JP5231456B2 - 新規化合物とその合成方法及びオイル添加剤 - Google Patents
新規化合物とその合成方法及びオイル添加剤 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims description 39
- 238000001308 synthesis method Methods 0.000 title claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 238000006467 substitution reaction Methods 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- -1 fluoride compound Chemical class 0.000 claims description 4
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 44
- 239000000654 additive Substances 0.000 description 19
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 230000000996 additive effect Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000005979 thermal decomposition reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 235000013024 sodium fluoride Nutrition 0.000 description 9
- 239000011775 sodium fluoride Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000003405 preventing effect Effects 0.000 description 7
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 6
- 238000002076 thermal analysis method Methods 0.000 description 6
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000002199 base oil Substances 0.000 description 4
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 2
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- ATSUEPJBZAPLRR-UHFFFAOYSA-N 1-phenoxycyclohexa-2,4-dien-1-amine Chemical compound O(C1=CC=CC=C1)C1(N)CC=CC=C1 ATSUEPJBZAPLRR-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004420 diamide group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000010729 system oil Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
- C10M147/04—Monomer containing carbon, hydrogen, halogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/003—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
一般式(2)
〔式中、kは1〜5の整数であり、nは1以上の整数である。〕
一般式(3)
〔式中、Yは酸素原子(O)、硫黄原子(S)、CO基、SO基又はSO2基を表わし、mは1〜10の整数である。フェニル基に有する2つの置換基の置換位置は、オルト位、メタ位、パラ位の何れでも良い。〕
一般式(1)
〔式中、Yは酸素原子(O)、硫黄原子(S)、CO基、SO基又はSO2基を表わし、kは1〜5の整数であり、mは1〜10の整数であり、nは1以上の整数である。フェニル基に有する2つの置換基の置換位置は、オルト位、メタ位、パラ位の何れでも良い。〕
本発明に係る新規化合物は、下記一般式(1)で示される化合物である。
本発明に係る合成方法は、下記一般式(2)で示される酸フロライド体、好ましくは下記一般式(4)で示される酸フロライド体と、下記一般式(3)で示されるジアミノ基を有する化合物を、ピリジン溶媒中で反応させて請求項1記載の一般式(1)で示される化合物を合成することを特徴とする。
常温において液体(融点−42℃、沸点115.5℃)
本発明のオイル添加剤は、各種基油(オイル)に添加できるが、好ましくはフッ素系オイルに添加した場合に、フッ素系オイルの熱分解防止性能効果がある。
例示化合物1−1(一般式(1)において、k=3、m=1、n=1、Yは酸素原子、置換位置はパラ位)の合成
1H-NMR(Pyridine-d5)
7.158(4H,s,-O-Ph-O-)
7.16〜7.19(4H,m, NH-Ph-O-Ph-O-Ph-NH)
7.90〜7.95(4H,m, NH-Ph-O-Ph-O-Ph-NH)
12.707, 12.726(2H,2s,NH×2)
7.16〜7.19、および7.90〜7.95のPhは下記化12或いは化13の何れかで表される。
-145.3(2F,m,-OCF(CF3)CF2-O-×2)
-131.1(2F,m,-O-CF(CF3)CO-NH-×2)
-129.79,-129.76(4F,2s,CF3CF2CF 2- ×2)
-83〜-80(26F※,m,CF 3CF 2CF2-×2,-OCF(CF 3)CF 2-O-×2,-O-CF(CF 3)CO-NH- ×2)
※ピークが重なっていて分離不能
例示化合物1−2(一般式(1)において、k=3、m=1、n=11、Yは酸素原子、置換位置はパラ位)の合成
1H-NMR(Perfluorobenzene/Pyridine-d5=3/1)
6.93(4H,d,J=8.8Hz,NH-Ph-O-Ph-O-Ph-NH)
6.9953(4H,s,-O-Ph-O-)
7.69(4H,d,J=8.6Hz,NH-Ph-O-Ph-O-Ph-NH)
11.9518(2H,s,NH×2)
6.93、7.69のPhは合成例1と同様に、上記化12或いは化13の何れかで表される。
-143.1(22F,m,-O-CF(CF3)CF2-O-×11×2)
-128〜-130(6F,m,-O-CF(CF3)CO-NH-×2, CF3 CF2CF 2-×2)
-78〜-81
(126F※,m,CF 3CF2CF 2-×2,-OCF(CF 3)CF 2-O-×11×2,-O-CF(CF 3)CO-NH-×2)
※ピークが重なっていて分離不能
例示化合物1−3(一般式(1)において、k=3、m=1、n=40、Yは酸素原子、置換位置はパラ位)の合成
1H-NMR(neat)
6.9(8H※,m,NH-Ph-O-Ph-O-Ph-NH)
7.3(4H,m,NH-Ph-O-Ph-O-Ph-NH)
8.0(2H,br.s,NH ×2)
※ピークが重なっていて分離不能
6.9、7.3のNHに結合しているPhは合成例1と同様に、上記化12或いは化13の何れかで表される。
-142(80F,m,-OCF(CF3)CF2-O-×40×2)
-128〜-130(6F,m,-O-CF(CF3)CO-NH-×2, CF3 CF2 CF 2-×2)
-77〜-81(416F,m, CF 3CF 2 CF2-×2,-OCF(CF 3) CF 2-O-×40×2,-O-CF(CF 3)CO-NH-×2)
例示化合物1−4(一般式(1)において、k=3、m=2、n=1、Yは酸素原子、置換位置はパラ位)の合成
ビス[4−(4−アミノフェノキシ)フェニル]エーテル(25.2g:一般式(3)において、m=2、Yは酸素原子、置換位置はパラ位の化合物、CAS No.13080−88−1)をピリジン200mLに溶解し、氷浴上にて、酸フロライド(n=1)79gをゆっくり滴下し、0℃〜室温にて、終夜撹拌した。
1H-NMR(Pyridine-d5)
7.159(8H※,s, NH-Ph-O-Ph-O-Ph-O-Ph-NH)
7.16〜7.20(4H,m, NH-Ph-O-Ph-O-Ph-O-Ph-NH)
7.91〜7.94(4H,m, NH-Ph-O-Ph-O-Ph-O-Ph-NH)
12.705,12.727(2H,2s,NH×2)
※ピークが重なっていて分離不能
7.16〜7.20、および7.91〜7.94のPhは上記化12或いは化13の何れかで表される。
-145.4(2F,m,-OCF(CF3)CF2-O-×2)
-131.1(2F,m,-O-CF(CF3)CO-NH-×2)
-129.78,-129.75(4F,2s, CF3CF2CF 2- ×2)
-84〜-79(26F※,m,CF 3CF 2CF2-×2,-OCF(CF 3)CF 2-0-×2,-0-CF(CF 3)CO-NH- ×2)
※ピークが重なっていて分離不能
本発明の添加剤が無添加である例
試料量 10mg
昇温速度 20℃/min
初期温度 25℃
最高温度 500℃
雰囲気ガス 無し
オイル「フォンブリンM30」に、合成例2の生成物を1wt%添加して、比較例1と同じ条件にて熱分析測定を行った。その結果を図2に示す。
オイル「フォンブリンM30」に、合成例2の生成物を3wt%添加して、比較例1と同じ条件にて熱分析測定を行った。その結果を図3に示す。
実施例1において、合成例2の化合物に代えて、合成例1の化合物を用いて比較例1と同じ条件にて熱分析測定を行った。その結果を図4に示す。
実施例2において、合成例2の化合物に代えて、合成例1の化合物を用いて比較例1と同じ条件にて熱分析測定を行った。その結果を図5に示す。
オイル「フォンブリンM30」に、一般式(1)(k=3、m=0、n=1、Y=酸素原子、パラ位)の生成物を1wt%添加して、比較例1と同じ条件にて熱分析測定を行った。その結果を図6に示す。
Claims (2)
- 下記一般式(2)で示される酸フロライド体と、下記一般式(3)で示されるジアミノ基を有する化合物を、ピリジン溶媒中で反応させて下記一般式(1)で示される化合物を合成することを特徴とする合成方法。
一般式(2)
〔式中、kは1〜5の整数であり、nは1以上の整数である。〕
一般式(3)
〔式中、Yは酸素原子(O)、硫黄原子(S)、CO基、SO基又はSO2基を表わし、mは1〜10の整数である。フェニル基に有する2つの置換基の置換位置は、オルト位、メタ位、パラ位の何れでも良い。〕
一般式(1)
〔式中、Yは酸素原子(O)、硫黄原子(S)、CO基、SO基又はSO2基を表わし、kは1〜5の整数であり、mは1〜10の整数であり、nは1以上の整数である。フェニル基に有する2つの置換基の置換位置は、オルト位、メタ位、パラ位の何れでも良い。〕
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US (1) | US8273919B2 (ja) |
EP (2) | EP2236490B1 (ja) |
JP (2) | JP5231456B2 (ja) |
CN (2) | CN103254975B (ja) |
WO (1) | WO2009096571A1 (ja) |
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US8273919B2 (en) * | 2008-02-01 | 2012-09-25 | Unimatec Co., Ltd. | Compound, synthesis method thereof, and oil additive |
JP2021037428A (ja) * | 2020-12-15 | 2021-03-11 | 株式会社三洋物産 | 遊技機 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5912708A (ja) * | 1982-07-15 | 1984-01-23 | Nippon Mektron Ltd | 消泡剤 |
JPH0288635A (ja) * | 1988-09-26 | 1990-03-28 | Hitachi Ltd | 表面改質剤及びそれを用いた表面改質方法 |
JPH051293A (ja) * | 1990-11-28 | 1993-01-08 | Hitachi Ltd | 摺動部を有する冷却構造体を備えた機器及びそれに用いるコンパウンド |
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SU783311A1 (ru) * | 1978-12-22 | 1980-11-30 | Предприятие П/Я В-8415 | Резинова композици на основе сополимера винилиденфторида |
US5157066A (en) * | 1988-09-26 | 1992-10-20 | Hitachi, Ltd. | Fluoroalkyl ether, surface modifying composition and method for modifying surface |
JP2855081B2 (ja) * | 1994-10-31 | 1999-02-10 | 信越化学工業株式会社 | アミド化合物の製造方法 |
ITMI20051081A1 (it) * | 2005-06-10 | 2006-12-11 | Solvay Solexis Spa | Lubrificanti fluorurati |
US8273919B2 (en) * | 2008-02-01 | 2012-09-25 | Unimatec Co., Ltd. | Compound, synthesis method thereof, and oil additive |
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JPH0288635A (ja) * | 1988-09-26 | 1990-03-28 | Hitachi Ltd | 表面改質剤及びそれを用いた表面改質方法 |
JPH051293A (ja) * | 1990-11-28 | 1993-01-08 | Hitachi Ltd | 摺動部を有する冷却構造体を備えた機器及びそれに用いるコンパウンド |
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EP2818536B1 (en) | 2018-04-11 |
CN103254975B (zh) | 2015-06-24 |
JPWO2009096571A1 (ja) | 2011-05-26 |
EP2236490B1 (en) | 2016-10-12 |
WO2009096571A1 (ja) | 2009-08-06 |
EP2818536A1 (en) | 2014-12-31 |
EP2236490A1 (en) | 2010-10-06 |
US20100210875A1 (en) | 2010-08-19 |
EP2236490A4 (en) | 2014-03-05 |
CN101932554A (zh) | 2010-12-29 |
CN101932554B (zh) | 2013-08-07 |
CN103254975A (zh) | 2013-08-21 |
JP2013067664A (ja) | 2013-04-18 |
US8273919B2 (en) | 2012-09-25 |
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