A facile method for generating designer block copolymers from functionalized lignin model compounds

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 4, 2014, Pages 569-573

  Holmberg, Angela L ^a   Stanzione, Joseph F ^a,b,c   Wool, Richard P ^a,b   Epps, Thomas H ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

^c Rowan University   (United States)

Author keywords

Biobased; Block copolymer; Lignin; RAFT; Renewable; Self assembly; Vanillin

Indexed keywords

BLOCK COPOLYMERS; CHAINS; HOMOPOLYMERIZATION; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

BIO-BASED; CONTROLLED POLYMERIZATION; PETROLEUM-BASED MATERIALS; RAFT; RENEWABLE; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; SMALL ANGLE X-RAY SCATTERING; VANILLIN;

LIGNIN;

EID: 84897988492     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400497a     Document Type: Article

References (40)

1. Hadjichristidis, N., Pispas, S., and Floudas, G. Block Copolymers: Synthetic Strategies, Physical Properties, and Applications; Wiley-Interscience: Hoboken, NJ, 2003.
2. Report on Carcinogens, 12 th ed.; U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program: Research Triangle Park, NC, 2011.
3. Mülhaupt, R. Green polymer chemistry and bio-based plastics: Dreams and reality Macromol. Chem. Phys. 2013, 214 (2) 159-174
4. Anastas, P.; Eghbali, N. Green chemistry: Principles and practice Chem. Soc. Rev. 2010, 39 (1) 301-312
5. Holmberg, A. L.; Stanzione, J. F., III; Wool, R. P.; Epps, T. H., III Bio-based block copolymer derived from lignin and plant oils. U.S. Provisional Patent Application 61/789,490, unpublished work, March 15, 2013.
6. Gandini, A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology Green Chem. 2011, 13 (5) 1061-1083
7. Jegers, H. E.; Klein, M. T. Primary and secondary lignin pyrolysis reaction pathways Ind. Eng. Chem. Process Des. Dev. 1985, 24 (1) 173-183
8. Brodin, I.; Sjöholm, E.; Gellerstedt, G. The behavior of kraft lignin during thermal treatment J. Anal. Appl. Pyrolysis 2010, 87 (1) 70-77
9. Mathers, R. T. How well can renewable resources mimic commodity monomers and polymers? J. Polym. Sci., Part A: Polym. Chem. 2012, 50 (1) 1-15
10. Mosnáček, J.; Yoon, J. A.; Juhari, A.; Koynov, K.; Matyjaszewski, K. Synthesis, morphology and mechanical properties of linear triblock copolymers based on poly(α-methylene-γ-butyrolactone) Polymer 2009, 50 (9) 2087-2094
11. Miyake, G. M.; Newton, S. E.; Mariott, W. R.; Chen, E. Y.-X. Coordination polymerization of renewable butyrolactone-based vinyl monomers by lanthanide and early metal catalysts Dalton Trans. 2010, 39 (29) 6710-6718
12. 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
13. Robertson, M. L.; Hillmyer, M. A.; Mortamet, A.-C.; Ryan, A. J. Biorenewable multiphase polymers MRS Bull. 2010, 35 (3) 194-200
14. Mialon, L.; Vanderhenst, R.; Pemba, A. G.; Miller, S. A. Polyalkylenehydroxybenzoates (PAHBs): Biorenewable aromatic/aliphatic polyesters from lignin Macromol. Rapid Commun. 2011, 32 (17) 1386-1392
15. da Silva, E. A. B.; Zabkova, M.; Araújo, J. D.; Cateto, C. A.; Barreiro, M. F.; Belgacem, M. N.; Rodrigues, A. E. An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin Chem. Eng. Res. Des. 2009, 87 (9) 1276-1292
16. 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
17. La Scala, J. J.; Sands, J. M.; Orlicki, J. A.; Robinette, E. J.; Palmese, G. R. Fatty acid-based monomers as styrene replacements for liquid molding resins Polymer 2004, 45 (22) 7729-7737
18. Greenberg, S. A.; Alfrey, T. Side chain crystallization of n -alkyl polymethacrylates and polyacrylates J. Am. Chem. Soc. 1954, 76 (24) 6280-6285
19. Wang, X. A.; He, X. J.; Huang, G. S.; Wu, J. R. Correlations between alkyl side chain length and dynamic mechanical properties of poly(n-alkyl acrylates) and poly(n-alkyl methacrylates) Polymer 2012, 53 (2) 665-672
20. Rogers, S. S.; Mandelkern, L. Glass transitions of the poly-(n -alkyl methacrylates) J. Phys. Chem. 1957, 61 (7) 985-990
21. Cho, K. Y.; Hwang, S. S.; Yoon, H. G.; Baek, K.-Y. Electroactive methacrylate-based triblock copolymer elastomer for actuator application J. Polym. Sci., Part A: Polym. Chem. 2013, 51 (9) 1924-1932
22. Fielding, L. A.; Derry, M. J.; Ladmiral, V.; Rosselgong, J.; Rodrigues, A. M.; Ratcliffe, L. P. D.; Sugihara, S.; Armes, S. P. RAFT dispersion polymerization in non-polar solvents: Facile production of block copolymer spheres, worms and vesicles in n -alkanes Chem. Sci. 2013, 4 (5) 2081-2087
23. 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
24. Chatterjee, D. P.; Mandal, B. M. The ATRP synthesis of the potential thermoplastic elastomer poly(methyl methacrylate)-b-(lauryl methacrylate)-b- (methyl methacrylate) hitherto unrealized by ionic polymerization Macromol. Symp. 2006, 240 (1) 224-231
25. Wang, S.; Kesava, S. V.; Gomez, E. D.; Robertson, M. L. Sustainable thermoplastic elastomers derived from fatty acids Macromolecules 2013, 46 (18) 7202-7212
26. Stanzione, J. F., III; Sadler, J. M.; La Scala, J. J.; Wool, R. P. Lignin model compounds as bio-based reactive diluents for liquid molding resins ChemSusChem 2012, 5 (7) 1291-1297
27. Semsarilar, M.; Perrier, S. 'Green' reversible addition-fragmentation chain-transfer (RAFT) polymerization Nat. Chem. 2010, 2 (10) 811-820
28. Han, X. Q.; Fan, J.; He, J. P.; Xu, J. T.; Fan, D. Q.; Yang, Y. L. Direct observation of the RAFT polymerization process by chromatography Macromolecules 2007, 40 (15) 5618-5624
29. Floudas, G.; Placke, P.; Štěpánek, P.; Brown, W.; Fytas, G.; Ngai, K. L. Dynamics of the ′strong′ polymer of n -lauryl methacrylate below and above the glass transition Macromolecules 1995, 28 (20) 6799-6807
30. Stanzione, J. F., III; Sadler, J. M.; La Scala, J. J.; Palmese, G. R.; Wool, R. P., The effect of methacrylated lignin model compound structure on the properties of high-performance polymers. In preparation, 2014.
31. Postma, A.; Davis, T. P.; Moad, G.; O'Shea, M. S. Thermolysis of RAFT-synthesized polymers. A convenient method for trithiocarbonate group elimination Macromolecules 2005, 38 (13) 5371-5374
32. Chong, B.; Moad, G.; Rizzardo, E.; Skidmore, M.; Thang, S. H. Thermolysis of RAFT-synthesized poly(methyl methacrylate) Aust. J. Chem. 2006, 59 (10) 755-762
33. Shapi, M. M. TG and DSC studies of some thermal properties and stability aspects of poly(acrylonitrile butadiene styrene), polystyrene and poly(acrylonitrile styrene) plastics Thermochim. Acta 1991, 175 (1) 25-34
34. Yao, Q.; Wilkie, C. A. How does cross-linking affect the thermal stability of polyisoprene? Polym. Degrad. Stab. 2000, 69 (3) 287-296
35. Jamshidi, K.; Hyon, S.-H.; Ikada, Y. Thermal characterization of polylactides Polymer 1988, 29 (12) 2229-2234
36. 2 atmosphere Iran. Polym. J. 2001, 10 (6) 371-376
37. Carrasco, F.; Pagès, P.; Gámez-Pérez, J.; Santana, O. O.; Maspoch, M. L. Processing of poly(lactic acid): Characterization of chemical structure, thermal stability and mechanical properties Polym. Degrad. Stab. 2010, 95 (2) 116-125
38. Matsen, M. W. Effect of architecture on the phase behavior of AB-type block copolymer melts Macromolecules 2012, 45 (4) 2161-2165
39. Dormidontova, E. E.; Lodge, T. P. The order-disorder transition and the disordered micelle regime in sphere-forming block copolymer melts Macromolecules 2001, 34 (26) 9143-9155
40. Barner-Kowollik, C. Handbook of RAFT Polymerization. Wiley-VCH: Weinheim, Germany, 2008.