JP6328200B2 - 置換フェニレン芳香族ジエステル - Google Patents
置換フェニレン芳香族ジエステル Download PDFInfo
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- JP6328200B2 JP6328200B2 JP2016185189A JP2016185189A JP6328200B2 JP 6328200 B2 JP6328200 B2 JP 6328200B2 JP 2016185189 A JP2016185189 A JP 2016185189A JP 2016185189 A JP2016185189 A JP 2016185189A JP 6328200 B2 JP6328200 B2 JP 6328200B2
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- hydrogen
- phenylene
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- -1 phenylene aromatic diesters Chemical class 0.000 title claims description 179
- 125000004432 carbon atom Chemical group C* 0.000 claims description 153
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 143
- 229910052739 hydrogen Inorganic materials 0.000 claims description 132
- 239000001257 hydrogen Substances 0.000 claims description 129
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical class 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052710 silicon Inorganic materials 0.000 claims description 46
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 239000010703 silicon Substances 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 36
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 33
- LVTPRIAGCBEGPW-UHFFFAOYSA-N (2-benzoyloxyphenyl) benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1OC(=O)C1=CC=CC=C1 LVTPRIAGCBEGPW-UHFFFAOYSA-N 0.000 description 27
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 21
- 150000005690 diesters Chemical class 0.000 description 18
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 13
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 6
- WYQIVZKSGGKUAX-UHFFFAOYSA-N phenanthrene-3-carboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)=CC=C3C=CC2=C1 WYQIVZKSGGKUAX-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229940050390 benzoate Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
- RZRJYURCNBXIST-UHFFFAOYSA-N 2-anthroic acid Chemical compound C1=CC=CC2=CC3=CC(C(=O)O)=CC=C3C=C21 RZRJYURCNBXIST-UHFFFAOYSA-N 0.000 description 4
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 4
- QQWGRZNQKYASSB-UHFFFAOYSA-N 6h-phenalene-2-carboxylic acid Chemical compound C1=CC2=CC(C(=O)O)=CC(C=CC3)=C2C3=C1 QQWGRZNQKYASSB-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- 0 Cc1c(*)c(*)c(*)c(C(Oc2cc(*)c(*)c(*)c2OC(c2c(*)c(*)c(*)c(*)c2*)=O)=O)c1O* Chemical compound Cc1c(*)c(*)c(*)c(C(Oc2cc(*)c(*)c(*)c2OC(c2c(*)c(*)c(*)c(*)c2*)=O)=O)c1O* 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- QTWYUOSZMIWHJV-UHFFFAOYSA-N phenanthrene-2-carboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C=C3C=CC2=C1 QTWYUOSZMIWHJV-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 3
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- OKDZLBJOKANSEH-UHFFFAOYSA-N (2-benzoyloxy-3,4,6-tripropylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=C(CCC)C(CCC)=CC(CCC)=C1OC(=O)C1=CC=CC=C1 OKDZLBJOKANSEH-UHFFFAOYSA-N 0.000 description 1
- NIZOHMCPEHFMFD-UHFFFAOYSA-N (2-benzoyloxy-3,4-dibutyl-6-ethylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=C(CCCC)C(CCCC)=CC(CC)=C1OC(=O)C1=CC=CC=C1 NIZOHMCPEHFMFD-UHFFFAOYSA-N 0.000 description 1
- AKLFFKAVQANIOU-UHFFFAOYSA-N (2-benzoyloxy-3,4-dicyclohexyl-6-ethylphenyl) benzoate Chemical compound C1CCCCC1C=1C(OC(=O)C=2C=CC=CC=2)=C(OC(=O)C=2C=CC=CC=2)C(CC)=CC=1C1CCCCC1 AKLFFKAVQANIOU-UHFFFAOYSA-N 0.000 description 1
- KBBSUXUOCLNPJP-UHFFFAOYSA-N (2-benzoyloxy-3,4-dicyclopentyl-6-methylphenyl) benzoate Chemical compound C1CCCC1C=1C(OC(=O)C=2C=CC=CC=2)=C(OC(=O)C=2C=CC=CC=2)C(C)=CC=1C1CCCC1 KBBSUXUOCLNPJP-UHFFFAOYSA-N 0.000 description 1
- HQPZVXOHEMNZEF-UHFFFAOYSA-N (2-benzoyloxy-3,4-dicyclopentyl-6-propylphenyl) benzoate Chemical compound C1CCCC1C=1C(OC(=O)C=2C=CC=CC=2)=C(OC(=O)C=2C=CC=CC=2)C(CCC)=CC=1C1CCCC1 HQPZVXOHEMNZEF-UHFFFAOYSA-N 0.000 description 1
- QCUQKNCNDADKKT-UHFFFAOYSA-N (2-benzoyloxy-3,4-diethyl-6-methylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=C(CC)C(CC)=CC(C)=C1OC(=O)C1=CC=CC=C1 QCUQKNCNDADKKT-UHFFFAOYSA-N 0.000 description 1
- AZZQVPURFIFMQR-UHFFFAOYSA-N (2-benzoyloxy-3,4-diethyl-6-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCC)=CC(CC)=C(CC)C=1OC(=O)C1=CC=CC=C1 AZZQVPURFIFMQR-UHFFFAOYSA-N 0.000 description 1
- BFNHHJVSSBUOIN-UHFFFAOYSA-N (2-benzoyloxy-3,5-dibutylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC(CCCC)=CC(CCCC)=C1OC(=O)C1=CC=CC=C1 BFNHHJVSSBUOIN-UHFFFAOYSA-N 0.000 description 1
- ZZLPIJBFQVIMOW-UHFFFAOYSA-N (2-benzoyloxy-3,5-dicyclopentylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1OC(=O)C=2C=CC=CC=2)=CC(C2CCCC2)=CC=1C1CCCC1 ZZLPIJBFQVIMOW-UHFFFAOYSA-N 0.000 description 1
- DWFZWUGWRJQMCX-UHFFFAOYSA-N (2-benzoyloxy-3,6-dibutylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC=C(CCCC)C=1OC(=O)C1=CC=CC=C1 DWFZWUGWRJQMCX-UHFFFAOYSA-N 0.000 description 1
- REDOAGSTSMHFLV-UHFFFAOYSA-N (2-benzoyloxy-3,6-dicyclopentylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1OC(=O)C=2C=CC=CC=2)=C(C2CCCC2)C=CC=1C1CCCC1 REDOAGSTSMHFLV-UHFFFAOYSA-N 0.000 description 1
- YUTUJILRZFHDAW-UHFFFAOYSA-N (2-benzoyloxy-3,6-diethyl-4-propan-2-ylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CC)=CC(C(C)C)=C(CC)C=1OC(=O)C1=CC=CC=C1 YUTUJILRZFHDAW-UHFFFAOYSA-N 0.000 description 1
- JDSLBYQSGQTOGS-UHFFFAOYSA-N (2-benzoyloxy-3,6-dimethyl-4-propan-2-ylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=C(C)C(C(C)C)=CC(C)=C1OC(=O)C1=CC=CC=C1 JDSLBYQSGQTOGS-UHFFFAOYSA-N 0.000 description 1
- ZFEOFDLIMRPKPL-UHFFFAOYSA-N (2-benzoyloxy-3,6-dimethyl-4-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=C(C)C(CCC)=CC(C)=C1OC(=O)C1=CC=CC=C1 ZFEOFDLIMRPKPL-UHFFFAOYSA-N 0.000 description 1
- MEZBWDFLLDWOLU-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-4,6-diethylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(CC)C=C(CC)C=1OC(=O)C1=CC=CC=C1 MEZBWDFLLDWOLU-UHFFFAOYSA-N 0.000 description 1
- VELOGQGYKZDGMH-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-4,6-dipropylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(CCC)C=C(CCC)C=1OC(=O)C1=CC=CC=C1 VELOGQGYKZDGMH-UHFFFAOYSA-N 0.000 description 1
- SWRWWAOUBDIXPL-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-4-cyclohexyl-6-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(C2CCCCC2)C=C(CCC)C=1OC(=O)C1=CC=CC=C1 SWRWWAOUBDIXPL-UHFFFAOYSA-N 0.000 description 1
- ZYJSEMOZCSJEJL-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-4-cyclopentyl-6-methylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(C2CCCC2)C=C(C)C=1OC(=O)C1=CC=CC=C1 ZYJSEMOZCSJEJL-UHFFFAOYSA-N 0.000 description 1
- FCGGQUQGMGBUEH-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-4-propan-2-yl-6-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(C(C)C)C=C(CCC)C=1OC(=O)C1=CC=CC=C1 FCGGQUQGMGBUEH-UHFFFAOYSA-N 0.000 description 1
- CIYLLYUXPCSVSD-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-cyclopentylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(C2CCCC2)=CC=1OC(=O)C1=CC=CC=C1 CIYLLYUXPCSVSD-UHFFFAOYSA-N 0.000 description 1
- LUDRDOVGJTVRER-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-ethylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(CC)=CC=1OC(=O)C1=CC=CC=C1 LUDRDOVGJTVRER-UHFFFAOYSA-N 0.000 description 1
- QUPAUVZKXPAWFZ-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-methylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(C)=CC=1OC(=O)C1=CC=CC=C1 QUPAUVZKXPAWFZ-UHFFFAOYSA-N 0.000 description 1
- IBWLVEOIWDOZGN-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-phenylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(C=2C=CC=CC=2)=CC=1OC(=O)C1=CC=CC=C1 IBWLVEOIWDOZGN-UHFFFAOYSA-N 0.000 description 1
- ZBIPVYLBUNDNEW-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-propan-2-ylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(C(C)C)=CC=1OC(=O)C1=CC=CC=C1 ZBIPVYLBUNDNEW-UHFFFAOYSA-N 0.000 description 1
- LMHPMNWVYHTCJS-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(CCC)=CC=1OC(=O)C1=CC=CC=C1 LMHPMNWVYHTCJS-UHFFFAOYSA-N 0.000 description 1
- UATQJAGZNLCMBC-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-5-tert-butylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=CC(C(C)(C)C)=CC=1OC(=O)C1=CC=CC=C1 UATQJAGZNLCMBC-UHFFFAOYSA-N 0.000 description 1
- MSLUKRBGBXPVRP-UHFFFAOYSA-N (2-benzoyloxy-3-butyl-6-ethyl-4-propylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC=1C(CCCC)=C(CCC)C=C(CC)C=1OC(=O)C1=CC=CC=C1 MSLUKRBGBXPVRP-UHFFFAOYSA-N 0.000 description 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HURSIASBWGCKKE-UHFFFAOYSA-N naphthalene naphthalene-1-carboxylic acid Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)O.C1=CC=CC2=CC=CC=C12 HURSIASBWGCKKE-UHFFFAOYSA-N 0.000 description 1
- DPSWVNZELZWTKT-UHFFFAOYSA-N naphthalene-1-carbonyl bromide Chemical compound C1=CC=C2C(C(=O)Br)=CC=CC2=C1 DPSWVNZELZWTKT-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- MQZJWWZUARZRCU-UHFFFAOYSA-N naphthalene-1-carbonyl fluoride Chemical compound C1=CC=C2C(C(=O)F)=CC=CC2=C1 MQZJWWZUARZRCU-UHFFFAOYSA-N 0.000 description 1
- LFDXHVHUFHJSMP-UHFFFAOYSA-N naphthalene-1-carbonyl iodide Chemical compound C1=CC=C2C(C(=O)I)=CC=CC2=C1 LFDXHVHUFHJSMP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- NPZDDYUXAQBRCJ-UHFFFAOYSA-M potassium;naphthalene-2-carboxylate Chemical compound [K+].C1=CC=CC2=CC(C(=O)[O-])=CC=C21 NPZDDYUXAQBRCJ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- WUJXROKYJRAVIO-UHFFFAOYSA-M sodium;naphthalene-2-carboxylate Chemical compound [Na+].C1=CC=CC2=CC(C(=O)[O-])=CC=C21 WUJXROKYJRAVIO-UHFFFAOYSA-M 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/12—Melt flow index or melt flow ratio
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
本出願は、2008年12月31日出願の米国仮特許出願第61/141,959号の優先権を主張し、その全内容が参照により本明細書中に組み込まれる。
、ジエステルを製造するための方法は、置換された芳香族ジオールを、反応条件下、置換された芳香族アシルハライドと反応させることを含む。反応により、R1〜R14が同じであるか、又は異なる構造(II)の置換された1,2−フェニレンジベンゾアートが形成される。R1〜R4の少なくとも1つ、R5〜R9の少なくとも1つ、及び、R10〜R14の少なくとも1つが、1個〜20個の炭素原子を有する非置換のヒドロカルビル基、1個〜20個の炭素原子を有する置換されたヒドロカルビル基、1個〜20個の炭素原子を有するアルコキシ基、ハロゲン及びそれらの組合せから選択される。
換のヒドロカルビル基、ハロヒドロカルビル基、ハロゲン、ケイ素含有ヒドロカルビル基及びそれらの組合せから選択される。R5〜R6、R8〜R11及びR13〜R14の少なくとも1つが、C1〜C6アルキル基、ハロゲン及びそれらの組合せから選択される。
ド:安息香酸、1−ナフトエ酸、2−ナフトエ酸、6H−フェナレン−2−カルボン酸、アントラセン−2−カルボン酸、フェナントレン−2−カルボン酸及び/又はフェナントレン−3−カルボン酸)が挙げられる。好適な芳香族アシルハライドのさらなる限定されない例としては、ベンゾイルクロリド、ベンゾイルフルオリド、ベンゾイルブロミド及びベンゾイルヨージド、ナフトイルクロリド、ナフトイルフルオリド、ナフトイルブロミド及びナフトイルヨージド、並びに、前記芳香族アシルハライドの任意の組合せが挙げられる。
それ以外の置換基のそれぞれが水素である。R5〜R14のそれぞれが水素である。別の実施形態において、水素でない、R1〜R4のそれぞれの基が、2個〜20個の炭素原子を有するアルキル基である。
方法であって、置換された芳香族ジオールを、反応条件下、置換された芳香族アシルハライドと反応させ、下記の構造(II)の置換された1,2−フェニレンジベンゾアートを形成することを含む方法が提供される:
るアルキル基である。
示す:R5がR10と対になり/対形成し、R6がR11と対になり/対形成し、R7がR12と対になり/対形成し、R8がR13と対になり/対形成し、R9がR14と対になり/対形成する。
1,2−フェニレンジエステルを含有する混合物が形成される。混合物は分離されてもよく、又は分離されなくてもよく、そして、触媒合成手順において使用することができる。
基でなく、且つ/又は、R7が、R12と同じ置換基でない置換された1,2−フェニレンジベンゾアートを得ることができる。
異なり、それぞれが、水素、1個〜20個の炭素原子を有する非置換のヒドロカルビル基、1個〜20個の炭素原子を有する置換されたヒドロカルビル基、1個〜20個の炭素原子を有するアルコキシ基、ハロゲン及びそれらの組合せから選択される。さらなる実施形態において、芳香族アシルハライドは置換され、R5〜R14の少なくとも1つが、1個〜20個の炭素原子を有する非置換のヒドロカルビル基、1個〜20個の炭素原子を有する置換されたヒドロカルビル基、1個〜20個の炭素原子を有するアルコキシ基、ハロゲン及びそれらの組合せから選択される。
1個〜20個の炭素原子を有する非置換のヒドロカルビル基、1個〜20個の炭素原子を有する置換されたヒドロカルビル基、1個〜20個の炭素原子を有するアルコキシ基、ハロゲン及びそれらの組合せから選択される。
ルキル基及びハロゲンから選択される。好適なC1〜C8アルキル基の限定されない例としては、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、i−ブチル及びt−ブチル、n−ペンチル、i−ペンチル、ネオペンチル、t−ペンチル、n−ヘキシル、並びに、2,4,4−トリメチルペンタン−2−イルが挙げられる。さらなる実施形態において、R5〜R14の少なくとも1つがC1〜C8アルキル基又はハロゲンである。
9、R10、R11、R13及びR14のそれぞれが水素である。
が水素である。
フェニレンジベンゾアート;5−イソプロピル−3−メチル−1,2−フェニレンジベンゾアート;5−ブチル−3−メチル−1,2−フェニレンジベンゾアート;5−イソブチル−3−メチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−メチル−1,2−フェニレンジベンゾアート;5−シクロペンチル−3−メチル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−3−メチル−1,2−フェニレンジベンゾアート;3−メチル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−メチルビフェニル−3,4−ジイルジベンゾアート;3−エチル−5−メチル−1,2−フェニレンジベンゾアート;3,5−ジエチル−1,2−フェニレンジベンゾアート;3−エチル−5−プロピル−1,2−フェニレンジベンゾアート;3−エチル−5−イソプロピル−1,2−フェニレンジベンゾアート;5−ブチル−3−エチル−1,2−フェニレンジベンゾアート;3−エチル−5−イソブチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−エチル−1,2−フェニレンジベンゾアート;5−シクロペンチル−3−エチル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−3−エチル−1,2−フェニレンジベンゾアート;3−エチル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−エチルビフェニル−3,4−ジイルジベンゾアート;5−メチル−3−プロピル−1,2−フェニレンジベンゾアート;5−エチル−3−プロピル−1,2−フェニレンジベンゾアート;3,5−ジプロピル−1,2−フェニレンジベンゾアート;5−イソプロピル−3−プロピル−1,2−フェニレンジベンゾアート;5−ブチル−3−プロピル−1,2−フェニレンジベンゾアート;5−イソブチル−3−プロピル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−プロピル−1,2−フェニレンジベンゾアート;5−シクロペンチル−3−プロピル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−3−プロピル−1,2−フェニレンジベンゾアート;3−プロピル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−プロピルビフェニル−3,4−ジイルジベンゾアート;3−イソプロピル−5−メチル−1,2−フェニレンジベンゾアート;5−エチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−イソプロピル−5−プロピル−1,2−フェニレンジベンゾアート;3,5−ジイソプロピルプロピル−1,2−フェニレンジベンゾアート;及び/又は5−ブチル−3−イソプロピル−1,2−フェニレンジベンゾアート;5−イソブチル−3−イソプロピル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−イソプロピル−1,2−フェニレンジベンゾアート;5−シクロペンチル−3−イソプロピル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−イソプロピル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−イソプロピルビフェニル−3,4−ジイルジベンゾアート;3−ブチル−5−メチル−1,2−フェニレンジベンゾアート;3−ブチル−5−エチル−1,2−フェニレンジベンゾアート;3−ブチル−5−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−5−イソプロピル−1,2−フェニレンジベンゾアート;3,5−ジブチル−1,2−フェニレンジベンゾアート;3−ブチル−5−イソブチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−ブチル−1,2−フェニレンジベンゾアート;3−ブチル−5−シクロペンチル−1,2−フェニレンジベンゾアート;3−ブチル−5−シクロヘキシル−1,2−フェニレンジベンゾアート;3−ブチル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−ブチルビフェニル−3,4−ジイルジベンゾアート;3−イソブチル−5−メチル−1,2−フェニレンジベンゾアート;5−エチル−3−イソブチル−1,2−フェニレンジベンゾアート;3−イソブチル−5−プロピル−1,2−フェニレンジベンゾアート;3−イソブチル−5−イソプロピル−1,2−フェニレンジベンゾアート;5−ブチル−3−イソブチル−1,2−フェニレンジベンゾアート;3,5−ジイソブチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−イソブチル−1,2−フェニレンジベンゾアート;5−シクロペンチル−3−イソブチル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−
3−イソブチル−1,2−フェニレンジベンゾアート;3−イソブチル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−イソブチルビフェニル−3,4−ジイルジベンゾアート;3−シクロペンチル−5−メチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−5−エチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−5−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−5−イソプロピル−1,2−フェニレンジベンゾアート;5−ブチル−3−シクロペンチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−5−イソブチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−シクロペンチル−1,2−フェニレンジベンゾアート;3,5−ジシクロペンチル−1,2−フェニレンジベンゾアート;5−シクロヘキシル−3−シクロペンチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−シクロペンチルビフェニル−3,4−ジイルジベンゾアート;3−シクロヘキシル−5−メチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−エチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−イソプロピル−1,2−フェニレンジベンゾアート;5−ブチル−3−シクロヘキシル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−イソブチル−1,2−フェニレンジベンゾアート;5−tert−ブチル−3−シクロヘキシル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−シクロペンチル−1,2−フェニレンジベンゾアート;3,5−ジシクロヘキシル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−5−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;5−シクロヘキシルビフェニル−3,4−ジイルジベンゾアート;5−メチルビフェニル−2,3−ジイルジベンゾアート;5−エチルビフェニル−2,3−ジイルジベンゾアート;5−プロピルビフェニル−2,3−ジイルジベンゾアート;5−イソプロピルビフェニル−2,3−ジイルジベンゾアート;5−ブチルビフェニル−2,3−ジイルジベンゾアート;5−イソブチルビフェニル−2,3−ジイルジベンゾアート;5−tert−ブチルビフェニル−2,3−ジイルジベンゾアート;5−シクロペンチルビフェニル−2,3−ジイルジベンゾアート;5−シクロヘキシルビフェニル−2,3−ジイルジベンゾアート;5−(2,4,4−トリメチルペンタン−2−イル)ビフェニル−2,3−ジイルジベンゾアート;及び/又は3,5−ジフェニル−1,2−フェニレンジベンゾアート。
アルキル基であり、且つ、R1〜R4のそれ以外のR基のそれぞれが水素である。R5〜R14のそれぞれが、水素、1個〜20個の炭素原子を有する非置換のヒドロカルビル基、ハロヒドロカルビル基、ハロゲン、ケイ素含有ヒドロカルビル基及びそれらの組合せから選択される。R2、R7及びR12のそれぞれが同時にt−ブチル基ではない。
基であるとき、R7及びR12はt−ブチル基ではない(又は、R7がt−ブチル基であるとき、R2及びR12はt−ブチル基ではない;又は、R12がt−ブチル基であるとき、R2及びR7はt−ブチル基ではない)。
及びそれらの組合せから選択される。
して含む。R1〜R14の他のR基はそれぞれが水素である。
1,2−フェニレンジベンゾアート;3−エチル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;6−メチル−3,4−ジプロピル−1,2−フェニレンジベンゾアート;3−イソプロピル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;3−イソブチル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−6−メチル−4−プロピル−1,2−フェニレンジベンゾアート;4−メチル−6−プロピルビフェニル−2,3−ジイルジベンゾアート;4−イソプロピル−3,6−ジメチル−1,2−フェニレンジベンゾアート;3−エチル−4−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;4−イソプロピル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;3,4−ジイソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−ブチル−4−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−イソブチル−4−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;6−イソプロピル−4−メチルビフェニル−2,3−ジイルジベンゾアート;4−ブチル−3,6−ジメチル−1,2−フェニレンジベンゾアート;4−ブチル−3−エチル−6−メチル−1,2−フェニレンジベンゾアート;4−ブチル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3,4−ジブチル−6−メチル−1,2−フェニレンジベンゾアート;4−ブチル−3−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロペンチル−6−メチル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロヘキシル−6−メチル−1,2−フェニレンジベンゾアート;4−ブチル−6−メチル−3−(2,4,4−トリメチルペンタン−2−イル)−1,2−フェニレンジベンゾアート;6−ブチル−4−メチルビフェニル−2,3−ジイルジベンゾアート;4−イソブチル−3,6−ジメチル−1,2−フェニレンジベンゾアート;3−エチル−4−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;4−イソブチル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;4−イソブチル−3−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−ブチル−4−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;3,4−ジイソブチル−6−メチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;6−イソブチル−4−メチルビフェニル−2,3−ジイルジベンゾアート;4−tert−ブチル−3,6−ジメチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−エチル−6−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−ブチル−6−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロペンチル−6−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロヘキシル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3,6−ジメチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−エチル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロペンチル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;3,4−ジシクロペンチル−6−メチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−シクロペンチル−6−メチル−1,2−
フェニレンジベンゾアート;6−シクロペンチル−4−メチルビフェニル−2,3−ジイルジベンゾアート;4−シクロヘキシル−3,6−ジメチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−エチル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−6−メチル−3−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−イソプロピル−6−メチル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロヘキシル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−イソブチル−6−メチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−シクロペンチル−6−メチル−1,2−フェニレンジベンゾアート;3,4−ジシクロヘキシル−6−メチル−1,2−フェニレンジベンゾアート;6−シクロヘキシル−4−メチルビフェニル−2,3−ジイルジベンゾアート;2,5−ジメチルビフェニル−3,4−ジイルジベンゾアート;2−エチル−5−メチルビフェニル−3,4−ジイルジベンゾアート;5−メチル−2−プロピルビフェニル−3,4−ジイルジベンゾアート;2−イソプロピル−5−メチルビフェニル−3,4−ジイルジベンゾアート;2−ブチル−5−メチルビフェニル−3,4−ジイルジベンゾアート;2−イソブチル−5−メチルビフェニル−3,4−ジイルジベンゾアート;2−シクロペンチル−5−メチルビフェニル−3,4−ジイルジベンゾアート;2−シクロヘキシル−5−メチルビフェニル−3,4−ジイルジベンゾアート;3,4−フェニル−6−メチル−1,2−フェニレンジベンゾアート;6−エチル−3,4−ジメチル−1,2−フェニレンジベンゾアート;3,6−ジエチル−4−メチル−1,2−フェニレンジベンゾアート;6−エチル−4−メチル−3−プロピル−1,2−フェニレンジベンゾアート;6−エチル−3−イソプロピル−4−メチル−1,2−フェニレンジベンゾアート;3−ブチル−6−エチル−4−メチル−1,2−フェニレンジベンゾアート;6−エチル−3−イソブチル−4−メチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−6−エチル−4−メチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−6−エチル−4−メチル−1,2−フェニレンジベンゾアート;4−エチル−6−メチルビフェニル−2,3−ジイルジベンゾアート;4,6−ジエチル−3−メチル−1,2−フェニレンジベンゾアート;3,4,6−トリエチル−1,2−フェニレンジベンゾアート;4,6−ジエチル−3−プロピル−1,2−フェニレンジベンゾアート;4,6−ジエチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−ブチル−4,6−ジエチル−1,2−フェニレンジベンゾアート;4,6−ジエチル−3−イソブチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4,6−ジエチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4,6−ジエチル−1,2−フェニレンジベンゾアート;4,6−ジエチルビフェニル−2,3−ジイルジベンゾアート;6−エチル−3−メチル−4−プロピル−1,2−フェニレンジベンゾアート;3,6−ジエチル−4−プロピル−1,2−フェニレンジベンゾアート;
6−エチル−3,4−ジプロピル−1,2−フェニレンジベンゾアート;6−エチル−3−イソプロピル−4−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−6−エチル−4−プロピル−1,2−フェニレンジベンゾアート;6−エチル−3−イソブチル−4−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−6−エチル−4−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−6−エチル−4−プロピル−1,2−フェニレンジベンゾアート;4−エチル−6−プロピルビフェニル−2,3−ジイルジベンゾアート;6−エチル−4−イソプロピル−3−メチル−1,2−フェニレンジベンゾアート;3,6−ジエチル−4−イソプロピル−1,2−フェニレンジベンゾアート;6−エチル−4−イソプロピル−3−プロピル−1,2−フェニレンジベンゾアート;6−エチル−3,4−ジイソプロピル−1,2−フェニレンジベンゾアート;3−ブチル−6−エチル−4−イソプロピル−1,2−フェニレンジベンゾアート;6−エチル−3−イソブチル−4−イソプロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−6−エチル−4−イソプロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−6−エチル−4−イソプロピル−1,2−フェニレンジベンゾアート;4−エチル−6−イソプロピルビフェニル−2,3−ジイルジベンゾア
ート;4−ブチル−6−エチル−3−メチル−1,2−フェニレンジベンゾアート;
4−ブチル−3,6−ジエチル−1,2−フェニレンジベンゾアート;4−ブチル−6−エチル−3−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−6−エチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3,4−ジブチル−6−エチル−1,2−フェニレンジベンゾアート;4−ブチル−6−エチル−3−イソブチル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロヘキシル−6−エチル−1,2−フェニレンジベンゾアート;6−ブチル−4−エチルビフェニル−2,3−ジイルジベンゾアート;6−エチル−4−イソブチル−3−メチル−1,2−フェニレンジベンゾアート;3,6−ジエチル−4−イソブチル−1,2−フェニレンジベンゾアート;6−エチル−4−イソブチル−3−プロピル−1,2−フェニレンジベンゾアート;6−エチル−4−イソブチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−ブチル−6−エチル−4−イソブチル−1,2−フェニレンジベンゾアート;6−エチル−3,4−ジイソブチル−1,2−フェニレンジベンゾアート;3−シクロペンチル−6−エチル−4−イソブチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−6−エチル−4−イソブチル−1,2−フェニレンジベンゾアート;4−エチル−6−イソブチルビフェニル−2,3−ジイルジベンゾアート;4−tert−ブチル−6−エチル−3−メチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3,6−ジエチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−6−エチル−3−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−6−エチル−3−イソプロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−ブチル−6−エチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−6−エチル−3−イソブチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロヘキシル−6−エチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−6−エチル−3−メチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3,6−ジエチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−6−エチル−3−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−6−エチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;4−シクロペンチル−6−エチル−3−イソブチル−1,2−フェニレンジベンゾアート;3,4−ジシクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−シクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;6−シクロペンチル−4−エチルビフェニル−2,3−ジイルジベンゾアート;4−シクロヘキシル−6−エチル−3−メチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3,6−ジエチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−6−エチル−3−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−6−エチル−3−イソプロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロヘキシル−6−エチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−6−エチル−3−イソブチル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−シクロペンチル−6−エチル−1,2−フェニレンジベンゾアート;3,4−ジシクロヘキシル−6−エチル−1,2−フェニレンジベンゾアート;6−シクロヘキシル−4−エチルビフェニル−2,3−ジイルジベンゾアート;5−エチル−2−メチルビフェニル−3,4−ジイルジベンゾアート;2,5−ジエチルビフェニル−3,4−ジイルジベンゾアート;5−エチル−2−プロピルビフェニル−3,4−ジイルジベンゾアート;5−エチル−2−イソプロピルビフェニル−3,4−ジイルジベンゾアート;2−ブチル−5−エチルビフェニル−3,4−ジイルジベンゾアート;5−エチル−2−イソブチルビフェニル−3,4−ジイルジベンゾアート;2−シクロペンチル−5−エチルビフェニル−3,4−ジイルジベンゾアート;2−シクロヘキシル−5−エチルビフェニル−3,4−ジイルジベンゾアート、5−エチル−2−(2,4,4−トリメチルペンタン−2−イル)ビフェニル−3
,4−ジイルジベンゾアート;3,4−ジフェニル−6−エチル−1,2−フェニレンジベンゾアート;3,4−ジメチル−6−プロピル−1,2−フェニレンジベンゾアート;3−エチル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;4−メチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;3−イソプロピル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−イソブチル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−メチル−6−プロピル−1,2−フェニレンジベンゾアート;6−メチル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;4−エチル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3,4−ジエチル−6−プロピル−1,2−フェニレンジベンゾアート;4−エチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−エチル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−エチル−6−プロピル−1,2−フェニレンジベンゾアート;4−エチル−3−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−エチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−エチル−6−プロピル−1,2−フェニレンジベンゾアート;6−エチル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;3−メチル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3−エチル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3,4,6−トリプロピル−1,2−フェニレンジベンゾアート;3−イソプロピル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3−ブチル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3−イソブチル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4,6−ジプロピル−1,2−フェニレンジベンゾアート;4,6−ジプロピルビフェニル−2,3−ジイルジベンゾアート;4−イソプロピル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−エチル−4−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;4−イソプロピル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;3,4−ジイソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−イソブチル−4−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;6−イソプロピル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;4−ブチル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−エチル−6−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3,4−ジブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;4−ブチル−3−シクロヘキシル−6−プロピル−1,2−フェニレンジベンゾアート;6−ブチル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;4−イソブチル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;3−エチル−4−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−イソブチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−イソブチル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;3,4−ジイソブチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロペンチル−4−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;6−イソ
ブチル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;4−tert−ブチル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−エチル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−ブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;4−tert−ブチル−3−シクロヘキシル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−エチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロペンチル−3−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;3,4−ジシクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;3−シクロヘキシル−4−シクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;6−シクロペンチル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;4−シクロヘキシル−3−メチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−エチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3,6−ジプロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−イソプロピル−6−プロピル−1,2−フェニレンジベンゾアート;3−ブチル−4−シクロヘキシル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−イソブチル−6−プロピル−1,2−フェニレンジベンゾアート;4−シクロヘキシル−3−シクロペンチル−6−プロピル−1,2−フェニレンジベンゾアート;3,4−ジシクロヘキシル−6−プロピル−1,2−フェニレンジベンゾアート;6−シクロヘキシル−4−プロピルビフェニル−2,3−ジイルジベンゾアート;2−メチル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2−エチル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2,5−ジプロピルビフェニル−3,4−ジイルジベンゾアート;2−イソプロピル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2−ブチル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2−イソブチル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2−シクロペンチル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;2−シクロヘキシル−5−プロピルビフェニル−3,4−ジイルジベンゾアート;及び/又は3,4−ジフェニル−6−プロピル−1,2−フェニレンジベンゾアート。
のでなければならない。反することが述べられる場合、文脈から暗黙的である場合、又は、当分野において慣例的である場合を除き、すべての部及びパーセントが重量に基づく。米国特許実務の目的のために、本明細書中で参照される特許、特許出願又は公開物はどれもその内容が、とりわけ当分野における合成技術、定義(本明細書中に提供されるどの定義とも矛盾にしない程度に)及び一般的知識に関して、本明細書によりそれらの全体において参照によって組み込まれる(或いは、それらの相当する米国対応版が参照によってそのように組み込まれる)。
インターポリマーには、コポリマー(これは通常、2つの異なるタイプのモノマー又はコモノマーから調製されるポリマーを示す)、ターポリマー(これは通常、3つの異なるタイプのモノマー又はコモノマーから調製されるポリマーを示す)、及び、テトラポリマー(これは通常、4つの異なるタイプのモノマー又はコモノマーから調製されるポリマーを示す)などが含まれるが、これらに限定されない。
Claims (2)
- (I)
下記の構造(II):
(式中、(A)R1〜R14は同じであるか、又は異なり;(B)R2は、2個〜20個の炭素原子を有するアルキル基であり、且つ、R1〜R4のそれ以外のR基のそれぞれが水素である;
(C)R5〜R14のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される;並びに
(D)R2、R7及びR12のそれぞれが同時にt−ブチル基ではない)
の置換フェニレン芳香族ジエステルと、
(II)
下記の構造(II):
(式中、(A)R 1 〜R 14 は同じであるか、又は異なり、R 1 、R 3 、R 4 のそれぞれが水素であり、R 2 は、1個〜20個の炭素原子を有するヒドロカルビル基である;
(B)R 7 及びR 12 の少なくとも1つが、ハロゲンと、ハロゲン、ケイ素又はアルコキシ基により場合により置換され得る、1個〜20個の炭素原子を有する第一級ヒドロカルビル基と、ハロゲン、ケイ素又はアルコキシ基により場合により置換され得る、1個〜20個の炭素原子を有する第二級ヒドロカルビル基とからなる群から選択される;並びに
(C)R 5 〜R 6 、R 8 〜R 11 及びR 13 〜R 14 のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される)の置換フェニレン芳香族ジエステルと、
(III)
下記の構造(II):
(式中、(A)R 1 〜R 14 は同じであるか、又は異なり、R 1 、R 3 、R 4 のそれぞれが水素であり、R 2 は、1個〜20個の炭素原子を有するヒドロカルビル基である;
(B)R 5 〜R 14 のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される;並びに
(C)R 5 〜R 6 、R 8 〜R 11 及びR 13 〜R 14 の少なくとも1つが、C 1 〜C 6 アルキル基と、ハロゲンと、それらの組合せとからなる群より選択される)
の置換フェニレン芳香族ジエステルと、
(IV)
下記の構造(II):
(式中、(A)R 1 〜R 14 は同じであるか、又は異なり、R 1 、R 2 及びR 4 のそれぞれが、2個〜20個の炭素原子を有するアルキル基と、2個〜20個の炭素原子を有するアルケニル基と、ハロヒドロカルビル基と、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される;並びに
(B)R 3 及びR 5 〜R 14 のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される)
の置換フェニレン芳香族ジエステルと、
(V)
下記の構造(II):
(式中、(A)R 1 〜R 14 は同じであるか、又は異なり、R 1 〜R 4 のそれぞれが、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される;並びに
(B)R 5 〜R 14 のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される)
の置換フェニレン芳香族ジエステルと、
(VI)
下記の構造(II):
(式中、(A)R 1 〜R 14 は同じであるか、又は異なり、R 1 〜R 14 のそれぞれが、水素と、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択される;並びに
(B)R 5 〜R 9 の少なくとも1つがそのそれぞれの対応する片方のR 10 〜R 14 と異なる)の置換フェニレン芳香族ジエステルと、
(VII)
下記の構造(IV):
(式中、(A)R 5 〜R 14 は同じであるか、又は異なり、R 1 及びR 4 のそれぞれが水素である;
並びに
(B)R 5 〜R 14 の少なくとも1つが、1個〜20個の炭素原子を有する非置換のヒドロカルビル基と、ハロヒドロカルビル基と、ハロゲンと、ケイ素含有ヒドロカルビル基と、それらの組合せとからなる群より選択され、且つ、R 7 及びR 12 のそれぞれが同時にメチル基ではない)の置換フェニレン芳香族ジエステルと
のうちの少なくとも1種類を含む、オレフィン系ポリマーの重合のためのチーグラー・ナッタプロ触媒組成物及び/又は触媒組成物。 - 前記(IV)の置換フェニレン芳香族ジエステルにおいてR7がR12と同じである、請求項1に記載のチーグラー・ナッタプロ触媒組成物及び/又は触媒組成物。
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BRPI0918346A2 (pt) * | 2008-12-31 | 2015-12-15 | Dow Global Technologies Llc | diéster aromático de fenileno substituído |
US8106138B2 (en) * | 2008-12-31 | 2012-01-31 | Dow Global Technologies Llc | Random propylene copolymer compositions, articles and process |
EP2655313B1 (en) * | 2010-12-21 | 2015-07-08 | W.R. Grace & Co.-Conn. | Process for production of high melt flow propylene-based polymer and product from same |
KR20140007411A (ko) * | 2011-03-01 | 2014-01-17 | 다우 글로벌 테크놀로지스 엘엘씨 | 다중-접촉 전촉매를 사용하여 벌크 밀도를 개선하는 방법 및 생성물 |
US20140012035A1 (en) * | 2011-03-29 | 2014-01-09 | Linfeng Chen | Production of Substituted Phenylene Aromatic Diesters |
US9133286B2 (en) | 2011-08-30 | 2015-09-15 | W. R. Grace & Co.-Conn | Production of substituted phenylene dibenzoate internal electron donor and procatalyst with same |
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