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WO2003080695A1 - Agent reticulant pouvant etre dilue dans l'eau - Google Patents

Agent reticulant pouvant etre dilue dans l'eau Download PDF

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Publication number
WO2003080695A1
WO2003080695A1 PCT/DE2003/000982 DE0300982W WO03080695A1 WO 2003080695 A1 WO2003080695 A1 WO 2003080695A1 DE 0300982 W DE0300982 W DE 0300982W WO 03080695 A1 WO03080695 A1 WO 03080695A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
dilutable
polyisocyanate
nco groups
group
Prior art date
Application number
PCT/DE2003/000982
Other languages
German (de)
English (en)
Inventor
Dieter Hille
Karsten Jahny
Paul Lamers
Original Assignee
Ppg Industries Lacke 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 Ppg Industries Lacke Gmbh filed Critical Ppg Industries Lacke Gmbh
Priority to EP03724850A priority Critical patent/EP1517936A1/fr
Priority to AU2003229271A priority patent/AU2003229271A1/en
Priority to DE10391698T priority patent/DE10391698D2/de
Publication of WO2003080695A1 publication Critical patent/WO2003080695A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
    • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
    • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8077—Oximes

Definitions

  • the present invention relates to a new water-dilutable crosslinker, and its use in automotive OEM painting.
  • crosslinking agent is understood here and below to mean those compounds which bring about a spatial linkage of polymer chains (or else polyfunctional monomers) to one another to form a network polymer (crosslinking).
  • Such a car paint layer generally consists of a total of four different layers (four-layer structure). These four layers are applied one after the other in separate painting systems.
  • the first layer which is located directly on the car sheet, is an electrophoretically applied layer (electrocoat layer, KTL layer), which is applied by electro-dip coating - mainly cathodic dip coating (KTL) - for corrosion protection and then baked.
  • the second layer located on the electrocoat layer and about 30 to 40 ⁇ m thick, is a so-called filler layer, which on the one hand offers protection against mechanical attacks (stone chip protection function) and on the other hand ensures a sufficient level of topcoat, ie smoothes the rough surface of the body shell for the subsequent topcoat and fills out minor bumps.
  • the paints used to produce this filler layer contain not only binders but also pigments.
  • the wettability of the pigments used has a decisive influence on the top coat level of the entire multi-layer coating and also on the gloss of the filler layer, as required by some automobile manufacturers.
  • the filler layer is largely created by application with electrostatic high-speed rotary bells and subsequent baking at temperatures above 130 ° C.
  • the third layer on the filler layer is the basecoat layer, which gives the body the desired color through the use of appropriate pigments.
  • the basecoat is applied in the conventional spraying process.
  • the layer thickness of this conventional basecoat is between about 12 and 25 ⁇ m depending on the color. This layer is usually applied in two process steps, especially with metallic effect paints.
  • the application is carried out by means of electrostatic high-speed rotary bells, followed by a second application by means of pneumatic atomization.
  • This layer is dried (when using an aqueous basecoat) with infrared radiators and / or by hot air convection.
  • the fourth and uppermost layer on the basecoat is the clearcoat, which is usually applied in one application using electrostatic high-speed rotary bells. It gives the body the desired shine and protects the basecoat from environmental influences (UV radiation, salt water, etc.). The basecoat and the clearcoat are then baked together.
  • the fillers used in the manufacture are still based to a considerable extent on solvents and reach a solids concentration of up to 60%. This high solids concentration ensures efficient application and thus a good top coat level of the finished multi-layer coating. Examples of such a conventional filler are mentioned in WO 01/02457.
  • water-soluble or water-dispersible OH-functional binders mostly those based on branched, saturated polyesters and / or on the basis of polyurethanes - are combined with water-dispersible, blocked polyisocyanates.
  • these blocked isocyanates they are modified with carboxyl groups. Dimethylolpropionic acid is very often used for this modification.
  • the carboxyl group-containing, blocked polyisocyanate thus produced is then neutralized with suitable amines, for example with dimethylethanolamine, and dispersed in water.
  • the object of the present invention is to provide a crosslinking agent which can be used in water-dilutable filler formulations, these water-dilutable filler formulations reaching a solids concentration of more than 50%.
  • Another object of the present invention is that the crosslinker does not degrade the overall property level of the filler formulation produced therewith in comparison with the prior art.
  • the stone chip resistance with good grindability is an essential property.
  • a water-dilutable crosslinker without free NCO groups and with at least two blocked NCO groups per molecule and a ratio of blocked NCO groups to OH groups of more than 3: I obtainable from the reaction of an alkanolamine with at least a partially blocked polyisocyanate with an NCO equivalent weight between 600 and 10,000 g / mol NCO (based on free NCO groups) to an intermediate product which has at least one urea bond resulting from the nitrogen atom of the alkanolamine and the free NCO group of the partially blocked polyisocyanate , followed by addition of a cyclic carboxylic acid anhydride with ring opening to the OH group of the intermediate derived from the alkanolamine.
  • blocking agent does not include the alkanolamine used, which reacts with the free NCO group of the partially blocked polyisocyanate to form a urea bond.
  • the choice of the NCO equivalent weight as a criterion for the partially blocked polyisocyanates that can be used ensures that the alkanolamine reacts with the partially blocked polyisocyanate in such a way as to ensure sufficient stability of the crosslinker in aqueous dispersion.
  • the starting components are implemented using the well-known methods of organic chemistry (see e.g. Plastics Manual, Volume 7: Polyurethane, published by Dr. Y. Oertel, Carl Hanser Verlag, Kunststoff, Vienna 1983).
  • reaction is carried out in the presence of water-miscible and volatile solvents which are inert to isocyanates.
  • Methyl ethyl ketone and / or acetone is preferably used.
  • the crosslinker thus obtained is converted into an aqueous phase by neutralizing the carboxyl groups with amines and / or amino alcohols.
  • suitable compounds are ammonia, tertiary amines, such as trimethylamine, triethylamine and / or amino alcohols, such as dimethylethanolamine, diethylethanolamine, methyldiethanolamine or triethanolamine.
  • Neutralization can take place in the organic phase or in the aqueous phase.
  • Dimethylethanolamine is preferably used as the neutralizing agent. If the crosslinking agent according to the invention is used in suitable water-dilutable filler formulations, a solids concentration of more than 50% can be achieved.
  • the crosslinker according to the invention is suitable in principle for crosslinking all resins which have OH groups and are compatible with it.
  • the layers produced from such filler formulations give the resulting multilayer coating an excellent topcoat level and very good stone chip resistance.
  • the partially blocked polyisocyanate is obtainable from
  • the partially blocked polyisocyanate thus obtainable still has an NCO equivalent weight between 600 and 10,000 g / mol NCO (based on free NCO groups).
  • Ethylene glycol diethylene glycol, triethylene glycol, tetraethylene glycol, hexaethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol can be used as diols for this purpose.
  • the diol is preferably selected from the group of hexanediol, neopentyglycol, 1, 4 - Dimethylolcyclohexane, ethylene glycol and propylene glycol.
  • Trimethylolpropane, glycerol, pentaerythritol, dipentaerythritol and / or di (trimethylolpropane) can be used as polyols.
  • the polyol is preferably selected from the group of trimethylolpropane and dimerized trimethylolpropane.
  • the object of the present invention is achieved by one of the aforementioned water-dilutable crosslinking agents which is present in a mixture with at least one additional polyisocyanate which has at least two completely blocked NCO groups per molecule, that is to say is at least difunctional.
  • This additional polyisocyanate is, in particular, one which has no carboxyl group and is consequently not water-dispersible by itself. Even if it is only a mixture of the crosslinking agent according to the invention with a non-water-dispersible polyisocyanate, the addition of the crosslinking agent according to the invention in an appropriate amount results in sufficient dispersibility and stability of the resulting mixture. This corresponding amount can easily be determined by a person skilled in the art by simple experiments.
  • a preferred process for the preparation of this mixture according to the invention is to start from an unblocked polyisocyanate and to react it with a suitable blocking agent in a stoichiometric ratio such that a sufficient number of free NCO groups remains to react with the alkanolamine and the Cyclic carboxylic acid anhydride to create enough free carboxyl groups with regard to stability and dispersibility of the finished, aqueous dispersion.
  • the ratio of crosslinking agent according to the invention to non-water-dispersible polyisocyanate is chosen such that the resulting mixture has an acid number of at least 15 mg KOH / g, in particular at least 25 mg KOH / g.
  • blocking agents include phenol, diethyl malonate, acetoacetic ester, butanone oxime and / or ⁇ -caprolactam.
  • the blocking agent is preferably selected from the group of methyl ethyl ketoxime, 3,5-dimethylpyrazole and ⁇ -caprolactam.
  • the cyclic carboxylic acid anhydride is preferably selected from the group of phthalic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, succinic anhydride and maleic anhydride.
  • the cyclic carboxylic anhydride trimellitic anhydride is very particularly preferred.
  • IPDI 3,5,5-Trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane
  • Desmodur W 4,4'-diisocyanatodicyclohexylmethane
  • 1,3-bis (l.) are preferably used as polyisocyanate having at least two free NCO groups -isocyanato-l -methylethyl) benzene (TMXDI), hexamethylene diisocyanate (HDI), diphenylmethane-4,4'-diisocyanate (MDI), 2,4- and / or 2,6-tolylene diisocyanate (TDI).
  • the polyisocyanate containing at least two free NCO groups can also be a polyisocyanate containing at least three free NCO groups, in particular 2,4,6-trioxo-1,3,5-tris (6-isocyanatohexyl) hexahydro-1,3. 5-triazine (Desmodur N3300).
  • alkanolamines can be used as alkanolamine.
  • the alkanolamines used according to the invention have a hydrogen atom bonded to the nitrogen atom. These include, for example, I-amino-3-propanol, I-amino-2-propanol (isopropanol-amine), I-amino-4-butanol, I-amino-5-pentanol, l, r-iminodi-2-propanol ( Diisopropanolamine), 2- (2-aminoethoxy) ethanol.
  • tertiary alkanolamines are not to be used.
  • Alkanolamines are preferably used in which at least one OH group of the alkanolamine is connected to the nitrogen atom via a substituted or unsubstituted alkyl group having 2 to 6 carbon atoms in the main chain.
  • Examples include aminobutanol, 1-amino-5-pentanol, aminohexanol, 2- (2-aminoethoxy) ethanol, isopropanolamine, diisopropanolamine, 2-amino-2-methyl-1-propanol and 2-amino-2 -methyl- 1, 3-propanediol to name.
  • Bis- (2-hydroxyethyl) amine (diethanolamine) and / or 1-amino-2-ethanol (monoethanolamine) are particularly preferably used as alkanolamine for the preparation of the crosslinking agent according to the invention.
  • the crosslinker according to the invention is particularly suitable for crosslinking OH-containing polymers, in particular in fillers based on saturated polyesters.
  • crosslinked lacquer films obtainable therefrom show improved properties in relation to the topcoat level and the stone chip resistance compared to comparable lacquer films of the prior art.
  • They can generally be spray painted, e.g. Compressed air, hot or airless spraying, or by electrostatic painting processes, e.g. by means of rapidly rotating bells (mini bells), electrostatic automatic or hand spray guns with air support, or by rollers, e.g. applied in a band painting process.
  • electrostatic painting processes e.g. by means of rapidly rotating bells (mini bells), electrostatic automatic or hand spray guns with air support, or by rollers, e.g. applied in a band painting process.
  • the reaction mixture was then heated to 80 ° C and the reaction continued for one hour.
  • the measured NCO content at this time was ⁇ 0.01%.
  • 65.9 g of trimellitic anhydride were added to this resin solution.
  • 61.1 g of dimethylethanolamine and 1374.3 g of deionized water were metered in, so that the temperature did not drop below 60 ° C.
  • a stable dispersion with an acid number of 30 mg KOH / g, a solids content of 50% and a viscosity of 30 mPas was obtained.
  • the mixture was predispersed in a dissolver for thirty minutes and then ground on a sand mill to a grain fineness ⁇ 10 ⁇ m. The temperature was kept below 40 ° C during the milling process.
  • Example 4.1 Preparation of a filler formulation according to the invention:
  • the filler was prepared by mixing 441 g of the pigment paste according to Example 3 and 313 g of a polyacrylate latex (manufactured according to US Pat. No. 5,830,928 with a solids content of 42%), 276 g of the crosslinking agent from Example I with 26 g of Cymel 325 and 20 g Butyl diglycol and 2.2 g of dimethylethanolamine and 37.6 g of deionized water.
  • the viscosity of the filler was 28 s with a solids content of 53%.
  • Example 4.2 Preparation of a filler formulation not according to the invention (comparative example): The filler was made by mixing 441 g of the pigment paste according to Example 3 and 313 g of a
  • Polyacrylate latex (manufactured according to US 5,830,928 with a solids content of 42%), 552 g of the
  • the viscosity of the filler was 27 s with a solids content of 43%.
  • customary and known steel test panels were used, which were coated with a 20 ⁇ m thick electrocoat, produced from a commercially available cationic electrocoat.
  • test panels were pneumatically coated with the filler according to Example 4.1 or 4.2.
  • the resulting filler layers were predried at 80 ° C for eight minutes and then for 20 minutes. long baked at a temperature of 140 ° C.
  • a filler layer with a layer thickness of 35 ⁇ m was obtained.
  • a commercially available conventional solid-color topcoat was applied pneumatically to the filler layer and after ten minutes of flashing off at room temperature and eight minutes of predrying at 80 ° C. for 30 minutes at 140 ° C.
  • the solid color coating of the resulting multi-layer coating had a layer thickness of 30 ⁇ m.
  • the solids determination was carried out in a convection oven by baking at a temperature of 120 ° C. For this, I g of the substance to be tested were applied to patent lids (diameter 75 mm), evenly distributed over the surface, and dried in the oven for one hour. The non-volatile content was then determined by weighing the lids back. A triple determination has been carried out.
  • the layer thickness was determined using the Surfix device from Phynix.
  • the degree of gloss was determined using the haze-gloss device from BYK Gardner at an angle of 60 °.
  • the stone chip resistance was tested using a stone chip tester according to VDA, model 508 from Erichsen GmbH + Co KG.
  • test sheets were bombarded twice with a pressure of 2 bar each with 500 g quenched iron shot "diamond", square, size 4-5 mm.
  • the pendulum hardness was determined using a pendulum hardness tester from BYK-Gardner.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un agent réticulant pouvant être dilué dans l'eau, ne comportant pas de groupes NCO libres, et comportant au moins deux groupes NCO bloqués par molécule, le rapport des groupes NCO bloqués sur les groupes OH étant supérieur à 3 : 1. L'agent réticulant selon l'invention peut être obtenu par mélange d'une alcanolamine avec au moins un polyisocyanate partiellement bloqué, de masse équivalente de NCO comprise entre 600 et 10.000 g/MolNCO (par rapport aux groupes NCO libres), de manière à obtenir un produit intermédiaire présentant au moins une liaison urée résultant de l'atome d'azote de l'alcanolamine et du groupe NCO libre du polyisocyanate partiellement bloqué, puis par addition d'un anhydride d'acide carboxylique cyclique au groupe OH provenant de l'alcanolamine, avec ouverture du cycle. L'invention concerne également l'utilisation dudit agent réticulant dans la peinture automobile.
PCT/DE2003/000982 2002-03-27 2003-03-25 Agent reticulant pouvant etre dilue dans l'eau WO2003080695A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP03724850A EP1517936A1 (fr) 2002-03-27 2003-03-25 Agent reticulant pouvant etre dilue dans l eau
AU2003229271A AU2003229271A1 (en) 2002-03-27 2003-03-25 Water-dilutable cross-linking agent
DE10391698T DE10391698D2 (de) 2002-03-27 2003-03-25 Wasserverdünnbarer Vernetzer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2002114027 DE10214027B4 (de) 2002-03-27 2002-03-27 Wasserverdünnbarer Vernetzer
DE10214027.8 2002-03-27

Publications (1)

Publication Number Publication Date
WO2003080695A1 true WO2003080695A1 (fr) 2003-10-02

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ID=28050955

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2003/000982 WO2003080695A1 (fr) 2002-03-27 2003-03-25 Agent reticulant pouvant etre dilue dans l'eau

Country Status (4)

Country Link
EP (1) EP1517936A1 (fr)
AU (1) AU2003229271A1 (fr)
DE (2) DE10214027B4 (fr)
WO (1) WO2003080695A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3021134B1 (fr) 2014-05-14 2023-01-06 Lg Electronics Inc Terminal mobile

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0355682A2 (fr) * 1988-08-19 1990-02-28 Hoechst Aktiengesellschaft Utilisation de résines de polyuréthanes pour compositions aqueuses de charges
EP0414099A2 (fr) * 1989-08-22 1991-02-27 BASF Aktiengesellschaft Produit de réaction, procédé pour sa préparation et un matériau sensible à la radiation ainsi obtenu
DE19849208A1 (de) * 1998-10-26 2000-04-27 Herberts Gmbh Wäßriges Zweikomponentenbeschichtungsmittel und dessen Verwendung bei der Mehrschichtlackierung
US6248225B1 (en) * 1998-05-26 2001-06-19 Ppg Industries Ohio, Inc. Process for forming a two-coat electrodeposited composite coating the composite coating and chip resistant electrodeposited coating composition
WO2002024778A2 (fr) * 2000-09-22 2002-03-28 Ppg Industries Ohio, Inc. Polyurethanes durcissables, revetements prepares a partir desdits polyurethanes et procede de production de ces elements

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2556621C2 (de) * 1975-12-16 1984-10-11 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von in Wasser dispergierbaren Polyhydroxylverbindungen
DE2845988C3 (de) * 1978-10-23 1981-10-08 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung kathodisch abscheidbarer Elektrotauchlackbindemittel
US4409381A (en) * 1981-12-28 1983-10-11 Ford Motor Company Novel diblocked diisocyanate urea urethane oligomers and coating compositions comprising same
JP3051938B2 (ja) * 1990-06-04 2000-06-12 関西ペイント株式会社 自己硬化性樹脂の製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0355682A2 (fr) * 1988-08-19 1990-02-28 Hoechst Aktiengesellschaft Utilisation de résines de polyuréthanes pour compositions aqueuses de charges
EP0414099A2 (fr) * 1989-08-22 1991-02-27 BASF Aktiengesellschaft Produit de réaction, procédé pour sa préparation et un matériau sensible à la radiation ainsi obtenu
US6248225B1 (en) * 1998-05-26 2001-06-19 Ppg Industries Ohio, Inc. Process for forming a two-coat electrodeposited composite coating the composite coating and chip resistant electrodeposited coating composition
DE19849208A1 (de) * 1998-10-26 2000-04-27 Herberts Gmbh Wäßriges Zweikomponentenbeschichtungsmittel und dessen Verwendung bei der Mehrschichtlackierung
WO2002024778A2 (fr) * 2000-09-22 2002-03-28 Ppg Industries Ohio, Inc. Polyurethanes durcissables, revetements prepares a partir desdits polyurethanes et procede de production de ces elements

Also Published As

Publication number Publication date
AU2003229271A1 (en) 2003-10-08
DE10214027A1 (de) 2003-10-16
EP1517936A1 (fr) 2005-03-30
DE10391698D2 (de) 2005-02-17
DE10214027B4 (de) 2004-09-30

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