JP2011084731A - 芳香族ポリエステル - Google Patents
芳香族ポリエステル Download PDFInfo
- Publication number
- JP2011084731A JP2011084731A JP2010190798A JP2010190798A JP2011084731A JP 2011084731 A JP2011084731 A JP 2011084731A JP 2010190798 A JP2010190798 A JP 2010190798A JP 2010190798 A JP2010190798 A JP 2010190798A JP 2011084731 A JP2011084731 A JP 2011084731A
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- JP
- Japan
- Prior art keywords
- group
- acid
- aromatic polyester
- aromatic
- dimethyl
- 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.)
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 274
- 229920000728 polyester Polymers 0.000 title claims abstract description 258
- 239000002253 acid Substances 0.000 claims abstract description 99
- 150000004820 halides Chemical class 0.000 claims abstract description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 sulfenato group Chemical group 0.000 claims description 74
- 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 72
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 238000004519 manufacturing process Methods 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 31
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 29
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 150000008065 acid anhydrides Chemical group 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 230000003287 optical effect Effects 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 238000005259 measurement Methods 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 7
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 7
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000005427 anthranyl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 abstract description 8
- 238000000465 moulding Methods 0.000 abstract description 7
- 125000004018 acid anhydride group Chemical group 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 54
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 16
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 15
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 235000010290 biphenyl Nutrition 0.000 description 14
- 239000004305 biphenyl Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 125000004185 ester group Chemical group 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002835 absorbance Methods 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
- 230000006866 deterioration Effects 0.000 description 8
- 239000012074 organic phase Substances 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
- 238000005406 washing Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 239000013307 optical fiber Substances 0.000 description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 description 4
- 238000005580 one pot reaction Methods 0.000 description 4
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 4
- 229920001230 polyarylate Polymers 0.000 description 4
- 238000006116 polymerization 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
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-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
- 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 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 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
- 238000004364 calculation method Methods 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- LAQYHRQFABOIFD-UHFFFAOYSA-N methoxyhydroquinone Natural products COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- SPALIFXDWQTXKS-UHFFFAOYSA-M tetrapentylazanium;bromide Chemical compound [Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SPALIFXDWQTXKS-UHFFFAOYSA-M 0.000 description 3
- SXAWRMKQZKPHNJ-UHFFFAOYSA-M tetrapentylazanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SXAWRMKQZKPHNJ-UHFFFAOYSA-M 0.000 description 3
- JYDIJFKNXHPWBJ-FBBRVDCYSA-M (s)-[(2r,4s,5r)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride Chemical compound [Cl-].C([C@H]([C@H](C1)C=C)C[C@@H]2[C@@H](O)C3=CC=NC4=CC=C(C=C43)OC)C[N+]21CC1=CC=CC=C1 JYDIJFKNXHPWBJ-FBBRVDCYSA-M 0.000 description 2
- NHEVNUARLCWEED-UHFFFAOYSA-N 1,4,5-Naphthalenetriol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1O NHEVNUARLCWEED-UHFFFAOYSA-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
- IKTPUTARUKSCDG-UHFFFAOYSA-N 1h-pyrazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1C=NNC=1C(O)=O IKTPUTARUKSCDG-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
- HXBBWWNXODCSPT-UHFFFAOYSA-N 2,2',6,6'-tetrahydroxy-1,1'-biphenyl Natural products OC1=CC=CC(O)=C1C1=C(O)C=CC=C1O HXBBWWNXODCSPT-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
- TXLWEPPRCDCHRB-UHFFFAOYSA-N 2,6-diiodobenzene-1,4-diol Chemical compound OC1=CC(I)=C(O)C(I)=C1 TXLWEPPRCDCHRB-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
- QFYYAIBEHOEZKC-UHFFFAOYSA-N 2-Methoxyresorcinol Chemical compound COC1=C(O)C=CC=C1O QFYYAIBEHOEZKC-UHFFFAOYSA-N 0.000 description 2
- DIMBHNJPNUATCU-OCAPTIKFSA-N 2-[(2r,6s)-6-(carboxymethyl)-1-methylpiperidin-2-yl]acetic acid Chemical compound CN1[C@@H](CC(O)=O)CCC[C@H]1CC(O)=O DIMBHNJPNUATCU-OCAPTIKFSA-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
- 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- GPJJASIJVRXZFI-UHFFFAOYSA-N 2-methoxyresorcinol Natural products COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-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
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- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 1
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- KTLFENNEPHBKJD-UHFFFAOYSA-K benzyl(trimethyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 KTLFENNEPHBKJD-UHFFFAOYSA-K 0.000 description 1
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- ZYAMRXZPHTVKCK-UHFFFAOYSA-N bis(1,2-benzoxazol-3-yl) benzene-1,3-dicarboxylate Chemical compound C1=CC=C2C(OC(=O)C=3C=CC=C(C=3)C(OC=3C4=CC=CC=C4ON=3)=O)=NOC2=C1 ZYAMRXZPHTVKCK-UHFFFAOYSA-N 0.000 description 1
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- KHXXVLXPONONRC-UHFFFAOYSA-N bis(1,3-benzothiazol-2-yl) benzene-1,3-dicarboxylate Chemical compound C1=CC=C2SC(OC(=O)C=3C=CC=C(C=3)C(OC=3SC4=CC=CC=C4N=3)=O)=NC2=C1 KHXXVLXPONONRC-UHFFFAOYSA-N 0.000 description 1
- DBZYLSSAYQSLSS-UHFFFAOYSA-N bis(1,3-benzothiazol-2-yl) benzene-1,4-dicarboxylate Chemical compound C1=CC=C2SC(OC(=O)C3=CC=C(C=C3)C(OC=3SC4=CC=CC=C4N=3)=O)=NC2=C1 DBZYLSSAYQSLSS-UHFFFAOYSA-N 0.000 description 1
- NRKJECQHRFBERQ-UHFFFAOYSA-N bis(2,4-dinitrophenyl) benzene-1,3-dicarboxylate Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=CC(C(=O)OC=2C(=CC(=CC=2)[N+]([O-])=O)[N+]([O-])=O)=C1 NRKJECQHRFBERQ-UHFFFAOYSA-N 0.000 description 1
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- HAAUMBWYMCCWFY-UHFFFAOYSA-N bis(cyanomethyl) benzene-1,4-dicarboxylate Chemical compound N#CCOC(=O)C1=CC=C(C(=O)OCC#N)C=C1 HAAUMBWYMCCWFY-UHFFFAOYSA-N 0.000 description 1
- HSLXOARVFIWOQF-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F HSLXOARVFIWOQF-UHFFFAOYSA-N 0.000 description 1
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- NQZKZGHOYUYCHU-UHFFFAOYSA-N boron;tetraethylazanium Chemical compound [B].CC[N+](CC)(CC)CC NQZKZGHOYUYCHU-UHFFFAOYSA-N 0.000 description 1
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
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- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 150000001735 carboxylic acids Chemical class 0.000 description 1
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940115457 cetyldimethylethylammonium bromide Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
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- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
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- MUYSADWCWFFZKR-UHFFFAOYSA-N cinchomeronic acid Chemical compound OC(=O)C1=CC=NC=C1C(O)=O MUYSADWCWFFZKR-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- QNUPENXMUJPLDQ-UHFFFAOYSA-M cyclopenta-1,3-diene;cyclopenta-1,3-dien-1-ylmethyl(trimethyl)azanium;iron(2+);bromide Chemical compound [Fe+2].[Br-].C=1C=C[CH-]C=1.C[N+](C)(C)CC1=CC=C[CH-]1 QNUPENXMUJPLDQ-UHFFFAOYSA-M 0.000 description 1
- JIXIGMAACRMMNM-UHFFFAOYSA-M cyclopenta-1,3-diene;cyclopenta-1,3-dien-1-ylmethyl(trimethyl)azanium;iron(2+);iodide Chemical compound [Fe+2].[I-].C=1C=C[CH-]C=1.C[N+](C)(C)C[C-]1C=CC=C1 JIXIGMAACRMMNM-UHFFFAOYSA-M 0.000 description 1
- UKJUSUHBFJPPBZ-UHFFFAOYSA-M cyclopenta-1,3-diene;cyclopenta-1,3-dien-1-ylmethyl-dodecyl-dimethylazanium;iron(2+);bromide Chemical compound [Fe+2].[Br-].C=1C=C[CH-]C=1.CCCCCCCCCCCC[N+](C)(C)CC1=CC=C[CH-]1 UKJUSUHBFJPPBZ-UHFFFAOYSA-M 0.000 description 1
- 229950000405 decamethonium Drugs 0.000 description 1
- HXWGXXDEYMNGCT-UHFFFAOYSA-M decyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)C HXWGXXDEYMNGCT-UHFFFAOYSA-M 0.000 description 1
- PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VWTINHYPRWEBQY-UHFFFAOYSA-N denatonium Chemical compound [O-]C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C[N+](CC)(CC)CC(=O)NC1=C(C)C=CC=C1C VWTINHYPRWEBQY-UHFFFAOYSA-N 0.000 description 1
- 229960001610 denatonium benzoate Drugs 0.000 description 1
- HTVKDVKYIFLRTI-UHFFFAOYSA-N dibenzofuran-1,2-dicarboxylic acid Chemical class C1=CC=C2C3=C(C(O)=O)C(C(=O)O)=CC=C3OC2=C1 HTVKDVKYIFLRTI-UHFFFAOYSA-N 0.000 description 1
- RBLSQHNMLLTHMH-UHFFFAOYSA-N dibenzofuran-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC(C(=O)O)=CC=C3OC2=C1 RBLSQHNMLLTHMH-UHFFFAOYSA-N 0.000 description 1
- VZNLJUXIEJLYJK-UHFFFAOYSA-N dibenzofuran-3,7-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C=C3OC2=C1 VZNLJUXIEJLYJK-UHFFFAOYSA-N 0.000 description 1
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- VYVZQLUQIJAVLK-UHFFFAOYSA-N dibenzothiophene-1,2-dicarboxylic acid Chemical class C1=CC=C2C3=C(C(O)=O)C(C(=O)O)=CC=C3SC2=C1 VYVZQLUQIJAVLK-UHFFFAOYSA-N 0.000 description 1
- GZLNXGRYYDFZDG-UHFFFAOYSA-N dibenzothiophene-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC(C(=O)O)=CC=C3SC2=C1 GZLNXGRYYDFZDG-UHFFFAOYSA-N 0.000 description 1
- NRNFKRFWZQQDMD-UHFFFAOYSA-M dichloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=C(Cl)Cl NRNFKRFWZQQDMD-UHFFFAOYSA-M 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- UMGXUWVIJIQANV-UHFFFAOYSA-M didecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC UMGXUWVIJIQANV-UHFFFAOYSA-M 0.000 description 1
- XRWMGCFJVKDVMD-UHFFFAOYSA-M didodecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC XRWMGCFJVKDVMD-UHFFFAOYSA-M 0.000 description 1
- CIPHWSAEUHAWLP-UHFFFAOYSA-N diethyl 1-phenylpyrrole-3,4-dicarboxylate Chemical compound C1=C(C(=O)OCC)C(C(=O)OCC)=CN1C1=CC=CC=C1 CIPHWSAEUHAWLP-UHFFFAOYSA-N 0.000 description 1
- GATNVKATWLZAGO-UHFFFAOYSA-N diethyl 1h-imidazole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=CNC(C(=O)OCC)=N1 GATNVKATWLZAGO-UHFFFAOYSA-N 0.000 description 1
- IEFLIZMMNNHRSB-UHFFFAOYSA-N diethyl 1h-indole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=CC=C2NC(C(=O)OCC)=CC2=C1 IEFLIZMMNNHRSB-UHFFFAOYSA-N 0.000 description 1
- ISQYBMUDGXFHAF-UHFFFAOYSA-N diethyl 1h-indole-2,6-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=C2NC(C(=O)OCC)=CC2=C1 ISQYBMUDGXFHAF-UHFFFAOYSA-N 0.000 description 1
- WXRSDHICEYICMV-UHFFFAOYSA-N diethyl 2,5-dibromobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC(Br)=C(C(=O)OCC)C=C1Br WXRSDHICEYICMV-UHFFFAOYSA-N 0.000 description 1
- AGTHLNPLTSEZRB-UHFFFAOYSA-N diethyl 2,5-dimethyl-1h-pyrrole-3,4-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C1C(=O)OCC AGTHLNPLTSEZRB-UHFFFAOYSA-N 0.000 description 1
- STTRQUYOVXLZBQ-UHFFFAOYSA-N diethyl 9h-carbazole-2,6-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=C2C3=CC=C(C(=O)OCC)C=C3NC2=C1 STTRQUYOVXLZBQ-UHFFFAOYSA-N 0.000 description 1
- ZHLUERBUZMUEJU-UHFFFAOYSA-N diethyl 9h-carbazole-3,6-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=C2C3=CC(C(=O)OCC)=CC=C3NC2=C1 ZHLUERBUZMUEJU-UHFFFAOYSA-N 0.000 description 1
- FKJCYDJJFIKYIK-UHFFFAOYSA-N diethyl piperidine-2,3-dicarboxylate Chemical compound CCOC(=O)C1CCCNC1C(=O)OCC FKJCYDJJFIKYIK-UHFFFAOYSA-N 0.000 description 1
- BZFYHGMPBYRDSW-UHFFFAOYSA-N diethyl piperidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1CNCC(C(=O)OCC)C1 BZFYHGMPBYRDSW-UHFFFAOYSA-N 0.000 description 1
- VIXPKJNAOIWFMW-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC VIXPKJNAOIWFMW-UHFFFAOYSA-M 0.000 description 1
- MLMNFXCRTCBAJT-UHFFFAOYSA-N dimethyl 1-methylpyrrole-2,5-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)N1C MLMNFXCRTCBAJT-UHFFFAOYSA-N 0.000 description 1
- MBPCNHQXWVYNJQ-UHFFFAOYSA-N dimethyl 1h-pyrazole-4,5-dicarboxylate Chemical compound COC(=O)C=1C=NNC=1C(=O)OC MBPCNHQXWVYNJQ-UHFFFAOYSA-N 0.000 description 1
- AKJAEUGFSVPHBU-UHFFFAOYSA-N dimethyl 1h-pyrrole-2,3-dicarboxylate Chemical compound COC(=O)C=1C=CNC=1C(=O)OC AKJAEUGFSVPHBU-UHFFFAOYSA-N 0.000 description 1
- QQPMGRCCMQUJJA-UHFFFAOYSA-N dimethyl 1h-pyrrole-2,4-dicarboxylate Chemical compound COC(=O)C1=CNC(C(=O)OC)=C1 QQPMGRCCMQUJJA-UHFFFAOYSA-N 0.000 description 1
- PMRHDIDDAMSGAA-UHFFFAOYSA-N dimethyl 1h-pyrrole-2,5-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)N1 PMRHDIDDAMSGAA-UHFFFAOYSA-N 0.000 description 1
- HEDIMOSXPHKSMJ-UHFFFAOYSA-N dimethyl 1h-pyrrole-3,4-dicarboxylate Chemical compound COC(=O)C1=CNC=C1C(=O)OC HEDIMOSXPHKSMJ-UHFFFAOYSA-N 0.000 description 1
- RDDWGNUSHLFXED-UHFFFAOYSA-N dimethyl 2,5-dichlorobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC(Cl)=C(C(=O)OC)C=C1Cl RDDWGNUSHLFXED-UHFFFAOYSA-N 0.000 description 1
- VUMPFOPENBVFOF-UHFFFAOYSA-N dimethyl 2-bromobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(Br)=C1 VUMPFOPENBVFOF-UHFFFAOYSA-N 0.000 description 1
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- ZPEBBUBSCOELHI-UHFFFAOYSA-M ethyltrimethylammonium iodide Chemical compound [I-].CC[N+](C)(C)C ZPEBBUBSCOELHI-UHFFFAOYSA-M 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
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- 229950006187 hexamethonium bromide Drugs 0.000 description 1
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- KIEOLZRKTOBVMX-UHFFFAOYSA-M hexyl-dimethyl-octylazanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(C)CCCCCC KIEOLZRKTOBVMX-UHFFFAOYSA-M 0.000 description 1
- MWSPFHZPVVWJCO-UHFFFAOYSA-M hydron;methyl(trioctyl)azanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC MWSPFHZPVVWJCO-UHFFFAOYSA-M 0.000 description 1
- ZHBDKVWQJKYIFF-UHFFFAOYSA-M hydron;tetrabutylazanium;difluoride Chemical compound F.[F-].CCCC[N+](CCCC)(CCCC)CCCC ZHBDKVWQJKYIFF-UHFFFAOYSA-M 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- CREVBWLEPKAZBH-UHFFFAOYSA-M hydron;tetraethylazanium;sulfate Chemical compound OS([O-])(=O)=O.CC[N+](CC)(CC)CC CREVBWLEPKAZBH-UHFFFAOYSA-M 0.000 description 1
- DWTYPCUOWWOADE-UHFFFAOYSA-M hydron;tetramethylazanium;sulfate Chemical compound C[N+](C)(C)C.OS([O-])(=O)=O DWTYPCUOWWOADE-UHFFFAOYSA-M 0.000 description 1
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- FZRBKIRIBLNOAM-WHVZTFIZSA-N kinoprene Chemical compound CC(C)CCCC(C)C\C=C\C(\C)=C\C(=O)OCC#C FZRBKIRIBLNOAM-WHVZTFIZSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])[H] 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
- 238000000691 measurement method Methods 0.000 description 1
- JHPHVAVFUYTVCL-UHFFFAOYSA-M methacholine chloride Chemical compound [Cl-].C[N+](C)(C)CC(C)OC(C)=O JHPHVAVFUYTVCL-UHFFFAOYSA-M 0.000 description 1
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- ROMWRJNZSHFGEK-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)benzoate Chemical compound COC(=O)CC1=CC=CC=C1C(=O)OC ROMWRJNZSHFGEK-UHFFFAOYSA-N 0.000 description 1
- HBWBVIDKBKOVEX-UHFFFAOYSA-N methyl 2-(4-methoxycarbonylpyridin-2-yl)pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(=O)OC)=C1 HBWBVIDKBKOVEX-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000000178 monomer Substances 0.000 description 1
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- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
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- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
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- IXHMHWIBCIYOAZ-UHFFFAOYSA-N styphnic acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1[N+]([O-])=O IXHMHWIBCIYOAZ-UHFFFAOYSA-N 0.000 description 1
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- HVDAPPODKZABKP-UHFFFAOYSA-M tetraethylazanium;fluoride;trihydrofluoride Chemical compound F.F.F.[F-].CC[N+](CC)(CC)CC HVDAPPODKZABKP-UHFFFAOYSA-M 0.000 description 1
- WGHUNMFFLAMBJD-UHFFFAOYSA-M tetraethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC[N+](CC)(CC)CC WGHUNMFFLAMBJD-UHFFFAOYSA-M 0.000 description 1
- PUZYNDBTWXJXKN-UHFFFAOYSA-M tetraethylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC[N+](CC)(CC)CC PUZYNDBTWXJXKN-UHFFFAOYSA-M 0.000 description 1
- YQIVQBMEBZGFBY-UHFFFAOYSA-M tetraheptylazanium;bromide Chemical compound [Br-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC YQIVQBMEBZGFBY-UHFFFAOYSA-M 0.000 description 1
- KCSOHLKZTZMKQA-UHFFFAOYSA-M tetraheptylazanium;iodide Chemical compound [I-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC KCSOHLKZTZMKQA-UHFFFAOYSA-M 0.000 description 1
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- ZCWKIFAQRXNZCH-UHFFFAOYSA-M tetramethylazanium;perchlorate Chemical compound C[N+](C)(C)C.[O-]Cl(=O)(=O)=O ZCWKIFAQRXNZCH-UHFFFAOYSA-M 0.000 description 1
- KJFVITRRNTVAPC-UHFFFAOYSA-L tetramethylazanium;sulfate Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]S([O-])(=O)=O KJFVITRRNTVAPC-UHFFFAOYSA-L 0.000 description 1
- KGPZZJZTFHCXNK-UHFFFAOYSA-M tetraoctylazanium;iodide Chemical compound [I-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC KGPZZJZTFHCXNK-UHFFFAOYSA-M 0.000 description 1
- FBLZDUAOBOMSNZ-UHFFFAOYSA-M tetrapentylazanium;iodide Chemical compound [I-].CCCCC[N+](CCCCC)(CCCCC)CCCCC FBLZDUAOBOMSNZ-UHFFFAOYSA-M 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- GKXDJYKZFZVASJ-UHFFFAOYSA-M tetrapropylazanium;iodide Chemical compound [I-].CCC[N+](CCC)(CCC)CCC GKXDJYKZFZVASJ-UHFFFAOYSA-M 0.000 description 1
- QYBBDSGVPGCWTO-UHFFFAOYSA-N thiophene-2,4-dicarboxylic acid Chemical compound OC(=O)C1=CSC(C(O)=O)=C1 QYBBDSGVPGCWTO-UHFFFAOYSA-N 0.000 description 1
- ZWWLLYJRPKYTDF-UHFFFAOYSA-N thiophene-3,4-dicarboxylic acid Chemical compound OC(=O)C1=CSC=C1C(O)=O ZWWLLYJRPKYTDF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- MJOPOXYNSSGQHL-UHFFFAOYSA-M trimethyl(2-naphthalen-2-yloxycarbonyloxyethyl)azanium;iodide Chemical compound [I-].C1=CC=CC2=CC(OC(=O)OCC[N+](C)(C)C)=CC=C21 MJOPOXYNSSGQHL-UHFFFAOYSA-M 0.000 description 1
- JMCRETWEZLOFQT-UHFFFAOYSA-M trimethyl(3-triethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCO[Si](OCC)(OCC)CCC[N+](C)(C)C JMCRETWEZLOFQT-UHFFFAOYSA-M 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- KPFRXMSETZXGKJ-UHFFFAOYSA-M trimethyl-[3-(trifluoromethyl)phenyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC(C(F)(F)F)=C1 KPFRXMSETZXGKJ-UHFFFAOYSA-M 0.000 description 1
- BFPOZPZYPNVMHU-UHFFFAOYSA-M trimethyl-[3-(trifluoromethyl)phenyl]azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC(C(F)(F)F)=C1 BFPOZPZYPNVMHU-UHFFFAOYSA-M 0.000 description 1
- VKZIUXSJJSEBAK-UHFFFAOYSA-M trimethyl-[3-(trifluoromethyl)phenyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC(C(F)(F)F)=C1 VKZIUXSJJSEBAK-UHFFFAOYSA-M 0.000 description 1
- FAPSXSAPXXJTOU-UHFFFAOYSA-L trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C FAPSXSAPXXJTOU-UHFFFAOYSA-L 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- LAGQNGWYNLUQRI-UHFFFAOYSA-N trioctylmethylammonium bis(trifluoromethylsulfonyl)imide Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC LAGQNGWYNLUQRI-UHFFFAOYSA-N 0.000 description 1
- IJGSGCGKAAXRSC-UHFFFAOYSA-M tris(2-hydroxyethyl)-methylazanium;hydroxide Chemical compound [OH-].OCC[N+](C)(CCO)CCO IJGSGCGKAAXRSC-UHFFFAOYSA-M 0.000 description 1
- 238000007039 two-step reaction 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
- C08G63/19—Hydroxy compounds containing aromatic rings
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- 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010190798A JP2011084731A (ja) | 2009-09-15 | 2010-08-27 | 芳香族ポリエステル |
| US13/496,215 US20120172570A1 (en) | 2009-09-15 | 2010-09-09 | Aromatic polyester |
| EP10817101A EP2479203A1 (en) | 2009-09-15 | 2010-09-09 | Aromatic polyester |
| PCT/JP2010/065535 WO2011033988A1 (ja) | 2009-09-15 | 2010-09-09 | 芳香族ポリエステル |
| TW099130996A TW201114803A (en) | 2009-09-15 | 2010-09-14 | Aromatic polyester |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009213757 | 2009-09-15 | ||
| JP2010190798A JP2011084731A (ja) | 2009-09-15 | 2010-08-27 | 芳香族ポリエステル |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011083713A Division JP5330447B2 (ja) | 2009-09-15 | 2011-04-05 | 芳香族ポリエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011084731A true JP2011084731A (ja) | 2011-04-28 |
| JP2011084731A5 JP2011084731A5 (enExample) | 2011-06-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010190798A Pending JP2011084731A (ja) | 2009-09-15 | 2010-08-27 | 芳香族ポリエステル |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20120172570A1 (enExample) |
| EP (1) | EP2479203A1 (enExample) |
| JP (1) | JP2011084731A (enExample) |
| TW (1) | TW201114803A (enExample) |
| WO (1) | WO2011033988A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014159562A (ja) * | 2013-01-24 | 2014-09-04 | Mitsubishi Gas Chemical Co Inc | ポリアリレート及びそれを用いた成形品 |
| WO2017078075A1 (ja) * | 2015-11-04 | 2017-05-11 | 三菱瓦斯化学株式会社 | 熱可塑性樹脂の製造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014115694A1 (ja) * | 2013-01-24 | 2014-07-31 | 三菱瓦斯化学株式会社 | ポリアリレート及びそれを用いた成形品 |
| WO2014160333A1 (en) * | 2013-03-13 | 2014-10-02 | Liquid Thermo Plastics, Inc. | Methods for preparation of polyester via base catalysis |
| JP6655543B2 (ja) * | 2014-10-03 | 2020-02-26 | 株式会社カネカ | ポリカーボネート用およびポリアリレート用流動性向上剤、ポリカーボネート樹脂組成物、ポリアリレート樹脂組成物、並びにその成形品 |
| US20200040180A1 (en) * | 2016-04-06 | 2020-02-06 | Kaneka Corporation | Polycarbonate resin composition and molded article thereof |
| EP3848415A4 (en) * | 2019-07-26 | 2021-10-06 | Kinte Materials Science and Technology Co., Ltd. | POLYESTER RESIN AND PROCESS FOR ITS MANUFACTURING, COATING AND WORKPIECE |
| CN115536825A (zh) * | 2022-11-15 | 2022-12-30 | 中国科学院长春应用化学研究所 | 一种氟催化剂催化酸酐和环氧的共聚方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4567247A (en) * | 1984-05-17 | 1986-01-28 | Celanese Corporation | Process for forming thermally stable thermotropic liquid crystalline polyesters of predetermined chain length utilizing aromatic hydroxyl monomer and/or aromatic amine monomer |
| JP2004131598A (ja) | 2002-10-10 | 2004-04-30 | Teijin Ltd | 全芳香族ポリエステルカーボネートおよびその製造方法 |
| JP4660183B2 (ja) | 2004-12-22 | 2011-03-30 | ユニチカ株式会社 | ポリアリレートの製造方法 |
| JP4452258B2 (ja) | 2006-05-30 | 2010-04-21 | 国立大学法人北海道大学 | ポリエステルからなる光ファイバー |
| JP2008214541A (ja) | 2007-03-06 | 2008-09-18 | Unitika Ltd | ポリアリレートおよびその製造方法 |
-
2010
- 2010-08-27 JP JP2010190798A patent/JP2011084731A/ja active Pending
- 2010-09-09 US US13/496,215 patent/US20120172570A1/en not_active Abandoned
- 2010-09-09 EP EP10817101A patent/EP2479203A1/en not_active Withdrawn
- 2010-09-09 WO PCT/JP2010/065535 patent/WO2011033988A1/ja not_active Ceased
- 2010-09-14 TW TW099130996A patent/TW201114803A/zh unknown
Non-Patent Citations (2)
| Title |
|---|
| JPN6010071472; 田畑昌祥,外6名: '芳香族ポリエステルによる高耐熱POFの作成' 高分子討論会予稿集 第58巻,第2号, 20090901, 第4473頁-第4474頁, 社団法人 高分子学会 * |
| JPN6010071473; 竹中康,外6名: '芳香族ポリエステルの分子設計による高耐熱透明樹脂の作成' 高分子討論会予稿集 第58巻,第2号, 20090901, 第4134頁, 社団法人 高分子学会 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014159562A (ja) * | 2013-01-24 | 2014-09-04 | Mitsubishi Gas Chemical Co Inc | ポリアリレート及びそれを用いた成形品 |
| WO2017078075A1 (ja) * | 2015-11-04 | 2017-05-11 | 三菱瓦斯化学株式会社 | 熱可塑性樹脂の製造方法 |
| US10654972B2 (en) | 2015-11-04 | 2020-05-19 | Mitsubishi Gas Chemical Company, Inc. | Method for producing thermoplastic resin |
| US10711100B2 (en) | 2015-11-04 | 2020-07-14 | Mitsubishi Gas Chemical Company, Inc. | Dihydroxy compound |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201114803A (en) | 2011-05-01 |
| EP2479203A1 (en) | 2012-07-25 |
| US20120172570A1 (en) | 2012-07-05 |
| WO2011033988A1 (ja) | 2011-03-24 |
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