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WO1999061506A1 - Revetements thermodurcissables a base de polyesters - Google Patents

Revetements thermodurcissables a base de polyesters Download PDF

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Publication number
WO1999061506A1
WO1999061506A1 PCT/US1998/027919 US9827919W WO9961506A1 WO 1999061506 A1 WO1999061506 A1 WO 1999061506A1 US 9827919 W US9827919 W US 9827919W WO 9961506 A1 WO9961506 A1 WO 9961506A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
agent
decalindimethanol
decalindicarboxylic
tetralindicarboxylic
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.)
Ceased
Application number
PCT/US1998/027919
Other languages
English (en)
Inventor
Philip Conrad Heidt
Matthew Lynn Elliott
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.)
Eastman Chemical Co
Original Assignee
Eastman Chemical Co
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 Eastman Chemical Co filed Critical Eastman Chemical Co
Priority to PCT/US1998/027919 priority Critical patent/WO1999061506A1/fr
Publication of WO1999061506A1 publication Critical patent/WO1999061506A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts

Definitions

  • This invention belongs to the field of polyester chemistry.
  • the invention relates to use of various decalin- and tetralin- diols and/or dicarboxyhc acids to form polyesters.
  • Such polyesters are useful in coating compositions.
  • 3,505,282 describes the use of tetralin derivatives to make high molecular weight linear thermoplastic polyesters.
  • the use of both decalin and tetralin derivatives have been extended into polyamides for applications, such as, molded articles, fibers, and films as described in U.S. Patent No. 3,534,002.
  • the use of both decalin and tetralin derivatives have been used in the above mentioned applications, the use of high molecular weight linear polyesters and polyamides severely restrict their use in thermosetting applications especially for use in coatings where high performance and low volatile organic compound (VOC) coatings are required.
  • VOC volatile organic compound
  • the use of properly designed bicyclic resin intermediates in a coatings composition in place of or in combination with commonly used aromatic, acyclic and monocycloaliphatic resin intermediates provides for coatings which are highly flexible while still maintaining excellent weathering, hardness, acid-etch, and stain resistance.
  • the invention provides oil-free polyester resin compositions containing bicycloaliphatic (eg. decalin) and/or bicycloaromatic (eg. tetralin) groups prepared by conventional direct polycondensation processes.
  • bicycloaliphatic eg. decalin
  • bicycloaromatic eg. tetralin
  • the invention further provides enamel coating compositions based on oil-free polyester resin compositions containing bicycloaliphatic and/or bicycloaromatic groups.
  • resin composition of the invention may be dissolved in conventional solvents or used as powders and further formulated into thermosetting coating compositions. Upon application to a substrate and subsequent curing, such coating compositions form films which exhibit excellent flexibility, hardness, weatherability, acid-etch, and stain resistance.
  • the present invention provides a curable polyester resin composition having a number average molecular weight of about 800 to about 5000 and a weight average molecular weight of about 1600 to about 50,000, and containing the polycondensation product of diol and a diacid of which either or both of the diol and the diacid is a decalin or tetralin derivative, as described below.
  • a polyester resin composition of the invention contains about 20-100 mol percent of a decalin or tetralin derivative of the diol or diacid based on the total mol percent of decalin and/or tetralin derivative present in the composition.
  • decalin is defined as “decahydronaphthalene” and further refers to all stereoisomers thereof and "tetralin” is defined as "1,2,3,4-tetrahydronaphthalene” and all stereoisomers thereof.
  • 2,6-decalindicarboxylic acid as used in this invention refers to 2,6-decahydronaphthalenedicarboxylic acid.
  • the structures of 2,6- decalindimethanol, 2,6-decalindicarboxylic acid (and derivatives), and 2,6- tetralindicarboxylic acid (and derivatives) are shown below as Figures 1, 2, and 3 respectively:
  • preferred diols are chosen from ethylene glycol; propylene glycol; 1,3-propanediol; 2-methyl-l,3- propanediol; 2,2-dimethyl-l,3-propanediol; 2-butyl-2-ethyl-l,3-propanediol; 2-ethyl-2- isobutyl-l,3-propanediol; 1,3-butanediol; 1 ,4-butanediol; 1,5-pentanediol; 2,2,4- trimethyl-l,3-pentanediol; 1,6-hexanediol; 2,4-dimethyl-2-ethyl-l,3-hexanediol; thiodiethanol; hydrogenated bisphenol A; 1,2-cyclohexanedimethanol; 1,3- cyclohexanedimethanol; 1
  • the more preferred diols are 2,6-decalindimethanol (DDM); 2,2- dimethyl-l,3-propanediol; 2-butyl-2-ethyl-l,3-propanediol; 1,6-hexanediol; 1,4- cyclohexanedimethanol; hydrogenated bisphenol A; and 3-hydroxy-2,2-dimethylpropyl 3-hydroxy-2,2-dimethylpropanoate.
  • DDM 2,6-decalindimethanol
  • 2,2- dimethyl-l,3-propanediol 2-butyl-2-ethyl-l,3-propanediol
  • 1,6-hexanediol 1,4- cyclohexanedimethanol
  • hydrogenated bisphenol A and 3-hydroxy-2,2-dimethylpropyl 3-hydroxy-2,2-dimethylpropanoate.
  • Triols and tetraols may also be used in the compositions of the invention.
  • Preferred triols include, but not limited to, trimethanolethane, trimethanolpropane, glycerol, and the like. The most preferred triol is trimethanolpropane (TMP).
  • TMP trimethanolpropane
  • a preferred tetraol is pentaerythritol.
  • preferred acids, esters and anhydrides thereof are chosen from succinic; glutaric; adipic; pimelic; suberic; azelaic; sebacic; dodecanedioic; phthalic; isophthalic; terephthalic; 1,2- cyclohexanedicarboxylic; 1,3-cyclohexanedicarboxylic; 1,4-cyclohexanedicarboxylic; methylhexahydrophthalic; ethylhexahydrophthalic; propylhexahydrophthalic; butylhexahydrophthalic; tetrahydrophthalic; methyltetrahydrophthalic, ethyltetrahydrophthalic; propyltetrahydrophthalic; butyltetrahydrophthalic; maleic; 1,2- decalindicarboxylic; 1,3-decalindicarboxylic; 1,4-decalindicar
  • the more preferred acids, esters and anhydrides thereof include adipic; isophthalic; 1,2-cyclohexanedicarboxylic; 1,3- cyclohexanedicarboxylic; 1,4-cyclohexanedicarboxylic; 2,6-decalindicarboxylic; and 2,6-tetralindicarboxylic.
  • the curable polyesters provided herein preferably have an acid number of not greater than 80 and a hydroxyl number of at least 10.
  • Suitable solvents for the curable enamel composition include xylenes, cyclohexanone, ketones (for example, methyl amyl ketone), 2-butoxyethanol, ethyl 3- ethoxypropionate, toluene, n-butanol, and other volatile inert solvents typically used in industrial baking (i.e. thermosetting) enamels.
  • Suitable crosslinking agents includes amino-resins, isocyanates, and epoxies.
  • amino crosslinking agent is preferably a melamine type crosslinking agent, i.e., a crosslinking agent having a plurality of -N(CH 2 OR 3 ) 2 functional groups, wherein R 3 is C,-C 4 alkyl, preferably methyl.
  • the crosslinking agent may be selected from compounds of the following formulae, wherein R 3 is independently C,-C alkyl:
  • preferred amino-crosslinking agents include hexamethoxymethylmelamine, tetramethoxy-methylbenzoguanamine, tetramethoxymethylurea, mixed butoxy/methoxy substituted melamines, and the like.
  • the most preferred amino-crosslinking agent is hexamethoxymethylmelamine.
  • Suitable polyisocyanate crosslinkers include aliphatic, cycloaliphatic, and aromatic polyisocyanates, such as, 1,6-hexamethylene diisocyanate; isophorone diisocyanate; toluene diisocyanate; 4,4'-biphenylene diisocyanate; bis cyclohexyl diisocyanate; 4,4'-biscyclohexyl dimethylmethane diisocyanate; 1,4-cyclohexylene diisocyanate; 1,3-cyclopentylene diisocyanate; 1, 3 -phenylene diisocyanate; 1,5- naphthalene diisocyanate; triphenylmethane triisocyanate; 1,3,5-benzene triisocyanate; 2,4,6-toluene triisocyanate; trimer of hexamethylene diisocyanate (DESMODUR N- 3390); an adduct of trimethylolpropane and
  • a crosslinkable enamel composition as described above, further comprising one or more leveling, rheology, and flow control agents, such as, silicones, fluorocarbons, or cellulosics; flatting agents; pigment wetting and dispersing agents; surfactants; ultraviolet absorbers; antioxidants; hindered amine light stabilizers; tinting pigments; defoaming and antifoaming agents; anti-settling, anti-sag and bodying agents; anti-skinning agents; anti- flooding and anti-floating agents; fungicides mildewcides; corrosion inhibitors; thickening agents; or coalescing agents.
  • one or more leveling, rheology, and flow control agents such as, silicones, fluorocarbons, or cellulosics; flatting agents; pigment wetting and dispersing agents; surfactants; ultraviolet absorbers; antioxidants; hindered amine light stabilizers; tinting pigments; defoaming and antifoaming agents; anti-settling, anti-sa
  • flatting agents examples include synthetic silica, available from the Davison Chemical Division of W.R. Grace & Company under the trademark SYLOID®; polypropylene, available from Hercules Inc., under the trademark HERCOFLAT®; synthetic silicate, available from J.M. Huber Corporation under the trademark
  • dispersing agents and surfactants include sodium bis(tridecyl) sulfosuccinnate, di(2-ethyl hexyl) sodium sulfosuccinnate, sodium dihexylsulfo- succinnate, sodium dicyclohexyl sulfosuccinnate, diamyl sodium sulfosuccinnate, sodium diisobutyl sulfosuccinnate, disodium iso-decyl sulfosuccinnate, disodium ethoxylated alcohol half ester of sulfosuccinnic acid, disodium alkyl amido polyethoxy sulfosuccinnate, tetrasodium N-(l,2-dicarboxy-ethyl)-N-oxtadecyl sulfosuccinnamate, disodium N-octasulfosuccinnamate, sulfated ethoxylated nony
  • viscosity, suspension, and flow control agents examples include polyaminoamide phosphate, high molecular weight carboxylic acid salts of polyamine amides, and alkyl amine salt of an unsaturated fatty acid, all available from B YK Chemie U.S.A. under the trademark ANTI TERRA®.
  • Further examples include polysiloxane copolymers, polyacrylate solution, cellulose esters, hydroxyethyl cellulose, hydrophobically-modified hydroxyethyl cellulose, hydroxypropyl cellulose, polyamide wax, polyolefin wax, carboxymethyl cellulose, ammonium polyacrylate, sodium polyacrylate, and polyethylene oxide.
  • fungicides examples include 4,4- dimethyloxazolidine, 3,4,4-trimethyloxazolidine, midified barium metaborate, potassium N-hydroxy-methyl-N-methyldithiocarbamate, 2-(thiocyanomethylthio) benzothiazole, potassium dimethyl dithiocarbamate, adamantane, N-(trichloromethylthio) phthalimide, 2,4,5, 6-tetrachloroisophthalonitrile, orthophenyl phenol, 2,4,5-trichlorophenol, dehydroacetic acid, copper naphthenate, copper octoate, organic arsenic, tributyl tin oxide, zinc naphthenate, and copper 8-quinolinate.
  • U.V. absorbers and U.V. light stabilizers include substituted benzophenone, substituted benzotriazole, hindered amine, and hindered benzoate, available from American Cyanamide Company under the tradename Cyasorb UV, and available from Ciba Geigy under the tradename Tinuvin, and diethyl-3-acetyl-4-hydroxy- benzyl-phosphonate, 4-dodecyloxy-2-hydroxy benzophenone, and resorcinol monobenzoate.
  • Such paint or coating additives as described above form a relatively minor proportion of the enamel composition, preferably about 0.05 weight % to about 5.00 weight %.
  • a curable enamel composition optionally containing one or more of the above-described additives, further comprising one or more pigments.
  • Pigments suitable for use in the enamel compositions envisioned by the present invention are the typical organic and inorganic pigments, well-known to one of ordinary skill in the art of surface coatings, especially those set forth by the Colour Index. 3d Ed., 2d Rev., 1982, published by the Society of Dyers and Colourists in association with the American Association of Textile Chemists and Colorists. Examples include but are not limited to the following: CI Pigment White 6 (titanium dioxide); CI Pigment Red 101 (red iron oxide); CI Pigment Yellow 42, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4
  • the curable enamel composition is then applied to the desired substrate or article, e.g., steel, aluminum, or galvanized sheeting (either primed or unprimed), heated (i.e., cured) to a temperature of about 140 C to about 175 C, for a time period of 5-60 minutes and subsequently allowed to cool.
  • the desired substrate or article e.g., steel, aluminum, or galvanized sheeting (either primed or unprimed)
  • heated i.e., cured
  • a shaped or formed article which has been coated with the thermosetting coating compositions of the present invention and cured.
  • Polyester resin prepared from 1.565 equivalents NPG glycol (Eastman Chemical Company), 0.470 equivalents TMP (Hoechst Celanese), and 1.55 equivalents DDA (2,6- decalindicarboxylic acid, Eastman Chemical Company). To the monomers was added 0.1 percent Fascat 4100 (Elf Atochem) based on resin yield and 0.5 moles of deionized water. Polycondensation materialized using a single-stage reaction whereby the temperature was increased approximately 10 °C every 35 minutes (once a temperature of 140 °C was reached) until a maximum of 230 °C was obtained and remain there until a final acid number of approximately 5 was obtained. The resin had a final acid number of
  • Polyester resin prepared from 7.792 equivalents NPG glycol, 0.913 equivalents TMP, 6.228 equivalents IPA (Amoco purified isophthalic acid), and 1.557 equivalents
  • Polyester resin prepared similarly to resin in Example 2 using 0.736 equivalents of NPG glycol, 0.184 equivalents of DDM (2,6-decalindimethanol, Eastman Chemical Company), 0.136 equivalents of TMP, 0.918 equivalents of DDA, 0.1 percent Fascat 4100, and 0.83 moles of deionized water.
  • a final acid number of 8.8, Mn 3790,
  • DMDD dimethyl 2,6-decalindicarboxylate
  • DBTO dibutyltin oxide
  • Polyester resin prepared using 10.34 equivalents NPG glycol, 2.95 equivalents TMP,
  • Polyester resin prepared using 4.807 equivalents NPG glycol, 1.787 equivalents TMP, 5.431 equivalents HHPA, 0.1 percent Fascat 4100, and 0.83 moles of deionized water. Once an initial temperature of 150 °C was obtained, the heating increased at such a rate as to maintain a condensate of 0.5 grams per minute to a maximum temperature of
  • Clear enamels were prepared using 35 parts of polyester resin of Example 1, 15 parts Resimene 745 (a hexamethoxymethylmelamine, Monsanto), 41 parts of a solvent blend (55% xylenes, 32% MAK, 6.5% Eastman EEP, 6.5% n-BuOH), 0.5 parts of a 30 percent solution of PTSA (p-toluenesulfonic acid) in t-PrOH, and 0.2 parts of a 30 percent solution of FC-430 (a flow control agent, 3M Company) in MAK. Coatings were prepared on iron phosphate treated 22 gauge polished steel panels (ACT, Advanced Coatings Technology, Inc.) using a number 50 wire- wrapped draw-down bar and cured at
  • Clear enamels were prepared from 35 parts resin of Example 5, 15 parts Resimene 745, 33 parts of a solvent blend (same solvent as used in Example A), 0.5 parts of a 30 percent solution of PTSA in z-PrOH, and 0.3 parts of a 30 percent solution of FC- 430 in MAK. Coatings were prepared on iron phosphate treated 22 gauge unpolished steel panels (Q-Panel Company) using a number 50 wire- wrapped draw-down bar and cured at 160 °C for 30 minutes in a forced-air oven.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des compositions de résine polyester sans huile dérivées du produit de polycondensation d'un diol et d'un diacide qui sont soit l'un, soit l'autre, soit les deux un dérivé de la décaline ou de la tétraline. L'invention concerne également des revêtements en émail renfermant de telles compositions de résine de polyester. Après application et polymérisation sur un substrat ou un article, ces compositions d'émail donnent des films dotés de propriétés remarquables sous l'angle de la souplesse, de la dureté, de la résistance aux intempéries, de l'attaque à l'acide et de la résistance aux taches.
PCT/US1998/027919 1998-12-30 1998-12-30 Revetements thermodurcissables a base de polyesters Ceased WO1999061506A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027919 WO1999061506A1 (fr) 1998-12-30 1998-12-30 Revetements thermodurcissables a base de polyesters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027919 WO1999061506A1 (fr) 1998-12-30 1998-12-30 Revetements thermodurcissables a base de polyesters

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WO1999061506A1 true WO1999061506A1 (fr) 1999-12-02

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001261799A (ja) * 2000-03-16 2001-09-26 Mitsubishi Gas Chem Co Inc 非晶質ポリエステル及び光学用材料
CN104312388A (zh) * 2014-11-26 2015-01-28 江苏博腾新材料股份有限公司 一种抗老化耐光涂料
KR20150124994A (ko) * 2013-03-05 2015-11-06 미츠비시 가스 가가쿠 가부시키가이샤 산소 흡수성 수지 조성물
WO2025019470A1 (fr) * 2023-07-19 2025-01-23 Eastman Chemical Company Compositions de revêtements en poudre thermodurcissables

Citations (5)

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Publication number Priority date Publication date Assignee Title
DE2704969A1 (de) * 1976-02-27 1977-09-01 Vianova Kunstharz Ag Verfahren zur herstellung verbesserter, durch energiereiche strahlung haertbarer ueberzugsmittel
JPS61243863A (ja) * 1985-04-23 1986-10-30 New Japan Chem Co Ltd 水性ポリエステルの製造方法
US5306567A (en) * 1992-11-27 1994-04-26 Eastman Kodak Company Thermosetting coating compositions
US5464909A (en) * 1995-03-24 1995-11-07 Eastman Chemical Company Powder coating having good UV resistance
EP0733687A2 (fr) * 1995-03-24 1996-09-25 Eastman Chemical Company Compositions de revêtements en poudre thermodurcissable

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2704969A1 (de) * 1976-02-27 1977-09-01 Vianova Kunstharz Ag Verfahren zur herstellung verbesserter, durch energiereiche strahlung haertbarer ueberzugsmittel
JPS61243863A (ja) * 1985-04-23 1986-10-30 New Japan Chem Co Ltd 水性ポリエステルの製造方法
US5306567A (en) * 1992-11-27 1994-04-26 Eastman Kodak Company Thermosetting coating compositions
US5464909A (en) * 1995-03-24 1995-11-07 Eastman Chemical Company Powder coating having good UV resistance
EP0733687A2 (fr) * 1995-03-24 1996-09-25 Eastman Chemical Company Compositions de revêtements en poudre thermodurcissable

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 106, no. 26, 29 June 1987, Columbus, Ohio, US; abstract no. 215596, XP002113765 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001261799A (ja) * 2000-03-16 2001-09-26 Mitsubishi Gas Chem Co Inc 非晶質ポリエステル及び光学用材料
KR20150124994A (ko) * 2013-03-05 2015-11-06 미츠비시 가스 가가쿠 가부시키가이샤 산소 흡수성 수지 조성물
EP2966125A4 (fr) * 2013-03-05 2016-11-02 Mitsubishi Gas Chemical Co Composition de résine absorbant l'oxygène
TWI632953B (zh) * 2013-03-05 2018-08-21 三菱瓦斯化學股份有限公司 氧吸收性樹脂組成物
US10150107B2 (en) 2013-03-05 2018-12-11 Mitsubishi Gas Chemical Company, Inc. Oxygen-absorbing resin composition
KR102174572B1 (ko) * 2013-03-05 2020-11-05 미츠비시 가스 가가쿠 가부시키가이샤 산소 흡수성 수지 조성물
CN104312388A (zh) * 2014-11-26 2015-01-28 江苏博腾新材料股份有限公司 一种抗老化耐光涂料
WO2025019470A1 (fr) * 2023-07-19 2025-01-23 Eastman Chemical Company Compositions de revêtements en poudre thermodurcissables

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