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Thiol-terminated hydroxy-functional polymer as a transtab toward polymer latex particles

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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.

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References

  1. Wichterle O, Lim D (1960) Nature 185:118

    Article  Google Scholar 

  2. Barrett GD, Constable IJ, Steward AD (1986) J Cataract Refract Surg 12:623

    CAS  Google Scholar 

  3. Menace R, Skorpik C, Juchem M, Scheidel W, Schranz RI (1989) J Cataract Refract Surg 15:264

    Google Scholar 

  4. Bennet HS, Wyricks AD, Lee SW, McNeil H (1976) J Stain Technol 51:71

    Google Scholar 

  5. Canal T, Peppas NA (1989) J Biomed Mater Res 23:1183

    Article  CAS  Google Scholar 

  6. Miyajima M, Okano T, Kim TSW, Higushi WI (1987) J Control Release 5:179

    Article  CAS  Google Scholar 

  7. Lewis AL, Cumming ZL, Stratford PW (2001) Biomaterials 22:99

    Article  CAS  Google Scholar 

  8. Carlemalm E (1984) Chemische Werke Lowi G.m.b.H, US patent 4424329

  9. Weiss KD (1997) Prog Polym Sci 22:203

    Article  CAS  Google Scholar 

  10. Guojun L, Carl KS, Nanxing H, Jian T (1996) Macromolecules 29:220

    Article  Google Scholar 

  11. Beers KL, Boo S, Gaynor SG, Matyjaszewski K (1999) Macromolecules 32:5772

    Article  CAS  Google Scholar 

  12. Weaver JVM, Bannister I, Robinson KL, Bories-Azeau X, Armes SP, Smallridge M, McKenna P (2004) Macromolecules 37:2395

    Article  CAS  Google Scholar 

  13. Guice KB, Marrou SR, Gondi RS, Sumerlin BS, Loo YL (2008) Macromolecules 41:4390

    Article  CAS  Google Scholar 

  14. Fujii S, Suzaki M, Kakigi Y, Aono K, Yusa S, Nakamura Y (2011) J Polym Sci A Polym Chem 49:1633

    Article  CAS  Google Scholar 

  15. Horák D, Karpíšek M, Turková J, Beneš M (1999) Biotechnol Prog 15:208

    Article  Google Scholar 

  16. Chen X, Armes SP (2003) Adv Mater 15:1558

    Article  CAS  Google Scholar 

  17. Ali AMI, Pareek P, Sewell L, Schmid A, Fujii S, Armes SP, Shirley IM (2007) Soft Matter 3:1003

    Article  CAS  Google Scholar 

  18. Li Y, Armes SP (2005) Macromolecules 38:8155

    Article  CAS  Google Scholar 

  19. Daniel MC, Astruc D (2004) Chem Rev 104:293

    Article  CAS  Google Scholar 

  20. Sardar R, Funston AM, Mulvaney P, Murray RW (2009) Langmuir 25:13840

    Article  CAS  Google Scholar 

  21. Lundblad RL (1995) Techniques in protein modification. CRC, Boca Raton

    Google Scholar 

  22. Hermanson GT (1996) Bioconjugate techniques. Academic, New York

    Google Scholar 

  23. Jocelyn PC (1987) Methods Enzymol 143:246

    Article  CAS  Google Scholar 

  24. Gilbert HF (1997) Bioelectrochem Princ Pract 5:256

    CAS  Google Scholar 

  25. Tsarevsky NV, Matyjaszewski K (2002) Macromolecules 35:9009

    Article  CAS  Google Scholar 

  26. Aliyar HA, Hamilton PD, Ravi N (2005) Biomacromolecules 6:204

    Article  CAS  Google Scholar 

  27. Tsarevsky NV, Matyjaszewski K (2005) Macromolecules 38:3087

    Article  CAS  Google Scholar 

  28. Plunkett KN, Berkowski KL, Moore JS (2005) Biomacromolecules 6:632

    Article  CAS  Google Scholar 

  29. Yoshizumi A, Kanayama N, Maehara Y, Ide M, Kitano H (1999) Langmuir 15:482

    Article  CAS  Google Scholar 

  30. Debora B, Karina LH, Benjamin AF, Heather DM (2004) J Am Chem Soc 126:15372

    Article  Google Scholar 

  31. Warren NJ, Muise C, Stephens A, Armes SP, Lewis AL (2012) Langmuir 28:2928

    Article  CAS  Google Scholar 

  32. Shu XZ, Liu Y, Palumbo F, Prestwich GD (2003) Biomaterials 24:3825

    Article  CAS  Google Scholar 

  33. Hisano N, Morikawa N, Iwata H, Ikada Y (1998) J Biomed Mater Res 40:115

    Article  CAS  Google Scholar 

  34. Matsusaki M, Yoshida H, Akashi M (2007) Biomaterials 28:2729

    Article  CAS  Google Scholar 

  35. Stevens MP (Edn) (1999) Polymer chemistry 3rd Edition: an introduction. Oxford University Press

  36. Fujii S, Minami H, Okubo M (2004) Colloid Polym Sci 282:569

    Article  CAS  Google Scholar 

  37. Fujii S, Kakigi Y, Suzaki M, Yusa S, Muraoka M, Nakamura Y (2009) J Polym Sci A Polym Chem 47:3431

    Article  CAS  Google Scholar 

  38. Lovell PA, El-Aasser MS (1997) Emulsion polymerization and emulsion polymers. Wiley, Chichester

    Google Scholar 

  39. Kawaguchi S, Ito K (2005) Adv Polym Sci 175:299

    Article  CAS  Google Scholar 

  40. Nakamura K, Fujimoto K, Kawaguchi H (1999) Colloids Surf A Physiochem Eng Asp 153:195

    Article  CAS  Google Scholar 

  41. Okubo M, Fujii S, Maenaka H, Minami H (2002) Colloid Polym Sci 280:183

    Article  CAS  Google Scholar 

  42. Kitano H, Kawabata J (1996) Macromol Chem Phys 197:1721

    Article  CAS  Google Scholar 

  43. Kitano H, Kawabata J, Muramoto T (1996) Macromol Chem Phys 197:3657

    Article  CAS  Google Scholar 

  44. Tauer K (1995) Polym Adv Technol 6:435

    Article  CAS  Google Scholar 

  45. Fujii S, Aono K, Suzaki M, Hamasaki S, Yusa S, Nakamura Y (2012) Macromolecules 45:2863

    Article  CAS  Google Scholar 

  46. Almog Y, Reich S, Levy MB (1982) Polym J 14:131

    Article  CAS  Google Scholar 

  47. Tseng CM, Lu YY, El-Aasser MS, Vanderhoff JW (1986) J Polym Sci Polym Chem Ed 24:2995

    Article  CAS  Google Scholar 

  48. Lok KP, Ober CK (1985) Can J Chem 63:209

    Article  CAS  Google Scholar 

  49. Ober CK, Lok KP, Hair ML (1985) J Polym Sci Lett Ed 23:103

    Article  CAS  Google Scholar 

  50. Lok KP, Ober CK (1987) Macromolecules 20:268

    Article  Google Scholar 

  51. Winnik MA, Lukas R, Chen WF, Furlong P, Croucher MD (1987) Macromol Chem Macromol Symp 10/11:483

    Article  Google Scholar 

  52. Paine AJ (1990) J Colloid Interface Sci 138:157

    Article  CAS  Google Scholar 

  53. Paine AJ (1990) Macromolecules 23:3104

    Article  CAS  Google Scholar 

  54. Paine AJ (1990) J Polym Sci Polym Chem Ed 18:2485

    Google Scholar 

  55. Napper DH (1997) J Colloid Interface Sci 58:390

    Article  Google Scholar 

  56. Pelton RH, Osterroth A, Brook MA (1990) J Colloid Interface Sci 137:120

    Article  CAS  Google Scholar 

  57. Pelton RH, Osterroth A, Brook MA (1991) J Colloid Interface Sci 147:523

    Article  CAS  Google Scholar 

  58. Dawkins JV, Taylor G (1979) Polymer 20:599

    Article  CAS  Google Scholar 

  59. Jialanella GL, Firer EM, Piirma I (1992) J Polym Sci A Polym Chem 30:1925

    Article  CAS  Google Scholar 

  60. Windsor C, Marazek Z, Winnie MA, Croucher MD, Riess G (1994) Eur Polym J 31:121

    Google Scholar 

  61. Canelas DA, Betts DE, DeSimone JM (1996) Macromolecules 29:2818

    Article  CAS  Google Scholar 

  62. Baines FL, Dionisio S, Billingham NC, Armes SP (1996) Macromolecules 29:3096

    Article  CAS  Google Scholar 

  63. Lepilleur C, Beckman EJ (1997) Macromolecules 30:745

    Article  CAS  Google Scholar 

  64. Giles MR, Griffiths RMT, Aguiar-Ricardo A, Silva MMCG, Howdle SM (2001) Macromolecules 34:20

    Article  CAS  Google Scholar 

  65. Shaffer KA, Jones TA, Canelas DA, DeSimone JM (1996) Macromolecules 29:2704

    Article  CAS  Google Scholar 

  66. Lacroix-Desmazes P, Guyot A (1996) Macromolecules 29:4508

    Article  CAS  Google Scholar 

  67. Kawaguchi S, Winnik MA, Ito K (1996) Macromolecules 29:4465

    Article  CAS  Google Scholar 

  68. Chen M-Q, Kishida A, Akashi M (1996) J Polym Sci Polym Chem 34:2213

    Article  CAS  Google Scholar 

  69. Dupin D, Fujii S, Armes SP, Reeve P, Baxter SM (2006) Langmuir 22:3381

    Article  CAS  Google Scholar 

  70. Brandrup EH, Immergut HA, Grulke EA (1999) Polymer handbook, 4th edn. Wiley, New York

    Google Scholar 

  71. Fedors RF (1974) Polym Eng Sci 14:147

    Article  CAS  Google Scholar 

  72. Bjorklund RB, Liedberg BJ (1986) J Chem Soc Chem Commun 1293

  73. Kawaguchi M, Sakata Y, Anada S, Kato T, Takahashi A (1994) Langmuir 10:538

    Article  CAS  Google Scholar 

  74. Lascelles SF, Armes SP (1997) J Mater Chem 7(8):1339

    Article  CAS  Google Scholar 

  75. Pathak S, Greci MT, Kwong RC, Mercado K, Prakash GKS, Olah GA, Thompson ME (2000) Chem Mater 12:1985

    Article  CAS  Google Scholar 

  76. Fujii S, Ryan AJ, Armes SP (2006) J Am Chem Soc 128:7882

    Article  CAS  Google Scholar 

  77. Fujii S, Iddon PD, Ryan AJ, Armes SP (2006) Langmuir 22:7512

    Article  CAS  Google Scholar 

  78. Kettlewell SL, Schmid A, Fujii S, Dupin D, Armes SP (2007) Langmuir 23:11381

    Article  CAS  Google Scholar 

  79. Fujii S, Mochizuki M, Aono K, Hamasaki S, Murakami R, Nakamura Y (2011) Langmuir 27:12902

    Article  CAS  Google Scholar 

  80. Binks BP, Horozov TS (2006) (Edn.) Colloidal particles at liquid interfaces, Cambridge University Press

  81. Fujii S, Read ES, Armes SP, Binks BP (2005) Adv Mater 17:1014

    Article  CAS  Google Scholar 

  82. Fujii S, Cai Y, Weaver JVM, Armes SP (2005) J Am Chem Soc 127:7304

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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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Correspondence to Syuji Fujii.

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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

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