JP2013508360A - 重水素化芳香族化合物を調製する方法 - Google Patents
重水素化芳香族化合物を調製する方法 Download PDFInfo
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- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 239000011903 deuterated solvents Substances 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004431 deuterium atom Chemical group 0.000 claims abstract description 14
- -1 aromatic hydrogen Chemical class 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 32
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 2
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
- 239000003341 Bronsted base Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000037353 metabolic pathway Effects 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
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Abstract
Description
(a)第1の重水素化溶媒に溶解または分散されている、芳香族水素を有する芳香族化合物を含む液体組成物を提供する工程と、
(b)1以下のpKaを有する第1の酸でこの液体組成物を処理して、第1の重水素化材料を生成させる工程と
を含み、芳香族水素に対する重水素原子の当量比が少なくとも2である、方法が提供される。
(d)第2の重水素化溶媒にこの第1の重水素化材料を溶解または分散させて、第2の液体組成物を生成させる工程と、
(e)1以下のpKaを有する第2の酸でこの第2の液体組成物を処理して、第2の重水素化材料を生成させる工程と
をさらに含む、前述した方法も提供される。
以下で記載された実施形態の詳細を扱う前に、幾つかの用語を定義し、説明する。
本方法は、
(a)第1の重水素化溶媒に溶解または分散されている、芳香族水素を有する芳香族化合物を含む液体組成物を提供する工程と、
(b)1以下の水中のpKaを有する第1の酸でこの液体組成物を処理して、第1の重水素化材料を生成させる工程と
を含み、ここで、芳香族水素に対する重水素原子の当量比は少なくとも2である。
(c)第1の重水素化材料を単離する工程、
(d)第2の重水素化溶媒に第1の重水素化材料を溶解または分散させて、第2の液体組成物を生成させる工程、および
(e)1以下のpKaを有する第2の酸でこの第2の液体組成物を処理して、第2の重水素化材料を生成させる工程
これらの実施例は、異なる芳香族化合物による本発明の方法を例示す。
NBPは、
この実施例および比較例は酸pKaの影響を例示している。
以下、本明細書に記載の主な態様につき列記する。
[1]
重水素化芳香族化合物を調製する方法であって、
(a)第1の重水素化溶媒に溶解または分散されている、芳香族水素を有する芳香族化合物を含む液体組成物を提供する工程と、
(b)1以下の水中のpKaを有する第1の酸で前記液体組成物を処理して、第1の重水素化材料を生成させる工程とを含み、
芳香族水素に対する重水素原子の当量比が少なくとも2である、方法。
[2]
前記当量比が2〜50の範囲内である、前記[1]に記載の方法。
[3]
前記当量比が10〜30の範囲内である、前記[1]に記載の方法。
[4]
前記芳香族化合物が、芳香族水素を有する少なくとも1個の炭化水素芳香族環を有する、前記[1]に記載の方法。
[5]
前記酸が重水素−酸である、前記[1]に記載の方法。
[6]
芳香族水素に対する重水素−酸の当量比が0.1〜10の範囲内ある、
前記[1]に記載の方法。
[7]
前記pKaが−2以下である、前記[1]に記載の方法。
[8]
工程(b)が室温および大気圧で行われる、前記[1]に記載の方法。
[9]
工程(b)が24時間以下にわたり行われる、前記[1]に記載の方法。
[10]
工程(b)が2時間以下にわたり行われる、前記[1]に記載の方法。
[11]
(c)前記第1の重水素化材料を単離する工程と、
(d)第2の重水素化溶媒に前記第1の重水素化材料を溶解または分散させて、第2の液体組成物を生成させる工程と、
(e)1以下のpKaを有する第2の酸で前記第2の液体組成物を処理して、第2の重水素化材料を生成させる工程と、
をさらに含む、前記[1]に記載の方法。
Claims (11)
- 重水素化芳香族化合物を調製する方法であって、
(a)第1の重水素化溶媒に溶解または分散されている、芳香族水素を有する芳香族化合物を含む液体組成物を提供する工程と、
(b)1以下の水中のpKaを有する第1の酸で前記液体組成物を処理して、第1の重水素化材料を生成させる工程と
を含み、芳香族水素に対する重水素原子の当量比が少なくとも2である、方法。 - 前記当量比が2〜50の範囲内である、請求項1に記載の方法。
- 前記当量比が10〜30の範囲内である、請求項1に記載の方法。
- 前記芳香族化合物が、芳香族水素を有する少なくとも1個の炭化水素芳香族環を有する、請求項1に記載の方法。
- 前記酸が重水素−酸である、請求項1に記載の方法。
- 芳香族水素に対する重水素−酸の当量比が0.1〜10の範囲内ある、請求項1に記載の方法。
- 前記pKaが−2以下である、請求項1に記載の方法。
- 工程(b)が室温および大気圧で行われる、請求項1に記載の方法。
- 工程(b)が24時間以下にわたり行われる、請求項1に記載の方法。
- 工程(b)が2時間以下にわたり行われる、請求項1に記載の方法。
- (c)前記第1の重水素化材料を単離する工程と、
(d)第2の重水素化溶媒に前記第1の重水素化材料を溶解または分散させて、第2の液体組成物を生成させる工程と、
(e)1以下のpKaを有する第2の酸で前記第2の液体組成物を処理して、第2の重水素化材料を生成させる工程と、
をさらに含む、請求項1に記載の方法。
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US25484309P | 2009-10-26 | 2009-10-26 | |
US61/254,843 | 2009-10-26 | ||
PCT/US2009/068924 WO2011053334A1 (en) | 2009-10-26 | 2009-12-21 | Method for preparing deuterated aromatic compounds |
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JP2013508360A true JP2013508360A (ja) | 2013-03-07 |
JP5662461B2 JP5662461B2 (ja) | 2015-01-28 |
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EP (1) | EP2493835A4 (ja) |
JP (1) | JP5662461B2 (ja) |
KR (1) | KR101538534B1 (ja) |
CN (1) | CN102574753B (ja) |
TW (1) | TW201114735A (ja) |
WO (1) | WO2011053334A1 (ja) |
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US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
WO2010114583A1 (en) | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
CN102510889B (zh) | 2009-09-29 | 2015-11-25 | E.I.内穆尔杜邦公司 | 用于发光应用的氘代化合物 |
WO2011059463A1 (en) | 2009-10-29 | 2011-05-19 | E. I. Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
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JP5662461B2 (ja) | 2015-01-28 |
CN102574753B (zh) | 2015-07-08 |
EP2493835A1 (en) | 2012-09-05 |
KR101538534B1 (ko) | 2015-07-21 |
TW201114735A (en) | 2011-05-01 |
KR20120101029A (ko) | 2012-09-12 |
EP2493835A4 (en) | 2015-07-15 |
WO2011053334A1 (en) | 2011-05-05 |
CN102574753A (zh) | 2012-07-11 |
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