ES2774388T3 - Procedimiento para producir celulosa nanocristalina funcionalizada y celulosa nanocristalina funcionalizada producida de ese modo - Google Patents
Procedimiento para producir celulosa nanocristalina funcionalizada y celulosa nanocristalina funcionalizada producida de ese modo Download PDFInfo
- Publication number
- ES2774388T3 ES2774388T3 ES15826572T ES15826572T ES2774388T3 ES 2774388 T3 ES2774388 T3 ES 2774388T3 ES 15826572 T ES15826572 T ES 15826572T ES 15826572 T ES15826572 T ES 15826572T ES 2774388 T3 ES2774388 T3 ES 2774388T3
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- Spain
- Prior art keywords
- nanocrystalline cellulose
- cellulose
- functionalized
- reaction mixture
- nanocrystalline
- 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.)
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- 229920001046 Nanocellulose Polymers 0.000 title claims abstract description 234
- 238000000034 method Methods 0.000 title claims abstract description 102
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- 230000008569 process Effects 0.000 claims abstract description 56
- 239000011541 reaction mixture Substances 0.000 claims abstract description 40
- 150000002978 peroxides Chemical class 0.000 claims abstract description 34
- 239000002159 nanocrystal Substances 0.000 claims abstract description 16
- 230000005855 radiation Effects 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
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- 239000011734 sodium Substances 0.000 claims description 17
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 description 4
- 229920001131 Pulp (paper) Polymers 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 4
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- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 4
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 3
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 3
- 229920000289 Polyquaternium Polymers 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- HGKOWIQVWAQWDS-UHFFFAOYSA-N bis(16-methylheptadecyl) 2-hydroxybutanedioate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CC(O)C(=O)OCCCCCCCCCCCCCCCC(C)C HGKOWIQVWAQWDS-UHFFFAOYSA-N 0.000 description 3
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- 229910052582 BN Inorganic materials 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
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- 229920002488 Hemicellulose Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
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- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 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
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
- C08B15/04—Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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| PCT/CA2015/050707 WO2016015148A1 (en) | 2014-07-28 | 2015-07-27 | Method for producing functionalized nanocrystalline cellulose and functionalized nanocrystalline cellulose thereby produced |
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| WO2018100062A1 (en) | 2016-11-30 | 2018-06-07 | Chanel Parfums Beaute | Sunscreen composition comprising nanocrystalline cellulose |
| EP3547998A1 (en) | 2016-11-30 | 2019-10-09 | Chanel Parfums Beauté | Cosmetic composition comprising nanocrystalline cellulose, method and use thereof |
| ES2927077T3 (es) * | 2016-11-30 | 2022-11-02 | Anomera Inc | Composición cosmética en polvo que comprende celulosa nanocristalina |
| EA201992400A1 (ru) * | 2017-04-07 | 2020-04-16 | Йисум Рисёч Девелопмент Кампани Оф Зэ Хибру Юниверсити Оф Джерузалем Лтд. | Композиции для ухода за волосами |
| KR102063545B1 (ko) * | 2018-06-11 | 2020-01-08 | 한국화학연구원 | 전자빔 조사를 통한 셀룰로오스 나노결정 추출방법 및 셀룰로오스 나노결정 분말 |
| WO2020163948A1 (en) * | 2019-02-15 | 2020-08-20 | Anomera Inc. | Nanoredispersible microparticles of dried cellulose nanocrystals and method of production thereof |
| CN110051558B (zh) * | 2019-04-10 | 2022-03-25 | 华南理工大学 | 一种防色彩迁移的植物微纳米纤维口红及其制备方法与应用 |
| CA3124455C (en) | 2019-05-10 | 2022-07-05 | Anomera Inc. | Microparticles of cellulose nanocrystals with pigment nanoparticles bound thereto and method of production thereof |
| CN114364365A (zh) * | 2019-05-10 | 2022-04-15 | 阿诺米拉公司 | 包含与蛋白聚集的纤维素纳米晶体的微粒以及其化妆品用途 |
| JP2022533055A (ja) * | 2019-05-10 | 2022-07-21 | アノメラ インコーポレイテッド | 多孔質セルロース微小粒子およびそれらの製造方法 |
| WO2021150477A1 (en) * | 2020-01-23 | 2021-07-29 | Dow Global Technologies Llc | Aqueous suncase formulation based on sulfated a crystalline cellulose spf booster |
| TWI736144B (zh) * | 2020-02-24 | 2021-08-11 | 臺灣塑膠工業股份有限公司 | 含有纖維素奈米纖維之外用組成物及其用途 |
| KR102611968B1 (ko) * | 2020-06-29 | 2023-12-08 | 연세대학교 산학협력단 | 고분산성 셀룰로오스 나노크리스탈을 이용한 핵산 약물 전달용 나노복합체 |
| CN114569582A (zh) * | 2022-01-18 | 2022-06-03 | 上海交通大学 | 一种酶制剂及其制备方法和用途 |
| CN114574285A (zh) * | 2022-01-18 | 2022-06-03 | 上海交通大学 | 一种精油的高内向乳液及其制备方法 |
| US12129314B1 (en) | 2024-01-31 | 2024-10-29 | King Faisal University | Ultrasound-assisted method for high-yield cellulose extraction from raw rice straw without the need for bleaching step |
| KR102766306B1 (ko) | 2024-09-10 | 2025-02-12 | 주식회사 더데이원랩 | 분산 안정성이 향상된 셀룰로오스 나노크리스탈 제조방법, 그로부터 제조된 셀룰로오스 나노크리스탈 및 이를 포함하는 연무 확산용 조성물 |
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| US2886416A (en) * | 1954-04-28 | 1959-05-12 | Columbia Southern Chem Corp | Preparation of hydrogen peroxide |
| CA2019675C (en) | 1989-07-07 | 1997-12-30 | John J. Tsai | Cationic polysaccharides and reagents for their preparation |
| US5349089A (en) * | 1989-07-07 | 1994-09-20 | National Starch And Chemical Investment Holding Corporation | Reagent for preparing polycationic polysaccharides |
| CA2080026A1 (en) | 1992-09-09 | 1994-03-10 | Alfred Wong | Novel method of bleaching of lignocelulosic pulp using persulphate |
| US6238521B1 (en) | 1996-05-01 | 2001-05-29 | Nalco Chemical Company | Use of diallyldimethylammonium chloride acrylamide dispersion copolymer in a papermaking process |
| US5769934A (en) * | 1997-01-15 | 1998-06-23 | Fmc Corporation | Method for producing microcrystalline cellulose |
| DE19842134A1 (de) | 1998-09-14 | 2000-04-13 | Merck Patent Gmbh | Pigment mit hoher Lichtdiffusion |
| US6544548B1 (en) * | 1999-09-13 | 2003-04-08 | Keraplast Technologies, Ltd. | Keratin-based powders and hydrogel for pharmaceutical applications |
| US7649089B2 (en) * | 2001-12-06 | 2010-01-19 | University Of Iowa Research Foundation | Biodegradable oxidized cellulose esters and their uses as microspheres |
| CN100509852C (zh) | 2002-07-26 | 2009-07-08 | Fmc有限公司 | 微晶纤维素的制造 |
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| NO20065147L (no) | 2006-11-08 | 2008-05-09 | Ntnu Tech Transfer As | Nanokompositter basert på cellulosewhiskers og celluloseplast |
| WO2010105357A1 (en) * | 2009-03-20 | 2010-09-23 | Fpinnovations | Cellulose materials with novel properties |
| WO2010116826A1 (ja) | 2009-03-30 | 2010-10-14 | 日本製紙株式会社 | セルロースナノファイバーの製造方法 |
| JP5330882B2 (ja) | 2009-03-30 | 2013-10-30 | 日本製紙株式会社 | セルロースゲル分散液の製造方法 |
| US8709203B2 (en) * | 2009-08-11 | 2014-04-29 | Fpinnovations | Fractionation of a waste liquor stream from nanocrystalline cellulose production |
| WO2011040547A1 (ja) | 2009-09-30 | 2011-04-07 | 日本製紙株式会社 | 紙製バリア材料 |
| CN102947345A (zh) * | 2009-12-15 | 2013-02-27 | 加拿大国家研究委员会 | 来自可再生生物质的纤维素纳米晶体 |
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| JP2012076231A (ja) | 2010-09-30 | 2012-04-19 | Nippon Paper Industries Co Ltd | 紙製ガスバリア材料 |
| JP6003080B2 (ja) | 2011-02-21 | 2016-10-05 | 三菱化学株式会社 | セルロース繊維およびセルロース繊維の製造方法 |
| WO2012119229A1 (en) * | 2011-03-08 | 2012-09-13 | The Royal Institution For The Advancement Of Learning/Mcgill University | Highly charge group-modified cellulose fibers which can be made into cellulose nanostructures or super-absorbing cellulosic materials and method of making them |
| WO2012132903A1 (ja) | 2011-03-30 | 2012-10-04 | 日本製紙株式会社 | セルロースナノファイバーの製造方法 |
| EP2756016A4 (en) * | 2011-09-13 | 2015-05-20 | Celluforce Inc | SUPRAMOLECULAR MATERIALS BASED ON NANOCRYSTALLINE CELLULOSE FOR THERMOPLASTIC POLYMER COMPOSITES AND THERMODURCIS |
| WO2013047218A1 (ja) * | 2011-09-30 | 2013-04-04 | 日本製紙株式会社 | セルロースナノファイバーの製造方法 |
| EP2776009B1 (en) | 2011-11-11 | 2017-02-15 | The Procter and Gamble Company | Surface treatment compositions including shielding salts |
| US20150027648A1 (en) * | 2012-03-14 | 2015-01-29 | Nippon Paper Industries Co., Ltd., | Method for producing anion-modified cellulose nanofiber dispersion |
| US20130274149A1 (en) * | 2012-04-13 | 2013-10-17 | Schlumberger Technology Corporation | Fluids and methods including nanocellulose |
| CN102675475B (zh) * | 2012-05-24 | 2014-08-13 | 东华大学 | 一种麻纤维羧基化纤维素纳米晶体的制备方法 |
| CN104704005A (zh) | 2012-10-16 | 2015-06-10 | 日本制纸株式会社 | 纤维素纳米纤维 |
| JP2016507629A (ja) * | 2013-02-20 | 2016-03-10 | セルフォース インコーポレイテッド | ナノ結晶性セルロースを含むチューナブルかつ応答性のフォトニックヒドロゲル |
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| CA3007655A1 (en) | 2016-02-04 |
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