Overview
Cyclohexylacrylamide (CHAA) is a specialty acrylamide derivative featuring a cyclohexyl substituent on the nitrogen atom. As a monomer, it plays a critical role in synthesizing polymers with tailored properties for advanced material applications. The compound's structure combines the reactivity of the acrylamide group with the hydrophobic characteristics of the cyclohexyl moiety, enabling unique material performance in engineered polymers. Industrial production typically involves the reaction of acryloyl chloride with cyclohexylamine under controlled conditions. CHAA is classified as a high-value chemical intermediate, primarily supplied to manufacturers in the specialty polymers sector. Its usage has grown in parallel with demand for functional hydrogels and temperature-resistant coatings.
Physical and Chemical Properties
CHAA presents as a crystalline solid with moderate thermal stability, decomposing at temperatures above 200°C. The cyclohexyl group introduces steric hindrance that slightly reduces polymerization kinetics compared to unsubstituted acrylamides, allowing better control in radical polymerization processes. Key reactivity stems from the electron-deficient vinyl bond, which participates readily in chain-growth polymerization. The amide group provides hydrogen bonding capacity, influencing polymer morphology. Solubility parameters make it compatible with common organic solvents like THF and DMF, though precipitation may occur in polar protic solvents at room temperature.
Main Applications
In hydrogel formulations, CHAA contributes to mechanical strength and controlled swelling behavior, particularly in biomedical applications such as contact lenses or drug delivery matrices. The hydrophobic cyclohexyl group modulates water absorption capacity while maintaining biocompatibility. The monomer is equally valuable in industrial coatings, where copolymers incorporating CHAA exhibit enhanced adhesion to low-energy surfaces like polyethylene. Advanced material applications include photoresist components for electronics manufacturing and molecular imprinting polymers for separation technologies. Recent R&D explores its use in stimuli-responsive polymers for sensor applications.
Safety and Storage
As a reactive monomer, CHAA requires careful handling to prevent unintended polymerization during storage. Commercial grades often contain 100-500 ppm of hydroquinone monomethyl ether (MEHQ) as inhibitor. Material Safety Data Sheets classify it as Hazard Category 4 for acute toxicity (oral) and skin irritation. Proper storage mandates oxygen-free atmospheres in amber glass or polyethylene-lined containers under refrigeration. Shelf life typically reaches 12 months when stored correctly. Firefighting measures for bulk quantities should use alcohol-resistant foam, as the compound may release toxic fumes (NOx, CO) during combustion.
B2B Procurement Guide
Industrial buyers should prioritize suppliers who provide detailed certificates of analysis including: monomer purity (HPLC), inhibitor content, residual solvent levels, and polymerization performance data. Technical grade (95-97% purity) suits some applications, while pharmaceutical or electronic uses demand ≥99% purity. Logistics require temperature-controlled shipping (2-10°C) with desiccant packs. MOQs typically start at 25kg for standard grades, with lead times of 4-8 weeks for custom synthesis. Price volatility depends on acrylonitrile feedstock markets. Consider dual sourcing for critical applications, as global production capacity remains concentrated in few specialized manufacturers.
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