JP5834390B2 - ジアシル誘導体の製造方法 - Google Patents
ジアシル誘導体の製造方法 Download PDFInfo
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- JP5834390B2 JP5834390B2 JP2010225471A JP2010225471A JP5834390B2 JP 5834390 B2 JP5834390 B2 JP 5834390B2 JP 2010225471 A JP2010225471 A JP 2010225471A JP 2010225471 A JP2010225471 A JP 2010225471A JP 5834390 B2 JP5834390 B2 JP 5834390B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- -1 chlorine ions Chemical class 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- 229920003235 aromatic polyamide Polymers 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UOFDVLCOMURSTA-UHFFFAOYSA-N 2-(2-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(O)=O UOFDVLCOMURSTA-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- OSUWBBMPVXVSOA-UHFFFAOYSA-N 4-(4-carbonochloridoylphenoxy)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=C(C(Cl)=O)C=C1 OSUWBBMPVXVSOA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AOFRNZNXMCOXHP-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(O)=O AOFRNZNXMCOXHP-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PCWKTVQPSYMIJT-UHFFFAOYSA-N O(C1=CC=C(C(=O)O)C=C1)C1(C(=O)O)CC=CC=C1 Chemical compound O(C1=CC=C(C(=O)O)C=C1)C1(C(=O)O)CC=CC=C1 PCWKTVQPSYMIJT-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- XMFCLBUQBWFZBP-UHFFFAOYSA-N bis(2-methylimidazol-1-yl)methanone Chemical compound CC1=NC=CN1C(=O)N1C(C)=NC=C1 XMFCLBUQBWFZBP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
で表されるジカルボン酸と、一般式(2)
体の製造方法である。
で表されるジカルボン酸と、式(2)
で表されるジアシル誘導体を製造し、反応終了後、単離するジアシル誘導体の製造方法である。
で表されるジカルボン酸において、Aは、単結合、SO2または酸素原子がより好ましく、酸素原子がさらに好ましい。Aが、単結合、SO2または酸素原子であると、ジアミンと重合して得られたポリマーを含む感光性樹脂組成物の露光感度が向上する。R1、R2は、メチル基、エチル基、プロピル基を表す。m、nおよびpは0〜2の整数を表し、0または1が好ましい。mが0、nが0、pが1であることがさらに好ましい。
1,1’−(4,4’−オキシジベンゾイル)ジイミダゾール
1,1’−(4,4’−オキシジベンゾイル)ジイミダゾール
温度計、三方コック、滴下ロート、攪拌機を備えた1Lの4つ口フラスコに窒素気流下、1,1’−カルボニルジイミダゾール(東京化成工業(株)社製)35.17g(0.217モル)とN,N−ジメチルホルムアミド(DMF) (ナカライテスク社製)178gを仕込んだ。4,4’−オキシ二安息香酸(東京化成工業(株)社製)25.04g(0.097モル)をDMF131gに溶解した溶液を滴下ロートから15分間で滴下した。67−69℃(30−36Torr)で溶媒を濃縮し、留出液が195gになった時点で濃縮を終了し、窒素気流下、10℃以下まで冷却し、アセトン(ナカライテスク社製)195gを滴下し、沈殿をろ過した。沈殿をイソプロパノール(ナカライテスク社製)50gで洗浄後、65℃で減圧乾燥し、1,1’−(4,4’−オキシジベンゾイル)ジイミダゾールを30.86g(収率:95%)得た。HPLC純度は99%であった。Fe及びNaの含有量を分析した結果、Fe、Na共に1ppm以下であった。
テレフタロイルジイミダゾール
1,1’−(4,4’−ジベンゾイル)ジイミダゾール
1,1‘−(4,4’−オキシジベンゾイル)ビス(2−メチルイミダゾール)
1,1’−(4,4’−オキシジベンゾイル)ジイミダゾール
温度計、三方コック、攪拌機、滴下ロートを備えた500mLの3つ口フラスコに窒素気流下、4,4’−オキシ二安息香酸(東京化成工業(株)社製)23.50g(0.091モル)、THF(ナカライテスク社製)200gを加え、室温で攪拌しながら、DMF(ナカライテスク社製)6滴を添加し、滴下ロートから塩化チオニル(ナカライテスク社製)23.8g(0.20モルを滴下した後、4時間加熱還流した。加熱してTHF110gを留去した後、冷却し、トルエン(ナカライテスク社製)37gを加えて攪拌し、不溶物をろ過した。ろ液を濃縮乾固して42.7gの4,4’−オキシジベンゾイルクロリドの粗体を得た。ここにTHF125gを加え溶解しTHF溶液を調製した。
Claims (4)
- 一般式(1)
で表されるジカルボン酸と、式(2)
で表されるジアシル誘導体を製造し、反応終了後、単離するジアシル誘導体の製造方法。 - mが0、nが0、pが1である請求項1に記載のジアシル誘導体の製造方法。
- Aが酸素原子である請求項1または2に記載のジアシル誘導体の製造方法。
- 一般式(1)
で表されるジカルボン酸と、式(2)
で表されるジアシル誘導体を製造し、反応終了後、単離して、水、アルコール類、ケトン類から選ばれる少なくとも1種類の溶媒で洗浄するジアシル誘導体の製造方法。
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JP2012077048A JP2012077048A (ja) | 2012-04-19 |
JP5834390B2 true JP5834390B2 (ja) | 2015-12-24 |
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Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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GB2324797A (en) * | 1997-05-02 | 1998-11-04 | Courtaulds Coatings | Hyperbranched polymers |
JP3357662B2 (ja) * | 1998-07-03 | 2002-12-16 | 大鵬薬品工業株式会社 | ナフタルイミドベンズアミド誘導体 |
US9188860B2 (en) * | 2007-09-06 | 2015-11-17 | Toray Industries, Inc. | Method for producing polyamide and resin composition |
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