WO2000034354A1 - Systeme de revetement a deux composants - Google Patents

Systeme de revetement a deux composants Download PDF

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Publication number
WO2000034354A1
WO2000034354A1 PCT/NL1999/000735 NL9900735W WO0034354A1 WO 2000034354 A1 WO2000034354 A1 WO 2000034354A1 NL 9900735 W NL9900735 W NL 9900735W WO 0034354 A1 WO0034354 A1 WO 0034354A1
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WIPO (PCT)
Prior art keywords
component
polymer
groups
functional
aryl
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Application number
PCT/NL1999/000735
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English (en)
Inventor
Rudolfus Antonius Theodorus Maria Van Benthem
Dick Adriaan Pons
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Dsm N.V.
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Publication date
Application filed by Dsm N.V. filed Critical Dsm N.V.
Priority to AU16962/00A priority Critical patent/AU1696200A/en
Publication of WO2000034354A1 publication Critical patent/WO2000034354A1/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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/60—Polyamides or polyester-amides
    • C08G18/606—Polyester-amides

Definitions

  • the present invention relates to a two- component coating system.
  • Two-component systems which can be cured at ambient temperatures are known. These systems can comprise, for example, a hydroxy-functional alkyd or polyester resin and as a crosslinking compound a polyisocyanate, a melamine/formaldehyde or a urea- formaldehyde resin.
  • the invention is characterized in that the two-component coating system comprises as a first component a linear or branched condensation polymer containing ester groups and at least one amide group in the backbone, having at least one hydroxyalkylamide endgroup, having a weight average molecular mass of > 800 g/mol and having a hydroxyl value between 20 and 400 mg KOH/gram resin and as a second component a compound that is capable of reacting with hydroxyl groups .
  • This two-component system shows a very good potlife, very good drying properties, good hardness properties and a relatively high solids content.
  • the condensation polymer has at least two hydroxyalkylamide endgroups .
  • a wide range of other desired properties can be obtained by the raw material selection.
  • Suitable compounds capable of reacting with hydroxyl groups are, for example, compounds containing an isocyanate group, compounds containing a methylolamine group, compounds containing an anhydride group compound containing a silane group, and compounds containing an epoxy group.
  • Suitable compounds containing a methylolamine group are, for example, melamine, urea, benzoguanime resins or an acrylate resin having N-methylolamide groups.
  • the polymer has at least two hydroxylamide endgroups .
  • the acid value of the first component generally ranges between 2 and 40 and ranges preferably between 5 and 10 mg KOH/gr resin.
  • the number average molecule weight (M n ) of the first component is at least 1000 and ranges generally between 1000 and 10000 and preferably between 1500 and 5000.
  • the glass transition temperature (Tg) of the first component is generally between 0°C and 90 °C and is preferably between 30 and 60°C.
  • the desired values for these product characteristics are depending of the specific selection of the first and second component.
  • the hydroxyl value of the first component ranges between 40 and 200 mg KOH/gram resin.
  • the curing reaction can take place at, for example, room temperature or at a temperature between, for example, 60 °C and 150 °C.
  • the condensation polymer contains at least two groups according to formula (I)
  • R4 R6 Y - C - C - O - H, H, (C!-C2o) (cyclo) alkyl ,
  • R! , R2 , R3 t R4 t ⁇ 5 anc j p6 may, independently of one another, be the same or different, H, (Cg-C ⁇ g) aryl or
  • the polymer contains at least two groups according to formula (II) :
  • B (C2-C24), optionally substituted, aryl or (cyclo) alkyl aliphatic diradical, and
  • R 1 , R2 , R3 r R4 t R5 anc j R6 may, independently of one another, be the same or different, H, (Cg-C ⁇ g) aryl or I ⁇ C Q ) (cyclo) alkyl radical.
  • the polymer containing hydroxyalkylamide groups is a polymer according to formula (III) :
  • Y - C - C - O - X 2 , H, (C; ⁇ -C2o) (cyclo) alkyl or
  • I I A - N - C - C - O - X 2 or OH
  • I I I I Y R 2 H B (C2-C24), optionally substituted, aryl or (cyclo) alkyl aliphatic diradical,
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may, independently of one another, be the same or different, H, (Cg-C_g) aryl or
  • R groups may together or with neighbouring carbon atoms form part of a cycloalkyl group.
  • the polymer containing ⁇ - hydroxyalkylamide groups is a polymer according to formula (IV) :
  • Y - C - C - 0 - X 2 , H, (C 1 -C 2 o) (cyclo) alkyl or
  • A - N - C - C - 0 - X 2 or OH
  • B ( C2-C20 ) ' optionally substituted, aryl or (cyclo) alkyl aliphatic diradical
  • I I X 1 - N - C - C - 0 - X 2
  • the polymer's ⁇ -hydroxyalkylamide functionality of the polymer is >. 6 and the polymer containing ⁇ -hydroxyalkylamide groups is a polymer represented by formula (V) :
  • R 3 and R ⁇ are (C2 . -C4) alkyl.
  • R 3 and R ⁇ are methyl or ethyl.
  • B may be saturated or unsaturated and preferably B is saturated.
  • B may be substituted with for example a (C_-C2 ) alkyl group, which may be saturated or unsaturated.
  • B may be for example a (methyl- ) 1 , 2- ethylene, (methyl- ) 1 , 2 -ethylidene, 1 , 3 -propylene, (methyl-) 1, 2-cyclohexyl, (methyl- ) 1 , 2 -phenylene, 1,3- phenylene, 1 , 4-phenylene, 2 , 3-norbornyl , 2 , 3 -norbornen- 5-yl and/or (methyl-) 1,2 cyclohex-4-enyl radical.
  • the polymer applied in the invention is generally a composition comprising higher and lower oligomers, which usually contains less than 50 wt.%, preferably less than 30 wt.%, of oligomers having a molecular weight smaller than 600.
  • the polymer can, for example, be obtained in a one-step procedure by reacting a cyclic anhydride and an alkanolamine, at a temperature between for example about 20°C and about 100°C, to form a ⁇ - hydroxyalkylamide, after which, at a temperature between, for example, 120°C and 250°C, a polyesteramide is obtained through polycondensation with water being removed through distillation.
  • the reaction can take place without a solvent, but also in water or in an organic solvent.
  • the removal of water through distillation can take place at 1 bar, in a vacuum or azeotropicall . Preferably the removal through distillation takes place azeotropically.
  • the cyclic anhydride is an anhydride according to formula (VI) :
  • Suitable cyclic anhydrides include phthalic anhydride, tetrahydrophthalic anhydride, naphtalenic dicarboxylic anhydride, hexahydrophthalic anhydride, 5-norbornene-2 , 3- dicarboxylic anhydride, norbornene-2 , 3 -dicarboxylic anhydride, naphtalenic dicarboxylic anhydride, 2- dodecene-1-yl-succinic anhydride, maleic anhydride, (methyl) succinic anhydride, glutaric anhydride, 4- methylphthalic anhydride, 4-methylhexahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride and the maleinised alkylester of an unsaturated fatty acid.
  • the alkanol is an alkanolamine according to formula (VII) :
  • I I Y - C - C - O - H or (C; ⁇ -C2o) (cyclo) alkyl ,
  • R 1 , R 2 , R 3 , R 4 , R5 an d R6 may, independently of one another, be the same or different, H, (Cg-C ⁇ g) aryl or (C].-C 8 ) (cyclo) alkyl radical or CH 2 OH.
  • the alkanolamine may be a monoalkanolamine, a dialkanolamine, a trialkanolamine or a mixture hereof .
  • linear polymers with a functionality of 2 can be obtained.
  • a linear or an entirely or partly branched polymer can be chosen, in which case the degree of branching can be set via the alkanolamines chosen. If a highly branched structure with a high functionality is desired, di- or trialkanolamines are used as the starting compound.
  • Suitable monoalkanolamines include ethanolamine, 1- (m) ethyl ethanolamine , n-butyl ethanolamine, l-(m) ethyl isopropanolamine, isobutanolamine , ⁇ -cyclohexanolamine, n-butyl isopropanolamine and n-propanolamine .
  • dialkanolamines are 3- amino-1 , 2-propanediol , 2-amino-l , 3 -propanediol diisobutanolamine (bis-2-hydroxy-l-butyl) amine) , di- ⁇ - cyclohexanolamine and diisopropanolamine (bis-2- hydroxy- 1 -propyl ) amine) .
  • a suitable trialkanolamine is, for example, tris (hydroxymethyl) aminomethane .
  • a ⁇ -alkyl-substituted ⁇ - hydroxyalkylamide is used.
  • examples are (di) isopropanolamine, cyclohexyl isopropanolamine, 1- (m) ethyl isopropanolamine, (di) isobutanolamine, di- ⁇ - cyclohexanolamine and/or n-butyl isopropanolamine. This results in polymer compositions with improved resistance to hydrolysis.
  • the anhydride : alkanolamine equivalent ratio is generally between 1.0:1.0 and 1.0:1.8.
  • this ratio is between 1:1.05 and 1:1.5.
  • the compound according to the invention can also be obtained via a reaction between an alkanolamine, as for example described above, and a compound containing one acid group and one activated acid group, after which a polyesteramide is obtained through polycondensation.
  • the compound containing an acid group and an activated acid group is preferably a compound according to formula (VIII) :
  • R 7 is a (C_-C ⁇ 2) branched or linear alkyl group .
  • alkyl esters such as, for example, mono (m) ethyl adipate and mono (m) ethyl sebacate, anhydrides and thioesters .
  • the compound according to the invention can also be obtained via a reaction between a cyclic anhydride, as for example described above, and an alcohol, after which the reaction product obtained reacts in situ with an alkanolamine and a polyesteramide is subsequently obtained through polycondensation .
  • suitable alcohols are (C ⁇ -C ⁇ g) alcohols .
  • butanol or 2-ethylhexanol are used.
  • the polymer may also contain carboxyl groups, in amounts of between 0.01 and 2.0 mg equivalent/gram of polymer.
  • the number of carboxylic acids present in the polymer can be controlled via the anhydride/alkanolamine ratio and via the degree of conversion. If an alkanolamine excess is used and the reaction is almost complete, less than 0.2 mg equivalent acid/gram of polymer is usually present.
  • carboxyl groups may in a subsequent step react with compounds containing one or more groups that can react with carboxylic acid, such as for example epoxy groups or ⁇ -hydroxyalkylamide groups.
  • the amount of carboxylic acid is preferably as low as possible, for example between 0.01 and 0.2 mg equivalent/gram of polymer.
  • the degree of branching and the functionality of the polymer are dependent on the starting materials and the molecular weight of the polymer.
  • a molecular weight higher than 2000 and the use of di- and/or trialkanolamines generally lead to highly branched structures with a functionality of 10.
  • the polyesteramide according to the invention can be obtained through polycondensation of mono- and/or bis-hydroxyalkylamides of bivalent carboxylic acids.
  • the monohydroxyalkylamides of bivalent carboxylic acids generally have the formula (IX) :
  • R 1 , R 2 , R 3 and R 4 may, independently of one another, be the same or different, H, (Cg-C]_o) aryl or (C ⁇ _- Cg) (cyclo) alkyl radical.
  • the polymer according to the invention generally comprises the amide and the ester groups alternating along the chain as follows:
  • the molar amount of amide bounds in the chain is higher than the amount of ester bounds.
  • the polymer according to the invention comprises at least 60% by weight of the products represented by the formulas (III)-(V).
  • composition according to the invention comprises also for example depoty amine groups having the formula (XI) :
  • R 1 , R 2 , R 3 and R 4 may, independently of one another, be the same or different, H, (C 6 -C ⁇ 0 ) aryl or (C ⁇ -C 8 ) (cyclo) alkyl radical. Also due to the presence in amounts of less than 10% by weight (of the total amount of anhydrides) of bisanhydrides in stead of the anhydrides according to formula (VI) it is possible that the polymer does not comprise only products according to formulas (III)- (V) .
  • the polymer according to the invention can be present both as an endgroup
  • the polyesteramide can react with a crosslinker compound, for example a compound containing isocyanate groups, for example, a diisocyanate, after which the isocyanate-functional polymer obtained reacts with a compound capable of reacting with isocyanates.
  • a crosslinker compound for example a compound containing isocyanate groups, for example, a diisocyanate
  • the diisocyanate can be a compound containing two or more isocyanate groups with different reactivities, for example an aliphatic diisocyanate with one sterically more accessible isocyanate group bound to a primary carbon atom and one sterically less accessible isocyanate group bound to a tertiary carbon atom.
  • diisocyanates examples include 1,4- diisocyanato-4 -methyl -pentane, 1 , 5-diisocyanato-5- methylhexane, 3 (4) -isocyanatomethyl-1- methylcyclohexylisocyanate, 1 , 6-diisocyanato-6-methyl- heptane, 1 , 5-diisocyanato-2 , 2 , 5-trimethylhexane and 1, 7-diisocyanato-3 , 7-dimethyloctane, and 1-isocyanato- 1-methyl-4- (4-isocyanatobut-2-yl) -cyclohexane, 1- isocyanato-1, 2 , 2-trimethyl-3- (2-isocyanato-ethyl) - cyclopentane, 1-isocyanato-l, 4-dimethyl-4- isocyanatomethyl -cyclohexane, 1-isocyanato-l,
  • the first component can also be combined in desired amounts together with one or more other polymers to obtain desired coating characteristics.
  • the first component being the hydroxyl functional condensation polymer is modified into a condensation polymer having another functionality, for example, an isocyanate functionality, an acid functionality, an
  • the hydroxyl functional condensation polymer can react with an amino acid to obtain the amine functional polymer.
  • the hydroxy functional condensation polymer can also react with a diisocyanate containing two or more isocyanate groups with different reactivities to obtain an isocyanate functional polymer.
  • the hydroxyl functional condensation polymer is (trans) esterified with an acid, for example an acetoacetic acid, an acid having unsaturations such as, for example, (meth) acrylic acid or an anhydride, to obtain an , ⁇ -unsaturated ester or a ⁇ -ketoacetic ester functionality.
  • the second component of the two-component system has to be selected from compounds capable of reacting with said functionalities.
  • Suitable compounds to react with the acid functional polymer are, for example, epoxy resins or acrylate resins having epoxy groups, adipic acid dihydrazide, polyaziridine or acid functional compounds .
  • Suitable compounds to react with the unsaturated ester functional polymer are, for example, amines, ⁇ -ketoesters, trimethylolpropane triacrylate and glutardialdehyde .
  • Suitable compounds to react with the ⁇ - ketoester functional polymer are, for example, (blocked) amines, and , ⁇ -unsaturated esters.
  • Suitable compounds to react with the isocyanate functional polymer are, for example, hydroxy or amine functional compounds.
  • the separate components of the two- component system can be mixed and applied at temperatures between 20°C and 180°C.
  • the system is very suitable for use at room temperature.
  • the compositions according to the present invention can be used on, for example, metal, wood and plastic substrates.
  • Waterbased polyesteramid resins can also be made by neutralisation of polyesteramid resins containing acid groups with a suitable amine and addition of water and a solvent, for example, butylglycol . These waterbased polyesteramid resins can be crosslinked with, for example, water dispersed melamine/formaldehyde, a glycoluril resin or a water dispersable (blocked) polyisocyanate compound at a temperature between, for example, 60°C and 150°C.
  • US-A-4123422 discloses an amide modified saturated polyester having an acid number of from about 0 to about 27, a hydroxyl number of from about 12 to about 360 and an amine number of from about 0.1 to about 6.5.
  • the amide modified saturated polyester polyols are useful as part of a two-package urethane coating system.
  • the coating system comprises at least one hydroxyl -terminated polyester resin with a hydroxyl number in the range from 20 to 200 mg KOH/g and a glass transition temperature of at least 40 °C, at least one carboxyl group containing, reversibly blocked polyisocyanate having at least two blocked isocyanate groups per molecule and an acid value of from 20 to 150 mg KOH/g, and at least one ⁇ -hydroxyalkyl -amide having at least two ⁇ -hydroxyalkylamide groups per molecule.
  • US-A-4123422 does not disclose a condensation polymer having the amide group in the backbone and also having an hydroxyalkylamide endgroup.
  • the present application is not directed to an amide modified saturated polyester as disclosed in US-A-4123422.
  • the invention will be elucidated with reference to the following non-limiting examples.
  • the reaction mixture was gradually heated, with stirring, to approx. 130 °C. After one hour at 130 °C, 175 grams of peanut fatty acid and 25 grams of benzoic acid are added to 272 gram of the reaction mixture and the mixture is gradually heated to 160 °C.
  • reaction water was removed by azeotropic distillation with xylene .
  • the polymer had an acid value of 1 (titrimetrically determined) and no more water could be removed by azeotropic distillation.
  • the polymer After cooling down to 100 °C the polymer is diluted with xylene to a solids content of about 60% w/w., 4,46 grams of succinic anhydride was added after a reaction time of 1 hour the resin had a acid value of 3 mg KOH/gram.
  • the polymer After cooling down to 100 °C the polymer is diluted with xylene to a solids content of about 60% w/w., 4.46 grams of succinic anhydride was added after a reaction time of 1 hour the resin had a acid value of 4 mg KOH/gram.
  • the reaction mixture was gradually heated, with stirring, to approx. 130 °C. After one hour at
  • the reaction water was removed by azeotropic distillation with xylene. After a total reaction time of 4 hours the polymer had an acid value of 1 (titrimetrically determined) and no more water could be removed by azeotropic distillation. After cooling down to 100 °C the polymer is diluted with xylene to a solids content of about 60% w/w., 14.3 grams of succinic anhydride was added after a reaction time of 1 hour the resin had a acid value of 15 mg KOH/gram. After cooling the product obtained was a yellow viscous mass.
  • the reaction mixture was gradually heated, with stirring, to approx. 130°C. After one hour at 130°C, 60 grams of benzoic acid are added to the reaction mixture and the mixture is gradually heated to 160°C.
  • reaction water was removed by azeotropic distillation with xylene. After a total reaction time of 4 hours the polymer had an acid value of about 1 (titrimetrically determined) and no more water could be removed by azeotropic distillation.
  • the polymer After cooling down to 100 °C the polymer is diluted with xylene to a solids content of about 60% w/w., 14.3 grams of succinic anhydride was added after a reaction time of 1 hour the resin had a acid value of 15 mg KOH/gram.
  • the lacquer composition as given in Table I was applied on a wood substrate as a 100 ⁇ m thick layer.
  • Example I was repeated with the difference that the polymer according to Experiment I was replaced by a short-oil alkyd resin based on a low rosin tall oil (Uralac AD-525X-60TM of DSM Resins)
  • the two component system according to the invention results in improved hardness properties.
  • the system according to the invention results in an improved chemical resistance, improved water resistance and in a faster hardness build-up. Furthermore, the solids content is much higher.
  • the metal coating based on the resin according to Example IV results in a fast drying system showing very good hardness properties.

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

Abstract

L'invention concerne un système à deux composants, comprenant comme premier composant un polycondensat linéaire ou ramifié, qui renferme dans son squelette des groupes ester et au moins un groupe amide, qui comporte au moins un groupe terminal hydroxyalkylamide, et qui a une masse moléculaire moyenne en poids ≥ 800 g/mol et un indice d'hydroxylation compris entre 20 et 400 mg KOH/g de résine; et comme second composant un composé capable de réagir avec les groupes hydroxyle.
PCT/NL1999/000735 1998-12-07 1999-12-02 Systeme de revetement a deux composants WO2000034354A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16962/00A AU1696200A (en) 1998-12-07 1999-12-02 Two-component coating system

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98204134 1998-12-07
EP98204134.5 1998-12-07

Publications (1)

Publication Number Publication Date
WO2000034354A1 true WO2000034354A1 (fr) 2000-06-15

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PCT/NL1999/000735 WO2000034354A1 (fr) 1998-12-07 1999-12-02 Systeme de revetement a deux composants

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011007003A1 (fr) 2009-07-16 2011-01-20 Dsm Ip Assets B.V. Résines et compositions de revêtement
CN104497835A (zh) * 2014-11-21 2015-04-08 广东巴德士化工有限公司 一种高温厚涂不起痱子的环保pu透明底漆

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123422A (en) * 1977-11-25 1978-10-31 Ppg Industries, Inc. Amide modified saturated polyester polyols and method of making
US4788255A (en) * 1986-09-29 1988-11-29 Ppg Industries, Inc. Powder coating compositions
US5538759A (en) * 1994-08-26 1996-07-23 Ems-Inventa Ag Epoxy-free, heat-curable coating system
DE19703952A1 (de) * 1996-07-12 1998-01-15 Inventa Ag beta-hydroxyalkylamidgruppenhaltige Ester, Verfahren zu deren Herstellung und Verwendung der Ester
WO1999016810A1 (fr) * 1997-10-01 1999-04-08 Dsm N.V. Polymere de condensation contenant des groupes hydroxylalkylamides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123422A (en) * 1977-11-25 1978-10-31 Ppg Industries, Inc. Amide modified saturated polyester polyols and method of making
US4788255A (en) * 1986-09-29 1988-11-29 Ppg Industries, Inc. Powder coating compositions
US5538759A (en) * 1994-08-26 1996-07-23 Ems-Inventa Ag Epoxy-free, heat-curable coating system
DE19703952A1 (de) * 1996-07-12 1998-01-15 Inventa Ag beta-hydroxyalkylamidgruppenhaltige Ester, Verfahren zu deren Herstellung und Verwendung der Ester
WO1999016810A1 (fr) * 1997-10-01 1999-04-08 Dsm N.V. Polymere de condensation contenant des groupes hydroxylalkylamides

Non-Patent Citations (2)

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Title
CHEMICAL ABSTRACTS, vol. 73, no. 20, 16 November 1970, Columbus, Ohio, US; abstract no. 100125v, XP002102232 *
W.J. SCHNEIDER ET AL.: "Poly(ester amides) from linseed and soybean oils for protecting coatings.", J. PAINT TECHNOL., vol. 42, no. 548, 1970, pages 493 - 7 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011007003A1 (fr) 2009-07-16 2011-01-20 Dsm Ip Assets B.V. Résines et compositions de revêtement
US20120183749A1 (en) * 2009-07-16 2012-07-19 Franciscus Johannes Marie Derks Resins and coating compositions
US8999494B2 (en) * 2009-07-16 2015-04-07 Dsm Ip Assets B.V. Resins and coating compositions
CN104497835A (zh) * 2014-11-21 2015-04-08 广东巴德士化工有限公司 一种高温厚涂不起痱子的环保pu透明底漆

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