JP4324163B2 - ポリエステル重合体の製造方法 - Google Patents
ポリエステル重合体の製造方法 Download PDFInfo
- Publication number
- JP4324163B2 JP4324163B2 JP2005503019A JP2005503019A JP4324163B2 JP 4324163 B2 JP4324163 B2 JP 4324163B2 JP 2005503019 A JP2005503019 A JP 2005503019A JP 2005503019 A JP2005503019 A JP 2005503019A JP 4324163 B2 JP4324163 B2 JP 4324163B2
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- polyester polymer
- acid
- mol
- ester
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims description 80
- 229920000728 polyester Polymers 0.000 title claims description 76
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 50
- 229910052717 sulfur Inorganic materials 0.000 claims description 50
- 239000011593 sulfur Substances 0.000 claims description 50
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 46
- -1 dicarboxylic acid compound Chemical class 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 238000012643 polycondensation polymerization Methods 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 47
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 46
- 230000003287 optical effect Effects 0.000 description 41
- 238000000034 method Methods 0.000 description 34
- 239000011347 resin Substances 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
- 238000000465 moulding Methods 0.000 description 25
- 239000002994 raw material Substances 0.000 description 24
- 230000009477 glass transition Effects 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000008188 pellet Substances 0.000 description 15
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 238000000748 compression moulding Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000012760 heat stabilizer Substances 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 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
- 238000005259 measurement Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000001444 catalytic combustion detection Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 229920006351 engineering plastic Polymers 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- PBWGCNFJKNQDGV-UHFFFAOYSA-N 6-phenylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(N)=C1C1=CC=CC=C1 PBWGCNFJKNQDGV-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(C2C(C3)CC1*C3C2)N Chemical compound CC1(C2C(C3)CC1*C3C2)N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229940090958 behenyl behenate Drugs 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000071 blow moulding Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000005443 coulometric titration Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 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
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229940071125 manganese acetate Drugs 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- PXDJXZJSCPSGGI-UHFFFAOYSA-N palmityl palmitate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- WXENKXQUTQFQIP-PLKIVWSFSA-N (2e,4e)-hexa-2,4-dienoic acid;octadecanoic acid Chemical compound C\C=C\C=C\C(O)=O.CCCCCCCCCCCCCCCCCC(O)=O WXENKXQUTQFQIP-PLKIVWSFSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GLCPRUJXNXWSRF-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,6-dicarboxylic acid Chemical compound C1C(C(O)=O)CCC2CC(C(=O)O)CCC21 GLCPRUJXNXWSRF-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- IBABXJRXGSAJLQ-UHFFFAOYSA-N 1,4-bis(2,6-diethyl-4-methylanilino)anthracene-9,10-dione Chemical compound CCC1=CC(C)=CC(CC)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(CC)C=C(C)C=C1CC IBABXJRXGSAJLQ-UHFFFAOYSA-N 0.000 description 1
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- KZYAYVSWIPZDKL-UHFFFAOYSA-N 1,4-diamino-2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Cl)C(Cl)=C2N KZYAYVSWIPZDKL-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-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
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- WZUNUACWCJJERC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)(CO)CO WZUNUACWCJJERC-UHFFFAOYSA-N 0.000 description 1
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- XJHYEZNHTVENQB-UHFFFAOYSA-N 2-[2,6-dibenzyl-4-[9-[3,5-dibenzyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC=3C=CC=CC=3)C(OCCO)=C(CC=3C=CC=CC=3)C=2)C=C(CC=2C=CC=CC=2)C(OCCO)=C1CC1=CC=CC=C1 XJHYEZNHTVENQB-UHFFFAOYSA-N 0.000 description 1
- HTIYWZRGYJCOQU-UHFFFAOYSA-N 2-[2,6-dibutyl-4-[9-[3,5-dibutyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound CCCCC1=C(OCCO)C(CCCC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CCCC)C(OCCO)=C(CCCC)C=2)=C1 HTIYWZRGYJCOQU-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- CAYZVGGMJCWXJQ-UHFFFAOYSA-N 2-[2-benzyl-4-(9H-fluoren-1-yl)phenoxy]ethanol Chemical compound OCCOC1=CC=C(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)C=C1CC1=CC=CC=C1 CAYZVGGMJCWXJQ-UHFFFAOYSA-N 0.000 description 1
- RSWNJYSWDLHAQZ-UHFFFAOYSA-N 2-[2-butan-2-yl-4-[9-[3-butan-2-yl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=C(OCCO)C(C(C)CC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C(C)CC)=C1 RSWNJYSWDLHAQZ-UHFFFAOYSA-N 0.000 description 1
- VYPZHMOPRNFKBI-UHFFFAOYSA-N 2-[2-ethyl-4-[9-[3-ethyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=C(OCCO)C(CC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC)C(OCCO)=CC=2)=C1 VYPZHMOPRNFKBI-UHFFFAOYSA-N 0.000 description 1
- RGMDGTAYZZQRBC-UHFFFAOYSA-N 2-[4-(4-oxo-1,3-benzoxazin-2-yl)phenyl]-1,3-benzoxazin-4-one Chemical compound C1=CC=C2OC(C3=CC=C(C=C3)C3=NC(C4=CC=CC=C4O3)=O)=NC(=O)C2=C1 RGMDGTAYZZQRBC-UHFFFAOYSA-N 0.000 description 1
- GPLGAPZOFUAGQL-UHFFFAOYSA-N 2-[4-[1-[4-(2-hydroxyethoxy)phenyl]-1-phenylethyl]phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C(C=1C=CC(OCCO)=CC=1)(C)C1=CC=CC=C1 GPLGAPZOFUAGQL-UHFFFAOYSA-N 0.000 description 1
- IODBYOUVGSFHER-UHFFFAOYSA-N 2-[4-[9-[3,5-diethyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]-2,6-diethylphenoxy]ethanol Chemical compound CCC1=C(OCCO)C(CC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC)C(OCCO)=C(CC)C=2)=C1 IODBYOUVGSFHER-UHFFFAOYSA-N 0.000 description 1
- FQAAHCMDCCKGDB-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-bis(2-methylpropyl)phenyl]fluoren-9-yl]-2,6-bis(2-methylpropyl)phenoxy]ethanol Chemical compound CC(C)CC1=C(OCCO)C(CC(C)C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC(C)C)C(OCCO)=C(CC(C)C)C=2)=C1 FQAAHCMDCCKGDB-UHFFFAOYSA-N 0.000 description 1
- YMHVCVNFCPTWAE-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-di(propan-2-yl)phenyl]fluoren-9-yl]-2,6-di(propan-2-yl)phenoxy]ethanol Chemical compound CC(C)C1=C(OCCO)C(C(C)C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=C(C(C)C)C=2)C(C)C)=C1 YMHVCVNFCPTWAE-UHFFFAOYSA-N 0.000 description 1
- IRTFFZWZLVOXMG-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]fluoren-9-yl]-2,6-dimethylphenoxy]ethanol Chemical compound CC1=C(OCCO)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(OCCO)=C(C)C=2)=C1 IRTFFZWZLVOXMG-UHFFFAOYSA-N 0.000 description 1
- ASSFXMFBALADJN-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-diphenylphenyl]fluoren-9-yl]-2,6-diphenylphenoxy]ethanol Chemical compound OCCOC1=C(C=2C=CC=CC=2)C=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 ASSFXMFBALADJN-UHFFFAOYSA-N 0.000 description 1
- XUMBDJVFYULJAB-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3,5-dipropylphenyl]fluoren-9-yl]-2,6-dipropylphenoxy]ethanol Chemical compound CCCC1=C(OCCO)C(CCC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CCC)C(OCCO)=C(CCC)C=2)=C1 XUMBDJVFYULJAB-UHFFFAOYSA-N 0.000 description 1
- QRCCWWMVEGTUOR-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-(2-methylpropyl)phenyl]fluoren-9-yl]-2-(2-methylpropyl)phenoxy]ethanol Chemical compound C1=C(OCCO)C(CC(C)C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC(C)C)C(OCCO)=CC=2)=C1 QRCCWWMVEGTUOR-UHFFFAOYSA-N 0.000 description 1
- HBTONAMIPDVQRI-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-phenylphenyl]fluoren-9-yl]-2-phenylphenoxy]ethanol Chemical compound OCCOC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 HBTONAMIPDVQRI-UHFFFAOYSA-N 0.000 description 1
- LDAHPWYXDVBMQV-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-propylphenyl]fluoren-9-yl]-2-propylphenoxy]ethanol Chemical compound C1=C(OCCO)C(CCC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CCC)C(OCCO)=CC=2)=C1 LDAHPWYXDVBMQV-UHFFFAOYSA-N 0.000 description 1
- OPJWPPVYCOPDCM-UHFFFAOYSA-N 2-ethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC OPJWPPVYCOPDCM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- KUYNRCIZTNCSRC-UHFFFAOYSA-N 3-[4-[9-[4-(3-hydroxypropoxy)phenyl]fluoren-9-yl]phenoxy]propan-1-ol Chemical compound C1=CC(OCCCO)=CC=C1C1(C=2C=CC(OCCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KUYNRCIZTNCSRC-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- QRTYJJNLCRSROQ-UHFFFAOYSA-N 4-[4-[9-[4-(4-hydroxybutoxy)phenyl]fluoren-9-yl]phenoxy]butan-1-ol Chemical compound C1=CC(OCCCCO)=CC=C1C1(C=2C=CC(OCCCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 QRTYJJNLCRSROQ-UHFFFAOYSA-N 0.000 description 1
- ZAAQJFLUOUQAOG-UHFFFAOYSA-N 4-benzyl-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=CC=CC=2)=C1 ZAAQJFLUOUQAOG-UHFFFAOYSA-N 0.000 description 1
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- UFNZMDCZLZUHRJ-UHFFFAOYSA-N CCC(CC1)C2C1CCCC2 Chemical compound CCC(CC1)C2C1CCCC2 UFNZMDCZLZUHRJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- QAEPIAHUOVJOOM-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC Chemical compound OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC QAEPIAHUOVJOOM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-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
- 239000007983 Tris buffer Substances 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- CGRTZESQZZGAAU-UHFFFAOYSA-N [2-[3-[1-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]-2-methylpropan-2-yl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-2-methylpropyl] 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCC(C)(C)C2OCC3(CO2)COC(OC3)C(C)(C)COC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 CGRTZESQZZGAAU-UHFFFAOYSA-N 0.000 description 1
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 1
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 1
- YWMLORGQOFONNT-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1 YWMLORGQOFONNT-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- IBKKMFMBXQARGV-UHFFFAOYSA-N [3-nonanoyloxy-2,2-bis(nonanoyloxymethyl)propyl] nonanoate Chemical compound CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC IBKKMFMBXQARGV-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- LBVBDLCCWCJXFA-UHFFFAOYSA-N adamantane-1,2-dicarboxylic acid Chemical compound C1C(C2)CC3CC1C(C(=O)O)C2(C(O)=O)C3 LBVBDLCCWCJXFA-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- KYQRDNYMKKJUTH-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)CC1C2 KYQRDNYMKKJUTH-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-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
- ZWRWUGGYDBHANL-UHFFFAOYSA-N butyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCC)OC1=CC=CC=C1 ZWRWUGGYDBHANL-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
- XYHMJVZAEWACCS-UHFFFAOYSA-N dimethyl 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,6-dicarboxylate Chemical compound C1C(C(=O)OC)CCC2CC(C(=O)OC)CCC21 XYHMJVZAEWACCS-UHFFFAOYSA-N 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- PXGLYSITKOROKV-UHFFFAOYSA-N dipropoxyphosphorylbenzene Chemical compound CCCOP(=O)(OCCC)C1=CC=CC=C1 PXGLYSITKOROKV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000002991 molded plastic Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- AJDJKHROQJQURF-UHFFFAOYSA-N phenanthrene-1,2-dicarboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1 AJDJKHROQJQURF-UHFFFAOYSA-N 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Images
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
- 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
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—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
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—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
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Artificial Filaments (AREA)
Description
ジカルボン酸またはそのエステル形成性誘導体とジヒドロキシ化合物からなるポリエステル重合体であって、ジヒドロキシ化合物が一般式(1)で示される化合物を含み、ジカルボン酸が脂環族ジカルボン酸及び芳香族ジカルボン酸もしくはこれらのエステル形成性誘導体を含み、ポリエステル重合体中のジエチレングリコールの量が6mol%以下であることを特徴とするポリエステル重合体を特徴とするポリエステル重合体。
これらのポリエステル重合体をディスク基板、レンズ、シート、フィルム、チューブ、又はファイバーに成形加工してなるポリエステル成形体である。
ポリマー中のジエチレングリコールが6mol%を超えると、耐熱性の指標であるガラス転移温度の低下や、屈折率の低下が大きくなり、ポリマーの特性の変化が大きくなり、光学樹脂として使用できなくなる。また、工業的に安定した品質のポリマーを経済的に提供しにくくなる。
これらの脂環族ジカルボン酸のエステル形成性誘導体としては、通常ポリエステルに用いられるジカルボン酸エステル形成性誘導体が挙げられ、例えばジメチルエステル、ジエチルエステル等のアルキルエステル等が挙げられる。
示差走査熱量計(セイコー電子 DSC−110)に試料約10mgを用いて、10℃/minの昇温速度で加熱して測定した。JIS K 7121(1987)に準拠して、ガラス転移温度Tgを求めた。
アタゴ社製アッベ屈折計 DR−M2で、波長589nmの干渉フィルターを用いD線での屈折率ndを測定した。測定試料は樹脂を160〜240℃でプレス成形し、厚み80〜150μmのフィルムを作成し、得られたフィルムを約8×20mmの短冊状に切り出し、測定試験片とした。界面液として1−ブロモナフタレンを用い20℃で測定した。
ブルカー社製DPX−400(400MHZ)のFT−NMR装置を用い、重水素化クロロホルムに試料を溶解し、テトラメチルシランを標品として混合し、プロトンNMRスペクトルを測定した。
試料調製
50mlの1−プロパノールを200mlの共栓フラスコに入れ、2.81gの水酸化カリウム、精秤した2gの樹脂チップをいれ、水冷している玉入冷却管を取り付け、攪拌しながら、2時間加熱還溜した。冷却後、水10mlを加え、7gのテレフタル酸を加え、1時間加熱還溜した。内部標準として、1%のテトラエチレングリコールジメチルエーテルの1−プロパノール溶液を5ml添加し、約5分攪拌。濾過したサンプルをガスクロマトグラフにより定量し、ジエチレングリコールの含有量を求めた。
硫酸成分に関しては、イオンクロマトグラフにより定量した。
試料調製
試料0.1gを20mlのメスフラスコに採取し、純水20mlでメスアップ後、超音波振動機にて10分間抽出した後、0.45μmのフィルターで濾過し、測定試料とした。
溶離液に7mmolのKOH水溶液を用い、カラムとしてAS−17(Dionex)を用い、定量を行った。
硫酸由来のイオウ含有量33PPMの1,4−シクロヘキサンジカルボン酸1mol(イーストマンケミカル社製)に対して、イオウ含有量7.7PPMの9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル社製、BPEF)0.8mol、エチレングリコール2.2molを原料とし、これらを反応槽に投入し、撹拌しながら常法に従って、室温から230℃に徐々に加熱してエステル化反応を行った。所定量の水を系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.002molと、着色を防止するため、リン酸トリメチルエステル0.0014molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、粘度の上昇を待ち、所定の攪拌トルクに到達後(約4時間後)反応を終了し、反応物を水中に押し出してペレットを得た。
原料組成比、含有イオウ量を表1に示すように変えた他は実施例1と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。いずれも均一透明なものが得られ、成形性も良好であった。
硫酸由来のイオウ含有量73PPMの1,4−シクロヘキサンジカルボン酸1mol(イーストマンケミカル社製)に対して、イオウ含有量7.7PPMの9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル社製)0.8mol、エチレングリコール2.2molを原料とし、これらを反応槽に投入し、撹拌しながら常法に従って、室温から230℃に徐々に加熱してエステル化反応を行った。所定量の水を系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.002molと、着色を防止するため、リン酸トリメチルエステル0.0014molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、粘度の上昇を待ったが、所定の攪拌トルクに到達しなかったので所定時間後(約4時間後)反応を終了し、反応物を水中に押し出してペレットを得た。
硫酸由来のイオウ含有量16PPMの1,4−シクロヘキサンジカルボン酸(イーストマンケミカル社製)1molに対して、イオウ含有量25PPMの9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン大阪ガスケミカル社製)0.8mol、エチレングリコール2.2molを原料とし、これらを反応槽に投入し、撹拌しながら常法に従って、室温から230℃に徐々に加熱してエステル化反応を行った。所定量の水を系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.002molと、着色を防止するため、リン酸トリメチルエステル0.0014molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、所定の攪拌トルクに到達後(約4時間後)反応を終了し、反応物を水中に押し出した。
原料組成比、含有イオウ量を表1に示すように変えた他は比較例1と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。比較例2と同様物性の低下が生じた。
原料組成比、含有イオウ量を表1に示すように変えた他は比較例1と同様な操作で製造したが、トルクが全く上昇せず、ステンレス製の攪拌翼が腐食された。着色した反応物が得られ、目的の重合体は得られなかった。
硫酸由来のイオウ含有量0PPMの1,4−シクロヘキサンジカルボン酸ジメチルエステル1mol(新日本理化社製)に対して、イオウ含有量10PPMの9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル社製)0.8mol、エチレングリコール2.2molを原料とし、触媒として、酢酸カルシウム0.0008mol、酢酸マンガン0.0002molを用い、これらを反応槽に投入し、撹拌しながら常法に従って、室温から230℃に徐々に加熱してエステル交換反応を行った。所定量のメタノールを系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.002molと、着色を防止するため、リン酸トリメチルエステル0.0014molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、粘度の上昇を待ち、所定の攪拌トルクに到達後(約4時間後)反応を終了し、反応物を水中に押し出してペレットを得た。
原料組成比、含有イオウ量を表1に示すように変えた他は実施例8と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。いずれも均一透明なものが得られ、成形性も良好であった。
原料組成比、含有イオウ量を表1に示すように変えた他は実施例10と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。実施例10に比べて、ガラス転移温度が10℃低くなり、物性の低下が生じた。
原料組成比、含有イオウ量を表1に示すように変えた他は実施例8と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。実施例8に比べて、ガラス転移温度が11℃低くなり、物性の低下が生じた。
原料組成比、含有イオウ量を表1に示すように変えた他は実施例9と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。実施例9に比べて、ガラス転移温度が8℃低くなり、物性の低下が生じた。
2,6−デカリンジカルボン酸ジメチルエステル1molに対して、9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル社製)0.55mol、エチレングリコール2.2molを原料とし、触媒として、酢酸カルシウム0.0008mol、酢酸マンガン0.0002molを用い、これらを反応槽に投入し、撹拌しながら常法に従って室温から230℃に徐々に加熱してエステル交換反応を行った。所定量のメタノールを系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.012molと、着色を防止するため、リン酸トリメチルエステル0.0018molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、粘度の上昇を待ち、所定の攪拌トルクに到達後(約2時間後)反応を終了し、反応物を水中に押し出してペレットを得た。
原料組成比を表1に示すように変えた他は実施例12と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。いずれも均一透明なものが得られた。
原料組成比を表1に示すように変えた他は実施例12と同様な操作でペレットを製造し、同様に評価した。結果を表1に示す。いずれも均一透明なものが得られたが、ガラス転移温度は実施例12に比べて12℃低いものとなり、物性が低下した。
硫酸由来のイオウ含有量33PPMの1,4−シクロヘキサンジカルボン酸0.5mol(イーストマンケミカル社製)と硫酸由来のイオウ含有量0PPMのテレフタル酸に対して、イオウ含有量7.7PPMの9,9−ビス[4−(2−ヒドロキシエトキシ)フェニル]フルオレン(大阪ガスケミカル社製、BPEF)0.75mol、エチレングリコール2.2molを原料とし、これらを反応槽に投入し、撹拌しながら常法に従って、室温から230℃に徐々に加熱してエステル化反応を行った。所定量の水を系外へ抜き出した後、重合触媒である酸化ゲルマニウム0.002molと、着色を防止するため、リン酸トリメチルエステル0.0014molとを投入して、昇温と減圧を徐々に行い、発生するエチレングリコールを抜きながら、加熱槽温度を270℃、真空度を133Pa(1Torr)以下に到達させた。この条件を維持し、粘度の上昇を待ち、所定の攪拌トルクに到達後(約4時間後)反応を終了し、反応物を水中に押し出してペレットを得た。
ジカルボン酸をテレフタル酸ジメチルエステルとし、9,9−ビス−(4−ヒドロキシエトキシフェニル)−フルオレンを0molとした他は実施8と同様にして反応させ、ペレットを得た。ガラス転移温度は75℃と低く、耐熱性が不十分であった。レンズを成形したところ、白濁し、レンズには使用できなかった。
Claims (2)
- ジカルボン酸またはそのエステル形成性誘導体からなるジカルボン酸化合物とジヒドロキシ化合物からポリエステル重合体を製造するに際して、原料のジカルボン酸化合物が含有されるイオウ量が50PPM以下であり、且つ脂環族ジカルボン酸および/またはそのエステル形成性誘導体を含むものであり、ジヒドロキシ化合物が含有されるイオウ量が20PPM以下であり、且つ一般式(1)で示される化合物を含むものであり、これらをエステル交換または直接エステル化する第一工程と、減圧しながら縮重合反応を行う第二工程を経て製造することを特徴とするポリエステル重合体の製造方法。
- ジカルボン酸またはそのエステル形成性誘導体からなるジカルボン酸化合物とジヒドロキシ化合物からポリエステル重合体を製造するに際して、原料のジカルボン酸化合物が含有されるイオウ量が50PPM以下であり、且つ脂環族ジカルボン酸および/またはそのエステル形成性誘導体、および芳香族ジカルボン酸および/またはそのエステル形成性誘導体を含むものであり、ジヒドロキシ化合物が含有されるイオウ量が20PPM以下であり、且つ一般式(1)で示される化合物を含むものであり、これらをエステル交換または直接エステル化する第一工程と、減圧しながら縮重合反応を行う第二工程を経て製造することを特徴とするポリエステル重合体の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003055250 | 2003-03-03 | ||
JP2003055250 | 2003-03-03 | ||
PCT/JP2004/002420 WO2004078824A1 (ja) | 2003-03-03 | 2004-02-27 | ポリエステル重合体およびその成形体およびポリエステル重合体の製造方法 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009095973A Division JP5271142B2 (ja) | 2003-03-03 | 2009-04-10 | ポリエステル重合体およびその成形体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2004078824A1 JPWO2004078824A1 (ja) | 2006-06-08 |
JP4324163B2 true JP4324163B2 (ja) | 2009-09-02 |
Family
ID=32958658
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005503019A Expired - Lifetime JP4324163B2 (ja) | 2003-03-03 | 2004-02-27 | ポリエステル重合体の製造方法 |
JP2009095973A Expired - Lifetime JP5271142B2 (ja) | 2003-03-03 | 2009-04-10 | ポリエステル重合体およびその成形体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009095973A Expired - Lifetime JP5271142B2 (ja) | 2003-03-03 | 2009-04-10 | ポリエステル重合体およびその成形体 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7538176B2 (ja) |
JP (2) | JP4324163B2 (ja) |
KR (1) | KR100712167B1 (ja) |
CN (1) | CN100395277C (ja) |
TW (1) | TWI249544B (ja) |
WO (1) | WO2004078824A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS615973B1 (ja) * | 1981-12-14 | 1986-02-22 | Fuji Photo Film Co Ltd | |
EP3909998A3 (en) | 2005-04-22 | 2022-03-16 | Mitsubishi Chemical Corporation | Biomass-resource-derived polyester and production process thereof |
JP2006321996A (ja) * | 2005-04-22 | 2006-11-30 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
JP2006321997A (ja) * | 2005-04-22 | 2006-11-30 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
US8859648B2 (en) * | 2005-05-25 | 2014-10-14 | Toray Industries, Inc. | Retardation film and polyester resin for optical use |
JP5233085B2 (ja) * | 2005-06-28 | 2013-07-10 | 東レ株式会社 | 光学用ポリエステル樹脂を含む液晶ディスプレイ用光学ポリエステルフィルム |
KR101403931B1 (ko) | 2005-08-18 | 2014-06-09 | 도레이 카부시키가이샤 | 적층 필름 및 성형체 |
JP5151186B2 (ja) * | 2006-03-08 | 2013-02-27 | 東レ株式会社 | 易表面賦形性シート用組成物、及びそれを用いて形成される易表面賦形性シート、易表面賦形性シート積層体、それを用いた表面賦形方法ならびに成形品。 |
JP2007262190A (ja) * | 2006-03-28 | 2007-10-11 | Toray Ind Inc | 光学用ポリエステル樹脂及びこれを含有したポリエステルフィルム |
JP2008111047A (ja) * | 2006-10-30 | 2008-05-15 | Mitsubishi Gas Chem Co Inc | ポリカーボネート樹脂の製造方法 |
JP2010100770A (ja) * | 2008-10-27 | 2010-05-06 | Mitsubishi Gas Chemical Co Inc | 熱可塑性樹脂の製造方法、ポリエステル樹脂及びポリカーボネート樹脂、ならびにそれらの用途 |
FR2969311B1 (fr) * | 2010-12-20 | 2013-01-18 | Rhodia Acetow Gmbh | Module de source lumineuse a led (diode electroluminescente) |
WO2012133873A1 (ja) | 2011-03-28 | 2012-10-04 | 帝人化成株式会社 | フルオレン誘導体からなる熱可塑性樹脂 |
JP6175268B2 (ja) * | 2013-04-10 | 2017-08-02 | 大阪ガスケミカル株式会社 | 耐湿性向上剤 |
JP6495075B2 (ja) * | 2014-04-01 | 2019-04-03 | 大阪ガスケミカル株式会社 | 位相差フィルム用ポリエステル樹脂 |
JP6530948B2 (ja) * | 2014-04-01 | 2019-06-12 | 大阪ガスケミカル株式会社 | 位相差フィルム用ポリエステル樹脂 |
JP2014133899A (ja) * | 2014-04-23 | 2014-07-24 | Mitsubishi Chemicals Corp | バイオマス資源由来ポリエステル製延伸フィルム |
JP6415519B2 (ja) * | 2016-11-17 | 2018-10-31 | 帝人株式会社 | フルオレン誘導体からなる熱可塑性樹脂 |
JP7507537B2 (ja) | 2019-01-25 | 2024-06-28 | 大和製罐株式会社 | ポリエステル樹脂及びその成形体 |
JP2022167814A (ja) * | 2021-04-23 | 2022-11-04 | 新光合成纎維股▲分▼有限公司 | 耐屈折性があるポリエステルフィルム及びその製造方法 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4904755A (en) * | 1989-01-23 | 1990-02-27 | Eastman Kodak Company | Low birefringent polyesters in optical devices |
US5202475A (en) | 1990-09-27 | 1993-04-13 | Eastman Kodak Company | Process for preparation of cyclohexanedicarboxylic acid |
EP0653451B1 (en) * | 1992-07-30 | 1999-02-17 | Kanebo, Ltd. | Polyester |
JP2843214B2 (ja) * | 1992-07-30 | 1999-01-06 | 鐘紡株式会社 | ポリエステル重合体およびその成形体 |
JP2843215B2 (ja) | 1992-07-30 | 1999-01-06 | 鐘紡株式会社 | ポリエステル重合体およびその成形体並びに成形体の製造方法 |
JP3106411B2 (ja) | 1992-12-21 | 2000-11-06 | 東和化成工業株式会社 | 1,4−シクロヘキサンジカルボン酸の製造方法 |
JP2559332B2 (ja) | 1993-12-10 | 1996-12-04 | 大阪瓦斯株式会社 | フルオレン誘導品の製造方法及びその精製方法 |
JPH0948842A (ja) * | 1995-08-02 | 1997-02-18 | Nippon Ester Co Ltd | コポリエステル |
JP3331121B2 (ja) * | 1996-05-17 | 2002-10-07 | カネボウ株式会社 | ポリエステル重合体およびその成形体 |
JP3750000B2 (ja) | 1996-06-26 | 2006-03-01 | 大阪瓦斯株式会社 | フェノキシエタノールの回収方法及びフルオレン誘導品の製造方法 |
KR100226191B1 (ko) * | 1997-04-03 | 1999-10-15 | 구광시 | 음료용 플라스틱 병 |
JP3318230B2 (ja) * | 1997-05-06 | 2002-08-26 | 帝人株式会社 | ポリエチレンナフタレート共重合体からなる写真フイルム用ベースフイルム |
JPH1160706A (ja) | 1997-08-13 | 1999-03-05 | Osaka Gas Co Ltd | ポリエステル重合体およびその製造方法 |
JP3795234B2 (ja) * | 1998-08-03 | 2006-07-12 | カネボウ株式会社 | ポリエステル重合体およびその成形体 |
JP2000256448A (ja) * | 1999-03-09 | 2000-09-19 | Nippon Ester Co Ltd | 共重合ポリエステル |
JP2000319366A (ja) | 1999-05-12 | 2000-11-21 | Osaka Gas Co Ltd | ポリエステル重合体及びその製造方法 |
JP2000327757A (ja) * | 1999-05-19 | 2000-11-28 | Osaka Gas Co Ltd | 電子写真感光体 |
-
2004
- 2004-02-27 WO PCT/JP2004/002420 patent/WO2004078824A1/ja active Application Filing
- 2004-02-27 US US10/547,350 patent/US7538176B2/en active Active
- 2004-02-27 JP JP2005503019A patent/JP4324163B2/ja not_active Expired - Lifetime
- 2004-02-27 CN CNB2004800057822A patent/CN100395277C/zh not_active Expired - Lifetime
- 2004-02-27 KR KR1020057016293A patent/KR100712167B1/ko active IP Right Grant
- 2004-03-02 TW TW093105340A patent/TWI249544B/zh active
-
2009
- 2009-04-10 JP JP2009095973A patent/JP5271142B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20070106053A1 (en) | 2007-05-10 |
JP2009185299A (ja) | 2009-08-20 |
KR100712167B1 (ko) | 2007-04-27 |
JPWO2004078824A1 (ja) | 2006-06-08 |
TWI249544B (en) | 2006-02-21 |
KR20050115259A (ko) | 2005-12-07 |
US7538176B2 (en) | 2009-05-26 |
CN100395277C (zh) | 2008-06-18 |
CN1756787A (zh) | 2006-04-05 |
WO2004078824A1 (ja) | 2004-09-16 |
TW200426172A (en) | 2004-12-01 |
JP5271142B2 (ja) | 2013-08-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5271142B2 (ja) | ポリエステル重合体およびその成形体 | |
JP4908781B2 (ja) | ポリエステル樹脂組成物および光学部品 | |
JP4384636B2 (ja) | ポリエステル樹脂組成物ならびに光学材料 | |
JP3331121B2 (ja) | ポリエステル重合体およびその成形体 | |
JP6102966B2 (ja) | ポリカーボネート共重合体 | |
JP5532531B2 (ja) | ポリカーボネート共重合体及びその製造方法 | |
KR20170005792A (ko) | 중축합으로 제조된 수지 및 수지 조성물 | |
JP2011080091A (ja) | ポリカーボネートの製造方法 | |
JP2977714B2 (ja) | ポリエステル成形体 | |
JPH07198901A (ja) | プラスチックレンズ用ポリエステル樹脂 | |
JP2843215B2 (ja) | ポリエステル重合体およびその成形体並びに成形体の製造方法 | |
JP2840211B2 (ja) | ポリエステル重合体及びその成形体 | |
JP2000319366A (ja) | ポリエステル重合体及びその製造方法 | |
JP2843214B2 (ja) | ポリエステル重合体およびその成形体 | |
JP3023279B2 (ja) | 光学材料用樹脂組成物および光学材料ならびに光学材料の製造法 | |
JP5585999B2 (ja) | ポリエステル樹脂組成物及び成形体 | |
TW202037632A (zh) | 熱塑性樹脂及其製造方法以及包含該熱塑性樹脂之光學透鏡 | |
JP2000119379A (ja) | 光学素子 | |
JP2854796B2 (ja) | ポリエステル重合体及びその成形体 | |
JP3101453B2 (ja) | ポリエステル共重合体 | |
JP2005023124A (ja) | 芳香族ポリカーボネート樹脂 | |
JPH0841304A (ja) | ポリエステル樹脂成形体及びその製造法 | |
JP2005041988A (ja) | ポリカーボネート樹脂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060314 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20080221 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20080221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20080221 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090210 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090410 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090519 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090605 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4324163 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120612 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120612 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150612 Year of fee payment: 6 |
|
EXPY | Cancellation because of completion of term |