Off-odor from styrene-butadiene coatings

An earlier off-odor problem that surfaced was the presence of 4-phenyl-cyclohexene in styrene-butadiene coated paper (Koszinowski et al. 1980). This compound was created by a Diels-Alder condensation reaction involving a molecule of styrene and butadiene and is differentiated by its odor from the isomeric 3 and 1-phenyl-cyclohex-ene compounds which cannot be formed by such a condensation reaction. The recognition threshold of this compound in the headspace over an aqueous solution lies around a concentration of 10 pg/kg (10 ppb). The typical odor of this compound at concentrations of 4-phenyl-cyclohexene in paper over 4 mg/kg (4 ppm) is easily identified. AGC determination in this concentration range is also possible without difficulty and its identification with MS using the relative molecular mass of 158 and one of the retro Diels-Alder decomposition product fragments at m/e = 104 (styrene) and mJe = 54 (butadiene) is definitely possible. 

From the investigation of different off-odor influencing factors it was determined that the off-odor problems in coated papers become more intense with increasing moisture content. 

---