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Structural features of functional polysiloxanes radical and ionic photo-curing for laser printing applications

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Abstract

The laser induced curing of acryloxy terminated ethyleneoxide dimethylsiloxane-ethyleneoxide ABA block copolymer (PDMS-AO) and (3-glycidoxypropyl)trimethoxysilane (GPTMS) was carried out with 2-hydroxy-2-methylpropiophenone as radical photoinitiator and p-(octyloxyphenyl)phenyliodonium hexafluoroantimonate as cationic photoinitiator, respectively. The cross-linking mechanisms for both mixtures were determined through monitoring of photocuring by SSNMR, FTIR and Raman spectroscopies. The obtained silicone rubbers were tested by swelling measurements and thermogravimetric analysis. In comparison with PDMS-AO, cross-linked GPTMS had slightly more cross-linking density (by approximately 20% more). The cross-linked GPTMS was more thermally stable in air than cured PDMS-AO (by c.a. 190° C) due to both mechanisms: epoxy polymerization and Si–O–Si formation. The possibility of laser printing with defined framework for PDMS-AO was successfully demonstrated that allows obtaining laser printed polymer objects.

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References

  1. Ngo TD, Kashani A, Imbalzano G (2018) Additive manufacturing (3D printing): A review of materials, methods, applications and challenges. Compos Part B Eng 143:172 –196 https://doi.org/10.1016/j.compositesb.2018.02.012

  2. Selimis A, Mironov V, Farsari M (2015) Direct laser writing: Principles and materials for scaffold 3D printing. Microelectron Eng 132:83–89 https://doi.org/10.1016/j.mee.2014.10.001

  3. Wu H, Fahy WP, Kim S (2020) Recent developments in polymers/polymer nanocomposites for additive manufacturing. Prog Mater Sci 111:100638 https://doi.org/10.1016/j.pmatsci.2020.100638

  4. Charoo NA, Barakh Ali SF, Mohamed EM (2020) Selective laser sintering 3D printing – an overview of the technology and pharmaceutical applications. Drug Dev Ind Pharm 46: 869–877 https://doi.org/10.1080/03639045.2020.1764027

  5. Palaganas J, Leon de AC, Mangadlao J (2017) Facile Preparation of Photocurable Siloxane Composite for 3D Printing Macromol. Mater Eng 302:1–9 https://doi.org/10.1002/mame.201600477

  6. Zhao T, Yu R, Li X (2019) A comparative study on 3D printed silicone-epoxy/acrylate hybrid polymers via pure photopolymerization and dual-curing mechanisms. J Mater Sci 54:5101–5111 https://doi.org/10.1007/s10853-018-3070-1

  7. Woods R, Feldbacher S, Zidar D (2014) 3D optical waveguides produced by two photon photopolymerisation of a flexible silanol terminated polysiloxane containing acrylate functional groups. Opt Mater Express 4:486 https://doi.org/10.1364/ome.4.000486

  8. Bhattacharjee N, Parra-Cabrera C, Kim YT (2018) Desktop-Stereolithography 3D-Printing of a Poly(dimethylsiloxane)-Based Material with Sylgard-184. Properties Adv Mater 30:1–7 https://doi.org/10.1002/adma.201800001

  9. Coenjarts CA, Ober CK (2004) Two-photon three-dimensional microfabrication of poly(dimethylsiloxane) elastomers. Chem Mater 16:5556–5558 https://doi.org/10.1021/cm048717z

  10. Rekštytė S, Malinauskas M, Juodkazis S (2013) Three-dimensional laser micro-sculpturing of silicone: towards bio-compatible scaffolds. Opt Express 21:17028 https://doi.org/10.1364/oe.21.017028

  11. Porter DA, Davis N, Krueger PS (2020) Additive manufacturing by material extrusion with medical grade silicone elastomers and IR laser curing. Rapid Prototyp J 26:145–155 https://doi.org/10.1108/RPJ-10-2018-0279

  12. Lub J, Hikmet RAM (2016) Silicone mixture containing acrylates for inkjet and dispenser 3D printing. Patent WO 134972 A1

  13. Kenney JA, Zhu B (2020) 3D printing method utilizing a photocurable silicone composition. Patent US 10155884 B2

  14. Park JJ, Lee EC (2020) Photocurable polysiloxane composition for 3d printing, and dental mold comprising same. Patent US 2020 0123326 A1

  15. Yang X, Jones A, Zhang J, et al (2020) Additive manufacturing of polymer derived ceramics. Adv Powder Metall Part Mater - 2019 Proc 2019 Int Conf Powder Metall Part Mater 351:716–725

  16. Folch A, Bhattacharjee N, Parra C (2020) PDMS resin for stereolithographic 3D-printing of PDMS. Patent US 0071525 A1

  17. Uysal E, Çakir M, Ekİcİ B (2019) Synthesizing UV Curable Silicon Acrylate Resins for SLA Type 3D Printers and Characterization of Mechanical , Thermal and Morphological Properties. JoCREST 5:47–56. https://doi.org/10.26579/jocrest-5.1.5

  18. Woods R, Feldbacher S, Zidar D (2013) Development and characterization of optoelectronic circuit boards produced by two-photon polymerization using a polysiloxane containing acrylate functional groups. Appl Opt 52:388–393 https://doi.org/10.1364/AO.52.000388

  19. Kim HK, Ju HT, Hong JW (2003) Characterization of UV-cured polyester acrylate films containing acrylate functional polydimethylsiloxane. Eur Polym J 39:2235–2241 https://doi.org/10.1016/S0014-3057(03)00133-2

  20. Davidson RS, Ellis R, Tudor S, Wilkinson SA (1992) The photopolymerization of acrylates and methacrylates containing silicon. Polymer (Guildf) 33:3031–3036 https://doi.org/10.1016/0032-3861(92)90091-A

  21. Yang J, Vitale A, Bongiovanni R, Nie J (2015) Synthesis and characterization of siloxane photopolymers used for microfluidic devices. New J Chem 39:2532–2540 https://doi.org/10.1039/c4nj01773k

  22. Zhang D, Xiao J, Guo Q, Yang J (2019) 3D-printed highly porous and reusable chitosan monoliths for Cu(II) removal. J Mater Sci 54:6728–6741 https://doi.org/10.1007/s10853-019-03332-y

  23. Lapomarda A, De Acutis A, Chiesa I (2020) Pectin-GPTMS-Based Biomaterial: Toward a Sustainable Bioprinting of 3D scaffolds for Tissue Engineering Application. Biomacromol 21:319–327 https://doi.org/10.1021/acs.biomac.9b01332

  24. Putzien S, Louis E, Nuyken O (2012) UV curing of epoxy functional hybrid silicones. J Appl Polym Sci 126:1188–1197 https://doi.org/10.1002/app.36864

  25. Jang M, Crivello JV (2003) Synthesis and cationic photopolymerization of epoxy-functional siloxane monomers and oligomers. J Polym Sci Part A Polym Chem 41:3056–3073 https://doi.org/10.1002/pola.10890

  26. Jia L, Yue Y, Wang D, Frances J-M (2019) Curable Silicone Composition. Patent WO 2019/232778 Al

  27. Crivello JV, Mao Z (1997) Synthesis of Novel Multifunctional Siloxane Oligomers Using Sol-Gel Techniques and Their Photoinitiated Cationic Polymerization. Chem Mater 9: 1554–1561 https://doi.org/10.1021/cm960591l

  28. Cardiano P, Sergi S, Lazzari M, Piraino P (2002) Epoxy-silica polymers as restoration materials. Polymer (Guildf) 43:6635–6640 https://doi.org/10.1016/S0032-3861(02)00677-8

  29. Crivello JV, Bi D (1994) The synthesis and cationic polymerization of multifunctional silicon-containing epoxy monomers and oligomers. J Polym Sci Part A Polym Chem 32:683–697 https://doi.org/10.1002/pola.1994.080320407

  30. Woods R, Feldbacher S, Langer G  (2011) Epoxy silicone based matrix materials for two-photon patterning of optical waveguides. Polymer (Guildf) 52:3031–3037 https://doi.org/10.1016/j.polymer.2011.04.052

  31. Quan H, Zhang T, Xu H (2020) Photo-curing 3D printing technique and its challenges. Bioact Mater 5:110–115 https://doi.org/10.1016/j.bioactmat.2019.12.003

  32. Stansbury JW, Dickens SH (2001) Determination of double bond conversion in dental resins by near infrared spectroscopy. Dent Mater 17:71–79 https://doi.org/10.1016/S0109-5641(00)00062-2

  33. Šapić IM, Bistričić L, Volovšek V (2009) DFT study of molecular structure and vibrations of 3-glycidoxypropyltrimethoxysilane. Spectrochim Acta Part A Mol Biomol Spectrosc 72:833–840 https://doi.org/10.1016/j.saa.2008.11.032

  34. Hamdani S, Longuet C, Perrin D (2009) Flame retardancy of silicone-based materials. Polym Degrad Stab 94:465–495 https://doi.org/10.1016/j.polymdegradstab.2008.11.019

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Funding

The work that focused on the silicone rubbers preparation and assessment of their properties was supported by the Russian Science Foundation (project 20–19-00256). Physicochemical measurements were performed at the Center for Optical and Laser Materials Research and the Center for Magnetic Resonance (all belonging to Saint Petersburg State University).

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Correspondence to Regina M. Islamova or Alina A. Manshina.

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Talianov, P.M., Rzhevskii, S.S., Pankin, D.V. et al. Structural features of functional polysiloxanes radical and ionic photo-curing for laser printing applications. J Polym Res 28, 37 (2021). https://doi.org/10.1007/s10965-021-02409-0

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