木质素纳米颗粒的制备及其功能化应用研究进展

doi:10.3969/j.issn.1673-5854.2020.05.008

Abstract

Abstract:

Lignin is a kind of abundant, cheap and sustainable natural biomass resource. Recently, converting lignin to functional nanomaterials has greatly broadened its application. Meanwhile, this conversion greatly solved the typical problems for traditional materials. Here, in this paper, several preparation methods including preparation of lignin functional nanoparticles such as self-assembly, mechanical method, polymerization assembly, freeze-drying carbonization, etc were introduced. And then their different applications in catalysts, additives, adsorbents, UV protection and anti-oxidation, sterilization, carrier materials, aggregation-inducing emmision materials, etc were described. Also, an outlook about the prospect of its application was presented. Developing controllable preparation and functional modification will facilitate the further application of lignin-based nanoparticles in the fields of environmental protection, energy, catalysis and biomedicine.

Key words: lignin, nanotechnology, functionalization, controllable, application

CLC Number:

TQ35
TB34

Xue LIU,Shujun LI,Shouxin LIU,Jian LI,Zhijun CHEN. Research Progress in Preparation and Functional Application of Lignin-based Nanoparticles[J]. Biomass Chemical Engineering, 2020, 54(5): 53-65.

Figures/Tables 7

Fig.1

Fig.2

Fig.3

Fig.4

Fig.5

Fig.6

Fig.7

References 59

1	王欢, 杨东杰, 钱勇, 等. 木质素基功能材料的制备与应用研究进展[J]. 化工进展, 2019, 38 (1): 434- 448.
2	熊福全, 王航, 韩雁明, 等. 木质素微纳米球的制备与应用研究现状[J]. 林业科学, 2019, 55 (8): 170- 175.
3	CALVO-FLORES F G , DOBADO J A . Lignin as renewable raw material[J]. ChemSusChem, 2010, 3 (11): 1227- 1235. doi: 10.1002/cssc.201000157
4	FRANGVILLE C , RUTKEVIČIUS M , RICHTER A P , et al. Fabrication of environmentally biodegradable lignin nanoparticles[J]. ChemPhyschem, 2012, 13 (18): 4235- 4243. doi: 10.1002/cphc.201200537
5	RICHTER A P , BHARTI B , ARMSTRONG H B , et al. Synthesis and characterization of biodegradable lignin nanoparticles with tunable surface properties[J]. Langmuir, 2016, 32 (25): 6468- 6477. doi: 10.1021/acs.langmuir.6b01088
6	YANG W J , FORTUNATI E , GAO D Q , et al. Valorization of acid isolated high yield lignin nanoparticles as innovative antioxidant/antimicrobial organic materials[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (3): 3502- 3514.
7	MA M S , DAI L , SI C L , et al. A facile preparation of super long-term stable lignin nanoparticles from black liquor[J]. ChemSusChem, 2019, 12 (24): 5239- 5245. doi: 10.1002/cssc.201902287
8	LU Q , ZHU M H , ZU Y G , et al. Comparative antioxidant activity of nanoscale lignin prepared by a supercritical antisolvent(SAS) process with non-nanoscale lignin[J]. Food Chemistry, 2012, 135 (1): 63- 67.
9	MYINT A A , LEE H W , SEO B , et al. One pot synthesis of environmentally friendly lignin nanoparticles with compressed liquid carbon dioxide as an antisolvent[J]. Green Chemistry, 2016, 18 (7): 2129- 2146. doi: 10.1039/C5GC02398J
10	QIAN Y , DENG Y H , QIU X Q , et al. Formation of uniform colloidal spheres from lignin, a renewable resource recovered from pulping spent liquor[J]. Green Chemistry, 2014, 16 (4): 2156- 2163. doi: 10.1039/c3gc42131g
11	LI H , DENG Y H , LIU B , et al. Preparation of nanocapsules via the self-assembly of kraft lignin:A totally green process with renewable resources[J]. ACS Sustainable Chemistry & Engineering, 2016, 4 (4): 1946- 1953.
12	LI H , DENG Y H , LIANG J Q , et al. Direct preparation of hollow nanospheres with kraft lignin:A facile strategy for effective utilization of biomass waste[J]. BioResources, 2016, 11 (2): 3073- 3083.
13	XIONG F Q , HAN Y M , WANG S Q , et al. Preparation and formation mechanism of renewable lignin hollow nanospheres with a single hole by self-assembly[J]. ACS Sustainable Chemistry & Engineering, 2017, 5 (3): 2273- 2281.
14	LINTINEN K , XIAO Y , BANGALORE ASHOK R , et al. Closed cycle production of concentrated and dry redispersible colloidal lignin particles with a three solvent polarity exchange method[J]. Green Chemistry, 2018, 20 (4): 843- 850. doi: 10.1039/C7GC03465B
15	SIPPONEN M H , LANGE H , AGO M , et al. Understanding lignin aggregation processes.A case study:Budesonide entrapment and stimuli controlled release from lignin nanoparticles[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (7): 9342- 9351.
16	LIU Z H , HAO N J , SHINDE S , et al. Defining lignin nanoparticle properties through tailored lignin reactivity by sequential organosolv fragmentation approach(SOFA)[J]. Green Chemistry, 2019, 21 (2): 245- 260.
17	LIEVONEN M , VALLE-DELGADO J J , MATTINEN M L , et al. A simple process for lignin nanoparticle preparation[J]. Green Chemistry, 2016, 18 (5): 1416- 1422. doi: 10.1039/C5GC01436K
18	AGO M , HUAN S Q , BORGHEI M , et al. High-throughput synthesis of lignin particles (~30 nm to ~2μm) via aerosol flow reactor:Size fractionation and utilization in pickering emulsions[J]. ACS Applied Materials & Interfaces, 2016, 8 (35): 23302- 23310.
19	MISHRA P K , WIMMER R . Aerosol assisted self-assembly as a route to synthesize solid and hollow spherical lignin colloids and its utilization in layer by layer deposition[J]. Ultrasonics Sonochemistry, 2017, 35, 45- 50. doi: 10.1016/j.ultsonch.2016.09.001
20	GILCA I A , POPA V I , CRESTINI C . Obtaining lignin nanoparticles by sonication[J]. Ultrasonics Sonochemistry, 2015, 23, 369- 375. doi: 10.1016/j.ultsonch.2014.08.021
21	AGUSTIN M B , PENTTILÄ P A , LAHTINEN M , et al. Rapid and direct preparation of lignin nanoparticles from alkaline pulping liquor by mild ultrasonication[J]. ACS Sustainable Chemistry & Engineering, 2019, 7 (24): 19925- 19934.
22	NAIR S S , SHARMA S , PU Y Q , et al. High shear homogenization of lignin to nanolignin and thermal stability of nanolignin-polyvinyl alcohol blends[J]. ChemSusChem, 2014, 7 (12): 3513- 3520. doi: 10.1002/cssc.201402314
23	NYPELÖ T E , CARRILLO C A , ROJAS O J . Lignin supracolloids synthesized from(W/O) microemulsions:Use in the interfacial stabilization of Pickering systems and organic carriers for silver metal[J]. Soft Matter, 2015, 11 (10): 2046- 2054. doi: 10.1039/C4SM02851A
24	CHEN N S , DEMPERE L A , TONG Z H . Synthesis of pH-responsive lignin-based nanocapsules for controlled release of hydrophobic molecules[J]. ACS Sustainable Chemistry & Engineering, 2016, 4 (10): 5204- 5211.
25	YIAMSAWAS D , BECKERS S J , LU H , et al. Morphology-controlled synthesis of lignin nanocarriers for drug delivery and carbon materials[J]. ACS Biomaterials Science & Engineering, 2017, 3 (10): 2375- 2383.
26	YIAMSAWAS D , BAIER G , THINES E , et al. Biodegradable lignin nanocontainers[J]. RSC Advances, 2014, 4 (23): 11661- 11663. doi: 10.1039/C3RA47971D
27	GONUGUNTA P , VIVEKANANDHAN S , MOHANTY A K , et al. A study on synthesis and characterization of biobased carbon nanoparticles from lignin[J]. World Journal of Nano Science and Engineering, 2012, 2 (3): 148- 153. doi: 10.4236/wjnse.2012.23019
28	BEISL S , MILTNER A , FRIEDL A . Lignin from micro-to nanosize:Production methods[J]. International Journal of Molecular Sciences, 2017, 18 (6): 1244- 1274. doi: 10.3390/ijms18061244
29	SIPPONEN M H , FAROOQ M , KOIVISTO J , et al. Spatially confined lignin nanospheres for biocatalytic ester synthesis in aqueous media[J]. Nature Communication, 2018, 9 (1): 2300- 2306. doi: 10.1038/s41467-018-04715-6
30	CAPECCHI E , PICCININO D , DELFINO I , et al. Functionalized tyrosinase-lignin nanoparticles as sustainable catalysts for the oxidation of phenols[J]. Nanomaterials, 2018, 8 (6): 438- 454. doi: 10.3390/nano8060438
31	熊福全, 韩雁明, 王思群, 等. 纳米木质素的制备及应用研究现状[J]. 高分子材料科学与工程, 2016, 32 (12): 156- 161.
32	QIAN Y , ZHANG Q , QIU X Q , et al. CO₂-responsive diethylaminoethyl-modified lignin nanoparticles and their application as surfactants for CO₂/N₂-switchable Pickering emulsions[J]. Green Chemistry, 2014, 16 (12): 4963- 4968. doi: 10.1039/C4GC01242A
33	DAI L , LI Y T , KONG F G , et al. Lignin-based nanoparticles stabilized pickering emulsion for stability improvement and thermal-controlled release of trans-resveratrol[J]. ACS Sustainable Chemistry & Engineering, 2019, 7 (15): 13497- 13504.
34	DEL SAZ-OROZCO B , OLIET M , ALONSO M V , et al. Formulation optimization of unreinforced and lignin nanoparticle-reinforced phenolic foams using an analysis of variance approach[J]. Composites Science and Technology, 2012, 72 (6): 667- 674. doi: 10.1016/j.compscitech.2012.01.013
35	JIANG C , HE H , JIANG H , et al. Nano-lignin filled natural rubber composites:Preparation and characterization[J]. Express Polymer Letters, 2013, 7 (5): 480- 493. doi: 10.3144/expresspolymlett.2013.44
36	LI Y L , WU M , WANG B , et al. Synthesis of magnetic lignin-based hollow microspheres:A highly adsorptive and reusable adsorbent derived from renewable resources[J]. ACS Sustainable Chemistry & Engineering, 2016, 4 (10): 5523- 5532.
37	LUO X G , LIU C , YUAN J , et al. Interfacial solid-phase chemical modification with mannich reaction and Fe(Ⅲ) chelation for designing lignin-based spherical nanoparticle adsorbents for highly efficient removal of low concentration phosphate from water[J]. ACS Sustainable Chemistry & Engineering, 2017, 5 (8): 6539- 6547.
38	MA Y Z , ZHENG D F , MO Z Y , et al. Magnetic lignin-based carbon nanoparticles and the adsorption for removal of methyl orange[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2018, 559, 226- 234. doi: 10.1016/j.colsurfa.2018.09.054
39	ZHANG Y C , NI S Z , WANG X J , et al. Ultrafast adsorption of heavy metal ions onto functionalized lignin-based hybrid magnetic nanoparticles[J]. Chemical Engineering Journal, 2019, 372, 82- 91. doi: 10.1016/j.cej.2019.04.111
40	QIAN Y , QIU X Q , ZHU S P . Sunscreen performance of lignin from different technical resources and their general synergistic effect with synthetic sunscreens[J]. ACS Sustainable Chemistry & Engineering, 2016, 4 (7): 4029- 4035.
41	QIAN Y , ZHONG X W , LI Y , et al. Fabrication of uniform lignin colloidal spheres for developing natural broad-spectrum sunscreens with high sun protection factor[J]. Industrial Crops and Products, 2017, 101, 54- 60. doi: 10.1016/j.indcrop.2017.03.001
42	TIAN D , HU J G , BAO J , et al. Lignin valorization:Lignin nanoparticles as high-value bio-additive for multifunctional nanocomposites[J]. Biotechnology for Biofuels, 2017, 10 (1): 192- 202.
43	XIONG F Q , WU Y Q , LI G Y , et al. Transparent nanocomposite films of lignin nanospheres and poly(vinyl alcohol) for UV-absorbing[J]. Industrial & Engineering Chemistry Research, 2018, 57 (4): 1207- 1212.
44	WANG B , SUN D , WANG H M , et al. Green and facile preparation of regular lignin nanoparticles with high yield and their natural broad-spectrum sunscreens[J]. ACS Sustainable Chemistry & Engineering, 2019, 7 (2): 2658- 2666.
45	POPA V I , CĂPRARU A , GRAMA S , et al. Nanoparticles based on modified lignins with biocide properties[J]. Cellulose Chemistry and Technology, 2011, 45 (3/4): 221- 226.
46	GǍLCĂ I A , CAPRARU A M , GRAMA S , et al. Agents for wood bioprotection based on natural aromatic compounds and their complexes with copper and zinc[J]. Cellulose Chemistry and Technology, 2011, 45 (3/4): 227- 231.
47	GǍLCĂ I A , POPA V I . Study on biocidal properties of some nanoparticles based on epoxy lignin[J]. Cellulose Chemistry and Technology, 2013, 47 (3/4): 239- 245.
48	YANG W , OWCZAREK J S , FORTUNATI E , et al. Antioxidant and antibacterial lignin nanoparticles in polyvinyl alcohol/chitosan films for active packaging[J]. Industrial Crops and Products, 2016, 94, 800- 811. doi: 10.1016/j.indcrop.2016.09.061
49	CAULEY A N , WILSON J N . Functionalized lignin biomaterials for enhancing optical properties and cellular interactions of dyes[J]. Biomaterials Science, 2017, 5 (10): 2114- 2121. doi: 10.1039/C7BM00518K
50	RICHTER A P , BROWN J S , BHARTI B , et al. An environmentally benign antimicrobial nanoparticle based on a silver-infused lignin core[J]. Nature Nanotechnology, 2015, 10 (9): 817- 823. doi: 10.1038/nnano.2015.141
51	FIGUEIREDO P , LINTINEN K , KIRIAZIS A , et al. In vitro evaluation of biodegradable lignin-based nanoparticles for drug delivery and enhanced antiproliferation effect in cancer cells[J]. Biomaterials, 2017, 121, 97- 108. doi: 10.1016/j.biomaterials.2016.12.034
52	ZHOU Y , HAN Y M , LI G Y , et al. Preparation of targeted lignin-based hollow nanoparticles for the delivery of doxorubicin[J]. Nanomaterials, 2019, 9 (2): 188- 200.
53	ZHOU Y , HAN Y M , LI G Y , et al. Effects of lignin-based hollow nanoparticle structure on the loading and release behavior of doxorubicin[J]. Materials, 2019, 12 (10): 1694- 1705. doi: 10.3390/ma12101694
54	ZHOU Y , HAN Y M , LI G Y , et al. Lignin-based hollow nanoparticles for controlled drug delivery:Grafting preparation using beta-cyclodextrin/enzymatic-hydrolysis lignin[J]. Nanomaterials, 2019, 9 (7): 997- 1007. doi: 10.3390/nano9070997
55	XUE Y Y , QIU X Q , WU Y , et al. Aggregation-induced emission:The origin of lignin fluorescence[J]. Polymer Chemistry, 2016, 7 (21): 3502- 3508. doi: 10.1039/C6PY00244G
56	MA Z M , LIU C , NIU N , et al. Seeking brightness from nature:J-aggregation-induced emission in cellulolytic enzyme lignin nanoparticles[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (3): 3169- 3175.
57	ZHAO H J , WANG Q J , DENG Y H , et al. Preparation of renewable lignin-derived nitrogen-doped carbon nanospheres as anodes for lithium-ion batteries[J]. RSC Advances, 2016, 6 (81): 77143- 77150. doi: 10.1039/C6RA17793J
58	李常青, 杨东杰, 席跃宾, 等. 二氧化硅/木质素多孔碳复合材料的制备及作为锂离子电池负极材料的性能[J]. 高等学校化学学报, 2018, 39 (12): 2725- 2733.
59	KAI D , TAN M J , CHEE P L , et al. Towards lignin-based functional materials in a sustainable world[J]. Green Chemistry, 2016, 18 (5): 1175- 1200. doi: 10.1039/C5GC02616D

[1]	Ruizhen WANG,Liuming SONG,Peng LIU,Kui WANG,Junming XU. Study of Lignin-based Surfactant [J]. Biomass Chemical Engineering, 2020, 54(3): 61-68.
[2]	Qian YANG,Guifeng LIU,Guomin WU,Zhenwu KONG. Research Progress of Lignin Chemical Degradation and Its Applications in Polymer Materials [J]. Biomass Chemical Engineering, 2020, 54(2): 40-50.
[3]	Jianan WANG,Ying YI,Yongjun BIAN,Yuanyuan MA,Zhiming LIU. Preparation, Characterization and Adsorption Performance of Hydroxymethylated Lignin/Cellulose Aerogel Particles [J]. Biomass Chemical Engineering, 2020, 54(1): 16-22.
[4]	Huanhuan MA,Yiling WAN,Lingxiang XIE,Fanrui MENG,Jianbin ZHOU. Structural Characterization and Pyrolysis Characteristics of Apricot Shell Lignin [J]. Biomass Chemical Engineering, 2019, 53(6): 27-32.
[5]	Jiaxing ZHOU,Zhiming LIU,Xu LI. Effect of Aluminum Hypophosphite Addition on Flame Retardancy of Alkali Lignin Based Polyurethane Foam [J]. Biomass Chemical Engineering, 2019, 53(2): 1-6.
[6]	Erqiang YIN,Shichao WANG,Hengxue XIANG,Zhe ZHOU,Meifang ZHU. Preparation and Properties of Melt-spun Kraft Hardwood Lignin-based Activated Carbon Fibers [J]. Biomass Chemical Engineering, 2019, 53(2): 26-34.
[7]	HU Ping, WANG Lifang, JIA Boran, LIU Ying, SHA Xiaoling, REN Shixue. Degradation Performances of Poly(vinylalcohol)/Wheat Straw Alkali Lignin Foaming Material with Formaldehyde Crosslinker [J]. bce, 2018, 52(4): 29-35.
[8]	GUO Tengfei, GAO Shishuai, WANG Chunpeng. Synthesis and Application of Melamine Urea Formaldehyde Monolithic Resin Modified by Enzymolysis Lignin [J]. bce, 2018, 52(3): 35-39.
[9]	WANG Shiwei, CHEN Keyu, WANG Qibao. Preparation and Emulsifying Performance of Acid-soluble Aminated Lignin [J]. bce, 2018, 52(2): 1-6.
[10]	WU Kai, YING Wenjun, ZHENG Zhifeng, SHI Zhengjun, YANG Haiyan, YANG Jing. Effect of Two Kinds of Lignin on Enzymatic Hydrolysis of Cellulose [J]. bce, 2018, 52(2): 29-34.
[11]	TAN Yang, MA Chunfu. Mechanism Study of Black Liquor Alkali Lignin Pyrolysis by Using TG-FTIR [J]. bce, 2018, 52(2): 35-41.
[12]	ZHAO Xinkun, LI Helong, SHE Diao, SUN Runcang. Status and Prospect of Lignin Model Compounds Synthesis [J]. bce, 2018, 52(1): 41-52.
[13]	SONG Yaoguang, LIU Junli, XU Wei, SUN Kang. Research Progress on Synthesis of Lignin-derived Mesoporous Carbon Materials via Template Strategy [J]. bce, 2018, 52(1): 60-68.
[14]	HU Yajie, FU Genque, YUE Panpan, LI Nan, PENG Feng, SUN Runcang. Research Progress on Preparation and Application of Amino Cellulose [J]. bce, 2017, 51(6): 48-54.
[15]	PENG Feng, FU Genque, WANG Xiaojun, HU Yajie, YUE Panpan. Isolation and Characterization of Water-soluble and Alkali-soluble Lignin from Bagasse [J]. bce, 2017, 51(4): 1-7.

Research Progress in Preparation and Functional Application of Lignin-based Nanoparticles

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 7

References 59

Related Articles 15

Recommended Articles

Metrics

Comments