Synthesis of new soluble aromatic poly(amide imide)s from unsymmetrical extended diamine containing phthalazinone moiety

Cheng, Lin; Jian, Xi Gao

doi:10.1002/app.20084

Cited by 51 publications

(22 citation statements)

References 20 publications

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“…To develop easily processable high performance polymers, modifications that increase the solubility while maintaining the thermal stability are of particular interest. One of the successful approaches to increase solubility and processability of polyamides is by the introduction of flexible bonds, [5][6][7][8][9] unsymmetric and less symmetric such as meta-or ortho-linkages, [10][11][12] alicyclic, 13,14 and kinked structures. 15 Another approach employed to increase the solubility of rigid-rod polyamide is by incorporation of the nonlinear moieties such as a bulky noncoplanar groups in the polymer backbone.…”

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confidence: 99%

Synthesis and Properties of Novel Fluorinated Polyamides Based on Noncoplanar Sulfoxide Containing Aromatic Bis(ether amine)

Shockravi¹,

Abouzari‐Lotf

Javadi³

et al. 2009

Polym. J.

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A novel sulfoxide containing bis(ether amine) monomer, 2,2 0 -sulfoxide-bis[4-methyl(2-trifluoromethyl)4-aminophenoxy) phenyl ether] (M2), was synthesized from the halogen displacement of 2-chloro-5-nitrobenzotrifluoride with dibenzosulfoxide (DH) in the presence of potassium carbonate, followed by catalytic reduction of bis(ether nitro) intermediate with Zinc/Ammonium chloride. A series of organic-soluble poly(ether amide)s (PA1-7) bearing sulfoxide and electronwithdrawing trifluoromethyl group were synthesized from bis(ether amine) with various aromatic diacids (1-7) via a direct polycondensation with triphenyl phosphite and pyridine. The resulting polymers had inherent viscosities ranging from 0.35 to 0.90 dL g À1 at a concentration of 0.5 g/dL in N,N-dimethylacetamide (DMAc) solvent at 25 C. All the polymers showed outstanding solubility and could be easily dissolved in amide-type polar aprotic solvents (e.g., N-methyl-2-pyrrolidone (NMP), DMAc, and N,N-dimethylformamide) and even dissolved in less polar solvents (e.g., pyridine, and tetrahydrofuran). Also these polymers could be cast into flexible and tough films from DMAc solutions. The glass-transition temperatures of these poly(sulfoxide ether amide)s were recorded between 160-220 C. 10% weight loss temperatures were recorded in the range of 400-505 C in nitrogen and 380-480 C in air atmosphere.

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confidence: 99%

Synthesis and Properties of Novel Fluorinated Polyamides Based on Noncoplanar Sulfoxide Containing Aromatic Bis(ether amine)

Shockravi¹,

Abouzari‐Lotf

Javadi³

et al. 2009

Polym. J.

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“…41 The solubility of polymer is greatly enhanced by the incorporation of phosphine oxide moiety and further by bulky -CF 3 groups, biphenyl phosphorus moiety and more flexible ether group are especially effective for high solubility. 36 The -CF 3 groups in polymer, 5d increase its solubility in organic solvents relative to other polymers due to combination of steric and electronic effects.…”

Section: 3c Solubility Of Poly(amide-imide)s In Organic Solventsmentioning

confidence: 99%

Synthesis and characterization of heat-resistant and soluble poly(amide-imide)s from unsymmetrical dicarboxylic acid containing 2-(triphenyl phosphoranylidene) moiety and various aromatic diamines

Agrawal

Narula

2015

J Chem Sci

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An unsymmetrical and non-coplaner heterocyclic phosphorus containing dicarboxylic acid monomer, (DCA-3) is successfully synthesized with high purity. A series of novel aromatic poly(amide-imide)s having ether or/sulphur or/fluorine or/phosphorus containing phenyl moieties in their backbone are then prepared via a direct phosphorylation polycondensation of synthesized dicarboxylic acid with various aromatic diamines. Chemical structures of DCA-3 as well as resulting polymers are confirmed by FT-IR, NMR spectroscopic techniques and elemental analysis. These polymers are readily soluble in a variety of aprotic polar solvents such as NMP, DMSO, DMAc and DMF, etc. UV spectra showed that all poy(amide-imide)s films exhibit high optical transparency. In addition, the glass transition temperatures (T g ) of these polymers were determined by differential scanning calorimetry and found in the range 271-346 • C. Furthermore, thermogravimetric analysis of these polymers showed good thermal stability, 10% weight loss at temperature in excess of 538 • C and char yield at 700 • C in nitrogen ranging from 68 to 79%. From wide-angle X-ray diffraction experiments, all polymers showed amorphous behaviour.

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“…Polyimide has been commercially available possessing good mechanical, thermal, and oxidative stabilities [3]. A problem occurs in the processing, namely the insolubility [4] of common organic solvents due to the rigidity of their backbone, the strong hydrogen bonding in aromatic polyimide, and the charge transfer complex formation in aromatic polyimides [5]. One way to improve solubility of the polymer membrane is to introduce a sulfonated group to the polymer structure; a sulfonated group not only improves solubility but also increases the proton conductivity as the presence of the sulfonated groups increases the proton hopping area [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of sulfonated poly(aromatic imide-co-aliphatic imide) (S-coPI) membrane for direct methanol fuel cells

2014

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A novel polymer electrolyte membrane (PEM) based on sulfonated poly(aromatic imide-co-aliphatic imide) (S-coPI) is synthesized by the polycondensation of 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride (BPTDA) with 4,4 0 -diaminodiphenylmethane (DDM), 4,4 0 -diaminodiphenylmethane-3,3 0 -disulfonic acid disodium salt (S-DDM), and adipic acid dihydrazide (ADH). The ADH is utilized to increase the flexibility of the backbone structure due to its aliphatic structure. The sulfonation degree of S-coPI is controlled by varying the mole ratio of DDM, S-DDM, and ADH. The S-DDM containing two sulfonated groups is confirmed by 1 H-NMR. S-coPI membranes are characterized by FT-IR to identify the characteristic peaks of the sulfonated group at 1,298, 1,159, 1,098, and 1,065 cm -1 . Thermogravimetric analysis is used to investigate the thermal stability of S-coPI; it undergoes 2 steps in the degradation process, one at 320°C which represents the decomposition of the sulfonated group and one at 560°C which represents the polymer backbone degradation. The S-coPI-3, with the highest sulfonation degree, possesses proton conductivity value of about 1.16 9 10 -2 S cm -1 . The methanol permeability of the S-coPI films are in the range of 3.864 9 10 -8 -6.521 9 10 -8 cm 2 s -1 , about 26-40 times lower than that of Nafion 117.

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Synthesis of new soluble aromatic poly(amide imide)s from unsymmetrical extended diamine containing phthalazinone moiety

Cited by 51 publications

References 20 publications

Synthesis and Properties of Novel Fluorinated Polyamides Based on Noncoplanar Sulfoxide Containing Aromatic Bis(ether amine)

Synthesis and Properties of Novel Fluorinated Polyamides Based on Noncoplanar Sulfoxide Containing Aromatic Bis(ether amine)

Synthesis and characterization of heat-resistant and soluble poly(amide-imide)s from unsymmetrical dicarboxylic acid containing 2-(triphenyl phosphoranylidene) moiety and various aromatic diamines

Synthesis and characterization of sulfonated poly(aromatic imide-co-aliphatic imide) (S-coPI) membrane for direct methanol fuel cells

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