Top

Published in:

18-11-2022 | Chemical routes to materials

Bacterial cellulose nanofibers modification with 3-(trimethoxysilyl)propyl methacrylate as a crosslinking and reinforcing agent for 3D printable UV-curable inks

Authors: Angelina P. Prosvirnina, Alexander N. Bugrov, Anatoliy V. Dobrodumov, Elena N. Vlasova, Veronika S. Fedotova, Alexandra L. Nikolaeva, Vitaly K. Vorobiov, Maria P. Sokolova, Michael A. Smirnov

Published in: Journal of Materials Science | Issue 44/2022

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

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.

Graphical Abstract

next article Droplet microfluidic synthesis of shape-tunable self-propelled catalytic micromotors and their application to water treatment

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

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):1962CrossRef

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-2020-0033CrossRef

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):3729–3749CrossRef

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/S11095-018-2531-1CrossRef

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/pharmaceutics12070620CrossRef

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/s40005-020-00499-4CrossRef

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):1398–1408CrossRef

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/aba2f7CrossRef

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/s10853-018-2407-0CrossRef

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/s10853-019-04186-0CrossRef

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-xCrossRef

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):6510–6520CrossRef

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.2019.101145CrossRef

14.

Okolie O, Stachurek I, Kandasubramanian B, Njuguna J (2007) Polymers 3D printing for hip implant applications: A Review. https://doi.org/10.3390/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/ma13010092CrossRef

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-xCrossRef

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.8b21268CrossRef

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/c8tb01757cCrossRef

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.2017.09.015CrossRef

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.2018.09.085CrossRef

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.2021.117976CrossRef

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-xCrossRef

23.

Mohd N, S Draman SF, N Salleh MS, Yusof NB (2017) Dissolution of cellulose in ionic liquid: A review. https://doi.org/10.1063/1.4975450

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/c3ta11130jCrossRef

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.2018.09.027CrossRef

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):1–9CrossRef

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/d1tb00624jCrossRef

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.0c11152CrossRef

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.2022.119475CrossRef

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/polym13183044CrossRef

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.202002914CrossRef

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/S1070427216050141CrossRef

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/jcs3020051CrossRef

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.0c00717CrossRef

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.2014.01.009CrossRef

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.2017.08.024CrossRef

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-yCrossRef

38.

Hasani M, Cranston ED, Westman G, Gray DG (2008) Cationic surface functionalization of cellulose nanocrystals. Soft Matter. https://doi.org/10.1039/b806789aCrossRef

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/10.1177/0892705705042600CrossRef

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/10.1163/156856189X00380CrossRef

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.9b01571CrossRef

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.0c01670CrossRef

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.2021.124064CrossRef

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.2010.10.047CrossRef

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.44348CrossRef

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/am3008399CrossRef

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.42906CrossRef

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.3476CrossRef

49.

Arkles B (2000) Silicon Compounds. Silicon Esters, Kirk-Othmer Encycl Chem Technol. https://doi.org/10.1002/0471238961.1909120901181112.a02CrossRef

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/10.1080/01694243.2014.980632CrossRef

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-XCrossRef

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. 3–42

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/10.1163/016942409X12586283821559CrossRef

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.2017.09.002CrossRef

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.2019.1686628CrossRef

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.2020.102298CrossRef

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-LnO_1.5 (Ln = Eu, Tb) nanoparticles: Comparison of their photoluminescence. J Lumin 207:157–168. https://doi.org/10.1016/j.jlumin.2018.11.011CrossRef

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)90005-1CrossRef

59.

Issa AA, Luyt AS (2019) Kinetics of alkoxysilanes and organoalkoxysilanes polymerization: A Review. Polym (Basel) 11:537. https://doi.org/10.3390/polym11030537CrossRef

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/10.1149/1.1830353CrossRef

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/b603020cCrossRef

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.2012.11.025CrossRef

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):4124–4142CrossRef

64.

Zanchetta E, Cattaldo M, Franchin G et al (2015) Stereolithography of SiOC ceramic microcomponents. Adv Mater. https://doi.org/10.1002/adma.201503470CrossRef

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.2010.10.072CrossRef

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/ma00009a050CrossRef

67.

French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896. https://doi.org/10.1007/s10570-013-0030-4CrossRef

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/nano12030537CrossRef

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.2016.05.065CrossRef

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.2018.03.086CrossRef

Title: Bacterial cellulose nanofibers modification with 3-(trimethoxysilyl)propyl methacrylate as a crosslinking and reinforcing agent for 3D printable UV-curable inks
Authors: Angelina P. Prosvirnina
Alexander N. Bugrov
Anatoliy V. Dobrodumov
Elena N. Vlasova
Veronika S. Fedotova
Alexandra L. Nikolaeva
Vitaly K. Vorobiov
Maria P. Sokolova
Michael A. Smirnov
Publication date: 18-11-2022
Publisher: Springer US
Published in: Journal of Materials Science / Issue 44/2022
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI: https://doi.org/10.1007/s10853-022-07902-5

Springer Professional

Abstract

Graphical Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 44/2022

Core–shell nanowires comprising silver@polypyrrole-derived pyrolytic carbon for high-efficiency microwave absorption

Co(OH)2 nanosheets anchored on CoB nanochains with enhanced electrochemical performance

Measurement and simulation of residual stresses in transient liquid phase bonded ferritic steels

Effect of annealing temperature on dual-structure coexisting precipitates in Cu–2.18Fe–0.03P alloy and softening mechanism at high temperature

Preparation and photocatalytic property of exfoliated poly(phenylenethiazolo[5,4‐d]thiazole) copolymers

A cross-scale analysis method for predicting the compressive mechanical properties of tin-based bearing alloy

Premium Partners