Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate explained

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.

Synthesis

It is formed by the Mannich reaction of 2,6-di-tert-butylphenol, cyanuric acid, and formaldehyde.

Properties and applications

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a high molecular weight additive, with low volatility. It is well suited to stabilising polyolefins against degradation caused by long term heat aging.^[1] It is an approved food contact material in the US.^[2]

See also

• 1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione - related phenolic antioxidant with a cyanurate core
• Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) - a commonly used phenolic polymer stabiliser

Notes and References

1. Gijsman . Pieter . Fiorio . Rudinei . Long term thermo-oxidative degradation and stabilization of polypropylene (PP) and the implications for its recyclability . Polymer Degradation and Stability . February 2023 . 208 . 110260 . 10.1016/j.polymdegradstab.2023.110260.
2. Web site: Inventory of Food Contact Substances Listed in 21 CFR . www.hfpappexternal.fda.gov . 4 December 2024.