Classifications

• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/02—Polycondensates containing more than one epoxy group per molecule
  • C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
• • 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
  • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• • 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
  • C08G63/91—Polymers modified by chemical after-treatment
• • 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
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31786—Of polyester [e.g., alkyd, etc.]

Definitions

• the present invention relates to outdoor durable coating compositions derived from tertiary carboxyl functional polyesters and/or polyglycidyl ester resin derived from said tertiary carboxyl functional poly- esters, to said tertiary carboxyl functional polyester resins themselves and especially linear resins, to a process for the preparation of the resins, to polyglycidylester resins obtainable by glycidating said tertiary carboxyl functional polyester resins. More in particular the invention relates to powder coating compositions, comprising said tertiary carboxyl functional polyester resins and/or said polyglycidylester resins and to cured products which have been obtained by using the indicated coating compositions and show improved outdoor properties.
• TGIC polyester/- triglycidylisocyanurate
• Powder coating compositions based on solid glycidylesters obtained by reaction of 2,2-bis- (4-hydroxyphenyl) propane (bisphenol A) and epichloro- hydrin are known already for a long time.
• the cured products prepared on the basis of these compositions are resistant against hydrolysis, however, they show a low ultraviolet resistance and are therefore not suitable for applications requiring a high quality outdoor durability such as building parts or automotive topcoats.
• EP-0720997A especially figure 1, from which it appears that powder coatings based on EPIKOTE (di-glycidyl ether of 2,2-bis- ( 4-hydroxyphenyl) propane) and a number of commercial polyester/acrylics resins only show moderate weathering resistance .
• Said tertiary carboxyl functional polyester resins and said polyglycidylester resins are particularly suitable for use in outdoor durable powder coating compositions, which are relatively environmentally friendly and which provide more in particular weathering resistant and acid resistant cured resin matrices.
• the backbones of the resins according to the present invention do not comprise any ester functions which are susceptible to hydrolysis under relatively mild conditions, and the polyester resins do not comprise any functionalities which are UV-sensitive.
• the end groups of the resins (i.e. in the backbone) according to the present invention are preferably carboxyl groups, especially secondary groups, but may also be hydroxyl groups, especially secondary groups, or, optionally, esterified hydroxyl groups.
• the present invention relates to tertiary carboxyl functional polyester resin obtainable by reaction of: a) at least one aliphatic compound A comprising aliphatic hydroxyl groups which may each independently be a primary or secondary hydroxyl group and a tertiary carboxyl group, b) optionally one or more hydroxyl compounds B, each compound comprising two aliphatic hydroxyl groups which may each independently be a primary or secondary hydroxyl group, c) at least one cycloaliphatic carboxylic acid compound C comprising two secondary aliphatic carboxyl groups or the anhydride thereof, d) optionally one or more dicarboxylic acid compounds D comprising two aliphatic carboxyl groups or the anhydride thereof, and e) optionally either one or more compounds E comprising one primary or secondary hydroxyl group and optionally a tertiary carboxyl group, or one or more monocarboxylic acid compounds G, comprising a primary or secondary carboxyl group, together with equivalent mole
• the compounds actually selected as A or B and F are the same, but in principle two or more different representatives of the group defined for A and B can be used actually as compounds A, B and F.
• Another aspect of the invention is formed by a process to prepare the hereinbefore specified polyester resins. Said process is preferably carried out until all, or substantially all, the non-tertiary carboxyl groups as initially present in the reaction mixture have reacted, or until all, or substantially all hydroxyl groups as initially present in the reaction mixture have reacted, depending on the equivalents starting material used. It will be appreciated that instead of the pure (or almost pure) compounds A, B, C, D, E, F and G, also mixtures of two or more compounds A, B, C, D, E, F and G may be used.
• the compounds A, B, C, D, E, F and G are straight or branched (cyclo) hydrocarbyl compounds and preferably are not substituted by any functional groups, but only comprise hydroxy and/or carboxyl groups .
• the term "substantially” as used above indicates that at least 92%, preferably at least 95%, more preferably at least 98%, still more preferably at least 99% of the original non-tertiary carboxyl groups or hydroxyl groups have reacted.
• the tertiary carboxyl functional polyester resins thus produced are practically free from non-tertiary carboxyl groups or hydroxyl groups when they have an acid value which corresponds to the theoretical value calculated on the basis of the amount of tertiary carboxyl groups of the reactants as initially present in the reaction mixture and the amount of reacting carboxyl and hydroxyl groups.
• the term "practically” is used herein to indicate a deviation from the theoretical value of
• the molecular weight distribution and number average molecular weight of the resin produced will depend on the specific reactants and the ratios applied in the process of the invention.
• the tertiary aliphatic groups present in compound A and optionally E practically do not react under the esterification conditions employed, glycidation of these tertiary aliphatic carboxyl groups with epihalohydrin can be performed under standard alkaline conditions whereby a polyglycidylester resin can be obtained which contains a low hydrolizable halogen content, usually lower than 0.5% by weight based on the total weight of the composition.
• the polyester resins of the present invention are particularly suitable for the preparation of powder coatings, in view of the absence of relatively low molecular products.
• the order of addition may be chosen in such a way (by first adding one equivalent of anhydride C to two equivalents of dihydroxyl compound A, followed after completion of the reaction by the remainder of the starting compounds included a second batch of A as component F) that the smallest molecule formed will always comprise two molecules of A and three molecules of C, thus having a molecular weight of at least 700. This means that after glycidation even the smallest molecule possible has a relatively high molecular weight, and thus a low toxiticity of the product is expected.
• the polyester intermediates used in the present invention are preferably linear products, as this will result in the highest Tg temperatures. Therefore, the starting compounds for said polyesters are preferably bi- functional with respect to the groups participating in the formation of the ester functions present in the resin backbone.
• the amount of polyfunctional compounds, especially three- and four-functional compounds is preferably less than 25 mol%, preferably less than 15 mol%, more preferably less than 5 mol% of the total amount of starting materials.
• the process which may be used to prepare the polyester resins of the present invention may be carried out according to conventional esterification methods, preferably by azeotropic condensation.
• the condensation is carried out by charging the starting compounds to the reactor, followed by reaction at a temperature between 120 and 220 °C, and the reaction is continued until the non-tertiary carboxyl groups as initially present in the reaction mixture have disappeared.
• the reaction is complete in 2 to 12 hours, often between 3 and 8 hours.
• compounds E or F and G are intended to be the end groups of the polymer chain, they are preferably added at the end of the reaction, as otherwise the compounds will also be incorporated into the chain.
• esterification catalysts such as dibutyltinoxide, paratoluenesulphonic acid, tin octoate, zinc octoate and lithium ricinoleate is not required, and preferably no catalyst is used. However, if desired, an esterification catalyst may be used.
• polyester resins of the present invention are suitably derived from compounds A selected from compounds comprising a tertiary aliphatic carboxyl group and two primary hydroxyl groups.
• Suitable compounds A are alkyl substituted dimethylol acetic acid compounds, the alkyl group being a linear or branched C]__]_2 alkyl group, especially a C]__4 alkyl group.
• a preferred compound A is dimethylolpropionic acid.
• the polyester resins of the present invention are suitably derived from compounds B selected from compounds comprising two aliphatic or cycloaliphatic hydroxyl groups.
• Suitable compounds B for use in the present invention include optionally branched aliphatic or cycloaliphatic compounds.
• compound B is a straight chain alpha, omega-alkanediol compound optionally substituted by one or more C ⁇ _4 alkyl groups, a cyclohexyl compound comprising two hydroxy groups attached to the cyclohexyl ring optionally substituted by one or more C ⁇ _ alkyl groups, e.g. 1, 4-cyclohexanediol, or a perhydro bisphenol compound, e.g.
• compound B is a straight chain alpha, omega-alkanediol compound comprising up to 8 carbon atoms optionally substituted by one or more methyl groups or cyclohexanediol optionally sub- stituted by one or more methyl groups.
• the polyester resins of the present invention are suitably derived from compounds C selected from compounds comprising two or three, preferably two, secondary carboxylic acid groups, or the anhydrides thereof.
• Suitable compounds C are for example hexahydrophthalic acid (HHPA) , methyl-hexahydrophthalic acid, decahydro- naphthalene dicarboxylic acid, endomethylenetetra- hydrophthalic acid, methylendomethylene-tetrahydro- phthalic acid, 1, 4-cyclohexanedicarboxylic acid and 1, 3-cyclohexanedicarboxylic acid or the anhydrides thereof, or combinations thereof.
• Preferred compounds C are cycloaliphatic dicarboxylic acids, especially cyclohexane dicarboxylic acid, optionally substituted by one or more methyl groups .
• HHPA especially the anhydride being particularly preferred.
• the polyester resins of the present invention are suitably derived from a compound D selected from aliphatic dicarboxylic acids or the corresponding anhydrides, especially an alpha, omega alkanedicarboxylic acid optionally substituted by one or more C__4 alkyl groups.
• a compound D selected from aliphatic dicarboxylic acids or the corresponding anhydrides, especially an alpha, omega alkanedicarboxylic acid optionally substituted by one or more C__4 alkyl groups.
• Especially D is an alpha, omega alkanedicarboxylic acid comprising between 4 and 14 carbon atoms in the alkane chain, especially between 6 and 10 carbon atoms.
• Very suitable compounds are suberic acid, azelaic acid, sebacic acid and 1,10 dodecanedicarboxylic acid.
• the compound E to be used in the present invention is suitably an aliphatic or cycloaliphatic alcohol, preferably comprising one to ten carbon atoms, optionally substituted by a tertiary carboxyl group.
• Suitable compounds E are propanol, iso-propanol, n-, s-, or i-butanol, amyl alcohol, cyclopentanol, cyclohexanol and hydroxypivalic acid.
• Compound E is a hydrocarbyl compound which does not comprise any other functional groups or substituents, except one hydroxyl groups and optionally one carboxyl group.
• compound E is hydroxypivalic acid.
• the compound F is suitably selected from the same groups of compounds as defined for A and B.
• a preferred compound F is a cyclohexanediol compound, especially 1, 4-cyclohexanediol, or dimethylolpropionic acid.
• the compound G to be used in the process of the present invention is suitably a (cyclo) hydrocarbyl group comprising only one carboxylic acid group.
• Compound G is especially an aliphatic or cycloaliphatic acid, more especially a secondary acid.
• Preferably compound G is a cycloaliphatic acid, more preferably a secondary cycloaliphatic acid.
• a preferred compound G is a cycloalkyl carboxylic acid, especially a C5-C8 cycloalkylcarboxylic acid, more preferably cyclohexyl carboxylic acid.
• compounds A, B, C, D, E, F, and G are hydrocarbyl groups comprising one or more hydroxyl and/or carboxyl groups .
• the compounds may or may not be substituted.
• the substituents should not deteriorate the outdoor durability of the cured product.
• the compounds are not substituted. It was found that in the formula for the molar ratio of the tertiary carboxyl functional polyesters according to the present invention the value of X is suitably between 3 and 12, preferably between 5 and 10, more preferably between 6 and 9.
• the value of K is up to 2 and L is up to 2 and preferably K and L have a value 2.
• the ratio A/ (A+B) is suitably at least 0.6, preferably at least 0.75, more preferably at least 0.9, still more preferably is 1.
• the ratio C/ (C+D) is at least 0.6, preferably at least 0.75, more preferably at least 0.9, still more preferably is 1.
• the molar amount of B is less than the molar amount of C.
• the present invention also relates to a process for the preparation of tertiary carboxyl functional polyester resin as defined herein before, by reaction of: a) at least one aliphatic compound A comprising two aliphatic hydroxyl groups which may each independently be a primary or secondary hydroxyl group and a tertiary carboxyl group, b) optionally one or more hydroxyl compounds B, each compound comprising two aliphatic hydroxyl groups which may each independently be a primary or secondary hydroxyl group, c) at least one cycloaliphatic carboxylic acid compound C comprising two secondary aliphatic carboxyl groups or the anhydride thereof, d) optionally one or more dicarboxylic acid compounds D comprising two aliphatic carboxyl groups or the anhydride thereof, and e) optionally either one or more compounds E comprising one primary or secondary hydroxyl group and optionally a ter
• the tertiary carboxyl functional polyester resins according to the present invention can be converted into polyglycidylester resins which form another aspect of the present invention. Said conversion can be carried out according to methods known in the art i.e. by reaction with an excess epihalohydrin in the presence of a suitable base and, optionally, a catalyst. Most conveniently epichlorohydrin is being used.
• European Patent Application No. 0447360 A disclosed glycidylesters which could be used in principle in outdoor durable coatings and in moulding compositions .
• strong alkaline conditions should be avoided during glycidation of these tricarboxylic acid adducts to avoid hydrolysis of the glycidyl ester formed and/or hydrolysis of one or more ester groups in the resin backbone.
• the glycidylester produced will contain a relatively high level of hydrolizable chlorine and/or will contain low molecular weight hydro- lysis products which might cause toxiticity problems.
• the high level of hydrolizable chlorine is reflected in example 2 of EP-A-0447360 which relates to the glycidation of the 2 : 1 adduct of hexahydrophthalic anhydride and dimethylolpropionic acid.
• the product obtained has a chlorine content of 1.5%.
• Such a high level of residual chlorine is undesirable in coating compositions.
• the glycidylesters reported in EP-A-0447360 are liquid, they cannot be applied in powder coating compositions.
• the tertiary carboxyl functional polyester resin and the polyglycidylester resin of the invention have been found to be both suitable for use in powder coating compositions, which in the cured state show improved outdoor durability and in particular improved weathering resistance and acid resistance. Moreover in view of the polymeric nature of the polyglycidylester resin of the invention a lower level of toxicity as compared to TGIC is foreseen and therefore they can advantageously be used as an alternative to TGIC in powder coatings.
• the curable powder coating compositions of the invention may be prepared by addition of a cross-linking resin to either the tertiary carboxyl functional polyester resin obtainable by the process of the present invention or to the polyglycidylester resin obtainable by glycidating said tertiary carboxyl functional polyester resin.
• the amount of cross-linking compound used in the powder coating compositions of the invention will normally be such so as to provide about equal amounts of reactive groups of the cross-linking compound and of the tertiary carboxyl groups present in the linear, tertiary carboxyl functional polyester resin or of the epoxy groups present in the polyglycidylester resin.
• Curing may be carried out at temperatures between 100 and 240 °C, preferably between 120 and 200 °C.
• Curing temperatures are lower than prior art compositions, usually by 20-40 °C, while resulting in the same degree of cross- linking. If necessary a catalyst may be used. Suitable curing times are between 5 and 60 minutes, especially between 10 and 30 minutes. Good results are usually obtained by curing at 140-160 °C for 15 minutes.
• Suitable cross-linking resins for use in combination with the tertiary carboxyl functional polyester resins of the present invention are for example outdoor durable epoxy resins, such as the polyglycidylester resins according to the present invention, the diglycidylesters of alpha, alpha ' -dibranched dicarboxylic acids as disclosed in European Patent Application publication number 0518,408 A and the polyglycidylesters based on polycarboxylic acids carrying two alkyl substituents on each of the alpha carbon atoms as disclosed in European patent application publication number 0366,205 A.
• outdoor durable epoxy resins such as the polyglycidylester resins according to the present invention, the diglycidylesters of alpha, alpha ' -dibranched dicarboxylic acids as disclosed in European Patent Application publication number 0518,408 A and the polyglycidylesters based on polycarboxylic acids carrying two alkyl substituents on each of the alpha carbon atoms as disclosed
• Suitable cross-linking resins for use in combination with the polyglycidylester resins of the present invention are for example the (corresponding) acid functional polyester resin of the present invention; solid polyacids such a sebacic acid, adipic acid, 1 , 12-dodecanedioic acid; anhydrides such as polyazeleic polyanhydride and trimellitic anhydride; acid functional polyesters such as the reaction product of one mole of trimethylolpropane and 3 moles of hexahydrophthalic anhydride, the reaction product of 1, 6-hexanediol with a molar excess of 1, 12-dodecanedioic acid, the reaction product of 4 moles 1, 10-decanedicarboxylic acid, 1.49 moles hexanediol, 0.47 moles 1 , 1, 1-tris- (hydroxy- methyl ) -propane and 0.27 moles pentaerythritol, the reaction product of 4 moles 1, 10-de
• Preferred curing agents are the acidic polyesters of the present invention and the reaction product of one mole of trimethylol- propane and 3 moles of hexahydrophthalic anhydride.
• the powder coating compositions of the present invention may further comprise a catalyst and optionally other additives, as known in the art to be suitable for use in powder coating compositions .
• Suitable catalyst are for example quaternary ammonium and phosphonium salts; metal salts/compounds such as for example stannous ( II ) octoate; basic compounds such as for example the imidazoles; and tertiary amines such as for example 1, 8-diazabicycloundecene .
• the amount of catalyst used will usually somewhere in the range of from 0.1 to 2% by weight based on the weight of the total powder coating composition.
• Example 1 The invention is illustrated by the following examples, however without restricting its scope to these specific embodiments.
• Example 1 The invention is illustrated by the following examples, however without restricting its scope to these specific embodiments.
• Hexahydrophthalic acid anhydride (7 moles), di- methylolpropionic acid (8 moles) and dodecane dicarboxylic acid (2 moles) were charged to a round bottom glass reactor, equipped with a mechanical stirrer, temperature control, nitrogen inlet and vacuum facilities. The mixture was stirred under nitrogen and heated to 150 °C. A vacuum of 950 mbar was applied. The temperature of the reaction mixture was increased in one hour to 200 °C and kept at 200 °C until the theoretical acid value was reached. The acid functional polyester was discharged and allowed to cool to room temperature. Acid value: 4.08 meq/g; mol. weight: 2451; m.p. 60-75 °C.
• Example 3 An acid functional polyester was prepared from hexahydrophthalic acid anhydride (5 moles), dimethylol propionic acid (4 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 1.
• Product acid value 4.13; weight 1453; m.p. 70-85 °C.
• Example 4 An acid functional polyester was prepared from hexahydrophthalic acid anhydride (5 moles), dimethylol propionic acid (4 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 1.
• Product acid value 4.13; weight 1453; m.p. 70-85 °C.
• Example 4 An acid functional polyester was prepared from hexahydrophthalic acid anhydride (5 moles), dimethylol propionic acid (4 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 1.
• Product acid value 4.13; weight 1453; m.p. 70-85 °C.
• Example 4 An acid functional polyester was prepared
• the corresponding glycidylester was prepared from a functional polyester derived from hydrogenated diphenylol propane (6 moles), hexahydrophthalic anhydride (9 moles), dimethylol propionic acid (2 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 2 of EP-0634434A (acid-functional polyester resin 1) .
• Precursor acid value 1.20; mol. weight 3340; m.p. 115- 125 °C; product: EGC 1120 mmol/kg; m.p. 85-90 °C.
• the corresponding glycidylester was prepared from a functional polyester derived from hydrogenated diphenylol propane (3 moles) hexahydrophthalic anhydride (9 moles), dimethylol propionic acid (5 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 2 of EP-0634434A.
• Precursor acid value 2.38; weight 2937; m.p. 99-120 °C; product: EGC 1.79; m.p. ⁇ 50 °C.
• Example 6 The corresponding glycidyl ester was prepared from a functional polyester, derived from hydrogenated diphenylol propane (3 moles), hexahydrophthalic anhydride (6 moles), dimethylol propionic acid (2 moles) and hydroxy pivalic acid (2 moles) in the way as described in example 2 of EP-0634434A.
• Precursor acid value 1.82; weight 2198; m.p. 105-115 °C; product: EGC 1.40; m.p. ⁇ 50 °C.
• Example 7 Example 7
• the corresponding glycidylester was prepared from a functional polyester, which had been earlier prepared from hydrogenated diphenylolpropane (6 moles), hexahydrophthalic acid anhydride (9 moles) and dimethylol propionic acid (4 moles) in the way as described in example 3 of EP-0720997A.
• Precursor acid value 1.19; mol. weight 3372; product: EGC 1170 mmol/kg; m.p. 80-90 °C.
• An acid functional polyester was made in the way as described in Example 1 using as starting material hydro- genated diphenylolpropane (4 moles), hexahydrophthalic acid anhydride (9 moles), dimethylol propionic acid (4 moles) and para-t-butylcylohexanol (2 moles) .
• Product properties acid value 1.32 mmol/kg; mol. weight 3036; m.p. 105-120 °C.
• the acid functional polyester was converted into the glycidyl ester by dissolving 1 carboxyl equivalent polyester in 8 moles epichlorohydrin and isopropylalcohol (same volume as ECH) .
• An epoxy functional polymer was prepared by reaction of the vinyl ester of a CIO Koch acid (Veova-10, is a trademark) (22 parts by weight), dimethylmaleonate (6.5 pbw), styrene (43.0 pbw), methylmethacrylate (11.5 pbw), glycidylmethacrylate (17.0 pbw) and di-tert.- butyl peroxide (2 pbw) .
• the vinyl ester of the Koch acid and dimethylmaleonate are charged to a glass reactor equipped with a mechanical stirrer, temperature control, nitrogen inlet, inlet tube for monomers and reflux condenser with direct reflow into the reactor. The reactor is heated to 155-170 °C.
• Coating compositions were made in the same way as described in EP-0720997A, Example 4.
• the TGIC based comparison example is based on the cured reaction product of TGIC with an equivalent amount of a commercial acid functional polyacrylate resin (URALAC 4200, DSM, based on terephthalic acid and glycol) .
• a commercial acid functional polyacrylate resin ULC 4200, DSM, based on terephthalic acid and glycol
• the acrylate based comparison example is based on glycidyl methacrylate (ex UCB) cross-linked with dodecane carboxylic acid (Synthacryl, Hoechst, acid value 300 mg KOH, M 2000, m.p. 80-90 °C) and an equivalent amount of melamine (MF) .
• the MEK resistance is measured by the number of double rubs with a MEK impregnated sample until the coating is damaged and the panel is visible.
• the hardness is measured according to the pendulum damping test (Konig hardness) according to ISO 1522-1973.
• the weathering resistance is measured according to the standard of the Society of Automotive Engineers (SAE J1960-1989) .
• SAE J1960-1989 The test method is designed to accelerate extreme environmental conditions outside a vehicle due to sunlight, heat and moisture (humidity, condensation or rain) .
• Use is made of an Atlas C165 Xenon Arc Weather-O-meter until a 50 percent gloss reduction is obtained.
• the acid resistance is measured by applying a droplet of 0.6 N H2SO4 on the coating at 50 °C for 90 minutes. The results are described on a scale of 1 to 5: 1-dissolved, 2-softening, 3-whitening, 4-traces, 5-no damage .

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• 1998
  • 1998-02-20 AU AU68246/98A patent/AU730241B2/en not_active Ceased
  • 1998-02-20 BR BR9807705-8A patent/BR9807705A/pt not_active Application Discontinuation
  • 1998-02-20 CA CA002281750A patent/CA2281750A1/en not_active Abandoned
  • 1998-02-20 NZ NZ336654A patent/NZ336654A/xx unknown
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