Synthesis of all-aromatic polyamides containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety

Jian, Xi Gao; Cheng, Lin

doi:10.1002/(sici)1099-0518(19990601)37:11<1565::aid-pola1>3.0.co;2-j

Cited by 27 publications

(4 citation statements)

References 20 publications

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“…Poly((1,2‐dihydro‐1‐oxo( 2H )‐phthalazine‐2,4‐diyl)‐1,4‐phenyleneoxy‐1,4‐phenylenesulfonyl‐1,4‐phenylene), the first phthalazinone‐containing polymer, was published in 1993 . Since that time many phthalazinone‐containing high‐performance polymers, such as poly(phthalazinone ether)s, polyamides, polyimides, and polyformal with good solubility and excellent thermal stability have been synthesized. These high‐performance polymers may have promising applications in passive optical waveguides, ultrafiltration and nanofiltration membranes, and functional membranes in the energy field, such as membranes for lithium‐ion batteries, anion exchange membrane materials for vanadium redox flow battery applications, thin films for dielectric energy storage, and proton exchange membrane materials for fuel cells …”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB‐type monomers

Gao

Long

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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Four different fluorinated methyl‐ and phenyl‐substituted 4‐(4‐hydroxyphenyl)‐2‐(pentafluorophenyl)‐phthalazin‐1(2H)‐ones, AB‐type phthalazinone monomers, have been successfully synthesized by nucleophilic addition–elimination reactions of methyl‐ and phenyl‐substituted 2‐((4‐hydroxy)benzoyl)benzoic acid with 1‐(pentafluorophenyl)hydrazine. Under mild reaction conditions, the AB‐type monomers underwent self‐condensation polymerization reactions successfully and gave fluorinated poly(phthalazinone ether)s with high molecular weights. Detailed structural characterization of the AB‐type monomers and fluorinated polymers was determined by 1H NMR, 19F NMR, FTIR, and GPC. The solubility, thermal properties, mechanical properties, water contact angles, and optical absorption of the polymers were evaluated. The polymers had high Tgs varying from 337 to 349 °C and decomposition temperatures (Td, 25 wt %) above 409 °C. Tough, flexible films were cast from THF and chloroform solutions. The films showed excellent tensile strengths ranging from 70 to 85 MPa with good hydrophobicities with water contact angles higher than 95.5 °C. The polymers had absorption edges below 340 nm and very low absorbance per cm at higher wavelengths 500–2500 nm. These results indicate that the polymers are promising as high performance materials, for example, membranes and hydrophobic materials. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1761–1770

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB‐type monomers

Gao

Long

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…In previous articles, we have described the synthesis of a series of poly(aromatic ether amide)s containing phthalazinone (DHPZ) moiety in the main chain [14][15][16]. The diamines and dicarboxylic acids derived from the DHPZ structure contain both twisted, non-coplanar architectures and flexible ether linkages.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Novel Aromatic Copolyamides Derived from 2-(4-carboxyphenyl)-4-[3-phenyl-4-(4-carboxyphenoxyl) phenyl]-phthalazinone

Liu¹,

Qin²,

Liu³

et al. 2006

High Performance Polymers

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A series of four novel aromatic copolyamides were synthesized by the direct polycondensation of 2-(4-carboxyphenyl)-4-[3-phenyl-4-(4-carboxyphenoxyl)phenyl]-phthalazinone (1) and terephthalic acid (TPA) with some commercial diamines. The inherent viscosities of the polyamides were between 0.91 and 2.77 dL g 11 . All the copolyamides showed an amorphous nature as evidenced by wide-angle X-ray diffraction. Introduction of the non-coplanar phthalazinone segments into the polymer main chains remarkably improved the solubility of aromatic copolyamides. Most of the copolymers were soluble in aprotic polar solvents, such as N-methyl-pyrrolidone (NMP), N,N-dimethylacetamide, and dimethylsulfoxide. These aromatic copolyamides showed high thermal properties associated with the glass transition temperatures (T g ) in the range of 261-307 2 C and 10% weight loss temperatures in N 2 over 481 2 C. Moreover, the T g values of the copolyamides increased with the increasing ratio of phthalazinone moiety in the main chain. Some polymer films cast from NMP solution had tensile strengths up to 244.4 MPa, initial moduli up to 5.08 GPa, and elongation at break values up to 9.9%.

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“…2 We have prepared the aromatic diamine and polyamides containing phthalazinone moiety. [3][4][5] The unique structural feature of the diamines lies in nonsymmetrical and kink non-coplanar conformation of monomer 1. Of particular interests is to investigate the effect of the non-symmetrical and kink non-coplanar but still rigid monomer functionality on the properties of the polymers.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of New Aromatic Polyamides Based on 1,2-Dihydro-2-(4-carboxylphenyl)-4-[4-(4-carboxylphenoxy)-3-methylphenyl]phthalazin-1-one

Cheng¹,

Ying

Yang

et al. 2005

Chin. J. Chem.

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A new monomer diacid, 1,2-dihydro-2-(4-carboxylphenyl)-4-[4-(4-carboxylphenoxy)-3-methylphenyl]phthalazin-1-one (3), was synthesized through the aromatic nucleophilic substitution reaction of a readily available unsymmetrical phthalazinone 1 bisphenol-like with p-chlorobenzonitrile in the presence of potassium carbonate in N,N-dimethylacetamide and alkaline hydrolysis. The diacid could be directly polymerized with various aromatic diamines 4a-4e using triphenyl phosphite and pyridine as condensing agents to give five new aromatic poly(ether amide)s 5a-5e containing the kink non-coplanar heterocyclic units with inherent viscosities of 1.30-1.54 dL/g. The polymers were readily soluble in a variety of solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), dimethylsulfoxide (DMSO), N-methyl-2-pyrrolidinone (NMP), and even in m-cresol and pyridine (Py). The transparent, flexible and tough films could be formed by solution casting. The glass transition temperatures T g were in the range of 286-317 ℃.

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Synthesis of all-aromatic polyamides containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety

Cited by 27 publications

References 20 publications

Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB‐type monomers

Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB‐type monomers

Synthesis and Properties of Novel Aromatic Copolyamides Derived from 2-(4-carboxyphenyl)-4-[3-phenyl-4-(4-carboxyphenoxyl) phenyl]-phthalazinone

Facile Synthesis of New Aromatic Polyamides Based on 1,2-Dihydro-2-(4-carboxylphenyl)-4-[4-(4-carboxylphenoxy)-3-methylphenyl]phthalazin-1-one

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