Molecular Design of Isocyanurate Core-Based Acrylates Undergoing Volume Expansion on Radical Photo-Polymerization

Area of Science:

• Polymer Chemistry
• Materials Science
• Organic Synthesis

Background:

• Volume changes during polymerization can lead to material defects and performance limitations.
• Acrylates are widely used monomers in radical polymerization processes.
• Isocyanurate structures offer unique properties and potential for tailored material characteristics.

Purpose of the Study:

• To synthesize novel isocyanurate-substituted acrylates.
• To investigate their volume change behavior during radical photo-polymerization.
• To understand the structure-property relationships governing polymerization-induced volume changes.

Main Methods:

• Synthesis of isocyanurate core-based diacrylates and acrylate monomers with benzyl bisurethane moieties.
• Radical photo-polymerization experiments.
• Analysis of volume changes using dilatometry or similar techniques.
• Investigating copolymerization with conventional diacrylates.

Main Results:

• The synthesized isocyanurate-substituted acrylates exhibit significant positive volume expansion upon radical photo-polymerization.
• Acrylates featuring benzyl bisurethane moieties demonstrated the largest volume expansion.
• Copolymerization of these expanding monomers with volume-shrinking diacrylates effectively restricted overall volume change.
• A correlation between monomer concentration, polymer structure, and volume change was established.

Conclusions:

• Isocyanurate-based acrylates, particularly those with benzyl bisurethane groups, are effective in inducing significant volume expansion during radical photo-polymerization.
• These monomers can be utilized to counteract the shrinkage typically observed in acrylate polymerization, leading to dimensionally stable polymers.
• The study provides insights into controlling polymerization-induced volume changes through molecular design and copolymerization strategies.