JP5219540B2 - フェノール性化合物及びその製造方法 - Google Patents
フェノール性化合物及びその製造方法 Download PDFInfo
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- 150000002989 phenols Chemical class 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 238000006482 condensation reaction Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229940079877 pyrogallol Drugs 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000010894 electron beam technology Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000003377 acid catalyst Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000001641 gel filtration chromatography Methods 0.000 description 5
- 238000001459 lithography Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 229960000587 glutaral Drugs 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 1
- AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- -1 n-propyl Alcohols Chemical class 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
[3]前記Xが、非置換のメチレン基、又は炭素数2〜6の非置換のアルキレン基である前記[1]又は[2]に記載のフェノール性化合物。
[4]前記Xが、メチレン基、エチレン基、プロピレン基、又はブチレン基である前記[3]に記載のフェノール性化合物。
[6]前記Xが、非置換のメチレン基、又は炭素数2〜6の非置換のアルキレン基である前記[5]に記載のフェノール性化合物の製造方法。
[7]前記Xが、メチレン基、エチレン基、プロピレン基、又はブチレン基である前記[6]に記載のフェノール性化合物の製造方法。
システム:東ソー社製、型番「HLC−8220」
検出器:型番「HLC−8200」、内蔵RI・UV−8200(280nm)
カラムオーブン温度:40℃
サンプルポンプ:流速;0.600ml/min、ポンプ圧;14.5mPa
リファレンスポンプ:流速;0.600ml/min、ポンプ圧;2.5mPa
カラム:昭和電工社製、商品名「Shodex Asahipak GF−510 HQ」+商品名「GF−310 HQ」×2
ガードカラム:昭和電工社製、商品名「Shodex Asahipak GF−1G 7B」
回転子を入れた50mLのナスフラスコに、ピロガロール2.5g(20mmol)及びエタノール4.5mLを入れ、ピロガロールをエタノールに溶解させた後、濃塩酸1.5mLを触媒として添加した。氷冷下、1,5−ペンタンジアール1.0g(5mmol)をゆっくりと滴下した後、80℃で48時間撹拌した。反応終了後、生成した固体を濾過し、メタノールで2回洗浄して、0.44gの白色の固体を得た。収率は28%(理論収量:1.58g)であった。得られた白色の固体についての構造確認を行った結果を以下に示す。また、赤外吸収スペクトル(IR)、核磁気共鳴スペクトル(1H−NMR)、及び質量分析(MALDI−TOF−MS)の測定結果を示すチャート、並びにゲル濾過クロマトグラフィー(GPC)による分析結果を示すクロマトグラム(溶出チャート)を図1〜4にそれぞれ示す。
3330(νOH);1605、1477、1466(νC=C(aromatic))
δ(ppm)=0.57〜2.41(b,36.0 H,Ha,Hb)、3.92〜4.69(m,12.0 H,Hc)、5.78〜7.10(m,12.0 H,Hd)、7.39〜9.34(m,36.0 H,He,Hf)
<計算値>EM:1896.57、[M+Na]+:1919.57、[M+K]+:1935.57
<実測値>[M+Na]+:1918.6、[M+K]+:1934.6
図1〜4に示す結果から、実施例1で得られた白色の固体は、大環状化合物であるものと推測される。そして、その構造は、いわゆるNoria型であるか、或いはTrimer型であると予想される。
回転子を入れた50mLのナスフラスコに、ピロガロール2.5g(20mmol)及びエタノール4.5mLを入れ、ピロガロールをエタノールに溶解させた後、濃塩酸1.5mLを触媒として添加した。氷冷下、1,5−ペンタンジアール1.0g(5mmol)をゆっくりと滴下した後、80℃で72時間撹拌した。種々の反応時間で分析試料をサンプリングし、ゲル濾過クロマトグラフィー(GPC)により反応の進行状況を追跡した。ゲル濾過クロマトグラフィー(GPC)による分析結果を示すクロマトグラム(溶出チャート)を図5に示す。なお、図5中、符号(a)〜(j)は、5min、10min、1h、3h、5h、8h、12h、24h、48h、及び72hの反応時間でサンプリングした分析試料を用いて得られた溶出チャートをそれぞれ示す。
Claims (7)
- 前記Xが、非置換のメチレン基、又は炭素数2〜6の非置換のアルキレン基である請求項1又は2に記載のフェノール性化合物。
- 前記Xが、メチレン基、エチレン基、プロピレン基、又はブチレン基である請求項3に記載のフェノール性化合物。
- 前記Xが、非置換のメチレン基、又は炭素数2〜6の非置換のアルキレン基である請求項5に記載のフェノール性化合物の製造方法。
- 前記Xが、メチレン基、エチレン基、プロピレン基、又はブチレン基である請求項6に記載のフェノール性化合物の製造方法。
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JP2004231858A (ja) * | 2003-01-31 | 2004-08-19 | Sumitomo Bakelite Co Ltd | フォトレジスト用樹脂及びフォトレジスト組成物 |
JP4895537B2 (ja) * | 2005-06-30 | 2012-03-14 | Jsr株式会社 | カリックスアレーン系ポリマー及びその製造方法 |
JP4657030B2 (ja) * | 2005-06-30 | 2011-03-23 | Jsr株式会社 | カリックスアレーン系誘導体及びそれを含有する組成物 |
JP5396738B2 (ja) * | 2007-05-09 | 2014-01-22 | 三菱瓦斯化学株式会社 | 感放射線性組成物、化合物、化合物の製造方法およびレジストパターン形成方法 |
JP5481017B2 (ja) * | 2007-05-09 | 2014-04-23 | 学校法人神奈川大学 | ラダーポリマー誘導体の製造方法 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |