JP6260532B2 - β−プロピオラクトン骨格を有する(メタ)アクリル酸エステル化合物およびその製造方法 - Google Patents
β−プロピオラクトン骨格を有する(メタ)アクリル酸エステル化合物およびその製造方法 Download PDFInfo
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- JP6260532B2 JP6260532B2 JP2014518345A JP2014518345A JP6260532B2 JP 6260532 B2 JP6260532 B2 JP 6260532B2 JP 2014518345 A JP2014518345 A JP 2014518345A JP 2014518345 A JP2014518345 A JP 2014518345A JP 6260532 B2 JP6260532 B2 JP 6260532B2
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- meth
- propiolactone
- reaction
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- 150000001875 compounds Chemical class 0.000 title claims description 73
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 32
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical group O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 49
- -1 ketene compound Chemical class 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229960000380 propiolactone Drugs 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 48
- 239000000463 material Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000178 monomer Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000007789 gas Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- UMNGRRUQHFCWGR-UHFFFAOYSA-N 2-oxopropyl 2-methylprop-2-enoate Chemical compound CC(=O)COC(=O)C(C)=C UMNGRRUQHFCWGR-UHFFFAOYSA-N 0.000 description 11
- 150000002596 lactones Chemical class 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- STGSWEVVDSCTQT-UHFFFAOYSA-N 1-(2-methyl-4-oxooxetan-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)C1(C)CC(=O)O1 STGSWEVVDSCTQT-UHFFFAOYSA-N 0.000 description 10
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- BBENZURCSWELJD-UHFFFAOYSA-N 3-oxobutan-2-yl 2-methylprop-2-enoate Chemical compound CC(=O)C(C)OC(=O)C(C)=C BBENZURCSWELJD-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000007664 blowing Methods 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- PXJIFTQUKQZGGX-UHFFFAOYSA-N (2-methyl-4-oxooxetan-2-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(C)CC(=O)O1 PXJIFTQUKQZGGX-UHFFFAOYSA-N 0.000 description 3
- HEHFACLCDJDCJN-UHFFFAOYSA-N 2-oxoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=O HEHFACLCDJDCJN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000012790 confirmation Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000002648 laminated material Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- JPYFSQGRZAVZRF-UHFFFAOYSA-N (4-oxooxetan-2-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC(=O)O1 JPYFSQGRZAVZRF-UHFFFAOYSA-N 0.000 description 2
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical compound CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- HDKKRASBPHFULQ-UHFFFAOYSA-N 3-Hydroxy-2-pentanone Chemical compound CCC(O)C(C)=O HDKKRASBPHFULQ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000005468 ion implantation Methods 0.000 description 2
- 150000002561 ketenes Chemical class 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical group CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- LLLCSBYSPJHDJX-UHFFFAOYSA-M potassium;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O LLLCSBYSPJHDJX-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- YDTHWNOACOCGNC-UHFFFAOYSA-N (2-oxooxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCC1C(=O)OC1 YDTHWNOACOCGNC-UHFFFAOYSA-N 0.000 description 1
- QSUJHKWXLIQKEY-UHFFFAOYSA-N (2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCOC1=O QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- FXRQXYSJYZPGJZ-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethenylbenzene Chemical compound CC(C)(C)OC=CC1=CC=CC=C1 FXRQXYSJYZPGJZ-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- VLGDSNWNOFYURG-UHFFFAOYSA-N 4-propyloxetan-2-one Chemical compound CCCC1CC(=O)O1 VLGDSNWNOFYURG-UHFFFAOYSA-N 0.000 description 1
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical group O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)(C(C)(C1(C)N)OC1=O)OC(C(*)=C)=O Chemical compound CC(*)(C(C)(C1(C)N)OC1=O)OC(C(*)=C)=O 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- 239000012267 brine Substances 0.000 description 1
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- 239000012295 chemical reaction liquid Substances 0.000 description 1
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- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002847 norbornane derivatives Chemical class 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N para-hydroxystyrene Natural products OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Description
式中、R1は水素またはメチルであり、R2、R3、R4、R5、およびR6は独立して、水素または炭素数1〜5のアルキルである。
式中、R1は水素またはメチルであり、R2、R3、R4、R5、およびR6は独立して、水素または炭素数1〜5のアルキルである。
ここで、R1は水素またはメチルであり、R2、R3、R4、R5、およびR6は独立して水素または炭素数1〜5のアルキルである。
ここで、R1、R2、R3、R4、R5、およびR6の定義は、前記と同じである。
ここで、R1、R2、R3、およびR4の定義は、前記と同じである。Xはハロゲンである。
β−メタクリロイルオキシメチル−β−メチル−β−プロピオラクトン(R1、R2=メチル、R3、R4、R5、R6=水素の化合物)の合成
窒素ガスで置換した2Lの四ツ口フラスコに、1−ヒドロキシ−2−プロパノン(和光純薬工業(株)社製、純度90.0%以上)50gを入れ、テトラヒドロフラン700gに溶解し、撹拌機、温度計、ジムロート冷却管を接続した。溶液を撹拌し約5℃に冷却した後、トリエチルアミン76.8gおよびヒドロキノン25mgを添加した。撹拌下、約5℃に冷却しながら塩化メタクリロイル(和光純薬工業(株)社製、純度97.0%以上)71.9gを徐々に滴下し、さらに3時間撹拌を継続してエステル化反応を行った。反応液は約5℃に保持しながら2N−塩酸を用いて酸洗浄後、酢酸エチル300mLを用いて2回抽出操作を行い、有機層を得た。有機層は10%炭酸水素ナトリウム水溶液、および飽和食塩水を用いて洗浄し、無水硫酸マグネシウムを用いて乾燥、濾別して反応粗液を得た。エバポレーターを用いて反応粗液から溶媒を留去し、85.5gの粗2−オキソプロピルメタクリレートを得た。NMRのプロトン比から求めた2−オキソプロピルメタクリレートの収量は67.1g(1−ヒドロキシ−2−プロパノンを基準として収率69.9%)であった。
α,α,β−トリメチル−β−メタクリロイルオキシメチル−β−プロピオラクトン(R1、R2、R5、R6=メチル、R3、R4=水素の化合物)の合成
1Lの四ツ口フラスコに、1−ヒドロキシ−2−プロパノン50gを入れトルエン485gに溶解し、ジメタクリル酸無水物(ALDRICH社製、純度94.0%)および4,4’−チオビス(6−t−ブチル−o−クレゾール)113gを0.5重量%添加し、撹拌機、温度計、ジムロート冷却管を接続した。撹拌し液温を45℃とした溶液にトリエチルアミン80gを滴下し、さらにN,N−ジメチル−4−アミノピリジン(和光純薬工業(株)社製、純度99.0%以上)0.75gをトルエン15gに溶解した溶液を滴下した。液温を50〜70℃の範囲に保ちながら、滴下開始から90分撹拌を継続し、メチルアルコール70gを添加し反応を停止した。反応液は1N−塩酸、10%炭酸ナトリウム水溶液、および飽和食塩水を用いて洗浄を行い、無水硫酸マグネシウムを用いて乾燥、濾別して反応粗液を得た。反応粗液はエバポレーターを用いて溶媒を留去した後、減圧蒸留してGC純度99.0%の2−オキソプロピルメタクリレート49.7g(1−ヒドロキシ−2−プロパノンを基準として収率51.9%)を得た。
β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトン(R1、R2、R3=メチル、R4、R5、R6=水素の化合物)の合成
2Lの四ツ口フラスコに、3−ヒドロキシ−2−ブタノン(東京化成工業(株)社製、純度95.0%以上)150gを入れ塩化メチレン750gに溶解し、撹拌機、温度計、ジムロート冷却管を接続した。溶液を撹拌し約5℃に冷却した後、トリエチルアミン190gおよびp−メトキシフェノール80mgを添加した。撹拌下、液温を約5℃に冷却しながら塩化メタクリロイル178gを4時間かけてゆっくり滴下し、さらに滴下終了後30分撹拌して反応させた。反応液は室温にて、1N−塩酸、10%炭酸ナトリウム水溶液、および飽和食塩水を用いて洗浄し、無水硫酸マグネシウムを用いて乾燥、濾別して反応粗液を得た。反応粗液はエバポレーターにより溶媒留去し、p−メトキシフェノールを80mg添加して減圧蒸留して、GC純度96.5%の3−オキソブタン−2−イルメタクリレート141g(3−ヒドロキシ−2−ブタノンを基準として収率53.1%)を得た。
β−メタクリロイルオキシメチル−β−プロピオラクトン(R1=メチル、R2、R3、R4、R5、R6=水素の化合物)の合成
2Lの四ツ口フラスコに、メタクリル酸カリウム(和光純薬工業(株)社製、純度98.0%)180gを入れN,N−ジメチルホルムアミド900gを加え、撹拌機、温度計、ジムロート冷却管を接続した。2−ブロモ−1,1−ジエトキシエタン(ALDRICH社製、純度97%)308g、p−メトキシフェノール0.9g、およびテトラメチルアンモニウムヨージド1.32gを添加して撹拌下150℃で2時間反応させた。反応液は室温まで冷却し沈殿を濾別後、N,N−ジメチルホルムアミドを留去し減圧蒸留して反応生成物174g(GC純度98.5%)を得た。得られた反応生成物のうち、19gを窒素ガスで置換した1Lの四ツ口フラスコに入れ、水430mLに撹拌して分散し、ハイドロキノン0.21g、1−フェニル−3−ピラゾリジノン(東京化成工業(株)社製、純度98.0%以上)0.41gおよび85%リン酸2.8gを加えて撹拌下70〜80℃で3時間反応させた。反応液は室温に冷却し、10%炭酸水素ナトリウム水溶液で中和し、ジエチルエーテルを用いて抽出を繰り返し、有機層を硫酸マグネシウムにより乾燥、濾別後、減圧蒸留して2−オキソエチルメタクリレート5.6g(メタクリル酸カリウムを基準として収率27.6%)を得た。
β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンのアルカリ水溶液に対する溶解性の確認
実施例3で得られたβ―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトン0.54gをサンプル管に量り取り、回転子を加えた後、2.5%TMAH水溶液(東京化成工業(株)社製10%水溶液を蒸留水で4倍希釈したもの)10.1g(β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンに対しTMAHが1当量)を加え、スターラー上で激しく撹拌した。1時間後、撹拌を止めて液の様子を観察すると油滴が分散していることを確認した。これを2N塩酸でクエンチし、ジエチルエーテル及び酢酸エチルで抽出を繰り返し、有機層をエバポレータで溶媒留去した。得られた濃縮残分0.59gをHPLCで分析したところ、アルカリ水溶液と反応する前と比べ、β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンが7.1%残っていた。
β,γ−ジメチル−β−メタクリロイルオキシ−γ−ブチロラクトンの合成
1Lの四ツ口フラスコに、実施例3で合成した3−オキソブタン−2−イルメタクリレート200gを入れ酢酸エチル460gを加え撹拌して溶液とし、撹拌機、温度計、ジムロート冷却管、ガス導入管を接続した。溶液を撹拌し水浴を用いて約30℃とした後、三フッ化ホウ素のジエチルエーテル錯体を基質に対して5.6mol%添加した。液温を約30℃に保ちながらケテンガスを基質に対して0.55当量/hの速度でガス導入管より溶液に通じ、GC分析により3−オキソブタン−2−イルメタクリレートが消失するまで反応を行った。4.5時間で反応は終結し、ケテンガスの吹き込みを止め、窒素ガスを通じることで残存するケテンを系外に除いた。
β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンと同じ元素組成を有するβ,γ−ジメチル−β−メタクリロイルオキシ−γ−ブチロラクトン0.54gを用い、実施例5と同様のアルカリ水溶液に対する溶解性の確認試験を行った。10.1gの2.5%のTMAH水溶液を用いた場合でも1時間後の溶液は均一となり、β―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンの残量は反応前と比べて0.6%であった。また、2.5%のTMAH水溶液を20.2g用いた場合には、HPLCにてβ―メチル−β−(メタクリロイルオキシエチル−1−イル)−β−プロピオラクトンは観察されなかった。
Claims (3)
- R1、R2、R3、R4、R5、およびR6が独立して、水素またはメチルである請求項1に記載のβ−プロピオラクトン骨格を有する(メタ)アクリル酸エステル化合物の製造方法。
- 式(2)で示されるカルボニル基を有する化合物と、式(3)で示されるケテン化合物を、応液温度を10℃以下で、テトラヒドロフランを含む溶媒中で反応させることを特徴とする請求項1に記載の式(1)で示されるβ−プロピオラクトン骨格を有する(メタ)アクリル酸エステル化合物の製造方法。
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US10090228B1 (en) | 2012-03-06 | 2018-10-02 | Amkor Technology, Inc. | Semiconductor device with leadframe configured to facilitate reduced burr formation |
US10811341B2 (en) | 2009-01-05 | 2020-10-20 | Amkor Technology Singapore Holding Pte Ltd. | Semiconductor device with through-mold via |
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US9978695B1 (en) | 2011-01-27 | 2018-05-22 | Amkor Technology, Inc. | Semiconductor device including leadframe with a combination of leads and lands and method |
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