Sustainable thermoplastic elastomers derived from fatty acids

Macromolecules

Volumn 46, Issue 18, 2013, Pages 7202-7212

  Wang, Shu ^a   Vajjala Kesava, Sameer ^b   Gomez, Enrique D ^b   Robertson, Megan L ^a  

^a UNIVERSITY OF HOUSTON   (United States)

^b The Pennsylvania State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELASTOMERIC BEHAVIOR; FUNCTIONALIZATIONS; MICROPHASE-SEPARATED MORPHOLOGY; ORDER-DISORDER TRANSITION TEMPERATURE; PROCESSING TEMPERATURE; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; SMALL ANGLE X-RAY SCATTERING; SPHERICAL MORPHOLOGIES;

MORPHOLOGY; PALM OIL; PHYSICAL PROPERTIES; POLYMERS; SOYBEAN OIL; STYRENE; TEMPERATURE; TENSILE TESTING; THERMOPLASTIC ELASTOMERS; TOOLS; TRANSMISSION ELECTRON MICROSCOPY;

BLOCK COPOLYMERS;

EID: 84884882577     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma4011846     Document Type: Article

References (96)

1. Holden, G.; Legge, N. R.; Quirk, R.; Schroeder, H. E. Thermoplastic Elastomers, 2 nd ed.; Hanser Publishers: Munich, 1996.
2. Weisz, P. B. Basic choices and constraints on long-term energy supplies Phys. Today 2004, 57 (7) 47-51
3. Xu, J.; Zhang, A.; Zhou, T.; Cao, X.; Xie, Z. A study on thermal oxidation mechanism of styrene-butadiene-styrene block copolymer (SBS) Polym. Degrad. Stab. 2007, 92 (9) 1682-1691
4. Cortizo, M. S.; Larsen, D. O.; Bianchetto, H.; Alessandrini, J. L. Effect of the thermal degradation of SBS copolymers during the ageing of modified asphalts Polym. Degrad. Stab. 2004, 86 (2) 275-282
5. Singh, R. P.; Desai, S. M.; Solanky, S. S.; Thanki, P. N. Photodegradation and stabilization of styrene-butadiene-styrene rubber J. Appl. Polym. Sci. 2000, 75 (9) 1103-1114
6. Prasad, A. V.; Singh, R. P. Photooxidative degradation of styrenic polymers: 13C-NMR and morphological changes upon irradiation J. Appl. Polym. Sci. 1998, 70 (4) 637-645
7. Meier, M. A. R.; Metzger, J. O.; Schubert, U. S. Plant oil renewable resources as green alternatives in polymer science Chem. Soc. Rev. 2007, 36, 1788-1802
8. Xia, Y.; Larock, R. C. Vegetable oil-based polymeric materials: synthesis, properties, and applications Green Chem. 2010, 12 (11) 1893-1909
9. Bhardwaj, R.; Mohanty, A. K. Advances in the properties of polylactides based materials: A review J. Biobased Mater. Bioenergy 2007, 1 (2) 191-209
10. Gallezot, P. Process options for converting renewable feedstocks to bioproducts Green Chem. 2007, 9 (4) 295-302
11. Wondraczek, H.; Kotiaho, A.; Fardim, P.; Heinze, T. Photoactive polysaccharides Carbohydr. Polym. 2011, 83 (3) 1048-1061
12. Wilbon, P. A.; Chu, F.; Tang, C. Progress in renewable polymers from natural terpenes, terpenoids, and rosin Macromol. Rapid Commun. 2013, 34 (1) 8-37
13. Gandini, A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology Green Chem. 2011, 13 (5) 1061-1083
14. Hiki, S.; Miyamoto, M.; Kimura, Y. Synthesis and characterization of hydroxy-terminated [RS]-poly(3 hydroxybutyrate) and its utilization to block copolymerization with L-lactide to obtain a biodegradable thermoplastic elastomer Polymer 2000, 41 (20) 7369-7379
15. Kelley, A. S.; Srienc, F. Controlling the polymer microstructure of biodegradable polyhydroxyalkanoates. In Biocatalysis in Polymer Science; Gross, R. A.; Cheng, H. N., Eds.; American Chemical Society: Washington, DC, 2003; Vol. 840, pp 124-127.
16. Chatterjee, D. P.; Mandal, B. M. Triblock thermoplastic elastomers with poly(lauryl methacrylate) as the center block and poly(methyl methacrylate) or poly(tert-butyl methacrylate) as end blocks. morphology and thermomechanical properties Macromolecules 2006, 39 (26) 9192-9200
17. Wanamaker, C. L.; O'Leary, L. E.; Lynd, N. A.; Hillmyer, M. A.; Tolman, W. B. Renewable-resource thermoplastic elastomers based on polylactide and polymenthide Biomacromolecules 2007, 8 (11) 3634-3640
18. Shin, J.; Martello, M. T.; Shrestha, M.; Wissinger, J. E.; Tolman, W. B.; Hillmyer, M. A. Pressure-sensitive adhesives from renewable triblock copolymers Macromolecules 2010, 44 (1) 87-94
19. Martello, M. T.; Hillmyer, M. A. Polylactide-poly(6-methyl-ε- caprolactone)-polylactide thermoplastic elastomers Macromolecules 2011, 44 (21) 8537-8545
20. Bueno-Ferrer, C.; Hablot, E.; Garrigós, M. d. C.; Bocchini, S.; Averous, L.; Jiménez, A. Relationship between morphology, properties and degradation parameters of novative biobased thermoplastic polyurethanes obtained from dimer fatty acids Polym. Degrad. Stab. 2012, 97 (10) 1964-1969
21. Shin, J.; Lee, Y.; Tolman, W. B.; Hillmyer, M. A. Thermoplastic elastomers derived from menthide and tulipalin A Biomacromolecules 2012, 13 (11) 3833-3840
22. Jiang, F.; Wang, Z.; Qiao, Y.; Wang, Z.; Tang, C. A novel architecture toward third-generation thermoplastic elastomers by a grafting strategy Macromolecules 2013, 46 (12) 4772-4780
23. Saralegi, A.; Rueda, L.; Fernández-d'Arlas, B.; Mondragon, I.; Eceiza, A.; Corcuera, M. A. Thermoplastic polyurethanes from renewable resources: effect of soft segment chemical structure and molecular weight on morphology and final properties Polym. Int. 2013, 62 (1) 106-115
24. Sonnenschein, M. F.; Ginzburg, V. V.; Schiller, K. S.; Wendt, B. L. Design, polymerization, and properties of high performance thermoplastic polyurethane elastomers from seed-oil derived soft segments Polymer 2013, 54 (4) 1350-1360
25. Shogren, R. L.; Petrovic, Z.; Liu, Z.; Erhan, S. Z. Biodegradation behavior of some vegetable oil-based polymers J. Polym. Environ. 2004, 12 (3) 173-178
26. Ronda, J. C.; Lligadas, G.; Galià, M.; Cádiz, V. Vegetable oils as platform chemicals for polymer synthesis Eur. J. Lipid Sci. Technol. 2011, 113 (1) 46-58
27. Lu, Y.; Larock, R. Novel polymeric materials from vegetable oils and vinyl monomers: preparation, properties, and applications ChemSusChem 2009, 2 (2) 136-147
28. Domb, A. J.; Nudelman, R. Biodegradable polymers derived from natural fatty acids J. Polym. Sci., Part A: Polym. Chem. 1995, 33 (4) 717-725
29. Jain, J. P.; Sokolsky, M.; Kumar, N.; Domb, A. J. Fatty acid based biodegradable polymer Polym. Rev. 2008, 48 (1) 156-191
30. Vilela, C.; Rua, R.; Silvestre, A. J. D.; Gandini, A. Polymers and copolymers from fatty acid-based monomers Ind. Crops Prod. 2010, 32 (2) 97-104
31. Metzger, J. O.; Bornscheuer, U. Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification Appl. Microbiol. Biotechnol. 2006, 71 (1) 13-22
32. Warwel, S.; Klaas, M. R. G. Chemo-enzymatic epoxidation of unsaturated carboxylic acids J. Mol. Catal. B: Enzym. 1995, 1 (1) 29-35
33. Gupta, A. P.; Ahmad, S.; Dev, A. Modification of novel bio-based resin-epoxidized soybean oil by conventional epoxy resin Polym. Eng. Sci. 2011, 51 (6) 1087-1091
34. Park, S. J.; Jin, F. L.; Lee, J. R. Synthesis and thermal properties of epoxidized vegetable oil Macromol. Rapid Commun. 2004, 25 (6) 724-727
35. Ionescu, M.; Petrovic, Z. S.; Wan, X. M. Ethoxylated soybean polyols for polyurethanes J. Polym. Environ. 2010, 18 (1) 1-7
36. Lligadas, G.; Ronda, J. C.; Galia, M.; Biermann, U.; Metzger, J. O. Synthesis and characterization of polyurethanes from epoxidized methyl oleate based polyether polyols as renewable resources J. Polym. Sci., Part A: Polym. Chem. 2006, 44 (1) 634-645
37. Campanella, A.; La Scala, J. J.; Wool, R. P. The use of acrylated fatty acid methyl esters as styrene replacements in triglyceride-based thermosetting polymers Polym. Eng. Sci. 2009, 49 (12) 2384-2392
38. Beers, K. L.; Matyjaszewski, K. The atom transfer radical polymerization of lauryl acrylate J. Macromol. Sci., Pure Appl. Chem. 2001, 38 (7) 731-739
39. Zhu, J.; Zhu, X. L.; Cheng, Z. P.; Lu, J. M.; Liu, F. Reversible addition-fragmentation chain-transfer polymerization of octadecyl acrylate J. Macromol. Sci., Pure Appl. Chem. 2003, A40 (9) 963-975
40. O'Leary, K. A.; Paul, D. R. Physical properties of poly(n-alkyl acrylate) copolymers. Part 1. Crystalline/crystalline combinations Polymer 2006, 47 (4) 1226-1244
41. Henna, P.; Larock, R. C. Novel thermosets obtained by the ring-opening metathesis polymerization of a functionalized vegetable oil and dicyclopentadiene J. Appl. Polym. Sci. 2009, 112 (3) 1788-1797
42. Mauldin, T. C.; Haman, K.; Sheng, X.; Henna, P.; Larock, R. C.; Kessler, M. R. Ring-opening metathesis polymerization of a modified linseed oil with varying levels of crosslinking J. Polym. Sci., Part A: Polym. Chem. 2008, 46 (20) 6851-6860
43. Henna, P. H.; Larock, R. C. Rubbery Thermosets by ring-opening metathesis polymerization of a functionalized castor oil and cyclooctene Macromol. Mater. Eng. 2007, 292 (12) 1201-1209
44. Mutlu, H.; Meier, M. A. R. Ring-opening metathesis polymerization of fatty acid derived monomers J. Polym. Sci., Polym. Chem. 2010, 48 (24) 5899-5906
45. 2 catalyst Catal. Sci. Technol. 2012, 2 (11) 2221-2223
46. 3 catalysts Appl. Catal., A 1999, 189 (2) 243-250
47. Dutta, P.; Gogoi, B.; Dass, N. N.; Sen Sarma, N. Efficient organic solvent and oil sorbent co-polyesters: Poly-9-octadecenylacrylate/methacrylate with 1 hexene React. Funct. Polym. 2013, 73 (3) 457-464
48. Bates, F. S.; Fredrickson, G. H. Block copolymers - designer soft materials Phys. Today 1999, 52 (2) 32
49. Nagpal, U.; Detcheverry, F. o. A.; Nealey, P. F.; de Pablo, J. J. Morphologies of linear triblock copolymers from Monte Carlo simulations Macromolecules 2011, 44 (13) 5490-5497
50. Matsen, M. W.; Thompson, R. B. Equilibrium behavior of symmetric ABA triblock copolymer melts J. Chem. Phys. 1999, 111 (15) 7139-7146
51. Lynd, N. A.; Hillmyer, M. A. Influence of polydispersity on the self-assembly of diblock copolymers Macromolecules 2005, 38 (21) 8803-8810
52. Lynd, N. A.; Meuler, A. J.; Hillmyer, M. A. Polydispersity and block copolymer self-assembly Prog. Polym. Sci. 2008, 33 (9) 875-893
53. Ruzette, A.-V.; Tencé-Girault, S.; Leibler, L.; Chauvin, F.; Bertin, D.; Guerret, O.; Gérard, P. Molecular disorder and mesoscopic order in polydisperse acrylic block copolymers prepared by controlled radical polymerization Macromolecules 2006, 39 (17) 5804-5814
54. Zhu, J.; Zhu, X.; Cheng, Z.; Lu, J.; Liu, F. Reversible addition-fragmentation chain-transfer polymerization of octadecyl acrylate J. Macromol. Sci., Part A: Pure Appl.Chem. 2003, 40 (9) 963-975
55. 4 in water Macromol. Chem. Phys. 2007, 208 (11) 1218-1227
56. Liénafa, L.; Monge, S.; Robin, J.-J. A versatile synthesis of poly(lauryl acrylate) using N-(n-octyl)-2-pyridylmethanimine in copper mediated living radical polymerization Eur. Polym. J. 2009, 45 (6) 1845-1850
57. Dutertre, F.; Pennarun, P.-Y.; Colombani, O.; Nicol, E. Straightforward synthesis of poly(lauryl acrylate)-b-poly(stearyl acrylate) diblock copolymers by ATRP Eur. Polym. J. 2011, 47 (3) 343-351
58. Srivastava, P. K.; Choudhary, V. N-(n-Alkyl)-2-pyridinemethanimine mediated atom transfer radical polymerization of lauryl methacrylate: Effect of length of alkyl group J. Appl. Polym. Sci. 2012, 125 (1) 31-37
59. Beers, K.; Matyjaszewski, K. The atom transfer radical polymerization of lauryl acrylate J. Macromol. Sci., Part A: Pure Appl.Chem. 2001, 38 (7) 731
60. Dziczkowski, J.; Chatterjee, U.; Soucek, M. Route to co-acrylic modified alkyd resins via a controlled polymerization technique Prog. Org. Coat. 2012, 73 (4) 355-365
61. Dziczkowski, J.; Soucek, M. D. A new class of acrylated alkyds J. Coat. Technol. Res. 2010, 7 (5) 587-602
62. Chatterjee, D. P.; Mandal, B. M. Facile atom transfer radical homo and block copolymerization of higher alkyl methacrylates at ambient temperature using CuCl/PMDETA/quaternaryammonium halide catalyst system Polymer 2006, 47 (6) 1812-1819
63. Buback, M.; Hesse, P.; Junkers, T.; Theis, T.; Vana, P. Chain-length-dependent termination in acrylate radical polymerization studied via pulsed-laser-initiated RAFT polymerization Aust. J. Chem. 2007, 60 (10) 779-787
64. Çayli, G.; Meier, M. A. R. Polymers from renewable resources: Bulk ATRP of fatty alcohol-derived methacrylates Eur. J. Lipid Sci. Technol. 2008, 110 (9) 853-859
65. Karaky, K.; Clisson, G.; Reiter, G.; Billon, L. Semicrystalline macromolecular design by nitroxide-mediated polymerization Macromol. Chem. Phys. 2008, 209 (7) 715-722
66. Qin, S. H.; Saget, J.; Pyun, J. R.; Jia, S. J.; Kowalewski, T.; Matyjaszewski, K. Synthesis of block, statistical, and gradient copolymers from octadecyl (meth)acrylates using atom transfer radical polymerization Macromolecules 2003, 36 (24) 8969-8977
67. Street, G.; Illsley, D.; Holder, S. J. Optimization of the synthesis of poly(octadecyl acrylate) by atom transfer radical polymerization and the preparation of all comblike amphiphilic diblock copolymers J. Polym. Sci., Polym. Chem. 2005, 43 (5) 1129-1143
68. Theis, A.; Feldermann, A.; Charton, N.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C. Living free radical polymerization (RAFT) of dodecyl acrylate: Chain length dependent termination, mid-chain radicals and monomer reaction order Polymer 2005, 46 (18) 6797-6809
69. Moad, G.; Rizzardo, E.; Thang, S. H. Toward living radical polymerization Acc. Chem. Res. 2008, 41 (9) 1133-1142
70. Jordan, E. F. Side-chain crystallinity. III. Influence of side-chain crystallinity on the glass transition temperatures of selected copolymers incorporating n-octadecyl acrylate or vinyl stearate J. Polym. Sci., Part A-1: Polym. Chem. 1971, 9 (11) 3367-3378
71. Konaganti, V. K.; Madras, G. Photocatalytic and thermal degradation of poly(methyl methacrylate), poly(butyl acrylate), and their copolymers Ind. Eng. Chem. Res. 2009, 48 (4) 1712-1718
72. Mahalik, J. P.; Madras, G. Effect of alkyl group substituents, temperature, and solvents on the ultrasonic degradation of poly(n-alkyl acrylates) Ind. Eng. Chem. Res. 2005, 44 (17) 6572-6577
73. Patton, D. L.; Mullings, M.; Fulghum, T.; Advincula, R. C. A facile synthesis route to thiol-functionalized α,ω-telechelic polymers via reversible addition fragmentation chain transfer polymerization Macromolecules 2005, 38 (20) 8597-8602
74. Legge, T. M.; Slark, A. T.; Perrier, S. Novel difunctional reversible addition fragmentation chain transfer (RAFT) agent for the synthesis of telechelic and ABA triblock methacrylate and acrylate copolymers Macromolecules 2007, 40 (7) 2318-2326
75. Bae, S.-k.; Lee, S.-Y.; Hong, S. C. Thiol-terminated polystyrene through the reversible addition-fragmentation chain transfer technique for the preparation of gold nanoparticles and their application in organic memory devices React. Funct. Polym. 2011, 71 (2) 187-194
76. Moad, G.; Rizzardo, E.; Thang, S. H. Living radical polymerization by the RAFT process Aust. J. Chem. 2005, 58 (6) 379-410
77. Lin, L. Y.; Lee, N. S.; Zhu, J.; Nyström, A. M.; Pochan, D. J.; Dorshow, R. B.; Wooley, K. L. Tuning core vs. shell dimensions to adjust the performance of nanoscopic containers for the loading and release of doxorubicin J. Controlled Release 2011, 152 (1) 37-48
78. Lovestead, T. M.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C. Scope for accessing the chain length dependence of the termination rate coefficient for disparate length radicals in acrylate free radical polymerization Macromol. Symp. 2007, 248, 82-93
79. O'Leary, K.; Paul, D. R. Copolymers of poly(n-alkyl acrylates): synthesis, characterization, and monomer reactivity ratios Polymer 2004, 45 (19) 6575-6585
80. Hsieh, H. W. S.; Post, B.; Morawetz, H. A crystallographic study of polymers exhibiting side-chain crystallization J. Polym. Sci., Polym. Phys. Ed. 1976, 14 (7) 1241-1255
81. Jordan, E. F.; Artymyshyn, B.; Speca, A.; Wrigley, A. N. Side-chain crystallinity. II. Heats of fusion and melting transitions on selected copolymers incorporating n-octadecyl acrylate or vinyl stearate J. Polym. Sci., Part A-1: Polym. Chem. 1971, 9 (11) 3349-3365
82. Jordan, E. F.; Feldeise, Dw; Wrigley, A. N. Side-chain crystallinity 0.1. Heats of fusion and melting transitions on selected homopolymers having long side chains J. Polym. Sci., Part A-1: Polym. Chem. 1971, 9 (7) 1835
83. O'Leary, K. A.; Paul, D. R. Physical properties of poly(n-alkyl acrylate) copolymers. Part 2. Crystalline/non-crystalline combinations Polymer 2006, 47 (4) 1245-1258
84. Fei, P.; Cavicchi, K. A. Synthesis and characterization of a poly(styrene-block-methylacrylate-random-octadecylacrylate-block-styrene) shape memory ABA triblock copolymer ACS Appl. Mater. Interfaces 2010, 2 (10) 2797-2803
85. Funaki, Y.; Kumano, K.; Nakao, T.; Jinnai, H.; Yoshida, H.; Kimishima, K.; Tsutsumi, K.; Hirokawa, Y.; Hashimoto, T. Influence of casting solvents on microphase-separated structures of poly(2-vinylpyridine)-block-polyisoprene Polymer 1999, 40 (25) 7147-7156
86. Hashimoto, T.; Kawamura, T.; Harada, M.; Tanaka, H. Small-angle scattering from hexagonally packed cylindrical particles with paracrystalline distortion Macromolecules 1994, 27 (11) 3063-3072
87. Widin, J. M.; Schmitt, A. K.; Schmitt, A. L.; Im, K.; Mahanthappa, M. K. Unexpected consequences of block polydispersity on the self-assembly of ABA triblock copolymers J. Am. Chem. Soc. 2012, 134 (8) 3834-3844
88. Eitouni, H. B.; Balsara, N. P. Thermodynamics of polymer blends. In Physical Properties of Polymers Handbook, 2 nd ed.; Mark, J. E., Ed.; Springer: New York, 2007.
89. Russell, T. P. Changes in polystyrene and poly(methyl methacrylate) interactions with isotopic substitution Macromolecules 1993, 26 (21) 5819-5819
90. Hammouda, B.; Bauer, B. J.; Russell, T. P. Small-angle neutron scattering from deuterated polystyrene/poly(butyl methacrylate) homopolymer blend mixtures Macromolecules 1994, 27 (8) 2357-2359
91. Ryu, D. Y.; Park, M. S.; Chae, S. H.; Jang, J.; Kim, J. K.; Russell, T. P. Phase behavior of polystyrene and poly(n-pentyl methacrylate) blend Macromolecules 2002, 35 (23) 8676-8680
92. Lewin, J. L.; Maerzke, K. A.; Schultz, N. E.; Ross, R. B.; Siepmann, J. I. Prediction of Hildebrand solubility parameters of acrylate and methacrylate monomers and their mixtures by molecular simulation J. Appl. Polym. Sci. 2010, 116 (1) 1-9
93. Fetters, L. J.; Lohse, D. J.; Milner, S. T.; Graessley, W. W. Packing length influence in linear polymer melts on the entanglement, critical, and reptation molecular weights Macromolecules 1999, 32 (20) 6847-6851
94. Roovers, J.; Toporowski, P. M. Characteristic ratio and plateau modulus of 1,2-polybutadiene-a comparison with other rubbers Rubber Chem. Technol. 1990, 63 (5) 734-746
95. Gotro, J. T.; Graessley, W. W. Model hydrocarbon polymers: rheological properties of linear polyisoprenes and hydrogenated polyisoprenes Macromolecules 1984, 17 (12) 2767-2775
96. Tong, J. D.; Leclère, P.; Doneux, C.; Brédas, J. L.; Lazzaroni, R.; Jéroîme, R. Morphology and mechanical properties of poly(methylmethacrylate)-b-poly(alkylacrylate)-b-poly(methylmethacrylate) Polymer 2001, 42 (8) 3503-3514