New poly(ether urethane)s based on lignin derived aromatic chemicals via A-B monomer approach: Synthesis and characterization

European Polymer Journal

Volumn 71, Issue , 2015, Pages 547-557

  Kuhire, Sachin S ^a   Avadhani, C V ^a   Wadgaonkar, Prakash P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

A B type monomer; Poly(ether urethane)s; Renewable resources; Self polycondensation

Indexed keywords

AROMATIC COMPOUNDS; ETHERS; LIGNIN; MONOMERS;

AROMATIC CHEMICALS; AROMATIC RINGS; HIGH MOLECULAR WEIGHT; PHENOLIC ACIDS; POLY(ETHER URETHANE)S; RENEWABLE RESOURCE; SYNTHESIS AND CHARACTERIZATIONS; VANILLIC ACIDS;

ESTERS;

EID: 84940516561     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2015.08.021     Document Type: Article

References (47)

1. H.-W. Engels, H.-G. Pirkl, R. Albers, R.W. Albach, J. Krause, A. Hoffmann, and et al. Polyurethanes: versatile materials and sustainable problem solvers for today's challenges Angew. Chem. Int. Ed. 52 2013 9422 9441 10.1002/anie.201302766
2. M. Desroches, M. Escouvois, R. Auvergne, S. Caillol, and B. Boutevin From vegetable oils to polyurethanes: synthetic routes to polyols and main industrial products Polym. Rev. 52 2012 38 79 10.1080/15583724.2011.640443
3. A.S. More, T. Lebarbé, L. Maisonneuve, B. Gadenne, C. Alfos, and H. Cramail Novel fatty acid based di-isocyanates towards the synthesis of thermoplastic polyurethanes Eur. Polym. J. 49 2013 823 833 10.1016/j.eurpolymj.2012.12.013
4. L. Hojabri, X. Kong, and S.S. Narine Novel long chain unsaturated diisocyanate from fatty acid: synthesis, characterization, and application in bio-based polyurethane J. Polym. Sci., A: Polym. Chem. 48 2010 3302 3310 10.1002/pola.24114
5. C.N.D. Neumann, W.D. Bulach, M. Rehahn, and R. Klein Water-free synthesis of polyurethane foams using highly reactive diisocyanates derived from 5-hydroxymethylfurfural Macromol. Rapid Commun. 32 2011 1373 1378 10.1002/marc.201100205
6. L. Hojabri, X. Kong, and S.S. Narine Fatty acid-derived diisocyanate and biobased polyurethane produced from vegetable oil: synthesis, polymerization, and characterization Biomacromolecules 10 2009 884 891 10.1021/bm801411w
7. R.J. González-Paz, C. Lluch, G. Lligadas, J.C. Ronda, M. Galià, and V. Cádiz A green approach toward oleic- and undecylenic acid-derived polyurethanes J. Polym. Sci., A: Polym. Chem. 49 2011 2407 2416 10.1002/pola.24671
8. A. Zlatanić, C. Lava, W. Zhang, and Z.S. Petrović Effect of structure on properties of polyols and polyurethanes based on different vegetable oils J. Polym. Sci., B: Polym. Phys. 42 2004 809 819 10.1002/polb.10737
9. V. Sharma, and P.P. Kundu Condensation polymers from natural oils Prog. Polym. Sci. 33 2008 1199 1215 10.1016/j.progpolymsci.2008.07.00
10. Y. Xia, and R.C. Larock Vegetable oil-based polymeric materials: synthesis, properties, and applications Green Chem. 12 2010 1893 1909 10.1039/C0GC00264J
11. F. Yu, P. Saha, P.W. Suh, and J.K. Kim Green polyurethane from dimer acid based polyether polyols: synthesis and characterization J. Appl. Polym. Sci. 132 2015 10.1002/app.4141
12. M.D. Zenner, Y. Xia, J.S. Chen, and M.R. Kessler Polyurethanes from isosorbide-based diisocyanates ChemSusChem 6 2013 1182 1185 10.1002/cssc.201300126
13. H.B. Abderrazak, A. Fildier, H.B. Romdhane, S. Chatti, and H.R. Kricheldorf Synthesis of new poly(ether ketone)s derived from biobased diols Macromol. Chem. Phys. 214 2013 1423 1433 10.1002/macp.201300015
14. M. Gomes, A. Gandini, A.J.D. Silvestre, and B. Reis Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols J. Polym. Sci., A: Polym. Chem. 49 2011 3759 3768 10.1002/pola.24812
15. C. Zeng, H. Seino, J. Ren, K. Hatanaka, and N. Yoshie Bio-based furan polymers with self-healing ability Macromolecules 46 2013 1794 1802 10.1021/ma3023603
16. D.V. Palaskar, A. Boyer, E. Cloutet, C. Alfos, and H. Cramail Synthesis of biobased polyurethane from oleic and ricinoleic acids as the renewable resources via the AB-type self-condensation approach Biomacromolecules 11 2010 1202 1211 10.1021/bm100233v
17. A.S. More, B. Gadenne, C. Alfos, and H. Cramail AB type polyaddition route to thermoplastic polyurethanes from fatty acid derivatives Polym. Chem. 3 2012 1594 1605 10.1039/C2PY20123B
18. F. Bachmann, J. Reimer, M. Ruppenstein, and J. Thiem Synthesis of a novel starch-derived AB-type polyurethane Macromol. Rapid Commun. 19 1998 21 26 10.1002/(SICI)1521-3927(19980101)19:1<21::AID-MARC21>3.0.CO;2-T
19. F.G. Calvo-Flores, and J.A. Dobado Lignin as renewable raw material ChemSusChem 3 2010 1227 1235 10.1002/cssc.201000157
20. S. Laurichesse, and L. Avérous Chemical modification of lignins: towards biobased polymers Prog. Polym. Sci. 39 2014 1266 1290 10.1016/j.progpolymsci.2013.11.004
21. J. Zakzeski, P.C.A. Bruijnincx, A.L. Jongerius, and B.M. Weckhuysen The catalytic valorization of lignin for the production of renewable chemicals Chem. Rev. 110 2010 3552 3599 10.1021/cr900354u
22. E. Ten, and W. Vermerris Recent developments in polymers derived from industrial lignin J. Appl. Polym. Sci. 132 2015 10.1002/app.4206
23. B.G. Harvey, A.J. Guenthner, W.W. Lai, H.A. Meylemans, M.C. Davis, L.R. Cambrea, and et al. Effects of o-methoxy groups on the properties and thermal stability of renewable high-temperature cyanate ester resins Macromolecules 48 2015 3173 3179 10.1021/acs.macromol.5b00496
24. H.A. Meylemans, T.J. Groshens, and B.G. Harvey Synthesis of renewable bisphenols from creosol ChemSusChem 5 2012 206 210 10.1002/cssc.201100402
25. F. Pion, P.-H. Ducrot, and F. Allais Renewable alternating aliphatic-aromatic copolyesters derived from biobased ferulic acid, diols, and diacids: sustainable polymers with tunable thermal properties Macromol. Chem. Phys. 215 2014 431 439 10.1002/macp.201300702
26. L. Mialon, R. Vanderhenst, A.G. Pemba, and S.A. Miller Polyalkylenehydroxybenzoates (PAHBs): biorenewable aromatic/aliphatic polyesters from lignin Macromol. Rapid Commun. 32 2011 1386 1392 10.1002/marc.201100242
27. M. Firdaus, and M.A.R. Meier Renewable co-polymers derived from vanillin and fatty acid derivatives Eur. Polym. J. 49 2013 156 166 10.1016/j.eurpolymj.2012.10.017
28. L. Mialon, A.G. Pemba, and S.A. Miller Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid Green Chem. 12 2010 1704 1706 10.1039/C0GC00150C
29. M. Fache, B. Boutevin, and S. Caillol Vanillin, a key-intermediate of biobased polymers Eur. Polym. J. 68 2015 488 502 10.1016/j.eurpolymj.2015.03.050
30. M. Fache, E. Darroman, V. Besse, R. Auvergne, S. Caillol, and B. Boutevin Vanillin, a promising biobased building-block for monomer synthesis Green Chem. 16 2014 1987 1998 10.1039/C3GC42613K
31. C. Aouf, J. Lecomte, P. Villeneuve, E. Dubreucq, and H. Fulcrand Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers Green Chem. 14 2012 2328 2336 10.1039/C2GC35558B
32. A.G. Pemba, J.A. Flores, and S.A. Miller Acetal metathesis polymerization (AMP): a method for synthesizing biorenewable polyacetals Green Chem. 15 2013 325 329 10.1039/C2GC36588J
33. A.G. Pemba, M. Rostagno, T.A. Lee, and S.A. Miller Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics Polym. Chem. 5 2014 3214 3221 10.1039/C4PY00178H
34. C. Wang, J. Sun, X. Liu, A. Sudo, and T. Endo Synthesis and copolymerization of fully bio-based benzoxazines from guaiacol, furfurylamine and stearylamine Green Chem. 14 2012 2799 2806 10.1039/C2GC35796H
35. C. Wang, C. Zhao, J. Sun, S. Huang, X. Liu, and T. Endo Synthesis and thermal properties of a bio-based polybenzoxazine with curing promoter J. Polym. Sci., A: Polym. Chem. 51 2013 2016 2023 10.1002/pola.26587
36. T. Periyasamy, S.P. Asrafali, and S. Muthusamy New benzoxazines containing polyhedral oligomeric silsesquioxane from eugenol, guaiacol and vanillin New J. Chem. 39 2015 1691 1702 10.1039/C4NJ02047B
37. A.S. Amarasekara, and A. Razzaq Vanillin-based polymers - part II: Synthesis of Schiff base polymers of divanillin and their chelation with metal ions ISRN Polym. Sci. 2012 2012 e532171 10.5402/2012/532171
38. E.A.B. Silva, M. Zabkova, J.D. Araújo, C.A. Cateto, M.F. Barreiro, and M.N. Belgacem An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin Chem. Eng. Res. Des. 87 2009 1276 1292 10.1016/j.cherd.2009.05.008
39. P.F.H. Harmsen, M.M. Hackmann, and H.L. Bos Green building blocks for bio-based plastics Biofuels Bioprod. Biorefin. 8 2014 306 324 10.1002/bbb.1468
40. J. Tuteja, H. Choudhary, S. Nishimura, and K. Ebitani Direct synthesis of 1,6-hexanediol from HMF over a heterogeneous Pd/ZrP catalyst using formic acid as hydrogen source ChemSusChem 7 2014 96 100 10.1002/cssc.201300832
41. C. Pang, J. Zhang, G. Wu, Y. Wang, H. Gao, and J. Ma Renewable polyesters derived from 10-undecenoic acid and vanillic acid with versatile properties Polym. Chem. 5 2014 2843 2853 10.1039/C3PY01546G
42. I.A. Pearl, and J.F. McCoy Reactions of vanillin and its derived compounds J. Am. Chem. Soc. 69 1947 3071 3072 10.1021/ja01204a043
43. T. Nakano, S. Terao, and K.H. Lee Nonalkaloidal constituents of buxus microphylla var. suffruticosa J. Pharm. Sci. 54 1965 1201 1203 10.1002/jps.2600540824
44. K. Kürschner, and P. Strohriegl Polymerizable liquid crystalline twin molecules: synthesis and thermotropic properties Liq. Cryst. 27 2000 1595 1611 10.1080/026782900750037167
45. A. Truscello, C. Gambarotti, M. Lauria, S. Auricchio, G. Leonardi, S. Shisodia, and A. Citterio One-pot synthesis of aryloxypropanediols from glycerol: towards valuable chemicals from renewable sources Green Chem. 15 2013 625 628 10.1039/c2gc36793a
46. 3/MgO Appl. Catal. A: Gen. 408 2011 125 129 10.1016/j.apcata.2011.09.010
47. A. Cornia, L. Gregoli, C. Danieli, A. Caneschi, R. Sessoli, R. Sorace, A. Barra, and W. Wernsdorfer Slow quantum relaxation in a tetrairon(III) single-molecule magnet Inorg. Chim. Acta 361 2008 3481 3488 10.1016/j.ica.2008.02.067