Abstract
Surgical adhesives consist on an attractive alternative to suturing or stapling since they can accomplish other tasks, such as haemostasis and the ability to seal air leakages. The application of adhesives would also reduce the surgeries procedure time since they represent an easier and faster method to establish tissue adhesion. The aim of this work was the development of a biodegradable urethane pre-polymer that presents the capacity of reacting with the amino groups present in the biological molecules. Urethanes based on polycaprolactone diol (PCL) were synthesized by reaction of the molecule either with isophorone diisocyanate (IPD-isocyanate) or hexamethylene diisocyanate (HDI-isocyanate). The characterization of the materials was accomplished by: ATR–FTIR (Attenuated Total Reflectance–Fourier Transform Infrared), determination of swelling capacity, stability of NCO groups in the presence of humidity conditions, reaction with aminated substrates (as a simulation of the living tissues) and determination of surface energy by contact angle measurement. The haemocompatibility of the PU was also evaluated by thrombosis and haemolysis tests.
Similar content being viewed by others
References
T. E. LIPATOVA, Adv. Polym. Sci. 79 (1986) 65
L. MONTANARO, C. R. ARCIOLA, E. CENNI, G. CIAPETTI, F. SAVIOLI, F. FILIPPINI and L. A. BARSANTI, Biomaterials 22 (2001) 59
C. J. DUNN and K. L. GOA, Drugs 58 (1999) 863
R. LERNER and N. S. BINUR, J. Surg. Res. 48 (1990) 165
F. H. SILVER, M. WANG and G. D. PINS, Biomaterials 16 (1995) 891
M. E. KING and A. Y. KINNEY, Nurse Pract. Oct. 24 (1999) 69, 70, 73, 74
T. HIDA, S. M. SHETA, A. D. PROIA and B. W. MCCUEN, Retina 8 (1988) 148
A. B. LEAHEY, J. D. GOTTSCH and W. J. STARK, Ophthalmology 100 (1993) 173
M. DONKERWOLCKE, F. BURNY and D. MUSTER, Biomaterials 19 (1998) 1461
S. MATSUDA, H. IWATA, N. SE, Y. IKADA, J. Biomed. Mater. Res. 45 (1999) 20
J. A. BINGLEY, M. A. H. GARDNER, E. GREGORY STAFFORD, T. K. MAU, P. G. POHLNER, R. K. W. TAM, H. JALALI, P. J. TESAR and M. F. O’BRIEN, Ann. Thorac. Surg. 69 (2000) 1764
A. T. NOSOV and A. A. POLIAKOV, Klin. Khir. 12 (1980) 16
I. V. KOMISSARENKO, I. M. KEBULADZE, A. G. LYSENKO and T. V. SHUMOVA, Klin. Khir. 12 (1985) 19
V. S. ZEMSKOV, V. I. BILETSKII, S. N. PANCHENKO, V. S. SHCHITOV and V. N. BLAGODAROV, Klin. Khir. 11 (1986) 3
H. Y. KWEON, M. K. YOO, I. K. PARK, T. H. KIM, H. C. LEE, H-S LEE, J-S OH, T. AKAIKE and C-S CHO, Biomaterials 24 (2003) 801
R. S. BEZWADA, D. D. JAMIOLKOWSKI, I. LEE, A. VISHVAROOP, J. PERSIVALE, S. TREKA-BENTHIN, M. ERNETA, J. SURYADEVARA, A. YANG and S. LIU, Biomaterials 16 (1995) 1141
P. D. DARNEY, S. E. MONROE, C. M. KLAISLE and A. ALVARADO, Am. J. Obstet. Gynecol. 160 (1989) 1292
G. GIAVARESI, M. TSCHON, V. BORSARI, J. H. DALY, J. J. LIGGAT, M. FINI, V. BONAZZI, A. NICOLINI, A. CARPI, M. MORRA, C. CASSINELLI and R. GIARDINO, Biomed. Pharmacother. 58 (2004) 411
K. TOMIHATA, M. SUZUKI, T. OKA and Y. IKADA, Polym. Degrad. Stab. 59 (1998) 13
A. SARASAM and S. MADIHALLY, Biomaterials 26 (2005) 5500
ACD – Anticoagulant Citrate Dextrose Solution, U.S. Pharmacopeia 23 (1995) 119
S. C. H. KWOK, J. WANG and P. K. CHU, Diam. Relat. Mater. 14 (2005) 78
E. CHIBOWSKI, Adv. Colloid Interf. Sci. 103 (2003) 149
DataPhysics Instruments GmbH Operating manual DataPhysics OCA (DataPhysics Instruments GmbH, Germany, 2002), p. 1
N. T. CORREIA, J. J. MOURA RAMOS, B. J. V. SARAMAGO and J. C. G. CALADO, J. Colloid Interf. Sci. 189 (1997) 361
ISO 10993-4 – Biological evaluation of medical devices – Part 4: Selection of tests for interaction with blood, February 1999
Y. IMAI and Y. NOSE, J. Biomed. Mater. Res. 6 (1972) 165
W. D., VILLAR, Chemistry and technology of polyurethanes (Vilar Consultoria, Brazil, 2004), Chap. 1.2
R. LOMOLDER, F. PLOGMANN and P. SPEIER, J. Coatings Technol. 69 (1997) 51
K. HILTUNEN, J. V. SEPPÄLÄ, M. HÄRKÖNEN, J. Appl. Polym. Sci. 64 (1997) 865
J. COMYN, F. BRADY, R. A. DUST, M. GRAHAM and A. HAWARD, Int. J. Adhesion Adhes 18 (1998) 51
R. GALE VENKATRAMAN, Biomaterials 19 (1998) 1119
A. KRATOCHVÍL and E. HRNČÍŘ, Physiol. Res. 50 (2001) 433
Z. CHANGSHENG, L. XIANGDONG, N. MOTOYOSHI and N. NORIO, Biomaterials 24 (2003) 3747
L. POUSSARD, F. BUREL, J.-P. COUVERCELLE, Y. MERHI, M. TABRIZIAN and C. BUNEL, Biomaterials 25 (2004) 3373
American Society for Testing and Materials – ASTM F 756-00 – Standard practices for assessment of haemolytic properties of materials, 2000
Acknowledgments
The authors would like to thank Fundação para a Ciência e Tecnologia for the financial support to P. Ferreira (SFRH/BD/1052/2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ferreira, P., Silva, A.F.M., Pinto, M.I. et al. Development of a biodegradable bioadhesive containing urethane groups. J Mater Sci: Mater Med 19, 111–120 (2008). https://doi.org/10.1007/s10856-007-3117-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10856-007-3117-3