Enhanced reactivity of monovinyl acrylates characterized by secondary functionalities toward photopolymerization and Michael addition: Contribution of intramolecular effects

被引：15

作者：

Kilambi, Harini ^{[1
]}

Stansbury, Jeffrey W. ^{[1
,2
]}

Bowman, Christopher N. ^{[1
,2
]}

机构：

[1] Univ Colorado, Dept Chem & Biol Engn, Boulder, CO 80309 USA

[2] Univ Colorado, Hlth Sci Ctr, Sch Dent, Biomat Res Ctr, Aurora, CO 80045 USA

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2008年 / 46卷 / 10期

关键词：

monomer; photopolymerization; radical polymerization;

D O I：

10.1002/pola.22660

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The contribution of intramolecular conformational effects and the role of certain secondary functionalities on the reactivity of acrylates toward Michael addition reaction have been examined. Michael addition studies of monovinyl acrylates with butyl mercaptopropionate were conducted in the presence of triethylamine as a catalyst. The Michael addition kinetics of traditional aliphatic acrylates such as hexyl acrylate and tetrahydrofurfural acrylate (THFFA) with acrylates characterized by carbamate, carbonate, and hydroxy functionalities were investigated. THFFA exhibited an approximately fivefold increase in the Michael addition kinetic constant relative to hexyl acrylate, while the incorporation of the carbonate, carbamate, and hydroxy secondary functionalities led to around one or two orders of magnitude rate enhancement in the Michael addition kinetics of these systems. Cyclic carbonate acrylate exhibited a three order of magnitude increase in the Michael addition kinetic constant.

引用

页码：3452 / 3458

页数：7