JP2019502767A - 高価値製品を生産するためのリグニンを用いたセルロースの機能化 - Google Patents
高価値製品を生産するためのリグニンを用いたセルロースの機能化 Download PDFInfo
- Publication number
- JP2019502767A JP2019502767A JP2018518613A JP2018518613A JP2019502767A JP 2019502767 A JP2019502767 A JP 2019502767A JP 2018518613 A JP2018518613 A JP 2018518613A JP 2018518613 A JP2018518613 A JP 2018518613A JP 2019502767 A JP2019502767 A JP 2019502767A
- Authority
- JP
- Japan
- Prior art keywords
- lignin
- fatty acid
- cellulose
- tofa
- particles
- 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.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/187—Preparation of cellulose ethers with olefinic unsaturated groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
- C09D101/26—Cellulose ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
- C09D101/26—Cellulose ethers
- C09D101/28—Alkyl ethers
- C09D101/286—Alkyl ethers substituted with acid radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D197/00—Coating compositions based on lignin-containing materials
- C09D197/005—Lignin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J101/00—Adhesives based on cellulose, modified cellulose, or cellulose derivatives
- C09J101/08—Cellulose derivatives
- C09J101/26—Cellulose ethers
- C09J101/28—Alkyl ethers
- C09J101/286—Alkyl ethers substituted with acid radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J197/00—Adhesives based on lignin-containing materials
- C09J197/005—Lignin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Materials For Medical Uses (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
「ナノ粒子」(NP)は、本発明の文脈では、500nm未満の直径を有する粒子を含むことが意図される。本発明では、主としてリグニンがナノサイズで使用されるが、ナノセルロースの使用は任意である。典型的には、セルロース繊維の長さは少なくとも1μm、好ましくは1〜30μmである。
TOFA−リグニンNPの調製のために、トール油脂肪酸改質リグニン試料TOFA−L−50およびTOFA−L−100をTHFに溶解した(工程1)。Milli Q水をゆっくりとその溶液に添加した(工程2)。その後、回転蒸発器を用いてTHFを蒸発させた(工程3)。この後、試料をセルロースアセテート透析膜(MWCO 1000Da)を用いて3日間水に対して透析した。2つの異なるバッチを、溶媒交換の時間を変更することによって調製した。
反応手順
試験試料の抗菌活性を、Mueller−Hinton II−ブロス中の改質CLSI M100−S19法を用いて分析した。試験試料からの2倍希釈液を培養液に調製し、一晩増殖させた細菌接種液と混合した。37℃で試料の増殖を、自動濁度計Bioscreenで48時間モニターした。最小阻害濃度(MIC)値および増殖阻害%値を計算した。
溶媒としてTHFを用いてTOFAリグニンナノ粒子(TLNP50およびTLNP100)を調製した。0.48gのTOFA−L−50またはTOFA−L−100を360mlのTHFに溶解した。480gのミリQ水を、室温で撹拌しながらその溶液にゆっくりと(30分間)添加した。その後、ロータリーエバポレーターを用いてTHFの主要部分を蒸発させ、最後に、3500Daの分離を有する膜を用いてTLNP懸濁液を透析した。水懸濁液中のリグニンナノ粒子の最終濃度は1mg/mlであった。
特許文献
国際公開第2006108637A2号
国際公開第2013050661A1号
国際公開第2015011364A2号
非特許文献
Hult, E.-L., Ropponen, J., Poppius-Levlin, K., Ohra-Aho, T., Tamminen, T., Industrial Crops and Products (2013), 50, 694-700
Qian, Y., Deng, Y., Qiu, X., Li, H., Yang, D., Green Chemistry (2014), 16(4), 2156-2163
Saastamoinen, P., Mattinen, M.-L., Hippi, U., Nousiainen, P., Sipila, J., Lille, M., Suurnakki, A., Pere, J., BioResources (2012), 7(4), 5749-5770
Aulin, C. and Stroem, G., Industrial & Engineering Chemistry Resaearch (2013), 52(7), 2582-2589
Claims (19)
- リグニン粒子の水性混合物を調製すること、
これらの粒子を脂肪酸を用いて改質すること、および
得られた脂肪酸改質リグニン粒子をセルロース繊維またはセルロース粒子と反応させること、
により、特徴づけられる、水溶液中のセルロースへのリグニンの共有結合のための方法。 - 前記リグニンが、軟材または硬材パルプから、好ましくはクラフトパルプから、そして最も適切にはリグノブーストリグニンから抽出された、単離されたリグニンから選択される、請求項1に記載の方法。
- 前記リグニンが、リグニンナノ粒子(NP)、好ましくは500nm未満、より好ましくは50〜300nm、最も好ましくは70〜200nmの直径を有するリグニンナノ粒子(NP)から選択される、請求項1または2に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸が、トール油脂肪酸(TOFA)を含有する、またはトール油脂肪酸(TOFA)から選択される、請求項1〜3のいずれか一項に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸が、脂肪酸混合物、例えば、80〜99重量%、好ましくは85〜99重量%の不飽和脂肪酸を含有するトール油脂肪酸(TOFA)から選択される、請求項1〜4のいずれか一項に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸が、脂肪酸混合物、例えば、0.1〜10重量%、好ましくは≦5重量%のロジン酸を含有し、最も好適には≦5重量%のロジン酸および不けん化物の合計含有量を含有するTOFAから選択される、請求項1〜5のいずれか一項に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸が、脂肪酸混合物、例えば、16〜20個の炭素原子を有する脂肪酸を主に含有するTOFAから選択され、その主成分が、好ましくは不飽和C18脂肪酸であり、最も好適にはオレイン酸(C18:1)、リノール酸(C18:2)、リノレン酸および/またはピノレン酸(どちらもC18:3)である、請求項1〜6のいずれか一項に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸が、脂肪酸混合物、例えば、10重量%以下のC18:3脂肪酸、20〜70重量%のC18:2脂肪酸および20〜70重量%のC18:1脂肪酸を含む脂肪酸を主に含有するTOFAから選択される、請求項1〜7のいずれか一項に記載の方法。
- 前記リグニンを改質するために使用される前記脂肪酸、例えば、TOFAが、前記リグニンとの反応の前に、対応する脂肪酸塩化物混合物に変換される、請求項1〜8のいずれか一項に記載の方法。
- その改質反応が、前記リグニン中の脂肪酸により、40〜100%、好ましくは50〜100%、最も適切には約50%または約100%の置換度を対象とする、請求項1〜9のいずれか一項に記載の方法。
- 前記水性混合物が、適切な有機溶媒、例えばテトラヒドロフラン(THF)中の脂肪酸改質リグニンの溶液に水を添加すること、および前記有機溶媒を蒸発させることによって達成される、請求項1〜10のいずれか一項に記載の方法。
- 前記セルロースが、前記反応の前にアリル化されている、請求項1〜11のいずれか一項に記載の方法。
- 前記脂肪酸改質リグニンと前記セルロースとの間の反応が、水溶液中で、過硫酸アンモニウム(APS)などのラジカル開始剤の助けを借りて行われる、請求項1〜12のいずれか一項に記載の方法。
- 前記脂肪酸改質リグニンと前記セルロースとの間の反応が、<100℃の温度、好ましくは約65℃または80℃の温度で行われる、請求項1〜13のいずれか一項に記載の方法。
- 請求項1〜14のいずれか一項に記載の方法により調製された脂肪酸−リグニン−セルロースを含有する従来の被覆材材料を含むことを特徴とする、抗菌性創傷被覆材。
- 1〜10mg/mlの前記脂肪酸−リグニン−セルロースを含有する溶液を含浸させた、請求項15に記載の抗菌性創傷被覆材。
- 請求項1〜14のいずれか一項に記載の方法により調製された1〜10mg/mlの前記脂肪酸−リグニン−セルロースを含有するコーティング混合物または接着剤混合物を含む、抗菌性コーティングまたは接着剤。
- 抗菌剤として使用するための、脂肪酸で改質されたリグニン粒子。
- リグニン中の脂肪酸によって40〜100%、好ましくは50〜100%、最も適切には約50%または約100%の置換度を有する、請求項18に記載の抗菌改質リグニン粒子。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI20155871 | 2015-11-25 | ||
FI20155871A FI126754B (en) | 2015-11-25 | 2015-11-25 | Functionalization of cellulose with lignin for the production of high added value products |
PCT/FI2016/050831 WO2017089657A1 (en) | 2015-11-25 | 2016-11-25 | Functionalization of cellulose with lignin to produce high-value products |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2019502767A true JP2019502767A (ja) | 2019-01-31 |
Family
ID=58688657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018518613A Pending JP2019502767A (ja) | 2015-11-25 | 2016-11-25 | 高価値製品を生産するためのリグニンを用いたセルロースの機能化 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20180327514A1 (ja) |
EP (1) | EP3380527A4 (ja) |
JP (1) | JP2019502767A (ja) |
KR (1) | KR102087724B1 (ja) |
CA (1) | CA2997666A1 (ja) |
FI (1) | FI126754B (ja) |
WO (1) | WO2017089657A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3228329B1 (en) * | 2016-04-06 | 2022-06-08 | UPM-Kymmene Corporation | A method for preparing a medical product comprising nanofibrillar cellulose and a medical product |
FR3080627B1 (fr) * | 2018-04-26 | 2021-02-26 | Porcher Ind | Composition d'adherisage pour textile et textile de renfort y relatif |
EP3932993A1 (en) * | 2020-07-01 | 2022-01-05 | Ren Fuel K2B AB | Lignin crosslinked with a polyunsaturated compound |
EP4238941A4 (en) | 2020-10-28 | 2024-05-22 | Lignum Inc | METHOD FOR PRODUCING AN ANTIBACTERIAL BIOFILLER AS AN ADDITIVE TO A PLASTIC AND ANTIBACTERIAL BIOFILLER PRODUCED THEREFOR AS AN ADDITIVE TO A PLASTIC |
KR102400400B1 (ko) | 2020-10-28 | 2022-05-20 | 주식회사 리그넘 | 플라스틱 첨가용 항균 바이오 충진제의 제조방법 및 이에 의해 제조된 플라스틱 첨가용 항균 바이오 충진제 |
CN115286836B (zh) * | 2022-02-09 | 2023-07-18 | 浙江科技学院 | 一种复合木质素纳米微球及其制备方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5080445B2 (ja) | 2005-04-13 | 2012-11-21 | アボット ゲーエムベーハー ウント コー. カーゲー | 超微粒子懸濁液及び超微粒子を穏やかに製造する方法並びにその使用 |
EP2150649B1 (en) * | 2007-05-09 | 2012-09-12 | Institute of Natural Fibres and Medicinal Plants | Cellulose fibre textiles containing nanolignins, a method of applying nanolignins onto textiles and the use of nanolignins in textile production |
US8772406B2 (en) * | 2009-08-06 | 2014-07-08 | Robert J. Linhardt | Synthetic wood composite |
JPWO2011099544A1 (ja) * | 2010-02-10 | 2013-06-13 | 日立化成株式会社 | 樹脂組成物、成形体及び複合成形体 |
DK2751169T3 (en) | 2011-10-07 | 2018-11-26 | Teknologian Tutkimuskeskus Vtt Oy | FUNCTIONALIZED LIGNIN AND METHOD OF PRODUCING SAME |
FI20125879A (fi) * | 2012-08-24 | 2014-02-25 | Upm Kymmene Corp | Menetelmä ligniinin esteröimiseksi ainakin yhden rasvahapon avulla |
EP2711396A1 (en) * | 2012-09-19 | 2014-03-26 | Annikki GmbH | Copolymerizable lignin derivatives |
FR3008904B1 (fr) | 2013-07-26 | 2015-07-31 | Inst Polytechnique Grenoble | Procede de formation d'une couche hydrophobe |
US10266688B2 (en) * | 2013-09-06 | 2019-04-23 | Teknologian Tutkimuskeskus Vtt Oy | Surface-modified cellulose nanofibres, bio composite resin composition and method for producing the same |
US20150232703A1 (en) * | 2014-02-18 | 2015-08-20 | Api Intellectual Property Holdings, Llc | Processes for producing lignin-coated hydrophobic cellulose, and compositions and products produced therefrom |
-
2015
- 2015-11-25 FI FI20155871A patent/FI126754B/en not_active IP Right Cessation
-
2016
- 2016-11-25 US US15/777,238 patent/US20180327514A1/en not_active Abandoned
- 2016-11-25 JP JP2018518613A patent/JP2019502767A/ja active Pending
- 2016-11-25 WO PCT/FI2016/050831 patent/WO2017089657A1/en active Application Filing
- 2016-11-25 KR KR1020187009913A patent/KR102087724B1/ko active IP Right Grant
- 2016-11-25 EP EP16868084.1A patent/EP3380527A4/en not_active Withdrawn
- 2016-11-25 CA CA2997666A patent/CA2997666A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CA2997666A1 (en) | 2017-06-01 |
KR102087724B1 (ko) | 2020-03-12 |
FI20155871A (fi) | 2017-05-15 |
KR20180051591A (ko) | 2018-05-16 |
US20180327514A1 (en) | 2018-11-15 |
WO2017089657A1 (en) | 2017-06-01 |
EP3380527A4 (en) | 2019-07-31 |
EP3380527A1 (en) | 2018-10-03 |
FI126754B (en) | 2017-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102087724B1 (ko) | 고부가가치 생산물을 생산하기 위한 리그닌으로 셀룰로오스의 작용화 | |
Chen et al. | Production of new cellulose nanomaterial from red algae marine biomass Gelidium elegans | |
Setälä et al. | Lignin nanoparticles modified with tall oil fatty acid for cellulose functionalization | |
Espino et al. | Isolation and characterization of cellulose nanocrystals from industrial by-products of Agave tequilana and barley | |
Kumari et al. | Cellulose nanofibers from lignocellulosic biomass of lemongrass using enzymatic hydrolysis: characterization and cytotoxicity assessment. | |
Juikar et al. | Extraction of nanolignin from coconut fibers by controlled microbial hydrolysis | |
Nazir et al. | Eco-friendly extraction and characterization of cellulose from oil palm empty fruit bunches | |
Missoum et al. | Antibacterial activity and biodegradability assessment of chemically grafted nanofibrillated cellulose | |
Chen et al. | Lignocellulose nanocrystals from pineapple peel: Preparation, characterization and application as efficient Pickering emulsion stabilizers | |
Benhamou et al. | Beneficiation of cactus fruit waste seeds for the production of cellulose nanostructures: extraction and properties | |
Shi et al. | Borneol-grafted cellulose for antifungal adhesion and fungal growth inhibition | |
Huang et al. | Hydrophobic and antibacterial textile fibres prepared by covalently attaching betulin to cellulose | |
WO2017105337A1 (en) | Manufacture of nanocellulose and intermediates thereof using oxalic acid dihydrate | |
JP2014511907A (ja) | マイクロおよびナノ結晶セルロースの製造方法 | |
Sadalage et al. | Production of microcrystalline cellulose and bacterial nanocellulose through biological valorization of lignocellulosic biomass wastes | |
Tian et al. | Bacterial cellulose/lignin nanoparticles composite films with retarded biodegradability | |
Jiang et al. | Enzymatic preparation of oxidized viscose fibers-based biosorbent modified with ε-polylysine for dyes removal and microbial inactivation | |
WO2019211871A1 (en) | A process for the preparation of essential oil modified nanocellulose and applications thereof | |
Aridi et al. | Effect of sodium hypochlorite concentration during pre-treatment on isolation of nanocrystalline cellulose from Leucaena leucocephala (Lam.) mature pods | |
Seth et al. | Enzyme-based green synthesis, characterisation, and toxicity studies of cellulose nanocrystals/fibres produced from the Vetiveria zizanioides roots agro-waste | |
Das et al. | Lignin-A green material for antibacterial application—A review | |
Cherian et al. | Non-cytotoxic, highly functionalized cellulose nanocrystals with high crystallinity and thermal stability derived from a novel agromass of Elettaria cardamomum, using a soft and benign mild oxalic acid hydrolysis | |
Laribi et al. | Low-cost carboxymethyl holocellulose and carboxymethyl cellulose from wheat straw | |
Liu et al. | Nanocomposites derived from licorice residues cellulose nanofibril and chitosan nanofibril: Effects of chitosan nanofibril dosage on resultant properties | |
Wyatt et al. | Thermal and mechanical properties of glycerol-based polymer films infused with plant cell wall polysaccharides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180410 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190416 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190710 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190911 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191009 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200303 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20201013 |