WO1985001695A1 - Compositions de revetement flexibles composees d'une couche de base et d'une couche transparente - Google Patents

Compositions de revetement flexibles composees d'une couche de base et d'une couche transparente Download PDF

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Publication number
WO1985001695A1
WO1985001695A1 PCT/US1983/001599 US8301599W WO8501695A1 WO 1985001695 A1 WO1985001695 A1 WO 1985001695A1 US 8301599 W US8301599 W US 8301599W WO 8501695 A1 WO8501695 A1 WO 8501695A1
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WO
WIPO (PCT)
Prior art keywords
basecoat
clearcoat
hydroxy
composition
flexible
Prior art date
Application number
PCT/US1983/001599
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English (en)
Inventor
Dolores J. Alexander
Kenneth R. Kurple
Panagiotis I. Kordomenos
Original Assignee
Ford Motor Company
Ford Motor Company Of Canada, Limited
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 Ford Motor Company, Ford Motor Company Of Canada, Limited filed Critical Ford Motor Company
Priority to AU22629/83A priority Critical patent/AU559366B2/en
Priority to PCT/US1983/001599 priority patent/WO1985001695A1/fr
Priority to JP58503733A priority patent/JPS61500173A/ja
Publication of WO1985001695A1 publication Critical patent/WO1985001695A1/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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • 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
    • C09D175/06—Polyurethanes from polyesters

Definitions

  • This invention relates to flexible basecoat/clearcoat coating systems which have excellent adherence to metal and plastic substrates and possess superior weathering properties.
  • Basecoat/clearcoat systems comprise a finish of a clearcoat top layer in film adherence to a basecoat that is in adherence to a substrate. More particularly, the invention relates to basecoat/clearcoat coating compositions which comprise hydroxy-containing urethane modified polyester, amine-aldehyde crosslinker, and, optionally, a high molecular weight linear polyurethane.
  • the hydroxy-containing urethane modified polyesters of the pigmented basecoat are made by reacting polyester polyol resins with isocyanate, while the novel hydroxy-containing urethane modified polyesters of the clearcoat are made from urethane modified diols reacted with polyol and diacid component.
  • U.S. Patent 3,882,189 and U.S. Patent 3,962,522 are exemplary of numerous patents which describe flexible coating compositions wherein the resin comprises polyurethane modified polyesters formed by reacting polyisocyanate with polyester polyols. These resins are cured with amine aldehyde crosslinkers. It is taught therein, that the presence of the urethane groups in the polymer significantly contributes to the flexibility as well as improved weathering properties, gloss, and abrasion resistance of the coating. However, while it is thus desirable to employ a substantial number of urethane groups in these resins, the amount which may be included in these types of resins is limited.
  • the basecoat/clearcoat coating composition of this invention is characterized in that: the clearcoat composition comprises:
  • hydroxy-containing urethane modified polyester having a number average molecular weight (M n ) of between about 1000 and about 10,000, (ii) having a hydroxyl number of between about 30 and about 200, and (iii) containing between about 1 and about 10 urethane groups per molecule, and being made from reactants comprising:
  • urethane modified diol made by reacting: (a) diol, and
  • acid component selected from dicarboxylic acids and anhydrides thereof.
  • the basecoat composition comprises:
  • hydroxyl-containing urethane modified polyester having a number average molecular weight (M n ) of between about 1000 and about 10,000, (ii) having a hydroxyl number of between about 50 and about 250, and (iii) containing between about 1 and about 7 urethane groups per molecule, and being made from reactants comprising:
  • hydroxy functional polyester prepared from a mixture of (a) polyhydroxy materials comprising diols and triols with (b) acid component selected from dicarboxylic acids and anhydrides thereof; and (2) diisocyanate; wherein in forming the hydroxyl functional polyester, the proportion of reactants (a) and (b) are selected so that the OH/COOH ratio is from about 6:2 to about 6:5; and wherein in forming the modified polyester, the proportion of hydroxy functional polyester (1) and the diisocyanate (2) are selected so as to provide from about 4:1 to about 10:1 hydroxyl/isocyanate groups;
  • the polyhydroxy materials (a) comprise the diols and triols in a hydroxyl equivalent ratio of from about 4:1 to about 1:4, more preferably this ratio is from about 3:1 to about 3:2.5.
  • the basecoat composition and the clearcoat composition may optionally individually comprise up to about 60 weight percent, based on the total weight of (A) and (B) of each composition, of a linear polyurethane having a number average molecular weight of between about 15,000 and about 40,000, preferably of between about 20,000 and about 30,000.
  • the flexible basecoat/clearcoat coating compositions of the invention of this application possess superior weathering properties as well as excellent adhesion to metal and plastic, thus making them well suited for use as coatings on various car components.
  • these improved weathering properties are a result of the clearcoat compositions of the basecoat/clearcoat coating composition of this application.
  • the urethane linkages are advantageously incorporated into the backbone of the modified polyester, since they are formed in an initial reaction of diisocyanate with the diol, rather than being incorporated into the polyester in a later reaction step as is done when forming prior art urethane polyester resins. It has now been found that the initial incorporation of the urethane linkage into the backbone of the modified polyester allows the formation of more flexible coatings with improved weathering properties, particularly suitable to form automotive basecoat/clearcoat coatings.
  • This invention is directed to flexible basecoat/clearcoat coating compositions which comprise hydroxy-containing urethane modified polyester crosslinkable with amine-aldehyde crosslinking agent.
  • the hydroxy-containing urethane modified polyesters of the basecoat are made by reacting polyester polyol resins with with isocyanate, while the hydroxy-containing urethane modified polyesters of the clearcoat are made from urethane modified diols reacted with polyol and diacid component.
  • Either or both of the basecoat and clearcoat composition may optionally include a high molecular weight linear polyurethane.
  • the hydroxy-containing urethane modified polyester of the clearcoat coating composition of this invention has a number average molecular weight (M n ) of between about 1000 and about 10,000, preferably between about 2000 and about 4000.
  • M n number average molecular weight
  • This modified polyester has a hydroxy number of between about 30 and about 200, preferably between about 50 and about 120. It also contains between about 1 and about 10 urethane groups per molecule.
  • One of the reactants used to form the hydroxy-containing urethane modified clearcoat polyester is a urethane modified diol which is made by reacting diol and diisocyanate.
  • the diols employed in making the urethane modified diol include, but are not limited to, alkylene glycols, such as butylene glycol, neopentyl glycol, 1,5,pentene glycol, 3-cyclohexene-1,1-dimethynol, and other glycols such as hydrogenated bisphenol A, caprolactone diol (i.e., the reaction product of caprolactone and ethylene glycol), hydroxy alkylated bisphenols, polyether glycols, e.g., poly(oxytetramethylene) glycol, polyester diols, e.g., 2, 2-dimethyl-3-hydroxypropyl-2, 2-dimethyl-3-hydroxypropionate, and the like.
  • alkylene glycols such as butylene glycol, neopentyl glycol, 1,5,pentene glycol, 3-cyclohexene-1,1-dimethynol
  • other glycols such as hydrogenated bis
  • Preferred diols are neopentyl glycol and 2,2-dimethyl-3-hydroxypropyl-2,2-dimethyl3-hydroxy-propionate, the latter material being commercially available as Esterdiol 204 (a trademark of and available from Union Carbide Corp., New York, N.Y.). While a number of types of diols have been mentioned above as suitable for use as the diol component in making the urethane modified diol of this invention, their disclosure is not meant to be limiting. A great many diols are known in the art. Selection of other diols which would be suitable for use in forming the urethane modified diol would be well within the skill of those in the art.
  • diols may also be employed in making the urethane modified diol.
  • the diisocyante employed in making the urethane modified diol may be essentially any diisocyanate. Many such organic diisocyanates are known in the art. Suitable diisocyanates include hydrocarbon diisocyanate or substituted hydrocarbon diisocyanate, such as 1,6-hexamethylene diisocyanate, isophorone diisocyanate, p-phenylene diisocyanate, biphenyl diisocyanate, toluene diisocyanate, and 3, 3-dimethyl-4,4-biphenylene diisocyanate.
  • the diisocyanate may be any of a number of aliphatic, cycloaliphatic, and aromatic diisocyanates, it is preferred that the diisocyanate be an aliphatic diisocyanate, such as 4,4-dicyclohexylmethanediisocyanate. As would be apparent to those skilled in the art, mixtures of various diisocyanates may also be employed at the diisocyanate component used in forming the urethane-modifying diol.
  • the polyol component used in forming the hydroxy-containing urethane modified polyester of the clearcoat comprises at least about 5 weight percent triol (based on the weight of the polyol component).
  • Preferred triols are conventional low molecular triols such as 1,2,6-hexene triol, 1,1,1-trimethylol propane, pentaerythritol, 3-(2-hydroxy-pro ⁇ oxy)-l, 2-pro ⁇ anediol and polycaprolactone triols, which are commercially available as, for example, PCP-301 (trademark. Union Carbide Corp., New York, N.Y.).
  • This polyol component may also comprise. in addition to the triols, other polyol materials such as diols or tetrols.
  • these other polyols when employed, consist of diols.
  • suitable diols which may be included in the polyol component are those which have been disclosed above as suitable for forming the urethane modified diol of the clearcoat.
  • Preferred diols for use in the polyol component are linear aliphatic type diols.
  • the polyol component may comprise materials such as diols in addition to the triols, the polyol component may consist essentially of triols. By employing diols in the polyol component in addition to the triols the flexibility of the coating composition is generally increased.
  • the polyol component to be used in forming the hydroxy-containing urethane modified polyester of the clearcoat will be dependent on the particular desired properties and application of the coating composition.
  • the polyol preferably comprises from about 10 to about 80 weight percent triols and from about 90 to about 20 weight percent diols.
  • the acid component which is used to form the modified polyester of the clearcoat comprises aliphatic, aromatic, cycloaliphalic dicarboxylic acids or anhydrides thereof.
  • Preferred dicarboxylic acids are the C 6 - C 12 acids, which include adipic, azelaic, sebasic, or dodecane dicarboxylic acid, or cyclohexanedicarboxylic acid. More preferably, the dicarboxylic acids employed are aliphatic dicarboxylic acids, most preferably additionally being linear. Mixtures of suitable acids and/or their anhydrides may also be used as the acid component in this invention.
  • the diol (a) and the diisocyanate (b) described above are combined and reacted, generally at an elevated temperature, so as to form the urethane modified diol.
  • the ratio of the diol to diisocyanate i.e., a molar excess of diol
  • This urethane modified diol is then combined and reacted with the polyol and acid components, generally in the presence of a catalyst and at elevated temperatures, so as to effect formation of a hydroxy-containing urethane modified polyester.
  • Suitable catalysts for the carboxy/hydroxy condensation reaction include such catalysts as tetraisopropyl titanate, strong acids such as p-toluene sulfonic acid, phosphoric acid, sulfuric acid and materials such as zinc oxide, antimony oxide (Sb 2 O 3 ) . and sodium acetate. Other catalysts will be apparent to those skilled in the art.
  • the hydroxy-containing urethane modified polyester of the basecoat co ating composition has a number average molecular weight (M n ) of between about 1,000 and about 10,000, preferably between about 2000 and about 4000. This modified polyester has a hydroxy number of between about 50 and about 250. It also contains between about 1 and about 7 urethane groups per molecule.
  • This modified polyester is made from hydroxy functional polyester and diisocyanate reacted in such proportions so as to provide from about 4 to about 10 hydroxyl groups per isocyanate group.
  • the hydroxy functional polyester is made from a mixture of (a) polyhydroxy materials comprising diols and triols with (b) acid component selected from dicarboxylic acids and anhydrides thereof.
  • the proportion of reactants (a) and (b) are selected so that the OH/COOH ratio is from about 6:2 to about 6:5.
  • the polyhydroxy materials comprise diols and triols in a hydroxyl equivalent ratio from about 4:1 to about 1:4, more preferably from about 3:1 to about 3:2.5.
  • hydroxyl equivalent ratio is meant the ratio of the hydroxyl equivalents of the diol to the hydroxyl equivalents of the triol.
  • the diols, triols, acid components and diisocyanates which are employed in forming the hydroxy-containing urethane modified polyester of the basecoat may be selected from such materials described above for making the hydroxy-containing urethane modified polyester of the clearcoat.
  • the polyhydroxy materials i.e., diols, triols and optionally tetrols, etc.
  • acid component reactants are combined and reacted, generally at elevated temperatures and in the presence of a catalyst, so as to effect formation of the hydroxy functional polyester.
  • Catalysts for the carboxyl/hydroxy condensation reaction are well known in the art. Exemplary of such carboxyl/hydroxy catalysts are those which have been disclosed above for use in the clearcoat formulation.
  • This hydroxy functional polyester is then modified by reaction with the diisocyanate, whereby urethane groups are incorporated into the polyester.
  • the reactions, whereby the hydroxy-containing urethane modified polyester of the basecoat or clearcoat are formed, are generally carried out in the presence of solvents commonly employed for coating formulations such as toluene, xylene, methyl amyl ketone, etc.
  • Another essential component of the coating compositions (basecoat and clearcoat) of this invention is an amine-aldehyde crosslinking agent.
  • Amine-aldehyde crosslinking agents suitable for crosslinking hydroxy. functional bearing materials are well known in the art. Typically, these crosslinking materials are product of reactions of melamine, or urea with formaldehyde and various alcohols containing up to and including 4 carbon atoms.
  • the amine-aldehyde crosslinking agents useful in this invention are amine-aldehyde resins such as the condensation products of formaldehyde with melamine, substituted melamine, urea, benzoguanamine or substituted benzoguanamine.
  • Preferred members of this class are methylated melamine-formaldehyde resins such as hexamethoxymethylmelamine.
  • the particularly preferred crosslinkers are the high solids melamine resins which have substantially 100 percent nonvolatile content as measured by the foil method at 45°C for 45 minutes. For the purposes of the preferred composition of this invention it should be recognized that it is important not to introduce extraneous diluents that lower the final solids content of the coating.
  • the amine-aldehyde materials function as a crosslinking agent in the compositions of the invention by reacting with the hydroxy functionality of the hydroxy-containing urethane modified polyester (A) and by reaction with the hydroxy functionality on the linear polyurethane, if such materials are included in the compositions.
  • the amine-aldehyde crosslinking agent is generally included in the coating composition in an amount of between about 5 and about 60, more preferably between about 20 and about 40 weight percent based on the weight of the hydroxy-containing urethane modified polyester present in the composition.
  • amine-aldehyde crosslinking agent to be employed in each composition is dependent on the desired properties of the coating compositions as well as its intended use as would be apparent to one skilled in the art.
  • the amounts of crosslinking agent to be employed in the basecoat composition and in the clearcoat composition are selected individually, i.e., the weight percent amounts of crosslinker employed in the basecoat composition and in the clearcoat composition of a particular basecoat/clearcoat system may be different or be similar.
  • crosslinking agents are the amino crosslinking agents sold by American Cyanamid Company, Wayne, N.J. under the trademark "Cymel”.
  • Cymel 301, 303,325, 1130, 1156, which are alkalated melamine aldehyde resins are useful in the compositions of this invention.
  • the crosslinking reactions are catalytically accelerated by acids.
  • One such catalyst for example which may be so employed is p-toluene sulfonic acid which when employed, is generally added to the composition in about .5% by weight based on the total weight of the amine-aldehyde crosslinker and the hydroxy-containing urethane modified polyester of the composition.
  • the basecoat coating composition of the invention also includes pigments, as noted above.
  • pigments are available and known for use in coating compositions by those skilled in the art.
  • the amount of pigment in the basecoat coating compositions may vary. Selection of the optimal amount of pigment to be included in the basecoat compositions would be dependent on, e.g., desired color, hiding requirements of the coating, etc., and would be within the skill of those in the art.
  • Optional Materials e.g., desired color, hiding requirements of the coating, etc., and would be within the skill of those in the art.
  • Additional materials which may be employed in the coating compositions of this invention include a high molecular weight linear polyurethane which has a number average molecular weight of between about 15,000 and about 40,000, preferably between about 20,000 and about 30,000. It may be made by reacting one of the above mentioned diisocyanates and diols, such as oligoester diol, polycaprolactone diol, polyoxypropylene diol, polyether diols, etc. Suitable high molecular weight linear polyurethane materials are commercially available, for example, as Spenlite L06-30S, (available from and a trademark of Spencer-Kellogg, Buffalo, New York).
  • the high molecular weight linear polyurethane may be employed in the compositions in amounts up to about 60 weight percent based on the total weight of the hydroxy-containing urethane modified polyester and crosslinking agent. When employed, it is preferred that they be included in the composition in amounts of between about 10%-60%, more preferably in amounts of about 30%-50% by weight as described. It has been found that by including these linear polyurethanes in the basecoat of these basecoat/clearcoat systems, the depth of color and metallic glamour of the system is improved. While this linear polyurethane, when employed, is generally preferably only included in the basecoat composition, it may be employed in either or both coats and the amounts employed are independently selected.
  • solvents used in the coating composition of this invention are those which are commonly used, e.g., to facilitate spray application at high solids content and include toluene, xylene, methylethyl ketone, acetone, 2-ethoxy-1-ethanol, diacetone alcohol, tetrahydrofuran, ethyl acetate, dimethylsuccinate, dimethylglutarate, dimethyladipate or mixtures thereof.
  • the solvent in which the hydroxy-containing urethane modified polyester is prepared may be employed as a solvent for the composition thus eliminating the need for drying the resin after preparation, if such is desired.
  • Typical of the ultraviolet light stabilizers that are useful in this invention are benzophenones such as dodecyl oxibenzophenone, 2,4-dihydroxybenzophenone, hydroxybenzophenones containing sulfonic groups, 2-4-dihydroxy-3'5'-ditertiary butyl benzophenone, 2,2',4',trihydroxy benzophenone esters of dicarboxylic acids, 2-hydroxy-4-acryloxyethoxybenzophenone, aliphatic mono esters of 2,2',4-trihydroxy-4' alkoxybenzophenone; 2-hydroxy-4-methoxy-2-carboxybenzophenone; triazoles such as 2-phenyl-4-(2'4'-dihydroxybenzoyl) - triazoles substituted benzotriazoles such as hydroxy-phenyltriazoles such as 2-(2'hydroxy-5'-methylphenyl) benzotriazole, 2-(2'-hydroxy-phenyl) benzotriazole, 2-(
  • Light Stabilizers to Kordomenos et al. These stabilizers contain the sterically hindered polyalkylpiperidine radical and at least two primary hydroxyl groups available for crosslinking with the amine-aldehyde component of the coating composition.
  • antioxidants which may be employed in the coating composition are tetrakis alkylene (di-alkyl hydroxy aryl) alkyl ester alkanes such as tetrakis methylene 3(3',5'-dibutyl-4' hydroxyphenyl) proprionate methane, reaction product of p-amino diphenylamine and glycidyl methacrylate, reaction product of n-hexyl-N'-phenylamine diamine and glycidyl methacrylate, pentaerythritol tetrakis (thioglycolate), trimethylol propane tris (thioglycolate), trimethylol ethane tris(thioglycoate), N-(4-anilino phenyl) acrylamide,
  • N-(4-anilinophenyl) maleamic acid N-(4-anilino ⁇ henyl) maleimide, alkylhydroxyphenyl groups bonded through carboalkoxy linkages to nitrogen atom of a heterocyclic nucleus containing an imidodicarbonyl group or an inidodithiocarbonyl group, 3,3 di tert, butyl-4-hydroxy cinnamonitrile, ethyl 3,5-di tert, hexyl-4-hydroxy- cinnamate, substituted benzyl esters of B-substituted hydroxy phenyl) propionic acids, bis (hydroxyphenyl alkylene) alkyl isocyanurate compounds, tetrakis hydroxy benzyl phosphonium halides alone or in combination with a dialkylthiodialkanoate, thioeimethylidyne tetrakisphenols alone or in combination with a dialkyl thio
  • the basecoat would preferably contain only a benzotriazole U.V. stabilizer such as Tinuvin 328 (a trademark of and commercially available from Ciba-Geigy, Ardsley, N.Y.) and the clearcoat would contain a benzotriazole U.V. stabilizer, e.g., Tinuvin 328, the polymeric hindered amine light stabilizer of the aforementioned concurrently filed application to Kordomenos et al, and an antioxidant, e.g., Irganox-1010 (available from and a trademark of Ciba-Geigy). While preferred combinations of stabilizers and antioxidants have been described, these teachings are not meant to be limiting. Selection of the optimal type of stabilizer and antioxidant which may be employed would be within the skill of one in the art.
  • Surface modifiers or wetting agents are common additives for liquid paint compositions. Exact mode of operation of these surface modifiers is not known but it is thought that their presence contributes to better adhesion of coating compositions to the surface being coated and helps formation of thin coatings, particularly on metal surfaces.
  • the choice of surface modifiers or wetting agents is dependent upon the type of surface to be coated. Selection of appropriate surface modifiers will be well within the skill of the artesian. Typical of these surface modifiers are polybutyl acrylate and a wide variety of silicon wetting agents which are commercially available.
  • NAD's such as described by Porter (S. Porter, Jr., and B.N. McBane, U.S. Patent 4,025,474, May 24, 1977). These particle dispersions may be included generally in an amount up to 15% by weight of the total composition.
  • Other types of NAD's such as described by D.L. Maker and S.C. Peng (U.S. Patent 3,814,721, June 4, 1974) or by S.K. Horvath (U.S. application Serial No. 292,853, filed August 14, 1981) also may be included in the coating compositions.
  • the coating composition can be applied by conventional methods known to those in the art. These methods include roll coating, spray coating, dipping or brushing and of course the particular application technique chosen with the particular substrate to be coating and the environment in which coating operation takes place.
  • Particular preferred techniques for applying these coating compositions is spray coating through the nozzle of the spray gun.
  • the mixture was kept at 93°C until there was no NCO group was observed in an infrared spectrum.
  • the batch was then thinned to 70% NV with methyl amyl ketone and had a viscosity of Z 1 .
  • the reaction mixture was cooled down to 149°C and 480 parts of xylene were added.
  • 480 parts of xylene were added.
  • the batch temperature dropped to 93°C
  • 320 gms of isophoroic diisocyanate were added in a period of one hour.
  • the mixture was kept at 93°C until there was no NCO group was observed in an infrared spectrum.
  • the batch was then thinned to 71.3% NV with methyl amyl ketone and had a viscosity of X+.
  • PCP-0301 polycaprolactone triol, trademark of Union Carbide, New York, N.Y.
  • 131 gms of adipic acid and 133 gms of phthalic anhydride, 3 gms of dibutyl tin oxide, and 215 gms of xylene were added.
  • the mixture was heated up to 204°C and water was distilled off until the acid number dropped below 10.
  • the batch was then thinned with 480 parts of methyl amyl ketone.
  • the final product had Z 5 viscosity at 70.1% NV and acid number 3.
  • Example IV Example IV
  • the mixture was heated up to 204°C and water and xylene was distilled off until the acid number dropped below 10.
  • the batch was then thinned with 480 parts of methyl amyl ketone.
  • the final product had Y viscosity at 72. % NV and acid number 7.0.
  • the mixture was heated up to 204°C and water and xylene was distilled off until the acid number dropped below 10.
  • the batch was then thinned with 480 parts of methyl amyl ketone.
  • the final product had Z 4 viscosity at 71.7% NV and acid number 0.8.
  • polycaprolactone triol trademark of Union Carbide
  • 263 gms of adipic acid 402 gms of dodeconoic acid, 4 gms of dibutyl tin oxide, and 200 gms of xylene were added.
  • the mixture was heated up to 204°C and water and xylene was distilled off until the acid number dropped below 10.
  • the batch was then thinned with 480 parts of methyl amyl ketone.
  • the final product had Z 1 + viscosity at 70.0% NV and acid number 5.2.
  • Spenlite L06-30S 1 100 100 Cymel 1130 2 46 46 46

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Abstract

Systèmes de revêtement flexible comprenant une couche de base et une couche transparente et présentant une excellente adhérence sur des supports métalliques et plastiques, ainsi qu'une résistance supérieure à l'action des agents atmosphériques. La composition de la couche transparente comprend un polyester modifié par un uréthane contenant un hydroxy, obtenu en faisant réagir un diol modifié par un uréthane avec un polyol et un composant diacide, réticulable avec des amine-aldéhydes. La composition de la couche de base comprend des polyesters modifiés par un uréthane contenant un hydroxy, obtenus en faisant réagir des polyesters fonctionnels hydroxy avec un diisocyanate, réticulable avec un amine-aldéhyde et un pigment. L'une ou l'autre, ou les deux, de ces compositions peuvent éventuellement comprendre un polyuréthane de poids moléculaire élevé.
PCT/US1983/001599 1983-10-13 1983-10-13 Compositions de revetement flexibles composees d'une couche de base et d'une couche transparente WO1985001695A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU22629/83A AU559366B2 (en) 1983-10-13 1983-10-13 Flexible basecoat/clearcoat coating compositions
PCT/US1983/001599 WO1985001695A1 (fr) 1983-10-13 1983-10-13 Compositions de revetement flexibles composees d'une couche de base et d'une couche transparente
JP58503733A JPS61500173A (ja) 1983-10-13 1983-10-13 可撓性の基礎被覆／透明被覆用の被覆剤組成物

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PCT/US1983/001599 WO1985001695A1 (fr) 1983-10-13 1983-10-13 Compositions de revetement flexibles composees d'une couche de base et d'une couche transparente

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
US6019993A (en) * 1993-03-30 2000-02-01 Omrix Biopharmaceuticals S.A. Virus-inactivated 2-component fibrin glue
WO2017096573A1 (fr) 2015-12-10 2017-06-15 Dow Global Technologies Llc Composition réticulable et revêtement fabriqué à partir de celle-ci

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GB761395A (en) * 1953-04-24 1956-11-14 Bayer Ag Diisocyanate-modified polyester elastomers
US3882189A (en) * 1971-05-20 1975-05-06 Ashland Oil Inc Polyester resins prepared from organic polyisocyanates and blends with other resins or monomers
US3962522A (en) * 1973-04-02 1976-06-08 Ppg Industries, Inc. Poly(esterurethane) coating cured with an aminoplast on a solid substrate
US4021505A (en) * 1975-03-20 1977-05-03 American Cyanamid Company Mar-resistant coating composition of reaction product of hydroxy-terminated urethane and melamine resin

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB761395A (en) * 1953-04-24 1956-11-14 Bayer Ag Diisocyanate-modified polyester elastomers
US3882189A (en) * 1971-05-20 1975-05-06 Ashland Oil Inc Polyester resins prepared from organic polyisocyanates and blends with other resins or monomers
US3962522A (en) * 1973-04-02 1976-06-08 Ppg Industries, Inc. Poly(esterurethane) coating cured with an aminoplast on a solid substrate
US4021505A (en) * 1975-03-20 1977-05-03 American Cyanamid Company Mar-resistant coating composition of reaction product of hydroxy-terminated urethane and melamine resin

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6019993A (en) * 1993-03-30 2000-02-01 Omrix Biopharmaceuticals S.A. Virus-inactivated 2-component fibrin glue
WO2017096573A1 (fr) 2015-12-10 2017-06-15 Dow Global Technologies Llc Composition réticulable et revêtement fabriqué à partir de celle-ci
EP3387080A4 (fr) * 2015-12-10 2019-05-15 Dow Global Technologies LLC Composition réticulable et revêtement fabriqué à partir de celle-ci

Also Published As

Publication number Publication date
AU2262983A (en) 1985-05-07
JPS61500173A (ja) 1986-01-30
AU559366B2 (en) 1987-03-05

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