Synthesis of functionalized polyisobutylenes using the propylene epoxide/TiCl4 initiating system

被引:15
作者
Albarran, Alejandra Alvarez [1 ]
Silantyeva, Elena [1 ]
Seo, Kwang Su [2 ]
Puskas, Judit E. [1 ,2 ]
机构
[1] Univ Akron, Dept Polymer Sci, Akron, OH 44325 USA
[2] Univ Akron, Dept Chem & Biomol Engn, Akron, OH 44325 USA
基金
美国国家科学基金会;
关键词
TRANSFER AGENTS INIFERS; CARBOCATIONIC POLYMERIZATION; TELECHELIC POLYMERS; SUBSTITUTION; ISOBUTYLENE; COPOLYMERS;
D O I
10.1039/c4py00363b
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
In this paper, we report the synthesis of symmetric and asymmetric telechelic polyisobutylenes (PIBs). A PIB with a primary hydroxy head group and an allyl end group (HO-PIB-Allyl, M-n = 4300 g mol(-1); M-w/M-n = 1.2) was synthesized by living carbocationic polymerization of isobutylene (IB) using propylene epoxide as an initiator and allyltrimethylsilane as a terminating agent. Thiol-ene click chemistry using 2-mercaptoethanol and 1,2-ethanedithiol yielded an asymmetric HO-PIB-SEt-OH (M-n = 4646 g mol(-1); M-w/M-n = 1.18) and a symmetric HO-PIB-OH (M-n, = 8594 g mol(-1); M-w/M-n = 1.2) respectively. A symmetric allyl telechelic PIB (M-n = 8669 g mol(-1); M-w/M-n = 1.2) was prepared by enzymatic transesterification of divinyl adipate with the primary hydroxy group of HO-PIB-Allyl.
引用
收藏
页码:4710 / 4714
页数:5
相关论文
共 16 条
[1]   Synthesis of nonsymmetric chain end functionalized polyisobutylenes [J].
Adekunle O. ;
Herbst F. ;
Hackethal K. ;
Binder W.H. .
Journal of Polymer Science, Part A: Polymer Chemistry, 2011, 49 (13) :2931-2940
[2]  
Chiang K.C. C., 2012, Polymer Preprints, V53, P365
[3]   NEW TELECHELIC POLYMERS AND SEQUENTIAL CO-POLYMERS BY POLYFUNCTIONAL INITIATOR-TRANSFER AGENTS (INIFERS) .7. SYNTHESIS AND CHARACTERIZATION OF ALPHA,OMEGA-DI(HYDROXY)POLYISOBUTYLENE [J].
IVAN, B ;
KENNEDY, JP ;
CHANG, VSC .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1980, 18 (11) :3177-3191
[4]   LIVING CARBOCATIONIC POLYMERIZATION .30. ONE-POT SYNTHESIS OF ALLYL-TERMINATED LINEAR AND TRI-ARM STAR POLYISOBUTYLENES, AND EPOXY-TELECHELIC AND HYDROXY-TELECHELIC THEREFROM [J].
IVAN, B ;
KENNEDY, JP .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1990, 28 (01) :89-104
[5]   Polyisobutylene-Based Polyurethanes with Unprecedented Properties and How They Came About [J].
Kang, Jungmee ;
Erdodi, Gabor ;
Kennedy, Joseph P. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (18) :3891-3904
[7]   Facile polyisobutylene functionalization via thiol-ene click chemistry [J].
Magenau, Andrew J. D. ;
Chan, Justin W. ;
Hoyle, Charles E. ;
Storey, Robson F. .
POLYMER CHEMISTRY, 2010, 1 (06) :831-833
[8]   Modification of segmented poly(ether urethanes) by incorporation of poly(isobutylene)glycol [J].
Mitzner, E ;
Goering, H ;
Becker, R ;
Kennedy, JP .
JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 1997, A34 (01) :165-178
[9]   A new general methodology for the syntheses of end-functional polyisobutylenes by nucleophilic substitution reactions [J].
Ojha, Umaprasana ;
Rajkhowa, Ritimoni ;
Agnihotra, Shrikant Rao ;
Faust, Rudolf .
MACROMOLECULES, 2008, 41 (11) :3832-3841
[10]   Comparison of the molecular weight and size measurement of polyisobutylenes by size exclusion chromatography/multi-angle laser light scattering and viscometry [J].
Puskas, JE ;
Chen, YH ;
Kulbaba, K ;
Kaszas, G .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (05) :1777-1783