Synthesis of biodegradable polymers from renewable resources

Polymer Chemistry - Tập 3 Số 4 - Trang 836-851
Mathieu J.‐L. Tschan1, Emilie Brûlé1, Pierre Haquette1, C.M. Thomas1
1Chimie ParisTech, UMR CNRS 7223, 11 rue Pierre et Marie Curie, Paris Cedex 05, France

Tóm tắt

Từ khóa


Tài liệu tham khảo

Okada, 2002, Prog. Polym. Sci., 27, 87, 10.1016/S0079-6700(01)00039-9

Williams, 2008, Polym. Rev., 48, 1, 10.1080/15583720701834133

Rass-Hansen, 2007, J. Chem. Technol. Biotechnol., 82, 329, 10.1002/jctb.1665

Weisz, 2004, Phys. Today, 57, 47, 10.1063/1.1784302

Zaldivar, 2001, Appl. Microbiol. Biotechnol., 56, 17, 10.1007/s002530100624

Mecking, 2004, Angew. Chem., Int. Ed., 43, 1078, 10.1002/anie.200301655

Thomas, 2011, Angew. Chem., Int. Ed., 50, 9244, 10.1002/anie.201103076

Li, 2011, J. Am. Chem. Soc., 133, 6910, 10.1021/ja200895s

Poliakoff, 2006, Science, 211, 810

Ragauskas, 2006, Science, 311, 484, 10.1126/science.1114736

Güner, 2006, Prog. Polym. Sci., 31, 633, 10.1016/j.progpolymsci.2006.07.001

Jenck, 2004, Green Chem., 6, 544, 10.1039/b406854h

Corma, 2007, Chem. Rev., 107, 2411, 10.1021/cr050989d

Biermann, 2000, Angew. Chem., Int. Ed., 39, 2206, 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO;2-P

Lichtenthaler, 2002, Acc. Chem. Res., 35, 728, 10.1021/ar010071i

Lucia, 2006, Can. J. Chem., 84, 960, 10.1139/v06-117

Mathers, 2012, J. Polym. Sci., Part A: Polym. Chem., 50, 1, 10.1002/pola.24939

Renewable and Sustainable Polymers, ed. G. F. Payne, and P. B. Smith, ACS Symposium Series, American Chemical Society, Washington DC, 2011

Monomers, Polymers and Composites from Renewable Resources, ed. M. N. Belgacem and A. Gandini, Elsevier, Amsterdam, 2008

Gross, 2002, Science, 297, 803, 10.1126/science.297.5582.803

Danner, 1999, Chem. Soc. Rev., 28, 395, 10.1039/a806968i

Dechy-Cabaret, 2004, Chem. Rev., 104, 6147, 10.1021/cr040002s

Drumright, 2000, Adv. Mater., 12, 1841, 10.1002/1521-4095(200012)12:23<1841::AID-ADMA1841>3.0.CO;2-E

Hiljanen-Vainio, 1996, Macromol. Chem. Phys., 197, 1503, 10.1002/macp.1996.021970427

Perego, 1996, Polymer, 59, 37

Tsuji, 1996, Macromol. Chem. Phys., 197, 3483, 10.1002/macp.1996.021971033

Sarasua, 1998, Macromolecules, 31, 3895, 10.1021/ma971545p

Thomas, 2010, Chem. Soc. Rev., 39, 165, 10.1039/B810065A

McLain, 1992, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 33, 463

Stevels, 1996, Macromolecules, 29, 6132, 10.1021/ma9605311

O'Keefe, 2001, J. Am. Chem. Soc., 123, 339, 10.1021/ja003537l

Reeve, 1994, Macromolecules, 27, 825, 10.1021/ma00081a030

Sarasua, 1998, Macromolecules, 31, 3895, 10.1021/ma971545p

Zheng, 2008, New J. Chem., 32, 2279, 10.1039/b812754a

Lian, 2007, Polyhedron, 26, 3817, 10.1016/j.poly.2007.04.022

Lian, 2007, Inorg. Chem., 46, 328, 10.1021/ic061749z

Wu, 2006, Coord. Chem. Rev., 250, 602, 10.1016/j.ccr.2005.07.010

Atwood, 1997, Coord. Chem. Rev., 165, 267, 10.1016/S0010-8545(97)00017-9

Spassky, 1996, Macromol. Chem. Phys., 197, 2627, 10.1002/macp.1996.021970902

Ovitt, 2000, J. Polym. Sci., Part A: Polym. Chem., 38, 4686, 10.1002/1099-0518(200012)38:1+<4686::AID-POLA80>3.0.CO;2-0

Radano, 2000, J. Am. Chem. Soc., 122, 1552, 10.1021/ja9930519

Zhong, 2002, Angew. Chem., Int. Ed., 41, 4510, 10.1002/1521-3773(20021202)41:23<4510::AID-ANIE4510>3.0.CO;2-L

Zhong, 2003, J. Am. Chem. Soc., 125, 11291, 10.1021/ja0347585

Nomura, 2002, J. Am. Chem. Soc., 124, 5938, 10.1021/ja0175789

Nomura, 2007, Chem.–Eur. J., 13, 4433, 10.1002/chem.200601308

Hormnirun, 2004, J. Am. Chem. Soc., 126, 2688, 10.1021/ja038757o

Alaaeddine, 2009, Organometallics, 28, 1469, 10.1021/om8010273

Bouyahyi, 2008, Organometallics, 27, 5815, 10.1021/om800651z

Ovitt, 1999, J. Am. Chem. Soc., 121, 4072, 10.1021/ja990088k

Pietrangelo, 2009, Chem. Commun., 2736, 10.1039/b902968k

Pietrangelo, 2010, J. Am. Chem. Soc., 132, 11649, 10.1021/ja103841h

Douglas, 2008, Angew. Chem., Int. Ed., 47, 2290, 10.1002/anie.200705033

Chamberlain, 2001, J. Am. Chem. Soc., 123, 3229, 10.1021/ja003851f

Rieth, 2002, J. Am. Chem. Soc., 124, 15239, 10.1021/ja020978r

Ovitt, 2002, J. Am. Chem. Soc., 124, 1316, 10.1021/ja012052+

Amgoune, 2006, Chem.–Eur. J., 12, 169, 10.1002/chem.200500856

Amgoune, 2007, Pure Appl. Chem., 79, 2013, 10.1351/pac200779112013

Liu, 2007, Organometallics, 26, 2747, 10.1021/om0700359

Amgoune, 2007, Macromol. Rapid Commun., 28, 693, 10.1002/marc.200600862

Ma, 2006, Angew. Chem., Int. Ed., 45, 7818, 10.1002/anie.200603178

Coady, 2012, ACS Macro Lett., 1, 19, 10.1021/mz2000048

Zhang, 2010, Macromolecules, 43, 1660, 10.1021/ma901776x

Connor, 2001, J. Am. Chem. Soc., 124, 914, 10.1021/ja0173324

Dove, 2006, Chem. Commun., 2881, 10.1039/b601393g

Zhang, 2007, J. Am. Chem. Soc., 129, 12610, 10.1021/ja074131c

Zhang, 2007, Macromolecules, 40, 4154, 10.1021/ma070316s

Miyake, 2011, Macromolecules, 44, 4116, 10.1021/ma2007199

Chen, 2009, Chem. Rev., 109, 5157, 10.1021/cr9000258

Rossum, 1998, Phytochemistry, 49, 723, 10.1016/S0031-9422(98)00199-X

Kato, 2009, Tetrahedron Lett., 50, 4751, 10.1016/j.tetlet.2009.06.018

Manzer, 2004, Appl. Catal., A, 272, 249, 10.1016/j.apcata.2004.05.048

Sauer, 2008, Trends Biotechnol., 26, 100, 10.1016/j.tibtech.2007.11.006

Stansbury, 1992, Dent. Mater., 8, 270, 10.1016/0109-5641(92)90098-W

Akkapeddi, 1979, Macromolecules, 12, 546, 10.1021/ma60070a002

Akkapeddi, 1979, Polymer, 20, 1215, 10.1016/0032-3861(79)90145-9

Ueda, 1982, J. Polym. Sci., Part A: Polym. Chem., 20, 2819

Sogah, 1987, Macromolecules, 20, 1473, 10.1021/ma00173a006

Lee, 1989, Macromolecules, 22, 21, 10.1021/ma00191a004

Van den Brink, 1999, J. Polym. Sci., Part A: Polym. Chem., 37, 3804, 10.1002/(SICI)1099-0518(19991015)37:20<3804::AID-POLA9>3.0.CO;2-B

Trumbo, 1991, Polym. Bull., 26, 271, 10.1007/BF00587969

Koinuma, 1982, Makromol. Chem., Rapid Commun., 3, 311, 10.1002/marc.1982.030030510

Uno, 2008, J. Power Sources, 178, 716, 10.1016/j.jpowsour.2007.11.088

Agarwal, 2011, Macromol. Chem. Phys., 212, 603, 10.1002/macp.201000673

Suenaga, 1984, Macromolecules, 17, 2913, 10.1021/ma00142a080

Pittman, Jr, 2003, J. Polym. Sci., Part A: Polym. Chem., 41, 1759, 10.1002/pola.10719

Qi, 2008, J. Polym. Sci., Part A: Polym. Chem., 46, 5929, 10.1002/pola.22909

C. J. Brandenbourg , WO 2004069926, 2004

Cockburn, 2010, Macromol. Chem. Phys., 211, 501, 10.1002/macp.200900553

Cockburn, 2011, Biomacromolecules, 12, 2319, 10.1021/bm200400s

Mosnáček, 2008, Macromolecules, 41, 5509, 10.1021/ma8010813

Mosnáček, 2009, Polymer, 50, 2087, 10.1016/j.polymer.2009.02.037

Juhari, 2010, Polymer, 51, 4806, 10.1016/j.polymer.2010.08.017

Miyake, 2010, Dalton Trans., 39, 6710, 10.1039/c001909g

Hu, 2010, Macromolecules, 43, 9328, 10.1021/ma101901y

Yasuda, 1993, Macromolecules, 26, 7134, 10.1021/ma00078a004

Boffa, 1994, Macromolecules, 27, 6993, 10.1021/ma00101a044

Xu, 2009, Chem.–Eur. J., 15, 846, 10.1002/chem.200802220

Xu, 2010, Organometallics, 29, 459

Stojcevic, 2004, Angew. Chem., Int. Ed., 43, 5523, 10.1002/anie.200460785

Miyake, 2010, Macromolecules, 43, 4902, 10.1021/ma100615t

Zhang, 2010, Angew. Chem., Int. Ed., 49, 10158, 10.1002/anie.201005534

Zhang, 2008, Macromolecules, 41, 36, 10.1021/ma702015w

Zhang, 2008, Macromolecules, 41, 6353, 10.1021/ma801125y

Stephan, 2010, Angew. Chem., Int. Ed., 49, 46, 10.1002/anie.200903708

Hu, 2011, J. Polym. Sci., Part A: Polym. Chem., 49, 2008, 10.1002/pola.24628

Zhou, 2010, Macromolecules, 43, 939, 10.1021/ma901402a

Biermann, 2011, Angew. Chem., Int. Ed., 50, 3854, 10.1002/anie.201002767

Eissen, 2002, Angew. Chem., Int. Ed., 41, 414, 10.1002/1521-3773(20020201)41:3<414::AID-ANIE414>3.0.CO;2-N

Metzger, 2004, C. R. Chim., 7, 569, 10.1016/j.crci.2003.12.003

Sylvestre, 2010, Actual. Chim., 338–339, 28

Langer, 2000, Acc. Chem. Res., 33, 94, 10.1021/ar9800993

A. J. Domb , O.Elmalak, V. R.Shastry, Z.Ta-Shma, D. M.Masters, L.Ringel, D.Teomim and R.Langer, in Handbook of Biodegradable Polymers, ed. A. J. Domb, J. Kost and D. M. Weisman, Harwood Academic, Chichester, England, 1997, p. 135

Stephens, 2000, J. Controlled Release, 63, 305, 10.1016/S0168-3659(99)00205-9

Domb, 1994, Polym. Biomater., 399

Domb, 1995, J. Polym. Sci., Part A: Polym. Chem., 33, 717, 10.1002/pola.1995.080330413

Miyagawa, 2005, Polymer, 46, 445, 10.1016/j.polymer.2004.11.031

Lu, 2006, Biomacromolecules, 7, 2692, 10.1021/bm060458e

Krasko, 2003, J. Polym. Sci., Part A: Polym. Chem., 41, 1059, 10.1002/pola.10651

Teomim, 1999, J. Biomed. Mater. Res., 45, 258, 10.1002/(SICI)1097-4636(19990605)45:3<258::AID-JBM14>3.0.CO;2-W

Teomin, 2001, Biomacromolecules, 2, 37, 10.1021/bm000081r

Matsumura, 1986, Makromol. Chem. Rapid Commun., 7, 369, 10.1002/marc.1986.030070609

Ebata, 2007, Macromol. Biosci., 7, 798, 10.1002/mabi.200700018

Wang, 2008, Biomacromolecules, 9, 615, 10.1021/bm7009152

Biermann, 2010, Macromol. Chem. Phys., 211, 854, 10.1002/macp.200900615

N. Williams , C.Lampard, J. T.Carter, S.Quinn, PCT Int. Appl., WO 2009080598 A1 20090702, 2009

Zulim Botage, 2009, J. Am. Oil Chem. Soc., 86, 419, 10.1007/s11746-009-1368-5

Esen, 2007, J. Appl. Polym. Sci., 103, 626, 10.1002/app.25155

Wool, 1998, Polym. Prepr., 39, 90

Galia, 2010, Eur. J. Lipid Sci. Technol., 112, 87, 10.1002/ejlt.200900096

J. T. Carter , S.Quinn, PCT Int. Appl., WO 2009080599 A1 20090702, 2009

S. Yoshiko , F.Masahiro, Jpn. Kokai Tokkyo Koho, JP 2005200563, 2005

R. L. Quirino and R. C.Larock, in Renewable and Sustainable Polymers, ed. G. F. Payne and P. B. Smith, ACS Symposium Series, American Chemical Society, Washington DC, 2011, pp. 37–59

Sharma, 2006, Prog. Polym. Sci., 31, 983, 10.1016/j.progpolymsci.2006.09.003

R. P. Wool , in Bio-Based Polymers and Composites, ed. R. P. Wool and X. S. Sun: Academic Press, Amsterdam, 2005; p. 114

Trevino, 2002, Prog. Org. Coat., 44, 49, 10.1016/S0300-9440(01)00223-5

Petrovic, 2002, Eur. J. Lipid Sci. Technol., 104, 293, 10.1002/1438-9312(200205)104:5<293::AID-EJLT293>3.0.CO;2-W

Petrovic, 2005, Biomacromolecules, 6, 713, 10.1021/bm049451s

Petrovic, 2000, J. Polym. Sci., Part A: Polym. Chem., 38, 4062, 10.1002/1099-0518(20001115)38:22<4062::AID-POLA60>3.0.CO;2-L

Hu, 2002, J. Appl. Polym. Sci., 84, 591, 10.1002/app.10311

Monteavaro, 2005, J. Am. Oil Chem. Soc., 82, 365, 10.1007/s11746-005-1079-0

Lozada, 2009, J. Appl. Polym. Sci., 113, 2552, 10.1002/app.30209

Guo, 2002, J. Polym. Environ., 10, 49, 10.1023/A:1021022123733

Petrovic, 2008, Polym. Int., 57, 275, 10.1002/pi.2340

Petrovic, 2005, Biomacromolecules, 6, 713, 10.1021/bm049451s

Andejelkovic, 2006, J. Agric. Food Chem., 54, 9535, 10.1021/jf0612124

Ionescu, 2007, J. Polym. Environ., 15, 237, 10.1007/s10924-007-0065-4

Lu, 2008, Biomacromolecules, 9, 3332, 10.1021/bm801030g

Lu, 2007, Biomacromolecules, 8, 3108, 10.1021/bm700522z

X Pan and D. C.Webster, Macromol. Rapid Commun., 2011, 32, 13241330

Jain, 2008, Polym. Rev., 48, 156, 10.1080/15583720701834232

Gross, 2001, Chem. Rev., 101, 2097, 10.1021/cr0002590

Kobayashi, 2001, Chem. Rev., 101, 3793, 10.1021/cr990121l

Bartra, 1991, J. Org. Chem., 56, 5132, 10.1021/jo00017a027

Keck, 1989, J. Org. Chem., 54, 896, 10.1021/jo00265a033

Keck, 2000, Tetrahedron Lett., 41, 8673, 10.1016/S0040-4039(00)01569-0

Rousseau, 1995, Tetrahedron, 51, 2777, 10.1016/0040-4020(94)01064-7

Roxburgh, 1995, Tetrahedron, 51, 9767, 10.1016/0040-4020(95)00629-M

Ruddick, 2002, J. Chem. Soc., Perkin Trans. 1, 5, 629, 10.1039/b110528k

Boden, 1985, J. Org. Chem., 50, 2394, 10.1021/jo00213a044

Duda, 2002, Macromolecules, 35, 4266, 10.1021/ma012207y

van der Meulen, 2008, Biomacromolecules, 9, 3404, 10.1021/bm800898c

Uyama, 1995, Macromolecules, 28, 7046, 10.1021/ma00125a002

Bisht, 1997, Macromolecules, 30, 2705, 10.1021/ma961869y

Taden, 2003, Macromol. Rapid Commun., 24, 512, 10.1002/marc.200390079

van der Mee, 2006, Macromolecules, 39, 5021, 10.1021/ma060668j

Namekawa, 1999, Int. J. Biol. Macromol., 25, 145, 10.1016/S0141-8130(99)00028-8

Veld, 2009, ChemBioChem, 10, 1330, 10.1002/cbic.200900128

Focarete, 2001, J. Polym. Sci., Part B: Polym. Phys., 39, 1721, 10.1002/polb.1145

de Geus, 2010, Polym. Chem., 1, 525, 10.1039/b9py00360f

Takwa, 2006, Macromol. Rapid Commun., 27, 1932, 10.1002/marc.200600527

Chen, 2008, Biomacromolecules, 9, 463, 10.1021/bm700949x

Nakayama, 2011, J. Appl. Polym. Sci., 121, 2098, 10.1002/app.33834

Zhong, 2000, Macromol. Chem. Phys., 201, 1329, 10.1002/1521-3935(20000801)201:12<1329::AID-MACP1329>3.0.CO;2-8

Nomura, 1994, Macromolecules, 27, 620, 10.1021/ma00080a046

Jedlinski, 1996, Macromol. Chem. Phys., 197, 2923, 10.1002/macp.1996.021970925

van. der Meulen, 2011, Macromolecules, 44, 4301, 10.1021/ma200685u

Slivniak, 2005, Biomacromolecules, 6, 1679, 10.1021/bm049194r

Quinzler, 2009, Chem. Commun., 5400, 10.1039/b912294j

Naughton, 1974, J. Am. Oil Chem. Soc., 51, 65, 10.1007/BF00000015

Trzaskowski, 2011, Macromol. Rapid Commun., 32, 1352, 10.1002/marc.201100319

Lu, 2010, J. Am. Chem. Soc., 132, 15451, 10.1021/ja107707v

Liu, 2011, Biomacromolecules, 12, 3291, 10.1021/bm2007554

ürünç, 2011, Macromol. Rapid Commun., 32, 1357, 10.1002/marc.201100280

G. Woods , in The ICI Polyurethanes Book, Wiley, New-York, 2nd edn, 1990

Satheesh Kumar, 2007, J. Appl. Polym. Sci., 105, 3153, 10.1002/app.24481

Lu, 2005, Carbohydr. Polym., 61, 174, 10.1016/j.carbpol.2005.04.013

Pfister, 2011, ChemSusChem, 4, 703, 10.1002/cssc.201000378

Petrovic, 2008, Polym. Rev., 48, 109, 10.1080/15583720701834224

Xia, 2011, Macromol. Rapid Commun., 32, 1331, 10.1002/marc.201100203

Neumann, 2011, Macromol. Rapid Commun., 32, 1373, 10.1002/marc.201100205

Palaskar, 2010, Biomacromolecules, 11, 1202, 10.1021/bm100233v

Boyer, 2010, Green Chem., 12, 2205, 10.1039/c0gc00371a

Amass, 1998, Polym. Int., 47, 89, 10.1002/(SICI)1097-0126(1998100)47:2<89::AID-PI86>3.0.CO;2-F

Albertsson, 2003, Biomacromolecules, 4, 1466, 10.1021/bm034247a

Carpentier, 2010, Macromol. Rapid Commun., 31, 1696, 10.1002/marc.201000114

A. P. Dove , Handbook of Ring-Opening Polymerization, 2009, p. 357

Khan, 2009, Polym. Int., 58, 296, 10.1002/pi.2531

Albertsson, 2008, Adv. Drug Delivery Rev., 60, 1077, 10.1016/j.addr.2008.02.007

Kamber, 2007, Chem. Rev., 107, 5813, 10.1021/cr068415b

Agarwal, 2000, Macromol. Rapid Commun., 21, 195, 10.1002/(SICI)1521-3927(20000301)21:5<195::AID-MARC195>3.0.CO;2-4

Spassky, 1994, Bull. Soc. Chim. Fr., 131, 504

Williams, 2007, Chem. Soc. Rev., 36, 1573, 10.1039/b614342n

Baker, 2008, Polym. Rev., 48, 64, 10.1080/15583720701834208

Lou, 2003, Macromol. Rapid Commun., 24, 161, 10.1002/marc.200390029

Vert, 1998, Polym. Degrad. Stab., 59, 169, 10.1016/S0141-3910(97)00158-4

Benabdillah, 1999, Macromolecules, 32, 8774, 10.1021/ma991101o

Marcincinova-Benabdiillah, 2001, Biomacromolecules, 2, 1279, 10.1021/bm015585j

Pinilla, 2003, Carbohydr. Res., 338, 549, 10.1016/S0008-6215(02)00528-1

Coulembier, 2006, Macromolecules, 39, 4001, 10.1021/ma060552n

Parzuchowski, 2006, Macromolecules, 39, 7181, 10.1021/ma061488c

Fernandez, 2006, Polymer, 47, 6501, 10.1016/j.polymer.2006.07.063

Liu, 2007, Macromolecules, 40, 6040, 10.1021/ma061839n

Haider, 2008, J. Polym. Sci., Part A: Polym. Chem., 46, 2891, 10.1002/pola.22615

Urakami, 2008, Biomacromolecules, 9, 592, 10.1021/bm701180r

Pounder, 2010, Polym. Chem., 1, 260, 10.1039/b9py00327d

Drew, 1927, J. Chem. Soc., 775, 10.1039/JR9270000775

M. Masato , JP 2002167430 A2 2002611, Japan, 2002

Tang, 2009, Chem. Commun., 941, 10.1039/B817658B

Lowe, 2011, Polym. Chem., 2, 702, 10.1039/C0PY00283F

de Carvalho, 2006, Food Chem., 95, 413, 10.1016/j.foodchem.2005.01.003

Stridsberg, 2002, Adv. Polym. Sci., 157, 41, 10.1007/3-540-45734-8_2

Wanamaker, 2007, Biomacromolecules, 8, 3634, 10.1021/bm700699g

Wanamaker, 2009, Biomacromolecules, 10, 443, 10.1021/bm801292v

Coates, 2004, Angew. Chem., Int. Ed., 43, 6618, 10.1002/anie.200460442

Darensbourg, 2007, Chem. Rev., 107, 2388, 10.1021/cr068363q

Brulé, 2011, Macromol. Rapid Commun., 32, 169, 10.1002/marc.201000524

Byrne, 2004, J. Am. Chem. Soc., 126, 11404, 10.1021/ja0472580

Brignou, 2010, Macromolecules, 43, 8007, 10.1021/ma1014098

Robert, 2011, Nat. Commun.