FI126754B - Selluloosan funktionalisointi ligniinillä korkea-arvoisten tuotteiden valmistamiseksi - Google Patents

Selluloosan funktionalisointi ligniinillä korkea-arvoisten tuotteiden valmistamiseksi Download PDF

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FI126754B
FI126754B FI20155871A FI20155871A FI126754B FI 126754 B FI126754 B FI 126754B FI 20155871 A FI20155871 A FI 20155871A FI 20155871 A FI20155871 A FI 20155871A FI 126754 B FI126754 B FI 126754B
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lignin
fatty acids
cellulose
tofa
fatty acid
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FI20155871A
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English (en)
Swedish (sv)
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FI20155871A (fi
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Arja Paananen
Geza Szilvay
Harri Setälä
Eva-Lena Hult
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Teknologian Tutkimuskeskus Vtt Oy
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Priority to FI20155871A priority Critical patent/FI126754B/fi
Priority to PCT/FI2016/050831 priority patent/WO2017089657A1/en
Priority to CA2997666A priority patent/CA2997666A1/en
Priority to KR1020187009913A priority patent/KR102087724B1/ko
Priority to EP16868084.1A priority patent/EP3380527A4/en
Priority to US15/777,238 priority patent/US20180327514A1/en
Priority to JP2018518613A priority patent/JP2019502767A/ja
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Publication of FI126754B publication Critical patent/FI126754B/fi

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    • 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

Claims (17)

1. Menetelmä ligniinin liittämiseksi kovalenttisesti selluloosaan vesiliuoksissa, tunnettu siitä, että valmistetaan ligniinipartikkelien vesipitoinen seos, modifioidaan näitä partikkeleita rasvahapoilla ja saatetaan saadut rasvahappomodifioidut ligniinipartikkelit reagoimaan selluloosakuitujen tai -partikkelien kanssa.
2. Patenttivaatimuksen 1 mukainen menetelmä, jolloin ligniini on valittu eristetystä ligniinistä, joka on uutettu havu- tai lehtipuumassasta, edullisesti sulfaattimassasta, ja sopivimmin se on Lignoboost-ligniiniä.
3. Patenttivaatimuksen 1 tai 2 mukainen menetelmä, jolloin ligniini on valittu ligniininanopartikkeleista (NP:t), joiden halkaisija on edullisesti alle 500 nm, edullisemmin 50-300 nm ja sopivimmin 70-200 nm.
4. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin ligniinin modifiointiin käytettävät rasvahapot sisältävät mäntyöljyn rasvahappoja (TOFA) tai ne on valittu mäntyöljyn rasvahapoista.
5. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin ligniinin modifiointiin käytettävät rasvahapot on valittu rasvahapposeoksista, esim. mäntyöljyn rasvahapoista (TOFA), jotka sisältävät 80-99 paino-%, edullisesti 85-99 paino-%, tyydyttymättö-miä rasvahappoja.
6. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin ligniinin modifiointiin käytettävät rasvahapot on valittu rasvahapposeoksista, esim. TOFA, jotka sisältävät hartsihappoja 0,1-10 paino-%, edullisesti < 5 paino-%, ja sopivimmin ne sisältävät hartsihappoja ja saippuoitumattomia aineksia yhteensä < 5 paino-%.
7. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin ligniinin modifiointiin käytettävät rasvahapot on valittu rasvahapposeoksista, esim. TOFA, jotka sisältävät pääasiassa rasvahappoja, joissa on 16-20 hiiliatomia, jolloin pääkomponentit ovat edullisesti tyydyttymättömiä C18-rasvahappoja ja sopivimmin pääkomponentteja ovat öljyhappo (Cl8:1), linolihappo (C18:2), linoleenihappo ja/tai pinoleenihappo (molemmat C18:3).
8. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin ligniinin modifiointiin käytettävät rasvahapot on valittu rasvahapposeoksista, esim. TOFA, jotka sisältävät pääasiassa rasvahappoja, joihin sisältyy enintään 10 paino-% C18:3-rasvahap-poja, 20-70 paino-% C18:2-rasvahappoja ja 20-70 paino-% Cl8:1-rasvahappoja.
9. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin ligniinin modifiointiin käytettävät rasvahapot, esim. TOFA, muutetaan vastaavien rasvahappokloridien seokseksi ennen reaktiota ligniinin kanssa.
10. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin modifiointire-aktion tavoitteeksi muodostetaan substituutioasteen saavuttaminen ligniinissä, joka on 40-100 %, edullisesti 50-100 %, sopivimmin noin 50 % tai noin 100 %.
11. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin vesipitoinen seos on saatu aikaan lisäämällä vettä rasvahappomodifioidun ligniinin liuokseen sopivassa orgaanisessa liuottimessa, esim. tetrahydrofuraanissa (THF),ja haihduttamalla orgaaninen liuotin.
12. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin selluloosa on allyloitu ennen reaktiota.
13. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä Jolloin rasvahappo-modifioidun ligniinin ja selluloosan välinen reaktio tapahtuu vesiliuoksessa ja apuna käytetään radikaali-initiaattoria, kuten ammoniumpersulfaattia (APS).
14. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin rasvahappo-modifioidun ligniinin ja selluloosan välinen reaktio tapahtuu < 100 °C:n lämpötilassa, edullisesti noin 65 tai 80 °C:n lämpötilassa.
15. Antimikrobiaalinen haavasidos, tunnettu siitä, että se käsittää tavanomaisen si-dosmateriaalin, joka sisältää jonkin patenttivaatimuksen 1-14 mukaisesti valmistettua ras-vahappo-ligniini-selluloosaa.
16. Patenttivaatimuksen 15 mukainen antimikrobiaalinen haavasidos, joka on kyllästetty liuoksella, joka sisältää 1-10 mg/ml mainittua rasvahappo-ligniini-selluloosaa.
17. Antimikrobiaalinen pinnoite tai tartunta-aine, tunnettu siitä, että se käsittää pin-noitusseoksen tai tartunta-aineseoksen, joka sisältää 1-10 mg/ml jonkin patenttivaatimuksen 1-14 mukaisesti valmistettua rasvahappo-ligniini-selluloosaa.
FI20155871A 2015-11-25 2015-11-25 Selluloosan funktionalisointi ligniinillä korkea-arvoisten tuotteiden valmistamiseksi FI126754B (fi)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FI20155871A FI126754B (fi) 2015-11-25 2015-11-25 Selluloosan funktionalisointi ligniinillä korkea-arvoisten tuotteiden valmistamiseksi
PCT/FI2016/050831 WO2017089657A1 (en) 2015-11-25 2016-11-25 Functionalization of cellulose with lignin to produce high-value products
CA2997666A CA2997666A1 (en) 2015-11-25 2016-11-25 Functionalization of cellulose with lignin to produce high-value products
KR1020187009913A KR102087724B1 (ko) 2015-11-25 2016-11-25 고부가가치 생산물을 생산하기 위한 리그닌으로 셀룰로오스의 작용화
EP16868084.1A EP3380527A4 (en) 2015-11-25 2016-11-25 FUNCTIONALIZATION OF CELLULOSE WITH LIGNIN TO MANUFACTURE HIGH QUALITY PRODUCTS
US15/777,238 US20180327514A1 (en) 2015-11-25 2016-11-25 Functionalization of cellulose with lignin to produce high-value products
JP2018518613A 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

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US (1) US20180327514A1 (fi)
EP (1) EP3380527A4 (fi)
JP (1) JP2019502767A (fi)
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CA (1) CA2997666A1 (fi)
FI (1) FI126754B (fi)
WO (1) WO2017089657A1 (fi)

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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

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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

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JP2019502767A (ja) 2019-01-31
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

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