Fluoropolímeros sintetizados por ATRP: Caracterización térmica y transiciones UV

Edward M.A. Guerrero Gutiérrez; Byron López-Mayorga; Giorgio E. A. López-Pardo; Allan Vásquez-Bolaños

doi:10.36829/63CTS.v12i2.1804

Authors

Edward M.A. Guerrero Gutiérrez Escuela de Ingeniería Química, Universidad de San Carlos de Guatemala https://orcid.org/0000-0002-5778-3953
Byron López-Mayorga Escuela de Química, Facultad de Ciencias Químicas y Farmacia, Universidad de San Carlos de Guatemala https://orcid.org/0000-0001-7165-6283
Giorgio E. A. López-Pardo Escuela de Ingeniería Química https://orcid.org/0000-0002-8060-6437
Allan Vásquez-Bolaños Departamento de Química, Facultad de Ciencias y Humanidades, Universidad del Valle de Guatemala https://orcid.org/0000-0003-3837-5046

DOI:

https://doi.org/10.36829/63CTS.v12i2.1804

Keywords:

ATRP, thermal transitions, initiator, functional group

Abstract

This investigation aimed to characterize and compare thermal degradation and UV absorption of two block fluoropolymers synthesized via Atom Transfer Radical Polymerization (ATRP). The block fluoropolymers are composed of poly(1-phenylethylene)-block-poly(2,3,4,5,6-pentafluorostyrene)-block-poly(2,2,3,4,4,4-hexafluorobutyl methacrylate) [PS-b-PFS-b-PHFBMA] and poly(4-fluorostyrene)-block-poly(1-phenylethylene)-block-poly(2,2,3,4,4,4-hexafluorobutyl methacrylate) [P4FS-b-PS-b-PHFBMA]. These polymers were chemically characterized using Fourier-Transform Infrared Spectroscopy with Attenuated Total Reflection (FTIR) and liquid Proton Nuclear Magnetic Resonance (¹H NMR). Thermal degradation was evaluated using thermogravimetric analysis (TGA), and UV absorption was measured using UV-vis spectroscopy. The results showed that P4FS-b-PS-b-PHFBMA exhibited an initial weight loss 47% greater than PS-b-PFS-b-PHFBMA. Additionally, PHFBMA incorporation reduced the degradation temperature by 48% and 1.9% for P4FS-b-PS-b-PHFBMA and PS-b-PFS-b-PHFBMA, respectively. Furthermore, upon incorporating PHFBMA into the polymer chain, an additional absorption at 315 nm was observed in the UV spectrum for both fluoropolymers. This research successfully synthesized a new triblock fluoropolymer (P4FS-b-PS-b-PHFBMA) via ATRP and highlights the importance of block polymer chemistry that induces changes in thermal degradation and light absorption in the UV-vis spectrum, which could impact the design of polymeric materials for industrial or technological applications, such as optoelectronic devices or thermal protection systems.

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References

Agboola, O., Sadiku, R., Mokrani, T., Amer, I., & Imoru, O. (2017). Polyolefins and the environment. En S. C. O. Ugbolue (Ed.), Polyolefin fibres structure, properties and industrial applications (2nd ed., pp. 89-133). Elsevier. https://doi.org/10.1016/B978-0-08-101132-4.00004-7

Ajroldi, G., Pianca, M., Fumagalli, M., & Moggi, G. (1989). Fluoroelastomers-dependence of relaxation phenomena on composition. Polymer, 30(12), 2180-2187. https://doi.org/10.1016/0032-3861(89)90246-2

Allen, N. S., & Edge, M. (1993). Fundamentals of polymer degradation and stabilization (1st ed.). Springer Dordrecht.

Alsulaim, G. M., & Elamin, A. A. (2023). Two promising methodologies for dealing with changes in optical and Electrical Properties of Polymer Electrolytes (SPEs). Journal of Composites Science, 7(6), Artículo 221. https://doi.org/10.3390/jcs7060221

Amec Foster Wheeler Environment & Infrastructure. (2017). Socio-economic analysis of the European fluoropolymer industry – executive summary. https://fluoropolymers.eu/wp-content/uploads/2023/12/Fluoropolymers_SEA_2017.pdf

Atanasov, V., Bürger, M., Lyonnard, S., Porcar, L., & Kerres, J. (2013). Sulfonated poly(pentafluorostyrene): Synthesis & characterization. Solid State Ionics, 252, 75-83. https://doi.org/10.1016/j.ssi.2013.06.010

Blanksby, S. J., & Ellison, G. B. (2003). Bond dissociation energies of organic molecules. Accounts of Chemical Research, 36(4), 255-263. https://doi.org/10.1021/ar020230d

Bosson, K., Marcasuzaa, P., Bousquet, A., Tovar, G. E. M., Atanasov, V., & Billon, L. (2022). Pentafluorostyrene-based block copolymers controlled self-assembly pattern: A platform paving the way to functional block copolymers. European Polymer Journal, 179, Artículo 111560. https://doi.org/10.1016/j.eurpolymj.2022.111560

Bronstein, H., Nielsen, C. B., Schroeder, B. C., & McCulloch, I. (2020). The role of chemical design in the performance of organic semiconductors. Nature Reviews Chemistry, 4(2), 66-77. https://doi.org/10.1038/s41570-019-0152-9

Chen, L., Huan, T. D., & Ramprasad, R. (2017). Electronic Structure of Polyethylene: Role of Chemical, Morphological and Interfacial Complexity. Scientific Reports, 7(1), Artículo 6128. https://doi.org/10.1038/s41598-017-06357-y

da Costa, H. M., Ramos, V. D., & de Oliveira, M. G. (2007). Degradation of polypropylene (PP) during multiple extrusions: Thermal analysis, mechanical properties and analysis of variance. Polymer Testing, 26(5), 676-684. https://doi.org/10.1016/j.polymertesting.2007.04.003

Dhanalakshmi, M., Losetty, V., Prabu, P., Yadav, C. H., & Reddy, A. V. B. (2026). Optical properties of polymer and biopolymer nanocomposites: Recent advances and applications. En M. Moniruzzaman & A. V. Bhaskar Reddy (Eds.), Polymer and biopolymer nanocomposites (pp. 171-191). Elsevier. https://doi.org/10.1016/B978-0-443-26625-6.00007-3

Dolui, S., Kumar, D., Banerjee, S., & Ameduri, B. (2021). Well-Defined Fluorinated Copolymers: Current Status and Future Perspectives. Accounts of Materials Research, 2(4), 242-251. https://doi.org/10.1021/accountsmr.1c00015

Dong, J., Sang, X., Yin, W., & Chen, X. (2023). Preparation of fluorinated epoxy‐phthalonitrile resins with excellent thermal stability and low dielectric constant. Journal of Applied Polymer Science, 140(12). https://doi.org/10.1002/app.53641

Drobny, J. G. (2008). Technology of fluoropolymers (2nd ed.). CRC Press. https://doi.org/10.1201/9781420063189

Dudhat, H., Islam, R., Mudila, H., Mittal, R., Minakshi, Kumar, D., & Kumar, A. (2026). Spectroscopic and microscopic characterizations of conjugated polymer nanocomposites. En M. Pandey & K. Deshmukh (Eds.), Conjugated polymer-based nanocomposites (pp. 93-129). Elsevier. https://doi.org/10.1016/B978-0-443-29011-4.00015-8

Dworakowska, S., Lorandi, F., Gorczyński, A., & Matyjaszewski, K. (2022). Toward Green Atom Transfer Radical Polymerization: Current Status and Future Challenges. Advanced Science, 9(19), Artículo 2106076. https:// doi.org/10.1002/advs.202106076

Ebnesajjad, S. (2015). From fundamentals to applications. En Fluoroplastics (pp. 12-23). Elsevier. https://doi.org/10.1016/B978-1-4557-3199-2.00003-3

Ebnesajjad, S. (2021). Introduction to fluoropolymers (2nd ed.). Elsevier. https://doi.org/10.1016/C2018-0-04702-7

Edwards, A. A., & Alexander, B. D. (2010). Organic Applications of UV-Visible Absorption Spectroscopy. En J. C. Lindon (Ed.), Encyclopedia of Spectroscopy and Spectrometry (2nd ed., pp. 2030-2039). Elsevier. https://doi.org/10.1016/B978-0-12-374413-5.00013-0

Eid, N., Gimello, O., Bonnet, A., Devisme, S., & Améduri, B. (2021). Chain-End Functionality: The Key Factor toward Fluoropolymer Thermal Stability. Macromolecules, 54(17), 7690-7701. https://doi.org/10.1021/acs.macromol.1c00453

El-Khiyami, S. S., Ismail, A. M., & Hafez, R. S. (2021). Characterization, Optical and Conductivity Study of Nickel Oxide Based Nanocomposites of Polystyrene. Journal of Inorganic and Organometallic Polymers and Materials, 31(11), 4313-4325. https://doi.org/10.1007/s10904-021-02041-x

Facchetti, A. (2007). Semiconductors for organic transistors. Materials Today, 10(3), 28-37. https://doi.org/10.1016/S1369-7021(07)70017-2

Feast, W. J., Lövenich, P. W., Puschmann, H., & Taliani, C. (2001). Synthesis and structure of 4,4′-bis(2,3,4,5,6-pentafluorostyryl)stilbene, a self-assembling J aggregate based on aryl-fluoroaryl interactions. Chemical Communications, (5), 505-506. https://doi.org/10.1039/B100002K

Garrigues Mateo, S. (2017). Organic Solvent-Based. En Reference module in chemistry, molecular sciences and chemical engineering. Encyclopedia of Analitical Science (3rd ed., pp. 110-120). Elsevier. https://doi.org/10.1016/B978-0-12-409547-2.14227-1

Groch, P., Czaja, K., & Sacher-Majewska, B. (2020). Thermal stability of ethylene copolymers with multi-alkenylsilsesquioxane comonomers synthesized by organometallic catalyst - Effect of copolymer structure. Polymer Degradation and Stability, 172, Artículo 109075. https://doi.org/10.1016/j.polymdegradstab.2020.109075

Guerrero-Gutiérrez, E. M. A. (2021). Effect of Sulfonated Block Copolymer on the Equilibrium and Thermal Properties of Sulfonated Fluoroblock Copolymer Blend Membranes. Ciencia, Tecnologí¬a y Salud, 8(1), 57-66. https://doi.org/10.36829/63CTS.v8i1.887

Guerrero‐Gutiérrez, E. M. A., Pérez‐Pérez, M., Newbloom, G. M., Pozzo, L. D., & Suleiman, D. (2017). Effect of block composition on the morphology and transport properties of sulfonated fluoroblock copolymer blend membranes. Polymer Engineering & Science, 57(11), 1262-1272. https://doi.org/10.1002/pen.24508

Guerrero-Gutiérrez, E. M. A., Pérez-Pérez, M., & Suleiman, D. (2015). Synthesis and characterization of sulfonated fluorinated block copolymer membranes with different esterified initiators for DMFC applications. Journal of Applied Polymer Science, 132(23). https://doi.org/10.1002/app.42046

Hanif, M., Lu, P., Li, M., Zheng, Y., Xie, Z., Ma, Y., Li, D., & Li, J. (2007). Synthesis, characterization, electrochemistry and optical properties of a novel phenanthrenequinone‐ alt ‐dialkylfluorene conjugated copolymer. Polymer International, 56(12), 1507-1513. https://doi.org/10.1002/pi.2286

Hansen, N. M. L., Gerstenberg, M., Haddleton, D. M., & Hvilsted, S. (2008). Synthesis, characterization, and bulk properties of amphiphilic copolymers containing fluorinated methacrylates from sequential copper‐mediated radical polymerization. Journal of Polymer Science Part A: Polymer Chemistry, 46(24), 8097-8111. https://doi.org/10.1002/pola.23107

Hanwell, M. D., Curtis, D. E., Lonie, D. C., Vandermeersch, T., Zurek, E., & Hutchison, G. R. (2012). Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. Journal of Cheminformatics, 4(1), Artículo 17. https://doi.org/10.1186/1758-2946-4-17

Henry, J. J. (2015). Heat stabilized polyvinylidene fluoride polymer composition (Patent WO/2015/048697).

Hestand, N. J., & Spano, F. C. (2018). Expanded Theory of H- and J-Molecular Aggregates: The Effects of Vibronic Coupling and Intermolecular Charge Transfer. Chemical Reviews, 118(15), 7069-7163. https://doi.org/10.1021/acs.chemrev.7b00581

Hu, Y.-H., & Chen, C.-Y. (2003). The effect of end groups on the thermal degradation of poly(methyl methacrylate). Polymer Degradation and Stability, 82(1), 81-88. https://doi.org/10.1016/S0141-3910(03)00165-4

Jancar, J., & Tochacek, J. (2011). Effect of thermal history on the mechanical properties of three polypropylene impact-copolymers. Polymer Degradation and Stability, 96(9), 1546-1556. https://doi.org/10.1016/j.polymdegradstab.2011.05.013

Jankova, K., & Hvilsted, S. (2003). Preparation of Poly(2,3,4,5,6-pentafluorostyrene) and block copolymers with styrene by ATRP. Macromolecules, 36(5), 1753-1758. https://doi.org/10.1021/ma021039m

Jayan, J. S., Vindhyasurumi, A., Lekshmi, A. G., & Appukuttan, S. (2023). Fluoropolymer nanocomposite membranes for gas separation applications. En Advanced Fluoropolymer Nanocomposites (pp. 485-528). Elsevier. https://doi.org/10.1016/B978-0-323-95335-1.00016-5

Jiang, H., Cao, Y., Yang, Q., Xian, L., Tao, Y., Chen, R., & Huang, W. (2020). Organic resonance materials: Molecular design, photophysical properties, and optoelectronic applications. The Journal of Physical Chemistry Letters, 11(18), 7739-7754. https://doi.org/10.1021/acs.jpclett.0c01571

Khodadadi Yazdi, M., Zarrintaj, P., Saeb, M. R., Mozafari, M., & Bencherif, S. A. (2024). Progress in ATRP-derived materials for biomedical applications. Progress in Materials Science, 143, Artículo 101248. https://doi.org/10.1016/j.pmatsci.2024.101248

Ko, K.-Y., & Hwang, S.-H. (2018). Monomer composition effects on thermal properties of transparent poly(methyl methacrylate- co -isobornyl methacrylate- co -cyclohexyl maleimide) terpolymers. Journal of Industrial and Engineering Chemistry, 59, 50-55. https://doi.org/10.1016/j.jiec.2017.10.004

Kochervinskii, V. V. (2006). Effect of chemical interactions in the metal-F system on the electric properties of fluoroelastomers. Mendeleev Communications, 16(6), 331-333. https://doi.org/10.1070/MC2006v016n06ABEH002319

Lamontagne, H. R., & Lessard, B. H. (2020). Nitroxide-Mediated Polymerization: A Versatile Tool for the Engineering of Next Generation Materials. ACS Applied Polymer Materials, 2(12), 5327-5344. https://doi.org/10.1021/acsapm.0c00888

Li, H., Zhang, Y., Wang, K., & Hu, Y. (2015). Composition with capability of providing thermal stability for polymer and application of composition.

Linker, T. M., Tiwari, S., Kumazoe, H., Fukushima, S., Kalia, R. K., Nakano, A., Ramprasad, R., Shimojo, F., & Vashishta, P. (2020). Field-Induced Carrier Localization Transition in Dielectric Polymers. The Journal of Physical Chemistry Letters, 11(2), 352-358. https://doi.org/10.1021/acs.jpclett.9b03147

Lv, J., & Cheng, Y. (2021). Fluoropolymers in biomedical applications: state-of-the-art and future perspectives. Chemical Society Reviews, 50(9), 5435-5467. https://doi.org/10.1039/D0CS00258E

Lyu, J., Li, Y., Li, Z., Johnson, M., Sosnowski, S., Szymanski, R., Matyjaszewski, K., & Wang, W. (2023). Active kinetic chain length: Guide for control in atom transfer radical polymerization. Chemical Engineering Journal, 474, Artículo 145548. https://doi.org/10.1016/j.cej.2023.145548

Ma, Y., Hu, C., Guo, H., Fan, L., Yang, S., & Sun, W.-H. (2018). Structure effect on transition mechanism of UV-visible absorption spectrum in polyimides: A density functional theory study. Polymer, 148, 356-369. https://doi.org/10.1016/j.polymer.2018.06.049

Mamand, D. M., Hussen, S. A., & Aziz, S. B. (2025). Green approach to synthesis polymer composites based on chitosan with desired linear and non-linear optical characteristics. Scientific Reports, 15(1), Artículo 3130. https://doi.org/10.1038/s41598-024-75953-6

Mamand, D. M., Muhammad, D. S., Aziz, S. B., Hama, P. O., Al-Asbahi, B. A., Ahmed, A. A. A., & Hassan, J. (2025). Enhanced optical properties of chitosan polymer doped with orange peel dye investigated via UV–Vis and FTIR analysis. Scientific Reports, 15(1), Artículo 3232. https://doi.org/10.1038/s41598-025-87425-6

Masood, T. Bin, Thygesen, S. S., Linares, M., Abrikosov, A. I., Natarajan, V., & Hotz, I. (2021). Visual Analysis of Electronic Densities and Transitions in Molecules. Computer Graphics Forum, 40(3), 287-298. https://doi.org/10.1111/cgf.14307

Matyjaszewski, K. (2012). Atom Transfer Radical Polymerization (ATRP): Current status and future perspectives. Macromolecules, 45(10), 4015-4039. https://doi.org/10.1021/ma3001719

Matyjaszewski, K. (2024). Current status and outlook for ATRP. European Polymer Journal, 211, Artículo 113001. https://doi.org/10.1016/j.eurpolymj.2024.113001

Mhaske, S. T., Mohanty, J. D., & Chugh, K. W. (2023). Fluoropolymers: Brief history, fundamental chemistry, processing, structure, properties, and applications. En K. Deshmukh & C. M. Hussain (Eds.), Advanced Fluoropolymer Nanocomposites (pp. 1-27). Elsevier. https://doi.org/10.1016/B978-0-323-95335-1.00006-2

Mishnev, M., Korolev, A., & Zadorin, A. (2024). Effect of thermal aging on viscoelastic behavior of thermosetting polymers under mechanical and cyclic temperature impact. Polymers, 16(3), Artículo 391. https://doi.org/10.3390/polym16030391

Moliton, A., & Hiorns, R. C. (2004). Review of electronic and optical properties of semiconducting π‐conjugated polymers: Applications in optoelectronics. Polymer International, 53(10), 1397-1412. https://doi.org/10.1002/pi.1587

Neese, F., Wennmohs, F., Becker, U., & Riplinger, C. (2020). The ORCA quantum chemistry program package. The Journal of Chemical Physics, 152(22). https://doi.org/10.1063/5.0004608

Nikolaidis, A. K., & Achilias, D. S. (2018). Thermal degradation kinetics and viscoelastic behavior of poly(methyl methacrylate)/organomodified montmorillonite nanocomposites prepared via in situ bulk radical polymerization. Polymers, 10(5), Artículo 491. https://doi.org/10.3390/polym10050491

Parkatzidis, K., Wang, H. S., Truong, N. P., & Anastasaki, A. (2020). Recent developments and future challenges in controlled radical polymerization: A 2020 Update. Chem, 6(7), 1575-1588. https://doi.org/10.1016/j.chempr.2020.06.014

Perrier, S., Jackson, S. G., Haddleton, D. M., & Ameduri, B. (2002). Preparation of fluorinated methacrylic copolymers by copper mediated living radical polymerization. Tetrahedron, 58, 4053-4059.

Pielichowski, K., Njuguna, J., & Majka, T. M. (2023a). Mechanisms of thermal degradation of polymers. En K. Pielichowski, J. Njuguna & T. M. Majka (Eds.), Thermal Degradation of Polymeric Materials (2nd, ed., pp. 9-11). Elsevier. https://doi.org/10.1016/B978-0-12-823023-7.00001-0

Pielichowski, K., Njuguna, J., & Majka, T. M. (2023b). Thermal degradation of high temperature-resistant polymers. En K. Pielichowski, J. Njuguna & T. M. Majka (Eds.), Thermal Degradation of Polymeric Materials (2nd ed., pp. 187-211). Elsevier. https://doi.org/10.1016/B978-0-12-823023-7.00003-4

Pielichowski, K., Njuguna, J., & Majka, T. M. (2023c). Thermal degradation of polymers, copolymers, and blends. En K. Pielichowski, J. Njuguna & T. M. Majka (Eds.), Thermal Degradation of Polymeric Materials (2nd ed., pp. 49-147). Elsevier. https://doi.org/10.1016/B978-0-12-823023-7.00016-2

Quirk, R. P., & Pickel, D. L. (2012). Controlled End-Group Functionalization (Including Telechelics). En K. Matyjaszewski & M. Möller (Eds.), Polymer science: A comprehensive reference (pp. 351-412). Elsevier. https://doi.org/10.1016/B978-0-444-53349-4.00168-0

Rahmani, S., Hooshyari, K., Jamalpour, S., Tohidian, M., Maroufkhani, M., Vakili, H., Nobakht, D., & Pourhossein, A. (2023). Thermal stability and thermomechanical properties of fluoropolymer nanocomposites. En K. Deshmukh & C. Mustansar-Hussain (Eds.), Advanced Fluoropolymer Nanocomposites (pp. 213-245). Elsevier. https://doi.org/10.1016/B978-0-323-95335-1.00018-9

Rantuch, P. (2022). The thermal degradation of polymer materials. En Ignition of polymers (pp. 1-43). https://doi.org/10.1007/978-3-031-13082-3_1

Ray, S., & Cooney, R. P. (2018). Thermal degradation of polymer and polymer composites. En M. Kutz (Ed.), Handbook of environmental degradation of materials (3rd ed., pp. 185-206). Elsevier. https://doi.org/10.1016/B978-0-323-52472-8.00009-5

Robert, E. Y., & Mark, A. P. (2018). Polymer compositions having improved properties of thermal stability, color, and/or flow (Patent WO/2019/018340). https://patentscope.wipo.int/search/es/detail.jsf?docId=WO2019018340

Scheirs, J. (1997). Modern fluoropolymers: High performance polymers for diverse applications. En J. Scheirs (Ed.). John Wiley & Sons. https://www.wiley.com/en-us/Modern+Fluoropolymers%3A+High+Performance+Polymers+for+Diverse+Applications-p-9780471970552

Shahab, S., Sheikhi, M., Filippovich, L., Khaleghian, M., Dikusar, E., Yahyaei, H., & Borzehandani, M. Y. (2018). Spectroscopic Studies (Geometry Optimization, E → Z Isomerization, UV/Vis, Excited States, FT-IR, HOMO-LUMO, FMO, MEP, NBO, Polarization) and Anisotropy of Thermal and Electrical Conductivity of New Azomethine Dyes in Stretched Polymer Matrix. Silicon, 10(5), 2361-2385. https://doi.org/10.1007/s12633-018-9773-8

Shimadzu Corporation. (2001). UV-2401 PC / UV-2501 PC UV-Vis Spectrophotometer Instruction Manual.

Soulestin, T., Ladmiral, V., Dos Santos, F. D., & Améduri, B. (2017). Vinylidene fluoride- and trifluoroethylene-containing fluorinated electroactive copolymers. How does chemistry impact properties? Progress in Polymer Science, 72, 16-60. https://doi.org/10.1016/j.progpolymsci.2017.04.004

S&P Global Commodity Insights. (2022). Chemical economics handbook - fluoropolymers.

Spano, F. C., & Silva, C. (2014). H- and J-Aggregate Behavior in Polymeric Semiconductors. Annual Review of Physical Chemistry, 65(1), 477-500. https://doi.org/10.1146/annurev-physchem-040513-103639

Tarasov, A. V., Alikhanian, A. S., & Arkhangel’skii, I. V. (2009). Chemical interaction of fluoropolymers with transition metals. Inorganic Materials, 45(7), 809-813. https://doi.org/10.1134/S002016850907019X

Truong, N. P., Jones, G. R., Bradford, K. G. E., Konkolewicz, D., & Anastasaki, A. (2021). A comparison of RAFT and ATRP methods for controlled radical polymerization. Nature Reviews Chemistry, 5(12), 859-869. https://doi.org/10.1038/s41570-021-00328-8

Wang, Y.-M., Kálosi, A., Halahovets, Y., Beneš, H., de los Santos Pereira, A., & Pop-Georgievski, O. (2024). Solvent effects on surface-grafted and solution-born poly[N -(2-hydroxypropyl)methacrylamide] during surface-initiated RAFT polymerization. Polymer Chemistry, 15(20), 2070-2080. https://doi.org/10.1039/D4PY00177J

Witkowski, A., Stec, A. A., & Hull, T. R. (2016). Thermal decomposition of polymeric materials. En M. J. Hurley (Ed.), SFPE Handbook of Fire Protection Engineering (5th ed., pp. 167-254). Springer. https://doi.org/10.1007/978-1-4939-2565-0_7

Wood Environment & Infrastructure Solutions. (2020). Socio-economic assessment of the US fluoropolymer industry. https://fluoropolymerpartnership.com/wp-content/uploads/2020/03/Socio-Economic-Assessment-of-the-US-Fluoropolymer-Industry-Executive-Summary.pdf

Xie, L.-H., Yin, C.-R., Lai, W.-Y., Fan, Q.-L., & Huang, W. (2012). Polyfluorene-based semiconductors combined with various periodic table elements for organic electronics. Progress in Polymer Science, 37(9), 1192-1264. https://doi.org/10.1016/j.progpolymsci.2012.02.003

Xu, W., Liu, H., Zhang, B., Gao, Y., Hao, L., & Wang, X. (2023). Synthesis and performance of novel fluoro acrylate polymer containing rigid cyclohexane group as a mesogenic core. Journal of Macromolecular Science, Part A, 60(12), 884-895. https://doi.org/10.1080/10601325.2023.2284794

Xu, Y., Li, Z., Zhu, K., Sun, X., Liu, Y., Xiong, S., Wu, Y., & Yang, Y. (2022). Thermal degradation behavior and gas phase flame-retardant mechanism of diamine-based polybenzoxazine/polyhexahydrotriazine interpenetrating polymer network. Polymer Degradation and Stability, 204, Artículo 110103. https://doi.org/10.1016/j.polymdegradstab.2022.110103

Yin, Q., Alcouffe, P., Beyou, E., Charlot, A., & Portinha, D. (2018). Controlled perfluorination of poly(2,3,4,5,6-pentafluorostyrene) (PPFS) and PPFS-functionalized fumed silica by thiol-para-fluoro coupling: Towards the design of self-cleaning (nano)composite films. European Polymer Journal, 102, 120-129. https://doi.org/10.1016/j.eurpolymj.2018.03.016