KR20150096671A - 폴리 알파-1,3-글루칸 에테르의 제조 - Google Patents
폴리 알파-1,3-글루칸 에테르의 제조 Download PDFInfo
- Publication number
- KR20150096671A KR20150096671A KR1020157016123A KR20157016123A KR20150096671A KR 20150096671 A KR20150096671 A KR 20150096671A KR 1020157016123 A KR1020157016123 A KR 1020157016123A KR 20157016123 A KR20157016123 A KR 20157016123A KR 20150096671 A KR20150096671 A KR 20150096671A
- Authority
- KR
- South Korea
- Prior art keywords
- glucan
- alpha
- poly
- polyalpha
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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- 150000002170 ethers Chemical class 0.000 title abstract description 79
- 238000002360 preparation method Methods 0.000 title abstract description 68
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- -1 ether compound Chemical class 0.000 claims abstract description 112
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 36
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 23
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 12
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- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
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- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 9
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- 150000004676 glycans Chemical class 0.000 description 6
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 6
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
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- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- UVECLJDRPFNRRQ-UHFFFAOYSA-N ethyl trifluoromethanesulfonate Chemical compound CCOS(=O)(=O)C(F)(F)F UVECLJDRPFNRRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- KRRYGFCJUCTWMH-UHFFFAOYSA-N fluorosulfonyloxyethane Chemical compound CCOS(F)(=O)=O KRRYGFCJUCTWMH-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 108090001082 glucan-binding proteins Proteins 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005517 mercerization Methods 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- MJYCCJGURLWLGE-UHFFFAOYSA-N propyl trifluoromethanesulfonate Chemical compound CCCOS(=O)(=O)C(F)(F)F MJYCCJGURLWLGE-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005820 transferase reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261740076P | 2012-12-20 | 2012-12-20 | |
| US201261740106P | 2012-12-20 | 2012-12-20 | |
| US201261740127P | 2012-12-20 | 2012-12-20 | |
| US201261740087P | 2012-12-20 | 2012-12-20 | |
| US201261740119P | 2012-12-20 | 2012-12-20 | |
| US61/740,127 | 2012-12-20 | ||
| US61/740,119 | 2012-12-20 | ||
| US61/740,076 | 2012-12-20 | ||
| US61/740,087 | 2012-12-20 | ||
| US61/740,106 | 2012-12-20 | ||
| PCT/US2013/075285 WO2014099724A1 (en) | 2012-12-20 | 2013-12-16 | Preparation of poly alpha-1,3-glucan ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150096671A true KR20150096671A (ko) | 2015-08-25 |
Family
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| Country | Link |
|---|---|
| EP (1) | EP2935339B1 (enExample) |
| JP (1) | JP6389470B2 (enExample) |
| KR (1) | KR20150096671A (enExample) |
| CN (1) | CN104854135B (enExample) |
| AU (1) | AU2013363174B2 (enExample) |
| CA (1) | CA2893950C (enExample) |
| CL (1) | CL2015001666A1 (enExample) |
| ES (1) | ES2740961T3 (enExample) |
| MX (1) | MX370288B (enExample) |
| MY (1) | MY168444A (enExample) |
| NZ (1) | NZ708491A (enExample) |
| PH (1) | PH12015501406B1 (enExample) |
| SG (1) | SG11201504397WA (enExample) |
| WO (1) | WO2014099724A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200024837A (ko) * | 2017-06-30 | 2020-03-09 | 듀폰 인더스트리얼 바이오사이언시스 유에스에이, 엘엘씨 | 다당류-엘라스토머 마스터배치 조성물 |
| JP2024517798A (ja) * | 2021-05-04 | 2024-04-23 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 不溶性アルファ－グルカンを含む組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT514137A1 (de) | 2013-04-05 | 2014-10-15 | Lenzing Akiengesellschaft | Polysaccharidfaser und Verfahren zu ihrer Herstellung |
| AT514468A1 (de) | 2013-06-17 | 2015-01-15 | Lenzing Akiengesellschaft | Hochsaugfähige Polysaccharidfaser und ihre Verwendung |
| AT514474B1 (de) | 2013-06-18 | 2016-02-15 | Chemiefaser Lenzing Ag | Polysaccharidfaser und Verfahren zu ihrer Herstellung |
| AU2014366222B2 (en) * | 2013-12-16 | 2018-07-19 | Nutrition & Biosciences USA 4, Inc. | Use of poly alpha-1,3-glucan ethers as viscosity modifiers |
| JP6559139B2 (ja) | 2013-12-18 | 2019-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | カチオン性ポリα−１，３−グルカンエーテル |
| EP3092267B1 (en) | 2014-01-06 | 2020-08-19 | DuPont Industrial Biosciences USA, LLC | Production of poly alpha-1,3-glucan films |
| WO2015109066A1 (en) | 2014-01-17 | 2015-07-23 | E. I. Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| US9714403B2 (en) | 2014-06-19 | 2017-07-25 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| EP3158043B1 (en) | 2014-06-19 | 2021-03-10 | Nutrition & Biosciences USA 4, Inc. | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| AU2015369929B2 (en) | 2014-12-22 | 2020-08-20 | Nutrition & Biosciences USA 4, Inc. | Polymeric blend containing poly alpha-1,3-glucan |
| AT518612B1 (de) * | 2015-02-06 | 2019-03-15 | Chemiefaser Lenzing Ag | Polysaccharid-Suspension, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO2016126685A1 (en) | 2015-02-06 | 2016-08-11 | E. I. Du Pont De Nemours And Company | Colloidal dispersions of poly alpha-1,3-glucan based polymers |
| CN107995923B (zh) | 2015-06-01 | 2021-11-02 | 营养与生物科学美国4公司 | 包含聚α-1,3-葡聚糖的胶体分散体的结构化的液体组合物 |
| CN107922512A (zh) * | 2015-08-28 | 2018-04-17 | 纳幕尔杜邦公司 | 苄基α‑(1→3)‑葡聚糖及其纤维 |
| US10731297B2 (en) | 2015-10-26 | 2020-08-04 | Dupont Industrial Biosciences Usa, Llc | Water insoluble alpha-(1,3-glucan) composition |
| US11230812B2 (en) | 2015-10-26 | 2022-01-25 | Nutrition & Biosciences Usa 4, Inc | Polysaccharide coatings for paper |
| JP7045313B2 (ja) | 2015-11-13 | 2022-03-31 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物 |
| JP6997706B2 (ja) | 2015-11-13 | 2022-01-18 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物 |
| WO2017083229A1 (en) | 2015-11-13 | 2017-05-18 | E. I. Du Pont De Nemours And Company | Glucan fiber compositions for use in laundry care and fabric care |
| US10895028B2 (en) | 2015-12-14 | 2021-01-19 | Dupont Industrial Biosciences Usa, Llc | Nonwoven glucan webs |
| AU2017286522B2 (en) * | 2016-06-13 | 2020-10-29 | Nutrition & Biosciences USA 4, Inc. | Detergent compositions |
| AU2017286524B2 (en) * | 2016-06-13 | 2021-09-23 | Nutrition & Biosciences USA 4, Inc. | Detergent compositions |
| AU2017362950B2 (en) * | 2016-11-16 | 2022-02-24 | Nutrition & Biosciences USA 4, Inc. | Cellulose/polysaccharide composites |
| KR20190082929A (ko) * | 2016-11-22 | 2019-07-10 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리알파-1,3-글루칸 에스테르 및 이로 제조된 물품 |
| JP7402045B2 (ja) * | 2016-12-16 | 2023-12-20 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 両親媒性多糖誘導体及びそれを含む組成物 |
| CN110198958B (zh) * | 2017-01-24 | 2022-04-26 | 营养与生物科学美国4公司 | 使用多糖生产沉淀碳酸钙的方法 |
| EP3676341B1 (en) * | 2017-09-01 | 2021-12-01 | Nutrition & Biosciences USA 4, Inc. | Latex compositions comprising polysaccharides |
| JP7343490B2 (ja) * | 2017-10-13 | 2023-09-12 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 流動性バルク粒状多糖 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000159806A (ja) * | 1998-11-24 | 2000-06-13 | Lion Corp | カルボキシメチル化ムタン並びに化粧料 |
| CN1133654C (zh) * | 1999-08-05 | 2004-01-07 | 武汉大学 | 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法 |
| CN1133653C (zh) * | 1999-08-05 | 2004-01-07 | 武汉大学 | 灵芝α-(1→3)-D-葡聚糖硫酸酯衍生物及其用途和制备方法 |
| CN100549079C (zh) * | 2003-07-09 | 2009-10-14 | 江崎格力高株式会社 | 含有α-1,4-葡聚糖和/或其修饰物的模压制品以及生产它们的方法 |
-
2013
- 2013-12-16 SG SG11201504397WA patent/SG11201504397WA/en unknown
- 2013-12-16 WO PCT/US2013/075285 patent/WO2014099724A1/en not_active Ceased
- 2013-12-16 NZ NZ70849113A patent/NZ708491A/en not_active IP Right Cessation
- 2013-12-16 CA CA2893950A patent/CA2893950C/en not_active Expired - Fee Related
- 2013-12-16 MY MYPI2015001373A patent/MY168444A/en unknown
- 2013-12-16 CN CN201380065899.9A patent/CN104854135B/zh active Active
- 2013-12-16 JP JP2015549524A patent/JP6389470B2/ja not_active Expired - Fee Related
- 2013-12-16 AU AU2013363174A patent/AU2013363174B2/en not_active Ceased
- 2013-12-16 KR KR1020157016123A patent/KR20150096671A/ko not_active Abandoned
- 2013-12-16 MX MX2015007768A patent/MX370288B/es active IP Right Grant
- 2013-12-16 ES ES13817801T patent/ES2740961T3/es active Active
- 2013-12-16 EP EP13817801.7A patent/EP2935339B1/en active Active
-
2015
- 2015-06-15 CL CL2015001666A patent/CL2015001666A1/es unknown
- 2015-06-18 PH PH12015501406A patent/PH12015501406B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200024837A (ko) * | 2017-06-30 | 2020-03-09 | 듀폰 인더스트리얼 바이오사이언시스 유에스에이, 엘엘씨 | 다당류-엘라스토머 마스터배치 조성물 |
| JP2024517798A (ja) * | 2021-05-04 | 2024-04-23 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 不溶性アルファ－グルカンを含む組成物 |
Also Published As
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|---|---|
| PH12015501406A1 (en) | 2015-09-14 |
| AU2013363174B2 (en) | 2017-08-03 |
| JP6389470B2 (ja) | 2018-09-12 |
| CA2893950C (en) | 2020-10-20 |
| NZ708491A (en) | 2019-10-25 |
| CN104854135B (zh) | 2018-06-22 |
| CA2893950A1 (en) | 2014-06-26 |
| WO2014099724A1 (en) | 2014-06-26 |
| CN104854135A (zh) | 2015-08-19 |
| MX370288B (es) | 2019-12-09 |
| AU2013363174A1 (en) | 2015-06-11 |
| PH12015501406B1 (en) | 2015-09-14 |
| EP2935339B1 (en) | 2019-05-15 |
| ES2740961T3 (es) | 2020-02-07 |
| MY168444A (en) | 2018-11-09 |
| JP2016503096A (ja) | 2016-02-01 |
| CL2015001666A1 (es) | 2015-10-02 |
| SG11201504397WA (en) | 2015-07-30 |
| MX2015007768A (es) | 2015-09-04 |
| EP2935339A1 (en) | 2015-10-28 |
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