Portal de Periódicos da CAPES

Synthesis, characterization, and stability of carbodiimide groups in carbodiimide-functionalized latex dispersions and films

2000; Wiley; Volume: 38; Issue: 5 Linguagem: Inglês

10.1002/(sici)1099-0518(20000301)38

1099-0518

Hung H. Pham, Mitchell A. Winnik,

Advanced Polymer Synthesis and Characterization

Journal of Polymer Science Part A: Polymer ChemistryVolume 38, Issue 5 p. 855-869 Article Synthesis, characterization, and stability of carbodiimide groups in carbodiimide-functionalized latex dispersions and films Hung H. Pham, Hung H. Pham Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6Search for more papers by this authorMitchell A. Winnik, Corresponding Author Mitchell A. Winnik [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, CanadaM5S 3H6Search for more papers by this author Hung H. Pham, Hung H. Pham Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6Search for more papers by this authorMitchell A. Winnik, Corresponding Author Mitchell A. Winnik [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, CanadaM5S 3H6Search for more papers by this author First published: 08 February 2000 https://doi.org/10.1002/(SICI)1099-0518(20000301)38:5 3.0.CO;2-YCitations: 12Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Cyclohexylcarbodiimidoethyl methacrylate (CCEMA) and t-butylcarbodiimidoethyl methacrylate (t-BCEMA) were prepared in a two-step synthesis. These monomers were then used to prepare carbodiimide-functionalized PBMA and PEHMA latex particles, employing two-stage emulsion polymerization, with the carbodiimide–methacrylate monomers being introduced only in the second stage under monomer-starved conditions. During emulsion polymerization, the carbodiimide moiety (NCN) was found to be unstable at pH 4, but stable when the pH of the dispersion was increased to 8, using NaHCO3 as the buffer. Survival of NCN group against hydrolysis during the polymerization, and during storage in the dispersion, was enhanced by using EHMA as the comonomer (more hydrophobic) and the t-butyl carbodiimide derivative. The t-butyl group provides more steric hindrance to the hydrolysis reaction. A decrease in the reaction temperature from 80°C to 60°C was also found to increase the extent of NCN group incorporation during emulsion polymerization. Under ideal conditions, more than 98% of the NCN groups in the monomer feed are successfully incorporated into the latex. When these latex particles are mixed with a COOH containing latex and allowed to dry, polymer diffusion leading to crosslinking occurs. Films annealed at 60°C reach a gel content of 60% in 10 h. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 855–869, 2000 REFERENCES AND NOTES 1 Bufkin, B. G.; Grawe, J. R. J Coat Technol 1978, 50, 41. CASWeb of Science®Google Scholar 2 O'Brien, R. M.; Brown, S. A.; Bufkin, B. G.; Grawe, J. R. J Coat Technol 1981, 53, 49. CASGoogle Scholar 3 Geurts, J. M.; van Es, J. J. G. S; German, A. L. Progr Org Coat 1996, 29(1–4), 107. 10.1016/S0300-9440(96)00623-6 CASWeb of Science®Google Scholar 4 Xu, J.; Dimonie, V. L.; Sudol, D. E.; Shafer, O. L.; El-Aasser, M. S. J Appl Polym Sci 1998, 69, 965, 977, 985. 10.1002/(SICI)1097-4628(19980801)69:5 3.0.CO;2-N CASWeb of Science®Google Scholar 5 Feng, J.; Pham, H. H.; Macdonald, P.; Winnik, M. A.; Guerts, J. M.; Zirkzee, H.; van Es, J. J. G. S.; German, A. L. J Coat Tech 1998, 70, 57. 10.1007/BF02730151 CASWeb of Science®Google Scholar 6 Taylor, J. W.; Bassett, D. R. ACS Symposium Series, 1997; Vol. 663, p 137. Google Scholar 7 Wicks Jr., Z. W. Film Formation. Federation Series on Coatings Technology, Blue Bell, PA, 1986. Google Scholar 8 Taylor, J. W.; Collins, M. J.; Bassett, D. R. U.S. Patent 5,371,148. Google Scholar 9 UCARLNK XL29SE, Union Carbide Corporation. Google Scholar 10 Taylor, J. W.; Bassett, D. R. Technology of Waterborne Coatings. J. E. Glass, Ed.; ACS Symposium Series 666, American Chemical Society, Washington, D.C., 1997; p 137. 10.1021/bk-1997-0663.ch008 Google Scholar 11 Xu, Z.; Lu, G.; Cheng, S.; Li, L. J Appl Polym Sci 1995, 56, 575. 10.1002/app.1995.070560506 CASWeb of Science®Google Scholar 12 Verstegen, J. M. G. Ph.D. Thesis, University of Eindhoven, 1998. Google Scholar 13 Zhao, C.; Wang, Y.; Hruska, Z.; Winnik, M. A. Macromolecules 1990, 23, 4082. 10.1021/ma00220a009 CASWeb of Science®Google Scholar 14 Feng, J. Ph.D. Thesis, University of Toronto, 1997. Google Scholar 15 27th Annual Short Course. Advances in Emulsion Polymerization and Latex Technology, Lehigh University, 1996; Vol. 1. Google Scholar 16 Williams, A.; Ibrahim, I. T. Chem Rev 1981, 81, 589. 10.1021/cr00046a004 CASWeb of Science®Google Scholar Citing Literature Volume38, Issue51 March 2000Pages 855-869 ReferencesRelatedInformation