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1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione

Chemical compound From Wikipedia, the free encyclopedia

1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione
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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.

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Synthesis

It can be synthesised in a 2-step manner. Firstly, 2,4-dimethyl-6-tert-butylphenol is reacted with formaldehyde and HCl (Blanc reaction) to generate a chloromethyl group in the less hindered meta position. This intermediate then reacts with cyanuric acid 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 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 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.

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Applications

Although it is compatible with polyolefins Antioxidant 1790 is a fairly expensive antioxidant and it is primarily used in speciality applications. It has good compatibility with the engineering plastics, high activity and low colour formation,[1] which makes it common choice in synthetic fibres (polyurethane, polyester and polyamide), particularly elastane.

See also

References

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