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Fading of Alizarin and Related Artists' Pigments by Atmospheric Ozone: Reaction Products and Mechanisms

Grosjean, Daniel and Whitmore, Paul M. and De Moor, C. Pamela and Cass, Glen R. and Druzik, James R. (1987) Fading of Alizarin and Related Artists' Pigments by Atmospheric Ozone: Reaction Products and Mechanisms. Environmental Science and Technology, 21 (7). pp. 635-643. ISSN 0013-936X. http://resolver.caltech.edu/CaltechAUTHORS:20140915-142330511

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Abstract

The colorants alizarin and Alizarin Crimson (a calcium- aluminum lake pigment) and their simple structural homologue anthraquinone were deposited on silica gel, cellulose, and Teflon substrates and exposed in the dark to ozone in purified air (~0.4 ppm O_3 for 95 days and ~10 ppm O_3 for 18-80 h). Exposed and control samples were analyzed by mass spectrometry. Alizarin Crimson reacted with ozone on all substrates, yielding phthalic acid {major), benzoic acid (minor), and other minor and unidentified products. Anthraquinone did not react with ozone irrespective of conditions. Alizarin did not react on Teflon or cellulose but reacted on silica gel to yield phthalic acid (major) and other products. A chemical mechanism responsible for the fading of these alizarin-related colorants by ozone is suggested that is consistent with the products distribution, the observed reactivity sequence, and the observed substrate-specific effects. The possible application of this work to predicting the ozone fastness of other alizarin-related pigments is discussed briefly.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://pubs.acs.org/doi/abs/10.1021/es00161a003PublisherArticle
http://dx.doi.org/10.1021/es00161a003DOIArticle
Additional Information:© 1987 American Chemical Society. Received for review June 23,1986. Accepted January 28,1987. Publication Date: July 1987. This work was supported by a contract with the Getty Conservation Institute, Marina del Rey, CA. Frank D. Preusser of the Getty Conservation Institute provided technical input throughout the course of this study. Scott Boyce of the California Institute of Technology carried out the solvent extractions. The mass spectroscopy analyses were performed by Dilip K. Sensharma and John Wells, Department of Chemistry, University of California, Los Angeles, CA. The XRF analysis of the Alizarin Crimson sample was performed at NEA, Inc., Portland, OR. Christina Conti prepared the several versions of the manuscript, and Nancy Tomer drafted the figures.
Group:Environmental Quality Laboratory
Funders:
Funding AgencyGrant Number
Getty Conservation Institute UNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Environmental Quality LaboratoryA-196
Record Number:CaltechAUTHORS:20140915-142330511
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140915-142330511
Official Citation:Fading of alizarin and related artists' pigments by atmospheric ozone: reaction products and mechanisms Daniel Grosjean, Paul M. Whitmore, C. Pamela. De Moor, Glen R. Cass, and James R. Druzik Environmental Science & Technology 1987 21 (7), 635-643
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:49723
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Sep 2014 21:47
Last Modified:15 Sep 2014 21:47

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