Thermosetting (bio)materials derived from renewable resources: A critical review

Progress in Polymer Science (Oxford)

Volumn 35, Issue 4, 2010, Pages 487-509

  Raquez, J M ^a,b   Deleglise M ^a   Lacrampe, M F ^a   Krawczak, P ^a  

^a ECOLE DES MINES DE DOUAI   (France)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

Biodegradability; Biomaterials; Chemical modifications; Renewable resource; Thermosetting materials

Indexed keywords

CRITICAL REVIEW; CROSS-LINKED POLYMERS; CROSS-LINKING DENSITY; HIGH PERFORMANCE PRODUCTS; LIGHT IRRADIATIONS; PHENOLICS; POLYURETHANE RESIN; RENEWABLE FEEDSTOCKS; RENEWABLE RESOURCE; THERMOSETTING MATERIALS;

BIODEGRADATION; BIOLOGICAL MATERIALS; BIOMATERIALS; CHEMICAL MODIFICATION; CROSSLINKING; EPOXY RESINS; FEEDSTOCKS; PHENOLS; POLYESTER RESINS; RESINS; THERMOSETS;

RENEWABLE ENERGY RESOURCES;

EID: 77649187982     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2010.01.001     Document Type: Review

References (214)

1. Guilleminot J., Comas-Cardona S., Kondo D., Binetruy C., and Krawczak P. Multiscale modelling of the composite reinforced foam core of a 3D sandwich structure. Comp Sci Technol 68 (2008) 1777-1786
2. Yousefi A., Lafleur P.G., and Gauvin R. Kinetic studies of thermoset cure reactions: a review. Polym Comp 18 (1997) 157-168
3. Feldman D. Composites, thermosetting polymers. In: Salamone J.C. (Ed). Polymeric materials encyclopaedia (1996), CRC Press, FL 277-278
4. Gourichon B., Deleglise M., Binetruy C., and Krawczak P. Dynamic void content prediction during radial injection in liquid composite molding. Composites Part A 39 (2008) 46-55
5. Krawczak P., and Pabiot J. Fracture mechanics applied to glass fibre/epoxy matrix interface characterization. J Compos Mater 29 (1995) 2230-2253
6. Comas-Cardona S., Groenenboom P., Binetruy C., and Krawczak P. A generic mixed FE-SPH method to address hydro-mechanical coupling in liquid composite moulding processes. Composites Part A 36 (2005) 1004-1010
7. Carfagna C., Amendola E., and Giamberini M. Liquid crystalline epoxy based thermosetting polymers. Prog Polym Sci 22 (1997) 1607-1647
8. Deleglise M., Binetruy C., and Krawczak P. Solution to filling time prediction issues for constant pressure driven injection in RTM. Composites Part A 36 (2005) 339-344
9. Mathews F.L. Techniques for manufacture of composites. In: Hollaway L. (Ed). Handbook of polymer composites for engineers (1994), Woodhead Publishing Limited, Cambridge, UK 71-102
10. Hayes B.S., and Seferis J.C. Modification of thermosetting resins and composites through preformed polymer particles: a review. Polym Comp 22 (2001) 451-467
11. Fernando G.F., and Degamber B. Process monitoring of fibre reinforced composites using optical fibre sensors. Int Mater Rev 51 (2006) 65-106
12. Raquez J.-M., Nabar Y., Narayan R., and Dubois P. New developments in biodegradable starch-based nanocomposites. Int Polym Process 22 (2007) 463-470
13. Kummerer K. Sustainable from the very beginning: rational design of molecules by life cycle engineering as an important approach for green pharmacy and green chemistry. Green Chem 9 (2007) 899-907
14. Raston C. Renewables and green chemistry. Green Chem 7 (2005) 57-157
15. Jenck J.F., Agterberg F., and Droescher M.J. Products and processes for a sustainable chemical industry: a review of achievements and prospects. Green Chem 6 (2004) 544-556
16. Frattini S. Demand is increasing for renewable resourced resins. JEC Composites Mag 45 38 (2008) 32-33
17. Stewart R. Going green: eco-friendly materials and recycling on growth paths. Plastics Eng 64 1 (2008) 16-23
18. Kaplan D.L. Biopolymers from renewable resources (1998), Springer, New York p. 1-417
19. Rabetafika H., Paquot M., and Dubois P. Les polymères issus du végétal: matériaux à propriétés spécifiques pour des applications ciblées en industrie plastique. Biotechnol Agron Soc Env 10 (2006) 185-196
20. Baumann H., Bühler M., Fochem H., Hirsinger F., Zoebelein H., and Falbe J. Natürliche Fette und Öle - nachwachsende Rohstoffe für die chemische Industrie. Angew Chem 100 (1988) 41-62
21. Gunstone F. Fatty acid & lipid chemistry (1996), Blackie Academic & Professional, New York p. 1-252
22. Sharmin E., Marghoob Ashraf S., and Ahmad S. Epoxidation, hydroxylation, acrylation and urethanation of Linum usitatissimum seed oil and its derivatives. Eur J Lipid Sci Technol 109 (2007) 134-146
23. Bussell GW. Maleinized fatty acid esters of 9-oxatetracyclo-4.4.1.-O,O-undecan-4-ol. US Patent 3,855,163; 1974.
24. Hodakowski LE, Osborn CL, Harris EB. Polymerizable epoxide-modified compositions. US Patent 4,119,640; 1978.
25. Meier M.A.R., Metzger J.O., and Schubert U.S. Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 36 (2007) 1788-1802
26. Sharma V.S., and Kundu P.P. Addition polymers from natural oils - a review. Prog Polym Sci 31 (2006) 983-1008
27. Biermann U., Friedt W., Lang S., Luhs W., Machmuller G., Metzger J.O., et al. New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew Chem Int Ed 39 (2000) 2206-2224
28. Derksen J.T.P., Cuperus F.P., and Kolster P. Renewable resources in coatings technology: a review. Prog Org Coat 27 (1996) 45-53
29. Mosiewicki M., Aranguren M.I., and Borrajo J. Mechanical properties of linseed oil monoglyceride maleate/styrene copolymers. J Appl Polym Sci 97 (2005) 825-836
30. Mosiewicki M., Rojas O., Sibaja M.R., Borrajo J., and Aranguren M.I. Aging study of linseed oil resin/styrene thermosets and their composites with wood flour. Polym Int 56 (2007) 875-881
31. Lu Y., and Larock R.C. Novel biobased nanocomposites from soybean oil and functionalized organoclay. Biomacromolecules 7 (2006) 2692-2700
32. Zhu L., and Wool R.P. Nanoclay reinforced bio-based elastomers: synthesis and characterization. Polymer 47 (2006) 8106-8115
33. William G.I., and Wool R.P. Composites from natural fibers and soy oil resins. Appl Compos Mater 7 (2000) 421
34. Stewart D. Lignin as a base material for materials applications: chemistry, application and economics. Ind Crops Prod 27 (2008) 202-207
35. Mapleston P. New technologies for a greener industry. Plastics Eng 64 1 (2008) 10-15
36. Drumright R.E., Gruber P.R., and Henton D.E. Polylactic acid technology. Adv Mater 12 (2000) 1841-1846
37. Lunt J. Large-scale production, properties and commercial applications of polylactic acid polymers. Polym Degrad Stab 59 (1998) 145-152
38. Suriyamongkol P., Weselake R., Narine S., Moloney M., and Shah S. Biotechnological approaches for the production of polyhydroxyalkanoates in microorganisms and plants - a review. Biotechn Adv 25 (2007) 148-175
39. King P., and Biotechnology. An industrial view. J Chem Technol Biotechnol 32 (1982) 2-8
40. Calo E., Maffezzoli A., Mele G., Martina F., Mazzetto S., Tarzia A., et al. Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and bio-composites. Green Chem 9 (2007) 754-759
41. Harrington H.J. Phenolics. In: Epel J.N., Margolis J.M., Newman S., and Seymour R.B. (Eds). Engineered materials handbook vol. 2 (1988), ASM International, Metals Park OH p. 242-5
42. Ghosh N.N., Kiskan B., and Yagci Y. Polybenzoxazines - new high performance thermosetting resins: synthesis and properties. Prog Polym Sci 32 (2007) 1344-1391
43. Nair C.P. Advances in addition-cure phenolic resins. Prog Polym Sci 29 (2004) 401-498
44. In: Gardziella A., Pilato L., and Knop A. (Eds). Phenolic resins, chemistry, applications, standardization, safety and ecology. 2nd ed. (2000), Springer, Heidelberg, NY 1-560
45. In: Knop A., and Pilato L. (Eds). Phenolic resins: chemistry applications and performance-future directions (1985), Springer, Heidelberg, NY 1-313
46. Phenli U. Phenolic resins. In: Salamone J.C. (Ed). Concise polymeric materials encyclopaedia (1999), CRC Press, Boca Raton, FL 94-96
47. Matsumoto A. Phenolic Resins. In: Salamone J.C. (Ed). Concise polymeric materials encyclopaedia (1999), CRC Press, Boca Raton, FL 1017-1019
48. Campbell A.G., and Walsh A.R. The present status and potential of kraft lignin-phenol-formaldehyde wood adhesives. J Adhes 18 (1985) 301-314
49. Yadav R., Devi A., Tripathi G., and Srivastava D. Optimization of the process variables for the synthesis of cardanol-based novolac-type phenolic resin using response surface methodology. Eur Polym J 43 (2007) 3531-3537
50. Tyman H.P., Johnson R.A., Muir M., and Rokhgar R. The extraction of natural cashew nut-shell liquid from the cashew nut (Anacardium occidentale). J Am Oil Chem Soc 66 (1989) 553-557
51. Wasserman D., and Dawson C.R. Cashew nutshell liquid. Ind Eng Chem 38 (1945) 396-399
52. Tyman H.P. Long-chain phenols. IV. Quantitative determination of the olefinic composition of the component phenols in cashew nut-shell liquid. J Chromatogr 111 (1975) 277-284
53. Tyman H.P. Long-chain phenols. V. Gas chromatographic analysis of cashew nut-shell liquid (Anacardium occidentale). J Chromatogr 111 (1975) 285-292
54. Phani Kumar P., Paramashivappa R., Vithayathil P.J., Subba Rao P.V., and Srinivasa Rao A. Process for isolation of cardanol from technical cashew (Anacardium occidentale L.) nut shell liquid. J Agric Food Chem 50 (2002) 4705-4708
55. Pillai C.K.S., Prasad V.S., Sudha J.D., Bera S.C., and Menon A.R.R. Polymeric resins from renewable resources. II. Synthesis and characterization of flame-retardant prepolymers from cardanol. J Appl Polym Sci 41 (1990) 2487-2501
56. Devi A., and Srivastava D. Studies on the blends of cardanol-based epoxidized novolac type phenolic resin and carboxyl-terminated polybutadiene (CTPB). Mater Sci Eng A458 (2007) 336-347
57. Yadav R., and Srivastava D. Kinetics of the acid-catalyzed cardanol-formaldehyde reactions. Mat Chem Phys 106 (2007) 74-81
58. Maffezzoli A., Calo E., Zurlo S., Mele G., Tarzia A., and Stifani C. Cardanol based matrix biocomposites reinforced with natural fibres. Comp Sci Technol 64 (2004) 839-845
59. Burke W.J., and Weatherbee C. 3,4-Dihydro-1,3,2H-benzoxazines. Reaction of polyhydroxybenzenes with N-methylolamines. J Am Chem Soc 72 (1950) 4691-4694
60. Turunen M., Alvila L., Pakkanen T.T., and Rainio J. Modification of phenol-formaldehyde resol resins by lignin, starch, and urea. J Appl Polym Sci 88 (2003) 582-588
61. Sena-Martins G., Almeida-Vara E., and Duarte J.C. Eco-friendly new products from enzymatically modified industrial lignins. Ind Crops Prod 27 (2008) 189-195
62. Lora J.H., and Glasser W.G. Recent industrial applications of lignin: a sustainable alternative to nonrenewable materials. J Polym Env 10 (2002) 39-48
63. Vazquez G., Rodriguez-Bona C., Freire S., Gonzalez-Alvarez J., and Antorrena G. Acetosolv pine lignin as copolymer in resins for manufacture of exterior grade plywoods. Bioresour Technol 70 (1999) 209-214
64. Sellers T., Lora J.H., and Okuma M. Organosolv-lignin-modified phenolics as strandboard binder. II. Strandboard manufacture and properties. Mokuzai Gakkaishi 40 (1994) 1073-1078
65. Cetin N.S., and Ozmen N. Use of organosolv lignin in phenol-formaldehyde resins for particleboard production. I. Organosolv lignin modified resins. Int J Adhes 22 (2002) 477-480
66. Rautio P., Bergvall U.A., Karonen M., and Salminen J.-P. Bitter problems in ecological feeding experiments: commercial tannin preparations and common methods for tannin quantifications. Biochem Syst Ecol 35 (2007) 257-262
67. Martinez S. Inhibitory mechanism of mimosa tannin using molecular modeling and substitutional adsorption isotherms. Mater Chem Phys 77 (2003) 97-102
68. Pizzi A., Mekleiham A., and Stephanou A. Induced accelerated autocondensation of polyflavonoid tannins for phenolic polycondensates. 2. Cellulose effect and application. J Appl Polym Sci 55 (1995) 929-933
69. Pena C., Larranaga M., Gabilondo N., Tejado A., Echeverria J.M., and Mondragon I. Synthesis and characterization of phenolic novolacs modified by chestnut and mimosa tannin extracts. J Appl Polym Sci 100 (2006) 4412-4419
70. Kim S., and Kim H.J. Curing behavior and viscoelastic properties of pine and wattle tannin-based adhesives studied by dynamic mechanical thermal analysis and FT-IR-ATR spectroscopy. J Adhes Sci Technol 17 (2003) 1369-1383
71. Ozacar M., Soykan C., and Sengil I.A. Studies on synthesis, characterization, and metal adsorption of mimosa and valonia tannin resins. J Appl Polym Sci 102 (2006) 786-797
72. Sowunmi S., Ebewele R.O., Peters O., and Conner A.H. Differential scanning calorimetry of hydrolysed mangrove tannin. Polym Int 49 (2000) 574-578
73. Sowunmi S., Ebewele R.O., Conner A.H., and River B.H. Fortified mangrove tannin-based plywood adhesive. J App Polym Sci 62 (1996) 577-584
74. Garro-Galvez J.M., and Riedl B. Pyrogallol-formaldehyde thermosetting adhesives. J Appl Polym Sci 65 (1997) 399-408
75. Mosiewicki M., Aranguren M.I., and Borrajo J. Thermal and mechanical properties of woodflour/tannin adhesive composites. J Appl Polym Sci 91 (2004) 3074-3082
76. Mosiewicki M., Aranguren M.I., Curvelo A.A.S., and Borrajo J. Effect of natural rubber on wood-reinforced tannin composites. J Appl Polym Sci 105 (2007) 1825-1832
77. Roberts A.D. Natural rubber science and technology (1988), Oxford University Press, Oxford p. 1-1136
78. Bode H.B., Kerkhoff K., and Jendrossek D. Bacterial degradation of natural and synthetic rubber. Biomacromolecules 2 (2001) 295-303
79. Wu Q., Selke S., and Mohanty A.K. Processing and properties of biobased blends from soy meal and natural rubber. Macromol Mater Eng 292 (2007) 1149-1157
80. Amaral-Labat G.A., Pizzi A., Goncalves A.R., Celzard A., Rigolet S., and Rocha G.J.M. Environment-friendly soy flour-based resins without formaldehyde. J Appl Polym Sci 108 (2008) 624-632
81. Lei H., Pizzi A., and Du G. Environmentally friendly mixed tannin/lignin wood resins. J Appl Polym Sci 107 (2008) 203-209
82. Ellis B. Chemistry and technology of epoxy resins (1993), Blackie Academic & Professional, Glasgow, UK p. 1-332
83. Puglisi J.S., and Chaudhari M.A. Epoxies (EP). In: Epel J.N., Margolis J.M., Newman S., and Seymour R.B. (Eds). Engineered materials handbook, vol. 2 (1988), ASM International, Metals Park, OH p. 240-1
84. Guner F.S., Yagci Y., and Erciyes A.T. Polymers from triglyceride oils. Prog Polym Sci 31 (2006) 633-670
85. Crivello J.V., Narayan R., and Sternstein S.S. Fabrication and mechanical characterization of glass fiber reinforced UV-cured composites from epoxidized vegetable oils. J Appl Polym Sci 64 (1997) 2073-2087
86. 2. J Am Oil Chem Soc 83 (2006) 635-640
87. Vlcek T., and Petrovic Z. Optimization of the chemoenzymatic epoxidation of soybean oil. J Am Oil Chem Soc 83 (2006) 247-252
88. Goud V.V., Patwardhan A.V., Dinda S., and Pradhan N.C. Epoxidation of karanja (Pongamia glabra) oil catalysed of acidic ion exchange ion exchange resin. Eur J Lipid Sci Technol 109 (2007) 575-584
89. Sperling L.H., Manson J.A., Qureshi S., and Fernandez A.M. Tough plastics and reinforced elastomers from renewable resource industrial oils. A short review. Ing Eng Chem Prod Res 20 (1981) 163-166
90. Liang G., and Chandrashekhara K. Cure kinetics and rheology characterization of soy-based epoxy resin system. J Appl Polym Sci 102 (2006) 3168-3180
91. Uyama H., Kuwabara M., Tsujimoto T., and Kobayashi S. Enzymatic synthesis and curing of biodegradable epoxide-containing polyesters from renewable resources. Biomacromolecules 4 (2003) 211-215
92. Shogren R.L., Petrovic Z., Liu Z.S., and Erhan S.Z. Biodegradation behavior of some vegetable oil-based polymers. J Polym Env 12 (2004) 173-178
93. Lligadas G., Ronda J.C., Galia M., and Cadiz V. Synthesis and properties of thermosetting polymers from a phosphorous-containing fatty acid derivative. J Polym Sci Part A Polym Chem 44 (2006) 5630-5644
94. Lligadas G., Ronda J.C., Galia M., and Cadiz V. Development of novel phosphorus-containing epoxy resins from renewable resources. J Polym Sci Part A Polym Chem 44 (2006) 6717-6727
95. Shabeer A., Sundararaman S., Chandrashekhara K., and Dharani L.R. Physicochemical properties and fracture behavior of soy-based resin. J Appl Polym Sci 105 (2007) 656-663
96. Earls J.D., White J.E., Dettloff M.L., and Null M.J. Development and evaluation of terminally epoxidized triglycerides for coatings applications. JCT Research 1 (2004) 243-245
97. Teng G., and Soucek M.D. Epoxidized soybean oil-based ceramer coatings. J Am Oil Chem Soc 77 (2000) 381-387
98. Zhu J., Chandrashekhara K., Flanigan V., and Kapila S. Curing and mechanical characterization of a soy-based epoxy resin system. J Appl Polym Sci 91 (2004) 3513-3518
99. Trumbo D.L., and Otto J.T. Epoxidized fatty acid-derived oxazoline in thermoset coatings. J Coat Technol Res 5 (2008) 107-111
100. Czub P. Application of modified natural oils as reactive diluents for epoxy resins. Macromol Symp 242 (2006) 60-64
101. Park S.J., Jin F.L., and Lee J.R. Effect of biodegradable epoxidized castor oil on physicochemical and mechanical properties of epoxy resins. Macromol Chem Phys 205 (2004) 2048-2054
102. Jin F.L., and Park S.J. Impact-strength improvement of epoxy resins reinforced with a biodegradable polymer. Mater Sci Eng A478 (2008) 402-403
103. Earls J.D., White J.E., Lopez L.C., Lysenlo Z., Dettloff M.L., and Null M.J. Amine-cured omega-epoxy fatty acid triglycerides: Fundamental structure-property relationships. Polymer 48 (2007) 712-719
104. Boquillon N. Use of an epoxidized oil-based resin as matrix in vegetable fibers-reinforced composites. J Appl Polym Sci 101 (2006) 4037-4043
105. Liu Z.S., Erhan S.Z., and Calvert P.D. Solid freeform fabrication of soybean oil-based composites reinforced with clay and fibers. J Am Oil Chem Soc 81 (2004) 605-610
106. Miyagawa H., Misra M., Drzal L.T., and Mohanty A.K. Biobased epoxy/layered silicate nanocomposites: thermophysical properties and fracture behavior evaluation. J Polym Environ 13 (2005) 87-96
107. Miyagawa H., Mohanty A., Drzal L.T., and Misra M. Effect of clay and alumina-nanowhisker reinforcements on the mechanical properties of nanocomposites from biobased epoxy: a comparative study. Ind Eng Chem Res 43 (2004) 7001-7009
108. Uyama H., Kuwabara M., Tsujimoto T., Nakano M., Usuki A., and Kobayashi S. Green nanocomposites from renewable resources: plant oil-clay hybrid materials. Chem Mater 15 (2003) 2492-2494
109. Lligadas G., Ronda J.C., Galia M., and Cadiz V. Bionanocomposites from renewable resources: epoxidized linseed oil-polyhedral oligomeric silsesquioxanes hybrid materials. Biomacromolecules 7 (2006) 3521-3526
110. Harani H., Fellahi S., and Bakar M. Toughening of epoxy resin using hydroxyl-terminated polyesters. J Appl Polym Sci 71 (1999) 29-38
111. Chikhi N., Fellahi S., and Bakar M. Modification of epoxy resin using reactive liquid (ATBN) rubber. Eur Polym J 38 (2002) 251-264
112. Cizravi J.C., and Subramaniam K. Thermal and mechanical properties of epoxidized natural rubber modified epoxy matrices. Polym Int 48 (1999) 889-895
113. Yamanaka K., Takagi Y., and Inoue T. Reaction-induced phase separation in rubber-modified epoxy resins. Polymer 30 (1989) 1839-1844
114. Hong S.G., and Chan C.K. The curing behaviors of the epoxy/dicyanamide system modified with epoxidized natural rubber. Thermochim Acta 417 (2004) 99-106
115. Gan S.N., and Hamid Z.A. Partial conversion of epoxide groups to diols in epoxidized natural rubber. Polymer 38 (1997) 1953-1956
116. Kallitsis J.K., Skafidas D.S., and Kalfoglou N.K. Blends of poly(ethylene terephthalate) with unmodified and maleic anhydride grafted acrylonitrile-butadiene-styrene terpolymer. Polymer 37 (1989) 3387-3395
117. Mohanty S., and Nando G.B. Characterization of ionomers formed in situ from miscible blends of poly (ethylene-co-acrylic acid) (PEA) and epoxidized natural rubber (ENR). Polymer 38 (1997) 1395-1402
118. Ratnam C.T., and Zaman K. Stabilization of poly(vinyl chloride)/epoxidized natural rubber (PVC/ENR) blends. Polym Degrad Stab 65 (1999) 99-105
119. Bibi A.N., Boscott D.A., Butt T., and Lehrle R.S. Improving the adhesion between rubber and nylon by either epoxidation of the rubber or chemical pre-treatment of the nylon. Eur Polym J 24 (1988) 1127-1131
120. Olsson A., Lindstrom M., and Iversen T. Lipase-catalyzed synthesis of an epoxy-functionalized polyester from the suberin monomer cis-9,10-epoxy-18-hydroxyoctadecanoic acid. Biomacromolecules 8 (2007) 757-760
121. Kolattukudy P.E. Polyesters in higher plants. Adv Bioch Eng Biotech 71 (2001) 1-69
122. Hirose S., Hatakeyama T., and Hatakeyama H. Synthesis and thermal properties of epoxy resins from ester-carboxylic acid derivative of alcoholysis lignin. Macromol Symp 197 (2003) 157-170
123. Hirano S. Chitin and chitosan as novel biotechnological materials. Polym Int 48 (1999) 732-734
124. Chiellini E., and Solaro R. Biodegradable polymeric materials. Adv Mater 8 (1996) 305-313
125. Kasaal M.R. A review of several reported procedures to determine the degree of N-acetylation for chitin and chitosan using infrared spectroscopy. Carbohydr Polym 71 (2008) 497-508
126. Kolhe P., and Kannan R.M. Improvement in ductility of chitosan through blending and copolymerization with PEG: FTIR investigation of molecular interactions. Biomacromolecules 4 (2003) 173-180
127. Chen M.C., Tsai H.W., Chang Y., Lai W.Y., Mi F.L., Liu C.T., et al. Rapidly self-expandable polymeric stents with a shape-memory property. Biomacromolecules 8 (2007) 2774-2780
128. Chattopadhyay D.K., and Raju K.V. Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32 (2007) 352-418
129. Narayan R., Chattopadhyay D.K., Sreedhar B., Raju K.V., Mallikarjuna N.N., and Aminabhavi T.M. Synthesis and characterization of cross-linked polyurethane dispersions based on hydroxylated polyesters. J Appl Polym Sci 99 (2006) 368-380
130. Caraculacu A.A., and Coseri S. Isocyanates in polyaddition processes, structure and reaction mechanisms. Prog Polym Sci 26 (2001) 799-851
131. Zia K.M., Bhatti H.N., and Bhatti I.A. Methods for polyurethane and polyurethane composites, recycling and recovery: a review. React Funct Polym 67 (2007) 675-692
132. Petrovic Z.S. Polyurethanes from vegetable oils. Polymer Rev 48 (2008) 109-155
133. Tamani B., Sohn S., and Wilkes G.L. Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks. J Appl Polym Sci 92 (2004) 883-891
134. Parzuchowski P.G., Jurczyk-Kowalska M., Ryszkowska J., and Rokicki G. Epoxy resin modified with soybean oil containing cyclic carbonate groups. J Appl Polym Sci 102 (2006) 2904-2914
135. Desai S., Thakore I.M., Sarawade B.D., and Devi S. Structure-property relationship in polyurethane elastomers containing starch as a cross-linker. Polym Eng Sci 40 (2000) 1200-1210
136. Zetterlund P., Hirose S., Hatakeyama T., Hatakeyama H., and Albertsson A.C. Thermal and mechanical properties of polyurethanes derived from mono- and disaccharides. Polym Int 42 (1997) 1-8
137. Melo B.N., and Pasa V.M.D. Thermal and morphological study of polyurethanes based on Eucalyptus tar pitch and castor oil. J Appl Polym Sci 92 (2004) 3287-3291
138. Araujo R.C.S., and Pasa V.M.D. Mechanical and thermal properties of polyurethane elastomers based on hydroxyl-terminated polybutadienes and biopitch. J Appl Polym Sci 88 (2003) 759-766
139. Melo B.N., and Pasa V.M.D. Composites based on eucalyptus tar pitch/castor oil polyurethane and short sisal fibers. J Appl Polym Sci 89 (2003) 3797-3802
140. Chang L.C., Xue Y., and Hsieh F.H. Dynamic-mechanical study of water-blown rigid polyurethane foams with and without soy flour. J Appl Polym Sci 80 (2001) 10-19
141. Chang L.C., Xue Y., and Hsieh F.H. Comparative study of physical properties of water-blown rigid polyurethane foams extended with commercial soy flours. J Appl Polym Sci 81 (2001) 2027-2035
142. Gao S., and Zhang L. Semi-interpenetrating polymer networks from castor oil-based polyurethane and nitrokonjac glucomannan. J Appl Polym Sci 81 (2001) 2076-2083
143. Gao S., Zhang L., and Huang Q. Effect of the synthesis route on the structure and properties of polyurethane/nitrokonjac glucomannan semi-interpenetrating polymer networks. J Appl Polym Sci 90 (2003) 1948-1954
144. Mohapatra D.K., Nayak P.L., and Lenka S. Polymers from renewable resources. XXI. Semi-interpenetrating polymer networks based on cardanol-formaldehyde-substituted aromatic compounds copolymerized resins and castor oil polyurethanes: synthesis, structure, scanning electron microscopy and XRD. J Polym Sci Part A Polym Chem 35 (1997) 3117-3124
145. Lu K.T., Liu C.T., and Lee H.L. Effect of nitrocellulose on the properties of PU-NC semi-IPN wood coatings. J Appl Polym Sci 89 (2003) 2157-2162
146. Huang J., and Zhang L. Structure and properties of regenerated cellulose films coated with polyurethane-nitrolignin graft-IPNs coating. J Appl Polym Sci 86 (2002) 1799-1806
147. Zhang L., and Huang J. Effects of hard-segment compositions on properties of polyurethane-nitrolignin films. J Appl Polym Sci 81 (2001) 3251-3259
148. Nayak P., Mishra D.K., Parida D., Sahoo K.C., Nanda M., Lenka S., et al. Polymers from renewable resources. IX. Interpenetrating polymer networks based on castor oil polyurethane poly(hydroxyethyl methacrylate): synthesis, chemical, thermal, and mechanical properties. J Appl Polym Sci 63 (1997) 671-679
149. Gong P., and Zhang L. Properties and interfacial bonding of regenerated cellulose films coated with polyurethane-chitosan IPN coating. J Appl Polym Sci 68 (1998) 1313-1319
150. Cao X., and Zhang L. Effects of molecular weight on the miscibility and properties of polyurethane/benzyl starch semi-interpenetrating polymer networks. Biomacromolecules 6 (2005) 671-677
151. Yeganeh H., and Hojati-Talemi P. Preparation and properties of novel biodegradable polyurethane networks based on castor oil and poly(ethylene glycol). Polym Degrad Stab 92 (2007) 480-489
152. Zhang L., Zhou J., Huang J., Gong P., Zhou Q., Zheng L., et al. Biodegradability of regenerated cellulose films coated with polyurethane/natural polymers interpenetrating polymer networks. Ind Eng Chem Res 38 (1999) 4284-4289
153. Silva R.V., Spinelli D., Bose Filho W.W., Claro Neto S., Chierice G.O., and Tarpani J.R. Fracture toughness of natural fibers/castor oils polyurethane composites. Comp Sci Technol 66 (2006) 1328-1355
154. Pechar T.W., Sohn S., Wilkes G.L., Ghosh S., Frazier C.E., Fornof A., et al. Characterization and comparison of polyurethane networks prepared using soybean-based polyols with varying hydroxyl content and their blends with petroleum-based polyols. J Appl Polym Sci 101 (2006) 1432-1443
155. Dusek K. Size of network chains. Macromolecules 17 (1984) 716-722
156. Ilavsky M., and Dusek M. The structure and elasticity of polyurethane networks. 1. Model networks of poly(oxypropylene) triols and diisocyanate. Polymer 24 (1982) 981-990
157. Zlatanic A., Petrovic Z.S., and Dusek K. Structure and properties of triolein-based polyurethane networks. Biomacromolecules 3 (2002) 1048-1056
158. Petrovic Z.S., Zhang W., and Javni I. Structure and properties of polyurethanes prepared from triglyceride polyols by ozonolysis. Biomacromolecules 6 (2005) 713-719
159. Kong X., and Narine S.S. Physical properties of canola oil based polyurethane networks. Biomacromolecules 8 (2007) 3584-3589
160. Kong X., and Narine S.S. Production of 9-hydroxynonanoic acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones. Biomacromolecules 9 (2008) 949-953
161. Narine S.S., and Kong X.H. Physical properties of polyurethane plastic sheets produced from polyols from canola oil. J Am Oil Chem Soc 84 (2007) 173-179
162. Lligadas G., Ronda J.C., Galia M., and Cadiz V. Novel silicon-containing polyurethanes from vegetable oils as renewable resources. Synthesis and properties. Biomacromolecules 7 (2006) 2420-2426
163. Lligadas G., Ronda J.C., Galia M., and Cadiz V. Polyurethane networks from fatty-acid-based aromatic triols: synthesis and characterization. Biomacromolecules 8 (2007) 1858-1864
164. Evtiouguina M., Barros-Timmons A., Cruz-Pinto J.J., Pascoal Neto C., Belgacem M.N., and Gandini A. Oxypropylation of cork and the use of the ensuing polyols in polyurethane formulations. Biomacromolecules 3 (2002) 57-62
165. Pavier C., and Gandini A. Oxypropylation of sugar beet pulp. 1. Optimisation of the reaction. Ind Crops Prod 12 (2000) 1-8
166. Pavier C., and Gandini A. Oxypropylation of sugar beet pulp. 2. Separation of the grafted pulp from the propylene oxide homopolymer. Carbohydr Polym 42 (2000) 13-17
167. Pavier C., and Gandini A. Urethanes and polyurethanes from oxypropylated sugar beet pulp. I. Kinetic study in solution. Eur Polym J 36 (2000) 1653-1658
168. Gandini A., and Belgacem M.N. Recent contributions to the preparation of polymers derived from renewable resources. J Polym Env 10 (2002) 105-114
169. Velasquez-Morales P., Le Nest J.F., and Gandini A. Polymer electrolytes derived from chitosan/polyether networks. Electrochim Acta 43 (1998) 1275-1279
170. Rogge T.M., Stevens C.V., Vandamme A., Booten K., Levecke B., D'hooge C., et al. Application of ethoxylated inulin in water-blown polyurethane foams. Biomacromolecules 6 (2005) 1992-1997
171. Bhunia H.P., Jana R.N., Basak A., Lenka S., and Nando G.B. Synthesis of polyurethane from cashew nut shell liquid (CNSL), a renewable resource. J Polym Sci Part A Polym Chem 36 (1998) 391-400
172. Suresh K.I., and Kishanprasad V.S. Synthesis, structure, and properties of novel polyols from cardanol and developed polyurethanes. Ind Eng Chem Res 44 (2005) 4504-4512
173. Dudgeon C.D. Unsaturated polyesters. In: Epel J.N., Margolis J.M., Newman S., and Seymour R.B. (Eds). Engineered materials handbook vol. 2 (1988), ASM International, Metals Park, OH p. 246-51
174. Guyot A., Landfester K., Schork F.J., and Wang C. Hybrid polymer latexes. Prog Polym Sci 32 (2007) 1439-1461
175. Penczek P., Czub P., and Pielichowski J. Unsaturated polyester resins: chemistry and technology. Adv Polym Sci 184 (2005) 1-95
176. Miyagawa H., Mohanty A.K., Burgueno R., Drzal L.T., and Misra M. Novel biobased resins from blends of functionalized soybean oil and unsaturated polyester resin. J Polym Sci Part B Polym Phys 45 (2007) 698-704
177. Noordover B.A., Duchateau R., van Benthem R.A., Ming W., and Koning C.E. Enhancing the functionality of biobased polyester coating resins through modification with citric acid. Biomacromolecules 8 (2007) 3860-3870
178. Thielemans W., and Wool R.P. Lignin esters for use in unsaturated thermosets: lignin modification and solubility modeling. Biomacromolecules 6 (2005) 1895-1905
179. Glasser W.G., and Jain R.K. Lignin derivatives. II. Functional ethers. Holzforschung 47 (1993) 225-233
180. van Haveren J., Oostveen E.A., Micciche F., Noordover B.A.J., Koning C.E., van Benthlem R.A., et al. Resins and additives for powder coatings and alkyd paints, based on renewable resources. J Coat Technol Res 4 (2007) 177-186
181. Andjelkovic D.D., Valverde M., Henna P., Li F., and Larock R.C. Novel thermosets prepared by cationic copolymerization of various vegetable oils-synthesis and their structure-property relationships. Polymer 46 (2005) 9674-9685
182. Vepari C., and Kaplan D.L. Silk as a biomaterial. Prog Polym Sci 32 (2007) 991-1007
183. De Graaf L.A. Denaturation of proteins from a non-food perspective. J Biotechnol 79 (2000) 299
184. Irissin-Mangata J., Bauduin G., Boutevin B., and Gontard N. New plasticizers for wheat gluten films. Eur Polym J 37 (2001) 1533-1541
185. Domenek S., Morel M.H., Redl A., and Guilbert S. Thermosetting of wheat protein based bioplastics: modeling of mechanism and material properties. Macromol Symp 197 (2003) 181-192
186. Brother G.H., and McKinney L.L. Protein plastics from soybean products. Ind Eng Chem 32 (1938) 1002-1003
187. Fritz R. Cottonseed meal in phenolic plastics. Ind Eng Chem 34 (1942) 1154-1157
188. Gross R.A., and Kalra B. Biodegradable polymers for the environment. Science 297 (2002) 803-807
189. Paetau I., Chen C.Z., and Jane J. Biodegradable plastic made from soybean products. 1. Effect of preparation and processing on mechanical properties and water absorption. Ind Eng Chem Res 33 (1994) 1821-1827
190. Paetau I., Chen C.Z., and Jane J. Biodegradable plastic made from soybean products. II. Effects of cross-linking and cellulose incorporation on mechanical properties and water absorption. J Polym Env 2 (1994) 211-217
191. Shih F.F. Interaction of soy isolate with polysaccharide and its effect on film properties. J Am Oil Chem Soc 71 (1994) 1281-1285
192. Sue H.J., Wang S., and Jane J.L. Morphology and mechanical behaviour of engineering soy plastics. Polymer 38 (1997) 5035-5040
193. Kumar R., Choudhary V., Mishra S., Varma I.K., and Mattiason B. Adhesives and plastics based on soy protein products. Ind Crops Prod 16 (2002) 155-172
194. Fraenakel-Conrat H., and Olcott H.S. Reaction of formaldehyde with proteins. VI. Cross-linking of amino groups with phenol, imidazole, or indole groups. J Biological Chem 174 (1948) 827-843
195. Vaz C., Van Doeveren P., Ylmaz G., de Graaf L., Reis R., and Cunha A. Processing and characterization of biodegradable soy plastics: effects of cross-linking with glyoxal and thermal treatment. J Appl Polym Sci 97 (2005) 604-610
196. Vaz C., Van Doeveren P., Reis R., and Cunha A. Soy matrix drug delivery systems obtained by melt-processing techniques. Biomacromolecules 4 (2003) 1520-1529
197. Santin M., Morris C., Standen G., Nicolais L., and Ambrosio L. New class of bioactive and biodegradable soybean-based bone fillers. Biomacromolecules 8 (2007) 2706-2711
198. Middleton E., Kanaswami C., and Theoharides T.C. The effects of plant flavonoids on mammalian cells:implications for inflammation, heart disease, and cancer. Pharmacol Rev 52 (2000) 673-751
199. Jerez A., Partal P., Martinez I., Gallegos C., and Guerrero A. Rheology and processing of gluten based bioplastics. Biochem Eng J 26 (2005) 131-138
200. Sartor G., and Johari G.P. Polymerization of a Vegetable protein. wheat gluten, and the glass-softening transition of its dry and reacted state. J Phys Chem 100 (1996) 19692-19701
201. Sun S., Song Y., and Zheng Q. Morphologies and properties of thermo-molded biodegradable plastics based on glycerol-plasticized wheat gluten. Food Hydrocolloids 21 (2007) 1005-1013
202. Reddy N., and Yang Y. Novel protein fibers from wheat gluten. Biomacromolecules 8 (2007) 638-643
203. Drack M., and Wimmer R. Woolrock-a material for technical use consisting of keratin. J Mat Sci 42 (2007) 6183-6187
204. Jerez A., Partal P., Martinez I., Gallegos C., and Guerrero A. Egg white-based bioplastics developed by thermomechanical processing. J Food Eng 82 (2007) 608-617
205. McDermott M.K., Chen T., Williams C.M., Markley K.M., and Payne G.F. Mechanical properties of biomimetic tissue adhesive based on the microbial transglutaminase-catalyzed cross-linking of gelatin. Biomacromolecules 5 (2004) 1270-1279
206. Martucci J.F., Ruseckaite R.A., and Vazquez A. Creep of glutaraldehyde-cross-linked gelatin films. Mater Sci Eng A435-436 (2006) 681-686
207. Shahidi F., Kamil Vidana Arachchi J., and Jeon Y. Food applications of chitin and chitosans. Trends Food Sci Tech 10 (1999) 37-51
208. Nair L.S., Starnes T., Ko J.W.K., and Laurencin C.T. Development of injectable thermogelling chitosan-inorganic phosphate solutions for biomedical applications. Biomacromolecules 8 (2007) 3779-3785
209. Berger J., Reist M., Chenite A., Felt-Baeyens O., Mayer J., and Gurny R. Pseudo-thermosetting chitosan hydrogels for biomedical application. Int J Pharma 288 (2005) 17-25
210. Chenite A., Chaput C., Wang D., Combes C., Buschmann M.D., Hoemann C.D., et al. Novel injectable neutral solutions of chitosan form biodegradable gels in situ. Biomaterials 21 (2000) 2155-2161
211. Schuetz Y.B., Gurny R., and Jordan O. A novel thermoresponsive hydrogel based on chitosan. Eur J Pharma Biopharma 68 (2008) 19-25
212. Teramoto N., and Shibata M. Trehalose-based thermosetting resins. I. Synthesis and thermal properties of trehalose vinylbenzyl ether. J Appl Polym Sci 91 (2004) 46-51
213. Teramoto N., and Shibata M. Synthesis and photocuring of cinnamoyl trehalose esters. Polym Adv Tech 18 (2007) 971-977
214. Uihlein A., Ehrenberger S., and Schebek L. Utilization options of renewable resources: a life cycle assessment of selected products. J Cleaner Product 16 (2008) 1306-1320