1,3,5-Triazine-2,4,6-triamine, polymer with formaldehyde, methylated
[CAS# 68002-20-0]

Identification

• Classification: Catalysts and additives >> Polymer
• Name: 1,3,5-Triazine-2,4,6-triamine, polymer with formaldehyde, methylated
• Synonyms: Hexakis(methoxymethyl)melamine
• Molecular Formula: C₁₅H₃₀N₆O₆
• Molecular Weight: 390.44
• CAS Registry Number: 68002-20-0
• EC Number: 614-203-2
• SMILES: COCN(COC)c1nc(nc(n1)N(COC)COC)N(COC)COC

Properties

• Solubility: 149.3 mg/L (25 °C water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.548, Calc.^*
• Melting point: 188.40 °C
• Boiling Point: 487.0±55.0 °C (760 mmHg), Calc.^*, 448.20 °C
• Flash Point: 248.3±31.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H315-H317-H318-H332-H351
• Safety Statements: P202-P280-P302+P352-P304+P340+P312-P305+P351+P338-P308+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	3	H226

Discovery and Applications

1,3,5-Triazine-2,4,6-triamine, polymer with formaldehyde, methylated, commonly known as methylated melamine-formaldehyde resin, is a synthetic thermosetting polymer widely employed in industrial and consumer applications. This material is derived from the reaction of melamine (1,3,5-triazine-2,4,6-triamine) with formaldehyde, with methylation steps included to improve solubility and processing characteristics. The resulting polymer exhibits remarkable chemical resistance, thermal stability, and surface hardness, making it highly versatile.

The discovery of melamine-formaldehyde polymers dates to the early 20th century, arising from studies into formaldehyde’s reactivity with various nitrogenous compounds. The introduction of methylation techniques allowed for enhanced formulation flexibility, enabling the production of tailored materials for specific applications. By the mid-20th century, methylated melamine-formaldehyde resins had become integral to industries ranging from construction to consumer goods.

One of the primary uses of this polymer is in the manufacture of high-pressure laminates. These laminates, often used for countertops, furniture, and flooring, are prized for their durability, stain resistance, and aesthetic appeal. The polymer acts as a binder for decorative and kraft papers, ensuring a robust and heat-resistant surface upon curing under high temperature and pressure.

In coatings, methylated melamine-formaldehyde resin is widely used as a crosslinking agent. Its ability to form strong covalent bonds with hydroxyl, amide, and carboxyl groups in polymers makes it ideal for use in automotive finishes, industrial paints, and protective coatings. The resulting films are characterized by their excellent hardness, gloss retention, and resistance to weathering.

Another critical application of this polymer lies in the molding of lightweight, durable plastic products. Items such as electrical components, kitchenware, and children’s toys are often made from melamine-based molding compounds, where the polymer provides mechanical strength and resistance to heat and chemicals.

The methylation process enhances the polymer's solubility in organic solvents, making it easier to integrate into different formulations. This has broadened its scope of applications, including use in adhesives, textile treatments, and paper coatings, where it imparts moisture resistance and dimensional stability.

Research into the environmental impact of melamine-formaldehyde polymers has prompted the development of more sustainable synthesis methods, focusing on reducing formaldehyde emissions and incorporating renewable feedstocks. Advances in this area ensure that these materials continue to meet the demands of modern industries while addressing sustainability concerns.

The combination of functional versatility and robustness ensures that 1,3,5-triazine-2,4,6-triamine, polymer with formaldehyde, methylated remains a cornerstone material in a variety of sectors, from construction and automotive to consumer products and beyond.

References

Guang Jia, Hongpeng You, Yuhua Zheng, Kai Liu, Ning Guo and Hongjie Zhang. Synthesis and characterization of highly uniform LuO:Ln3+ (Ln = Eu, Er, Yb) luminescent hollow microspheres, CrystEngComm, 2010, 12, 2943.