Synthesis and characterization of cycloaliphatic hydrophilic polyurethanes, modified with l-ascorbic acid, as materials for soft tissue regeneration

• Published in: Materials Science & Engineering C 2017-06, Vol.75, p.671-681
• Main Authors: Kucinska-Lipka, J., Gubanska, I., Strankowski, M., Cieśliński, H., Filipowicz, N., Janik, H.
• Format: Article
• Language: English
• Subjects: Acrylamides - chemistry; Aliphatic compounds; Ascorbic acid; Ascorbic Acid - chemistry; Ascorbic Acid - pharmacology; Biocompatibility; Biodegradation; Biomedical materials; Butanediol; Butylene Glycols - chemistry; Calorimetry; Canola oil; Chemical structure; Chemical synthesis; Contact angle; Cyanates - chemistry; Differential scanning calorimetry; Distilled water; Enthalpy; Flora; Fourier transforms; Glass transition temperature; Heat measurement; Humans; Hydrophobicity; Infrared spectroscopy; l-Ascorbic acid; Magnetic resonance spectroscopy; Materials science; Materials Testing; Melting; NMR; Nuclear magnetic resonance; Parameter modification; Phosphates; Physicochemical properties; Polyurethane; Polyurethane resins; Polyurethanes - chemical synthesis; Polyurethanes - chemistry; Polyurethanes - pharmacology; Regeneration; Regeneration (physiology); Regenerative medicine; Saline water; Soft tissues; Spectroscopy; Tissue engineering; Tissue regeneration; Vitamin C
• ISSN: 0928-4931; 1873-0191
• DOI: 10.1016/j.msec.2017.02.052

In this paper we described synthesis and characteristic of obtained hydrophilic polyurethanes (PURs) modified with ascorbic acid (commonly known as vitamin C). Such materials may find an application in the biomedical field, for example in the regenerative medicine of soft tissues, according to ascorbic acid wide influence on tissue regeneration Flora (2009), Szymańska-Pasternak et al. (2011), Taikarimi and Ibrahim (2011), Myrvik and Volk (1954), Li et al. (2001), Cursino et al. (2005) . Hydrophilic PURs were obtained with the use of amorphous α,ω-dihydroxy(ethylene-butylene adipate) (dHEBA) polyol, 1,4-butanediol (BDO) chain extender and aliphatic 4,4′-methylenebis(cyclohexyl isocyanate) (HMDI). HMDI was chosen as a nontoxic diisocyanate, suitable for biomedical PUR synthesis. Modification with l-ascorbic acid (AA) was performed to improve obtained PUR materials biocompatibility. Chemical structure of obtained PURs was provided and confirmed by Fourier transform infrared spectroscopy (FTIR) and Proton nuclear magnetic resonance spectroscopy (1HNMR). Differential scanning calorimetry (DSC) was used to indicate the influence of ascorbic acid modification on such parameters as glass transition temperature, melting temperature and melting enthalpies of obtained materials. To determine how these materials may potentially behave, after implementation in tissue, degradation behavior of obtained PURs in various chemical environments, which were represented by canola oil, saline solution, distilled water and phosphate buffered saline (PBS) was estimated. The influence of AA on hydrophilic-hydrophobic character of obtained PURs was established by contact angle study. This experiment revealed that ascorbic acid significantly improves hydrophilicity of obtained PUR materials and the same cause that they are more suitable candidates for biomedical applications. Good hemocompatibility characteristic of studied PUR materials was confirmed by the hemocompatibility test with human blood. Microbiological tests were carried out to indicate the microbiological sensitivity of obtained PURs. Results of performed studies showed that obtained AA-modified PUR materials may find an application in soft tissue regeneration. [Display omitted] •PURs of cycloaliphatic diisocyanate (HMDI) and amorphous polyol are suitable for soft tissue regeneration.•L-ascorbic acid, used in this study as a PUR modifier, improved hydrophilic character of obtained PURs.•Hemocompatibility of obtained PURs