N-Methylolacrylamide
[CAS# 924-42-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: N-Methylolacrylamide
• Synonyms: N-(Hydroxymethyl)-2-propenamide; N-(Hydroxymethyl)acrylamide
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.10
• CAS Registry Number: 924-42-5
• EC Number: 213-103-2
• SMILES: C=CC(=O)NCO

Properties

• Water solubility: <0.1 g/100 mL at 20.5 °C
• Density: 1.1±0.1 g/mL, Calc.^*
• Melting point: 75-79 °C (Expl.)
• Index of Refraction: 1.451, Calc.^*
• Boiling Point: 210.0±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 111.2±17.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H302-H315-H317-H319-H340-H350-H361-H361f-H372-H413
• Safety Statements: P203-P260-P261-P264-P264+P265-P270-P272-P273-P280-P301+P316-P301+P317-P302+P352-P305+P351+P338-P318-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Germ cell mutagenicity	Muta.	1B	H340
Carcinogenicity	Carc.	1B	H350
Acute toxicity	Acute Tox.	3	H301
Reproductive toxicity	Repr.	2	H361
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361f
Carcinogenicity	Carc.	2	H351
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Carcinogenicity	Carc.	1A	H350
Specific target organ toxicity - single exposure	STOT SE	2	H371
Germ cell mutagenicity	Muta.	1A	H340

Discovery and Applications

N-Methylolacrylamide is an organic compound derived from acrylamide, with a methylol group (-CH2OH) attached to the nitrogen atom of the amide group. It is primarily used as a chemical intermediate in the production of various polymeric materials and has applications in fields such as textiles, coatings, and water treatment.

The compound was first synthesized in the mid-20th century, and its development was part of a broader effort to modify acrylamide for various industrial uses. Its ability to form cross-linked polymers makes it particularly valuable in the creation of coatings, adhesives, and other materials that require durable and flexible properties.

N-Methylolacrylamide is commonly used in the textile industry, where it serves as a cross-linking agent for fabrics. When applied to textiles, it enhances their resistance to wrinkles, shrinkage, and fading, improving the durability and longevity of the fabrics. The cross-linking properties also contribute to the fabric’s ability to retain its shape and structure during repeated washing.

In addition to textiles, N-methylolacrylamide is used in the formulation of water-based coatings and paints. The polymerization of N-methylolacrylamide can enhance the properties of the coating, such as adhesion, flexibility, and water resistance. This makes it a popular ingredient in industrial coatings, which are applied to a wide variety of surfaces, including metals, wood, and plastics.

N-methylolacrylamide also finds applications in the water treatment industry, where it acts as a flocculant. In this role, it is used to help remove suspended solids from water, promoting the aggregation of particles into larger clumps that can then be easily removed through sedimentation or filtration. This application is important in both industrial water treatment and the treatment of wastewater, contributing to the purification of water used in various processes.

In the field of polymer chemistry, N-methylolacrylamide is used in the synthesis of polyacrylamide-based polymers. These polymers are widely employed in applications such as oil recovery, paper manufacturing, and water purification. The cross-linking ability of N-methylolacrylamide makes it an essential component in the production of water-soluble polymers that require enhanced mechanical strength and stability.

Overall, N-methylolacrylamide is an important industrial chemical with a broad range of applications, particularly in textiles, coatings, and water treatment. Its ability to form cross-linked polymers allows for the creation of durable, flexible materials with enhanced performance characteristics. As such, it remains a valuable substance in various manufacturing and processing industries.

References

2024. Antimicrobial Finishing of Cotton Fabric with N-MA Based on Plasma-Induced Grafting. Fibers and Polymers, 25(9).
DOI: 10.1007/s12221-024-00676-4

2023. Synthesis and characterization of starch-stabilized polyvinyl acetate-N-methylol acrylamide polymer-based wood adhesive. Journal of the Indian Academy of Wood Science, 20(1).
DOI: 10.1007/s13196-023-00312-3

2023. Stimuli-responsive electrospun nanofibers for drug delivery, cancer therapy, wound dressing, and tissue engineering. Journal of Nanobiotechnology, 21(1).
DOI: 10.1186/s12951-023-01987-z