Chemical modification of lignins: Towards biobased polymers

Progress in Polymer Science - Tập 39 - Trang 1266-1290 - 2014
Stéphanie Laurichesse1, Luc Avérous1
1BioTeam/ICPEES-ECPM, UMR 7515, Université de Strasbourg, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France

Tài liệu tham khảo

Luong, 2012, An eco-friendly and efficient route of lignin extraction from black liquor and a lignin-based copolyester synthesis, Polym Bull, 68, 879, 10.1007/s00289-011-0658-x Gandini, 2008, The state of the art, 1 Taylor, 2008, Biofuels and the biorefinery concept, Energy Policy, 36, 4406, 10.1016/j.enpol.2008.09.069 Pickett, 2008 1966, vol. 59 Phillips, 1934, The chemistry of lignin, Chem Rev, 14, 103, 10.1021/cr60047a005 Schulze, 1857, Beitrage zur Kenntniss des lignins, Chem Zentr, 21, 321 Sarkanen, 1971 Benedikt, 1890, Über eine quantitative reaction des Lignins, Monatsh Chem, 11, 260, 10.1007/BF01540738 Adler, 1977, Lignin chemistry-past, present and future, Wood Sci Technol, 11, 169, 10.1007/BF00365615 McCarthy, 1999, Lignin chemistry, technology, and utilization: a brief history, 742, 2 Brunow, 2004, Methods to reveal the structure of lignin, 89 Freudenberg, 1959, Biosynthesis and constitution of lignin, Nature, 183, 1152, 10.1038/1831152a0 Freudenberg, 1921, Cellulose, Ber Dtsch Chem Ges, 54B, 767, 10.1002/cber.19210540426 Chakar, 2004, Review of current and future softwood kraft lignin process chemistry, Ind Crops Prod, 20, 131, 10.1016/j.indcrop.2004.04.016 Freudenberg, 1965, Lignin: its constitution and formation from p-hydroxycinnamyl alcohols, Science, 48, 595, 10.1126/science.148.3670.595 Ludwig, 1964, Lignin. XII. The high resolution nuclear magnetic resonance spectroscopy of protons in compounds related to lignin, J Am Chem Soc, 86, 1186, 10.1021/ja01060a046 Nimz, 1974, Beech lignin-proposal of a constitutional scheme, Angew Chem Int Ed Engl, 13, 313, 10.1002/anie.197403131 Lindberg, 1989, Specialty polymers from lignin, 397, 190 Hatakeyama, 2010, Lignin structure, properties, and applications, Adv Polym Sci, 232, 1, 10.1007/12_2009_12 Lora, 2002, Recent industrial applications of lignin: a sustainable alternative to nonrenewable materials, J Polym Environ, 10, 39, 10.1023/A:1021070006895 Sarkanen, 1982, Lignin, 19. Kraft lignin component conformation and associated complex configuration in aqueous alkaline solution, Macromolecules, 15, 1098, 10.1021/ma00232a027 Glasser, 1983, The chemistry of several novel bioconversion lignins, J Agric Food Chem, 31, 921, 10.1021/jf00119a001 Glasser, 1999, Classification of lignin according to chemical and molecular structure, 742, 216 Sarkanen, 1981, Lignin. 18. Associative effects among organosolv lignin components, Macromolecules, 14, 426, 10.1021/ma50003a037 Li, 1997, The first 85% kraft lignin-based thermoplastics, J Polym Sci Part B Polym Phys, 35, 1899, 10.1002/(SICI)1099-0488(19970915)35:12<1899::AID-POLB5>3.0.CO;2-L 1999, 742 Lin, 1992 Boerjan, 2003, Lignin biosynthesis, Annu Rev Plant Biol, 54, 519, 10.1146/annurev.arplant.54.031902.134938 Dorrestijn, 2000, The occurrence and reactivity of phenoxyl linkages in lignin and low rank coal, J Anal Appl Pyrolysis, 54, 153, 10.1016/S0165-2370(99)00082-0 Freudenberg, 1968 Chen, 2003, Macromolecular lignin replication: a mechanistic working hypothesis, Phytochem Rev, 2, 235, 10.1023/B:PHYT.0000046173.38194.ba Ralph, 2004, Lignins: natural polymers from oxidative coupling of 4-hydroxyphenyl-propanoids, Phytochem Rev, 3, 29, 10.1023/B:PHYT.0000047809.65444.a4 Sarkanen, 1971, Classification and distribution, 43 Hu, 2002 Hu, 2008 Cazacu, 2013, Advances concerning lignin utilization in new materials, vol. 18, 255 Windeisen, 2012, Lignin as building unit for polymers, 255 Hatakeyama, 1969, Variation of infrared spectra with temperature for lignin and lignin model compounds, Tappi, 52, 1724 Yoshida, 1987, Fractionation of kraft lignin by successive extraction with organic solvents, II. Thermal properties of kraft lignin fractions, Holzforschung, 41, 171, 10.1515/hfsg.1987.41.3.171 Goring, 1963, Thermal softening of lignin, hemicelluloses and cellulose, Pulp Paper Mag Can, 62, 517 Irvine, 1984, The glass transitions of lignin and hemicellulose and their measurement by differential thermal analysis, Tappi, 67, 118 Bouajila, 2006, Some laws of a lignin plasticization, J Appl Polym Sci, 102, 1445, 10.1002/app.24299 Hatakeyama, 2005, 171 Nguyen, 1981, Thermal analysis of lignocellulosic materials, part I. Unmodified materials, Polym Rev, 20, 1 Nguyen, 1981, Thermal analysis of lignocellulosic materials, part II. Modified materials, Polym Rev, 21, 1 Jakab, 1995, Thermogravimetry/mass spectrometry study of six lignins within the scope of an international round robin test, J Anal Appl Pyrolysis, 35, 167, 10.1016/0165-2370(95)00907-7 Brebu, 2010, Thermal degradation of lignin – a review, Cellul Chem Technol, 44, 353 Nassar, 1984, Mechanism of thermal decomposition of lignin, Wood Fiber Sci, 16, 441 Niemi, 2011, Fractionation of organic and inorganic compounds from black liquor by combining membrane separation and crystallization, Chem Eng Technol, 34, 593, 10.1002/ceat.201000520 Smolarski, 2012 Fernando, 2006, Biorefineries: current status, challenges, and future direction, Energy Fuels, 20, 1727, 10.1021/ef060097w Clark, 2012, Green chemistry, biofuels, and biorefinery, Annu Rev Chem Biomol Eng, 3, 183, 10.1146/annurev-chembioeng-062011-081014 Vázquez, 1997, The influence of pulping conditions on the structure of acetosolv eucalyptus lignins, J Wood Chem Technol, 17, 147, 10.1080/02773819708003124 Baumberger, 2007, Molar mass determination of lignins by size-exclusion chromatography: towards standardisation of the method, Holzforschung, 61, 459, 10.1515/HF.2007.074 Marton, 1964, Molecular weight of kraft lignin, Tappi, 47, 471 Tomani, 2011, Integration of lignin removal into a kraft pulp mill and use of lignin as a biofuel, Cellul Chem Technol, 45, 533 Hamaguchi, 2013, Effects of hemicellulose extraction on the kraft pulp mill operation and energy use: review and case study with lignin removal, Chem Eng Res Des, 91, 1284, 10.1016/j.cherd.2013.02.006 Öhman, 2011 Öhman, 2010 Tomani, 2009, vol. 4, 2347 Tomani, 2010, The lignoboost process, Cellul Chem Technol, 44, 53 Vishtal, 2011, Challenges in industrial applications of technical lignins, BioResources, 6, 3547, 10.15376/biores.6.3.3547-3568 Nimz, 1983, Lignin-based wood adhesives, vol. 1 Sannigrahi, 2009, Lignin structural modifications resulting from ethanol organosolv treatment of loblolly pine, Energy Fuels, 24, 683, 10.1021/ef900845t El Hage, 2009, Characterization of milled wood lignin and ethanol organosolv lignin from miscanthus, Polym Degrad Stab, 94, 1632, 10.1016/j.polymdegradstab.2009.07.007 Ferrer, 2013, Acetosolv pulping for the fractionation of empty fruit bunches from palm oil industry, Bioresour Technol, 132, 115, 10.1016/j.biortech.2012.12.189 Shukry, 2008, Some physical properties of acetosolv lignins from bagasse, J Appl Polym Sci, 109, 434, 10.1002/app.28059 Delmas, 2008, Vegetal refining and agrichemistry, Chem Eng Technol, 31, 792, 10.1002/ceat.200800052 Kham, 2005, Delignification of wheat straw using a mixture of carboxylic acids and peroxoacids, Ind Crops Prod, 21, 9, 10.1016/j.indcrop.2003.12.002 Quoc Lam, 2001, A new procedure for the destructuring of vegetable matter at atmospheric pressure by a catalyst/solvent system of formic acid/acetic acid. Applied to the pulping of triticale straw, Ind Crops Prod, 14, 139, 10.1016/S0926-6690(01)00077-2 Wörmeyer, 2011, Comparison of different pretreatment methods for lignocellulosic materials, part II: influence of pretreatment on the properties of rye straw lignin, Bioresour Technol, 102, 4157, 10.1016/j.biortech.2010.11.063 Lora, 2008, Industrial commercial lignins: sources, properties and applications, 225 Gosselink, 2004, Analytical protocols for characterisation of sulphur-free lignin, Ind Crops Prod, 19, 271, 10.1016/j.indcrop.2003.10.008 Gosselink, 2004, Characterisation and application of NovaFiber lignin, Ind Crops Prod, 20, 191, 10.1016/j.indcrop.2004.04.021 Pouteau, 2003, Antioxidant properties of lignin in polypropylene, Polym Degrad Stab, 81, 9, 10.1016/S0141-3910(03)00057-0 Domenek, 2013, Potential of lignins as antioxidant additive in active biodegradable packaging materials, J Polym Environ, 21, 692, 10.1007/s10924-013-0570-6 Vinardell, 2008, Potential applications of antioxidant lignins from different sources, Ind Crops Prod, 27, 220, 10.1016/j.indcrop.2007.07.011 Falkehag, 1975, Lignin in materials, J Appl Polym Sci Appl Polym Symp, 28, 247 De Chirico, 2003, Flame retardants for polypropylene based on lignin, Polym Degrad Stab, 79, 139, 10.1016/S0141-3910(02)00266-5 Yu, 2006, Polymer blends and composites from renewable resources, Prog Polym Sci, 31, 576, 10.1016/j.progpolymsci.2006.03.002 Bismarck, 2006, Green composites as Panacea? Socio-economic aspects of green materials, Environ Dev Sustain, 8, 445, 10.1007/s10668-005-8506-5 Pouteau, 2004, Lignin-polymer blends: evaluation of compatibility by image analysis, C R Biol, 327, 935, 10.1016/j.crvi.2004.08.008 Myrvold, 2008, A new model for the structure of lignosulphonates, part 1. Behaviour in dilute solutions, Ind Crops Prod, 27, 214, 10.1016/j.indcrop.2007.07.010 Myrvold, 2007, The polyelectrolyte behavior of randomly branched lignosulfonates, Tappi J, 6, 10 Lin, 2011, Structure and properties of poly(butylene succinate) filled with lignin: a case of lignosulfonate, J. Appl Polym Sci, 121, 1717, 10.1002/app.33754 Li, 2011, Preparation and properties of biodegradable sodium lignosulfonate/poly(vinyl alcohol) blend films, Adv Mater Res, 160-162:, 676, 10.4028/www.scientific.net/AMR.160-162.676 Erdocia, 2012, Organosolv black liquor hydrolysis to obtain low molecular weight phenolic compounds, Chem Eng Trans, 29, 535 Amen-Chen, 2001, Production of monomeric phenols by thermochemical conversion of biomass: a review, Bioresour Technol, 79, 277, 10.1016/S0960-8524(00)00180-2 Pandey, 2011, Lignin depolymerization and conversion: a review of thermochemical methods, Chem Eng Technol, 34, 29, 10.1002/ceat.201000270 Swain, 2011, Biomass to liquid: a prospective challenge to research and development in 21st century, Renew Sustain Energy Rev, 15, 4917, 10.1016/j.rser.2011.07.061 McKendry, 2002, Energy production from biomass (part 2): conversion technologies, Bioresour Technol, 83, 47, 10.1016/S0960-8524(01)00119-5 Hamaguchi, 2012, Alternative technologies for biofuels production in kraft pulp mills-potential and prospects, Energies, 5, 2288, 10.3390/en5072288 Zakzeski, 2010, The catalytic valorization of lignin for the production of renewable chemicals, Chem Rev, 110, 3552, 10.1021/cr900354u Zakzeski, 2011, Lignin solubilization and aqueous phase reforming for the production of aromatic chemicals and hydrogen, ChemSusChem, 4, 369, 10.1002/cssc.201000299 Nowakowski, 2010, Lignin fast pyrolysis: results from an international collaboration, J Anal Appl Pyrolysis, 88, 53, 10.1016/j.jaap.2010.02.009 Mohan, 2006, Pyrolysis of wood/biomass for bio-oil: a critical review, Energy Fuels, 20, 848, 10.1021/ef0502397 Leonowicz, 1999, Biodegradation of lignin by white rot fungi, Fungal Genet Biol, 27, 175, 10.1006/fgbi.1999.1150 Brebu, 2012, Co-pyrolysis of LignoBoost® lignin with synthetic polymers, Polym Degrad Stab, 97, 2104, 10.1016/j.polymdegradstab.2012.08.024 Araújo, 2010, Vanillin production from lignin oxidation in a batch reactor, Chem Eng Res Des, 88, 1024, 10.1016/j.cherd.2010.01.021 Villar, 2001, Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant, Wood Sci Technol, 35, 245, 10.1007/s002260100089 Bd Silva, 2009, An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin, Chem Eng Res Des, 87, 1276, 10.1016/j.cherd.2009.05.008 Hocking, 1997, Synthetic flavoring from spent sulfite liquor, J Chem Educ, 79, 1055, 10.1021/ed074p1055 Tarabanko, 1995, Influence of lignin origin on the efficiency of the catalytic oxidation of lignin into vanillin and syringaldehyde, Russ Chem Bull, 44, 367, 10.1007/BF00702154 Tarabanko, 2013, Separation of vanillin and syringaldehyde produced from lignins, Sep Sci Technol, 48, 127, 10.1080/01496395.2012.673671 Stanzione, 2012, Vanillin-based resin for use in composite applications, Green Chem, 14, 2346, 10.1039/c2gc35672d Amarasekara, 2012, Vanillin based polymers: I. An electrochemical route to polyvanillin, Green Chem, 14, 2395, 10.1039/c2gc35645g Mialon, 2011, Polyalkylenehydroxybenzoates (PAHBs): biorenewable aromatic/aliphatic polyesters from lignin, Macromol Rapid Commun, 32, 1386, 10.1002/marc.201100242 Mialon, 2010, Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid, Green Chem, 12, 1704, 10.1039/c0gc00150c Aouf, 2012, Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers, Green Chem, 14, 2328, 10.1039/c2gc35558b Jasiukaityte-Grojzdek, 2012, Lignin structural changes during liquefaction in acidified ethylene glycol, J Wood Chem Technol, 32, 342, 10.1080/02773813.2012.698690 Li, 2012, Preparation of polyurethane foams based on liquefied corn stalk enzymatic hydrolysis lignin, J Biobased Mater Bioenergy, 6, 51, 10.1166/jbmb.2012.1197 Lee, 2012, Properties of phenol-formaldehyde resins prepared from phenol-liquefied lignin, J Appl Polym Sci, 124, 4782 Kobayashi, 2004, Analysis on residue formation during wood liquefaction with polyhydric alcohol, J Wood Sci, 50, 407, 10.1007/s10086-003-0596-9 Lin, 1997, Molecular weights and molecular weight distributions of liquefied wood obtained by acid-catalyzed phenolysis, J Appl Polym Sci, 64, 351, 10.1002/(SICI)1097-4628(19970411)64:2<351::AID-APP16>3.0.CO;2-3 Jin, 2011, Liquefaction of lignin by polyethyleneglycol and glycerol, Bioresour Technol, 102, 3581, 10.1016/j.biortech.2010.10.050 Zhang, 2011, Investigation of liquefied wood residues based on cellulose, hemicellulose, and lignin, J Appl Polym Sci, 123, 850, 10.1002/app.34521 Liu, 2006, Preparation and characterization of demethylated lignin-polyethylenimine adhesives, J Adhes, 82, 593, 10.1080/00218460600766632 Truter, 1994, Cold-setting wood adhesives from kraft hardwood lignin, J Appl Polym Sci, 51, 1319, 10.1002/app.1994.070510719 Gonçalves, 2001, Hydroxymethylation and oxidation of organosolv lignins and utilization of the products, Bioresour Technol, 79, 103, 10.1016/S0960-8524(01)00056-6 Hu, 2011, Methods to improve lignin's reactivity as a phenol substitute and as replacement for other phenolic compounds: a brief review, BioResources, 6, 3515, 10.15376/biores.6.3.Hu Mu, 2009, Study on composite adhesive of hydroxymethylated lignosulfonate/phenol-formaldehyde resin with low free formaldehyde, Chem Ind Forest Prod, 29, 38 Mansouri, 2007, Lignin-based polycondensation resins for wood adhesives, J Appl Polym Sci, 103, 1690, 10.1002/app.25098 Mansouri, 2011, Synthetic-resin-free wood panel adhesives from mixed low molecular mass lignin and tannin, Eur J Wood Wood Prod, 69, 221, 10.1007/s00107-010-0423-0 Mansouri, 2011, Study of chemical modification of alkaline lignin by the glyoxalation reaction, BioResources, 6, 4523, 10.15376/biores.6.4.4523-4536 Navarrete, 2012, Study on lignin-glyoxal reaction by MALDI-TOF and CP-MAS 13C-NMR, J Adhes Sci Technol, 26, 1069, 10.1163/016942410X550030 El Mansouri, 2007, Lignin-based wood panel adhesives without formaldehyde, Holz Roh Werkst, 65, 65, 10.1007/s00107-006-0130-z Schneider, 2004, Furfuryl alcohol lignin adhesive, Ind Bioprocess, 26, 10 da Silva, 2013, Adding value to lignins isolated from sugarcane bagasse and Miscanthus, Ind Crops Prod, 42, 87, 10.1016/j.indcrop.2012.04.040 Ramires, 2010, Biobased composites from glyoxal-phenolic resins and sisal fibers, Bioresour Technol, 101, 1998, 10.1016/j.biortech.2009.10.005 Cheng, 2012, Synthesis of biobased phenolic resins/adhesives with methylolated wood-derived bio-oil, J Appl Polym Sci, 126, E430, 10.1002/app.35655 Zhang, 2013, Preparation and properties of lignin–phenol–formaldehyde resins based on different biorefinery residues of agricultural biomass, Ind Crops Prod, 43, 326, 10.1016/j.indcrop.2012.07.037 Arend, 1998, Modern variants of the Mannich reaction, Angew Chem Int Ed Engl, 37, 1044, 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E Matsushita, 2003, Reactivity of a condensed-type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin, J Wood Sci, 49, 166, 10.1007/s100860300026 Yue, 2011, Improved interfacial bonding of PVC/Wood-flour composites by lignin amine modification, BioResources, 6, 2022, 10.15376/biores.6.2.2022-2034 Huo, 2012, Crosslinking kinetics of the formation of lignin-aminated polyol-based polyurethane foam, J Appl Polym Sci, 125, 152, 10.1002/app.35401 Kudanga, 2010, Reactivity of long chain alkylamines to lignin moieties: implications on hydrophobicity of lignocellulose materials, J Biotechnol, 149, 81, 10.1016/j.jbiotec.2010.06.020 Zhang, 2001, Effects of nitrolignin on mechanical properties of polyurethane-nitrolignin films, J Appl Polym Sci, 80, 1213, 10.1002/app.1206 Huang, 2002, Effects of NCO/OH molar ratio on structure and properties of graft-interpenetrating polymer networks from polyurethane and nitrolignin, Polymer, 43, 2287, 10.1016/S0032-3861(02)00028-9 Zhang, 2001, Effects of hard-segment compositions on properties of polyurethane-nitrolignin films, J Appl Polym Sci, 81, 3251, 10.1002/app.1780 Gandini, 2002, Lignins as macromonomers for polyesters and polyurethanes, 57 Nahmany, 2004, Chemoselectivity in reactions of esterification, Org Biomol Chem, 2, 1563, 10.1039/b403161j Guo, 1992, Polyesters from lignin: 1. The reaction of kraft lignin with dicarboxylic acid chlorides, Polym Int, 27, 17, 10.1002/pi.4990270104 Guo, 1991, Polyesters from lignin 2. The copolyesterification of kraft lignin and polyethylene glycols with dicarboxylic acid chlorides, Eur Polym J, 27, 1177, 10.1016/0014-3057(91)90053-Q Fang, 2011, Preparation and application of dimer acid/lignin graft copolymer, BioResources, 6, 2874, 10.15376/biores.6.3.2874-2884 Firdaus, 2012, Renewable co-polymers derived from vanillin and fatty acid derivatives, Eur Polym J, 49, 156, 10.1016/j.eurpolymj.2012.10.017 Thiebaud, 1995, Solvent-free wood esterification with fatty acid chlorides, Bioresour Technol, 52, 169, 10.1016/0960-8524(95)00018-A Thiebaud, 1997, Properties of wood esterified by fatty-acid chlorides, Bioresour Technol, 59, 103, 10.1016/S0960-8524(96)00160-5 Saito, 2012, Turning renewable resources into value-added polymer: development of lignin-based thermoplastic, Green Chem, 14, 3295, 10.1039/c2gc35933b Sivasankarapillai, 2011, Synthesis and properties of lignin-highly branched poly (ester-amine) polymeric systems, Biomass Bioenergy, 35, 919, 10.1016/j.biombioe.2010.11.002 Sivasankarapillai, 2012, Lignin valorization by forming toughened lignin-co-polymers: development of hyperbranched prepolymers for cross-linking, Biomass Bioenergy, 47, 99, 10.1016/j.biombioe.2012.09.057 Sailaja, 2010, Mechanical and thermal properties of compatibilized composites of polyethylene and esterified lignin, Mater Des, 31, 4369, 10.1016/j.matdes.2010.03.046 Xiao, 2001, Chemical modification of lignins with succinic anhydride in aqueous systems, Polym Degrad Stab, 71, 223, 10.1016/S0141-3910(00)00133-6 Doczekalska, 2007, Modification of sawdust from pine and beech wood with the succinic anhydride, Holz Roh Werkst, 65, 187, 10.1007/s00107-006-0152-6 Thielemans, 2005, Lignin esters for use in unsaturated thermosets: lignin modification and solubility modeling, Biomacromolecules, 6, 1895, 10.1021/bm0500345 Ahvazi, 2011, Preparation of lignopolyols from wheat straw soda lignin, J Agric Food Chem, 59, 10505, 10.1021/jf202452m Effendi, 2008, Production of renewable phenolic resins by thermochemical conversion of biomass: a review, Renew Sustain Energy Rev, 12, 2092, 10.1016/j.rser.2007.04.008 That, 1996, Cardanol-lignin-based polyurethanes, Polym Int, 41, 13, 10.1002/(SICI)1097-0126(199609)41:1<13::AID-PI557>3.0.CO;2-8 Sadeghifar, 2012, Toward thermoplastic lignin polymers, part I: selective masking of phenolic hydroxyl groups in kraft lignins via methylation & oxypropylation chemistries, Ind Eng Chem Res, 51, 16713, 10.1021/ie301848j Wu, 1984, Engineering plastics from lignin. I. Synthesis of hydroxypropyl lignin, J Appl Polym Sci, 29, 1111, 10.1002/app.1984.070290408 Fernandes, 2008, The bulk oxypropylation of chitin and chitosan and the characterization of the ensuing polyols, Green Chem, 10, 93, 10.1039/B711648A Evtiouguina, 2000, The oxypropylation of cork residues: preliminary results, Bioresour Technol, 73, 187, 10.1016/S0960-8524(99)00158-3 Evtiouguina, 2001, Urethanes and polyurethanes based on oxypropylated cork: 1. Appraisal and reactivity of products, Polym Int, 50, 1150, 10.1002/pi.760 de Menezes, 2009, Self-reinforced composites obtained by the partial oxypropylation of cellulose fibers, 2. Effect of catalyst on the mechanical and dynamic mechanical properties, Cellulose, 16, 239, 10.1007/s10570-008-9271-z Pavier, 2000, Oxypropylation of sugar beet pulp, 1. Optimisation of the reaction, Ind Crops Prod, 12, 1, 10.1016/S0926-6690(99)00039-4 Pavier, 2000, Oxypropylation of sugar beet pulp, 2. Separation of the grafted pulp from the propylene oxide homopolymer, Carbohydr Polym, 42, 13, 10.1016/S0144-8617(99)00124-1 Pavier, 2000, Urethanes and polyurethanes from oxypropylated sugar beet pulp, I. Kinetic study in solution, Eur Polym J, 36, 1653, 10.1016/S0014-3057(99)00245-1 Aniceto, 2012, Biomass-based polyols through oxypropylation reaction, ChemSusChem, 5, 1358, 10.1002/cssc.201200032 Glasser, 1984, Engineering plastics from Lignin, II. Characterization of hydroxyalkyl lignin derivatives, J Appl Polym Sci, 29, 1815, 10.1002/app.1984.070290533 Ionescu, 2005 Argyropoulos, 1994, Quantitative phosphorus-31 NMR analysis of lignins, a new tool for the lignin chemist, J Wood Chem Technol, 14, 45, 10.1080/02773819408003085 Argyropoulos, 1994, Quantitative phosphorus-31 NMR analysis of six soluble lignins, J Wood Chem Technol, 14, 65, 10.1080/02773819408003086 Argyropoulos, 1995, 31P NMR in wood chemistry: a review of recent progress, Res Chem Intermed, 21, 373, 10.1007/BF03052265 Nadji, 2005, Oxypropylation of lignins and preparation of rigid polyurethane foams from the ensuing polyols, Macromol Mater Eng, 290, 1009, 10.1002/mame.200500200 Cateto, 2009, Optimization study of lignin oxypropylation in view of the preparation of polyurethane rigid foams, Ind Eng Chem Res, 48, 2583, 10.1021/ie801251r Li, 2012, Ethanol organosolv lignin-based rigid polyurethane foam reinforced with cellulose nanowhiskers, RSC Adv, 2, 3347, 10.1039/c2ra00646d Li, 2012, Kraft lignin-based rigid polyurethane foam, J Wood Chem Technol, 32, 210, 10.1080/02773813.2011.652795 Kelley, 1988, Engineering plastics from lignin, XV. Polyurethane films from chain-extended hydroxypropyl lignin, J Appl Polym Sci, 36, 759, 10.1002/app.1988.070360403 Hatakeyama, 2013, Glass transition temperature of polyurethane foams derived from lignin by controlled reaction rate, J Therm Anal Calorim, 8 pages Thring, 2004, Molecular weight effects of the soft segment on the ultimate properties of lignin-derived polyurethanes, Int J Polym Mater, 53, 507, 10.1080/00914030490267627 Thring, 1997, Polyurethanes from Alcell® lignin, Biomass Bioenergy, 13, 125, 10.1016/S0961-9534(97)00030-5 Vanderlaan, 1998, Polyurethanes from Alcell® lignin fractions obtained by sequential solvent extraction, Biomass Bioenergy, 14, 525, 10.1016/S0961-9534(97)10058-7 Cateto, 2008, Monitoring of lignin-based polyurethane synthesis by FTIR-ATR, Ind Crops Prod, 27, 168, 10.1016/j.indcrop.2007.07.018 Delebecq, 2013, On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane, Chem Rev, 113, 80, 10.1021/cr300195n Sarkar, 2001, Thermal stability of lignin-hydroxy-terminated polybutadiene copolyurethanes, Polym Degrad Stab, 73, 169, 10.1016/S0141-3910(01)00084-2 Sarkar, 2001, Synthesis and characterization of lignin-HTPB copolyurethane, Eur Polym J, 37, 1391, 10.1016/S0014-3057(00)00264-0 Bonini, 2005, Polyurethanes and polyesters from lignin, J Appl Polym Sci, 98, 1451, 10.1002/app.22277 Hatakeyama, 1989, High-performance polymers from lignin degradation products, 397, 205 Hatakeyama, 1990, High-performance materials from lignocellulose, 466 Kouisni, 2011, Kraft lignin recovery and its use in the preparation of lignin-based phenol formaldehyde resins for plywood, Cellul Chem Technol, 45, 515 El Mansouri, 2011, Synthesis and characterization of kraft lignin-based epoxy resins, BioResources, 6, 2492, 10.15376/biores.6.3.2492-2503 Yin, 2012, Preparation and properties of lignin-epoxy resin composite, BioResources, 7, 5737, 10.15376/biores.7.4.5737-5748 Sun, 2007, Comparative study on the curing kinetics and mechanism of a lignin-based-epoxy/anhydride resin system, Polymer, 48, 330, 10.1016/j.polymer.2006.10.047 Ismail, 2010, Synthesis and thermal properties of ester-type crosslinked epoxy resins derived from lignosulfonate and glycerol, Polym Int, 59, 181, 10.1002/pi.2705 Faruk, 2013, Continuous extrusion foaming of lignin enhanced thermoplastic polyurethane (TPU), J Biobased Mater Bioenergy, 7, 309, 10.1166/jbmb.2013.1365 Cinelli, 2013, Green synthesis of flexible polyurethane foams from liquefied lignin, Eur Polym J, 49, 1174, 10.1016/j.eurpolymj.2013.04.005 Pan, 2013, Effect of replacing polyol by organosolv and kraft lignin on the property and structure of rigid polyurethane foam, Biotechnol Biofuels, 6, 10.1186/1754-6834-6-12 Ciobanu, 2004, Properties of lignin–polyurethane films prepared by casting method, Ind Crops Prod, 20, 231, 10.1016/j.indcrop.2004.04.024 Kim, 2010, Preparation of a thermoresponsive lignin-based biomaterial through atom transfer radical polymerization, Biomacromolecules, 11, 981, 10.1021/bm901455p Gao, 2012, Synthesis of lignin nanofibers with ionic-responsive shells: water-expandable lignin-based nanofibrous mats, Biomacromolecules, 13, 3602, 10.1021/bm301039f Matyjaszewski, 2012, Atom transfer radical polymerization (ATRP): current status and future perspectives, Macromolecules, 45, 4015, 10.1021/ma3001719 Wang, 2011, Combining renewable gum rosin and lignin: towards hydrophobic polymer composites by controlled polymerization, J Polym Sci Part A Polym Chem, 49, 3728, 10.1002/pola.24809 Kadla, 2002, Lignin-based carbon fibers for composite fiber applications, Carbon, 40, 2913, 10.1016/S0008-6223(02)00248-8 Norberg, 2013, A new method for stabilizing softwood kraft lignin fibers for carbon fiber production, J Appl Polym Sci, 128, 3824, 10.1002/app.38588 Qin, 2012, Carbon fibers based on pyrolytic lignin, J Appl Polym Sci, 126, E203, 10.1002/app.36554 Nordström, 2013, A new softening agent for melt spinning of softwood kraft lignin, J Appl Polym Sci, 129, 1274, 10.1002/app.38795 Warren, 2006, Low-cost carbon fiber – will the market develop?, Compos Technol, 12, 7 Maradur, 2012, Preparation of carbon fibers from a lignin copolymer with polyacrylonitrile, Synth Met, 162, 453, 10.1016/j.synthmet.2012.01.017 Inone-Kauffmann, 2009, ARBOFORM® – a lignin-based thermoplastic, Int Sugar J, 111, 10