Synthesis and Characterization of a Ring-Opening Oxaspiro Comonomer by a Novel Catalytic Method for Denture Base Resins

Abstract

Background: 3,9-Dimethylene-1,5,7,11-tetraoxaspiro[5,5]undecane (DMTOSU) is a double ring-opening monomer that exhibits expansion upon polymerization and may be used as a denture base resin's comonomer to offset or minimize polymerization shrinkage. It's synthesis by transesterification reaction (TE) catalyzed by distannoxane is not reported in the literature. The synthesis became the prime concern because this monomer is hardly available commercially. Purpose: The purpose is to confirm the DMTOSU synthesis and compare the synthesized monomers obtained by two different catalytic processes through Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopies. Materials and Methods: Scheme I synthesis was by TE catalyzed by dichlorotetrabutyl distannoxane (DCBS) yielding M1 monomer. Scheme II synthesis was catalyzed by dibutyltin oxide-carbon disulfide (DBTO-CS 2 ) yielding M2 monomer. Results: The appearance of a characteristic peak at 1212 cm −1 in FTIR spectrum, a doublet at δ 4.95 in 1 H-NMR spectrum and a peak at δ 117.12 in 13 C-NMR spectrum confirmed the synthesis of DMTOSU-M1catalyzed by DCBS, which is not significantly different from DMTOSU-M2 catalyzed by DBTO-CS 2 . Conclusion: The catalytic action of DCBS is a successful alternative to the DBTO-CS 2 catalysis in DMTOSU synthesis.

Isolation and Identification of Cytotoxic Compounds Present in Biomaterial Life®

“…This study also highlights the utility of chemical techniques for developing and evaluating biomaterials, which have often a complex constitution with dozens of components [ 32 , 33 , 34 ]. Additionally, chemical reactions occur during their manipulation, application, and later when in contact with the living tissues [ 19 , 35 , 36 ].…”

Development and Dental Applications of Spiro Expanding Monomers as Antishrinkage Additives

“…[134,[137][138][139] The addition of ring-opening spiro EMs in denture base materials to form copolymers has a great influence on the dimensional accuracy. [64] Ranganathan, Vikraman and co-workers synthesized 3,9-dimethylene-1,5,7,11-tetraoxaspiro [5,5]undecane (DMTOSU) by transesterification reaction (TE) catalyzed by distannoxane, [140] which was not reported in the literature and added DMTOSU in denture base resin for thermal curing to form P(MMA-Co-DMTOSU) copolymer. [141] The FTIR spectroscope showed that the increase of the carbonyl peak, the disappearance of the spiro peak and the appearance of the ether bond, confirming the occurrence of ring-opening polymerization.…”