High‐molecular‐weight fluorinated aromatic polyformal containing a phthalazinone moiety

Li, Xiuhua; Hay, Allan S.

doi:10.1002/pola.21763

Cited by 7 publications

(4 citation statements)

References 12 publications

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“…Therefore, the phthalazinone monomer is used for preparing high-performance engineering plastics. [17][18][19] In the present work, a new series of poly(arylene ether ether ketone ketone) copolymers containing the phthalazinone unit (SPAEEKK-D) were prepared from commercially available monomers BFBB, DHNS, and DHPZ. Although there are a number of studies on PEM materials containing the phthalazinone unit, we are not aware of any that have attempted to compare its effect on polymer properties in comparison with other monomer units.…”

Section: Introductionmentioning

confidence: 99%

Comparative effect of phthalazinone units in sulfonated poly(arylene ether ether ketone ketone) copolymers as proton exchange membrane materials

Kim¹,

Guiver²

2007

J. Polym. Sci. A Polym. Chem.

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A new series of aromatic poly(arylene ether ether ketone ketone) copolymers containing pendant sulfonic acid groups (SPAEEKK-D) were synthesized from commercially available monomers 1,3-bis(4-fluorobenzoyl)-benzene, sodium 6,7-dihydroxy-2-naphthalenesulfonate, and 4-(4-hydroxyphenyl)-2,3-phthalazin-1-one (DHPZ). Structure-property relationships of the phthalazinone SPAEEKK-D series poly(arylene ether ether ketone ketone) copolymer were compared with copolymers SPAEEKK-B and SPAEEKK-H containing different diols such as 4,4 0 -biphenol and hydroquinone, respectively, prepared in our earlier work. Ion exchange capacity (IEC w , weight-based; IEC v , volume-based), thermal stabilities, swelling, proton and methanol transport properties of the membranes were investigated in relation to their structures and compared with those of perfluorinated ionomer (Nafion 117). The SPAEEKK-D membrane incorporating the phthalazinone monomer DHPZ showed relatively lower water uptake and methanol permeability compared with earlier SPAEEKK-B and SPAEEKK-H membranes incorporating biphenol and hydroquinone monomers, respectively. Inclusion of phthalazinone in the SPAEEKK-D copolymers led to lower water absorption, enabling increased proton exchange concentrations in the hydrated polymer matrix that resulted in more desirable membrane properties for future direct methanol fuel cell applications. The SPAEEKK-D membranes also showed improved mechanical and thermal properties and oxidative stability compared with the earlier SPAEEKK-B and -H membranes.

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Section: Introductionmentioning

confidence: 99%

Comparative effect of phthalazinone units in sulfonated poly(arylene ether ether ketone ketone) copolymers as proton exchange membrane materials

Kim¹,

Guiver²

2007

J. Polym. Sci. A Polym. Chem.

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“…Polyformals (or polyformaldehydes) also known as polyacetals define a polymer category that can be represented by the chemical structure drawn in Figure 1 where R is a divalent aliphatic sequence [ 1 , 2 , 3 ] or divalent aromatic specie [ 4 , 5 ] including halogenated derivative [ 4 , 6 , 7 , 8 , 9 ]. In the case of aromatic polyacetals, R can contain only one cycle (phenylene) and is eventually substituted as in the case of methylphenylene, dimethylphenylene, chlorophenylene [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Optimized Synthesis According to One-Step Process of a Biobased Thermoplastic Polyacetal Derived from Isosorbide

et al. 2016

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This paper describes both the synthesis and characterization of a biobased and non-aromatic polyacetal produced from the reaction between isosorbide and methylene chloride. The reaction was conducted in an aprotic dipolar and harmless solvent using a one-step, fast and economical procedure. The chemical composition of this polymer was investigated using Nuclear Magnetic Resonance and Fourier Transform Infra-Red spectroscopies. The molecular weights were examined by size exclusion chromatography and MALDI-TOF spectrometry. The synthesis conditions (concentration, mixing speed, solvent nature, stoichiometry, addition mode of one reactan) were found to strongly influence both polymer architecture and reaction yield. Under moderated stirring conditions, the polyacetal was characterized by a larger amount of macro-cycles. Inversely, under higher intensity mixing and with an excess of methylene chloride, it was mainly composed of linear chains. In this latter case, the polymeric material presented an amorphous morphology with a glass transition temperature (T g ) close to 55˝C. Its degradation temperature was evaluated to be close to 215˝C using thermogravimetry according to multi-ramp methodology. The chemical approach and the physicochemical properties are valuable in comparison with that characteristic of other isosorbide-based polyacetals.

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“…4 The rigid asymmetric phenyl-phthalazinone structures in the polymer main chains improve the solubility of the resulting polymers with maintaining excellent thermostability, high glass transition temperature and mechanical properties. [5][6][7][8][9][10][11] These high performance polymers have been widely used in industrial applications, such as optical wave guides lms, ultraltration and nanoltration membranes, and lithium-ion batteries functional lms, anion exchange membrane materials used for vanadium redox ow battery applications, dielectric energy storage thin lms, and proton exchange membrane materials for fuel cells. [12][13][14][15][16][17] On the other side, DHPZ can be used as a acceptor due to the C]N bond and lactam of the phthalazinone structure.…”

Section: Introductionmentioning

confidence: 99%

Donor–acceptor copolymers containing the phthalazinone–thiophene structure synthesized by classical nucleophilic aromatic polymerization

et al. 2015

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A series of new donor-acceptor copolymers based on a novel monomer containing phthalazinone and thiophene structures, were synthesized by classical nucleophilic displacement step polymerization reaction, and then were fully characterized. Their thermal, optical, electrochemical properties and quantum chemical calculations were investigated in detail. The comparisons between the linkage of ketone/di-ketone/sulfone groups and phenyl/naphthalene groups in the resulting polymer backbone were carried out to explore the relationship of the structure and the properties in the polymer system. The number average molecular weights of the resulting copolymers are 15 kDa-24 kDa. All of the copolymers are stable up to 441 C, and their 5% weight loss temperatures are higher than 489 C. Their optical band gap and HOMO energy levels vary from 2.36 eV to 2.76 eV and À5.16 eV to À5.51 eV, respectively. The soluble copolymers obtained exhibit blue-fluorescence. Their photoluminescence quantum yield ranges from 0.04 to 0.28 in N-methyl-2-pyrrolidone. These non-ether bond polymers may be potential candidates in photoelectric application. † Electronic supplementary information (ESI) available: 1 H-NMR and 13 C-NMR spectrum of M2 and polymers, MALDI-TOF, IR, DSC, CV and HPLC-MS spectrum of M2, DSC and CV curves of polymers, solubility table of monomers and copolymers in organic solvent. See Scheme 1 Synthetic route of poly(phthalazinone ether)s. Scheme 2 Synthesis of Di-NH capped monomers M1 and M2. Scheme 3 Synthetic route and structures of copolymers. 30446 | RSC Adv., 2015, 5, 30445-30455 This journal is

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High‐molecular‐weight fluorinated aromatic polyformal containing a phthalazinone moiety

Cited by 7 publications

References 12 publications

Comparative effect of phthalazinone units in sulfonated poly(arylene ether ether ketone ketone) copolymers as proton exchange membrane materials

Comparative effect of phthalazinone units in sulfonated poly(arylene ether ether ketone ketone) copolymers as proton exchange membrane materials

Optimized Synthesis According to One-Step Process of a Biobased Thermoplastic Polyacetal Derived from Isosorbide

Donor–acceptor copolymers containing the phthalazinone–thiophene structure synthesized by classical nucleophilic aromatic polymerization

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