Abstract
Hydroxy-functional macrodisulfides have been synthesized by atom transfer radical polymerization of 2-hydroxyethyl methacrylate or 2-hydroxypropyl methacrylate in 2-propanol. Mean degrees of polymerization of the polymer chains beside the disulfide were fixed at 30, 60, and 90; since ATRP has reasonably good living character, the molecular weight distribution is relatively narrow. Furthermore, the macrodisulfides were reduced to synthesize corresponding thiol-terminated polymers with relatively narrow molecular weight distributions. 1H nuclear magnetic resonance and gel permeation chromatography were used to characterize the macrodisulfides and thiol-terminated polymers in terms of their chemical structure, molecular weight, and polydispersity, respectively. Dispersion polymerizations of styrene using the thiol-terminated hydroxy-functional polymers as a transtab (chain transfer agent + colloidal stabilizer) in ethanol resulted in colloidally stable submicrometer-sized polystyrene latex particles. Scanning electron microscopy, Fourier transform infrared spectroscopy, and elemental microanalysis were used to characterize the particles in terms of their morphologies, particle sizes and their distributions, and chemical compositions.
References
Wichterle O, Lim D (1960) Nature 185:118
Barrett GD, Constable IJ, Steward AD (1986) J Cataract Refract Surg 12:623
Menace R, Skorpik C, Juchem M, Scheidel W, Schranz RI (1989) J Cataract Refract Surg 15:264
Bennet HS, Wyricks AD, Lee SW, McNeil H (1976) J Stain Technol 51:71
Canal T, Peppas NA (1989) J Biomed Mater Res 23:1183
Miyajima M, Okano T, Kim TSW, Higushi WI (1987) J Control Release 5:179
Lewis AL, Cumming ZL, Stratford PW (2001) Biomaterials 22:99
Carlemalm E (1984) Chemische Werke Lowi G.m.b.H, US patent 4424329
Weiss KD (1997) Prog Polym Sci 22:203
Guojun L, Carl KS, Nanxing H, Jian T (1996) Macromolecules 29:220
Beers KL, Boo S, Gaynor SG, Matyjaszewski K (1999) Macromolecules 32:5772
Weaver JVM, Bannister I, Robinson KL, Bories-Azeau X, Armes SP, Smallridge M, McKenna P (2004) Macromolecules 37:2395
Guice KB, Marrou SR, Gondi RS, Sumerlin BS, Loo YL (2008) Macromolecules 41:4390
Fujii S, Suzaki M, Kakigi Y, Aono K, Yusa S, Nakamura Y (2011) J Polym Sci A Polym Chem 49:1633
Horák D, Karpíšek M, Turková J, Beneš M (1999) Biotechnol Prog 15:208
Chen X, Armes SP (2003) Adv Mater 15:1558
Ali AMI, Pareek P, Sewell L, Schmid A, Fujii S, Armes SP, Shirley IM (2007) Soft Matter 3:1003
Li Y, Armes SP (2005) Macromolecules 38:8155
Daniel MC, Astruc D (2004) Chem Rev 104:293
Sardar R, Funston AM, Mulvaney P, Murray RW (2009) Langmuir 25:13840
Lundblad RL (1995) Techniques in protein modification. CRC, Boca Raton
Hermanson GT (1996) Bioconjugate techniques. Academic, New York
Jocelyn PC (1987) Methods Enzymol 143:246
Gilbert HF (1997) Bioelectrochem Princ Pract 5:256
Tsarevsky NV, Matyjaszewski K (2002) Macromolecules 35:9009
Aliyar HA, Hamilton PD, Ravi N (2005) Biomacromolecules 6:204
Tsarevsky NV, Matyjaszewski K (2005) Macromolecules 38:3087
Plunkett KN, Berkowski KL, Moore JS (2005) Biomacromolecules 6:632
Yoshizumi A, Kanayama N, Maehara Y, Ide M, Kitano H (1999) Langmuir 15:482
Debora B, Karina LH, Benjamin AF, Heather DM (2004) J Am Chem Soc 126:15372
Warren NJ, Muise C, Stephens A, Armes SP, Lewis AL (2012) Langmuir 28:2928
Shu XZ, Liu Y, Palumbo F, Prestwich GD (2003) Biomaterials 24:3825
Hisano N, Morikawa N, Iwata H, Ikada Y (1998) J Biomed Mater Res 40:115
Matsusaki M, Yoshida H, Akashi M (2007) Biomaterials 28:2729
Stevens MP (Edn) (1999) Polymer chemistry 3rd Edition: an introduction. Oxford University Press
Fujii S, Minami H, Okubo M (2004) Colloid Polym Sci 282:569
Fujii S, Kakigi Y, Suzaki M, Yusa S, Muraoka M, Nakamura Y (2009) J Polym Sci A Polym Chem 47:3431
Lovell PA, El-Aasser MS (1997) Emulsion polymerization and emulsion polymers. Wiley, Chichester
Kawaguchi S, Ito K (2005) Adv Polym Sci 175:299
Nakamura K, Fujimoto K, Kawaguchi H (1999) Colloids Surf A Physiochem Eng Asp 153:195
Okubo M, Fujii S, Maenaka H, Minami H (2002) Colloid Polym Sci 280:183
Kitano H, Kawabata J (1996) Macromol Chem Phys 197:1721
Kitano H, Kawabata J, Muramoto T (1996) Macromol Chem Phys 197:3657
Tauer K (1995) Polym Adv Technol 6:435
Fujii S, Aono K, Suzaki M, Hamasaki S, Yusa S, Nakamura Y (2012) Macromolecules 45:2863
Almog Y, Reich S, Levy MB (1982) Polym J 14:131
Tseng CM, Lu YY, El-Aasser MS, Vanderhoff JW (1986) J Polym Sci Polym Chem Ed 24:2995
Lok KP, Ober CK (1985) Can J Chem 63:209
Ober CK, Lok KP, Hair ML (1985) J Polym Sci Lett Ed 23:103
Lok KP, Ober CK (1987) Macromolecules 20:268
Winnik MA, Lukas R, Chen WF, Furlong P, Croucher MD (1987) Macromol Chem Macromol Symp 10/11:483
Paine AJ (1990) J Colloid Interface Sci 138:157
Paine AJ (1990) Macromolecules 23:3104
Paine AJ (1990) J Polym Sci Polym Chem Ed 18:2485
Napper DH (1997) J Colloid Interface Sci 58:390
Pelton RH, Osterroth A, Brook MA (1990) J Colloid Interface Sci 137:120
Pelton RH, Osterroth A, Brook MA (1991) J Colloid Interface Sci 147:523
Dawkins JV, Taylor G (1979) Polymer 20:599
Jialanella GL, Firer EM, Piirma I (1992) J Polym Sci A Polym Chem 30:1925
Windsor C, Marazek Z, Winnie MA, Croucher MD, Riess G (1994) Eur Polym J 31:121
Canelas DA, Betts DE, DeSimone JM (1996) Macromolecules 29:2818
Baines FL, Dionisio S, Billingham NC, Armes SP (1996) Macromolecules 29:3096
Lepilleur C, Beckman EJ (1997) Macromolecules 30:745
Giles MR, Griffiths RMT, Aguiar-Ricardo A, Silva MMCG, Howdle SM (2001) Macromolecules 34:20
Shaffer KA, Jones TA, Canelas DA, DeSimone JM (1996) Macromolecules 29:2704
Lacroix-Desmazes P, Guyot A (1996) Macromolecules 29:4508
Kawaguchi S, Winnik MA, Ito K (1996) Macromolecules 29:4465
Chen M-Q, Kishida A, Akashi M (1996) J Polym Sci Polym Chem 34:2213
Dupin D, Fujii S, Armes SP, Reeve P, Baxter SM (2006) Langmuir 22:3381
Brandrup EH, Immergut HA, Grulke EA (1999) Polymer handbook, 4th edn. Wiley, New York
Fedors RF (1974) Polym Eng Sci 14:147
Bjorklund RB, Liedberg BJ (1986) J Chem Soc Chem Commun 1293
Kawaguchi M, Sakata Y, Anada S, Kato T, Takahashi A (1994) Langmuir 10:538
Lascelles SF, Armes SP (1997) J Mater Chem 7(8):1339
Pathak S, Greci MT, Kwong RC, Mercado K, Prakash GKS, Olah GA, Thompson ME (2000) Chem Mater 12:1985
Fujii S, Ryan AJ, Armes SP (2006) J Am Chem Soc 128:7882
Fujii S, Iddon PD, Ryan AJ, Armes SP (2006) Langmuir 22:7512
Kettlewell SL, Schmid A, Fujii S, Dupin D, Armes SP (2007) Langmuir 23:11381
Fujii S, Mochizuki M, Aono K, Hamasaki S, Murakami R, Nakamura Y (2011) Langmuir 27:12902
Binks BP, Horozov TS (2006) (Edn.) Colloidal particles at liquid interfaces, Cambridge University Press
Fujii S, Read ES, Armes SP, Binks BP (2005) Adv Mater 17:1014
Fujii S, Cai Y, Weaver JVM, Armes SP (2005) J Am Chem Soc 127:7304
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This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Soft-Interface Science” from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
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Fujii, S., Yamashita, S., Kakigi, Y. et al. Thiol-terminated hydroxy-functional polymer as a transtab toward polymer latex particles. Colloid Polym Sci 291, 1171–1180 (2013). https://doi.org/10.1007/s00396-012-2845-1
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DOI: https://doi.org/10.1007/s00396-012-2845-1