Novel polyketones with pendant imidazolium groups as nanodispersants of hydrophobic antibiotics

Abstract

In this work, we present a new method to nanodisperse the pH-sensitive antibiotics oxolinic acid and flumequine by the use of a pH-sensitive synthetic polyketone derivative with amphiphilic characteristics. The pH-sensitive polymer bears imidazolium residues on pendant groups as weak acids, and its solvophobic properties can be tuned by changing the pH. While the antibiotics are soluble in water at pHs higher than 7.0 for flumequine and 8.4 for oxolinic acid, and the polymer is soluble in water at pHs lower than 5.5, nanoprecipitates presenting hydrodynamic radius of 35-100 nm and positive zeta potential containing both the polymer and any of the antibiotics are formed at pH 6.8 by mixing stock solutions whose pH has been adjusted to 5.4 for the polymer and higher than 10 for the antibiotics. The out-of-equilibrium process occurring upon mixing both solutions produces pH changing, molecular arrangement, and a controlled collapse of the system in the form of nano-and submicron particles. The driving forces for the arrangements are found among hydrophobic forces, long-range electrostatic interactions, and short range aromatic-aromatic interactions.

Thermally Switchable Electrically Conductive Thermoset rGO/PK Self-Healing Composites

“…In addition, it can be also carried out without any solvent or in various organic solvents depending on the physical and chemical properties of the amine compound [ 20 ]. A variety of primary amines can be used, making this synthesis a fast, cheap, and appealing approach to create polymers with almost any desired pendant functional group [ 21 , 22 ]. Self-healing thermosets have been efficiently prepared by modifying polyketone with furan groups which can undergo thermally reversible Diels-Alder reactions with maleimides compounds [ 16 , 17 , 23 , 24 ].…”

Porous polyelectrolyte materials with controlled luminescence properties based on aromatic‐aromatic interactions with rhodamine B

“…Aromatic‐aromatic interactions between aromatic polyelectrolytes (ArPEL) and complementary charged aromatic counterions (ArC) have been a field of study in our group for the last 15 years 1‐14 . In aqueous solution, these short‐ and medium‐range interactions are additional to long‐range electrostatic interactions and involve close contact between the interacting polymeric aromatic moieties and the ArC, producing ion pairs and the release of water from their respective hydration sphere.…”

“…Both ArC and ArPEL properties are modified when interacting through aromatic‐aromatic interactions. Among them, we can mention redox, 15 acid‐base, 4,9,11,16 luminescent, 10,14 and aggregation properties 2,7,10,16,17 . Due to that, special functional formulations could be projected, both in the liquid and in the solid states.…”

Mechanical properties and electrical surface charges of microfibrillated cellulose/imidazole-modified polyketone composite membranes

“…These thermoplastic polymers offer several advantages over others. PKs can be chemically modified by Paal-Knorr reaction under mild experimental conditions, where high-conversion degree (up to 80%) of 1,4 dicarbonyl groups can be obtained [37]. This results in the introduction of numerous functional groups including amine and imidazole moieties along the backbone structure of PKs [37].…”

“…PKs can be chemically modified by Paal-Knorr reaction under mild experimental conditions, where high-conversion degree (up to 80%) of 1,4 dicarbonyl groups can be obtained [37]. This results in the introduction of numerous functional groups including amine and imidazole moieties along the backbone structure of PKs [37]. The Paal-Knorr reaction is a simple and inexpensive route that introduces pyrrole rings along with other functional or multi-functional groups into the macromolecular structure of PKs [37][38][39][40].…”