JP6432306B2 - 含フッ素オレフィンを構成成分とする共沸様組成物 - Google Patents
含フッ素オレフィンを構成成分とする共沸様組成物 Download PDFInfo
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- JP6432306B2 JP6432306B2 JP2014237179A JP2014237179A JP6432306B2 JP 6432306 B2 JP6432306 B2 JP 6432306B2 JP 2014237179 A JP2014237179 A JP 2014237179A JP 2014237179 A JP2014237179 A JP 2014237179A JP 6432306 B2 JP6432306 B2 JP 6432306B2
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- 239000000203 mixture Substances 0.000 title claims description 169
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- 229910052731 fluorine Inorganic materials 0.000 title description 16
- 239000011737 fluorine Substances 0.000 title description 16
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- 239000002736 nonionic surfactant Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 1
- MZWNCLBFMIGBPH-UHFFFAOYSA-N aniline N,N-dimethylaniline Chemical compound NC1=CC=CC=C1.CN(C)C1=CC=CC=C1 MZWNCLBFMIGBPH-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 239000003093 cationic surfactant Substances 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
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- 229940043279 diisopropylamine Drugs 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
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- 230000004907 flux Effects 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
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- 239000000976 ink Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
- C07C21/073—Dichloro-alkenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
- C11D7/30—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/5059—Mixtures containing (hydro)chlorocarbons
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
[発明1]
(Z)−1,2−ジクロロ−3,3,3−トリフルオロプロペン(1223Z)と(E)−1,2−ジクロロ−エチレン(t−DCE)からなる、共沸(様)組成物。
[発明2]
0.0001モル%〜40モル%の1223Zと99.9999モル%〜60モル%のt−DCEとからなる、発明1に記載の共沸(様)組成物。
[発明3]
10モル%〜40モル%の1223Zと90モル%〜60モル%のt−DCEとからなる、発明1又は発明2に記載の不燃性の共沸(様)組成物。
[発明4]
(Z)−1,2−ジクロロ−3,3,3−トリフルオロプロペン(1223Z):20モル%、(E)−1,2−ジクロロ−エチレン(t−DCE):80モル%からなる共沸組成物。
[発明5]
発明1から発明4のいずれかに記載の共沸(様)組成物と、少なくとも一つの追加成分を含む液体組成物。
[発明6]
発明1から発明4のいずれかに記載の共沸(様)組成物と、該共沸(様)組成物に対して、10ppm〜30質量%の追加成分を少なくとも一つ含む、液体組成物。
[発明7]
発明1から発明6のいずれかに記載の共沸(様)組成物ないし液体組成物を含む、洗浄用溶剤。
[発明8]
発明1から発明6のいずれかに記載の共沸(様)組成物ないし液体組成物を、被洗浄物体に接触させる工程を含む、該被洗浄物体を洗浄する方法。
本発明の共沸(様)組成物(あるいは、該共沸(様)組成物を含む液体組成物)は、精密機械部品、電子材料(プリント基板、液晶表示器、磁気記録部品、半導体材料等)、樹脂加工部品、光学レンズ、衣料品などから異物、油脂、グリース、ワックス、フラックス、インキ等を除去するのに好適である。前述の通り、本発明の共沸(様)組成物は不燃性であり、適度な流動性や溶解性を有するので、異物(パーティクルなど)を洗い流したり、又は溶解したりして、除去できる。洗浄の手法は特に限定されないが、精密機械部品、電子材料などに本発明の共沸(様)組成物(あるいは、該共沸(様)組成物を含む液体組成物)を浸漬して汚れを洗い流す、ウェスでふき取る、スプレー洗浄を行う、などの方法が挙げられ、これらを組み合わせて使用しても良い。超音波洗浄機内に当該共沸(様)組成物を入れ、その液中に洗浄対象の物品を浸漬させ、超音波洗浄処理することは、特に好ましい態様の1つである。
セプタム、攪拌子、−10℃の冷媒が流せるジムロートを備えた50mL三つ口フラスコに、表1記載のモル濃度になるように1223Zとt−DCEを合わせて25mL仕込んだ。ジムロート上部には合成ゼオライト管を取り付けた。フラスコをオイルバスに浸し、攪拌しながら還流するまで加熱した。還流が開始してから一時間以上経過して組成が安定した後、セプタムからガスタイトシリンジで気相部をサンプリングして、ガスクロマトグラフィー分析した。液相部は同様に注射針を備えたポリプロピレン製シリンジを用いて、約1mLをサンプリングし、予め氷水で冷却した2mLバイアル瓶に移した後、ガスクロマトグラフィー分析を実施した。表1においては予め作成した検量線を用いてモル%表記とした。また、図1は横軸に1223Zの液相部組成、縦軸に1223Zの気相部組成をとり、表1の結果をプロットした。第一成分の1223Zが40モル%〜99.9999モル%、第二成分のt−DCEが0.0001〜60モル%の範囲において、気相部と液相部の組成が実質的に変化しない共沸組成物または共沸様組成物であることが明らかとなった。
日本工業規格JIS K2265−1「引火点の求め方−第1部:タグ密閉法」に準拠して、1223Zとt−DCEの混合液体の引火点をそれぞれ測定した。引火点測定には、自動引火点測定器atg−8l(田中科学機器製作株式会社)を使用した。各組成における測定結果を表2に示す。1223Zとt−DCEの共沸または共沸様組成物の範囲において、大気圧力条件下で引火点がないことが観測された。
<洗浄試験>
市販の25mLメスシリンダーを11mLの目盛り線で切断した。直径:約7.2mm×長さ:約40mmの清浄な硝子棒の質量を測定後、表記載のオイルに2分間浸漬し、10分間立てて液切した(過剰についたオイルを除去した)後、質量(ガラス棒+初期付着オイル)を測定後、前記のメスシリンダーに入れた。以下の表2に記載の組成が1233Z 20モル%、t−DCE 80モル%の共沸様組成物を10mLの液面まで仕込み、20℃の水を満たした小型超音波洗浄機(シチズン製SW5800)の中央部に立てた。超音波を照射すると時間と共に共沸様組成物が揮発し、8mLの目盛り線になった時点で、メスシリンダー内の液をガスクロマトグラフで分析した。その結果、全ての実施例1の実験例において、2mL揮発したにも関わらず、洗浄前後の液組成は実質に同一であった。すなわち、実機洗浄において、実施例1で用いた共沸様組成物は、部分的に揮発しても残液の組成が実質的に変化しない共沸様組成であることが示された。次にガラス棒を乾燥させて質量(ガラス棒と残存オイルとの総質量)を測定して、油除去率(残存オイルの質量÷初期付着オイルの質量×100[%])を求めると共に、拡大鏡で硝子の表面を観察した。その結果、全ての実施例において油除去率が100%であり、拡大鏡観察結果においては、油分の残存が認められなかったため良好と判断された。各実施例の結果を以下の表3に示す。
Claims (8)
- (Z)−1,2−ジクロロ−3,3,3−トリフルオロプロペン(1223Z)と(E)−1,2−ジクロロ−エチレン(t−DCE)からなる、共沸(様)組成物。
- 0.0001モル%〜40モル%の1223Zと99.9999モル%〜60モル%のt−DCEとからなる、請求項1に記載の共沸(様)組成物。
- 10モル%〜40モル%の1223Zと90モル%〜60モル%のt−DCEとからなる、請求項1又は請求項2に記載の不燃性の共沸(様)組成物。
- (Z)−1,2−ジクロロ−3,3,3−トリフルオロプロペン(1223Z):20モル%、(E)−1,2−ジクロロ−エチレン(t−DCE):80モル%からなる共沸組成物。
- 請求項1から請求項4のいずれかに記載の共沸(様)組成物と、少なくとも一つの追加成分を含む液体組成物。
- 請求項1から請求項4のいずれかに記載の共沸(様)組成物と、該共沸(様)組成物に対して、10ppm〜30質量%の追加成分を少なくとも一つ含む、液体組成物。
- 請求項1から請求項6のいずれかに記載の共沸(様)組成物ないし液体組成物を含む、洗浄用溶剤。
- 請求項1から請求項6のいずれかに記載の共沸(様)組成物ないし液体組成物を、被洗浄物体に接触させる工程を含む、該被洗浄物体を洗浄する方法。
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CN201580062994.2A CN107001997B (zh) | 2014-11-21 | 2015-10-20 | 以含氟烯烃为构成成分的类共沸组合物 |
US15/528,318 US10344250B2 (en) | 2014-11-21 | 2015-10-20 | Azeotropic composition having fluorine-containing olefin as constituent |
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JPH02221389A (ja) | 1989-02-23 | 1990-09-04 | Asahi Glass Co Ltd | バフ研磨洗浄剤 |
JPH02222469A (ja) | 1989-02-23 | 1990-09-05 | Asahi Glass Co Ltd | レジスト剥離剤 |
JPH02221962A (ja) | 1989-02-23 | 1990-09-04 | Asahi Glass Co Ltd | レジスト現像剤 |
JPH02222496A (ja) | 1989-02-23 | 1990-09-05 | Asahi Glass Co Ltd | ドライクリーニング用洗浄剤 |
JPH02221388A (ja) | 1989-02-23 | 1990-09-04 | Asahi Glass Co Ltd | 脱脂洗浄剤 |
JPH02222702A (ja) | 1989-02-23 | 1990-09-05 | Asahi Glass Co Ltd | 付着水除去用溶剤 |
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EP2271725B1 (en) * | 2008-05-07 | 2018-02-21 | The Chemours Company FC, LLC | Compositions comprising 2,3,3,3-tetrafluoropropene and 1,1,1-trifluoropropene |
EP2280916B1 (en) | 2008-05-12 | 2019-04-17 | Arkema Inc. | Compositions of hydrochlorofluoroolefins |
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US20120304686A1 (en) * | 2011-06-02 | 2012-12-06 | E. I. Du Pont De Nemours And Company | Absorption cycle system having dual absorption circuits |
JP6119757B2 (ja) | 2012-09-21 | 2017-04-26 | セントラル硝子株式会社 | 1,2−ジクロロ−3,3,3−トリフルオロプロペンの製造方法 |
JP6183370B2 (ja) | 2012-09-21 | 2017-08-23 | セントラル硝子株式会社 | 1,2−ジクロロ−3,3,3−トリフルオロプロペンの製造方法 |
US9879164B2 (en) | 2013-01-25 | 2018-01-30 | Trane International Inc. | Refrigerant additives and compositions |
GB2527015A (en) * | 2013-03-15 | 2015-12-09 | Trane Int Inc | Lubricant defoaming additives and compositions |
-
2014
- 2014-11-21 JP JP2014237179A patent/JP6432306B2/ja active Active
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2015
- 2015-10-20 WO PCT/JP2015/079494 patent/WO2016080133A1/ja active Application Filing
- 2015-10-20 US US15/528,318 patent/US10344250B2/en active Active
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CN107001997B (zh) | 2019-07-26 |
JP2016098334A (ja) | 2016-05-30 |
WO2016080133A1 (ja) | 2016-05-26 |
CN107001997A (zh) | 2017-08-01 |
US10344250B2 (en) | 2019-07-09 |
US20170321167A1 (en) | 2017-11-09 |
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