JPWO2010047244A1 - エポキシ化合物およびその製造方法 - Google Patents
エポキシ化合物およびその製造方法 Download PDFInfo
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- JPWO2010047244A1 JPWO2010047244A1 JP2009548528A JP2009548528A JPWO2010047244A1 JP WO2010047244 A1 JPWO2010047244 A1 JP WO2010047244A1 JP 2009548528 A JP2009548528 A JP 2009548528A JP 2009548528 A JP2009548528 A JP 2009548528A JP WO2010047244 A1 JPWO2010047244 A1 JP WO2010047244A1
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- carbon atoms
- epoxy compound
- hydrocarbon group
- hydrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
- 239000004593 Epoxy Substances 0.000 title claims abstract description 80
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 29
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 125000004185 ester group Chemical group 0.000 claims abstract description 12
- 125000001033 ether group Chemical group 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 28
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 20
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical class C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 150000004714 phosphonium salts Chemical group 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 230000000382 dechlorinating effect Effects 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 abstract description 13
- 239000003822 epoxy resin Substances 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 20
- SDPHOMMVBSJKJF-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-phenoxyaniline Chemical compound C1OC1CN(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CC1CO1 SDPHOMMVBSJKJF-UHFFFAOYSA-N 0.000 description 20
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000007363 ring formation reaction Methods 0.000 description 12
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- 238000004821 distillation Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
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- 239000002994 raw material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- INXUJOKBROPPQH-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-2-phenoxyaniline Chemical compound C1OC1CN(C=1C(=CC=CC=1)OC=1C=CC=CC=1)CC1CO1 INXUJOKBROPPQH-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
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- IGPJWIGZKUSTID-UHFFFAOYSA-N 2-(2-methylphenoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1N(CC1OC1)CC1OC1 IGPJWIGZKUSTID-UHFFFAOYSA-N 0.000 description 6
- LXXSTDMIWLEGAF-UHFFFAOYSA-N 4-(4-methylphenoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1=CC(C)=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 LXXSTDMIWLEGAF-UHFFFAOYSA-N 0.000 description 6
- LSSWPDUBLAOHKT-UHFFFAOYSA-N 4-(4-nitrophenoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 LSSWPDUBLAOHKT-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
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- 230000035484 reaction time Effects 0.000 description 6
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- 230000008025 crystallization Effects 0.000 description 5
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 5
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- JYJPXACGURQSCB-UHFFFAOYSA-N 2-(2-methylphenoxy)aniline Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1N JYJPXACGURQSCB-UHFFFAOYSA-N 0.000 description 4
- UCSYVYFGMFODMY-UHFFFAOYSA-N 3-phenoxyaniline Chemical compound NC1=CC=CC(OC=2C=CC=CC=2)=C1 UCSYVYFGMFODMY-UHFFFAOYSA-N 0.000 description 4
- VPCGOYHSWIYEMO-UHFFFAOYSA-N 4-(4-methylphenoxy)aniline Chemical compound C1=CC(C)=CC=C1OC1=CC=C(N)C=C1 VPCGOYHSWIYEMO-UHFFFAOYSA-N 0.000 description 4
- ASAOLTVUTGZJST-UHFFFAOYSA-N 4-(4-nitrophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 ASAOLTVUTGZJST-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- OVZZXYZBKCKJIN-UHFFFAOYSA-N 1-chloro-3-(n-(3-chloro-2-hydroxypropyl)-4-phenoxyanilino)propan-2-ol Chemical compound C1=CC(N(CC(O)CCl)CC(CCl)O)=CC=C1OC1=CC=CC=C1 OVZZXYZBKCKJIN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 C*c1ccccc1 Chemical compound C*c1ccccc1 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 239000012847 fine chemical Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
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- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- JXISYIGTYKLVAC-UHFFFAOYSA-N potassium sodium ethanolate propan-1-olate Chemical compound [O-]CC.[Na+].[O-]CCC.[K+] JXISYIGTYKLVAC-UHFFFAOYSA-N 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- XOGCTUKDUDAZKA-UHFFFAOYSA-N tetrapropylphosphanium Chemical compound CCC[P+](CCC)(CCC)CCC XOGCTUKDUDAZKA-UHFFFAOYSA-N 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- IKANSXQHJXBNIN-UHFFFAOYSA-N trimethyl(octadecyl)phosphanium Chemical compound CCCCCCCCCCCCCCCCCC[P+](C)(C)C IKANSXQHJXBNIN-UHFFFAOYSA-N 0.000 description 1
- NVQBNLRCSAEYHZ-UHFFFAOYSA-N trimethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](C)(C)C NVQBNLRCSAEYHZ-UHFFFAOYSA-N 0.000 description 1
- YGDBTMJEJNVHPZ-UHFFFAOYSA-N trimethyl(propyl)phosphanium Chemical compound CCC[P+](C)(C)C YGDBTMJEJNVHPZ-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
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Abstract
Description
下記式で示されるエポキシ化合物、
下記式で示されるエポキシ化合物
で示されるフェノキシアニリン誘導体とエピクロロヒドリンを反応させ、下記式
で示されるエポキシ化合物を製造する方法である。
で示されるジクロロヒドリン体とアルカリ化合物を反応させ、脱塩化水素することによりジエポキシ化合物にする。
温度計、滴下漏斗、冷却管および攪拌機を取り付けた四つ口フラスコに、エピクロロヒドリンを610.6g(6.6mol)仕込み、四つ口フラスコの内部を窒素で置換した。4−フェノキシアニリンの粉末203.7g(1.1mol)をエタノール1018.5gに溶解させた。エピクロロヒドリンの温度を70℃まで上げて、4−フェノキシアニリンのエタノール溶液を4時間かけて滴下した。さらに、6時間撹拌しながら70℃で反応させ、4−フェノキシ−N,N−ビス(2−ヒドロキシ−3−クロロプロピル)アニリンを生成させた。
実施例1で得られた褐色の粘性液体を、100Paの圧力下、250℃の温度で単蒸留したところ、純度96.1%(GC area%)の4−フェノキシ−N,N−ジグリシジルアニリンを得た(黄色の粘性液体)。
δ2.59(dd,2H)、2.80(dd,2H)、3.15−3.21(m,2H)、3.41(dd,2H)、3.73(dd,2H)、6.81(d,2H)、6.93−7.03(m,5H)、7.25−7.30(m,2H) 。
エタノールを用いず、4−フェノキシアニリンの粉末203.7g(1.1mol)を加えたこと以外は、実施例1と同様に実施した。4−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が304.7g(純度56.4%(GC area%))が得られた。4−フェノキシ−N,N−ジグリシジルアニリンの純分換算収率(4−フェノキシアニリン基準)は、52.5%であった。
エタノール1018.5gをトルエン1018.5gに変更したこと以外は、実施例1と同様に実施した。付加反応が起こらず、目的の中間物である4−フェノキシ−N,N−ビス(2−ヒドロキシ−3−クロロプロピル)アニリンは得られなかった。
温度計、冷却管および攪拌機を取り付けた四つ口フラスコに、エピクロロヒドリンを610.6g(6.6mol)、2−プロパノールを509.3g仕込み、四つ口フラスコの内部を窒素で置換した。温度を60℃まで上げて、4−フェノキシアニリン203.7g(1.1mol)の粉末を3時間かけて添加した。さらに温度を80℃まで上げて18時間撹拌しながら80℃で反応させ、4−フェノキシ−N,N−ビス(2−ヒドロキシ−3−クロロプロピル)アニリンを生成させた。
実施例4において、2−プロパノールを用いなかったこと以外は、実施例4と同様に実施した。4−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が312.8g(純度96.6%(GC area%))が得られた。4−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(4−フェノキシアニリン基準)は92.4%であった。
実施例4において、硫酸水素テトラブチルアンモニウム11.2g(0.033mol)を臭化エチルトリフェニルホスホニウム12.3g(0.033mol)に変更したこと以外は、実施例4と同様に実施した。4−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が315.0g(純度96.7%(GC area%))が得られた。4−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(4−フェノキシアニリン基準)は93.1%であった。
実施例4において、硫酸水素テトラブチルアンモニウムを添加しなかったこと以外は、実施例4と同様に実施した。4−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が294.4g(純度45.1%(GC area%))が得られた。4−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(4−フェノキシアニリン基準)は40.6%であった。
温度計、滴下漏斗、冷却管および攪拌機を取り付けた四つ口フラスコに、2−プロパノールを509.3g、48%水酸化ナトリウム水溶液275g(3.3mol)、4−フェノキシアニリン203.7g(1.1mol)を仕込み、四つ口フラスコの内部を窒素で置換した。温度を80℃まで上げてエピクロロヒドリンを610.6g(6.6mol)を1時間かけて添加した。さらに80℃で18時間撹拌しながら反応させた。
実施例4において、4−フェノキシアニリンの粉末203.7g(1.1mol)を4−(4−メチルフェノキシ)アニリン219.2g(1.1mol)に変更したこと以外は、実施例4と同様に実施した。4−(4−メチルフェノキシ)−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が339.1g(純度97.5%(GC area%))が得られた。4−(4−メチルフェノキシ)−N,N−ジグリシジルアニリンの純度換算収率(4−(4−メチルフェノキシ)アニリン基準)は96.5%であった。
δ2.30(s,3H)、2.59(dd,2H)、2.80(dd,2H)、3.17−3.19(m,2H)、3.41(dd,2H)、3.72(dd,2H)、6.78−6.94(m,6H)、7.08(d,2H)。
実施例4において、4−フェノキシアニリンの粉末203.7g(1.1mol)を、4−(4−ニトロフェノキシ)アニリン253.2g(1.1mol)に、付加反応の反応時間を33時間に変更したこと以外は、実施例4と同様に実施した。4−(4−ニトロフェノキシ)−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が357.8g(純度92.5%(LC area%))が得られた。4−(4−ニトロフェノキシ)−N,N−ジグリシジルアニリンの純度換算収率(4−(4−ニトロフェノキシ)アニリン基準)は87.9%であった。
δ2.61(dd,2H)、2.84(dd,2H)、3.20−3.22(m,2H)、3.44(dd,2H)、3.80(dd,2H)、6.85−6.99(m,6H)、8.17(d,2H)。
実施例4において、4−フェノキシアニリンの粉末203.7g(1.1mol)を2−フェノキシアニリン203.7g(1.1mol)に、付加反応の反応時間を47時間に変更したこと以外は、実施例4と同様に実施した。2−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色の粘性液体が320.2g(純度94.5%(GC area%))が得られた。2−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(2−フェノキシアニリン基準)は92.5%であった。
δ2.46(dd,2H)、2.64(dd,2H)、2.96−3.03(m,2H)、3.23(dd,2H)、3.52(dd,2H)、6.90−7.13(m,6H)、7.20−7.30(m,3H)。
実施例11において、エピクロロヒドリンの添加量を1221.2g(13.2mol)に変更し、2−プロパノール509.3gをプロピレングリコールモノメチルエーテル509.3gに変更し、付加反応の反応時間を21時間、付加反応の温度を110℃に変更したこと以外は、実施例11と同様に実施した。2−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色の粘性液体が319.3g(純度97.1%(GC area%))が得られた。2−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(2−フェノキシアニリン基準)は94.8%であった。
実施例4において、4−フェノキシアニリンの粉末203.7g(1.1mol)を2−(2−メチルフェノキシ)アニリン219.2g(1.1mol)に、付加反応の熟成時間を32時間に変更したこと以外は、実施例4と同様に実施した。2−(2−メチルフェノキシ)−N,N−ジグリシジルアニリンを主成分とする褐色粘性液体が336.5g(純度96.2%(GC area%))が得られた。2−(2−メチルフェノキシ)−N,N−ジグリシジルアニリンの純度換算収率(2−(2−メチルフェノキシ)アニリン基準)は94.5%であった。
δ2.31(s,3H)、2.50(dd,2H)、2.69(dd,2H)、3.06―3.07(m,2H)、3.29(dd,2H)、3.56(dd,2H)、6.74(dd,2H)、6.93−7.12(m,4H)、7.21−7.25(m,2H)。
実施例4において、4−フェノキシアニリンの粉末203.7g(1.1mol)を3−フェノキシアニリン203.7g(1.1mol)に、付加反応の反応時間を30時間に変更したこと以外は、実施例4と同様に実施した。3−フェノキシ−N,N−ジグリシジルアニリンを主成分とする褐色の粘性液体が319.8g(純度97.5%(GC area%))が得られた。3−フェノキシ−N,N−ジグリシジルアニリンの純度換算収率(3−フェノキシアニリン基準)は95.3%であった。
δ2.55(dd,2H)、2.78(dd,2H)、3.13−3.18(m,2H)、3.43(dd,2H)、3.72(dd,2H)、6.35(dd,1H)、6.47(s,1H)、6.54(dd,1H)、7.01−7.03(m,2H)、7.09(dd,1H)、7.17(t,1H)、7.31−7.34(m,2H) 。
実施例1で得られた4−フェノキシ−N,N−ジグリシジルアニリン60重量部とビスフェノールA変性エポキシ樹脂(jER828、ジャパンエポキシレジン(株)製)40重量部の混合物に対し、硬化剤として、メタキシレンジアミン(MXDA、三菱ガス化学(株)製)41重量部を、均一に混合して液状組成物を調製した。この液状組成物を金型に注型し140℃で2時間加熱して、硬化させた。硬化物で試験片を作成した。硬化物を、動的粘弾性測定装置(DMA)(ユービーエム(株)製 Rheogel−E4000)で、昇温速度:2℃/min.として、弾性率を測定した。
本発明のエポキシ化合物の製造方法は、下記式
で示されるフェノキシアニリン誘導体とエピクロロヒドリンを反応させ、下記式
で示されるエポキシ化合物を製造する方法である。
で示されるジクロロヒドリン体とアルカリ化合物を反応させ、脱塩化水素することによりジエポキシ化合物にする。
Claims (16)
- R1が、水素、炭素数1〜4の脂肪族炭化水素基、または、炭素数6〜9の芳香族炭化水素基である請求項1記載のエポキシ化合物。
- R2が、水素、炭素数1〜4の脂肪族炭化水素基、炭素数6〜9の芳香族炭化水素基、または、ニトロ基である請求項1記載のエポキシ化合物。
- R1が、水素である請求項1記載のエポキシ化合物。
- R2が、水素、メチル基、または、ニトロ基である請求項1記載のエポキシ化合物。
- 下記一般式
- フェノキシアニリン誘導体とエピクロロヒドリンを、アルコールを含む溶媒中で反応させる請求項9記載のエポキシ化合物の製造方法。
- ジクロロヒドリン体をジエポキシ化合物にする際に、第四級アンモニウム塩および/または第四級ホスフォニウム塩を共存させる請求項11記載のエポキシ化合物の製造方法。
- R1が、水素または炭素数1〜4の脂肪族炭化水素基である請求項9に記載のエポキシ化合物の製造方法。
- R2が、水素、炭素数1〜4の脂肪族炭化水素基、または、ニトロ基である請求項9に記載のエポキシ化合物の製造方法。
- R1が、水素である請求項9に記載のエポキシ化合物の製造方法。
- R2が、水素、メチル基、または、ニトロ基である請求項9に記載のエポキシ化合物の製造方法。
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US (1) | US8415490B2 (ja) |
EP (1) | EP2341092B1 (ja) |
JP (1) | JP4775804B2 (ja) |
KR (1) | KR101578046B1 (ja) |
CN (1) | CN101910235B (ja) |
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EP2412742B1 (en) * | 2009-03-24 | 2014-12-17 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material, prepreg, and fiber-reinforced composite material |
JP2012219081A (ja) * | 2011-04-12 | 2012-11-12 | Toray Fine Chemicals Co Ltd | 高純度ジグリシジルアミン系エポキシ化合物およびその製造方法 |
CN102225920A (zh) * | 2011-04-15 | 2011-10-26 | 姜堰市扬子江化工有限公司 | 六缩水甘油基三氨基三苯胺及其制备方法 |
JPWO2013089006A1 (ja) * | 2011-12-15 | 2015-04-27 | 東レ・ファインケミカル株式会社 | グリシジルアミン系エポキシ化合物の製造方法 |
JP5935339B2 (ja) * | 2012-01-17 | 2016-06-15 | 東レ株式会社 | 電子機器用接着剤組成物 |
JP2014201520A (ja) * | 2013-04-01 | 2014-10-27 | 東レ・ファインケミカル株式会社 | ジグリシジルアミン系エポキシ化合物の製造方法 |
US9694518B2 (en) * | 2014-06-20 | 2017-07-04 | The Regents Of The University Of Michigan | Breath-activated images and anti-counterfeit authentication features formed of nanopillar arrays |
US20180134837A1 (en) * | 2015-06-19 | 2018-05-17 | Toray Industries, Inc. | Epoxy resin composition, prepreg and fiber-reinforced composite material |
JP2018159053A (ja) * | 2017-03-21 | 2018-10-11 | 東レ・ファインケミカル株式会社 | 多官能グリシジルアミン型エポキシ化合物の製造方法 |
JP7061538B2 (ja) * | 2018-08-31 | 2022-04-28 | 東レ・ファインケミカル株式会社 | ジグリシジルアミン系エポキシ化合物の精製方法 |
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US4487948A (en) | 1983-03-23 | 1984-12-11 | Celanese Corporation | Polyglycidyl hindered aromatic amines |
US4814414A (en) | 1986-04-17 | 1989-03-21 | Amoco Corporation | Epoxy resins based on tetraglycidyl diamines |
JPH01125374A (ja) | 1987-04-17 | 1989-05-17 | Union Carbide Corp | テトラグリシジルジアミンを基剤とするエポキシ樹脂 |
JPH07292315A (ja) | 1994-04-21 | 1995-11-07 | Abc Trading Co Ltd | ハイブリッド型プレポリマーを主剤とする塗材及び製造方法 |
GB9520704D0 (en) * | 1995-10-10 | 1995-12-13 | Secr Defence | High temperature epoxy resins |
TW487697B (en) * | 1996-07-19 | 2002-05-21 | Nissan Chemical Ind Ltd | Method for producing purified epoxy compound |
JP2003113223A (ja) | 2001-10-05 | 2003-04-18 | Nippon Kayaku Co Ltd | 高純度液状エポキシ樹脂及びその製法、エポキシ樹脂組成物及びその硬化物 |
JP2003119244A (ja) | 2001-10-12 | 2003-04-23 | Nippon Kayaku Co Ltd | 高純度液状エポキシ樹脂の製法、エポキシ樹脂組成物及びその硬化物 |
JP2004263153A (ja) | 2003-03-04 | 2004-09-24 | Ebara Corp | スルホン酸基を有するアミン硬化型エポキシ樹脂電解質および製造法 |
JP4636238B2 (ja) * | 2004-11-30 | 2011-02-23 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
EP2412742B1 (en) | 2009-03-24 | 2014-12-17 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material, prepreg, and fiber-reinforced composite material |
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US8415490B2 (en) | 2013-04-09 |
KR20110071049A (ko) | 2011-06-28 |
TW201026677A (en) | 2010-07-16 |
CA2707897A1 (en) | 2010-04-29 |
WO2010047244A1 (ja) | 2010-04-29 |
EP2341092A1 (en) | 2011-07-06 |
BRPI0905991B1 (pt) | 2019-07-30 |
AU2009307505A1 (en) | 2010-04-29 |
AU2009307505B2 (en) | 2013-12-12 |
CA2707897C (en) | 2016-01-19 |
ES2455741T3 (es) | 2014-04-16 |
CN101910235A (zh) | 2010-12-08 |
KR101578046B1 (ko) | 2015-12-16 |
TWI460167B (zh) | 2014-11-11 |
CN101910235B (zh) | 2012-06-13 |
EP2341092B1 (en) | 2014-03-26 |
BRPI0905991A2 (pt) | 2015-06-30 |
JP4775804B2 (ja) | 2011-09-21 |
US20110040111A1 (en) | 2011-02-17 |
EP2341092A4 (en) | 2012-06-06 |
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