Soluble Polyamides and Polyimides Functionalized with Benzo‐15‐Crown‐5‐Pendant Groups

Maya, Eva M.; Lozano, Ángel E.; Campa, José G. de la; Abajo, Javier de

doi:10.1002/marc.200300092

Cited by 45 publications

(24 citation statements)

References 20 publications

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“…Furthermore, the polymerization of a diamine monomer containing a benzo-15-crown-5 moiety with different diacid dichlorides and dianhydrides under low-temperature polymerization conditions leads to soluble aromatic polyamides and polyimides. 11 However, the threading through the crown cavity has been proposed for gelation in polymers with higher membered crown ether ring moieties. [12][13][14] In principle, the gel, or physical network, could be attributed to the threading of cyclic polyamides or oligoamides by segments of another polymer chain during polymerization to yield polyrotaxanes or polycatenanes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of new aromatic polyamides bearing crown ethers and acyclic ethylene oxide units in the pendant structure. III. Benzo‐18‐crown‐6 systems and their open‐chain counterparts

Carpintero¹,

Schwarz²,

García³

et al. 2006

J. Polym. Sci. A Polym. Chem.

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We report the synthesis and characterization of 10 novel polyamides containing the benzo-18-crown-6 subunit and its dipodal counterpart, along with their properties, and a comparison with homologous polyamides bearing benzo-12-crown-4, benzo-15-crown-5, and the corresponding dipodal systems. The anomalous polymerization of some of the diacid monomers, that leads to insoluble gels under standard Yamazaki polymerization conditions, is described. The gel formation has been attributed to the threading of cyclic oligoamides with a growing polyamide chain to yield rotaxanes, polyrotaxanes, catenanes, or polycatenanes. Polyamide macrocycles have been characterized with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. A route to avoid gel formation, consisting of a lower initial monomer concentration, is also described, along with the polymer properties of the polyamides obtained, including the chemical characterization, mechanical behavior, water sorption, morphology, diffusion data, and permeability of membranes prepared with these polymers.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of new aromatic polyamides bearing crown ethers and acyclic ethylene oxide units in the pendant structure. III. Benzo‐18‐crown‐6 systems and their open‐chain counterparts

Carpintero¹,

Schwarz²,

García³

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…[1][2][3][4][5] However, with the quick development of high technology fields especially in microelectronic industry, common polyimides cannot meet the sharply increasing demands for polyimides with outstanding combined properties because of their shortcoming in processability owing to their insolubility in organic solvents and high melting temperature. 6,7 Thus, to utilize the thermal stability of polyimides for further applications and also to take advantage of other properties of polyimide such as high chain rigidity, packing density, and polar chain interactions, it will be desirable to synthesize soluble and/or melt-processable polyimides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel soluble pyridine‐containing polyimides based on 4‐phenyl‐2,6‐bis[4‐(4‐aminophenoxy)phenyl]‐pyridine and various aromatic dianhydrides

Wang

Gong

et al. 2007

J of Applied Polymer Sci

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A new kind of pyridine-containing aromatic diamine monomer, 4-phenyl-2,6-bis[4-(4-aminophenoxy)phenyl]-pyridine (PAPP), was successfully synthesized by a modified chichibabin reaction of benzaldehyde and a substituted acetophenone, 4-(4-nitrophenoxy)-acetophenone (NPAP), followed by a reduction of the resulting dinitro compound 4-phenyl-2,6-bis[4-(4-nitrophenoxy)phenyl]-pyridine (PNPP) with Pd/C and hydrazine monohydrate. The aromatic diamine was employed to synthesize a series of new pyridine-containing polyimides by polycondensation with various aromatic dianhydrides in Nmethy-2-pyrrolidone (NMP) via the conventional two-step method, i.e., ring-opening polycondensation forming the poly (amic acid)s and further thermal or chemical imidization forming polyimides. The inherent viscosities of the resulting polyimides were in the range of 0.79-1.13 dL/g, and most of them were soluble in common organic solvents such as N,N-dimethylacetamide (DMAc), NMP, and tetrahydrofuran (THF), etc. Meanwhile, strong and flexible polyimide films were obtained, which had good thermal stability, with the glass transition temperatures (T g ) of 268-3388C and the temperature at 5% weight loss of 521-5488C in air atmosphere, as well as outstanding mechanical properties with tensile strengths of 89.2-112.1 MPa and elongations at break of 9.5-15.4%. The polyimides also were found to possess low dielectric constants ranging from 2.53 to 3.11.

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“…[3][4] For this purpose many efforts on chemical modifications of polyimides have been done, such as introduction of flexible linkages in their backbone, or incorporation of bulky side groups which results in good solubility and processability of the polyimides. [5][6][7][8][9][10][11] Synthesis of poly(amide-imide)s (PAIs) by incorporating amide functionality at regular intervals in the polyimide main chain is also used. Replacement of polyimides by copolyimides such as poly(amide-imide)s (PAIs) may be useful to tackle the intractability of polyimides [12][13] and among them poly(amide-imide)s (PAIs) can improve the solubility.…”

Section: Introductionmentioning

confidence: 99%

New optically active and thermally stable poly(amide-imide)s containing N,N'-(Bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-alanine and aromatic diamines: synthesis and characterization

Faghihi¹,

Absalar²,

Hajibeygi³

2009

J. Braz. Chem. Soc.

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Cinco novas poliamidas-iminas (PAIs) oticamente ativas 6a-e foram preparadas pela reação de policondensação direta da N, N´-(biciclo[2,2,2]octa-7-eno-2,3,5,6-tetracarboxila)-bis-L-alanina 4 com várias diaminas aromáticas 5a-e usando solventes polares apróticos como a N-metil-2-pirrolidona (NMP). Neste procedimento, trifenil fosfito (TPP) e piridina foram usados como agentes de condensação para formar poliamidas-imidas através dos sais de N-fosfônio-piridina. Todos os polímeros foram obtidos com rendimentos quantitativos com uma viscosidade intrínseca entre 0,29-0,46 dL g -1 , sendo altamente solúveis em solventes polares apróticos como N,N-dimetil Five new optically active poly(amide-imide)s (PAIs) 6a-e were prepared by direct polycondensation reaction of the newly synthesized N,N´-(bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-alanine 4 with various aromatic diamines 5a-e using polar aprotic solvents such as N-methyl-2-pyrrolidone (NMP). In this technique triphenyl phosphite (TPP) and pyridine were used as condensing agents to form poly(amide-imide)s through the N-phosphonium salts of pyridine. All of the polymers were obtained in quantitative yields with inherent viscosities between 0.29-0.46 dL g -1 and were highly soluble in polar aprotic solvents such as N,N-dimethyl acetamide (DMAc), N,N-dimethyl formamide (DMF), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP) and solvents such as sulfuric acid. They were fully characterized by means of 1 H NMR, FTIR spectroscopy, elemental analyses, inherent viscosity, solubility test, specific rotation and thermal properties of these polymers were investigated using thermogravimetric analysis techniques (TGA and DTG).

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Soluble Polyamides and Polyimides Functionalized with Benzo‐15‐Crown‐5‐Pendant Groups

Cited by 45 publications

References 20 publications

Synthesis and characterization of new aromatic polyamides bearing crown ethers and acyclic ethylene oxide units in the pendant structure. III. Benzo‐18‐crown‐6 systems and their open‐chain counterparts

Synthesis and characterization of new aromatic polyamides bearing crown ethers and acyclic ethylene oxide units in the pendant structure. III. Benzo‐18‐crown‐6 systems and their open‐chain counterparts

Synthesis and characterization of novel soluble pyridine‐containing polyimides based on 4‐phenyl‐2,6‐bis[4‐(4‐aminophenoxy)phenyl]‐pyridine and various aromatic dianhydrides

New optically active and thermally stable poly(amide-imide)s containing N,N'-(Bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-alanine and aromatic diamines: synthesis and characterization

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