WO2001043966A1 - Autodepositing coating composition and process and coated metal articles therefrom - Google Patents
Autodepositing coating composition and process and coated metal articles therefrom Download PDFInfo
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- WO2001043966A1 WO2001043966A1 PCT/US2000/033996 US0033996W WO0143966A1 WO 2001043966 A1 WO2001043966 A1 WO 2001043966A1 US 0033996 W US0033996 W US 0033996W WO 0143966 A1 WO0143966 A1 WO 0143966A1
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- WIPO (PCT)
- Prior art keywords
- general formula
- group
- hydrogen
- acid
- moiety
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- 0 C**(/C=C/C(C)(/C=C1/C(O2)=O)O)/C=C1/C2=O Chemical compound C**(/C=C/C(C)(/C=C1/C(O2)=O)O)/C=C1/C2=O 0.000 description 1
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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
- B05D7/142—Auto-deposited coatings, i.e. autophoretic coatings
- B05D7/144—After-treatment of auto-deposited coatings
Definitions
- This invention relates to a coating composition that provides metal surfaces with an excellent corrosion resistance, adherence, and heat resistance, to a process 5 for coating metal surfaces; and to coated metals. More particularly, this invention relates to a water-based autodepositing coating composition — comprising water-dis- persible or water-soluble organic resin, acid, and oxidizing agent and/or metal ions — that has the ability to provide metal surfaces with an excellent corrosion resistance, adherence, and heat resistance.
- the metal surfaces can be, for example, 0 iron, galvanized, or aluminum surfaces, particularly ferriferous surfaces, and the desirable properties are imparted thereto by successive operations of forming an uncured organic resin coating on the metal surface by effecting contact between the metal surface and the aforesaid autodepositing coating composition, optionally rinsing the resulting coated metal surface with water, and drying the coated or rinsed 5 coated metal surface, preferably with the application of heat.
- the invention also relates to a coating process and to coated metal articles of manufacture.
- this coating formation is achieved by the chemical activity of the coating composition at the metal 0 surface (metal ions eluted from the metal surface by etching acting on the resin particles to induce deposition thereof on the metal surface), this technology is distinguished from electrodeposition by its ability to efficiently form a resin coating on metal surfaces without the external application of electricity.
- Another advantage enjoyed by this technology is that it does not require a pretreatment such as phosphat- ing and can therefore provide a shorter treatment sequence than, for example, elec- trodeposition coating processes.
- Japanese Laid Open Patent Application (PCT) Number Hei 3-505841 505,841/1991
- PCT Japanese Laid Open Patent Application
- a coating treatment for metal surfaces in which the metal surface is treated with a vinylidene chloride resin-based aqueous coating composition and the corrosion resistance of the vinylidene chloride resin is then upgraded by exposing the uncured resin coating prior to its thermal drying to an alkaline aqueous solution.
- This treatment does offer the advantage of not using toxic hexavalent chromium in the chemical treatment that produces an excellent corrosion resistance and adherence in the organic resin coating formed on the metal surface.
- the base component of the organic resin coating is vinylidene chloride resin, which has a poor heat resistance notwithstanding its excellent corrosion resistance.
- An object of this invention is to provide an autodepositing coating composition that can form a simultaneously highly heat-resistant, strongly adherent, and highly corrosion-resistant organic resin coating on metal surfaces (e.g., iron, zinc coating, and aluminum) and that can do so without requiring the use of a chemical treatment (post-treatment).
- Another object of this invention is to provide a process for coating metal surfaces to achieve these same purposes.
- an autodepositing coating composition that comprises water-soluble or water-dispersible anionic polyester resin molecules that can be formed by condensing at least (a) a polyhydric alcohol component and (b) an acid component.
- the invention also provides a process for coating metal surfaces by forming an uncured organic resin coating on the surface of a metal by contacting the metal surface with an autodepositing coating composition as described above, optionally rinsing the coated metal surface with water, and drying the coated metal surface, preferably with the application of heat.
- the invention provides articles of manufacture that comprise coated metal surfaces formed by such a process.
- At least part of the aforesaid polyhydric alcohol component (a) preferably is selected from the group consisting of: (a.1 ) aliphatic polyhydric alcohols that conform to the immediately following general formula (1 ): in which R T represents a divalent organic moiety that: - contains from 1 to 10 carbon atoms; may be either straight-chain or branched; and is one of an unsubstituted alkylene moiety and a partially substituted alkylene moiety in which each substituent is either a hydroxyl moiety or a halo moiety; and (a.2) aromatic polyhydric alcohols that conform to the immediately following general formula (2):
- each of m and n independently is an integer with a value of at least one; - 2 ⁇ (m+n) ⁇ 6; and each of R 2 , R 3 , R 4 , and R 5 is independently either hydrogen or methyl.
- polyhydric alcohols that conform to general formula (1 ) when the moiety represented by Ri is "branched", meaning that this moiety includes at least one carbon atom that is covalently bonded by single bonds to at least three, or more preferably to four, other carbon atoms.
- the single most preferred type of branched polyhydric alcohol is 2,2-dimethyl-1 ,3-propanediol (more commonly called neopentyl glycol).
- polyhydric alcohols that include a branched R, moiety in their molecules and conform to general formula (1 ) as described above preferably constitute a molar percentage of the total moles of polyhydric alcohols in the monomer mixture that is at least, with increasing preference in the order given, 1 , 3, 5, or 9 and independently preferably is not more than, with increasing preference in the order given, 80, 75, 70, 65, 60, 55, or 51.
- At least part of the aforesaid acid component (b) is preferably selected from the group consisting of: (b.1 ) aliphatic compounds that conform to the immediately following general formula (3):
- each of Xi and X 2 is independently selected from the group consisting of hydrogen and alkyl moieties that have not more than 10 carbon atoms in each alkyl moiety; and R 6 represents a divalent organic moiety that: may be straight-chain or branched; has from 1 to 30 carbon atoms; and -- is either an unsubstituted alkylene moiety or a partially substituted alkylene moiety in which each substituent conforms to the general formula -COOX 3 , wherein X 3 is selected from the group consisting of hydrogen and alkyl moieties that have not more than 10 carbon atoms in each alkyl moiety; (b.2) aromatic carboxylic acids and esters and salts thereof that conform to the immediately following general formula (4):
- each of X 4 and X 5 is independently selected from the group consisting of hydrogen and alkyl moieties that have not more than 3 carbon atoms; and each of Y ⁇ , Y 2 , Y 3 , and Y 4 is independently selected from the group consisting of: hydrogen; moieties conforming to the general formula -COOX 6 , wherein X ⁇ is selected from the group consisting of hydrogen, alkyl moieties having not more than three carbon atoms, Na, K, Ca, Ba, Li, and NH 4 ; and moieties conforming to the general formula S0 3 Z ⁇ , wherein Zi is selected from the group consisting of hydrogen, Na, K, (b.3) aromatic anhydrides that conform to the immediately following general formula (5)
- each of Y 5 and Y 6 is independently selected from the group consisting of: hydrogen; moieties conforming to the general formula -COOX 6 ; and moieties conforming to the general formula -SO 3 Z 1 , each of X 6 and Zi having the same meaning as in part (b.2) above; (b.4) the anhydride of pyromeliitic acid, which has the immediately following chemical formula (6):
- each of Y 7 , Y ⁇ , Yg, and Y 10 is independently selected from the group consisting of hydrogen and moieties conforming to the general formula -COOXs, X ⁇ being selected from the group consisting of hydrogen and alkyl moieties with not more than 3 carbon atoms; and (b.6) compounds that would conform to general formula (4) except for having: one additional ring substituent having the general formula -COOX 9 , wherein X 9 is selected from the group consisting of hydrogen, alkyl moieties having not more than three carbon atoms, Na, K, Ca, Ba, Li, and NH 4 ; and no Y 4 moiety.
- X 9 is selected from the group consisting of hydrogen, alkyl moieties having not more than three carbon atoms, Na, K, Ca, Ba, Li, and NH 4 ; and no Y 4 moiety.
- X 9 is selected from the group consisting of hydrogen, alkyl moieties having not more than three carbon atoms, Na,
- component (a) are monomers that are not part of either of the preferred groups of substances as defined in one of parts (a.1 ) and (a.2) as described above; and, independently, not more than, with increasing preference in the order given, 20, 15, 10, or 5 mole % of the monomer residues in the polyester resin used in a composition according to this invention for component (b) are monomers that are not part of any of the preferred groups of substances as defined in one of m parts (b.1 ) through (b.6) as described above.
- the molar ratio of hydroxyl moieties to the total of carboxyl and carboxylate moieties preferably is at least, with increasing preference in the order given, 0.50:1.00, 0.60:1.00, 0.70:1.00, 0.80:1.00, 0.90:1.00, 0.95:1.00, or 0.98:1.00 and independently preferably is not more than, with increasing preference in the order given, 1.50:1.00, 1.40:1.00, 1.30:1.00, 1.20:1.00, 1 .15:1.00, 1.10:1.00, 1.08:1.00, 1.06:1.00, 1.04:1.00, or 1.02:1.00.
- Suitable polyhydric alcohols of type (a.1 ) are specifically exemplified by ethyl- ene glycol, neopentyl glycol, dibromoneopentyl glycol, 1 ,2-propanediol, 1 ,3-propane- diol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,5-pentanediol, 1 ,6-hexanediol, 3-methylpen- tanediol, 1 ,4-cyclohexanedimethanol, 3-methyl-1 ,5-pentanediol, 2-methyl-1 ,3-pro- panediol, 2,2-dimethyl-1 ,3-propanediol, glycerol, pentaerythritol, trimethylolethane, and trimethylolpropane.
- Suitable polyhydric alcohols of type (a.2) are specifically exemplified by the ethylene oxide adducts of bisphenol A, the propylene oxide adducts of bisphenol A, the ethylene oxide adducts of bisphenol F, and the propylene oxide adducts of bisphenol F.
- the aliphatic carboxylic acids, salts, and esters that conform to general formula (3) are specifically exemplified by succinic acid, methylsuccinic acid, ethyl- succinic acid, butylsuccinic acid, the monomethyl ester of succinic acid, the dimethyl ester of succinic acid, the monoethyl ester of succinic acid, the diethyl ester of succinic acid, the monobutyl ester of succinic acid, the dibutyl ester of succinic acid, glutaric acid, methylglutaric acid, ethylglutaric acid, butylglutaric acid, the monomethyl ester of glutaric acid, the dimethyl ester of glutaric acid, the monoethyl ester of glutaric acid, the diethy
- Aromatic carboxylic acids, salts, and esters that conform to general formula (4) are specifically exemplified by terephthalic acid, the monomethyl ester of tere- phthalic acid, the dimethyl ester of terephthalic acid, the monoethyl ester of terephthalic acid, the diethyl ester of terephthalic acid, isophthalic acid, the monomethyl ester of isophthalic acid, the dimethyl ester of isophthalic acid, 5-sulfoisophthalic acid, salts of 5-sulfoisophthalic acid (e.g., the Li, Na, and K salts), dimethyl 5-sulfo- isophthalate, the salts of dimethyl 5-sulfoisophthalate (e.g., the Li, Na, K, Ca, Ba, and NH salts), trimellitic acid, the 1 ,4-dimethyl ester of thmellitic acid, pyromeliitic acid, the 1 ,4-
- Naphthalene-nucleus containing compounds that conform to general formula 7 are specifically exemplified by 1 ,2-naphthalenedicarboxylic acid, the dimethyl ester of 1 ,2-naphthalenedicarboxyiic acid, 1 ,3-naphthalenedicarboxylic acid, the dimethyl ester of 1 ,3-naphthalenedicarboxylic acid, 1 ,4-naphthalenedicarboxylic acid, the dimethyl ester of 1 ,4-naphthalenedicarboxylic acid, 1 ,5-naphthalenedicarboxylic acid, the dimethyl ester of 1 ,5-naphthalenedicarboxylic acid, 1 ,6-naphthalenedicarboxylic acid, the dimethyl ester of 1 ,6-naphthalenedicarboxylic acid, 1 ,7-naphthalene- dicarboxyiic acid, the dimethyl ester of 1 ,7-naphthalenedicarboxylic
- At least 60 % of moles of the total acid component are selected from the group consisting of compounds conforming to general formula (4), general formula (5), and formula (6).
- not more than 40 % of moles of the total acid component consists of selections from the group consisting of - molecules conforming to general formula (4) when at least one of Yi through
- Y 4 in general formula (4) represents:
- -COOX 6 and X 6 is selected from the group consisting of hydrogen, Na, K, Ca, Ba, Li, or NH 4 ; or
- -SO 3 .Z 1 and Z ⁇ is selected from the group consisting of hydrogen, Na, K, Ca, Ba, Li, and NH 4 ); and molecules conforming to general formula (5) when (b)-3 in which at least one of Y 5 and Y 6 in general formula (5) represents:
- -COOX7 and X 7 is selected from the group consisting of hydrogen, Na, K, Ca, Ba, Li, and NH 4 ; or -- -SO3Z2 and Z 2 is selected from the group consisting of hydrogen, Na,
- the weight average molecular weight of the polyester resin used by this invention may range from 3,000 to 50,000.
- the polyester resin used by this invention can be prepared by subjecting the above-described polyhydric alcohol component and acid component to an este ⁇ fica- tion (or transeste ⁇ fication) reaction at a temperature in the range from 140 to 300
- a polyester resin used in this invention preferably is anionic.
- anionic surfactant can be added as the aforementioned surfactant in order to impart anionicity.
- Said anionic surfactant can be exemplified by alkylbenzenesulfo- nates, alkyl disulfates, alkyl diphenyl ether disulfonates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene aryl ether sulfates, carboxylate surfactants, phos- phate surfactants, naphthalenesulfonic acid/formaldehyde condensates, and polycar- boxylate surfactants.
- the anionic surfactant should be added within a range that makes possible a stable dispersion of the polyhydric alcohol component/acid component condensate in water.
- Nonionic surfactant may be added on an optional basis within a range that does not impair the objects of the invention.
- Suitable nonionic surfactants are exemplified by polyoxyethylene alkyl ethers wherein the alkyl is, for example, octyl, decyl, lauryl, stearyl, or oleyl; polyoxyethylene alkylphenyl ethers wherein the alkyl is, for example, octyl or nonyl; and polyoxyeth- ylene-polyoxypropylene block polymers.
- Water-soluble resin containing sulfonic acid moieties and/or salts thereof, carboxyl moieties and/or salts thereof, and/or phos- phoric acid moieties and/or salts thereof may also be added.
- Sufficient anionicity for stability of the aqueous solution and/or dispersion of a polymer used in this invention can also be conferred by the presence in the acid component (b) of a sufficient fraction of one or more selections from: preferred subgroup (b.2) in which at least one of Yi through Y 4 in general formula (4) is:
- -COOX ⁇ and X 6 represents hydrogen, Na, K, Ca, Ba, Li, or NH 4 ; or -SO 3 Z 1 and Z 1 represents hydrogen, Na, K, Ca, Ba, Li, or NH 4 ; and preferred subgroup (b.3) in which at least one of Y 5 and Y 6 in general formula (5) is: -- -COOX and X represents hydrogen, Na, K, Ca, Ba, Li, or NH 4 ; or
- the autodepositing coating composition of this invention can be obtained by intermixing water-dispersible or water-soluble polyester resin obtained as described above with acid and oxidizing agent and optionally a compound that supplies metal ions and adding additional water as necessary.
- Said acid can be exemplified by at least one selection from fluorozirconic acid, fluorotitanic acid, fluorosilicic acid, fluoro- boric acid, hydrofluoric acid, phosphoric acid, and nitric acid. Hydrofluoric acid is particularly preferred for the acid.
- Suitable as the oxidizing agent are, for example, potassium permanganate, hydrogen peroxide, and sodium nitrite, among which hy- drogen peroxide is particularly preferred.
- the compound that can supply metal ions is not critical as long as it is stable in the coating composition.
- This metal ions source can be exemplified by ferric nitrate, ferric fluoride, ferrous phosphate, and co- baltous nitrate, with ferric fluoride being particularly preferred.
- the content of the organic resin in the water-based coating composition used by this invention is preferably from 5 to 550 g/l and more preferably is from 50 to 100 g/l.
- the acid concentration is preferably from 0.1 to 5.0 g/l and more preferably is from 0.5 to 3.0 g/l.
- the concentration of the oxidizing agent is preferably from 0.01 to 3.0 g/l and more preferably is from 0.03 to 1.0 g/l.
- a metal ions source it is preferably used in a concentration not exceeding 50 g/l as the metal ions and more preferably is used at from 1.0 to 5.0 g/l as the metal ions.
- the technique employed to coat metal surfaces with the water-based coating composition of this invention is not critical, but immersion is particularly preferred.
- the treatment temperature and the treatment time again are not critical, but suitable conditions in the case of immersion are immersion for 10 to 300 seconds and preferably 30 to 180 seconds in coating composition maintained within a temperature range from 15 to 30 °C and preferably from 20 to 25 °C. Treatment outside these ranges is less likely to achieve the objects of this invention.
- the coating weight of inventive coating composition on the metal surface is not critical, but the post-drying film thickness of the organic resin coating preferably is from 5 to 40 micrometres (this unit being hereinafter usually abbreviated as " ⁇ m") and more preferably is from 10 to 25 ⁇ m.
- ⁇ m this unit being hereinafter usually abbreviated as " ⁇ m"
- the desired coating performance often is not obtained at a film thickness below 5 ⁇ m, while films thicker than 40 ⁇ m are prone to blistering, which substantially impairs the quality of the appearance.
- Coating treatment according to the present invention comprises a process in which: preferably, prior to application of the coating composition the metal surface is degreased and rinsed with water; necessarily, an uncured organic resin coating is formed on the metal surface using a coating composition including the polymer condensate of components (a) and (b) as described above; preferably, the coated metal surface is subsequently rinsed with water; and necessarily, the coating or rinsed coating is dried, preferably with the application of heat. While the drying temperature and time are not critical, the drying temperature preferably is from 80 to 200 °C and more preferably is from 100 to 180 °C, and the drying time preferably is from 5 to 60 minutes and more preferably is from 10 to 30 minutes. Treatment outside these ranges is less likely to achieve the objects of this invention.
- the coating composition of this invention may contain a coalescing agent, as known in the autodeposition art, in an amount that is not more than 10 % by weight of the organic resin solids
- This coalescing agent can be, for example, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monopropyl ether, t ⁇ methylpentanediol isobutyr- ate, and 2-ethylhexyl diglycol.
- the coating composition optionally may also contain the above-described anionic surfactant and/or nonionic surfactant, with the goal of maintaining an even better coating composition stability
- the coating composition optionally may also contain pigments, for example, carbon black, phthalocyanine blue, phthalocyanme green, and barium sulfate.
- the water-based autodepositing coating composition used by this invention must contain anionic polyester resin as described above, but it may also contain — within a range that does not impair the objects of this invention — other water- dispersible or water-soluble organic res ⁇ n(s) such as acrylic resin, urethane resin, epoxy resin, melamine resin, or phenolic resin.
- water-based autodepositing coating composition according to the present invention to coat metal surfaces and particularly ferriferous metal surfaces functions to impart thereto an excellent corrosion resistance, adherence, and heat resistance and does so without any post-treatment (chemical treatment of the uncured resin film prior to drying).
- test panel thus prepared was subjected to a 500-hour salt-spray test in accordance with Japanese Industrial Standard ("JIS") Z-2371. Peeling with tape was carried out after salt-spray exposure, and the peel width (both sides, maximum, in miliimeter(s)) from the cross cut was evaluated.
- JIS Japanese Industrial Standard
- the monomers used to make the polyester resins used by this invention are reported in Table 1. Amounts of 1.0 mole of total acid monomer(s) as shown in Tab- le 1 , 2.0 moles of total alcohol monomer(s) as shown in Table 1 , and, as catalysts, 0.25 gram of calcium acetate and 0.10 gram of n-butyl titanate were introduced into a 1.0 liter size round bottom flask fitted with a Claisen adapter and an air-cooled condenser. The interior of the system was purged with nitrogen, followed by heating to 180 °C and melting of the contents. The temperature of the interior of the flask was then raised to 200 °C, and the flask contents were stirred for approximately 2 hours while heating at this temperature.
- the temperature was subsequently raised to 260 °C, after about 15 minutes the interior of the flask was evacuated to a pressure of 0.5 millimeters of mercury, and reaction was continued for approximately 3 hours. Then the reaction products were cooled under a nitrogen current and removed from the flask after cooling was complete.
- the water-based resin emulsion was made by mixing the reaction products thus made with sufficient water to give a final solids content of 25 % solids in the emulsion and sufficient aqueous ammonia to bring the final pH of the solution within the range from 6.0 - 7.0, all the components of this mixture being stirred together for 2 hours while heating to 100 °C in an autoclave.
- the molecular weights of the polymers formed were measured by gel permeation chromatography, using a ShodexTM GPC KF-803 column with an inside diameter of 8 millimeters and a length of 300 millimeters, tetrahydrofuran as eluent, and polystyrene as the molecular weight standard.
- the resulting weight-average molecu- lar weights are also shown in Table 1 .
- Water-based coating compositions were prepared that contained: for both comparative examples, 1.00 g/l of hydrofluoric acid, 3.0 g/l of ferric fluoride, and 0.10 g/l of hydrogen peroxide; for Comparative Example 1 only, 130 g/l of RhoplexTM WL- 91 acrylic resin from Rohm and Haas, which is reported by its supplier to contain 41.5 % of non-volatile solids; and for Comparative Example 2 only, 109 g/l of DaranTM SL143 vinylidene chloride-type resin from W. R. Grace, which is reported by its supplier to contain 55 % resin solids.
- compositions were used under the same conditions as for Examples 1 to 9 to produce coated panels, except that for Comparative Example 2 only, the following process conditions were changed or added: immersion in the autodepositing composition was 150 seconds instead of 180 seconds; after water-rinsing, there was an added operation of immersion of the uncured organic resin coating for 1 minute in an aqueous solution of ammonium bicarbonate with a pH value of 8.0; and drying was at 110 instead of 180 °C. The coating performance tests were run on the resulting panels. The results of the evaluation testing performed in the working and comparative examples are reported in Table 3.
- Example 1 which employed an acrylic resin, gave a poor corrosion resistance.
- Comparative Example 2 which employed a vinylidene chloride-type resin, gave a poor heat resistance.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/168,205 US20030212181A1 (en) | 1999-12-17 | 2000-12-15 | Autodepositing coating composition and process and coated metal articles therefrom |
CA002395072A CA2395072A1 (en) | 1999-12-17 | 2000-12-15 | Autodepositing coating composition and process and coated metal articles therefrom |
EP00989269A EP1268191A4 (en) | 1999-12-17 | 2000-12-15 | Autodepositing coating composition and process and coated metal articles therefrom |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JPH11/358257 | 1999-12-17 | ||
JP35825799A JP3860693B2 (en) | 1999-12-17 | 1999-12-17 | Self-depositing type coating composition, method for coating metal surface, and coated metal material |
Publications (1)
Publication Number | Publication Date |
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WO2001043966A1 true WO2001043966A1 (en) | 2001-06-21 |
Family
ID=18458358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2000/033996 WO2001043966A1 (en) | 1999-12-17 | 2000-12-15 | Autodepositing coating composition and process and coated metal articles therefrom |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1268191A4 (en) |
JP (1) | JP3860693B2 (en) |
CN (1) | CN1259152C (en) |
CA (1) | CA2395072A1 (en) |
WO (1) | WO2001043966A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004076024A (en) * | 2002-08-09 | 2004-03-11 | Nippon Paint Co Ltd | Aluminum base material treatment method and product |
US20080160199A1 (en) * | 2006-12-01 | 2008-07-03 | Manesh Nadupparambil Sekharan | High peroxide autodeposition bath |
JP6043689B2 (en) * | 2013-07-31 | 2016-12-14 | 日本パーカライジング株式会社 | Self-deposition type coating composition for various metal materials and method for producing the same, metal material having organic resin film and method for producing the same |
EP3397402B1 (en) | 2015-12-31 | 2023-05-24 | Henkel AG & Co. KGaA | Low bake autodeposition coatings |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4366195A (en) * | 1979-03-27 | 1982-12-28 | Amchem Products, Inc. | Formation of polymeric coatings |
US5380590A (en) * | 1992-09-16 | 1995-01-10 | Teijin Limited | Water-dispersible aromatic polyester, aqueous dispersion thereof and polyester film coated therewith which permits fast adhesion |
US5510417A (en) * | 1992-04-21 | 1996-04-23 | Toyo Boseki Kabushiki Kaisha | Aqueous polyester dispersion suitable for use as a coating composition |
US5760112A (en) * | 1994-02-23 | 1998-06-02 | Henkel Corporation | Water-borne autodepositing coating compositions |
US5853944A (en) * | 1998-01-13 | 1998-12-29 | Xerox Corporation | Toner processes |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ138993A3 (en) * | 1992-07-15 | 1994-02-16 | Herberts & Co Gmbh | Aqueous, thermosetting coating composition, process of its preparation and use |
JPH0938573A (en) * | 1995-07-25 | 1997-02-10 | Nippon Parkerizing Co Ltd | Coating method for metal surface |
JP3736958B2 (en) * | 1998-01-14 | 2006-01-18 | 日本パーカライジング株式会社 | Corrosion-resistant coating method for metal surfaces |
-
1999
- 1999-12-17 JP JP35825799A patent/JP3860693B2/en not_active Expired - Fee Related
-
2000
- 2000-12-15 CA CA002395072A patent/CA2395072A1/en not_active Abandoned
- 2000-12-15 EP EP00989269A patent/EP1268191A4/en not_active Withdrawn
- 2000-12-15 WO PCT/US2000/033996 patent/WO2001043966A1/en not_active Application Discontinuation
- 2000-12-15 CN CN 00136616 patent/CN1259152C/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4366195A (en) * | 1979-03-27 | 1982-12-28 | Amchem Products, Inc. | Formation of polymeric coatings |
US5510417A (en) * | 1992-04-21 | 1996-04-23 | Toyo Boseki Kabushiki Kaisha | Aqueous polyester dispersion suitable for use as a coating composition |
US5380590A (en) * | 1992-09-16 | 1995-01-10 | Teijin Limited | Water-dispersible aromatic polyester, aqueous dispersion thereof and polyester film coated therewith which permits fast adhesion |
US5760112A (en) * | 1994-02-23 | 1998-06-02 | Henkel Corporation | Water-borne autodepositing coating compositions |
US5853944A (en) * | 1998-01-13 | 1998-12-29 | Xerox Corporation | Toner processes |
Non-Patent Citations (1)
Title |
---|
See also references of EP1268191A4 * |
Also Published As
Publication number | Publication date |
---|---|
JP3860693B2 (en) | 2006-12-20 |
JP2001172560A (en) | 2001-06-26 |
EP1268191A1 (en) | 2003-01-02 |
CN1300644A (en) | 2001-06-27 |
CN1259152C (en) | 2006-06-14 |
EP1268191A4 (en) | 2003-02-12 |
CA2395072A1 (en) | 2001-06-21 |
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