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WO2002085999A1 - Compositions pulverulentes thermodurcissables pour revetements - Google Patents

Compositions pulverulentes thermodurcissables pour revetements Download PDF

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Publication number
WO2002085999A1
WO2002085999A1 PCT/EP2002/004294 EP0204294W WO02085999A1 WO 2002085999 A1 WO2002085999 A1 WO 2002085999A1 EP 0204294 W EP0204294 W EP 0204294W WO 02085999 A1 WO02085999 A1 WO 02085999A1
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WO
WIPO (PCT)
Prior art keywords
acid
mole
neopentyl glycol
thermosetting compositions
group containing
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
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PCT/EP2002/004294
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English (en)
Inventor
Luc Moens
Nele Knoops
Daniel Maetens
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UCB SA
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UCB SA
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Filing date
Publication date
Application filed by UCB SA filed Critical UCB SA
Publication of WO2002085999A1 publication Critical patent/WO2002085999A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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

Definitions

  • thermosetting powder compositions comprising a mixture of an isophthalic acid and neopentyl glycol hydroxypivalate rich carboxyl functionalised polyester along with a ⁇ -hydroxyalkylamide group containing cross-linking agent.
  • the invention also relates to the use of said compositions for the preparation of powdered paints and varnishes for the making of coatings and to coatings obtained therewith.
  • Thermosetting powder compositions are well known in the art and are widely used as paints and varnishes for coating the most various articles.
  • the advantages of these powder coatings are numerous; on the one hand, the problems associated with solvents are completely eliminated, and on the other hand, the powders are used without any loss since only the powder in direct contact with the substrate is retained on the article, the excess powder being, in principle, entirely recoverable and reusable.
  • the powder coating compositions are preferred to coating compositions in the form of solutions in organic solvents.
  • thermosetting powder compositions have already been widely used in the coating of domestic electrical appliances, automobile industry accessories, and the like. They generally contain a thermosetting organic binder, fillers, pigments, catalysts and various additives used to adapt their properties to their intended use.
  • thermosetting powder compositions There are various types of thermosetting powder compositions.
  • the best known compositions contain either a mixture of carboxyl group-containing polymers, such as a carboxyl group-containing polyester or polyacrylate, and epoxy compounds, such as triglycidyl isocyanurate, glycidyl group-containing acrylic copolymers or ⁇ - hydroxyalkylamides or a mixture of hydroxyl group-containing polymers, most often a hydroxyl group-containing polyester, with blocked or non-blocked isocyanates, melamine resins, and the like.
  • carboxyl group-containing polymers such as a carboxyl group-containing polyester or polyacrylate
  • epoxy compounds such as triglycidyl isocyanurate, glycidyl group-containing acrylic copolymers or ⁇ - hydroxyalkylamides or a mixture of hydroxyl group-containing polymers, most often a hydroxyl group-containing polyester, with blocked or non-blocked isocyanates,
  • polyesters are usually prepared from aromatic dicarboxylic acids, mainly terephthalic acid and isophthalic acid and optionally a minor proportion of aliphatic or cycloaliphatic dicarboxylic acids, and from various polyols such as ethylene glycol, neopentyl glycol, 1 ,6- hexanediol, trimethylolpropane, and the like.
  • aromatic dicarboxylic acids mainly terephthalic acid and isophthalic acid and optionally a minor proportion of aliphatic or cycloaliphatic dicarboxylic acids
  • polyols such as ethylene glycol, neopentyl glycol, 1 ,6- hexanediol, trimethylolpropane, and the like.
  • polyesters and the powders derived from them often are used because of their remarkable weatherability characteristics.
  • These polyesters mostly are derived from isophthalic acid, being the most important acid constituent among others and are commonly used with triglycidyl isocyanurate (TGIC) as the cross-linking agent.
  • TGIC triglycidyl isocyanurate
  • TGIC presents problems of health and security. Indeed, TGIC is relatively toxic (Rat Oral LD50 of 0,4 g/kg) and is mutagenic according to the Ames Mutagenicity Test.
  • ⁇ -hydroxyalkylamides As a non toxic alternative to TGIC, ⁇ -hydroxyalkylamides have been used for the cross- linking of powders containing carboxyl-bearing polyesters. But the use of ⁇ -hydroxyalkylamides brings about new problems due to its high reactivity and to the fact that water is liberated during it's reaction with carboxyl groups.
  • Powder paints comprising as a binder a carboxylic acid group containing polyester and a ⁇ -hydroxyalkylamides group containing cross-linking agent, produce water upon curing, ' thus creating bubbles in the coating especially when relatively thick layers are applied. Gas bubbles remaining in the coating reduce the adherence and the protective effect of the coating. In order to reduce or even avoid these gas bubbles remaining in the coating, two solutions, being either reducing the melt viscosity of the powder, or slackening the reactivity of the binder system can be envisaged. Yet, incorporation of considerable amounts of plasticising constituents in the binder system often reduces outdoor durability of the cured paint.
  • EP 649890 claims powder coating compositions comprising a ⁇ -hydroxyalkylamides cross- linking agent and an acid functional polyester having an acid number ranging from 15 through 70 mg KOH/g which is substantially based on dicarboxylic acid units containing 80 to 100% mole of isophthalic acid, on glycols containing at least 50% mole of branched aliphatic glycols with at least 4 carbon atoms and on monomers having a functionality of three, in an amount from 2 to 8% mole based on the total amount of dicarboxylic acids and glycols.
  • thermosetting powder coating compositions derived from carboxyl functional isophthalic acid rich amorphous polyesters is the use of semi- crystalline acid functional polyesters as co-reactable part of the carboxylic acid amorphous resin in a binder along with a polyepoxy compound or a ⁇ -hydroxyalkylamides, such as claimed in e.g. WO 91 / 14745.
  • a careful selection of the proper combination of amorphous and semi-crystalline resins, respectively, enables for flexible and weatherable powder coating compositions derived from carboxyl functional isophthalic acid rich polyesters, as far as particular process conditions for mixing, extrusion and grinding are exercised and appropriate storage conditions of the powder thus obtained, are considered.
  • the solution presented in this invention to mix a semi-crystalline acid functional polyesters with a carboxyl functional amorphous polyester represents a technical complication.
  • thermosetting powders which comprise a carboxyl group-containing polyester and a ⁇ -hydroxyalkylamides.
  • the polyester may comprise isoththalic or terephthalic acid and has a functionality less than 2, obtained by the addition in the polyester of monofunctional acids or alcohols. Due to the low functionality of the polyester, its reactivity is reduced, which brings about a better flow during the melting of the powder on the substrate. Nevertheless, as the polyester has some non-reactive end groups which do not participate in the cross-linking reaction during the formation of the coating, the latter has a reduced solvent resistance and a reduced flexibility.
  • the powder coating compositions comprising the binder of the present invention, based on a carboxylic acid group containing amorphous isophthalic acid and neopentyl glycol hydroxypivalate rich polyester in combination with a ⁇ -hydroxyalkylamide group containing cross-linking agent, give paint films proving outstanding degassing properties at a film thickness of up to about 200 ⁇ m for a curing time of from 15 seconds to 50 minutes at curing temperatures from 140 to 250°C.
  • the powdered thermosetting compositions of the inventioin produce coatings proving very smooth coatings, exhibiting excellent outdoor durability and flexibility, without any defects possibly originated from volatile compounds.
  • neopentyl glycol hydroxypivalate flexibilises powder coatings derived from isophthalic acid rich polyesters, nor of the unexpected effect of the neopentyl glycol hydroxypivalate containing isophthalic acid rich resins on the degassing properties of the paint films derived from powder formulations containing these resins in combination with a ⁇ -hydroxyalkylamide cross-linking agent.
  • thermosetting compositions for coatings characterised in that they comprise: a) a carboxylic acid group containing polyester composed of polycarboxylic units containing from 80 to 100% mole of isophthalic acid and from 0 to 20% mole of another aliphatic, cycloaliphatic or aromatic polyacid, and of a polyol constituent comprising from 10 to
  • neopentyl glycol hydroxypivalate 60% mole of neopentyl glycol hydroxypivalate, from 40 to 90% mole of neopentyl glycol and from 0 to 30% mole and preferably from 0 to 20% mole of another aliphatic and/or cycloaliphatic polyol; b) a ⁇ -hydroxyalkylamides group containing cross-linking agent. If no other aliphatic and/or cycloaliphatic polyol are used in the synthesis of the polyester of the invention, instead of neopentyl glycol hydroxypivalate, use can be made of an amount of hydroxypivalic acid corresponding to the amount of neopentyl glycol.
  • hydroxypivalic acid is first allowed to react with the corresponding amount of neopentyl glycol before the other polyols are put into reaction.
  • the carboxyl functional amorphous polyester of the present invention further is characterised by: an acid number from 15 to 70 mg KOH/g, preferably from 20 to 50 mg KOH/g and more preferably from 25 to 35 mg KOH/g - a number averaged molecular weight ranging from 1600 to 8600, preferably from 2200 to 7000 and more preferably from 3200 to 6500 as measured by gel permeation chromatography (GPC) a glass transition temperature Tg from 40 to 80°C and preferably from 50 to 70°C as measured by differential scanning calorimetry (DSC) according to ASTM D3418 with a heating gradient of 20°C per minute an ICI (cone/plate) viscosity accordingly to ASTM D4287, measured at 200°C ranging from 5 to 15000 mPa.s
  • the acid constituent of the amorphous polyester is for 80 to 100% mole composed of isophthalic acid and for 0 to 20% mole of another polyacid constituent selected from one or more aliphatic, cycloaliphatic or aromatic polyacids, such as: fumaric acid, maleic acid, phthalic anhydride, terephthalic acid, 1,4- cyclohexanedicarboxylic acid, 1 ,3-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, succinic acid, adipic acid, glutaric acid, pimelic acid, suberic acid, azealic acid, sebacic acid, 1, 12-dodecanedioic acid, trimellitic acid or pyromellitic acid, etc., or the corresponding anhydrides.
  • another polyacid constituent selected from one or more aliphatic, cycloaliphatic or aromatic polyacids, such as: fumaric acid, maleic acid,
  • the glycol constituent of the amorphous polyester is for 10 to 60% mole composed of neopentyl glycol hydroxypivalate, for 40 to 90% mole composed of neopentyl glycol and for 0 to 30% mole and preferably for 0 to 20% mole of another polyol constituent selected from one or more aliphatic or cycloaliphatic polyol such as ethylene glycol, propylene glycol, 1 ,4-butanediol, 1,6-hexanediol, 1,4-cyclohexanediol, 1,4- cyclohexanedimethanol, 2-methyl-l,3-propanediol, hydrogenated Bisphenol A, 2-butyl-2- ethyl- l,3-propanediol, trimethylolpropane, ditrimethylolpropane, pentaerythrytol, etc.
  • another polyol constituent selected from one or more aliphatic or cycl
  • the polyester according to the present invention is composed of polycarboxylic acid units containing from SO to 100% mole of isophthalic acid, from 0 to 20% mole of terephthalic acid and/or 1,4-cyclohexanedicarboxylic acid and from 0 to 15% mole of trimellitic anhydride or pyromellitic anhydride, and of polyol constituents containing from 10 to 60% mole of neopentyl glycol hydroxypivalate, from 40 to 90% mole of neopentyl glycol and from 0 to 20% mole of trimethylolpropane or pentaerythrytol.
  • the carboxylic acid group containing amorphous polyester is prepared using conventional esterification techniques well known in the art.
  • the polyester is prepared according to a procedure consisting of one or more reaction steps.
  • polyesters For the preparation of these polyesters, a conventional reactor equipped with a stirrer, an inert gas (nitrogen) inlet, a thermocouple, a distillation column connected to a water-cooled condenser, a water separator and a vacuum connection tube is used.
  • the esterification conditions used to prepare the polyesters are conventional, namely a standard esterification catalyst, such as dibutyltin oxide, dibutyltin dilaurate, n-butyltin trioctoate, sulphuric acid or a sulphonic acid, can be used in an amount from 0.05 to 1.50% by weight of the reactants and optionally, colour stabilisers, for example, phenolic antioxidants such as Irganox 1010 (Ciba) or phosphonite- and phosphite-type stabilisers such as tributylphosphite, can be added in an amount from 0 to 1% by weight of the reactants.
  • a standard esterification catalyst such as dibutyltin oxide, dibutyltin dilaurate, n-butyltin trioctoate, sulphuric acid or a sulphonic acid
  • colour stabilisers for example, phenolic antioxidants such as Irganox 1010
  • Polyesterification is generally carried out at a temperature which is gradually increased from 130°C to about 190 to 250°C, first under normal pressure, then, when necessary, under reduced pressure at the end of each process step, while maintaining these operating conditions until a polyester is obtained, which has the desired hydroxyl and /or acid number.
  • the degree of esterification is followed by determining the amount of water formed in the course of the reaction and the properties of the obtained polyester, for example the hydroxyl number, the acid number, the molecular weight or the viscosity.
  • the carboxyl group containing amorphous polyester, as described above, is part of a binder system along with a ⁇ -hydroxyalkylamide group containing cross-linking agent, in the preparation of powder coating compositions for use as paint or clear lacquer.
  • Suitable ⁇ -hydroxyalkylamide cross-linking agents are those which contain at least one, preferably two bis( ⁇ -hydroxyalkyl)amide groups.
  • Commercial products are available, such as N,N,N',N'-tetrakis-(2-hydroxyethyl)-adipamide, known under the tradename Primid XL-552 and N,N,N',N'-tetrakis-(2-hydroxypropyl)-adipamide, known under the tradename Primid QM1260 for example.
  • the ⁇ -hydroxyalkylamide group containing cross-linking agent described herein above is used in an amount from 0.25 to 1.40 preferably from 0.60 to 1.05 equivalent of carboxyl group present in the amorphous polyester per equivalent of ⁇ -hydroxyalkyl groups.
  • compositions within the scope of the present invention can also include flow control agents such as Resiflow PV5 (Worlee), Modaflow (Monsanto), Acronal 4F (BASF), etc., and degassing agents such as benzoin (BASF) etc.
  • flow control agents such as Resiflow PV5 (Worlee), Modaflow (Monsanto), Acronal 4F (BASF), etc.
  • degassing agents such as benzoin (BASF) etc.
  • UV-light absorbers such as Tinuvin 900 (Ciba), hindered amine light stabilisers represented by Tinuvin 144 (Ciba), other stabilising agents such as Tinuvin 312 and 1 130 (Ciba), antioxidants such as Irganox 1010 (Ciba) and stabilisers from the phosphonite or phosphite type can be added.
  • a variety of dyes and pigments can be utilised in the composition of this invention.
  • useful pigments and dyes are: metallic oxides such as titaniumdioxide, ironoxide, zincoxide and the like, metal hydroxides, metal powders, sulphides, sulphates, carbonates, silicates such as ammoniumsilicate, carbon black, talc, china clay, barytes, iron blues, leadblues, organic reds, organic maroons and the like.
  • the components of the composition according to the invention may be mixed by dry blending in a mixer or blender (e.g. drum mixer).
  • the premix is then homogenised at temperatures ranging from 70 to 150°C in a single screw extruder such as the BUSS-Ko- Kneter or a double screw extruder such as the PRISM or APV.
  • the extrudate when cooled down, is grounded to a powder with a particle size ranging from 10 to 150 ⁇ m.
  • the powdered composition may be deposited on the substrate by use of a powder gun such as an electrostatic CORONA gun or TRIBO gun.
  • well known methods of powder deposition such as the fluidised bed technique can be used. After deposition the powder is heated to a temperature between 140 and 250°C, causing the particles to flow and fuse together to form a smooth, uniform, continuous, uncratered coating on the substrate surface.
  • a mixture of 232.8 parts of neopentyl glycol, 232.8 parts of neopentyl glycol hydroxypivalate and 16.7 parts of trimethylolpropane is placed in a conventional four neck round bottom flask equipped with a stirrer, a distillation column connected to a water cooled condenser, an inlet for nitrogen and a thermometer attached to a thermoregulator.
  • the flask contents are heated, while stirring under nitrogen, to a temperature of circa 130°C at which point 643.6 parts of isophthalic acid and 2.5 parts of n-butyltintrioctoate are added.
  • the heating is continued gradually to a temperature of 230°C.
  • Water is distilled from the reactor from 180°C on. When distillation under atmospheric pressure stops, a vacuum of 50 mm Hg is gradually applied. After three hours at 230°C and 50 mm Hg, following characteristics are obtained:
  • a mixture of 270.9 parts of neopentyl glycol, 180.6 parts of neopentyl glycol hydroxypivalate and 16.7 parts of trimethylolpropane is placed in a reactor as for Example 1.
  • a temperature of 130°C 130.6 parts of terephthalic acid, 413.5 parts of isophthalic acid and 2.5 parts of n-butyltintrioctoate are added.
  • the reaction is continued at 220°C under atmospheric pressure until about 95% of the theoretical amount of water is distilled and a transparent hydroxyl functionalised prepolymer with following characteristics is obtained:
  • Example 1 Adopting the procedure of Example 1 as series of examples, accordingly the present invention, (Ex. 3 - Ex. 6) as well as a series of comparative examples (Comp. Ex. 1 - Comp. Ex. 3) were prepared.
  • the monomer composition as well as the resin characteristics are given in table 1.
  • Example 9 The polyesters as illustrated above, are then formulated to a powder accordingly to one of the formulations as mentioned below.
  • the powders are prepared first by dry blending of the different components and then by homogenisation in the melt using a PRISM 16 mm L/D 15/ 1 twin screw extruder at an extrusion temperature of 85°C.
  • the homogenised mix is then cooled and grinded in an
  • the powders according to the present invention (Ex. 10 to 17) thus prove to satisfy a combination of properties, such as outstanding flexibility, gloss and flow, giving a very good surface aspect, which till now hardly could be obtained altogether.
  • polyester resins answering a composition as claimed in this invention allow for paint coating without any defects or pinholing at a thickness of up to 200 ⁇ m.
  • powder formulations answering e.g. examples 10, 12, 15, 17, allow for paint films of 200 ⁇ m with outstanding flow and without showing any pinhole or other defect .
  • the powder coating compositions of the present invention prove to satisfy an excellent outdoor resistance comparable to the currently used nowadays commercial polyester based powders.
  • I 0.77 W/m 2 /nm
  • UV-B 313 nm lamps where unwanted or unnatural chemical reactions are induced, as described in "Analysis of Test Methods for UV Durability Predictions of Polymer Coatings” from Courtaulds Coatings Ltd. as presented during the XXth International Conference in Organic Coatings/Science and Technology (Athens, Greece, 07/94) or as described in the Technical Bulletin L8006 from Q- Panel or by N. Patel, JOCCA 3, 104, (1991).
  • the panels used in the Q-UV are chromated aluminium ones. Table 4
  • powder compositions according to the present invention containing as a binder a combination of the carboxyl functional polyester according to the present invention along with a ⁇ -hydroxyalkylamide cross-linking agent prove upon application and curing an unique combination of properties such as a good flexibility, outstanding flow and gloss and a remarkable weatherability.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des compositions pulvérulentes thermodurcissables pour revêtements, comprenant un groupe acide carboxylique contenant un polyester à base d'un constituant polyacide comprenant entre 80 et 100% en mole d'acide isophtalique et entre 0 et 20% en mole, d'un autre polyacide aliphatique, cycloaliphatique ou aromatique, ainsi qu'un constituant polyol comprenant entre 10 et 60% en mole de néopentyl glycol hydroxypivalate, entre 40 et 90% en mole de néopentyl glycol et entre 0 et 30% en mole et de préférence entre 0 et 20% en mole d'un autre polyol aliphatique et/ou cycloaliphatique. L'agent réticulant du polyester est un composé contenant un groupe β-hydroxyalkylamide. Les revêtements obtenus avec ces poudres sont très lisses, sans petits trous ou d'autres défauts et manifestent une excellente durabilité et flexibilité à l'extérieur.
PCT/EP2002/004294 2001-04-25 2002-04-18 Compositions pulverulentes thermodurcissables pour revetements Ceased WO2002085999A1 (fr)

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EP01110267 2001-04-25
EP01110267.0 2001-04-25

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WO2002085999A1 true WO2002085999A1 (fr) 2002-10-31

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010094811A1 (fr) * 2009-03-27 2010-08-26 Dsm Ip Assets B.V. Composition de revêtement en poudre comprenant un polyester et un bêta-hydroxyalkylamide servant d'agent de réticulation
US7955655B2 (en) * 2002-02-18 2011-06-07 Kansai Paint Co., Ltd. Coating compositions and method of forming coating film
CN104277207A (zh) * 2014-10-31 2015-01-14 安徽神剑新材料股份有限公司 一种超耐候低温固化型聚酯树脂
CN104292443A (zh) * 2014-10-31 2015-01-21 安徽神剑新材料股份有限公司 一种超耐候低温固化型聚酯树脂的制备方法
CN111138642A (zh) * 2019-12-27 2020-05-12 广东银洋环保新材料有限公司 一种微波炉内层粉末涂料用聚酯树脂及其制备方法和粉末涂料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6090268A (ja) * 1983-10-21 1985-05-21 Toyobo Co Ltd 塗装鋼板用塗料組成物
WO1994011451A1 (fr) * 1992-11-13 1994-05-26 Dsm N.V. PEINTURE PULVERULENTE A BASE DE POLYMERES A FONCTION D'ACIDE ET DE COMPOSES DE β-HYDROXYALKYLAMIDE
JPH10204376A (ja) * 1997-01-21 1998-08-04 Nippon Ester Co Ltd 粉体塗料用ポリエステル樹脂及び組成物
WO1999040143A1 (fr) * 1998-02-09 1999-08-12 Ucb S.A. Polyester contenant des groupes carboxyle tertiaires, son procede de preparation et compositions thermodurcissables en poudre le contenant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6090268A (ja) * 1983-10-21 1985-05-21 Toyobo Co Ltd 塗装鋼板用塗料組成物
WO1994011451A1 (fr) * 1992-11-13 1994-05-26 Dsm N.V. PEINTURE PULVERULENTE A BASE DE POLYMERES A FONCTION D'ACIDE ET DE COMPOSES DE β-HYDROXYALKYLAMIDE
JPH10204376A (ja) * 1997-01-21 1998-08-04 Nippon Ester Co Ltd 粉体塗料用ポリエステル樹脂及び組成物
WO1999040143A1 (fr) * 1998-02-09 1999-08-12 Ucb S.A. Polyester contenant des groupes carboxyle tertiaires, son procede de preparation et compositions thermodurcissables en poudre le contenant

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Title
PATENT ABSTRACTS OF JAPAN vol. 009, no. 233 (C - 304) 19 September 1985 (1985-09-19) *
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 13 30 November 1998 (1998-11-30) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7955655B2 (en) * 2002-02-18 2011-06-07 Kansai Paint Co., Ltd. Coating compositions and method of forming coating film
WO2010094811A1 (fr) * 2009-03-27 2010-08-26 Dsm Ip Assets B.V. Composition de revêtement en poudre comprenant un polyester et un bêta-hydroxyalkylamide servant d'agent de réticulation
US9169419B2 (en) 2009-03-27 2015-10-27 Dsm Ip Assets B.V. Powder coating composition comprising a polyester and a β-hydroxyalkylamide as crosslinker
CN104277207A (zh) * 2014-10-31 2015-01-14 安徽神剑新材料股份有限公司 一种超耐候低温固化型聚酯树脂
CN104292443A (zh) * 2014-10-31 2015-01-21 安徽神剑新材料股份有限公司 一种超耐候低温固化型聚酯树脂的制备方法
CN111138642A (zh) * 2019-12-27 2020-05-12 广东银洋环保新材料有限公司 一种微波炉内层粉末涂料用聚酯树脂及其制备方法和粉末涂料

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