Synthese von neuen monomeren schwefelhaltigen acryl‐ und methacrylsäureamid‐derivaten aus 3‐thiazolinen

Abstract

Acrylamides containing heteroatoms N, S or 0 are effective compounds to influence the properties of polymers. On the one hand they determine the chemical and physical behaviour of the synthetic materials, on the other hand they offer new possible applications for such compounds. In this paper a synthetic method affording a new class of monomers prepared from simple educts is described. Thus, 3-thiazolines 3 are allowed to react with alkenoyl chlorides (e. g. acryloyl chloride) to give 3-alkenoyl-4-chlorothiazolidines. Upon hydrolysis the 3-alkenoyl-4-hydroxythiazolidines 6a-d, 7a, b, 8a-d and 9a, b are obtained. Starting from 3-alkenoyl-4-chlorothiazolidines, several 3-alkenoyl-4-methoxythiazolidines 6 e, f, 7 c and 9 c have been synthesized, too. EinleitungAcrylamid-Derivate konnen zum Einfiihren vernetzungsfahiger funktioneller Gruppen dienen und werden zur Herstellung ofentrocknender Alkydharze verwendet I). Es gibt zahlreiche Moglichkeiten Harze herzustellen, die zusatzliche funktionelle Gruppen tragen. Diese funktionellen Gruppen konnen entweder wahrend der Polymerisation von Vinylverbindungen oder danach im fertigen Uberzug unter Ausbildung von homoopolaren Bindungen reagieren. Als funktionalisierte Monomere kommen dabei N-Hydroxyalkyl-oder N-Alkoxyalkyl-Derivate (1) des Acrylamids oder des Methacryl-1 amids zum Einsatz, z.B. N-(Hydroxymethy1)acrylamid (la, R' = R2 = H), N-(Hydroxymethy1)methacrylamid (1 b, R' = H, R2 = CH,), N(Methoxymethy1)methacrylamid ( l c , R' = CH,, R2 = CH,) und N-(1sobutoxymethyl)acrylamid (1 d, R' = CH,CH(CH,),, R2 = H).In dieser Arbeit berichten wir uber die ersten Versuche zur Synthese neuer heterocyclischer monomerer Acrylamid-Derivate 2 (X = S). Uber die Synthese der entsprechenden Oxazolidin-Derivate (2; X = 0) erscheint eine getrennte Arbeit.

Oxa‐ and Thiazolidine‐Containing Polymers Derived via the Asinger Four‐Component Reaction: the Ring Matters

“…These cyclic imines were used as precursors to prepare α,ω‐diene monomers M1 and M2 . According to a procedure established in our group, the iminic CN bond was functionalized by adding 10‐undecenoyl chloride yielding chloroamides. This reactive species was quenched in situ with 10‐undecenol and triethylamine to obtain monomers M1 and M2 in good yields (83% and 78%, respectively) after purification by flash chromatography.…”