JPH0328464B2 - - Google Patents
Info
- Publication number
- JPH0328464B2 JPH0328464B2 JP2704283A JP2704283A JPH0328464B2 JP H0328464 B2 JPH0328464 B2 JP H0328464B2 JP 2704283 A JP2704283 A JP 2704283A JP 2704283 A JP2704283 A JP 2704283A JP H0328464 B2 JPH0328464 B2 JP H0328464B2
- Authority
- JP
- Japan
- Prior art keywords
- organic
- insulating paint
- solvent
- acid
- electrically insulating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 59
- 239000003973 paint Substances 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 22
- 229930003836 cresol Natural products 0.000 claims description 22
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 10
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005456 alcohol based solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000010292 electrical insulation Methods 0.000 claims description 3
- 239000004210 ether based solvent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims 1
- 229960004106 citric acid Drugs 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- -1 metaxylene diamine Chemical class 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- GZOKBPPGHUGEHR-UHFFFAOYSA-N 1-methoxy-3-methylbutan-1-ol Chemical compound COC(O)CC(C)C GZOKBPPGHUGEHR-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- HHAPGMVKBLELOE-UHFFFAOYSA-N 2-(2-methylpropoxy)ethanol Chemical compound CC(C)COCCO HHAPGMVKBLELOE-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- AXLYZWOJUAFUIW-UHFFFAOYSA-N 2-methylpropanoic acid;2,3,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)=O.CC(C)C(C)(O)C(C)CO AXLYZWOJUAFUIW-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960004543 anhydrous citric acid Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- ZNFNDZCXTPWRLQ-UHFFFAOYSA-N butane-1,1,1-tricarboxylic acid Chemical compound CCCC(C(O)=O)(C(O)=O)C(O)=O ZNFNDZCXTPWRLQ-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Description
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The present invention relates to an electrical insulating paint and a method for producing the same, and in particular to a highly concentrated polyesteramide resin electrical insulating paint that can reduce the use of organic solvents and a method for producing the same. The present invention relates to an achievable polyesteramide resin electrical insulation coating and a method for producing the same. Conventional electrical insulating paints (hereinafter simply referred to as insulating paints) are mainly made by dissolving film-forming resins such as polyester resins and polyesterimide resins in organic solvents mainly consisting of cresol solvents such as cresol and phenol. However, the film-forming resin content in these insulating paints is at most 20 to 40%.
Stay at %. From the viewpoints of resource conservation, work environment improvement, and pollution prevention, it is desirable to reduce the amount of organic solvents that make up the remaining 60 to 80%, and there has been a demand for the development of high-concentration insulating paints. Furthermore, the above-mentioned cresol solvents have problems in terms of odor and toxicity, and it has been desired to develop an insulating coating that does not use cresol solvents. The present inventors have conducted intensive studies to meet the above requirements, and as a result have arrived at the present invention, which will be described below. By utilizing the shape of the insulating paint, we succeeded in obtaining an insulating paint that not only maintains good properties as a heat-resistant insulating paint, but also achieves high concentration and is soluble in non-cresol solvents. That is, the insulating paint of the present invention contains organic polycarboxylic acids selected from the group consisting of organic polycarboxylic acids, organic polycarboxylic acid anhydrides, and organic polycarboxylic acid lower alkyl esters, an organic polyhydric alcohol, and citric acid. It is characterized by consisting of a polyesteramide resin obtained by reacting with an organic diamine and an organic solvent. Examples of the organic polycarboxylic acids used in the present invention include succinic acid, adipic acid, sebacic acid,
Examples include phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, butanetricarboxylic acid, hemimellitic acid, pyromellitic acid, benzophenonetetracarboxylic acid, naphthalene dicarboxylic acid, and the like. Furthermore, anhydrides and lower alkyl esters of these acids can also be used as the organic polycarboxylic acids in the present invention. One type of these organic polycarboxylic acids may be used, or two or more types may be used in combination as appropriate. Examples of the organic polyhydric alcohol used in the present invention include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, neopentylene glycol, butanediol, glycerin, trimethylolpropane, tris( Examples include 2-hydroxyethyl) isocyanurate and pentaerythritol. One type of these organic polyhydric alcohols may be used, or two or more types may be used in combination. As mentioned above, the citric acid used in the present invention is an oxytricarboxylic acid having one hydroxyl group and three carboxyl groups in the molecule, but usually contains 1 hydroxyl group and 3 carboxyl groups in the molecule.
It is often commercially available as a crystal with a molecular weight of 210. In the present invention, both citric acid not containing water of crystallization and citric acid containing water of crystallization can be used. Examples of the organic diamine used in the present invention include hexamethylene diamine, octamethylene diamine, metaphenylene diamine, paraphenylene diamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,
Examples include 4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenylpropane, metaxylene diamine, paraxylene diamine, 1,4-diaminocyclohexane, 2,2'-diaminodiethyl ether, and guanamine. One type of these organic diamines may be used, or two or more types may be used in combination as appropriate. As the organic solvent used in the present invention, it is preferable to use a non-cresol solvent. The insulating coating of the present invention is soluble in non-cresol solvents. Examples of the cresol solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether,
Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monobutyl ether, 3-methylmethoxybutanol, 2,3,4-trimethyl 1,3-pentanediol monoisobutyrate,
Examples include glycol ether solvents such as ethylene glycol monoisobutyl ether, alcohol solvents such as benzyl alcohol, acetone alcohol, and diacetone alcohol, and isophorone. Among these, the general formula R 1 O (CHR 2 â
Glycol ether solvents represented by CH 2 O) o (R 1 is a lower alkyl group, R 2 is hydrogen or a methyl group, n is an integer of 1 to 3) are particularly suitable. These are 1
Seeds may be used, but two or more types are usually used in combination.
Further, an aromatic hydrocarbon solvent such as xylene may be used in combination as long as it does not cause turbidity. However, in the present invention, gresol solvents such as cresol, phenol, and xylenol may be used as the organic solvent. This is because even if these cresol solvents are used, the amount of organic solvent used can be reduced according to the present invention, and an insulating coating with high concentration can be obtained. Although one type of cresol solvent may be used, a mixed solvent of two or more types is usually used. Also in this case, an aromatic hydrocarbon solvent such as xylene may be used in combination within a range that does not cause turbidity. It is preferable to add a crosslinking agent to the electrically insulating paint of the present invention as appropriate from the viewpoint of improving the performance of the paint film. Specific examples of crosslinking agents include tetrabutyl titanate, tetraisopropyl titanate,
Examples include tetraphenyl titanate, or organic titanium compounds obtained by chelating these compounds with triethanolamine, ethyl acetoacetate, acetylacetone, or the like. The polyesteramide resin according to the present invention is not particularly limited in its production method, but is preferably selected from the group consisting of organic polycarboxylic acids, organic polycarboxylic acid anhydrides, and organic polycarboxylic acid lower alkyl esters. It is preferable to esterify an organic polycarboxylic acid and an organic polyhydric alcohol to obtain a polyester polyol, and then react the obtained polyester polyol with citric acid and an organic diamine, thereby achieving particularly high concentration. Moreover, it is possible to obtain a non-cresol solvent insulating coating with good properties. Next, each step of a preferred method for producing the polyesteramide resin insulation coating of the present invention will be described in detail. First, in the step of esterifying organic polycarboxylic acids and organic polyhydric alcohol, the blending ratio of the organic polycarboxylic acid component and the organic polyhydric alcohol component is adjusted so that the organic polyhydric alcohol component is in excess. Make it react. That is, both components are blended so that the ratio of total number of hydroxyl groups to total number of carboxy groups in the reaction mixture is 1.2 to 2.5, preferably 1.4 to 2.0.
If this ratio is too small, there is a risk of gelation before the reaction progresses sufficiently, and if it is too large, unreacted organic polyhydric alcohol will remain, which is not preferable. When carrying out this esterification reaction, a transesterification catalyst or a polycondensation catalyst is used. For example, organic acid salts such as acetates of lead, zinc, cadmium, cobalt, manganese, magnesium, etc., oxides of lead, antimony, etc., tetraalkyl titanates, etc. can be used. The amount used is 0.03 to 0.2 relative to the organic polycarboxylic acid component.
% by weight, preferably 0.05-0.15%. The esterification reaction is carried out in a conventional manner by raising the temperature of the reaction mixture to 160 to 200°C and reacting until the desired acid value is reached. The reaction is stopped when the acid value of the esterified product reaches 20 to 100, preferably 30 to 50. If the acid value of the produced polyester polyol is less than 20, the viscosity of the final polyester amide will be high, and if the acid value is 100 or more, the molecular weight will be too small and the performance of the paint film will be poor. Next, citric acid and an organic diamine are added to the polyester polyol obtained as described above and reacted to form a polyester amide. The blending ratio of citric acid is 5 to 50 mol%, preferably 10 to 40 mol%, based on the total number of moles of the organic polycarboxylic acid components used to obtain the polyester polyol. If the blending ratio of citric acid deviates from this range, the effect of using citric acid cannot be fully demonstrated, and if the blending ratio of citric acid is too small, the heat resistance of the paint film will not improve, while on the other hand, if the blending ratio of citric acid is too high, If it becomes too much, the paint film becomes hard, which is not preferable. The ratio of organic diamine used is 50% to citric acid.
~250 mol%, preferably 80-200 mol%.
If the proportion of organic diamine is too small, many unreacted carboxyl groups remain in the polyesteramide produced, resulting in a decrease in the performance of the paint film. Furthermore, if the proportion of organic diamine used is too large, the resulting polyesteramide will become too three-dimensional, resulting in poor solubility. The reaction of polyester polyol with citric acid and organic diamine is usually carried out when the temperature of the polyester polyol obtained in the above-mentioned esterification reaction is
After the temperature reaches 150â or below, add a predetermined amount of citric acid and organic diamine, and heat to 150-220â, preferably 180-220â.
The reaction is carried out at a temperature of 200° C. for several hours to several hours, and the reaction is stopped when the acid value reaches 15 to 100, preferably 20 to 40. For example, add citric acid and organic diamine to a polyester polyol that has reached a temperature of 150°C or less, raise the temperature to 150 to 190°C over 2 to 5 hours, and keep at this temperature for several hours until the specified acid value is reached. At that point, heating is stopped and some or all of the solvent is added to stop the reaction. If the acid value of the produced polyesteramide is less than 15, the molecule of the polyesteramide is too large and the viscosity of the paint becomes high. Furthermore, if the acid value exceeds 100, the insulation performance of the paint film deteriorates because the polyesteramide has not grown into molecules of sufficient size. Finally, if desired, a crosslinking agent is added at a temperature of 80°C or lower to obtain the desired high-concentration polyesteramide resin coating. The amount of the crosslinking agent added is usually 0.2 to 3.0% by weight based on the metal content relative to the resin content. If the amount of the crosslinking agent added is too small, the performance of the paint film will be insufficient, and if it is too large, the viscosity of the paint will increase markedly over time and the paint film will become hard, which are both undesirable. The present invention will be further explained in detail with reference to Examples and Comparative Examples below. Example 1 Trimellitic anhydride was added to a four-necked flask equipped with a stirrer, a thermometer, and a condenser with a measuring tube.
192g (1 mol), isophthalic acid 99.6g (0.6 mol), adipic acid 58.4g (0.4 mol), ethylene glycol 124g (2 mol), 1,4-butanediol 72.1g (0.8 mol), glycerin 110.5g (1.2 mol), xylol (reaction solvent) 30g and zinc acetate
0.18 g was charged, and the temperature was raised from room temperature to 150°C over 1 hour while stirring. Distillation started at 150â. Raise the temperature from 150â to 180â in 3 hours to 185
When kept at â for 2 hours, 99 g was distilled out to obtain a pale yellow transparent resin with an acid value of 55.1. Heating was stopped, and when the temperature of the resulting resin had fallen to 140°C, 76.8 g (0.4 mol) of anhydrous citric acid and 118.8 g (0.6 mol) of 4,4'-diaminodiphenylmethane were added, and heating was started again. The temperature was raised to 190°C over 2 hours, and the reaction was continued at this temperature for 1.5 hours. 11g of water distilled out, acid value
A reddish-brown resin of 23.6 was obtained. The heating was stopped, and 200 g of Hisolve DB (diethylene glycol monobutyl ether manufactured by Toho Chemical Industries, Ltd.), 225 g of ethylene glycol monomethyl ether, and 75 g of xylol were added to prepare a resin solution. Next, when the temperature drops to 80â or less, TBT100 [trade name of tetrabutyl titanate manufactured by Nippon Soda Co., Ltd.]. 22.5g of titanium (14%) dissolved in 22.5g of ethylene glycol monoethyl ether was gradually added over about 30 minutes. After the addition is complete, continue stirring for approximately 30 minutes. The obtained paint has a non-volatile content (200â x 2 hours)
The viscosity (at 30°C) was 59.6% and 28 poise. Table 1 shows an overview of the raw material formulation, synthesis conditions, and physical properties of the paint in Example 1. Example 2 Using an apparatus similar to that in Example 1, 153.6 g (0.8 mol) of trimellitic anhydride and 132.8 g (0.8 mol) of isophthalic acid were prepared.
g (0.8 mol), adipic acid 58.4 g (0.4 mol), ethylene glycol 155 g (2.5 mol), 1,4-butanediol 63.1 g (0.7 mol), glycerin 55.3
(0.6 mol), 30 g of xylol (reaction solvent), and 0.3 g of zinc acetate, and heated from room temperature while stirring.
The temperature was raised to 150°C in 1 hour. Distillation started at 150â. Raise the temperature from 150â to 185â in 3 hours
When kept at 185° C. for 2 hours, 101 g was distilled out, yielding a pale yellow transparent resin with an acid value of 43. Heating was stopped, and when the temperature of the resulting resin had fallen to 140°C, 63 g (0.3 mol) of citric acid and 118.8 g (0.6 mol) of 4,4'-diaminodiphenylmethane were added, and heating was started again. The temperature was raised to .degree. C. over 2 hours, and the reaction was continued at this temperature for 2.5 hours. 12g of water distilled out, acid value
A reddish-brown resin of 22.8 was obtained. The heating was stopped, and 498 g of cresol and 91 g of xylene were added to prepare a resin solution. Next, when the temperature fell below 80°C, a solution of 20g of TBT100 dissolved in 20g of cresol was gradually added over about 30 minutes. After the addition was complete, stirring was continued for an additional 30 minutes. The resulting paint had a nonvolatile content (200°C x 2 hours) of 51.6% and a viscosity (30°C) of 29 poise. Similar to Example 1, Table 1 summarizes the raw material formulation, synthesis conditions, and paint physical properties of Example 2. Examples 3 to 10 Paints were prepared using the same equipment and procedure as in Examples 1 and 2, using the raw materials and synthesis conditions shown in the Examples 3 to 10 columns of Table 1. The physical properties of the obtained paint are also shown in Table 1. Comparative Example In the same apparatus as in Examples 1 to 10, 430.8 g of dimethyl terephthalate, 93 g of ethylene glycol, 76.8 g of glycerin and 0.4 g of zinc acetate were prepared.
A polyester resin obtained by reacting the following in a conventional manner was diluted with a mixed solvent of cresol/xylene=8/2, and 12 g of TBT100 was added to prepare a polyester resin paint. The non-volatile content of this paint is 35
%, and the viscosity was 28 poise. The polyester amide resin paints obtained in Examples 1 to 10 and the polyester resin paints obtained in Comparative Examples were coated on a copper wire with a conductor diameter of 1.0 mm using a 7 m long furnace. Upper temperature 470
â, middle temperature 420â, bottom temperature 370â, linear speed 24m/
An insulated wire was manufactured by baking the wire seven times in minutes using the die method. The performance of each insulated wire obtained was as shown in Table 2.
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The performance of the insulated wire obtained in Example 10 was no inferior to that of a known polyester insulated wire. That is, according to the present invention, a non-cresol solvent can be used and an excellent insulated wire with a high concentration can be obtained, which has great industrial value.
Claims (1)
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ïŒé èšèŒã®é»æ°çµ¶çžå¡æã®è£œé æ¹æ³ã[Scope of Claims] 1. Organic polycarboxylic acids selected from the group consisting of organic polycarboxylic acids, organic polycarboxylic acid anhydrides, and organic polycarboxylic acid lower alkyl esters, organic polyhydric alcohols, and citric acid. An electrical insulation paint consisting of a polyesteramide resin obtained by reacting with an organic diamine and an organic solvent. 2 The organic solvent is a non-cresol solvent, and has the general formula R 1 O (CHR 2 - CH 2 O) o H (where R 1 is a lower alkyl group, R 2 is a hydrogen or methyl group, and n is 1 to 3). 50 glycol ether solvents (integers)
The electrical insulation paint according to claim 1, which is a non-cresol solvent containing ~100%. 3. The electricity according to claim 2, wherein the organic solvent used in combination with the glycol ether solvent is a non-cresol solvent selected from the group consisting of alcohol solvents, isophorone, and aromatic hydrocarbon solvents. Insulating paint. 4. The electrically insulating paint according to claim 1, which is obtained by adding a crosslinking agent to a resin solution consisting of a polyesteramide resin and an organic solvent. 5. The electrically insulating paint according to claim 1, wherein the polyesteramide resin has an acid value of 15 to 100. 6. The electrically insulating paint according to claim 5, which has an acid value of 20 to 40. 7 An organic polycarboxylic acid selected from the group consisting of an organic polycarboxylic acid, an organic polycarboxylic acid anhydride, and an organic polycarboxylic acid lower alkyl ester is subjected to an esterification reaction with an organic polyhydric alcohol to obtain a polyester polyol. A method for producing a polyester amide resin electrical insulating paint, which comprises reacting the obtained polyester polyol with citric acid and an organic diamine to obtain a polyester amide resin, and dissolving the resin in an organic solvent to obtain an electrical insulating paint. . 8. The method for producing an electrically insulating paint according to claim 7, wherein the polyester polyol has an acid value of 20 to 100. 9. The method for producing an electrically insulating paint according to claim 7, wherein 5 to 50 mol% of citric acid is used based on the acid component of the polyester polyol. 10 The acid value of polyesteramide resin is 15 to 100
A method for producing an electrically insulating paint according to claim 7. 11 Claim 1 having an acid value of 20 to 40
A method for producing an electrically insulating paint according to item 0. 12 The organic solvent is a non-cresol solvent, and has the general formula R 1 O (CHR 2 - CH 2 O) o H (wherein R 1 is a lower alkyl group, R 2 is a hydrogen or methyl group, and n is 1 to 3
(an integer of )
The method for producing an electrically insulating paint according to claim 7, wherein the electrically insulating paint contains 50 to 100% of a non-cresol solvent. 13 Claim 1, wherein the organic solvent used in combination with the glycol ether solvent is a non-cresol solvent selected from the group consisting of alcohol solvents, isophorone, and aromatic hydrocarbon solvents.
2. A method for producing an electrically insulating paint according to item 2.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2704283A JPS59155477A (en) | 1983-02-22 | 1983-02-22 | Electrical insulating coating and its preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2704283A JPS59155477A (en) | 1983-02-22 | 1983-02-22 | Electrical insulating coating and its preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59155477A JPS59155477A (en) | 1984-09-04 |
JPH0328464B2 true JPH0328464B2 (en) | 1991-04-19 |
Family
ID=12210006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2704283A Granted JPS59155477A (en) | 1983-02-22 | 1983-02-22 | Electrical insulating coating and its preparation |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59155477A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9027793D0 (en) * | 1990-12-21 | 1991-02-13 | Ucb Sa | Polyester-amides containing terminal carboxyl groups |
-
1983
- 1983-02-22 JP JP2704283A patent/JPS59155477A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS59155477A (en) | 1984-09-04 |
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