NO860440L - PROCEDURE FOR THE PREPARATION OF POWDER COATING MATERIALS BASED ON AN EPOXY RESIN AND A CARBOXYLED POLYESTER. - Google Patents
PROCEDURE FOR THE PREPARATION OF POWDER COATING MATERIALS BASED ON AN EPOXY RESIN AND A CARBOXYLED POLYESTER.Info
- Publication number
- NO860440L NO860440L NO860440A NO860440A NO860440L NO 860440 L NO860440 L NO 860440L NO 860440 A NO860440 A NO 860440A NO 860440 A NO860440 A NO 860440A NO 860440 L NO860440 L NO 860440L
- Authority
- NO
- Norway
- Prior art keywords
- polyester resin
- carboxylated
- mixture
- parts
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 17
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 17
- 238000000576 coating method Methods 0.000 title claims description 24
- 239000011248 coating agent Substances 0.000 title claims description 21
- 239000000463 material Substances 0.000 title claims description 21
- 229920000728 polyester Polymers 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title 1
- 229920001225 polyester resin Polymers 0.000 claims abstract description 46
- 239000004645 polyester resin Substances 0.000 claims abstract description 46
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 9
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000004593 Epoxy Substances 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims abstract description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 5
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000011654 magnesium acetate Substances 0.000 claims abstract description 5
- 229940069446 magnesium acetate Drugs 0.000 claims abstract description 5
- 235000011285 magnesium acetate Nutrition 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 5
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims abstract description 4
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims abstract description 4
- 239000004246 zinc acetate Substances 0.000 claims abstract description 4
- 239000008199 coating composition Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical group CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical group CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
Den foreliggende oppfinnelse angår en fremgangsmåteThe present invention relates to a method
for fremstilling av et pulverformig belegningsmateriale, nær-mere bestemt en fremgangsmåte for fremstilling av et belegningsmateriale på basis av en epoxyharpiks og en carboxylert polyester, hvilket belegningsmateriale lar seg varmherde hurtig ved lav temperatur under dannelse av en film med gode mekaniske egenskaper og et godt utseende av overflaten. for the production of a powdery coating material, more specifically a method for the production of a coating material based on an epoxy resin and a carboxylated polyester, which coating material can be heat-cured quickly at a low temperature while forming a film with good mechanical properties and a good appearance of the surface.
Pulverformige belegg krever ingen anvendelse av organiske oppløsningsmidler, hvilket medfører den fordel at man unngår forurensningsproblemer og likeledes unngår de hygie-niske og sikkerhetsmessige problemer som er forbundet med bruk av organiske oppløsningsmidler. Dessuten medfører fraværet av et oppløsningsmiddel den ytterligere og meget vesentlige fordel som ligger i de økonomiske besparelser. Dessverre mot-virkes alle disse fordeler av at disse pulvere krever høy herdetemperatur, hvilket resulterer i filmer med et relativt dårlig overflateutseende og dårlige mekaniske egenskaper. Powder coatings do not require the use of organic solvents, which has the advantage of avoiding pollution problems and also avoiding the hygienic and safety problems associated with the use of organic solvents. Moreover, the absence of a solvent entails the further and very significant advantage of economic savings. Unfortunately, all these advantages are counteracted by the fact that these powders require a high curing temperature, which results in films with a relatively poor surface appearance and poor mechanical properties.
For å utvide anvendelsesområdet for pulverformige belegningsmaterialer er det ønskelig å senke herdetemperaturen og å korte inn varmebehandlingstiden, slik at man på den ene side unngår den brune misfarvning av filmen og på den annen side unngår forvridning av underlaget som påføres filmen, hvilket gjenspeiles i en generell svekking av det ferdige produkts mekaniske egenskaper. I praksis er det bare tre faktorer som kan varieres for å overvinne disse vanskeligheter: harpiksen, sammensetningen av herdekatalysatoren og arten av herdeakseleratoren. In order to expand the application area of powder coating materials, it is desirable to lower the curing temperature and to shorten the heat treatment time, so that on the one hand the brown discoloration of the film is avoided and on the other hand the distortion of the substrate applied to the film is avoided, which is reflected in a general weakening of the finished product's mechanical properties. In practice, only three factors can be varied to overcome these difficulties: the resin, the composition of the curing catalyst, and the nature of the curing accelerator.
Pulverformige belegningsmaterialer som for tiden er kjent, består av en blanding på basis av systemet epoxyharpiks og carboxylert polyesterharpiks. Det er velkjent at disse harpikser, som er reaktive som følge av tilstedeværelsen av epoxygrupper og carboxylerte grupper, kan varmherdes ved hjelp av herdekatalysatorer. De hittil best kjente fremgangsmåter går ut på å blande epoxyharpiksen og den carboxylerte polyesterharpiks og deretter sette herdekatalysatoren til blandingen og underkaste denne ternære blanding en varmebehandling. Forbindelser som er kjent for å virke som en katalysator for reaksjonen mellom epoxygrupper og carboxylgrupper, er spesielt de forbindelser som inneholder et tertiært nitrogenatom, og disse velges blant dimethylbenzylamin og triethylendiamin og kvartære ammoniumsalter, såsom tetraethylammoniumklorid. Imidlertid medfører bruken av disse katalysatorer for fremstilling av pulverformige belegningsmaterialer de ulemper at de ikke i tilstrekkelig grad nedsetter herdetemperaturen og således forårsaker en brunlig misfarvning av malingfilmen. Dessuten endrer de malingfilmens overflate i stor grad og fører til dannelse av et belegg med middelmådige mekaniske egenskaper. Det er derfor behov for belegningsmaterialer på basis av epoxy-harpikser og carboxylert polyesterharpiks som kan varmherdes så hurtig som mulig og ved en temperatur som er så lite for-høyet som mulig. Powder coating materials currently known consist of a mixture based on the system epoxy resin and carboxylated polyester resin. It is well known that these resins, which are reactive due to the presence of epoxy groups and carboxylated groups, can be heat-cured by means of curing catalysts. The hitherto best known methods involve mixing the epoxy resin and the carboxylated polyester resin and then adding the curing catalyst to the mixture and subjecting this ternary mixture to a heat treatment. Compounds known to act as a catalyst for the reaction between epoxy groups and carboxyl groups are especially those compounds containing a tertiary nitrogen atom, and these are selected from dimethylbenzylamine and triethylenediamine and quaternary ammonium salts, such as tetraethylammonium chloride. However, the use of these catalysts for the production of powdery coating materials entails the disadvantages that they do not sufficiently reduce the curing temperature and thus cause a brownish discoloration of the paint film. Moreover, they change the surface of the paint film to a great extent and lead to the formation of a coating with mediocre mechanical properties. There is therefore a need for coating materials based on epoxy resins and carboxylated polyester resin that can be heat-cured as quickly as possible and at a temperature that is as little elevated as possible.
Det er nu funnet frem til løsninger på disse problemer, slik at det kan oppnås pulverformige belegningsmaterialer som gir belegg med et tilfredsstillende utseende av overflaten og gode mekaniske egenskaper. Solutions to these problems have now been found, so that powdery coating materials can be obtained which provide coatings with a satisfactory appearance of the surface and good mechanical properties.
I henhold til oppfinnelsen tilveiebringes det således en fremgangsmåte for fremstilling av et pulverformig belegningsmateriale som lar seg varmherde, og som består av en blanding av epoxyharpiks og polyesterharpiks, en herdekatalysator og en herdeakselerator. Fremgangsmåten utmerker seg ved at materialet fremstilles ved at man blander den carboxylerte polyesterharpiks inneholdende herdekatalysatoren og herdeåkse-leratoren for epoxyharpiks-polyesterharpiks-systemet, idet blandingen varmherdes, og katalysatoren, som på forhånd tilsettes den carboxylerte polyesterharpiks, utgjøres av lithiumacetat, sinkacetat, magnesiumacetat eller tetraethylammoniumbromid anvendt hver for seg eller i blanding med hverandre, According to the invention, a method is thus provided for the production of a powdery coating material which can be heat-cured, and which consists of a mixture of epoxy resin and polyester resin, a curing catalyst and a curing accelerator. The method is characterized by the fact that the material is produced by mixing the carboxylated polyester resin containing the curing catalyst and the curing accelerator for the epoxy resin-polyester resin system, the mixture being heat-cured, and the catalyst, which is added to the carboxylated polyester resin in advance, consists of lithium acetate, zinc acetate, magnesium acetate or tetraethylammonium bromide used separately or in mixture with each other,
og akseleratoren, som på forhånd settes til den carboxylerte polyesterharpiks, utgjøres av 2-methylimidazol, 1-methylimidazol, 2-fenylimidazol, 2-isopropylimidazol eller imidazol. and the accelerator, which is added in advance to the carboxylated polyester resin, consists of 2-methylimidazole, 1-methylimidazole, 2-phenylimidazole, 2-isopropylimidazole or imidazole.
I henhold til et annet karakteristisk trekk ved fremgangsmåten ifølge oppfinnelsen skal mengden av katalysator som anvendes i den carboxylerte polyesterharpiks, ikke overskride 2,2 vekt%, beregnet på vekten av den carboxylerte polyesterharpiks, og mengden av akselerator ikke overskride 0,3 vekt%, beregnet på vekten av den carboxylerte polyesterharpiks. According to another characteristic feature of the method according to the invention, the amount of catalyst used in the carboxylated polyester resin should not exceed 2.2% by weight, calculated on the weight of the carboxylated polyester resin, and the amount of accelerator should not exceed 0.3% by weight. calculated on the weight of the carboxylated polyester resin.
Ved bruk av en slik fremgangsmåte blir det mulig å fremstille belegg som ikke er farvede, og som har en overflate med godt utseende og har gode mekaniske egenskaper. Ved hjelp av denne fremgangsmåte er det også mulig å korte inn herde-tiden og å nedsette herdetemperaturen. Det har videre vist seg at forhåndstilsetning av herdekatalysatoren og herdeakseleratoren til den carboxylerte polyesterharpiks muliggjør en bedre dispersjon og følgelig fører til at man unngår gulnings-fenomenet. By using such a method, it becomes possible to produce coatings which are not coloured, and which have a surface with a good appearance and have good mechanical properties. Using this method, it is also possible to shorten the curing time and to lower the curing temperature. It has also been shown that prior addition of the curing catalyst and curing accelerator to the carboxylated polyester resin enables a better dispersion and consequently leads to the avoidance of the yellowing phenomenon.
Ved utførelsen av fremgangsmåten ifølge oppfinnelsen tilsettes herdekatalysatoren og herdeakseleratoren på forhånd under fremstillingen av den carboxylerte polyesterharpiks. Herdekatalysatoren består av lithiumacetat, sinkacetat, magnesiumacetat eller tetraethylammoniumbromid, hvilke kan anvendes hver for seg eller i blanding. Den anvendes i en mengde som ikke overskrider 2,2 vekt%, og fortrinnsvis i en mengde som er mindre enn 0,8 vekt%, beregnet på vekten av den carboxylerte polyester. Materialene som benyttes, er kommersielt lithiumacetat, som krystalliserer med to molekyler vann; magnesiumacetat, som krystalliserer med fire molekyler vann. Herdeakseleratoren som anvendes, utgjøres av 3-methylimidazol, 1-methylimidazol, 2-fenylimidazol, 2-isopropylimidazol eller imidazol, som benyttes i en mengde av høyst 0,3 vekt%, fortrinnsvis i en mengde som er mindre enn 0,15 vekt%, beregnet på vekten av den carboxylerte polyesterharpiks. When carrying out the method according to the invention, the curing catalyst and the curing accelerator are added in advance during the production of the carboxylated polyester resin. The curing catalyst consists of lithium acetate, zinc acetate, magnesium acetate or tetraethylammonium bromide, which can be used individually or in a mixture. It is used in an amount which does not exceed 2.2% by weight, and preferably in an amount which is less than 0.8% by weight, calculated on the weight of the carboxylated polyester. The materials used are commercial lithium acetate, which crystallizes with two molecules of water; magnesium acetate, which crystallizes with four molecules of water. The hardening accelerator used consists of 3-methylimidazole, 1-methylimidazole, 2-phenylimidazole, 2-isopropylimidazole or imidazole, which is used in an amount of no more than 0.3% by weight, preferably in an amount that is less than 0.15% by weight , calculated on the weight of the carboxylated polyester resin.
I henhold til et viktig karakteristisk trekk ved fremgangsmåten ifølge oppfinnelsen settes herdekatalysatoren og herdekaseleratoren til blandingen av carboxylert polyesterharpiks og epoxyharpiks. Det har således vist seg at man ved å gå frem på denne måte oppnår et belegg som lar seg varmherde ved en lavere temperatur og i løpet av kortere tid. According to an important characteristic feature of the method according to the invention, the curing catalyst and the curing accelerator are added to the mixture of carboxylated polyester resin and epoxy resin. It has thus been shown that by proceeding in this way, a coating is obtained which can be heat-cured at a lower temperature and in a shorter time.
Som følge derav gjør fremgangsmåten det mulig å oppnå pulverformige belegningsmaterialer som ikke er farvede, og som har et attraktivt overflateutseende. As a result, the method makes it possible to obtain powdery coating materials which are not colored and which have an attractive surface appearance.
De carboxylerte polyestere som anvendes i henhold til oppfinnelsen, fremstilles under anvendelse av alle de kjente utgangsmaterialer for fremstilling av carboxylerte polyestere. The carboxylated polyesters used according to the invention are produced using all the known starting materials for the production of carboxylated polyesters.
at det også tilsettes en kjent mykner, f.eks. adipinsyre,that a known plasticizer is also added, e.g. adipic acid,
som benyttes i en mengde av høyst 15 vekt%, beregnet på total-mengden av alle de øvrige bestanddeler som benyttes for fremstillingen av de carboxylerte polyestere. Bestanddelene som benyttes for fremstilling av de carboxylerte polyestere som inngår i fremgangsmåten ifølge oppfinnelsen, velges som i og for seg kjent blant minst én polyol og en eller flere mettede polycarboxylsyrer eller polycarboxylsyreanhydrider. Som polyoler som kan benyttes, skal nevnes ethylenglycol, neopentylglycol, propylenglycol, dipropylenglycol, 1,4-cyclohexandimethanol, trimethylolpropan, diethylenglycol, 1,4-butan-diol, trimethylolpropan, pentaerythritol, bisfenol A og propyl-oxyethylen eller hydroxypropylen. Som mettede polycarboxylsyrer eller polycarboxylsyreanhydrider skal nevnes terefthalsyre, which is used in an amount of no more than 15% by weight, calculated on the total amount of all the other components used for the production of the carboxylated polyesters. The components used for the production of the carboxylated polyesters included in the method according to the invention are selected, as is known per se, from at least one polyol and one or more saturated polycarboxylic acids or polycarboxylic anhydrides. As polyols that can be used, mention should be made of ethylene glycol, neopentyl glycol, propylene glycol, dipropylene glycol, 1,4-cyclohexanedimethanol, trimethylolpropane, diethylene glycol, 1,4-butane-diol, trimethylolpropane, pentaerythritol, bisphenol A and propyloxyethylene or hydroxypropylene. As saturated polycarboxylic acids or polycarboxylic anhydrides should be mentioned terephthalic acid,
trimellitsyre, isofthalsyre, tetrahydrofthalsyre, hexahydrof-thalsyre og ravsyreanhydrider, osv. trimellitic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid and succinic anhydrides, etc.
Epoxyharpiksene som benyttes ved fremgangsmåten ifølge oppfinnelsen, er kjente harpikser som fremstilles f.eks. ut fra bisfenol A og epiklorhydrin. Faste harpikser med en mole-kylvekt på mellom 1000 og 2000 og med en epoxyekvivalent på mellom 500 og 1000 foretrekkes. The epoxy resins used in the method according to the invention are known resins which are produced, e.g. from bisphenol A and epichlorohydrin. Solid resins with a molecular weight of between 1000 and 2000 and with an epoxy equivalent of between 500 and 1000 are preferred.
Carboxylert-polyesterharpiksene som er særlig anvende-lige for anvendelse ved fremgangsmåten ifølge oppfinnelsen, velges blant dem som har et syretall på fortrinnsvis mellom 60 og 120 og et mykningspunkt mellom 80 og 120°C. Ved bruk av harpikser med mykningspunkt høyere enn 120°C oppstår det problemer under ekstruderingen, fordi polyesterharpiksen og epoxyharpiksen ikke har samme viskositet. Bruk av en carboxylert-polyesterharpiks med mykningspunkt lavere enn 80°C resulterer i smeltefenomener, hvilket forårsaker vanskeligheter under bearbeidelsen. The carboxylated polyester resins which are particularly useful for use in the method according to the invention are selected from those which have an acid value of preferably between 60 and 120 and a softening point between 80 and 120°C. When using resins with a softening point higher than 120°C, problems arise during extrusion, because the polyester resin and the epoxy resin do not have the same viscosity. Using a carboxylated polyester resin with a softening point lower than 80°C results in melting phenomena, which causes difficulties during processing.
Ved utførelsen av fremgangsmåten ifølge oppfinnelsen gjøres det bruk av et vektforhold mellom epoxybestanddelen og carboxylert-polyester-bestanddelen som er mellom 0,6 og 1,5, og som fortrinnsvis er i området rundt 1. When carrying out the method according to the invention, use is made of a weight ratio between the epoxy component and the carboxylated polyester component which is between 0.6 and 1.5, and which is preferably in the region of 1.
Belegningsmaterialene som fåes ved fremgangsmåten ifølge oppfinnelsen, kan inneholde kjente additiver, såsom et utbred- ningsmiddel, fyllstoffer, pigmenter, værbestandighetsbeford-rende midler og lignende. Materialene fremstilles på konven-sjonell måte ved at man blander, i tørr tilstand, epoxyharpiksen og carboxylert-polyester-harpiksen inneholdende herdekatalysatoren og akseleratoren og eventuelle additiver, f.eks. i en mølle eller i en blander, hvoretter man homogeniserer materialet varmt i en knamaskin utstyrt med en roterende skrue. Etter avkjøling blir det dannede produkt knust og finmalt The coating materials obtained by the method according to the invention may contain known additives, such as a spreading agent, fillers, pigments, weatherproofing agents and the like. The materials are produced in a conventional manner by mixing, in a dry state, the epoxy resin and the carboxylated polyester resin containing the curing catalyst and accelerator and any additives, e.g. in a mill or in a mixer, after which the material is homogenized hot in a kneader equipped with a rotating screw. After cooling, the formed product is crushed and finely ground
i en mølle og deretter siktet. De fremstilte pulverformige materialer kan påføres på mange artikler, under anvendelse av konvensjonelle metoder, såsom ved belegging i et fluidi-sert skikt, ved elektrostatisk sprøytebelegging, ved belegging med sprøytepistol, osv. in a mill and then sieved. The manufactured powdery materials can be applied to many articles, using conventional methods, such as by coating in a fluidized bed, by electrostatic spray coating, by coating with a spray gun, etc.
De følgende eksempler illustrerer oppfinnelsen. The following examples illustrate the invention.
Eksempel 1Example 1
De følgende materialer innføres i en reaktor utstyrt med en rører, et termometer og en termostatstyrt kolonne: The following materials are introduced into a reactor equipped with a stirrer, a thermometer and a thermostatically controlled column:
124 deler ethylenglycol124 parts ethylene glycol
1,872 deler neopentylglycol1.872 parts of neopentyl glycol
272 deler 1,4-cyclohexandimethanol272 parts 1,4-cyclohexanedimethanol
134 deler trimethylolpropan134 parts trimethylolpropane
3,320 deler terefthalsyre3.320 parts terephthalic acid
292 deler adipinsyre292 parts adipic acid
6,63 deler av et tinnsalt markedsført under varemerket "Fascat" av firmaet M.T.; dette salt er en for-es tringskatalysator. 6.63 parts of a tin salt marketed under the trademark "Fascat" by the firm M.T.; this salt is a catalytic converter.
Reaksjonsblandingen tillates å reagere i 10 timer ved temperatur inntil 250°C. Etter avkjøling til 190°C innføres The reaction mixture is allowed to react for 10 hours at a temperature of up to 250°C. After cooling to 190°C, introduce
18 deler lithiumacetat og18 parts lithium acetate and
615 deler trimellitsyreanhydrid i reaktoren. 615 parts trimellitic anhydride in the reactor.
Reaksjonsblandingen tillates å stabilisere seg ved 180°C i 1 time, hvoretter 6 deler 2-methylimidazol tilsettes. Reaksjonsblandingen holdes ved denne temperatur i 20 minutter. The reaction mixture is allowed to stabilize at 180°C for 1 hour, after which 6 parts of 2-methylimidazole are added. The reaction mixture is kept at this temperature for 20 minutes.
Det oppnås en carboxylert-polyesterharpiks med de føl-gende egenskaper: A carboxylated polyester resin with the following properties is obtained:
syretall: 80acid number: 80
hydroxyltall: 3hydroxyl number: 3
mykningspunkt: 111°C.softening point: 111°C.
50 vektdeler av carboxylert-polyesterharpiksen blandes med 50 vektdeler av en fast epoxyharpiks fremstilt ut fra bisfenol A og epiklorhydrin. Denne epoxyharpiks har en mole-kylvekt på 1770, en epoxyekvivalent på 810 og et epoxytall. på 0,128. 0,36 del av et strømningsforbedrende middel (mar-kedsført under varemerket Modaflow<®>av Monsanto Company) 50 parts by weight of the carboxylated polyester resin are mixed with 50 parts by weight of a solid epoxy resin made from bisphenol A and epichlorohydrin. This epoxy resin has a molecular weight of 1770, an epoxy equivalent of 810 and an epoxy number. of 0.128. 0.36 part of a flow enhancer (marketed under the trademark Modaflow<®>by Monsanto Company)
og 66,66 deler titanoxyd settes til blandingen av harpikser. and 66.66 parts of titanium oxide are added to the mixture of resins.
Bestanddelene tørrblandes i en valsemølle i 15 minutter og smeltehomogeniseres deretter i en "Ko-kneader", som er knamaskin av fabrikat Buss. Etter avkjøling blir produktet knust og finmalt i en mølle og deretter siktet for fjerne den fraksjon som er størren lOO^um. The ingredients are dry-mixed in a roller mill for 15 minutes and then melt-homogenized in a "Ko-kneader", which is a kneading machine made by Buss. After cooling, the product is crushed and finely ground in a mill and then sieved to remove the fraction larger than 100 µm.
Belegningsmaterialene påføres ved hjelp av en sprøyte-pistol på avfettede metallplater, slik at det fåes en film av tykkelse 50-70^um. Beleggets egenskaper er angitt i tabell 1. The coating materials are applied by means of a spray gun to degreased metal plates, so that a film of thickness 50-70 µm is obtained. The properties of the coating are listed in table 1.
Eksempel 2Example 2
Eksempel 1 gjentas, men det benyttes 248 deler ethylenglycol istedenfor 124 deler, 438 deler adipinsyre istedenfor 292 deler og 9 deler 2-methylimidazol istedenfor 6 deler. Example 1 is repeated, but 248 parts of ethylene glycol are used instead of 124 parts, 438 parts of adipic acid instead of 292 parts and 9 parts of 2-methylimidazole instead of 6 parts.
Det fåes en carboxylert-polyesterharpiks med de følgende egenskaper: A carboxylated polyester resin with the following properties is obtained:
syretall: 70acid number: 70
hydroxyltall: 2 8hydroxyl number: 2 8
mykningspunkt: 96°C.softening point: 96°C.
Denne carboxylert-polyesterharpiks blandes så med de samme bestanddeler som dem benytteti eksempel 1. Det fåes en film hvis egenskaper er angitt i tabell 1. This carboxylated polyester resin is then mixed with the same components as those used in example 1. A film is obtained whose properties are indicated in table 1.
Eksempel 3Example 3
Eksempel 2 gjentas, men det benyttes 692 deler trimellitsyreanhydrid istedenfor 615 deler og 6 deler 2-methylimidazol istedenfor 9 deler. Example 2 is repeated, but 692 parts of trimellitic anhydride are used instead of 615 parts and 6 parts of 2-methylimidazole instead of 9 parts.
Det fåes en carboxylert-polyesterharpiks med de følgende egenskaper: A carboxylated polyester resin with the following properties is obtained:
syretall: 85,8acid number: 85.8
hydroxyltall: 1,8hydroxyl number: 1.8
mykningspunkt: 103°Csoftening point: 103°C
Denne carboxylert-polyesterharpiks blandes så med de samme bestanddeler som dem benyttet i-eksempel 1. Det fåes - This carboxylated polyester resin is then mixed with the same ingredients as those used in example 1. It is obtained -
en film hvis egenskaper er angitt i tabell 1.a film whose properties are listed in Table 1.
Eksempel 4Example 4
Den følgende rekke forsøk utføres i sammenligningsøye-med: a. En carboxylert-polyesterharpiks fremstilles i henhold til eksempel 1 ut fra de følgende bestanddeler: The following series of tests are carried out for the sake of comparison: a. A carboxylated polyester resin is prepared according to example 1 from the following components:
2,318 deler propylenglycol2.318 parts propylene glycol
3,735 deler isofthalsyre3.735 parts isophthalic acid
365 deler adipinsyre365 parts adipic acid
7,4 deler av samme tinnsalt som det der ble benyttet 1 eksempel 1. 7.4 parts of the same tin salt as that used in Example 1.
Etter en reaksjon som angitt i eksempel 1 og etter avkjøling tilsettes 960 deler trimellitsyreanhydrid. After a reaction as indicated in example 1 and after cooling, 960 parts of trimellitic anhydride are added.
Det fåes polyesterharpiks med de følgende egenskaper: Polyester resin is obtained with the following properties:
syretall: 84acid number: 84
hydroxyltall: 24hydroxyl number: 24
mykningstall: 93°Csoftening point: 93°C
Denne carboxylert-polyesterharpiks blandes så med de samme bestanddeler som dem der ble anvendt i eksempel 1. Det fåes en film hvis egenskaper er angitt i tabell 2. This carboxylated polyester resin is then mixed with the same ingredients as those used in example 1. A film is obtained whose properties are indicated in table 2.
b. Carboxylert-polyesterharpiksen erholdt i eksempelb. The carboxylated polyester resin obtained in Example
4a anvendes for fremstilling av en film. Før filmen fremstilles settes 9 deler 2-methylimidazol til den pulverformige blanding av carboxylert polyester og epoxyharpiks. Egenskapene av den fremstilte film er oppført i tabell 2. 4a is used for the production of a film. Before the film is produced, 9 parts of 2-methylimidazole are added to the powdery mixture of carboxylated polyester and epoxy resin. The properties of the produced film are listed in Table 2.
c. På tilsvarende måte utføres eksempel 4b, idet imidlertid 2-methylimidazolen erstattes med 18 deler lithiumacetat. Egenskapene av den fremstilte film er oppført i tabell 2 • c. Example 4b is carried out in a similar manner, but the 2-methylimidazole is replaced with 18 parts of lithium acetate. The properties of the produced film are listed in table 2 •
Eksempel 5 Example 5
Under anvendelse av en fremgangsmåte identisk med den benyttet i eksempel 1 fremstilles en carboxylert polyester med de følgende egenskaper: Using a method identical to that used in example 1, a carboxylated polyester with the following properties is produced:
syretall: 63,5acid number: 63.5
hydroxyltall: 2,5hydroxyl number: 2.5
mykningspunkt: 113°C.softening point: 113°C.
De følgende materialer settes til 50 vektdeler av den således fremstilte polyesterharpiks: diverse katalysatorer i varierende mengder og 0,15 vektdel 2-methylimidazol. 50 vektdeler av den erholdte carboxylert-polyesterharpiks blandes med 50 vektdeler av den samme epoxyharpiks som den benyttet i eksempel 1, og med 1,2 vektdeler av det samme strømnings-forbedrende middel og 50 vektdeler av det samme titanoxyd. The following materials are added to 50 parts by weight of the thus produced polyester resin: various catalysts in varying amounts and 0.15 parts by weight of 2-methylimidazole. 50 parts by weight of the obtained carboxylated polyester resin is mixed with 50 parts by weight of the same epoxy resin as used in example 1, and with 1.2 parts by weight of the same flow-improving agent and 50 parts by weight of the same titanium oxide.
Etter påføring med en sprøytepistol fåes belegg hvis egenskaper er angitt i tabell 3. Katalysatormengdene er uttrykt i prosent, beregnet på vekten av harpiksen. After application with a spray gun, a coating is obtained whose properties are indicated in table 3. The catalyst amounts are expressed as a percentage, calculated on the weight of the resin.
Eksempel 6 Example 6
Eksempel 4 gjentas, under anvendelse av kun lithiumacetat som katalysator, idet katalysatoren anvendes i samme mengde som i eksempel 1, og under anvendelse av diverse imida-zoler, som benyttes i en mengde av 0,1 del pr. 100 deler av harpiksblandingen. Example 4 is repeated, using only lithium acetate as catalyst, the catalyst being used in the same amount as in example 1, and using various imidazoles, which are used in an amount of 0.1 part per 100 parts of the resin mixture.
Tabell 4 viser egenskapene av dé belegg som oppnås. Table 4 shows the properties of the coating that is obtained.
Egenskapene er angitt i henhold til de samme standar-der som dem angitt i tabell 1. The properties are specified according to the same standards as those specified in table 1.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8501771A FR2577231B1 (en) | 1985-02-08 | 1985-02-08 | PROCESS FOR THE PREPARATION OF POWDER COATING COMPOSITIONS BASED ON AN EPOXY RESIN AND A CARBOXYL POLYESTER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO860440L true NO860440L (en) | 1986-08-11 |
Family
ID=9316060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860440A NO860440L (en) | 1985-02-08 | 1986-02-07 | PROCEDURE FOR THE PREPARATION OF POWDER COATING MATERIALS BASED ON AN EPOXY RESIN AND A CARBOXYLED POLYESTER. |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0194904B1 (en) |
| JP (1) | JPS61183367A (en) |
| CN (1) | CN1003646B (en) |
| AT (1) | ATE42315T1 (en) |
| CA (1) | CA1264882A (en) |
| DE (1) | DE3662902D1 (en) |
| DK (1) | DK61586A (en) |
| FI (1) | FI860565A (en) |
| FR (1) | FR2577231B1 (en) |
| NO (1) | NO860440L (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920182A (en) * | 1987-12-18 | 1990-04-24 | Ciba-Geigy Corporation | Epoxy resin compositions containing polyester flexibilizer and metallocene complex initiator |
| DE4038681A1 (en) * | 1990-12-05 | 1992-06-11 | Basf Lacke & Farben | POWDER LACQUER AND THE USE THEREOF FOR THE INTERNAL COATING OF PACKAGING CONTAINERS AND FOR WELDING SEALING |
| DE4141776A1 (en) * | 1991-12-18 | 1993-06-24 | Hoechst Ag | CURABLE BINDING AGENT AND METHOD FOR THE PRODUCTION THEREOF |
| NL9400182A (en) * | 1994-02-04 | 1995-09-01 | Dsm Nv | Powder paint. |
| GB9901485D0 (en) | 1999-01-22 | 1999-03-17 | Swan Thomas & Co Ltd | Improvements in or relating to powdered coating compositions |
| US6576718B1 (en) * | 1999-10-05 | 2003-06-10 | General Electric Company | Powder coating of thermosetting resin(s) and poly(phenylene ethers(s)) |
| JP2002020683A (en) * | 2000-07-05 | 2002-01-23 | Sumitomo Bakelite Co Ltd | Epoxy resin powder coating |
| CN100384955C (en) * | 2004-09-06 | 2008-04-30 | 上海盛伦化工有限公司 | Antibacterial epoxy-polyester powdery coating with fast curing under low-temperature and production thereof |
| DE102005042822A1 (en) * | 2005-09-09 | 2007-03-22 | Degussa Ag | Low firing temperature hybrid powder coating composition for semi-glossy to matte coatings |
| CN100347250C (en) * | 2005-10-10 | 2007-11-07 | 湘潭市至诚涂料有限公司 | Cryogenic curing powdery coating for heat-sensitive substrate material |
| FR3000075B1 (en) * | 2012-12-21 | 2015-11-13 | Arkema France | CATALYTIC SYSTEMS FOR DEFORMABLE THERMOSETTING RESINS |
| CN103601872B (en) * | 2013-11-21 | 2015-07-29 | 天津翔盛粉末涂料有限公司 | A kind ofly reduce the catalyzer that end group is the saturated polyester resin solidification value of carboxyl |
| CN109627427A (en) * | 2018-11-19 | 2019-04-16 | 天津翔盛新材料有限公司 | A kind of preparation method of low viscosity epoxy resin and super levelling powdery paints |
| CN112409882A (en) * | 2020-11-13 | 2021-02-26 | 湖南太子化工涂料有限公司 | Epoxy resin and carboxyl polyester powder coating and preparation method thereof |
| CN115093776A (en) * | 2022-07-08 | 2022-09-23 | 广东睿智环保科技有限责任公司 | Antibacterial powder coating for MDF heat transfer printing and application method thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1391527A (en) * | 1963-05-02 | 1965-03-05 | Shell Int Research | Process for curing polyepoxides and resulting products |
| US3689444A (en) * | 1971-04-23 | 1972-09-05 | Celanese Coatings Co | Latent catalysts for one-component epoxy resin/anhydride compositions |
| JPS5949260B2 (en) * | 1975-08-27 | 1984-12-01 | 日本エステル （株） | Polyester resin composition for powder coatings |
| DE2641108C2 (en) * | 1976-09-13 | 1978-05-18 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Accelerator combination for the crosslinking of powder coating binders |
| IT1076226B (en) * | 1977-01-17 | 1985-04-27 | Sir Soc Italiana Resine Spa | SOLID CROSS-LINKABLE COMPOSITIONS INCLUDING A POLYESTER RESIN AND AN EPOXY RESIN |
| US4370452A (en) * | 1981-01-12 | 1983-01-25 | The Goodyear Tire & Rubber Company | Process to induce rapid curing of a copolyester resin with epoxide compounds and a composition formed for that process |
-
1985
- 1985-02-08 FR FR8501771A patent/FR2577231B1/en not_active Expired
-
1986
- 1986-01-29 EP EP86400190A patent/EP0194904B1/en not_active Expired
- 1986-01-29 DE DE8686400190T patent/DE3662902D1/en not_active Expired
- 1986-01-29 AT AT86400190T patent/ATE42315T1/en not_active IP Right Cessation
- 1986-02-07 DK DK61586A patent/DK61586A/en not_active Application Discontinuation
- 1986-02-07 JP JP61025639A patent/JPS61183367A/en active Pending
- 1986-02-07 CN CN86100991.6A patent/CN1003646B/en not_active Expired
- 1986-02-07 NO NO860440A patent/NO860440L/en unknown
- 1986-02-07 FI FI860565A patent/FI860565A/en not_active Application Discontinuation
- 1986-02-07 CA CA000501387A patent/CA1264882A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61183367A (en) | 1986-08-16 |
| FR2577231A1 (en) | 1986-08-14 |
| CN86100991A (en) | 1986-08-20 |
| FI860565A (en) | 1986-08-09 |
| CA1264882A (en) | 1990-01-23 |
| ATE42315T1 (en) | 1989-05-15 |
| DK61586A (en) | 1986-08-09 |
| CN1003646B (en) | 1989-03-22 |
| DE3662902D1 (en) | 1989-05-24 |
| FI860565A0 (en) | 1986-02-07 |
| EP0194904B1 (en) | 1989-04-19 |
| DK61586D0 (en) | 1986-02-07 |
| EP0194904A1 (en) | 1986-09-17 |
| FR2577231B1 (en) | 1987-09-11 |
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