2-(N,N-Dimethylamino)ethyl acrylate (DMAEA) is a monofunctional amino acrylate used to introduce tertiary amine functionality into polymers and copolymers. Its structure combines a polymerizable acrylate group with a dimethylaminoethyl substituent whose tertiary amine can be protonated or chemically quaternized.
DMAEA is used in the synthesis of ionizable and charge-modifiable polymers, including systems investigated for pH-dependent behavior and controlled cationic functionality. Polymer properties depend on comonomer composition, molecular weight, degree of ionization or quaternization, counterion, pH, ionic strength, and processing conditions.
Synonyms: 2-(Dimethylamino)ethyl acrylate; dimethylaminoethyl acrylate; acrylic acid 2-(dimethylamino)ethyl ester; DMAEA.
Key Properties
- Monofunctional amino acrylate monomer
- Tertiary amine functionality
- Purity by GC: ≥98.0%
- CAS number: 2439-35-2
- Molecular formula: C7H13NO2
- Linear formula: H2C=CHCO2CH2CH2N(CH3)2
- Molecular weight: 143.1 g/mol
- Appearance: colorless to light yellow to light orange clear liquid
- Refractive index: 1.438
- MEHQ inhibitor: approximately 1000 ppm
- Storage temperature: 4°C
- Polysciences catalog number: 02257
Applications
Amine-Functional Polymer & Copolymer Synthesis
DMAEA is used to introduce pendant tertiary amine groups into acrylic polymers and copolymers. Monomer composition can be varied to control the concentration of ionizable amine functionality within the resulting polymer.
pH-Responsive Polymer Research
The tertiary amine groups in DMAEA-derived polymers can undergo reversible protonation as solution pH changes. Changes in ionization can alter polymer charge density, intermolecular interactions, solubility, chain conformation, and solution behavior.
Cationic & Quaternized Polymer Development
The tertiary amine can be quaternized to form a permanently charged quaternary ammonium group. This chemistry provides a route to polymers with controlled cationic functionality for studies involving ionic interactions and polyelectrolyte behavior.
Controlled Radical Polymerization
DMAEA has been investigated in reversible addition-fragmentation chain-transfer (RAFT) polymerization for the preparation of polymers with controlled molecular-weight characteristics. Reaction conditions should be selected with consideration of monomer conversion, inhibitor concentration, polymer architecture, and the tertiary amine functionality.
Polymerization & Formulation Considerations
- DMAEA contains one polymerizable acrylate group and one pendant tertiary amine
- The tertiary amine is neutral in its unprotonated form; protonation produces a positively charged ammonium group
- Quaternization can convert the tertiary amine to permanently charged quaternary ammonium functionality
- MEHQ is present at approximately 1000 ppm to inhibit premature polymerization during storage
- Account for inhibitor concentration when establishing radical initiation and polymerization conditions
- pH, ionic strength, counterion, and degree of protonation can influence polymer behavior in solution
- Ester hydrolysis can alter the composition and charge characteristics of DMAEA-containing polymers under aqueous conditions
- Do not substitute DMAEMA or a diethylaminoethyl monomer without evaluating changes in polymerization and polymer properties
Properties of DMAEA-containing polymers depend on the complete polymer composition and environment rather than DMAEA content alone. Molecular weight, comonomer sequence, architecture, degree of ionization, ionic strength, pH, and hydrolysis can influence solution behavior and intermolecular interactions.
Application Tips
- Account for the approximately 1000 ppm MEHQ inhibitor when designing radical polymerization experiments
- Use clean, dry equipment compatible with acrylate monomers and tertiary amines
- Control pH when polymer ionization or charge state is an experimental variable
- Characterize monomer conversion and copolymer composition when establishing new polymerization conditions
- Evaluate hydrolytic stability when DMAEA-containing polymers will remain in aqueous media for extended periods
- Use controlled small-scale reactions when establishing new initiator or chain-transfer-agent conditions
- Protect working quantities from contamination, excessive heat, and unintended polymerization
Handling & Storage
- Store at 4°C in a cool, well-ventilated location
- Keep the container tightly closed when not in use
- Keep away from heat, sparks, flames, and other ignition sources
- Handle in a chemical fume hood or with effective local ventilation
- Wear protective gloves, safety glasses, and suitable protective clothing
- Avoid breathing vapors, mist, or spray
- Prevent contact with the skin and eyes
- Avoid release to the environment
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FAQ
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1. What is DMAEA used for?
DMAEA is an amine-functional acrylate monomer used to introduce tertiary amine groups into polymers and copolymers. It is particularly relevant to research involving ionizable, pH-responsive, charge-modifiable, and cationic polymer systems.
2. Is DMAEA an acrylate or a methacrylate?
DMAEA is an acrylate. Its polymerizable group is derived from acrylic acid. It should not be confused with 2-(N,N-dimethylamino)ethyl methacrylate, commonly abbreviated DMAEMA.
3. Is DMAEA the same as DMAEMA?
No. DMAEA is 2-(N,N-dimethylamino)ethyl acrylate, whereas DMAEMA is the corresponding methacrylate. DMAEMA contains an additional methyl substituent on the polymerizable carbon-carbon double bond, which can affect polymerization kinetics and the properties of the resulting polymers.
4. Is dimethylaminoethyl acrylate the same as diethylaminoethyl acrylate?
No. DMAEA contains two methyl substituents on the tertiary amine nitrogen. A diethylaminoethyl analog contains ethyl substituents instead and is a chemically distinct monomer.
5. Is DMAEA a cationic monomer?
The tertiary amine in unprotonated DMAEA is neutral. Protonation converts it to a positively charged ammonium species, and quaternization can introduce permanent cationic charge.
6. Why are DMAEA-containing polymers pH responsive?
The pendant tertiary amine groups can reversibly protonate as pH changes. This alters polymer charge density and can influence solubility, ionic interactions, chain conformation, and other solution properties.
7. What are the purity and CAS number of DMAEA?
DMAEA has a purity of ≥98.0% by GC and CAS number 2439-35-2. It contains approximately 1000 ppm MEHQ as a polymerization inhibitor.
8. How can I request a larger quantity of DMAEA?
For larger-volume requirements, use the bulk-quote option.
Safety & Documentation
DMAEA requires controlled handling because of its acute toxicity and corrosivity. Use effective ventilation and appropriate protective gloves, eye protection, and protective clothing, and avoid breathing vapors or mist. Store at 4°C and keep away from ignition sources. Refer to the Safety Data Sheet, product specification, and lot-specific Certificate of Analysis for complete handling, storage, disposal, and quality information.
