JP4832559B2

JP4832559B2 - ポリエステル及びその製造法

ポリエステル及びその製造法 Download PDF

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Publication number: JP4832559B2
Authority: JP; Japan
Prior art keywords: acid; polyester; dimethyl; group; formula
Prior art date: 2009-09-14
Legal status : Expired - Fee Related

Application number

JP2009212108A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009299073A5 (enExample

JP2009299073A (ja

Inventor

昌祥田畑

隆喜山▲ざき▼

Current Assignee

NATIONAL UNIVERSITY CORPORATION MURORAN INSTITUTE OF TECHNOLOGY

Nitta Corp

Original Assignee

NATIONAL UNIVERSITY CORPORATION MURORAN INSTITUTE OF TECHNOLOGY

Nitta Corp

Priority date

2009-09-14

Filing date

2009-09-14

Publication date

2011-12-07

2009-09-14 Application filed by NATIONAL UNIVERSITY CORPORATION MURORAN INSTITUTE OF TECHNOLOGY, Nitta Corp filed Critical NATIONAL UNIVERSITY CORPORATION MURORAN INSTITUTE OF TECHNOLOGY

2009-09-14 Priority to JP2009212108A priority Critical patent/JP4832559B2/ja

2009-12-24 Publication of JP2009299073A publication Critical patent/JP2009299073A/ja

2010-04-22 Publication of JP2009299073A5 publication Critical patent/JP2009299073A5/ja

2011-12-07 Application granted granted Critical

2011-12-07 Publication of JP4832559B2 publication Critical patent/JP4832559B2/ja

Status Expired - Fee Related legal-status Critical Current

2026-05-30 Anticipated expiration legal-status Critical

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229920000728 polyester Polymers 0.000 title claims abstract description 92
238000000034 method Methods 0.000 title claims description 22
239000002253 acid Substances 0.000 claims abstract description 95
125000003118 aryl group Chemical group 0.000 claims abstract description 26
150000004820 halides Chemical class 0.000 claims abstract description 19
239000013307 optical fiber Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 8
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 24
239000000460 chlorine Chemical group 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 21
239000011737 fluorine Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
150000008065 acid anhydrides Chemical class 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 13
239000000463 material Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
239000012776 electronic material Substances 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
239000011248 coating agent Substances 0.000 claims 1
239000002305 electric material Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
230000003647 oxidation Effects 0.000 abstract description 2
238000007254 oxidation reaction Methods 0.000 abstract description 2
150000008064 anhydrides Chemical group 0.000 abstract 1
150000005846 sugar alcohols Polymers 0.000 abstract 1
-1 alkoxysulfinyl group Chemical group 0.000 description 40
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 29
229920000642 polymer Polymers 0.000 description 22
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 19
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 17
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
235000010290 biphenyl Nutrition 0.000 description 14
239000004305 biphenyl Substances 0.000 description 13
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
238000010521 absorption reaction Methods 0.000 description 9
239000011162 core material Substances 0.000 description 9
RJWLXGOSIRVRAR-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 6
150000002009 diols Chemical class 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 5
238000005253 cladding Methods 0.000 description 5
238000004040 coloring Methods 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
239000004926 polymethyl methacrylate Substances 0.000 description 5
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 5
KRIDOPOPBBSDNT-UHFFFAOYSA-N 2,4,5-trimethyl-1,3-benzenediol Natural products CC1=CC(O)=C(C)C(O)=C1C KRIDOPOPBBSDNT-UHFFFAOYSA-N 0.000 description 4
RCNCKKACINZDOI-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-diol Chemical compound CC1=CC(O)=CC(O)=C1C RCNCKKACINZDOI-UHFFFAOYSA-N 0.000 description 4
VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 description 4
FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 4
QENPJKGENOZEEJ-UHFFFAOYSA-N 5-heptylbenzene-1,3-diol Chemical compound CCCCCCCC1=CC(O)=CC(O)=C1 QENPJKGENOZEEJ-UHFFFAOYSA-N 0.000 description 4
OYXWBGYHDYVIDT-UHFFFAOYSA-N 5-nonylbenzene-1,3-diol Chemical compound CCCCCCCCCC1=CC(O)=CC(O)=C1 OYXWBGYHDYVIDT-UHFFFAOYSA-N 0.000 description 4
GHVHDYYKJYXFGU-UHFFFAOYSA-N Beta-Orcinol Chemical compound CC1=CC(O)=C(C)C(O)=C1 GHVHDYYKJYXFGU-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 4
OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
WLJWDDUTPNYDHW-UHFFFAOYSA-N 2-butylbenzene-1,3-diol Chemical compound CCCCC1=C(O)C=CC=C1O WLJWDDUTPNYDHW-UHFFFAOYSA-N 0.000 description 3
WLZCXHMBJHCRFH-UHFFFAOYSA-N 2-methoxy-3-methylbenzene-1,4-diol Chemical compound COC1=C(C)C(O)=CC=C1O WLZCXHMBJHCRFH-UHFFFAOYSA-N 0.000 description 3
SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 3
YYEWRNLQOAIQDL-UHFFFAOYSA-N 4-phenylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 YYEWRNLQOAIQDL-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WJJMNDUMQPNECX-UHFFFAOYSA-N Dipicolinic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000004691 alkyl thio carbonyl group Chemical group 0.000 description 3
125000006267 biphenyl group Chemical group 0.000 description 3
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 3
238000005259 measurement Methods 0.000 description 3
LAQYHRQFABOIFD-UHFFFAOYSA-N methoxyhydroquinone Natural products COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
RNUBJWUYDSOLNB-OLQVQODUSA-N (2r,6s)-6-carboxy-1-methylpiperidin-1-ium-2-carboxylate Chemical compound CN1[C@@H](C(O)=O)CCC[C@H]1C(O)=O RNUBJWUYDSOLNB-OLQVQODUSA-N 0.000 description 2
GXAVBFNRWXCOPY-UHFFFAOYSA-N 1,4-dihydroxy-2,6-dimethoxybenzene Chemical compound COC1=CC(O)=CC(OC)=C1O GXAVBFNRWXCOPY-UHFFFAOYSA-N 0.000 description 2
JLUIOEOHOOLSJC-UHFFFAOYSA-N 1H-Pyrrole-2,5-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)N1 JLUIOEOHOOLSJC-UHFFFAOYSA-N 0.000 description 2
OEUSNWDYXDEXDR-UHFFFAOYSA-N 1h-pyrrole-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=CNC=1C(O)=O OEUSNWDYXDEXDR-UHFFFAOYSA-N 0.000 description 2
MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
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 2
BXJGUBZTZWCMEX-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diol Chemical compound CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 description 2
JVJFVMOQYXFIPC-UHFFFAOYSA-N 2,4,5,6-tetramethylbenzene-1,3-diol Chemical compound CC1=C(C)C(O)=C(C)C(O)=C1C JVJFVMOQYXFIPC-UHFFFAOYSA-N 0.000 description 2
WSKJIXLOKYWORS-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diol Chemical compound CC1=CC(C)=C(O)C(C)=C1O WSKJIXLOKYWORS-UHFFFAOYSA-N 0.000 description 2
NOBVPWXWXQOUSS-UHFFFAOYSA-N 2,4-dibromobenzene-1,3-diol Chemical compound OC1=CC=C(Br)C(O)=C1Br NOBVPWXWXQOUSS-UHFFFAOYSA-N 0.000 description 2
IELUPRVYGHTVHQ-UHFFFAOYSA-N 2,6-dibromohydroquinone Chemical compound OC1=CC(Br)=C(O)C(Br)=C1 IELUPRVYGHTVHQ-UHFFFAOYSA-N 0.000 description 2
UCKIUOTYKUQDMA-UHFFFAOYSA-N 2,8-diethylnonanedioic acid Chemical compound CCC(C(O)=O)CCCCCC(CC)C(O)=O UCKIUOTYKUQDMA-UHFFFAOYSA-N 0.000 description 2
YZGMIRBFYCQNRH-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzene-1,3-diol Chemical compound OCCC1=C(O)C=CC=C1O YZGMIRBFYCQNRH-UHFFFAOYSA-N 0.000 description 2
LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
AWVUCTKJHRJORG-VMPITWQZSA-N 2-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=CC=C1C(O)=O AWVUCTKJHRJORG-VMPITWQZSA-N 0.000 description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
DSYHFOPTZRKGJP-UHFFFAOYSA-N 2-ethyl-4-methylbenzene-1,3-diol Chemical compound CCC1=C(O)C=CC(C)=C1O DSYHFOPTZRKGJP-UHFFFAOYSA-N 0.000 description 2
DWVXFVWWARTDCQ-UHFFFAOYSA-N 2-ethylbenzene-1,3-diol Chemical compound CCC1=C(O)C=CC=C1O DWVXFVWWARTDCQ-UHFFFAOYSA-N 0.000 description 2
VJIDDJAKLVOBSE-UHFFFAOYSA-N 2-ethylbenzene-1,4-diol Chemical compound CCC1=CC(O)=CC=C1O VJIDDJAKLVOBSE-UHFFFAOYSA-N 0.000 description 2
NCTHQZTWNVDWGT-UHFFFAOYSA-N 2-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=C(O)C=CC=C1O NCTHQZTWNVDWGT-UHFFFAOYSA-N 0.000 description 2
BRIDIXYUUCVCGI-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diol Chemical compound COC1=CC(O)=C(C)C=C1O BRIDIXYUUCVCGI-UHFFFAOYSA-N 0.000 description 2
AFISIXRORMDOSK-UHFFFAOYSA-N 2-methoxy-6-propylbenzene-1,4-diol Chemical compound CCCC1=CC(O)=CC(OC)=C1O AFISIXRORMDOSK-UHFFFAOYSA-N 0.000 description 2
RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 2
ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
HHSCZZZCAYSVRK-UHFFFAOYSA-N 2-octylbenzene-1,3-diol Chemical compound CCCCCCCCC1=C(O)C=CC=C1O HHSCZZZCAYSVRK-UHFFFAOYSA-N 0.000 description 2
XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 2
XDCMHOFEBFTMNL-UHFFFAOYSA-N 2-propylbenzene-1,3-diol Chemical compound CCCC1=C(O)C=CC=C1O XDCMHOFEBFTMNL-UHFFFAOYSA-N 0.000 description 2
NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
YAVVHVRMNIDVOQ-UHFFFAOYSA-N 3,4-dinitrobenzene-1,2-diol Chemical compound OC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O YAVVHVRMNIDVOQ-UHFFFAOYSA-N 0.000 description 2
RGUZWBOJHNWZOK-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2-diol Chemical compound CC1=CC=C(C)C(O)=C1O RGUZWBOJHNWZOK-UHFFFAOYSA-N 0.000 description 2
BWBGEYQWIHXDKY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=CC(O)=C1 BWBGEYQWIHXDKY-UHFFFAOYSA-N 0.000 description 2
PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 2
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 2
PGXNXIDCWHOGRR-UHFFFAOYSA-N 3-propyl-5-sulfanylphenol Chemical compound CCCC1=CC(O)=CC(S)=C1 PGXNXIDCWHOGRR-UHFFFAOYSA-N 0.000 description 2
URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
KXAKDOWCKQHQIQ-UHFFFAOYSA-N 4,5,6-trimethylbenzene-1,3-diol Chemical compound CC1=C(C)C(O)=CC(O)=C1C KXAKDOWCKQHQIQ-UHFFFAOYSA-N 0.000 description 2
ATSSDICPUSGNHX-UHFFFAOYSA-N 4,6-di(propan-2-yl)benzene-1,3-diol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C=C1O ATSSDICPUSGNHX-UHFFFAOYSA-N 0.000 description 2
IYDQSPIOJHDHHO-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-diol Chemical compound CC1=CC(C)=C(O)C=C1O IYDQSPIOJHDHHO-UHFFFAOYSA-N 0.000 description 2
KJFMXIXXYWHFAN-UHFFFAOYSA-N 4,6-ditert-butylbenzene-1,3-diol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C=C1O KJFMXIXXYWHFAN-UHFFFAOYSA-N 0.000 description 2
ANTLBIMVNRRJNP-UHFFFAOYSA-N 4-(2-phenylethyl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1CCC1=CC=CC=C1 ANTLBIMVNRRJNP-UHFFFAOYSA-N 0.000 description 2
WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 2
NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 2
YLNRSZMAMFXDQE-UHFFFAOYSA-N 4-(4-methylpentyl)benzene-1,3-diol Chemical compound CC(C)CCCC1=CC=C(O)C=C1O YLNRSZMAMFXDQE-UHFFFAOYSA-N 0.000 description 2
HFLGBNBLMBSXEM-UHFFFAOYSA-N 4-Ethyl-1,2-benzenediol Chemical compound CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 description 2
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AQAUDKNQTMSRIM-UHFFFAOYSA-N dimethyl 1,5-dioxoanthracene-2,3-dicarboxylate Chemical compound C1=CC(=O)C2=CC3=CC(C(=O)OC)=C(C(=O)OC)C(=O)C3=CC2=C1 AQAUDKNQTMSRIM-UHFFFAOYSA-N 0.000 description 1
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ZUSILSFEVFLXMM-UHFFFAOYSA-N dimethyl 1-phenylpyrazole-3,5-dicarboxylate Chemical compound N1=C(C(=O)OC)C=C(C(=O)OC)N1C1=CC=CC=C1 ZUSILSFEVFLXMM-UHFFFAOYSA-N 0.000 description 1
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HTNRFPCXIYXRNG-UHFFFAOYSA-N dimethyl 3,4-dioxoanthracene-1,2-dicarboxylate Chemical compound C1=CC=C2C=C(C(=O)C(C(C(=O)OC)=C3C(=O)OC)=O)C3=CC2=C1 HTNRFPCXIYXRNG-UHFFFAOYSA-N 0.000 description 1
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DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
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FRDVFHGIAVOMOK-UHFFFAOYSA-N diphenyl pyridine-3,5-dicarboxylate Chemical compound C=1N=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FRDVFHGIAVOMOK-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SUNVJLYYDZCIIK-UHFFFAOYSA-N durohydroquinone Chemical compound CC1=C(C)C(O)=C(C)C(C)=C1O SUNVJLYYDZCIIK-UHFFFAOYSA-N 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
HTDVZCAGLAKZHY-TXEJJXNPSA-N ethyl 2-[(2s,6r)-6-(2-ethoxy-2-oxoethyl)-1-methylpiperidin-2-yl]acetate Chemical compound CCOC(=O)C[C@H]1CCC[C@@H](CC(=O)OCC)N1C HTDVZCAGLAKZHY-TXEJJXNPSA-N 0.000 description 1
JRSOAUOHTHOAOP-UHFFFAOYSA-N ethyl 2-[4-(2-ethoxy-2-oxoethyl)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(CC(=O)OCC)C=C1 JRSOAUOHTHOAOP-UHFFFAOYSA-N 0.000 description 1
CEYYGKGMMIZUSW-UHFFFAOYSA-N ethyl 2-[4-[4-(2-ethoxy-2-oxoethyl)phenyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1C1=CC=C(CC(=O)OCC)C=C1 CEYYGKGMMIZUSW-UHFFFAOYSA-N 0.000 description 1
NQAJKEFVVKYKNC-UHFFFAOYSA-N ethyl 4-(4-ethoxycarbonyl-2-methylphenyl)-3-methylbenzoate Chemical compound CC1=CC(C(=O)OCC)=CC=C1C1=CC=C(C(=O)OCC)C=C1C NQAJKEFVVKYKNC-UHFFFAOYSA-N 0.000 description 1
HIJANTBLVKZYLU-UHFFFAOYSA-N ethyl 4-[(4-ethoxycarbonylphenyl)disulfanyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1SSC1=CC=C(C(=O)OCC)C=C1 HIJANTBLVKZYLU-UHFFFAOYSA-N 0.000 description 1
ANUSOIHIIPAHJV-UHFFFAOYSA-N fenticlor Chemical compound OC1=CC=C(Cl)C=C1SC1=CC(Cl)=CC=C1O ANUSOIHIIPAHJV-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
JOTDFEIYNHTJHZ-UHFFFAOYSA-N furan-2,4-dicarboxylic acid Chemical compound OC(=O)C1=COC(C(O)=O)=C1 JOTDFEIYNHTJHZ-UHFFFAOYSA-N 0.000 description 1
SYLAFCZSYRXBJF-UHFFFAOYSA-N furan-3,4-dicarboxylic acid Chemical compound OC(=O)C1=COC=C1C(O)=O SYLAFCZSYRXBJF-UHFFFAOYSA-N 0.000 description 1
PUZSUVGRVHEUQO-UHFFFAOYSA-N gentisyl alcohol Chemical compound OCC1=CC(O)=CC=C1O PUZSUVGRVHEUQO-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000009413 insulation Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
150000002531 isophthalic acids Chemical class 0.000 description 1
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239000010410 layer Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-N 0.000 description 1
CGTYPNOFVGYUED-UHFFFAOYSA-N methyl 2-(2-methoxycarbonylphenyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1C(=O)OC CGTYPNOFVGYUED-UHFFFAOYSA-N 0.000 description 1
FNBAPAFWWYCASO-VAWYXSNFSA-N methyl 2-[(e)-2-(2-methoxycarbonylphenyl)ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1\C=C\C1=CC=CC=C1C(=O)OC FNBAPAFWWYCASO-VAWYXSNFSA-N 0.000 description 1
OOFQERBTJQWPID-UHFFFAOYSA-N methyl 2-[2-(2-methoxycarbonylphenyl)ethyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1CCC1=CC=CC=C1C(=O)OC OOFQERBTJQWPID-UHFFFAOYSA-N 0.000 description 1
KMSRAOIMKYBLAT-UHFFFAOYSA-N methyl 3-(2-methoxycarbonylpyridin-3-yl)pyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1C1=CC=CN=C1C(=O)OC KMSRAOIMKYBLAT-UHFFFAOYSA-N 0.000 description 1
GNKWTWFGKVDMPC-UHFFFAOYSA-N methyl 3-[2-(3-methoxycarbonylphenyl)ethyl]benzoate Chemical compound COC(=O)C1=CC=CC(CCC=2C=C(C=CC=2)C(=O)OC)=C1 GNKWTWFGKVDMPC-UHFFFAOYSA-N 0.000 description 1
QAQYBHOZQQRJBA-UHFFFAOYSA-N methyl 4-(2-methoxy-2-oxoethyl)benzoate Chemical compound COC(=O)CC1=CC=C(C(=O)OC)C=C1 QAQYBHOZQQRJBA-UHFFFAOYSA-N 0.000 description 1
CGARGJZZBOHMIZ-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=CC=C(C(=O)OC)C=C1 CGARGJZZBOHMIZ-UHFFFAOYSA-N 0.000 description 1
BKRIRZXWWALTPU-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)OC)C=C1 BKRIRZXWWALTPU-UHFFFAOYSA-N 0.000 description 1
FAFKIXPMYWNHGF-UHFFFAOYSA-N methyl 4-[(4-methoxycarbonylphenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CC1=CC=C(C(=O)OC)C=C1 FAFKIXPMYWNHGF-UHFFFAOYSA-N 0.000 description 1
VCKIQSATAZPKJV-UHFFFAOYSA-N methyl 4-[2-(4-methoxycarbonylphenyl)ethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCC1=CC=C(C(=O)OC)C=C1 VCKIQSATAZPKJV-UHFFFAOYSA-N 0.000 description 1
NJAYXDBLSXUUGN-UHFFFAOYSA-N methyl 6-(5-methoxycarbonylpyridin-2-yl)pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)OC)C=N1 NJAYXDBLSXUUGN-UHFFFAOYSA-N 0.000 description 1
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239000011259 mixed solution Substances 0.000 description 1
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DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
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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
KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
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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
MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
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