N-acylhydrazone Derivative-Loaded Cellulose Acetate Films: Thermoanalytical, Spectroscopic, Mechanical and Morphological Characterization
Abstract
:1. Introduction
2. Materials and Methods
2.1. Material
2.2. Preparation of Cellulose Acetate Films with and without JR19
2.3. Physicochemical Characterization
2.3.1. Bending Resistance Test
2.3.2. Tensile Test
2.3.3. Optical Microscopy (OM)
2.3.4. Scanning Electron Microscopy (SEM)
2.3.5. Thermal Analysis
Differential Scanning Calorimetry (DSC)
Thermogravimetry (TG) and Its Derivative (DTG)
2.3.6. Fourier Transform Infrared Spectroscopy (FTIR)
2.3.7. X-ray Diffraction (XRD)
3. Results and Discussion
3.1. Development of Cellulose Acetate Films with JR19
3.2. Bending Resistance
3.3. Tensile Test
3.4. Optical Microscopy
3.5. Scanning Electron Microscopy (SEM)
3.6. Thermal Analysis by Differential Scanning Calorimetry (DSC) and Thermogravimetry and Its Derivative (TG/DTG)
3.7. Fourier Transform Infrared Spectroscopy (FTIR)
3.8. X-ray Diffraction (XRD)
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
References
- George, B.; Suchithra, T.V. Plant-derived bioadhesives for wound dressing and drug delivery system. Fitoterapia 2019, 137. [Google Scholar] [CrossRef]
- Pillai, O.; Panchagnula, R. Polymers in Drug Delivery Omathanu Pillai and Ramesh Panchagnula. Curr. Opin. Chem. Biol. 2001, 5, 447–451. [Google Scholar] [CrossRef]
- Du, H.; Liu, W.; Zhang, M.; Si, C.; Zhang, X.; Li, B. Cellulose nanocrystals and cellulose nanofibrils based hydrogels for biomedical applications. Carbohydr. Polym. 2019, 209, 130–144. [Google Scholar] [CrossRef] [PubMed]
- Liu, W.; Du, H.; Zhang, M.; Liu, K.; Liu, H.; Xie, H.; Zhang, X.; Si, C. Bacterial Cellulose-Based Composite Scaffolds for Biomedical Applications: A Review. ACS Sustain. Chem. Eng. 2020, 8, 7536–7562. [Google Scholar] [CrossRef]
- Gonçalves, S.M.; dos Santos, D.C.; Motta, J.F.G.; Santos, R.R. dos; Chávez, D.W.H.; Melo, N.R. de Structure and functional properties of cellulose acetate films incorporated with glycerol. Carbohydr. Polym. 2019, 209, 190–197. [Google Scholar] [CrossRef]
- Khoshnevisan, K.; Maleki, H.; Samadian, H.; Shahsavari, S.; Sarrafzadeh, M.H.; Larijani, B.; Dorkoosh, F.A.; Haghpanah, V.; Khorramizadeh, M.R. Cellulose acetate electrospun nanofibers for drug delivery systems: Applications and recent advances. Carbohydr. Polym. 2018, 198, 131–141. [Google Scholar] [CrossRef]
- Candido, R.G.; Godoy, G.G.; Gonçalves, A. Characterization and application of cellulose acetate synthesized from sugarcane bagasse. Carbohydr. Polym. 2017, 167, 280–289. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- De Freitas, R.R.M.; Senna, A.M.; Botaro, V.R. Influence of degree of substitution on thermal dynamic mechanical and physicochemical properties of cellulose acetate. Ind. Crops Prod. 2017, 109, 452–458. [Google Scholar] [CrossRef]
- Puls, J.; Wilson, S.A.; Hölter, D. Degradation of Cellulose Acetate-Based Materials: A Review. J. Polym. Environ. 2011, 19, 152–165. [Google Scholar] [CrossRef] [Green Version]
- Tedeschi, G.; Guzman-Puyol, S.; Paul, U.C.; Barthel, M.J.; Goldoni, L.; Caputo, G.; Ceseracciu, L.; Athanassiou, A.; Heredia-Guerrero, J.A. Thermoplastic cellulose acetate oleate films with high barrier properties and ductile behaviour. Chem. Eng. J. 2018, 348, 840–849. [Google Scholar] [CrossRef]
- Białopiotrowicz, T.; Jańczuk, B. The wettability of a cellulose acetate membrane in the presence of bovine serum albumin. Appl. Surf. Sci. 2002, 201, 146–153. [Google Scholar] [CrossRef]
- Mostafa, N.A.; Farag, A.A.; Abo-dief, H.M.; Tayeb, A.M. Production of biodegradable plastic from agricultural wastes. Arab. J. Chem. 2018, 11, 546–553. [Google Scholar] [CrossRef] [Green Version]
- Edgar, K.J. Cellulose esters in drug delivery. Cellulose 2007, 14, 49–64. [Google Scholar] [CrossRef]
- Dąbrowska, A.K.; Spano, F.; Derler, S.; Adlhart, C.; Spencer, N.D.; Rossi, R.M. The relationship between skin function, barrier properties, and body-dependent factors. Ski. Res. Technol. 2018, 24, 165–174. [Google Scholar] [CrossRef] [Green Version]
- Moura, L.I.F.; Dias, A.M.A.; Carvalho, E.; De Sousa, H.C. Recent advances on the development of wound dressings for diabetic foot ulcer treatment-A review. Acta Biomater. 2013, 9, 7093–7114. [Google Scholar] [CrossRef] [Green Version]
- Wiegand, C.; Hipler, U.C. Polymer-based biomaterials as dressings for chronic stagnating wounds. Macromol. Symp. 2010, 294, 1–13. [Google Scholar] [CrossRef]
- Devi, N.; Dutta, J. Preparation and characterization of chitosan-bentonite nanocomposite films for wound healing application. Int. J. Biol. Macromol. 2017, 104, 1897–1904. [Google Scholar] [CrossRef]
- Atmani, H.; Aboulouard, A.; Bakkardouch, F.E.; Laallam, L.; Jouaiti, A.; El idrissi, M. Physical and chemical aspects of the interaction of chitosan and cellulose acetate with ions Ca2+ and K+ using DFT methods. J. Mol. Model. 2021, 27, 1–12. [Google Scholar] [CrossRef]
- De Moraes, A.D.T.O.; de Miranda, M.D.S.; Jacob, Í.T.T.; da Amorim, C.A.C.; de Moura, R.O.; da Silva, S.Â.S.; Soares, M.B.P.; de Almeida, S.M.V.; de Souza, T.R.C.L.; de Oliveira, J.F.; et al. Synthesis, in vitro and in vivo biological evaluation, COX-1/2 inhibition and molecular docking study of indole-N-acylhydrazone derivatives. Bioorg. Med. Chem. 2018, 26, 5388–5396. [Google Scholar] [CrossRef]
- Tian, B.; He, M.; Tan, Z.; Tang, S.; Hewlett, I.; Chen, S.; Jin, Y.; Yang, M. Synthesis and Antiviral Evaluation of New N-acylhydrazones Containing Glycine Residue. Chem. Biol. Drug Des. 2011, 77, 189–198. [Google Scholar] [CrossRef]
- Gorantla, V.; Gundla, R.; Jadav, S.S.; Anugu, S.R.; Chimakurthy, J.; Nidasanametla, S.K.; Korupolu, R. Molecular hybrid design, synthesis and biological evaluation of N-phenyl sulfonamide linked N-acyl hydrazone derivatives functioning as COX-2 inhibitors: New anti-inflammatory, anti-oxidant and anti-bacterial agents. New J. Chem. 2017, 41, 13516–13532. [Google Scholar] [CrossRef]
- Rozada, A.M.F.; Rodrigues-Vendramini, F.A.V.; Gonçalves, D.S.; Rosa, F.A.; Basso, E.A.; Seixas, F.A.V.; Kioshima, É.S.; Gauze, G.F. Synthesis and antifungal activity of new hybrids pyrimido[4,5-d] pyridazinone-N-acylhydrazones. Bioorg. Med. Chem. Lett. 2020, 30, 12244. [Google Scholar] [CrossRef]
- De Almeida, P.S.V.B.; Pereira, T.M.; Kummerle, A.E.; Guedes, G.P.; Silva, H.; de Oliveira, L.L.; Neves, A.P. New Ru(II)–DMSO complexes containing coumarin-N-acylhydrazone hybrids: Synthesis, X-ray structures, cytotoxicity and antimicrobial activities. Polyhedron 2019, 171, 20–31. [Google Scholar] [CrossRef]
- Cerqueira, J.V.; Meira, C.S.; de Santos, E.S.; de Aragão França, L.S.; Vasconcelos, J.F.; Nonaka, C.K.V.; de Melo, T.L.; dos Santos Filho, J.M.; Moreira, D.R.M.; Soares, M.B.P. Anti-inflammatory activity of SintMed65, an N-acylhydrazone derivative, in a mouse model of allergic airway inflammation. Int. Immunopharmacol. 2019, 75. [Google Scholar] [CrossRef] [PubMed]
- De Cordeiro, N.M.; Freitas, R.H.C.N.; Fraga, C.A.M.; Fernandes, P.D. New 2-amino-pyridinyl-N-acylhydrazones: Synthesis and identification of their mechanism of anti-inflammatory action. Biomed. Pharmacother. 2020, 123. [Google Scholar] [CrossRef]
- ASTM American Society for Testing and Materials. D 882-02: Standard Test Method for Tensile Properties of Thin Plastic Sheeting. ASTM Int. 2002, 14, 1–10. [Google Scholar]
- Tanaka, S.; Iwata, T.; Iji, M. Long/short chain mixed cellulose esters: Effects of long acyl chain structures on mechanical and thermal properties. ACS Sustain. Chem. Eng. 2017, 5, 1485–1493. [Google Scholar] [CrossRef]
- Khatri, P.; Desai, D.; Shelke, N.; Minko, T. Role of plasticizer in membrane coated extended release oral drug delivery system. J. Drug Deliv. Sci. Technol. 2018, 44, 231–243. [Google Scholar] [CrossRef]
- Wanderley, D.M.S.; Melo, D.F.; Silva, L.M.; Souza, J.W.L.; Pina, H.V.; Lima, D.B.; Amoah, S.K.S.; Borges, S.M.P.; Fook, M.V.L.; Moura, R.O.; et al. Biocompatibility and mechanical properties evaluation of chitosan films containing an N-acylhydrazonic derivative. Eur. J. Pharm. Sci. 2020, 155, 105547. [Google Scholar] [CrossRef]
- Sasikala, L.; Durai, B.; Rathinamoorthy, R. Manuka honey loaded chitosan hydrogel films for wound dressing applications. Int. J. PharmTech Res. 2013, 5, 1774–1785. [Google Scholar]
- Bano, I.; Ghauri, M.A.; Yasin, T.; Huang, Q.; Palaparthi, A.D.S. Characterization and potential applications of gamma irradiated chitosan and its blends with poly(vinyl alcohol). Int. J. Biol. Macromol. 2014, 65, 81–88. [Google Scholar] [CrossRef] [PubMed]
- Kouchak, M.; Handali, S.; Naseri Boroujeni, B. Evaluation of the Mechanical Properties and Drug Permeability of Chitosan/Eudragit RL Composite Film. Osong Public Health Res. Perspect. 2015, 6, 14–19. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Gao, Y.; Wang, X.; Li, X.; Dai, H. An antibacterial composite film based on cellulose acetate/TiO2 nanoparticles. New J. Chem. 2020, 44, 20751–20758. [Google Scholar] [CrossRef]
- Evans, N.D.; Oreffo, R.O.C.; Healy, E.; Thurner, P.J.; Man, Y.H. Epithelial mechanobiology, skin wound healing, and the stem cell niche. J. Mech. Behav. Biomed. Mater. 2013, 28, 397–409. [Google Scholar] [CrossRef] [Green Version]
- Liu, H.; Adhikari, R.; Guo, Q.; Adhikari, B. Preparation and characterization of glycerol plasticized (high-amylose) starch-chitosan films. J. Food Eng. 2013, 116, 588–597. [Google Scholar] [CrossRef]
- Stachowiak, N.; Kowalonek, J.; Kozlowska, J. Effect of plasticizer and surfactant on the properties of poly(vinyl alcohol)/chitosan films. Int. J. Biol. Macromol. 2020, 164, 2100–2107. [Google Scholar] [CrossRef] [PubMed]
- Wu, S.; Qin, X.; Li, M. The structure and properties of cellulose acetate materials: A comparative study on electrospun membranes and casted films. J. Ind. Text. 2014, 44, 85–98. [Google Scholar] [CrossRef]
- Cobo, F.N.; Faria-Tisher, P.C.S.; Duarte, J.L.; Carvalho, G.M. Preparation and characterization of microporous cellulose acetate films using breath figure method by spin coating technique. Cellulose 2017, 24, 4981–4995. [Google Scholar] [CrossRef]
- Stenzel, M.H.; Barner-Kowollik, C.; Davis, T.P. Formation of Honeycomb-Structured, Porous Films via Breath Figures with Different Polymer Architectures. J. Polym. Sci. Part A Polym. Chem. 2006, 44, 7207–7224. [Google Scholar] [CrossRef]
- Srinivasarao, M.; Collings, D.; Philips, A.; Patel, S. Three-dimensionally ordered array of air bubbles in a polymer film. Science 2001, 292, 79–83. [Google Scholar] [CrossRef] [Green Version]
- Yu, B.; Cong, H.; Li, Z.; Yuan, H.; Peng, Q.; Chi, M.; Yang, S.; Yang, R.; Ranil Wickramasinghe, S.; Tang, J. Fabrication of highly ordered porous membranes of cellulose triacetate on ice substrates using breath figure method. J. Polym. Sci. Part B Polym. Phys. 2015, 53, 552–558. [Google Scholar] [CrossRef]
- Xiong, X.; Lin, M.; Zou, W. Honeycomb Structured Porous Films Prepared by the Method of Breath Figure: History and Development. Curr. Org. Chem. 2012, 15, 3706–3718. [Google Scholar] [CrossRef]
- Coty, J.B.; Martin, C.; Telò, I.; Spitzer, D. Use of Spray Flash Evaporation (SFE) technology to improve dissolution of poorly soluble drugs: Case study on furosemide nanocrystals. Int. J. Pharm. 2020, 589, 119827. [Google Scholar] [CrossRef] [PubMed]
- Gigliobianco, M.R.; Casadidio, C.; Censi, R.; Di Martino, P. Nanocrystals of poorly soluble drugs: Drug bioavailability and physicochemical stability. Pharmaceutics 2018, 10, 134. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Rahimpour, A.; Madaeni, S.S.; Ghorbani, S.; Shockravi, A.; Mansourpanah, Y. The influence of sulfonated polyethersulfone (SPES) on surface nano-morphology and performance of polyethersulfone (PES) membrane. Appl. Surf. Sci. 2010, 256, 1825–1831. [Google Scholar] [CrossRef]
- Jaganathan, S.K.; Mohandas, H.; Sivakumar, G.; Kasi, P.; Sudheer, T.; Avineri Veetil, S.; Murugesan, S.; Supriyanto, E. Enhanced blood compatibility of metallocene polyethylene subjected to hydrochloric acid treatment for cardiovascular implants. Biomed Res. Int. 2014, 2014. [Google Scholar] [CrossRef]
- Mirabedini, S.M.; Rahimi, H.; Hamedifar, S.; Mohsen Mohseni, S. Microwave irradiation of polypropylene surface: A study on wettability and adhesion. Int. J. Adhes. Adhes. 2004, 24, 163–170. [Google Scholar] [CrossRef]
- Delgado, J.F.; Peltzer, M.A.; Wagner, J.R.; Salvay, A.G. Hydration and water vapour transport properties in yeast biomass based films: A study of plasticizer content and thickness effects. Eur. Polym. J. 2018, 99, 9–17. [Google Scholar] [CrossRef]
- Paolicelli, P.; Petralito, S.; Varani, G.; Nardoni, M.; Pacelli, S.; Di Muzio, L.; Tirillò, J.; Bartuli, C.; Cesa, S.; Casadei, M.A.; et al. Effect of glycerol on the physical and mechanical properties of thin gellan gum films for oral drug delivery. Int. J. Pharm. 2018, 547, 226–234. [Google Scholar] [CrossRef]
- Ganesan, P. Natural and bio polymer curative films for wound dressing medical applications. Wound Med. 2017, 18, 33–40. [Google Scholar] [CrossRef]
- Jantrawut, P.; Chaiwarit, T.; Jantanasakulwong, K.; Brachais, C.H.; Chambin, O. Effect of plasticizer type on tensile property and in vitro indomethacin release of thin films based on low-methoxyl pectin. Polymers (Basel) 2017, 9, 289. [Google Scholar] [CrossRef] [PubMed]
- Kendouli, S.; Khalfallah, O.; Sobti, N.; Bensouissi, A.; Avci, A.; Eskizeybek, V.; Achour, S. Modification of cellulose acetate nanofibers with PVP/Ag addition. Mater. Sci. Semicond. Process. 2014, 28, 13–19. [Google Scholar] [CrossRef]
- Amaral, H.R.; Cipriano, D.F.; Santos, M.S.; Schettino, M.A.; Ferreti, J.V.T.; Meirelles, C.S.; Pereira, V.S.; Cunha, A.G.; Emmerich, F.G.; Freitas, J.C.C. Production of high-purity cellulose, cellulose acetate and cellulose-silica composite from babassu coconut shells. Carbohydr. Polym. 2019, 210, 127–134. [Google Scholar] [CrossRef] [PubMed]
- Senna, A.M.; De Menezes, A.J.; Botaro, V.R. Estudo da densidade de ligações cruzadas em géis superabsorventes obtidos do acetato de celulose. Polimeros 2013, 23, 59–64. [Google Scholar] [CrossRef]
- Pola, C.C.; Medeiros, E.A.A.; Pereira, O.L.; Souza, V.G.L.; Otoni, C.G.; Camilloto, G.P.; Soares, N.F.F. Cellulose acetate active films incorporated with oregano (Origanum vulgare) essential oil and organophilic montmorillonite clay control the growth of phytopathogenic fungi. Food Packag. Shelf Life 2016, 9, 69–78. [Google Scholar] [CrossRef]
- Pandey, M.K.; Khan, A.R.; Saxena, A.K. Synthesis and thermal analysis of phosphonitrile-core-bearing aromatic nitriles for high-temperature applications. J. Therm. Anal. Calorim. 2017, 129, 1453–1462. [Google Scholar] [CrossRef]
- Ke, H.; Pang, Z.; Peng, B.; Wang, J.; Cai, Y.; Huang, F.; Wei, Q. Thermal energy storage and retrieval properties of form-stable phase change nanofibrous mats based on ternary fatty acid eutectics/polyacrylonitrile composite by magnetron sputtering of silver. J. Therm. Anal. Calorim. 2016, 123, 1293–1307. [Google Scholar] [CrossRef]
- Konnola, R.; Nair, C.P.R.; Joseph, K. Cross-linking of carboxyl-terminated nitrile rubber with polyhedral oligomeric silsesquioxane: Cure kinetics. J. Therm. Anal. Calorim. 2016, 123, 1479–1489. [Google Scholar] [CrossRef]
- Wanderley, D.M.S.; Melo, D.F.; Silva, L.M.; Silva, W.C.; Correia, L.P.; Oshiro-Junior, J.A.; Fook, M.V.L.; Moura, R.O.; Lima, R.S.C.; Damasceno, B.P.G.L. Physical–chemical characterization of N-acylhydrazone derivative chitosan films using spectroscopic and thermoanalytical techniques. J. Therm. Anal. Calorim. 2019, 138, 3789–3796. [Google Scholar] [CrossRef]
- Wojnarowska, Z.; Grzybowska, K.; Adrjanowicz, K.; Kaminski, K.; Paluch, M.; Hawelek, L.; Wrzalik, R.; Dulski, M.; Sawicki, W.; Mazgalski, J.; et al. Study of the amorphous glibenclamide drug: Analysis of the molecular dynamics of quenched and cryomilled material. Mol. Pharm. 2010, 7, 1692–1707. [Google Scholar] [CrossRef]
- Thakral, N.K.; Zanon, R.L.; Kelly, R.C.; Thakral, S. Applications of Powder X-ray Diffraction in Small Molecule Pharmaceuticals: Achievements and Aspirations. J. Pharm. Sci. 2018, 107, 2969–2982. [Google Scholar] [CrossRef]
- Da Meireles, C.S.; Filho, G.R.; Fernandes Ferreira, M.; Cerqueira, D.A.; Assunção, R.M.N.; Ribeiro, E.A.M.; Poletto, P.; Zeni, M. Characterization of asymmetric membranes of cellulose acetate from biomass: Newspaper and mango seed. Carbohydr. Polym. 2010, 80, 954–961. [Google Scholar] [CrossRef]
- Shaikh, H.M.; Pandare, K.V.; Nair, G.; Varma, A.J. Utilization of sugarcane bagasse cellulose for producing cellulose acetates: Novel use of residual hemicellulose as plasticizer. Carbohydr. Polym. 2009, 76, 23–29. [Google Scholar] [CrossRef]
- Chen, Y.; Qiu, Y.; Chen, W.; Wei, Q. Electrospun thymol-loaded porous cellulose acetate fibers with potential biomedical applications. Mater. Sci. Eng. C 2020, 109, 110536. [Google Scholar] [CrossRef] [PubMed]
- Leuner, C.; Dressman, J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50, 47–60. [Google Scholar] [CrossRef]
Sample | Thickness (mm) | Tensile Strenght (Mpa) | Deformation (%) |
---|---|---|---|
BF | 0.132 ± 0.016 | 2.966 ± 0.52 | 5.834 ± 1.72 |
JR19F | 0.137 ± 0.019 | 3.672 ± 1.45 | 6.556 ± 2.88 |
DSC | TG | |||||
---|---|---|---|---|---|---|
Sample | Events | Tpeak (°C) | ΔH (J g−1) | Phases | Temperature Range (°C) | Mass (%) |
JR19 | 1 2 3 | 198.40 201.64 253.11 | 41.92 159.40 59.88 | 1 2 3 4 | 30.00–140.71 140.71–253.74 253.74–462.40 462.40–748.31 | 5.97 3.81 33.51 56.3 |
ACT | 1 2 | 51.05 233.00 | 185.4 6.322 | 1 2 | 30.66–151.66 256.59–441.86 | 9.216 84.40 |
ACT:JR19 | 1 2 3 | 75.05 195.61 200.67 | 18.94 33.22 55.02 | 1 2 3 4 | 39.17–110.07 110.07–228.23 228.23–295.34 295.34–424.85 | 2.097 3.545 11.76 47.08 |
BF | 1 2 | 59.09 247.66 | 347.2 25.92 | 1 2 3 | 30.66–117.63 117.63–269.82 284.95–413.51 | 25.32 51.81 15.62 |
JR19F | 1 2 3 | 71.34 200.04 257.87 | 349.6 86.50 47.16 | 1 2 3 | 29.72–114.79 114.79–272.66 272.66–432.41 | 30.73 45.05 16.26 |
Band Position (cm−1). | Attribution |
---|---|
3480 | O–H stretch |
2940 | Asymmetric stretch of CH3 |
1730 | Ester carbonyl stretch |
1635 | Water deformation |
1430 | Asymmetric strain of CH2 |
1360 | Asymmetric strain of CH3 |
1230 | Acetate C–O–O stretch |
1030 | C–O stretch |
890 | Stretching of the glycosidic bond |
Band (cm−1) | Attribution |
---|---|
3280 | N-H stretch |
2959 | C-H stretch |
2264 | Nitrile stretch (C≡N) |
1667 | Axial strain C=O of amide |
741 | Aromatic ring of the indol group |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Assis, A.C.L.d.; Moreira, L.M.C.d.C.; Rocha, B.P.; Pereira, M.R.B.; de Melo, D.F.; Moura, R.O.d.; Azevedo, E.P.d.; Oshiro-Junior, J.A.; Damasceno, B.P.G.d.L. N-acylhydrazone Derivative-Loaded Cellulose Acetate Films: Thermoanalytical, Spectroscopic, Mechanical and Morphological Characterization. Polymers 2021, 13, 2345. https://doi.org/10.3390/polym13142345
Assis ACLd, Moreira LMCdC, Rocha BP, Pereira MRB, de Melo DF, Moura ROd, Azevedo EPd, Oshiro-Junior JA, Damasceno BPGdL. N-acylhydrazone Derivative-Loaded Cellulose Acetate Films: Thermoanalytical, Spectroscopic, Mechanical and Morphological Characterization. Polymers. 2021; 13(14):2345. https://doi.org/10.3390/polym13142345
Chicago/Turabian StyleAssis, Amaro César Lima de, Lívia Maria Coelho de Carvalho Moreira, Beatriz Patrício Rocha, Milena Raissa Bezerra Pereira, Demis Ferreira de Melo, Ricardo Olímpio de Moura, Eduardo Pereira de Azevedo, João Augusto Oshiro-Junior, and Bolívar Ponciano Goulart de Lima Damasceno. 2021. "N-acylhydrazone Derivative-Loaded Cellulose Acetate Films: Thermoanalytical, Spectroscopic, Mechanical and Morphological Characterization" Polymers 13, no. 14: 2345. https://doi.org/10.3390/polym13142345