
a.College of Materials Science & Engineering, Beijing Institute of Petrochemical Technology, Beijing 102617, China
b.Lanzhou Petrochemical Research Center, Petrochina, Lanzhou 730060, China
c.Beijing Key Laboratory of Specialty Elastomer Composite Materials, Beijing Institute of Petrochemical Technology, Beijing 102617, China
zhaoming888@bipt.edu.cn (M.Z.)
wuyibo@bipt.edu.cn (Y.B.W.)
Scan for full text
Jing Li, Kang-Da Wu, Huang Shan, et al. Synthesis and Properties of Hydroxytelechelic Polyisobutylenes by End Capping with
Jing Li, Kang-Da Wu, Huang Shan, et al. Synthesis and Properties of Hydroxytelechelic Polyisobutylenes by End Capping with
The low-activity cationic monomer ,tert,-butyl-dimethyl-(4-methyl-pent-4-enyloxy)-silane was synthesized by Grignard reaction and hydroxyl-protection reaction. Living polyisobutylene chains were initially synthesized by controlled cationic polymerization and then capped with ,tert,-butyl-dimethyl-(4-methyl-pent-4-enyloxy)-silane. The hydrolysis of these polyisobutylenes end capped with ,tert,-butyl-dimethyl-(4-methyl-pent-4-enyloxy)-silane gave rise to hydroxytelechelic polyisobutylene. NMR analysis confirmed that the hydrolysis was complete. Results also showed that a low polymerization temperature favored the participation of ,tert,-butyl-dimethyl-(4-methyl-pent-4-enyloxy)-silane in the end-capping reaction. Moreover, polyisobutylene-based polyurethane exhibited greater acid resistance than commercial polyurethane.
Carbocationic polymerizationPolyisobutyleneHydrolysisPolyisobutylene-based polyurethane
Jerome, R.; Henrioulle-granville, M.; Boutevin, B.; Robin, J. J . Telechelic polymers: Synthesis characterization and applications . Prog. Polym. Sci. , 1991 . 16 837 -906 . DOI:10.1016/0079-6700(91)90012-Ahttp://doi.org/10.1016/0079-6700(91)90012-A .
Wu, Y. X.; Tan, Y. X.; Wu, G. Y . Kinetic investigation of the carbocationic polymerization of isobutylene with the H2O/TiCl4/ED initiating system . Macromolecules , 2002 . 35 3801 -3805 . DOI:10.1021/ma011664bhttp://doi.org/10.1021/ma011664b .
Vasilenko, I. V.; Frolov, A. N.; Kostjuk, S. V . Cationic polymerization of isobutylene using AlCl3OBu2 as a coinitiator: Synthesis of highly reactive polyisobutylene . Macromolecules , 2010 . 43 5503 -5507 . DOI:10.1021/ma1009275http://doi.org/10.1021/ma1009275 .
Liu, Q.; Wu, Y. X.; Zhang, Y.; Yan, P. F.; Xu, R. W . A cost-effective process for highly reactive polyisobutylenes via cationic polymerization coinitiated by AlCl3 . Polymer , 2010 . 51 5960 -5969 . DOI:10.1016/j.polymer.2010.10.012http://doi.org/10.1016/j.polymer.2010.10.012 .
Liu, Q.; Wu, Y. X.; Yan, P. F.; Xu, R. W . Polyisobutylene with high exo-olefin content via β-H elimination in the cationic polymerization of isobutylene with H2O/FeCl3/dialkyl ether initiating system . Macromolecules , 2011 . 44 1866 -1875 . DOI:10.1021/ma1027017http://doi.org/10.1021/ma1027017 .
Kumar, R.; Dimitrov, P.; Bartelson, K. J.; Emert, J.; Faust, R . Polymerization of isobutylene by GaCl3 or FeCl3/ether complexes in nonpolar solvents . Macromolecules , 2012 . 45 8598 -8603 . DOI:10.1021/ma3017585http://doi.org/10.1021/ma3017585 .
Dimitrov, P.; Emert, J.; Faust, R . Polymerization of isobutylene by AlCl3/ether complexes in nonpolar solvent . Macromolecules , 2012 . 45 3318 -3325 . DOI:10.1021/ma3003856http://doi.org/10.1021/ma3003856 .
Dimitrov, P.; Emert, J.; Hua, J.; Keki, S.; Faust, R . Mechanism of isomerization in the cationic polymerization of isobutylene . Macromolecules , 2015 . 44 1831 -1840. .
Kumar, R.; Emert, J.; Faust, R . The polymerization of isobutylene catalyzed by FeCl3·i-Pr2O complex prepared in non-halogenated solvents . Polym. Bull. , 2015 . 72 49 -60 . DOI:10.1007/s00289-014-1258-3http://doi.org/10.1007/s00289-014-1258-3 .
Li, X. N.; Wu, Y. B.; Zhang, J. H.; Li, S. X.; Zhang, M.; Yang, D.; Wang, H.; Shang, Y. W.; Guo, W. L.; Yan, P. H . Synthesis of highly reactive polyisobutylenes via cationic polymerization in ionic liquids: Characteristics and mechanism . Polym. Chem. , 2019 . DOI: 10.1039/C8PY01141A DOI:10.1039/C8PY01141Ahttp://doi.org/10.1039/C8PY01141A .
Iván, B.; Kennedy, J. P . Living carbocationic polymerization. XXX. One-pot synthesis of allyl-terminated linear and tri-arm star polyisobutylenes, and epoxy- and hydroxyl-telechelics therefrom . J. Polym. Sci., Part A: Polym. Chem. , 1990 . 28 89 -104 . DOI:10.1002/pola.1990.080280107http://doi.org/10.1002/pola.1990.080280107 .
Deodhar, T. J.; Keszler, B. L.; Kennedy, J. P . Quantitative preparation of allyl telechelicpolyisobutylene under reflux conditions . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 1784 -1789 . DOI:10.1002/pola.28529http://doi.org/10.1002/pola.28529 .
Yang, B.; Storey, R. F . Chain-end functionalization of living polyisobutylene via an end-quenching comonomer that terminates by indanyl ring formation . Macromolecules , 2018 . 51 (17 ):6552 -6560 . DOI:10.1021/acs.macromol.8b01338http://doi.org/10.1021/acs.macromol.8b01338 .
Kennedy, J. P.; Smith, R. A . New telechelic polymers and sequential copolymers by polyfunctional initiator-transfer agents (inifers). II. Synthesis and characterization of α,ω-di(tert-chloro)polyisobutylenes . J. Polym. Sci., Part A: Polym. Chem. , 1980 . 18 1523 -1537 . DOI:10.1002/pol.1980.170180509http://doi.org/10.1002/pol.1980.170180509 .
Kwon, Y.; Kennedy, J. P . Polymerizability, copolymerizability, and properties of cyanoacrylate-telechelicpolyisobutylenes I: Three-arm star cyanoacrylate-telechelicpolyisobutylene . Polym. Adv. Technol. , 2007 . 18 800 -807 . DOI:10.1002/pat.v18:10http://doi.org/10.1002/pat.v18:10 .
Ojha, U.; Rajkhowa, R.; Agnihotra, S. R.; Faust, R . A new general methodology for the syntheses of end-functional polyisobutylenes by nucleophilic substitution reactions . Macromolecules , 2008 . 41 3832 -3841 . DOI:10.1021/ma7027209http://doi.org/10.1021/ma7027209 .
Albarran, A. A.; Silantyeva, E.; Seo, K. S.; Puskas, J. E . Synthesis of functionalized polyisobutylenes using the propylene epoxide/TiCl4 initiating system . Polym. Chem. , 2014 . 5 4710 -4714 . DOI:10.1039/C4PY00363Bhttp://doi.org/10.1039/C4PY00363B .
Iván, B.; Kennedy, J. P.; Chang, V. S. C . New telechelic polymers and sequential copolymers by polyfunctional initiator-transfer agents (inifers). VII. Synthesis and characterization of α,ω-di(hydroxy)polyisobutylene . J. Polym. Sci., Part A: Polym. Chem. , 1980 . 18 3177 -3191 . DOI:10.1002/pol.1980.170181104http://doi.org/10.1002/pol.1980.170181104 .
Magenau, A. J. D.; Chan, J. W.; Hoyle, C. E.; Storey, R. F . Facile polyisobutylene functionalization via thiol-ene click chemistry . Polym. Chem. , 2010 . 1 831 -833 . DOI:10.1039/c0py00094ahttp://doi.org/10.1039/c0py00094a .
Puskas, J. E.; Brister, L. B.; Michel, A. J.; Lanzendorfer, M. G.; Jamieson, D.; Pattern, W. G . Novel substituted epoxide initiators for the carbocationic polymerization of isobutylene . J. Polym. Sci., Part A: Polym. Chem. , 2000 . 38 444 -452 . DOI:10.1002/(ISSN)1099-0518http://doi.org/10.1002/(ISSN)1099-0518 .
Puskas, J. E.; Chen, Y.; Tomkins, M . Investigation of the effect of epoxide structure on the initiation efficiency in isobutylene polymerizations initiated by epoxide/TiCl4 systems . Eur. Polym. J. , 2003 . 39 (11 ):2147 -2153 . DOI:10.1016/S0014-3057(03)00149-6http://doi.org/10.1016/S0014-3057(03)00149-6 .
Chen, C. J.; Bozzelli, J. W . Analysis of tertiary butyl radical + O2, isobutene + HO2, isobutene + OH, and isobutene-OH adducts + O2: A detailed tertiary butyl oxidation mechanism . J. Phys. Chem. A , 1999 . 103 9731 -9769 . DOI:doi.org/10.1021/jp991227nhttp://doi.org/doi.org/10.1021/jp991227n .
Castano, M.; Beckera, M. L.; Puskas, J. E . New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene . Polym. Chem. , 2014 . 5 5436 -5442 . DOI:10.1039/C4PY00569Dhttp://doi.org/10.1039/C4PY00569D .
Puskas, J. E.; Chen, Y. H.; Yaser, D.; Donna, P . Polyisobutylene-based biomaterials . J. Polym. Sci., Part A: Polym. Chem. , 2004 . 42 3091 -3109 . DOI:10.1002/(ISSN)1099-0518http://doi.org/10.1002/(ISSN)1099-0518 .
Pinchuk, L.; Wilson, G. J.; Barry, J. J.; Schoephoerster, R. T.; Parel, J. M.; Kennedy, J. P . Medical applications of poly(styrene-block-isobutylene-block-styrene) ("SIBS") . Biomaterials , 2008 . 29 448 -460 . DOI:10.1016/j.biomaterials.2007.09.041http://doi.org/10.1016/j.biomaterials.2007.09.041 .
Puskas, J. E.; Muñoz-Robledo, L. G.; Hoerr, R. A.; Foley, J.; Schmidt, S. P.; Evancho-Chapman, M.; Dong, J. P.; Frethem, C.; Haugstad, G . Drug-eluting stent coatings . Wiley Interdiscip. Rev.: Nanomed. Nanobiotechnol. , 2010 . 1 451 -462. .
Kennedy, J. P . From thermoplastic elastomers to designed biomaterials . J. Polym. Sci., Part A: Polym. Chem. , 2005 . 43 (2951 ):2963 .
Kennedy, J. P.; Richard, G. C . Polyisobutylene-toughened poly(methyl methacrylate). 1. Synthesis, characterization, and tensile properties of PMMA-l-PIB networks . Macromolecules , 1993 . 26 567 -571 . DOI:10.1021/ma00056a002http://doi.org/10.1021/ma00056a002 .
Speckhard, T. A.; Gibson, P. E.; Cooper, S. L.; Chang, V. S. C.; Kennedy, J. P . Properties of polyisobutylene polyurethane block copolymers: 2. Macroglycols produced by the ‘inifer’ technique . Polymer , 1985 . 26 55 -69 . DOI:10.1016/0032-3861(85)90057-6http://doi.org/10.1016/0032-3861(85)90057-6 .
Mitzner, E.; Goering, H.; Becker, R.; Kennedy, J. P . Modification of segmented poly(ether urethanes) by incorporation of poly(isobutylene)glycol . J. Macromol. Sci., Part A , 1997 . 34 165 -178 . DOI:10.1080/10601329708014944http://doi.org/10.1080/10601329708014944 .
Mitzner, E.; Groth, T . Modification of poly(ether urethane)elastomers by incorporation of poly(isobutylene)glycol. Relation between polymer properties and thrombogenicity . J. Biomater. Sci. Polym. Ed. , 1996 . 7 1105 -1118 . DOI:10.1163/156856296X00598http://doi.org/10.1163/156856296X00598 .
Jewrajka, S. K.; Kang, J.; Erdodi, G.; Kennedy, J. P.; Yilgor, E.; Yilgor, I . Polyisobutylene-based polyurethanes. II. Polyureas containing mixed PIB/PTMO soft segments . J. Polym. Sci., Part A: Polym. Chem. , 2010 . 47 2787 -2797. .
Erdodi, G.; Kang, J.; Kennedy, J. P.; Yilgor, E.; Yilgor, I . Polyisobutylene-based polyurethanes. III. Polyurethanes containing PIB/PTMO soft co-segments . J. Polym. Sci., Part A: Polym. Chem. , 2010 . 47 5278 -5290. .
Kang, J.; Erdodi, G.; Kennedy, J. P . Polyisobutylene-based polyurethanes with unprecedented properties and how they came about . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 3891 -3904 . DOI:10.1002/pola.24839http://doi.org/10.1002/pola.24839 .
Kim, M. S.; Faust, R . Synthesis of poly(ε-caprolactone-b-isobutylene) diblock copolymer and poly(ε-caprolactone-b-isobutylene-b-ε-caprolactone) triblock copolymer . Polym. Bull. , 2002 . 48 127 -134 . DOI:10.1007/s00289-002-0019-xhttp://doi.org/10.1007/s00289-002-0019-x .
Storey, R. F.; Brister, L. B.; Sherman, J. W . Structural characterization of poly(ε-caprolactone) and poly(ε-caprolactone-b-isobutylene-b-ε-caprolactone) block copolymers by MALDI-TOF mass spectrometry . J. Macromol. Sci. Part A , 2001 . 38 107 -122 . DOI:10.1081/MA-100103337http://doi.org/10.1081/MA-100103337 .
Sipos, L.; Zsuga, M.; Deák, G . Synthesis of poly(L-lactide)-block-polyisobutylene-block-poly(L-lactide), a new biodegradable thermoplastic elastomer . Macromol. Rapid. Commun. , 1995 . 16 935 -940 . DOI:10.1002/marc.1995.030161209http://doi.org/10.1002/marc.1995.030161209 .
Craig, J. C.; Everhart, E. T . A convenient procedure for isolation of alcohols after cleavage of protective groups with tetra-n-butylammonium fluoride . Synth. Commun. , 2010 . 20 2147 -2150. .
Wu, Y. B.; Ren, P.; Guo, W. L.; Li, S. X.; Yang, X. P.; Shang, Y. W . Living cationic sequential block copolymerization: Synthesis and characterization of poly(4-(2-hydroxyethyl)styrene-b-isobutylene-b-4-(2-hydroxyethyl)styrene) triblock copolymers . Polym. J. , 2010 . 42 268 -272 . DOI:10.1038/pj.2009.339http://doi.org/10.1038/pj.2009.339 .
Ren, P.; Wu, Y. B.; Guo, W. L.; Li, S. X.; Chen, Y . ABA triblock copolymers with pendant hydroxyl groups prepared by controlled cationic polymerization and their use as delivery carrier for paclitaxe . Chinese J. Polym. Sci. , 2013 . 31 285 -293 . DOI:10.1007/s10118-013-1216-9http://doi.org/10.1007/s10118-013-1216-9 .
Wu, Y. B.; Li, K.; Xiang, D.; Zhang, M.; Yang, D.; Zhang, J. H.; Mao, J.; Wang, H.; Guo, W. L . Surface immobilization of heparin on functional polyisobutylene-based thermoplastic elastomer as a potential artificial vascular graft . Appl. Surf. Sci. , 2018 . 445 8 -15 . DOI:10.1016/j.apsusc.2018.03.048http://doi.org/10.1016/j.apsusc.2018.03.048 .
Wu, Y. B.; Guo, W. L.; Li, S. X.; Gong, H. Q . Synthesis and characterization of poly {4-[2-(tert-butyldimethylsiloxy)ethyl]styrene} and its hydrolysis derivative . Chinese J. Polym. Sci. , 2009 . 27 399 -405 . DOI:10.1142/S0256767909004060http://doi.org/10.1142/S0256767909004060 .
0
Views
0
Downloads
0
CSCD
Publicity Resources
Related Articles
Related Author
Related Institution
京公网安备11010802024621