WO2002066541A1 - Procede de fabrication d'un polyester dendritique a terminaison carboxy - Google Patents

Procede de fabrication d'un polyester dendritique a terminaison carboxy Download PDF

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Publication number
WO2002066541A1
WO2002066541A1 PCT/SE2002/000263 SE0200263W WO02066541A1 WO 2002066541 A1 WO2002066541 A1 WO 2002066541A1 SE 0200263 W SE0200263 W SE 0200263W WO 02066541 A1 WO02066541 A1 WO 02066541A1
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WO
WIPO (PCT)
Prior art keywords
acid
anhydride
dendritic polyester
polyester
tri
Prior art date
Application number
PCT/SE2002/000263
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English (en)
Inventor
Bo Pettersson
Håkan BJÖRNBERG
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Perstorp Specialty Chemicals Ab
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Publication of WO2002066541A1 publication Critical patent/WO2002066541A1/fr

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    • 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/003—Dendrimers
    • 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
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Definitions

  • the present invention relates to a process for manufacture of a carboxy terminated dendritic polyester. Said process comprises ring opening addition of at least one anhydride of a di, tri or polyfunctional carboxylic acid to at least one sur katalysator functional dendritic polyester.
  • the present invention relates to a powder coating composition comprising a carboxy terminated dendritic polyester obtainable by said process and the use of said carboxy terminated dendritic polyester in a resin composition.
  • Carboxy functional polyesters are a type of polyesters, which in recent years have expanded rapidly in powder coating applications. They are today typically used as main resins for many powder coatings and are cured with either epoxy resins, low molecular epoxy compounds, such as triglycidyl isocyanurate (TGIC) or alkanol adipates and amides of for instance the
  • Carboxy functional polyesters used today offer good chemical resistance, good outdoor durability and good surface finish. They do not contain solvents, thus offering environmentally friendly coatings and are furthermore comparatively inexpensive. Hence, carboxy functional polyesters are attractive in a large number of coating applications.
  • Carboxy functional polyesters currently used in powder coatings suffer, however, from being highly viscous and having fairly low carboxy functionality. This in turn means high curing temperatures and long curing times to obtain coatings with high surface finish (good flow) and sufficient chemical resistance (chemical conversion).
  • the high curing temperatures limit the type of substrates possible to coat with carboxy functional polyesters and the long curing times limit the productivity rate since line speeds have to be kept low.
  • Tg glass transition temperature
  • sur katalysator functional dendritic polyesters built up from an alcohol, epoxide, acid or anhydride core and AB 2 monomers, such as di, tri or polyhydroxy acids, can when being converted to carboxy functionality with aromatic or hydrogenated aromatic
  • the ring opening of anhydrides with terminal alcohols to yield an ester and a terminal carboxylic acid group is a well known technique to provide carboxylic acid functionality to a polyester backbone.
  • Ring opening of aromatic and hydrogenated aromatic (cycloaliphatic) anhydrides are usually performed at relatively high temperatures, such as 150-175°C or even higher as disclosed in for instance "Alkyd Resin Technology” chapter “Temperature of Reaction” T.C. Patton, Interscience Publishers, 1962. It is not, using conventional reaction conditions for ring opening of said anhydrides, possible to yield a carboxy functional dendritic polyester of the type herein disclosed.
  • a process for production of a carboxy functional dendritic polyester has quite surprisingly been obtained, which due to precise temperature control allows incorporation of carboxy functionality based on inherently rigid anhydrides.
  • a reaction temperature close to the melting point of the aromatic anhydride and being in the interval of 130-145°C it has surpringly been possible in high yields to produce sur katalysator terminated dendritic polyesters.
  • a carboxy terminated dendritic polyester obtained according to the invention have a Tg significantly above the hydroxy functional dendritic polyester, onto which the aromatic acid is grafted.
  • the present invention accordingly refers to a process for production of a carboxy terminated dendritic polyester.
  • Said process comprises ring opening addition of at least one anhydride of a di, tri or polyfunctional aromatic and/or cycloaliphatic carboxylic acid to at least one hydroxy functional dendritic polyester having a hydroxyl value of at least 50 mg KOH/g.
  • the ring opening addition is performed at a molar ratio anhydride to hydroxyl groups of between 0.2, such as 0.3 or 0.5, to 1 and 1 to 1 and at a reaction temperature of 130-150°C.
  • the thus yielded carboxy terminated dendritic polyester may accordingly have one or more residual hydroxyl groups.
  • Yielded carboxy terminated dendritic polyester has, furthermore, a softening point of at least 20°C, such as 20-60°C and/or a glass transition temperature of at least 35°C, such as 40-80°C or preferably 45-65°C, and a preferred acid value of at least 50, such as 80-250, mg KOH/g.
  • Said at least one anhydride is in preferred embodiments an anhydride selected from the group consisting of ⁇ -phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, trimellitic anhydride and/or hexachloroendomethylene tetrahydrophthalic anhydride.
  • the process of the present invention may comprise an additional ring opening addition, whereby an obtained carboxy terminated polyester, having at least one residual hydroxyl group, in addition to said at least one aromatic or cycloaliphatic anhydride, is terminated by reaction with at least one anhydride of an aliphatic saturated or unsaturated di, tri or polyfunctional carboxylic acid.
  • Said at least one anhydride of said aliphatic saturated or unsaturated di, tri or polyfunctional carboxylic acid is in the most preferred embodiments for instance maleic anhydride and/or succinic anhydride and said additional ring opening addition is most suitably performed at a temperature of 90-110°C.
  • the hydroxy functional dendritic polyester subjected to said ring opening addition of at least one anhydride of a di, tri or polyfunctional aromatic and/or cycloaliphatic carboxylic acid has a preferred glass transition temperature of at least 20°C, preferably at least 30°C, and is built up from ester or polyester units optionally in combination with ether or polyether units.
  • said at least one hydroxy functional dendritic polyester include dendritic polymers built up from a monomeric or polymeric core, having at least one reactive hydroxyl or epoxide group, to which core are added 1-20, preferably 2-8, branching generations built up from at least one monomeric or polymeric branching chain extender having at least three reactive groups of which at least two are hydroxyl groups and at least one is a carboxyl or anhydride group, and optionally at least one spacing generation being built up from at least one spacing chain extender, which spacing chain extender has two reactive groups of which one is a hydroxyl group and one is a carboxyl or anhydride group or which spacing chain extender is an inner ether, such as a lactone, thereof.
  • the hydroxy functional dendritic polyester may furthermore be partially chain stopped and/or functionalised by means of reaction between said polyester and a compound preferably selected from the group consisting of aliphatic or cycloaliphatic saturated or unsaturated monofunctional carboxylic acids or anhydrides threreof, aromatic monofunctional carboxylic acids or anhydrides thereof, diisocyanates, oligomers and adducts of diisocyanates, glycidyl esters of monofunctional carboxylic acids or anhydrides, glycidyl ethers of monofunctional alcohols, adducts of aliphatic or cycloaliphatic saturated or unsaturated mono, di, tri or polyfunctional carboxylic acids or adducts of corresponding anhydrides, adducts of aromatic mono, di, tri or polyfunctional carboxylic acids or adducts of corresponding anhydrides, epoxides of unsaturated monocarboxylic acids or corresponding triglycerides, carboxy functional a
  • Suitable compounds used for said chain stopping or said functionalisation are advantegously exemplified by compounds such as formic acid, acetic acid, propionic acid, butanoic acid, hexanoic acid, acrylic acid, methacrylic acid, crotonic acid, lauric acid, linseed fatty acid, soybean fatty acid, tall oil fatty acid, dehydrated castor fatty acid, capric acid, caprylic acid, benzoic acid, behenic acid, montanoic acid, /?-tert.butylbenzoic acid, abietic acid, sorbic acid, l-chloro-2,3-epoxypropane, l,4-dichloro-2,3-e ⁇ oxybutane, epoxidised soybean fatty acid, phenyl isocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, hexamethylene diisocyanate,
  • Suitable compounds used for said chain stopping or functionalisation are found among for instance compounds such as maleates or succinates of glycerol monoallylether, trimethylolethane monoallylether, trimethylolpropane monoallyl ether, glycerol diallyl ether, trimethylolethane diallyl ether, trimethylolpropane diallyl ether, pentaerythritol diallylether or pentaerythritol triallyl ether.
  • Said hydroxy functional dendritic polyester may, furthermore be partially functionalised by means of reaction between said polyester and at least one epihalohydrine or allylhalide, such as epichlorohydrine and allylchloride and/or allylbromide.
  • epihalohydrine or allylhalide such as epichlorohydrine and allylchloride and/or allylbromide.
  • Embodiments of said monomeric or polymeric core, having said at least one hydroxyl or epoxide group include mono, di, tri or polyfunctional alcohols or ether alcohols, such as adducts between at least one mono, di, tri or polyfunctional alcohol and at least one alkylene oxide, such as ethylene, propylene and/or butylene oxide, and mono, di, tri or polyfunctional epoxides, such as glycidyl esters of monofunctional carboxylic acids, glycidyl ethera of mono, di, tri or polyfunctional alcohols, mono, di or triglycidyl substituted isocyanurates and glycidyl ethers of condensation products between at least one phenol and at least one aldehyde or ketone.
  • mono, di, tri or polyfunctional alcohols or ether alcohols such as adducts between at least one mono, di, tri or polyfunctional alcohol and at least one alkylene oxide, such as ethylene, propylene and/or but
  • Said core is in said preferred embodiments of said hydroxy functional dendritic polyester suitably and preferably selected among 5-ethyl-5-hydroxymethyl-l,3-dioxane, 5,5-dihydroxymethyl-l,3-dioxane, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, pentanediol, neopentyl glycol, 1,3-propanediol, 2-methyl-2-propyl- 1 ,3-propanediol, 2-ethyl-2-butyl- 1 ,3-propanediol, cyclohexanedimethanol, trimethylolpropane, trimethylolethane, glycerol, erythritol, anhydroennea-heptitol, ditrimethylolpropane, ditrimethylolethane, pentaerythritol, methylglucoside,
  • Embodiments of said at least one monomeric or polymeric branching chain extender is preferably selected from the group consisting of 2,2-dimethylolpropionic acid, ⁇ , ⁇ -bis- (hydroxymethyl)butyric acid, ⁇ , ⁇ , -tris(hydroxymethyl)acetic acid, ⁇ , ⁇ -bis(hydroxy- methyl)valeric acid, ⁇ , ⁇ -bis(hydroxy)propionic acid, 3,5-dihydroxybenzoic acid, ⁇ , ⁇ -dihydroxypropionic acid, hep tonic acid, citric acid, d- or /-tartaric acid, dihydroxymaloic acid and d-gluconic acid.
  • Said at least one optional spacing chain extender is preferably an aliphatic, cycloaliphatic or aromatic monohydroxyfunctional monocarboxylic acid or anhydride or is an inner ether, such as a lactone, of such an acid.
  • Preferred species of said optional spacing chain extender include hydroxyacetic acid, hydroxyvaleric acid, hydroxypropionic acid, hydroxypivalic acid, glycolide, ⁇ -valerolactone, ⁇ -propiolactone and ⁇ -caprolactone.
  • the present invention refers to a powder coating composition comprising an intimate blend of
  • At least one binder composition comprising (a) at least one carboxy terminated dendritic polyester obtainable by the process disclosed above and (b) at least one aliphatic, cycloaliphatic or aromatic polymer, such as a polymer selected from the group consisting of an epoxy, a polyester, an acrylic and/or a blocked urethane polymer, and
  • At least one co-reactant preferably selected from the group consisting of for instance monomeric or polymeric bisphenol A or F type glycidyl ethers, glycidyl ethers of the Novolac
  • thermoplastic resins obtained from acidic condensation of phenols and formaldehyde type, triglycidyl isocyanurates, other monomeric or polymeric glycidyl ethers and esters and alkanol amides of the PRIMID® (EMS Chemie, Switzerland) type, and optionally (iii) at least one flow and/or leveling agent and/or at least one degasser.
  • Said binder composition is in preferred embodiments present in an amount of 40-95% by weight, whereby said component (i) preferably is present in said binder composition in an amount of 5-100% by weight and said component (ii) preferably in an amount of 1-90% by weight.
  • the optional flow and/or levelling agent and/or the optional degasser are/is suitably each and independently present in an amount of 0-2% by weight.
  • the powder coating composition may, furthermore additionally comprise at least one catalyst, filler, colouring agent, corrosion inhibitor, biocide, plasticiser, UN stabiliser and/or UN absorber.
  • the present invention relates to the use of a carboxy terminated dendritic polyester obtainable by disclosed process in resin compositions, such as binder compositions for coatings, including powder coatings, such as low gloss powder coatings, whereby said carboxy terminated dendritic polyester provides and/or aids in matting and/or works as a matting agent.
  • Examples 1-8 refer to preparation of carboxy terminated dendritic polyesters. Said polyeters are prepared according to embodiments of the process of the present invention.
  • a hydroxy functional dendritic polyester (Boltorn ® H20, Perstorp Chemicals AB, Sweden), nominally having 16 hydroxyl groups, a nominal molecular weight of 1750 and a tetrafunctional core, was partially end capped with propionic acid at a molar ratio said hydroxyl groups to acid groups of 1:0.25 and at a temperature of 130°C. Obtained intermediate product was subsequently subjected to ring opening addition of phthalic anhydride at a molar ratio said hydroxyl groups to anhydride groups of 1:0.75. Phthalic anhydride was charged at
  • Example 2 The same hydroxy functional dendritic polyester as in Example 1 (Boltorn ® H20, Perstorp Chemicals AB, Sweden) was subjected to ring opening addition of phthalic anhydride at a molar ratio hydroxyl groups to anhydride groups of 1:0.6. The polyester was heated to 130°C and phthalic anhydride was charged at said temperature. A weak exotherm was observed and the reaction temperature was kept at 135-140°C until the ring opening addition was completed.
  • a hydroxy functional dendritic polyester (Boltorn ® H30, Perstorp Chemicals AB, Sweden), nominally having 32 hydroxyl groups, a nominal molecular weight of 3607 and a tetrafunctional core, was partially end capped with propionic acid at a molar ratio said hydroxyl groups to acid groups of 1:0.25 and at a temperature of 130°C. Obtained intermediate product was subsequently subjected to ring opening addition of phthalic anhydride at a molar ratio said hydroxyl groups to anhydride groups of 1:0.6. Phthalic anhydride was charged at
  • Example 3 The same hydroxy functional dendritic polyester as in Example 3 (Boltorn ® H30, Perstorp Chemicals AB, Sweden) was subjected to ring opening addition of phthalic anhydride at a molar ratio hydroxyl groups to anhydride groups of 1:1. The polyester was heated to 130°C and phthalic anhydride was charged at said temperature. A weak exotherm was observed and the reaction temperature was kept at 135-140°C until the ring opening addition was completed. Obtained product was now cooled to room temperature.
  • a hydroxy functional dendritic polyester (Boltorn ® range, Perstorp Chemicals AB, Sweden), nominally having 32 hydroxyl groups, a nominal molecular weight of 4048 and a flexible tetrafunctional core, was partially end capped with propionic acid at a molar ratio said hydroxyl groups to acid groups of 1:0.25 and at a temperature of 130°C. Obtained intermediate product was subsequently subjected to ring opening addition of phthalic anhydride at a molar ratio said hydroxyl groups to anhydride groups of 1:0.75. Phthalic anhydride was charged at
  • Example 5 The same hydroxy functional dendritic polyester as in Example 5 (Boltorn ® range, Perstorp Chemicals AB, Sweden) was subjected to ring opening addition of phthalic anhydride at a molar ratio hydroxyl groups to anhydride groups of 1:0.6. The polyester was heated to 130°C and phthalic anhydride was charged at said temperature. A weak exotherm was observed and the reaction temperature was kept at 135-140°C until the ring opening addition was completed.
  • a hydroxy functional dendritic polyester (Boltorn ® range, Perstorp Chemicals AB, Sweden) nominally having 16 hydroxyl groups, a nominal molecular weight of 2190 and a flexible tetrafunctional core, was partially end capped with propionic acid at a molar ratio said hydroxyl groups to acid groups of 1:0.25 and at a temperature of 130°C. Obtained intermediate product was subsequently subjected to ring opening addition of phthalic anhydride at a molar ratio said hydroxyl groups to anhydride groups of 1:0.6. Phthalic anhydride was charged at 130°C. A weak exotherm was observed and the reaction temperature was kept at 135-140°C until the ring opening addition was completed. Obtained product was now cooled to room temperature.
  • Example 7 The same hydroxy functional dendritic polyester as in Example 7 (Boltorn ® range, Perstorp Chemicals AB, Sweden) was subjected to ring opening addition of phthalic anhydride at a molar ratio hydroxyl groups to anhydride groups of 1:1. The polyester was heated to 130°C and phthalic anhydride was charged at said temperature. A weak exotherm was observed and the reaction temperature was kept at 135-140°C until the ring opening addition was completed.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

L'invention concerne un procédé de production d'un polyester dendritique à terminaison carboxy. Ce procédé comprend l'ouverture de cycle d'au moins un anhydride d'un acide carboxylique cycloaliphatique et/ou aromatique di-, tri- ou polyfonctionnel à au moins un polyester dendritique fonctionnel hydroxy comportant une valeur hydroxyle d'au moins 50 mg KOH/g. Cette ouverture de cycle est effectuée selon un rapport molaire de l'anhydride sur les groupes hydroxyle compris entre 0,2/1 et 1/1, à une température de réaction située entre 130 et 150°C.Le polyester dendritique à terminaison carboxy obtenu présente une température de transition vitreuse d'au moins 35°C. L'invention selon d'autres aspects concerne une composition de revêtement de poudre comprenant le polyester dendritique à terminaison carboxy pouvant être obtenu par ce procédé et l'utlisation de ce polyester dans une composition de résine.
PCT/SE2002/000263 2001-02-16 2002-02-15 Procede de fabrication d'un polyester dendritique a terminaison carboxy WO2002066541A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0100503A SE518592C2 (sv) 2001-02-16 2001-02-16 Förfarande för framställning av en karboxylterminerad dendritisk polyester, pulverytbeläggningskomposition framställd enligt förfarandet, samt dess användning
SE0100503-2 2001-02-16

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Cited By (15)

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EP1798266A2 (fr) * 2004-10-08 2007-06-20 BASF Coatings Japan Ltd. Composition de resine a groupes hydroxyle pour revetements, composition de revetement, procede de revetement de finition et article revetu
WO2009115580A2 (fr) * 2008-03-20 2009-09-24 National University Of Ireland, Galway Dendrimères et applications de dendrimères
WO2009156400A1 (fr) 2008-06-23 2009-12-30 Sicpa Holding Sa Encre pour l'impression intaglio comprenant des dendrimères
WO2010013638A1 (fr) * 2008-07-29 2010-02-04 日立化成工業株式会社 Agent de durcissement de résine époxy, composition de résine époxy, matériau durci de celle-ci et dispositif à semi-conducteurs optiques
US7666331B2 (en) 2005-08-31 2010-02-23 Transitions Optical, Inc. Photochromic article
WO2011014284A1 (fr) * 2009-07-30 2011-02-03 E. I. Du Pont De Nemours And Company Procédé de production d’un revêtement présentant une valeur de brillant voulue
WO2017053379A1 (fr) * 2015-09-25 2017-03-30 Eastman Chemical Company Polymères contenant du cyclobutanediol et un acide 2,2-bis(hydroxyméthyl)alkylcarboxylique
US9988553B2 (en) 2016-02-22 2018-06-05 Eastman Chemical Company Thermosetting coating compositions
US10011737B2 (en) 2016-03-23 2018-07-03 Eastman Chemical Company Curable polyester polyols and their use in thermosetting soft feel coating formulations
US20190185701A1 (en) * 2017-12-20 2019-06-20 Ppg Industries Ohio, Inc. Ultradurable coating composition
US10676565B2 (en) 2015-05-19 2020-06-09 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
CN112011257A (zh) * 2020-07-31 2020-12-01 擎天材料科技有限公司 专用车粉末涂料用聚酯树脂及其制备方法和应用
CN113801307A (zh) * 2021-08-31 2021-12-17 擎天材料科技有限公司 一种易消光型聚酯树脂及其制备方法和应用
CN114276525A (zh) * 2021-12-30 2022-04-05 优卡化学(上海)有限公司 一种高支化聚酯产物、触变复合物及涂料
CN114835911A (zh) * 2022-05-18 2022-08-02 中南民族大学 山梨醇型超支化聚酯、制备方法、应用及聚丙烯复合材料

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EP1070748A1 (fr) * 1999-07-20 2001-01-24 E.I. Du Pont De Nemours And Company Compositions de revêtement en poudre, méthode de préparation et utilisation
WO2001046296A1 (fr) * 1999-12-22 2001-06-28 Basf Corporation Macromolecule de polyol hyperramifie, procede de fabrication et revetement contenant cette macromolecule
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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1798266A4 (fr) * 2004-10-08 2007-10-31 Basf Coatings Japan Ltd Composition de resine a groupes hydroxyle pour revetements, composition de revetement, procede de revetement de finition et article revetu
EP1798266A2 (fr) * 2004-10-08 2007-06-20 BASF Coatings Japan Ltd. Composition de resine a groupes hydroxyle pour revetements, composition de revetement, procede de revetement de finition et article revetu
US7666331B2 (en) 2005-08-31 2010-02-23 Transitions Optical, Inc. Photochromic article
WO2009115580A2 (fr) * 2008-03-20 2009-09-24 National University Of Ireland, Galway Dendrimères et applications de dendrimères
WO2009115580A3 (fr) * 2008-03-20 2010-03-18 National University Of Ireland, Galway Dendrimères et applications de dendrimères
US8540813B2 (en) 2008-06-23 2013-09-24 Sicpa Holding Sa Intaglio printing ink comprising dendrimers
WO2009156400A1 (fr) 2008-06-23 2009-12-30 Sicpa Holding Sa Encre pour l'impression intaglio comprenant des dendrimères
KR101636587B1 (ko) * 2008-07-29 2016-07-05 히타치가세이가부시끼가이샤 에폭시 수지 경화제, 에폭시 수지 조성물, 그 경화물 및 광반도체장치
TWI464192B (zh) * 2008-07-29 2014-12-11 Hitachi Chemical Co Ltd An epoxy resin hardener, an epoxy resin composition, a cured product thereof, and an optical semiconductor device
CN104693419A (zh) * 2008-07-29 2015-06-10 日立化成工业株式会社 环氧树脂固化剂、环氧树脂组合物、其固化物以及光半导体装置
WO2010013638A1 (fr) * 2008-07-29 2010-02-04 日立化成工業株式会社 Agent de durcissement de résine époxy, composition de résine époxy, matériau durci de celle-ci et dispositif à semi-conducteurs optiques
KR20110055481A (ko) * 2008-07-29 2011-05-25 히다치 가세고교 가부시끼가이샤 에폭시 수지 경화제, 에폭시 수지 조성물, 그 경화물 및 광반도체장치
WO2011014284A1 (fr) * 2009-07-30 2011-02-03 E. I. Du Pont De Nemours And Company Procédé de production d’un revêtement présentant une valeur de brillant voulue
US10676565B2 (en) 2015-05-19 2020-06-09 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
US10526444B2 (en) 2015-09-25 2020-01-07 Eastman Chemical Company Polymers containing cyclobutanediol and 2,2-bis(hydroxymethyl)alkylcarboxylic acid
WO2017053379A1 (fr) * 2015-09-25 2017-03-30 Eastman Chemical Company Polymères contenant du cyclobutanediol et un acide 2,2-bis(hydroxyméthyl)alkylcarboxylique
CN108026256A (zh) * 2015-09-25 2018-05-11 伊士曼化工公司 包含环丁二醇和2,2-双(羟甲基)烷基羧酸的聚合物
US9988553B2 (en) 2016-02-22 2018-06-05 Eastman Chemical Company Thermosetting coating compositions
US10011737B2 (en) 2016-03-23 2018-07-03 Eastman Chemical Company Curable polyester polyols and their use in thermosetting soft feel coating formulations
US20190185701A1 (en) * 2017-12-20 2019-06-20 Ppg Industries Ohio, Inc. Ultradurable coating composition
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