CN105008401A - 聚α-1，3-葡聚糖酯和由其所得膜的制备 - Google Patents
聚α-1，3-葡聚糖酯和由其所得膜的制备 Download PDFInfo
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- CN105008401A CN105008401A CN201380073853.1A CN201380073853A CN105008401A CN 105008401 A CN105008401 A CN 105008401A CN 201380073853 A CN201380073853 A CN 201380073853A CN 105008401 A CN105008401 A CN 105008401A
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- dextran
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- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 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
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| US201261746335P | 2012-12-27 | 2012-12-27 | |
| US201261746338P | 2012-12-27 | 2012-12-27 | |
| US201261746328P | 2012-12-27 | 2012-12-27 | |
| US61/746335 | 2012-12-27 | ||
| US61/746328 | 2012-12-27 | ||
| US61/746338 | 2012-12-27 | ||
| PCT/US2013/076919 WO2014105698A1 (en) | 2012-12-27 | 2013-12-20 | Preparation of poly alpha-1,3-glucan esters and films therefrom |
Publications (1)
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|---|---|
| CN105008401A true CN105008401A (zh) | 2015-10-28 |
Family
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Family Applications (1)
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| CN201380073853.1A Pending CN105008401A (zh) | 2012-12-27 | 2013-12-20 | 聚α-1，3-葡聚糖酯和由其所得膜的制备 |
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| US (3) | US9278988B2 (https=) |
| EP (1) | EP2938639B1 (https=) |
| JP (1) | JP6261610B2 (https=) |
| KR (1) | KR20150100702A (https=) |
| CN (1) | CN105008401A (https=) |
| AU (1) | AU2013370663B2 (https=) |
| BR (1) | BR112015015528A8 (https=) |
| CA (1) | CA2895132A1 (https=) |
| CL (1) | CL2015001853A1 (https=) |
| ES (1) | ES2736042T3 (https=) |
| MX (1) | MX370287B (https=) |
| MY (1) | MY170135A (https=) |
| NZ (1) | NZ708558A (https=) |
| PH (1) | PH12015501541A1 (https=) |
| SG (2) | SG11201504218XA (https=) |
| WO (2) | WO2014105696A1 (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105026467A (zh) * | 2013-12-20 | 2015-11-04 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯膜和它们的制备方法 |
| CN110248966A (zh) * | 2016-11-22 | 2019-09-17 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯及由其制成的制品 |
| CN111051444A (zh) * | 2017-09-01 | 2020-04-21 | 杜邦工业生物科学美国有限责任公司 | 包含多糖的胶乳组合物 |
| CN111788266A (zh) * | 2018-02-26 | 2020-10-16 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN115667477A (zh) * | 2020-06-10 | 2023-01-31 | 宝洁公司 | 包含聚α-1,3-葡聚糖酯的产品 |
| CN116589606A (zh) * | 2022-12-01 | 2023-08-15 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
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| AU2015204026B2 (en) | 2014-01-06 | 2018-08-16 | Nutrition & Biosciences USA 4, Inc. | Production of poly alpha-1,3-glucan films |
| US10106626B2 (en) | 2014-01-17 | 2018-10-23 | Ei Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| AU2015206354A1 (en) * | 2014-01-17 | 2016-07-21 | E. I. Du Pont De Nemours And Company | Production of gelled networks of poly alpha-1,3-glucan formate and films therefrom |
| WO2015200596A1 (en) * | 2014-06-26 | 2015-12-30 | E. I. Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ester films |
| EP3237454B1 (en) | 2014-12-22 | 2020-08-12 | DuPont Industrial Biosciences USA, LLC | Polymeric blend containing poly alpha-1,3-glucan |
| ES2803024T3 (es) | 2015-02-06 | 2021-01-22 | Dupont Ind Biosciences Usa Llc | Dispersiones coloidales de polímeros basados en poli-alfa-1,3-glucano |
| EP3303411B1 (en) | 2015-06-01 | 2020-11-18 | DuPont Industrial Biosciences USA, LLC | Structured liquid compositions comprising colloidal dispersions of poly alpha-1,3-glucan |
| BR112017028167A2 (pt) | 2015-06-30 | 2018-08-28 | Du Pont | composição e método de produção de composto |
| CN108350660B (zh) * | 2015-10-26 | 2022-04-29 | 营养与生物科学美国4公司 | 水不溶性α-(1，3→葡聚糖)组合物 |
| CA2997563C (en) | 2015-10-26 | 2022-03-22 | E. I. Du Pont De Nemours And Company | Polysaccharide coatings for paper |
| WO2017083228A1 (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 |
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| 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 |
| KR102486203B1 (ko) | 2016-07-22 | 2023-01-11 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 다당류를 포함하는 폴리우레탄 중합체 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1283632A (zh) * | 1999-08-05 | 2001-02-14 | 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 |
| TW504525B (en) * | 1999-01-25 | 2002-10-01 | Du Pont | Polysaccharide fibers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501886A (en) * | 1982-08-09 | 1985-02-26 | E. I. Du Pont De Nemours And Company | Cellulosic fibers from anisotropic solutions |
| 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 |
| JP4584146B2 (ja) | 2003-07-09 | 2010-11-17 | 江崎グリコ株式会社 | α−１，４−グルカンおよび／またはその修飾物を含む成型物およびその製造方法 |
| US8642757B2 (en) | 2011-09-09 | 2014-02-04 | E I Du Pont De Nemours And Company | High titer production of highly linear poly (α 1,3 glucan) |
| US9080195B2 (en) | 2011-09-09 | 2015-07-14 | E I Du Pont De Nemours And Company | High titer production of poly (α 1,3 glucan) |
| NZ708558A (en) * | 2012-12-27 | 2019-10-25 | Du Pont | Preparation of poly alpha-1,3-glucan esters and films therefrom |
| BR112015015609B1 (pt) * | 2012-12-27 | 2021-04-06 | Nutrition & Biosciences USA 4, Inc. | Filmes e método para a preparação de um filme de éster de poli alfa-1,3-glucano |
-
2013
- 2013-12-20 NZ NZ70855813A patent/NZ708558A/en not_active IP Right Cessation
- 2013-12-20 MY MYPI2015701718A patent/MY170135A/en unknown
- 2013-12-20 SG SG11201504218XA patent/SG11201504218XA/en unknown
- 2013-12-20 KR KR1020157017106A patent/KR20150100702A/ko not_active Abandoned
- 2013-12-20 WO PCT/US2013/076905 patent/WO2014105696A1/en not_active Ceased
- 2013-12-20 WO PCT/US2013/076919 patent/WO2014105698A1/en not_active Ceased
- 2013-12-20 US US14/136,226 patent/US9278988B2/en active Active
- 2013-12-20 CN CN201380073853.1A patent/CN105008401A/zh active Pending
- 2013-12-20 CA CA2895132A patent/CA2895132A1/en not_active Abandoned
- 2013-12-20 ES ES13821334T patent/ES2736042T3/es active Active
- 2013-12-20 BR BR112015015528A patent/BR112015015528A8/pt not_active Application Discontinuation
- 2013-12-20 MX MX2015008463A patent/MX370287B/es active IP Right Grant
- 2013-12-20 JP JP2015550693A patent/JP6261610B2/ja active Active
- 2013-12-20 US US14/136,168 patent/US20140187766A1/en not_active Abandoned
- 2013-12-20 EP EP13821334.3A patent/EP2938639B1/en active Active
- 2013-12-20 AU AU2013370663A patent/AU2013370663B2/en not_active Ceased
-
2014
- 2014-06-26 SG SG11201505127QA patent/SG11201505127QA/en unknown
-
2015
- 2015-06-26 CL CL2015001853A patent/CL2015001853A1/es unknown
- 2015-07-08 PH PH12015501541A patent/PH12015501541A1/en unknown
-
2016
- 2016-03-02 US US15/058,406 patent/US10000580B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW504525B (en) * | 1999-01-25 | 2002-10-01 | Du Pont | Polysaccharide fibers |
| CN1283632A (zh) * | 1999-08-05 | 2001-02-14 | 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 |
Non-Patent Citations (5)
| Title |
|---|
| G•奥迪安: "《聚合反应原理》", 30 June 1987, 科学出版社 * |
| KOZO OGAWA ET AL.: "X-ray diffraction data for (1→3)-α-d-glucan triacetate", 《CARBOHYDRATE POLYMERS》 * |
| 张惟杰: "《糖复合物生化研究技术 第二版》", 31 October 1994, 浙江大学出版社 * |
| 王孟钟 等: "《胶粘剂应用手册》", 30 November 1987, 化学工业出版社 * |
| 胡玉洁: "《天然高分子材料改性与应用》", 31 July 2003, 北京：化学工业出版社 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105026467A (zh) * | 2013-12-20 | 2015-11-04 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯膜和它们的制备方法 |
| CN110248966A (zh) * | 2016-11-22 | 2019-09-17 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯及由其制成的制品 |
| CN110248966B (zh) * | 2016-11-22 | 2023-02-17 | 营养与生物科学美国4公司 | 聚α-1，3-葡聚糖酯及由其制成的制品 |
| CN111051444A (zh) * | 2017-09-01 | 2020-04-21 | 杜邦工业生物科学美国有限责任公司 | 包含多糖的胶乳组合物 |
| CN111788266A (zh) * | 2018-02-26 | 2020-10-16 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN111788266B (zh) * | 2018-02-26 | 2023-08-22 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN115667477A (zh) * | 2020-06-10 | 2023-01-31 | 宝洁公司 | 包含聚α-1,3-葡聚糖酯的产品 |
| CN116589606A (zh) * | 2022-12-01 | 2023-08-15 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
| CN116589606B (zh) * | 2022-12-01 | 2024-05-28 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
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| EP2938639A1 (en) | 2015-11-04 |
| KR20150100702A (ko) | 2015-09-02 |
| US10000580B2 (en) | 2018-06-19 |
| BR112015015528A8 (pt) | 2019-10-22 |
| ES2736042T3 (es) | 2019-12-23 |
| WO2014105696A1 (en) | 2014-07-03 |
| JP6261610B2 (ja) | 2018-01-17 |
| SG11201504218XA (en) | 2015-07-30 |
| AU2013370663A1 (en) | 2015-06-18 |
| US9278988B2 (en) | 2016-03-08 |
| SG11201505127QA (en) | 2015-07-30 |
| US20160251453A1 (en) | 2016-09-01 |
| EP2938639B1 (en) | 2019-05-01 |
| MX370287B (es) | 2019-12-09 |
| JP2016505692A (ja) | 2016-02-25 |
| MY170135A (en) | 2019-07-06 |
| WO2014105698A1 (en) | 2014-07-03 |
| BR112015015528A2 (pt) | 2017-07-11 |
| PH12015501541B1 (en) | 2015-10-05 |
| MX2015008463A (es) | 2015-09-23 |
| NZ708558A (en) | 2019-10-25 |
| AU2013370663B2 (en) | 2017-07-27 |
| PH12015501541A1 (en) | 2015-10-05 |
| US20140187767A1 (en) | 2014-07-03 |
| CL2015001853A1 (es) | 2015-10-30 |
| CA2895132A1 (en) | 2014-07-03 |
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