Functionalization of polyesters with multiple B vitamins

Abstract

A method to covalently attach combinations of six different B vitamins provided an avenue to new functional thermosets without multi-step coupling reactions. The melt polymerization strategy required no organic solvent and facilitated covalent attachment of OH (B 1 , B 2 , B 5 , B 6 ) or COOH (B 7 , B 9 ) groups on B vitamins via Fischer esterification. Characterization of model reactions with LC/MS, FTIR, and GPC confirmed covalent attachment. Based on control experiments, B vitamins demonstrated unexpected thermal stability and appreciable solubility in the melt polymerization. This approach was demonstrated with citric acid and diglycerol, but has wide-ranging potential for other polar monomers with negative octanolwater partition coefficients (LogP).

Quantitative Measurements of Polymer Hydrophobicity Based on Functional Group Identity and Oligomer Length

“…Recently, combined experimental and computational approaches with LogP oct values have demonstrated the ability to discern hydrophobicity of anhydride monomer libraries, polyacrylate homopolymers, star polymers, postpolymer modification, polyester electrolytes, solubility of B vitamins in melt polymerizations, and diblock copolymers for crystallization driven self-assembly (CDSA) . The wide-ranging usefulness of partition coefficients stems from LogP oct values being proportional to the Gibbs free energy (Δ G ). , Consequently, LogP oct values have potential to create a more accurate picture of hydrophobicity than calculations involving solubility parameters (δ), like Hildebrand and Hansen values, which depend on enthalpy (Δ H ) and molar volume ( V m ).…”

“…As the structural diversity of petroleum − and renewable − monomers continues to expand, understanding and predicting hydrophobicity for various permutations of oxygen atoms leads to challenges. Consequently, an opportunity exists to rank common functional groups, like ethers, carbonates, esters, anhydrides, and acetals. − We hypothesize that functional groups with oxygen atoms exert a major influence on hydrophobicity and suggest that using the C:O ratio or size of alkyl substituents oversimplifies assessment when comparing structurally diverse monomers. For instance, will functional groups with the same number of oxygen atoms, like esters and acetals, have differing amounts of hydrophobicity?…”

Application or function of citric acid in drug delivery platforms

“…Based on the structure of the used B vitamin the covalently grafting occurred through the present functional groups in the structure of the CA and DG. This procedure for covalent attachment of biological molecules has many potential advantages that could provide a beneficial avenue for designing the new interesting DDSs for the delivery of therapeutic agents 184 . Aspirin is a commonly used drug for curing pain and fever or inflammation.…”

“…This procedure for covalent attachment of biological molecules has many potential advantages that could provide a beneficial avenue for designing the new interesting DDSs for the delivery of therapeutic agents. 184 Aspirin is a commonly used drug for curing pain and fever or inflammation. Oral administration is the usual approach for aspirin administration; however, the main side-effect of this procedure is gastrointestinal bleeding.…”

Dyeing to Degrade: A Bioplastics Experiment for College and High School Classrooms

“…As a continuation of our efforts to develop green polymer experiments for the high school and college laboratory curricula, − a collaboration was established with Professor Robert Mathers, who coauthored an article describing the synthesis of a biodegradable thermoset polymer from citric acid and glycerol . In recognizing the nontoxic, economical, simplistic (no solvent or catalyst required), and sustainable attributes of this chemistry, Mathers began exploring the potential of citric acid in his undergraduate classrooms and undergraduate research projects. , As we collaboratively began to investigate the viability of implementing the use of citric acid and glycerol in our teaching laboratories, beginning at the college level, we saw merit in developing a discovery-based experiment by combining the citric acid chemistry with our work in starch-based samples. We previously developed an experiment titled Make It and Break It for the high school curriculum, which explores the differences among corn, potato, and tapioca starch plastic films prepared in water and acid (either vinegar or HCl, depending on the instruction level) and the effects on physical properties and tensile strength from additives such as glycerol, glue, and sugar .…”