Development of Infection Resistant Polyurethane Biomaterials Using Textile Dyeing Technology

Abstract

Infection is a major complication when using biomaterials such as polyurethane in the clinical setting. The purpose of this study was to develop a novel infection resistant polyurethane biomaterial using textile dyeing technology. This procedure results in incorporation of the antibiotic into the polymer, resulting in a slow, sustained release of antibiotic from the material over time, without the use of exogenous binder agents. Polycarbonate based urethanes were synthesized that contained either a non-ionic (bdPU) or anionic (cPU) chain extender within the polymer backbone and cast into films. The fluoroquinolone antibiotic ciprofloxacin (Cipro) was applied to bdPU and cPU using textile dyeing technology, with Cipro uptake determined by absorbance reduction of the "dyebath." These dyed bdPU/cPU samples were then evaluated for prolonged Cipro release and antimicrobial activity by means of spectrophotometric and zone of inhibition assays, respectively. Cipro release and antimicrobial activity by dyed cPU segments that were aggressively washed persisted over 9 days, compared with dyed bdPU and dipped cPU control segments that lasted < 24 hours. Dyed cPU segments, which remained in a static wash solution, maintained antimicrobial activity for 11 days (length of study), whereas controls again lost antimicrobial activity within 24 hours. Thus, application of Cipro to the cPU polymer by means of dyeing technology results in a slow sustained release of antibiotic with persistent bacteriocidal properties over extended periods of time.

Development of an infection‐resistant bifunctionalized Dacron biomaterial

“…Due to the structural similarities between the dyes and certain antibiotics, antibiotic dyeing paralleled the dyeing process where more color meant more dye uptake 29. Literature on the mechanisms of dyeing (their structural composition and interactions with various fibers) is well known, with the foundation of small molecule incorporation into textile materials well established 27, 28.…”

“…Fluoroquinolone antibiotics are ideal for application using dyeing technology due to their heat stability, low molecular weight, low‐dose killing capacity, and broad‐spectrum antimicrobial activity. Additionally, fluoroquinolone antibiotics such as Cipro cover a majority of the Gram‐positive and negative bacteria that are encountered in a typical biomaterial infection, specifically Staphylococcus aureus and Staphylococcus epidermidis 29. The initial dyeing conditions that were used in this study were based on those exemplified in a practical dye application process:30 a liquor ratio of 20:1, a pH of 8, a dyeing temperature of 70°C, 5% owf, and a dyeing time of 4 h. These conditions were employed in a manner that mimicked a standard dyeing process, using a dye bath and constant mixing conditions to maximize the uptake of dye.…”

Soy-castor oil based polyols prepared using a solvent-free and catalyst-free method and polyurethanes therefrom

“…The OH of the polyols were determined using the Unilever method. 21 The acid number of the polyols were determined by AOCS Official Method Te 1a-64. The molecular weight was determined using a THF-eluted GPC equipped with a refractive index detector.…”

Reduction of Epoxidized Vegetable Oils: A Novel Method to Prepare Bio‐Based Polyols for Polyurethanes

“…The chemical structure of the vegetable oils and their derived polyols were analyzed by 1 H NMR spectroscopy using a Varian spectrometer (Palo Alto, CA) at 300 MHz and by FT‐IR spectroscopy using a Nicolet 460 FT‐IR spectrometer (Madison, WI). The OH values of the polyols were titrated according to the Unilever method . The acid numbers of the polyols were determined by AOCS Official Method Te 1a‐64.…”