RU2630666C2 - Способ получения содержащего мальтит сиропа - Google Patents
Способ получения содержащего мальтит сиропа Download PDFInfo
- Publication number
- RU2630666C2 RU2630666C2 RU2014135341A RU2014135341A RU2630666C2 RU 2630666 C2 RU2630666 C2 RU 2630666C2 RU 2014135341 A RU2014135341 A RU 2014135341A RU 2014135341 A RU2014135341 A RU 2014135341A RU 2630666 C2 RU2630666 C2 RU 2630666C2
- Authority
- RU
- Russia
- Prior art keywords
- maltose
- amylase
- syrup
- alpha
- dry matter
- Prior art date
Links
- 239000006188 syrup Substances 0.000 title claims abstract description 51
- 235000020357 syrup Nutrition 0.000 title claims abstract description 51
- 235000010449 maltitol Nutrition 0.000 title claims abstract description 31
- 239000000845 maltitol Substances 0.000 title claims abstract description 30
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 title claims abstract description 28
- 229940035436 maltitol Drugs 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims abstract description 74
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 24
- 229920002472 Starch Polymers 0.000 claims abstract description 20
- 239000008107 starch Substances 0.000 claims abstract description 20
- 235000019698 starch Nutrition 0.000 claims abstract description 20
- 235000013336 milk Nutrition 0.000 claims abstract description 16
- 239000008267 milk Substances 0.000 claims abstract description 16
- 210000004080 milk Anatomy 0.000 claims abstract description 16
- 108010028688 Isoamylase Proteins 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 101710117655 Maltogenic alpha-amylase Proteins 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 108090000637 alpha-Amylases Proteins 0.000 claims description 50
- 102000004139 alpha-Amylases Human genes 0.000 claims description 38
- 229940024171 alpha-amylase Drugs 0.000 claims description 38
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 27
- 239000008103 glucose Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- 102000003925 1,4-alpha-Glucan Branching Enzyme Human genes 0.000 claims description 11
- 108090000344 1,4-alpha-Glucan Branching Enzyme Proteins 0.000 claims description 11
- 108010019077 beta-Amylase Proteins 0.000 claims description 11
- 238000005194 fractionation Methods 0.000 claims description 11
- 238000007873 sieving Methods 0.000 claims description 6
- 238000005115 demineralization Methods 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- 229920002245 Dextrose equivalent Polymers 0.000 claims description 4
- 230000002328 demineralizing effect Effects 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract description 5
- 239000000600 sorbitol Substances 0.000 abstract description 5
- XJCCHWKNFMUJFE-CGQAXDJHSA-N Maltotriitol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H](O)[C@@H](O)CO)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 XJCCHWKNFMUJFE-CGQAXDJHSA-N 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 23
- 150000002482 oligosaccharides Chemical class 0.000 description 11
- 229920001542 oligosaccharide Polymers 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/22—Preparation of compounds containing saccharide radicals produced by the action of a beta-amylase, e.g. maltose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/16—Preparation of compounds containing saccharide radicals produced by the action of an alpha-1, 6-glucosidase, e.g. amylose, debranched amylopectin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/12—Disaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12000624.2 | 2012-01-31 | ||
| EP12000624 | 2012-01-31 | ||
| EP12001377 | 2012-02-29 | ||
| EP12001377.6 | 2012-02-29 | ||
| PCT/IB2013/000962 WO2013114223A2 (en) | 2012-01-31 | 2013-01-24 | Maltitol enriched products |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2014135341A RU2014135341A (ru) | 2016-03-27 |
| RU2630666C2 true RU2630666C2 (ru) | 2017-09-11 |
Family
ID=47605465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014135341A RU2630666C2 (ru) | 2012-01-31 | 2013-01-24 | Способ получения содержащего мальтит сиропа |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20150024437A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2809793B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6177804B2 (cg-RX-API-DMAC7.html) |
| CN (2) | CN104080919A (cg-RX-API-DMAC7.html) |
| BR (1) | BR112014018642B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2863356A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2014009227A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2630666C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013114223A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201406356B (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3038618B1 (fr) * | 2015-07-06 | 2017-08-25 | Roquette Freres | Procede de fabrication de maltitol presentant un rendement ameliore |
| US9911012B2 (en) * | 2015-09-25 | 2018-03-06 | International Business Machines Corporation | Overlapping, discrete tamper-respondent sensors |
| CN106798312A (zh) * | 2015-11-26 | 2017-06-06 | 山东福田药业有限公司 | 一种氢化淀粉水解物及其制备方法 |
| US11342922B1 (en) | 2020-12-21 | 2022-05-24 | Advanced Micro Devices, Inc. | Direct bi-directional gray code counter |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1935330A1 (de) * | 1968-07-12 | 1970-10-01 | Hayashibara Co | Verfahren zur Herstellung von Maltit |
| US4487198A (en) * | 1982-07-28 | 1984-12-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a high-purity maltose |
| US6346400B1 (en) * | 1998-12-29 | 2002-02-12 | Roquette Freres | Process for the preparation of a maltose-rich syrup |
| JP2002101896A (ja) * | 2000-07-25 | 2002-04-09 | Nisshi:Kk | マルトース液の製造方法 |
| RU2425892C2 (ru) * | 2009-09-30 | 2011-08-10 | Государственное образовательное учреждение высшего профессионального образования "Московский государственный университет прикладной биотехнологии" | Способ получения мальтозного сиропа |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3708396A (en) * | 1968-01-23 | 1973-01-02 | Hayashibara Co | Process for producing maltitol |
| JPS527487A (en) * | 1975-07-04 | 1977-01-20 | Agency Of Ind Science & Technol | Preparation of high-purity maltose |
| JPS53119812A (en) * | 1977-03-24 | 1978-10-19 | Nippon Shiryo Kogyo Kk | Process for preparing high purity multitole |
| JP3602903B2 (ja) | 1995-05-02 | 2004-12-15 | 東和化成工業株式会社 | 結晶マルチトール及びそれを含有する含蜜結晶の製造方法 |
| JP4711471B2 (ja) * | 1996-07-05 | 2011-06-29 | 三菱商事フードテック株式会社 | 結晶マルチトール及びそれを含有する含蜜結晶の製造方法 |
| CA2529508C (en) * | 2003-07-18 | 2013-08-27 | Cargill Incorporated | Process for preparing maltitol enriched products |
| CN100480393C (zh) * | 2004-08-10 | 2009-04-22 | 华南理工大学 | 高纯度麦芽糖制品的生产方法 |
| CN1986821A (zh) * | 2005-12-22 | 2007-06-27 | 张乃东 | 高纯度晶体状麦芽糖醇的制备方法 |
| FR2905705B1 (fr) | 2006-09-08 | 2011-11-04 | Syral | Procede d'obtention d'un sirop a haute teneur en maltitol et sirop ainsi obtenu |
| KR100868329B1 (ko) * | 2007-02-01 | 2008-11-12 | 씨제이제일제당 (주) | 효소를 이용한 고분지 아밀로오스 및 아밀로펙틴클러스터의 제조방법 |
-
2013
- 2013-01-24 US US14/375,445 patent/US20150024437A1/en not_active Abandoned
- 2013-01-24 BR BR112014018642-1A patent/BR112014018642B1/pt active IP Right Grant
- 2013-01-24 RU RU2014135341A patent/RU2630666C2/ru active
- 2013-01-24 JP JP2014555342A patent/JP6177804B2/ja active Active
- 2013-01-24 CN CN201380007135.4A patent/CN104080919A/zh active Pending
- 2013-01-24 WO PCT/IB2013/000962 patent/WO2013114223A2/en not_active Ceased
- 2013-01-24 CN CN201911065473.9A patent/CN110669803A/zh active Pending
- 2013-01-24 CA CA2863356A patent/CA2863356A1/en not_active Abandoned
- 2013-01-24 EP EP13725757.2A patent/EP2809793B1/en active Active
- 2013-01-24 MX MX2014009227A patent/MX2014009227A/es not_active Application Discontinuation
-
2014
- 2014-08-28 ZA ZA2014/06356A patent/ZA201406356B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1935330A1 (de) * | 1968-07-12 | 1970-10-01 | Hayashibara Co | Verfahren zur Herstellung von Maltit |
| US4487198A (en) * | 1982-07-28 | 1984-12-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a high-purity maltose |
| US6346400B1 (en) * | 1998-12-29 | 2002-02-12 | Roquette Freres | Process for the preparation of a maltose-rich syrup |
| JP2002101896A (ja) * | 2000-07-25 | 2002-04-09 | Nisshi:Kk | マルトース液の製造方法 |
| RU2425892C2 (ru) * | 2009-09-30 | 2011-08-10 | Государственное образовательное учреждение высшего профессионального образования "Московский государственный университет прикладной биотехнологии" | Способ получения мальтозного сиропа |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2809793A2 (en) | 2014-12-10 |
| EP2809793B1 (en) | 2019-10-30 |
| JP2015505469A (ja) | 2015-02-23 |
| CN104080919A (zh) | 2014-10-01 |
| CN110669803A (zh) | 2020-01-10 |
| MX2014009227A (es) | 2014-11-10 |
| BR112014018642B1 (pt) | 2021-10-13 |
| ZA201406356B (en) | 2016-01-27 |
| BR112014018642A2 (pt) | 2017-07-11 |
| RU2014135341A (ru) | 2016-03-27 |
| CA2863356A1 (en) | 2013-08-08 |
| WO2013114223A3 (en) | 2014-01-23 |
| JP6177804B2 (ja) | 2017-08-09 |
| WO2013114223A2 (en) | 2013-08-08 |
| US20150024437A1 (en) | 2015-01-22 |
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