WO2008093228A1 - Apprêts et technique d'application faisant intervenir de tels apprêts - Google Patents

Apprêts et technique d'application faisant intervenir de tels apprêts Download PDF

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Publication number
WO2008093228A1
WO2008093228A1 PCT/IB2008/000230 IB2008000230W WO2008093228A1 WO 2008093228 A1 WO2008093228 A1 WO 2008093228A1 IB 2008000230 W IB2008000230 W IB 2008000230W WO 2008093228 A1 WO2008093228 A1 WO 2008093228A1
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WO
WIPO (PCT)
Prior art keywords
coat
paint
mass
component
coat paint
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PCT/IB2008/000230
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English (en)
Inventor
Toshiya Kitamura
Original Assignee
Basf Coatings Japan Ltd.
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
Priority claimed from JP2007018562A external-priority patent/JP2008184521A/ja
Priority claimed from JP2007018563A external-priority patent/JP2008184522A/ja
Application filed by Basf Coatings Japan Ltd. filed Critical Basf Coatings Japan Ltd.
Publication of WO2008093228A1 publication Critical patent/WO2008093228A1/fr

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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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/002—Priming paints
    • 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
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/26—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment
    • C09D123/28—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C09D123/286—Chlorinated polyethylene

Definitions

  • the invention concerns primers which have excellent adhesion on plastic base materials and especially polyolefin base materials, and which have excellent adhesion with the surface paint film when recoating (repainting) without sanding, and a method of coating in which these primers are used.
  • Polyolefin moldings are often used as parts of automobile outer panels and domestic electrical goods for example and more recently recycled polyolefin moldings have been reused.
  • a primer which contains a chlorinated polyolefin is used in those cases where a two-liquid type topcoat paint which includes a polyisocyanate compound is used as the topcoat paint of a polyolefin molding in order to improve the adhesion of the top-coat paint film on the polyolefin molding.
  • the recoating with primer and top-coat paint can be carried out on a paint film which has not been ground (unsanded) without grinding the paint film which is to be repaired.
  • the inter-layer adhesion of the under-layer paint film and the recoated primer is inadequate.
  • Paint compositions which have as essential components (A) chlorinated polyolefin resin which has a chlorine content of from 10 to 50 mass%, (B) acrylic modified chlorinated polyolefin resin, (C) acrylic resin and/or polyester resin of weight average molecular weight from 2,000 to 50,000 and hydroxyl group value from 10 to 90 mgKOH/g and (D) isocyanate compound in which the ratio of the isocyanate equivalent and the hydroxyl group equivalent [Isocyanate Equ.]/[Hydroxyl Group Equ.] is from 0.5/1.0 to 1.2/1.0 and in which, of the total mass (solid fractions) of the (A), (B) and (C) components, the (A) component accounts for from 3 to 20 mass%, the (B) component accounts for from 5 to 40 mass% and the (C) component accounts for from 40 to 92 mass% are known as two-liquid type paint compositions which have an excellent high gloss appearance, weather resistance, solvent resistance and coating operability and provide excellent adhesion on being coated directly without the
  • resin compositions for coating purposes which have good adhesion on polyolefin base materials which are characterized in that they include as essential components (1 ) polymer which has acetoacetoxy groups in a side chain which has been obtained by polymerizing or copolymerizing an acetoacetoxy group containing monomers with other copolymerizable monomers, as required, in the presence of from 5 to 50 parts by weight of a chlorinated polyolefin resin of chlorine content from 15 to 50 wt% and (2) isocyanate compound are known as resin compositions for coating purposes which have excellent paint storage stability and with which paint films which have excellent adhesion, hot water resistance and gasoline resistance can be formed and which can be coated directly without the need for any pre-treatment such as coating with primer etc. on polyole
  • a primer for use on plastics which is characterized in that it contains (A) chlorinated polyolefin which has a chlorine content of from 16 to 22 wt% and which is of molecular weight from 30,000 to
  • (B) blocked polyisocyanate where an isocyanurate-type aliphatic and/or alicyclic polyisocyanate has been blocked with malonic acid di-alkyl ester and acetoacetic acid ester and (C) polyol resin is known as a primer for use on plastics which has excellent adhesion on polyolefin base material moldings and excellent recoat adhesion on paint films (for example, see Patent Citation 3).
  • the adhesion is good when the polyolefin-based base material molding or paint film has been sanded, there is a problem in that the recoat adhesion is inadequate in the absence of sanding.
  • the present invention is intended to provide primers which have excellent adhesion on plastic base materials, and especially on polyolefin base materials, and which have excellent inter-layer adhesion with underlying paint films, and especially urethane resin-based top-coat paint films, on recoating (repainting), and to provide a method of coating in which these primers are used.
  • the inventor has discovered that by adding a low molecular weight diol and a hardening catalyst to a composition which contains a specified chlorinated polyolefin resin and blocked polyisocyanate compound or a specified hydroxyl group containing polymer diol resin the recoat adhesion on a molding comprising a plastic base material such as a polyolefin base material or a paint film is greatly improved, and the invention is based upon this discovery.
  • the present invention provides a primer which is characterized in that it contains (A) chlorinated polyolefin resin which has a chlorine content of from 5 to 50 mass% and a weight average molecular weight of from 1 ,000 to 100,000, (B) blocked polyisocyanate compound, or
  • the present invention also provides a method for coating plastic moldings which is characterized in that the abovementioned primer and a top-coat paint are coated sequentially on the plastic molding, baked and hardened and a top-coat paint film is formed.
  • the present invention also provides a method for coating plastic moldings which is characterized in that the abovementioned primer and a top-coat paint are coated sequentially on the plastic molding, baked and hardened and then the abovementioned primer and a top-coat paint are coated sequentially on the top-coat paint film, baked and hardened. Furthermore, the present invention provides a method for coating a molding which is characterized in that the abovementioned primer and a top-coat paint are coated sequentially, baked and hardened on the top-coat paint film of a molding on which a top-coat paint has been coated and hardened.
  • the present invention also provides a method for coating a molding in which, in the abovementioned methods for coating a molding, the top-coat paint is a two-liquid type urethane resin paint of the one-coat type.
  • the present invention also provides a method for coating a molding in which, in the abovementioned methods for coating a molding, the top-coat paint comprises two layers, namely a base-coat paint film and a clear paint film, and at least the clear paint is a two-liquid type urethane resin paint.
  • the present invention also provides a method for coating a molding in which, in the abovementioned methods for coating a molding, the top-coat paint comprises three layers, namely a colored base- coat paint film, a pearl base-coat paint film and a clear paint film, and at least the clear paint is a two-liquid type urethane resin paint.
  • a primer of this invention it is possible to obtain paint films which have excellent adhesion of the primer paint film on a plastic base material, and especially a polyolefin base material, and paint films which have excellent inter-layer adhesion of the primer paint film with a urethane resin-based top-coat paint film which forms the base when recoating
  • the (A) component chlorinated polyolefin resin which is used in the invention has a chlorine content of from 5 to 50 mass%, preferably of from
  • the weight average molecular weight of the (A) component chlorinated polyolefin resin is from 1 ,000 to 100,000, preferably from 5,000 to 90,000, and most desirably from 10,000 to 80,000. If the weight average molecular weight exceeds 100,000 then problems arise in that the coating operability becomes poor, and in those cases where it is less than 1 ,000 the resin itself lacks cohesive strength and so a problem arises in that a normal paint film cannot be obtained.
  • Resins where a polymer resin which has a polyolefin resin as the main skeleton has been modified with chlorine can be cited as examples of the (A) component chlorinated polyolefin resin.
  • the (A) component chlorinated polyolefin resin As well as polyethylene resins, polypropylene resins and the like, modified polyolefin resins which have been modified with maleic anhydride or the like, and polyolefin-based polymer compounds which have hydroxyl groups, carboxyl groups, methacryloyl groups, acryloyl groups or epoxy groups, for example, at the ends of the molecules or in the molecular chains can also be cited as examples of the polyolefin resin.
  • the (B) component is a blocked isocyanate compound
  • actual examples of the (A) component chlorinated polyolefin resin that can be used include chlorinated polyethylene resins, chlorinated polypropylene resins, chlorinated ethylene/propylene copolymers, chlorinated ethylene/ vinyl acetate copolymers and modified resins where acid anhydrides such as maleic anhydride and the like have been copolymerized in these chlorinated polyolefin resins.
  • the (B) component is a blocked isocyanate compound
  • a commercial product can be used for the (A) component chlorinated polyolefin resin.
  • the (B) component blocked polyisocyanate compound which can be used in the invention is a compound where the isocyanate groups of a polyisocyanate compound which has two or more isocyanate groups in one molecule have been blocked with a blocking agent. When the blocking agent is eliminated the blocked polyisocyanate compound can be expected to react with the (C) component diol, but basically it fulfills the role of raising the affinity with the top-coat paint film.
  • polyisocyanate compound No particular limitation is imposed upon the polyisocyanate compound provided that it is one which has been used conventionally in coating applications, and various types of polyisocyanate can be used.
  • polyisocyanate such as the aromatic polyisocyanates and aliphatic or alicyclic polyisocyanates, for example, can be used as polyisocyanates of this type.
  • polyisocyanates can be used as prepolymers of the biuret type, the adduct type or the isocyanurate type for example.
  • the use of an aliphatic polyisocyanate is preferred from the viewpoint of weatherability.
  • One type of polyisocyanate can be used on its own, or a mixture of polyisocyanates can be used.
  • the means which are used to block the polyisocyanate compound can be selected appropriately according to the elimination temperature, and they include oximes, active methylene compound, malonic acid dialkyl esters, acetoacetic acid esters, ⁇ -caprolactam, ⁇ -diketone and the like.
  • the (B) component polyol resin which can be used in the invention fulfills the role of heightening the adhesion of the primer paint film on a top-coat paint and, in the case where a hardening agent is used in the top-coat paint, and especially where the top-coat paint is a urethane resin-based paint, it fulfills the role of heightening the cohesive strength by reacting with the polyisocyanate which migrates from the urethane resin-based paint.
  • the (B) component polyol resin has a hydroxyl group value of from 30 to 120 mgKOH/g and preferably of from 40 to 70 mgKOH/g and a weight average molecular weight of from 5,000 to 50,000 and preferably of from 7,000 to 20,000. If the hydroxyl group value of said resin is less than 30 mgKOH/g then the adhesion is reduced due to an inadequate crosslink density in the paint film which is obtained, and if it exceeds 120 mgKOH/g then the storage stability of the primer is reduced due to the reduced compatibility with the chlorinated polyolefin resin (A).
  • the (B) component polyol resin preferably has an acid value of from 0 to 25 mgKOH/g and most desirably it has an acid value of from 0 to 10 mgKOH/g. If the acid value of the (B) component polyol resin exceeds 25 mgKOH/g then the compatibility with the chlorinated polyolefin resin is reduced with the result that the storage stability of the paint is reduced and this is undesirable.
  • polyol resins which have the abovementioned properties can be used for the (B) component polyol resin, and these include acrylic polyol resins and polyester polyol resins.
  • the acrylic polyol resins can be obtained by means of polymerization or copolymerization based on polymerizable unsaturated monomers which contain a hydroxyl group with (meth)acrylic acid esters and/or other copolymerizable monomers as required.
  • Examples of the polymerizable unsaturated monomers which contain a hydroxyl group include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate and hydroxybutyl (meth)acrylate.
  • the alkyl alcohol residues which have from 1 to 18 carbon atoms with which the (meth)acrylates are formed may be any alcohol residue which has a linear chain, branched chain or cyclic alkyl group. One of these may be used, or a combination of two or more types can be used.
  • copolymerizable (meth)acrylic acid based esters include (meth)acrylic acid alkyl esters such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl
  • (meth)acrylate hexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2- ethylhexyl (meth)acrylate and dodecyl (meth)acrylate; cyclic hydrocarbon esters of (meth)acrylic acid such as adamantine methacrylate and isobornyl (meth)acrylate; and aromatic hydrocarbon esters of (meth)acrylic acid such as phenyl (meth)acrylate.
  • One of these can be used, or a combination of two or more types can be used.
  • copolymerizable polymerizable unsaturated monomers include Hosmer (trade name, produced by the Unichemical Co.), epoxy group containing (meth)acrylates such as glycidyl (meth)acrylate 3,4- epoxycyclohexylmethyl methacrylate and 3, 4-epoxycyclohexyl methyl acrylate; polymerizable double bond containing aromatic compounds such as styrene, ⁇ -methylstyrene and p-vinyltoluene; acrylamide compounds such as methacrylamide, acrylamide, N,N-dimethylmethacrylamide and N.N-dimethylacrylamide; 2,2,6,6-tetramethyl-4-piperidyl acrylate; and aliphatic vinyl ether compounds such as ethyl vinyl ether, isopropyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2- ethylhexyl vinyl
  • they also include 2,3-dihydrofuran; trimethoxysilylpropyl (meth)acrylate; maleic acid anhydride esters, itaconic acid anhydride esters, maleic acid esters, fumaric acid esters; acrylonitrile; allyl group containing compounds such as allyl glycidyl ether; alkyl esters of crotonic acid such as methyl crotonate, ethyl crotonate and propyl crotonate; aliphatic carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl pivalate, vinyl crotonate, vinyl caprylate, vinyl laurate and vinyl stearate; and aromatic carboxylic acid vinyl esters such as vinyl benzoate, vinyl cinnamate and vinyl p-t-butylbenzoate.
  • Aronix M-5300 trade name, produced by the Toa Gosei Kagaku Kogyo Co.
  • phthalic acid mono-hydroxyethyl acrylate for example, Aronix M-5400 (trade name, produced by the Toa Gosei Kag
  • copolymerizable (meth)acrylic acid esters and other copolymerizable unsaturated monomers are not essential components, and they can be selected and used appropriately, as required, in the design of a paint film depending on the base material and the intended use.
  • radical polymerization is ideal from the industrial point of view.
  • Organic peroxides such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxycarbonate, t-butyl peroxypivaloate, t- hexyl peoxy-2-ethylhexanoate and methyl ethyl ketone peroxide, and azo- based initiators such as 2,2'-bisazo(2,4-dimethylvaleronitrile), 2,2'-azobis(2- methylpropionitrile) (AIBN) and 2,2'-azobis(2-methyl)butyronitrile) can be cited as examples of polymerization initiators which can be used for radical polymerization.
  • the initiator is not limited to these examples.
  • One of these radical polymerization initiators can be used, or a combination of two or more types can be used.
  • a reaction temperature during radical polymerization of from 60 to 150 0 C is generally preferred. If the temperature is less than 60 0 C then the radical polymerization initiator is unlikely to break down and the reaction is unlikely to proceed, and if it exceeds 150° then even though the radical polymerization initiator is broken down and radicals are produced, they have a very short lifetime and it is unlikely that the growth reaction will proceed effectively.
  • the polymerization time is dominated by the reaction temperature and other conditions and cannot be fixed, but a time of from 2 to 6 hours is generally satisfactory.
  • the (B) component polyester polyol resins can be obtained by reacting polybasic acids with polyhydric alcohols.
  • the polybasic acids include phthalic acid anhydride, terephthalic acid anhydride, isophthalic acid, maleic acid anhydride, phthalic acid, trimellitic acid anhydride, methylenetricyclohexene tricarboxylic acid anhydride, pyro- mellitic acid anhydride, itaconic acid, adipic acid, sebacic acid, azelaic acid, hexahydrophthalic acid anhydride, hymic acid anhydride, succinic acid anhydride and hettoic acid anhydride.
  • polybasic acid can be used or two or more types can be used.
  • polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, neopentyl glycol, butylene glycol, hexanediol, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol and the like, and the lactone such as caprolactone adducts of these alcohols.
  • One type of polyhydric alcohol can be used, or two or more types can be used.
  • polyester polyol resins can also be modified with mono-basic acids, fatty acids, oil components and the like. Moreover, the introduction of hydroxyl groups into said polyester polyol resins is carried out easily with polyhydric alcohols which have three or more hydroxyl groups in one molecule.
  • One type of (B) component polyol resin can be used, or a combination of two or more types can be used.
  • the proportions of the (A) component and the (B) component included are such that, with respect to the total mass of the solid fractions of the (A) component and the (B) component, there is from 50 to 90 mass% of the (A) component and from 50 to 10 mass% of the (B) component. Preferably there is from 60 to 80 mass% of the (A) component and from 40 to 20 mass% of the (B) component.
  • the abovementioned proportions of the (A) component and the (B) component included respectively are the proportions of the resin solid fractions of the (A) component and the (B) component included respectively.
  • the resin solid fractions are the residues on heating measured using the method described in JIS K5601-1-2.
  • the (C) component diol which is used in the invention fulfills the role of improving the ability of the chlorinated polyolefin resin to wet a plastic material and, when recoating, it fulfills the role of heightening the ability to wet the top-coat paint film, and especially a urethane resin-based top-coat paint film, which forms the base, and heightens adhesion.
  • the weight average molecular weight of the (C) component diol is from 120 to 1 ,000, and preferably from 120 to 800.
  • the (C) component low molecular weight diol examples include dipropylene glycol, triethylene glycol, hydrogenated bisphenol A and the like. Furthermore, diols which are the reaction products of dibasic acids and an excess of a diol, and lactone such as caprolactone adducts with these diols and the like can also be used as the (C) component low molecular weight diol.
  • diols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, butanediol, neopentyl glycol, pentanediol, hexanediol, heptanediol, octanediol, butylethylpropanediol, cyclohexanediol, cyclohexanedimethanol and phenyldimethanol.
  • dibasic acids examples include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azeleic acid, sebacic acid, terephthalic acid, isophthalic acid, hexahydro- terephthalic acid, maleic acid, fumaric acid and the like, and the acid anhydrides of these dibasic acids.
  • monoglycidyl compounds such as butyl glycidyl ether, 2-ethylhexyl glycidyl ether, sec-butylphenol glycidyl ether, neodecanoic acid glycidyl ester and the like which include a mono-glycidyl group.
  • the proportion of the (C) component included is from 0.5 to 12 mass%, preferably from 1 to 10 mass%, and most desirably from 1.5 to 8 mass%, with respect to the total mass of the resin solid fractions of the (A) component and the (B) component. If the proportion of the (C) component included is less than 0.5 mass% then the adhesion of the primer paint film on the top-coat paint film, and especially a urethane resin-based top-coat paint film, which forms the base is inadequate, and in those cases where it exceeds 12 mass% the storage stability of the primer falls as the compatibility with the main chlorinated polyolefin resin which forms the (A) component falls, and this is undesirable.
  • the proportion of the (C) component included is the proportion of the effective component of the (C) component included, and here the effective component means in those cases where it has been diluted with a solvent or the like the component not including the solvent or the like.
  • the (D) component hardening catalyst which is used in the invention should be a catalyst which promotes the reaction of the (C) component diol with the reactive component which is included in the top-coat paint film which forms the base and in particular it is preferably a catalyst which is used in urethane resins.
  • the top-coat paint film which forms the base is a urethane resin-based paint film the reaction of the hydroxyl groups of the primer layer of the recoat with the unreacted isocyanate of the urethane resin-based top-coat paint film which forms the base is promoted and the adhesion at the time of un-sanded recoating is improved.
  • the (D) component hardening catalyst is, for example, a tin compound or a zinc compound.
  • tin compounds include tin halides such as tin chloride and tin bromide, and organo-tin compounds such as dibutyltin diacetate and dibutyltin dilaurate and the like
  • zinc compounds include zinc halides such as zinc chloride and zinc bromide and zinc salts of organic acids such as zinc octylate, zinc laurate and the like.
  • tin compound or zinc compound, or a combination of two or more types may be used for the hardening reaction catalyst, and other hardening reaction catalysts may be used conjointly.
  • the proportion of the (D) component included is from 0.01 to 1.5 mass%, preferably from 0.02 to 1.0 mass%, and most desirably from 0.05 to 0.8 mass% with respect to the total mass of the resin solid fractions of the (A) component and the (B) component. If the proportion of the (D) component is less than 0.01 mass% then the promoting effect on the hardening reaction is not realized satisfactorily, and in those cases where it exceeds 1.5 mass% a reduction in the recoat adhesion thought to be due to excessive hardening of the paint film arises, and this is undesirable. Moreover, the proportion of the (D) component included is the proportion of the effective component of the (D) component which is included and the effective component in cases where it has been diluted with a solvent or the like signifies the component not including the solvent or the like.
  • Liquid epoxy resins of low molecular weight, color pigments, true pigments, organic solvents and various types of additive can also be used, as required, in a primer of this invention.
  • color pigments include organic pigments such as the azo-lake based pigments, phthalocyanine pigments, indigo-based pigments, perynone-based pigments, perylene-based pigments, quinophthalone-based pigments, dioxazine-based pigments, quinacridone-based pigments and the like and inorganic pigments such as chrome yellow, yellow iron oxide, red iron oxide, titanium dioxide and the like.
  • the true pigments include kaolin, talc and the like.
  • the organic solvent provided that the various components can be dissolved therein, but those which do not react with isocyanate compounds are preferred in case that the (B) component is a blocked polyisocyanate.
  • examples include aliphatic hydrocarbons such as n-hexane, n-heptane and n-octane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform and carbon tetrachloride, ethers such as dibutyl ether, tetrahydrofuran and 1 ,4-dioxane, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, and esters such as ethyl acetate, n-propyl acetate and n-butyl acetate.
  • One of these solvents may be used, or a combination of two or more types can be used. No particular limitations are imposed upon the method of compounding the various components or the method of adding luster pigments, color pigments, organic solvents and the various types of additive and resin, and a variety of methods can be used, and the order of mixing and the addition order can also be varied.
  • Coating with a coating machine as generally used, such as a machine of the air spray, airless spray, electrostatic air spray, flow-coating or dip-coating type for example, or with a brush after adjusting the primer to the desired viscosity by warming and adding organic solvent, as required, can be used as a suitable method of coating in which a primer of this invention is used, but air spray coating is preferred.
  • the dry paint film thickness of the primer paint film is preferably of from 2 to 15 ⁇ m and most desirably of from 4 to 10 ⁇ m.
  • the top-coat paint is preferably coated wet-on-wet without baking the primer.
  • the top-coat paint may be a paint of the one-coat type, the two-coat type or the three-coat type, and a two-liquid type urethane resin paint is preferred for the paint which forms the uppermost paint film layer. No particular limitation is imposed upon the urethane resin-based top-coat paint, but it should be such that the paint film is formed by the reaction between a polyol and an isocyanate compound.
  • the top-coat paints of the one-coat type may be solid paints or paints which have a metallic tone.
  • the dry paint film thickness of the topcoat paint is preferably from 15 to 40 ⁇ m, and most desirably from 20 to 35 ⁇ m.
  • the two-coat type paints are generally combinations of a colored base-coat paint or a pearlescent base-coat paint, such as a metallic base- coat paint, and a clear paint, and the dry paint film thickness of the base- coat paint is preferably from 10 to 20 ⁇ m and the dry film thickness of the clear paint is preferably from 20 to 40 ⁇ m, and most desirably from 25 to 35 ⁇ m.
  • the three-coat type paints are generally combinations of a colored base-coat paint, a pearlescent base-coat paint and a clear paint, and the dry paint film thickness of the colored base-coat paint is preferably from 5 to 15 ⁇ m, the dry film thickness of the pearlescent base-coat paint is preferably from 5 to 15 ⁇ m, and the dry film thickness of the clear paint is preferably from 20 to 40 ⁇ m, and most desirably from 25 to 35 ⁇ m. In those cases where these paints are over-painted they are preferably all painted wet-on-wet in the unhardened state.
  • Baking and drying conditions for a urethane resin-based top-coat paint of from 5 minutes to 3 days at from 20 to 150 0 C are preferred, and conditions of from 10 to 30 minutes at from 80 to 140 0 C are more desirable.
  • the moldings which are coated with a primer of this invention may be, for example, moldings comprising polyolefin base materials such as polyethylene and polypropylene, and plastic base materials which include polyolefins.
  • the primer can also be used on moldings comprising plastic base materials such as ABS resin, PC resin, nylon and the like.
  • Recoating (repainting) in this invention includes, for example, methods in which a primer of this invention and a top-coat paint are coated sequentially and baked and hardened on a molding on which a top-coat paint has been coated and hardened to form a top-coat paint film, and methods in which recoating is carried out in those cases where dust has been deposited or there is failure of the paint film after a primer of this invention and a top-coat paint have been coated sequentially and baked and hardened on a plastic molding.
  • said primer is coated again after removing the dust and without sanding the whole top-coat paint film and the primer and the top-coat paint should be coated sequentially and baked in essentially the same way as on the first occasion.
  • recoating can be carried out even if part of the top-coat paint film which forms the base has peeled away, and a paint film which has excellent adhesion can be obtained by coating the primer and top-coat paint sequentially and baking.
  • these include automobiles and automobile parts (for example bodies, bumpers, spoilers, mirrors, wheels and interior decorative parts, which are made of a variety of materials), metal sheets such as steel sheets, bicycles, bicycle parts, materials used on roads (for example guard rails, traffic signs, sound-deadening walls and the like), materials used in tunnels (for example side wall panels and the like), ships, railway rolling stock, aircraft, musical instruments, domestic electrical goods, building materials, containers, office accessories, sports accessories, toys and the like.
  • the primer was stored for 10 days at 4O 0 C and its state was evaluated on the basis of the following criteria. O: No abnormality observed ⁇ : Slight separation observed X: Pronounced separation observed
  • a top-coat paint of which the viscosity had been adjusted to a Ford cup #4 (25°C) viscosity of 12 seconds with a diluting solvent (butyl acetate/xylene 70/30 (ratio by mass) solvent mixture) was air spray coated wet-on-wet over a primer paint film which had been coated in such a way as to form a dry film thickness of from 6 to 8 ⁇ m on a commercial black polyolefin plate essentially as described above and left to stand for 5 minutes at room temperature and then dried by being maintained at 90 0 C for 20 minutes.
  • the coating was carried out wet-on-wet in all cases, including the two-coat and three-coat types, in such a way that the dry paint film thickness of the top-coat paint was 25 ⁇ m in the case of a one- coat paint, and in the case of the base paint of a two-coat type the dry paint film thickness was 15 ⁇ m, in the case of the colored base-coat paint of a three-coat type the dry paint film thickness was 10 ⁇ m and in the case of the pearl base-coat paint of a three-coat type the dry paint film thickness was 8 ⁇ m, and in the case of the clear paint the dry film thickness was 30 ⁇ m.
  • the coated sheets obtained were left to stand for 60 minutes at room temperature and then 11 cuts were made with a cutter knife in the paint film in the length and width directions with a spacing of 2 mm to provide 100 squares, peeling was carried out with cellophane tape and the state of peeling was evaluated on the basis of the criteria indicated below.
  • the coating was carried out wet-on-wet in all cases, including the two-coat and three-coat types, in such a way that the dry paint film thickness of the top-coat paint was 25 ⁇ m in the case of a one-coat type paint, and in the case of the base paint of a two-coat type the dry paint film thickness was 15 ⁇ m, in the case of the colored base-coat paint of a three-coat type the dry paint film thickness was 10 ⁇ m and in the case of the pearl base-coat paint of a three-coat type the dry paint film thickness was 8 ⁇ m, and in the case of the clear paint the dry film thickness was 30 ⁇ m.
  • the coated sheet was left to stand for 24 hours at room temperature and then the primer and top-coat paint were coated wet-on-wet with an air spray in essentially the same way as on the first occasion and left to stand for 5 minutes at room temperature and dried for 20 minutes at 8O 0 C.
  • the coated sheets obtained were left to stand for 60 minutes at room temperature and then 11 cuts were made with a cutter knife in the paint film in the length and width directions with a spacing of 2 mm to provide 100 squares, peeling was carried out with cellophane tape and the state of peeling was evaluated on the basis of the criteria indicated below.
  • Resin syntheses were carried out in the same way as in Example of Resin Production 1 with the raw materials shown in Table 1 and the diol resin solutions C-2 to C-4 shown in Table 1 were obtained.
  • the raw material "Cardura E-10" in Table 1 is a mono-glycidyl ester of versatic acid (produced by the Japan Epoxy Resin Co.).
  • Chlorinated polypropylene resin solution (trade name "Hardren CY9122", produced by the Toyo Kasei Kogyo Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 50,000 to 60,000, resin solid fraction 20%) (525 parts), 99 parts of Typake CR-90 (titanium oxide, produced by the lshihara Sangyo Co.), 0.1 part of pigment black FW200 beads (carbon black, produced by the Degussa Co.) and 0.9 part of TSY-1 (yellow pigment, produced by the Toda Pigment Co.) were introduced into a dispersing container and dispersed until the particle size was less than 15 ⁇ m.
  • Typake CR-90 titanium oxide, produced by the lshihara Sangyo Co.
  • pigment black FW200 beads carbon black, produced by the Degussa Co.
  • TSY-1 yellow pigment, produced by the Toda Pigment Co.
  • the primers P-2 to P-17 shown in Tables 2 and 3 were obtained in the same way as in Example of Primer Production 1.
  • Pigment Black FW200 Beads Carbon black, produced by the Degussa Co.
  • PRINTEX L Electrically conductive carbon black, produced by the Degussa Co.
  • TSY-1 Yellow pigment, produced by the Toda Pigment Co.
  • Hardren CY9122 Produced by the Toyo Kasei Kogyo Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 50,000 to 60,000, residue on heating 20 mass%.
  • Superclon 892L Produced by the Nippon Seishi Chemical Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 60,000 to 70,000, residue on heating 20 mass%.
  • Desmodure BL3175 Produced by the Sumitomo Beyer Urethane Co., HDI isocyanurate blocked with MEK oxime, NCO content 11.2 mass%, residue on heating 75 mass%.
  • Desmodure BL3272MPA Produced by the Sumitomo Beyer Urethane Co., HDI isocyanurate blocked with ⁇ -caprolactam, NCO content 10.2 mass%, residue on heating 72 mass%.
  • Desmodure BL4265SN Produced by the Sumitomo Beyer Urethane Co., IPDI isocyanurate blocked with MEK oxime, NCO content 8.9 mass%, residue on heating 65 mass%.
  • Acrylic resin LB-9020 (produced by the BASF Coatings Japan Co., residue on heating 55 mass%, hydroxyl group value 56 mgKOH/g) (45.5 parts), 24 parts of Typake CR-90 (titanium oxide, produced by the lshihara Sangyo Co.), 0.1 part of Pigment Black FW200 beads (carbon black, produced by the Degussa Co,) and 0.6 part of TSY-1 (yellow pigment, produced by the Toda Pigment Co.) were introduced into a dispersing container and dispersed until the particle size was less than 10 ⁇ m.
  • the dispersion On reaching the target particle size the dispersion was stopped and 0.2 part of the surface controlling agent Modaflow (produced by the Monsanto Co., acrylic copolymer, residue on heating 100 mass%), 10 parts of xylene and 13.2 parts of butyl acetate were added and stirred thoroughly in a Disper to prepare the uniform main component of the two-liquid top-coat paint T- 1 for one-coat purposes.
  • Sumidure N75 (produced by the Sumitomo Beyer Co., polyisocyanate resin, residue on heating 75 %, NCO content 16.5 mass%) was used as the hardening agent and this was mixed in the proportions of 93.6 parts of the main component and 6.4 parts of the hardening agent and stirred until the mixture was uniform immediately before coating and then used.
  • Acrylic resin LB-9020 (produced by the BASF Coatings Japan Co., residue on heating 55 mass%, hydroxyl group value 56 mgKOH/g) (45.5 parts), 6 parts of the rheology control agent LC-0988 (produced by the BASF Coatings Japan Co., inorganic-based, residue on heating 10 mass%), 2.5 parts of the aluminum flake pigment Alpaste TCR3040 (trade name, produced by the Toyo Aluminum Co., residue on heating 80 mass%, average particle diameter (D 50 ) 17 ⁇ m, average thickness 0.8 ⁇ m), 3 parts of Alpaste 6340NS (trade name, produced by the Toyo Aluminum Co., residue on heating 71 mass%, average particle diameter (D 50 ) 13 ⁇ m, average thickness 0.29 ⁇ m), 3.3 parts of Desmodure BL3175 (trade name, produced by the Sumitomo Beyer Urethane Co., HDI isocyanurate blocked with MEK oxime, NCO content 11.2 mass%, residue on heating 75 mass%)
  • the one-liquid type metallic base-coat paints for two-coat purposes T-3 and T-4 shown in Table 4 were prepared in the same way as in Example of Top-coat Paint Production 2.
  • the main component of the two-liquid type metallic base-coat for two-coat purposes T-5 was prepared by mixing the raw materials shown in Table 4 except for the Sumidure N75 and stirring uniformly in the same way as in Example of Top-coat Paint Production 2.
  • Sumidure N75 as the hardening agent was mixed in the proportions of 96.5 parts of the main component and 3.5 parts of hardening agent immediately before coating, stirred until uniform and used.
  • the main component of a two-liquid type colored base-coat coat for three-coat purposes T-6 was prepared by dispersing the pigment shown in Table 4 and adding the raw materials except for the Sumidure N75 in the same way as in Example of Top-coat Paint Production 1 and stirring uniformly.
  • Sumidure N75 as the hardening agent was mixed in the proportions of 96.5 parts of the main component and 3.5 parts of hardening agent immediately before coating, stirred until uniform and used.
  • the pigment shown in Table 4 was dispersed and the remaining raw materials were added and stirred uniformly in the same way as in Example of Top-coat Paint Production 6 to prepare the one-liquid type colored base- coat paint for three-coat purposes T-7.
  • the main component of the two-liquid type pearl base-coat paint for three-coat purposes T-8 was prepared in the same way as in Example of
  • Top-coat Paint Production 5 except that the aluminum pigment was replaced with a peal pigment.
  • Sumidure N-75 as the hardening agent was mixed in the proportions of 96.5 parts of the main component and 3.5 parts of hardening agent immediately before coating, stirred until uniform and used.
  • the one-liquid type pearl base-coat paint for three-coat purposes T- 9 was prepared in the same way as in Example of Top-coat Paint Production 2 except that the aluminum pigment was replaced with peal pigment.
  • Example of Top-coat Paint Production 10 (Clear paint)
  • the surface control agent Modaflow (0.2 part) and 4.8 parts of butyl acetate were mixed with 80 parts of the acrylic resin LB-9040 (produced by the BASF Coatings Japan Co., residue on heating 55 mass%, hydroxyl group value 78 mgKOH/g) and stirred for 10 minutes in a Disper to prepare the uniform main component of the two-liquid type clear paint T-10.
  • Sumidure N-75 as the hardening agent was mixed in the proportions of 85 parts of the main component and 15 parts of hardening agent immediately before coating, stirred until uniform and used. Table 5 ⁇
  • Alpaste TCR3040 Aluminum pigment produced by the Toyo Aluminum Co., residue on heating 80 mass%, average particle diameter (D 50 ) 17 ⁇ m
  • Alpaste 6340NS Alignment 6340NS (Aluminum pigment produced by the Toyo Aluminum Co., residue on heating 71 mass%, average particle diameter (D 50 ) 13 ⁇ m,
  • Yuban 122 Produced by the Mitsui Kagaku Co., butylated melamine resin, residue on heating 60 mass%
  • Tests were carried out essentially in the same way as in Example 1 except that the top-coat paint was replaced with the combination shown in Table 5, and the results of the evaluations are shown in Table 5.
  • Butylethylpropanediol (187.3 parts), 18.8 parts of trimethylolpropane, 94 parts of 1 ,6-hexanediol, 31.3 parts of phthalic acid anhydride and 295.2 parts of adipic acid were introduced into a glass flask of capacity 2 L which had been furnished with a thermometer and a stirrer and after slowly raising the temperature to 14O 0 C, the temperature was raised to 190 0 C over a period of 3 hours. The mixture was maintained at 190 0 C for 2 hours and then, after the esterification reaction proceeded, the temperature was raised to 210 0 C over a period of 2 hours and the esterification reaction was carried out until the resin acid value fell below 10. The resin so obtained was cooled, 373.4 parts of xylene were added and the polyester polyol resin solution B-1 of weight average molecular weight 14,000, hydroxyl group value 45, acid value 8 and solid fraction 60 mass% was obtained.
  • Resin synthesis was carried out in the same way as in Example of Production 5 with the raw materials shown in Table 2a and the polyester polyol resin solution B-2 shown in Table 2a was obtained.
  • Xylene (300 parts) was introduced into a glass flask of capacity 2 L which had been furnished with a thermometer, a stirrer, a reflux condenser and a monomer drip- feed device and the temperature was slowly raised and reflux was achieved.
  • Resin syntheses were carried out in the same way as in Example of Production 7 with the raw materials shown in Table 3a and the acrylic polyol resin solutions B-4 to B-8 shown in Table 3a were obtained.
  • Chlorinated polypropylene resin solution (trade name "Hardren CY9122", produced by the Toyo Kasei Kogyo Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 50,000 to 60,000, resin solid fraction 20%) (525 parts), 99 parts of Typake CR-90 (titanium oxide, produced by the lshihara Sangyo Co.), 0.1 part of pigment black FW200 beads (carbon black, produced by the Degussa Co.) and 0.9 part of TSY-1 (yellow pigment, produced by the Toda Pigment Co.) were introduced into a dispersing container and dispersed until the particle size was less than 15 ⁇ m.
  • Typake CR-90 titanium oxide, produced by the lshihara Sangyo Co.
  • pigment black FW200 beads carbon black, produced by the Degussa Co.
  • TSY-1 yellow pigment, produced by the Toda Pigment Co.
  • Type CR-90 Titanium oxide, produced by the lshihara Sangyo Co.
  • Acicular Electrically Conductive Titanium Oxide Electrically conductive titanium oxide, produced by the lshihara Sangyo Co.
  • Pigment Black FW200 Beads Carbon black, produced by the Degussa Co.
  • PRINTEX L Electrically conductive carbon black, produced by the Degussa Co.
  • TSY-1 Yellow pigment, produced by the Toda Pigment Co.
  • Hardren CY9122 Produced by the Toyo Kasei Kogyo Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 50,000 to 60,000, residue on heating 20%.
  • Superclon 892L Produced by the Nippon Seishi Chemical Co., maleic anhydride modified chlorinated polypropylene resin, chlorine content 22 mass%, weight average molecular weight from 60,000 to 70,000, residue on heating 20%.
  • Acrylic resin LB-9020 (produced by the BASF Coatings Japan Co., residue on heating 55 mass%, hydroxyl group value 56 mgKOH/g) (45.5 parts), 24 parts of Typake CR-90 (titanium oxide, produced by the lshihara Sangyo Co.), 0.1 part of Pigment Black FW200 beads (carbon black, produced by the Degussa Co.) and 0.6 part of TSY-1 (yellow pigment, produced by the Toda Pigment Co.) were introduced into a dispersing container and dispersed until the particle size was less than 10 ⁇ m.
  • the dispersion On reaching the target particle size the dispersion was stopped and 0.2 part of the surface controlling agent Modaflow (produced by the Monsanto Co., acrylic copolymer, residue on heating 100 mass%), 10 parts of xylene and 13.2 parts of butyl acetate were added and stirred thoroughly in a Disper to prepare the uniform main component of the two-liquid top-coat paint T- 1 for one-coat purposes.
  • Sumidure N75 (produced by the Sumitomo Beyer Co., polyisocyanate resin, residue on heating 75 mass%, NCO content 16.5 mass%) was used as the hardening agent and this was mixed in the proportions of 93.6 parts of the main component and 6.4 parts of the hardening agent and stirred until the mixture was uniform immediately before coating and then used.
  • Acrylic resin LB-9020 (produced by the BASF Coatings Japan Co., residue on heating 55 mass%, hydroxyl group value 56 mgKOH/g) (45.5 parts), 6 parts of the rheology control agent LC0988 (produced by the BASF Coatings Japan Co., inorganic-based, residue on heating 10 mass%) 2.5 parts of the aluminum flake pigment Alpaste TCR3040 (trade name, produced by the Toyo Aluminum Co., residue on heating 80 mass%, average particle diameter (D 50 ) 17 ⁇ m, average thickness 0.8 ⁇ m), 3 parts of Alpaste 6340NS (trade name, produced by the Toyo Aluminum Co., residue on heating 71 mass%, average particle diameter (D 50 ) 13 ⁇ m, average thickness 0.29 ⁇ m), 3.3 parts of Desmodure BL3175 (trade name, produced by the Sumitomo Beyer Urethane Co., HDI isocyanurate blocked with MEK oxime, NCO content 11.2 mass%, residue of heating 75 mass%),
  • the main component of the two-liquid type metallic base-coat for two-coat purposes T-5 was prepared by mixing the raw materials shown in
  • the main component of a two-liquid type colored base-coat coat for three-coat purposes T-6 was prepared by dispersing the pigment shown in Table 6a and adding the raw materials except for the Sumidure N75 in the same way as in Example of Top-coat Paint Production 1 and stirring uniformly.
  • Sumidure N75 as the hardening agent was mixed in the proportions of 96.5 parts of the main component and 3.5 parts of hardening agent immediately before coating, stirred until uniform and used.
  • the main component of the two-liquid type pearl base-coat coat for three-coat purposes T-8 was prepared in the same way as in Example of
  • the one-liquid type pearl base-coat coat for three-coat purposes T-9 was prepared in the same way as in Example of Top Coat Paint Production 2 except that the aluminum pigment was replaced with pearl pigment.
  • Example of Top-coat Paint Production 10 (Clear Paint)
  • the surface control agent Modaflow (0.2 part) and 4.8 parts of butyl acetate were mixed with 80 parts of the acrylic resin LB-9040 (produced by the BASF Coatings Japan Co., residue of heating 55 mass%, hydroxyl group value 78 mgKOH/g) and stirred for 10 minutes in a Disper to prepare the uniform main component of the two-liquid type clear paint T-10.
  • Sumidure N-75 as the hardening agent was mixed in the proportions of 85 parts of the main component and 15 parts of hardening agent immediately before coating, stirred until uniform and used. Table 7a
  • Alpaste TCR3040 Aluminum pigment produced by the Toyo Aluminum Co., residue on heating 80 mass%, average particle diameter (D 50 ) 17 ⁇ m
  • Alpaste 6340NS Alignment 6340NS (Aluminum pigment produced by the Toyo Aluminum Co., residue on heating 71 mass%, average particle diameter (D 50 ) 13 ⁇ m
  • Yuban 122 Produced by the Mitsui Kagaku Co., butylated melamine resin, residue on heating 60 mass%
  • Tests were carried out essentially in the same way as in Example 1a except that the top-coat paint was replaced with the combination shown in Table 7a, and the results of the evaluations are shown in Table 7a.
  • the primers of the present invention have excellent storage stability and coating operability, the adhesion of the first top-coat paint film is excellent and, furthermore, it is possible to obtain paint films where there is excellent adhesion of a recoated paint film.
  • Examples 8 to 12 in Table 5 and Examples 8a to 12a in Table 7a had somewhat reduced adhesion of a recoat paint film, but this was of a level which was not a problem in practical terms.

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Abstract

Apprêt présentant un très bon pouvoir adhésif sur un matériau de base plastique, et avec laquelle l'adhérence inter-couche avec le film de peinture formant la base d'une nouvelle application (peinture de réfection) est excellente; et technique d'application faisant intervenir cet apprêt. Apprêt caractérisé en ce qu'il contient (A) une résine de polyoléfine chlorée ayant une teneur en chlore comprise entre 5 et 50 % en masse et un poids moléculaire moyen compris entre 1 000 et 100 000; (B) un composé polyisocyanate bloqué, ou une résine de polyol ayant une valeur de groupe hydroxyle comprise entre 30 et 120 mkg OH/g et un poids moléculaire moyen compris entre 5 000 et 50 000; (C) un diol dont le poids moléculaire moyen est compris entre 120 et 1 000; et (D) un catalyseur de durcissement. Cet apprêt se caractérise en outre en ce que les proportions par rapport à la masse totale des fractions solide de résine du composant (A) et du composant (B) dans lesquelles ces composants sont inclus se situent entre 0,5 et 12% en masse du composant (C) et entre 0,1 et 1,5 % en masse du composant (D).
PCT/IB2008/000230 2007-01-29 2008-01-28 Apprêts et technique d'application faisant intervenir de tels apprêts WO2008093228A1 (fr)

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JP2007018562A JP2008184521A (ja) 2007-01-29 2007-01-29 プライマー及びそれを用いた塗装方法
JP2007018563A JP2008184522A (ja) 2007-01-29 2007-01-29 プライマー及びそれを用いた塗装方法
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009093097A1 (fr) * 2008-01-23 2009-07-30 Basf Coatings Japan Ltd. Apprêts et procédé de formation d'un revêtement dans lequel ils sont utilisés

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04372641A (ja) * 1991-06-20 1992-12-25 Sanyo Chem Ind Ltd 変性塩素化ポリオレフィンからなるバインダ−
JPH08134400A (ja) * 1994-11-09 1996-05-28 Hitachi Chem Co Ltd 塗料用樹脂組成物及び塗料
JPH08325350A (ja) * 1995-03-31 1996-12-10 Daicel Huels Ltd 熱硬化性樹脂組成物
JP2000265109A (ja) * 1999-03-18 2000-09-26 Toyota Motor Corp ポリプロピレン塗装用プライマー組成物
EP1600484A1 (fr) * 2003-03-04 2005-11-30 Kansai Paint Co., Ltd. Composition blanche de revetement primaire conductrice et procede de formation de film de revetement multicouche

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Publication number Priority date Publication date Assignee Title
JPH04372641A (ja) * 1991-06-20 1992-12-25 Sanyo Chem Ind Ltd 変性塩素化ポリオレフィンからなるバインダ−
JPH08134400A (ja) * 1994-11-09 1996-05-28 Hitachi Chem Co Ltd 塗料用樹脂組成物及び塗料
JPH08325350A (ja) * 1995-03-31 1996-12-10 Daicel Huels Ltd 熱硬化性樹脂組成物
JP2000265109A (ja) * 1999-03-18 2000-09-26 Toyota Motor Corp ポリプロピレン塗装用プライマー組成物
EP1600484A1 (fr) * 2003-03-04 2005-11-30 Kansai Paint Co., Ltd. Composition blanche de revetement primaire conductrice et procede de formation de film de revetement multicouche

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Title
DATABASE WPI Week 199306, Derwent World Patents Index; AN 1993-048661, XP002480186 *
DATABASE WPI Week 199631, Derwent World Patents Index; AN 1996-306844, XP002480183 *
DATABASE WPI Week 199708, Derwent World Patents Index; AN 1997-083503, XP002480185 *
DATABASE WPI Week 200064, Derwent World Patents Index; AN 2000-659235, XP002480184 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009093097A1 (fr) * 2008-01-23 2009-07-30 Basf Coatings Japan Ltd. Apprêts et procédé de formation d'un revêtement dans lequel ils sont utilisés
US8728582B2 (en) 2008-01-23 2014-05-20 Basf Coatings Japan Ltd. Primers and a method of coating in which they are used

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