N,N-Dimethylacrylamide: A Versatile Monomer in Modern Chemistry

Introduction

N, N-Dimethylacrylamide is a widely used chemical compound in the field of polymer chemistry and material science. Known for its versatile properties, N, N-DIMETHYLACRYLAMIDE has garnered significant attention from researchers and industry professionals alike. As a monomer, N, N-DIMETHYLACRYLAMIDE is often employed in the synthesis of various polymers, which are crucial components in the production of materials with specific physical and chemical properties. This article delves into the details of N, N-Dimethylacrylamide, discussing its structure, properties, applications, and proper storage methods, to provide valuable insights for professionals in the chemical field.

Figure 1 Characteristics of N, N-Dimethylacrylamide

Structure and Properties

N, N-Dimethylacrylamide (C6H11NO), also known as 2-Propenamide, N, N-dimethyl-, is an organic compound characterized by an amide group bonded to a carbon-carbon double bond. The compound's structure features an acryloyl group attached to an amide nitrogen that is substituted by two methyl groups. This unique molecular arrangement gives N, N-DIMETHYLACRYLAMIDE distinct chemical and physical properties, making it a highly attractive monomer in polymer synthesis.

Physical Properties:

Molecular Weight: 113.16 g/mol

Appearance: N, N-DIMETHYLACRYLAMIDE is a colorless, clear liquid at room temperature.

Boiling Point: Approximately 170-172°C.

Melting Point: -20°C.

Density: 0.962 g/cm³ at 20°C.

Solubility: N, N-DIMETHYLACRYLAMIDE is highly soluble in water, alcohol, and other polar solvents. Its solubility in water enhances its applicability in aqueous polymerization processes.

Refractive Index: 1.465 at 20°C.

Chemical Properties:

N, N-DIMETHYLACRYLAMIDE's chemical reactivity stems from its acrylamide structure, which enables it to undergo polymerization reactions. It is susceptible to free radical polymerization, making it a key component in the production of a wide range of copolymers and homopolymers. Additionally, the N, and N-dimethyl groups in the molecule contribute to its hydrophilicity, further enhancing its suitability for various applications, particularly in water-soluble polymer systems.

Composition

The chemical composition of N, N-Dimethylacrylamide is simple yet effective for various applications. The presence of an amide group (–CONH2) linked to a carbon-carbon double bond makes N, N-DIMETHYLACRYLAMIDE a reactive monomer capable of forming polymer chains. The two methyl groups attached to the nitrogen atom in the amide structure provide steric hindrance, which can influence the polymerization behavior and the final properties of the polymer.

N, N-DIMETHYLACRYLAMIDE can act as a monomer in homopolymerization, forming poly(N, N-dimethyl acrylamide) (PN, N-DIMETHYLACRYLAMIDE). It can also be used in copolymerization with other monomers, such as acrylic acid, acrylamide, or methacrylates, to tailor the properties of the resulting polymer. The balance of hydrophilicity and chemical reactivity in N, N-DIMETHYLACRYLAMIDE makes it an attractive candidate for various polymer formulations.

Applications

N, N-Dimethylacrylamide has found extensive use across multiple industries due to its versatile nature. Its ability to polymerize with other monomers allows for the creation of polymers with customized properties, making it a key component in products ranging from hydrogels to coatings.

1. Biomedical Applications:

N, N-DIMETHYLACRYLAMIDE is a key monomer in the production of hydrogels used in biomedical applications. Hydrogels made from N, N-DIMETHYLACRYLAMIDE-based polymers are highly water-absorbent and can be used in wound dressings, contact lenses, and drug delivery systems. The hydrophilic nature of N, N-DIMETHYLACRYLAMIDE-based hydrogels enables them to retain moisture and provide a biocompatible environment, which is essential for medical applications.

2. Water Treatment:

In the field of water treatment, N, N-DIMETHYLACRYLAMIDE is used to synthesize water-soluble polymers that serve as flocculants, coagulants, and dispersants. These polymers help in the removal of suspended particles and impurities from water, making the treatment process more efficient. N, N-DIMETHYLACRYLAMIDE-based polymers are preferred in water treatment due to their high solubility and effectiveness in a wide pH range.

3. Oil and Gas Industry:

In the oil and gas industry, N, N-DIMETHYLACRYLAMIDE is utilized in the production of drilling fluids and enhanced oil recovery agents. The water-soluble polymers derived from N, N-DIMETHYLACRYLAMIDE improve the viscosity and stability of drilling fluids, which helps in reducing friction and preventing wellbore collapse during drilling operations. Additionally, N, N-DIMETHYLACRYLAMIDE-based polymers can be used in enhanced oil recovery processes to increase the extraction of oil from reservoirs.

4. Adhesives and Coatings:

N, N-DIMETHYLACRYLAMIDE-based polymers are also employed in the formulation of adhesives and coatings. Their ability to form strong, flexible bonds makes them ideal for use in adhesives for various substrates. In coatings, N, N-DIMETHYLACRYLAMIDE-based polymers provide excellent adhesion, durability, and resistance to environmental factors such as moisture and UV radiation. These properties make them suitable for protective coatings in the automotive, construction, and electronics industries.

5. Textile Industry:

In the textile industry, N, N-DIMETHYLACRYLAMIDE is used to produce water-soluble polymers that serve as fabric softeners, antistatic agents, and dye-fixation agents. These polymers enhance the quality and durability of textiles by improving their resistance to wear and tear, reducing static cling, and ensuring vibrant, long-lasting colors.

Storage and Handling

Proper storage and handling of N, N-Dimethylacrylamide are critical to ensure its stability and prevent unwanted polymerization. N, N-DIMETHYLACRYLAMIDE should be stored in tightly sealed containers, preferably made of materials resistant to chemical corrosion, such as stainless steel or high-density polyethylene (HDPE). It is recommended to store N, N-DIMETHYLACRYLAMIDE in a cool, dry, and well-ventilated area away from direct sunlight, heat sources, and incompatible materials, such as strong oxidizing agents.

The stability of N, N-DIMETHYLACRYLAMIDE can be maintained by storing it at low temperatures, typically below 25°C. In some cases, inhibitors such as hydroquinone or methoxyphenol (MEHQ) may be added to N, N-DIMETHYLACRYLAMIDE to prevent premature polymerization during storage. Regular monitoring of the inhibitor concentration is essential to ensure the continued stability of the compound.

When handling N, N-DIMETHYLACRYLAMIDE, appropriate personal protective equipment (PPE) should be worn, including gloves, goggles, and lab coats, to prevent contact with the skin and eyes. In case of accidental spills or leaks, the affected area should be ventilated, and the spill should be contained and cleaned using absorbent materials such as sand or vermiculite.

Reference

[1] Akhmetzhan A, Myrzakhmetova N, Amangeldi N, et al. A short review on the N, N-Dimethylacrylamide-based hydrogels[J]. Gels, 2021, 7(4): 234.

[2] Algi M P, Okay O. Highly stretchable self-healing poly (N, N-dimethylacrylamide) hydrogels[J]. European polymer journal, 2014, 59: 113-121.