JP6468199B2 - ポリエステル樹脂組成物およびその製造方法 - Google Patents
ポリエステル樹脂組成物およびその製造方法 Download PDFInfo
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- JP6468199B2 JP6468199B2 JP2015556281A JP2015556281A JP6468199B2 JP 6468199 B2 JP6468199 B2 JP 6468199B2 JP 2015556281 A JP2015556281 A JP 2015556281A JP 2015556281 A JP2015556281 A JP 2015556281A JP 6468199 B2 JP6468199 B2 JP 6468199B2
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- polyester resin
- copper
- nitrogen
- resin composition
- compound
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- 229920001225 polyester resin Polymers 0.000 title claims description 158
- 239000004645 polyester resin Substances 0.000 title claims description 158
- 239000000203 mixture Substances 0.000 title claims description 104
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 106
- -1 copper halide Chemical class 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229910052802 copper Inorganic materials 0.000 claims description 78
- 239000010949 copper Substances 0.000 claims description 78
- 239000003446 ligand Substances 0.000 claims description 38
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 35
- 239000013522 chelant Substances 0.000 claims description 34
- 238000006068 polycondensation reaction Methods 0.000 claims description 33
- 150000003512 tertiary amines Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 20
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 16
- 150000002009 diols Chemical class 0.000 claims description 16
- 150000001879 copper Chemical class 0.000 claims description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 11
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 11
- 239000002994 raw material Substances 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 claims description 5
- 239000011112 polyethylene naphthalate Substances 0.000 claims description 5
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 4
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005750 Copper hydroxide Substances 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005751 Copper oxide Substances 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 43
- 230000007062 hydrolysis Effects 0.000 description 20
- 238000006460 hydrolysis reaction Methods 0.000 description 20
- 230000000694 effects Effects 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000013329 compounding Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 229910052787 antimony Inorganic materials 0.000 description 7
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000005749 Copper compound Substances 0.000 description 5
- 150000001880 copper compounds Chemical class 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000004699 copper complex Chemical class 0.000 description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 3
- MRLFFZIIRRKXBJ-UHFFFAOYSA-N bis(4-hydroxybutyl) benzene-1,4-dicarboxylate Chemical compound OCCCCOC(=O)C1=CC=C(C(=O)OCCCCO)C=C1 MRLFFZIIRRKXBJ-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910000410 antimony oxide Inorganic materials 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 2
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000005487 naphthalate group Chemical group 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 2
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical class [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- VFQCMEFEOOIYNK-UHFFFAOYSA-N 1,2,3,4-tetrakis(2,4-ditert-butyl-5-methylphenyl)-5-phenylbenzene Chemical compound C(C)(C)(C)C1=C(C=C(C(=C1)C(C)(C)C)C)C=1C(=C(C(=C(C=1)C1=CC=CC=C1)C1=C(C=C(C(=C1)C)C(C)(C)C)C(C)(C)C)C1=C(C=C(C(=C1)C)C(C)(C)C)C(C)(C)C)C1=C(C=C(C(=C1)C)C(C)(C)C)C(C)(C)C VFQCMEFEOOIYNK-UHFFFAOYSA-N 0.000 description 1
- DMDRBXCDTZRMHZ-UHFFFAOYSA-N 1,4-bis(2,4,6-trimethylanilino)anthracene-9,10-dione Chemical compound CC1=CC(C)=CC(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C=C1C DMDRBXCDTZRMHZ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- LZFNKJKBRGFWDU-UHFFFAOYSA-N 3,6-dioxabicyclo[6.3.1]dodeca-1(12),8,10-triene-2,7-dione Chemical compound O=C1OCCOC(=O)C2=CC=CC1=C2 LZFNKJKBRGFWDU-UHFFFAOYSA-N 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 238000005266 casting Methods 0.000 description 1
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- 239000000919 ceramic Substances 0.000 description 1
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- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- 229940116318 copper carbonate Drugs 0.000 description 1
- IBTMPTAQMGFDPW-UHFFFAOYSA-L copper octacosanoate Chemical compound [Cu++].CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O IBTMPTAQMGFDPW-UHFFFAOYSA-L 0.000 description 1
- LPELUJWALHFHRA-UHFFFAOYSA-L copper tridecanoate Chemical compound C(CCCCCCCCCCCC)(=O)[O-].[Cu+2].C(CCCCCCCCCCCC)(=O)[O-] LPELUJWALHFHRA-UHFFFAOYSA-L 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical compound [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 description 1
- CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 1
- PUHAKHQMSBQAKT-UHFFFAOYSA-L copper;butanoate Chemical compound [Cu+2].CCCC([O-])=O.CCCC([O-])=O PUHAKHQMSBQAKT-UHFFFAOYSA-L 0.000 description 1
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- OBITVTZBIATBCL-UHFFFAOYSA-L copper;decanoate Chemical compound [Cu+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O OBITVTZBIATBCL-UHFFFAOYSA-L 0.000 description 1
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- NVNJDKNLESDRQF-UHFFFAOYSA-L copper;docosanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O NVNJDKNLESDRQF-UHFFFAOYSA-L 0.000 description 1
- JDPSPYBMORZJOD-UHFFFAOYSA-L copper;dodecanoate Chemical compound [Cu+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O JDPSPYBMORZJOD-UHFFFAOYSA-L 0.000 description 1
- NQDSPXCXIOLFGI-UHFFFAOYSA-L copper;heptanoate Chemical compound [Cu+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O NQDSPXCXIOLFGI-UHFFFAOYSA-L 0.000 description 1
- GYPBUYJSHBFNEJ-UHFFFAOYSA-L copper;hexadecanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GYPBUYJSHBFNEJ-UHFFFAOYSA-L 0.000 description 1
- UBJRVPRGUGQWGH-UHFFFAOYSA-L copper;icosanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCC([O-])=O UBJRVPRGUGQWGH-UHFFFAOYSA-L 0.000 description 1
- HZULDDWVCRWYCB-UHFFFAOYSA-L copper;nonanoate Chemical compound [Cu+2].CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O HZULDDWVCRWYCB-UHFFFAOYSA-L 0.000 description 1
- VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 1
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- NBPFTDFXKORRKN-UHFFFAOYSA-L copper;pentanoate Chemical compound [Cu+2].CCCCC([O-])=O.CCCCC([O-])=O NBPFTDFXKORRKN-UHFFFAOYSA-L 0.000 description 1
- GSCLWPQCXDSGBU-UHFFFAOYSA-L copper;phthalate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O GSCLWPQCXDSGBU-UHFFFAOYSA-L 0.000 description 1
- PJBGIAVUDLSOKX-UHFFFAOYSA-N copper;propanedioic acid Chemical compound [Cu].OC(=O)CC(O)=O PJBGIAVUDLSOKX-UHFFFAOYSA-N 0.000 description 1
- LZJJVTQGPPWQFS-UHFFFAOYSA-L copper;propanoate Chemical compound [Cu+2].CCC([O-])=O.CCC([O-])=O LZJJVTQGPPWQFS-UHFFFAOYSA-L 0.000 description 1
- ZISLUDLMVNEAHK-UHFFFAOYSA-L copper;terephthalate Chemical compound [Cu+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 ZISLUDLMVNEAHK-UHFFFAOYSA-L 0.000 description 1
- GOBQJWZGIQHYFF-UHFFFAOYSA-L copper;tetradecanoate Chemical compound [Cu+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GOBQJWZGIQHYFF-UHFFFAOYSA-L 0.000 description 1
- XCKXYAJAIPORLM-UHFFFAOYSA-L copper;undecanoate Chemical compound [Cu+2].CCCCCCCCCCC([O-])=O.CCCCCCCCCCC([O-])=O XCKXYAJAIPORLM-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
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- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical compound CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- CTCOPPBXAFHGRB-UHFFFAOYSA-N ethanolate;germanium(4+) Chemical compound [Ge+4].CC[O-].CC[O-].CC[O-].CC[O-] CTCOPPBXAFHGRB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- KEMQGTRYUADPNZ-UHFFFAOYSA-M margarate Chemical compound CCCCCCCCCCCCCCCCC([O-])=O KEMQGTRYUADPNZ-UHFFFAOYSA-M 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
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- ZMCZWKGAWRLZNP-UHFFFAOYSA-N methyl-oxo-phenyltin Chemical compound C[Sn](=O)C1=CC=CC=C1 ZMCZWKGAWRLZNP-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- IIQJBVZYLIIMND-UHFFFAOYSA-J potassium;antimony(3+);2,3-dihydroxybutanedioate Chemical compound [K+].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O IIQJBVZYLIIMND-UHFFFAOYSA-J 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- JGOJQVLHSPGMOC-UHFFFAOYSA-N triethyl stiborite Chemical compound [Sb+3].CC[O-].CC[O-].CC[O-] JGOJQVLHSPGMOC-UHFFFAOYSA-N 0.000 description 1
- LOAWHQCNQSFKDK-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC.CC[Sn](CC)CC LOAWHQCNQSFKDK-UHFFFAOYSA-N 0.000 description 1
- OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
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- C08K5/00—Use of organic ingredients
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
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- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
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- C08G63/183—Terephthalic acids
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/02—Elements
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
- C08K3/11—Compounds containing metals of Groups 4 to 10 or of Groups 14 to 16 of the Periodic Table
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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- C08K5/00—Use of organic ingredients
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Description
本発明の実施形態で使用されるポリエステル樹脂は、ジカルボン酸またはそのエステル形成性誘導体、およびジオールを主原料として重縮合して得られる。ここで、主原料とは、ポリマー中のジカルボン酸、そのエステル形成性誘導体、およびジオールとの構成単位が、合計で80モル%以上であることを示す。この構成単位の合計は、より好ましくは90モル%以上、さらに好ましくは95モル%以上、最も好ましくは100モル%である。
本発明の実施形態では、ポリエステル樹脂を製造する際に銅を含む化合物を配合することが重要である。この銅を含む化合物は後述する含窒素化合物とともに銅錯体を形成することで本発明の効果を発現すると考えられる。
上記銅を含む化合物を配合することで、ポリエステル樹脂の酸価低減効果および耐加水分解性向上効果が期待できることは知られているが、銅を含む化合物を配合するだけでは、脱炭酸活性が低く、配合量を増やしても十分な酸価低減効果および耐加水分解性向上効果が得られないことがある。本発明では、銅に配位能力のある含窒素複素環構造または3級アミン構造を有する含窒素化合物を配合し、銅錯体とすることで、脱炭酸活性、およびポリエステル樹脂への分散性が向上することが見出された。その結果、発明者らは、ポリエステル樹脂の酸価が低くなることにより、耐加水分解性と透明性に優れるポリエステル樹脂を得ることに成功した。
本発明の実施形態において、効率的に酸価を低減させるためには、含窒素複素環構造または3級アミン構造を有する含窒素化合物を、銅を含む化合物の銅原子を基準として0.001〜4のモル比(含窒素化合物/銅を含む化合物の銅原子)でポリエステル樹脂に配合することが好ましい。モル比(含窒素化合物/銅を含む化合物の銅原子)は、0.01以上がより好ましく、0.1以上がさらに好ましく、0.4以上が最も好ましい。モル比(含窒素化合物/銅を含む化合物の銅原子)は、2以下がより好ましく、1以下がさらに好ましく、0.4以下が最も好ましい。モル比(含窒素化合物/銅を含む化合物の銅原子)を0.001以上とすることで、ポリエステル樹脂組成物のヘイズが大きくなるのを抑制できるので好ましい。一方、モル比(含窒素化合物/銅を含む化合物の銅原子)を4以下とすることで、銅に対する含窒素複素環構造または3級アミン構造を有する含窒素化合物が過剰となることがなく、ポリエステルの加水分解性を抑制させることができるので好ましい。
本発明の実施形態で使用されるジカルボン酸またはそのエステル形成性誘導体、およびジオールを主原料として得られるポリエステル樹脂の製造方法は、次の2段階の工程から成る。以降、エステル形成誘導体としてジカルボン酸アルキルエステルを用いた場合を記載する。すなわち、(A)エステル化反応、または(B)エステル交換反応からなる1段階目の工程と、それに続く(C)重縮合反応からなる2段階目の工程である。
本発明の実施形態のポリエステル樹脂組成物では、先に述べた銅を含む化合物と含窒素化合物を配合することで、ポリエステル樹脂組成物に含まれるポリエステル樹脂の酸価が13eq/t以下のポリエステル樹脂組成物を得ることができる。より耐加水分解性を向上させるためには、ポリエステル樹脂の酸価が10eq/t以下が好ましく、7eq/t以下がより好ましい。最も好ましくは2eq/t以下である。ここで、ポリエステル樹脂の酸価は、通常0eq/t以上である。ここで、ポリエステル樹脂以外の重縮合触媒、銅を含む化合物、含窒素化合物、添加剤等の合計配合量が1重量%未満である場合には、ポリエステル樹脂組成物をオルトクレゾール溶媒に溶解して、0.02規定の水酸化ナトリウム水溶液を用いて、25℃で滴定して求めた酸価を、ポリエステル樹脂の酸価と定義する。
・SKケミカル社製テレフタル酸ジメチル
・日本触媒社製エチレングリコール
・BASF社製1,4−ブタンジオール
・関東化学社製酢酸マグネシウム4水和物
・関東化学社製三酸化アンチモン
・関東化学社製リン酸トリメチル
・関東化学社製ヨウ化銅
・アルドリッチ社製1,10−フェナントロリン
・STREM CHEMICALS社製酢酸銅(I)
・関東化学社製酢酸銅(II)
・アルドリッチ社製硫酸銅5水和物
・関東化学社製2,2’−ビピリジル
・東京化成工業社製N、N、N'、N''、N''−ペンタメチルジエチレントリアミン
・和光純薬工業社製テトラ−n−ブトキシチタネート
ポリエステル樹脂組成物に含まれるポリエステル樹脂の数平均分子量は、以下に示す条件のゲルパーミエーションクロマトグラフィーにより算出した。
ポンプ:Waters 515(Waters製)
検出器:示差屈折率計 Waters 410(Waters製)
カラム:Shodex HFIP−806M(2本)+HFIP−LG
溶媒:ヘキサフルオロイソプロパノール(0.005N−トリフルオロ酢酸ナトリウム添加)
流速:1.0ml/min
試料注入量:0.1ml
温度:30℃
分子量校正:ポリメチルメタクリレート。
ポリエステル樹脂組成物をオルトクレゾールに30mg/Lの濃度で溶解させ、0.02規定の水酸化ナトリウム水溶液を用いて、25℃で自動滴定装置(平沼産業社製、COM−550)にて測定した。
ポリエステル樹脂組成物を140℃で16時間真空乾燥したペレットを、280℃でプレスし、厚さ1mmのプレートとした後に、高度加速寿命試験装置(エスペック社製、EHS−411)を用いて、121℃、100%RHの高湿度条件下で24時間保持した。処理前の数平均分子量に対する処理後の数平均分子量の保持率(%)を算出した。
ポリエステル樹脂組成物2gを20mlのオルトクロロフェノール/1,1,2,2‐テトラクロロエタンの3/2(容積比)混合溶液に溶解し、光路長20mmのセルを用い、ヘイズメーター(スガ試験機社製 HZ−1)を用いて、積分球式光電光度法にて測定した。
テレフタル酸ジメチル100重量部とエチレングリコール60重量部、および酢酸マグネシウム4水和物0.06重量部を混合した。その後、混合物を150℃、窒素雰囲気下で溶融後、攪拌しながら240℃まで4時間かけて昇温し、メタノールを留出させ、その後、エステル交換反応を行うことにより、ビス(ヒドロキシエチル)テレフタレートを得た。
実施例2〜13、15〜16および比較例1〜7、12
銅を含む化合物の種類と配合量および/または含窒素キレート配位子の種類と配合量を変更する以外は、実施例1と同様の方法でポリエステル樹脂組成物を得た。
テレフタル酸100重量部と1,4−ブタンジオール100重量部、およびテトラ−n−ブトキシチタネート0.06重量部を混合した。混合物を100℃、窒素雰囲気下で溶融後、攪拌しながら、圧力87kPaの減圧下にてエステル化反応を開始した。その後、混合物を230℃まで昇温し、230℃でエステル化反応を行った。エステル化反応の反応時間を240分間とし、ビス(ヒドロキシブチル)テレフタレートを得た。
銅を含む化合物の配合量を変更し、重縮合反応温度を245℃から255℃に変更した以外は、実施例17と同様の方法でポリエステル樹脂組成物を得た。
含窒素化合物を配合しないこと以外は、実施例17と同様の方法でポリエステル樹脂組成物を得た。
ヨウ化銅(I)と含窒素化合物を配合しないこと以外は、実施例17と同様の方法でポリエステル樹脂組成物を得た。
ヨウ化銅(I)を配合しないこと以外は、実施例17と同様の方法でポリエステル樹脂組成物を得た。
重縮合反応温度を245℃から255℃に変更した以外は、比較例9と同様の方法でポリエステル樹脂組成物を得た。
Claims (14)
- ジカルボン酸またはそのエステル形成性誘導体、およびジオールを主原料として、重縮合によって得られるポリエステル樹脂に、銅を含む化合物ならびに、含窒素複素環構造または3級アミン構造を有する含窒素キレート配位子を配合してなるポリエステル樹脂組成物であって、
銅を含む化合物を、銅原子基準でポリエステル樹脂100gあたり0.001〜0.3mmol配合し、
ポリエステル樹脂組成物2gを20mlのフェノール/1,1,2,2−テトラクロロエタンの3/2(容積比)混合溶液に溶解し、光路長20mmのセルを用いて測定したポリエステル溶液ヘイズが2.3%以下であることを特徴とするポリエステル樹脂組成物。 - 前記含窒素キレート配位子を、ポリエステル樹脂100gあたり0.001〜10mmol配合してなる請求項1に記載のポリエステル樹脂組成物。
- 銅を含む化合物の銅原子に対して、前記含窒素キレート配位子を、0.001〜4のモル比(含窒素キレート配位子/銅を含む化合物の銅原子)で配合してなる請求項1または2に記載のポリエステル樹脂組成物。
- 銅を含む化合物が、有機銅塩、無機銅塩、銅ハロゲン化物、銅酸化物、および銅水酸化物から選ばれる少なくとも1種である請求項1〜3のいずれか1項に記載のポリエステル樹脂組成物。
- 前記含窒素キレート配位子が、2,2’−ビピリジルの部分構造を有する化合物、1,10−フェナントロリンの部分構造を有する化合物、またはN、N、N'、N'−テトラメチルエチレンジアミンの部分構造を有する化合物である請求項1〜4のいずれか1項に記載のポリエステル樹脂組成物。
- 前記含窒素キレート配位子が、2,2’−ビピリジル、または1,10−フェナントロリンであることを特徴とする請求項5に記載のポリエステル樹脂組成物。
- 前記ポリエステル樹脂がポリエチレンテレフタレート、ポリプロピレンテレフタレート、ポリブチレンテレフタレートおよびポリエチレンナフタレートから選ばれる少なくとも1種である請求項1〜6のいずれか1項に記載のポリエステル樹脂組成物。
- 前記ポリエステル樹脂の数平均分子量が5000〜100000である請求項1〜7のいずれか1項に記載のポリエステル樹脂組成物。
- 前記ポリエステル樹脂の酸価が13eq/t以下であることを特徴とする請求項1〜8のいずれか1項に記載のポリエステル樹脂組成物。
- ジカルボン酸またはそのエステル形成性誘導体、およびジオールをエステル化反応またはエステル交換反応させ、次いで重縮合反応させて、請求項1記載のポリエステル樹脂を製造する際に、エステル化反応、エステル交換反応、および重縮合反応のいずれかの工程で、銅を含む化合物ならびに含窒素複素環構造または3級アミン構造を有する含窒素キレート配位子を配合するポリエステル樹脂組成物の製造方法。
- 得られるポリエステル樹脂100gあたり、銅を含む化合物を銅原子基準で、0.001〜0.3mmol配合する請求項10に記載のポリエステル樹脂組成物の製造方法。
- 得られるポリエステル樹脂100gあたり、前記含窒素キレート配位子を、0.001〜10mmol配合する請求項10または11に記載のポリエステル樹脂組成物の製造方法。
- 銅を含む化合物に含まれる銅原子に対して、前記含窒素キレート配位子を0.001〜4のモル比(含窒素キレート配位子/銅を含む化合物の銅原子)で配合する請求項10〜12のいずれか1項に記載のポリエステル樹脂組成物の製造方法。
- ジカルボン酸および/またはそのエステル形成性誘導体、並びにジオールを主原料とし、重縮合によって得られるポリエステル樹脂と、
銅を含む化合物と、
含窒素複素環構造と3級アミン構造との少なくとも一方を有する含窒素キレート配位子と、
を含むポリエステル樹脂組成物であって、
銅を含む化合物を、銅原子基準でポリエステル樹脂100gあたり0.001〜0.3mmol配合し、
ポリエステル樹脂組成物2gを20mlのフェノール/1,1,2,2−テトラクロロエタンの3/2(容積比)混合溶液に溶解し、光路長20mmのセルを用いて測定したポリエステル溶液ヘイズが2.3%以下であることを特徴とするポリエステル樹脂組成物。
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