1,3,5-Tris(4-(''tert''-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione (abbreviated here as Antioxidant 1790) is a speciality antioxidant used to stabilise plastics and synthetic fibres.

Synthesis

It can be synthesised in a 2-step manner. Firstly, 2,4-dimethyl-6-tert-butylphenol is reacted 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

HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a s ...

( Blanc reaction) to generate a chloromethyl group in the less hindered meta position. This intermediate then reacts with

cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...

to give the desired product.

Properties

As each phenol group contains only a single t-butyl group they are considered to have low

steric hindrance Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is generally a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivi ...

and thus high activity. Arranging three of these around an isocyanurate core gives a compound with a sufficiently high boiling point that it is not volatilised out of the plastic during

plastic extrusion Plastics extrusion is a high-volume manufacturing process in which raw plastic is melted and formed into a continuous profile. Extrusion produces items such as pipe/tubing, weatherstripping, fencing, deck railings, window frames, plastic ...

and moulding (up to 320 °C in the case of PA). The isocyanurate core also promotes a high level of crystallinity, which greatly reduces extraction of the antioxidant into water.

Applications

Although it is compatible with

polyolefins A polyolefin is a type of polymer with the general formula (CH2CHR)n where R is an alkyl group. They are usually derived from a small set of simple olefins ( alkenes). Dominant in a commercial sense are polyethylene and polypropylene. More specia ...

Antioxidant 1790 is a fairly expensive antioxidant and it is primarily used in speciality applications. It has good compatibility with the

engineering plastic Engineering plastics are a group of plastic materials that have better mechanical or thermal properties than the more widely used commodity plastics (such as polystyrene, polyvinyl chloride, polypropylene and polyethylene). Engineering plastic ...

s, high activity and low colour formation, which makes it common choice in

synthetic fibres Synthetic fibers or synthetic fibres (in British English; see spelling differences) are fibers made by humans through chemical synthesis, as opposed to natural fibers that are directly derived from living organisms, such as plants like cotton or ...

(polyurethane, polyester and polyamide), particularly

elastane Spandex, Lycra, or elastane is a synthetic fiber known for its exceptional elasticity. It is a polyether- polyurea copolymer that was invented in 1958 by chemist Joseph Shivers at DuPont. Name The name ''spandex'', which is an anagram of th ...

References

{{DEFAULTSORT:Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione, 1,3,5- Tert-butyl compounds 3-Hydroxyphenyl compounds Triazines Triols Triketones Phenol antioxidants

Synthesis

Properties

Applications

See also

References