Copolyarylates containing phthalazinone and cardo moieties: An attempt toward the balance between thermal resistance and solubility
A series of copolyarylates containing phthalazinone and cardo moieties are synthesized by interfacial polymerization of terephthaloyl dichloride with bisphenol monomers including 2,4‐(4‐hydroxyphenyl)‐2,3‐phthalazin‐1‐one, 9,9‐bis(4‐hydroxyphenyl) fluorene, and phenolphthalein. The intrinsic viscosi...
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| Published in: | Journal of polymer science (2020) Vol. 61; no. 22; pp. 2954 - 2964 |
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| Abstract | A series of copolyarylates containing phthalazinone and cardo moieties are synthesized by interfacial polymerization of terephthaloyl dichloride with bisphenol monomers including 2,4‐(4‐hydroxyphenyl)‐2,3‐phthalazin‐1‐one, 9,9‐bis(4‐hydroxyphenyl) fluorene, and phenolphthalein. The intrinsic viscosity and number average molecular weight of copolyarylates are in the range of 0.71–1.01 dL g
−1
and 16.3–28.4 kDa, respectively, indicating the formation of medium molecular weight copolymers. The effects of phthalazinone and cardo moieties on the solubility and thermal resistance of copolyarylates are discussed in detail. With only phthalazinone moieties, the polyarylate has high thermal resistance with the glass transition temperature (
T
g
) of 335 °C, but poor solubility. The introduction of cardo moieties enables the produced copolyarylates readily soluble in chloroform, 1,1,2,2‐tetrachloroethane, and
N
‐methyl‐2‐pyrrolidone, for they not only increase the free volume of intermolecular chains but also lead to a fractional reduction in the structural stiffness of copolymers. Although the decrease in structural stiffness is related to a decrease in
T
g
value, fortunately, the rigid cardo and phthalazinone moieties allow the thermal resistance of copolyarylate to reach the leading level among (co)polyarylates. In addition, the resulting copolyarylates have good tensile properties. These copolyarylates have important application prospects in the high thermal‐resistant material industry. |
|---|---|
| AbstractList | A series of copolyarylates containing phthalazinone and cardo moieties are synthesized by interfacial polymerization of terephthaloyl dichloride with bisphenol monomers including 2,4‐(4‐hydroxyphenyl)‐2,3‐phthalazin‐1‐one, 9,9‐bis(4‐hydroxyphenyl) fluorene, and phenolphthalein. The intrinsic viscosity and number average molecular weight of copolyarylates are in the range of 0.71–1.01 dL g
−1
and 16.3–28.4 kDa, respectively, indicating the formation of medium molecular weight copolymers. The effects of phthalazinone and cardo moieties on the solubility and thermal resistance of copolyarylates are discussed in detail. With only phthalazinone moieties, the polyarylate has high thermal resistance with the glass transition temperature (
T
g
) of 335 °C, but poor solubility. The introduction of cardo moieties enables the produced copolyarylates readily soluble in chloroform, 1,1,2,2‐tetrachloroethane, and
N
‐methyl‐2‐pyrrolidone, for they not only increase the free volume of intermolecular chains but also lead to a fractional reduction in the structural stiffness of copolymers. Although the decrease in structural stiffness is related to a decrease in
T
g
value, fortunately, the rigid cardo and phthalazinone moieties allow the thermal resistance of copolyarylate to reach the leading level among (co)polyarylates. In addition, the resulting copolyarylates have good tensile properties. These copolyarylates have important application prospects in the high thermal‐resistant material industry. A series of copolyarylates containing phthalazinone and cardo moieties are synthesized by interfacial polymerization of terephthaloyl dichloride with bisphenol monomers including 2,4‐(4‐hydroxyphenyl)‐2,3‐phthalazin‐1‐one, 9,9‐bis(4‐hydroxyphenyl) fluorene, and phenolphthalein. The intrinsic viscosity and number average molecular weight of copolyarylates are in the range of 0.71–1.01 dL g−1 and 16.3–28.4 kDa, respectively, indicating the formation of medium molecular weight copolymers. The effects of phthalazinone and cardo moieties on the solubility and thermal resistance of copolyarylates are discussed in detail. With only phthalazinone moieties, the polyarylate has high thermal resistance with the glass transition temperature (Tg) of 335 °C, but poor solubility. The introduction of cardo moieties enables the produced copolyarylates readily soluble in chloroform, 1,1,2,2‐tetrachloroethane, and N‐methyl‐2‐pyrrolidone, for they not only increase the free volume of intermolecular chains but also lead to a fractional reduction in the structural stiffness of copolymers. Although the decrease in structural stiffness is related to a decrease in Tg value, fortunately, the rigid cardo and phthalazinone moieties allow the thermal resistance of copolyarylate to reach the leading level among (co)polyarylates. In addition, the resulting copolyarylates have good tensile properties. These copolyarylates have important application prospects in the high thermal‐resistant material industry. |
| Author | Liu, Qian Li, Hailong Jian, Xigao Xu, Peiqi Zhang, Shouhai Che, Xuefu Lv, Fei Sun, Fanchen Feng, Huimei Wang, Danhui |
| Author_xml | – sequence: 1 givenname: Peiqi orcidid: 0000-0002-6273-3555 surname: Xu fullname: Xu, Peiqi organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 2 givenname: Qian surname: Liu fullname: Liu, Qian organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 3 givenname: Danhui surname: Wang fullname: Wang, Danhui organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 4 givenname: Hailong surname: Li fullname: Li, Hailong organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 5 givenname: Fei surname: Lv fullname: Lv, Fei organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 6 givenname: Huimei surname: Feng fullname: Feng, Huimei organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 7 givenname: Fanchen surname: Sun fullname: Sun, Fanchen organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 8 givenname: Xuefu surname: Che fullname: Che, Xuefu organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 9 givenname: Shouhai orcidid: 0000-0002-1533-7402 surname: Zhang fullname: Zhang, Shouhai organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China – sequence: 10 givenname: Xigao surname: Jian fullname: Jian, Xigao organization: State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Liaoning Province Technology Innovation Center of High Performance Resin Materials, Liaoning Key Laboratory of Polymer Science and Engineering, Dalian Key Laboratory of Membrane Materials and Processes School of Chemical Engineering, Dalian University of Technology Dalian People's Republic of China |
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| Cites_doi | 10.1016/S0032-3861(96)00924-X 10.1002/pola.22890 10.1177/0954008320912314 10.1016/j.orgel.2012.08.003 10.1016/j.seppur.2021.118739 10.1002/pol.1973.180111003 10.1007/s13233-017-5029-5 10.1177/0954008317734033 10.1039/b417402j 10.1002/chem.200400860 10.1038/nmat4638 10.1002/pi.5879 10.1007/s10965-011-9757-5 10.1016/j.memsci.2007.08.026 10.1177/09540083231155067 10.1002/app.32914 10.1016/j.memsci.2007.11.038 10.1039/b000793p 10.1016/j.cclet.2007.03.030 10.1016/j.reactfunctpolym.2016.05.005 10.1016/j.polymer.2019.122047 10.1016/j.eurpolymj.2004.04.014 10.1016/j.conbuildmat.2012.06.005 10.1016/j.memsci.2015.05.061 10.1016/j.jscs.2010.10.006 10.1016/j.eurpolymj.2004.03.006 10.1002/app.45704 10.1039/c3py20935k 10.1016/j.eurpolymj.2019.04.019 10.1039/B614214A 10.1002/app.32162 10.1007/s10965-011-9588-4 10.1016/j.polymer.2009.07.030 10.1016/j.eurpolymj.2020.110205 10.1021/acs.jpcb.0c09322 10.1016/j.memsci.2005.01.021 |
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| SubjectTerms | Chloroform Copolymers Dichlorides Glass transition temperature Heat transfer Molecular chains Molecular weight Phenolphthalein Polyarylates Solubility Stiffness Tensile properties Thermal resistance |
| Title | Copolyarylates containing phthalazinone and cardo moieties: An attempt toward the balance between thermal resistance and solubility |
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