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US20040192817A1 - Curable compositions - Google Patents

Curable compositions Download PDF

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Publication number
US20040192817A1
US20040192817A1 US10/701,858 US70185803A US2004192817A1 US 20040192817 A1 US20040192817 A1 US 20040192817A1 US 70185803 A US70185803 A US 70185803A US 2004192817 A1 US2004192817 A1 US 2004192817A1
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US
United States
Prior art keywords
composition
molecular weight
polyol
hydroxy
polyisocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/701,858
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English (en)
Inventor
Thomas Staunton
Weilin Tang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sherwin Williams Co
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to US10/701,858 priority Critical patent/US20040192817A1/en
Assigned to SHERWIN-WILLIAMS COMPANY, THE reassignment SHERWIN-WILLIAMS COMPANY, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TANG, WEILIN, STAUNTON, THOMAS J.
Publication of US20040192817A1 publication Critical patent/US20040192817A1/en
Priority to US11/199,693 priority patent/US7279525B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/281—Monocarboxylic acid compounds
    • 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
    • C08G18/08—Processes
    • C08G18/089—Reaction retarding agents
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
    • C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/6262—Polymers of nitriles derived from alpha-beta ethylenically unsaturated carboxylic acids
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • This invention relates to a curable composition
  • a solvent solution of a mixture comprising:
  • a metal catalyst such as a tin compound, for accelerating the isocyanate/hydroxyl reaction
  • compositions of this invention are especially useful as coatings and may typically be utilized as primers, topcoats or as clearcoats and/or basecoats in clearcoat/basecoat compositions and are especially useful in spray applications.
  • the combination of these materials provides fast reacting, durable coatings having extended pot-life and excellent cure.
  • the compositions of this invention could also be utilized as adhesives, elastomers and plastics.
  • propionic acid due to its ease of handling and evaporation rate, has special utility in spray applications and ambient air cures.
  • propionic acid has shown superior performance, especially in high solid spray applications, compared to other similar organic acids such as acetic acid.
  • Two-component curable mixtures comprising polyisocyanates and active hydrogen-containing compounds, such as polyols or polyamines, are well-known in the art to provide excellent performance and cure at low temperatures.
  • active hydrogen-containing compounds such as polyols or polyamines
  • 4,184,031 teaches the use of a composition of matter comprising a metallo organic compound and a carboxylic acid, or a compound convertible thereto, such as a carboxylic anhydride, by reaction with an active hydrogen compound.
  • U.S. Pat. No. 4,341,689 teaches polyurethanes catalyzed by amines and metal compounds in the presence of pot-life extending amounts of acetic or formic acid, but expressly teaches that propionic acid is not useful due to its slow vaporization.
  • This invention also relates to the process of spray application of the solvent borne curable composition and its subsequent cure by exposure to heat, or preferably for certain applications, at ambient temperatures.
  • This invention involves a multi-component curable composition which is reactive upon mixing of the components and which comprises the solvent borne mixture of
  • the hydroxy functional acrylic polymer will be a “film-forming polymer” that can form a film from evaporation of any carrier or solvent.
  • the curable composition of this invention When utilized as a coating or an adhesive, the curable composition of this invention will be used in combination with about 5 to about 80%, and preferably 10 to about 40%, by weight of an inert solvent. It is especially preferred that the curable composition will have a sprayable viscosity less than about 25 seconds, and especially less than about 20 seconds, when measured by a #2 Zahn cup and when formulated to a VOC level of 3.5#/gallon. It is convenient to provide the curable composition as a multicomponent system which is reactive upon mixing the components. Generally, the active hydrogen-containing components and the polyisocyanate component will be maintained in separate packages and mixed just prior to use.
  • the pot-life of the mixture can be significantly extended without adversely affecting cure or other properties of the final cured product.
  • the metal catalyst can be incorporated into either component, or into a diluting solvent ahead of time, but is generally preferred to add the propionic acid to the active hydrogen-containing portion or the diluting solvent rather than the polyisocyanate portion.
  • an object of this invention to provide a method for extending the pot-life of solvent borne mixtures of polyisocyanates and active hydrogen-containing materials by incorporating propionic acid into the mixture. It is a further object of this invention to provide curable, reactive compositions having extended pot-life. Another object of this invention is to provide curable compositions which are useful as primers, topcoats or clearcoats and/or basecoats in clearcoat/basecoat compositions. A preferred object is to provide curable compositions comprising (on a weight solids basis of the vehicle solids):
  • the hydroxy-functional acrylic polymers useful in this invention will have an average of at least two active hydrogen groups per molecule and a number average molecular weight less than about 3,000, and preferably less than about 2,400.
  • the hydroxy-functional acrylic polymers can be conveniently prepared by free radical polymerization techniques as is well known in the art.
  • the acrylic polymers are typically prepared by the addition polymerization of one or more monomers. At least one of the monomers will contain, or can be reacted to produce, a reactive hydroxyl group.
  • hydroxy-functional monomers include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxybutyl acrylate, 4-hydroxypentyl acrylate, 2-hydroxyethyl ethacrylate, 3-hydroxybutyl methacrylate, 2-hydroxyethyl chloroacrylate, diethylene glycol methacrylate, tetraethylene glycol acrylate, para-vinyl benzyl alcohol, etc.
  • the hydroxy-functional monomers would be copolymerized with one or more monomers having ethylenic unsaturation such as:
  • esters of acrylic, methacrylic, crotonic, tiglic, or other unsaturated acids such as: methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, ethylhexyl acrylate, amyl acrylate, 3,5,5-trimethylhexyl acrylate, methyl methacrylate, ethylmethacrylate, propyl methacrylate, dimethylaminoethyl methacrylate, isobomyl methacrylate, ethyl tiglate, methyl crotonate, ethyl crotonate, etc.;
  • vinyl compounds such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl benzoate, vinyl m-chlorobenzoate, vinyl p-methoxybenzoate, vinyl alpha-chloroacetate, vinyl toluene, vinyl chloride, etc.;
  • styrene-based materials such as styrene, alpha-methyl styrene, alpha-ethyl styrene, alpha-bromo styrene, 2,6-diclorostyrene, etc.;
  • allyl compounds such as allyl chloride, allyl acetate, allyl benzoate, allyl methacrylate, etc.;
  • (v) other copolymerizable unsaturated monomers such as ethylene acrylonitrile, methacrylonitrile, dimethyl maleate, isopropenyl acetate, isopropenyl isobutyrate, acrylamide, methacrylamide, dienes such as 1,3-butadiene, and halogenated materials such as 2-(N-ethylperflourooctenesulfonamido)ethyl(meth)acrylate.
  • the polymers are conveniently prepared by conventional free radical addition polymerization techniques. Frequently, the polymerization will be initiated by conventional initiators known in the art to generate a free radical such as azobis(isobutyronitrile), cumene hydroperoxide, t-butyl perbenzoate, etc. Typically, the monomers are heated in the presence of the initiator at temperatures ranging from about 35° C. to about 200° C., and especially 75° C. to 150° C., to effect the polymerization. The molecular weight of the polymer can be controlled, if desired, by the monomer selection, reaction temperature and time, and/or the use of chain transfer agents as is well known in the art.
  • the low molecular weight polyol diluents useful in this invention will typically have number average molecular weights less than about 1,000 and preferably less than about 500 and will include polyether polyols, polycaprolactone polyols and saturated and unsaturated polyols.
  • Representative polyol diluents include diols such as ethylene glycol, dipropylene glycol, 2,2,4-trimethyl 1,3-pentanediol, neopentyl glycol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, 1,4-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-bis(2-hydroxyethoxy)cyclohexane, trimethylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, decamethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, norbornylene glyco
  • Polyisocyanates useful in the compositions of this invention have an average of at least about two isocyanate groups per molecule.
  • Representative polyisocyanates having two or more isocyanate groups per molecule include the aliphatic compounds such as ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, 1,2-propylene, 1,2-butylene, 2,3-butylene, 1,3-butylene, ethylidene and butylidene diisocyanates; the cycloalkylene compounds such as 3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate, and the 1,3-cyclopentane, 1,3-cyclohexane, and 1,2-cyclohexane diisocyanates; the aromatic compounds such as m-phenylene, p-phenylene, 4,4′-diphenyl, 1,5-naphthalene and 1,4-naphthalene diisocyanates; the alipha
  • the ratio of equivalents of isocyanate to active hydrogen can be widely varied within the practice of this invention.
  • the polyisocyanate will typically be present at a level to provide about 0.3 to about 2.0, and preferably about 0.7 to about 1.3 equivalents of isocyanate for each equivalent of active hydrogen from the acrylic resin and polyol diluent.
  • the curable compositions of this invention can be cured at temperatures ranging from about room temperature up to about 350° F.
  • the advantages of using propionic acid are particularly apparent in relatively low temperature cures near ambient room temperature.
  • the curable compositions can be used as clear coatings or they may contain pigments as is well known in the art.
  • Representative opacifying pigments include white pigments such as titanium dioxide, zinc oxide, antimony oxide, etc. and organic or inorganic chromatic pigments such as iron oxide, carbon black, phthalocyanine blue, etc.
  • the coatings may also contain extender pigments such as calcium carbonate, clay, silica, talc, etc.
  • the coatings may also contain other additives such as flow agents, catalysts, solvents, ultraviolet light absorbers, etc.
  • Typical metal catalysts for the reaction between the polyisocyanate and the active hydrogen-containing material include tin, zinc and copper materials such as dibutyl tin dilaurate, zinc octoate, and copper naphthenate.
  • Organometallic tin compounds, such as dibutyltin dilaurate, are preferred in the practice of this invention.
  • the coatings of this invention may typically be applied to any substrate such as metal, plastic, wood, glass, synthetic fibers, etc. by brushing, dipping, roll coating, flow coating, spraying or other method conventionally employed in the coating industry.
  • Spraying is the especially preferred process and while it is not our intent to be bound by theory, it is believed that the volatilization of the coating during spraying at ambient temperatures causes some, but not all, of the propionic acid to evaporate, while the rest evaporates gradually from the film.
  • propionic acid apparently allows the film to remain open, even for high solid applications, long enough for sufficient solvent evaporation to minimize die-back and solvent popping and other potential film problems.
  • the substrates may be primed prior to application of the coatings of this invention.
  • curable compositions of this invention relate to their use as clearcoats and/or basecoats in clearcoat/basecoat formulations.
  • Low VOC clearcoats are an especially useful application of this invention.
  • Clearcoat/basecoat systems are well known, especially in the automobile industry where it is especially useful to apply a pigmented basecoat, which may contain metallic pigments, to a substrate and allow it to form a film followed by the application of a clearcoat.
  • the basecoat composition may be any of the polymers known to be useful in coating compositions including the reactive compositions of this invention.
  • One useful polymer basecoat includes the acrylic addition polymers, particularly polymers or copolymers of one or more alkyl esters of acrylic acid or methacrylic acid, optionally together with one or more other ethylenically unsaturated monomers. These polymers may be of either the thermoplastic type or the thermosetting, crosslinking type which contain hydroxyl or amine or other reactive functionality which can be crosslinked.
  • Suitable acrylic esters for either type of polymer include methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, ethyl acrylate, butyl acrylate , vinyl acetate, acrylonitrile, acrylamide, styrene, vinyl chloride, etc.
  • suitable functional monomers which can be used in addition to those already mentioned include acrylic or methacrylic acid, hydroxy ethyl acrylate, 2-hydroxy propyl methacrylate, glycidyl acrylate, tertiary-butyl amino ethyl methacrylate, etc.
  • the basecoat composition may, in such a case, also contain a crosslinking agent such as a polyisocyanate, a polyepoxide, or a nitrogen resin such as a condensate of an aldehyde such as formaldehyde with a nitrogeneous compound such as urea, melamine or benzoguanamine or a lower alkyl ether of such a condensate.
  • a crosslinking agent such as a polyisocyanate, a polyepoxide, or a nitrogen resin
  • a condensate of an aldehyde such as formaldehyde with a nitrogeneous compound such as urea, melamine or benzoguanamine or a lower alkyl ether of such a condensate.
  • Other polymers useful in the basecoat composition include vinyl copolymers such as copolymers of vinyl esters of inorganic or organic acids, such as vinyl chloride, vinyl acetate, vinyl propionate, etc., which cop
  • polymers useful in the manufacture of the basecoat include alkyd resins or polyesters which can be prepared in a known manner by the condensation of polyhydric alcohols and polycarboxylic acids, with or without the inclusion of natural drying oil fatty acids as described elsewhere in this specification.
  • the polyesters or alkyds may contain a proportion of free hydroxyl and/or groups which are available for reaction, if desired with suitable crosslinking agents as discussed above.
  • the basecoat composition may also contain minor amounts of a cellulose ester, to alter the drying or viscosity characteristics of the basecoat.
  • the basecoat will include pigments conventionally used for coating compositions and after being applied to a substrate, which may or may not previously have been primed, the basecoat will be allowed sufficient time to form a polymer film which will not be lifted during the application of the clearcoat.
  • the basecoat may be heated or merely allowed to air-dry to form the film.
  • the basecoat will be allowed to dry for about 1 to 20 minutes before application of the clearcoat.
  • the clearcoat is then applied to the surface of the basecoat, and the system can be allowed to dry at room temperature or, if desired, can be force dried by baking the coated substrate at temperatures typically ranging up to about 350° F.
  • the clearcoat may contain ultraviolet light absorbers such as hindered phenols or hindered amines at a level ranging up to about 6% by weight of the vehicle solids as is will known in the art.
  • the clearcoat can be applied by any application method known in the art, but preferably will be spray applied. If desired, multiple layers of basecoat and/or clearcoat can be applied. Typically, both the basecoat and the clearcoat will each be applied to give a dry film thickness of about 0.2 to about 6, and especially about 0.5 to about 3.0, mils.
  • novel reactive compositions taught herein could be used as a basecoat, in which case the clearcoat could also comprise the novel reactive coatings taught herein, or the polymers taught herein as being useful as basecoat formulations could be utilized as clearcoats.
  • a representative acrylic polymer was prepared by the free radical polymerization reaction of the following materials in the presence of aromatic naphtha and N-butyl acetate Raw Material Parts by Weight T-Amylethylhexylperoxycarbonate 34.14 Methyl Methacrylate 106.17 Butyl Acrylate 159.14 Hydroxy Ethyl Methacrylate 151.11 Styrene 110.95 Methacrylic Acid 3.27
  • a clearcoating was prepared by admixing the following materials: Raw Material Parts by Weight Acrylic Resin of Example 1 44.15 1,4-Cyclohexanedimethanol 7.21 n-butyl acetate 4.84 ethyl acetate 13.96 Tinuvin ® 292 (light stabilizer from Ciba-Geigy) 1.44 Tinuvin ® 384 (UV absorber from Ciba-Geigy) 1.44 Dibutyltin dilaurate 0.02 Ethyl 3-ethoxypropionate 4.69 Butyl propionate 6.53 Byk TM 300 (flow agent from Byk Chemie) 0.43 Propionic acid 0.72
  • This clearcoating was admixed with 45.17 parts of a 75.2% weight solids solution of Tolonate® HDT LV polyisocyanate acetate in n-butyl (sold by Rhodia) and spray applied over a previously applied basecoat and exhibited excellent flow and leveling, and minimum die-back or solvent popping.
  • a primer formulation was prepared as follows: Raw Material Parts by Weight Acrylic Polymer 1 36.64 n-butyl acetate 2.04 Tone ® 310 polycaprolactone polyol 10.76 From Union Carbide Disperbyk ® 161 dispersant from Byk-Chemie 4.0 Butyl propionate 2.04 Carbon black 0.42 Kaolin clay 11.42 Titanium dioxide 46.58 Barium sulfate 30.77 Dibutyl tin dilaurate 1.50 Propionic acid 0.30 Methyl isobutyl ketone 2.04
  • This pigmented primer/surfacer showed excellent pot life, and when spray applied to a metal substrate showed excellent flow and cure properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Epoxy Resins (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US10/701,858 2002-11-05 2003-11-05 Curable compositions Abandoned US20040192817A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/701,858 US20040192817A1 (en) 2002-11-05 2003-11-05 Curable compositions
US11/199,693 US7279525B2 (en) 2002-11-05 2005-08-09 Curable compositions

Applications Claiming Priority (2)

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US42414602P 2002-11-05 2002-11-05
US10/701,858 US20040192817A1 (en) 2002-11-05 2003-11-05 Curable compositions

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US (2) US20040192817A1 (de)
EP (1) EP1569977B1 (de)
CN (1) CN100351280C (de)
AT (1) ATE398146T1 (de)
AU (1) AU2003287530A1 (de)
BR (1) BR0316023B1 (de)
CA (1) CA2504486C (de)
DE (1) DE60321595D1 (de)
ES (1) ES2304537T3 (de)
MX (1) MXPA05004903A (de)
WO (1) WO2004041894A1 (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050038204A1 (en) * 2003-08-14 2005-02-17 Walters David N. Increased pot-life urethane coatings
US20060089453A1 (en) * 2004-10-26 2006-04-27 Pajerski Anthony D Water-borne dispersions of oil modified urethane polymers
US20060217472A1 (en) * 2005-03-11 2006-09-28 Staunton Thomas J Scratch resistant curable coating composition
US20070190257A1 (en) * 2006-02-10 2007-08-16 Gia Huynh-Ba Coating compositions having improved early hardness
US20080032057A1 (en) * 2006-08-02 2008-02-07 Ford Motor Company Coating compositions and methods of applying the same
US20090246534A1 (en) * 2008-04-01 2009-10-01 The Sherwin-Williams Company Curable compositions

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8461234B2 (en) * 2003-03-14 2013-06-11 Eastman Chemical Company Refinish coating compositions comprising low molecular weight cellulose mixed esters
US8039531B2 (en) * 2003-03-14 2011-10-18 Eastman Chemical Company Low molecular weight cellulose mixed esters and their use as low viscosity binders and modifiers in coating compositions
US8124676B2 (en) * 2003-03-14 2012-02-28 Eastman Chemical Company Basecoat coating compositions comprising low molecular weight cellulose mixed esters
US7585905B2 (en) * 2003-03-14 2009-09-08 Eastman Chemical Company Low molecular weight cellulose mixed esters and their use as low viscosity binders and modifiers in coating compositions
CN101405339B (zh) * 2006-03-17 2010-08-25 木本股份有限公司 聚酯系薄膜用粘合剂组合物及使用其的光学薄膜
US20080085953A1 (en) * 2006-06-05 2008-04-10 Deepanjan Bhattacharya Coating compositions comprising low molecular weight cellulose mixed esters and their use to improve anti-sag, leveling, and 20 degree gloss
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US7279525B2 (en) 2007-10-09
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ATE398146T1 (de) 2008-07-15
CN1720276A (zh) 2006-01-11
CA2504486C (en) 2010-05-11
US20060052525A1 (en) 2006-03-09
BR0316023B1 (pt) 2014-07-01
MXPA05004903A (es) 2005-07-22
WO2004041894A1 (en) 2004-05-21
DE60321595D1 (de) 2008-07-24
EP1569977B1 (de) 2008-06-11
AU2003287530A1 (en) 2004-06-07
CN100351280C (zh) 2007-11-28
BR0316023A (pt) 2005-09-13
EP1569977A1 (de) 2005-09-07

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