All Issue

2021 Vol.53, Issue 2 Preview Page
Preparation of Lignin-based Poly(m-aminobenzenesulfonic acid) Copolymers

리그닌 기반 Poly(m-aminobenzenesulfonic acid) 공중합체 제조

Jin Ho Bae1
,
Liang Liang An1
,
Jiansong Chen1
,
Ji Won Heo1
,
Song-Yi Han2
,
Yong Sik Kim3†
배진호 1
,
안량량 1
,
진건송 1
,
허지원 1
,
한송이 2
,
김용식 3†
1Department of Paper Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University
2Institute of Forest Science, College of Forest and Environmental Sciences, Kangwon National University
3Department of Paper Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University
1강원대학교 산림환경과학대학 제지공학과, 학생
2강원대학교 산림과학연구소, 연구교수
3강원대학교 산림환경과학대학 제지공학과, 교수
†Corresponding author: E-Mail: yongsikk@kangwon.ac.kr (Address: Department of Paper Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University, Chuncheon, 24341, Republic of Korea)
30 April 2021. pp. 65-73
PDF XML Citation
Abstract

In this study, the lignin-based poly(m-aminobenzenesulfonic acid) (PABS) copolymer was prepared via a successive two-step synthesis reaction to be used as a precursor for high-value-added biomaterials. Chemical structure analyses such as 1H NMR, FT-IR, elemental contents, and molecular size of PABS confirmed the presence of aromatic amine groups and sulfonic acid groups with Mn 17,400 g/mol. The yield and chemical structure were analyzed by separating the lignin-based PABS prepared by graft polymerization into water-soluble and insoluble lignin-based PABS. Presence of the lignin and PABS functional groups was verified and the yield of the lignin-based PABS copolymer with insoluble lignin-based PABS was high. Therefore, it was confirmed that the compound was mainly composed of the water-insoluble lignin-based PABS copolymer. Moreover, the thermal decomposition temperature of the resulting insoluble lignin-based PABS copolymer was approximately 30℃ higher than that of lignin, indicating improved thermal stability.

Keywords
Kraft lignin
poly(m-aminobenzenesulfonic acid)
grafting
lignin-based copolymer
References

Literature Cited

1

Jin, Z. F., Katsumata, K. S., Lam, T. B. T., and Liyama, K., Covalent linkages between cellulose and lignin in cell walls of coniferous and nonconiferous woods, Biopolymers 83(2):103-110 (2006).

10.1002/bip.20533
2

Braun, J. L., Holtman, K. M., and Kadla, J. F., Lignin-based carbon fibers: Oxidative thermostabilization of kraft lignin, Carbon 43(2):385-394 (2005).

10.1016/j.carbon.2004.09.027
3

Hu, J. J., Zhang, Q. G., and Lee, D. J., Kraft lignin biorefinery: A perspective, Bioresource Technology 247:1181-1183 (2018).

10.1016/j.biortech.2017.08.169
4

Suparn, O., Covington, A. D., Phillips, P. S., and Evans, C. S., An innovative new application for waste phenolic compounds: Use of Kraft lignin and naphthols in leather tanning, Resources, Conservation and Recycling 45(2):114-127 (2005).

10.1016/j.resconrec.2005.02.005
5

Demuner, I. F., Colodette, J. L., Demuner, A. J., and Jardim, C. M., Biorefinery review: Wide-reaching products through Kraft lignin, Bioresources 14(3):7543-7581 (2019).

10.15376/biores.14.3.Demuner
6

Dessbesell, L., Paleologou, M., Leitch, M., Pulkki, R., and Xu, C., Global lignin supply overview and kraft lignin potential as an alternative for petroleum-based polymers, Renewable and Sustainable Energy Reviews 123: (2020).

10.1016/j.rser.2020.109768
7

Lewis, N. G,. A 20th century roller coaster ride: a short account of lignification, Current Opinion in Plant Biology 2(2):153-162 (1999).

10.1016/S1369-5266(99)80030-2
8

Sarkanen, K. V. and Ludwig, C. H., Lignin: occurrence, formation, structure and reactions. Wiley/Interscience, New York, pp. 95–240.

9

Chakar, F. S. and Ragauskas, A. J., Review of current and future softwood kraft lignin process chemistry, Industrial Crops and Products 20(2):131-141 (2004).

10.1016/j.indcrop.2004.04.016
10

Wen, J. L., Sun, Z. J., Sun, Y. C., Sun, S. N., Sun, S. N., Xu, F., and Sun, R. C., Structural characterization of alkali-extractable lignin fractions from bamboo, Journal of Biobased Materials and Bioenergy 4(4):408-428 (2010).

10.1166/jbmb.2010.1111
11

Park, S. Y., Kim, J. Y., Yoon, H. J., and Choi, J. W., Fractionation of lignin macromolecules by sequential organic solvents systems and their characterization for further valuable applications, International Journal of Biological Macromolecules 106:793-802 (2018).

10.1016/j.ijbiomac.2017.08.069
12

Chen, C., Jin, D. X., Ouyang, X. P., Zhao, L. S., Qiu, X. Q., and Wang, F. R., Effect of structural characteristics on the depolymerization of lignin into phenolic monomers, Fuel 223:366-372 (2018).

10.1016/j.fuel.2018.03.041
13

Choi, C. S., Bae, J. H., Park, J. H., Seo, J. H., and Kim, Y. S., Characterization of fractionated hardwood Kraft lignin with organic solvents, Journal of Korea TAPPI 50(6):42-53 (2018).

10.7584/JKTAPPI.2018.12.50.6.42
14

Seo, J. H., Bae, J. H., Choi, C. S., Lee, H. W., Jeong, H. S., and Kim, Y. S., Studies on the physical and chemical properties of lignins extracted from various pretreatment methods, Journal of Korea TAPPI 50(5):76-85 (2018).

10.7584/JKTAPPI.2018.10.50.5.76
15

Yoo, Y. H., Bae, J. H., An, L. L., Chen, J. S., and Kim, Y. S., Preparation of Cellulose Nanocrystal-based Poly (m-aminobenzenesulfonate) Copolymer for Heavy Metal Cr (VI) Adsorption, Journal of Korea TAPPI 52(6):110-122 (2020).

10.7584/JKTAPPI.2020.12.52.6.110
16

Park, E. B., Kim, K. J., and Jeong, H. R., Synthesis, structure determination, and biological evaluation of phenylsulfonyl hydrazide derivatives as potential anti-inflammatory agents, Bioorganic & Medicinal Chemistry Letters 26(21):5193-5197 (2016).

10.1016/j.bmcl.2016.09.070
17

Praddep, S., Arunraj, L., and Dhatchinamurthy, L., Synthesis and characterization of poly m-amino benzene sulfonic acid for sensor applications, Journal of NanoScience and NanoTechnology 2(4):390-393 (2014).

18

Terraza, C. A., Tagle, L. H., Concha, F., and Poblete, L., Synthesis and characterization of new bi-functional monomers based on germarylene or silarylene units: 4,4′-(R1R2-silylene) bis(phenyl chloroformates) and 4,4′-(R1R2-germylene)bis(phenyl chloroformates), Desined Monomers and Polymers 10(3):253-261 (2012).

10.1163/156855507780949209
19

Ali, M. A., Shaharyar, M., and Siddiqui, A. A., Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives, European Journal of Medicinal Chemistry 42(2):268-275 (2007).

10.1016/j.ejmech.2006.08.004
20

Ji, Y., Yang, X. L., Ji, Z., Zhu, L. H., Ma, N. N., Chen, D. J., Jia, X. B., Tang, J. M., and Cao, Y. L., DFT-Calculated IR Spectrum Amide Ⅰ,Ⅱ and Ⅲ Band Contributions of N-Methylacetamide Fine Components, ACS Omega 5(15):8572-8578 (2020).

10.1021/acsomega.9b04421
Information
  • Publisher :Korea Technical Association of The Pulp and Paper Industry
  • Publisher(Ko) :한국펄프종이공학회
  • Journal Title :Journal of Korea TAPPI
  • Journal Title(Ko) :펄프종이기술
  • Volume : 53
  • No :2
  • Pages :65-73
  • Received Date : 2021-04-04
  • Revised Date : 2021-04-18
  • Accepted Date : 2021-04-21
  • DOI :https://doi.org/10.7584/JKTAPPI.2021.04.53.2.65
Journal Informaiton Journal of Korea TAPPI Journal of Korea TAPPI
Online Submission
  • scopus
  • NRF
  • KOFST
  • crossref crossmark
  • crossref cited-by
  • crosscheck
  • orcid
Journal Informaiton Journal Informaiton - close