Cinnamyl methacrylate (CMA) is an aromatic methacrylate monomer containing both methacrylate and cinnamyl carbon-carbon double bonds. It is used in polymer synthesis when additional photoreactive unsaturation is required within a methacrylate-based system.
Polymerization behavior depends on the reaction mechanism and conditions. Free-radical polymerization of cinnamyl methacrylate has been reported to involve cyclization as well as vinyl propagation, while polymers and copolymers containing residual cinnamyl unsaturation can undergo crosslinking upon UV irradiation.
Key Properties
- Photocrosslinking methacrylate monomer
- Aromatic monomer with methacrylate and cinnamyl unsaturation
- Assay (GC): ≥95% (mixed isomers)
- CAS number: 31736-34-2
- Molecular formula: C13H14O2
- Linear formula: C6H5CH=CHCH2OCOC(CH3)=CH2
- Molecular weight: 202.3 g/mol
- Appearance: clear, colorless to pale yellow liquid
- Boiling point: 141°C at 3 mmHg
- Refractive index: 1.446
- MEHQ inhibitor: approximately 100 ppm
- Storage temperature: 4°C
- Polysciences catalog number: 02092
Applications
Functional Polymer & Copolymer Synthesis
Cinnamyl methacrylate is used in the synthesis of polymers and copolymers containing cinnamyl functionality. It has been studied under both radical and anionic polymerization conditions, including copolymerization with other methacrylate monomers.
Photocrosslinkable Polymer Films
Polymers and copolymers derived from cinnamyl methacrylate have been shown to crosslink upon UV irradiation when sufficient photoreactive unsaturation remains in the polymer. Crosslinking behavior depends on polymer structure, residual cinnamyl functionality, film geometry, and irradiation conditions.
Photosensitive Polymer Research
Cinnamyl methacrylate is useful in research involving photosensitive polymer systems in which changes in network structure are induced after polymer formation. The extent of photochemical crosslinking should be characterized for the specific polymer composition and processing conditions.
Copolymerization Studies
Cinnamyl methacrylate can be used to investigate comonomer incorporation, reactivity ratios, sequence distribution, residual unsaturation, and the relationship between polymerization conditions and subsequent photocrosslinking behavior.
Polymerization & Photocrosslinking Considerations
- Methacrylate and cinnamyl double bonds can participate differently depending on the polymerization mechanism
- Free-radical polymerization can involve cyclization in addition to conventional vinyl propagation
- Do not assume quantitative retention of cinnamyl unsaturation after polymerization
- Residual unsaturation should be characterized when subsequent UV crosslinking is required
- Account for the approximately 100 ppm MEHQ inhibitor when establishing radical polymerization conditions
- Control UV wavelength, irradiance, exposure time, and film thickness during photocrosslinking studies
- Evaluate polymer composition, conversion, and network formation under the intended experimental conditions
The polymerization route can affect the structure of the resulting polymer and the amount of photoreactive unsaturation available for subsequent crosslinking. Polymer architecture and irradiation conditions should therefore be considered together when developing a photocrosslinkable system.
Application Tips
- Define whether the experimental objective is polymer formation, retention of cinnamyl unsaturation, or subsequent photocrosslinking
- Account for MEHQ when selecting initiator concentration and reaction conditions
- Use controlled polymerization conditions appropriate for the selected comonomers and initiation method
- Characterize monomer conversion and residual unsaturation using suitable analytical methods
- Control unintended UV exposure when residual photoreactivity must be retained before a planned crosslinking step
- Establish UV exposure conditions experimentally for each polymer composition and sample geometry
- Begin with small-scale reactions when evaluating new polymerization or photocrosslinking conditions
Handling & Storage
- Store at 4°C in a well-ventilated location
- Keep the container tightly closed when not in use
- Use with good laboratory ventilation or in a chemical fume hood
- Wear protective gloves, safety glasses, and suitable protective clothing
- Avoid unnecessary skin and eye contact
- Wash hands thoroughly after handling
- Avoid release to the environment
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FAQ
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1. What is cinnamyl methacrylate used for?
Cinnamyl methacrylate is used in polymer and copolymer synthesis when cinnamyl functionality and subsequent photochemical crosslinking are of interest. It is particularly relevant to photocrosslinkable polymer and photosensitive materials research.
2. What functional groups are present in cinnamyl methacrylate?
Cinnamyl methacrylate contains a methacrylate ester, a cinnamyl carbon-carbon double bond, and an aromatic phenyl group. The molecule therefore contains two distinct unsaturated sites whose reactivity depends on the polymerization mechanism and conditions.
3. How does cinnamyl methacrylate support photocrosslinking?
Polymers containing residual cinnamyl unsaturation can undergo crosslinking upon UV irradiation. The extent of crosslinking depends on how much cinnamyl unsaturation remains after polymerization, as well as polymer structure, chain mobility, sample geometry, and irradiation conditions.
4. Does free-radical polymerization leave all cinnamyl groups intact?
No. Free-radical polymerization of cinnamyl methacrylate has been reported to involve cyclization as well as vinyl propagation. The amount of residual cinnamyl unsaturation therefore depends on the polymerization pathway and should be measured when it is important to subsequent photocrosslinking.
5. Is cinnamyl methacrylate a single isomer?
No. The assay specification is ≥95% by GC as mixed isomers. Researchers for whom stereochemical composition is important should account for the mixed-isomer composition when designing experiments and interpreting results.
6. Does cinnamyl methacrylate contain a polymerization inhibitor?
Yes. The material contains approximately 100 ppm MEHQ. The inhibitor concentration should be considered when establishing radical polymerization conditions.
7. What package size is available?
Cinnamyl methacrylate is available in a 5 g package. For larger quantities, use the bulk-quote option.
Safety & Documentation
Use cinnamyl methacrylate with good laboratory ventilation and wear protective gloves, safety glasses, and suitable protective clothing. Store at 4°C and keep the container tightly closed when not in use. Refer to the Safety Data Sheet, product specification, and lot-specific Certificate of Analysis for complete handling, storage, disposal, and quality information.
