Study on the surface-modification of nano-hydroxyapatite with lignin and the corresponding nanocomposite with poly (lactide-co-glycolide)

doi:10.1007/s11705-020-1970-5

Front. Chem. Sci. Eng.

2021, Vol. 15

Issue (3) : 630-642 https://doi.org/10.1007/s11705-020-1970-5

RESEARCH ARTICLE

Study on the surface-modification of nano-hydroxyapatite with lignin and the corresponding nanocomposite with poly (lactide-co-glycolide)

Haojie Ding^1,^2,³, Liuyun Jiang^1,^2,³(

), Chunyan Tang^1,^2,³, Shuo Tang^1,^2,³, Bingli Ma^1,^2,³, Na Zhang^1,^2,³, Yue Wen^1,^2,³, Yan Zhang^1,^2,³, Liping Sheng^1,^2,³, Shengpei Su^1,^2,³, Xiang Hu⁴(

)

¹. National & Local Joint Engineering Laboratory for New Petro-Chemical Materials and Fine Utilization of Resources, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China
². Key Laboratory of Sustainable Resources Processing and Advanced Materials, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China
³. Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China
⁴. State Key Laboratory Developmental Biology of Freshwater Fish, School Life Science, Hunan Normal University, Changsha 410081, China

Download: PDF(7943 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

To obtain nano-hydroxyapatite/poly(lactide-co-glycolide) (n-HA/PLGA) nanocomposite with superior mechanical properties, here, lignin was chosen to surface-modify for n-HA through co-precipitation method. The different reaction conditions of reaction time, phosphorus source, and the lignin addition amount were studied by fourier transformation infrared spectra, X-ray diffraction, the intuitionistic dispersion experiment, transmission electron microscope and thermal gravimetric analysis. The reaction mechanism and the best appropriate reaction condition were obtained. More importantly, the results of electromechanical universal tester, scanning electron microscope, differential scanning calorimetric analyzer, polarized optical microscopy and dynamic mechanical analysis confirmed that the obtained n-HA could greatly increase the mechanical strength of PLGA, owing to the excellent dispersion and promotion crystallization effect. Moreover, in vitro cell culture experimental results indicated that the n-HA surface-modified by lignin was favorable to improve the cell biocompatibility of PLGA. The study suggested that the introduction of lignin was a novel method to acquire a highly dispersed n-HA, which would provide a new idea to achieve the n-HA/PLGA nanocomposite as bone materials in future, and it would pave the way towards a new application of lignin in biomedical field.

Keywords nanocomposite poly (lactide-co-glycolide) hydroxyapatite mechanical property

Corresponding Author(s): Liuyun Jiang,Xiang Hu

Just Accepted Date: 27 September 2020 Online First Date: 21 December 2020 Issue Date: 10 May 2021

Cite this article:

Haojie Ding,Liuyun Jiang,Chunyan Tang, et al. Study on the surface-modification of nano-hydroxyapatite with lignin and the corresponding nanocomposite with poly (lactide-co-glycolide)[J]. Front. Chem. Sci. Eng., 2021, 15(3): 630-642.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-020-1970-5
https://academic.hep.com.cn/fcse/EN/Y2021/V15/I3/630

Fig.1 FTIR spectra of samples: (a) lignin, (b) HA, (c) L-HA (Bl), (d) r-L-HA, (e) L-HA (P₂O₅), (f) L-HA (3 h), (g) L-HA (1 h), (h) L-HA (0 h), and (i) L-HA (1 h, 7.5 g).

Fig.2 XRD spectraof the samples: (a) HA, (b) r-L-HA, (c) L-HA(P₂O₅), (d) L-HA (3 h), (e) L-HA (1 h), (f) L-HA (0 h), (g) L-HA (1 h, 7.5 g).

Tab.1 Crystallite parameters of the samples

Fig.3 (A) The intuitionistic dispersion photographs: (a) HA, (b) r-L-HA, (c) L-HA (P₂O₅), (d) L-HA (3 h), (e) L-HA (1 h), (f) L-HA (0 h), (g) L-HA (1 h, 7.5 g), (h) L-HA (Bl) and (B) TGA curves of samples.

Fig.4 TEM micrographs of the samples.

Fig.5 Tensile strengths of the samples: (a) pure PLGA, (b) n-HA/PLGA, (c) L-HA (Bl)/PLGA, (d) L-HA (0 h)/PLGA, (e) L-HA (1 h)/PLGA, (f) L-HA (1 h, 7.5 g)/PLGA.

Fig.6 (A) SEM micrographs, (B) DSC cooling curves and (C) DSC second heating curves of the samples: (a) pure PLGA, (b) n-HA/PLGA, (c) L-HA (Bl)/PLGA, (d) L-HA (0 h)/PLGA, (e) L-HA (1 h)/PLGA, (f) L-HA (1 h, 7.5 g)/PLGA.

Fig.7 POM photographs of samples at 120 °C: (a) pure PLGA, (b) n-HA/PLGA, (c) L-HA (Bl)/PLGA, (d) L-HA (0 h)/PLGA, (e) L-HA (1 h)/PLGA, and (f) L-HA (1 h, 7.5 g)/PLGA.

Fig.8 (A) Storage modulus (E') versus temperature and (B) Mechanical loss factor (tand) versus temperature of the samples: (a) pure PLGA, (b) n-HA/PLGA, (c) L-HA (Bl)/PLGA, (d) L-HA (0 h)/PLGA, (e) L-HA (1 h)/PLGA, and (f) L-HA (1 h, 7.5 g)/PLGA.

Fig.9 (A) The fluorescence picture and (B) absorption coefficient MTT method of samples: (a) PLGA, (b) n-HA/PLGA (10%), (c) L-HA (0 h)/PLGA (3%), and (d) L-HA (0 h)/PLGA (10%).

1	H X Diao, Y F Si, A P Zhu, L J Ji, H C Shi. Surface modified nano-hydroxyapatite/poly (lactide acid) composite and its osteocyte compatibility. Materials Science and Engineering C, 2012, 32(7): 1796–1801 https://doi.org/10.1016/j.msec.2012.04.065
2	F L Jin, R R Hu, S J Park. Improvement of thermal behaviors of biodegradable poly (lactic acid) polymer: a review. Composites. Part B, Engineering, 2019, 164: 287–296 https://doi.org/10.1016/j.compositesb.2018.10.078
3	P L Lai, D W Hong, C T Y Lin, L H Chen, W J Chen, I M Chu. Effect of mixing ceramics with a thermosensitive biodegradable hydrogel as composite graft. Composites. Part B, Engineering, 2012, 43(8): 3088–3095 https://doi.org/10.1016/j.compositesb.2012.04.057
4	A Haider, D Versace, K C Gupta, I K Kang. Pamidronic acid-grafted nHA/PLGA hybrid nanofiber scaffolds suppress osteoclastic cell viability and enhance osteoblastic cell activity. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2016, 4(47): 7596–7604 https://doi.org/10.1039/C6TB02083F
5	X T Shi, Y J Wang, L Ren, Y H Gong, D A Wang. Enhancing alendronate release from a novel PLGA/hydroxyapatite microspheric system for bone repairing applications. Pharmaceutical Research, 2009, 26(2): 422–430 https://doi.org/10.1007/s11095-008-9759-0
6	J Li, X L Lu, Y F Zheng. Effect of surface modified hydroxyapatite on the tensile property improvement of HA/PLA composite. Applied Surface Science, 2008, 255(2): 494–497 https://doi.org/10.1016/j.apsusc.2008.06.067
7	J O Akindoyo, M D H Beg, S Ghazali, H P Heim, M Feldmann. Effects of surface modification on dispersion, mechanical, thermal and dynamic mechanical properties of injection molded PLA-hydroxyapatite composites. Composites. Part A, Applied Science and Manufacturing, 2017, 103: 96–105 https://doi.org/10.1016/j.compositesa.2017.09.013
8	L Y Jiang, L X Jiang, C D Xiong, L J Xu, Y Li. Effect of L-lysine-assisted surface-grafting for nano-hydroxyapatite on mechanical properties and in vitro bioactivity of poly(lactic acid-co-glycolic acid). Journal of Biomaterials Applications, 2016, 30(6): 750–758 https://doi.org/10.1177/0885328215584491
9	L Y Jiang, C D Xiong, D L Chen, L X Jiang, X B Pang. Effect of n-HA with different surface-modified on the properties of n-HA/PLGA composite. Applied Surface Science, 2012, 259: 72–78 https://doi.org/10.1016/j.apsusc.2012.06.091
10	L Y Jiang, C D Xiong, L X Jiang, L J Xu. Effect of HA with different grain size range on the crystallization behaviors andmechanical property of HA/PLGA composite. Thermochimica Acta, 2013, 565: 52–57 https://doi.org/10.1016/j.tca.2013.05.004
11	D Y Mao, Q Li, N N Bai, H Z Dong, D K Li. Porous stable poly(lactic acid)/ethyl cellulose/hydroxyapatite composite scaffolds prepared by a combined method for bone regeneration. Carbohydrate Polymers, 2018, 180: 104–111 https://doi.org/10.1016/j.carbpol.2017.10.031
12	L Musilova, A Mracek, A Kovalcik, P Smolka, A Minarik, P Humpolicek, R Vicha, P Ponizil. Hyaluronan hydrogels modified by glycinated Kraft lignin: morphology, swelling, viscoelastic properties and biocompatibility. Carbohydrate Polymers, 2018, 181: 394–403 https://doi.org/10.1016/j.carbpol.2017.10.048
13	H J Ding, L Y Jiang, B L Ma, S P Su. Preparation of a highly dispersed nano-hydroxyapatite by a new surfacemodificationstrategy used for a reinforce filler for poly(lactic-co-glycolide). Industrial & Engineering Chemistry Research, 2018, 57(50): 17119–17128 https://doi.org/10.1021/acs.iecr.8b03258
14	N Supanchaiyamat, K Jetsrisuparb, J T N Knijnenburg, D C W Tsang, A J Hunt. Lignin materials for adsorption: current trend, perspectives and opportunities. Bioresource Technology, 2019, 272: 570–581 https://doi.org/10.1016/j.biortech.2018.09.139
15	H Z Chen. Chemical composition and structure of natural lignocellulose. In: Biotechnology of Lignocellulose. Berlin: Springer International Publishing, 2014, 25–71
16	X J Zhan, C Cai, Y X Pang, F Y Qin, H M Lou, J H Huang, X Q Qiu. Effect of the isoelectric point of pH-responsive lignin-based amphoteric surfactant on the enzymatic hydrolysis of lignocelluloses. Bioresource Technology, 2019, 283: 112–119 https://doi.org/10.1016/j.biortech.2019.03.026
17	Y Meng, J Lu, Y Cheng, Q Li, H S Wang. Lignin-based hydrogels: a review of preparation, properties, and application. International Journal of Biological Macromolecules, 2019, 135: 1006–1019 https://doi.org/10.1016/j.ijbiomac.2019.05.198
18	Y Z Tao, Y T Guan. Study of chemical composition of lignin and its application. Journal of Fuel Cell Science and Technology, 2003, 1: 42–55 (in Chinese)
19	Y X Pang, X Bao. Influence of temperature, ripening time and calcination on the morphology and crystallinity of hydroxyapatite nanoparticles. Journal of the European Ceramic Society, 2003, 23(10): 1697–1704 https://doi.org/10.1016/S0955-2219(02)00413-2
20	H Elhendawi, R M Felfel, B M A Elhady, F M Reicha. Effect of synthesis temperature on the crystallization and growth of in situ prepared nanohydroxyapatite in chitosan matrix. ISRN Biomaterials, 2014: 1–8
21	P P Wang, C H Li, H Y Gong, X R Jiang, H Q Wang, K X Li. Effects of synthesis conditions on the morphology of hydroxyapatite nanoparticles produced by wet chemical process. Powder Technology, 2010, 203(2): 315–321 https://doi.org/10.1016/j.powtec.2010.05.023
22	M Bayani, S Torabi, A Shahnaz, M Pourali. Main properties of nanocrystalline hydroxyapatite as a bone graft material in treatment of periodontal defects: a review of literature. Biotechnology, Biotechnological Equipment, 2017, 31(2): 215–220 https://doi.org/10.1080/13102818.2017.1281760
23	T Turki, M Othmani, J L Bantignies, K Bouzouita. Hydroxyapatite-phosphonoformic acid hybrid compounds prepared by hydrothermal method. Applied Surface Science, 2014, 290: 327–331 https://doi.org/10.1016/j.apsusc.2013.11.076
24	M A Sawpan, K L Pickering, A Fernyhough. Improvement of mechanical performance of industrial hemp fibre reinforced polylactide biocomposites. Composites. Part A, Applied Science and Manufacturing, 2011, 42(3): 310–319 https://doi.org/10.1016/j.compositesa.2010.12.004
25	B J Zhang, L He, Z W Han, X G Li, W Zhi, W Zheng, Y D Mu, J Weng. Enhanced osteogenesis of multilayered pore-closed microsphere-immobilized hydroxyapatite scaffold via sequential delivery of osteogenic growth peptide and BMP-2. Journal of Materials Chemistry B, 2017, 5(41): ‏ 8238–8253
26	X Y Yuan, B S Zhu, G S Tong, Y Su, X Y Zhu. Wet-chemical synthesis of Mg-doped hydroxyapatite nanoparticles by step reaction and ion exchange processes. Journal of Macromolecular Science, Part B: Physics, 2013, 1(47): 6551–6559
27	P J Shi, M Liu, F J Fan, C P Yu, W H Lu, M Du. Characterization of natural hydroxyapatite originated from fish bone and its biocompatibility with osteoblasts. Materials Science and Engineering C, 2018, 90: 706–712 https://doi.org/10.1016/j.msec.2018.04.026
28	M S Fernando, R M de Silva, K M N de Silva. Synthesis, characterization, and application of nano hydroxyapatite and nanocomposite of hydroxyapatite with granular activated carbon for the removal of Pb2+ from aqueous solutions. Applied Surface Science, 2015, 351: 95–103 https://doi.org/10.1016/j.apsusc.2015.05.092
29	L X Jiang, L Y Jiang, C Ma, C T Han, C D Xiong, L J Xu. Preparation and characterization of nano-hydroxyapatite/PLGA composites with novel surface-modified nano-hydroxyapatite. Journal of Inorganic Materials, 2013, 28(7): 751–756 (in Chinese)
30	D Ando, F Nakatsubo, H Yano. Thermal stability of lignin in ground pulp (GP) and the effect of lignin modification on GP’s thermal stability: TGA experiments with dimeric lignin model compounds and milled wood lignins. Holzforschung, 2019, 73(5): 493–499 https://doi.org/10.1515/hf-2018-0137
31	Z K Hong, P B Zhang, C L He, X Y Qiu, A X Liu, L Chen, X Chen, X B Jing. Nano-composite of poly(L-lactide) and surface grafted hydroxyapatite: Mechanical properties and biocompatibility. Biomaterials, 2005, 26(32): 296–6304 https://doi.org/10.1016/j.biomaterials.2005.04.018
32	H Y Zhang, J R Choi, S J Park. Enhancing the heat and load transfer efficiency by optimizing the interface of hexagonal boron nitride/elastomer nanocomposites for thermal management applications. Polymer, 2018, 143: 1–9 https://doi.org/10.1016/j.polymer.2018.03.067
33	H Y Zhang, J R Choi, S J Park. Interlayer polymerization in amine-terminated macromolecular chain-grafted expanded graphite for fabricating highly thermal conductive and physically strong thermoset composites for thermal management applications. Composites. Part A, Applied Science and Manufacturing, 2018, 109: 498–506 https://doi.org/10.1016/j.compositesa.2018.04.001
34	D D Yang, W Liu, H M Zhu, G Wu, S C Chen, X L Wang, Y Z Wang. Toward super-tough poly(L-lactide) via constructing pseudo-cross-link network in toughening phase anchored by stereocomplex crystallites at the interface. ACS Applied Materials & Interfaces, 2018, 10(31): 26594–26603 https://doi.org/10.1021/acsami.8b06343
35	D D Xuan, Y F Zhou, W Y Nie, P P Chen. Sodium alginate-assisted exfoliation of MoS2 and its reinforcement in polymer nanocomposites. Carbohydrate Polymers, 2017, 144: 25–32 https://doi.org/10.1016/j.carbpol.2016.08.052
36	Y C Guo, S He, K Yang, Y Xue, X H Zuo, Y J Yu, Y Liu, C C Chang, M H Rafailovich. Enhancing the mechanical properties of biodegradable polymer blends using tubular nanoparticle stitching of the interfaces. ACS Applied Materials & Interfaces, 2016, 8(27): 17565–17573 https://doi.org/10.1021/acsami.6b05698
37	A Jankovic, S Erakovic, C Ristoscu, N Mihailescu, L Duta, A Visan, G E Stan, A C Popa, M A Husanu, C R Luculescu, et al. Structural and biological evaluation of lignin addition to simple and silver-doped hydroxyapatite thin films synthesized by matrix-assisted pulsed laser evaporation. Journal of Materials Science. Materials in Medicine, 2015, 26(1): 1–14 https://doi.org/10.1007/s10856-014-5333-y

[1]	Hossein Abdolmohammad-Zadeh, Arezu Salimi. A magnetic adsorbent based on salicylic acid-immobilized magnetite nano-particles for pre-concentration of Cd(II) ions[J]. Front. Chem. Sci. Eng., 2021, 15(2): 450-459.
[2]	Mostafa R. Shirdar, Nasim Farajpour, Reza Shahbazian-Yassar, Tolou Shokuhfar. Nanocomposite materials in orthopedic applications[J]. Front. Chem. Sci. Eng., 2019, 13(1): 1-13.
[3]	Dongjie Yang, Shengyu Wang, Ruisheng Zhong, Weifeng Liu, Xueqing Qiu. Preparation of lignin/TiO₂ nanocomposites and their application in aqueous polyurethane coatings[J]. Front. Chem. Sci. Eng., 2019, 13(1): 59-69.
[4]	Peizhen Duan, Juan Shen, Guohong Zou, Xu Xia, Bo Jin. Biomimetic mineralization and cytocompatibility of nanorod hydroxyapatite/graphene oxide composites[J]. Front. Chem. Sci. Eng., 2018, 12(4): 798-805.
[5]	Walter Kaminsky. *Polyolefin-nanocomposites with special properties by in-situ* polymerization**[J]. Front. Chem. Sci. Eng., 2018, 12(3): 555-563.
[6]	Jiaojiao Shang, Guo Yao, Ronghui Guo, Wei Zheng, Long Gu, Jianwu Lan. Synthesis and characterization of biodegradable thermoplastic elastomers derived from N′,N-bis (2-carboxyethyl)-pyromellitimide, poly(butylene succinate) and polyethylene glycol[J]. Front. Chem. Sci. Eng., 2018, 12(3): 457-466.
[7]	Muhammad I. Asghar, Sakari Lepikko, Janne Patakangas, Janne Halme, Peter D. Lund. Comparative analysis of ceramic-carbonate nanocomposite fuel cells using composite GDC/NLC electrolyte with different perovskite structured cathode materials[J]. Front. Chem. Sci. Eng., 2018, 12(1): 162-173.
[8]	A. F. D’ Intino,B. de Caprariis,M.L. Santarelli,N. Verdone,A. Chianese. Best operating conditions to produce hydroxyapatite nanoparticles by means of a spinning disc reactor[J]. Front. Chem. Sci. Eng., 2014, 8(2): 156-160.
[9]	W. Widiyastuti, Adhi Setiawan, Sugeng Winardi, Tantular Nurtono, Heru Setyawan. Particle formation of hydroxyapatite precursor containing two components in a spray pyrolysis process[J]. Front Chem Sci Eng, 2014, 8(1): 104-113.
[10]	Yang YU, Hong ZHANG, Hong SUN, Dandan XING, Fanglian YAO. Nano-hydroxyapatite formation via co-precipitation with chitosan-g-poly(N-isopropylacrylamide) in coil and globule states for tissue engineering application[J]. Front Chem Sci Eng, 2013, 7(4): 388-400.
[11]	M. ABDELLAHI, M. ZAKERI, H. BAHMANPOUR. Events and reaction mechanisms during the synthesis of an Al₂O₃-TiB₂ nanocomposite via high energy ball milling[J]. Front Chem Sci Eng, 2013, 7(2): 123-129.
[12]	Xiaojing ZHANG, Weixin ZHANG, Zeheng YANG, Zhao ZHANG. Nanostructured hollow spheres of hydroxyapatite: preparation and potential application in drug delivery[J]. Front Chem Sci Eng, 2012, 6(3): 246-252.
[13]	Vishal MATHUR, Manasvi DIXIT, K.S. RATHORE, N. S. SAXENA, K.B. SHARMA. Morphological and mechanical characterization of a PMMA/CdS nanocomposite[J]. Front Chem Sci Eng, 2011, 5(2): 258-263.
[14]	QI Dongming, YANG Lei, WU Minghua, SHAO Jianzhong, BAO Yongzhong. Dispersion of “guava-like” silica/polyacrylate nanocomposite particles in polyacrylate matrix[J]. Front. Chem. Sci. Eng., 2008, 2(2): 127-134.
[15]	XU Kaqiu, XU Jiale, WANG Yuhong. Preparation and property of porous hydroxyapatite as an inorganic dispersant used in suspension polymerization[J]. Front. Chem. Sci. Eng., 2008, 2(1): 49-54.

Viewed

Full text

Abstract

Cited

Shared

Discussed