Spectral and thermal investigation of designed terpolymers bearing p-acetylpyridine oxime moieties having excellent antimicrobial properties

Abstract

A new monomer, (E)-4-acetylpyridine oxime (APO), was prepared by reaction of 4-acetylpyridine and hydroxylamine hydrochloride. Its terpolymers with 4-hydroxyacetophenone (HA)/4-hydroxybenzaldehyde (HB) and formaldehyde (F) were synthesized by using an acid catalyst in 1:1:5 M proportions. The synthesized monomer (APO) and its terpolymers were identified by FT-IR and 1 H NMR spectroscopic data. The apparent number average molecular weight and viscosities were determined by gel permeation chromatography and Ubbelohde viscometer, respectively. Thermal stability of these resins was determined by differential scanning calorimetry (DSC). The activation energy (E a ) values of the thermal decompsition were investigated with thermogravimetric analysis (TGA) by isoconversional Flynn-Wall-Ozawa method. Empirical kinetic models, as well as generalized master plots, were applied to explain the degradation mechanisms of terpolymers. The terpolymers strongly inhibited the growth of a wide variety of microorganisms, including Grampositive, Gram-negative bacteria and fungi.

Spectral and Thermal Characterization of Halogen-Bonded Novel Crystalline Oligo(p-bromoacetophenone formaldehyde)

“…The activation energy, E a , during thermal degradation was computed by the Kissinger method. − The Kissinger equation is − β T d 2 = prefix− ln nobreak0em.25em⁡ italicA italicR italicE normala + 1 italicT normald italicE normala italicR where β is heating rate; T d , the decomposition temperature; R , the gas constant; and E a , the activation energy.…”

Simple and efficient synthesis with theoretical calculations of novel N-halamine monomers

“…In conclusion: novel styrenic monomers with potential biocidal activity: 5,5dimethyl-3-(4-vinylbenzyl) imidazo-lidine-2,4-dione (1), 1-(4-vinylbenzyl)-1′,3′-dihydrospiro-[imidazolidine-4,2′-indene]-2,5-dione (2), and 1-(4-vinylbenzyl)-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (3) and their N-chlorinated forms 1-chloro-5,5-dimethyl-3-(4-vinylbenzyl)imidazolidine-2,4-dione (1-Cl), 3-chloro-1-(4-vinylbenzyl)-1′,3′dihydrospiro[imidazolidine-4,2′-indene]-2,5-dione (2-Cl), and 3-chloro-1-(4-vinylbenzyl)-3′,4′-dihydro-1′H-spiro [imidazolidine-4,2′-naphthalene]-2,5-dione (3-Cl) were synthesized in simple and efficient procedures with good yields and high purities. All of the resulting compounds were characterized by FTIR and NMR spectroscopy, and in all cases, the spectra were found to be in consistent with the expected structures.…”

“…During the past decade, the great interest has been devoted to biocidal polymers, which are able to kill pathogenic microorganisms or at least are characterized by the high resistance to microbial attack. [1][2][3][4][5][6][7][8][9][10] Polystyrene, is the thermoplastic material applied in numerous industrial branches, and its properties are well known since many years and are often modified for manufacturing the modern plastics with completely different properties than origin polymer. [11][12][13][14] On the other hand, hydantoins represent a group of compounds which over the past few years has also attracted great attention because of their diverse biological activities including antibacterial, antiviral, fungicidal, herbicidal, analgesic, antiarythmic, antihypertensive, antidiabetic, HDL/cholesterol modulating, anticonvulsant, and cancer chemotherapeutic activity.…”

“…The present study is to report the synthesis of novel free radical polymerizable spirohydantoin-containing styrene-types monomers designed for biocidal materials preparation : 5,5-dimethyl-3-(4-vinylbenzyl) imidazo-lidine-2,4-dione (1), 1-(4-vinylbenzyl)-1′,3′-dihydrospiro-[imidazolidine-4,2′-indene]-2,5-dione (2), and 1-(4-vinylbenzyl)-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (3) and their N-chlorinated form(1-Cl, 2-Cl, 3-Cl). Monomers 1 and 1-Cl have been prepared as a model compounds to verify the procedure.…”

Preparation and characterization of bio-based terpolymer derived from vanillin oxime, formaldehyde, and p-hydroxyacetophenone

“…[5] Moreover, p-chloroacetophenone oxime, p-hydroxy benzaldehyde oxime, 4-acetylpyridine oxime, and 8-hydroxyquinioline-based terpolymers were synthesized in the presence of an acid with excellent biocidal properties. [6][7][8][9][10][11] The oxime click reaction is shown to be a straightforward methodology for the synthesis of PEGpolysaccharide di-block copolymers. The method is applicable to unmodified polysaccharides with a reductive end as demonstrated for dextran, hyaluronic acid, and chitosan.…”