Pendant propargyloxy-functionalized aromatic (co)polycarbonates: synthesis, thermal crosslinking and chemical modification

References

• Brunelle, D. J.; Korn, M. R. Advances in Polycarbonates; American Chemical Society: Washington, DC, 2005.
   Google Scholar
• Moeller, M.; Matyjaszewski, K. Polymer Science: A Comprehensive Reference, 1st ed.; Elsevier B.V.: Amsterdam, The Netherlands, 2012.
   Google Scholar
• Schmidhauser, J.; Sybert, P. D. Nonbisphenol a Polycarbonates. J. Macromol. Sci. – Polym. Rev. 2001, 41, 325–367. DOI: 10.1081/MC-100107861.
   Web of Science ®Google Scholar
• Koelewijn, S. F.; Van Den Bosch, S.; Renders, T.; Schutyser, W.; Lagrain, B.; Smet, M.; Thomas, J.; Dehaen, W.; Van Puyvelde, P.; Witters, H.; Sels, B. F. Sustainable Bisphenols from Renewable Softwood Lignin Feedstock for Polycarbonates and Cyanate Ester Resins. Green Chem. 2017, 19, 2561–2570. DOI: 10.1039/C7GC00776K.
   Web of Science ®Google Scholar
• Harvey, B. G.; Guenthner, A. J.; Meylemans, H. A.; Haines, S. R. L.; Lamison, K. R.; Groshens, T. J.; Cambrea, L. R.; Davis, M. C.; Lai, W. W. Renewable Thermosetting Resins and Thermoplastics from Vanillin. Green Chem. 2015, 17, 1249–1258. DOI: 10.1039/C4GC01825G.
   Web of Science ®Google Scholar
• De Leo, V.; Casiello, M.; Deluca, G.; Cotugno, P.; Catucci, L.; Nacci, A.; Fusco, C.; D’Accolti, L. Concerning Synthesis of New Biobased Polycarbonates with Curcumin in Replacement of Bisphenol a and Recycled Diphenyl Carbonate as Example of Circular Economy. Polymers 2021, 13, 361. DOI: 10.3390/polym13030361.
   PubMed Web of Science ®Google Scholar
• Harvey, B. G.; Guenthner, A. J.; Koontz, T. A.; Storch, P. J.; Reams, J. T.; Groshens, T. J. Sustainable Hydrophobic Thermosetting Resins and Polycarbonates from Turpentine. Green Chem. 2016, 18, 2416–2423. DOI: 10.1039/C5GC02893K.
   Web of Science ®Google Scholar
• Hoeks, T.; Medhi, M.; Mir, A. A.; Alli, A.; Shaikh, G. Synthesis and Characterization of Photo- Crosslinkable Copoly (Carbonate-Ester) S (PCE) Derived from P-Hydroxy Cinnamic Acid (P-HCA) and Bisphenol A (BPA). J. Macromol. Sci. Part A 2019, 56, 812–820. DOI: 10.1080/10601325.2019.1607752.
   Web of Science ®Google Scholar
• Ichake, A. B.; Nagane, S. S.; Jadhav, U. A.; Torris, A.; Grau, E.; Cramail, H.; Wadgaonkar, P. P. Synthesis and Characterization of Partially Biobased Aromatic (Co)Polycarbonates Containing Biphenylene Units and Pendant Pentadecyl Chains. Macro Chem. Phys. 2022, 223, 2100449. DOI: 10.1002/macp.202100449.
   Web of Science ®Google Scholar
• Yuan, L.; He, L.; Zhang, X.; Liu, J.; Zhang, D.; Udayabhaskararao, T.; Yang, F.; Zhao, Y.; Wang, D.; Zhao, H. Dynamic Postpolymerization Modification Based on Knoevenagel Adducts of Meldrum’s Acid. Macromolecules 2022, 55, 6102–6109. DOI: 10.1021/acs.macromol.2c00422.
   Web of Science ®Google Scholar
• Espeel, P.; Du Prez, F. E. Click”-Inspired Chemistry in Macromolecular Science: Matching Recent Progress and User Expectations. Macromolecules 2015, 48, 2–14. DOI: 10.1021/ma501386v.
   Web of Science ®Google Scholar
• Blasco, E.; Sims, M. B.; Goldmann, A. S.; Sumerlin, B. S.; Barner-Kowollik, C. Barner-Kowollik, C. 50th Anniversary Perspective: Polymer Functionalization. Macromolecules 2017, 50, 5215–5252. DOI: 10.1021/acs.macromol.7b00465.
   Web of Science ®Google Scholar
• Geng, Z.; Shin, J. J.; Xi, Y.; Hawker, C. J. Click Chemistry Strategies for the Accelerated Synthesis of Functional Macromolecules. J. Polym. Sci 2021, 59, 963–1042. DOI: 10.1002/pol.20210126.
   Web of Science ®Google Scholar
• Kuhire, S. S.; Talanikar, A. A.; Tawade, B. V.; Nagane, S. S.; Wadgaonkar, P. P. Partially Bio-Based Furyl-Functionalized Organosoluble Poly(Ether Ether Ketone)s. Polym. Int. 2021, 70, 1038–1047. DOI: 10.1002/pi.6160.
   Web of Science ®Google Scholar
• Mollah, M. S. I.; Seo, D. W.; Islam, M. M.; Lim, Y. D.; Cho, S. H.; Shin, K. M.; Kim, J. H.; Kim, W. G. Synthesis and Characterization of Grafted Silicone Polycarbonates. J. Macromol. Sci. Part A Pure Appl. Chem. 2011, 48, 400–408. DOI: 10.1080/10601325.2011.562735.
   Web of Science ®Google Scholar
• Xin, Y.; Sakamoto, J.; Van Der Vlies, A. J.; Hasegawa, U.; Uyama, H. Phase Separation Approach to a Reactive Polycarbonate Monolith for “Click” Modifications. Polymer 2015, 66, 52–57. DOI: 10.1016/j.polymer.2015.04.008.
   Web of Science ®Google Scholar
• Caldwell, J. R.; Jackson, W. J. Polycarbonates Cross-Linked by Aromatic Azides or Diazides. US3215667, November 2, 1965.
   Google Scholar
• Rosenberg, J. E.; Rome, D.; Morin, P.; Tooby, R.; Persson, D.; Lager, E. Cross-Linkable Aromatic Polycarbonate. EP2391666B1, August 28, 2013.
   Google Scholar
• Chan, J. W.; Shin, J.; Hoyle, C. E.; Bowman, C. N.; Lowe, A. B. Synthesis, Thiol-Yne “Click” Photopolymerization, and Physical Properties of Networks Derived from Novel Multifunctional Alkynes. Macromolecules 2010, 43, 4937–4942. DOI: 10.1021/ma1004452.
   Web of Science ®Google Scholar
• Hoogenboom, R. Thiol-Yne Chemistry: A Powerful Tool for Creating Highly Functional Materials. Angew. Chem. Int. Ed. Engl. 2010, 49, 3415–3417. DOI: 10.1002/anie.201000401.
   PubMed Web of Science ®Google Scholar
• Binder, W. H.; Sachsenhofer, R. Click” Chemistry in Polymer and Material Science: An Update. Macromol. Rapid Commun. 2008, 29, 952–981. DOI: 10.1002/marc.200800089.
   Web of Science ®Google Scholar
• Ma, L.; Lin, Y.; Tan, H.; Zheng, J.; Liu, F.; Zhang, G.; Liu, J.; Tang, T. Highly Efficient Synthesis and Characterization of Multiarm and Miktoarm Star-Long-Branched Polymers via Click Chemistry. RSC Adv. 2015, 5, 34466–34474. DOI: 10.1039/C5RA02168E.
   Web of Science ®Google Scholar
• Morgan, P. W. Linear Condensation Polymers from Phenolphthalein and Related Compounds. J. Polym. Sci. A Gen. Pap. 1964, 2, 4707–4707. DOI: 10.1002/pol.1964.100021037.
   Web of Science ®Google Scholar
• Schnell, H. Linear Aromatic Polyesters of Carbonic Acid. Ind. Eng. Chem. 1959, 51, 157–160. DOI: 10.1021/ie50590a038.
   Web of Science ®Google Scholar
• Boyles, D. A.; Filipova, T. S.; Bendler, J. T.; Longbrake, G.; Reams, J. Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units. Macromolecules 2005, 38, 3622–3629. DOI: 10.1021/ma048616m.
   Web of Science ®Google Scholar
• Kim, K. H.; Moon, J. Y.; Ha, D. H.; Park, D. W. Synthesis of Aromatic Polyesters Using Polymeric Catalysts Having Quaternary Ammonium Salt Groups. React. Kinet. Catal. Lett. 2002, 75, 385–395. DOI: 10.1023/A:1015223718354.
   Google Scholar
• Kamps, J. H.; Groote, R.; Baus, M.; Vermeulen, H.; Hoeks, T.; van der Heijden, R.; Sijbesma, R. P.; Heuts, J. P. A. Activated Carbonates: Enabling the Synthesis of Differentiated Polymers via Solution Carbonation. Eur. Polym. J. 2020, 135, 109901. DOI: 10.1016/j.eurpolymj.2020.109901.
   Web of Science ®Google Scholar
• Woo, B. G.; Choi, K. Y.; Song, K. H.; Lee, S. H. Melt Polymerization of Bisphenol-A and Diphenyl Carbonate in a Semibatch Reactor. J. Appl. Polym. Sci. 2001, 80, 1253–1266. DOI: 10.1002/app.1211.
   Web of Science ®Google Scholar
• Verma, S.; Maher, D. M.; Nagane, S. S.; Tawade, B. V.; Wadgaonkar, P. P. Thermally Crosslinkable and Chemically Modifiable Aromatic Polyesters Possessing Pendant Propargyloxy Groups. J. Polym. Sci. Part A Polym. Chem. 2019, 57, 588–597. DOI: 10.1002/pola.29297.
   Web of Science ®Google Scholar
• Sun, S. J.; Liao, Y. C.; Chang, T. C. Studies on the Synthesis and Properties of Thermotropic Liquid Crystalline Polycarbonates. VII. Liquid Crystalline Polycarbonates and Poly(ester-Carbonate)s Derived from Various Mesogenic Groups. J. Polym. Sci. A Polym. Chem. 2000, 38, 1852–1860. DOI: 10.1002/(SICI)1099-0518(20000515)38:10 < 1852::AID-POLA720 > 3.0.CO;2-J.
   Web of Science ®Google Scholar
• Marks, M. J.; Munjal, S.; Namhata, S.; Scott, D. C.; Bosscher, F.; De Letter, J. A.; Klumperman, B. Randomly Branched Bisphenol a Polycarbonates. I. Molecular Weight Distribution Modeling, Interfacial Synthesis, and Characterization. J. Polym. Sci. A Polym. Chem. 2000, 38, 560–570. DOI: 10.1002/(SICI)1099-0518(20000201)38:3 < 560::AID-POLA21 > 3.0.CO;2-N.
   Web of Science ®Google Scholar
• Maher, D. M.; Nagane, S. S.; Jadhav, U. A.; Salunkhe, P. H.; Tawade, B. V.; Wadgaonkar, P. P. A New Cardo Bisphenol Monomer Containing Pendant Azido Group and the Resulting Aromatic Polyesters. J. Polym. Sci. Part A: Polym. Chem. 2019, 57, 1516–1526. DOI: 10.1002/pola.29414.
   Web of Science ®Google Scholar
• Douglas, W. E.; Overend, A. S. Curing Reactions in Acetylene Terminated Resins-I. Uncatalyzed Cure of Arylpropargyl Ether Terminated Monomers. Eur. Polym. J. 1991, 27, 1279–1287. DOI: 10.1016/0014-3057(91)90066-W.
   Web of Science ®Google Scholar
• Kimura, K.; Nishichi, A.; Yamashita, Y. Synthesis of Thermally Crosslinkable Fluorine-Containing Poly(Arylene Ether Ketone)s - II. Propargyl Ether Terminated Poly(Arylene Ether Ketone)s. Polym. Adv. Technol. 2004, 15, 313–319. DOI: 10.1002/pat.476.
   Web of Science ®Google Scholar
• Prieto, S.; Galià, M.; Cádiz, V. Crosslinking of Poly(Epibromohydrin) Containing the Aryl Prop-2-Ynyl Ether Terminated Side Goup. Macromol. Chem. Phys. 1998, 199, 1291–1300. DOI: 10.1002/macp.1998.021990705.
   Web of Science ®Google Scholar
• Nair, C.; Bindu, R. L.; Krishnan, K.; Ninan, K. N. Ether Resins: Synthesis and Structure–Thermal Property Correlations. Eur. Polym. J. 1999, 35, 235–246. DOI: 10.1016/S0014-3057(98)00110-4.
   Web of Science ®Google Scholar
• Douglas, W. E.; Overend, A. S. Curing Reactions in Acetylene-Terminated Resins. Part 2.-Differential Scanning Calorimetric, Thermal Gravimetric and Thermomechanical Analytical Study of Catalysed Cure of an Aryl Prop-2-Ynyl Ether-Terminated Monomer. J. Mater. Chem. 1993, 3, 27–31. DOI: 10.1039/JM9930300027.
   Web of Science ®Google Scholar
• Holub, M. E. F. Curable Polycarbonate Compositions. US3770697A, November 6, 1973.
   Google Scholar
• Marks, M. J.; Newton, J.; Bales, S. E. Branching by Reactive End Groups. III. Synthesis, Branching, and Analysis Ofm-Ethynylphenol/p-T-Butylphenol-Coterminated Bisphenol a Polycarbonates. J. Polym. Sci. A Polym. Chem. 2000, 38, 2352–2358. DOI: 10.1002/1099-0518(20000701)38:13 < 2352::AID-POLA70 > 3.0.CO;2-K.
   Web of Science ®Google Scholar
• Glaser, C. Untersuchungen Über Einige Derivate Der Zimmtsäure. Ann. Chem. Pharm. 1870, 154, 137–171. DOI: 10.1002/jlac.18701540202.
   Google Scholar
• Sonogashira, K. Development of Pd–Cu Catalyzed Cross-Coupling of Terminal Acetylenes with sp2-Carbon Halides. J. Organomet. Chem 2002, 653, 46–49. DOI: 10.1016/S0022-328X(02)01158-0.
   Web of Science ®Google Scholar
• Weiss, H. M.; Touchette, K. M. Bromide Assisted Addition of Hydrogen Bromide to Alkynes and Allenes. J. Chem. Soc. Perkin Trans. 1998, 6, 1523–1528. DOI: 10.1039/a703569a.
   Google Scholar
• Duxbury, C. J.; Cummins, D.; Heise, A. Glaser Coupling of Polymers: Side-Reaction in Huisgens “‘Click ’” Coupling Reaction and Opportunity for Polymers with Focal Diacetylene Units in Combination with ATRP. J. Polym. Sci. Part A Polym. Chem. 2009, 47, 3795–3802. DOI: 10.1002/pola.
   Web of Science ®Google Scholar
• Brown, H. C.; Zweifel, G. The Hydroboration of Acetylenes-A Convenient Conversion of Internal Acetylenes to Cis Olefins of High Purity and of Terminal Acetylenes to Aldehydes. J. Am. Chem. Soc. 1959, 81, 1512–1512. DOI: 10.1021/ja01515a058.
   Web of Science ®Google Scholar
• Lowe, A. B. Thiol-Yne “Click” /Coupling Chemistry and Recent Applications in Polymer and Materials Synthesis and Modi Fi Cation. Polymer 2014, 55, 5517–5549. DOI: 10.1016/j.polymer.2014.08.015.
   Web of Science ®Google Scholar
• Arslan, M.; Pulido, B. A.; Nunes, S. P.; Yagci, Y. Functionalization of Poly(Oxindole Biphenylylene) Membranes by Photoinduced Thiol-Yne Click Chemistry. J. Memb. Sci. 2020, 598, 117673. DOI: 10.1016/j.memsci.2019.117673.
   Web of Science ®Google Scholar
• Arslan, M.; Bicak, T. C.; Pulido, B. A.; Nunes, S. P.; Yagci, Y. Post Modification of Acetylene Functional Poly(Oxindole Biphenylylene) by Photoinduced CuAAC. Eur. Polym. J. 2018, 100, 298–307. DOI: 10.1016/j.eurpolymj.2018.02.009.
   Web of Science ®Google Scholar
• Shen, L.; Cheng, J.; Zhang, J. Reworkable Adhesives: Healable and Fast Response at Ambient Environment Based on Anthracene-Based Thiol-Ene Networks. Eur. Polym. J. 2020, 137, 109927. DOI: 10.1016/j.eurpolymj.2020.109927.
   Web of Science ®Google Scholar
• Olofsson, K.; Malkoch, M.; Hult, A. Facile Synthesis of Dopa-Functional Polycarbonates via Thiol-Ene-Coupling Chemistry towards Self-Healing Gels. J. Polym. Sci. Part A: Polym. Chem. 2016, 54, 2370–2378. DOI: 10.1002/pola.28111.
   Web of Science ®Google Scholar