Anal Bioanal Chem (2011) 400:1473–1491
DOI 10.1007/s00216-011-4822-9
ORIGINAL PAPER
The identification of synthetic organic pigments in modern
paints and modern paintings using pyrolysis-gas
chromatography–mass spectrometry
Joanna Russell & Brian W. Singer & Justin J. Perry &
Anne Bacon
Received: 10 January 2011 / Revised: 17 February 2011 / Accepted: 19 February 2011 / Published online: 17 March 2011
# Springer-Verlag 2011
Abstract A collection of more than 70 synthetic organic
pigments were analysed using pyrolysis-gas chromatogra-
phy–mass spectrometry (Py-GC–MS). We report on the
analysis of diketo-pyrrolo-pyrrole, isoindolinone and per-
ylene pigments which are classes not previously reported as
being analysed by this technique. We also report on a
number of azo pigments (2-naphthol, naphthol AS, arylide,
diarylide, benzimidazolone and disazo condensation pig-
ments) and phthalocyanine pigments, the Py-GC–MS
analysis of which has not been previously reported. The
members of each class were found to fragment in a
consistent way and the pyrolysis products are reported.
The technique was successfully applied to the analysis of
paints used by the artist Francis Bacon (1909–1992), to
simultaneously identify synthetic organic pigments and
synthetic binding media in two samples of paint taken
from Bacon’s studio and micro-samples taken from three of
his paintings and one painting attributed to him.
Keywords Py-GC–MS . Francis Bacon . Synthetic organic
pigment . Pyrolysis . Art . Mass spectrometry
Introduction
Over the twentieth century, increasing numbers of synthetic
organic pigments have been introduced and used in
J. Russell : B. W. Singer : A. Bacon
School of Arts and Social Sciences, Northumbria University,
Newcastle upon Tyne NE1 8ST, UK
B. W. Singer (*) : J. J. Perry
School of Life Sciences, Northumbria University,
Newcastle upon Tyne NE1 8ST, UK
e-mail: brian.singer@northumbria.ac.uk
industrial, household and artists’ paints. Conservators,
conservation scientists and art historians often wish to
identify the pigments present in a work of art; however, the
identification of modern organic pigments often presents
greater difficulties to the analyst compared with that of
inorganic artists’ pigments. The elemental analysis techni-
ques which have been proven so useful for the identifica-
tion of inorganic pigments are not so effective with organic
pigments, where the range of elements is small. In addition,
these pigments often have very small particle sizes,
meaning optical microscopy cannot be used effectively.
Many have high tinting strength, meaning a low concen-
tration of pigment is needed to colour the paint so little will
be present for analysis. The rapid development of new
organic pigments also complicates identification, as this has
led to a far greater range of different colorants being used in
artists’ paints than was the case with traditional pigments.
A wide variety of different methods have been described
for the analysis of synthetic organic pigments. The large
number of different structures means there is often a lack of
reference data to aid in identification, especially given the
spread of methods and research. A recent review described
the different classes of synthetic organic pigments before
going on to discuss methods for their identification [1].
Other reviews discuss the history, synthesis and uses of
specific classes of pigments, and also include information
on methods of identification. Such papers have been
published on the subject of azo pigments [2], phthalocya-
nine and quinacridone pigments [3] and arylide yellows [4].
Techniques which have been applied to the identification of
modern organic pigments include: Fourier transform infra-
red spectroscopy (FTIR) [5–8], Raman spectroscopy [8–
11], pyrolysis-gas chromatography–mass spectrometry (Py-
GC–MS) [7, 12–14], direct temperature mass spectrometry
[5, 7, 15, 16] and laser desorption (ionisation) mass
1474
spectrometry (LDMS) [16–19]. Whilst the use of high-
performance liquid chromatography (HPLC) for analysis of
organic pigments is well-established for natural organic
lakes [20–22], the use of HPLC is limited to those few
modern synthetic organic pigments which are soluble in
chromatographic solvents [23–25]. There is, hence, a real
need for methods which detect and identify pigments which
are not soluble in these solvents.
Py-GC–MS has been shown to be a useful technique for
the identification of synthetic paint binders [26–28] and has
also been applied to the identification of organic pigments [7,
12–14]. In most cases, the findings were applied to the
analysis of tubes of artists’ paints [7, 13, 14]. Application of
this technique to works of art has not been extensive though
the finding of the azo pigments: PR3, PR9, PY73, PY74 and
also PR170, by Curie point Py-GC–MS, in samples taken
variously from works by the artists: Patrick Caulfield, David
Hockney, Frank Stella and Gillian Ayres have been reported
[7]. Many subclasses of azo pigments have a common
skeletal structure, differing only in the substituents placed on
the phenyl rings, to impart variations in properties such as
colour, solubility and stability. The fragmentation of each
subclass therefore often follows a common pattern.
Here, we report the results of Py-GC–MS studies for a
greater range of synthetic organic pigments than previously
studied. We have expanded the list of pyrolysis data on azo
and disazo pigments significantly by 39 commonly used
examples. We have introduced new spectral data on two
phthalocyanine pigments and 13 pigments distributed over
three classes of pigments not previously mentioned with
regard to analytical pyrolysis.
We also report here how Py-GC–MS has been used for
the analysis of organic pigments in paints used by twentieth
century artist Francis Bacon (1909–1992) and also in
minute fragments of paint taken from his works as a proof
of the worth of this technique. Francis Bacon is an iconic
figure in twentieth century British art and there is much
interest surrounding his work. In particular, his recent
centenary has generated several high-profile exhibitions
and publications [29–31]. Samples from a selection of his
paintings have been analysed using our technique proving
that it is capable of analysing heterogeneous micro-samples
of modern paints. Additionally, Bacon’s studio is now
preserved at Dublin City Gallery, The Hugh Lane, and this
Fig. 1 Structure of 2-naphthol pigment (left), with fragments produced by pyrolysis (right)
J. Russell et al.
methodology has also been applied to artists’ materials
found there. Finally, we show that it is possible to use our
Py-GC–MS method to link materials from a studio to those
used in an artwork, and furthermore to identify the organic
pigments present. This work is part of a larger study,
currently in progress, examining Bacon’s materials in a
considerable number of his works spanning his career.
Experimental
Reference pigment samples
Samples of synthetic organic pigments were collected from
a number of different suppliers, as indicated below. Many
of these were obtained from the Tate Conservation Science
Department’s collection.
PR4, PR12, PR14, PR147, PR149, PR176, PR185, PR188,
PR208, PR214, PO36, PO62, PY3, PY73, PY81, PY97,
PY120, PY126, PY175 PBr25 and PBr41 kindly donated by
Clariant (Leeds, UK; HQ, Muttenz, Switzerland); PR1 by
Acros Organics (Geel, Belgium); PR2 by Heubach GmbH
(Langelsheim, Germany); PR3, PR5, PY1 by ICI Paints
(Slough, UK); PR6, PR178, PR221, PY13 by BASF (Ludwig-
shafen, Germany); PR8 by Hangzhou Yingshanhua Pigment
Chemical Co. Ltd. (Hangzhou, China); PR9, PR112, PR144,
PR166, PR170, PR175, PR179, PR254, PR255, PR264, PO61,
PO73, PY6, PY74, PY109, PY110, PY151, PY154, PY173,
PG7, PG36, PB15:6, PBr23 by Kremer Pigmente (Aichstetten,
Germany); PR17, PR22, PY12, PY14, PY17, PY65, PY83 by
Sun Chemical (Parsippany, USA); PR23, PO16, PY75, PY127
by Lansco Colors (Pearl River, USA); PR31 by Dainippon Ink
& Chemicals (Tokyo, Japan); PR123, PR190 by Bayer
Corporation (Pittsburgh, USA); PY2 by Sansui Pigment Ind.
Co. Ltd. (Osaka, Japan); PY55 by Albion Colours (Halifax,
UK); PY87 L by Cornelissen & Son (London, UK).
Pyrolysis-GC–MS of reference pigment samples
Pyrolysis-gas chromatography–mass spectrometry was car-
ried out on a Thermo Finnigan Focus GC Gas Chromato-
graph, with Thermo TR-5 15 m column, coupled to a DSQ II
mass spectrometer, fitted with a Pyrola 2000 platinum
filament pyrolyser.
The identification of synthetic organic pigments in modern paints 1475

Table 1 Products from Py-GC–MS of 2-naphthol pigments

CI Namea 2-Naphthol Intact molecule Product a Product b Other products

PR1 X1 =H, X2 =NO2 + (144, 115) +++ (143, 293, 115)

PR3 [13, 14, 22] X1 =NO2, X2 =CH3 + (144, 115) +++ (143, 275, 115, 307) + (65, 137, 91) ++ (152, 106, 77) Unidentified product
(260, 231, 202): ++
PR4 [13, 14] X1 =Cl, X2 =NO2 + (144, 115) +++ (143, 327, 115) + (111, 157, 75) +++ (172, 90, 63)
PR6 X1 =NO2, X2 =Cl ++ (111, 157, 75) +++ (172, 126, 99) Benzofurazan
(154, 124, 156): +
Unidentified product
(279, 254): ++
PO5 [13] X1 =NO2, X2 =NO2 ++ (144, 115) ++ (168, 76, 122) +++ (183, 153, 91) Unidentified product
(291, 189, 217): ++
a
References to Py-GC–MS analysis by other authors

A micro-sample of each pigment (approximately 0.5 mm
in diameter) was placed on the platinum filament of the
pyrolyser, which was then replaced in the pyrolysis
chamber. The pyrolysis chamber was heated to 175 °C,
and pyrolysis was carried out at 600 °C for 2 s, for the
majority of pigment samples. Pyrolysis was repeated at the
higher temperature of 800 °C for 2 s with a fresh sample for
pigments which did not give clear results at the lower
temperature. The inlet temperature of the GC was main-
tained at 250 °C. The gas flow rate was 1.5 ml/min with a
split flow of 75 ml/min and split ratio of 50. An initial
temperature of 40 °C was used, held for 2 min, then ramped
at 10 °C/min to 250 °C. This temperature was then held for
5 min further. The MS transfer line was held at 260 °C and
the ion source at 260 °C. Fragments were recognised using
a library of standards (US National Institute of Standards
and Technology, NIST MS Search 2.0).
Paint samples
studio have been catalogued in a database and given an
identification number, as indicated below.
Sample 1 was a flake of orange paint taken from a paint
tin labelled ‘Carson’s Sunway Colours Vinyl Matt, Yellow
Tint Bestobell Paints Ltd. Mitcham, Surrey’ (database no.
RM98F205:32). Sample 2 was a flake of orange paint from
a tin labelled ‘ICI Dulux Trade Vinyl Matt Emulsion The
Professional Choice Colour Dimensions Extra Deep Base’
(database no. RM98F131:49).
Paint samples from paintings included: an orange flake
from Francis Bacon, Figure with Cricket Pads, dating from
c.1982, owned by the Estate of Francis Bacon (sample 3); a
yellow flake from an unfinished, partially destroyed canvas,
Francis Bacon, Untitled: figure study with yellow back-
ground (database no. RM98F65), c.1971 (sample 4); dark
green paint flakes from Untitled: (Sketch for a Portrait), c.
1967, attributed to Francis Bacon, private owner (sample 5);
and Francis Bacon, Study for Figure VI, 1956–1957 owned
by The Hatton Gallery, University of Newcastle (sample 6).

Micro-samples were taken from two tins of orange paint Pyrolysis-GC–MS of paint samples
found in Francis Bacon’s studio and from four paintings.
The contents of Bacon’s studio have been preserved at An extremely small flake of each of the paints, approximate
Dublin City Gallery, The Hugh Lane. All items in the diameter is 0.2 mm, was placed, in turn, on the platinum

Fig. 2 Structure of naphthol AS pigment (left), with fragments produced by pyrolysis (right)
Table 2 Products from Py-GC–MS of naphthol AS pigments
1476

CI namea Substituents Products Other products

X1 X2 X3 Y1 Y2 Y3 a b c d

PR2 Cl H Cl H H H ++ (146, 148, 111) +++ (161, 163, 63) + (93, 66) + (119, 91) Dimer of a/b: +
PR5 [7, 14, 22] OCH3 H SO2N OCH3 OCH3 Cl +++ (171, 228, 107) +++ (122, 258, 186) + (172, 187, 144) + (213, 198, 170) (235, 270, 305)
(C2H5)2
PR8 CH3 H NO2 H Cl H ++ (65, 137, 91) ++ (152, 106, 77) +++ (127, 129, 65) ++ (153, 125, 155)
PR9 [7, 13] Cl H Cl OCH3 H H ++ (146, 148, 111) +++ (161, 163, 99 + (108, 123, 80) ++ (149, 134, 120) Dimer of a/b: +
PR12 [13] CH3 NO2 H CH3 H H ++ (91, 137, 65) ++ (152, 122, 77) +++ (106, 107, 77) ++ (133, 104, 78) (235, 270, 305)
PR14 NO2 Cl H CH3 H H ++ (111, 157, 75) ++ (172, 126, 174) +++ (106, 107, 77) +++ (133, 104, 78)
PR17 CH3 H NO2 CH3 H H ++ (65, 137, 91) +++ (152, 77, 79) ++ (106, 107, 77) +++ (133, 104, 78)
PR22 CH3 H NO2 H H H ++ (91, 137, 65) +++ (152, 106, 77) +++ (93, 66, 65) ++ (119, 91, 64)
PR23 OCH3 H NO2 H H NO2 + (153, 122, 92) +++ (168, 153, 122) ++ (65, 138, 92) + (164, 134, 90)
PR31 OCH3 H CONHC6H5 H H NO2 ++ (135, 227, 92) +++ (150, 242, 122) ++ (65, 138, 92) Aniline: + (93, 66, 65)
Isocyanatobenzene: +
(119, 91, 64)
PR112 [7, 13, 14] Cl Cl Cl CH3 H H ++ (182, 180, 145) +++ (195, 197, 124) + (106, 107, 77) ++ (104, 133, 105) d with 2-naphthol: +
(277, 107, 171)
Dimer of a/b: +
(340, 305, 368)
PR147 OCH3 H CONHC6H5 CH3 H Cl + (135, 227, 92) ++ (150, 242, 122) +++ (141, 106, 143) ++ (167, 138, 132)
PR170 [7, 13] H CONH2 H OC2H5 H H +++ (137, 108, 80) ++ (135, 163, 79) d with 2-naphthol: ++
(137, 171, 307)
PR188 [13] COOCH3 H CONHC6H3Cl2 OCH3 H H ++ (163, 288, 135) +++ (178, 303, 338) ++ (108, 123, 80) ++ (149, 106, 134) Dichlorobenzenamine
from substituent on
X ring: ++ (161,
163, 99)
a
References to Py-GC–MS analysis by other authors
J. Russell et al.
The identification of synthetic organic pigments in modern paints
Fig. 3 Structure of disazo condensation pigment (left), with fragments produced by pyrolysis (right)
ribbon filament and Py-GC–MS was carried out using the
method described above in order to yield information
regarding both the organic pigments and binders.
Scanning electron microscopy–energy dispersive X-ray
analysis
Similarly, small flakes of each of the samples to be analysed
for inorganic extenders were either mounted on carbon pads
on aluminium stubs or mounted in cross sections prepared
from fast-setting acrylic resins. Images and elemental analysis
of each sample was achieved by energy dispersive X-ray
Table 3 Products from Py-GC–MS of disazo condensation pigments
1477
(EDX) analysis using a FEI Quanta 200 environmental
scanning electron microscope coupled with an Oxford Instru-
ments INCA energy dispersive spectra analyser.
FTIR analysis
A micro-sample of each paint was placed onto the diamond
window of a Durascope diamond ATR attachment linked to
a Perkin Elmer 1000 Fourier transform infrared spectrom-
eter. Each sample was pressed down against the window
using a metal anvil and scanned 16 times. The background
scan was automatically subtracted.
1478 J. Russell et al.

Fig. 4 Structure of benzimidazo-

lone pigment (left), with
fragments produced by
pyrolysis (right)

Table 4 Products from Py-GC–MS of benzimidazolone (naphthol AS) pigments

CI name Substituents Products Other

X1 X2 X3 a b

PR175 COOCH3 H H ++ (105, 77, 136) +++ (119, 151, 92)

PR176 OCH3 H CONHC6H5 ++ (135, 227, 92) +++ (150, 242, 122) Aniline: +++ (93, 66)
Isocyanatobenzene: +++
(119, 91, 64)
PR185 OCH3 SO2NHCH3 CH3 ++ (120, 215, 121) +++ (135, 230, 136)
PR208 COOC4H9(n) H H ++ (105, 123, 77) +++ (119, 193, 137)
PBr25 Cl H Cl ++(146, 148, 111) +++(161, 163, 126) Dimer of a and b: +
(235, 270, 307)

Fig. 5 Structure of arylide pigment (left), with fragments produced by pyrolysis (right)
Table 5 Products from Py-GC–MS of arylide pigments

CI nameb Substituents Products Other

X1 X2 X3 Y1 Y2 Y3 Aca a b c D

PY1 NO2 CH3 H H H H + (43, 69, 54) + (91, ++ (93, 66) +++ (119, 91, 64) Benzofurazan from X ring: +
[13] 137, 65) (134, 77, 105)
PY2 NO2 Cl H CH3 CH3 H + +++ (overlap) Benzofurazan from X ring: +
(121, 120, 106) (147, 132, 118) (124, 154, 126)
PY3 NO2 Cl H Cl H H + +++ (127, 129, 65) ++ (153, 155, 125) Benzofurazan from X ring: +
[13] (124, 154, 126)
c and methyl group: +
(140, 141, 77)
PY6 NO2 Cl H H H H ++ + (172, 126, 63) ++ (93, 66) ++ (119, 91, 64) Benzofurazan from X ring: +
(124, 154, 156)
PY65 NO2 OCH3 H OCH3 H H ++ ++ (153, 107) + (168, 153, 122) +++ (108, 123, 80) ++ (149, 106, 120) Benzofurazan from X ring: ++
(150, 120, 77)
PY73 NO2 Cl H OCH3 H H + + (172, 126, 99) +++ (108, 80, 65) ++ (149, 106, 134) Benzofurazan from X ring: ++
[7, 14] (124, 154, 156)
The identification of synthetic organic pigments in modern paints

PY74 OCH3 NO2 H OCH3 H H ++ + (168, 153, 122) +++ (108, 123, 80) ++ (149, 134, 106) a and NCO group: +++
[13] (194, 164, 77)
PY75 NO2 Cl H H OC2H5 H ++ ++ (111, ++ (172, 126, 99) +++ (108, 109, 137) ++ (135, 163, 79) Benzofurazan from X ring: ++
157, 75) (154, 124, 156)
c and methyl group: ++
(122, 151, 94)
PY97 OCH3 SO2NHC6H5 OCH3 OCH3 Cl OCH3 ++ ++ (168, 308, 122) +++ (172, 187, 144) +++ (198, 213, 200) a and NCO group: ++
[13] (239, 334, 148)
a
Acetyl cyanide
b
References to Py-GC–MS analysis by other authors
1479
1480 J. Russell et al.

Fig. 6 Structure of benzimidazolone (arylide) pigment (left), with fragments produced by pyrolysis (right)

Table 6 Products from Py-GC–MS of benzimidazolone (arylide) pigments

CI name Substituents Products Other

X1 X2 X3 X4 Aca a b

PY120 H COOCH3 H COOCH3 + (43, 69, 54) ++ (163, 194, 135) +++ (209, 178, 150) a with isocyanate group: +
(204, 235, 161)
Unidentified product: ++
(234, 203, 276)
PY151 COOH H H H +++ Benzene: ++ (78, 77)
Aniline: ++ (93, 66, 65)
Isocyanatobenzene: +
(119, 64, 91)
2 unidentified products: +
(118, 160, 91) (160, 145, 118)
PY154 CF3 H H H + ++ (146, 145, 127) ++ (114, 161, 141) a with isocyanate group: +++
(187, 168, 145)
Unidentified product: +++
(186, 166, 228)
PY175 COOCH3 H H COOCH3 + + (163, 194, 135) ++ (209, 177, 150) a with isocyanate group: ++
(204, 235, 144)
Unidentified product: +++
(234, 203, 245)
PO36 NO2 H Cl H ++ ++ (111, 75, 157) +++ (172, 126, 99) Benzofurazan from X ring: ++
(124, 154, 126)
Unidentified product: +
(241, 170)
PO62 H H NO2 H ++ + (77, 123, 51) ++ (138, 65, 108) a with isocyanate group: +
(134, 164)
Unidentified product: +++
(163, 133, 205)
a
Acetyl cyanide

Fig. 7 Structure of diarylide

pigment showing fragmentation
pattern
Table 7 Products from Py-GC–MS of diarylide pigments

CI nameb Substituents Products c+NCO c+NH2 c+di-NCO c+NCO+NH2

X1 X2 X3 Y1 Y2 Aca a b c

PY12 H H H Cl H + (43, +++ (93, ++ (119, 91, 64) + (263, 265, 200) + (237, 239, 167) + (278, 280, 215)
69, 54) 66, 65)
PY13 CH3 CH3 H Cl H ++ +++ + (263, 265, 200) + (237, 239, 167)
[13] (overlap)
(121, (147, 118, 132)
120, 106)
PY14 CH3 H H Cl H +++ +++ (106, ++ (104, 133, 105) + (263, 265, 200) + (304, 306, 241) + (278, 280, 215)
107, 77)
PY17 OCH3 H H Cl H + +++ (108, ++ (149, 106, 134) + (263, 265, 200) + (237, 239, 167) + (278, 280, 215)
123, 80)
PY55 H CH3 H Cl H ++ +++ (106, ++ (133, 104, 132) (+) (222, 224, 152) + (263, 265, 200) + (278, 280, 215)
107, 77)
PY81 CH3 CH3 H Cl Cl ++ +++ (120, ++ (147, 132, 118) + (333, 331, 261) + (307, 305, 235) + (374, 372, 302) + (348, 346, 276)
121, 106)
PY83 OCH3 Cl OCH3 Cl H ++ +++ (172, ++ (198, 213, 200) + (304, 306, 241) + (278, 280, 215)
[13] 187, 144)
The identification of synthetic organic pigments in modern paints

PY87 OCH3 H OCH3 Cl H ++ +++ (138, ++ (164, 179, 136) + (263, 265, 200) + (237, 239, 167)
153, 110)
PY126 H H H Cl H ++ +++ (93, ++ (119, 91, 64) ++ (263, 265, 200) + (237, 239, 167) ++ (304, 306, 241) + (278, 280, 215)
H OCH3 H 66, 65)
PO16 H H H OCH3 H ++ +++ (93, +++ (119, 91, 64) + (255, 212) ++ (296, 253, 210)
66, 65)
a
Acetyl cyanide
b
References to Py-GC–MS analysis by other authors
1481
1482 J. Russell et al.

Fig. 8 Structure of diketo-

pyrrolo-pyrrole pigment (left),
with fragments produced by
pyrolysis (right)

Polarised light microscopy similar to a product observed to be produced from arylide

The samples were treated with dichloromethane to dissolve
or soften any binder present and crushed between glass
slides to separate the pigment particles and mounted on
microscope slides with Meltmount® 1.66 resin and exam-
ined with a James Swift MP3500A polarising microscope
using methodology developed by McCrone [32] and
modified by others [33, 34].
pigment PO1 [13]. Our results are summarised in Table 1.
In this and all following tables, the number of +’s show the
relative amount of each product, classified according to the
percentage abundance of the peak in relation to the most
intense peak in the pyrogram: +++=60–100% abundance, ++=
15–60%, +=less than 15% but at least three times the height of
the noise, (+)=product not always seen.
Naphthol AS pigments

Results of reference pigment analysis
Azo pigments
Azo pigments are prepared by the coupling of a diazo
compound with an electron rich aromatic compound. These
pigments can be grouped according to this coupling
component.
2-Naphthol pigments
Results obtained for the pyrolysis of this class follow the
pattern found previously for PR3, PR4 and PR5 [13], with
2-naphthol being produced, as well as the benzene and
aniline from the coupling component frequently appearing
(Fig. 1). We found that in some cases the pigment molecule
did not readily fragment, and a peak from the intact
molecule was the most abundant peak seen in the
chromatogram (PR1, PR3 and PR4). In addition, cyclisa-
tion appeared to occur in PR6, where a nitro group is
adjacent to the azo bond, giving a benzofurazan product,
These pigments, patented in 1911 [35], are prepared using
2-hydroxy-3-naphthoic acid N-arylamide as the coupling
component. They are more lightfast and solvent fast than
the 2-naphthol class, and some have an additional amide
group on the diazo component. Many of these pigments,
including PR112, PR146, PR170 and PR188, have been
used in artists’ paints, for example PR188 was used in
‘Winsor Red’ oil paint until at least 1997 [36].
Under the conditions detailed above, the 2-naphthol product,
reported elsewhere for a number of pigments of this type [13],
was not normally seen, or only as a very minor product. We
confirmed that the pigments of this type generally produced
up to four products, two products (a substituted benzene and
aniline) from the diazo component, and the aniline and
occasionally isocyanate from the coupling component in
varying proportions (Fig. 2). Additional products were
identified in some cases, with a commonly observed m/z
value corresponding to the dimerisation of two fragments.
Those pigments with an additional phenyl ring often broke
down to give further products from the diazo functionalized
component. The results are summarised in Table 2.

Table 8 Products from Py-GC–MS of diketo-pyrrolo-pyrrole pigments

CI name X Product a Product b Other products

PR254 –Cl ++ (112, 114, 77) +++ (139, 137, 102) ? (mw-43): ++ (313, 315, 250)
PR255 –H ++ (78, 77) +++ (103, 76, 50) ? (mw-43): ++ (245, 216, 189)
PR264 –C6H5 ++ (154, 153, 76) +++ (179, 178, 151) Benzene: ++ (78, 77)
PO73 –C(CH3)3 ++ (119, 91, 134) +++ (133, 148, 105)
The identification of synthetic organic pigments in modern paints 1483

Fig. 9 Structure of phthalocya-

nine pigment (left), with frag-
ment produced by pyrolysis
(right)

Disazo condensation pigments diisocyanate or amine-isocyanate substituted Y ring. The

These pigments, in use since the 1950s [35], have a similar
structure to the naphthol AS pigments, but here two
naphthol-azo structures are linked by a central benzene
ring. As with naphthol AS pigments, pyrolysis produces
substituted benzenes and benzenamines from the X-
substituted rings (Fig. 3). In a few cases, products were
also detected from the central aromatic group—a diamine,
results are summarised in Table 3.
PR144, PR166 and PR214 are structurally very similar,
differing only in the substituents on the central Y ring, so
give identical a and b products. Therefore these cannot be
distinguished using Py-GC–MS alone, as the products from
the Y ring were very minor and not seen in all cases. PBr41
also gives similar a and b products, differing only in the
positions of the substituents. Different isomers such as

Fig. 10 Pyrogram of PG7

phthalo green, Kremer. Pyroly-
sis temperature of 800 °C; insert
shows mass spectrum of peak 3.
1, Chlorobenzene; 2, C6(CN)
Cl5; and 3, C6(CN)2Cl4)
1484 J. Russell et al.

Fig. 11 Pyrogram of PG36

Phthalo green, yellowish,
Kremer. Pyrolysis temperature
of 800°C. 1, Chlorobenzene; 2,
bromobenzene; 3,
C6(CN)2Br2Cl2; 4,
C6(CN)2Br3Cl; and 5,
C6(CN)2Br4)

these were not always unambiguously identified by MS Arylide pigments

using the NIST library and differed little in retention times.
Benzimidazolone (naphthol AS) pigments
Benzimidazolone pigments are another similar class devel-
oped in the 1960s, using 5-(2-hydroxy-3-naphthoyl)-amino-
benzimidazolone as the coupling component. An example
used in artists’ paints is PR176, found in Royal Talens
‘Carmine’ Oil colour [37].
The benzimidazolone pigments fragment in a similar
way to the naphthol AS pigments, but only products from
the diazo end of the molecule were identified. These
consistently gave the two products shown in Fig. 4. The
results are summarised in Table 4.
The first synthetic organic yellow pigments were intro-
duced to the market in 1910 [4, 35], and were azo pigments
using acetoaceticarylides as the coupling component. These
fragment in a similar way to the naphthol AS pigments,
producing amine and isocyanate products from the coupling
component and in some cases amines from the diazo
component, see Fig. 5 and Table 5. In addition, these
pigments produce acetyl cyanide, which emerges with a
short retention time in the pyrogram. An apparent cyclisa-
tion to form a benzofurazan product was previously
reported [13] for PO1 and a similar benzofurazan product
was identified here from pigments having a nitro group in
the X1 position.

Table 9 Products from Py-GC–MS of phthalocyanine pigments

CI namea X Product a Other products

PB15:6 [13] H + (128, 101, 75)

PG7 14–15 Cl +++ (4 Cl) (266, 264, 229) Product a with 1 CN group substituted
by Cl : + (275, 277, 240)
PG36 4–9 Br, 8–2 Cl +++ (4 Br) (444, 442, 284) Chlorobenzene ++ (112, 114, 77)
+++ (3 Br, 1 Cl) (400, 398, 240) Bromobenzene ++ (156, 158, 77)
++ (2 Br, 2 Cl) (354, 356, 276)
a
References to Py-GC–MS analysis by other authors
The identification of synthetic organic pigments in modern paints
Fig. 12 Structure of isoindolinone pigment (left), with fragments produced by pyrolysis (right)
Benzimidazolone (arylide) pigments
Benzimidazolone pigments were introduced in 1975 [35]
and are based on the arylide yellow structure, using the
coupling component 5-acetoacetylamino-benzimidazolone.
As with the benzimidazolone (naphthol AS) pigments,
only products from the diazo moeity of the molecule were
identified (Fig. 6). These results are summarised in Table 6.
Diarylide pigments
On pyrolysis of diarylide pigments (introduced in the 1930s
[35]), the fragmentation of the coupling component is
similar to that of the arylide yellows and most also produce
a series of minor biphenyl products from the central diazo
component, (Fig. 7; Table 7).
Diketo-pyrrolo-pyrrole pigments
Diketo-pyrrolo-pyrrole pigments are the most recently devel-
oped class of pigments to have importance in artists’ materials.
The first pigments were introduced in the early 1980s [38].
Table 10 Products from Py-GC–MS of isoindolinone pigments
1485
Two examples, PR254 and R255, are now used in Winsor &
Newton oil colours, replacing the PR188 used earlier.
Py-GC–MS of diketo-pyrrolo-pyrrole pigments have not
previously been reported. We found that pyrolysis products
could only be identified from these pigments if the
pyrolysis was carried out at the higher temperature of
800 °C. These pigments produced substituted benzenes and
benzonitriles (Fig. 8; Table 8).
Phthalocyanine pigments
Phthalocyanine pigments are some of the most successful
organic pigments, and some of the first to be widely
introduced to artists’ paints. Copper phthalocyanine blue,
PB15, was first introduced to the market in 1935, and
chlorinated copper phthalocyanine green, PG7 was first
prepared in 1938 [3]. These pigments have been used in
artists’ paints since before 1940 [39] and continue in use
today. Copper polybromochloro phthalocyanine green
PG36, a yellower shade of green, was introduced in 1959.
Py-GC–MS of phthalocyanine pigments gave identifi-
able signature compounds when pyrolysis was carried out
1486
O O
a a
X N N X
O O
Fig. 13 Structure of perylene pigment
at 800 °C. In all cases, a product is seen from the benzene
ring plus two nitrile groups (Fig. 9). In PB15, this was the
only identified product, but gave only a small peak. The
halogenated phthalocyanines PG7 and PG36 gave much
more intense peaks for the equivalent product (Figs. 10 and
11). In addition the variation in substitution pattern for
PG36 leads to a series of products with different numbers
of chlorine and bromine atoms (Table 9).
Isoindolinone pigments
The isoindolinone pigments were introduced in the mid-1960s
[35]. They all include the isoindoline ring, but different
members of the group show some variation from the generic
structure shown (Fig. 12), mainly in the structure of the
central linking ring(s). Pyrolysis gives X-substituted ben-
zenes, sometimes including a nitrile group, from the
isoindolinone groups, and in some cases also benzenes from
the central aromatic group (Fig. 12; Table 10).
Table 11 Products from Py-GC–MS of perylene pigments
J. Russell et al.
Perylene pigments
Perylene compounds first found use as pigments in 1950
and range in colour from red through brown to black [35].
Perylene pigments again required a pyrolysis temperature
of 800 °C to give identifiable signature compounds.
Products result only from the outer X substituents, not
from the central polycyclic structure (Fig. 13). PR179,
where X is a methyl group, did not give any identifiable
pyrolysis products (Table 11).
Discussion of reference pigment analysis
The fragmentation of the reference pigments generally
followed a predictable pattern among members of each
group. In the majority of cases, at least two main
signature compounds were identified, which could be
used to identify the pigment. However, some pyrolysis
products are produced from a large number of pigments,
for example aniline and isocyanatobenzene were found
as a pair of products in at least 15 red, orange and
yellow pigments tested. Often, these were the most
abundant products; therefore in such cases, it becomes
important to identify some of the lesser products to
narrow the field. A few pigments cannot be easily
distinguished by this method, for example PR144,
PR166 and PR214 which all gave the same principal
products.
The identification of synthetic organic pigments in modern paints 1487

Table 12 Products from Py-GC–

Product Pigment
MS of sample 1: Carson’s
orange paint
Yellow pigment extracted with dichloromethane Isocyanatobenzene PY1
Aniline PY1
Chloroaniline PY3
1-Chloro-4-isocyanato benzene PY3
5-Methylbenzofurazan PY1
1-Methyl-3-nitrobenzene PY1
4-Methyl-2-nitrobenzenamine PY1
Red–orange residue Dichlorobenzene PR144/166/214
Dichlorobenzamine PR144/166/214

It has been reported that while Py-GC–MS can successfully
detect azo pigments, the largest class of organic pigments used
in modern paints, it is far less successful in identifying
phthalocyanines, quinacridones, benzimidazolones, dioxa-
zines, or any other class of organic pigment [15]. For this,
and other reasons, other techniques such as LDMS have been
favoured recently for analysis of modern organic pigments in
paints and from paintings [15–19]. We have found though,
that for the diketo-pyrrolo-pyrrole, perylene and phthalocya-
nine pigments, the use of a platinum ribbon filament and a
pyrolysis temperature, of 800 °C, enabled the identification of
signature pyrolysis products. For azo and isoindolinone
pigments both pyrolysis temperatures (600 and 800 °C) gave
similar results, with the same pyrolysis products being
identified, though often in different proportions. The higher
temperature tended to produce a greater proportion of higher
molecular weight compounds. We were unsuccessful in
recording useful data for quinacridones and some other
polycyclic pigments at any temperature. Rehorek and Plum
[40] have also discovered the necessity of varying the
pyrolysis temperature between 500 and 800 °C for optimising
the production of pyrolysis products from different azo dyes.
Results of analysis of examples of Francis Bacon’s
paints and works
Analysis of studio paints using Py-GC–MS
An orange paint flake from a paint tin labelled ‘Carson’s
Sunway Colours Vinyl Matt, Yellow Tint Bestobell Paints
Ltd. Mitcham, Surrey’ (sample 1) was subjected to
pyrolysis at 600 °C. The pyrogram showed several products
which appear to be from more than one organic pigment.
Polarised light microscopy of the sample revealed that the
paint contained a mixture of yellow and orange–red
pigments. It was found that a yellow pigment could be
extracted from the sample using dichloromethane, leaving
the red/orange colour behind. In this way, the pigments
were separated to be analysed individually by pyrolysis
(Table 12).
Py-GC–MS showed that PY1was the principal yellow
pigment, with a smaller amount of PY3 mixed in.
Comparative FTIR confirmed the presence of PY1. In the
orange residue, the pyrogram showed two peaks which can
be matched with the principal products from either PR144,
PR166 or PR214. These pigments are structurally very
similar and are not distinguished, using pyrolysis as their
signature compounds are identical.
An orange paint flake from a tin labelled ‘ICI Dulux
Trade Vinyl Matt Emulsion the Professional Choice Colour
Dimensions Extra Deep Base’ (sample 2) was analysed.
The Dulux paint was also found to have more than one
organic pigment. Again, a yellow pigment was extracted
using dichloromethane. And identified by pyrolysis at 600 °
C as PY74 (Table 13). This result was confirmed using
comparative FTIR. The orange residue was also analysed
using Py-GC–MS, but no products from an organic pigment
were identified (Table 13), as the remaining red/orange
pigment did not readily pyrolyse. Also signals from the
kaolin and chalk extenders in the residue prevented the
interpretation of any signals pertaining to the remaining red

Table 13 Products from Py-

GC–MS of Sample 2: Dulux Product Pigment
orange paint
Yellow pigment extracted with dichloromethane 2-Methoxybenzenamine PY74
1-Isocyanato-2-methoxybenzene PY74
1-Isocyanato-2-methoxy-4-nitrobenzene PY74
2-Methoxy-4-nitrobenzenamine PY74
Red–orange residue No clear product from pigment pyrolysis ?
1488 J. Russell et al.

Table 14 Products from Py-GC–MS of sample 3: orange paint from when analyzed for compounds yielding fragments of m/z=
Figure with Cricket Pads
265.5–266.5 Da (Fig. 15), thus again, suggestive of the
Product Pigment presence of PG7.
The Py-GC–MS analysis also allowed identification of
Isocyanatobenzene PY1 the binders, as well as the pigments. Also, the presence of
Aniline PY1 palmitic and stearic acids in the chromatogram of the green
Dichlorobenzene PR144/166/214 paint from Untitled: (Sketch for a Portrait), c.1967
Chloroaniline PY3 (Fig. 14) indicates an oil binder which was confirmed
1-Chloro-4-isocyanato benzene PY3 using a previously reported GC–MS method [41]. Samples
5-Methylbenzofurazan PY1 were also analysed using polarised light microscopy, SEM–
3,4-Dichlorobenzenamine PR144/166/214 EDX and FTIR to identify all components of the paint. For
4-Methyl-2-nitrobenzenamine PY1 example, EDX analysis confirmed the presence of copper
and chlorine in samples 5 and 6 and also indicated barium
and sulphur from the inorganic extenders in these samples.
The results are summarised in Table 16.

or orange pigment in the FTIR spectrum of the residue and

hence this material remains unidentified.
Analysis of samples from paintings
The orange paint from the background of Figure with
Cricket Pads, c.1982 by Francis Bacon (sample 3) also
appeared to contain more than one organic pigment. Py-
GC–MS identified PY1 mixed with PY3, as well as two
pyrolysis products indicative of a sample from PR144,
PR166 or PR214 (Table 14). This indicated a close
similarity to the constituents of sample 1.
A yellow paint from the background of the unfinished,
slashed canvas, Untitled: figure study with yellow back-
ground, c.1971 (sample 4) yielded pyrolysis products
(Table 15) from the pigment PY1, together with those from
a PVA binder.
The green paint from Untitled: (Sketch for a Portrait),
c1967, a partially destroyed work, attributed to Francis
Bacon (sample 5), on pyrolysis yielded tetrachloro-1,2-
dicyanobenzene and also chlorobenzene (Fig. 14) which are
both found after pyrolysis of PG7 (Fig. 10). A similar green
paint, giving a similar result for FTIR and EDX analysis, on
a known work by Bacon, Study for Figure VI, 1956-7
(sample 6) was subjected to Py-GC–MS. The pyrogram
showed the presence of tetrachloro-1,2-dicyanobenzene
Table 15 Products from Py-GC–MS of sample 4: yellow paint from
Untitled: figure study with yellow background
Product Pigment
Discussion of analysis of examples of Francis Bacon’s
paints and works
The orange paint from Figure with Cricket Pads (sample 3)
was found to have the same components as the tin of
Carson’s orange paint from the studio (sample 1), with the
same binder, extenders and pigments. It therefore seems
likely that the Carson’s orange paint is the same as that used
on the painting. Two further tins of orange paint with the
same labelling have been found in the studio, indicating that
the same paint may have been used on several occasions. A
bright orange of this type is used in the backgrounds of a
number of Bacon’s paintings from the 1970s and 1980s. This
methodology was able to show the presence of a signature
pyrolysis compound for PG7 (tetrachloro-1,2-dicyanoben-
zene), even when the sample size was extremely small. This
green colour has been widely used in a number of works by
Bacon, was given the nickname ‘Belcher’s green’ by the
artist [42] and was demonstrated here to be present in a work
attributed to Bacon, thus demonstrating the contribution that
chemical microanalysis may make towards authentication of
artworks.
Learner reports that Py-GC–MS can be useful in the
analysis of micro-samples from paintings, simultaneously
revealing information regarding both polymeric binders and
main classes of azo pigments [7], and we have demonstrat-
ed that Py-GC–MS using a ribbon filament pyrolyser can
extend this utility to include phthalocyanine pigments and
potentially diketo-pyrrolo-pyrrole, perylene, benzimidazo-
lone and isoindolinone pigments

Isocyanatobenzene PY1
Aniline PY1 Conclusions
5-Methylbenzofurazan PY1
4-Methyl-2-nitrobenzenamine PY1
Pyrolysis-GC–MS has previously been shown to be a useful
technique for the identification of synthetic organic pigments
The identification of synthetic organic pigments in modern paints 1489

Fig. 14 Pyrogram of green

paint from Untitled: Portrait of
man in green clothing, attributed
to Francis Bacon; pyrolysis
temperature of 800 °C; insert
shows mass spectrum of peak 2.
1, Chlorobenzene; 2,
C6(CN)2Cl4; 3, palmitic acid
(from the oil binder); and 4,
stearic acid (from the oil binder)

Fig. 15 Pyrogram of green

paint from Study for Fig. 6, by
Francis Bacon; pyrolysis tem-
perature of 800 °C. Display
mass range: m/z 265.5 to 266.5;
insert shows mass spectrum of
peak 1. 1, C6(CN)2Cl4)
1490
Table 16 Results of analysis of paint samples
Sample Bindera
1 Carson’s Sunway Colours Vinyl Matt, Yellow Tint PVA
2 ICI Dulux Trade Vinyl Matt Emulsion Acrylic copolymer
(MMA-2-EHA)
3 Orange paint from Figure with Cricket Pad, c1982, PVA
Francis Bacon
4 Yellow paint from Untitled:(figure study with PVA
yellow background), c1971, Francis Bacon
5 Green paint from Untitled: (Sketch for a Portrait), Oil
c 1967, attributed to Francis Bacon
6 Green paint from Study for Portrait VI, 1956–7, Oil
Francis Bacon
a
Py-GC–MS and FTIR
b
FTIR, PLM and SEM–EDX
and the usefulness of the technique has been expanded here.
Pyrolysis products are reported from several pigment groups
not previously studied, widening its field of application to
diketo-pyrrolo-pyrrole (including PR254, PR255, PR264 and
PO73), perylene (including PR123, PR149, PR178, PR179
and PR190) and isoindolinone pigments (including PY109,
PY110, PY173 and PO61). Products from the pyrolysis of a
greater range of azo pigments (including PR1, PR2, PR6,
PR8, PR14, PR17, PR22, PR23, PR31, PR147, PR175,
PR176, PR185, PR208, PBr25, PY2, PY6, PY65, PY75,
PY120, PY151, PY154, PY175, PO36 and PO62), disazo
pigments (including PR144, PR166, PR214, PR221, PBr23,
PBr41, PY12, PY14, PY17, PY55, PY81, PY87, PY126 and
PO16) and a greater range of phthalocyanine pigments
(including PG7 and PG36) are also reported, which should
provide useful reference data. Many fragments are produced
by more than one pigment, but the combination of pyrolysis
products will allow most pigments to be identified uniquely.
It is wise to recognise the possible limitations of Py-GC–
MS for the identification of pigments in modern works of art.
The very large number of pigments that may have been used
in artists’ and household paints complicates identification. In
paint samples, only the most abundant product(s) might be
picked up in the analysis, due to the low concentration of
pigment in comparison to binding media and extenders,
meaning that there may be several possible candidates. In this
case, the use of another complimentary technique such as
FTIR can be invaluable, and this technique helped to confirm
the findings in the Bacon case studies reported above. The low
pigment concentration is a greater problem for smaller
samples [43]. Mixtures of pigments can also complicate
identification, but we have shown that physical separation of
pigments using solvent extraction can aid this process.
J. Russell et al.
Inorganic pigments/extendersb Organic pigmentsa
Chalk PY1
Kaolin PY3
Titanium white PR144/PR166
Chalk PY74
Kaolin
Chalk PY1
Kaolin PY3
Titanium white PR144/PR166
Titanium white Kaolin PY1
Barium sulphate PG7
Barium sulphate PG7
We have confirmed that Py-GC–MS-based methodol-
ogy like that outlined above is applicable to the analysis
of the micro-samples that may be removed ethically from
valuable works of art. Furthermore, we have demonstrat-
ed that the green phthalocyanine pigment PG7 can be
pyrolyzed and its signature fragments recognised in
micro-samples taken from works of art. We have
demonstrated that pigments found on works of art can
be matched with pigments in paints from the artist’s
studio, or other known works by the artist, using this
technique, which could, therefore, have potential use in
the authentication of art. The Py-GC–MS technique
described should be seen to be complementary to
established LDMS methodology [44], for use in forensic
studies where paint examination is required.
Acknowledgements The authors would like to thank the Estate of
Francis Bacon for funding this project (and permission to sample the
latter’s paintings) and also Dublin City Gallery (The Hugh Lane) and
The Hatton Gallery (Newcastle University, Newcastle). We would like
to thank the Tate, London and Clariant for the supply of pigment
samples as well as Dr. Clive Foster (FujiFilm UK, Ltd.) for helpful
comments.
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