Novel polyarylates containing phthalazinone moieties (PAR-PH) were synthesized and characterized by co-solvent interfacial polymerization based on 4-(4′-hydroxyphenyl)-2,3-phthalazin-1-one (DHPZ) and isophthaloyl chloride (IPC). Effects of inorganic bases, monomer concentration, phase transfer catalysts and co-solvents on the interfacial polymerization reaction were investigated. When the organic phase solvent was cyclohexane with 3% butanone and 18-crown-6 was the phase transfer catalyst, PAR-PH achieved a maximum intrinsic viscosity (ηint) up to 0.52 dL/g. For some organic phase solvents of alkanes and chlorinated hydrocarbons, the addition of co-solvents increased the ηint of the polymer. PAR-PH exhibit excellent thermal resistance due to the introduction of rigid twisted phthalazinone moieties into the polymer main chains, with glass transition temperature (Tg) of 275°C. The 5% thermal weight loss temperature of PAR-PH was 463°C in N2 and residual mass ratios at 800°C of 52.0%, demonstrating excellent thermal stability.
LuHLiDZhangY, et al.Design of low dielectric constant and high transparent polyarylate containing spiral ring. Polymer2021; 228: 123948.
2.
WangZLiuYWangB, et al. Study on the synthesis of soluble copolymer polyarylate from asymmetric bisphenol A derivative (2,2‐bis(4‐hydroxyphenyl)butane/9,9‐bis(4‐hydroxyphenyl)fluorene) monomer. J Appl Polym Sci2023; 140(28): e54044.
3.
XuPLiuQWangD, et al.Copolyarylates containing phthalazinone and cardo moieties: an attempt toward the balance between thermal resistance and solubility. J Polym Sci2023; 61(22): 2954–2964.
4.
ZhangYYanGYangJ, et al. Design of polyarylates containing tert‐butyl cyclohexyl bulky side group with high transparency and low dielectric properties. J Appl Polym Sci2023; 140(25): e53975.
5.
ZhangYYanGZhangG, et al.Synthesis of high transparency polyarylates containing cyclohexane group. Polymer2020; 186: 122047.
6.
LiuPZengLYeG, et al. Bisphenol A-based co-polyarylates: synthesis, properties and thermal decomposition mechanism. J Polym Res2013; 20(10): 279–288.
7.
LiuPWuTShiM, et al.Synthesis and characterization of readily soluble polyarylates derived from either 1,1-bis(4-hydroxyphenyl)-1-phenylethane or tetramethylbisphenol A and aromatic diacid chlorides. J Appl Polym Sci2011; 119(4): 1923–1930.
8.
YangCHsiaoS. Preparation and properties of brominated poly(arylcarboxylate)s via interfacial polycondensation. J Polym Sci, Polym Chem Ed1990; 28(4): 871–886.
9.
WaghmarePBPathakPDeshmukhSA, et al.Synthesis and characterization of copolyarylates using tin octoate as a catalyst. J Appl Polym Sci2006; 101(1): 70–77.
10.
ShingteRDChatterjeeDTawadeBV, et al.Aromatic polyesters containing cardo perhydrocumyl cyclohexylidene groups: synthesis, characterization and gas permeation study. J Macromol Sci2019; 56(2): 136–145.
11.
ChamkureYKSharmaRK. New organosoluble polyarylates containing pendent fluorene units: synthesis, characterization and thermal behaviour. J Polym Res2019; 26(1): 17–29.
12.
ZhangYLeiZYanG, et al.Syntheses and properties of novel polyarylates with ethyl units as a side group. Mater Today Commun2021; 28: 102643.
13.
LathaGMurugavelSC. Synthesis and characterization of cardo poly(ether-ester)s containing 1,1-bis (4-hydroxyphenyl) cyclohexane in the main chain. Polym Bull2016; 73(11): 3237–3253.
14.
PengCWuJLiuJ, et al.Synthesis and optical properties of new fluorinated second-order nonlinear optical copolymers: an attempt toward the balance between solubility and long-term alignment stability. Polym Chem2013; 4(9): 2703.
WangZHuJWangB, et al.Synthesis and properties of copolyarylates containing phenol red units. J Appl Polym Sci2022; 140(7): 53465.
17.
HonkhambePNAvadhaniCVWadgaonkarPP, et al.Synthesis and characterization of new aromatic polyesters containing biphenyl side groups. J Appl Polym Sci2007; 106(5): 3105–3110.
18.
HonkhambePNBiyaniMVBhairamadgiNS, et al.Synthesis and characterization of new aromatic polyesters containing pendent naphthyl units. J Appl Polym Sci2010; 117(5): 2545–2552.
19.
RahmatpourA. Synthesis and characterization of new aliphatic polyesters containing methanodinaphtho[1,3]dioxocin part. J Appl Polym Sci2011; 120(6): 3357–3362.
20.
GuanXNieHWangH, et al.High-solubility aromatic polyesters with fluorene and phthalein groups: synthesis and property. High Perform Polym2020; 32(8): 933–944.
21.
GuanXNieHWangH, et al.High‐performance soluble copolyarylate based on phenolphthalein: synthesis, characterization and properties. Polym Int2019; 68(10): 1729–1738.
22.
WangZLiuYWangB, et al.Synthesis and properties of novel block-structured polyarylates containing fluorene: a two-step interface polymerization. New J Chem2024; 48(23): 10497–10506.
23.
WangJLiaoGLiuC, et al.Poly(ether imide)s derived from phthalazinone‐containing dianhydrides. J Polym Sci, Polym Chem Ed2004; 42(23): 6089–6097.
24.
LiuCZhangSWangM, et al.Synthesis and characterization of poly(ether amide)s containing bisphthalazinone and ether linkages. Chin Chem Lett2005; 16(4): 437–439.
25.
LiuQZhangSWangZ, et al.Poly(aryl ether ketone ketone)s containing diphenyl-biphthalazin-dione moieties with excellent thermo-mechanical performance and solubility. Eur Polym J2021; 143: 110205.
26.
XuPZhangSLiuQ, et al.Polyarylates containing phthalazinone moieties with excellent thermal resistance. High Perform Polym2023; 35(6): 571–580.
27.
WangTZhangSLiuQ, et al.Synthesis of copoly(aryl ester)s containing phthalazinone moieties by interfacial polymerization. Mat Sci Eng R2019; 33: 495–498.
28.
GhoshAKJeongBHHuangXF, et al.Impacts of reaction and curing conditions on polyamide composite reverse osmosis membrane properties. J Membr Sci2008; 311(1-2): 34–45.
29.
HailemariamRHChoiJDamtieMM, et al.Enhancing performances of polyamide thin film composite membranes via co-solvent assisted interfacial polymerization. Desalination2022; 524: 115481.
30.
MansourpanahYMadaeniSSRahimpourA. Fabrication and development of interfacial polymerized thin-film composite nanofiltration membrane using different surfactants in organic phase; study of morphology and performance. J Membr Sci2009; 343(1-2): 219–228.
31.
AbubshaitSAKassabRRAl-ShehriAH, et al.Synthesis and reactions of some novel 4-biphenyl-4-(2H)-phthalazin-1-one derivatives with an expected antimicrobial activity. J Saudi Chem Soc2011; 15(1): 59–65.
32.
HuQLiDLiuS, et al.Effects of alkali on the polyester membranes based on cyclic polyphenols for nanofiltration. Desalination2022; 533: 115774.
33.
WuXChenTDongG, et al.A critical review on polyamide and polyesteramide nanofiltration membranes: emerging monomeric structures and interfacial polymerization strategies. Desalination2024; 577: 117379.
34.
YuanSZhangGZhuJ, et al.Design and fabrication of nanofiltration membranes based on intrinsic porous monomer resorcin[4]arene. Desalination2021; 500: 114861.
35.
ZhangHXieFZhaoZ, et al.Novel poly(ester amide) membranes with tunable crosslinked structures for nanofiltration. ACS Appl Mater Interfaces2022; 14(8): 10782–10792.
36.
ZhengJLiuYZhuJ, et al.Sugar-based membranes for nanofiltration. J Membr Sci2021; 619: 118786.
37.
ChehardoliGBahmaniA. The role of crown ethers in drug delivery. Supramol Chem2019; 31(4): 221–238.
38.
LeeJWangRBaeTH. A comprehensive understanding of co-solvent effects on interfacial polymerization: interaction with trimesoyl chloride. J Membr Sci2019; 583: 70–80.
39.
WangYChangHJiangS, et al.An efficient co-solvent tailoring interfacial polymerization for nanofiltration: enhanced selectivity and mechanism. J Membr Sci2023; 677: 121615.
40.
ZhangJLiuQLiZ, et al.Novel soluble N-heterocyclic poly(aryl ether ketone)s containing pendant biphenyl groups performing excellent thermal and mechanical performance. Polymer2024; 309: 127425.
41.
LiZLiuQZhuoL, et al.A poly(aryl ether sulfone) containing bis-phthalazinone with high thermal resistance. ACS Appl Polym Mater2024; 6(14): 8505–8513.
42.
RahulDSDeepshikhaCBhausahebVT, et al.Aromatic polyesters containing cardo perhydrocumyl cyclohexylidene groups: synthesis, characterization and gas permeation study. J Macromol Sci2019; 56(2): 136–145.
43.
SamadhanSNSachinSKUdayAJ, et al.Design and synthesis of aromatic polyesters bearing pendant clickable maleimide groups. J Polym Sci, Polym Chem Ed2019; 57: 630–640.
44.
SavitaVDeepakMMSamadhanSN, et al.Thermally crosslinkable and chemically modifiable aromatic polyesters possessing pendant propargyloxy groups. J Polym Sci, Polym Chem Ed2019; 57: 588–597.
45.
KnijnenbergAWeiserESStClairTL, et al.Synthesis and characterization of aryl ethynyl terminated liquid crystalline oligomers and their cured polymers. Macromolecules2006; 39: 6936–6943.
46.
JiaxinLYangWTaoP, et al.Self-generation of a nanofibrous structure enables facile preparation and processing of a liquid crystalline polymeric composite with intrinsic flame retardancy. ACS Appl Mater Interfaces2024; 16: 34229–34239.
