Preparation of Polyesteramides Based on Aliphatic Amine-Containing Phenol Derivatives via Interfacial Polymerization

Byung-Hoon Kim; Chil-Won Lee; Myoung-Seon Gong

Macromolecular Research, Vol.11, No.5, 328-333, October, 2003

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Preparation of Polyesteramides Based on Aliphatic Amine-Containing Phenol Derivatives via Interfacial Polymerization

Byung-Hoon Kim, Chil-Won Lee, and Myoung-Seon Gong^†

Department of Chemistry, Dankook University, Cheonan, Chungnam 330-714, Korea

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A series of polyesteramides with randomly introduced ester/amide group ratio of 50/50 were newly synthesized by reacting terephthaloyl chloride, isophthaloyl chloride and sebacoyl chloride with tyramine and tyrosine. The polymerization was carried out by interfacial polymerization in two phase solvent systems, which gave various polyesteramides with moderate molecular weights in good yields. The chemical structures of the polymers were confirmed by ¹H NMR, IR and elemental analysis. Tyrosine based polyesteramide was degraded thermally around 290 ℃ to give the polyesteramide, which was obtainable from tyramine. Thermal stability and degradation behaviors were examined by differential scanning calorimetry and thermogravimetric analyses.

Keywords:polyesteramide;tyramine;tyrosine;decarboxylation;interfacial polymerization

[References]

Bori C, Sorta E, Zotteri L, Polymer, 16, 565 (1975)
vanHutten PF, Magnus RM, Gaymans RJ, Polymer, 34, 4193 (1993)
Yu C, Mielewczyk SS, Breslauer KJ, Kohn J, Biomaterials, 20, 265 (1999)
Tangpasuthadol V, Pendharker SM, Kohn J, Biomaterials, 21, 2371 (2000)
Tangpasuthadol V, Pendharker SM, Peterson RC, Kohn J, Biomaterials, 21, 2379 (2000)
Jeong HM, Mooen SW, Jho JY, Ahn TO, Polymer, 39(2), 459 (1998)
Serrano PJM, vandeWerff BA, Gaymans RJ, Polymer, 39(1), 83 (1998)
Serrano PJ, Thuss E, Gaymans RJ, Polymer, 38(15), 3893 (1997)
Guang L, Gaymans RJ, Polymer, 38(19), 4891 (1997)
Alla A, Rodriguezgalan A, Deilarduya AM, Munozguerra S, Polymer, 38(19), 4935 (1997)
Wallenfels K, Rieser J, Ertel W, Thieme K, Angew. Chem.-Int. Edit., 15, 261 (1976)
Kim BG, Lee SJ, Gong MS, Korea Polym. J., 3(1), 41 (1995)
Cho JH, Gong MS, Kil DS, Korea Polym. J., 8(5), 209 (2000)
Noh AS, Geum N, Gong MS, Polym. J., 33, 150 (2001)
Geum N, Gong MS, Bull. Korean Chem. Soc., 21, 1111 (2000)
Lee CW, Geum N, Gong MS, Polym. J., 33, 486 (2001)
Kim BH, Lee CW, Ko J, Chang HG, Gong MS, Bull. Korean Chem. Soc., 23, 845 (2002)
LangeDean JA, Handbook of Chemistry, 13th ed., McGraw-Hill, New York, pp. 5, 18-60 (1985)
Dickinson BL, Polyarylate, Modern Plastics Encyclopedia, McGarw-Hill, New York, Vol. 59 (10A), pp. 61 (1982)
Conix AJ, U.S. Patent, 3,216,970 (1965)
Temin SC, Interfacial Synthesis, Marcel Dekker Inc., New York, Vol. 11, pp. 27-63 (1977)
Cho HG, Choi SH, Gong MS, Macromolecules, 26, 6654 (1993)
Patai S, The Chemistry of Carboxylic Acids and Esters, John Wiley & Sons, Inc., London, pp. 923-1064 (1969)

[Related Articles]

[1] Bori C, Sorta E, Zotteri L, Polymer, 16, 565 (1975)

[2] vanHutten PF, Magnus RM, Gaymans RJ, Polymer, 34, 4193 (1993)

[3] Yu C, Mielewczyk SS, Breslauer KJ, Kohn J, Biomaterials, 20, 265 (1999)

[4] Tangpasuthadol V, Pendharker SM, Kohn J, Biomaterials, 21, 2371 (2000)

[5] Tangpasuthadol V, Pendharker SM, Peterson RC, Kohn J, Biomaterials, 21, 2379 (2000)

[6] Jeong HM, Mooen SW, Jho JY, Ahn TO, Polymer, 39(2), 459 (1998)

[7] Serrano PJM, vandeWerff BA, Gaymans RJ, Polymer, 39(1), 83 (1998)

[8] Serrano PJ, Thuss E, Gaymans RJ, Polymer, 38(15), 3893 (1997)

[9] Guang L, Gaymans RJ, Polymer, 38(19), 4891 (1997)

[10] Alla A, Rodriguezgalan A, Deilarduya AM, Munozguerra S, Polymer, 38(19), 4935 (1997)

[11] Wallenfels K, Rieser J, Ertel W, Thieme K, Angew. Chem.-Int. Edit., 15, 261 (1976)

[12] Kim BG, Lee SJ, Gong MS, Korea Polym. J., 3(1), 41 (1995)

[13] Cho JH, Gong MS, Kil DS, Korea Polym. J., 8(5), 209 (2000)

[14] Noh AS, Geum N, Gong MS, Polym. J., 33, 150 (2001)

[15] Geum N, Gong MS, Bull. Korean Chem. Soc., 21, 1111 (2000)

[16] Lee CW, Geum N, Gong MS, Polym. J., 33, 486 (2001)

[17] Kim BH, Lee CW, Ko J, Chang HG, Gong MS, Bull. Korean Chem. Soc., 23, 845 (2002)

[18] LangeDean JA, Handbook of Chemistry, 13th ed., McGraw-Hill, New York, pp. 5, 18-60 (1985)

[19] Dickinson BL, Polyarylate, Modern Plastics Encyclopedia, McGarw-Hill, New York, Vol. 59 (10A), pp. 61 (1982)

[20] Conix AJ, U.S. Patent, 3,216,970 (1965)

[21] Temin SC, Interfacial Synthesis, Marcel Dekker Inc., New York, Vol. 11, pp. 27-63 (1977)

[22] Cho HG, Choi SH, Gong MS, Macromolecules, 26, 6654 (1993)

[23] Patai S, The Chemistry of Carboxylic Acids and Esters, John Wiley & Sons, Inc., London, pp. 923-1064 (1969)