WO1998040442A1 - Verfahren zur herstellung kratzfester beschichtungen, insbesondere zur herstellung von mehrschichtlackierungen - Google Patents
Verfahren zur herstellung kratzfester beschichtungen, insbesondere zur herstellung von mehrschichtlackierungen Download PDFInfo
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- WO1998040442A1 WO1998040442A1 PCT/EP1998/001265 EP9801265W WO9840442A1 WO 1998040442 A1 WO1998040442 A1 WO 1998040442A1 EP 9801265 W EP9801265 W EP 9801265W WO 9840442 A1 WO9840442 A1 WO 9840442A1
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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
Definitions
- the present invention relates to a method for producing scratch-resistant coatings, in particular scratch-resistant multi-layer coatings.
- the present invention also relates to coating compositions suitable for this process.
- This article proposes to increase the scratch resistance of the clear lacquer coatings by incorporating siloxane macromonomers, since these siloxane macromonomers lead to an increased homogeneity of the clear lacquer surface and above 60 ° C. to an improved plastic flow. Furthermore, for example from Loren W. Hill, Journal of Coatings Technology, Vol. 64, No. 808, May 1992, pages 29 to 41, the relationship between memory module and crosslink density is known. However, this article does not contain any instructions or information on how scratch-resistant coatings can be obtained.
- non-aqueous clear lacquers based on hydroxyl-containing acrylate resins and isocyanates for the production of multi-layer lacquers are known, in which the resulting coatings are characterized by improved scratch resistance and good distinguish other usage properties.
- these clear coats there is a desire for an even better scratch resistance.
- the present invention is therefore based on the object of providing a method for producing coatings with a further improved scratch resistance.
- the coating agents used in this process should also be suitable as a clear lacquer and / or topcoat for producing a multi-layer coating, in particular in the motor vehicle sector. Furthermore, the coating agents have a high gloss and good chemical and weather resistance.
- the objective assessment of the scratch resistance of the hardened coating should be possible based on physical parameters regardless of the test method selected. This method should be practically applicable for determining the physical parameters and should enable the character of the scratch resistance to be characterized as adequately as possible with sufficient accuracy.
- This object is surprisingly achieved by a process for producing scratch-resistant coatings, which is characterized in that coating agents are used which
- a memory module E 'in the rubber-elastic range of at least 10 7 ' ⁇ Pa and a loss factor tan ⁇ at 20 ° C of at least 0.05, the memory module E 'and the loss factor tan ⁇ with the dynamic mechanical thermal analysis have been measured on homogeneous free films with a layer thickness of 40 + 10 ⁇ m,
- binder one or more polyacrylate resins with a hydroxyl number of 100 to 240, preferably more than 160 to 220 and particularly preferably 170 to 200, an acid number of 0 to 35, preferably 0 to 25, and a number average molecular weight of 1,500 to 10,000, preferably 2,500 to 5,000, as well
- the present application also relates to a process for producing a scratch-resistant multilayer coating and to coating compositions suitable for this process.
- DMTA dynamic mechanical thermal analysis
- the coating agent is selected so that the cured coating agent has a storage modulus E 'of at least 10 7 ' Pa, preferably of at least 10 7 'Pa, particularly preferably of at least 10 7 ' 7 Pa, in the rubber-elastic range has a loss factor at 20 ° C. of at least 0.05, preferably of at least 0.07, the memory module E 'and the loss factor tan ⁇ have been measured using dynamic mechanical thermal analysis on homogeneous free films with a layer thickness of 40 _ + 10 ⁇ m.
- the loss factor tan ⁇ is defined as the quotient of the loss module E "and the memory module E '.
- Dynamic mechanical thermal analysis is a generally known measurement method for determining the viscoelastic properties of coatings and is described, for example, in Murayama, T., Dynamic Mechanical Analysis of Polymeric Material, Esevier, New York, 1978 and Loren W. Hill , Journal of Coatings Technology, Vol. 64, No. 808, May 1992, pages 31 to 33.
- the measurements can be carried out, for example, using the MK II, MK III or MK IV devices from Rheometrics Scientific.
- the storage module E 'and the loss factor tan ⁇ are measured on homogeneous free films.
- the free films are produced in a known manner by applying and curing the coating agent on substrates to which the coating agent does not adhere. Glass, Teflon and in particular polypropylene may be mentioned as examples of suitable substrates.
- Polypropylene has the advantage of good availability and is therefore normally used as a carrier material.
- the layer thickness of the free films used for the measurement is generally 40 + _ 10 ⁇ m.
- the special selection of the coating compositions based on the value of the storage module in the rubber-elastic range and the loss factor at 20 ° C. of the cured coating compositions makes it possible in a simple manner the provision of coating agents with the desired good scratch resistance, since both parameters can be determined by simple DMTA measurements.
- the coating compositions of the invention used in the process for producing scratch-resistant coatings contain, as binders, one or more polyacrylate resins with a hydroxyl number of 100 to 240, preferably more than 160 to 220 and particularly preferably 170 to 200, an acid number of 0 to 35, preferably 0 to 25, and a number average molecular weight of 1,500 to 10,000, preferably 2,500 to
- the monomer composition selected in each case also influences, for example, these viscoelastic parameters of the cured coating.
- that takes Storage module E ' generally decreases with increasing styrene content of the acrylate resins.
- acrylate resins as binders which contain a maximum of 15% by weight, based on the total weight of all monomers of the acrylate resin, of copolymerized vinylaromatic hydrocarbons, in particular styrene.
- acrylate resins with as many primary hydroxyl groups as possible are preferably used as binders in the coating compositions of the invention (at least 50% to 100% of the OH groups are particularly preferably primary OH groups), since they are more complete than secondary OH groups of the primary OH groups, an increase in the storage module E 'of the cured coatings is also possible.
- Acrylate resins with a glass transition temperature of at most 70 ° C., particularly preferably with a glass transition temperature of -40 to +30 ° C., are furthermore preferably used as binders.
- the glass transition temperature can be determined by the person skilled in the art with the aid of the formula
- T Q glass transition temperature of the polymer
- W n proportion by weight of the nth monomer
- TQ ⁇ glass transition temperature of the homopolymer from the nth monomer
- binders are also preferred
- Acrylic resins are used, which are available by (a) 25 to 62, preferably 41 to 57% by weight of 4-hydroxy-n-butyl acrylate or 4-hydroxy-n-butyl methacrylate or a mixture of 4-hydroxy-n-butyl acrylate and 4-hydroxy-n-butyl methacrylate,
- component (c) are polymerized to the polyacrylate resin, the sum of the proportions by weight of components (a), (b), (c), (d) and (e) always giving 100% by weight and the composition of component (c) thus is selected so that when component (c) is polymerized alone, a poly methacrylate resin with a glass transition temperature of 0 to +80, preferably 0 to + 60 ° C., is obtained.
- the preparation of the polyacrylate resins preferably used according to the invention can generally be carried out known polymerization process.
- Polymerization processes for the production of polyacrylate resins are generally known and have been described many times (see, for example: Houben-Weyl, Methods of Organic Chemistry, 4th Edition, Volume 14/1, pages 24 to 255 (1961)).
- the polyacrylate resins which are preferably used according to the invention are produced in particular with the aid of the solution polymerization process.
- An organic solvent or solvent mixture is usually initially introduced and heated to boiling.
- the monomer mixture to be polymerized and one or more polymerization initiators are then continuously added to this organic solvent or solvent mixture.
- the polymerization takes place at temperatures between 100 and 160 ° C., preferably between 130 and 150 ° C.
- Free radical initiators are preferably used as the polymerization initiators.
- the type and amount of initiator are usually chosen so that the available radicals are as constant as possible at the polymerization temperature during the feed phase.
- initiators which can be used are: dialkyl peroxides, such as di-tert-butyl peroxide, dicumyl peroxide; Hydroperoxides such as cumene hydroperoxide, tert-butyl hydroperoxide; Perester, like tert. Butyl perbenzoate, tert-butyl perpivalate, tert-butyl per-3, 5, 5-trimethylhexanoate, tert. Butyl per-2-ethylhexanoate; Bisazo compounds such as azobisisobutyro .itril.
- the polymerization conditions (reaction temperature, feed time of the monomer mixture, amount and type of organic solvents and polymerization initiators, possible concomitant use of molecular weight regulators, such as mercaptans, thiol glycolic acid esters and hydrogen chloride) are selected so that the polyacrylate resins preferably used are a number-average molecular weight. Specular weight of 1500 to 10,000, preferably 2500 to 5000 (determined by gel chromatography using a polystyrene standard).
- the acid number of the polyacrylate resins used according to the invention can be adjusted by the person skilled in the art by using appropriate amounts of component (d). The same applies to the setting of the hydroxyl number. It can be controlled via the amount of component (a) and (b) used.
- 4-Hydroxy-n-butyl acrylate, 4-hydroxy-n-butyl methacrylate or a mixture of 4-hydroxy-n-butyl acrylate and 4-hydroxy-n-butyl methacrylate is used as component (a).
- 4-Hydroxy-n-butyl acrylate is preferably used as component (a).
- polyacrylate component (a) are also suitable as polyacrylate component (a) are the hydroxy-functional compounds mentioned in European patent application EP 0 767 185 and in US Pat. Nos. 5,480,943, 5,475,073 and 5,534,598.
- component (b) provided that when polymerizing component (b) alone a polyacrylate resin with a glass transition temperature of 0 to +80, preferably 0 to + 60 ° C is obtained - in principle any of (a) Various hydroxyl-containing esters of acrylic acid or methacrylic acid or a mixture of such monomers can be used. Examples include: hydroxyalkyl esters of acrylic acid, such as Hydroxyethyl acrylate and hydroxypropyl acrylate and hydroxyalkyl esters of methacrylic acid, e.g. Hydroxyethyl methacrylate and hydroxypropyl methacrylate, as well as the esterification products of hydroxyalkyl (meth) acrylates with one or more ⁇ -caprolactone molecules.
- hydroxyalkyl esters of acrylic acid such as Hydroxyethyl acrylate and hydroxypropyl acrylate
- methacrylic acid e.g. Hydroxyethyl methacrylate and hydroxypropyl
- component (c) can be any aliphatic or cycloaliphatic ester of methacrylic acid having at least 4 carbon atoms in the alcohol radical or a mixture of such monomers, different from (a) and (b). be set.
- Examples include: aliphatic esters of methacrylic acid with 4 to 20 carbon atoms in the alcohol radical, such as n-butyl, isobutyl, tert-butyl, 2-ethylhexyl, stearyl and lauryl methacrylate and cycloaliphatic esters of methacrylic acid such as.
- B. Cyclohexyl methacrylate The composition of component (c) is selected so that when component (c) is polymerized alone, a polymethacrylate resin with a glass transition temperature of 0 to +80 ° C., preferably 0 to + 60 ° C., is obtained.
- any ethylenically unsaturated carboxylic acid or a mixture of ethylenically unsaturated carboxylic acids can be used as component (d).
- Acrylic acid and / or methacrylic acid are preferably used as component (d).
- any ethylenically unsaturated monomer or a mixture of such monomers other than (a), (b), (c) and (d) can be used as component (e).
- monomers that can be used as component (s) are: vinyl aromatic hydrocarbons, such as styrene, ⁇ -alkylstyrene and vinyl toluene, amides of acrylic acid and methacrylic acid, such as e.g. Methacrylamide and acrylamide; Nitriles of methacrylic acid and acrylic acid; Vinyl ether and vinyl ester.
- Vinylaromatic hydrocarbons, in particular styrene are preferably used as component (e).
- the composition of component (e) is preferably selected so that, when component (e) is polymerized alone, a polymer with a glass transition temperature of +70 to +120, preferably +80 to + 100 ° C., is obtained.
- the coating compositions used in the process for producing scratch-resistant coatings contain, as crosslinking agents, one or more free or blocked isocyanates and / or triazine-based components which crosslink with the hydroxyl groups of the binder with the formation of ethers and / or esters. If blocked isocyanates are present, the coating compositions according to the invention are one-component (1K) clearcoats. If free isocyanates are present, the coating compositions according to the invention are two-component (2K) clearcoats.
- any polyisocyanate or a mixture of such polyisocyanates that can be used in the paint field can be used as the crosslinking agent, provided that the cured coatings have the above-mentioned viscoelastic properties.
- polyisocyanates whose isocyanate groups are bound to aliphatic or cycloaliphatic radicals are preferred. Examples of such polyisocyanates.
- TXDI 1,3- and 1,4-bis (isocyanatomethyl) cyclohexane and adducts of these polyisocyanates with polyols, especially low molecular weight polyols, such as trimethylolpropane and polyisocyanates containing isocyanurate groups and / or biuret groups and derived from these polyisocyanates.
- Particularly preferred polyisocyanates are hexamethylene diisocyanate and isophorone diisocyanate, isocyanurate and / or biuret group-containing polyisocyanates derived from these diisocyanates, which preferably contain more than 2 isocyanate groups in the molecule, and reaction products of hexamethylene diisocyanate and isophorone diisocyanate or a mixture of hexamethylene diisocyanate and isocyanate diisocyanate and 3 to 0.5 equivalents of a low molecular weight polyol with a molecular weight of 62 to 500, preferably from 104 to 204, in particular a triol, such as trimethylolpropane, used.
- a low molecular weight polyol with a molecular weight of 62 to 500, preferably from 104 to 204, in particular a triol, such as trimethylolpropane, used.
- any blocking agent which can be used for blocking polyisocyanates and has a sufficiently low blocking temperature can be used to block the polyisocyanates.
- blocking agents are well known to the person skilled in the art and need not be explained in more detail here.
- Blocked polyisocyanates are preferably used which contain isocyanate groups blocked both with a blocking agent (I) and with a blocking agent (II), where
- the blocking agent (I) is a dialkyl malonate or a mixture of dialkyl malonates
- the blocking agent (II) is a CH-acidic blocking agent different from (I), an oxime or a mixture of these blocking agents and
- the equivalent ratio between the isocyanate groups blocked with (I) and the isocyanate groups blocked with (II) between 1.0: 1.0 and 9.0: 1.0, preferably between 8.0: 2.0 and 6.0: 4 , 0, particularly preferably between 7.5: 2.5 and 6.5: 3.5.
- Dialkylmalonates or a mixture of dialkylmalonates are used as blocking agents (I). Dialkylmalonates each having 1 to 6 carbon atoms in the alkyl radicals are mentioned as examples of dialkylmalonates which can be used, such as dimethyl malonate and diethyl malonate, diethyl malonate being preferred.
- the blocking agents (II) used are blocking agents and oximes containing active methylene groups other than (I) and mixtures of these blocking agents.
- blocking agents (II) are: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or dodecyl esters of acetoacetic acid, acetone oxime, methyl - ethyl ketoxime, acetyl acetone, formaldoxime, acetaldoxime, benzophenoxime, acetoxime and diisobutyl ketoxime.
- the blocking agent (II) used is preferably an alkyl acetic acid ester having 1 to 6 carbon atoms in the alkyl radical or a mixture of such real acetoacetic acid alkyl esters or a ketoxime or a mixture of ketoximes.
- Alkyl acetate or methyl ethyl ketoxime are particularly preferably used as blocking agents (II).
- Dimethylpyrazole and / or triazoles can also be used as further blocking agents.
- the crosslinkers which react with the hydroxyl groups of the binder to form ether are aminoplast resins.
- Aminoplast resins are well known to the person skilled in the art and are offered by many companies as sales products. These are condensation products from aldehydes, in particular formaldehyde, and for example urea, melamine, guanamine and benzoguanamine.
- the aminoplast resins contain alcohol groups, preferably methylol groups, which as a rule are partially or preferably completely etherified with alcohols. Especially with low alcohols, especially melamine-formaldehyde resins etherified with methanol or butanol.
- triazine-based crosslinkers which react with the hydroxyl groups of the binder to form ester groups are transesterification crosslinkers, such as preferably tris (alkoxycarbonylamino) triazine or the like, as also described, for example, in EP-A-604 922.
- the coating compositions according to the invention are aqueous or preferably conventional, i.e. based on organic solvents.
- Solvents suitable for the production of conventional clear coats are e.g. the solvents used to manufacture the acrylic resins.
- the transparent coating compositions used according to the invention contain no or only transparent pigments.
- the coating compositions can also contain other common additives, such as light stabilizers, leveling agents, etc.
- pigmented coating compositions that are not transparent can also be produced.
- in principle all organic or inorganic pigments or mixtures of these which are suitable for the production of pigmented lacquers can be used
- Pigments are used.
- pigments that can be used are: azo pigments (e.g. Pigment Red 57: 1, Pigment Yellow 1, Pigment Yellow 13 and Pigment Red 7), phthalocyanine pigments (e.g. Pigment Blue 15: 3 and phthalocyanine green), carbonyl pigments (e.g. Pigment Red 88, Pigment Red 177, Pigment Yellow 123, Pigment Violet 19, Pigment Yellow 24 and Pigment Orange 51 or 52), dioxazine pigments (e.g.
- Pigment Violet 23 titanium dioxide, carbon black, black iron oxide (magnetite, triiron tetroxide), red iron oxide ( Hematite, dieisen trioxide), iron oxide yellow (iron oxide hydroxide), iron oxide brown (mixed pigment of iron oxide red, iron oxide yellow and iron oxide black), chrome oxide green (dichromium trioxide), nickel titanium yellow, chrome titanium yellow and cobalt blue.
- effect pigments such as Metal flake pigments, in particular aluminum flake pigments and pearlescent pigments are used.
- binders, crosslinking agents and the pigment or the mixture of pigments are generally used in amounts such that the binder or binders are present in an amount of 39 to 90, preferably 45 to 75, by weight .-%, the or the crosslinking agent in an amount of 9 to 60, preferably 20 to 50 wt .-% and that
- the coating compositions according to the invention can be applied to glass and a wide variety of metal substrates, e.g. Aluminum, steel, various iron alloys etc. are applied. They are preferably used as a clear or topcoat in the field of automotive painting (automotive serial painting and - when using free isocyanates - also in the area of automotive refinishing). Of course, in addition to application to a wide variety of metals, the coating compositions can also be applied to other substrates, such as wood, paper, plastics, mineral substrates, etc. be applied. They are also used in the coating of packaging containers and in the coating of foils for the furniture industry etc. applicable.
- metal substrates e.g. Aluminum, steel, various iron alloys etc.
- the coating compositions can also be applied to other substrates, such as wood, paper, plastics, mineral substrates, etc. be applied. They are also used in the coating of packaging containers and in the coating of foils for the furniture industry etc. applicable.
- the coating compositions according to the invention are preferably used as a topcoat in processes for producing a multi-layer coating, in particular in the field of automotive series coating.
- the present invention therefore also relates to a process for the production of multi-layer coatings, in which
- a coating agent according to the invention is used as the topcoat.
- step (1) of the process according to the invention in principle all pigmented basecoats suitable for the production of two-coat paint systems can be used.
- Such basecoats are well known to those skilled in the art.
- Both water-dilutable basecoats and basecoats based on organic solvents can be used.
- Suitable basecoats are described, for example, in US-A-3,639,147, DE-A-33 33 072, DE-A-38 14 853, GB-A-2 012 191, US-A-3,953,644, EP-A-260 447, DE-A-39 03 804, EP-A-320 552, DE-A-36 28 124, US-A-4,719,132, EP-A-297 576, EP-A-69 936, EP-A-89 497, EP-A-195 931, EP-A-228 003, EP-A-38 127 and DE-A-28 18 100. These patent documents also contain further information about the base coat / clear coat method in question to find.
- stage (2) of the process according to the invention the basecoat film applied in stage (1) is dried, i.e. at least some of the organic solvents or water is removed from the basecoat film in an evaporation phase.
- the basecoat film is usually dried at temperatures from room temperature to 80 ° C.
- topcoat of the invention is then applied and the basecoat and topcoat are cured together, usually by heating to temperatures of 120 to 155 ° C. for a period of 20 to 40 minutes.
- a suitable choice of crosslinkers means that even lower firing temperatures as usual in the field of repair and plastic painting, from below 100 ° C, preferably below 80 ° C, possible.
- the coatings produced using the coating compositions according to the invention are distinguished by a scratch resistance which is markedly improved compared to conventional coatings.
- the scratch resistance of the cured coatings can be determined, for example, with the help of the BASF brush test described in FIG. 2 on page 28 of the article by P. Betz and A. Bartelt, Progress in Organic Coatings, 22 (1993), pages 27-37 However, with regard to the weight used (2000 g instead of the 280 g mentioned there), the following can be assessed.
- the paint surface is damaged with a screen fabric that is loaded with a mass.
- the screen fabric and the varnish surface are wetted liberally with a detergent solution.
- the test panel is moved back and forth under the sieve mesh in a lifting motion by means of a motor drive.
- the panels are stored at room temperature for at least 2 weeks after application of the paints before the test is carried out.
- the test specimen is eraser covered with nylon sieve mesh (No. 11, 31 ⁇ m mesh size, Tg 50 ° C) (4.5 x 2.0 cm, wide side perpendicular to the direction of scratching).
- the coating weight is 2000 g.
- the screen mesh is renewed before each test, whereby the running direction of the mesh is parallel to the scratch direction.
- a pipette approx. 1 ml of a freshly stirred 0.25% Persil solution is applied in front of the eraser.
- the number of revolutions of the motor is set so that 80 double strokes are carried out in a time of 80 s.
- the remaining washing liquid is rinsed off with cold tap water and the test panel is blown dry with compressed air.
- the gloss is measured according to DIN 67530 before and after damage (measuring direction perpendicular to the scratch direction).
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Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/380,524 US6410646B1 (en) | 1997-03-07 | 1998-03-06 | Method for producing scratch resistant coatings, especially for producing multi-layer enamels |
BR9808204-3A BR9808204A (pt) | 1997-03-07 | 1998-03-06 | Processo para preparação de revestimentos à prova de arranhões, particularmente para preparação de laqueamentos com múltiplas camadas |
JP53918398A JP2001514692A (ja) | 1997-03-07 | 1998-03-06 | 耐引掻性被覆、殊に多層塗装の製造のための方法 |
EP98913655A EP0964896A1 (de) | 1997-03-07 | 1998-03-06 | Verfahren zur herstellung kratzfester beschichtungen, insbesondere zur herstellung von mehrschichtlackierungen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19709465.1 | 1997-03-07 | ||
DE19709465A DE19709465C2 (de) | 1997-03-07 | 1997-03-07 | Beschichtungsmittel, Verfahren zur Herstellung von Mehrschichtlackierungen und Verwendung der Beschichtungsmittel hierfür |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/380,524 A-371-Of-International US6410646B1 (en) | 1997-03-07 | 1998-03-06 | Method for producing scratch resistant coatings, especially for producing multi-layer enamels |
US10/083,811 Division US6620884B2 (en) | 1997-03-07 | 2002-02-27 | Method for producing scratch resistant coatings, especially for producing multi-layer enamels |
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Publication Number | Publication Date |
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WO1998040442A1 true WO1998040442A1 (de) | 1998-09-17 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP1998/001265 WO1998040442A1 (de) | 1997-03-07 | 1998-03-06 | Verfahren zur herstellung kratzfester beschichtungen, insbesondere zur herstellung von mehrschichtlackierungen |
Country Status (6)
Country | Link |
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US (2) | US6410646B1 (de) |
EP (1) | EP0964896A1 (de) |
JP (1) | JP2001514692A (de) |
BR (1) | BR9808204A (de) |
DE (1) | DE19709465C2 (de) |
WO (1) | WO1998040442A1 (de) |
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DE10305115A1 (de) * | 2003-02-07 | 2004-09-02 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
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1998
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- 1998-03-06 US US09/380,524 patent/US6410646B1/en not_active Expired - Fee Related
- 1998-03-06 JP JP53918398A patent/JP2001514692A/ja active Pending
- 1998-03-06 BR BR9808204-3A patent/BR9808204A/pt not_active IP Right Cessation
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2002
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US7446142B2 (en) * | 2001-08-16 | 2008-11-04 | Basf Coatings Ag | Thermal coating materials and coating materials that can be cured thermally and using actinic radiation and the use thereof |
DE10305119A1 (de) * | 2003-02-07 | 2004-08-26 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE10305115A1 (de) * | 2003-02-07 | 2004-09-02 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE10305119B4 (de) * | 2003-02-07 | 2007-02-22 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE10305115B4 (de) * | 2003-02-07 | 2007-02-22 | Basf Coatings Ag | Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
KR101103194B1 (ko) * | 2003-04-24 | 2012-01-04 | 누플렉스 레진스 비브이 | 코팅재 조성물 |
Also Published As
Publication number | Publication date |
---|---|
US6410646B1 (en) | 2002-06-25 |
US6620884B2 (en) | 2003-09-16 |
DE19709465A1 (de) | 1998-09-17 |
JP2001514692A (ja) | 2001-09-11 |
US20020095012A1 (en) | 2002-07-18 |
EP0964896A1 (de) | 1999-12-22 |
DE19709465C2 (de) | 2001-07-12 |
BR9808204A (pt) | 2000-05-16 |
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