Reactivity assays of surface hydroxyl chain ends of poly(ethylene terephthalate) (PET) film and membranes using original 3H- and fluorine-labeled derivatization reagents

Macromolecules

Volumn 29, Issue 10, 1996, Pages 3552-3559

  Mougenot, Patrick ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; ASSAYS; CELL CULTURE; CHEMICAL ACTIVATION; PLASTIC FILMS; POLYMERIC MEMBRANES; POROUS MATERIALS; SCINTILLATION COUNTERS; SURFACES; X RAY PHOTOELECTRON SPECTROSCOPY;

DERIVATIZATION; FLUORINE TAGS; LIQUID SCINTILLATION COUNTING; LYSINE; SULFONATE ESTERS; SURFACE HYDROXYL CHAIN ENDS; TOSYLATION; TRIFLUOROETHYLLYSINAMIDE;

POLYETHYLENE TEREPHTHALATES;

EID: 0030572159     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9513224     Document Type: Article

References (63)

1. Silver, F. H. Biomaterials, Medical Devices and Tissue Engineering, an Integrated Approach; Chapman and Hall: London, 1994
2. (a) Williams, D. Concise Encyclopedia of Medical and Dental Materials; Pergamon Press: Oxford, U.K., 1990.
3. (b) Szycher, M. High Performance Biomaterials: a Comprehensive Guide to Medical and Pharmaceutical Applications; Technomic Publishing Co.: Lancaster, Basel, 1991.
4. (a) Sergen-Engelen, T.; Delistrie, V.; Schneider, Y.-J. Biochem. Pharmacol. 1993, 46, 1393.
5. (b) Halleux, C.; Schneider. Y.-J. J. Cell. Physiol. 1994, 158, 17.
6. (a) Engers, G. H.; Feijen, J. Int. J. Artif. Organs 1991, 14, 199.
7. (b) Ikada, Y. Biomaterials 1994, 15, 725.
8. (a) Jozefonvicz, J.; Jozefowicz, M. Actual. Chim. 1990, 157.
9. (b) Silver, F.; Doillon C. Polymers; Biocompatibility, Interaction of Biological and Implantable Materials, Vol. I; VCH Publishers, Inc.: New York, 1989.
10. (a) Hirano, Y.; Hayashi, T.; Goto, K.; Nakajima, A. Polym. Bull. 1991, 26, 363.
11. (b) Glass, J. R.; Craig, W. S.; Dickerson, K.; Pierschbacher, M. D. Mater. Res. Soc. Symp. Proc. 1992, 252, 331.
12. (c) Hubbell, J. A. Cardiovasc. Pathol. 1993, 2 (3, Suppl.)121S.
13. Weetall, H. H. J. Biomed. Mater. Res. 1970, 4, 597.
14. Goodman, I. Biotechnological Applications of Proteins and Enzymes; Bohzak, Z., Sharon, N., Eds.; Academic Press: New York, 1977, p 156.
15. Ohshiro, T.; Kosaki, G. Artif. Organs 1980, 4, 58.
16. Oliveira, E. A.; Silva, M. P. C.; Figueiredo, Z. M. B.; Carvalho, L. B., Jr. Appl. Bioehem. Biotechnol. 1989, 22, 109.
17. (a) Massia, S. P.; Hubbell, J. A. Ann. N.Y. Acad. Sci, 1990, 589, 261.
18. (b) Massia, S. P.; Hubbell, J. A. J. Biomed. Mater. Res. 1991, 25, 223.
19. (c) Hubbell, J. A.; Massia, S. P.; Desai, N. P.; Drumheller, P. D. BioTechnology 1991, 9, 568.
20. (d) Hubbell, J. A.; Massia, S. P.; Drumheller, P. D.; Herbert, C. B.; Lyckman, A. W. Polym. Mater. Sci. Eng. 1992, 66, 30.
21. Bùi, L. N.; Thompson, M.; McKeown, N. B.; Romashin, A. D.; Kalman, P. G. Analyst 1993, 118, 463.
22. Bonzon, N.; Lefebvre, F.; Ferre, N.; Daculsi, G.; Rabaud, M. Biomaterials 1995, 16, 747.
23. (a) Marchand-Brynaert, J.; Deldime, M.; Dupont, I.; Dewez, J.-L.; Schneider, Y.-J. J. Colloid Interface Sci. 1995 173, 236.
24. (b) Deldime, M.; Dewez, J.-L.; Schneider, Y.-J.; Marchand-Brynaert, J. Appl. Surf. Sci. 1995, 90, 1.
25. Mougenot, P.; Koch, M.; Dupont, I.; Schneider, Y. -J.; Marchand-Brynaert, J. J. Colloid Interface Sci. 1996, 177, 162.
26. (a) Clark, D. T. Pure Appl. Chem. 1982, 54, 415.
27. (b) Morra, M.; Ochiello, E.; Garbassi, F. Spectroscopy Europe; VCH Publisheres: Weinheim, 1993; Vol. 5, p 10.
28. (a) Batich, C. D.; Wendt, R. C. Chemical Labels to Distinguish Surface Functional Groups Using X-ray Photoelectron Spectroscpy (ESCA); ACS Symposium Series; American Chemical Society: Washington DC. 1981, 162, 221.
29. (b) Everhart, D. S.; Reilly, C. N. Anal. Chem. 1981, 53, 665.
30. (c) Chilkoti, A.; Ratner, B. D.; Briggs, D. Chem. Mater. 1991, 3, 51.
31. (d) Ameen, A. P.; Ward. R. J.; Short, R. D.; Beamson, G.; Briggs, D. Polymer 1993, 34, 1795.
32. (a) Xu, G.-F.; Bergbeiter, D. E.; Letton, A. Chem. Mater. 1992, 4, 1240.
33. (b) McCarthy, T. J. Chimia 1990, 44, 316.
34. Legras, R.; Jongen, Y. Eur. Patent W087/05850, 1986 (French).
35. (a) Keller, O.; Keller, W. E.; Van Look, G.; Wersin, G. Org. Synth 1985, 63, 160.
36. (b) Einhorn, J.; Einhorn, C.; Luche, J.-L. Synlett 1991, 37.
37. (a)Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 4475.
38. (b). Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
39. Bodansky, M.; Bodansky, A. The Practice of Peptide Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1994.
40. Anderson, G. W.; Zimmerman, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1964, 86, 1839.
41. (a) Dourtoglou, V.; Ziegler, J.-C.; Gross, B. Tetrahedron Lett. 1978, 19, 1269.
42. (b) Dourtoglou, V.; Gross, B.; Lambropouloa, V.; Zioudrou, C. Synthesis 1983, 572.
43. (c) Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
44. (a) Sayigh, A. A. R.; Ulrich; H. U.S. Patent 3, 492,331, 1970; (Chem. Abstr. 1970, 72, 78652.
45. (a) Sayigh, A. A. R.; Ulrich; H. U.S. Patent 3, 492,331, 1970; (Chem. Abstr. 1970, 72, 78652.
46. (b) Richter, R.; Ulrich, H. In Chemistry of Cyanates and Isocyanates; Pataï, S., Ed.; John Wiley and Sons New York, 1977; pp 619-818.
47. Nowick, J. S.; Powell, N. A.; Nguyen, T. M.; Noronha, G. J. Org. Chem. 1991, 57, 7364.
48. Massia, S. P.; Hubbell, J. A. Anal. Biochem. 1990, 187, 292.
49. (a) S/C calcd = 0.025/0.975 × 10 + 0.025 × 17) = 0.00246 (S/C experim = 0.00242).
50. (b) S/C calcd = 0.02/(0.98 × 10 + 0.02 × 17) = 0.00197 (S/C experim = 0.00193).
51. (a) F/C calcd = 3 × 0.01/(0.99 × 10 + 0.01 × 18) = 0.0029 (F/C experim = 0.0028).
52. (b) F/C calcd = 3 × 0.014/(0.986 × 10 + 0.014 × 18) = 0.0042 (F/C experim = 0.0041).
53. (a) F/C calcd = 7 × 0.006/(0.994 × 10 + 0.006 × 24) = 0.00416 (F/C experim = 0.00406).
54. (b) F/C calcd = 7 × 0.013/(0.987 × 10 + 0.013 × 24) = 0.00893 (F/C experim = 0.00882).
55. (c) F/C calcd = 7 × 0.02/(0-98 × 10 + 0.02 × 24) = 0.01362 (F/C experim = 0.01379).
56. Ryder, K. S.; Morris, D. G.; Cooper, J. M. J. Chem. Soc., Chem. Commun. 1995, 1471.
57. F/C calcd = 7 × 0.005/(0.996 × 10 + 0.005 × 24) = 0.00347. The starting sample contained 1.3% of fluorine tag (entry 12); the final sample contained 0.5% of fluorine tag (entry 15), C corresponding thus to 62% of ester tranformation with loss of heptafluorobutyl alcohol.
58. Mark, H. F.; Bikales, N. M.; Overberger, C. G.; Menges, G.; Kroachwitz, J. I. Encyclopedia of Polymer Science and Engineering; Wiley-Interacience: New York, 1985.
59. 2.
60. 2.
61. a; that is to say 0.3% of the XPS analyzed volume.
62. 3; that is to say 13% of the XPS analysed volume.
63. Massia, S. P.; Hubbell, J. A. J. Cell Biol. 1991, 114, 1089.