Preparation and characterization of new photoactive polyamides containing 4‐(4‐dimethylaminophenyl)urazole units

4‐(4‐dimethylaminophenyl)‐1,2,4‐triazolidine‐3,5‐dione ( DAPTD ) was prepared from 4‐dimethylaminobenzoic acid in five steps. The compound DAPTD was reacted with excess acetyl chloride in N,N‐dimethylacetamide (DMAc) solution and gave 1,2‐bisacetyl‐4‐[4‐(dimethylaminophenyl)]‐1,2,4‐triazolidine‐3,5‐dione as a model compound. Solution polycondensation reactions of monomer with succinyl chloride (SucC), suberoyl chloride (SubC), and sebacoyl chloride (SebC) were performed under conventional solution polymerization techniques in the presence of triethylamine and pyridine as a catalyst in N‐methylpyrrolidone (NMP) and led to the formation of novel aliphatic polyamides. These novel polyamides have inherent viscosities in the range of 0.09–0.21 dL/g in N,N‐dimethylformamide (DMF) at 25°C. Fluorimetric studies of the model compound as well as polymers were performed. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 947–954, 2007     

Preparation of new poly(amide–imide)s with chiral architectures via direct polyamidation reaction

N‐trimellitylimido‐L ‐methionine ( 3 ) was prepared by reaction of trimellitic anhydride ( 1 ) with ‐L ‐methionine ( 2 ) in acetic acid solution at refluxing temperature. This diacid was reacted with thionyl chloride, and N‐trimellitylimido‐L ‐methionine diacid chloride ( 4 ) was obtained in quantitative yield. The resulting diacid chloride was reacted with p‐aminobenzoic acid in dry acetone and bis(p‐aminobenzoic acid)‐N‐trimellitylimido‐L ‐methionine ( 5 ) was obtained as a novel optically active amide–imide diacid monomer in high yield. The direct polycondensation of amide–imide diacid monomer 5 with several aromatic diamines was carried out with tosyl chloride (TsCl)/pyridine (Py)/dimetheylformamide (DMF) system. The resulting thermally stable poly(amide–imide)s (PAIs) were obtained in good yields and inherent viscosities ranging between 0.24 and 0.46 dL g^?1 and were characterized with FTIR, ¹H NMR, CHN, and TGA techniques. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 1248–1254, 2007     

Synthesis of Photoactive Polyureas Derived from 4-(4-Dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione and Diisocyanates

Summary 4-(4-Dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione (DAPTD) was prepared from 4-dimethylaminobenzoic acid in five steps. The reaction of monomer DAPTD with n-isopropylisocyanate was performed at room temperature in N,N-dimethylacetamide (DMAc) solution and the resulting bis-urea derivative was obtained in high yield and was finally used as a model compound for polymerization reaction. The step-growth polymerization reactions of monomer with hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI) and toluene-2,4-diisocyanate (TDI) were performed in DMAc solution in the presence of pyridine, triethylamine or dibutyltin dilurate as catalysts. Some physical properties and structural characterization of these novel polyureas are reported. Fluorimetric studies of the model compound as well as polymers were performed.     

Study on morphology,thermal, mechanical and Cd(II) adsorption properties of PVC/α-MnO<Subscript>2</Subscript>-stearic acid nanocomposites: production and application

Alpha manganese dioxide nanorods (α-MnO₂) were successfully functionalized with stearic acid (SA) by solvothermal method to prevent agglomeration. The α-MnO₂-SA nanorods were employed as a filler for the preparation of poly(vinyl chloride) (PVC) nanocomposite (NC) films with different percentages (1, 3 and 5 wt%). The morphology, mechanical and thermal properties of the obtained NCs were investigated. The results showed that α-MnO₂-SA can effectively improve the properties of PVC. The enhancement in properties of the NCs was attributed to the improved interfacial bonding by modification. Also, these NCs were used as adsorbent for removal of cadmium ions. Our finding suggests that the PVC/α-MnO₂-SA NCs are good candidates for efficient Cd(??) removal from the wastewater.     

Efficient functionalization of multi‐walled carbon nanotubes with p‐aminophenol and their application in the fabrication of poly(amide‐imide)‐matrix composites

The ultrasonically assisted preparation and characterization of poly(amide‐imide) (PAI) composites containing functionalized multi‐walled carbon nanotubes (MWCNTs) are reported. To improve the dispersion in and compatibility with the polymer matrix, the MWCNTs were surface‐modified with p‐aminophenol (p‐AP) under microwave irradiation. The process is fast, one‐pot, easy and results in a high degree of functionalization as well as dispersibility in organic solvents. The p‐AP‐functionalized MWCNTs (MWCNTs‐AP) were analysed by means of field emission and transmission electron microscopy, Fourier transform infrared spectroscopy, X‐ray diffraction and thermogravimetric analysis (TGA). The results consistently confirm the formation of p‐AP functionalities on MWCNTs which are able to undergo additional reactions, while the structure of the MWCNTs remains relatively intact. MWCNTs‐AP/PAI hybrid films were prepared with various MWCNTs‐AP contents (5–15 wt%) using a solution‐casting technique. Microscopic observations show that the dispersion of the MWCNTs‐AP is improved as a result of the organic groups on the MWCNT surface and functional groups in the PAI structure. The properties of the obtained composites were characterized extensively using the aforementioned techniques. TGA results show that the hybrid films exhibit a good thermal stability. Tensile mechanical testing was performed for the prepared composites, the results of which indicate an increase in the elastic modulus and tensile strength with increasing MWCNTs‐AP content. © 2013 Society of Chemical Industry     

Synthesis and biodegradability assessment of poly(amide-imide)s containing N-trimellitylimido-l-amino acid and 5-(2-benzimidazole)-1,3-phenylenediamine

This paper addressed construction and biodegradability assessment of chiral synthetic poly(amide-imide)s (PAI)s. These polymers were prepared by polycondensation reaction of chiral diacids; N-trimellitylimido-S-valine (7a), and N-trimellitylimido-l-leucine (7b) with 5-(2-benzimidazole)-1,3-phenylenediamine (4) in the presence of tetrabutylammonium bromide as a green media under microwave irradiation. The morphology observations of the aforementioned polymers exhibit that these macromolecules are nanostructured particle and so, good candidate as carrier for biomedical application. Furthermore, in vitro toxicity and soil biodegradability test of the different synthetic diacids (7a, 7b) and the obtained PAIs were employed to evaluate the biological activity of these materials. In Petri plate technique, the monomers and obtained polymers exposed on glass lamels were all colonized by fungal saprophytes and due to this invasion, a weight loss up to 35 % was observed in the material. The soil burial test and measuring dehydrogenase activity revealed that the aforementioned monomers and polymers are biologically active and probably biodegradable under the soil. Normal wheat seedling growth took place in the vials containing the aforesaid monomers and polymers. It could be concluded that the synthesized monomers and their polymers are biologically active, and they are nontoxic to ecosystems and natural environments.     

A straightforward preparation and characterization of novel poly(vinyl alcohol)/organoclay/silver tricomponent nanocomposite films

In the present investigation, novel poly(vinyl alcohol)/organoclay/silver (PVA/OMMT/Ag) tricomponent nanocomposite (NC) films with different compositions were prepared by solution intercalation method under ultrasonic irradiation process. The NC films were obtained by mixing a colloidal solution consisting of Ag nanoparticles (NPs) (3, 5, 7 and 9 wt%) with a water solution of PVA and OMMT (10 wt%) via solution casting method. The scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction, Fourier transform infrared spectroscopy, and thermogravimetric analysis (TGA) were utilized to characterize the morphology and properties of the PVA/OMMT/Ag NC films. TGA confirmed that the heat stability of the nanocomposite was improved. The enhancement in the thermal properties of the hybrid materials was due to strong hydrogen bonding between OH groups of PVA, free acid functionalized groups of OMMT, and the Ag NPs. SEM and TEM results also showed that the OMMT and Ag NPs were dispersed homogeneously in the PVA matrix on nanoscale.     

Novel chiral poly(amide-imide)/surface modified SiO2 nanocomposites based on N-trimellitylimido-l-methionine: Synthesis and a morphological study

In the present investigation, novel poly(amide-imide) (PAI)/SiO₂ nanocomposites (NCs) containing l-methionine moiety in the main chain were prepared via a simple and fast ultrasonic irradiation process. PAI was synthesized by direct poly condensation reaction of N-trimellitylimido-l-methionine with 4,4′-diamino diphenylether in molten tetra-n-butyl ammonium bromide/triphenyl phosphite as a green condensing agent. Due to the high surface energy and tendency for agglomeration, the surface of SiO₂ NPs was modified with chiral diacid. The obtained NCs were characterized by Fourier transform-infrared (FT-IR) spectroscopy, thermogravimetry analysis, X-ray powder diffraction, field emission-scanning electron microscopy (FE-SEM), and transmission electron microscopy (TEM). The FT-IR spectroscopy indicated that the chiral diacid as the coupling agent was attached on the surface of SiO₂ NPs. FE-SEM, and TEM images showed that SiO₂ NPs were dispersed rather homogeneously in the PAI matrix.