Abstract
Azo-bis(isobutyroamidoxime) was synthesized and used as functionalized initiator to prepare a liquid isoprene bearing amidoxime end groups via radical polymerization. The polymer was characterized by FT-IR, Gel Permeation Chromatography and NMR. In particular, the structure of the polymer was investigated using 1D and 2D NMR techniques. The distribution of the different isoprene units (1,4-trans, 1,4-cis, 1,2 and 3,4), as well as the structure of the amidoxime end-groups was determined. It was found that the structure of the end groups was governed by the steric hindrance of the initiator. Only 1,4 and 4,1 functionalized end units were evidenced, with a majority of 4,1 end units.
Similar content being viewed by others
References
Kresta JE (ed) (1982) Reaction injection moulding and fast polymerization reactions. Plenum Press, New York
Mezhikovskii SM, Arinstein AE, Deberdeev RY (2005) Oligomeris state of substance. Nauka, Moscow
Atlantic Richfield Co. Patent US 2,136,157 (1972)
Boutevin B, David G, Boyer C (2007) Adv Polym Sci 206:31–135
Vilar WD, Moutinho MTM, Menezes SMC, Coutinho FMB (1997) Polym Bull 38:319–325
Pinazzi C, Legeay G, Brosse JC (1975) Makromol Chem 176:1307–1322
Odian G (2004) Principles of polymerization, 4th edn. Wiley, Singapore
Grishchenko V, Boiko V, Svistova E, Yatsimirskaya T, Valuev V, Dmitrieva T (1992) J Appl Polym Sci 46:2081–2087
Allen G, Bevington JC, Booth C, Price C (1989) Comprehensive polymer science: the synthesis, characterization, reactions & applications of polymers. Pergamon Press, Oxford
Bielawski CW, Benitez D, Grubbs RY (2003) JACS 125:8424–8425
Dubkov KA, Semikolenov SV, Barushkin DE, Echevskaya LG, Matsko MA, Ivanov DP, Zakharov VA, Parmon VN, Panov GI (2006) J Pol Sci A Polym Chem 44(8):2510–2520
Reyx D, Campistron I (1997) Angew Makromol Chem 247:197–211
Kebir N, Morandi G, Campistron L, Laguerre A, Pilard JF (2005) Polymer 46(18):6844–6854
Egawa H, Nakayama M, Nonaka T, Sugihara E (1987) J Appl Polym Sci 33:1993–2005
Kise H, Sato H (1985) Makromol Chem 186:2449–2454
Kubota H, Shigehisa Y (1995) J Appl Polym Sci 56:147–151
Lin WP, Lu Y, Zeng HM (1993) J Appl Polym Sci 47:45–52
Arranz F, Sanchez-Chaves M, Gallego MM (1994) Angew Makromol Chem 218:183–196
Sahiner N, Pekel N, Güven O (1998) Radiat Phys Chem 52:271–276
Güler H, Sahiner N, Ayçik G, Güven O (1997) J Appl Polym Sci 66:2475–2480
Abdel-Rahman AAH, Atta AM, El Aassy IE, Ahmed FY, Hamza MF (2011) J Disp Sci Tech 32(2):224–234
Caykara T, Cakar F, Demirci S (2011) Polym Int 60(1):141–145
Hazer O, Kartal S (2009) Anal Sci 25:547–551
Braun D, Cherdon H, Kern W (1972) Techniques of polymer synthesis and characterization. Wiley-Interscience, NewYork
Tanaka Y, Takeuchi Y, Kobayashi M, Tadokoro H (1971) J Polym Sci 9:43
Pinazzi C, Soutif JC, Brosse JC (1975) Eur Polym J 11:523–525
Burel F, Oulyadi H, Bunel C (2000) Int J Pol Anal Char 6:193–212
Pham QT (1981) Makromol Chem 182:1167–1176
Chen HY (1962) Anal Chem 34:1134
Duch MW, Grant DM (1970) Macromolecules 3:165–174
Tanaka Y, Sato H, Seimiya T (1975) Polym J 7:264–266
Gronski W, Murayama N, Cantow HJ, Myyamoto T (1976) Polymer 17:358–360
Tanaka Y, Sato H (1976) Polymer 17:113–116
Tanaka Y, Sato H (1976) Polymer 17:413–418
Sato H, Ono A, Tanaka Y (1977) Polymer 18:580–586
Silverstein RM, Webster FX (1998) Spectrometric identification of organic compounds, 6th edn. Wiley, New York
Dorman DE, Jautelat M, Roberts JD (1971) J Org Chem 36:2757
Brandrup J, Immergut EH, Grulke EA, Abe A, Bloch DR (2005) Polymer handbook, 4th edn. Wiley, New York
Acknowledgement
Authors wish to acknowledge National Academy of Sciences of Ukraine (NASU) and French National Scientific Research Center (CNRS) for financial support. Project N°189961.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Burel, F., Oulyadi, H., Bunel, C. et al. Synthesis and structural characterization of a liquid polyisoprene bearing amidoxime end groups. J Polym Res 18, 2265–2273 (2011). https://doi.org/10.1007/s10965-011-9640-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10965-011-9640-4