Composite resins based on novel and highly reactive bisglycidyl methacrylate monomers

Abstract

Three new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene (MB‐Phe‐OH), 1,4‐bis(2‐hydroxy‐3‐methacryloxypropoxy)2‐cis‐butene (MB‐Cis‐OH), and 1,7‐bis(2‐hydroxy‐3‐methacryloxypropoxy)heptane (MB‐1,7‐OH); were synthesized and used as Bis‐GMA/TEGDMA (bisphenolglycidyl methacrylate/triethylene glycol dimethacrylate) composite resin additives. Flexural properties and double bond conversion of the dental resins composed of silanizated inorganic filler and organic matrices containing new monomers were evaluated. The composite resins formulated, using the monomers MB‐Cis‐OH and MB‐1,7‐OH, have mechanical properties and double bond conversion comparable with those of Bis‐GMA/TEGDMA composite resin used as control. The composite containing the new monomer MB‐Phe‐OH has better flexural properties (flexural strength 65.01 MPa and flexural modulus 5675.91 MPa) than the control composite resin (flexural strength 52.85 MPa and flexural modulus 4879.72 MPa); this could be attributed to the molecular structure of the monomer and its high double bond conversion level of 74.19%. The new bisglycidyl methacrylate monomer MB‐Phe‐OH could be potentially useful in the development of new organic matrices for dental composite resins with high double bond conversion and enhanced mechanical properties. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40971.

Photopolymerizable bisallylcarbonate and bisacrylic monomers useful in the formulation of dental composite resins and in the crosslinking of methyl methacrylate

“…We were interested in the synthesis of bisallylcarbonate and bisacrylic monomers as Bis‐GMA eluents as partial or total alternatives for the substitution of TEGMA in the formulation of new dental composite resins with enhanced or similar mechanical properties to those currently available . In addition, the presence of two double bonds in the structure of the monomers allowed them to be used as crosslinking agents of acrylic monomers such as MMA.…”

Adhesive Resins with High Shelf-Life Stability Based on Tetra Unsaturated Monomers with Tertiary Amines Moieties

“…The TTMEE and TTAC were synthesized according to a methodology described elsewhere [7]: 1.0 g (2.36 mmol) of 4,4 -methylenebis (N,N-diglycidylaniline) was dissolved in 80 mL of ethyl acetate and placed in a two-necked round-bottom flask equipped with a magnetic stirring bar and a reflux condenser, under constant agitation. Next, 1.2 mL (28.4 mmol) of methacrylic acid, for TTME, or acrylic acid for TTAC, 2 wt.% of triethylamine and 5 ppm of hydroquinone were added (Figure 1).…”

Effect of replacing UDMA by a new tetramethacrylate monomer on the properties of dental resin composite

“…Despite the partial substitutions of one of the monomers in the organic matrix, the resins show improved mechanical properties. 24,25 Despite having several drawbacks, BisGMA and UDMA are the most used base monomers in DRC. The use of UDMA in the formulation of BisGMA-free DRC has increased.…”