Polychlorinated biphenyl contamination of paints containing polycyclic- and Naphthol AS-type pigments

Environ Sci Pollut Res Int. 2015 Oct;22(19):14478-88. doi: 10.1007/s11356-014-2985-6. Epub 2014 May 10.

Abstract

This study reports the concentrations and congener partners of polychlorinated biphenyls (PCBs) in commercially available paints. Polycyclic-type pigments containing dioxazine violet (pigment violet (PV) 23, PV37) and diketopyrrolopyrrole (PR254, PR255) were found to contain PCB-56, PCB-77, PCB-40, PCB-5, and PCB-12, and PCB-6, PCB-13, and PCB-15, respectively, as major congeners. Dioxazine violet is contaminated with by-products during synthesis from o-dichlorobenzene, which is used as a solvent during synthesis, and diketopyrrolopyrrole is contaminated with by-products during synthesis from p-chlorobenzonitrile. The concentration of PCBs in paint containing PV23 or PV37 was 0.050-29 mg/kg, and toxic equivalency (TEQ) values ranged 1.1-160 pg-TEQ/g. The concentration of PCBs in paint containing PR254 or PR255 was 0.0019-2.4 mg/kg. Naphthol AS is an azo-type pigment, and PCB-52 was detected in paint containing pigment red (PR) 9 with 2,5-dichloroaniline as its source. PCB-146, PCB-149, and PCB-153 were identified from paint containing PR112 produced from 2,4,5-trichloroaniline, as major congeners. These congeners have chlorine positions similar to aniline, indicating that these congeners are by-products obtained during the synthesis of pigments. The concentrations of PCBs in paints containing PR9 and PR112 were 0.0042-0.43 and 0.0044-3.8 mg/kg, respectively. The corresponding TEQ for PR112 was 0.0039-8.6 pg-TEQ/g.

Keywords: By-product; Congeners; Diketopyrrolopyrrole; Dioxazine violet; Naphthol AS; Pigments; Polychlorinated biphenyls.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coloring Agents / analysis*
  • Coloring Agents / chemistry
  • Environmental Pollutants / analysis*
  • Environmental Pollutants / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Limit of Detection
  • Molecular Structure
  • Naphthols / analysis*
  • Naphthols / chemistry
  • Paint / analysis*
  • Paint / standards
  • Polychlorinated Biphenyls / analysis*
  • Polychlorinated Biphenyls / chemistry
  • Polycyclic Aromatic Hydrocarbons / analysis*
  • Polycyclic Aromatic Hydrocarbons / chemistry

Substances

  • Coloring Agents
  • Environmental Pollutants
  • Naphthols
  • Polycyclic Aromatic Hydrocarbons
  • Polychlorinated Biphenyls
  • naphthol AS