Bacterial cellulose nanofibers modification with 3-(trimethoxysilyl)propyl methacrylate as a crosslinking and reinforcing agent for 3D printable UV-curable inks
Source abstract
Abstract
Cellulose nanofibers (CNF) produced by bacterial were functionalized along the surface with 3-(trimethoxysilyl)propyl methacrylate (TMSPM). The chemical and crystalline structure of the material was confirmed with NMR, FTIR, EDX and XRD methods. Modified CNF were used as a crosslinker and reinforcer for polymerizable deep eutectic solvent (DES) based on acrylic acid and choline chloride. Dispersions of modified nanofibers in DES were applied as UV-curable ink for 3D printing. It was shown that shielding of -OH groups of the cellulose surface with TMSPM increased the quality of 3D printed filaments due to reduced CNF agglomeration. At the same time, surface methacrylic groups copolymerize with acrylic acid forming crosslinked ion gel. Elastic moduli of the prepared ion gels were identical to those of gels based on unmodified CNF and crosslinked with N,N`-methylenebisacrylamide. However, strength and the ultimate elongation of the material prepared in this work were 1.05 ± 0.08 MPa at 2700% that is significantly higher than those of the material prepared with unmodified CNF.
Source: expertdata · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Advanced Cellulose Research Studies · Electrospun Nanofibers in Biomedical Applications · biodegradable polymer synthesis and properties
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (70)
Show source-provided references
1. Cakmak AM, Unal S, Sahin A, Oktar FN, Sengor M, Ekren N, Gunduz O, Kalaskar DM (2020) 3D printed polycaprolactone/gelatin/bacterial cellulose/hydroxyapatite composite scaffold for bone tissue engineering. Polymers 12(9):196210.3390/polym12091962 ↗
2. Zhou S, Zhou S, Zhou Q et al (2020) Design and preparation of 3D printing intelligent poly N,N'-dimethylacrylamide hydrogel actuators. E-Polym 20:273–281. https://doi.org/10.1515/epoly-2020-003310.1515/epoly-2020-0033 ↗
3. Beheshtizadeh N, Lotfibakhshaiesh N, Pazhouhnia Z, Hoseinpour M, Nafari M (2020) A review of 3D bio-printing for bone and skin tissue engineering: a commercial approach. J Mater Sci 55(9):3729–374910.1007/s10853-019-04259-0 ↗
4. Vithani K, Goyanes A, Jannin V et al (2019) An overview of 3D printing technologies for soft materials and potential opportunities for lipid-based drug delivery systems. Pharm Res. https://doi.org/10.1007/S11095-018-2531-110.1007/S11095-018-2531-1 ↗
5. Aguilar-De-leyva Á, Linares V, Casas M, Caraballo I (2020) 3D printed drug delivery systems based on natural products. Pharmaceutics 12:1–20. https://doi.org/10.3390/pharmaceutics1207062010.3390/pharmaceutics12070620 ↗
6. Hasan N, Rahman L, Kim SH et al (2020) Recent advances of nanocellulose in drug delivery systems. J Pharm Investig 50:553–572. https://doi.org/10.1007/s40005-020-00499-410.1007/s40005-020-00499-4 ↗
7. Yamasaki A, Kunitomi Y, Murata D, Sunaga T, Kuramoto T, Sogawa T, Misumi K (2018) Osteochondral regeneration using constructs of mesenchymal stem cells made by bio three-dimensional printing in mini-pigs. J Orthop Res 37(6):1398–140810.1002/jor.24206 ↗
8. Janarthanan G, Shin HS, Kim IG et al (2020) Self-crosslinking hyaluronic acid-carboxymethylcellulose hydrogel enhances multilayered 3D-printed construct shape integrity and mechanical stability for soft tissue engineering. Biofabrication. https://doi.org/10.1088/1758-5090/aba2f710.1088/1758-5090/aba2f7 ↗
9. Jiang Y, Zhou J, Yang Z et al (2018) Dialdehyde cellulose nanocrystal/gelatin hydrogel optimized for 3D printing applications. J Mater Sci 53:11883–11900. https://doi.org/10.1007/s10853-018-2407-010.1007/s10853-018-2407-0 ↗
10. Jiang Y, Zhou J, Shi H et al (2020) Preparation of cellulose nanocrystal/oxidized dextran/gelatin (CNC/OD/GEL) hydrogels and fabrication of a CNC/OD/GEL scaffold by 3D printing. J Mater Sci 55:2618–2635. https://doi.org/10.1007/s10853-019-04186-010.1007/s10853-019-04186-0 ↗
11. Jiang Y, Zhou J, Feng C et al (2020) Rheological behavior, 3D printability and the formation of scaffolds with cellulose nanocrystals/gelatin hydrogels. J Mater Sci 55:15709–15725. https://doi.org/10.1007/s10853-020-05128-x10.1007/s10853-020-05128-x ↗
12. Berglund L, Rakar J, Junker JP, Forsberg F, Oksman K (2020) Utilizing the natural composition of brown seaweed for the preparation of hybrid ink for 3D printing of hydrogels. ACS Appl Bio Mater 3(9):6510–652010.1021/acsabm.0c00920 ↗
13. Ng WL, Chua CK, Shen YF (2019) Print me an organ! why we are not there yet. Prog Polym Sci 97:101145. https://doi.org/10.1016/j.progpolymsci.2019.10114510.1016/j.progpolymsci.2019.101145 ↗
14. Okolie O, Stachurek I, Kandasubramanian B, Njuguna J (2007) Polymers 3D printing for hip implant applications: A Review. https://doi.org/10.3390/polym1211268210.3390/polym12112682 ↗
15. Velu R, Calais T, Jayakumar A, Raspall F (2019) A comprehensive review on bio-nanomaterials for medical implants and feasibility studies on fabrication of such implants by additive manufacturing technique. Mater (Basel). https://doi.org/10.3390/ma1301009210.3390/ma13010092 ↗
16. Suo H, Chen Y, Liu J et al (2021) 3D printing of biphasic osteochondral scaffold with sintered hydroxyapatite and polycaprolactone. J Mater Sci 56:16623–16633. https://doi.org/10.1007/s10853-021-06229-x10.1007/s10853-021-06229-x ↗
17. Xu W, Molino BZ, Cheng F et al (2019) On low-concentration inks formulated by nanocellulose assisted with gelatin methacrylate (GelMA) for 3D printing toward wound healing application. ACS Appl Mater Interfaces 11:8838–8848. https://doi.org/10.1021/acsami.8b2126810.1021/acsami.8b21268 ↗
18. Xu C, Zhang Molino B, Wang X et al (2018) 3D printing of nanocellulose hydrogel scaffolds with tunable mechanical strength towards wound healing application. J Mater Chem B 6:7066–7075. https://doi.org/10.1039/c8tb01757c10.1039/c8tb01757c ↗
19. Li L, Zhu Y, Yang J (2018) 3D bioprinting of cellulose with controlled porous structures from NMMO. Mater Lett 210:136–138. https://doi.org/10.1016/j.matlet.2017.09.01510.1016/j.matlet.2017.09.015 ↗
20. Altun E, Ekren N, Kuruca SE, Gunduz O (2019) Cell studies on electrohydrodynamic (EHD)-3D-bioprinted bacterial cellulose\polycaprolactone scaffolds for tissue engineering. Mater Lett 234:163–167. https://doi.org/10.1016/j.matlet.2018.09.08510.1016/j.matlet.2018.09.085 ↗
21. Shin S, Hyun J (2021) Rheological properties of cellulose nanofiber hydrogel for high-fidelity 3D printing. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2021.11797610.1016/j.carbpol.2021.117976 ↗
22. Klar V, Pere J, Turpeinen T et al (2019) Shape fidelity and structure of 3D printed high consistency nanocellulose. Sci Rep 9:1–10. https://doi.org/10.1038/s41598-019-40469-x10.1038/s41598-019-40469-x ↗
23. Mohd N, S Draman SF, N Salleh MS, Yusof NB (2017) Dissolution of cellulose in ionic liquid: A review. https://doi.org/10.1063/1.497545010.1063/1.4975450 ↗
24. Wang Q, Cai J, Zhang L et al (2013) A bioplastic with high strength constructed from a cellulose hydrogel by changing the aggregated structure. J Mater Chem A 1:6678–6686. https://doi.org/10.1039/c3ta11130j10.1039/c3ta11130j ↗
25. Dai L, Cheng T, Duan C et al (2019) 3D printing using plant-derived cellulose and its derivatives: A review. Carbohydr Polym 203:71–86. https://doi.org/10.1016/j.carbpol.2018.09.02710.1016/j.carbpol.2018.09.027 ↗
26. Mietner JB, Jiang X, Edlund U, Saake B, Navarro JR (2021) 3D printing of a bio-based ink made of cross-linked cellulose nanofibrils with various metal cations. Sci Rep 11(1):1–910.1038/s41598-021-85865-4 ↗
27. Monfared M, Mawad D, Rnjak-Kovacina J, Stenzel MH (2021) 3D bioprinting of dual-crosslinked nanocellulose hydrogels for tissue engineering applications. J Mater Chem B 9:6163–6175. https://doi.org/10.1039/d1tb00624j10.1039/d1tb00624j ↗
28. Lai CW, Yu SS (2020) 3D Printable strain sensors from deep eutectic solvents and cellulose nanocrystals. ACS Appl Mater Interfaces 12:34235–34244. https://doi.org/10.1021/acsami.0c1115210.1021/acsami.0c11152 ↗
29. Vorobiov VK, Sokolova MP, Bobrova NV et al (2022) Rheological properties and 3D-printability of cellulose nanocrystals/deep eutectic solvent electroactive ion gels. Carbohydr Polym 290:119475. https://doi.org/10.1016/j.carbpol.2022.11947510.1016/j.carbpol.2022.119475 ↗
30. Smirnov MA, Fedotova VS, Sokolova MP et al (2021) Polymerizable choline-and imidazolium-based ionic liquids reinforced with bacterial cellulose for 3D-printing. Polym (Basel) 13:3044. https://doi.org/10.3390/polym1318304410.3390/polym13183044 ↗
31. Müller LAE, Zimmermann T, Nyström G et al (2020) Mechanical properties tailoring of 3D printed photoresponsive nanocellulose composites. Adv Funct Mater 30:1–9. https://doi.org/10.1002/adfm.20200291410.1002/adfm.202002914 ↗
32. Buyanov AL, Gofman IV, Bozhkova SA et al (2016) Composite hydrogels based on polyacrylamide and cellulose: Synthesis and functional properties. Russ J Appl Chem 89:772–779. https://doi.org/10.1134/S107042721605014110.1134/S1070427216050141 ↗
33. Ferreira FV, Lona LMF, Pinheiro IF et al (2019) Polymer composites reinforced with natural fibers and nanocellulose in the automotive industry: A short review. J Compos Sci. https://doi.org/10.3390/jcs302005110.3390/jcs3020051 ↗
34. Ma Q, Mohawk D, Jahani B et al (2020) UV-Curable cellulose nanofiber-reinforced soy protein resins for 3D printing and conventional molding. ACS Appl Polym Mater 2:4666–4676. https://doi.org/10.1021/acsapm.0c0071710.1021/acsapm.0c00717 ↗
35. Poaty B, Vardanyan V, Wilczak L et al (2014) Modification of cellulose nanocrystals as reinforcement derivatives for wood coatings. Prog Org Coat 77:813–820. https://doi.org/10.1016/j.porgcoat.2014.01.00910.1016/j.porgcoat.2014.01.009 ↗
36. Lepetit A, Drolet R, Tolnai B et al (2017) Alkylation of microfibrillated cellulose–A green and efficient method for use in fiber-reinforced composites. Polym 126:48–55. https://doi.org/10.1016/j.polymer.2017.08.02410.1016/j.polymer.2017.08.024 ↗
37. Stenstad P, Andresen M, Tanem BS, Stenius P (2008) Chemical surface modifications of microfibrillated cellulose. Cellulose 15:35–45. https://doi.org/10.1007/s10570-007-9143-y10.1007/s10570-007-9143-y ↗
38. Hasani M, Cranston ED, Westman G, Gray DG (2008) Cationic surface functionalization of cellulose nanocrystals. Soft Matter. https://doi.org/10.1039/b806789a10.1039/b806789a ↗
39. Botaro VR, Gandini A, Belgacem MN (2005) Heterogeneous chemical modification of cellulose for composite materials. J Thermoplast Compos Mater 18:107–117. https://doi.org/10.1177/089270570504260010.1177/0892705705042600 ↗
40. Maldas D, Kokta BV (1989) Improving adhesion of wood fiber with polystyrene by the chemical treatment of fiber with a coupling agent and the influence on the mechanical properties of composites. J Adhes Sci Technol 3:529–539. https://doi.org/10.1163/156856189X0038010.1163/156856189X00380 ↗
41. Krishnamurthy M, Lobo NP, Samanta D (2020) Improved hydrophobicity of a bacterial cellulose surface: click chemistry in action. ACS Biomater Sci Eng 6:879–888. https://doi.org/10.1021/acsbiomaterials.9b0157110.1021/acsbiomaterials.9b01571 ↗
42. Kono H, Uno T, Tsujisaki H et al (2020) Nanofibrillated bacterial cellulose surface modified with methyltrimethoxysilane for fiber-reinforced composites. ACS Appl Nano Mater 3:8232–8241. https://doi.org/10.1021/acsanm.0c0167010.1021/acsanm.0c01670 ↗
43. Cabral MVS, Carneiro AMP, Maior RMS et al (2021) Customized price-quality microcrystalline cellulose for developing cementitious composites with improved mechanical properties. Constr Build Mater 300:124064. https://doi.org/10.1016/j.conbuildmat.2021.12406410.1016/j.conbuildmat.2021.124064 ↗
44. Lin N, Huang J, Chang PR et al (2011) Surface acetylation of cellulose nanocrystal and its reinforcing function in poly(lactic acid). Carbohydr Polym 83:1834–1842. https://doi.org/10.1016/j.carbpol.2010.10.04710.1016/j.carbpol.2010.10.047 ↗
45. Chartrand A, Lavoie J-M, Huneault MA (2016) Surface modification of microcrystalline cellulose (MCC) and its application in LDPE-based composites. J Appl Polym Sci 134:44348. https://doi.org/10.1002/app.4434810.1002/app.44348 ↗
46. Yuan B, Chen Q, Ding W-Q et al (2012) Copolymer coatings consisting of 2-methacryloyloxyethyl phosphorylcholine and 3-methacryloxypropyl trimethoxysilane via ATRP to improve cellulose biocompatibility. ACS Appl Mater Interfaces 4:4031–4039. https://doi.org/10.1021/am300839910.1021/am3008399 ↗
47. Kobe R, Yoshitani K, Teramoto Y (2016) Fabrication of elastic composite hydrogels using surface-modified cellulose nanofiber as a multifunctional crosslinker. J Appl Polym Sci 133:1–8. https://doi.org/10.1002/app.4290610.1002/app.42906 ↗
48. Bugrov AN, Zavialova AY, Smyslov RY et al (2018) Luminescence of Eu3+ ions in hybrid polymer-inorganic composites based on poly(methyl methacrylate) and zirconia nanoparticles. Luminescence 33:837–849. https://doi.org/10.1002/bio.347610.1002/bio.3476 ↗
49. Arkles B (2000) Silicon Compounds. Silicon Esters, Kirk-Othmer Encycl Chem Technol. https://doi.org/10.1002/0471238961.1909120901181112.a0210.1002/0471238961.1909120901181112.a02 ↗
50. Yeo JS, Hwang SH (2015) Preparation and characteristics of polypropylene-graft-maleic anhydride anchored micro-fibriled cellulose: Its composites with polypropylene. J Adhes Sci Technol 29:185–194. https://doi.org/10.1080/01694243.2014.98063210.1080/01694243.2014.980632 ↗
51. Abdelmouleh M, Boufi S, Belgacem MN et al (2004) Modification of cellulosic fibres with functionalised silanes: Development of surface properties. Int J Adhes Adhes 24:43–54. https://doi.org/10.1016/S0143-7496(03)00099-X10.1016/S0143-7496(03)00099-X ↗
52. Gandini A, Belgacem MN (2011) Modifying cellulose fiber surfaces in the manufacture of natural fiber composites. In: Interface engineering of natural fibre composites for maximum performance. Elsevier, pp. 3–4210.1533/9780857092281.1.3 ↗
53. Pantoja M, Velasco F, Broekema D et al (2010) The influence of pH on the hydrolysis process of γ-methacryloxypropyltrimethoxysilane, analyzed by FT-IR, and the silanization of electrogalvanized steel. J Adhes Sci Technol 24:1131–1143. https://doi.org/10.1163/016942409X1258628382155910.1163/016942409X12586283821559 ↗
54. Matinlinna JP, Lung CYK, Tsoi JKH (2018) Silane adhesion mechanism in dental applications and surface treatments: a review. Dent Mater 34:13–28. https://doi.org/10.1016/j.dental.2017.09.00210.1016/j.dental.2017.09.002 ↗
55. Nikolaeva MN, Bugrov AN, Bezrukova MA et al (2020) Reduced graphene oxide resistance in composites with polystyrene of different molecular masses. Fuller Nanotub Carbon Nanostruct 28:163–167. https://doi.org/10.1080/1536383X.2019.168662810.1080/1536383X.2019.1686628 ↗
56. Ahangaran F, Navarchian AH (2020) Recent advances in chemical surface modification of metal oxide nanoparticles with silane coupling agents: a review. Adv Colloid Interface Sci 286:102298. https://doi.org/10.1016/j.cis.2020.10229810.1016/j.cis.2020.102298 ↗
57. Bugrov AN, Smyslov RY, Anan’eva TD, et al (2019) Soluble and insoluble polymer-inorganic systems based on poly(methyl methacrylate), modified with ZrO2-LnO1.5 (Ln = Eu, Tb) nanoparticles: Comparison of their photoluminescence. J Lumin 207:157–168. https://doi.org/10.1016/j.jlumin.2018.11.01110.1016/j.jlumin.2018.11.011 ↗
58. Brinker CJ (1988) Hydrolysis and condensation of silicates: Effects on structure. J Non Cryst Solids 100:31–50. https://doi.org/10.1016/0022-3093(88)90005-110.1016/0022-3093(88)90005-1 ↗
59. Issa AA, Luyt AS (2019) Kinetics of alkoxysilanes and organoalkoxysilanes polymerization: A Review. Polym (Basel) 11:537. https://doi.org/10.3390/polym1103053710.3390/polym11030537 ↗
60. Mabboux P-Y, Gleason KK (2005) Chemical bonding structure of low dielectric constant Si:O:C:H films characterized by solid-state NMR. J Electrochem Soc 152:F7. https://doi.org/10.1149/1.183035310.1149/1.1830353 ↗
61. Guo Z, Pereira T, Choi O et al (2006) Surface functionalized alumina nanoparticle filled polymeric nanocomposites with enhanced mechanical properties. J Mater Chem 16:2800–2808. https://doi.org/10.1039/b603020c10.1039/b603020c ↗
62. Morales-Acosta MD, Alvarado-Beltrán CG, Quevedo-López MA et al (2013) Adjustable structural, optical and dielectric characteristics in sol–gel PMMA–SiO2 hybrid films. J Non Cryst Solids 362:124–135. https://doi.org/10.1016/J.JNONCRYSOL.2012.11.02510.1016/J.JNONCRYSOL.2012.11.025 ↗
63. Ganicz T, Olejnik K, Rózga-Wijas K, Kurjata J (2020) New method of paper hydrophobization based on starch-cellulose-siloxane interactions. BioRes 15(2):4124–414210.15376/biores.15.2.4124-4142 ↗
64. Zanchetta E, Cattaldo M, Franchin G et al (2015) Stereolithography of SiOC ceramic microcomponents. Adv Mater. https://doi.org/10.1002/adma.20150347010.1002/adma.201503470 ↗
65. Castro C, Zuluaga R, Putaux JL et al (2011) Structural characterization of bacterial cellulose produced by gluconacetobacter swingsii sp. from Colombian agroindustrial wastes. Carbohydr Polym 84:96–102. https://doi.org/10.1016/j.carbpol.2010.10.07210.1016/j.carbpol.2010.10.072 ↗
66. Persson J, Chanzy H, Sugiyama J (1991) Combined infrared and electron diffraction study of the polymorphism of native celluloses. Macromolecules 24:2461–2466. https://doi.org/10.1021/ma00009a05010.1021/ma00009a050 ↗
67. French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896. https://doi.org/10.1007/s10570-013-0030-410.1007/s10570-013-0030-4 ↗
68. Kono H, Tsujisaki H, Tajima K (2022) Reinforcing poly(methyl methacrylate) with bacterial cellulose nanofibers chemically modified with methacryolyl groups. Nanomaterials 12:537. https://doi.org/10.3390/nano1203053710.3390/nano12030537 ↗
69. Kobe R, Iwamoto S, Endo T et al (2016) Stretchable composite hydrogels incorporating modified cellulose nanofiber with dispersibility and polymerizability: Mechanical property control and nanofiber orientation. Polymer 97:480–486. https://doi.org/10.1016/J.POLYMER.2016.05.06510.1016/J.POLYMER.2016.05.065 ↗
70. Niu J, Wang J, Dai X et al (2018) Dual physically crosslinked healable polyacrylamide/cellulose nanofibers nanocomposite hydrogels with excellent mechanical properties. Carbohydr Polym 193:73–81. https://doi.org/10.1016/j.carbpol.2018.03.08610.1016/j.carbpol.2018.03.086 ↗