4,4'-Methylenebis(N-sec-butylaniline)
[CAS# 5285-60-9]

Identification

• Classification: Pharmaceutical intermediate >> Diphenylamine intermediate
• Name: 4,4'-Methylenebis(N-sec-butylaniline)
• Synonyms: N-butan-2-yl-4-[[4-(butan-2-ylamino)phenyl]methyl]aniline
• Molecular Formula: C₂₁H₃₀N₂
• Molecular Weight: 310.48
• CAS Registry Number: 5285-60-9
• EC Number: 226-122-6
• SMILES: CCC(C)NC1=CC=C(C=C1)CC2=CC=C(C=C2)NC(C)CC

Properties

• Solubility: 0.06903 mg/L (25 °C water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.581, Calc.^*
• Melting point: 143.50 °C
• Boiling Point: 458.2±38.0 °C (760 mmHg), Calc.^*, 404.47 °C
• Flash Point: 272.3±18.6 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H317-H373-H400-H410
• Safety Statements: P260-P261-P264-P270-P272-P273-P280-P301+P317-P302+P352-P319-P321-P330-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1B	H317
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

4,4'-Methylenebis(N-sec-butylaniline), commonly known as MBBA, is an organic compound that has garnered attention in the field of polymer chemistry and materials science. The substance was first synthesized in the mid-20th century as part of research efforts aimed at developing advanced polymers with enhanced properties. Its structure consists of two N-sec-butylaniline groups linked by a methylene bridge, which contributes to its unique chemical behavior and functionality.

The discovery of 4,4'-Methylenebis(N-sec-butylaniline) was driven by the need for effective curing agents and hardeners in epoxy resins. The compound exhibits excellent reactivity with epoxy functional groups, making it a valuable component in the formulation of thermosetting plastics. Its ability to promote cross-linking in epoxy systems allows for the development of materials with improved mechanical properties, chemical resistance, and thermal stability.

One of the primary applications of MBBA is in the manufacturing of high-performance adhesives and coatings. These formulations benefit from the compound's capability to enhance adhesion strength and durability, particularly in demanding environments where exposure to moisture, heat, and chemicals is a concern. The incorporation of 4,4'-Methylenebis(N-sec-butylaniline) into adhesive formulations results in products that demonstrate superior bond strength and longevity, making them suitable for use in industries such as automotive, aerospace, and construction.

In addition to its role in adhesives, 4,4'-Methylenebis(N-sec-butylaniline) is also utilized in the production of composite materials. When used as a curing agent in epoxy resins, it facilitates the formation of highly cross-linked networks that provide excellent structural integrity. These properties make composites containing MBBA ideal for applications in aerospace components, sporting goods, and industrial equipment where high strength-to-weight ratios are essential.

Another significant application of this compound is in the field of coatings. The use of 4,4'-Methylenebis(N-sec-butylaniline) in coating formulations improves resistance to abrasion, impact, and chemical exposure, thereby extending the lifespan of coated surfaces. This is particularly advantageous in automotive finishes and industrial coatings, where durability and aesthetic quality are critical.

The versatility of 4,4'-Methylenebis(N-sec-butylaniline) is further enhanced by its compatibility with various polymer systems. It can be blended with different resins to tailor the properties of the final product according to specific application requirements. This adaptability has made MBBA a favored choice among formulators seeking to optimize the performance of their materials.

Despite its numerous benefits, the use of 4,4'-Methylenebis(N-sec-butylaniline) must be approached with caution due to potential health and safety concerns associated with amine compounds. Appropriate handling practices and safety measures are essential to mitigate any risks associated with exposure during production and application.

Ongoing research aims to explore further applications of 4,4'-Methylenebis(N-sec-butylaniline) in emerging fields such as nanocomposites and bio-based materials. As sustainability becomes increasingly important in material development, the potential for using MBBA in environmentally friendly formulations represents an exciting avenue for future innovation.

In conclusion, 4,4'-Methylenebis(N-sec-butylaniline) plays a crucial role in advancing polymer technology, particularly in the development of high-performance adhesives, coatings, and composite materials. Its discovery and subsequent applications reflect the evolving landscape of material science, driven by the demand for durable and efficient products in various industries.

References

2019. The Influence of the Amount of Rigid Blocks on the Physical and Mechanical Properties of Sealants and Coatings on the Basis of Polyurea. Polymer Science, Series D, 12(2).
DOI: 10.1134/s1995421219020205

2018. Bioaccumulation of sediment-associated substituted phenylamine antioxidants in Tubifex tubifex and Lampsilis siliquoidea. Ecotoxicology, 27(4).
DOI: 10.1007/s10646-018-1931-7