Mechanism of accelerated photofading of thioether anthraquinone dyes in styrene butadiene resins

• Published in: Journal of applied polymer science 1988-08, Vol.36 (5), p.1205-1219
• Main Authors: Paine, Anthony J., Winnik, Françoise M., Bocking, Victor
• Format: Article
• Language: English
• Subjects: Applied sciences; Chemical industry and chemicals; Dyes, pigments; Exact sciences and technology; Industrial chemicals
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.1988.070360520

Many anthraquinone dyes fade in visible light up to 100 times faster in styrene butadiene copolymers than in polyester resins or polystyrene. A mechanistic investigation of the photofading of 1,5‐dihydroxy‐2,6‐diisobutyl‐4‐thiophenylanthraquinone has established that the dye sensitizes formation of singlet oxygen, a very reactive species, which attacks the double bonds in the styrene butadiene, resulting in extensive chain cleavage and peroxide formation. The major process is the oxidation of the polymer, and the dye fading is a minor process whereby the dye is apparently attacked by polymeric peroxides. The mechanism appears to be general for anthraquinone dyes, especially those with thioether, amino, hydroxy, or double‐bond functionality. Unfortunately the fading is unaffected by most anticxidant stabilizers: the best result achieved was a doubling of half‐life with 1 wt% Spinuvex A‐36. This is still insufficient to give colored styrene butadiene copolymer resins the intrinsic dye stability available in other polymers, rendering styrene butadiene unsuitable for applications requiring high photostability of anthraquinone dyes.