ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Bis[4-bis(2,3-epoxypropylamino)phenyl]methane (3) was shown to undergo homopolymerization when heated without or with an accelerator such as N,N-dimethylbenzylamine (10). When 3 was polymerized without accelerator, no ether formation was found. A new type of curing process involving opening of the epoxy ring by reaction at the phenyl ring in ortho position to the tertiary amino substituent allows one to explain the formation of compounds containing the 3-hydroxy-1,2,3,4-tetrahydroquinoline moiety. The corresponding derivatives 4-7 were isolated for the first time and their structures established by different spectroscopic methods such as 1H, 13C, 2D δ-δ NMR, and FT-IR. Intermolecular reaction at the orthocarbon of the tertiary amino group with an epoxy group may explain the resin formation by curing 3 without accelerator. Polymerization of 3 with accelerator 10 led to polyetherification. This result may be explained in terms of difference in the reactivity of the tertiary amines 3 and 10 towards the epoxy group. The former gives an unstable “zwitterion” by reaction at the nucleophilic carbon, subsequently leading to the stable hydroquinoline system by proton transfer. The latter also gives an unstable “zwitterion” by reaction at the nucleophilic nitrogen, however, it induces epoxy ring-opening polymerization due to the lack of intramolecular stabilization. Moreover, the results suggest that the hydroxyl functions, formed in the absence of an accelerator, do not react with epoxides under the studied conditions.
Additional Material:
9 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1989.021900213
