting method according to the invention.
- the clear lacquer layer is cured thermally and with actinic radiation after its application.
- the hardening can take place after a certain rest period. It can have a duration of 30 s to 2 h, preferably 1 min to 1 h and in particular 1 min to 30 min.
- the idle time is used, for example, for the course and degassing of the clear lacquer layer or for the evaporation of volatile constituents such as solvents, water or carbon dioxide if the coating material has been applied with supercritical carbon dioxide as a solvent.
- the rest period can be supported and / or shortened by using elevated temperatures up to 80 ° C, provided that there is no damage or changes to the clear coat, such as premature crosslinking.
- curing takes place with actinic radiation with UV radiation or electron beams. If necessary, it can be carried out or supplemented with actinic radiation from other radiation sources.
- actinic radiation with UV radiation or electron beams.
- it can be carried out or supplemented with actinic radiation from other radiation sources.
- work is preferably carried out under an inert gas atmosphere. This can be ensured, for example, by supplying carbon dioxide and / or nitrogen directly to the surface of the clear lacquer layer.
- the usual xmd known radiation sources and optical auxiliary measures are used for hardening with actinic radiation.
- suitable radiation sources are high-pressure or low-pressure mercury vapor lamps, which may be doped with lead in order to open a radiation window up to 385 ⁇ m, or electron beam sources.
- Their arrangement is known in principle and can be adapted to the conditions of the workpiece and the process parameters. For complicated shaped workpieces like those for If car bodies are intended, the areas (shadow areas) which are not directly accessible to the beam, such as cavities, folds and other undercuts due to construction, with point, small area or Rxmdum radiators combined with an automatic movement device for irradiating cavities or edges can be (partially) cured.
- the substrate When curing the layer (s) made of the coating material according to the invention with actinic radiation, the substrate can rest or be guided past the radiation source at a suitable speed. If the substrate is moved, a advance speed in the range from 1 to 10 m / min, particularly preferably 2 to 8 m / min ⁇ md, in particular 3 to 6 m / min, has proven to be advantageous.
- the UV lamps preferably have 100 to 200 w / cm, particularly preferably 120 to 190 w / cm and in particular 140 to 180 w / cm.
- the curing can take place in stages, i. H. by multiple exposure or exposure to actinic radiation. This can also take place alternately, i. that is, alternately cured with UV beam xmg and electron beam xmg.
- the thermal curing also has no special features in terms of method, but is carried out according to the customary and known methods such as heating in a forced air oven or irradiation with IR lamps. As with the hardening with actinic radiation, thermal curing can also be carried out in stages. The thermal curing is advantageously carried out at a temperature of 50 to 100 ° C., particularly preferably 80 to 100 ° C. and in particular 90 to 100 ° C. for a time of 1 minute to 2 hours, particularly preferably 2 minutes to 1 hour and in particular 3 to 30 min. If substrates are used that are thermally highly resilient, the thermal crosslinking can also be carried out at temperatures above 100 ° C. In general, it is advisable not to exceed temperatures of 180 ° C., preferably 160 ° C. and in particular 140 ° C.
- Thermal curing and curing with actinic radiation are used together. These methods can be used simultaneously or alternately. If the two curing methods are used alternately, thermal curing can be started, for example, and curing with actinic radiation can be ended. In other cases, it may prove advantageous to start and end the curing with actinic radiation.
- the person skilled in the art can determine the hardening method which is most advantageous for the individual case on the basis of his general specialist knowledge, if necessary with the aid of simple preliminary tests. In the vast majority of cases, it proves advantageous to first carry out the curing with actinic radiation and then to carry out the thermal curing.
- the clearcoat materials according to the invention can also be part of the multi-layer paint systems according to the invention.
- the coating material according to the invention is not applied to the primed or unprimed substrates, but rather to at least one color and / or effect basecoat layer made of a pigmented coating material that is curable thermally and optionally with actinic radiation.
- basecoats in particular waterborne basecoats, are suitable as coating material for the production of the basecoat film.
- Suitable waterborne basecoats are from the patents EP 0 089 497 AI, EP 0 256 540 AI, EP 0 260 447 AI, EP 0 297 576 AI, WO 96/12747, EP 0 523 610 AI, EP 0 228 003 AI, EP 0 397 806 AI, EP 0 574 417 AI, EP 0 531 510 AI, EP 0 581 211 AI, EP 0 708 788 AI, EP 0 593 454 AI, DE 43 28 092 AI, EP 0 299 148 AI, EP 0 394 737 AI, EP 0 590 484 AI, EP 0 234 362 AI, EP 0 234 361 AI, EP 0 543 817 AI, WO 95/14721, EP 0 521 928 AI, EP 0 522 420 AI, EP 0 522 419 AI, EP 0 649 865 AI, EP 0 536 712 AI, EP 0 596 460 AI, EP 0
- the clearcoats and multicoat paint systems of the invention have good scratch resistance, intercoat adhesion, weather stability and chemical stability, an excellent optical property profile and an extraordinarily high reflow.
- a wet-in-wet coating xmd curable with actinic radiation was applied to the basecoat film in a wet film thickness that resulted in a film thickness of 35 ⁇ m after the clear coat was completely cured.
- the coating material consisted of 136 parts by weight of an aliphatic urethane acrylate based on the isocyanurate of hexamethylene diisocyanate, which contained 12.5% by weight of isocyanate groups and had an average functionality with respect to the acrylate groups of 3.5, 47.9 parts by weight of 2,4-diethyloctanediol.
- the resulting basecoat and clearcoat layer were cured with UV radiation (3,000 mJ / cm 2 ) after a rest period of 6 min at 50 ° C. xmd then baked at 160 ° C. for 45 min.
- the adhesion of the multicoat paint system of the invention was determined after storage for 24 hours at room temperature after the cross-cut test according to DIN 53151 (2 mm) [rating 0 to 5]. There was no release: Note GT0.
- the scratch resistance of the multilayer coating on the test panels was determined after two weeks of storage at room temperature with the aid of the method shown in FIG. 2 on page 28 of the article by P. Betz and A. Bartelt, Progress in Organic Coatings, 22 (1 93), pages 27-37, BASF brush tests described, but modified with regard to the weight used (2000 g instead of the 280 g mentioned there), were assessed as follows:
- the paint surface was damaged with a sieve fabric that was loaded with a mass.
- the screen fabric and the varnish surface were wetted liberally with a detergent solution.
- the test panel was moved back and forth under the screen fabric in a lifting motion by means of a motor drive.
- test specimen was eraser covered with nylon sieve mesh (No. 11, 31 ⁇ m mesh size, Tg 50 ° C.) (4.5 ⁇ 2.0 cm, wide side perpendicular to the direction of scratching).
- the coating weight was 2000 g.
- the multi-layer coating according to the invention corresponded to the multi-layer coatings which were produced with the aid of conventional and known two-component (2K) clearcoats.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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DE50003129T DE50003129D1 (de) | 1999-05-29 | 2000-05-26 | Thermisch und mit aktinischer strahlung härtbarer beschichtungsstoff und seine verwendung |
BR0011059A BR0011059A (pt) | 1999-05-29 | 2000-05-26 | Material de revestimento endurecìvel termicamente e com radiação actìnica e sua utilização |
JP2001500714A JP2003501512A (ja) | 1999-05-29 | 2000-05-26 | 熱硬化可能および化学線で硬化可能な被覆材料ならびにその使用 |
US09/926,532 US6716891B1 (en) | 1999-05-29 | 2000-05-26 | Coating material that can be cured thermally or by actinic radiation, and its use |
EP20000929556 EP1190004B1 (de) | 1999-05-29 | 2000-05-26 | Thermisch und mit aktinischer strahlung härtbarer beschichtungsstoff und seine verwendung |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19924674A DE19924674C2 (de) | 1999-05-29 | 1999-05-29 | Thermisch und mit aktinischer Strahlung härtbarer Beschichtungsstoff und seine Verwendung |
DE19924674.2 | 1999-05-29 |
Publications (1)
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WO2000073395A1 true WO2000073395A1 (de) | 2000-12-07 |
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ID=7909602
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PCT/EP2000/004807 WO2000073395A1 (de) | 1999-05-29 | 2000-05-26 | Thermisch und mit aktinischer strahlung härtbarer beschichtungsstoff und seine verwendung |
Country Status (7)
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US (1) | US6716891B1 (de) |
EP (1) | EP1190004B1 (de) |
JP (1) | JP2003501512A (de) |
BR (1) | BR0011059A (de) |
DE (2) | DE19924674C2 (de) |
ES (1) | ES2204596T3 (de) |
WO (1) | WO2000073395A1 (de) |
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-
2000
- 2000-05-26 US US09/926,532 patent/US6716891B1/en not_active Expired - Fee Related
- 2000-05-26 EP EP20000929556 patent/EP1190004B1/de not_active Expired - Lifetime
- 2000-05-26 WO PCT/EP2000/004807 patent/WO2000073395A1/de active IP Right Grant
- 2000-05-26 JP JP2001500714A patent/JP2003501512A/ja active Pending
- 2000-05-26 ES ES00929556T patent/ES2204596T3/es not_active Expired - Lifetime
- 2000-05-26 BR BR0011059A patent/BR0011059A/pt not_active IP Right Cessation
- 2000-05-26 DE DE50003129T patent/DE50003129D1/de not_active Expired - Fee Related
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EP0540884A1 (de) * | 1991-10-08 | 1993-05-12 | Herberts Gesellschaft mit beschränkter Haftung | Verfahren zur Herstellung von Mehrschichtlackierungen unter Verwendung von radikalisch und/oder kationisch polymerisierbaren Klarlacken |
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Cited By (8)
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US7312255B2 (en) * | 2001-03-05 | 2007-12-25 | Chemetall Gmbh | Water-based coating mixture, method for application of corrosion protection layer with said mixture, substrates coated thus and use thereof |
US6954680B2 (en) | 2001-07-13 | 2005-10-11 | Siemens Aktiengesellschaft | Method and system for the electronic provision of services for machines via a data communication link |
US7098257B2 (en) * | 2001-08-16 | 2006-08-29 | Heinz-Peter Rink | Coating materials that can be cured thermally and by actinic radiation, and the use thereof |
US7713445B2 (en) | 2002-04-20 | 2010-05-11 | Chemetall Gmbh | Mixture for applying a non-corrosive, thin polymer coating which can be shaped in a low-abrasive manner, and method for producing the same |
US7736538B2 (en) | 2002-04-20 | 2010-06-15 | Chemetall Gmbh | Mixture for applying a non-corrosive, polymer coating which can be shaped in a low-abrasive manner, and method for producing the same |
EP2767564B1 (de) | 2007-08-17 | 2016-10-05 | PPG Industries Ohio Inc. | Klarlackzusammensetzung |
EP2183298B1 (de) | 2007-08-17 | 2017-10-04 | PPG Industries Ohio, Inc. | Verfahren zur herstellung einer mehrlagigen beschichtung mit strahlungshärtbaren polyen-/polythiolbeschichtungszusammensetzungen |
EP2767564B2 (de) † | 2007-08-17 | 2020-01-08 | PPG Industries Ohio Inc. | Klarlackzusammensetzung |
Also Published As
Publication number | Publication date |
---|---|
BR0011059A (pt) | 2002-03-05 |
EP1190004A1 (de) | 2002-03-27 |
DE19924674C2 (de) | 2001-06-28 |
US6716891B1 (en) | 2004-04-06 |
DE19924674A1 (de) | 2000-11-30 |
EP1190004B1 (de) | 2003-07-30 |
ES2204596T3 (es) | 2004-05-01 |
JP2003501512A (ja) | 2003-01-14 |
DE50003129D1 (de) | 2003-09-04 |
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