Synthesis and characterization of novel polyurethanes based on 1,3‐bis(hydroxymethyl) benzimidazolin‐2‐one and 1,3‐bis(hydroxymethyl) benzimidazolin‐2‐thione hard segments

Novel polyurethanes (PUs) based on 1,3‐bis(hydroxymethyl) benzimidazolin‐2‐one and 1,3‐bis(hydroxymethyl) benzimidazolin‐2‐thione as hard segments with two aromatic diisocyanates, viz., 4,4′‐diphenylmethane diisocyanate and toluene 2,4‐diisocyanate, were prepared. Polymer structures were established by Fourier transform infrared and nuclear magnetic resonance spectroscopy. Morphology of the PUs was studied by differential scanning calorimetry and thermogravimetry. All PUs contain domains of crystalline and amorphous structures as indicated by X‐ray diffraction experiments. Furthermore, polymers were insoluble in the majority of organic solvents and, hence, their solution characterization was not possible. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 98: 2236–2244, 2005     

Synthesis and characterization of 2‐oxazoline‐benzoxazine compound and its polymer

A novel 2‐oxazoline‐benzoxazine (POB) was synthesized with 2‐(hydroxylphenyl)‐2‐oxazoline, 1,3,5‐triphenylhexahydro‐1,3,5‐triazine and paraformaldehyde. The chemical structure of the monomer was confirmed by FTIR, ¹H‐NMR, ¹³C‐NMR, and MS. The curing behavior of the monomer was studied by DSC and FTIR, and the ring opening reaction of the monomer was found to occur from 187.5°C. The results of DMA and TGA demonstrated that the thermal properties of polymer for POB monomer (P‐m) are better than polymer for POB precursor (P‐p), because that the oligomer in benzoxazine precursor decreased the perfection of the polymer's network structure; it was also found that the thermal properties of P‐m and P‐p are much better than the common polybenzoxazine and the composite material of benzoxazine and 2‐oxazoline. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci , 2008.     

Synthesis and characterization of novel polyimides derived from 2‐amino‐5‐(4‐aminophenyl)‐thiazole

A new kind of aromatic unsymmetrical diamine monomer containing thiazole ring, 2‐amino‐5‐(4‐aminophenyl)‐thiazole (AAPT), was synthesized. A series of novel polyimides were prepared by polycondensation of AAPT with various aromatic dianhydrides by one‐step polyimidation process. The synthesized polyimides had inherent viscosity values of 0.36–0.69 dL/g and were easily dissolved in highly dipolar solvents. Meanwhile, strong and flexible polyimide films were obtained, which have good thermal and thermo‐oxidative stability with the glass transition temperatures (T_g) of 276.7–346.1°C, the temperature at 5% weight loss of 451–492°C in nitrogen and 422–440°C in air, as well as have outstanding mechanical properties with the tensile strengths of 94–122 MPa, elongations at breakage of 5–18%. These films also had dielectric constants of 3.12–3.38 at 10 MHz. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

New foamed plastic based on polyetherols obtained from 6‐aminouracil,ethylene carbonate,and propylene oxide

Polyetherols with 1,3‐pyrimidine ring including both oxyethylene and oxypropylene groups were obtained in reactions of 6‐aminouracil with ethylene carbonate and propylene oxide. The structure of the products was analyzed by spectral methods. Some physical properties of polyetherols were investigated. The polyetherols were used as polyol components to obtain polyurethane foams. Some properties of the foams such as apparent density, absorption of water, linear dimensions stability, thermal resistance, and compression strength were investigated. The foams obtained show an improved thermal stability. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Polyurethane foams with 1,3‐pyrimidine ring

Attempts of obtaining of polyurethane foams using polyetherols with 1,3‐pyrimidine ring (obtained in reactions of 6‐aminouracil with oxiranes) are reported. Properties of the foams are investigated, especially their thermal stability. The foams show an improved thermal stability up to 200°C for a long time. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Synthesis and properties of novel poly(benzimidazopyrrolone amide)s containing pyridine moieties

A series of new poly(benzimidazopyrrolone amide) (PPA) copolymers were synthesized by a two‐step procedure, which was the solution polycondensation of a novel pyridine‐containing tetraamine with various aromatic dianhydrides at a room temperature and cyclization of the resulting prepolymers at a high temperature, respectively. The resulting prepolymers from the solution polycondensation, that is, poly(amide amino acid)s (PAAAs), had inherent viscosities of 0.82–0.91 dL/g; then, tough and flexible PPA films could be successfully prepared by the casting of the PAAA solutions onto a glass substrate followed by thermal curing with a program temperature procedure up to 350°C. The obtained PPA films exhibited not only excellent thermal properties with onset decomposition temperatures in the range 502–521°C, glass‐transition temperatures in the range 299–337°C, and residual weight retentions at 700°C in air of 29.1–34.8% but also good mechanical properties with tensile strengths of 102.1–115.9 MPa and elongations at break of 6.8–7.4%. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

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

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 N‐methy‐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 268–338°C and the temperature at 5% weight loss of 521–548°C 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. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 212–219, 2007     

Synthesis of 3′,4′‐disubstituted terthiophenes. Characterization and electropolymerization. I. 3′,4′‐dibromo‐2,2′:5′,2″‐terthiophene in photovoltaic display

Recent studies on conducting polymers have demonstrated that polymers of 3‐substituted thiophene produce very stable compounds. Although this kind of substitution improves the regularity, structural defects still exist. To overcome this drawback, the polymerization of 3,4‐disubstituted thiophene is proposed as a convenient way of synthesizing regular, highly conjugated conductive polymers. Our interest is thus focused on the synthesis of tetra‐substituted thiophene derivatives, their polymerization, electrochemical properties, spectral characteristics, oxidizing potential, and the feasibility of photocells development. In this article, we report the synthesis and characterization of 3′,4′‐dibromo‐2,2′:5′,2″‐terthiophene which, as such or modified, may be a good starting product for obtaining new monomers of 3′,4′‐disubstituted terthiophenes, that would allow the effect of the substituents on the properties of the respective polymers to be studied. In addition, the monomer was electropolymerized and the resulting deposit was electrochemically and morphologically characterized. Two conclusions were drawn: first, more uniform and homogeneous layers than those of polythiophene are obtained; second, the thin layers of the polymer, electron acceptors, absorb in the visible. Finally, photocells were assembled to investigate their photovoltaic effect. Although the so prepared solar cells showed some photovoltaic effect, the yield was low.© 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 5314–5321, 2006     

Syntheses and characterization of polystyrene‐supported 2,5‐dimercapto‐1,3,4‐thiodiazole and its sorption behavior for Pd(II), Pt(IV), and Au(III)

A type of chelating resin crosslinking polystyrene‐supported 2,5‐dimercapto‐1,3,4‐thiodiazole (also called bismuththiol I, BMT), containing sulfur and nitrogen atoms, was prepared. The structure of PS‐BMT was confirmed by FTIR, elemental analysis, and X‐ray photoelectron spectroscopy (XPS). Adsorption of Pd(II), Pt(IV), and Au(III) was investigated. The capacity of PS‐BMT to adsorb Pd(II) and Pt(IV) was 0.190 and 0.033 mmol/g, respectively. The adsorption dynamics of Pd(II) showed that adsorption was controlled by liquid film diffusion and that the apparent activation energy, E_a, was 32.67 kJ/mol. The Langmuir model was better than the Freundlich model in describing the isothermal process of Pd(II), and the ΔG, ΔH, and ΔS values calculated were ?0.33 kJ/mol, 26.29 kJ/mol, and 87.95 J mol^?1 K^?1, respectively. The mechanisms of adsorption of Pd(II), Pt(IV), and Au(III) were confirmed by XPS. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 631–637, 2006     

Polyetherols obtained from 6‐aminouracil and ethylene carbonate

The reactions of 6‐aminouracil with ethylene carbonate were investigated. Potassium carbonate or 1,4‐diazabicyclo[2.2.2]octane was used as a catalyst. An excess of ethylene carbonate was applied in the syntheses. In this way, polyetherols with 1,3‐pyrimidine rings in their structure were prepared. The structure of the products was analyzed with infrared, proton nuclear magnetic resonance, and matrix‐assisted laser desorption/ionization time‐of‐flight techniques. Some physical properties and the thermal stability of the prepared polyetherols were investigated. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007     

Aromatic polyimides from m‐phenylene diamines containing pendant groups: Synthesis and characterization

Two diamine monomers, 4‐[4‐(1‐methyl‐1‐phenylethyl)phenoxy]‐1,3‐diamino benzene and 4‐{4‐[(4‐methylphenyl)sulfonyl]phenoxy}‐1,3‐diamino benzene, were synthesized, and both diamines were polycondensed with three commercial dianhydrides to obtain aromatic polyimides containing pendant groups. The polyimides were characterized by solubility tests, viscosity measurements, IR, ¹H‐NMR, and ¹³C‐NMR spectroscopy, X‐ray diffraction studies, and thermogravimetric analysis. The polyimides had inherent viscosities of 0.33–0.58 dL/g in m‐cresol at 30 ± 0.1°C. All the polyimides were amorphous and were soluble in solvents such as N,N‐dimethylacetamide, N‐methyl‐2‐pyrrolidone, N,N‐dimethylformamide, and m‐cresol. Thermogravimetric analysis of the polyimides indicated no weight loss below 410°C under a nitrogen atmosphere. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 1377–1384, 2005     

Synthesis and applications of oligoetherols with perhydro‐1,3,5‐triazine ring and boron

A new method of preparation of oligoetherols containing perhydro‐1,3,5‐triazine rings and boron atoms is presented. The oligoetherols were obtained in the reaction of 1,3,5‐tris(2‐hydroxyethyl) isocyanurate with boric acid followed by reaction with alkylene carbonates. The structure and physical properties of the products render them good candidate for preparing the polyurethane foams. The foams were obtained and their properties were compared with those synthesized from isocyanuric acid and alkylene carbonates. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Synthesis and properties of novel poly(coumarin‐amide)s

A novel monomer diacid, 6,6′‐methylenebis(2‐oxo‐2H‐chromene‐3‐carboxylic acid), was synthesized and used in a direct polycondensation reaction with various aromatic diamines in N‐methyl‐2‐pyrrolidone solution containing dissolved LiCl and CaCl₂, using triphenyl phosphite and pyridine as condensing agents to give a series of novel heteroaromatic polyamides containing photosensitive coumarin groups in the main chain. Polyamide properties were investigated by DSC, TGA, GPC, wide‐angle X‐ray scattering, viscosity, and solubility measurements. The copolymers were soluble in aprotic polar solvents, and their inherent viscosities varied between 0.49 and 0.78 dL g^?1. The weight‐average and number‐average molecular weights, measured by gel permeation chromatography, were 27,500–43,900 g mol^?1 and 46,500–66,300 g mol^?1, respectively, and polydispersities in the range of 1.48–1.69. The aromatic polyamides showed glass‐transition temperatures (T_g) ranging from 283 to 329°C and good thermal properties evidenced by no significant weight loss up to 380°C and 10% weight loss recorded above 425°C in air. All the polyamides exhibited an amorphous nature as evidenced by wide‐angle X‐ray diffraction and demonstrated a film forming capability. Water uptake values up to 3.35% were observed at 65% relative humidity. These polymers exhibited strong UV‐vis absorption maxima at 357–369 nm in DMSO solution, and no discernible photoluminescence maxima were detected by exciting with 365 nm. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis and characterization of alternate copolymers constructed by 1,3‐bis(diphenylsilyl)‐2,2,4,4‐tetraphenylcyclodisilazane units with oligo‐dimethylsiloxane segments

1,3‐Dichloro‐1,1,3,3‐tetraphenyldisilazane (DCTPS) with 71.6% yield was synthesized by the reaction of hexaphenylcyclotrisilazane (HPCT) with Ph₂SiCl₂ catalyzed by dibutyltin dilaurate. A ring‐closure reaction of DCTPS was carried out with BuLi in xylene–hexane mixture solvent; 1,3‐bis(chlorodiphenylsilyl)‐2,2,4,4‐tetraphenyl‐cyclodisilazane (BcPTPC) with 73.2% yield was obtained. Hydrolysis of BcPTPC in ether–triethylamine solvent resulted in 71.9% yield of 1,3‐bis(diphenylhydroxysilyl)‐2,2,4,4‐tetraphenylcyclodisilazane (B_HPTPC). By condensation polymerization of B_HPTPC with α,ω‐bis(diethylamino)‐oligo‐dimethylsiloxane, a kind of alternate copolymer constructed by 1,3‐bis(diphenylsilyl)‐2,2,4,4‐tetraphenylcyclodisilazane units with oligo‐dimethylsiloxane segments [P(BPTPC‐alt‐ODMS)] was synthesized. BcPTPC, B_HPTPC as well as P(BPTPC‐alt‐ODMS) were characterized by ²⁹Si‐NMR spectra, FT‐IR spectra, and elemental analysis. DGA study shows that P(BPTPC‐alt‐ODMS)s are thermally stable. The thermal decomposition onsets of P(BPTPC‐alt‐ODMS)s are all above 520°C. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 1484–1490, 2005     

Synthesis and characterization of novel polyfuran/poly(2‐iodoaniline) conducting composite

The electrically conducting polyfuran/poly(2‐iodoaniline) (PFu/P2IAn) and P2IAn/PFu composites were prepared by chemical oxidative polymerization using polyfuran and poly(2‐iodoaniline) in HCl and CHCl₃ media. The conductivities of composites were determined as a function of the amount of guest polymer. It was found out that the conductivities of P2IAn/PFu composites increased 100‐fold, whereas the conductivities of PFu/P2IAn composites did not show a specific increase. The composite compositions were altered by varying guest polymer feed ratios during preparation. Generally, the electrical conductivities of P2IAn/PFu composites increased with increasing the amount of PFu. Homopolymers and composites were further characterized thermally, employing thermogravimetry (TGA) and morphologically employing scanning electron microscopy (SEM). Further evidences concerning the polymer structures were obtained by FTIR and UV‐vis spectroscopies and magnetic susceptibility measurements. TGA results revealed that PFu/P2IAn among the homopolymers (PFu and P2IAn) and P2IAn/PFu composite have the highest thermal stability. The composites synthesized varying the host and the guest polymer order have different conductivities, morphological structures, and thermal properties. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 2823–2830, 2003     

Synthesis of chemically modified chitosan with 2,5‐dimercapto‐1,3,4‐thiodiazole and its adsorption abilities for Au(III), Pd(II), and Pt(IV)

A new chemically modified chitosan hydrogel with 2,5‐dimercapto‐1,3,4‐thiodiazole (CTS‐DMTD) has been synthesized. The structure of CTS‐DMTD was confirmed by elemental analysis and FTIR. It was found that adsorption capacities were significantly affected by the pH of solution, with optimum pH values of 3.0 for Au(III), 2.0 for Pd(II) and Pt(IV). The saturated adsorption capacities were 198.5 mg/g for Au(III), 16.2 and 13.8 mg/g for Pd(II) and Pt(IV), respectively. Langmuir and Freundlich isotherm adsorption models were applied to analyze the experimental data. The results showed that adsorption isotherms of Pd(II) and Pt(IV) could be well described by the Langmuir equation. The adsorption kinetic investigations indicated that the kinetic data correlated well with the pseudo‐second‐order model. The recovery experimental data showed that CTS‐DMTD had a higher affinity toward Au(III), Pd(II), and Pt(IV) in the coexistence system containing Cu(II), Fe(III), Cd(II), Ni(II), Mg(II), and Zn(II). The studies of desorption were carried out using various reagents and the optimum effect was obtained using thiourea. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

New heteroaromatic polyazomethines containing naphthyridine moieties: Synthesis,characterization, and biological screening

A new series of heteroaromatic polyazomethines containing 1,8‐naphthyridine moieties in the polymer backbone were synthesized with a solution polycondensation technique. A new heteroaromatic monomer containing 1,8‐naphthyridine moieties (4‐ethoxy‐2,7‐dicarboxaldehyde‐1,8‐naphthyridine) was synthesized with an analogous synthetic sequence and confirmed by elemental and spectral data. The resulting polymers were characterized by elemental, spectral analyses, solubility and viscometry measurements. All the synthesized polyazomethines had better solubility in polar aportic solvents. The thermal properties of those polymers were evaluated by thermogravimetric analysis, differential thermogravimetry, and differential thermal analysis measurements and correlated to their structural units. All the polymers had nearly similar maximum polymer decomposition temperatures, which were in the range 557–577°C. A very large difference between the glass transitions (92–222°C) was observed. In addition, with gel permeation chromatography, the molecular weight determination of selected examples of those polymers was evaluated. The values of the average molecular weight for polyazomethines 7 _b and 7 _c were 34,914 and 24,859, respectively. On the other hand, the biological screening of all of the synthesized polyazomethines was performed in variety of bacteria and fungi. Most of the polyazomethines showed a significant influence against Gram‐negative bacteria. The minimum inhibitory concentration of the most active polymers was 0.05 mg/mL. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and characterization of new polyureas derived from 4‐(4′‐Methoxyphenyl)urazole

4‐(4′‐Methoxyphenyl)urazole (MPU) was prepared from 4‐methoxybenzoic acid in five steps. The reaction of monomer MPU with n‐isopropylisocyanate was performed at room temperature in N,N‐dimethylformamide solution, and the resulting bis‐urea derivative was obtained in high yield and was finally used as a model for polymerization reaction. The step‐growth polymerization reactions of monomer MPU with hexamethylene diioscyanate, isophorone diioscyanate, and toluene‐2,4‐diioscyanate were performed in N,N‐dimethylacetamide solution in the presence of pyridine as a catalyst. The resulting novel polyureas have an inherent viscosity (η_inh) in a range of 0.07–0.21 dL/g in DMF and sulfuric acid at 25°C. These polyureas were characterized by IR, ¹H‐NMR, elemental analysis, and TGA. Some physical properties and structural characterization of these novel polyureas are reported. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 1141–1146, 2002     

Synthesis and characterization of novel polyurethanes based on N1,N4‐bis[(4‐hydroxyphenyl)methylene]succinohydrazide hard segment

This article deals with the synthesis and characterization of novel polyurethanes (PUs) by the reaction between two aromatic diisocyanates (4,4′‐diphenylmethane diisocyanate and tolylene 2,4‐diisocyanate) and two aliphatic diisocyanates (isophorone diisocyanate and hexamethylene diisocyanate) with N¹,N⁴‐bis[(4‐hydroxyphenyl)methylene]succinohydrazide, which acted as hard segment. UV–vis, FTIR, ¹H NMR, ¹³C NMR, and DSC/TGA analytical technique has been used to determine the structural characterization and thermal properties of the hard segmented PUs. X‐ray diffraction revealed that PUs contained semicrystalline and amorphous regions that varied depending upon the nature of the backbone structures. PUs were soluble in polar aprotic solvents. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Solid‐state synthesis and characterization of polyaniline/nano‐TiO2 composite

Polyaniline/nano‐TiO₂ composites with the content of nano‐TiO₂ varying from 6.2 wt % to 24.1 wt % were prepared by using solid‐state synthesis method at room temperature. The structure and morphology of the composites were characterized by the Fourier transform infrared (FTIR) spectra, ultraviolet‐visible (UV–vis) absorption spectra, X‐ray diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The electrochemical performances of the composites were investigated by galvanostatic charge–discharge measurement, cyclic voltammetry (CV), and electrochemical impedance spectroscopy (EIS). The results from FTIR and UV–vis spectra showed that the composites displayed higher oxidation and doping degree than pure PANI. The XRD and morphological studies revealed that the inclusion of nano‐TiO₂ particles hampered the crystallization of PANI chains in composites, and the composites exhibited mixed particles from free PANI particles and the nano‐TiO₂ entrapped PANI particles. The galvanostatic charge–discharge measurements indicated that the PANI/nano‐TiO₂ composites had higher specific capacitances than PANI. The composite with 6.2 wt % TiO₂ had the highest specific capacitance among the composites. The further electrochemical tests on the composite electrode with 6.2 wt % TiO₂ showed that the composite displayed an ideal capacitive behavior and good rate ability. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012