EP1023403A1 - Revetements en poudre a impression de couleur dependant de l'angle d'observation - Google Patents

Revetements en poudre a impression de couleur dependant de l'angle d'observation

Info

Publication number
EP1023403A1
EP1023403A1 EP98948874A EP98948874A EP1023403A1 EP 1023403 A1 EP1023403 A1 EP 1023403A1 EP 98948874 A EP98948874 A EP 98948874A EP 98948874 A EP98948874 A EP 98948874A EP 1023403 A1 EP1023403 A1 EP 1023403A1
Authority
EP
European Patent Office
Prior art keywords
powder
mol
effect coating
coated
crystalline
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Withdrawn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
EP98948874A
Other languages
German (de)
English (en)
Inventor
Bernd Dewald
Andreas Stohr
Axel Schönfeld
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant 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 Clariant GmbH filed Critical Clariant GmbH
Publication of EP1023403A1 publication Critical patent/EP1023403A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/36—Pearl essence, e.g. coatings containing platelet-like pigments for pearl lustre
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • C09D5/032—Powdery paints characterised by a special effect of the produced film, e.g. wrinkle, pearlescence, matt finish

Definitions

  • the invention relates to powder coatings with a brilliant color impression depending on the viewing angle, hereinafter
  • Powder effect coating called, process for their preparation and their use.
  • cLCP cholesteric liquid-crystalline polymer
  • liquid-crystalline phase is known for the fact that non-liquid-crystalline components cannot be dissolved or stably dispersed in it and are known to those skilled in the art under the names "chalking” and "crater formation” Phenomena occur, so that it is generally not possible to work with stabilizers and auxiliaries.
  • the object of the present invention was to develop easy-to-process effect coating systems and in particular effect basecoats which can be processed similarly to a classic powder coating and which have a good flow.
  • the present invention relates to a powder effect coating with a color impression dependent on the viewing angle, consisting essentially of one or more cholesteric liquid-crystalline polymers and at least one leveling additive from the group of hydroxylated polyester resins, polyacrylates and acrylate copolymers.
  • the powder effect coatings according to the invention contain cholesteric liquid-crystalline polymers (cLCPs) which have a helical superstructure.
  • this superstructure means that the material no longer has the anisotropy of mechanical properties which is customary in nematic liquid-crystal polymers.
  • the material shows pronounced
  • all cholesteric liquid-crystalline main chain polymers or combined main chain / side group polymers can be used as cLCP.
  • Cholesteric backbone polymers are generally made from a chiral component as well as from hydroxy carboxylic acids and / or a combination of dicarboxylic acids and diols. As a rule, the polymers consist essentially of aromatic constituents. However, it is also possible aliphatic and cycloaliphatic components, such as cyclohexanedicarboxylic acid.
  • cholesteric liquid-crystalline main chain polymers consisting essentially of a) 0 to 99 mol% of one or more compounds from the group of aromatic hydroxycarboxylic acids, cycloaliphatic hydroxycarboxylic acids and aromatic aminocarboxylic acids; b) 0 to 49.5 mol% of one or more compounds from the group of aromatic dicarboxylic acids and cycloaliphatic dicarboxylic acids; c) 0 to 49.5 mol% of one or more compounds from the group of aromatic diols, cycloaliphatic diols and aromatic diamines; d) 1 to 40 mol%, preferably 2 to 25 mol%, of chiral, bifunctional comonomers; e) 0 to 5 mol% of a branchable component with more than two functional groups, the total amount being 100 mol% and the sum of a), b) and c) being 60 to 99 mol%.
  • the polymers can also contain components with more than two functional groups, such as, for example, dihydroxybenzoic acids, trihydroxybenzenes or trimellitic acid. These components act as a branching point in the polymer and may only be added in small concentrations, for example 0 to 5 mol%, in order to avoid crosslinking of the material.
  • cLCP particularly preferred as cLCP are polymers containing camphoric acid and / or isosorbide as the chiral component and p-hydroxybenzoic acid and / or 2-hydroxy-6-naphthoic acid and / or terephthalic acid and / or isophthalic acid and / or hydroquinone and / or resorcinol and / or 4 , 4'-Dihydroxybiphenyl and / or 2,6-naphthalenedicarboxylic acid.
  • the chiral comonomers are preferably used in an enantiomerically pure form. When using enantiomer mixtures of a comonomer, care must be taken that an enantiomer form is present in an effective excess.
  • the monomers used according to the invention can either be used directly, or it is also possible to use expedient precursors which react under the following reaction conditions to give the desired monomers. For example, instead of N- (4-
  • the polycondensation can be carried out using all polycondensation processes known to the person skilled in the art.
  • the polycondensation processes known to the person skilled in the art.
  • the polycondensation processes known to the person skilled in the art.
  • the polycondensation processes known to the person skilled in the art.
  • the monomers are preferably linked via ester bonds (polyester) and / or via amide bonds (polyesteramide / polyamide), but the linkage can also take place via other types of linkage known to the person skilled in the art, for example polyesterimide.
  • Molecular weight monomers from groups b) to d) or those listed To use components with more than two functional groups in an excess necessary to achieve a defined molecular weight. Furthermore, the molecular weight can be influenced by using monofunctional monomers.
  • carboxylic acids other carboxylic acid derivatives known to the person skilled in the art, such as, for example, acid chlorides or carboxylic acid esters, can also be used.
  • carboxylic acid derivatives known to the person skilled in the art, such as, for example, acid chlorides or carboxylic acid esters
  • hydroxy components corresponding hydroxy derivatives, such as, for example, the acetylated hydroxy compounds, can also be used.
  • polymer building blocks described can also contain further substituents, such as methyl, methoxy or halogen.
  • cholesteric liquid-crystalline polymers by mixing colorless and / or colored nematic and / or cholesteric liquid-crystalline polymers.
  • the color of the powder effect coating can be varied within a wide range and precisely adjusted.
  • the main chain polymers have a very low solubility, so that their molecular weights cannot be determined using customary methods (GPC, light scattering).
  • the intrinsic viscosity of the polymers in a solution of pentafluorophenol / hexafluoroisopropanol can be used as a measure of the molecular weight.
  • Polymers with an intrinsic viscosity between 0.1 dl / g and 10 dl / g are suitable.
  • the preferred main chain polymers have high thermal stability and, due to their low solubility, excellent stability compared to the solvents used in paints. They therefore make crosslinking reactions after application to the substrate surface superfluous. This not only makes the application much easier, but also the synthesis.
  • the systems which are also known for commercially available powder coatings can be used as leveling additives. These can be, for example, hydroxylated polyester resins or polyacrylates or copolymers with acrylate components. These compounds can be used in pure form or else adsorbed on silica gel. Leveling additives based on acrylate or methacrylate are preferred.
  • the structure of the powder effect coatings according to the invention differs significantly from the commercially available powder coatings, which consist of a binder and colorants, crosslinking agents and flow aids dispersed therein.
  • the invention also relates to a process for producing a powder effect coating with a color impression which is dependent on the viewing angle, characterized in that the leveling additive is incorporated into the cholesteric LCP, e.g. is dispersed, this mixture is optionally converted into a finely divided powder, which is applied to the object to be coated using a powder coating process and is converted into a film with a color impression which is dependent on the viewing angle by thermal treatment.
  • the leveling additive is incorporated into the cholesteric LCP, e.g. is dispersed, this mixture is optionally converted into a finely divided powder, which is applied to the object to be coated using a powder coating process and is converted into a film with a color impression which is dependent on the viewing angle by thermal treatment.
  • the cholesteric LCPs are usually obtained as granules during synthesis.
  • the leveling additives can be incorporated in the melt using methods known to the person skilled in the art, such as kneading or extrusion, for example.
  • the cholesteric LCPs usually show a very high one
  • the leveling additives are the cholesteric LCP in concentrations between 0.01 to 5 wt .-%, preferably 0.05 to 1, 5 wt .-% and particularly preferably 0.2 to 0.5 wt .-% added. If the active substance makes up only a fraction of the additive or the active substance is adsorbed on silica gel, for example, a correspondingly higher proportion may also be expedient.
  • Grinding units of all types and embodiments are suitable for producing the polymer powder containing the leveling additive.
  • the required grain size can be achieved in one process step or in several sub-steps in the same or different mill types. If the desired minimum fineness and particle size distribution are not achieved directly by the grinding process carried out, it is advisable to subject the regrind to sieving or classification processes during the grinding process or after the grinding process in order to guarantee the desired minimum fineness and to obtain a desired optimal grain size fraction.
  • grinding units are, for example, vibrating, vibrating disc, disc, planet, centrifugal,
  • Mortar, ball, cross beater, beater rotor, cutting, hammer, knife, rotor stator, baffle plate and in particular ultra-centrifugal, universal, pen and air jet mills are suitable.
  • wet grinding can also be carried out in ball, sand, vibrating or pearl mills.
  • the polymer powder obtained after the grinding process is electrostatically charged during the actual spraying process. This happens at
  • Corona process by passing the powder past a loaded corona.
  • the powder itself is charged.
  • the principle of frictional electricity is used in the triboelectric or electrokinetic process.
  • the powder receives an electrostatic charge in the sprayer, that of the charge of the friction partner, generally a hose or a
  • Spray tube (for example made of polytetrafluoroethylene), is opposite.
  • the Electrostatic charging leads to a high degree of separation of the powder on the object to be coated.
  • the powder layer is heated to temperatures above the softening point of the powder, at which the polymers form a homogeneous film and form the helical superstructures.
  • the temperature at which the formation of the helical structure begins is referred to below as the chiralization temperature.
  • the special optical properties of the powder effect coatings according to the invention are only observed when the molecules form the helical structure above the chiralization temperature of the polymer. In many cases, the transition to the cholesteric phase already takes place during the synthesis of the polymers.
  • the wavelength of the selective reflection of the cLCPs used according to the invention is determined by the pitch of the helical structure.
  • the pitch depends on the structure of the polymer, the melt viscosity, the presence of solvents and in particular on the twisting power of the chiral monomer ("helical twisting power"). It is also a function of temperature. Accordingly, the pitch of the helix can also be adjusted via the temperature. By rapidly cooling the coated substrates, the pitch of the helix and thus the
  • the flame spraying process Another preferred option for coating objects with powdery substances is the flame spraying process.
  • the powder is fluidized with a carrier gas (e.g. in a fluidized bed) and fed to the central nozzle of a flame spray gun.
  • a fuel gas / oxygen mixture is generated in the flame spray gun, which is burned in many small flames arranged in a ring around the center.
  • the powdery particles melt and are then deposited on the object to be coated as droplets, which flow together to form a film in the course of the spraying process.
  • This method offers the particular advantage that the melting process is integrated into the spraying process, so that the coating can be applied to the object and the film formed in one work step.
  • Another preferred embodiment for powder coating is the vortex sintering process.
  • a fluidized bed is generated in a suitable container using a carrier gas and the polymer powder according to the invention.
  • the object to be coated is heated in a separate heating chamber to the temperature necessary for the coating, and after this temperature has been reached, it is immersed in the fluidized bed for a certain time. Powdery particles stick to the surface of the object, melt, flow into a film and form the helical structure. In some cases it is advantageous to subject the coated object to a further temperature treatment in order to form the film and
  • This method also has the particular advantage that the melting process is integrated into the coating process, so that the coating can be applied to the object, the orientation of the polymer molecules and the film formation in one step.
  • the particle shape and thus the flowability of the powder and the particle size distribution of the powder are of great importance. Preference is given to particles which come as close as possible to the spherical shape and which have a narrow grain size distribution. Depending on the type of mill used, the grinding processes result in narrower or wider particle size distributions. In some cases, it is advantageous to connect a sieving, classification or screening process to the grinding in order to achieve the smallest possible particle size distribution.
  • the grain size must be adapted to the desired layer thickness of the powder effect coating, the type of object to be coated and the application method used. If thin layers of lacquer are required on the object to be coated, a medium one is required
  • Particle size of the powder between 1 and 100 microns, preferably between 15 and 80 microns to strive. If thick layers are desired on the object, as are normally applied during fluid sintering and flame spraying, then an average particle size between 80 and 300 ⁇ m, preferably 100 to 250 ⁇ m, is advantageous. When whirling and flame spraying, particular attention must be paid to compliance with the grain size limits. Particles that are too small are heated too much by the high flame temperatures and charred or are blown away by the gas flow. On the other hand, particles that are too coarse are not melted completely and cannot orient themselves optimally during the subsequent film formation. In exceptional cases, however, it can also be advantageous to use a grain size distribution outside this range.
  • the powder effect coatings according to the invention can be applied to a wide variety of substrates.
  • these can be objects made of natural and synthetic materials such as wood, plastics, metal or glass. If the effect coating is applied without a pre-coating, it is recommended to apply it in a layer thickness that covers the surface. Of course, several layers can also be applied or semi-transparent coatings can be produced.
  • the coating of the body or of body parts of motor vehicles is particularly preferred.
  • the powder effect coating is applied to metal or plastic substrates. These are usually pre-coated.
  • plastic substrates can be provided with a plastic primer, and metallic substrates generally have an electrophoretically applied primer and optionally one or more further lacquer layers, such as a filler layer.
  • Dark substrates are particularly preferred.
  • underground is not only to be understood as meaning a substrate provided with a dark lacquer layer on its surface, but also a substrate which is colored in itself, for example a plastic substrate or a metal substrate coated with a dark oxide layer.
  • dark lacquer layers are electrophoretic or primers applied by spray or powder coating, plastic primers, filler and stone chip protection layers or also plain-colored base and top coat layers. Examples of dark ones
  • the powder coatings according to the invention can also be applied to light substrates or in opaque layers. However, the color impression, which depends on the viewing angle, is only weakly expressed.
  • the powder effect coatings according to the invention can be coated with a clear lacquer by customary methods. In principle, all known clearcoats or transparent pigmented coating agents are suitable as clearcoats. Both solvent-containing one-component or two-component lacquers and preferably water-dilutable clear lacquers and in particular conventional powder lacquers can be used here.
  • the clearcoat contains further auxiliaries which improve the surface properties of the coated objects. Examples include UV stabilizers and light stabilizers that protect the layers underneath from degradation reactions.
  • the powder effect coatings according to the invention can be produced in a few simple process steps, in high yield and without the occurrence of non-recyclable waste and can be applied by all technically known methods for powder coating without the use of solvents or other conventional binders. In addition to being easy to process, they are characterized by high temperature stability, solvent and
  • parts mean parts by weight.
  • 1, 4: 3,6-Dianhydro-D-sorbitol (isosorbide) are in a reactor with 52326 parts Acetic anhydride added and flushed with a gentle stream of nitrogen. The mixture is heated to 140 ° C. with stirring in the course of 15 minutes and this temperature is maintained for 30 minutes. The temperature is then raised to 335 ° C. within 165 minutes and the melt is stirred at this temperature for a further 30 minutes. Acetic acid begins to distill off at approx. 220 ° C. The nitrogen purge is then stopped and a vacuum is applied. The melt is stirred for a further 30 minutes under vacuum (approx. 5 mbar). It is then aerated with nitrogen and the polymer is discharged and pelletized using an extruder.
  • the polymer melts at 158 ° C and has a greenish golden color from a vertical viewing angle. The color already appears during the condensation in a vacuum and is retained after cooling.
  • Example 1 70 g of the cholesteric LCP prepared in Example 1 are mixed with 0.5% by weight of a hydroxylated polyester, e.g. "®Additol 496" (commercially available from VIANOVA RESINS, 55247 Mainz-Kastel, Boelckestrasse 26), added and mixed for 30 minutes at 200 ° C. in a laboratory kneader. The mixture is then removed from the kneader. The mixture is pre-milled on a granulator to a grain size ⁇ 2mm. The final grinding takes place on a high-performance ultracentrifugal mill with a 0.08 mm sieve separation.
  • a hydroxylated polyester e.g. "®Additol 496” (commercially available from VIANOVA RESINS, 55247 Mainz-Kastel, Boelckestrasse 26)
  • Example 1 70 g of the cholesteric LCP produced in Example 1 are mixed with 0.5% by weight of an acrylate copolymer, for example "®BYK 361" (commercially available from BYK Chemie GmbH, 46462 Wesel) and in one at 30 ° C. Laboratory kneader mixed. The mixture is then removed from the kneader. The mixture is pre-milled on a granulator to a grain size ⁇ 2mm. The final grinding takes place on a high-performance ultracentrifugal mill with a 0.08 mm sieve separation.
  • an acrylate copolymer for example "®BYK 361” (commercially available from BYK Chemie GmbH, 46462 Wesel)
  • Example 4 Preparation of a sprayable LCP powder 70 g of the cholesteric LCP produced in Example 1 are mixed with 0.5% by weight of a polyacrylate adsorbed on silicon dioxide, e.g. "(DResiflow PV5" (commercially available from WORLEE Chemie GmbH, 21481 Lauenburg) and mixed for 30 minutes at 200 ° C. in a laboratory kneader. The mixture is then removed from the kneader. The mixture is pre-milled on a granulator to a particle size of ⁇ 2 mm The final grinding takes place on a high-performance ultracentrifugal mill with a 0.08 mm sieve separation.
  • a polyacrylate adsorbed on silicon dioxide e.g. "(DResiflow PV5" (commercially available from WORLEE Chemie GmbH, 21481 Lauenburg)
  • the mixture is then removed from the kneader.
  • the mixture is pre-milled on a granulator to a
  • Example 5 Production of a powder effect coating with a triboelectric spray gun:
  • Example 2 The powder produced in Example 2 is filled into the powder container of the "®Tribostar" spraying device from Intec, Dortmund.
  • the sprayer is equipped with a standard spray pipe and an inner star rod.
  • This spray device is used to coat an aluminum plate primed with a black powder coating in a spray booth from Intec, Dortmund, with high powder throughput and a spray pressure of 3 bar, by crosswise application.
  • the coated sheet is heated to 220 ° C. for 5 minutes and then the sheet is immersed in water.
  • a homogeneous film is obtained which exhibits a brilliant, greenish-golden color from a vertical viewing angle and a brilliant, greenish-blue color from an oblique viewing angle.
  • Example 6 Production of a powder effect coating with a corona spray gun:
  • Example 2 The powder produced in Example 2 is filled into the powder container of a corona spray gun from Intec, Dortmund. To the electrodes of the Spray gun is applied a voltage of 35 kV. This sprayer is used to coat an aluminum sheet primed with a black powder coating in a spray booth from Werner & Pfleiderer, Stuttgart, with medium powder throughput, by crosswise application. To form a film, the coated sheet is heated to 220 ° C. for 5 minutes and then the sheet is immersed in water. A homogeneous film is obtained which exhibits a brilliant, greenish-golden color from a vertical viewing angle and a brilliant, greenish-blue color from an oblique viewing angle.
  • Example 7 Production of a powder effect coating with a triboelectric spray gun:
  • Example 3 The powder produced in Example 3 is poured into the powder container of the "Tribostar" spraying device from Intec, Dortmund.
  • the sprayer is equipped with a standard spray pipe and an inner star rod.
  • This spray device is used to coat an aluminum plate primed with a black powder coating in a spray booth from Intec, Dortmund, with high powder throughput and a spray pressure of 3 bar, by crosswise application.
  • the coated sheet is heated to 220 ° C. for 5 minutes and then the sheet is immersed in water.
  • a homogeneous film is obtained which exhibits a brilliant, greenish-golden color from a vertical viewing angle and a brilliant, greenish-blue color from an oblique viewing angle.
  • Example 8 Production of a powder effect coating with a triboelectric spray gun:
  • Example 3 The powder produced in Example 3 is poured into the powder container of the "Tribostar" spraying device from Intec, Dortmund.
  • the sprayer is equipped with a standard spray pipe and an inner star rod.
  • This spray device is used to coat an aluminum plate primed with a black powder coating in a spray booth from Intec, Dortmund, with high powder throughput and a spray pressure of 3 bar, by crosswise application. That becomes film formation coated sheet heated to 240 ° C for 5 minutes and then immersed in water.
  • a homogeneous film is obtained which exhibits a brilliant, greenish-golden color from a vertical viewing angle and a brilliant, greenish-blue color from an oblique viewing angle.
  • Example 9 Production of a powder effect coating with a triboelectric spray gun:
  • Example 4 The powder produced in Example 4 is poured into the powder container of the "Tribostar" spraying device from Intec, Dortmund.
  • the sprayer is equipped with a standard spray pipe and an inner star rod.
  • This spray device is used to coat an aluminum plate primed with a black powder coating in a spray booth from Intec, Dortmund, with high powder throughput and a spray pressure of 3 bar, by crosswise application.
  • the coated sheet is heated to 220 ° C. for 5 minutes and then the sheet is immersed in water.
  • a homogeneous film is obtained which exhibits a brilliant, greenish-golden color from a vertical viewing angle and a brilliant, greenish-blue color from an oblique viewing angle.
  • Example 10 Production of a powder effect coating with a triboelectric spray gun:
  • Example 4 The powder produced in Example 4 is poured into the powder container of the "Tribostar" spraying device from Intec, Dortmund.
  • the sprayer is equipped with a standard spray pipe and an inner star rod.
  • This spray device is used to coat an aluminum plate primed with a black powder coating in a spray booth from Intec, Dortmund, with high powder throughput and a spray pressure of 3 bar, by crosswise application.
  • the coated sheet is heated to 240 ° C. for 5 minutes and then the sheet is immersed in water. A homogeneous film is obtained, which under vertical viewing angle shows a brilliant, greenish golden color and from an oblique viewing angle shows a brilliant, greenish blue color.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des revêtements à effet en poudre dont l'impression de couleur dépend de l'angle d'observation. Les revêtements en poudre selon l'invention sont constitués pratiquement d'un ou de plusieurs polymères à cristaux liquides cholestériques, ainsi que d'au moins un additif de mélange du groupe des résines polyesters, polyacrylates et copolymères acrylates hydroxylés.
EP98948874A 1997-09-08 1998-08-26 Revetements en poudre a impression de couleur dependant de l'angle d'observation Withdrawn EP1023403A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1997139260 DE19739260A1 (de) 1997-09-08 1997-09-08 Pulverbeschichtungen mit vom Betrachtungswinkel abhängigem Farbeindruck
DE19739260 1997-09-08
PCT/EP1998/005425 WO1999013012A1 (fr) 1997-09-08 1998-08-26 Revetements en poudre a impression de couleur dependant de l'angle d'observation

Publications (1)

Publication Number Publication Date
EP1023403A1 true EP1023403A1 (fr) 2000-08-02

Family

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EP98948874A Withdrawn EP1023403A1 (fr) 1997-09-08 1998-08-26 Revetements en poudre a impression de couleur dependant de l'angle d'observation

Country Status (4)

Country Link
EP (1) EP1023403A1 (fr)
JP (1) JP2001515944A (fr)
DE (1) DE19739260A1 (fr)
WO (1) WO1999013012A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6710103B2 (en) 2001-09-27 2004-03-23 Basf Corporation Curable, powder-based coating composition including a color effect-providing pigment
US20030059598A1 (en) * 2001-09-27 2003-03-27 Norris William C. Coating system and method for coating a substrate with a powder-based coating composition including a color effect-providing pigment
EP2284215A3 (fr) * 2005-03-18 2011-06-15 Battelle Memorial Institute Résine polyuréthan
CN112724804A (zh) * 2020-12-29 2021-04-30 老虎表面技术新材料（清远）有限公司 一种具有变色效果的粉末涂料组合物及其涂层

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3828876A1 (de) * 1988-08-25 1990-03-08 Henkel Kgaa Verwendung von copolymeren von langkettigen alkylacrylaten mit n-haltigen olefinen als verlaufmittel fuer pulverlacke
DE4430919A1 (de) * 1994-08-31 1996-03-07 Daimler Benz Ag Lack, insbsondere Pulverlack zum Lackieren der Oberflächen von Substraten, insbesondere von Fahrzeugkarosserien
DE19505161A1 (de) * 1995-02-16 1996-08-22 Daimler Benz Ag Effektlack bzw. Effektlackierung, insbesondere für Kraftfahrzeugkarosserien

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9913012A1 *

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Publication number Publication date
WO1999013012A1 (fr) 1999-03-18
JP2001515944A (ja) 2001-09-25
DE19739260A1 (de) 1999-03-11

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