P-Hydroxyphenyl-2-oxazoline

Polymerization of macromonomers by cationic ring-opening polymerization Macromonomer has been prepared from 2-(p-hydroxyphenyl)-2-oxazoline and ethylene oxide using n-butyl lithium to initiate the anionic polymerization of EO 16I). The living chains were terminated with CH3I or H20 yielding macromonomers with Mn = 1,010 and M = 1,930, respectively ... 

Prior to the work with m- and p-(hydroxyphenyl)-2-oxazolines, the only... 

Recently both the research group of Saegusa and Kobayashi, and our research group became engaged in the use of the two functional groups of m- and p-(hydroxyphenyl)-2-oxazolines for the development of new functional pol3rmers. It is the purpose of this paper to review the work of both groups in this area. 

An aromatic polyformal was also prepared from bisphenol-A and methylene chloride by phase-transfer-catalyzed etherification in the presence of 2-(p-hydroxyphenyl)-2-oxazoline as an encapping agent. A polyformal with two oxazoline chain ends was obtained. When a mixture of DMSO and CH2CI2 was used as a solvent rather than only CH2CI2, a pol3nner with both oxazoline and... 

Two new synthetic methods for the preparation of functional polymers containing 2-oxazoline pendant groups were developed. The first concerns the synthesis of m- and p-vinylbenzyl ethers of 2-(p-hydroxyphenyl)-2-oxazoline, followed by their radical poljnnerization. 2-(p-Hydroxyphenyl)-2-oxazo-line was reacted with a mixture of m- and p-chloromethylstyrene (60% m and 40% p) under phase transfer catalysis conditions at room temperature. The m-and p-vinylbenzyl ethers of 2-(p-hydroxyphenyl)-2-oxazoline obtained were separated by selective crystallization from methanol. Radical polymerization of these ethers was carried out in dioxane at 60 C, giving polymers with pendant 2-oxazoline groups. 

Figure 4. 200 MHz H-NMR spectrum (CDCl ) of the p-vinylbenzyl ether of 2-(p-hydroxyphenyl)-2-oxazoline. 

Schemes 64 and 65 outline the synthesis of bifunctional telechelic macromolecules using methylene chloride as a comonomer or chain extender. In the first procedure, the phenolic polymer chain ends are end capped with an electrophilic compound containing a functional group such as p-chloromethylstyrene. The order of the rate constants shown in Scheme 64 is self-explanatory. In the second procedure, the chloromethyl ether chain ends are end capped with a nucleophilic compound containing a functional group such as 2-(p-hydroxyphenyl)-2-oxazoline. " ...

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