Azlactones alkenyl oligomers

The overall reaction of alkenyl azlactones (J ) and amine-terminated oligomers -6 is depicted in Equation 1, with actual reactants listed in Table 1. 

In summary, the reaction of alkenyl azlactones with amine-terminated oligomers has been found to be an excellent method for preparing the corresponding (meth)acrylamide-terminated oligomers. The reaction is characterized by a very simple synthetic sequence in which equivalent quantities of reactants are mixed at room temperature with no catalyst reactions are complete to the almost exclusion of side reactions within 16-18 hours. Furthermore, the reaction is a nucleophilic addition. This is the same manner in which nucleophiles react with isocyanates and epoxides. Indeed, this nucleophilic addition mode of reaction which involves no by-products likely accounts for the widespread use of these latter functional groups by industry. In comparison with isocyanate and epoxide, amine nucleophiles react with azlactones at controlled and predictable rates, intermediate between the very reactive isocyanate and the slow reacting epoxide. 

FUNCTIONAL, TELECHELIC POLYMERS DERIVED FROM REACTIONS OF NUCLEOPHILIC OLIGOMERS AND ALKENYL AZLACTONES, PART II MULTIAZLACTONES-ALTERNATIVES TO ISOCYANATE AND EPOXY RESINS ... 

Both in Chapter 10 and this chapter, we have described new techniques for the preparation of functional, telechelic oligomers and polymers based on reactions of alkenyl azlactones (Scheme 10). Nucleophilic ring-opening reactions can be utilized for the preparation of fluid acrylamides for potential use in a variety of free radical curable resin systems whereas, Michael addition leads to fluid multiazlactones which may be subsequently cured via nucleophilic addition. Further investigations concerning the chemistry and practical utility of these novel resin systems are ongoing in our laboratories. 

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