Plant oil renewable resources as green alternatives in polymer science

Chemical Society Reviews

Volumn 36, Issue 11, 2007, Pages 1788-1802

  Meier, Michael A R ^a   Metzger, Jürgen O ^b   Schubert, Ulrich S ^c,d  

^a UNIVERSITY OF APPLIED SCIENCES EMDEN LEER   (Germany)

^b UNIVERSITY OF OLDENBURG   (Germany)

^c EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^d FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34848880727     PISSN: 03060012     EISSN: 14604744     Source Type: Journal    
DOI: 10.1039/b703294c     Document Type: Article

References (136)

1. M. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem., Int. Ed. 2002, 41, 414-436
2. Report of the United Nations Conference on Environment and Development, Rio de Janeiro, 1992; http://www.un.org/esa/sustdev
3. G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106, 4044-4098
4. G. A. Olah, A. Goeppert and G. K. S. Prakash, Beyond Oil and Gas: The Methanol Economy, WILEY–VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
5. J. O. Metzger, Angew. Chem., Int. Ed. 2006, 45, 5045-5047
6. German Federal Ministry of Food, Agriculture and Consumer Protection, Agency of Renewable Resources, http://www.fnr.de
7. G. Heisterberg-Moutsis, R. Heinz, T. F. Wolf, D. J. Harper, D. James, R. P. Mazzur and V. Kettler, ‘Floor Coverings’, in Ullmann’s encyclopedia of industrial chemistry, Online Edn., WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany
8. The Lipid Handbook, ed. F. D. Gunstone, Taylor & Francis Ltd, United Kingdom, 2004
9. J. O. Metzger, U. Bornscheuer, Appl. Microbiol. Biotechnol. 2006, 71, 13-22
10. F. S. Günera, Y. Yagčı, A. T. Erciyes, Prog. Polym. Sci. 2006, 31, 633-670
11. C. M. Byrne, S. D. Allen, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2004, 126, 11404-11405
12. J. Mallégol, J. Lemaire, J.-L. Gardette, Prog. Org. Coat. 2000, 39, 107-113
13. J. Mallégol, J.-L. Gardette, J. Lemaire, J. Am. Oil Chem. Soc. 1999, 76, 967-976
14. J. Mallégol, J.-L. Gardette, J. Lemaire, J. Am. Oil Chem. Soc. 2000, 77, 249-255
15. J. Mallégol, J.-L. Gardette, J. Lemaire, J. Am. Oil Chem. Soc. 2000, 77, 257-263
16. S. Asadauskas, S. Z. Erhan, J. Am. Oil Chem. Soc. 2001, 78, 1029-1035
17. E. N. Frankel, Prog. Lipid Res. 1980, 19, 1-22
18. F. Li, R. C. Larock, J. Appl. Polym. Sci. 2001, 80, 658-670
19. F. Li, R. C. Larock, Polym. Adv. Technol. 2002, 13, 436-449
20. Z. Liu, B. K. Sharma, S. Z. Erhan, Biomacromolecules 2007, 8, 233-239
21. J. W. Gooch, Lead-Based Paint Handbook, Kluwer Academic Publishers, New York, Boston, Dordrecht, London, Moscow, 2002
22. J. van Haveren, E. A. Oostveen, F. Micciche, J. G. J. Weijnen, Eur. Coat. J. 2005, 1–2, 16-19
23. U. Biermann, W. Friedt, S. Lang, W. Lühs, G. Machmüller, J. O. Metzger, M. Rüsch gen Klaas, H. J. Schäfer, M. P. Schneider, Angew. Chem., Int. Ed. 2000, 39, 2206-2224
24. Z. S. Petrovic, A. Zlatanic, C. C. Lava, Eur. J. Lipid Sci. Technol. 2002, 104, 293-299
25. J. La Scala, R. P. Wool, J. Am. Oil Chem. Soc. 2002, 79, 373-378
26. G. Du, A. Tekin, E. G. Hammond, L. Keith Wooa, J. Am. Oil Chem. Soc. 2004, 81, 477-480
27. A. E. Gerbase, J. R. Gregório, M. Martinelli, M. C. Brasil, A. N. F. Mendes, J. Am. Oil Chem. Soc. 2002, 79, 179-181
28. G. J. Piazza, T. A. Foglia, J. Am. Oil Chem. Soc. 2005, 82, 481-485
29. C. Orellana-Coca, S. Camocho, D. Adlercreutz, B. Mattiasson, R. Hatti-Kaul, Eur. J. Lipid Sci. Technol. 2005, 107, 864-870
30. T. Vlček, Z. S. Petrović, J. Am. Oil Chem. Soc. 2006, 83, 247-252
31. M. Rüsch gen Klaas, S. Warwel, Ind. Crops Prod. 1999, 9, 125-132
32. I. Hilker, D. Bothe, J. Prüss, H.-J. Warnecke, Chem. Eng. Sci. 2001, 56, 427-432
33. J. Xu, Z. Liu, S. Z. Erhan, C. J. Carriere, J. Am. Oil Chem. Soc. 2002, 79, 593-596
34. J. Xu, Z. Liu, S. Z. Erhan, C. J. Carriere, J. Am. Oil Chem. Soc. 2004, 81, 813-816
35. R. Raghavachar, R. J. Letasi, P. V. Kola, Z. Chen, J. L. Massingill, J. Am. Oil Chem. Soc. 1999, 76, 511-516
36. S.-J. Park, F.-L. Jin, J.-R. Lee, J.-S. Shin, Eur. Polym. J. 2005, 41, 231-237
37. A. E. Gerbase, C. L. Petzhold, A. P. O. Costa, J. Am. Oil Chem. Soc. 2002, 79, 797-802
38. J. V. Crivello, R. Narayan, Chem. Mater. 1992, 4, 692-699
39. G. Lligadas, J. C. Ronda, M. Galià, V. Cádiz, J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 6717-6727
40. S.-J. Park, F.-L. Jin, J.-R. Lee, Macromol. Chem. Phys. 2004, 205, 2048-2054
41. S.-J. Park, F.-L. Jin, J.-R. Lee, Macromol. Rapid Commun. 2004, 25, 724-727
42. M. A. de Luca, M. Martinelli, M. M. Jacobi, P. L. Becker, M. F. Ferrão, J. Am. Oil Chem. Soc. 2006, 83, 147-151
43. G. Teng, M. D. Soucek, J. Am. Oil Chem. Soc. 2000, 77, 381-387
44. A. Overeem, G. J. H. Buisman, J. T. P. Derksen, F. P. Cuperus, L. Molhoek, W. Grisnich, C. Goemans, Ind. Crops Prod. 1999, 10, 157-165
45. G. Lligadas, J. C. Ronda, M. Galià, V. Cádiz, J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5630-5644
46. G. Lligadas, L. Callau, J. C. Ronda, M. Galià, V. Cádiz, J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 6295-6307
47. G. Lligadas, J. C. Ronda, M. Galià, V. Cádiz, Biomacromolecules 2006, 12, 3521-3526
48. H. Uyama, M. Kuwabara, T. Tsujimoto, M. Nakano, A. Usuki, S. Kobayashi, Chem. Mater. 2003, 15, 2492-2494
49. A. Zlatanić, C. Lava, W. Zhang, Z. S. Petrović, J. Polym. Sci., Part B: Polym. Phys. 2003, 42, 809-819, Chem. Eng. News, 2007, 85, pp. 20–21
50. L. L. Monteavaro, E. O. da Silva, A. P. O. Costa, D. Samios, A. E. Gerbase, C. L. Petzhold, J. Am. Oil Chem. Soc. 2005, 82, 365-371
51. G. Lligadas, J. C. Ronda, M. Galià, U. Biermann, J. O. Metzger, J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 634-645
52. G. Lligadas, J. C. Ronda, Marina Galià, V. Cádiz, Biomacromolecules 2006, 7, 2420-2426
53. K. M. Doll, S. Z. Erhan, J. Agric. Food Chem. 2005, 53, 9608-9614
54. K. M. Doll, S. Z. Erhan, Green Chem. 2005, 7, 849-854
55. B. Tamami, S. Sohn, G. L. Wilkes, G. L. B. Tamami, J. Appl. Polym. Sci. 2004, 92, 883-891
56. S. N. Khot, J. J. Lascala, E. Can, S. S. Morye, G. I. Williams, G. R. Palmese, S. H. Kusefoglu, R. P. Wool, J. Polym. Sci., Part A: Polym. Chem. 2001, 82, 703-723
57. H. Esen, S. Küsefoğlu, R. Wool, J. Appl. Polym. Sci. 2007, 103, 626-633
58. H. Esen, S. H. Küsefoğlu, J. Appl. Polym. Sci. 2003, 89, 3882-3888
59. T. Eren, S. H. Küsefoğlu, R. Wool, J. Appl. Polym. Sci. 2003, 90, 197-202
60. T. Eren, S. H. Küsefoğlu, J. Appl. Polym. Sci. 2005, 97, 2264-2272
61. T. Eren, S. H. Küsefoğlu, J. Appl. Polym. Sci. 2004, 91, 2700-2710
62. K. Hill, Pure Appl. Chem. 2000, 72, 1255-1264
63. http://www.cognis.com/CognisOleochemicals/what-we-offer/ozone-acids
64. H. Noureddini, M. Kanabur, J. Am. Oil Chem. Soc. 1999, 76, 305-312
65. E. Antonelli, R. D’Aloisio, M. Gambaro, T. Fiorani, C. Venturello, J. Org. Chem. 1998, 63, 7190-7206
66. E. Santacesaria, A. Sorrentino, F. Rainone, M. Di Serio, F. Speranza, Ind. Eng. Chem. Res. 2000, 39, 2766-2771
67. M. A. Oakley, S. Woodward, K. Coupland, D. Parker, C. Temple-Heald, J. Mol. Catal. A: Chem. 1999, 150, 105-111
68. D. Teomim, A. Nyska, A. J. Domb, J. Biomed. Mater. Res. 1999, 45, 258-267
69. T. Tsujimoto, H. Uyama, S. Kobayashi, Macromol. Biosci. 2002, 2, 329-335
70. S. C. Cermak, T. A. Isbell, J. Am. Oil Chem. Soc. 2001, 78, 557-565
71. S. C. Cermak, T. A. Isbell, J. Am. Oil Chem. Soc. 2004, 81, 297-303
72. M. Peláeza, C. Orellanaa, A. Marquésa, M. Busquetsb, A. Guerreroc, A. Manresa, J. Am. Oil Chem. Soc. 2003, 80, 859-866
73. R. E. Harry-O kuru, T. A. Isbell, D. Weisleder, J. Am. Oil Chem. Soc. 2001, 78, 219-222
74. H. Baumann, M. Bühler, H. Bochem, F. Hirsinger, H. Zoebelein, J. Falbe, Angew. Chem., Int. Ed. Engl. 1988, 27, 41-62
75. H. Guobin, L. Zuyu, Y. Suling, Y. Rufeng, J. Am. Oil Chem. Soc. 1996, 73, 1109-1112
76. Y. Deng, X.-D. Fan, J. Waterhouse, J. Appl. Polym. Sci. 1999, 73, 1081-1088
77. X.-D. Fan, Y. Deng, J. Waterhouse, P. Pfromm, W. W. Carr, J. Appl. Polym. Sci. 1999, 74, 1563-1570
78. T. Eren, S. H. Küsefoğlu, J. Appl. Polym. Sci. 2004, 94, 2475-2488
79. S. P. Bunker, R. P. Wool, J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 451-458
80. U. Biermann, J. O. Metzger, Fat Sci. Technol. 1990, 92, 133-134
81. F. Li, Z. Zhang, S. E. Friberg, P. A. Aikens, J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2863-2872
82. J. J. La Scala, J. M. Sands, J. A. Orlicki, E. J. Robinette, G. R. Palmese, Polymer 2004, 45, 7729-7737
83. M. Okubo, T. Fujibayashi, A. Terada, Colloid Polym. Sci. 2005, 283, 793-798
84. E. M. S. Van Hamersveld, J. J. G. S. Van Es, A. L. German, F. P. Cuperus, P. Weissenborn, A.-C. Hellgren, Prog. Org. Coat. 1999, 35, 235-246
85. E. M. S. Van Hamersveld, J. J. G. S. Van Es, F. P. Cuperus, Colloids Surf., A: Physicochemical and Engineering Aspects 1999, 153, 285-296
86. X.-M. Liu, L.-S. Wang, Biomaterials 2004, 25, 1929-1936
87. S. Warwel, F. Brüse, C. Demes, M. Kunz, M. Rüschgen Klaas, Chemosphere 2001, 43, 39-48
88. Q. Tian, R. C. Larock, J. Am. Oil Chem. Soc. 2002, 79, 479-488
89. S. Warwel, F. Brüse, C. Demes, M. Kunz, Ind. Crops Prod. 2004, 20, 301-309
90. J. C. Mol, Top. Catal. 2004, 27, 97-104
91. http://www.materia-inc.com/news.html
92. R. Pederson and Y. Schrodi, Book of Abstracts, 98th AOCS Annual Meeting & Expo, Quebec, Canada, May 13–16, 2007, p. 99
93. M. Szwarc, Nature 1956, 178, 1168-1169
94. K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921-2990
95. M. Kamigaito, T. Ando, M. Sawamoto, Chem. Rev. 2001, 101, 3689-3745
96. C. J. Hawker, A. W. Bosman, Eva Harth, Chem. Rev. 2001, 101, 3661-3688
97. C. Barner-Kowollik, T. P. Davis, J. P. A. Heuts, M. A H. Stenzel, P. Vana, M. Whittaker, J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 365-375
98. Y. Yagči, M. A. Tasdelen, Prog. Polym. Sci. 2006, 31, 1133-1170
99. N. Hadjichristidis, H. Iatroua, M. Pitsikalisa, J. Mays, Prog. Polym. Sci. 2006, 31, 1068-1132
100. N. Hadjichristidis, M. Pitsikalis, S. Pispas, H. Iatrou, Chem. Rev. 2001, 101, 3747-3792
101. A. D. Jenkins, P. Kratochvil, R. F. T. Stepto, U. W. Suter, Pure Appl. Chem. 1996, 68, 2287-2311
102. K. Matyjaszewski, J. Phys. Org. Chem. 1995, 8, 197-207
103. V. Raghunadh, D. Baskaran, S. Sivaram, J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 875-882
104. B. C. Anderson, G. D. Andrews, P. Arthur, Jr., H. W. Jacobson, L. R. Melby, A. J. Playtis, W. H. Sharkey, Macromolecules 1981, 14, 1599-1601
105. O. Nakagawa, N. Fujimoto, T. Nishiura, T. Kitayama, K. Hatada, Polym. Bull. 1992, 29, 579-586
106. D. Y. Sogah, W. R. Hertler, O. W. Webster, G. M. Cohen, Macromolecules 1987, 20, 1473-1488
107. B. Sannigrahi, P. P. Wadgaonkar, J. C. Sehra, S. Sivaram, J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 1999-2007
108. S. Warwel, B. Wiege, E. Fehling, M. Kunz, Macromol. Chem. Phys. 2001, 202, 849-855
109. V. Raghunadh, D. Baskaran, S. Sivaram, Polymer 2004, 45, 3149-3155
110. D. P. Chatterjee, B. M. Mandal, Polymer 2006, 47, 1812-1819
111. W. Xu, X. Zhu, Z. Cheng, J. Chen, J. Appl. Polym. Sci. 2003, 90, 1117-1125
112. P. J. Saikia, A. Goswami, S. D. Baruah, J. Appl. Polym. Sci. 2002, 85, 1236-1245
113. R. Hoogenboom, U. S. Schubert, Green Chem. 2006, 8, 895-899
114. H. Huang, R. Hoogenboom, M. A. M. Leenen, P. Guillet, A. M. Jonas, U. S. Schubert, J.-F. Gohy, J. Am. Chem. Soc. 2006, 128, 3784-3788
115. J. Thornton, Pandora’s Poison: Chlorine, Health, and a New Environmental Strategy, MIT Press, Cambridge, 2000
116. European Biodiesel Board, http://www.ebb-eu.org/stats.php
117. http://www.osti.gov/bridge
118. M. McCoy, Chem. Eng. News 2007, 85
119. http://www.cargill.com/news/news_releases/070508_ashlandjv.htm
120. P. Wittlich, A. Themann, K.-D. Vorlop, Biotechnol. Lett. 2001, 23, 463-466
121. Industrial environmental performance metrics: challenges and opportunities, (ed.: Committee on Industrial Environmental Performance Metrics, National Academy of Engineering, National Research Council), National Academy Press, Washington, D.C., 1999, 85–105
122. J. A. Cano-Ruiz, G. J. McRae, Annu. Rev. Energy Environ. 1998, 23, 499-536
123. A. Azapagic, S. Perdan, Trans. IChemE 2000, 78, 243-261
124. A. D. Curzons, D. J. C. Constable, D. N. Mortimer, V. L. Cunningham, Green Chem. 2001, 3, 1-6
125. M. Patel, Energy 2003, 28, 721-740
126. A. Diehlmann, G. Kreisel, Farbe + Lack 2000, 106, 101-105
127. F. N. Jones, ‘Alkyd resins’ in Ullmann’s encyclopedia of industrial chemistry, Online Edn., WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany
128. P. Frankl and F. Rubik, Life cycle assessment in industry and business: adoption patterns, applications and implications, Springer Verlag, Berlin, Heidelberg, 2000
129. I. Boustead, Eco-profiles of the European Plastics Industry, Reports for the European Centre for Plastics in the Environment, 1993–1996, http://lca.apme.org
130. M. Patel, C. Bastioli, L. Marini, E. Würdinger, Biopolymers 2003, 10, 409-452
131. M. Stalmans, H. Berenbold, J. L. Berna, L. Cavalli, A. Dillarstone, M. Franke, F. Hirsinger, D. Janzen, K. Kosswig, D. Postlethwaite, T. Rappert, C. Renta, D. Scharer, K.-P. Schick, W. Schul, H. Thomas, R. Van Sloten, Tenside Surfactants Deterg. 1995, 32, 84-109
132. Y. Li, E. Griffing, M. Higgins, M. Overcash, J. Food Proc. Eng. 2006, 29, 429-445
133. S. Yusoff, S. B. Hansen, Int. J. Life Cycle Assess. 2007, 12, 50-58
134. A. Niederl, M. Narodoslawsky, ACS Symp. Ser. 2006, 921, 239-252
135. A. Hansen, M. Flake, T. Dettmer, R. Bock, Mater. Des. 2006, 26, 571-577
136. D. Kahlich, U. Wiechern and J. Lindner, ‘Propylene Oxide’, in Ullmann’s encyclopedia of industrial chemistry, Online Edn., WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany