N-Vinylcaprolactam
[CAS# 2235-00-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-Vinylcaprolactam
• Synonyms: 1-Ethenylazepan-2-one; 1-Vinylhexahydro-2H-azepin-2-one; 1-Ethenylhexahydro-2H-azepin-2-one
• Molecular Formula: C₈H₁₃NO
• Molecular Weight: 139.19
• CAS Registry Number: 2235-00-9
• EC Number: 218-787-6
• SMILES: C=CN1CCCCCC1=O

Properties

• Density: 1.029 g/mL
• Melting point: 35-38 °C (dec.)
• Boiling point: 128 °C (21 mmHg)
• Refractive index: 1.
• Flash point: 101 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H317-H319-H335-H372-H373
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

N-Vinylcaprolactam, commonly referred to as NVCL, is an important vinyl monomer that has attracted significant attention in the fields of polymer chemistry and materials science. This compound is derived from caprolactam, which is primarily known as a precursor for nylon production. The introduction of a vinyl group at the nitrogen atom enables NVCL to undergo polymerization, leading to the formation of a variety of functional polymers with desirable properties.

The discovery of N-vinylcaprolactam can be traced back to research on lactam derivatives in the mid-20th century, as chemists sought to develop new monomers for the synthesis of polymers with tailored characteristics. The ability of NVCL to polymerize readily through radical polymerization techniques has made it a versatile building block in the production of diverse materials. Its unique structure combines both the features of a lactam and a vinyl group, which contributes to its reactivity and compatibility with other monomers.

One of the primary applications of N-vinylcaprolactam is in the production of thermoresponsive polymers. When polymerized, NVCL exhibits a lower critical solution temperature (LCST) behavior, which means that the solubility of the polymer in water decreases with increasing temperature. This property is particularly useful in applications such as drug delivery, where NVCL-based polymers can respond to physiological temperature changes, allowing for controlled release of therapeutic agents. Such thermoresponsive behavior is advantageous in biomedical applications, as it can enhance the effectiveness of drug formulations while minimizing side effects.

In addition to its role in drug delivery systems, N-vinylcaprolactam is employed in the synthesis of various coatings and adhesives. Its ability to form films upon polymerization contributes to the development of protective coatings that offer excellent adhesion, chemical resistance, and durability. These characteristics make NVCL-based coatings suitable for applications in automotive, aerospace, and construction industries, where long-lasting performance is critical.

Moreover, N-vinylcaprolactam has been utilized in the formulation of superabsorbent materials. By incorporating NVCL into hydrophilic polymer matrices, researchers have developed products capable of absorbing significant amounts of water and other liquids. This application is particularly relevant in personal care products, such as diapers and feminine hygiene products, where high absorbency is essential.

Despite its many beneficial applications, the use of N-vinylcaprolactam is not without challenges. The polymerization process can lead to the formation of unwanted by-products, and the handling of vinyl compounds requires careful attention due to their potential health and safety risks. Researchers continue to explore safer and more efficient polymerization methods to optimize the use of NVCL while ensuring environmental compliance and worker safety.

Ongoing research into N-vinylcaprolactam focuses on expanding its applications and enhancing its properties. Innovative formulations and copolymerization strategies aim to develop novel materials with specific functionalities, catering to the growing demand in various industries. The ability to tailor the properties of NVCL-based polymers positions them as valuable materials in advanced technologies.

The discovery and application of N-vinylcaprolactam exemplify the significance of vinyl monomers in the development of functional materials. Its roles in drug delivery, coatings, and absorbent materials underscore the impact of chemical innovations in addressing contemporary challenges across multiple sectors.

References

2024. Poly(chitosan-N-vinylcaprolactam-methacrylic acid) microgels as microreactor for Ag(I) ions extraction and in-situ silver nanoparticles formation to reduce the toxins. *International Journal of Biological Macromolecules*, 283.
DOI: 10.1016/j.ijbiomac.2024.136906

2024. Preparation of Thermo-sensitive oxidizable N-vinylcaprolactam-based terpolymers and their self-assembling property. *Journal of Polymer Research*, 31(2).
DOI: 10.1007/s10965-024-03909-5

1959. Synthesis of n-vinylcaprolactam by the indirect-vinylation method. *Bulletin of the Academy of Sciences of the USSR, Division of chemical science*, 8(5).
DOI: 10.1007/bf00915915