JP5704736B1 - フルオレン構造を有するポリカーボネート樹脂の解重合方法 - Google Patents
フルオレン構造を有するポリカーボネート樹脂の解重合方法 Download PDFInfo
- Publication number
- JP5704736B1 JP5704736B1 JP2014196252A JP2014196252A JP5704736B1 JP 5704736 B1 JP5704736 B1 JP 5704736B1 JP 2014196252 A JP2014196252 A JP 2014196252A JP 2014196252 A JP2014196252 A JP 2014196252A JP 5704736 B1 JP5704736 B1 JP 5704736B1
- Authority
- JP
- Japan
- Prior art keywords
- fluorene
- polycarbonate resin
- group
- bis
- weight
- 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.)
- Active
Links
- 229920005668 polycarbonate resin Polymers 0.000 title claims abstract description 53
- 239000004431 polycarbonate resin Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 40
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims abstract description 15
- -1 alcohol fluorenes Chemical class 0.000 claims abstract description 43
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 14
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 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 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 22
- 239000007864 aqueous solution Substances 0.000 abstract description 7
- 239000002699 waste material Substances 0.000 abstract description 7
- 239000007858 starting material Substances 0.000 abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 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 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000013078 crystal Substances 0.000 description 20
- 238000000354 decomposition reaction Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000539 dimer Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229960002479 isosorbide Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SEAMZPPCCXCLAU-UHFFFAOYSA-N 2-[2-[9-[2-(2-hydroxyethoxy)-4-methylphenyl]fluoren-9-yl]-5-methylphenoxy]ethanol Chemical compound OCCOC1=C(C=CC(=C1)C)C1(C2=CC=CC=C2C=2C=CC=CC1=2)C1=C(C=C(C=C1)C)OCCO SEAMZPPCCXCLAU-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 238000011403 purification operation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- GPGBVWNYNZYQAK-UHFFFAOYSA-N 2-[2,6-ditert-butyl-4-[9-[3,5-ditert-butyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound OCCOC1=C(C=C(C=C1C(C)(C)C)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C(=C1)C(C)(C)C)OCCO)C(C)(C)C)C(C)(C)C GPGBVWNYNZYQAK-UHFFFAOYSA-N 0.000 description 1
- YBHWVDKCKDWQBX-UHFFFAOYSA-N 2-[2-cyclohexyl-4-[9-[3-cyclohexyl-4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound OCCOC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OCCO)=CC=2)C2CCCCC2)C=C1C1CCCCC1 YBHWVDKCKDWQBX-UHFFFAOYSA-N 0.000 description 1
- MDOBPGJMVOGJQP-UHFFFAOYSA-N 2-[4-(9h-fluoren-1-yl)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C21 MDOBPGJMVOGJQP-UHFFFAOYSA-N 0.000 description 1
- RTPBWJWNNQGUII-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-2,6-dimethylphenyl]fluoren-9-yl]-3,5-dimethylphenoxy]ethanol Chemical compound OCCOC1=CC(=C(C(=C1)C)C1(C2=CC=CC=C2C=2C=CC=CC1=2)C1=C(C=C(C=C1C)OCCO)C)C RTPBWJWNNQGUII-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
- HFKGBZQCCOAKRX-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)-3-methoxyphenyl]fluoren-9-yl]-2-methoxyphenoxy]ethanol Chemical compound OCCOC1=C(C=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC(=C(C=C1)OCCO)OC)OC HFKGBZQCCOAKRX-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
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- ZJNKCNFBTBFNMO-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)-5,7-dimethyl-1-adamantyl]phenol Chemical compound C1C(C)(C2)CC(C3)(C)CC1(C=1C=CC(O)=CC=1)CC23C1=CC=C(O)C=C1 ZJNKCNFBTBFNMO-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-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
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- PCLSSBBQFFDGBN-UHFFFAOYSA-M C(O)([O-])=O.[Na+].C(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O Chemical compound C(O)([O-])=O.[Na+].C(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O PCLSSBBQFFDGBN-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- JMMSLMMJRMCXPW-UHFFFAOYSA-N OC.OC.C1CC2CCC1C2 Chemical compound OC.OC.C1CC2CCC1C2 JMMSLMMJRMCXPW-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- RVIZJROSQMQZCG-UHFFFAOYSA-N adamantane-1,2-diol Chemical compound C1C(C2)CC3CC1C(O)C2(O)C3 RVIZJROSQMQZCG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000012691 depolymerization reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000012266 salt solution Substances 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014196252A JP5704736B1 (ja) | 2013-10-07 | 2014-09-26 | フルオレン構造を有するポリカーボネート樹脂の解重合方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013210052 | 2013-10-07 | ||
| JP2013210052 | 2013-10-07 | ||
| JP2014196252A JP5704736B1 (ja) | 2013-10-07 | 2014-09-26 | フルオレン構造を有するポリカーボネート樹脂の解重合方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP5704736B1 true JP5704736B1 (ja) | 2015-04-22 |
| JP2015096596A JP2015096596A (ja) | 2015-05-21 |
Family
ID=52812948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014196252A Active JP5704736B1 (ja) | 2013-10-07 | 2014-09-26 | フルオレン構造を有するポリカーボネート樹脂の解重合方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP5704736B1 (zh) |
| KR (1) | KR20160067877A (zh) |
| CN (1) | CN105593199B (zh) |
| TW (1) | TWI582139B (zh) |
| WO (1) | WO2015053130A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015196676A (ja) * | 2014-04-03 | 2015-11-09 | 田岡化学工業株式会社 | フルオレン構造を有するポリエステル樹脂からビスフェノールフルオレン類を回収する方法 |
| JP2016204265A (ja) * | 2015-04-15 | 2016-12-08 | 帝人株式会社 | モノマーの製造方法 |
| JP2016204271A (ja) * | 2015-04-16 | 2016-12-08 | 田岡化学工業株式会社 | フルオレン構造を含む樹脂からビスフェノールフルオレン類を回収する方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5879456B1 (ja) * | 2015-11-20 | 2016-03-08 | 帝人株式会社 | モノマーの製造方法 |
| CN106432797A (zh) * | 2016-08-08 | 2017-02-22 | 桂林市春晓环保科技有限公司 | 一种废旧交联聚碳酸酯的回收工艺 |
| WO2019116798A1 (ja) * | 2017-12-12 | 2019-06-20 | 田岡化学工業株式会社 | フルオレン骨格を有する（メタ）アクリレート化合物 |
| WO2021132419A1 (ja) | 2019-12-27 | 2021-07-01 | 三菱瓦斯化学株式会社 | 再生樹脂の製造方法 |
| WO2024014448A1 (ja) * | 2022-07-15 | 2024-01-18 | 大阪ガスケミカル株式会社 | フルオレン骨格を有する樹脂の解重合法、その生成物および用途 |
| JP7393592B1 (ja) | 2022-07-15 | 2023-12-06 | 大阪ガスケミカル株式会社 | フルオレン骨格を有する樹脂の解重合法、その生成物および用途 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08220781A (ja) * | 1995-02-16 | 1996-08-30 | Matsushita Electric Ind Co Ltd | 電荷輸送層用塗料と、それを用いて得られる電子写真用感光体及びその製造方法 |
| JPH10259151A (ja) * | 1997-03-18 | 1998-09-29 | Res Inst For Prod Dev | ポリカ−ボネ−トより炭酸ジアルキルとビスフェノ−ルとを得る方法 |
| JP2003301098A (ja) * | 2002-04-09 | 2003-10-21 | Teijin Chem Ltd | 芳香族ポリカーボネート樹脂組成物 |
| JP2008291052A (ja) * | 2007-05-22 | 2008-12-04 | Teijin Chem Ltd | 精製した芳香族ジヒドロキシ化合物のアルカリ金属水酸化物水溶液を回収する方法 |
| JP2009173844A (ja) * | 2008-01-28 | 2009-08-06 | Osaka Gas Co Ltd | フルオレン系ポリエステルオリゴマー及びその製造方法 |
| JP2011195514A (ja) * | 2010-03-19 | 2011-10-06 | Teijin Chem Ltd | 芳香族ジヒドロキシ化合物のアルカリ金属水酸化物水溶液の回収方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4016536B1 (zh) | 1961-08-24 | 1965-07-29 | ||
| JP2005126358A (ja) * | 2003-10-23 | 2005-05-19 | Teijin Chem Ltd | 廃芳香族ポリカーボネートから芳香族ジヒドロキシ化合物金属塩水溶液を得る方法 |
| CN101407450A (zh) * | 2008-05-14 | 2009-04-15 | 青岛科技大学 | 废聚碳酸酯材料化学回收方法 |
| JP5230015B2 (ja) * | 2009-07-27 | 2013-07-10 | 田岡化学工業株式会社 | フルオレン誘導体の製造法 |
-
2014
- 2014-09-26 JP JP2014196252A patent/JP5704736B1/ja active Active
- 2014-09-30 KR KR1020167010756A patent/KR20160067877A/ko not_active Application Discontinuation
- 2014-09-30 CN CN201480054873.9A patent/CN105593199B/zh active Active
- 2014-09-30 WO PCT/JP2014/076051 patent/WO2015053130A1/ja active Application Filing
- 2014-10-03 TW TW103134570A patent/TWI582139B/zh active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08220781A (ja) * | 1995-02-16 | 1996-08-30 | Matsushita Electric Ind Co Ltd | 電荷輸送層用塗料と、それを用いて得られる電子写真用感光体及びその製造方法 |
| JPH10259151A (ja) * | 1997-03-18 | 1998-09-29 | Res Inst For Prod Dev | ポリカ−ボネ−トより炭酸ジアルキルとビスフェノ−ルとを得る方法 |
| JP2003301098A (ja) * | 2002-04-09 | 2003-10-21 | Teijin Chem Ltd | 芳香族ポリカーボネート樹脂組成物 |
| JP2008291052A (ja) * | 2007-05-22 | 2008-12-04 | Teijin Chem Ltd | 精製した芳香族ジヒドロキシ化合物のアルカリ金属水酸化物水溶液を回収する方法 |
| JP2009173844A (ja) * | 2008-01-28 | 2009-08-06 | Osaka Gas Co Ltd | フルオレン系ポリエステルオリゴマー及びその製造方法 |
| JP2011195514A (ja) * | 2010-03-19 | 2011-10-06 | Teijin Chem Ltd | 芳香族ジヒドロキシ化合物のアルカリ金属水酸化物水溶液の回収方法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015196676A (ja) * | 2014-04-03 | 2015-11-09 | 田岡化学工業株式会社 | フルオレン構造を有するポリエステル樹脂からビスフェノールフルオレン類を回収する方法 |
| JP2016204265A (ja) * | 2015-04-15 | 2016-12-08 | 帝人株式会社 | モノマーの製造方法 |
| JP2016204271A (ja) * | 2015-04-16 | 2016-12-08 | 田岡化学工業株式会社 | フルオレン構造を含む樹脂からビスフェノールフルオレン類を回収する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105593199A (zh) | 2016-05-18 |
| KR20160067877A (ko) | 2016-06-14 |
| CN105593199B (zh) | 2017-07-28 |
| TW201518347A (zh) | 2015-05-16 |
| WO2015053130A1 (ja) | 2015-04-16 |
| JP2015096596A (ja) | 2015-05-21 |
| TWI582139B (zh) | 2017-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5704736B1 (ja) | フルオレン構造を有するポリカーボネート樹脂の解重合方法 | |
| JP5721300B1 (ja) | フルオレン構造を含む樹脂からビスフェノールフルオレン類を回収する方法 | |
| JP6210555B2 (ja) | フルオレン構造を有するポリエステル樹脂からビスフェノールフルオレン類を回収する方法 | |
| KR20140131511A (ko) | ９，９-비스(4-(2-히드록시에톡시)페닐)플루오렌의 제조방법, 그의 결정체 및 그의 결정체의 제조방법 | |
| JP6372857B2 (ja) | フルオレン構造を含む樹脂からビスフェノールフルオレン類を回収する方法 | |
| JP2022085144A (ja) | ビスフェノールの製造方法および再生ポリカーボネート樹脂の製造方法 | |
| JP5879456B1 (ja) | モノマーの製造方法 | |
| US8202960B1 (en) | Bisphenol compounds and methods of making | |
| JP2013216582A (ja) | ビスフェノール類のビスヒドロキシエチルエーテルの製造方法 | |
| JP6016303B2 (ja) | フルオレン骨格を有するキサンテン化合物の製造方法 | |
| JP2010024248A (ja) | フルオレン誘導体 | |
| JP2016138071A (ja) | ビスフェノール類ビスヒドロキシエチルエーテルの製造方法 | |
| JP6442352B2 (ja) | モノマーの製造方法 | |
| JP7524721B2 (ja) | ビスフェノールの製造方法および再生ポリカーボネート樹脂の製造方法 | |
| JP2024032229A (ja) | ビスフェノールの製造方法及び再生ポリカーボネート樹脂の製造方法 | |
| JPWO2016002607A1 (ja) | 新規なビス（ヒドロキシアルコキシフェニル）ジフェニルメタン類 | |
| JP4272123B2 (ja) | 廃芳香族ポリカーボネートから精製された芳香族ジヒドロキシ化合物のアルカリ水溶液を得る方法 | |
| JP2011046623A (ja) | 新規なエポキシ化合物 | |
| WO2024014448A1 (ja) | フルオレン骨格を有する樹脂の解重合法、その生成物および用途 | |
| JP7393592B1 (ja) | フルオレン骨格を有する樹脂の解重合法、その生成物および用途 | |
| JP2023108258A (ja) | 芳香族ジオール類および脂肪族ジオール類の回収方法 | |
| US20240228736A1 (en) | A Process for Preparing a Monoester of Terephthalic Acid and Its Derivatives | |
| JP2008037827A (ja) | ケタールビスフェノール類の製造方法 | |
| JPWO2004035513A1 (ja) | 新規な４，４’−ジヒドロキシフェニル−ビシクロヘキセン類 | |
| JP2022159218A (ja) | ビスナフトエ酸誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150126 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20150126 |
|
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20150217 |
|
| 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: 20150220 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150220 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5704736 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |