JP6817972B2 - 環状有機無水物を用いるポリα−１，３−グルカンエステルの調製 - Google Patents
環状有機無水物を用いるポリα−１，３−グルカンエステルの調製 Download PDFInfo
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- JP6817972B2 JP6817972B2 JP2017567776A JP2017567776A JP6817972B2 JP 6817972 B2 JP6817972 B2 JP 6817972B2 JP 2017567776 A JP2017567776 A JP 2017567776A JP 2017567776 A JP2017567776 A JP 2017567776A JP 6817972 B2 JP6817972 B2 JP 6817972B2
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- 229920005640 poly alpha-1,3-glucan Polymers 0.000 title claims description 216
- 150000008064 anhydrides Chemical class 0.000 title claims description 80
- 125000004122 cyclic group Chemical group 0.000 title claims description 73
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- 238000002360 preparation method Methods 0.000 title description 12
- -1 ester compound Chemical class 0.000 claims description 84
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229920001503 Glucan Polymers 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
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- 238000006467 substitution reaction Methods 0.000 claims description 13
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 6
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JPFGFRMPGVDDGE-UHFFFAOYSA-N Leucrose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)(CO)OC1 JPFGFRMPGVDDGE-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 238000001212 derivatisation Methods 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical class COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- ZVUUAOZFEUKPLC-UHFFFAOYSA-N 3-ethyl-4-methylfuran-2,5-dione Chemical compound CCC1=C(C)C(=O)OC1=O ZVUUAOZFEUKPLC-UHFFFAOYSA-N 0.000 description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 3
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- USHIMSBZXQNBLI-UHFFFAOYSA-N dioxane;ethanol Chemical compound CCO.C1CCOOC1 USHIMSBZXQNBLI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 108090001082 glucan-binding proteins Proteins 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000157 polyfructose Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
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| US62/186,570 | 2015-06-30 | ||
| PCT/US2016/038909 WO2017003808A1 (en) | 2015-06-30 | 2016-06-23 | Preparation of poly alpha-1,3-glucan esters using cyclic organic anhydrides |
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| BR112019004207B1 (pt) | 2016-10-28 | 2023-04-18 | Nutrition & Biosciences Usa 4, Inc | Composição de borracha e artigo |
| CN110167969A (zh) | 2016-11-16 | 2019-08-23 | 纳幕尔杜邦公司 | 包含多糖的模制制品 |
| CN109983067B (zh) | 2016-11-16 | 2022-11-15 | 营养与生物科学美国4公司 | 纤维素/多糖复合材料 |
| US20230192905A1 (en) | 2016-11-22 | 2023-06-22 | E I Du Pont De Nemours And Company | Polyalpha-1,3-glucan esters and articles made therefrom |
| US11248314B2 (en) | 2016-11-22 | 2022-02-15 | Nutrition & Biosciences USA 4, Inc. | Process for making polyacrylonitrile fibers |
| JP2020514426A (ja) | 2016-11-22 | 2020-05-21 | デュポン・インダストリアル・バイオサイエンシーズ・ユーエスエイ・エルエルシー | 多糖のＩｎ Ｓｉｔｕ官能化およびその組成物 |
| JP2020508952A (ja) | 2017-01-24 | 2020-03-26 | デュポン・インダストリアル・バイオサイエンシーズ・ユーエスエイ・エルエルシー | 多糖を使用した沈降炭酸カルシウムの製造プロセス |
| KR102174849B1 (ko) | 2017-07-26 | 2020-11-05 | 엘지전자 주식회사 | 유니버설 조인트와 이를 구비하는 노브 조립체 및 가전기기 |
| EP3609949A1 (en) | 2017-06-30 | 2020-02-19 | DuPont Industrial Biosciences USA, LLC | Polysaccharide-elastomer masterbatch compositions |
| JP7295846B2 (ja) * | 2017-09-01 | 2023-06-21 | 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 | 多糖類を含むラテックス組成物 |
| JP2020533498A (ja) | 2017-09-13 | 2020-11-19 | デュポン・インダストリアル・バイオサイエンシーズ・ユーエスエイ・エルエルシー | 多糖を含む不織ウェブ |
| WO2019118674A1 (en) | 2017-12-14 | 2019-06-20 | E. I. Du Pont De Nemours And Company | Alpha-1,3-glucan graft copolymers |
| EP3728466B1 (en) | 2018-02-26 | 2021-09-15 | Nutrition & Biosciences USA 4, Inc. | Blends of polyesters and polysaccharides |
| CN113574074B (zh) | 2018-10-25 | 2023-03-21 | 营养与生物科学美国第四公司 | α-1,3-葡聚糖接枝共聚物 |
| CN116134054A (zh) | 2020-06-04 | 2023-05-16 | 营养与生物科学美国4公司 | 右旋糖酐-α-葡聚糖接枝共聚物及其衍生物 |
| CA3178617A1 (en) | 2020-06-10 | 2021-12-16 | Mark Robert Sivik | A laundry care or dish care composition comprising a poly alpha-1,6-glucan ester |
| EP4165091A1 (en) | 2020-06-10 | 2023-04-19 | Nutrition & Biosciences USA 4, Inc. | Poly alpha-1,6-glucan esters and compositions comprising same |
| US20240117275A1 (en) | 2021-01-29 | 2024-04-11 | Danisco Us Inc. | Compositions for cleaning and methods related thereto |
| US20240199766A1 (en) | 2021-02-19 | 2024-06-20 | Nutrition & Biosciences USA 4, Inc. | Oxidized polysaccharide derivatives |
| 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 |
| CN118679189A (zh) * | 2022-02-10 | 2024-09-20 | 日东电工株式会社 | β-1,3-葡聚糖衍生物的制造方法 |
| WO2023183280A1 (en) | 2022-03-21 | 2023-09-28 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising insoluble alpha-glucan |
| JP2025523007A (ja) | 2022-07-11 | 2025-07-17 | 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 | 両親媒性グルカンエステル誘導体 |
| EP4622465A1 (en) | 2022-11-23 | 2025-10-01 | Nutrition & Biosciences USA 4, Inc. | Hygienic treatment of surfaces with compositions comprising hydrophobically modified alpha-glucan derivative |
| CN115975398B (zh) * | 2022-12-07 | 2024-04-16 | 崇左南方水泥有限公司 | 一种透气薄膜专用纳米碳酸钙的制备方法 |
| WO2024129951A1 (en) | 2022-12-16 | 2024-06-20 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| WO2024163584A1 (en) | 2023-02-01 | 2024-08-08 | Danisco Us Inc. | Subtilisin variants and methods of use |
| WO2024163695A1 (en) | 2023-02-01 | 2024-08-08 | The Procter & Gamble Company | Detergent compositions containing enzymes |
| WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
| WO2025072416A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
| WO2025072417A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
| WO2025117349A1 (en) | 2023-11-28 | 2025-06-05 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| WO2025199079A1 (en) | 2024-03-20 | 2025-09-25 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
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| EP1165867B1 (en) * | 1999-01-25 | 2004-04-14 | E.I. Du Pont De Nemours And Company | Polysaccharide fibers |
| WO2014048505A1 (en) * | 2012-09-28 | 2014-04-03 | Entonik Holding Ag | Lithium- ion battery |
| WO2015094402A1 (en) * | 2013-12-20 | 2015-06-25 | E. I. Du Pont De Nemours And Company | Films of poly alpha-1,3-glucan esters and method for their preparation |
| JP6261610B2 (ja) | 2012-12-27 | 2018-01-17 | 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 | ポリα−１，３−グルカンエステルの調製及びそれからのフィルム |
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2016
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| ES2811340T3 (es) | 2021-03-11 |
| EP3317304B1 (en) | 2020-06-03 |
| AU2016285548A1 (en) | 2017-12-21 |
| KR20180021844A (ko) | 2018-03-05 |
| US11225530B2 (en) | 2022-01-18 |
| AU2016285548B2 (en) | 2020-04-16 |
| BR112017028167A2 (pt) | 2018-08-28 |
| EP3317304A1 (en) | 2018-05-09 |
| US20200347152A1 (en) | 2020-11-05 |
| CN107849155A (zh) | 2018-03-27 |
| WO2017003808A1 (en) | 2017-01-05 |
| JP2018519395A (ja) | 2018-07-19 |
| US20180155455A1 (en) | 2018-06-07 |
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