Synthesis,structural characterization,and antiproliferative/cytotoxic effects of a novel modified poly(maleic anhydride-co-vinyl acetate)/doxorubicin conjugate

Polymer Bulletin - Drug carrier, poly(maleic anhydride-co-vinyl acetate) (MAVA or poly[MA-co-VA]) copolymer, was traditionally synthesized by free radical chain polymerization reaction, in methyl...     

Synthesis,characterization and cytotoxicity of novel modified poly[(maleic anhydride)‐ co‐(vinyl acetate)]/noradrenaline conjugate

Poly[(maleic anhydride)‐co‐(vinyl acetate)] (MAVA) copolymer was synthesized by free radical polymerization reaction, in methyl ethyl ketone at 80 °C, using benzoyl peroxide as the initiator. The copolymer was then modified with a biomolecule, noradrenaline (NA). The modification reaction was performed at 70 °C in dimethylformamide containing triethylamine as the catalyst. The modified polymer was named MAVA/NA. Structural characterization of the copolymer and the modified product was carried out by Fourier transform infrared (FTIR) and ¹H NMR and ¹³C NMR spectroscopy. The FTIR, ¹H NMR and ¹³C NMR spectra confirmed that NA was successfully covalently bound to the MAVA copolymer backbone. Surface morphology was visualized by atomic force microscopy. The cumulative release of NA from MAVA/NA was determined in phosphate buffered saline solution for 7 days at 37 °C and compared with MAVA. Cytotoxicity of the MAVA/NA was evaluated by using a mouse fibroblast cell line (L929). Results obtained indicated that MAVA/NA had almost no toxicity and no negative effect on cell viability at 250 µg mL^?1 concentration. © 2012 Society of Chemical Industry     

Synthesis and property characterization of cassava starch grafted poly[acrylamide-co-(maleic acid)] superabsorbent via γ-irradiation

Graft copolymerizations of acrylamide and maleic acid onto cassava starch by a simultaneous irradiation technique using γ-rays as an initiator were carried out. Various important parameters of total dose, dose rate, monomer-to-cassava starch ratio and maleic acid content were studied. Addition of 2% w w⁻¹ diprotic acid of maleic acid into the reaction mixture yields a saponified starch graft copolymer with a water absorption in distilled water as high as 2256 g g⁻¹ of its dried weight. The water absorption of these saponified graft copolymers in saline and buffer solutions was also measured. The water absorption depends largely on the cationic type and concentration of these solutions in terms of ionic strength. This research explains a charge transfer mechanism for graft copolymerization of maleic acid and acrylamide onto cassava starch, and describes the influential parameters that affect grafting efficiency and water absorption.     

Synthesis of modified poly(ethylene terephthalate) fibers with antibacterial properties and their characterization

Poly(ethylene terephthalate) (PET) fibers were grafted with vinyl monomers by utilizing benzoyl peroxide. Grafted PET fibers were modified in optimized conditions with several functional groups such as amine, chlorine, hydrogen peroxide_, and triclosan to gain antibacterial feature. The second part of this study comprised examination of the antibacterial features of PET fibers via use of Staphylococcus aureus (ATCC 29213) and Escherichia coli (ATCC 25922) bacteria. Kirby-Bauer test is used to study antibacterial properties. The longest zone diameter for Trc-GMA-g-PET fibers was 56?mm for E. Coli whereas the biggest diameter for S. aureus bacteria was 130?mm with Trc-MMA-g-PET fibers.     

Synthesis,characterization, and gas transport properties of novel iptycene-based poly[bis(benzimidazobenzisoquinolinones)]

Two novel iptycene-based tetramine monomers were successfully synthesized by nucleophilic aromatic substitution of triptycene-1,4-diol and pentiptycene-6,13-diol with 5-chloro-2-nitro-aniline, followed by reduction, respectively. These monomers were polymerized with 4,4-binaphthyl-1,1,8,8-tetracarboxylic dianhydride to obtain two novel iptycene-based poly[bis(benzimidazobenzisoquinolinones)]s (PBIBI–TPD and PBIBI–PPD) by a one-step, high-temperature solution polycondesation. Incorporation of iptycene groups especially the pentiptycene group in the polymer backbones improved their solubility and thermal stability. The resulting membranes exhibited good gas permeability owing to the high internal free volume elements introduced by the iptycene groups as well as high gas selectivity due to the restricted local segmental mobility arising from the interlocking of these groups in the polymer backbone. The membrane of PBIBI–PPD showed high CO₂ permeability (112 barrer) and moderately good CO₂/N₂ and CO₂/CH₄ selectivity (22 and 31) for mixed gas separation.     

Preparation and characterization of a novel antibacterial acrylate polymer composite modified with capsaicin

A novel antibacterial acrylate polymer composite modified with capsaicin was successfully synthesized by a two-step reaction. Capsaicin and acryloyl chloride were firstly esterified, and then applied to solution polymerization with acrylate monomers and styrene. The yield of the esterified products was about 85.3%. The polymer was characterized by Fourier transform infrared spectroscopy (FTIR), gel permeation chromatography (GPC), thermogravimetric analysis (TGA), contact angle (CA) and antibacterial ring tests. The number-average molecular weight (M_n) of the polymer was 27214, based on the capsaicin-acrylate dosage of 6.5 wt%. The TGA revealed a stable thermal property. The contact angles of the polymers films on tinplate increased from 77.5° to 86.2° with the increasing amount of capsaicin-acrylate. The antibacterial tests demonstrated excellent antimicrobial capability of the polymers.     

Synthesis,characterization, and in vitro biocompatibility study of novel disulfide cross‐linked hydrogels based on poly(amic acid)

In this study, novel disulfide cross‐linked hydrogels were designed and synthesized. First, ethylenediaminetetraacetic dianhydride reacted with butanediamine and amino‐terminated polyethylene glycol via N‐acylation reaction to give biocompatible poly(amic acid) (PAA) with pendant carboxyl groups; then, the amino groups of cystamine reacted with carboxyl groups of PAA to generate disulfide cross‐linked network polymer (PAA‐SS). Fourier transform infrared spectroscopy, ¹H nuclear magnetic resonance imaging, gel permeation chromatography with multiangle laser light scattering, potentiometric titration, rheology, hydrolytic degradation, morphology, porosity, and in vitro biocompatibility studies were used to qualitatively and quantitatively characterize the obtained polymers. The results indicated that the equilibrium swelling ratio of the PAA‐SS decreased with the increase in Rm. The PAA‐SS provided good mechanical strength to maintain their integrity, and the storage modules (G′) of the hydrogels can be adjusted by Rm. The PAA‐SS presented co‐continuum pores, and the pore size correlated with the cross‐linking degree. The degradation of PAA‐SS could be controlled by regulating the concentration of dithiothreitol. Particularly, the PAA‐SS possessed an excellent biocompatibility, as the average proliferating rate of osteoblasts on PAA‐SS was appreciably higher than that on PAA and glass coverslips. In conclusion, the above obtained results demonstrate that the performance of the PAA‐SS outbalance and facilitate the application in biomedical region, particularly in bone tissue regeneration. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 40930.     

Synthesis and characterization of modified poly(aspartic acid) and its performance as a formaldehyde adsorbent

A modified poly(aspartic acid) (PASPTU) as an efficient formaldehyde adsorbent is successfully prepared by grafting poly(aspartic acid) (PASP) with threonine and urea. The graft copolymer is characterized by means of nuclear magnetic resonance, Fourier transform infrared spectroscopy, and gel permeation chromatography. Its formaldehyde adsorbent property is measured. The optimal adsorption process is as follows: synthesis temperature was 40 °C, molar ratio of PSI, threonine, and urea was 1:0.6:0.4 and adsorption time was 3.0 h. In above condition, the formaldehyde adsorbent efficiency of the copolymer was nearly 100% when the PASPTU dosage was 0.5 g. The Langmuir and Freundlich adsorption isotherms are used to study the adsorption process of formaldehyde. The findings show that PASPTU has excellent formaldehyde adsorbent efficiency. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 45798.     

Synthesis,characterization and properties of poly(butylene succinate) modified with rosin maleopimaric acid anhydride

Huge hydrogenated phenanthrene ring segments were introduced into the main chain of poly(butylene succinate) by polymerization of succinic acid (SA), 1,4‐butanediol (BD) and rosin maleopimaric acid anhydride (RMA), which was obtained from maleic rosin. The chemical structure and composition of the copolyesters were determined with the aid of ¹H‐NMR, FTIR and elemental analysis. The thermal properties, crystallization behaviour and mechanical properties of the copolyester were then investigated using differential scanning calorimetry (DSC), wide‐angle X‐ray diffraction (WAXD), polarized light microscopy (PLM) and mechanical testing. With increasing content of hydrogenated phenanthrene ring segments, the melting temperature, the crystallization temperature and the relative degree of crystallinity decreased gradually, but the elongation at break and the notched impact strength of poly(butylene succinate) were enhanced without a significant deterioration of tensile strength. Copyright © 2006 Society of Chemical Industry     

Synthesis, characterization polymerization and antibacterial properties of novel thiophene substituted acrylamide

Ethyl 2-acrylamido-4,5,6,7-tetrahydrobenzo [b] thiophene-3-carboxylate (ETTCA) has been synthesized and its structure has been elucidated by elemental analysis and spectral tools. Free radical polymerization of (ETTCA) has been conducted in several solvents using azobisisobutyronitrile (AIBN) as an initiator. The kinetic parameters of polymerization of the ETTCA were investigated, and it was found that the polymerization reaction follows the conventional free radical scheme. The overall activation energy of polymerization ΔE was determined (ΔE = 45.11 kJ mol⁻¹). The copolymerization of ETTCA with three conventional monomers was carried out in dioxane at 65 °C. The monomer reactivity ratios for the copolymerization of ETTCA with methyl methacrylate (MMA), vinyl acetate (VA) and vinyl ether (VE) were calculated. Thermal stability of the ETTCA polymer and its copolymers were investigated by thermogravimetric analysis. It has been found that the prepared polymer (PETTCA) and its copolymers with VA have moderate biological activity and highly dependent on the copolymer composition.     

Synthesis and characterization of a novel soil stabilizer based on biodegradable poly(aspartic acid) hydrogel

A novel soil stabilizer based on poly-amino acid - polyaspartic acid (PASP) and its copolymer which modified by xanthan gum (XG) was studied to increase soil particle compressive strength and resistance to wind erosion. Due to its unique property, the stabilizer aggregated individual soil particles and formed crust. The sample compressive strength increased from 0.175 to 0.612 MPa and the wind erosion modulus reduced from 22.43 to 10.56 g·m⁻²·min⁻¹ after the 1% PASP hydrogel was applied by 1.67 Lm⁻² (1 cm of crust). The soil water content was higher than the control due to the polymer’s excellent water-retaining property. The polymer had no negative influence on seed germination and growth. The biodegradability experiment showed that PASP was easy to biodegrade and therefore it was safe to apply in the field. This work was presented at 13 ^th YABEC symposium held at Seoul, Korea, October 20–22, 2007.     

Synthesis and characterization of a novel fibrous antibacterial fiber with organophorsphor functional groups

A novel antibacterial fiber named ethyltriphenylphosphonium bromide‐polyacrylonitrile fiber (ETPB‐PANF) was synthesized by chemical modification of PANF reacted with ETPB. The PANF was first immersed in NaOH solution to get Na‐PANF with ? COONa groups. Na‐PANF was then reacted with ETPB to get the final fiber. During the process of synthesis, this article investigated on the initial concentration of ETPB, the contact time, the reaction temperature, and the pH of the solution that may have effect on the properties of ETPB‐PANF. ETPB‐PANF was characterized by Fourier transform infrared spectroscopy, thermo gravimetric analyzer, scanning electron microscope, and X‐ray photoelectron spectroscopy, and the releasing amount of ETPB from ETPB‐PANF was examined by inductively coupled plasma atomic emission spectrometry. The antibacterial activity of ETPB‐PANF was examined against Escherichia coli and Staphylococci aureus by improved shake flask method in sterile saline. The results showed that organophorsphor functional groups have been successfully grafted on PANF, and ETPB‐PANF showed good antibacterial abilities for E. coli and S. aureus. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 40935.     

Synthesis and characterization of a novel polyesteramide from modified jatropha seed oil,dimer acid and ethylenediamine as hot melt adhesive

This work deals with the synthesis and characterization of a novel polyesteramide (PEA) hot melt adhesive (HMA) using dimer acid, ethylenediamine, and modified jatropha seed oil. Jatropha seed oil was initially reacted with diethanolamine to prepare N,N-bis(2-hydroxyethyl) jatropha oil fatty amide (HEJA), having hydroxyl end groups. HEJA was reacted with dimer acid as a partial replacement of ethylenediamine. Ethylenediamine was replaced up to 30% by HEJA, on molar basis. Prepared PEA HMAs were characterized for mechanical, thermal, rheological, and adhesion properties. Increased replacement of ethylenediamine by HEJA led to decreased tensile strength, melting temperature, enthalpy of melting, crystallization temperature, enthalpy of crystallization, glass transition temperature, lap shear strength, T-peel strength, and viscosity. This was due to the reduction in hydrogen bond formation capacity, and thus the intermolecular forces of attraction of the ester and secondary amide linkages as compared to primary amide linkages, and the increased distance between ester linkages as compared to the primary amide linkages, was caused due to the bulky nature of HEJA. However, HMAs prepared using HEJA will have better low temperature flexibility due to low T_g; and better adhesion process due to the lower viscosity and melting temperature.     

Synthesis,characterization and in vitro degradation of poly(ester-anhydride)s based on succinic acid and 1,6-bis-p-carboxyphenoxyhexane

This paper describes synthesis and characteristics of functional poly(ester-anhydride)s bearing allyl pendant groups. The polymers were obtained by polycondensation of 1,6-bis-p-carboxyphenoxyhexane (CPH) and oligo(3-allyloxy-1,2-propylene succinate) terminated with carboxyl groups (OSAGE). The carboxyl groups in OSAGE and in CPH were converted to mixed anhydride groups by acetylation with acetic anhydride. After that, prepolymers thus obtained were condensed in vacuum to yield poly(ester-anhydride)s. The structure of copolymers was confirmed by NMR spectroscopy. Influence of molecular weight of OSAGE as well as of the CPH and OSAGE content on selected properties of poly(ester-anhydride)s was examined. Poly(ester-anhydride)s were subjected to hydrolytic degradation at 37 °C, in aqueous phosphate buffer solution of pH 7.41 (PBS). The course of degradation was monitored by determination of weight loss of samples and ¹H NMR. Fracture surfaces of samples during degradation were examined by scanning electron microscopy.     

Synthesis,characterization, and properties of novel poly(ether urea)s

Two diamines, 2,6‐bis(4‐aminophenoxy)pyridine and 2,6‐bis(5‐amino‐1‐naphenoxy)pyridine, were prepared through the nucleophilic aromatic substitution reaction of 4‐aminophenol and 5‐amino‐1‐naphthol, respectively, with 2,6‐dichloropyridine. Poly(ether urea)s were synthesized through the polyaddition reactions of these diamines with aromatic, semiaromatic, and cycloaliphatic diisocyanates. All the monomers and polymers were fully characterized, and physical properties of the polymers, including the thermal behavior, thermal stability, solubility, and solution viscosity, were studied. The polyureas showed improved thermal stability. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 961–965, 2004     

Synthesis and characterization of maleic acid polymer for use as scale deposits inhibitors

The problem of scale formation in oil field production facilities is encountered as a result of mixing of injection water (Lias) rich in sulfate with formation water (Ordovicien) rich in barium. 1 A large number of methods have been developed for the prevention of these deposits. In this work, poly(maleic acid) was studied to ascertain its suitability as an inhibitor of barium sulfate scale deposits. It was synthesized by a free radical solution polymerization. Two different initiators were used namely a potassium persulfate and a redox system composed of potassium persulfate/sodium‐hypophosphite monohydrate. Their concentrations were varied to obtain low‐molecular weight polymers. Physical and chemical properties of the polymers obtained were measured by infrared and UV/VIS spectrometry, solubility test, viscosimetry, refractometry, and liquid chromatography. The effectiveness of poly (maleic acid) formulations as scale inhibitor was studied by turbidimetric tests. The most effective inhibitor formulation was found to be that based on poly(maleic acid) prepared via a redox initiating system. This polymer, used at a concentration of 3 ppm, presented the highest effectiveness namely 96% and 88% at room and oil well temperature, respectively, when compared with two commercial inhibitors. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis and characterization of hydrophobically modified poly(vinyl alcohol)

Summary Two different routes for the preparation of hydrophobically modified poly(vinyl alcohol), PVA are reported. The first method involves the formation of the polymeric alcoholate. An alkylhalide and propanesultone are coupled with the polymer in two subsequent steps of the Williamson ether synthesis. The product is a hydrophobically modified polymer with anionic functionality. The other method proceeds via a 1,4 addition of acrylamide and the Hoffman degradation of the amide to an amine. In the next step, the amine is alkylated with an alkylhalide. The polymers are characterised by quantitative ¹HNMR spectroscopy and titration. Received: 14 January 1999/Revised version: 19 April 1999/Accepted: 19 April 1999     

Synthesis and characterization of novel poly(arylenevinylene) derivative

The new poly(arylenevinylene) derivative composed naphthalene phenylene vinylene backbone was developed. The theoretical calculation showed that the model compound of the obtained polymer was highly distorted between the stryl and naphthalene units as well as between the backbone and fluorene side units. The polymer was synthesized by the palladium catalyzed Suzuki coupling reaction with 2,6‐(1′,2′‐ethylborate)‐1,5‐dihexyloxynaphtalene and 1,2‐bis(4′‐bromophenyl)‐1‐(9″,9″‐dihexyl‐3‐fluorenyl)ethene. The structure of the polymer was confirmed by ¹H NMR, IR, and elemental analysis. The weight–average molecular weight of the polymer is 29,800 with the polydispersity index of 1.87. The new polymer showed good thermal stability with high T_g of 195°C. The bright blue fluorescence (λ_max = 475 nm) was observed both in solution and film of new polymer with naphthalene phenylene vinylene backbone. Double layer LED devices with the configuration of ITO/PEDOT/polymer/LiF/Ca/Al showed a turn‐on voltage at around 4.5 V, the maximum luminance of 150 cd/m², and the maximum efficiency of 0.1 cd/A. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Synthesis,characterization and properties of a castor oil modified biodegradable poly(ester amide) resin

A biodegradable poly(ester amide) resin was synthesized from N,N-bis(2-hydroxy ethyl) fatty amide of castor oil with maleic anhydride, phthalic anhydride and isophthalic acid (100:30:35:35 mole ratio) by the polycondensation process. The fatty amide of the oil was obtained for the first time with 95% yield. The chemical structure of the synthesized resin was characterized by spectroscopic techniques like FTIR, ¹H NMR and ¹³C NMR. Various physical properties such as acid value, saponification value, iodine value, specific gravity and viscosity of the resin were also determined. Further the rheological behavior, studied in the steady shear mode showed shear thinning behavior of the resin. The epoxy cured poly(ester amide) thermoset using poly(amido amine) hardener exhibited better properties than with the cycloaliphatic amine hardener cured system. TGA studies also revealed higher thermal stability of the former system than the latter. In vitro-biodegradation study of the poly(ester amide) thermoset using Pseudomonas aeruginosa and Bacillus subtilus bacteria revealed superior biodegradability of the thermoset using the former bacterial strain. Excellent chemical resistance against various chemical media including alkali was observed for epoxy-poly(amido amine) cured poly(ester amide) resin over epoxy-cycloaliphatic amine one. The epoxy-poly(amido amine) cured poly(ester amide) thermoset thus has the potential to be used as surface coating material.