Biodegradable poly (Ester Amide) S: Synthesis and applications

Biodegradable Polymers: Processing, Degradation and Applications

Volumn , Issue , 2011, Pages 207-272

  Rodríguez Galán, Alfonso ^a   Franco, Lourdes ^a   Puiggalí, Jordi ^a  

^a UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

Biodegradation; Biomedical applications; Drug delivery systems; Poly(ester amide)s; Renovable sources; Tssue engineering

Indexed keywords

EID: 84892031911     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (201)

1. Okada, M. Chemical synthesis of biodegradable polymers. Progress in Polymer Science, 2000, 27, 87-133.
2. Lips, PAM; Dijkstra, PJ. Biodegradable Polymers for Industrials applications, CRC Press, Boca Raton, 2005, Ch. 5, pp. 109-139.
3. Coin, I; Dolling, R; Krause, E; Bienert, M; Beyermann, M; Sferdean, CD; Carpino, LA. Depsipeptide methodology for solid-phase peptide synthesis: Circumventing side reactions and development of an automated technique via depsidipeptide units. Journal of Peptide Science 2010, 16, 223-230.
4. Stawikowski, M; Cudic, P. Depsipeptide synthesis. In: Fields GB, editor. Series: Methods in Molecular Biology: Peptide characterization and application protocols, Vol. 386. Humana Press; Totowa, New Jersey USA: 2007. pp. 321-339.
5. Chadwick, AF; Pascu, E. The resolution and rates of hydrolysis of D, L-a-bromopropionic acid and its glycine derivatives. Journal of the Chemical Society, 1943, 65, 392-402.
6. Wang, D; Feng, XD. Copolymerization of ε-caprolactone with (3S) -3-[(benzyloxycarbonyl) methyl]morpholine-2, 5-dione and the C-13 NMR sequence analysis of the copolymer. Macromolecules, 1998, 31, 3824-3831.
7. Zhang, GD; Wang, D; Feng, XD. Preliminary study of hydrogen bonding in (3S) -3-[(benzyloxycarbonyl) methyl]morpholine-2, 5-dione and its effect on polymerization. Macromolecules, 1998, 31, 6390-6092.
8. In't Veld, PJA; Dijkstra, PJ; Feijen, J. Synthesis of biodegradable polyesteramides with pendant functional groups, Macromolecular Chemistry and Physics, 1992, 193, 2713-2730.
9. Vinsova, J. Morpholine-2, 5-diones. Their preparation and exploitation. Chemicke Listy, 2001, 95, 22-27.
10. Hartwig, W; Schoellkopf, U. Asymmetrische Synthesen über heterocyclische Zwischenstufen, XVI. Enantioselektive Synthese von a-Alkyl-a-phenylglycinen durch Alkylieren von an C-6 chiral substituierten 3, 6-Dihydro-3-phenyl-2#-1, 4-oxazin-2-onen. Liebigs Annalen der Chemie, 1982, 1952-1970.
11. Kardassis, G; Brungs, P; Nothhelfer, C; Steckhan, E. Electrogenerated chiral cationic glycine equivalents-Part 2: Chiral 3-methoxy-2, 5-morpholinediones from (S) -cz-hydroxy acids and dimethyl aminomalonate. Tetrahedron, 1998, 54, 3479-3488.
12. Nissen, D; Gilon, C; Goodmann, M. Polydepsipeptides. 4. Synthesis of the alternating polydepsipeptides poly (Ala-Lac) and poly (Val-Lac). Macromolecular Chemistry Supplement, 1975, 1, 23-53.
13. In't Veld, PJA. Biodegradable polyesteramide. Dissertation University of Twente, Netherlands, 1992.
14. Helder, J; Kohn, FE; Sato, S; Van den Berg, JW; Feijen, J. Synthesis of poly[oxyethylidenecarbonylimino (2-oxoethylene)] [poly (glycine-D, L-lactic acid)] by ring opening polymerization. Macromolecular Chemistry Rapid Communication, 1985, 6, 9-14.
15. Shakaby, SW; Koelmel, DF. Copolymers ofp-dioxanone and 2, 5-morpholinediones and surgical devices formed therefrom having accelerated absorption characteristics. EP 0086613 A1 (1983).
16. In't Veld, PJA; Ye, WP; Klap, R; Dijkstra, PJ; Feijen, J. Copolymerization of ε-caprolactone and morpholine-2, 5-dione derivatives. Macromolecular. Chemistry and Physics, 1992, 193, 1927-1942.
17. Samyn, C; Van Beylen, M. Polydepsipeptides: Ring-opening polymerization of 3-methyl-2, 5-morpholinedione, 3, 6-dimethyl-2, 5-morpholinedione and copolymerization thereof with D, L-lactide. Macromolecular Chemistry Macromolecular Symposia, 1988, 19, 225-234.
18. Feng, Y; Klee, D; Höcker, H. Biodegradable block copolymers with poly (ethylene oxide) and poly (glycolic acid-valine) blocks. Journal of Applied Polymer Science, 2002, 86, 2916-2919.
19. Feng, Y; Knüfermann, J; Klee, D; Höcker, H. Enzyme-catalyzed ring-opening polymerization of 3 (S) -isopropyl-morpholine-2, 5-dione. Macromolecular Rapid Communications, 1999, 20, 88-90.
20. Feng, Y; Knüfermann, J; Klee, D; Höcker, H. Lipase-catalyzed ring-opening polymerization of 3 (S) -isopropyl-morpholine-2, 5-dione. Macromolecular Chemistry and Physics, 1999, 200, 1506-1514.
21. Feng, Y; Klee, D; Keul, H; Höcker, H. Lipase-catalyzed ring-opening polymerization of morpholine-2, 5-dione derivatives: A novel route to the synthesis of poly (ester amide) s. Macromolecular Chemistry and Physics, 2000, 201, 2670-2675.
22. Robertz, B; Keul, H; Höcker, H. Polymerization of 5-aza-1-oxa-cycloundecan-4, 11-dione; a mechanistic study. Macromolecular Chemistry and Physics. 1999, 200, 1041-1046.
23. Fey, T; Keul, H; Höcker, H. Interconversion of alternating poly (ester amide) s and cyclic ester amides from adipic anhydride and α, ω-amino alcohols. Macromolecular Chemistry and Physics, 2003, 204, 591-599.
24. Fey, T; Keul, H; Höcker, H. Ring-opening polymerization of the cyclic ester amide derived from adipic anhydride and 1-amino-5-pentanol. Macromolecules, 2003, 36, 3882-3889.
25. Fey, T.; Keul, H.; Höcker, H. Ring-opening polymerization of the cyclic ester amide derived from adipic anhydride and 1-amino-5-hexanol in melt and in solution. Macromolecular Symposia, 2004, 215, 307-324.
26. Robertz, B; Keul, H; Höcker, H. Synthesis of cyclo (amide-ester) s by ring-expansion of #-(acyl) -lactams. Macromolecular Chemistry and Physics 1999, 200, 1034-1045.
27. Goodman, I; Valavanidis, A. Copolyesteramides-I. Anionic copolymers of ω-laurolactam with «=-caprolactone. European Polymer Journal 1984, 20, 241-247.
28. Goodman, I; Vachon, RN. Copolyesteramides-II. Anionic copolymers of ι-caprolactam with í-caprolactone. Preparation and general properties. European Polymer Journal 1984, 20, 529-537.
29. Goodman, I; Vachon, RN. Copolyesteramides-III. Anionic copolymers of f-caprolactam with ϊ-caprolactone. Crystalline character and mechanical properties. European Polymer Journal, 1984, 20, 539-547.
30. Nakayama, A; Higashi, T; Yalcayama, A; Iyoda, J; Ukita, M; Hayashi, K; Yamamoto, N. Biodegradability of copolymers of ε-caprolactone with lactams. Chemistry Express, 1993, 8, 181-4.
31. Gonsalves, KE; Chen, X; Cameron, JA. Degradation of nonalternating poly (ester amide) s, Macromolecules, 1992, 25, 3309-3312.
32. Draye, AC; Persenaire, O; Broze K, J; Roda, J; Kosek, T; Dubois, Ph. Thermogravimetric analysis of poly (s-caprolactam) and poly[(s-caprolactam-co-(s-caprolactone) polymers. Polymer, 2001, 42, 8325-8332.
33. Michaeli, W; Grefenstein, A; Frings, W. Synthesis of polystyrene and styrene copolymers by reactive extrusion. Advanced Polymer Technology, 1993, 12, 25-33.
34. Kim, BJ; White, JL. Continuous polymerization of lactam-lactone block copolymers in a twin-screw extruder. Journal of Applied Polymer Science, 2003, 88, 1429-1437.
35. Kim, BJ; White, JL. Anionic Copolymerization of lauryl lactam and polycaprolactone for the production of a poly (ester amide) triblock copolymer. Journal of Applied Polymer Science, 2003, 90, 3797-3805.
36. Li, MX; Zhuo, RX; Qu, FQ. Synthesis and characterization of novel biodegradable poly (ester amide) with ether linkage in the backbone chain. Journal of Polymer Science: Part A: Polymer Chemistry, 2002, 40, 4550-4555.
37. Montané, J; Armelin, E; Asín, L; Rodríguez-Galán, A; Puiggalí, J. Comparative degradation data of polyesters and related poly (ester amide) s derived from 1, 4-butanediol, sebacic acid, and α-amino acids. Journal of Applied Polymer Science, 2002, 85, 1815-1824.
38. Asín, L; Armelin, E; Montané, J; Rodríguez-Galán, A; Puiggalí, J. Sequential poly (ester amide) s based on glycine, diols, and dicarboxylic acids: thermal polyesterification versus interfacial polyamidation. Characterization of polymers containing stiff unit. Journal of Polymer Science Part A: Polymer Chemistry, 2001, 39, 4283-4293.
39. Kohn, J; Langer, R. Polymerization reactions involving the side chain of α-L-amino acids. Journal of American Chemical Society, 1987, 109, 817-820.
40. Bezemer, JM; Oude Weme, P; Grijpma, DW; Dijkstra, PJ; van Blitterswijk, CA; Feijen, J. Amphiphilic poly (ether ester amide) multiblock copolymers as biodegradable matrices for the controlled release of proteins. Journal of Biomedical Materials Research, 2000, 52, 8-17.
41. Lips, PAM; Broos, R; van Heeringen, MJM; Dijkstra, PJ; Feijen, J. Synthesis and characterization of poly (ester amide) s containing crystallizable amide segments. Polymer, 2005, 46, 7823-7833.
42. Lips, PAM; Broos, R; van Heeringen, MJM; Dijkstra, PJ; Feijen, J. Incorporation of different crystallizable amide blocks in segmented poly (ester amide) s. Polymer 2005, 46, 7834-7842.
43. Timmermann, R; Dujardin, R; Koch, R. Thermoplastisch verarbeitbare und biologish abbaubare aliphatische polyesteramide. DE 43 27 024 A1 (1995).
44. Timmermann, R; Dujardin, R; Koch, R. Thermoplastic processible and biodegradable aliphatic polyesteramides, US 5, 644, 020 (1997).
45. Timmermann, R; Grigat, E; Koch, R. BAK 1095 and BAK 2195: completely biodegradable synthetic thermoplastics. Polymer Degradation and Stability, 1998, 59, 223-226.
46. Botines, E; Rodríguez-Galán, A; Puiggalí, J. Poly (ester amide) s derived from 1, 4-butanediol, adipic acid and 1, 6-aminohexanoic acid: Characterization and degradation studies. Polymer, 2002, 43, 6073-6084.
47. Morgan, PW. (1965). Condensation Polymers by Interfacial and Solution Methods, John Wiley and Sons Inc. New York.
48. Starks, CM. Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. Journal of American Chemical Society, 1971, 93, 195-199.
49. Paredes, N; Rodríguez-Galán, A; Puiggalí, J. Synthesis and characterization of a family of biodegradable poly (ester amide) s derived from glycine. Journal of Polymer Science Part A: Polymer Chemistry, 1998 36, 1271-1282.
50. Paredes, N; Casas, MT; Puiggalí, J. Poly (ester amide) s derived from glycine, even-numbered diols, and dicarboxylic acids: Considerations on the packing. Journal of Polymer Science Part B: Polymer Physics, 2001, 39, 1036-1045.
51. Paredes, N; Casas, MT; Puiggalí, J; Lotz, B. Structural data on the packing of poly (ester amide) s derived from glycine, hexanediol and odd-numbered dycrboxylic acids. Journal of Polymer Science Part B: Polymer Physics, 1999, 37, 2521-2533.
52. Han, SI; Kim, BS; Kang, SW; Shirai, H; Im, SS. Cellular interactions and degradation of aliphatic poly (ester amide) s derived from glycine and/or 4-amino butyric acid. Biomaterials, 2003, 24, 3453-3462.
53. Lee, SY; Park, JW; Yoo, YT; Im, SS. Hydrolytic degradation behaviour and microstructural changes of poly (ester-co-amide) s. Polymer Degradation and Stability, 2002, 78, 63-71.
54. Kim, HW; Chung, CW; Kim, SS; Kim, YB; Rhee, YH. Preparation and cell compatibility of acrylamide-grafted poly (3-hydroxyoctanoate). International Journal of Biological Macromolecules, 2002, 30, 129-35.
55. Paredes, N; Rodríguez-Galán, A; Puiggalí, J; Peraire, C. Studies on the biodegradation and biocompatibility of a new poly (ester amide) derived from L-alanine. Journal of Applied Polymer Science, 1998, 69, 1537-1549.
56. Rodríguez-Galán, A; Fuentes, L; Puiggalí, J. Studies on the degradability of a poly (ester amide) derived from L-alanine, 1, 12-dodecanediol and 1, 12-dodecanedioic acid. Polymer, 2000, 41, 5967-5970.
57. Reeve, MS; McCarthy, SP; Downey, MJ; Gross, RA. Polylactid stereochemistry: effect on enzymic degradability. Macromolecules, 1994, 27, 825-831.
58. Abe, H; Matsubara, I; Doi, Y; Hori, Y; Yamaguchi, A. Physical properties and enzymic degradability of Poly (3-hydroxybutyrate stereoisomers with different stereoregularities. Macromolecules, 1994, 27, 6018-6025.
59. Nagata, M. Synthesis and enzymatic degradation of poly (ester-amide) stereocopolymers derived from alanine. Macromolecular Chemistry and Physics, 1999, 200, 2059-2064.
60. Rodríguez-Galán, A; Pelfort, M; Aceituno, JE; Puiggali, J. Comparative studies on the degradability of poly (ester amide) s derived from L-and L, D-alanine. Journal of Applied Polymer Science, 1999, 74, 2312-2320.
61. Castaldo, L; de Candia, F; Maglio, G; Palumbo, R; Strazza, G. Synthesis and physico-mechanical properties of aliphatic polyesteramides. Journal of Applied Polymer Science, 1982, 27, 1809-1822.
62. Armelin, E; Franco, L; Rodríguez-Galán, A; Puiggalí, J. Study on the degradability of poly (ester amide) s related to nylons and polyesters 6, 10 or 12, 10. Macromolecular Chemistry and Physics, 2002, 203, 48-58.
63. Luckachan, GE; Pillai, CKS. Random multiblock poly (ester amide) s containing poly (L-lactide) and cycloaliphatic amide segments: synthesis and biodegradation studies. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44, 3250-3260.
64. Vanhaecht, B; Willem, R; Biesemans, M; Goderis, B; Basiura, M; Magusin, PCMM.; Dolbnya, I; Koning, CE. A WAXD and solid-state NMR study on cocrystallization in partially cycloaliphatic polyamide 12. 6-based copolymers. Macromolecules, 2004, 37, 421-428.
65. Vanhaecht, B; Goderis, B; Magusin, PCMM; Mezari, B; Dolbnya, I; Koning, CE. Stereochemistry driven distribution of 1, 4-diaminocyclohexane residues over the crystalline and amorphous phase in copolyamides 4. 14/1, 4-DACH. 14. A solid-state NMR and temperature-dependent WAXD study. Macromolecules, 2005, 38, 6048-6055.
66. Lecomte, HA; Liggat, JJ; Curtis, ASG. Synthesis and characterization of novel biodegradable aliphatic poly (ester amide) s containing cyclohexane units. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44, 1785-1795.
67. Katsarava, R; Beridze, V; Arabuli, N; Kharadze, D; Chu, CC; Won, CY. Amino acid-based bioanalogous polymers. Synthesis, and study of regular poly (ester amide) s based on bis (a-amino acid) α, ω-alkylene diesters, and aliphatic dicarboxylic acids. Journal of Polymer Science Part A: Polymer Chemistry, 1999, 37, 391-407.
68. Katsarava, R. Active polycondensation: From peptide chemistry to amino acid based biodegradable polymers. Macromolecular Symposia, 2003, 199, 419-429.
69. Fan, Y; Kobayashi, M; Kise, H. Synthesis and biodegradation of poly (ester amide) s containing amino acid residues: The effect of the stereoisomeric composition of L-and D-phenylalanines on the enzymatic degradation of the polymers. Journal of Polymer Science Part A: Polymer Chemistry, 2002, 40, 385-392.
70. Koyama, E; Sanda, F; Endo, T. Polycondensations of hydroxycarboxylic acids derived from optically active aminoalcohols and acid anhydrides-Synthesis of functional poly (ester-amide) s. Journal of Polymer Science Part A: Polymer Chemistry, 1997, 35, 345-352.
71. Fey, T; Keul, H; Höcker, H. Alternating poly (ester amide) s from glutaric anhydride and α, ω-aminoalcohols: synthesis and thermal properties. e-Polymers 2003, no. 001.
72. Koyama, E; Sanda, F; Endo, T. Polycondensations of dicarboxylic acids and diols derived from optically active amino alcohols. Journal of Polymer Science Part A: Polymer Chemistry, 1997, 35, 2925-2934.
73. Hsiao, SH; Leu, WT. Synthesis and properties of novel aromatic poly (ester-amide) s derived from 1, 5-bis (3-aminobenzoyloxy) naphthalene and aromatic dicarboxylic acids. Polymer International, 2005, 54, 392-400.
74. Kulkarni, SM; Kelkar, AA; Chaudhari, RV. Synthesis of polyesteramides by a new palladium catalyzed carbonylation-polycondensation reaction. Chemical Communications, 2001, 1276-1277.
75. Epple, M; Kirschnick, H. The thermally induced solid-state polymerization reaction in halogenoacetates. Chemische Berichte 1996, 129, 1123-1129.
76. Schwarz, K; Epple, M. A detailed characterization of polyglycolide prepared by solidstate polycondensation reaction. Macromolecular Chemistry and Physics 1999, 200, 2221-2229.
77. Epple, M; Kirschnick, H. Oligomerization and Polymerization in Sodium Salts of Chlorocarboxylic Acids. Liebigs Annalen der Chemie, 1997, 81-85.
78. Hezberg, O; Epple, M. Formation of Polyesters by Thermally Induced Polymerization Reactions of Molecular Solids. European Journal of Inorganic Chemistry, 2001, 6, 1395-1406.
79. Roby MS; Jiang Y. Polyesteramides with amino acid-derived groups alternating with α-hydroxiacid-derived groups and surgical articles made therefrom. US 005, 914, 387 A (1999).
80. Rodríguez-Galán, A; Vera, M; Franco, L; Puiggalí, J. Synthesis of poly (ester amide) s derived from glycolic acid and the amino acids: β-alanine or α-aminobutyric acid. Macromolecular Chemistry and Physics, 2003, 204, 2078-2089.
81. Vera, M; Rodríguez-Galán, A; Puiggalí, J. New method of synthesis of poly (ester amide) s derived from the incorporation of glycolic acid residues into aliphatic polyamide. Macromolecular Rapid Communications, 2004, 25, 812-817.
82. Vera, M; Franco, L; Puiggalí, J. Synthesis and characterization of poly (glycolic acid-alt-6-aminohexanoic acid) and poly (glycolic acid-alt-11-aminoundecanoic acid). Macromolecular Chemistry and Physics, 2004, 205, 1782-1792.
83. Ramis, X; Salla, JM; Puiggalí, J. Kinetic studies on the thermal polymerization of N-chloroacetyl-11-aminoundecanoate potassium salt. Journal of Polymer Science Part A: Polymer Chemistry, 2005, 43, 1166-1176.
84. Botines, E; Franco, L; Ramis, X; Puiggalí, J. Synthesis of poly (glycolic acid-alt-12-aminododecanoic acid): The thermal polymerization kinetics of sodium N-chloroacetyl-12-aminododecanoate. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44, 1199-1213.
85. Botines, E; Casas, MT; Puiggalí, J. Alternating poly (ester amide) s of glycolic acid and ω-amino acids: Crystalline morphology and main crystallographic data. Journal of Polymer Science Part B: Polymer Physics, 2007, 45, 815-825.
86. Botines, E; Franco, L; Puiggalí, J. Thermal stability and degradation studies of alternating poly (ester amide) s derived from glycolic acid and ω-amino acids. Journal of Applied Polymer Science, 2006, 102, 5545-5558.
87. del Valle, LJ; Sepulcro, F; Gámez, A; Rodríguez-Galán, A; Puiggalí, J. New poly (ester amide) s containing glycolic acid units: Evaluation of biocompatibility. Currents Trends in Polymer Science, 2008, 12, 27-32.
88. Vera, M; Admetlla, M; Rodríguez-Galán, A; Puiggalí, J. Synthesis, characterization and degradation studies of sequential poly (ester amide) s derived from glycolic acid, 1, 6-hexanediamine and aliphatic dicarboxylic acids. Polymer Degradation and Stability, 2005, 89, 21-32.
89. Barrows, TH. Synthetic absorbable surgical devices of polyester amides and process for making them. EP 030822 (1998).
90. Barrows, TH. Process for preparing synthetic absorbable poly (esteramides). US 4, 529, 792 (1985).
91. Barrows, TH; Truong, MUS. Bioabsorbable poly (esteramide) and method for making same. WO 12814 (1993).
92. Douhi, A; Fradet, A. Study of bulk chain coupling reactions. III. Reaction between bisoxazolines or bisoxazlines and carboxy-terminated oligomers. Journal of Polymer Science. Part A: Polymer Chemistry, 1995, 33, 691-699.
93. Chalamet, Y; Taha, M. Carboxyl terminated polyamide 12 chain extension using a dioxazoline coupling agent. Journal of Polymer Science. Part A: Polymer Chemistry, 1997, 35, 3697-3705.
94. Pó, R; Abis, L; Fiocca, L; Mansanis, R. Synthesis and characterization of poly (ester-amide) s from bis (2-oxazoline) s, anhydrides, and diols. Macromolecules, 1995, 28, 5699-5705.
95. Pó, R; Fiocca, L; Abis, L. Copolymerization of bis (2-oxazoline) s, anhydrides, and diols or diamines. Reaction mechanisms and polymer properties. Journal of Polymer Science. Part A: Polymer Chemistry, 1997, 35, 3241-3248.
96. Mansour, I; Alouani, K; Chauveau, E; Martin, V; Schiets, F; Mercier, R. Synthesis and characterisation of poly (ester-amide) s from aromatic bisoxazoline precursors. European Polymer Journal, 2010, 46, 814-820.
97. Luston, J; Kronek, J; Markus, O; Janigova, I; Böhme, F. Synthesis and polymerization reactions of cyclic imino ethers. 3. Poly (ester amide) s of the AA+BB type on the basis of 2-oxazolines. Polymers for Advanced Technologies, 2007, 18, 165-172.
98. Chevallier, P; Soutif, JC; Brosse, JC; Rincón-Guerrero, A. Poly (amide-ester) s from 2, 6-pyridine dicarboxylic acid and ethanolamine derivatives for metal ion complexation. Synthesis via bis (2-oxazoline) -diacid reaction. European Polymer Journal, 1998, 34, 767-778.
99. Jakisch, L; Böhme, F; Komber, H; Pompe, G. Synthesis and thermal polymerization of aromatic 2-oxazolines containing carboxylic groups. Macromolecular Rapid Communication, 1999, 20, 256-260.
100. Tuominen, J; Seppälä, JV. Synthesis and characterization of lactic acid based poly (ester-amide). Macromolecules, 2000, 33, 3530-3535.
101. Borriello, A, Nicolais, L, Fang, X, Huang, SJ; Scola, DA. Synthesis of poly (amide-ester) s by microwave methods. Journal of Applied Polymer Science, 2007, 103, 1952-1958.
102. Borriello, A, Nicolais, L, Huang, SJ. Poly (amide-ester) s derived from dicarboxylic acid and aminoalcohol. Journal of Applied Polymer Science, 2005, 95, 362-368.
103. Fang, X; Hutcheon, R; Scola, DA. Microwave Syntheses of Poly (s-caprolactam-co-s-caprolactone). Journal of Polymer Science: Part A: Polymer Chemistry, 2000, 38, 1379-1390.
104. Jokhadze, G; Machaidze, M; Panosyan, H; Chu, CC; Katsarava, R. Synthesis and characterization of functional elastomeric poly (ester amide) s copolymers. Journal of Biomaterials Science, Polymer Edition, 2007, 18, 411-438.
105. Chu, CC; Katsarava, R. Elastomeric functional biodegradable copolyester amides and copolyester urethanes. US 6, 503, 538 B1 (2003).
106. Guo, K; Chu, CC. Synthesis, characterization, and biodegradation of copolymers of unsaturated and saturated poly (ester amide) s. Journal of Polymer Science, Part A: Polymer Chemistry, 2007, 45, 1595-1606.
107. Guo, K; Chu, CC. Biodegradation of unsaturated poly (ester-amide) s and their hydrogels, Biomaterials, 2007, 28, 3284-3294.
108. Guo, K; Chu, CC; Chkhaidze, E; Katsarava, R. Synthesis and characterization of novel biodegradable unsaturated poly (ester amide) s. Journal of Polymer Science, Part A: Polymer Chemistry, 2005, 43, 1463-1477.
109. Guo, K; Chu, CC. Copolymers of unsaturated and saturated poly (ether ester amide) s: Synthesis, characterization, and biodegradation. Journal of Applied Polymer Science, 2008, 110, 1858-1869.
110. Guo, K.; Chu, CC. Controlled release of paclitaxel from biodegradable unsaturated poly (ester amide) s/poly (ethylene glycol) diacrylate hydrogels. Journal Biomaterials Science, Polymer Edition, 2007, 18, 489-504.
111. De Wit, MA; Wang, Z; Atkins, KM; Mequanint, K; Gillies, ER. Synthesis, characterization, and functionalization of poly (ester amide) s with pendant amine functional groups. Journal of Polymer Science, Part A: Polymer Chemistry, 2008, 46, 6376-6392.
112. Vera, M; Franco, L; Puiggali, J. Synthesis of poly (ester amide) s with lateral groups from a bulk polycondensation reaction with formation of sodium chloride salts. Journal of Polymer Science, Part A: Polymer Chemistry, 2008, 46, 661-667.
113. Atkins, KM; Lopez, D; Knight, DK; Mequanint, K; Gillies, ER. A versatile approach for the syntheses of poly (ester amide) s with pendant functional groups. Journal of Polymer Science, Part A: Polymer Chemistry, 2009, 47, 3757-3772.
114. de Wit, MA; Wang, ZX; Atkins, KM; Mequanint, K; Gillies, ER. Synthesis, characterization, and functionalization of poly (ester amide) s with pendant amine functional groups. Journal of Polymer Science, Part A: Polymer Chemistry. 2009, 47, 6376-6392.
115. Deng, M; Wu, J; Reinhart-King, CA; Chu, CC. Synthesis and characterization of biodegradable poly (ester amide) s with pendant amine functional groups and in vitro cellular response. Biomacromolecules, 2009, 10, 3037-3047.
116. Pang, X; Chu, CC. Synthesis, characterization and biodegradation of functionalized amino acid-based poly (ester amide) s. Biomaterials, 2010, 31, 3745-3754.
117. Horwitz, JA; Shum, KM; Bodle, JC; Deng, M; Chu, CC; Reinhart-King, CA. Biological performance of biodegradable amino acid-based poly (ester amide) s: Endothelial cell adhesion and inflammation in vitro. Journal of Biomedical Materials Research Part A, 2010, 95, 371-380.
118. Bettinger, CJ; Bruggeman, JP; Borenstein, JT; Langer, RS. Amino alcohol-based degradable poly (ester amide) elastomers. Biomaterials, 2008, 29, 2315-2325.
119. Barrera, DA; Zylstra, E; Lansbury, PT; Langer, R. Synthesis and RGD peptide modification of a new biodegradable copolymer: Poly (lactic acid-co-lysine). Journal American Chemical Society, 1993, 115, 11010-11011.
120. Ouchi, T; Nozaki, T; Ishikawa, A; Fujimoto, I; Ohya, Y. Synthesis and enzymatic hydrolysis of lactic acid-depsipeptide copolymers with functionalized pendant groups. Journal of Polymer Science, Part A: Polymer Chemistry, 1997, 35, 377-383.
121. John, G; Tsuda, S; Morita, M. Synthesis and modification of new biodegradable copolymers: Serine/glycolic acid based copolymers, Journal of Polymer Science, Part A: Polymer Chemistry, 1997, 35, 1901-1907.
122. Wang, D; Feng, XD. Synthesis of poly (glycolic acid-alt-L-aspartic acid) from a morpholine-2, 5-dione derivative, Macromolecules, 1997, 30, 5688-5692.
123. Rypaâcïek, F; Sïtefko, I; Machovaâ, L; Kubies, D; Brus, J. Synthesis of ester-amide copolymers from lactones and N-carboxyanhydrides, Polymer Preprints, 1998, 39, 126-127.
124. Guo, K; Chu, CC; Chkhaidze, E; Katsarava, R. Synthesis and characterization of novel biodegradable unsaturated poly (ester amide) s. Journal of Polymer Science Part A: Polymer Chemistry, 2005, 43, 1463-1477.
125. Guo, K; Chu, CC. Synthesis, characterization, and biodegradation of copolymers of unsaturated and saturated poly (ester amide) s. Journal of Polymer Science Part A: Polymer Chemistry, 2007, 45, 1595-1606.
126. Guo, K; Chu, CC. Copolymers of unsaturated and saturated poly (ether ester amide) s: Synthesis, characterization, and biodegradation. Journal of Applied Polymer Science, 2008, 110, 1858-1869.
127. Guo, K; Chu, CC. Biodegradation of unsaturated poly (ester-amide) s and their hydrogels. Biomaterials, 2007, 28, 3284-3294.
128. Guo, K; Chu, CC. Synthesis and characterization of novel biodegradable unsaturated poly (ester amide) /poly (ethylene glycol) diacrylate hydrogel. Journal of Polymer Science Part A: Polymer Chemistry, 2005, 43, 3932-3944.
129. Ai, Y; Shi, Z; Guo, W. A new type of unsaturated poly (ester-amide): Synthesis and compressive strength. Materials and Design, 2009, 30, 892-895.
130. Ai, Y; Shi, Z; Guo, W; Xie, S. Synthesis and characterization of a potential material as internal fixation of bone fracture. Materials Science and Engineering, 2009, 29, 1001-1005.
131. Ai, Y; Shi, Z; Guo, W. Calcium Polyphosphate Fibers/Unsaturated Poly (ester-amide) Composites for Bone-Fixation Materials. Polymer Composites, 2009, 30, 1119-1124.
132. Bezemer, JM; Weme, PO; Grijpma, DW; Dijkstra, PJ; Bilitterseijk, CA; Feijen, J. Amphiphilic poly (ether ester amide) multiblock copolymers as biodegradable matrices for the controlled release of proteins. Journal of Biomedical Materials Research, 2000, 52, 8-17.
133. Wang, L; Wang, Y; Cao, D. Synthesis and characterization of new unsaturated degradable poly (ether ester amide) s containing ethylene oxide moieties. Journal of Macromolecular Science Part A: Pure and Applied Chemistry, 2009, 46, 282-289.
134. Xiao, C; He, Y. Tailor-made unsaturated poly (esteramide) network that contains monomeric lactate sequences. Polymer International, 2007, 56, 816-819.
135. Patel, HS; Panchal, KK. Novel unsaturated polyester amide resins based on epoxy resins. Polymer-Plastics Technology and Engineering, 2004, 43, 1177-1185.
136. Villuendas, I; Iribarren, JI; Muňoz-Guerra, S. Poly (ester amide) s derived from L-tartaric acid and amino alcohols. i. Regic polymers. Macromolecules, 1999, 32, 8015-8023.
137. Regaňo, C; Martínez de Ilarduya, A; Iribarren, JI; Muňoz-Guerra, S. Poly (ester amide) s derived from L-tartaric acid and amino alcohols. ii. Aregic polymers. Journal of Polymer Science: Part A: Polymer Chemistry, 2000, 38, 2687-2696.
138. Regaňo, C; Marín, R; Alla, A; Iribarren, JI; Martínez de Ilarduya, A; Muňoz-Guerra, S. Crystallization and crystal structure of poly (ester amide) s derived from L-tartaric acid. Journal of Polymer Science, Part B: Polymer Physics, 2007, 45, 116-125.
139. Villuendas, I; Molina, I; Regaňo, C; Bueno, M; Martínez de Ilarduya, A; Galbis, JA; Muňoz-Guerra, S. Hydrolytic degradation of poly (ester amide) s made from tartaric and succinic acids: Influence of the chemical structure and microstructure on degradation rate. Macromolecules, 1999, 32, 8033-80.
140. Alla, A; Rodríguez-Galán, A; Muňoz-Guerra, S. Hydrolytic and enzymatic degradation of copoly (ester amide) s based on L-tartaric and succinic acids. Polymer, 2000, 41, 6995-700.
141. Pérez-Rodríguez, A; Alla, A; Fernández-Santín, JM; Muňoz-Guerra, S. Poly (ester amide) s derived from tartaric and succinic acids: changes in structure and properties upon hydrolytic degradation. Journal of Applied Polymer Science, 2000, 78, 486-494.
142. Molina Pinilla, I; Bueno Martinez, M; Galbis Pérez, JA. Synthesis of a Stereoregular Poly (ester amide) Derived from L-Arabinose. Macromolecules, 1995, 28, 3766-3770.
143. Molina Pinilla, I; Bueno Martínez, M; Zamora Mata, F; Galbis, JA. Synthesis and properties of stereoregular poly (ester amides) derived from carbohydrates. Journal of Polymer Science, Part A: Polymer Chemistry, 1998, 36, 67-77.
144. Molina Pinilla, I; Bueno Martínez, M; Zamora Mata, F; Galbis, JA. Hydrolytic degradation of poly (ester amides) derived from carbohydrates. Macromolecules, 1997, 30, 3197-3203.
145. Molina Pinilla, I; Bueno Martínez, M; Zamora Mata, F; Galbis, JA. Carbohydrate-based copolymers. Synthesis and characterization of copoly (ester amide) s containing L-arabinose units. Macromolecules, 2002, 35, 2977-2984.
146. Gomurashvili, Z; Kricheldorf, HR; Katsarava, R. Amino acid based bioanalogous polymers. Synthesis and study of new poly (ester amide) s composed of hydrophobic α-amino acids and dianhydrohexitoles. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 2000, 37, 215-227.
147. Okada, M; Yamada, M; Yokoe, M; Aoi, K. Biodegradable polymers based on renewable resources. V. Synthesis and biodegradation behavior of poly (ester amide) s composed of 1, 4:3, 6-dianhydro-D-glucitol, α-amino acid, and aliphatic dicarboxylic acid units. Journal of Applied Polymer Science, 2001, 81, 2721-2734.
148. Landis, GC; Turnell, WG; Yumin, Y. Delivery of ophthalmologic agents to the exterior or interior of the eye. US 0, 292, 476 A1 (2007).
149. Ahmad, S; Ashraf, SM; Zafar, F. Development of Linseed Oil Based Polyesteramide without Organic Solvent at Lower Temperature. Journal of Applied Polymer Science, 2007, 104, 1143-1148.
150. Kozlowska, A; Ukielski, R. New type of thermoplastic multiblock elastomers. Poly (ester-block-amide) s based on oligoamide 12 and oligoester prepared from dimerized fatty acid. European Polymer Journal, 2004, 40, 2767-2772.
151. Sasaki, S; Miyauchi, M. Journal of the Agricultural Chemical Society of Japan. 1942, 18, 54.
152. Kropa, EL. Fatty acids fatty amines alkanolamines soaps. US. 2, 440, 516 (1948).
153. Chelnokova, GN.; Koshak, VV. Sbornik Stateipo Obshchei Khimii, 1953, 2, 1070-1075.
154. Dachs, K; Kutepow, NV; Wilhelm, H; Jaeckel, K.; Detzer, H. Verfahren zur herstllung von transparenten polyamiden. DE 1, 050, 053 (1959).
155. Kibler, CJ; Bell, A; Smith, JG. Linear polyesters of 1, 4-cyclohexane-dimethanol and hydroxycarboxylic acids. US 3, 033, 822 (1962).
156. Vera, M; Almontassir, A; Rodríguez-Galán, A; Puiggalí, J. Synthesis and characterization of a new degradable poly (ester amide) derived from 6-amino-1-hexanol and glutaric acid. Macromolecules, 2003, 36, 9784-9796.
157. Fey, T; Hölscher, M; Keul, H; Höcker, H. Alternating poly (ester amide) s from succinic anhydride and α, ω-amino alcohols: synthesis and thermal characterization. Polymer International, 2003, 52, 1625-1632.
158. Huang, SJ. Encyclopedia of Polymer Science and Engineering, Wiley Interscience, New York, 1985, Vol. 2, pp. 220-244.
159. Huang, SJ; Kim, SH. Poly (amide-ester) s from p-aminobenzoic acid. Polymer International, 1998, 46, 172-176.
160. Sudha, JD; Pillai, CKS. Hydrogen-bonded thermotropic liquid-crystalline polyester-amides from bis (hydroxy alkamido) aranes: Synthesis and properties. Journal of Polymer Science Part A: Polymer Chemistry, 2003, 41, 335-346.
161. Krystyna, B; Wiec, TL; Jedlinski, Z. Bulletin of Polish Academy Science Chemistry, 1989, 37, 3-4.
162. Sudha, JD. Synthesis and characterization of hydrogen-bonded thermotropic liquid crystalline aromatic-aliphatic poly (ester-amide) s from amido diol. Journal of Polymer Science Part A: Polymer Chemistry, 2000, 38, 2469-2486.
163. Lozano, M; Franco, L; Rodríguez-Galán, A; Puiggalí, J. Poly (ester amide) s derived from 1, 4-butanediol, adipic acid and 6-aminohexanoic acid Part III: substitution of adipic acid units by terephthalic acid units. Polymer Degradation and Stability, 2004, 85, 595-604.
164. Chiellini E; Bizzarri R; Bonaguidi, P; Talamelli P; Solaro, R. Multifunctional hydrophilic polymers. Journal of Macromolecular Science, Part A, 1999, 36, 901-915.
165. Wang, L; Wang, Y; Ren, L. Synthesis and characterization of novel biodegradable aromatic-aliphatic poly (ester amide) s containing ethylene oxide moieties. Journal of Applied Polymer Science, 2008, 109, 1310-1318.
166. Sacripante, GG; McAneny, TB. Polyesteramide-siloxane toner and developer compositions. US 5, 401, 601 (1995).
167. Sharma, B; Azim, A; Azim, H; Gross, RA; Zini, E; Focarete, ML; Scandola, M. Enzymatic synthesis and solid-state properties of aliphatic polyesteramides with polydimethylsiloxane blocks. Macromolecules, 2007, 40, 7919-7927.
168. Barbato, F; la Rotonda, MI; Maglio, G; Palumbo, R; Quaglia, F. Biodegradable microspheres of novel segmented poly (ether-ester-amide) s based on poly (s-caprolactone) for the delivery of bioactive compounds. Biomaterials, 2001, 22, 1371-1378.
169. Ostacolo, L; Russo, P; de Rosa, G; la Rotonda, MI; Maglio, G; Nese, G; Spagnuolo, G; Rengo, S; Oliva, A; Quaglia, F. Poly (ether ester amide) microspheres for protein delivery: Influence of copolymer composition on technological and biological properties. Macromolecular Bioscience, 2008, 8, 682-689.
170. Guo, K; Chu, CC. Biodegradable and injectable paclitaxel-loaded poly (ester amide) s microspheres: Fabrication and characterization. Journal of Biomedical Materials Research Part B-Applied Biomaterials, 2009, 89, 491-500.
171. Vera, M; Puiggali, J; Coudane, J. Microspheres from new biodegradable poly (ester amide) s with different ratios of L-and D-alanine for controlled drug delivery. Journal of Microencapsulation, 2006, 23, 686-697.
172. Qian, ZY; Li, S; He, Y; Zihang, HL; Liu, XB. Preparation of biodegradable polyesteramide microspheres. Colloid and Polymer Science, 2004, 282, 1083-1088.
173. Ouchi, T; Hamada, A; Ohya, Y. Biodegradable microspheres having reactive groups prepared from L-lactic acid-depsipeptide copolymers. Macromolecular Chemistry and Physics, 1999, 200, 436-441.
174. Ouchi, T; Ohya, Y. Design of lactide copolymers as biomaterials. Journal of Polymer Science, Part A: Polymer Chemistry, 2004, 42, 453-462.
175. Ouchi, T; Toyohara, M; Arimura, H; Ohya, Y. Preparation of poly (L-lactide) -based microspheres having a cationic or anionic surface using biodegradable surfactants. Biomacromolecules. 2002, 3, 885-888.
176. Lee, SH; Szinai, I; Carpenter, K; Katsarava, R; Jokhadze, G; Chu, CC; Huang, Y; Verbeken, E; Bramwell, O; De Scheerder, I; Hong, MK. In-vivo biocompatibility evaluation of stents coated with a new biodegradable elastomeric and functional polymer. Coronary Artery Disease. 2002, 13, 237-41.
177. DesNoyer, JR; Pacetti, SD; Hossainy, SFA; Kleiner, L; Tang, Y; Zhang, G. Poly (ester amide) filler blends for modulation of coating properties. US 0, 249, 801 A1 (2007).
178. Huang, Y; Wang, L; Li, S; Liu, X; Lee, K; Verbeken, E; van de Werf, F; de Scheerder, I. Stent-based tempamine delivery on neointimal formation in a porcine coronary model. Acute Cardiac Care. 2006, 8, 210-216.
179. Pacetti, SD; DesNoyer, JR. Biologically absorbable coatings for implantable devices based on poly (ester amides) and methods for fabricating the same. US 1, 952, 830 (2008).
180. Trollsas, MO; Lim, F; Ngo, MH; Hossainy, SFA. Biodegradable poly (ester-amide) and poly (amide) coatings for implantable medical devices with enhanced bioabsorption times. US 0, 047, 319 A1 (2010).
181. Han, DK; Hubbell JA. Synthesis of polymer network scaffolds from L-lactide and poly (ethylene glycol) and their interaction with cells. Macromolecules, 1997, 30, 6077-6083.
182. John, G; Morita, M. Synthesis and characterization of photo-cross-linked networks based on L-lactide/serine copolymers. Macromolecules, 1999, 32, 1853-1858.
183. Pang, X; Chu, CC. Synthesis, characterization and biodegradation of poly (ester amide) s based hydrogels. Polymer, 2010, 51, 4200-4210.
184. Ferre, T; Franco, L; Rodriguez-Galan, A; Puiggali, J. Poly (ester amide) s derived from 1, 4-butanediol, adipic acid and 6-aminohexanoic acid. Part II: Composition changes and fillers. Polymer, 2003, 44, 6139-52.
185. Averous, L; Fringant, C. Association between plasticized starch and polyesters: processing and performances of injected biodegradable systems. Polymer Engineering & Science, 2001, 41, 727-34.
186. Martin, O; Averous, L. Comprehensive experimental study of a starch/polyesteramide coextrusion, Journal of Applied Polymer Science, 2002, 86, 2586-600.
187. Willett, JL; Felker, FC. Tensile yield properties of starch-filled poly (ester amide) materials. Polymer, 2005, 46, 3035-3042.
188. Mohanty, AK; Khan, MA; Hinrichsen, G. Influence of chemical surface modification on the properties of biodegradable jute fabrics-polyester amide composites. Composites: Part A, 2000, 31, 143-150.
189. Krook, M; Albertsson, AC; Gedde, UW; Hedenqvist, MS. Barrier and mechanical properties of montmorillonite/polyesteramide nanocomposites. Polymer Engineering & Science, 2002, 42, 1238-1246.
190. Liu, X.; Zou, Y; Cao, G; Luo, D. The preparation and properties of biodegradable polyesteramide composites reinforced with nano-CaCO3 and nano-SiO2. Materials Letters, 2007, 61, 4216-4221.
191. Morales, L; Franco, L; Casas, MT; Puiggali, J. Poly (ester amide) /clay nanocomposites prepared by in situ polymerization of the sodium salt of N-chloroacetyl-6-Aminohexanoic Acid. Journal of Polymer Science Part A: Polymer Chemistry, 2009, 47, 3616-3629.
192. Morales, L; Franco, L; Casas, MT; Puiggali, J. Crystallization studies on a clay nanocomposite prepared from a degradable poly (ester amide) constituted by glycolic acid and 6-aminohexanoic acid. Polymer Engineering & Science, 2010, in press.
193. Hsu, YG; Chang, LF; Wang, CP. Organic-inorganic hybrid materials based on the incorporation of nanoparticles of polysilicic acid (nPSA) with organic polymers. Curing of unsaturated poly (amide-ester) resin in the presence of nPSA. Materials Science and Engineering, 2004, 367, 205-21.
194. Lendlein, A; Kelch, S. Shape-memory polymers as stimuli-sensitive implant materials. ClinicalHemorheologyMicrocirculation, 2005, 32, 105-116.
195. Feng, Y; Behl, M; Kelch, S; Lendlein, A. Biodegradable multiblock copolymers based on oligodepsipeptides having shape-memory properties. Macromolecular Bioscience, 2009, 9, 45-54.
196. Chen, X; Zhong, H; Jia, I; Ling, J; Tang, R; Qiao, J; Zhang, Z. Polyesteramides used for hot melt adhesives: Synthesis and effect of inherent viscosity on properties. Journal of Applied Polymer Science, 2001, 81, 2696-2701.
197. Chen, G; Hoffman, AS. Graft copolymers that exhibit temperature-induced phase transitions over a wide range of pH. Nature, 1995, 373, 49-52.
198. Jeong, B; Kim, SW; Bae, YH. Thermosensitive sol-gel reversible hydrogels. Advanced Drug Delivery Review, 2002, 54, 37-51.
199. Feil, H; Bae, YH; Feijan, J; Kim, SW. Effect of comonomer hydrophilicity and ionization on the lower critical solution temperature of N-isopropylacrylamide copolymers. Macromolecules, 1993, 26, 2496-2500.
200. Ebara, M; Aoyagi, T; Sakai, K; Okano, T. Introducing reactive carboxyl side chains retains phase transition temperature sensitivity in N-isopropylacrylamide copolymer gels. Macromolecules, 2000, 33, 8312-8316.
201. Ohya, Y; Toyohara, M; Sasakawa, M; Arimura, H; Ouchi, T. Thermosensitive biodegradable polydepsipeptide. Macromolecular Bioscience, 2005, 5, 273-276.