JP5856572B2 - セルロース系材料から構成物質を抽出、単離する方法 - Google Patents
セルロース系材料から構成物質を抽出、単離する方法 Download PDFInfo
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- JP5856572B2 JP5856572B2 JP2012556585A JP2012556585A JP5856572B2 JP 5856572 B2 JP5856572 B2 JP 5856572B2 JP 2012556585 A JP2012556585 A JP 2012556585A JP 2012556585 A JP2012556585 A JP 2012556585A JP 5856572 B2 JP5856572 B2 JP 5856572B2
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- 238000003763 carbonization Methods 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- DPNGWXJMIILTBS-UHFFFAOYSA-N dehydronornicotine Natural products C1CCN=C1C1=CC=CN=C1 DPNGWXJMIILTBS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
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- 229920006158 high molecular weight polymer Polymers 0.000 description 1
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- 238000012432 intermediate storage Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 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
- 238000010327 methods by industry Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000008368 mint flavor Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
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- 210000000653 nervous system Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 210000003901 trigeminal nerve Anatomy 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/115—Natural spices, flavouring agents or condiments; Extracts thereof obtained by distilling, stripping, or recovering of volatiles
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/241—Extraction of specific substances
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/241—Extraction of specific substances
- A24B15/245—Nitrosamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Extraction Or Liquid Replacement (AREA)
- Manufacture Of Tobacco Products (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Mwt:分子量、BPt:沸点、Mpt:融点
(a)抽出物を供するための条件下でセルロース系材料を超臨界流体と接触させる工程と、
(b)抽出物から不溶性材料を除去する工程と、
(c)1つ以上の単離された構成成分を供するために蒸留によって抽出物を分留する工程とを含む。
(i)超臨界CO2抽出
約5kgのタバコを超臨界CO2で抽出した。その刻まれたくず状タバコを表3に示す条件下でCO2抽出プラントを使用して抽出した。
蒸留されるタバコ抽出物(416.65g)は、ろう状の固体を含む水を多く含む懸濁液であった。抽出物の水分量は、80%と見積もられた。蒸留工程を以下に説明する。
1.水の除去を含む第1段階は、130ミリバール、100°Cでシステムを作動させることによって行われた。粗タバコ抽出物の水の量の見積もりから予測されたように、61.4gの残渣が、246gの蒸留物(留分1)と共に、即ち20:80の比で得られた。
2.段階1からの残渣は、さらに2ミリバールの圧力、初期温度150°Cを140°Cに下げて精留し(留分2を得るために)、その際に残渣の炭化が発生し、そして温度を130°Cに下げた(留分3を得るために)。
第1蒸留工程によって246.0gの留分1(1613/01蒸留物、79.9%)が得られた。
B[a]P:0.8ng/g
TSNA類
NAB:140.55ng/g(0.1405μg/g)
NAT:2473.78ng/g(2.474μg/g)
NNK:1791.49ng/g(1.791μg/g)
NNN:3539.25ng/g(3.539μg/g)
合計TSNA含有量:7945.07ng/g(7.945μg/ml)
ニコチン:1085.1mg/ml
B[a]P:<28.11ng/ml
総TSNA量:5.69μg/ml
b[a]P(最大5ng/gの濃度まで)の量の測定方法
要約すると、2gのテストサンプルをメタノールKOHに抽出し、液/液分離を利用して洗浄する。このサンプルをガスクロマトグラフィー質量分析(GCMS)し、水分を補正し、乾式重量基準のng/gを測定する。
抽出溶媒
約500mlのメタノールと100mlの水に60gのKOHを入れる。この混合物を冷えるまで撹拌し、容量の低下をメタノールを加えて補正する。
ジメチルホルムアミド(DMF)/H2O溶液
水100mlと約500mlのDMFを使用。この混合物をよく振って、放冷する。放冷した後、量の低下をさらにDMFを加えて補正する。
飽和塩化ナトリウム溶媒
500mlのH2Oに塩化ナトリウムをすべて溶解しないように充分な量を加える。よく振る。
10%不活性シリカ
活性シリカ200gをPETE密閉キャップを有する1Lのショット瓶(schott bottle)に入れ、ガラスストッパーを挿入する。水20mlを5mlのアリコートで瓶に入れ、添加と添加の間は瓶を転がす。平衡になるように瓶を少なくとも2時間、放置する。
内部標準スパイキング溶液(Internal Standard Spiking Solution、ISTD)
10mlのISTD原液をシクロヘキサン(濃度10ng/ml)で希釈する。
原液A(B[a]P濃度=500ng/ml):シクロヘキサン中100ng/μlのB[a]P0.5mlをHPLCグレードのシクロヘキサンで100mlに希釈
原液B(B[a]P濃度=50ng/ml):10mlの原液AをHPLCメタノールで100mlに希釈
ISTD原液(B[a]P_D12濃度=500ng/ml):シクロヘキサン中100ng/μlの重水素化された0.5mlのB[a]Pを100mlのHPLグレードのシクロヘキサンで希釈する。
下記の表に示した量のISTD原液と原液BをHPLCグレードのシクロヘキサンで50mlに調製する。
各セットの抽出のために参照タバコ(2R4F;www.2r4f.com)のサンプルを対照タバコとして抽出しなければならない。
2g(±0.01g)のサンプルを1mlの内部標準スパイキング溶液に添加する。60mlのメタノールKOHを加え、栓をする。さらにこれを振ってから、60°Cの水槽に2時間置き、時々振る。その後取り除いて、ドラフトに入れ、冷却する。
約5mlのシクロヘキサンを分液漏斗に入れる。ガラスウールの栓を有する漏斗を分液漏斗の上部に置き、抽出物をガラスウールを通して分液漏斗内にろ過する。三角フラスコと漏斗を約100mlのシクロヘキサンですすぐ。分液漏斗に栓をし、激しく振る。2層分離させて、メタノール層(底層)を別の容器に移す。シクロヘキサン層を別の容器に移す。メタノール層を分液漏斗に戻し、さらに100mlのシクロヘキサンを加え、激しく振る。2つの層に分離させる。メタノール層を処分し、最初のシクロヘキサン層を漏斗に戻す。
分液漏斗中のシクロヘキサンに約50mlの水を加え、よく振る。2層分離させ、底の方にある水層を処分する。これを3回繰り返す。振っている間にエマルジョンが形成され、これは分離させている際に処分することができる。水での洗浄がすべて終わった後、残りのシクロヘキサン層をターボヴァップ(turbovap)管に写し、この管を40°Cのターボヴァップに移し、抽出物を約50mlにブローダウンする。
50mlのシクロヘキサンを分液漏斗に写し、同量のDMF/H2Oを分液漏斗に加え、激しく振る。2層分離させる。DMF/H2O(底層)をフラスコに移す。さらに50mlのDMF/H2Oを分液漏斗に加え、よく振る。2層分離させ、DMF/H2O(底層)を他の容器に移す。上のシクロヘキサン層を処分する。
分液漏斗をシクロヘキサンで数回すすぎ、すべての残留物を除去する。混合したDMF/H2O抽出物を分液漏斗に移す。同量のシクロヘキサンと50mlの飽和塩化ナトリウム溶液を加える。よく振る。2層分離させ、これら2つの層の間に塩の層が形成され、DMF/H2O層(底)層を処分する。ガラス漏斗にガラスウールの栓をゆっくりと置き、約2〜3cmの粒状無水硫酸ナトリウムを漏斗に入れる。漏斗をターボヴァップ管に入れ、硫酸ナトリウムを介してシクロヘキサン層をターボヴァップ管内にろ過する。40°Cのターボヴァップ内で約10mlにサンプルをブローダウンする。
10%の不活性シリカを5g(±0.05g)を秤量し、約10mlのシクロヘキサンを加えると、スラリーが形成される。これをガラスのコラムに移し、シリカが洗い流されるまでコラム内でビーカーをすすぐ。底から2cmになるまで粒状の硫酸ナトリウムを加える。コラムの下にターボヴァップ管を置く。サンプル10mlをコラム内に注ぎ、シクロヘキサンをコラムを介してターボヴァップ管内にろ過する。元のターボヴァップ管を約50mlのシクロヘキサンですすぎ、これをシリカに触れないように注意してコラムに移す。さらにシクロヘキサン100mlをゆっくり加え、コラムからB[a]Pを溶出させる。
重水素化B[a]PとB[a]P応答領域(response area)の応答比を標準のB[a]P濃度に対してプロットすることによって校正曲線を作成することができ、傾きと切片が算出される。
(応答比−切片)x内部標準濃度 ng/ml=B[a]Png/ml
傾き
最終サンプル量(ml)xB[a]P(ng/ml)=B[a]P湿重量基準
湿ったサンプルの重量(g)
湿ったサンプルのB[a]Pのng/gx100=乾燥基準のB[a]Pのng/g
(100−水分%)
タバコ中のTSNA類の定量を液体クロマトグラフィー−タンデム質量分析計(LC−MS/MS)を使用して行うことができる。
Claims (16)
- セルロース系材料から構成成分を抽出し、単離する方法であって、該方法は、
(a)抽出物を得るための条件下でセルロース系材料を超臨界流体と接触させる工程と、
(b)得られた抽出物から不溶性材を取り除く工程と、
(c)減圧下の蒸留によって抽出物を精留して1つ以上の分離された構成成分を供する工程とを含む方法。 - 工程(a)で使用される超臨界流体が二酸化炭素であることを特徴とする請求項1記載の方法。
- 工程(a)中の温度が約40°Cで、工程(a)中の圧力が約30MPaであることを特徴とする請求項2記載の方法。
- さらに工程(b)の前に水を除去する工程を含むことを特徴とする請求項1乃至3いずれか1項記載の方法。
- 工程(c)が80〜150°C、好ましくは90〜120°C、より好ましくは100〜110°Cの温度で実施される第1の蒸留工程を含むことを特徴とする請求項1乃至4いずれか1項記載の方法。
- 工程(c)が90〜130ミリバール、好ましくは100〜110ミリバール、より好ましくは100ミリバールの圧力で実施される第1の蒸留工程を含むことを特徴とする請求項1乃至5いずれか1項記載の方法。
- 工程(c)が1つ以上のさらなる蒸留工程を含むことを特徴とする請求項1乃至6いずれか1項記載の方法。
- 第1の追加の蒸留工程が1〜5ミリバール、好ましくは1〜3ミリバール、最も好ましくは2ミリバールの圧力および/または110〜180°C、より好ましくは120〜160°C、最も好ましくは135〜155°Cの初期温度で実施され、110〜150°C、好ましくは140°Cに初期温度を下げることを特徴とする請求項7記載の方法。
- 第2の追加の蒸留工程が1〜5ミリバール、好ましくは1〜3ミリバール、最も好ましくは2ミリバールの圧力および/または110〜180°C、より好ましくは120〜160°C、最も好ましくは135〜155°Cの初期温度で実施され、110〜140°C、好ましくは130°Cに初期温度を下げることを特徴とする請求項7または8記載の方法。
- セルロース系材料がモウズイカ、クローブ、ミント、茶、ユーカリまたはカモミールから得られることを特徴とする請求項1乃至9いずれか1項記載の方法。
- セルロース系材料がタバコ葉身であることを特徴とする請求項10記載の方法。
- 単離された構成成分が、これら構成成分が単離されたセルロース系材料と比較して、または同等の濃縮および/または処理された際にこれら構成成分が単離されたセルロース系材料と比較して、ニコチン、1つ以上のニトロサミン類またはベンゾピレンの内の1つ以上を実質的に含まないか、またはこれら化合物の1つ以上の量が減少していることを特徴とする請求項1乃至11いずれか1項記載の方法。
- 抽出された構成成分が実質的にニコチン、1つ以上のニトロサミン類および/またはベンゾピレンを含まないことを特徴とする請求項1乃至12いずれか1項記載の方法。
- 抽出された構成成分が0.1μg/ml未満の量のニトロサミン類および/または25mg/ml未満の量のニコチンおよび/または2ng/g未満の量のベンゾピレンを含むことを特徴とする請求項13記載の方法。
- 分離された構成成分がクマリン、プレゴン、ピペロナール、トランス−アネトール、サフロール、メチルオイゲノールまたはミリスチシンの内の1つ以上であることを特徴とする請求項1乃至14いずれか1項記載の方法。
- セルロース系材料から構成成分を抽出するための装置であって、該装置は、セルロース系材料から1つ以上の溶出を抽出するのに充分な条件下でセルロース系材料を超臨界流体と接触させて抽出物とラフィネートを形成するための手段と、抽出物をラフィネートから分離するための手段と、抽出物中の1つ以上の溶出を減圧下で分離するための蒸留手段とを含む装置。
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JP2015536149A (ja) * | 2012-11-26 | 2015-12-21 | ブリティッシュ アメリカン タバコ (インヴェストメンツ) リミテッドBritish Americantobacco (Investments) Limited | タバコ材料の処理 |
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JP2015536149A (ja) * | 2012-11-26 | 2015-12-21 | ブリティッシュ アメリカン タバコ (インヴェストメンツ) リミテッドBritish Americantobacco (Investments) Limited | タバコ材料の処理 |
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BR112012022593B1 (pt) | 2023-11-07 |
AU2011225887A1 (en) | 2012-09-20 |
EP2544560A1 (en) | 2013-01-16 |
NZ602076A (en) | 2013-08-30 |
ZA201206532B (en) | 2018-12-19 |
KR101959966B1 (ko) | 2019-03-20 |
AR080478A1 (es) | 2012-04-11 |
CL2012002435A1 (es) | 2013-07-12 |
MY160867A (en) | 2017-03-31 |
KR20160140985A (ko) | 2016-12-07 |
CA2790971A1 (en) | 2011-09-15 |
US20130160777A1 (en) | 2013-06-27 |
JP2013521007A (ja) | 2013-06-10 |
KR101851731B1 (ko) | 2018-04-24 |
GB201003887D0 (en) | 2010-05-12 |
CN102781264A (zh) | 2012-11-14 |
RU2566902C2 (ru) | 2015-10-27 |
TW201138920A (en) | 2011-11-16 |
US9022040B2 (en) | 2015-05-05 |
EP2544560B1 (en) | 2017-12-20 |
CN102781264B (zh) | 2016-10-19 |
UA109652C2 (uk) | 2015-09-25 |
KR20130007600A (ko) | 2013-01-18 |
PL2544560T3 (pl) | 2018-06-29 |
AU2011225887B2 (en) | 2013-12-05 |
WO2011110843A1 (en) | 2011-09-15 |
CA2790971C (en) | 2015-12-08 |
HUE036219T2 (hu) | 2018-06-28 |
BR112012022593A2 (pt) | 2016-08-30 |
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