Hexa(methoxymethyl)melamine (HMMM) is a

hemiaminal ether In organic chemistry, a hemiaminal (also carbinolamine) is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: . R can be hydrogen or an alkyl group. Hemiaminals are intermediat ...

commonly used as a

crosslinking agent In chemistry and biology, a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...

in the production of

coatings A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints and ...

and

rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Types of polyisoprene ...

items. It is produced via the reaction of

melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer (chemistry), trimer of cyanamide, with a 1,3,5-Triazine, 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives ha ...

with

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

and excess

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

, with the later also acting as a solvent for the reaction. It can be considered as a monomeric intermediate in the formation of

melamine resin Melamine resin or melamine formaldehyde (also shortened to melamine) is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. ...

. Hexamethoxymethylmelamine is used along with

resorcinol Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or ''meta- (chemistry), meta''-isomer). Resorcinol crystallizes from benzene as co ...

in the production of vehicle tires, where it improves adhesion between the rubber and the steel reinforcing cords. As it has some water solubility it slowly leaches out of the rubber; particularly from the particles formed as the tires wear-down through use. Road runoff then introduces it into urban waters, where it has become a contaminant of emerging concern.

References

{{Reflist Triazines

See also

References