Synthesis of hydrophilic polyurethane particles in non-aqueous inverse miniemulsions

Abstract

It is shown that it is possible to synthesize high molecular weight hydrophilic polyurethane particles by reacting either tolylene-2,4-diisocyanate or isophorone diisocyanate and oligoethylene glycol (M n ∼200 g mol−1) in non-aqueous inverse emulsions. This procedure offers the advantage that the formation of polyurea can be prevented in consequence of the absence of water in the emulsion. Apparent molecular weights of hydrophilic polyurethane as high as 19,000 g mol−1 (M n) were obtained.

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References

  1. 1.

    Lamba NMK, Woodhouse KA, Cooper SL (1998) Polyurethane for biomedical applications Ed. CRC Press, Boca Raton, p 205

    Google Scholar 

  2. 2.

    Liu D, Meyerhoff ME, Goldberg HD, Brown RB (1993) Anal Chim Acta 274:37

    Article  CAS  Google Scholar 

  3. 3.

    Shin JH, Yoon SY, Yoon IJ, Choi SH, Lee SD, Nam HN, Cha GS (1998) Sensor Actuat B Chem 50:19

    Article  Google Scholar 

  4. 4.

    Hill FB Jr, Langerak EO, Prucino LJ, Remington WR (1951) EP 731071, DuPont

  5. 5.

    Windemith E, Schnell H, Bayer O (1951) DBP 974371. Farbf, Bayer

    Google Scholar 

  6. 6.

    Lan PN, Corneillie S, Schacht E, Davies M, Shard A (1996) Biomaterials 17:2273

    Article  CAS  Google Scholar 

  7. 7.

    Kojio K, Mitsui Y, Furukawa M (2009) Polymer 50:3693

    Article  CAS  Google Scholar 

  8. 8.

    Diagnostic Biosensor Polymers (1994) ACS Symp Ser 556:84

    Article  Google Scholar 

  9. 9.

    Arshady R, George MH (1993) Polym Eng Sci 33:865

    Article  CAS  Google Scholar 

  10. 10.

    Jong L, Saam JC (1996) ACS Symp Ser 624:332

    Article  CAS  Google Scholar 

  11. 11.

    Saam JC (1998) J Polym Sci A 36:341

    Article  CAS  Google Scholar 

  12. 12.

    Manabe K, Sun XM, Kobayashi S (2001) J Am Chem Soc 123:10101

    Article  CAS  Google Scholar 

  13. 13.

    Manabe K, Limura S, Sun XM, Kobayashi S (2002) J Am Chem Soc 124:11971

    Article  CAS  Google Scholar 

  14. 14.

    Molberg M, Crespy D, Rupper P, Nüesch F, Manson JA, Löwe C, Opris DM (2010) Adv Funct Mater 20:3280

    Article  CAS  Google Scholar 

  15. 15.

    Crespy D, Landfester K (2010) Beilstein J Org Chem 6:1132

    Article  CAS  Google Scholar 

  16. 16.

    Tiarks F, Landfester K, Antonietti M (2001) J Polym Sci A 39:2250

    Article  Google Scholar 

  17. 17.

    Barrere M, Landfester K (2003) Macromolecules 36:5119

    Article  CAS  Google Scholar 

  18. 18.

    Zanetti-Ramos BG, Lemos-Senna E, Soldi V, Borsali R, Cloutet E, Cramail H (2006) Polymer 47:8080

    Article  CAS  Google Scholar 

  19. 19.

    Li CY, Li YH, Hsieh KH, Chiu WY (2008) J Appl Polym Sci 107:840

    Article  CAS  Google Scholar 

  20. 20.

    Du YZ, Xu JG, Wang L, Yuan H, Hu FQ (2009) Eur Polym J 45:1397

    Article  CAS  Google Scholar 

  21. 21.

    Li CY, Chiu WY, Don TM (2005) J Polym Sci A 43:4870

    Article  CAS  Google Scholar 

  22. 22.

    Landfester K, Pawelzik U, Antonietti M (2005) Polymer 46:9892

    Article  CAS  Google Scholar 

  23. 23.

    Wang CP, Chu FX, Guyot A, Gauthier C, Boisson F (2006) J Appl Polym Sci 101:3927

    Article  CAS  Google Scholar 

  24. 24.

    Li CY, Chiu WY, Lee CF (2007) e-Polymers 015

  25. 25.

    Koenig A, Ziener U, Schaz A, Landfester K (2007) Macromol Chem Phys 208:155

    Article  CAS  Google Scholar 

  26. 26.

    Torini L, Argillier F, Zydowicz N (2005) Macromolecules 38:3225

    Article  CAS  Google Scholar 

  27. 27.

    Johnsen H, Schmid RB (2007) J Microencapsul 24:731

    Article  CAS  Google Scholar 

  28. 28.

    Gaudin F, Sintes-Zydowicz N (2008) Coll Surf A Phys Eng 331:133

    Article  CAS  Google Scholar 

  29. 29.

    Crespy D, Landfester K (2005) Macromolecules 38:6882

    Article  CAS  Google Scholar 

  30. 30.

    Crespy D, Landfester K (2007) Macromol Chem Phys 208:457

    Article  CAS  Google Scholar 

  31. 31.

    Crespy D, Landfester K (2009) Polymer 50:1616

    Article  CAS  Google Scholar 

  32. 32.

    Crespy D, Stark M, Hoffmann-Richter C, Ziener U, Landfester K (2007) Macromolecules 40:3122

    Article  CAS  Google Scholar 

  33. 33.

    Müller K, Klapper M, Müllen K (2007) Coll Polym Sci 285:1157

    Article  Google Scholar 

  34. 34.

    Poller RC, Retout SP (1979) J Organomet Chem 173:C7

    Article  CAS  Google Scholar 

  35. 35.

    Windholz M (ed) (1983) The Merck Index, Tenth Edition, An Encyclopedia of Chemicals, Drugs, and Biologicals. MERCK & CO., INC., Rahway

    Google Scholar 

  36. 36.

    Dean JA (Editor) (1999) Lange’s Handbook of Chemistry, 15th Edition, McGraw-Hill, New York

  37. 37.

    CRC Handbook of chemistry and physics 87th ed (2006) CRC, Boca Raton

  38. 38.

    ExxonMobil Chemical (2006) Product properties

  39. 39.

    Schlaad H, Kukula H, Rudloff J, Below I (2001) Macromolecules 34:4302

    Article  CAS  Google Scholar 

  40. 40.

    Kubitz KA (1957) Analyt Chemistry 29:814

    Article  CAS  Google Scholar 

  41. 41.

    Rogers ME, Long TE, Turner SR (2003) Synthetic Methods in Step-Growth Polymers. In: Rogers ME, Long TE (eds). Wiley, New York

  42. 42.

    Saunders JH, Frisch KC (1962) Polyurethanes Chemistry and Technology Part I, Interscience Publishers, New York; page 170: “Aliphatic isocyanates are generally less reactive than are the aromatic isocyanates”

  43. 43.

    Coutinho FMB, Rocha MCG (1991) Eur Polym J 27:213

    Article  CAS  Google Scholar 

  44. 44.

    Manu SK, Sekkar V, Scariah KJ, Varghese TL, Mathew S (2008) J Appl Polym Sci 110:908

    Article  CAS  Google Scholar 

  45. 45.

    Hablot E, Zheng D, Bouquey M, Avérous L (2008) Macromol Mater Eng 293:922

    Article  CAS  Google Scholar 

  46. 46.

    Bantu B, Pawar GM, Wurst K, Decker U, Schmidt AM, Buchmeister MR (2009) Eur J Inorg Chem 2009:1970

    Article  Google Scholar 

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Acknowledgments

We gratefully acknowledge Petra Räder, Gunnar Glaser and Katrin Kirchhoff, and Christine Rosenauer, Ute Heinz, and Sandra Seywald for the DSC, electron microscopy, and GPC measurements, respectively. We would like also to thank Dr. Anja Kröger-Brinkmann for interesting discussions and Dr. Eyk Schreiber for testing the isocyanate titration.

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Correspondence to Daniel Crespy.

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Herrmann, C., Crespy, D. & Landfester, K. Synthesis of hydrophilic polyurethane particles in non-aqueous inverse miniemulsions. Colloid Polym Sci 289, 1111–1117 (2011). https://doi.org/10.1007/s00396-011-2430-z

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Keywords

  • Miniemulsion
  • Nanoparticle
  • Non-aqueous emulsion
  • Polyaddition
  • Polyurethane