51293-89-1Relevant articles and documents
Developing non-isocyanate urethane-methacrylate photo-monomers for 3D printing application
Bakhshi, Hadi,Meyer, Wolfdietrich,Singh, Neelima
, p. 44103 - 44110 (2020)
Urethane-methacrylate photo-monomers were prepared via a non-isocyanate route for the 3D printing application. The monomers were synthesized through reacting aliphatic amines, i.e. 1,6-hexanediamine, 1,4-butanediol bis(3-aminopropyl) ether, or n-butylamine, with cyclic carbonates, i.e. ethylene carbonate or propylene carbonate, followed by the methacrylation of the generated hydroxylurethanes. The effects of the chemical structure of monomers on their photo-reactivity and physicomechanical properties of the cured samples were studied. Propylene carbonate generated side methyl groups within the urethane block, which significantly limited the crystallization of the monomers resulting in high photo-reactivity (Rp,max = 6.59 × 10-2 s-1) and conversion (DBCtotal = 85%). The ether bonds of 1,4-butanediol bis(3-aminopropyl) ether decreased the intermolecular hydrogen bonding between urethane blocks, which not only improved the photo-reactivity (Rp,max = 8.18 × 10-2 s-1) and conversion (DBCtotal = 86%) of the monomer but led to a high crosslinking density (νc = 5140 mol m-3) and more flexibility for the cured sample. An ink was developed based on the monomers and successfully 3D printed on a digital light processing machine. In the absence of toxic isocyanates and tin compounds, the non-isocyanate route can be employed to develop urethane-methacrylates with desirable photo-reactivity and physicomechanical properties as good candidates to formulate inks for 3D printing of biomedical materials.
Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization: Steady-state evaluation
Berchtold, Kathryn A.,Nie, Jun,Stansbury, Jeffrey W.,Hacioglu, Bilge,Beckel, Eric R.,Bowman, Christopher N.
, p. 3165 - 3179 (2007/10/03)
Experimental investigations were made into the effects of monomer structure and functionality on free-radical polymerization kinetics. A more comprehensive understanding of how structural characteristics, monomer traits, and polymerization conditions influence the polymerization mechanisms and network evolution was desired. Variations in the nature of the monomers' secondary functionality and the terminal substitution were the primary variables examined. The three factors hypothesized as important to the advantageous polymerization characteristics observed are hydrogen bonding, hydrogen abstraction, and the electronic characteristics of the monomer. The experimental evaluations presented clearly demonstrate that each of these mechanisms contributes to the reactivity of these monomers and the networks that they form. The combination of these factors leads to cross-linked network formation and enhanced polymerization kinetics, i.e., monovinyl monomers with reactivities that rival those of commonly used divinyl monomers.
