Chemical Modification of Natural and Synthetic Polyesters
Prof. Dr. Emo Chiellini
- [email protected]
- +39-050-918299 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorDr. Ranieri Bizzarri
- [email protected]
- +39-050-3139643 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorDr. Federica Chiellini
- [email protected]
- +39-050-3139641 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorProf. Dr. Emo Chiellini
- [email protected]
- +39-050-918299 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorDr. Ranieri Bizzarri
- [email protected]
- +39-050-3139643 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorDr. Federica Chiellini
- [email protected]
- +39-050-3139641 | Fax: +39-50-28438
University of Pisa, Chemistry and Industrial Chemistry Department, Via Risorgimento 35, Pisa, Italy, I-56126
Search for more papers by this authorAbstract
- Historical Outline and Introductory Remarks
- Malic Acid-based Polyesters
- Poly(α-Malic Acid) and its Copolymers
- Poly(β-Malic Acid) and Poly(alkyl malolactonate)s
- Polyesters with Pendant Amine Groups
- Poly(l-Serine Ester)s
- Poly(lactic acid-co-lysine)
- Functionalization of Poly(ɛ-caprolactone)
- Synthesis of Functional Monomers by the Bayer–Villiger Oxidation of Cyclohexanones
- Post-modification of Functional PCL
- Functional Poly(ester amide)s
- Functional Polyesters by Miscellaneous Polymerization Methods
- Synthesis of Functional Polyesters by Michael-type Reaction
- Synthesis of Functional Polyesters from Protected Polyhydroxylated Monomeric Precursors
- Telechelic Polyesters
- Role of Polymerization Mechanism
- Anionic ROP
- Coordinative ROP
- Coordinative ROP Initiated by Aluminum Alkoxides
- Coordinative ROP Initiated by other Metal Compounds
- Functional Microbial Polyesters
- Concluding Remarks
References
- Abe, C., Taima, Y., Nakamura, Y., Doi, Y. (1990) New bacterial copolyester of 3-hydroxyalkanoates and 3-hydroxy-ω-fluoroalkanoates produced by Pseudomonas oleovorans, Polym. Commun. 31, 404–406.
- Angeloni, A. S., Laus, M., Castellari, C., Galli, G., Ferruti, P., Chiellini, E. (1985) Liquid crystalline poly(β-aminoester)s containing different mesogenic groups, Makromol. Chem. 186, 977–997.
- Angeloni, A. S., Laus, M., Caretti, D., Chiellini, E., Galli, G. (1990) Chiral liquid-crystalline poly(ester/β-sulfoxide)s by asymmetric oxidation of prochiral nematic poly(ester/β−sulfoxide)s, Makromol. Chem. 191, 2787–2793.
- Arnold, L. D., Kalantar, T. H., Vederas, J. C. (1985) Conversion of serine to stereochemically pure β-substituted α-amino acids via β-lactones, J. Am. Chem. Soc. 107, 7105–7109.
- Arnold, S. C., Lenz, R. W. (1986) Synthesis of stereoregular poly(alkyl malolactonates), Macromol. Symp. 6, 285–303.
- Barakat, I., Dubois, P., Jerome, R., Teyssie, P. (1991) Living polymerization and selective end functionalization of ɛ-caprolactone using zinc alkoxides as initiators, Macromolecules 24, 6542–6545.
- Barakat, I., Dubois, P., Jerome, R., Teyssie, P. (1993) Macromolecular engineering of polylactones and polylactides. X. Selective end-functionalization of poly(d,l)-lactide, J. Polym. Sci. Polym. Chem. Ed. 31, 505–514.
- Barakat, I., Dubois, P., Jerome, R., Teyssie, P., Goethals, E. (1994) Macromolecular engineering of polylactones and polylactides. XV. Poly(d,l)-lactide macromonomers as precursors of biocompatible graft copolymers and bioerodible gels, J. Polym. Sci. Polym. Chem. Ed. 32, 2099–2110.
- Barakat, I., Dubois, P., Grandfils, C., Jerome, R. (1996) Macromolecular engineering of polylactones and polylactides. XXI. Controlled synthesis of low molecular weight polylactide macromonomers, J. Polym. Sci. Polym. Chem. Ed. 34, 497–502.
-
Barakat, I.,
Dubois, P.,
Grandfils, C.,
Jerome, R.
(1999)
Macromolecular engineering of polylactones and polylactides. XXV. Synthesis and characterization of bioerodible amphiphilic network and their use as controlled drug delivery system,
J. Polym. Sci. Polym. Chem. Ed. 37,
2401–2411.
10.1002/(SICI)1099-0518(19990715)37:14<2401::AID-POLA14>3.0.CO;2-9 CAS Web of Science® Google Scholar
- Barbaud, C., Cammas-Marion, S., Guerin, P. (1999) Poly(-malic acid) derivatives with non-charged hydrophilic lateral groups: synthesis and characterization, Polym. Bull. 43, 297–304.
- Barenberg, S. A., Brash, J. L., Narayan, R., Redpath, A. E. (1990) Degradable Materials – Perspectives, Issues, and Opportunities, Boca Raton, FL, USA: CRC Press.
- Barrera, D. A., Zylstra, E., Jr., Lansbury, P. T., Langer, R. (1993) Synthesis and RGD peptide modification of a new biodegradable copolymer: poly(lactic acid-co-lysine), J. Am. Chem. Soc. 115, 11010–11011.
- Barrera, D. A., Zylstra, E., Lansbury, P. T., Langer, R. (1995) Copolymerization and degradation of poly(lactic acid-co-lysine), Macromolecules 28, 425–432.
- Barton, D. H. R., Magnus, P. D., Smith, G., Streckert, G., Zurr, D. (1972) Experiments on the synthesis of tetracycline. Part XI. Oxidation of ketone acetals and ethers by hydride transfer, J. Chem. Soc., Perkin Trans. 1, 542–552.
- Bear, M. M., Mallarde, D., Langlois, V., Randriamahefa, S., Bouvet, O., Guerin, P. (1999) Natural and artificial functionalized biopolyesters. II. Medium-chain length polyhydroxyoctanoates from Pseudomonas strains, J. Environ. Polym. Degrad. 7, 179–184.
- Benvenuti, M., Lenz, R. W. (1991) Polymerization and copolymerization of β-butyrolactone and benzyl-β-malolactonate by aluminoxane catalysts, J. Polym. Sci. Polym. Chem. Ed. 29, 793–805.
- Bitritto, M. M., Bell, J. P., Brenckle, G. M., Huang, S. J., Knox, J. R. (1979) Synthesis and biodegradation of polymers derived from α-hydroxy acids, J. Appl. Polym. Sci.-Appl. Polym. Symp. 35, 405–414.
- Bizzarri, R., Chiellini, F., Solaro, R., Chiellini, E., Cammas-Marion, S., Guerin, P. (2001) Synthesis and Characterization of New Malolactonate Polymers and Copolymers for Biomedical Applications (submitted).
- Boutault, K., Cammas, S., Huet, F., Guerin, P. (1995) Polystereoisomers with two stereogenic centers of malic acid 2-methylbutyl ester configurational structure/properties relationship, Macromolecules 28, 3516–3520.
- Braud, C., Bunel, C., Vert, M., Bouffard, P., Clabaut, M., Delpech, B. (1982) 28th IUPAC International Symposium on Macromolecules, Amherst, MA, USA.
- Braud, C., Bunel, C., Garreau, H., Vert, M. (1983) Evidence for the amphiphilic structure of partially hydrogenolyzed poly(β-malic acid benzyl ester), Polym. Bull. 9, 198–203.
- Braud, C., Bunel, C., Vert, M. (1985) Poly(β-malic acid): a new polymeric drug-carrier. evidence for degradation in vitro, Polym. Bull. 13, 293–297.
- Brunelle, D. J. (1993) Ring-Opening Polymerization, Munich: Hanser.
- Cammas, S., Renard, I., Boutault, K., Guerin, P. (1993) A novel synthesis of optically active 4-benzyloxy- and 4-alkyloxycarbonyl-2-oxetanones, Tetrahedron: Asymmetry 4, 1925–1930.
- Cammas, S., Renard, I., Girault, J. P., Guerin, P. (1994a) Poly(β-3-methylmalic acid): a new degradable functional polyester with two stereogenic centers in the main chain, Polym. Bull. 33, 148–158.
- Cammas, S., Boutault, K., Huet, F., Guerin, P. (1994b) 4-Alkyloxycarbonyl-2-oxetanones with two stereogenic centers as precursors of malic acid alkyl esters polystereoisomers, Tetrahedron: Asymmetry 5, 1589–1597.
- Cammas, S., Bear, M.-M., Moine, L., Escalup, R., Ponchel, G., Kataoka, K., Guerin, P. (1999) Polymers of malic acid and 3-alkylmalic acid as synthetic PHAs in the design of biocompatible hydrolyzable devices, Int. J. Biol. Macromol. 25, 273–282.
- Cammas-Marion, S., Guerin, P. (2000) Design of malolactonic acid esters with a large spectrum of specified pendant groups in the engineering of biofunctional and hydrolyzable polyesters, Macromol. Symp. 153, 167–186.
- Caron, A., Braud, C., Bunel, C., Vert, M. (1990) Blocky structure of copolymers obtained by Pd/C-catalysed hydrogenolysis of benzyl protecting groups as shown by sequence-selective hydrolytic degradation in poly(β-malic acid) sequences, Polymer 31, 1797–1802.
- Chedron, H., Ohse, H., Korte, F. (1962) Die Polymerisation von Lactonen, Makromol. Chem. 56, 179–194.
- Chiellini, E., Solaro, R. (1992) New synthetic functional polyester, Macromol. Symp. 54/55, 483–494.
- Chiellini, E., Solaro, R. (1993) New bioerodible-biodegradable hydrophilic polymers, ChemTech 7, 29–36.
- Chiellini, E., Solaro, R. (1995) Macromol. Symp., Multifunctional Bioerodible/Biodegradable Polymeric Materials 98, 803–824.
- Chiellini, E., Solaro, R. (1996a) Biodegradable polymeric materials, Advanced Materials 3, 305–313.
- Chiellini, E., Solaro, R. (1996b) Functional synthetic and semisynthetic polymers in biomedical applications, in: Advanced Biomaterials in Biomedical Engineering and Drug Delivery Systems ( N. Ogata, S. W. Kim, J. Feijen, T. Okano, Eds.), Tokyo: Springer-Verlag, 355–368.
- Chiellini, E., Galli, G., Angeloni, A. S., Laus, M., Pellegrini, R. (1987) Chiral liquid crystal polymers VIII. Thermotropic poly(ester-β-sulphide)s based on variously spaced twin p-oxybenzoate diads, Liquid Crystals 2, 529–537.
- Chiellini, E., Galli, G., Angeloni, A. S., Laus, M. (1990a) Chiral liquid-crystalline polymers. XI. Thermotropic behavior and chiroptical properties in solution of a new series of optically active poly(ester β-sulfide)s, J. Polym. Sci. Polym. Chem. Ed. 28, 3541–3550.
-
Chiellini, E.,
Galli, G.,
Angeloni, A. S.,
Laus, M.
(1990b)
Synthesis and chemical modification of chiral liquid-crystalline poly(ester β-sulphide)s,
ACS Symp. Ser. 6,
79–92.
10.1021/bk-1990-0435.ch006 Google Scholar
- Chiellini, E., Galli, G., Po, R. (1990c) Chiral liquid crystalline polymers, Polym. Bull. 23, 397–402.
- Chiellini, E., Faggioni, S., Solaro, R. (1990d) Polyesters based on glyceric acid derivatives as potential biodegradable materials, J. Bioact. Compat. Polym. 5, 16–29.
- Chiellini, E. E., Giannasi, D., Solaro, R., Chiellini, E., Fernandes, E. G. (1998) Hybrid polymeric hydrogels for the controlled release of protein drugs: DSC investigation of water structure, in: Frontiers in Biomedical Polymer Application ( R. M. Ottenbrite, E. Chiellini, D. Cohn, C. Migliaresi, J. Sunamoto, Eds.), Lancaster, PA, USA: Technomic Publishing Company, Inc., 13–26.
-
Chiellini, E.,
Gil, H.,
Braunegg, G.,
Buchert, J.,
Gatenholm, P.,
Van der Zee, M.
(2001a)
Biorelated Polymers – Sustainable Polymer Science and Technology, New York, USA: Kluwer Academic/Plenum Publishers.
10.1007/978-1-4757-3374-7 Google Scholar
- Chiellini, E., Sunamoto, J., Migliaresi, C., Ottenbrite, R. M., Cohn, D. (2001b) Biomedical Polymers and Polymer Therapeutics, New York, USA: Kluwer Academic/Plenum Publishers.
- Chiellini, F., Petrucci, F., Ranucci, E., Solaro, R. (2001a) Polymeric hydrogels in drug release, in: Biomedical Polymers and Polymer Therapeutics ( E. Chiellini, J. Sunamoto, C. Migliaresi, R. M. Ottenbrite, D. Cohn, Eds.), New York, USA: Kluwer Academic/Plenum Publishers, 63–74.
- Chiellini, F., Schmaljohann, D., Chiellini, E., Ober, C. K., Solaro, R (2001b) (submitted).
-
Cook, A. D.,
Hrkach, J. S.,
Gao, N. N.,
Johnson, I. M.,
Pajvani, U. B.,
Cannizzaro, S. M.,
Langer, R.
(1997)
Characterization and development of RGD-peptide-modified poly(lactic acid-co-lysine) as an interactive, resorbable biomaterial,
J. Biomed. Mater. Res. 35,
513–523.
10.1002/(SICI)1097-4636(19970615)35:4<513::AID-JBM11>3.0.CO;2-C CAS PubMed Web of Science® Google Scholar
- Curley, J. M., Hazer, B., Lenz, R., Fuller, C. (1996) Production of poly(3-hydroxyalkanoate)s containing aromatic substituents by Pseudomonas oleovorans, Macromolecules 29, 1762–1766.
- Davis, G. W., Hill, E. S. (1982) Polyester fiber, in: Encyclopedia of Chemical Technology ( R. E. Kirk, D. F. Othmer, Eds.), New York: John Wiley & Sons, 531–549.
-
Dawes, E. A.
(1990)
Novel Biodegradable Microbial Polymers, Dordrecht: Kluwer Academic Publishers.
10.1007/978-94-009-2129-0 Google Scholar
- Degee, P., Dubois, P., Jerome, R., Teyssie, P. (1992a) Macromolecular engineering of polylactones and polylactides. 9. Synthesis, characterization, and application of ω-primary amine poly(ɛ-caprolactone), Macromolecules 25, 4242–4248.
- Degee, P., Dubois, P., Jerome, R., Teyssie, P. (1992b) Synthesis and characterization of biocompatible and biodegradable poly(ɛ-caprolactone-β-γ-benzylglutamate) diblock copolymer, J. Polym. Sci. Polym. Chem. Ed. 31, 275–278.
- Detrembleur, C., Mazza, M., Halleux, O., Lecomte, P., Mecerreyes, D., Hedrick, J. L., Jerome, R. (2000a) Ring-opening polymerization of γ-bromo-ɛ-caprolactone: a novel route to functionalized aliphatic polyesters, Macromolecules 33, 14–18.
- Detrembleur, C., Mazza, M., Lou, X., Halleux, O., Lecomte, P., Mecerreyes, D., Hedrick, J. L., Jerome, R. (2000b) New functional aliphatic polyesters by chemical modification of copolymers of ɛ-caprolactone with γ-(2-bromo-2-methylpropionate)-ɛ-caprolactone, γ-bromo-ɛ-caprolactone, and a mixture of β- and γ-ene-ɛ-caprolactone, Macromolecules 33, 7751–7760.
- DiBenedetto, L. J., Huang, S. J. (1989) Biodegradable hydroxylated polymers as controlled release agents, ACS Polym. Prep. 30, 403.
- DiBenedetto, L. J., Huang, S. J. (1994) Poly(alkylene tartrate)s as controlled release agents, Polym. Degrad. Stab. 45, 249–255.
- Doi, Y. (1990) Microbial Polyesters, New York, USA: VCH.
- Doi, Y., Abe, C. (1990) Biosynthesis and characterization of a new bacterial copolyester of 3-hydroxyalkanoates and 3-hydroxy-ω-chloroalkanes, Macromolecules 23, 3705–3707.
- Dubois, P., Jerome, R., Teyssie, P. (1989) Macromolecular engineering of polylactones and polylactides. I. End-functionalization of poly(ɛ-caprolactone), Polym. Bull. 22, 475–482.
- Dubois, P., Jerome, R., Teyssie, P. (1991a) Aluminium alkoxides: a family of versatile initiators for the ring-opening polymerization of lactones and lactides, Macromol. Symp. 42/43, 103–116.
- Dubois, P., Jerome, R., Teyssie, P. (1991b) Macromolecular engineering of polylactones and polylactides. 3. Synthesis, characterization, and applications of poly(ɛ-caprolactone) macromonomers, Macromolecules 24, 977–981.
- Dubois, P., Degee, P., Jerome, R., Teyssie, P. (1993) Macromolecular engineering of polylactones and polylactides. 11. Synthesis and use of alkylaluminium dialkoxides and dithiolates as promoters of hydroxy telechelic poly(ɛ-caprolactone) and α,ω-dihydroxy triblock copolymers containing outer polyester blocks, Macromolecules 26, 2730–2735.
- Dubois, P., Zhang, J. X., Jerome, R., Teyssie, P. (1994) Macromolecular engineering of polylactones and polylactides. 13. Synthesis of telechelic polyesters by coupling reactions, Polymer 35, 4998–5004.
- Dubois, P., Degee, P., Ropson, N., Jerome, R. (1997) Macromolecular Design of Polymeric Materials, New York: Marcel Dekker, 247.
- Eguiburu, J. L., Fernandez-Berridi, M. J., Roman, J. S. (1995) Functionalization of poly(l-lactide) macromonomers by ring-opening polymerization of l-lactide initiated with hydroxyethyl methacrylate-aluminium alkoxides, Polymer 36, 173–179.
- Fietier, I., Borgne, A. L., Spassky, N. (1990) Synthesis of functional polyesters derived from serine, Polym. Bull. 24, 349–353.
- Fritzsche, X. K., Lenz, R. W., Fuller, R. C. (1990a) An unusual bacterial polyester with a phenyl pendant group, Makromol. Chem. 191, 1957–1965.
- Fritzsche, K., Lenz, R. W. and Fuller, R. C. (1990b) Production of Unsaturated Polyesters by Pseudomonas oleovorans, Int. J. Biol. Macromol. 12, 85–91.
- Galli, G., Laus, M., Angeloni, A. S., Ferruti, P., Chiellini, E. (1983) Thermotropic poly(β-aminoester)s containing azoxy groups, Macromol. Rapid Commun. 4, 681–686.
- Galli, G., Chiellini, E., Laus, M., Angeloni, A. S. (1989) Thermotropic liquid crystalline poly(ester β-sulfide)s based on twin hexamethylene-spaced p-oxybenzyl diads, Macromolecules 22, 1120–1124.
- Galli, G., Chiellini, E., Laus, M., Angeloni, A. S. (1991) Structural effects on the mesomorphic behaviour of thermotropic liquid crystal poly(ester β-sulphide)s, Eur. Polym. J. 27, 237–241.
- Gelbin, M. E., Kohn, J. (1993) Synthesis and polymerization of N-Z-L-serine-β-lactone and serine hydroxybenzotriazole active esters, J. Am. Chem. Soc. 1993, 3962–3965.
- Goethals, E. J. (1993) Telechelic polymers by ring-opening polymerization, in: Ring-Opening Polymerization ( D. J. Brunelle, Ed.), Munich: Hanser, 295–307.
- Guerin, P., Vert, M. (1987) Enantiomeric purity of R(+) and S(-) benzyl malolactonate monomers as determined by 250 MHz 1H-nuclear magnetic resonance, Polym. Commun. 28, 11–13.
- Guerin, P., Vert, M., Braud, C., Lenz, R. W. (1985) Optically active poly(β-malic acid), Polym. Bull. 14, 187–192.
- Inoue, S., Aida, T. (1993) Living polymerization of acrylic monomers with aluminioporphyrin, Macromol. Symp. 32, 255–265.
- in't Veld, P. J. A., Dijkstra, P. J., Lochem, J. H. V., Feijen, J. (1990) Synthesis of alternating polydepsipeptides by ring-opening polymerization of morpholine-2,5-dione derivatives, Makromol. Chem. 191, 1813–1825.
- in't Veld, P. J. A., Wei-Ping, Y., Klap, R., Dijkstra, P. J., Feijen, J. (1992a) Copolymerization of ɛ-caprolactone and morpholine-2,5-dione derivatives, Makromol. Chem. 193, 1927–1942.
- in't Veld, P. J. A., Dijkstra, P. J., Feijen, J. (1992b) Synthesis of biodegradable polyesteramides with pendant functional groups, Makromol. Chem. 193, 2713–2730.
- Jarm, V., Fles, D. (1977) Polymerization and properties of optically active α-(p-substituted benzenesulfonamido)-β-lactones, J. Polym. Sci. Polym. Chem. Ed. 15, 1061–1071.
- Jedlinski, Z., Kowalczuk, M., Kurcok, P. (1992) Polymerization of β-lactones initiated by alkali metal naphthalenides. A convenient route to telechelic polymers, J.M.S.-Pure Appl. Chem. A29, 1223–1230.
- Kim, O., Gross, R., Hammar, W. J., Newmark, R. A. (1996) Microbial synthesis of poly(β-hydroxyalkanoates) containing fluorinated side-chain substituents, Macromolecules 29, 4572–4581.
- Kim, Y. B., Lenz, R. W., Fuller, R. C. (1991) Preparation and characterization of poly(β-hydroxyalkanoate)s obtained from Pseudomonas oleovorans grown with mixtures of 5-phenylvaleric acid and n-alkanoic acids, Macromolecules 24, 5256–5260.
- Kim, Y. B., Lenz, R. W., Fuller, R. C. (1992) Poly(β-hydroxyalkanoate) copolymers containing brominated repeating units produced by Pseudomonas oleovorans, Macromolecules 25, 1852–1857.
- Kim, Y. B., Lenz, R. W., Fuller, R. C. (1995) Poly(3-hydroxyalkanoate)s containing unsaturated repeating units produced by Pseudomonas oleovorans, J. Polym. Sci. Polym. Chem. Ed. 33, 1367–1374.
- Kimura, Y., Shirotani, K., Yamane, H., Kitao, T. (1988) Ring-opening polymerization of 3(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione: a new route to a poly(α-hydroxy acid) with pendant carboxyl groups, Macromolecules 21, 3338–3340.
- Kimura, Y., Shirotani, K., Yamane, H., Kitao, T. (1993) Copolymerization of 3(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione and l-lactide: a facile synthetic method for functionalized bioabsorbable polymer, Polymer 34, 1741–1748.
- Kirk, R. E., Othmer, D. F. (1991) Encyclopedia of Chemical Technology, Volume 1 ( J. I. Kroschwitz, M. Howe-Grant, Eds.), New York: John Wiley & Sons.
- Kohn, J., Langer, R. (1996) Bioresorbable and bioerodible materials, in: Biomaterials Science ( B. D. Ratner, A. S. Hoffmann, F. S. Schoen, J. E. Lemons, Eds.), San Diego, CA: Academic Press, 64–73.
- Kurcok, P., Matuszowicz, A., Jedlinski, Z. (1995) Anionic polymerization of β-lactones initiated with potassium hydride. A convenient route to polyester macromonomer, Macromol. Rapid Commun. 16, 201–206.
- Laus, M., Angeloni, A. S., Galli, G., Chiellini, E. (1988) Liquid-crystalline poly(β-aminoester)s. Thermotropic mesomorphism and degradability in solution, Makromol. Chem. 189, 743–754.
- Laus, M., Angeloni, A. S., Galli, G., Chiellini, E. (1990) The molecular weight effect on the mesomorphic behaviours of liquid-crystalline poly(ester-β-sulfide)s, Makromol. Chem. 191, 147–154.
- Leboucher-Durand, M.-A., Langlois, V., Guerin, P. (1996) 4-Carboxy-2-oxetanone as a new chiral precursor in the preparation of functionalized racemic or optically active poly(malic acid) derivatives, Polym. Bull. 36, 35–41.
- Lecomte, P., Detrembleur, C., Lou, X., Mazza, M., Halleux, O., Jerome, R. (2000) Novel functionalization routes of poly(ɛ-caprolactone), Macromol. Symp. 157, 47–60.
-
Lee, S. Y.
(1996)
Bacterial polyhydroxyalkanoates,
Biotechnol. Bioeng. 49,
1–14.
10.1002/(SICI)1097-0290(19960105)49:1<1::AID-BIT1>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
-
Lenz, R. W.
(1993)
Biodegradable polymers, in: Biopolymers I ( N. A. Peppas, R. S. Langer, Eds.), Berlin, Germany: Springer-Verlag,
1–40.
10.1007/BFb0027550 Google Scholar
- Lenz, R. W., Johns, D. B., Vert, M., Camps, M., Boileau, S. (1986) Recent investigation on the polymerization reactions of β-lactones and the synthesis of poly(β-malic acid), ACS Polym. Prep. 27, 175–176.
- Lenz, R. W., Kim, B. W., Ulmer, H. W., Fritsche, K., Knee, E., Fuller, R. C. (1990) Functionalized poly(β-hydroxyalkanoate)s produced by bacteria, in: Novel Biodegradable Microbial Polymers ( E. A. Dawes, Ed.), London: Kluwer Academic Publishers, 23–37.
- Lofgren, A., Albertsson, A.-C., Dubois, P., Jerome, R. (1995) Recent advances in ring-opening polymerization of lactones and related compounds, J.M.S.-Pure Appl. Chem. C35, 379–418.
- Matsumura, S., Beppu, H., Toshima, K. (1998) Enzymatic preparation of malate-based polycarboxylates having higher molecular weights by copolymerization with lactone, Chem. Lett. 249–250.
-
Mecerreyes, D.,
Jerome, R.
(1999)
From living to controlled aluminium alkoxide mediated ring-opening polymerization of (di)lactones, a powerful tool for the macromolecular engineering of aliphatic polyesters,
Macromol. Chem. Phys. 200,
2581–2590.
10.1002/(SICI)1521-3935(19991201)200:12<2581::AID-MACP2581>3.0.CO;2-P CAS Web of Science® Google Scholar
- Mecerreyes, D., Atthoff, B., Boduch, K. A., Trollsas, M., Hedrick, J. L. (1999a) Unimolecular combination of an atom transfer radical polymerization initiator and a lactone monomer as a route to new graft copolymers, Macromolecules 32, 5175–5182.
-
Mecerreyes, D.,
Dahan, D.,
Lecomte, P.,
Dubois, P.,
Demonceau, A.,
Noels, A. F.,
Jerome, R.
(1999b)
Ring-opening methathesis polymerization of new α-norborneyl poly(ɛ-caprolactone) macromonomers,
J. Polym. Sci. Polym. Chem. Ed. 37,
2447–2455.
10.1002/(SICI)1099-0518(19990715)37:14<2447::AID-POLA19>3.0.CO;2-9 CAS Web of Science® Google Scholar
- Mecerreyes, D., Humes, J., Miller, R. D., Hedrick, J. L., Detrembleur, C., Lecomte, P., Jerome, R., Roman, J. S. (2000a) First example of an unsymmetrical difunctional monomer polymerizable by two living/controlled methods, Macromol. Rapid Commun. 21, 779–784.
- Mecerreyes, D., Miller, R. D., Hedrick, J. L., Detrembleur, C., Jerome, R. (2000b) Ring-opening polymerization of 6-hydoxynon-8-enoic acid lactone: novel biodegradable copolymers containing allyl pendent groups, J. Polym. Sci. Polym. Chem. Ed. 38, 870–875.
- Mitsunobu, O. (1981) The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products, Synthesis 1–28.
- Moine, L., Cammas, S., Amiel, C., Guerin, P., Sebille, B. (1997) Polymers of malic acid conjugated with the 1-adamantyl moiety as lipophilic pendant group, Polymer 38, 3121–3127.
- Mulzer, J., Bruntrup, G., Chucholowski, A. (1979) Competition in the three-component synthesis triphenylphosphine/azo ester/3-hydroxy-carboxylic acid: OH-versus COOH-activation, Angew. Chem. Int. Edn. Engl. 18, 622–623.
- Ouchi, T., Fujino, A. (1989) Synthesis of poly(α-malic acid) and its hydrolysis behaviour in vitro, Makrom. Chem. 190, 1523–1530.
- Pachence, J. M., Kohn, J. (1997) Biodegradable polymers for tissue engineering, in: Principles of Tissue Engineering ( R. P. Lanza, R. Langer, W. L. Chick, Eds.), Georgetown, TX: Landes Co., Academic Press, Inc., 273–293.
- Pitt, C. G. (1990) Poly-e-caprolactone and its copolymers, in: Biodegradable Polymers as Drug Delivery Systems ( M. Chasin, R. Langer, Eds.), New York: Marcel Dekker, 71–120.
- Pitt, C. G., Gu, Z.-W., Ingram, P., Hendren, R. W. (1987) The synthesis of biodegradable polymers with functional side chains, J. Polym. Sci. Polym. Chem. Ed. 25, 955–966.
-
Platè, N.A.
(1973)
Some problems in the reactivity of macromolecules, in Reactions on Polymers ( J. A. Moore, Ed.), Dordrecht: D. Reidel Publishing Co.,
169–187.
10.1007/978-94-010-2678-9_11 Google Scholar
- Portier, Y., Nawrath, C., Somerville, C. (1995) Production of polyhydroxyalkanoates, a family of biodegradable plastics and elastomers, in bacteria and plants, Biotechnology 13, 142–150.
- Quirk, R. P., Kim, J. (1993) Macromonomers and macroinitiators, in: Ring-Opening Polymerization ( D. J. Brunelle, Ed.), Munich: Hanser, 264–293.
- Renard, I., Cammas, S., Langlois, V., Bourbouze, R., Guerin, P. (1996) Poly(β-3-methyl malic acid), an hydrolyzable polyester: access to tailor-made derivatives with defined configurational structures and study of in vitro compatibility, ACS Polym. Prep. 37, 137–138.
- Rossignol, H., Boustta, M., Vert, M. (1999) Synthetic poly(β-hydroxyalkanoates) with carboxylic acid or primary amine pendent groups and their complexes, Int. J. Biol. Macromol. 25, 255–264.
-
SaintPierre, T.,
Chiellini, E.
(1987)
Biodegradability of synthetic polymers used for medical and pharmaceutical applications. Part 2. Backbone hydrolysis,
Bioactive Compatible Polymers 2,
4–8.
10.1177/088391158700200101 Google Scholar
- Scholz, C., Fuller, R. C., Lenz, R. W. (1994) Production of poly(β-hydroxyalkanoate)s with β-substituents containing terminal ester groups by Pseudomonas oleovorans, Macromol. Chem. Phys. 195, 1405–1421.
- Solaro, R., Bemporad, L., Chiellini, E. (1991) Novel hydroxyl containing polyesters and related polymers viable to the formulation of drug release systems, in: Synthetic Polymers as Drug Carriers. Interactions with Blood ( A. Baszkin, P. Ferruti, M. A. Marchisio, M. C. Tanzi, Eds.), Brescia, Italy: ALFA, 71–77.
- Sosnowski, S., Slomkowsky, S., Penczec, S. (1991) Telechelic poly(ɛ-caprolactone) terminated at both ends with OH groups and its derivatization, Makromol. Chem. 192, 2730–2738.
- Stassin, F., Halleux, O., Dubois, P., Detrembleur, C., Lecomte, P., Jerome, R. (2000) (Triethylsilyloxy)-ɛ-caprolactone and γ-ethylene ketal-ɛ-caprolactone: a route to hetero-graft copolyesters, Macromol. Symp. 153, 27–39.
- Steinbuchel, A., Valentin, M. E. (1995) Diversity of bacterial polyhydroxyalkanoic acids, FEMS Microbiol. Lett. 128, 219–228.
- Storey, R. F., Sherman, J. W. (1996) Novel synthesis of (carboxylic acid)-telechelic poly(ɛ-caprolactone), ACS Polym. Prep. 37, 624–625.
- Storey, R. F., Warren, S. C., Allison, C. J., Wiggins, J. S. (1993) Synthesis of bioresorbable networks from methacrylate-endcapped polyesters, Polymer 34, 4365–4372.
- Tian, D., Dubois, P., Grandfils, C., Jerome, R. (1997a) Ring-opening polymerization of 1,4,8-trioxaspiro[4,6]-9-undecanone: a new route to aliphatic polyesters bearing functional pendent groups, Macromolecules 30, 406–409.
- Tian, D., Dubois, P., Jerome, R. (1997b) Macromolecular engineering of polylactones and polylactides. 23. Synthesis and characterization of biodegradable and biocompatible homopolymers and block copolymers based on 1,4,8-trioxa[4,6]spiro-9-undecanone, Macromolecules 30, 1947–1954.
- Tian, D., Dubois, P., Jerome, R. (1997c) Macromolecular engineering of polylactones and polylactides. 22. Copolymerization of ɛ-caprolactone and 1,4,8-trioxaspiro[4,6]-9-undecanone initiated by aluminium isopropoxide, Macromolecules 30, 2575–2581.
- Tian, D., Dubois, P., Jerome, R. (1998) Ring-opening polymerization of 1,4,8-trioxaspiro-[4,6]-9-undecanone: a route to novel molecular architectures for biodegradable aliphatic polyesters, Macromol. Symp. 130, 217–227.
- Trollsas, M., Hedrick, J. L., Dubois, P., Jerome, R. (1998) Synthesis of acid-functional asymmetric aliphatic polyester, J. Polym. Sci. Polym. Chem. Ed. 36, 1345–1348.
- Vert, M., Lenz, R. W. (1979) Preparation and properties of poly-β-malic acid: a functional polyester of potential biomedical importance, ACS Polym. Prep. 20, 608–611.
- Yamaoka, T., Hotta, Y., Kobayashi, K., Kimura, Y. (1999) Synthesis and properties of malic acid-containing functional polymers, Int. J. Biol. Macromol. 25, 265–271.
- Yasuda, T., Aida, T., Inoue, S. (1983) Living polymerization of β-lactone catalyzed by (tetraphenylporphinato)aluminium chloride. structure of the living end, Macromolecules 16, 1792–1796.
- Yasuda, T., Aida, T., Inoue, S. (1984) Synthesis of end-reactive polymers with controlled molecular weight by metalloporphyrin catalyst, J. Macromol. Sci.-Chem. A21, 1035–1047.
- Zhou, Q.-X., Kohn, J. (1990) Preparation of poly(l-serine ester): a structural analogue of conventional poly(l-serine), Macromolecules 23, 3399–3406.
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