Synthesis and thermal properties of novel silicone resins containing phthalonitrile groups

References

• Badshah, A.; Kessler, M. R.; Heng, Z.; Zaidi, J. H.; Hameed, S.; Hasan, A. An Efficient Approach to Prepare Ether and Amide-Based Self-Catalyzed Phthalonitrile Resins. Polym. Chem. 2013, 4, 3617. DOI: 10.1039/c3py00237c.
   Web of Science ®Google Scholar
• Dominguez, D. D.; Keller, T. M. Low-Melting Phthalonitrile Oligomers: Preparation, Polymerization and Polymer Properties. High Perform. Polym. 2016, 18, 283–304. DOI: 10.1177/0954008306060143.
   Google Scholar
• Laskoski, M.; Keller, T. M.; Qadri, S. B. Direct Conversion of Highly Aromatic Phthalonitrile Thermosetting Resins into Carbon Nanotube Containing Solids. Polymer. 2007, 48, 7484–7489. DOI: 10.1016/j.polymer.2007.11.003.
   Web of Science ®Google Scholar
• Yu, G.; Liu, C.; Zhou, H.; Wang, J.; Lin, E.; Jian, X. Synthesis and Characterization of Soluble Copoly(Arylene Ether Sulfone Phenyl-s-Triazine)s Containing Phthalazinone Moieties in the Main Chain. Polymer. 2009, 50, 4520–4528. DOI: 10.1016/j.polymer.2009.07.030.
   Web of Science ®Google Scholar
• Nar, I.; Gül, A.; Sivaev, I. B.; Hamuryudan, E. Cobaltacarborane Functionalized Phthalocyanines: Synthesis, Photophysical, Electrochemical and Spectroelectrochemical Properties. Synth. Met. 2015, 210, 376–385. DOI: 10.1016/j.synthmet.2015.10.021.
   Web of Science ®Google Scholar
• Wang, A-r.; Dayo, A. Q.; Zu, L-w.; Xu, Y-l.; Lv, D.; Song, S.; Tang, T.; Liu, W-b.; Wang, J.; Gao, B-c Bio-Based Phthalonitrile Compounds: Synthesis, Curing Behavior, Thermomechanical and Thermal Properties. React. Funct. Polym. 2018, 127, 1–9. DOI: 10.1016/j.reactfunctpolym.2018.03.017.
   Web of Science ®Google Scholar
• Zhao, F.; Liu, R.; Yu, X.; Naito, K.; Qu, X.; Zhang, Q. A High Temperature Polymer of Phthalonitrile‐Substituted Phosphazene with Low Melting Point and Good Thermal Stability. J. Appl. Polym. Sci. 2015, 132, 132. DOI: 10.1002/app.42606.
   Web of Science ®Google Scholar
• Guo, H.; Chen, Z.; Zhang, J.; Yang, X.; Zhao, R.; Liu, X. Self-Promoted Curing Phthalonitrile with High Glass Transition Temperature for Advanced Composites. J. Polym. Res. 2012, 19, 19. DOI: 10.1007/s10965-012-9918-1.
   Web of Science ®Google Scholar
• Laskoski, M.; Clarke, J. S.; Neal, A.; Harvey, B. G.; Ricks‐Laskoski, H. L.; Hervey, W. J.; Daftary, M. N.; Shepherd, A. R.; Keller, T. M. Sustainable High‐Temperature Phthalonitrile Resins Derived from Resveratrol and Dihydroresveratrol. ChemistrySelect 2016, 1, 3423–3427. DOI: 10.1002/slct.201600304.
   Web of Science ®Google Scholar
• Li, Q.; Zhang, S.; Ye, J.; Liu, X. Multiple Catalytic Polymerization of Phthalonitrile Resin Bearing Benzoxazine Moiety: Greatly Reduced Curing Temperature. Eur. Polym. J. 2022, 180, 111472. DOI: 10.1016/j.eurpolymj.2022.111472.
   Web of Science ®Google Scholar
• Cao, G. P.; Chen, W. J.; Wei, J. J.; Li, W. T.; Liu, X. B. Synthesis and Characterization of a Novel Bisphthalonitrile Containing Benzoxazine. eXPRESS Polym. Lett. 2007, 1, 512–518. DOI: 10.3144/expresspolymlett.2007.73.
   Web of Science ®Google Scholar
• Du, R.; Li, W.; Liu, X. Synthesis and Thermal Properties of Bisphthalonitriles Containing Aromatic Ether Nitrile Linkages. Polym. Degrad. Stab. 2009, 94, 2178–2183. DOI: 10.1016/j.polymdegradstab.2009.09.006.
   Web of Science ®Google Scholar
• Sheng, L.; Zeng, J.; Xing, S.; Yin, C.; Yang, J.; Yang, Y.; Xiao, J. A New Resin with Improved Processability and Thermal Stability. High Perform. Polym. 2016, 29, 13–25. DOI: 10.1177/0954008315626806.
   Web of Science ®Google Scholar
• Yang, X.; Lei, Y.; Zhong, J.; Zhao, R.; Liu, X. Preparation and Thermal Properties of Novel Phthalonitrile Oligomer Containing Biphenyl Ethernitrile/Bisphthalonitrile Blends. J. Appl. Polym. Sci. 2010, 119, 882–887. DOI: 10.1002/app.32783.
   Web of Science ®Google Scholar
• Zhai, Q.; Wu, X.; Zhao, S.; Zhou, C. Curing Kinetics Study by FTIR Spectroscopy and Properties Analysis of Methyl Silicone Resin Membrane. Silicon. 2020, 12, 2761–2768. DOI: 10.1007/s12633-019-00369-1.
   Web of Science ®Google Scholar
• Bajpai, P.; Bajpai, M. Development of a High Performance Hybrid Epoxy Silicone Resin for Coatings. Pigm. Resin Technol. 2010, 39, 96–100. DOI: 10.1108/03699421011028680.
   Web of Science ®Google Scholar
• Chen, L.; Chen, G. H.; Lu, L. Piezoresistive Behavior Study on Finger‐Sensing Silicone Rubber/Graphite Nanosheet Nanocomposites. Adv. Funct. Mater. 2007, 17, 898–904. DOI: 10.1002/adfm.200600519.
   Web of Science ®Google Scholar
• Huang, W.; Zhang, Y.; Yu, Y.; Yuan, Y. Studies on UV‐Stable Silicone–Epoxy Resins. J. Appl. Polym. Sci. 2007, 104, 3954–3959. DOI: 10.1002/app.26188.
   Web of Science ®Google Scholar
• Ma, S.; Liu, W.; Hu, C.; Wang, Z.; Tang, C. Toughening of Epoxy Resin System Using a Novel Dendritic Polysiloxane. Macromol. Res. 2010, 18, 392–398. DOI: 10.1007/s13233-010-0408-1.
   Web of Science ®Google Scholar
• Özgümüş, S.; İyim, T. B.; Acar, I.; Küçükoğlu, E. Synthesis of Novel Silicone Modified Acrylic Resins and Their Film Properties. Polym. Adv. Techs. 2007, 18, 213–219. DOI: 10.1002/pat.857.
   Web of Science ®Google Scholar
• Pan, Z.; Zhu, S.; Zhu, L.; Kang, Y.; Huang, B. Synthesis of High Refractive Index Epoxy Modified Methyl Phenyl Silicone Resin and Amine Phenyl Silicone Resin for LEDs Packaging. Silicon. 2019, 12, 1379–1389. DOI: 10.1007/s12633-019-00231-4.
   Web of Science ®Google Scholar
• Wu, C.; Li, W.; Gao, D.; Jia, M. Study of Resistance of Silicone Resin to Heat and Irradiation. Polym. Plast. Technol. Eng. 2009, 48, 1094–1100. DOI: 10.1080/03602550903147213.
   Web of Science ®Google Scholar
• Wu, C.-B.; Jin, Y.-H.; Li, W.; Gao, D.-H.; Jia, M.-Q. Synthesis and Characterization of a Silicone Resin with Silphenylene Units in Si–O–Si Backbones II. High Perform. Polym. 2010, 22, 959–973. DOI: 10.1177/0954008309347660.
   Web of Science ®Google Scholar
• Xiang, H.; Ge, J.; Cheng, S.; Han, H.; Cui, S. Synthesis and Characterization of Titania/MQ Silicone Resin Hybrid Nanocomposite via Sol–Gel Process. J. Sol Gel Sci. Technol. 2011, 59, 635–639. DOI: 10.1007/s10971-011-2538-0.
   Web of Science ®Google Scholar
• Xu, Y.; Long, J.; Zhang, R.; Du, Y.; Guan, S.; Wang, Y.; Huang, L.; Wei, H.; Liu, L.; Huang, Y. Greatly Improving Thermal Stability of Silicone Resins by Modification with POSS. Polym. Degrad. Stab. 2020, 174, 109082. DOI: 10.1016/j.polymdegradstab.2020.109082.
   Web of Science ®Google Scholar
• Kızılcan, N.; Akar, A. Modification of Cyclohexanone–Formaldehyde Resins with Silicone Tegomers. J. Appl. Polym. Sci. 2005, 98, 97–101. DOI: 10.1002/app.22044.
   Web of Science ®Google Scholar
• Wu, Z.; Shen, L. Y.; Tong, W.; Xia, F.; Zhang, Y. Q. Preparation and Properties Research of Modified Silicone Resin. J. Test. Eval. 2017, 45, 1535–1542. DOI: 10.1520/JTE20160127.
   Web of Science ®Google Scholar
• Zhu, Q.; Wang, Z.; Zeng, H.; Yang, T.; Wang, X. Effects of Graphene on Various Properties and Applications of Silicone Rubber and Silicone Resin. Compos. A Appl. Sci. Manuf. 2021, 142, 106240. DOI: 10.1016/j.compositesa.2020.106240.
   Web of Science ®Google Scholar
• Li, C.; Ma, Z.; Zhang, X.; Fan, H.; Wan, J. Silicone-Modified Phenolic Resin: Relationships between Molecular Structure and Curing Behavior. Thermochim. Acta. 2016, 639, 53–65. DOI: 10.1016/j.tca.2016.07.011.
   Web of Science ®Google Scholar
• Li, S.; Han, Y.; Chen, F.; Luo, Z.; Li, H.; Zhao, T. The Effect of Structure on Thermal Stability and Anti-oxidation Mechanism of Silicone Modified Phenolic Resin. Polym. Degrad. Stab. 2016, 124, 68–76. DOI: 10.1016/j.polymdegradstab.2015.12.010.
   Web of Science ®Google Scholar
• Mejía, M. C.; Palacio, J.; Murillo, E. A. Comb-Shaped Silicone-Alkyd Resins with High Solid Content. Prog. Org. Coat. 2017, 105, 336–341. DOI: 10.1016/j.porgcoat.2017.02.002.
   Web of Science ®Google Scholar
• Murillo, E. A.; López, B. L.; Brostow, W. Thermal, Hydrolytic, Anticorrosive, and Tribological Properties of Alkyd‐Silicone Hyperbranched Resins with High Solid Content. J. Appl. Polym. Sci. 2011, 124, 3591–3599. DOI: 10.1002/app.34611.
   Web of Science ®Google Scholar
• Xiong, G.; Kang, P.; Zhang, J.; Li, B.; Yang, J.; Chen, G.; Zhou, Z.; Li, Q. Improved Adhesion, Heat Resistance, Anticorrosion Properties of Epoxy Resins/POSS/Methyl Phenyl Silicone Coatings. Prog. Org. Coat. 2019, 135, 454–464. DOI: 10.1016/j.porgcoat.2019.06.017.
   Web of Science ®Google Scholar
• Yan, L.; Zhang, B.; Wang, Y.; Zhou, C.; Li, R.; Luo, W.; Chen, Y.; Zou, H.; Liang, M. The Improvement of Thermal Stability and Adhesion of Silicone Rubber Composites Modified by Phenolic Epoxy Resin. J. Macromol. Sci. A. 2019, 56, 506–512. DOI: 10.1080/10601325.2019.1584858.
   Web of Science ®Google Scholar
• Zhang, H.; Yan, Z.; Yang, Z.; Mu, Q.; Peng, D.; Zhao, H. Synthesis, Curing and Thermal Properties of the Low Melting Point Phthalonitrile Resins Containing Glycidyl Groups. Polym. Bull. 2022, 80, 725–738. DOI: 10.1007/s00289-021-04037-6.
   Web of Science ®Google Scholar
• Liu, Q.; Bao, X.; Deng, S.; Cai, X. The Investigation of Methyl Phenyl Silicone Resin/Epoxy Resin Using Epoxy-Polysiloxane as Compatibilizer. J. Therm Anal. Calorim. 2014, 118, 247–254. DOI: 10.1007/s10973-014-4017-7.
   Web of Science ®Google Scholar
• Bershtein, V.; Fainleib, A.; Yakushev, P.; Kirilenko, D.; Gusakova, K.; Markina, D.; Melnychuk, O.; Ryzhov, V. High Temperature Phthalonitrile Nanocomposites with Silicon Based Nanoparticles of Different Nature and Surface Modification: Structure, Dynamics, Properties. Polymer. 2019, 165, 39–54. DOI: 10.1016/j.polymer.2019.01.020.
   Web of Science ®Google Scholar
• Ren, D.; Li, K.; Chen, L.; Chen, S.; Han, M.; Xu, M.; Liu, X. Modification on Glass Fiber Surface and Their Improved Properties of Fiber-Reinforced Composites via Enhanced Interfacial Properties. Compos. B Eng. 2019, 177, 107419. DOI: 10.1016/j.compositesb.2019.107419.
   Web of Science ®Google Scholar
• Zhao, X.; Lei, Y.; Zhao, R.; Zhong, J.; Liu, X. Preparation and Properties of Halogen‐Free Flame‐Retarded Phthalonitrile–Epoxy Blends. J. Appl. Polym. Sci. 2011, 123, 3580–3586. DOI: 10.1002/app.34877.
   Web of Science ®Google Scholar
• Jing, X.; Zhao, Y.; Wen, H.; Xu, Z. Interactions between Low-Density Polyethylene (LDPE) and Polypropylene (PP) during the Mild Cracking of Polyolefin Mixtures in a Closed-Batch Reactor. Energy Fuels. 2013, 27, 5841–5851. DOI: 10.1021/ef401376m.
   Web of Science ®Google Scholar
• Zhu, B.; Wu, Y.; Reese, H. H.; Katsoulis, D. E.; McGarry, F. J. Silicone‐Organic Resin Hybrid Matrix Composites. Macro Mater. Eng. 2006, 291, 1052–1060. DOI: 10.1002/mame.200600042.
   Web of Science ®Google Scholar
• Jia, P.; Liu, H.; Wang, Y.; Cai, X. A Novel Epoxy-Functionalized Hyperbranched Polysiloxane (HPSi) Endowing Methyl Phenyl Silicone Resin (Si603)/Epoxy Systems with Enhanced Compatibility and Fire Retardancy Performance. RSC Adv. 2015, 5, 97413–97421. DOI: 10.1039/C5RA18399E.
   Web of Science ®Google Scholar