Developments in metal-containing polyurethanes, co-polyurethanes and polyurethane ionomers

Journal of Macromolecular Science - Polymer Reviews

Volumn 45, Issue 3, 2005, Pages 231-261

  Jayakumar, R ^a   Nanjundan, S ^b   Prabaharan, M ^a  

^a UNIVERSITY OF MINHO   (Portugal)

^b ANNA UNIVERSITY   (India)

Author keywords

Metal containing polyurethanes; Poly(urethane ester)s; Poly(urethane ether)s; Poly(urethane ether ester)s; Poly(urethane imide)s; Poly(urethane urea)s; Polyurethane ionomers

Indexed keywords

ADDITIVES; GROWTH (MATERIALS); IMPREGNATION; IONOMERS; SOLUBILITY; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

METAL-CONTAINING POLYURETHANES; POLY(URETHANE-ESTER)S; POLY(URETHANE-ETHER)S; POLY(URETHANE-ETHER-ESTER)S; POLY(URETHANE-IMIDE)S; POLY(URETHANE-UREA)S; POLYURETHANE IONOMERS;

POLYURETHANES;

EID: 23944477329     PISSN: 15321797     EISSN: None     Source Type: Journal    
DOI: 10.1081/MC-200067721     Document Type: Article

References (100)

1. Saunders, J.H. and Frisch, K.C. (1962) Polyurethane. Part I. Chemistry; Interscience: New York, Chapter 6.
2. Woods, G. (1990) The ICI Polyurethane Book; John Wiley & Sons Ltd: Chichester, Chapter 1.
3. Comstock, M.J. (1981) Urethane Chemistry and Applications. ACS Symposium Series, No. 172, American Chemical Society: Washington, D.C., Chapter 1.
4. Keiji, I. (1987) Handbook of Polyurethane Resins. Nikkan Kosyo Shimmbun: Tokyo, Japan, Chapter 1.
5. Hepburn, C. (1991) Polyurethane Elastomers, 2nd Ed.; Elsevier: Amsterdam.
6. Meckel, W., Goyert, W., and Wieder, W. (1987) Thermoplastic Elastomers. Legge, N.R., Holden, G., and Schroeder, H.E. (eds.), Hanser: New York, Chapter 2.
7. Matsuda, H. and Kanaoka, K. (1995) Stability, cure properties, and applicability as one part as adhesives of system of divalent metal salts of mono(hydroxyethyl)phthalate-anhydride-bisepoxide. J. Appl. Polym. Sci., 30(6): 1229-1239.
8. Matsuda, H. (1979) Adhesives from divalent metal salts of mono(hydroxyethylphthalate), anhydride and bisepoxides. J. Appl. Polym. Sci., 23(10): 2603-2610.
9. Matsuda, H. (1976) Synthesis of polyesters by using divalent metal salts of mono(hydroxyethyl)phthalate: Metal-containing polyesters from such metal salts, anhydride and epoxide. J. Appl. Polym. Sci., 14(7): 1783-1795.
10. Nair, P.R., Nair, C.P.R., and Francis, D.J. (1997) Polyurethanes with polybutyl acrylate grafts via macromonomer technique: Thermal and mechanical properties. Eur. Polym. J., 33(1): 89-95.
11. Matsuda, H. and Takechi, S. (1990) Synthesis and properties of polyureas from divalent metal salts of p-aminobenzoic acid, diamine and diisocyanate. J. Polym. Sci., Part-A. Polym Chem. Ed., 28(9): 1895-1908.
12. Matsuda, H. (1977) Metal-containing crosslinked polyester resins by combined polyesterification and polymerization of curable mixtures based on divalent metal salts of mono(hydroxyethyl)phthalate. J. Polym. Sci., Part-A. Polym Chem. Ed., 15(14): 2239-2253.
13. Jian, J., Ren-Tianj, J., Yung-Xing, Q., Bao-Lin, C., and Lin-Xian, F. (1999) Synthesis and in-vitro blood compatibility of polyurethane modified by amino acid (II) polyurethane-graft-propyl sodium sulfonate polyethylene glycol. Gaodeng Xueniao Huaxuc Xuebao, 20(6): 1974-1977.
14. Razumova, L.L., Smurova, E.V., Veretennikora, A.A., Krivandin, V.A., and Zaikov, G.E. (1998) The stability of segmented polyurethanes allowed for contact with blood, and the development structures of colloid level sizes in them at long incubation in blood serum. Polym Med, 10(1): 103-109.
15. Manners, I. (2002) Ring opened polyferrocenes: Metal-containing polymers material science, self assembly and nanostructure applications. Polym Mater Sci Eng., 86(1): 85-86.
16. Okkema, A.Z. and Cooper, S.L. (1991) Effect of carboxylate and/or sulphonate ion incorporation on the physical and blood-contacting properties of polyetherurethane. Bio. Mat., 12(8): 668-676.
17. Silver, J.H. et al. (1992) Anticoagulant effects of sulphonated polyurethanes. Bio. Mat., 13(6): 339-344.
18. Matsuda, H. (1983) Preparation and copolymerization of methacrylate-terminated ionic liquid rubbers. J. Macromol. Sci., Pure Appl Chem., A19(1): 1-6.
19. Matsuda, H. (1974) Synthesis of polymers by using divalent metal salts of mono(hydroxyethyl)phthalate: Metal-containing polyurethanes. J. Polym. Sci., Part A. Polym. Chem. Ed., 12(2): 455-468.
20. Matsuda, H. (1977) Synthesis of polymers by using divalent metal salts of mono(hydroxyethyl)phthalate: Metal-containing three dimensional polyesters from metal salts, pyromellitic dianhydride and epoxide. J. Macromol. Sci., Pure Appl Chem., A11(2): 431-477.
21. Matsuda, H. (1978) Metal-containing cured polyesters from divalent metal salts of mono (hydroxyethyl)phthalate, biester, anhydrides and monoepoxide. J. Appl. Polym. Sci., 22(12): 3371-3386.
22. Matsuda, H. (1978) Synthesis of metal-containing cured resins from divalent metal salts of mono(hydroxyethyl)phthalate, anhydride and bisepoxides. J. Appl. Polym. Sci., 22(9): 2093-2108.
23. Durairaj, B. and Rao, K.V. (1980) Synthesis of some new metal-containing polyurethanes. Eur. Polym. J, 16(4): 941-944.
24. Kothandaraman, H., Rao, K.V., Ragavan, A., and Chandrasekaran, V. (1983) Metal-containing polyurethanes. Polym. Bull., 13(2): 353-356.
25. Rajalingam, P., Radhakrishnan, G., Devanathan, S.B., Selvi, K.T., and Rao, K.V. (1989) Synthesis of new metal-containing diols for polyurethanes. Acta Polym., 41(11): 560-564.
26. Rajalingam, P., Radhakrishnan, G., Vasudevan, C., Selvi, K.T., and Rao, K.V. (1990) Synthesis and characterization of new metal-containing diols for polyurethanes. Polym. Commun., 31(1): 243-246.
27. Arun Prasath, R. and Nanjundan, S. (1998) Synthesis and characterization of metal-containing polyurethanes and polyurethane-ureas based on new divalent metal salts of mono(hydroxybutyl)phthalate. J. Macromol. Sci., Pure Appl. Chem., A35(5): 821-842.
28. Arun Prasath, R., Jayakumar, R., and Nanjundan, S. (2000) Synthesis and characterization of polyurethanes and polyurethane-ureas based on zinc salts of mono(hydroxybutyl)phthalate. J. Macromol. Sci., Pure Appl. Chem., A37(5): 469-488.
29. Jayakumar, R., Lee, Y.S., Rajkumar, M., and Nanjundan, S. (2004) Synthesis, characterization and antibacterial activity of metal containing polyurethanes. J. Appl. Polym. Sci., 91(1): 288-295.
30. Jayakumar, R., Rajkumar, M., Nagendran, R., and Nanjundan, S. (2001) Studies on metal-containing polyurethanes based on divalent metal salts of mono(hydroxyethoxyethyl) phthalate. J. Macromol. Sci., Pure Appl. Chem., A38(9): 869-888.
31. Jayakumar, R., Rajkumar, M., Nagendran, R., and Nanjundan, S. (2002) Synthesis and characterization of metal-containing polyurethanes with antibacterial activity. J. Appl. Polym. Sci., 85(6): 1194-1206.
32. Jayakumar, R., Lee, Y.S., and Nanjundan, S. (2003) Studies on metal-containing copolyurethanes. Reac. Func. Polym., 55(3): 267-276.
33. Jayakumar, R., Lee, Y.S., and Nanjundan, S. (2004) Studies on metal-containing copolyurethanes based on mono(hydroxyethoxyethyl)phthalate. Int. J. Polym. Ana. Ch., in press.
34. Arun Prasath, R. and Nanjundan, S. (1999) Synthesis and characterization of metal-containing polyurethanes and polyurethane-ureas. Eur. Polym. J., 35(11): 1939-1948.
35. Arun Prasath, R., Vijayanand, P.S., and Nanjundan, S. (2000) Studies on polyurethanes and polyurethane-ureas derived from divalent metal salts of mono(hydroxybutyl)hexolate. Polym. Int., 49(11): 1464-1472.
36. Nishijima, Y. and Fukushina, M. (1973) Kobunshi Kagaku, 30(1): 13-20.
37. Lipatova, T.E., Bakalo, L.A., and Sivotinskaya, A.L. (1975) The reaction of the urethane group with organotin catalysts, Synthesis and physical chemistry of urethanes. In Soviet progress in polyurethanes; Technomic publication: 99-102, Section II, Chapter 17.
38. Lipatov, Y.S. and Kosyanchuck, L.F. (1998) Effect of the nature of diisocyanate fragments on the structure of segmented linear and metal-cross-linked polyurethanes. Vyso. Soedin. Seriya A & Seriya B, 40(12): 2022-2028.
39. Banks, M., Ebdon, J.R., and Johnson, M. (1993) Influence of covalently bound phosphorous-containing groups on the flamrnability of poly(vinyl alcohol), poly(ethylene-co-vinyl alcohol) and low-density polyethylene. Polymer, 34(21): 4547-4556.
40. Nair, C.P.R., Clouet, G., and Guilbert, Y. (1989) Flame and thermal resistance of phosphorous functionalized poly(methylmethacrylate) and polystyrene. Polym. Deg. Stab., 26(4): 305-331.
41. Sato, M. and Yokoyama, M. (1979) Preparation of phosphorous-containing polymers-XV. Preparation of phosphorous-containing polyamide-imides from N,N′-bis(4-carboxyphthalimido)-3,3′-diphenylalkylphosphine oxide and aromatic diacetamides. Eur. Polym. J., 15(1): 75-79.
42. Ignatious, F., Sein, A., Cabasso, I., and Smid, J. (1993) Novel carbamoyl phosphanate monomers and polymers from unsaturated isocyanates. J. Polym. Sci. Part A: Polym. Chem., 31(1): 239-247.
43. Banerjee, S., Palit, K., and Maiti, S. (1994) Phosphorous-containing polymers. III. Polyimido-phosphanates. J. Polym. Sci. Part A: Polym. Chem., 32(2): 219-227.
44. Maiti, S., Banerjee, S., and Palit, K. (1993) Phosphorous-containing polymers. Prog. Polym. Sci., 18(2): 227-261.
45. Liu, Y.L., Hsiue, G.H., Lan, C.W., and Chiu, Y.S. (1997) Flame-retardant polyurethanes from phosphorous-containing isocyanates. J. Polym. Sci. Part A: Polym. Chem., 35(9): 1769-1780.
46. Wadim, B. (1976) Flame retardant polyurethane from polymeric halogenated organo phosphorous diols-flexible foams. US 3945954, 19760323, US 519441, 19741031, Uniroyal Inc.
47. Kakati, D.K., Gosain, R., and George, M.H. (1994) New polyurethane ionomers containing phosphonate groups. Polymer, 35(2): 398-402.
48. Troev, K. et al. (1996) Synthesis of phosphorous-containing polyurethanes without use of isocyanates. J. Polym. Sci. Part A: Polym. Chem., 34(4): 621-631.
49. Liaw, D.J. and Lin, S.P. (1996) Phosphorous-containing polyurethanes based on bisphenol-AF prepared by N-alkylation. J. Appl. Polym. Sci., 61(2): 315-319.
50. Kultys, A. and Pikus, S. (2001) Polyurethanes containing sulphur. III. New thermoplastic HDI-based segmented polyurethanes with diphenylmethane unit in their structure. J. Polym. Sci. Part A: Polym. Chem., 39(10): 1733-1742.
51. 2+ ions and their complexes with crown ethers. Polym. Sci. Series, A45(7): 644-649.
52. Acharya, V., Prabha, C.R., and Murthy, C.N. (2003) Synthesis and characterization of metal incorporated polyurethanes for potential bio-medical applications. J. Polym. Mat., 20(1): 83-89.
53. Georgoussis, G. et al. (2000) Structure-property relationships in segmented polyurethanes with metal chelates in the main chain. Eur. Polym. J., 36(6): 1113-1126.
54. Chen, L., Yu, H., and Yang, C.Z. (1997) The study of metal-Schiff base coordinated polyurethane. Polym. Adv. Tech., 8(6): 335-338.
55. Yamazaki, E., Hanahata, H., Hiwatari, J., and Kitahama, Y. (1997) Segmented poly(urethane-urea)s synthesized directly from isocyanated-terminated prepolymers and masked diamines II. Kinetic and mechanistic study of polymerization reactions. Polymer, J., 29(10): 811-820.
56. Matsuda, H. (1974) Synthesis of polymers by using divalent metal salts of mono(hydrox-yethyl)phthalate: Metal-containing polyurethane-ureas. J. Polym. Sci. Part A: Polym. Chem., 12(2): 469-481.
57. Rajalingam, P. and Radhakrishnan, G. (1992) Synthesis and characterization of metal-containing polyurethane-ureas. Polymer, 33(10): 2214-2216.
58. Jayakumar, R., Arun Prasath, R., and Nanjundan, S. (2002) Studies in zinc-containing polyurethanes and polyurethane-ureas. J. Macromol. Sci., Pure Appl. Chem., A39(8): 853-877.
59. Jayakumar, R., Radhakrishnan, S., and Nanjundan, S. (2003) Studies on poly(urethane-urea)s based on zinc salt of mono(hydroxyethoxyethyl)phthalate. Reac. Func. Polym., 57(1): 23-31.
60. Jayakumar, R., Lee, Y.S., and Nanjundan, S. (2003) Synthesis and characterization of calcium-containing poly(urethane-urea)s. J. Appl. Polym. Sci., 90(13): 3488-3496.
61. Jayakumar, R. and Nanjundan, S. (2004) Calcium-containing poly(urethane-urea)s: Synthesis spectral and thermal studies. J. Polym. Sci. Part A: Polym. Chem., 42(8): 1809-1819.
62. Matsuda, H. and Takechi, S. (1991) Synthesis and properties of halo-telechelic polyurethane-ureas from divalent metal salts of p-aminobenzoic acid, diamine, diethylene glycols, and diisocyanates. J. Polym. Sci. Part A: Polym. Chem., 29(1): 83-91.
63. Chantarasiri, N., Damrongkosit, T., Jangwong, W., Sridaeng, D., and Suebphan, S. (2004) Synthesis, characterization and thermal properties of metal-containing polyurethane-ureas from hexadentate Schiff base metal complexes. Eur. Polym. J., 40(8): 1867-1874.
64. Hayashi, K., Takano, H., Matsuda, T., and Umezu, M. (1985) Mechanical stability of elasto-meric polymers for blood pumb applications. J. Biomed. Mater. Res., 19(2): 179-193.
65. Jayakumar, R., Lee, Y.S., and Nanjundan, S. (2003) Studies on calcium-containing poly(urethane-ether)s. J. Polym. Sci. Part A: Polym. Chem., 41(18): 2865-2878.
66. Jayakumar, R., Lee, Y.S., and Nanjundan, S. (2004) Synthesis and coating characteristics of novel-calcium containing poly(urethane-ether)s. J. Appl. Polym. Sci., 92(2): 710-721.
67. Jayakumar, R. and Nanjundan, S. (2003) Studies on zinc-containing poly(urethane-ether)s. Polym. J., 35(9): 734-739.
68. Jayakumar, R. and Nanjundan, S. (2005) Synthesis of zinc-containing poly(urethane-ether)s based on mono(hydroxypentyl)phthalate. Eur. Polym. J., 41(7): 1623-1629.
69. Arun Prasath, R., Nanjundan, S., Pakula, T., and Klapper, M. (2004) Synthesis and characterization of calcium containing poly(urethane-ether)s. Eur. Polym. J., 40(8): 1767-1778.
70. Arun Prasath, R., Nanjundan, S., Pakula, T., and Klapper, M. (2004) Thermal and mechanical behavior of calcium containing copolyurethanes. Polym. Deg. Sta., 85(2): 911-923.
71. Zuo, M., Xiang, Q., and Takeichi, T. (1998) Preparation and properties of novel poly(urethane-imide)s. Polymer, 39(26): 6883-6889.
72. Yeganeh, H., Barikani, M., and Khodabadi, F.N. (2000) Synthesis and properties of novel thermoplastic poly(urethane-imide)s. Eur. Polym. J., 36(10): 2207-2211.
73. Yeganeh, H. and Shamekhi, M.A. (2004) Poly(urethane-imide-imide), a new generation of thermoplastic polyurethane elastomers with enhanced thermal stability. Polymer, 45(2): 359-365.
74. Zuo, M. and Takechi, T. (1997) Novel method for the preparation of poly(urethane-imide)s and their properties. J. Polym. Sci. Polym. Chem., 35(17): 3745-3753.
75. Gnarajan, T.P., Nasar, A.S., Iyer, N.P., and Radhakrishnan, G.J. (2000) Synthesis of poly(urethane-imide) using aromatic secondary amine-blocked polyurethane prepolymer. J. Polym. Sci. Polym. Chem., 38(22): 4032-4037.
76. Lin, M.F., Shu, Y.C., Tsen, W.C., and Chuang, F.S. (1999) Synthesis of polyurethane-imide (PU-imide) copolymers with different dianhydrides and their properties. Polym. Int., 48(6): 433-445.
77. Chen, J., Zhang, J., Zhu, T., Hua, Z., Chen, Q., and Yu, X. (2001) Blends of thermoplastic poly-urethane and polyether-polyimide: preparation and properties. Polymer, 42(4): 1493-1500.
78. Zuo, M. and Takeichi, T. (1999) Preparation and characterization of poly(urethane-imide) films prepared from reactive polyimide and polyurethane prepolymer. Polymer, 40(18): 5153-5160.
79. Deligoz, H., Yalcinyuva, T., and Ozgumus, S. (2005) A novel type of Si-containing poly(urethane-imide)s; synthesis, characterization and electrical properties. Eur. Polym. J., 41(4): 771-781.
80. George, M.H., Arshady, R., Kakati, D.K., Al-Shahib, W., and Gosain, R. (1996) Polyurethane ionomers. In Polym. Mater. Encycl. Salamone, J.C. (ed.), CRC Press, Inc.: New York, Vol. 19 6972.
81. Ramesh, S., Tharanikkarasu, K., Mahesh, G.N., and Radhakrishnan, G. (1998) Synthesis, physicochemical characterization, and applications of polyurethane ionomers: A review. J.M.S.-Rev. Macromol. Chem. Phys., C38(3): 481-509.
82. Xiao, H.X. and Frisch, K.C. (1995) Advances in Urethane Ionomers. 257-276. Technomic: Westport, CT.
83. Institute of Chemical Industry. (1991) Polyurethane Elastomers; 3rd Ed.; Chem. Ind. Pub.: Beijing, China.
84. Arnold, R.G., Nelson, J.A., and Verbanc, J.J. (1957) Chem. Rev., 57(1): 47-57.
85. Oertel, G. (1985) Polyurethane Handbook; 122-157. Hanser Publisher: New York.
86. Ulrich, H. (1997) Urethane Polymers, Encycl. Chem. Tech.; Kroschwitz, J.I. and Mary, H.G. (eds.), John Wiley and Sons: New York, Vol. 24, 695.
87. Chao, D.Y., Kuo, W.J., Wang, N.H., Lee, C.L., and Yang, K.H. (1998) Study of the synthesis and physical properties of fire-resistant polyurethane ionomers. J. Appl. Polym. Sci., 67(1): 19-26.
88. Lam, P.K.H., George, M.H., and Barrieja, J.A. (1991) New polyurethane ionomers-containing phosphate groups. Polym. Comm., 32(3): 80-82.
89. Mequanint, K., Sanderson, R., and Pasch, H. (2002) Thermogravimetric study of phosphated polyurethanes. Polym. Degrad. Stab., 77(1): 121-128.
90. Ding, Y., Register, R.A., Yang, C.Z., and Cooper, S.L. (1989) Synthesis and characterization of sulphonated polyurethane ionomers based on toluene diisocyanate. Polymer, 30(7): 1204-1212.
91. Ding, Y., Register, R.A., Yang, C.Z., and Cooper, S.L. (1989) Small-angle X-ray scattering from sulphonated polyurethane ionomers based on toluene diisocyanate. Polymer, 30(7): 1213-1220.
92. Ding, Y., Register, R.A., Yang, C.Z., and Cooper, S.L. (1989) Effect of cation local structure on the physical properties of sulphonated polyurethane ionomers based on toluene diisocyanate. Polymer, 30(7): 1221-1226.
93. Wang, X., Li, H., Tang, X., and Chang, F.C. (1999) Synthesis and characterizations of soft-segment ionic polyurethanes. J. Polym. Sci. Part B: Polym. Phys., 37(8): 837-845.
94. Wei, X. and Yu, X. (1997) Synthesis and properties of sulphonated polyurethane ionomers with anions in the polyether soft segments. J. Polym. Sci. Part B: Polym. Phys., 35(2): 225-232.
95. Xu, H.S. and Yang, C.Z. (1995) The ionic conductivity property of sulfonated polyethylene oxide polyurethane ionomers. J. Polym. Sci. Polym. Phys., 33(5): 745-751.
96. Robila, G., Buruiana, T., and Buruiana, E.C. (1995) Sulfonated polyurethane ionomers in solution. Angew. Makromol. Chem., 231(1): 25-33.
97. Visser, S.A. and Cooper, S.L. (1991) Comparison of the physical-properties of carboxylated and sulfonated model polyurethane ionomers. Macromolecules, 24(9): 2576-2583.
98. Ding, J.F., Xue, G., Yang, C.Z., and Chen, R.S. (1992) Dynamic mechanical analysis of sulfonated polyurethane ionomers. J. Appl. Polym. Sci., 45(6): 1087-1092.
99. 2+. Angew. Makromol. Chem., 22(11): 61-65.
100. Mirceva, A. and Malavasic, T. (1996) Bromine-containing polyurethane ionomers. Polym. Bull., 36(2): 189-196.