Conversion of technical lignins to functional materials with retained polymeric properties

Journal of Wood Science

Volumn 61, Issue 3, 2015, Pages 230-250

  Matsushita, Yasuyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Functional material; Lignin based materials; Technical lignin

Indexed keywords

CHEMICAL MODIFICATION; FUNCTIONAL MATERIALS; PAPER AND PULP INDUSTRY;

COMPLEXES STRUCTURE; DISPERSANTS; LIGNIN-BASED MATERIAL; LIGNOSULFONATES; NATIVE LIGNINS; PROPERTY; PULP AND PAPER INDUSTRY; STRUCTURAL VARIATIONS; TECHNICAL LIGNIN; THERMAL RECYCLING;

LIGNIN;

EID: 84929963193     PISSN: 14350211     EISSN: 16114663     Source Type: Journal    
DOI: 10.1007/s10086-015-1470-2     Document Type: Article

References (254)

1. Sjöström E (1992) Lignin. Wood chemistry fundamentals and applications, 2nd edn. Academic press, San Diego, pp 71–89
2. Laurichesse S, Avérous L (2014) Chemical modification of lignins: towards biobased polymers. Prog Polym Sci 39:1266–1290
3. Freudenberg K (1959) Biosynthesis and constitution of lignin. Nature 183:1152–1155
4. Hu L, Pan H, Zhou Y, Zhang M (2011) Methods to improve lignin’s reactivity as a phenol substitute and as replacement for other phenolic compounds: a brief review. Bioresour 6:1–11
5. Månsson P (1983) Quantitative determination of phenolic and total hydroxy groups in lignins. Holzforschung 37:143–146
6. EI Mansouri NE, Salvadó J (2007) Analytical methods for determining functional groups in various technical lignins. Ind Crop Prod 26:116–124
7. EI Mansouri NE, Salvadó J (2006) Structural characterization of technical lignins for the production of adhesives: application to lignosulfonate, kraft, soda-anthraquinone, organosolv and ethanol process lignin. Ind Crop Prod 24:8–16
8. Ponomarenko J, Dizhbite T, Lauberts M, Viksna A, Dobele G, Bikovens O, Telysheva G (2014) Characterization of softwood and hardwood LignoBoost kraft lignins with emphasis on their antioxidant activity. Bioresources 9:2051–2068
9. West MA, Hickson AC, Mattinen ML, Lloyd-Jones G (2014) Evaluating lignins as enzyme substrates: insights and methodological recommendations from a study of laccase-catalyzed lignin polymerization. Bioresources 9:2782–2796
10. Sjöström E (1992) Wood pulping. Wood chemistry fundamentals and applications, 2nd edn. Academic press, San Diego, pp 114–164
11. Ekeberg D, Gretland KS, Gustafsson J, Bråten SM, Fredheim GE (2006) Characterisation of lignosulphonates and kraft lignin by hydrophobic interaction chromatography. Anal Chim Acta 565:121–128
12. Pan X, Saddler JN (2013) Effect of replacing polyol by organosolv and kraft lignin on the property and structure of rigid polyurethane foam. Biotechnol Biofuel 6:12–21
13. Alonso MV, Rodríguez JJ, Oliet M, Rodríguez F, García J, Gilarranz MA (2001) Characterization and structural modification of ammonic lignosulfonate by methylolation. J Appl Polym Sci 82:2661–2668
14. 2 incubation. Appl Microbiol Biotechnol 97:10309–10320
15. Ye DZ, Zhang MH, Gan LL, Li QL, Zhang X (2013) The influence of hydrogen peroxide initiator concentration on the structure of eucalyptus lignosulfonate. Int J Biol Macromole 60:77–82
16. Sannigrahi P, Ragauskas AJ, Miller SJ (2010) Lignin structural modifications resulting from ethanol organosolv treatment of loblolly pine. Energy Fuel 24:683–689
17. Pan X, Arato C, Gilkes N, Gregg D, Mabee W, Pye K, Xiao Z, Zhang X, Saddler J (2005) Biorefining of softwoods using ethanol organosolv pulping: preliminary evaluation of process streams for manufacture of fuel-grade ethanol and co-products. Biotech Bioeng 90:473–481
18. EI Mansouri NE, Vilaseca J F, Salvadó J (2012) Structural changes in organosolv lignin during its reaction in an alkaline medium. J Appl Polym Sci 126:E213–E220
19. Benar P, Goncçalves AR, Mandelli D, Schuchardt U (1999) Eucalyptus organosolv lignins: study of the hydroxymethylation and use in resol. Bioresour Technol 68:11–16
20. Kin Z (1990) The acetolysis of beech wood. Tappi J 73:237–238
21. Delmas GH, Benjelloun-Mlayah B, Bigot YL, Delmas M (2011) Functionality of wheat straw lignin extracted in organic acid media. J Appl Polym Sci 121:491–501
22. Gellerstedt G, Lindfors EL (1984) Structural changes in lignin during kraft pulping. Holzforschung 38:151–158
23. 13C-NMR-spectra and molecular weight distributions. Holzforschung 40(suppl):51–60
24. Nilvebrant NO, Ragauskas A, Dyer T, Kleen M (2001) Lignin-extractives-complexes may disturb analysis of isolated lignins by NMR. In: Proceedings of the 11th International Symposium on Wood and Pulping Chemistry, Nice, France, vol 1, pp 139–142
25. Balakshin MY, Capanema EA, Chen AL, Gracz HS (2003) Elucidation of the structures of residual and dissolved pine kraft lignins using an HMQC NMR technique. J Agric Food Chem 51:6116–6127
26. Gierer J, Lindeberg O (1980) Reactions of lignin during sulfate pulping. Part XIX. Isolation and identification of new dimers from a spent sulfate liquor. Acta Chem Scand B34:161–170
27. Berthold F, Gellerstedt G (1993) Reactive structures formed during the initial phase of kraft cook. In: Proceedings of the 7th International Symposium on Wood and Pulping Chemistry, Beijing, China, vol 3, pp 160–163
28. Gierer J, Norén I, Wännström S (1987) Formation of condensation products on treatment of nom-phenolic lignin units of the β-aryl ether type with alkali. Model studies on a novel mode of alkaline lignin condensation. Holzforschung 41:79–82
29. 13C-NMR spectra of kraft lignins. Holzforschung 37:237–244
30. 13C correlation 2D NMR-spectroscopy. Holzforschung 54:302–308
31. Sipilä J, Wiik C, Koli K, Filpponen I, Karhunen P, Maunu SL, Liitiä T (2001) Mordan NMR techniques and model experiments in search for changes in the chemical structure of lignin during pulping. In: Proceedings of the 11th International Symposium on Wood and Pulping Chemistry, Nice, France, vol 1, pp 9–12
32. Terashima N, Araki H, Suganuma N (1977) Radiotracer experiments on lignin reactions II: the behavior of lignin in kraft pulping process (in Japanese). Mokuzai Gakkaishi 23:343–347
33. Niemelä K, Alén R, Sjöström E (1985) The formation of carboxylic acids during kraft and kraft-anthraquinone pulping of birch wood. Holzforschung 39:167–172
34. Löwendahl L, Peterson G, Sanuelson O (1978) Phenolic compounds in kraft black liquor. Svensk Papperstidn 81:392–396
35. Niemelä K, Sjöström E (1985) Identification of α-hydroxy-syringylalkanoic acids in birch kraft black liquors. Holzforschung 39:365–366
36. Gierer J, Wännström S (1984) Formation of alkali-stable C-C bonds between lignin and carbohydrate fragments during kraft pulping. Holzforschung 38:181–184
37. Gierer J, Wännström S (1986) Formation of ether bonds between lignin and carbohydrates during alkaline pulping process. Holzforschung 40:347–352
38. Westermark U, Samuelsson B, Lundquist K (1995) Homolytic cleavage of the β-ester bond in phenolic β-O-4 structures in wood lignin and in guaiacylglycerol-β-guaiacyl ether. Res Chem Intermed 21:343–352
39. Tsutsumi Y, Kondo R, Imamura H (1993) Reaction of syringylglycerol-β-syringyl ether type of lignin model compounds in alkaline medium. J Wood Chem Technol 13:25–42
40. Sipilä J, Brunow G, Ämmälahti E, Kilpeläinen I, Bujanovic B, Hortling B (1999) On the chemical structure of lignins in situ and in pulps revealed by multidimensional NMR studies. In: Proceedings of the 10th international symposium on wood and pulping chemistry, Yokohama, Japan, vol 1, pp 364–367
41. Sipilä J, Brunow G, Tunninen P, Niemi T, Åhlgren A (1997) Degradation of quinone methides via β-ether hemolysis—An important reaction the chemistry of hardwood lignins? In: Proceedings of the 9th International Symposium on Wood and Pulping Chemistry, Montreal, Canada, Oral, pp B2-1–B2-4
42. Mortimer RD (1982) The formation of coniferyl alcohol during alkaline delignification with anthraquinone. J Wood Chem Technol 2:383–415
43. Kondo R, McCarthy JL (1985) Condensation of lignins with coniferyl alcohol in alkaline aqueous solutions. J Wood Chem Technol 5:37–52
44. Taneda H, Nakano J, Hosoya S, Chang HM (1987) Stability of α-ether type model compounds during chemical pulping processes. J Wood Chem Technol 7:485–498
45. Lindberg JJ, Tylli H, Majani C (1964) Notes on the molecular weight and the fractionation of lignins with organic solvents. Paperi Puu 46:521–526
46. Helm RF, Toikka M, Li K, Brunow G (1997) Lignin model glycosides: preparation and optical resolution. J Chem Soc Perkin Trans 1(1997):533–537
47. Goliath M, Lindgren BO (1961) Reactions of thiosulphate during sulphite cooking. Part 2. Mechanism of thiosulfate sulphidation of vanillyl alcohol. Svensk Papperstidning 64:469–471
48. Gierer J (1970) The reactions of linin during pulping. Adescription and comparison of conventional pulping process. Svensk Papperstidning 73:571–596
49. Gellerstedt G, Gierer J (1971) The reactions of lignin during acidic sulphite pulping. Svensk Papperstidning 74:117–127
50. Glennie DW (1971) Reactions in sulfite pulping. In: Sarkanen KV, Ludwig CH (eds) Lignins occurrence, formation, structure and reactions. Wiley Interscience, New York, pp 597–694
51. Meshitsuka G, Nakano J (1972) Studies on double bonds in lignosulphonate: existence of chalcone structure in lignosulphonate. Pulp Paper Mag Can 73:61–64
52. Brudin S, Schoenmakers P (2010) Analytical methodology for sulfonated lignins. J Sep Sci 33:439–452
53. Araki H, Kachi S, Terashima N (1977) Radiotracer experiments on lignin reactions III: the behavior of lignin in acidic sulfite pulping process (in Japanese). Mokuzai Gakkaishi 23:348–352
54. Sakakibara A (1980) A structure model of softwood lignin. Wood Sci Technol 14:89–100
55. 13C NMR data of benzylsulfonic acids—model compounds for lignosulfonate. Magn Reson Chem 46:299–305
56. Gardon JL, Mason SG (1955) Physicochemical studies of lignosulphonates II: behavior as polyelectrolytes. Can J Chem 33:1491–1501
57. Rezanowich A, Goring DAI (1960) Polyelectrolyte expansion of a lignin sulfonate microgel. J Colloid Sci 15:452–471
58. Goring DAI (1971) Polymer properties of lignin and lignin derivatives. In: Sakanen KV, Ludwig CH (eds) Lignins, occurrence, formation, structure and reactions. Wiley Interscience, New York, pp 695–768
59. Kontturi AK, Kontturi A, Niinikoski P (1991) Transport of lignosulphonates under an external electric field. J Chem Soc Faraday Trans 87:1779–1783
60. Myrvold BO (2008) A new model for the structure of lignosulphonates. Part 1. Behaviour in dilute solutions. Ind Crop Prod 27:214–219
61. Pye EK, Lora JH (1991) The Alcell™ process. A proven alternative to kraft pulping. Tappi J 74:113–118
62. Sarkanen KV (1990) Chemistry of solvent pulping. Tappi J 73(10):215–219
63. Shimada K, Hosoya S, Ikeda T (1997) Condensation reactions of softwood and hardwood lignin model compounds under organic acid cooking conditions. J Wood Chem Technol 17:57–72
64. Liu Y, Carriero S, Pye K, Argyropoulos DS (2000) A comparison of the structural changes occurring in lignin during Alcell and kraft pulping of hardwoods and softwoods. In: Grasser WG, Norhey RA, Schultz TP (eds) ACS Symposium Series 742 Lignin: historical, biological, and materials perspectives. American Chemical Society, Washington, DC, pp 447–464
65. Young RA, Davis JL (1986) Organic acid pulping of wood. Part II. Acetic acid pulping of aspen. Holzforschung 40:99–108
66. Davis JL, Young RA, Deodhar SS (1986) Organic acid pulping of wood III. Acetic acid pulping of spruce. Mokuzai Gakkaishi 32:905–914
67. Sano Y, Maeda H, Sakashita Y (1989) Pulping of wood at atmospheric pressure I: pulping of hardwoods with aqueous acetic acid containing a small amount of organic sulfonic acid. Mokuzai Gakkaishi 35:991–995
68. Sano Y, Nakamura M, Shimamoto S (1990) Pulping of wood at atmospheric pressure II: pulping of birch of wood with aqueous acetic acid containing a small amount of sulfuric acid. Mokuzai Gakkaishi 36:207–211
69. Parajó JC, Alonso JL, Vázquez D (1993) On the behavior of lignin and hemicelluloses during the acetosolv processing of wood. Bioresour Technol 46:233–240
70. Shukry N, Fadel SM, Agblevor FA, EI-Kalyoubi SF (2008) Some physical properties of acetosolv lignins from bagasse. J Appl Poly Sci 109:434–444
71. Davis JL, Nakatsubo F, Murakami K, Umezawa T (1987) Organic acid pulping of wood IV: reactions of arylglycerol-β-guaiacyl ethers. Mokuzai Gakkaishi 33:478–486
72. Yasuda S, Ito N (1987) Behavior of lignin in organic acid pulping I: reaction of arylglycerol-β-aryl ethers with acetic acid. Mokuzai Gakkaishi 33:708–715
73. Yasuda S (1988) Behavior of lignin in organic acid pulping II: reaction of phenylcoumaran and 1,2-diaryl-1,3-propanediol with acetic acid. J Wood Chem Technol 8:155–164
74. Erismann NM, Freer J, Baeza J, Durán N (1994) Organosolv pulping VII: delignification selectivity of formic acid pulping of Eucalyptus grandis. Bioresour Technol 47:247–256
75. Forss KG, Fuhrmann A (1979) Finnish plywood, particleboard, and fireboard made with a lignin-base adhesive. Forest Prod J 29:39–43
76. Forss FG, Fuhrmann A (1976) KARATEX-the lignin-based adhesive for plywood, particle board and fibre board. Pap Puu 58:817–824
77. Marton J, Marton T, Falkchag SI, Adler E (1966) Alkali-catalyzed reactions of formaldehyde with lignins. In: Marton J (ed) Lignin structure and reactions., Advances in Chemistry Series 59American Chemical Society, Washington, DC, pp 125–144
78. Zhao LW, Griggs BF, Chen CL, Gratzl JS (1994) Utilization of softwood kraft lignin as adhesive for the manufacture of reconstituted wood. J Wood Chem Technol 14:127–145
79. Gupta RC, Sehgal VC (1979) Effect of viscosity and molecular weight of lignin-phenolformaldehyde resin on the glue adhesion strength of plywood. Holzforsch Holzverwert 31:7–9
80. Klašnja B, Kopitovič S (1992) Lignin–phenol–formaldehyde resins as adhesives in the production of plywood. Holz Roh Werkst 50:282–285
81. Kazayawako JSM, Riedle B, Poiquin J, Barry AO, Matuana LM (1992) A lignin–phenol–formaldehyde binder for particle board. Part 1. Thermal characteristics. Holzforschung 46:257–262
82. Moubarik A, Grimi N, Boussetta N, Pizzi A (2013) Isolation and characterization of lignin from Moroccan sugar cane bagasse: production of Phenol-formaldehyde wood adhesives. Ind Crop Prod 45:296–302
83. Hamidreza S, Fan GM (2014) Lignin in straw and its applications as an adhesive. Int J Adhes Adhes 48:92–101
84. Peng W, Riedl B, Barry O (1993) Study on the kinetics of lignin methylolation. J Appl Polym Sci 48:1757–1763
85. Budin D, Suša L, Volčič J (1990) Application of modified lignosulfonates ini adhesives for insulation board manufacture based mineral wool. J Wood Chem Technol 10:531–542
86. Ayla VC (1982) Properties and decomposition of lignins isolated by means of an alcoholic-water-mixture VII: utilization of ethanol-water lignins as a glue for wood. Holzforschung 36:93–98
87. Vázquez G, Antorrena G, González J, Mayor J (1995) Lignin–phenol–formaldehyde adhesives for exterior grade plywoods. Bioresour Technol 51:187–192
88. Vázquez G, González J, Freire S, Antorrena G (1997) Effect of chemical modification of lignin on the glue bond performance of lignin-phenol resins. Bioresour Technol 60:191–198
89. Sano Y, Ichikawa A (1987) Preparation of lignin-based phenol resin adhesives from solvolysis lignins. Mokuzai Gakkaishi 33:42–46
90. Sano Y, Yamane N (1987) Preparation of lignin-based resorcinol resin adhesives from solvolysis lignins. Mokuzai Gakkaishi 33:47–52
91. Dolenko AJ, Clarke MR (1978) Resin binders from kraft lignin. For Prod J 28:41–47
92. Alonso MV, Oliet M, Rodríguez F, Astarloa G, Echeverría JM (2004) Use of a methylolated softwood ammonium lignosulfonate as partial substitute of phenolin resol resins manufacture. J Appl Polym Sci 94:643–650
93. Malutan T, Nicu R, Popa VI (2008) Contribution to the study of hydroxymethylation reaction of alkali lignin. BioResour 3:13–20
94. Nimz H (1969) Condensation reactions of lignin. Reaction of lignin model compounds with resorcinol and hydrochloric acid. Holzforschung 23:84–88
95. Kratzl K, Oburger M (1980) Condensation reactions of lignin model compounds with phenol under acid catalysis. Holzforschung 34:11–16
96. Kratzl K, Oburger M (1980) Condensation reactions of lignin model compounds with phenol under acid catalysis. Part II. Holzforschung 34:191–196
97. Funaoka M, Abe I (1987) Phenyl nucleus-exchange method for the degradation of lignin. Wood Sci Technol 21:261–279
98. Yasuda S, Tachi M, Takagi Y (1989) Phenolization of red pine sulfuric acid lignin and guaiacyl sulfuric acid lignin model in the presence of sulfuric acid catalyst. Mokuzai Gakkaishi 35:513–520
99. Funaoka M, Fukatsu S (1996) Characteristics of lignin structural conversion in a phase-separative reaction system composed of cresol and sulfuric acid. Holzforschung 50:245–252
100. Lin L, Yao Y, Shiraishi N (2001) Liquefaction mechanism of β-O-4 lignin model compound in the presence of phenol under acid catalysis. Holzforschung 55:617–624
101. Gierer J, Pettersson I (1977) Studies on the condensation of lignins in alkaline media. Part II. The formation of stilbene and arylcoumaran structures through neighbouring group participation reactions. Can J Chem 55:593–599
102. Gierer J, Lindeberg O (1979) Studies on the condensation of lignins in alkaline media. Part III. The formation of stilbenes, aryl coumarins and diaryl methanes on treatment of spruce wood meal with alkali and white liquor in the presence of xylenols. Acta Chem Scand B33:580–622
103. Kabayashi A, Haga T, Sato K (1966) On the reaction of thiolignin with phenol (in Japanese). Mokuzai Gakkaishi 12:305–310
104. Kabayashi A, Haga T, Sato K (1967) On the properties of tholignin modified with phenol as a raw material of phenolic resin (in Japanese). Mokuzai Gakkaishi 13:306–312
105. Kabayashi A, Haga T, Sato K (1967) On the reaction between phenol modified thiolignin and hexamethylenetetramine (in Japanese). Mokuzai Gakkaishi 13:312–318
106. Shashi JSP, Singh SV, Gupta RC (1982) Kinetics and mechanism of lignin formaldehyde resinification reaction. Cellul Chem Technol 16:511–522
107. Hayashi A, Nakamura Y, Urkita T (1967) Demethylation of lignosulphonate during the gelling reaction with dichromate. Mokuzai Gakkaishi 13:194–197
108. Olivares M, Guzmán JA, Natho A, Saavedra A (1988) Kraft lignin utilization in adhesives. Wood Sci Technol 22:157–165
109. Gupta RC, Singh SP, Shashi J (1978) Phenol-formaldehyde adhesives for plywood. Holzforsch Holzverwet 30:6–9
110. An XN (1995) Demethylated kraft lignin as a substitute for phenol in wood adhesive. Chem Ind Forest Prod 15:36–42
111. Wu S, Zhen H (2001) Characteristics of demethylated wheat straw soda lignin and its utilization in lignin-based phenolic formaldehyde resins. Cellul Chem Technol 35:253–262
112. Lundquist K (2001) Lignin reactions in neutral, acidic and alkaline media. In: Proceedings of the 11th International Symposium on Wood and Pulping Chemistry, Nice, France, vol 1, pp 1–4
113. Matsushita Y, Jo EK, Inakoshi R, Yagami S, Takamoto N, Fukushima K, Lee SC (2013) Hydrothermal reaction of sulfuric acid lignin generated as a by-product during bioethanol production using lignocellulosic materials to convert bioactive agents. Ind Crop Prod 42:181–188
114. Chen CM (1995) Gluability of kraft lignin copolymer resins on bonding southern pine plywood. Holzforschung 49:153–157
115. Cheng S, Yuan Z, Leitch M, Anderson M, Xu CC (2013) Highly efficiency de-polymerization of organosolve lignin using a catalytic hydrothermal process and production of phenolic resin/adhesives with the depolymerized lignin as a substitute for phenol a high substitution ratio. Ind Crop Prod 44:315–322
116. Shintani K, Sano Y, Sasaya T (1994) Preparation of moderate-temperature setting adhesives from softwood kraft lignin. Holzforschung 48:337–342
117. Shintani K, Sano Y (1995) Preparation of kraft lignin-based cold-setting wood adhesives. Holzforschung 49:351–357
118. Auad ML, Zhao L, Shen H, Nutt SR, Sorathia U (2007) Flammability properties and mechanical performance of epoxy modified phenolic foams. J Appl Polym Sci 104:1399–1407
119. Hu L, Zhou Y, Zhang M, Liu R (2012) Characterization and properties of a lignosulfonate-based phenolic foam. Bioresour 7:554–564
120. Hu L, Zhou Y, Liu R, Zhang M, Yang X (2013) Synthesis of foaming resol resin modified with oxidatively degraded lignosulfonate. Ind Crop Prod 44:364–366
121. Koch VH, Krause F, Steffan R, Woelk HU (1983) Herstellung von Phenolharzen unter Verwendung von Stärkeprodukten. Starch/Stärke 35:304–313
122. Zhang L, Zheng Y, Zhang Y, Lin T (2013) Effect of starch and lignin on physico-chemical properties of phenol–starch resin and its resin core sand. Starch/Stärke 65:666–678
123. Oliveira W, Glasser WG (1994) Multiphase Materials with lignin. 11. Starlike copolymers with caprolactone. Macromolecules 27:5–11
124. Hirose S, Hatakeyama T, Izuta Y, Hatakeyama H (2002) TG-FTIR studies on lignin-based polycaprolactones. J Therm Anal Calorimetry 70:853–860
125. Matsushita Y, Inomata T, Takagi Y, Hasegawa T, Fukushima K (2011) Conversion of sulfuric acid lignin generated during bioethanol production from lignocellulosic materials into polyesters with ε-caprolactone. J Wood Sci 57:214–218
126. Matsushita Y, Inomata T, Hasegawa T, Fukushima K (2009) Solubilization and functionalization of sulfuric acid lignin generated during bioethanol production from woody biomass. Bioresour Technol 100:1024–1026
127. Chung YL, Olsson JV, Li RJ, Frank CW, Waymouth RM, Billington SL, Sattely ES (2013) A renewable lignin-lactide copolymer and application in biobased composites. ACS Sustain Chem Eng 1:1231–1238
128. Guo ZX, Gandini A, Pla F (1992) Polyesters from lignin. 1: the reaction of kraft lignin with dicarboxylic acid chlorides. Polym Int 27:17–22
129. Guo ZX, Gandini A (1991) Polyesters from lignin-2. The copolyesterification of kraft lignin and polyethylene glycols with dicarboxylic acid chlorides. Eur Polym J 27:1177–1180
130. Luong ND, Binh NTT, Duong LD, Kim DO, Kim DS, Lee SH, Kim BJ, Lee YS, Nam JD (2012) An eco-friendly and efficient route of lignin extraction from black liquor and a llignin-based copolyester synthesis. Polym Bull 68:879–890
131. Fang R, Cheng XS, Lin WS (2011) Preparation and application of dimer acid/lignin graft copolymer. Bioresour 6:2874–2884
132. Saito T, Brown RH, Hunt MA, Pickel DL, Pickel JM, Messman JM, Baker FS, Keller M, Naskar AK (2012) Turning renewable resources into value-added polymer: development of lignin-based thermoplastic. Green Chem 14:3295–3303
133. Sivasankarapillai G, McDonald AG (2011) Synthesis and properties of lignin-highly brached poly(ester-amine) polymeric systems. Biomass Bioenergy 35:919–931
134. Sivasankarapillai G, McDonald AG, Li H (2012) Lignin valorization by forming toughened lignin-co-polymers: development of hyperbranched prepolymers for cross-linking. Biomass Bioenergy 47:99–108
135. Hirose S, Hatakeyama T, Hatakeyama H (2005) Curing and glass transition of epoxy resins from ester-carboxylic acid derivatives of mono-and disaccharides, and alcoholysis lignin. Macromol Symp 224:343–353
136. Ismal TNMT, Hassan HA, Hirose S, Taguchi Y, Hatakeyama T, Hatakeyama H (2010) Synthesis and thermal properties of ester-type crosslinked epoxy resins derived from lignosulfonate and glycerol. Polym Int 59:181–186
137. Ahvazi B, Wojciechwicz O, Ton-That TM, Hawari J (2011) Preparation of lignopolyols from wheat straw soda lignin. J Agric Food Chem 59:10505–10516
138. Hatakeyama T, Izuta Y, Hirose S, Hatakeyama H (2002) Phase transition of lignin-based polycaprolactones and their polyurethane derivatives. Polymer 43:1177–1182
139. Hofmann K, Glasser WG (1993) Engineering plastics from lignin. 21. Synthesis and properties of epoxidized lignin-poly(propylene oxide) copolymers. J Wood Chem Technol 13:73–95
140. Simionescu CI, Cazacu G, Macoveanu MM (1987) Lignin-epoxy resins II: physical and chemical characterization. Cellul Chem Technol 21:525–534
141. Simionescu CI, Rusan V, Turta KI, Bobcova SA, Macoveanu MM, Cazacu G (1993) Synthesis and characterization of some iron-lignosulfonate-base epoxy resins. Cellul Chem Technol 27:627–644
142. Zhao B, Chen G, Liu Y, Hu K, Wu R (2001) Synthesis of lignin base epoxy resin and its characterization. J Matt Sci Lett 20:859–862
143. Uraki Y, Ishikawa N, Nishida M, Sano Y (2001) Preparation of amphiphilic lignin derivative as a cellulase stabilizer. J Wood Sci 47:301–307
144. Nishida M, Uraki Y, Sano Y (2003) Lignin gel with unique swelling property. Bioresour Technol 88:81–83
145. Homma H, Kubo S, Yamada T, Matsushita Y, Uraki Y (2008) Preparation and characterization of amphiphilic lignin derivatives as surfactants. J Wood Chem Technol 28:270–282
146. Delmas GH, Benjelloun-Mlayah B, Bigot YL, Delmas M (2013) Biolignin™ based epoxy resins. J Appl Polym Sci 127:1863–1972
147. Nonaka Y, Tomita B, Hatano Y (1997) Synthesis of lignin/epoxy resins in aqueous systems and their properties. Holzforschung 51:183–187
148. Homma H, Kubo S, Yamada T, Koda K, Matsushita Y, Uraki Y (2010) Conversion of technical lignins to amphiphilic derivatives with high surface activity. J Wood Chem Technol 30:164–174
149. Aso T, Koda K, Kubo S, Yamada T, Nakajima I, Uraki Y (2013) Preparation of novel lignin-based cement dispersants from isolated lignins. J Wood Chem Technol 33:286–298
150. Lin X, Zhou M, Wang S, Lou H, Yang D, Qiu X (2014) Synthesis, structure, and dispersion property of novel lignin-based polyoxyethylene ether from kraft lignin and poly(ethylene glycol). ACS Sustain Chem Eng 2:1902–1909
151. Kubo S, Yamada T, Hashida K, Ono H (2007) Grafting of ethylene glycol chains in lignin during the solvolysis for biomass conversion using ethylene carbonate/ethylene glycol system. Chem Lett 36:502–503
152. Lin J, Kubo S, Yamada T, Koda K, Uraki Y (2012) Chemical thermostabilization for the preparation of carbon fibers from softwood lignin. BioResources 7:5634–5646
153. Lin J, Koda K, Kubo S, Yamada T, Enoki M, Uraki Y (2014) Improvement of mechanical properties of softwood lignin-based carbon fibers. J Wood Chem Technol 34:111–121
154. Saraf VP, Glasser WG (1984) Engineering plastics from lignin III: structure property relationships in solution cast polyurethane films. J Appl Polym Sci 29:1831–1841
155. Wu LCF, Glasser WG (1984) Engineering plastics from lignin I: synthesis of hydroxypropyl lignin. J Appl Polym Sci 29:1111–1123
156. Glasser WG, Barnett CA, Rials TG, Saraf VP (1984) Engineering plastics from lignin II: characterization of hydroxylalkyl lignin derivatives. J Appl Polym Sci 29:1815–1830
157. Nadji H, Bruzzèse C, Belgacem MN, Benaboura A, Gandini A (2005) Oxypropylation of lignins and preparation of rigid polyurethane foams from the ensuing polyols. Macromol Mater Eng 290:1009–1016
158. Huang J, Zhang L (2002) Effects of NCO/OH molar ratio on structure and properties of graft-interpenetrating polymer networks from polyurethane and nitrolignin. Polymer 43:2287–2294
159. Saraf VP, Glasser WG, Wilkes GL, McGrath JE (1985) Engineering plastics from lignin VI: property relationships of PEG-containing polyurethane networks. J Appl Polym Sci 30:2207–2224
160. Saraf VP, Glasser WG, Wilkes GL (1985) Engineering plastics from lignin VII: structure property relationships of poly(butadiene glycol)-containing polyurethane networks. J Appl Polym Sci 30:3809–3823
161. Tan TTM (1996) Cardanol–lignin–based polyurethanes. Polym Int 41:13–16
162. Evtuguin DV, Andreolety JP, Gandini A (1998) Polyurethanes based on oxygen-organosolv lignin. Eur Polym J 34:1163–1169
163. Zarubin YM, Deineko IP, Evtuguin DV, Robert A (1989) Delignification by oxygen in acetone-water media. Tappi J 72:163168
164. Kelly SS, Glasser WG, Ward TC (1988) Engineering plastics from lignin XIV: characterization of chain-extended hydroxypropyl lignins. J Wood Chem Technol 8:341–359
165. Kelly SS, Glasser WG, Ward TC (1988) Engineering plastics from lignin XV: polyurethane films from chain-extended hydroxypropyl lignin. J Appl Polym Sci 36:759–772
166. Yoshida H, Mörck R, Kringstad KP, Hatakeyama H (1987) Kraft lignin in polyurethanes I: mechanical properties on polyurethanes from a kraft lignin-polyether triol polymeric MDI system. J Appl Polym Sci 24:1187–1198
167. Hatakeyama H, Hatakeyama T (2005) Environmentally compatible hybrid-type polyurethane foams containing saccharide and lignin components. Macromol Symp 224:219–226
168. Hatakeyama H, Kato N, Nanbo T, Hatakeyama T (2012) Water absorbent polyurethane composites derived from molasses and lignin filled with microcrystalline cellulose. J Mater Sci 47:7254–7261
169. Hatakeyama T, Asano Y, Hatakeyama H (2003) Mechanical and thermal properties of rigid polyurethane foams derived from sodium lignosulfonate mixed with diethlene-, triethylene- and polyethylene glycols. Macromol Symp 197:171–180
170. Asano Y, Hatakeyama H, Hatakeyama T (2003) Thermal and mechanical properties of sodium lignosulfonate-based rigid polyurethane foams prepared with three kinds of polyols. Sen’i Gakkaishi 59:465–470
171. Sarkar S, Adhikari B (2001) Synthesis and characterization of lignin-HTPB copolyurethane. Eur Polym J 37:1391–1401
172. Sarkar S, Adhikari B (2001) Thermal stability of lignin–hydroxy-terminated polybutadiene copolyurethanes. Polym Degrad Stab 73:169–175
173. Kelly SS, Ward TC, Glasser WG (1990) Multiphase materials with lignin VIII: interpenetrating polymer networks from polyurethanes and polymethyl methacrylate. J Appl Polym Sci 41:2813–2828
174. Koshijima T, Muraki E (1964) Radiation grafting of methyl methacrylate onto lignin (in Japanese). Mokuzai Gakkaishi 10:110–115
175. Koshijima T, Muraki E (1964) Degradation of lignin-methy methacrylate graft copolymer by γ-ray irradiation (in Japanese). Mokuzai Gakkaishi 10:116–119
176. Koshijima T, Muraki E (1966) Solvent effects upon radical-induced graft copolymerization of styrene onto lignin (in Japanese). Mokuzai Gakkaishi 12:139–144
177. Koshijima T (1966) Oxidation of lignin-stylene graftpolymer. Mokuzai Gakkaishi 12:144–150
178. Koshijima T, Muraki E (1968) Radical grafting on lignin. Part 1. Radiation-induced grafting of Styrene onto hydrochloric acid lignin. J Polym Sci Part A-1 6:1431–1440
179. Koshijima T, Muraki E (1967) Radical grafting on lignin II: grafting of styrene onto lignin by initiators. Mokuzai Gakkaishi 13:355–359
180. Phillips PB, Brown W, Stannett VT (1971) The graft copolymerization of stylene and lignin I: hydrochloric acid lignin. J Appl Polym Sci 15:2929–2940
181. Phillips PB, Brown W, Stannett VT (1972) The graft copolymerization of styrene and lignin II: kraft softwood lignin. J Appl Polym Sci 16:1–14
182. Meister JJ, Patil DR (1984) Properties and applications of lignin-acrylamide graft copolymer. J Appl Polym Sci 29:3457–3477
183. Meister JJ, Chen MJ (1991) Graft 1-phenylethlene copolymers of lignin. 1. Synthesis and proof of copolymerization. Macromolecule 24:6843–6848
184. Cunha CD, Deffieux A, Fontanille M (1993) Synthesis and polymerization of lignin-based macromonomers III: radical copolymerization of lignin-based macromonomers with methy methacrylate. J Appl Polym Sci 48:819–831
185. Nam C, Koshijima T, Muraki E, Maku T (1971) Graft copolymerization of methyl methacrylate onto lignosulfonate by H2O2-Fe(II) redox system I: preparation and characterization of the graft copolymer. J Polym Sci Part A-1 9:855–866
186. Chen R, Kokta BV, Valade JL (1979) Graft copolymerization of lignosulfonate and styrene. J Appl Polym Sci 24:1609–1618
187. Chen R, Kokta BV, Valade JL (1980) Study on the graft copolymerization of lignosulfonate and acrylic monomers. J Appl Polym Sci 25:2211–2220
188. Kim YS, Kadla JF (2010) Preparation of a thermoresponsive lignin-base biomaterial through atom transfer radical polymerization. Biomactomolecule 11:981–988
189. Gao G, Dallmeyer JI, Kadla JF (2012) Synthesis of lignin nanofibers with ionic-responsive shells: water-expandable lignin-based nanofibrous mats. Biomacromolecule 13:3602–3610
190. Gao G, Karaaslan MA, Kadla JF, Ko F (2014) Enzymatic synthesis of ionic responsive lignin nanofibers through surface poly(N-isopropylacrylamide) immobilization. Green Chem 16:3890–3898
191. Scripture ED Jr (1937) Indurating composition for concrete. US Patent 2,081,642
192. Scripture ED Jr (1938) Hardening and waterproofing composition for concrete or mortar. US Patent 2,127,451
193. Scripture ED Jr (1939) Cement mix. US Patent 2,169,980
194. Scripture ED Jr (1941) Cement composition. US Pat 2(229):311
195. Mark JG (1938) Concrete and hydraulic cement. US Patent 2,141,570
196. Ernsberger FM, France WG (1945) Portland cement dispersion by adsorption of calcium lignosulfonate. Ind Eng Chem 37:596–600
197. Uchikawa H, Hanehara S, Sawaki D (1997) The role of steric repulsive force in the dispersion of cement particles in fresh paste prepared with organic admixture. Cem Concr Res 27:37–50
198. Matsushita Y, Imai M, Iwatsuki A, Fukushima K (2008) The relationship between surface tension and the industrial performance of water-soluble polymers prepared from acid hydrolysis lignin, a saccharification by-product from woody materials. Bioresour Technol 99:3024–3028
199. Lou H, JiK Lin H, PangY Deng Y, QiuX Zhang H, Xie Z (2012) Effect of molecular weight of sulphonated acetone-formaldehyde condensate on its adsorption and dispersion properties in cementitious system. Cem Concr Res 42:1043–1048
200. Ji D, Luo Z, He M, Shi Y, Gu X (2012) Effect of both grafting and blending modifications on the performance of lignosulphonate-modified sulphanilic acid–phenol–formaldehyde condensates. Cem Concr Res 42:1199–1206
201. Mollah MYA, Palta P, Hess TR, Vempati RK, Cocke DL (1995) Chemical and physical effects of sodium lignosulfonate superplasticizer on the hydration of Portland cement and solidification/stabilization consequences. Cem Concr Res 25:671–682
202. Mollah MYA, Yu W, Schennach R, Cocke DL (2000) A fourier transform infrared spectroscopic investigation of the early hydration of Portland cement and the influence of sodium lignosulfonate. Cem Concr Res 30:267–273
203. Zhang T, Shang S, Yin F, Aishah A, Salmiah A, Ooi TL (2001) Adsorptive behavior of surfactants on surface of Portland cement. Cem Concr Res 31:1009–1015
204. Matsushita Y, Yasuda S (2005) Preparation and evaluation of lignosulfonates as a dispersant for gypsum paste from acid hydrolysis lignin. Bioresour Technol 96:465–470
205. Yang D, Qiu X, Zhou M, Lou H (2007) Properties of sodium lignosulfonate as dispersant of coal water slurry. Energy Convers Manag 48:2433–2438
206. Stránĕl O, Sebök T (1997) Relationships between the properties of ligninsulphonates and parameters of modified samples with cement binders. Part I. Characterizing ligninsulphonates and studying their sorption properties. Cem Concr Res 27:185–191
207. Sebök T, Stránĕl O (1999) Relationships between the properties of lignosulphonates and parameters of modified samples with cement binders. Part II. Study of relationships between molar parameters of lignosulphonates and characteristics of the samples tested. Cem Concr Res 29:591–594
208. Stránĕl O, Sebök T (1999) Relationships between the properties of ligninsulphonates and prameters of modified samples with cement binders. Part III. Determination of sulphonated compounds content, characteristic of sulphonation, sorption studies. Cem Concr Res 29:1769–1772
209. Sebök T, Stránĕl O (2000) Relationships between the properties of ligninsulphonates and parameters of modified samples with cement binders. Part IV. Influence of sulphonated compounds and sulphonation characteristics on the properties of mortar samples. Cem Concr Res 30:511–515
210. Shandra S, Björnström J (2002) Influence of cement and superplasticizers type and dosage on the fluidity of cement mortars-Part I. Cem Concr Res 32:1605–1611
211. Takahashi S, Hattori M, Morimoto M, Uraki Y, Yamada T (2014) Performance of softwood soda-anthraquinone lignin as water-reducing chemical admixture in concrete. J Wood Chem Technol 34:31–38
212. Nadif A, Hunkeler D, Käuper P (2002) Sulfur-free lignins from alkaline pulping tested in mortar for use as mortar additives. Bioresour Technol 84:49–55
213. Baker DA, Gallego NC, Baker FS (2012) On the characterization and spinning of an organic-purified lignin toward the manufacture of low-cost carbon fiber. J Appl Polym Sci 124:227–234
214. Baker DA, Rials TG (2013) Recent advances in low-cost carbon fiber manufacture from lignin. J Appl Polym Sci 130:713–728
215. Tomizuka I, Kurita T, Tanaka Y, Watanabe O (1971) Voids in the carbon fibers produced from lignin and PVA. Yogyo-Kyokai-Shi 79:460–469
216. Johnson DJ, Tomizuka I, Watanabe O (1975) The fine structure of lignin-based carbons. Carbon 13:321–325
217. Kadla JF, Kubo S, Venditti RA, Gilbert RD, Compere AL, Griffith W (2002) Lignin-based carbon fibers for composite fiber applications. Carbon 40:2913–2920
218. Kubo S, Kadla JF (2005) Kraft lignin/poly(ethylene oxide) blends: effect of lignin structure on miscibility and hydrogen bonding. J Appl Polym Sci 98:1437–1444
219. Kubo S, Kadla JF (2005) Lignin-based carbon fibers: effect of synthetic polymer blending on fiber properties. J Polym Environ 13:97–105
220. Kubo S, Ishikawa N, Uraki Y, Sano Y (1997) Preparation of lignin fibers from softwood acetic acid lignin: relationship between fusibility and the chemical structure of lignin. Mokuzai Gakkaishi 43:655–662
221. Brodin I, Ernstsson M, Gellerstedt G, Sjöholm E (2012) Oxidative stabilisation of kraft lignin for carbon fibre production. Holzforschung 66:141–147
222. Nordström Y, Norberg I, Sjöholm E, Drougge R (2013) A new softening agent for melt spinning of softwood kraft lignin. J Appl Polym Sci 129:1274–1279
223. Nordström Y, Joffe R, Sjöholm E (2013) Mechanical characterization and application of weibull statistics to the strength of softwood lignin-based carbon fibers. J Appl Polym Sci 130:3689–3697
224. Braun JL, Holtman KM, Kadla JF (2005) Lignin-based carbon fibers: oxidative thermostabilization of kraft lignin. Carbon 43:385–394
225. Norberg I, Nordström Y, Drougge R, Gellerstedt G, Sjöholm E (2012) A new method for stabilizing softwood kraft lignin fibers for carbon fiber production. J Appl Polym Sci 128:3824–3830
226. Maradur SP, Kim CH, Kim SY, Kim BH, Kim WC, Yang KS (2012) Preparation of carbon fibers from a lignin copolymer with polyacrylonitrile. Synth Met 162:453–459
227. Brodin I, Sjöholm E, Gellerstedt G (2010) The behavior of kraft lignin during thermal treatment. J Anal Appl Pyrolysis 87:70–77
228. Uraki Y, Kubo S, Nigo N, Sano Y, Sasaya T (1995) Preparation of carbon fibers from organbosolv lignin obtained by aqueous acetic acid pulping. Holzforschung 49:343–350
229. Kubo S, Uraki Y, Sano Y (1998) Pretreatment of carbon fibers from softwood lignin by atmospheric acetic acid pulping. Carbon 36:1119–1124
230. Sudo K, Shimizu K (1992) A new carbon fiber from lignin. J Appl Polym Sci 44:127–134
231. Sudo K, Shimizu K, Nakashima N, Yokoyama A (1993) A new modification method of exploded lignin for the preparation of a carbon fiber precursor. J Appl Polym Sci 48:1485–1491
232. Foston M, Nunnery GA, Meng X, Sun Q, Baker FS, Ragauskas A (2013) NMR a critical tool to study the production of carbon fiber from lignin. Carbon 52:65–73
233. Luscombe DK, Nicholls PJ (1973) Acute and subacute oral toxicity of AHR-2438B, a purified sodium lignosulphonate, in rats. Food Cosmet Toxicol 11:229–237
234. Anonymous (2008) Summary and conclusion of the 69th meeting of Joint FAO/WHO Expert Committee on Food Additives, Food and Agricultural Organization of United Nations and World Health Organization, Rome, Italy
235. Vocac JA, Alphin RS (1968) Effects and mechanism of action of a lignosulphonate on experimental gastric ulceration in rats. Eur J Pharmcol 4:99–102
236. Tollner TL, Overstreet JW, Li MW, Meyers SA, Yudin AI, Salinas ER, Cherr GN (2002) Lignosulfonic acid blocks in vitro fertilization of macaque oocytes when sperm are treated either before or after capacitation. J Andrology 23:889–898
237. Suzuki H, Tochikura TS, Iiyama K, Yamazaki S, Yamamoto N, Toda S (1989) Lignosulfonate, a water-solubilized lignin from the waste liquor of the pulping process, inhibits the infectivity and cytopathic effects of human immunodeficiency virus in vitro. Agric Biol Chem 53:3369–3372
238. Suzuki H, Iiyama K, Okubo A, Yamazaki S, Toda S (1989) Lignosulfonate from waste liquor of pulping process activates murine macrophages and causes proliferation of bone marrow cells. Agric Biol Chem 53:1197–1199
239. Suzuki H, Iiyama K, Yoshida O, Yamazaki S, Yamamoto N (1990) Structural characterization of immunoactive and antiviral water-solubilized lignin in an extract of the culture medium of Lentinus edodes mycelia (LEM). Agric Biol Chem 54:479–487
240. Sakagami H, Oh-hara T, Kohda K, Kawazoe Y (1991) Lignified materials as a potential medicinal resource. IV. Dehydrogenation polymers of some phenylpropanoids and their capacity to stimulate polymorphonuclear cell iodination. Chem Pharm Bull 39:950–955
241. Nakashima H, Murakami T, Yamamoto N, Naoe T, Kawazoe Y, Konno K, Sakagami H (1992) Lignified materials as a potential medicinal resource V: aniti-HIV (human immunodeficiency virus) activity of some synthetic lignins. Chem Pharm Bull 40:2102–2105
242. Mitsuhashi S, Kishimoto T, Uraki Y, Okamoto T, Ubukata M (2008) Low molecular weight lignin suppresses activation of NF-κB and HIV-1 promoter. Bioorgan Med Chem 16:2645–2650
243. Wang Z, Zhu JY, Fu Y, Qin M, Shao Z, Jiang J, Yang F (2013) Lignosulfonate-mediated cellulase adsorption enhanced enzymatic saccharification of lignocellulose through weakening nonproductive binding to lignin. Biotechnol Biofuel 6:156–165
244. Zhou H, Lou H, Yang D, Zhu JY, Qiu X (2013) Lignosulfonate to enhance enzymatic saccharification of lignocelluloses: role of molecular weight and substrate lignin. Ind Eng Chem Res 52:8464–8470
245. Lou H, Zhou H, Li X, Wang M, Zhu JY, Qiu X (2014) Understanding the effects of lignosulfonate on enzymatic saccharification of pure cellulose. Cellulose 21:1351–1359
246. Räihä M, Sundman V (1975) Characterization of lignosulfonate-induced phenol oxidase activity in the atypical white-rot fungus Polyporus dichrous. Arch Microbiol 105:73–76
247. Premjet S, Ohtani Y, Sameshima K (1994) Bacterial cellulose production by Acetobacer xylinum ATCC 10245 in a new culture medium with a sulfite pulping waste fraction. Sen-i Gakkaishi 50:124–128
248. Premjet S, Ohtani Y, Sameshima K (1994) The contribution of high molecular lignosulfonate to the powerful bacterial cellulose production system with Acetobacter xylinum ATCC 10245. Sen-i Gakkaishi 50:458–463
249. Premjet S, Ohtani Y, Sameshima K (1996) X-ray diffraction diagram of the bacterial cellulose membrane produced by Acetobacter xylinum in the medium with lignosulfonate. Sen-i Gakkaishi 52:169–174
250. Keshk S, Sameshima K (2006) Influence of lignosulfonate on crystal structure and productivity of bacterial cellulose in a static culture. Enzym Microbial Technol 40:4–8
251. Bardant TB, Oikawa C, Nojiri M, Koda K, Sudiyani Y, Yamada T, Uraki Y (2010) Improvement of saccharification of empty fruit bunch and Japanese cedar pulps with an amphiphilic lignin derivative (in Japanese). Mokuzai Gakkaishi 56:420–426
252. Fukushima K, Terashima N (1991) Heterogeneity in formation of lignin 14 Formation and structure of ligninin differentiating xylem of Ginko biloba. Holzforschung 45(Apr):87–94
253. Sarkanen KV, Hergert HL (1971) Classification and distribution. In: Sarkanen KV, Ludwig CH (eds) Lignins: occurrence, formationstructure and reactions. Wiley-Interscience, New York, pp 43–94
254. Fukushima K, Terashima N (1991) Heterogeneity in formation of lignin. 15. Formation and structure of lignin in compression wood of Pinus thunbergii studied by microautoradiography. J Wood Sci Technol 25:371–381