New uracil derivatives as antioxidants for natural rubber

Abstract

Purpose

Evaluation of uracil and/or benzothiazol derivatives as antioxidants in natural rubber mixes.

Design/methodology/approach

Cyanoacetylurea 1, as a precursor, was prepared at a good yield from widely available, low‐cost chemicals. Compound 1 was treated with triethylorthoformate and amine derivatives in one pot reaction affording the target uracil derivative 3. Replacement of the cyano group in 1 by benzothiazol led to obtaining the interesting N‐hydroxy uracils containing benzothiazole moiety 5 at a good yield. Some of the compounds prepared was selected and were evaluated as antioxidants in natural rubber mixes. The rheometric characteristic of the compounded rubber and the physico‐mechanical properties of the vulcanizates were determined.

Findings

The cure rate index, tensile strength and modulus increased while the equilibrium swelling decreased, i.e. compound 5 behaved as a secondary accelerator. The rubber vulcanizates were subjected to thermal oxidative ageing at 90°C for up to seven days. It has been found that uracil and/or benzothiazol derivatives can protect natural rubber vulcanizates against oxidative deterioration.

Research limitations/implications

The compounds prepareds were difficult to dissolve, they needed solvents with high boiling points, e.g. DMF, DMSO to be dissolved and even then they are not completely dissolved.

Practical implications

Uracil and or benzothiazol derivatives have many industrial applications.

Originality/value

The new compounds were prepared from very cheap and widely available chemicals. The compounds synthesised showed good antioxidant behaviour in comparison with the commercial antioxidant (phenyl‐β‐naphthyl amine) industrially used.

Citation

Yakout, E.M.A. and El‐Sabbagh, S.H. (2007), "New uracil derivatives as antioxidants for natural rubber", Pigment & Resin Technology, Vol. 36 No. 4, pp. 224-234. https://doi.org/10.1108/03699420710761825