JP2015534497A - 液状陽イオン交換体としての分枝鎖状脂肪酸 - Google Patents
液状陽イオン交換体としての分枝鎖状脂肪酸 Download PDFInfo
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- 125000005842 heteroatom Chemical group 0.000 description 1
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- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- IIUXHTGBZYEGHI-UHFFFAOYSA-N iso-margaric acid Natural products CC(C)CCCCCCCCCCCCCC(O)=O IIUXHTGBZYEGHI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
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- 231100001228 moderately toxic Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
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- 238000007747 plating Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000006152 selective media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 238000000638 solvent extraction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/04—Processes using organic exchangers
-
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
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- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
- C02F2001/425—Treatment of water, waste water, or sewage by ion-exchange using cation exchangers
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F2101/38—Organic compounds containing nitrogen
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
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- C07—ORGANIC CHEMISTRY
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- C07C209/84—Purification
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
Description
α=C相1/C相2
に従って、分配係数を用いて記載される。特殊な分配係数は、Kow、P値とも呼称される、であり、これは、オクタノール相と水相との間の化合物の分配平衡を特徴付ける:
Kow=P=Cオクタノール/C水
高い工業的需要があった、水溶液中で生理的pHで正電荷を有する有機化合物の例は、12−アミノラウリン酸(ALS)およびその誘導体、殊にそのメチルエステル(ALSME)である。ALSは、ポリマーを製造する際の重要な出発生成物である。従来、ALSは、化石原料から出発して、ブタジエンを三量体化し、引き続き水素化してシクロドデカンを形成させ、引き続き酸化してシクロドデカノンとし、ヒドロキシラウリンと反応させ、かつ引き続きベックマン転位により合成されるラウリンラクタムにより、低い収量を有するプロセスにおいて製造される。ALSまたはALSMEをバイオテクノロジーにより製造する、大いに期待される手段は、ドイツ連邦共和国特許第10200710060705号明細書中に記載されている。
a)有機化合物を含有する水溶液および疎水性有機溶液を準備する工程、その際に後者の疎水性有機溶液は、液状疎水性陽イオン交換体を含み、
b)前記水溶液と前記疎水性有機溶液とを接触させる工程、および
c)前記疎水性有機溶液を前記水溶液から分離する工程
を含み、
その際に前記液状疎水性陽イオン交換体は、少なくとも1個のアルキル置換基を有する飽和アルカン酸であり、
その際に前記有機化合物は、少なくとも1個の正電荷およびゼロの正味の電荷量または正の正味の電荷量を有する有機化合物である、水溶液から有機化合物を除去する方法によって解決される。
NR2R3H+−A−COOR1 (I)または
NR2R3H+−A−NR4R5H+ (II)
〔式中、R1は、水素、メチル、エチル、プロピル、イソプロピルまたは負電荷であり、
Aは、有利に非置換でありかつ直鎖状である、少なくとも3個、有利に少なくとも6個、特に有利に8個の炭素原子を有するアルキレン基であり、および
R2、R3、R4およびR5は、それぞれ、互いに独立して、水素、メチル、エチルおよびプロピルを含む群から選択されている〕の化合物である方法によって解決される。
前記疎水性有機溶液が、液状疎水性陽イオン交換体を含み、
前記液状疎水性陽イオン交換体が、少なくとも1個のアルキル置換基を有する飽和アルカン酸であり、および
前記有機化合物が、少なくとも1個の正電荷およびゼロの正味の電荷量または正の正味の電荷量を有する有機化合物である、前記反応混合物によって解決される。
NR2R3H+−A−COOR1 (I)または
NR2R3H+−A−NR4R5H+ (II)
〔式中、R1は、水素、メチル、エチル、プロピル、イソプロピルまたは負電荷であり、
Aは、有利に非置換でありかつ直鎖状である、少なくとも3個、有利に少なくとも6個、特に有利に8個の炭素原子を有するアルキレン基であり、および
R2、R3、R4およびR5は、それぞれ、互いに独立して、水素、メチル、エチルおよびプロピルを含む群から選択されている〕の化合物である、反応混合物によって解決される。
NR2R3H+−A−COOR1 (I)または
NR2R3H+−A−NR4R5H+ (II)
〔式中、R1は、水素、メチル、エチル、プロピル、イソプロピルまたは負電荷であり、
Aは、有利に非置換でありかつ直鎖状である、少なくとも3個、有利に少なくとも6個、特に有利に8個の炭素原子を有するアルキレン基である〕の化合物である。Aは、式(II)において記載された2個の置換基で少なくとも置換されている、分枝鎖状または非分枝鎖状の、直鎖状または環式のアルカンまたは芳香族化合物もしくはヘテロ芳香族化合物であることができる。特に好ましい実施態様において、有機化合物は、式IIの化合物であり、かつAは、式−(CH2)n−のアルキレン鎖であり、上記式中、nは、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39または40であり、さらに、特に好ましくは、R2=R3=R4=R5=R6=R7=Hであり、かつR2、R3、R4およびR5は、そのつど、互いに独立して、水素、メチル、エチルおよびプロピルを含む群から選択されている。好ましい実施態様において、前記有機化合物は、アミノラウリン酸またはそのエステル、好ましくは、そのメチルエステルである。
Claims (19)
- 水溶液から有機化合物を除去する方法であって、工程
a)有機化合物を含有する水溶液および疎水性有機溶液を準備する工程、その際に後者の疎水性有機溶液は、液状疎水性陽イオン交換体を含み、
b)前記水溶液と前記疎水性有機溶液とを接触させる工程、および
c)前記疎水性有機溶液を前記水溶液から分離する工程
を含み、
その際に前記液状疎水性陽イオン交換体は、有利に少なくとも12個の炭素原子を含む、少なくとも1個のアルキル置換基を有する飽和アルカン酸であり、
その際に前記有機化合物は、少なくとも1個の正電荷およびゼロの正味の電荷量または正の正味の電荷量を有する有機化合物である、前記方法。 - 前記有機化合物は、式
NR2R3H+−A−COOR1 (I)または
NR2R3H+−A−NR4R5H+ (II)
〔式中、R1は、水素、メチル、エチル、プロピル、イソプロピルまたは負電荷であり、
Aは、有利に非置換でありかつ直鎖状である、少なくとも3個、有利に少なくとも6個、特に有利に8個の炭素原子を有するアルキレン基であり、および
R2、R3、R4およびR5は、それぞれ、互いに独立して、水素、メチル、エチルおよびプロピルを含む群から選択されている〕の化合物である、請求項1記載の方法。 - 工程b)での水溶液中のpH値は、6〜8、有利に6.2〜7.2である、請求項1または2記載の方法。
- 前記工程b)での液状陽イオン交換体対有機化合物の物質量比率は、少なくとも1である、請求項1から3までのいずれか1項に記載の方法。
- 有機溶液対水溶液の容量比は、1:10〜10:1である、請求項1から4までのいずれか1項に記載の方法。
- 液状陽イオン交換体は、式(H3C)2CH−(CH2)n−COOHの分枝鎖状脂肪酸またはその非プロトン化された形であり、かつnは、少なくとも4、有利に少なくとも8でありかつ最も有利には14である、請求項1から5までのいずれか1項に記載の方法。
- 液状陽イオン交換体は、環式置換基以外のものだけを含む分枝鎖状脂肪酸である、請求項1から6までのいずれか1項に記載の方法。
- 前記水溶液は、さらに物質代謝活性細胞を含む、請求項1から7までのいずれか1項に記載の方法。
- 前記有機化合物は、細胞、有利に細菌細胞に対して毒性の化合物である、請求項8記載の方法。
- 前記有機溶剤は、さらに少なくとも1つの有機溶剤、有利に脂肪酸および/または脂肪酸エステルを含む、請求項1から9までのいずれか1項に記載の方法。
- 前記疎水性有機溶液は、液状疎水性陽イオン交換体を20〜80%、有利に25〜75%の容量割合で含有する、請求項10記載の方法。
- 前記有機化合物は、1,4−ブタンジアミン、1,5−ペンタンジアミン、1,6−ヘキサンジアミン、1,8−オクタンジアミン、1,14−テトラデカンジアミン、1,18−オクタデカンジアミン、2−メチル−1,5−ジアミノペンタン、2,2−ジメチル−1,5−ジアミノペンタン、4,4’−ジアミノジシクロヘキシルメタン、3,3’−ジメチル−4,4’−ジアミノジシクロヘキシルメタン、3,3’,5,5’−テトラメチル−4,4’−ジアミノジシクロヘキシルメタン、m−キシリレンジアミンまたはp−キシリレンジアミン、2.2.4−トリメチルヘキサメチレンジアミンまたは2.4.4−トリメチルヘキサメチレンジアミン、1.4−ジアミノシクロヘキサン、4.4’−ジアミノジシクロヘキシルプロパン、イソホロンジアミン、メタキシリレンジアミンおよびパラキシリレンジアミンを含む群からのジアミンである、請求項1から11までのいずれか1項に記載の方法。
- 前記工程b)での温度は、28〜70℃、有利に30〜37℃である、請求項1から12までのいずれか1項に記載の方法。
- 前記有機化合物を含有する水溶液と疎水性有機溶液とを含む反応混合物であって、
前記疎水性有機溶液が、液状疎水性陽イオン交換体を含み、
前記液状疎水性陽イオン交換体が、有利に少なくとも12個の炭素原子を含む、少なくとも1個のアルキル置換基を有する飽和アルカン酸であり、および
前記有機化合物が、少なくとも1個の正電荷およびゼロの正味の電荷量または正の正味の電荷量を有する有機化合物である、前記反応混合物。 - 前記有機化合物が式
NR2R3H+−A−COOR1 (I)または
NR2R3H+−A−NR4R5H+ (II)
〔式中、R1は、水素、メチル、エチル、プロピル、イソプロピルまたは負電荷であり、
Aは、有利に非置換でありかつ直鎖状である、少なくとも3個、有利に少なくとも6個、特に有利に8個の炭素原子を有するアルキレン基であり、および
R2、R3、R4およびR5は、それぞれ、互いに独立して、水素、メチル、エチルおよびプロピルを含む群から選択されている〕の化合物である、請求項14記載の反応混合物。 - 前記液状疎水性陽イオン交換体が式(H3C)2CH−(CH2)n−COOHの分枝鎖状脂肪酸またはその非プロトン化された形であり、かつnが少なくとも4、有利に少なくとも8でありかつ最も有利には14である、請求項14または15記載の反応混合物。
- 前記液状陽イオン交換体が、環式置換基以外のものだけを含む分枝鎖状脂肪酸である、請求項14から16までのいずれか1項に記載の反応混合物。
- 前記水溶液が、さらに物質代謝活性細胞を含む、請求項14から17までのいずれか1項に記載の反応混合物。
- 前記有機化合物が、ブタンジアミン、1,5−ペンタンジアミン、1,6−ヘキサンジアミン、1,8−オクタンジアミン、1,14−テトラデカンジアミン、1,18−オクタデカンジアミン、2−メチル−1,5−ジアミノペンタン、2,2−ジメチル−1,5−ジアミノペンタン、4,4’−ジアミノジシクロヘキシルメタン、3,3’−ジメチル−4,4’−ジアミノジシクロヘキシルメタン、3,3’,5,5’−テトラメチル−4,4’−ジアミノジシクロヘキシルメタン、m−キシリレンジアミンまたはp−キシリレンジアミン、2.2.4−トリメチルヘキサメチレンジアミンまたは2.4.4−トリメチルヘキサメチレンジアミン、1.4−ジアミノシクロヘキサン、4.4’−ジアミノジシクロヘキシルプロパン、イソホロンジアミン、メタキシリレンジアミンおよびパラキシリレンジアミンを含む群からのジアミンである、請求項14から18までのいずれか1項に記載の反応混合物。
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EP12181153.3 | 2012-08-21 | ||
EP12181153.3A EP2700448A1 (de) | 2012-08-21 | 2012-08-21 | Verzweigte Fettsäuren als flüssige Kationenaustauscher |
PCT/EP2013/065563 WO2014029577A1 (de) | 2012-08-21 | 2013-07-24 | Verzweigte fettsäuren als flüssige kationenaustauscher |
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JP2015527826A Active JP6305404B2 (ja) | 2012-08-21 | 2013-07-24 | 液状陽イオン交換体としての分枝鎖状脂肪酸 |
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US (1) | US9919303B2 (ja) |
EP (2) | EP2700448A1 (ja) |
JP (1) | JP6305404B2 (ja) |
KR (1) | KR102114695B1 (ja) |
CN (1) | CN104540588B (ja) |
BR (1) | BR112015003537B1 (ja) |
ES (1) | ES2710934T3 (ja) |
HK (1) | HK1208198A1 (ja) |
MX (1) | MX363186B (ja) |
SG (2) | SG10201701336XA (ja) |
WO (1) | WO2014029577A1 (ja) |
Families Citing this family (5)
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EP2602328A1 (de) * | 2011-12-05 | 2013-06-12 | Evonik Industries AG | Verfahren zur Oxidation von Alkanen unter Verwendung einer AlkB Alkan 1-Monooxygenase |
EP2700448A1 (de) | 2012-08-21 | 2014-02-26 | Evonik Industries AG | Verzweigte Fettsäuren als flüssige Kationenaustauscher |
EP2746400A1 (de) | 2012-12-21 | 2014-06-25 | Evonik Industries AG | Herstellung von Aminen und Diaminen aus einer Carbonsäure oder Dicarbonsäure oder eines Monoesters davon |
EP2759598A1 (de) | 2013-01-24 | 2014-07-30 | Evonik Industries AG | Verfahren zur Herstellung von alpha, omega-Alkandiol |
CN108298744B (zh) * | 2018-03-16 | 2021-02-09 | 天津市海跃水处理高科技有限公司 | 一种养殖废水的非生化深度处理方法 |
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-
2012
- 2012-08-21 EP EP12181153.3A patent/EP2700448A1/de not_active Withdrawn
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2013
- 2013-07-24 EP EP13739729.5A patent/EP2888046B1/de active Active
- 2013-07-24 US US14/419,580 patent/US9919303B2/en active Active
- 2013-07-24 KR KR1020157003992A patent/KR102114695B1/ko active IP Right Grant
- 2013-07-24 SG SG10201701336XA patent/SG10201701336XA/en unknown
- 2013-07-24 ES ES13739729T patent/ES2710934T3/es active Active
- 2013-07-24 MX MX2015002183A patent/MX363186B/es unknown
- 2013-07-24 JP JP2015527826A patent/JP6305404B2/ja active Active
- 2013-07-24 CN CN201380044331.9A patent/CN104540588B/zh active Active
- 2013-07-24 SG SG11201501142XA patent/SG11201501142XA/en unknown
- 2013-07-24 BR BR112015003537-0A patent/BR112015003537B1/pt active IP Right Grant
- 2013-07-24 WO PCT/EP2013/065563 patent/WO2014029577A1/de active Application Filing
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- 2015-09-14 HK HK15108956.8A patent/HK1208198A1/xx unknown
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JPS5772935A (en) * | 1980-10-06 | 1982-05-07 | Miles Lab | Extraction of organic acid |
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SG10201701336XA (en) | 2017-03-30 |
JP6305404B2 (ja) | 2018-04-04 |
SG11201501142XA (en) | 2015-04-29 |
KR102114695B1 (ko) | 2020-05-25 |
BR112015003537B1 (pt) | 2021-10-19 |
US20150209775A1 (en) | 2015-07-30 |
MX2015002183A (es) | 2015-05-07 |
ES2710934T3 (es) | 2019-04-29 |
EP2888046A1 (de) | 2015-07-01 |
CN104540588A (zh) | 2015-04-22 |
US9919303B2 (en) | 2018-03-20 |
EP2888046B1 (de) | 2018-11-14 |
WO2014029577A1 (de) | 2014-02-27 |
EP2700448A1 (de) | 2014-02-26 |
CN104540588B (zh) | 2017-03-01 |
MX363186B (es) | 2019-03-13 |
KR20150046034A (ko) | 2015-04-29 |
HK1208198A1 (en) | 2016-02-26 |
BR112015003537A2 (pt) | 2021-05-11 |
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