Cyclic Methacrylate Tetrahydropyrimidinones: Synthesis, Properties, (Co)Polymerization

Area of Science:

• Polymer Chemistry
• Organic Synthesis
• Materials Science

Background:

• Biocidal polymers are crucial for controlling microbial growth in various applications.
• Radical polymerization of methacrylate guanidine monomers is a developing area for novel biocidal materials.

Purpose of the Study:

• To identify and characterize a cyclic byproduct formed during the radical polymerization of novel biocidal methacrylate guanidine monomers.
• To synthesize and optimize the production of the identified byproduct and its methacrylate salt.
• To explore the polymerization of the methacrylate salt for potential applications in tailored biocide polymers.

Main Methods:

• Radical polymerization
• Spectroscopic characterization (1H and 13C NMR)
• Pyrolysis chromatography
• Synthesis optimization
• Homopolymerization and copolymerization in aqueous media

Main Results:

• Discovery and identification of 2-imino-5-methyltetrahydropyrimidin-4(1H)-one (THP) as a cyclic byproduct.
• Successful synthesis and characterization of the methacrylate salt of THP (MTHP).
• Optimized synthesis conditions for high yields of THP and MTHP.
• Achieved moderate to high yields in MTHP homopolymerization and copolymerization with diallyldimethylammonium chloride in aqueous solutions.

Conclusions:

• The identified cyclic byproduct (THP) and its methacrylate salt (MTHP) are viable monomers for polymerization.
• The polymerization of MTHP offers a promising route to novel, tailored biocide polymers with potential antimicrobial applications.
• This research expands the scope of functional monomers for developing advanced polymeric biocides.