USE OF SUBSTITUTED ALLYLIC SULFIDES TO PREPARE END-FUNCTIONAL POLYMERS OF CONTROLLED MOLECULAR-WEIGHT BY FREE-RADICAL POLYMERIZATION

被引：105

作者：

MEIJS, GF ^{[1
]}

MORTON, TC ^{[1
]}

RIZZARDO, E ^{[1
]}

THANG, SH ^{[1
]}

机构：

[1] CSIRO,DIV CHEM & POLYMERS,PRIVATE BAG 10,CLAYTON,VIC 3168,AUSTRALIA

来源：

MACROMOLECULES | 1991年 / 24卷 / 12期

关键词：

D O I：

10.1021/ma00012a033

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Substituted allylic sulfides 1b-f and 2d were utilized as chain-transfer agents to prepare low molecular weight polystyrene and poly(methyl methacrylate) capped with carboxy, hydroxy, trialkoxysilyl, or amino groups. End-functional polymers, prepared with ethyl alpha-(((carboxymethyl)thio)methyl)acrylate (2b) or alpha-(((carboxymethyl)thio)methyl)acrylic acid (11b), were capped with both a carboxy group and an acrylate moiety. Low molecular weight alpha,omega-dicarboxypolystyrene or poly(methyl methacrylate) were readily obtained by chain transfer with 11b. alpha-Hydroxy-omega-carboxy- and alpha,omega-dihydroxy-terminated polystyrene, poly(methyl methacrylate), and poly(butyl acrylate) were prepared with alpha-(((2-hydroxyethyl)thio)methyl)-acrylic acid (11d) and 2-hydroxyethyl alpha-(((2-hydroxyethyl)thio)methyl)acrylate (12d), respectively, while N-phthalimidoethyl alpha-(((2-hydroxyethyl)thio)methyl)acrylate (13d) was used to prepare polymers terminated at one end with hydroxy and at the other with a phthalamido group. H-1 NMR or IR spectroscopy, titration, or derivatization was used to confirm the presence of the end groups.

引用

页码：3689 / 3695

页数：7

共 15 条

[1] CARBETHOXYALLYLATION USING RADICAL CHEMISTRY [J].

BARTON, DHR ;

CRICH, D .

TETRAHEDRON LETTERS, 1984, 25 (26) :2787-2790

[2] THE INVENTION OF NEW RADICAL CHAIN-REACTIONS .12. IMPROVED METHODS FOR THE ADDITION OF CARBON RADICALS TO SUBSTITUTED ALLYLIC GROUPS [J].

BARTON, DHR ;

CRICH, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1613-1619

[3]

BROSSE JC, 1987, ADV POLYM SCI, V81, P167

[4] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[5]

CORNER T, 1984, ADV POLYM SCI, V62, P95

[6]

Fieser L. F., 1967, REAGENTS ORGANIC SYN, P191

[7] CHAIN TRANSFER IN THE POLYMERISATION OF STYRENE .3. THE REACTIVITIES OF HYDROCARBONS TOWARD THE STYRENE RADICAL [J].

GREGG, RA ;

MAYO, FR .

DISCUSSIONS OF THE FARADAY SOCIETY, 1947, 2 :328-342

[8] SYNTHESES OF METHYL METHACRYLATE-STEARYL METHACRYLATE GRAFT CO-POLYMERS AND CHARACTERIZATION BY INVERSE GAS-CHROMATOGRAPHY [J].

ITO, K ;

USAMI, N ;

YAMASHITA, Y .

MACROMOLECULES, 1980, 13 (02) :216-221

[9] SYNTHESIS OF BLOCK, GRAFT, SEGMENTED AND ION-CONTAINING CO-POLYMERS [J].

MCGRATH, JE .

PURE AND APPLIED CHEMISTRY, 1983, 55 (10) :1573-1581

[10] PREPARATION OF CONTROLLED MOLECULAR-WEIGHT, OLEFIN-TERMINATED POLYMERS BY FREE-RADICAL METHODS - CHAIN TRANSFER USING ALLYLIC SULFIDES [J].

MEIJS, GF ;

RIZZARDO, E ;

THANG, SH .

MACROMOLECULES, 1988, 21 (10) :3122-3124

← 1 2 →