Abstract
A light-colored hydroxypropyl sulfonated alkali lignin (HSAL) was synthesized based on pine alkali lignin (AL) by grafted-sulfonation and crosslinking reaction processes. The reactions were evaluated by gel-permeation chromatography (GPC), infrared (IR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy. The sulfonic group content and the molecular weight (Mw) of HSAL significantly increased, while the phenolic hydroxyl groups diminished by around 80% compared to AL. The color of HSAL turned to light yellow compared to the dark brown color of AL, that is, it stained less the fiber. The dispersity, heat stability, and dye uptake of dye bath with HSAL was significantly improved compared to sodium lignosulfonate, sulfomethylated AL, and dispersants of the naphthalene series.
Acknowledgments
The authors would like to acknowledge the financial support of the National Basic Research Program of China 973 (2012CB215302), the National Natural Science Foundation of China (21436004), International S&T Cooperation Program of China (2013DFA41670), and the Fundamental Research Funds for the Central Universities (2014ZP0003).
References
Bu, L., Xing, Y., Yu, H., Gao, Y., Jiang, J. (2012) Comparative study of sulfite pretreatments for robust enzymatic saccharification of corn cob residue. Biotechnol. Biofuels 5:87.10.1186/1754-6834-5-87Search in Google Scholar PubMed PubMed Central
Capanema, E.A., Balakshin, M.Y., Chen, C.-L., Gratzl, J.S., Kirkman, A.G. (2002) Oxidative ammonolysis of technical lignins. Part 3. Effect of temperature on the reaction rate. Holzforschung 56:402–415.10.1515/HF.2002.063Search in Google Scholar
Chirkova, J., Andersone, I., Irbe, I., Spince, B., Andersons, B. (2011) Lignins as agents for bio-protection of wood. Holzforschung 65:497–502.10.1515/hf.2011.092Search in Google Scholar
Choi, J.H., Kang, M.J. (2006) Preparation of nano disperse dyes from nanoemulsions and their dyeing properties on ultramicrofiber polyester. Fiber. Polym. 7:169–173.10.1007/BF02908262Search in Google Scholar
Dilling, P. (1984) Color reduction process for non-sulfonated lignin, US Patent 4486346.Search in Google Scholar
Dilling, P. (1988) Effect of cation type on lignosulfonate dispersant performance in disperse dye systems. Text. Chem. Color. 20:17–22.Search in Google Scholar
Dilling, P., Huguenin, S.B. (1999) High activity sulfonated lignin dye dispersants, US Patent 5980589.Search in Google Scholar
Dilling, P., Prazak, G. (1977) Process for making sulfonated lignin surfactants, US Patent 4001202.Search in Google Scholar
Dilling, P., Samaranayake, G.S. (1999) Mixtures of amine modified lignin with sulfonated lignin for disperse dye, US Patent 5989299.Search in Google Scholar
Faix O. (1992) Fourier transform infrared spectroscopy. In: Methods in Lignin Chemistry, Lin SY, Dence CW (Eds.). Springer, Berlin, 83–109.10.1007/978-3-642-74065-7_7Search in Google Scholar
Ge, Y., Wei, Q., Li, Z. (2014) Preparation and evaluation of the free radical scavenging activities of nanoscale lignin biomaterials. Bioresources 9:6699–6706.10.15376/biores.9.4.6699-6706Search in Google Scholar
Geng, X.F., Hu, X.Q., Xia, J.J., Jia, X.C. (2013) Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants. Appl. Surf. Sci. 271:284–290.10.1016/j.apsusc.2013.01.185Search in Google Scholar
Giles, C.H. (1981) The surface properties of dyes. Rev. Prog. Color. Relat. Top. 11:89–100.10.1111/j.1478-4408.1981.tb03718.xSearch in Google Scholar
Heitner, C., Dimmel, D., Schmidt, J. Lignin and Lignans: Advances in Chemistry. CRC press, Boca Raton, 2010.Search in Google Scholar
Hofrichter, M., Fritsche, W. (1997) Depolymerization of low-rank coal by extracellular fungal enzyme systems. III. In vitro depolymerization of coal humic acids by a crude preparation of manganese peroxidase from the white-rot fungus Nematoloma frowardii b19. Appl. Microbiol. Biotechnol. 47:566–571.10.1007/s002530050974Search in Google Scholar
Huynh, L., Beattie, D.A., Fornasiero, D., Ralston, J. (2006) Effect of polyphosphate and naphthalene sulfonate formaldehyde condensate on the rheological properties of dewatered tailings and cemented paste backfill. Miner. Eng. 19:28–36.10.1016/j.mineng.2005.05.001Search in Google Scholar
Imsgard, F., Falkehag, S., Kringstad, K. On Possible Chromophoric Structures in Spruce Wood. CRC press, Boca Raton, 1971.Search in Google Scholar
Jakobsons, J., Hortling, B., Erins, P., Sundquist, J. (1995) Characterization of alkali soluble fraction of steam exploded birch wood. Holzforschung 49:51–59.10.1515/hfsg.1995.49.1.51Search in Google Scholar
Kissa, E. (1990a) Partitioning and stability of aqueous dispersions. Effect of electrolytes on the stability of aqueous dye dispersions. Langmuir 6:1217–1221.10.1021/la00097a003Search in Google Scholar
Kissa, E. (1990b) Partitioning and stability of aqueous dispersions. Particle size of dye dispersions. Langmuir 6:478–481.10.1021/la00092a030Search in Google Scholar
Lemarchand, C., Couvreur, P., Vauthier, C., Costantini, D., Gref, R. (2003) Study of emulsion stabilization by graft copolymers using the optical analyzer Turbiscan. Int. J. Pharm. 254:77–82.10.1016/S0378-5173(02)00687-7Search in Google Scholar
Li, P., Yang, D., Lou, H., Qiu, X. (2008) Study on the stability of coal water slurry using dispersion-stability analyzer. J. Fuel. Cell. Sci. Tech. 36:524–529.10.1016/S1872-5813(08)60033-XSearch in Google Scholar
Lin, S.Y. (1980) Process for reduction of lignin color, US Patent 4184845.Search in Google Scholar
Lin, S.Y. Methods in Lignin Chemistry. Springer-Verlag, Berlin, 1992.10.1007/978-3-642-74065-7Search in Google Scholar
Lou, H.M., Lai, H.R., Wang, M.X., Pang, Y.X., Yang, D.J., Qiu, X.Q., Wang, B., Zhang, H.B. (2013) Preparation of lignin-based superplasticizer by graft sulfonation and investigation of the dispersive performance and mechanism in a cementitious system. Ind. Eng. Chem. Res. 52:16101–16109.10.1021/ie402169gSearch in Google Scholar
Qian, Y., Deng, Y., Li, H., Qiu, X. (2014) Reaction-free lignin whitening via a self-assembly of acetylated lignin. Ind. Eng. Chem. Res. 53:10024–10028.10.1021/ie5010338Search in Google Scholar
Qin, Y., Yang, D., Guo, W., Qiu, X. (2015) Investigation of grafted sulfonated alkali lignin polymer as dispersant in coal-water slurry. J. Ind. Eng. Chem. doi, 10.1016/j.jiec.2014.12.034.10.1016/j.jiec.2014.12.034Search in Google Scholar
Sakkayawong, N., Thiravetyan, P., Nakbanpote, W. (2005) Adsorption mechanism of synthetic reactive dye wastewater by chitosan. J. Colloid. Interf. Sci. 286:36–42.10.1016/j.jcis.2005.01.020Search in Google Scholar
Shin, E.W., Rowell, R.M. (2005) Cadmium ion sorption onto lignocellulosic biosorbent modified by sulfonation: the origin of sorption capacity improvement. Chemosphere 60:1054–1061.10.1016/j.chemosphere.2005.01.017Search in Google Scholar PubMed
Tejado, A., Pena, C., Labidi, J., Echeverria, J., Mondragon, I. (2007) Physico-chemical characterization of lignins from different sources for use in phenol–formaldehyde resin synthesis. Bioresour. Technol. 98:1655–1663.10.1016/j.biortech.2006.05.042Search in Google Scholar
Xu, Q., Qin, M., Shi, S., Jin, L., Fu, Y. (2006) Structural changes in lignin during the deinking of old newsprint with laccase–violuric acid system. Enzyme. Microb. Tech. 39:969–975.10.1016/j.enzmictec.2006.01.031Search in Google Scholar
Yang, D., Qiu, X.Q., Zhou, M.S., Lou, H.M. (2007) Properties of sodium lignosulfonate as dispersant of coal water slurry. Energ. Convers. Manage. 48:2433–2438.10.1016/j.enconman.2007.04.007Search in Google Scholar
Yiqin Yang, Z.L. (2004) Study on preparation of dye dispersant by modified craftlignin. Chem. Ind. Forest Prod. 23:32–37.Search in Google Scholar
Yuan, T., He, J., Xu, F., Sun, R. (2009) Fractionation and physico-chemical analysis of degraded lignins from the black liquor of Eucalyptus pellita KP-AQ pulping. Polym. Degrad. Stabil. 94:1142–1150.10.1016/j.polymdegradstab.2009.03.019Search in Google Scholar
Zhou, H., Yang, D., Wu, X., Deng, Y., Qiu, X. (2012) Physicochemical properties of sodium lignosulfonates (NaLS) modified by laccase. Holzforschung 66:825–832.10.1515/hf-2011-0189Search in Google Scholar
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