Contact Dermatitis Lehner Are A Source of Problematic Substances Such As Dibutyl Phthalate

Contact Dermatitis • Original Article COD
Contact Dermatitis
Black tattoo inks are a source of problematic substances

such as dibutyl phthalate
Karin Lehner1,2 , Francesco Santarelli1 , Rudolf Vasold2 , Burkhard König2 , Michael Landthaler1
and Wolfgang Bäumler1
1 Department of Dermatology, University of Regensburg, 93042 Regensburg, Germany and 2 Department of Organic Chemistry, University of Regensburg,
93042 Regensburg, Germany
doi:10.1111/j.1600-0536.2011.01947.x
Summary Background. Tattooing has recently become increasingly popular. Using tiny needles,
tattooists place the tattoo ink in the dermis along with numerous unknown ingredients.
Most tattoos consist of black inks, which are predominantly composed of soot products
(carbon black with polycyclic aromatic hydrocarbons).
Objectives. Black tattoos cause skin problems, including allergic reactions, but the
responsible substance frequently remains unknown.
Material/methods. We applied gas chromatograph–mass spectrometry analysis to
search for hazardous compounds in 14 different commercially available black tattoo ink
samples.
Results. The analysis revealed that all inks contained the softener substance dibutyl
phthalate (0.12–691.2 μg/g). Some of the inks contained hexachloro-1,3-butadiene
(0.08–4.52 μg/g), metheneamine (0.08–21.64 μg/g), dibenzofuran (0.02–1.62 μg/g),
benzophenone (0.26–556.66 μg/g), and 9-fluorenone (0.04–3.04 μg/g).
Conclusion. The sensitizing agent dibutyl phthalate acts directly on keratinocytes
and can drive Th2 responses following skin exposure via induction of thymic stromal
lymphopoietin gene expression. Hexachloro-1,3-butadiene is genotoxic in vitro and 9-
fluorenone is cytotoxic, generating reactive oxygen species under light exposure. The
substances found in the inks might be partially responsible for adverse skin reactions to
tattoos.
Key words: black inks; dibenzofuran; gas chromatography; health problems;

phthalate; tattoo.
In recent years, tattoos have become very popular and permanent make-up. The list of ingredients on black
worldwide, and millions of people have mainly black- tattoo inks is usually missing or incomplete. Frequently,
coloured tattoos. Despite the increasing number of tat- there is no information on packaging, such as expiration
tooed individuals, there are currently few requirements, date, conditions of use, warnings, or the guarantee of
little legislation and few criteria for the safety of tattoos sterility of the contents. Risk assessment should be an
essential part of protecting human health, and this also
applies to tattoos.
Correspondence: Professor Wolfgang Bäumler, Department of Dermatology, Tattooing is a practice whereby a pigment suspension
University of Regensburg, 93042 Regensburg, Germany. Tel: +49-941- is deposited in the dermis by intradermal injection of
944-9607; Fax: +49-941-944-9647. E-mail: [email protected]
the inks with tiny solid needles. As black inks are pro-
regensburg.de
duced by imperfect combustion, they consist mainly of
Conflicts of interest: The authors have declared no conflicts. Funding: The carbon black. It is therefore unsurprising that such black
work was funded by the Deutsche Forschungsgemeinschaft (DFG).
inks contain high amounts of polycyclic aromatic hydro-
Accepted for publication 3 May 2011 carbons (PAHs) and phenol. As previously reported, we
© 2011 John Wiley & Sons A/S • Contact Dermatitis, 65, 231–238 231
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BLACK TATTOO INKS • LEHNER ET AL.
established an extraction procedure for the determination H). As an internal standard (ISTD), hexamethylbenzene
and quantification of 20 different PAHs in various com- was obtained from Sigma Aldrich and prepared as a
mercially available black tattoo suspensions by using 0.2 mg/ml stock solution in acetonitrile.
liquid chromatography detection (1).
Tattoo inks are not distributed by pharmaceutical com- Extraction procedure and sample preparation
panies, and in many countries regulation regarding such As previously reported with PAH extraction, we used
inks is still lacking. In Germany, the first tattoo regulation ultrasonic treatment of a defined amount of black ink
appeared in 2009; it prohibits the use of azo pigments that suspension with benzene/acetone and centrifugation (1).
can be cleaved to hazardous aromatic amines. With black The procedure was performed in triplicate. The residual
tattoo inks, PAHs and other substances can be introduced compounds were resolved in 1 ml of acetonitrile, filtered
into the skin, and this might be responsible for the health with a polytetrafluoroethylene filter (CHROMAFIL®,
problems associated with tattoos (2). O-20/15, organic, pore size 0.2 μm; Machery-Nagel,
Therefore, we investigated black tattoo inks again Düren, Germany), and analysed with the ISTD method,
by using gas chromatography (GC)–mass spectrometry using GC–MS analysis. The selected compounds were
(MS) analysis, and searched for other substances in 14 previously detected in a qualitative GC–MS run of the ink
commercially available tattoo inks that might have the extract samples.
potential to be harmful for humans.
Chromatography analysis
Materials and Methods Analysis was performed with an Agilent Technologies

GC/MS System, consisting of 7890 A GC and 5975C Inert
Materials
XL EI/CI MSD with a CTC Pal Autosampler. Method set-
tings: injection volume, 1.00 μl; He flow, 1 ml/min. Oven
Fourteen commercially available black tattoo inks were program: 40 ◦ C for 3 min, then 15 ◦ C/min to 280 ◦ C for
purchased from different tattoo suppliers in Europe, 5 min, then 25 ◦ C/min to 300 ◦ C for 5 min with splitless
the United States, and Asia: Tribal Black (Body Cult mode (1 min); injector temperature 250 ◦ C. Transfeline
Tattoo Supply); Schwarz (Rotring); Black Magic (Faber); temperature: 300 ◦ C. The column used was an Agi-
Liner-Black (Infernal Colour); Diabolo Genesis (Deep lent HP-5MS (30 m × 250 μm × 0.25 μm). Qualification
Colours!); Pitch Black (Scream Ink); Tattoo Outlining and quantification were performed with an Agilent MSD
Ink (Kuro Sumi); True Black (Intenze Prod); National ChemStation E.02.00.493 and NIST Mass Spectral Search
Pelikan (Pelikan); Sailor Jerry (Deep Colours!); Ink Black Program for the NIST/EPA/NIH Mass Spectral Library
(Nova Ink); New Intense Black (Lynx); Black Liner Ink Version 2.0f, 23 July 2008. For Matchfactor NIST > 900,
(Spaulding); and Calcutta Black (Spaulding). a substance was regarded as clearly identified.
Standard substances, including hexachloro-1,3- The concentrations of the investigated substances were
butadiene (HCBD), dibenzofuran (DBF), hexamethylene- quantified with the ISTD method. For each compound (i),
tetramine (HET), 9-fluorenone (9F), benzophenone (BP) the calibration factor (CFi ) was determined in a calibration
and dibutyl phthalate (DBP), were detected by MS run (single-level calibration). The respective concentra-
(GC – MS) and obtained from Sigma Aldrich (Steinheim, tion of the ISTD was chosen to be in the range of the
Germany) as analytical pure standards. The references concentration of the substances.
with a 1.0 mg/ml stock solution in acetonitrile were
fTr mK · aTr
k
combined to obtain a 0.88 mg/ml calibration solution. CFi = = Ki (1)
The purity of each standard was approximately 98% as fi mTr · aiK
reported by the manufacturer.
Where fTr is the response factor of the ISTD, mKi is the
The solvents used for extraction of PAHs, including
mass of compound i in solution k, mKTr and the mass of the
benzene and acetone, were of reagent grade, and were k
ISTD in solution k. aTr is the area of ISTD in solution k,
obtained from Merck (Darmstadt, Germany). Acetonitrile K
and ai is the area of compound i in solution k.
as a solvent for GC analysis was of gradient-grade quality
for liquid chromatography (LiChroSolv, Darmstadt, Ger-
many). Millipore water as a solvent for HPLC analysis was Results
freshly produced with a Milli-Q Advantage A10 system
(TOC 5 ppb; Millipore, Molsheim, France). All substances Quantitatively determined ingredients
were dissolved in 1 ml of acetonitrile and subjected to Stock solutions (0.88 mg/ml) of each substance (HCBD,
ultrasonic treatment (Bandelin Sonorex Super RK 103 HET, DBF, DBP, 9F, and BP), which were qualitatively
232 © 2011 John Wiley & Sons A/S • Contact Dermatitis, 65, 231–238
Table 2. Chemical structures of identified and quantified ingredients

in black tattoo inks
Fig. 1. Chromatography of the quantified substances. The

retention times of the substances were 10.444 min
(hexachloro-1,3-butadiene), 10.519 min (metheneamine),
13.229 min (dibenzofuran), 14.101 min (benzophenone),
14.982 min (9-fluorenone), and 16.349 min (dibutyl phthalate),
and the retention time of the internal standard
(hexamethylbenzene) was 12.642 min.
detected in a first GC run, were measured with the ISTD

method to calibrate the system. Figure 1 shows clear
separation of HCBD, BP, HET, 9F, DBF, and DBP. The
corresponding retention times (RTs) of the substance
peaks are listed in Table 1, with hexamethylbenzene
(RT 12.608 min; 0.2 mg/ml) as ISTD. The chemical
structures of these substances are shown in Table 2. The
substances have some extended UV-active ring structures,
a urotropine skeletal structure, or a six-fold chlorinated Table 3. The total amounts of quantified ingredients found in black
tattoo inks
butadiene.
The total amounts of all clearly identified ingredients Ink∗ Total amount∗ (μg/g)
in selected black tattoo inks are shown in Table 3. After
1 96.08
three repetitions of the extraction procedure, the values
2 42.38
ranged from 0.18 to 716.94 μg/g. A detailed list of 3 21.28
the quantified ink ingredients is given in Table 4. DBP 4 25.76
was definitely quantified in all ink samples. The total 5 0.48
amounts ranged from 0.12 to 691.2 μg/g. The six- 6 13.04
fold chlorinated butadiene (HCBD) was found in six ink 7 0.24
8 164.88
samples, with a total amount of 0.08–4.52 μg/g. High
9 14.86
amounts of benzophenone (BP) were extracted, ranging 10 0.18
from 0.26 μg/g for ink sample 14 up to 556.66 μg/g for 11 556.78
ink sample 11. BP was detected in all ink extract samples 12 14.92
13 716.94
14 6.12
Table 1. Retention time of the substances
∗ Names of traders and substances can be obtained from the authors.
Retention time (min) Reference substance
10.405 Hexachloro-1,3-butadiene except for samples 5, 7, and 10. Ink samples 2 and 13
10.486 Hexamethylenetetramine contained all specified ingredients.
13.189 Dibenzofuran
14.075 Benzophenone
14.939 9-Fluorenone Qualitatively determined ingredients
16.321 Dibutyl phthalate
Besides the six quantified ingredients, GC showed further
12.608 ISTD: hexamethylbenzene
peaks in several ink chromatograms. By use of the NIST
ISTD, internal standard. database for MSD analysis, additional compounds could
Table 4. The amounts of the quantified ingredients found in black chromatography technology (1). Using the established
tattoo inks (μg/g) extraction procedure (3), we found total concentrations
Ink HCBD Methenamine DBF BP 9-F DBP of PAHs in the different inks ranging from 0.14 to
201 μg/g. Even benz(a)pyrene, a known carcinogen, was
1 –∗ 0.32 0.04 95.34 0.04 0.34
found in four ink samples at a mean concentration of
2 0.08 0.14 1.62 34.74 3.04 2.76
3 0.30 — 0.02 19.94 0.62 0.40
0.3 ± 0.2 μg/g.
4 0.50 — 0.06 19.38 1.24 4.58 At the same time, we performed a nationwide survey
5 — — — — — 0.48 in German-speaking countries to determine the incidence
6 — 0.44 0.12 12.0 0.20 0.24 of health problems associated with tattooed skin (2). First,
7 — 0.08 — — 0.02 0.14
the survey showed that tattooed people have many (28%;
8 — — — 164.7 — 0.18
9 0.82 — 0.04 6.20 0.90 6.90 ≥4) and large (36%; ≥900 cm2 ) tattoos requiring the
10 — — — — — 0.18 injection of several grams of tattoo inks into skin, which
11 — — — 556.66 — 0.12 partly spread in the human body and probably stay
12 4.52 — — 7.92 0.24 2.24 lifelong in human tissue (2). However, it is possible that
13 1.00 21.64 0.02 2.96 0.16 691.20
14 — — — 0.26 1.80 5.68
people who like tattoos might have been more willing to
participate in such a survey.
BP, benzophenone; DBF, dibenzofuran; DBP, dibutyl phthalate; The participants described skin problems (67.5%) or
HCBD, hexachloro-1,3-butadiene; 9F, 9-fluorenone.
∗ Value below detection limit. systemic reactions (6.6%) directly after tattooing and
related to the tattooing process. Six per cent of participants
Table 5. Qualitatively detected ingredients in black tattoo inks complained of persisting skin problems at the site of the
tattoo, such as itching, burning, skin papules, small
Ink Other ingredients nodules, eczema, and redness of skin (erythema). In
1 3,6-Dimethyl-1 heptyn-3-ol addition, 1.3% reported burning and itching of tattooed
2 1,6-Hexandiole skin when it was exposed to solar radiation (‘light
3 1,6-Hexandiole sensitivity’).
4 Oleamide∗ ; 7-hexyl-2-oxepanone
In light of these skin reactions, we analysed the extracts
5 Propylene glycol; 7-hexyl-2-oxepanone
6 Propylene glycol of such black tattoo inks in more detail by using GC–MS
7 —† analysis to identify potential irritants or allergens. We
8 1,1 Oxybis-2-propanol; 2,2 oxybis-1-propanol found HCBD, HET, DBF, DBP, 9F, and BP, which were
9 7-Hexyl-2-oxepanone definitely quantified (Table 4). GC analysis and the NIST
10 Oleamide∗ ; 7-hexyl-2-oxepanone
database revealed the presence of other substances in
11 7-Hexyl-2-oxepanone
12 Oleamide∗ ; 7-hexyl-2-oxepanone the black inks that could be not clearly identified and
13 Carbitol cellosolve‡ 1,2,3,4-tetrahydro-1-phenyl-naphthalene quantified (Table 5).
14 7-Hexyl-2-oxepanone Below, we describe the usual sources of particular
∗ Oleamide: IUPAC name (Z)-9-octadecenamide. substances, and their effects in vitro and in the body,
† Value below detection limit. where known, with special regard to the skin. Any other
‡ Carbitol cellosolve: IUPAC name 2-(2-ethoxyethoxy) ethanol.
health concerns regarding the substances are listed in
Table 6.
be identified, for example alcohol-containing substances
such as 3,6-dimethyl-1-heptyn-3-ol, 1,6-hexandiole,
propylene glycol, and carbitol cellosolve, as well as sub-
Table 6. Assessment of other health risks
stances such as oleamide, 7-hexyl-2-oxepanone, and urea
(Table 5). Figure 2 shows a GC chromatogram of ink Dibutyl phthalate Genotoxic (4), teratogenic (5, 6)
sample 13 as an example. Among quantitatively and Hexachloro-1,3-butadiene Genotoxic (7), carcinogenic (8),
qualitatively detected ingredients, the chromatogram still classified by the US EPA as a
possible human carcinogen
shows peaks that could not clearly be identified with the
(Group C) (9)
NIST database. Dibenzofuran Not classifiable as to human
carcinogenicity (Group D) (10)
Hexamethylenetetramine Possibly genotoxic (11)
Discussion Benzophenone Some evidence of carcinogenic
activity (12)
Recently, we investigated commercially available black
9-Fluorenone None
inks regarding PAHs by using high-performance liquid
(a)
(b)
Fig. 2. Chromatograms of ink sample 13 (a) and ink sample 2 (b) showing additional substances that were either qualitatively determined or
remained unknown. PAH, polycyclic aromatic hydrocarbon.
Dibutyl phthalate in the adjuvant effect during skin sensitization (18). This
In principle, synthetic materials, for example polyvinyl- may reflect the connection between skin irritation and
chloride, contain several additives to provide special skin allergies. TRPA1 and TRPV1 may play a central
physicochemical handling properties, such as softness, role by transmitting noxious stimuli to the brain and
elasticity, and plasticity (13). These synthetic materials immune cells, such as antigen-presenting cells, by sens-
are used in wallpapers, cloths, toys, plastic films, and ing noxious compounds. Immunohistochemical analysis
artificial leather. Such phthalates are also present in of skin after epicutaneous application of DBP showed a
dispersions and lacquers. transient decrease in the number of C-type lectin-positive
Thymic stromal lymphopoietin (TSLP) is an epithelial- macrophages in the dermis (19).
derived cytokine expressed primarily in the lung, skin, and Our results clearly show that DBP is present in all of
intestine, in response to inflammation, tissue damage, or the black inks under investigation, with concentrations
Toll-like receptor ligation (14). In recent studies, it was up to 691 μg/g. When skin is tattooed, the black inks,
shown that DBP is capable of inducing expression of TSLP together with DBP, enter the skin. In this way, DBP
in the skin (15, 16). Allergic contact dermatitis caused by contacts nearly all skin cells that may trigger TSLP. An
DBP has been described (17). animal model showed, for coloured tattoo pigments, that
In immunological experiments, DBP has been empir- such pigments can be partially transported to lymph
ically included in the solvent system for fluorescein nodes (20). Therefore, other ingredients of tattoo inks,
isothiocyanate (18). A study showed that stimulation such as DBP, might be transported away from the
of sensory neurons via TRPA1 and TRPV1 is involved skin.
Hexachloro-1,3-butadiene formaldehyde and formaldehyde-releasing agents (30).

The chlorinated alkene HCBD is found predominantly The formaldehyde-releaser HET, as a preservative in
as a byproduct from the manufacture of chlorinated cosmetics, must not exceed a maximum authorized con-
solvents and related products. The substance was used centration of 0.15% (31). In addition, HET is known
as a fumigant for treating Phylloxera infection in the to cause respiratory allergies (30). In tattooing, HET is
former Soviet Union, and to a lesser extent in southern placed into the skin at concentrations up to 21.6 μg/g.
Europe (21).
Rabbits have been epicutaneously exposed to pure Benzophenone
HCBD (0.25–1.00 mg/kg) for 8 hr. HCBD has been found
BP, an aromatic ketone (diphenyl ketone), is an important
to be a skin penetrant and highly acutely toxic substance.
compound in organic photochemistry and perfumery, as
HCBD led to epidermal and dermal necrosis, whereas
well as in organic synthesis. In the field of food packaging,
the cutaneous changes increased with time for up to
5 weeks. The rabbits showed damage to the skin, liver, BP is used as an initiator compound for hardening of
and kidneys (22). Out of the 14 black ink samples, we printing inks by ultraviolet (UV) irradiation. Because of
found HCBD in six samples, with concentrations up to its volatile behaviour, BP is found in food.
4.5 μg/g. So far, there are no case reports showing toxicity According to the European Food Safety Authority
of HCBD in humans. (EFSA), BP is characterized as irritant but not geno-
toxic (32). A similar molecule is benzophenone-3 (2-
hydroxy-4-methoxy-benzophenone), which is frequently
Dibenzofuran used in sunscreens. It can cause photocontact allergy
DBF is the backbone of polychlorinated DBFs, which and other types of hypersensitivity reactions, such as
belong to the group of dioxin-like chemicals (23), and is contact allergy, photocontact urticaria, contact urticaria,
listed in the US Environmental Protection Agency (US
EPA) Toxic Substances Control Act (24). DBF is found
as a combustion product in various percentages from
the incomplete combustion of coal biomass, refuse, diesel
fuel, and residual oil, as well as tobacco smoke (25). DBF
is frequently used as wood preservative.
Out of the 14 black ink samples, we found DBF in seven
samples, with concentrations up to 1.62 μg/g. We only
detected the backbone of polychlorinated DBFs, and we
cannot decide whether the chlorine atoms were present
or cleaved prior to our investigations. The frequently
described dermal, hepatic, and gastrointestinal health
problems in humans are related to the brominated or
chlorinated DBFs (26, 27).
In particular, little to no information is available on
the effects of DBF exposure of skin. The information that
does exist shows that short-term exposure to DBF can
cause skin, eye, nose and throat irritation (28). Clear
data in the medical literature about DBF are lacking,
and the concentration in tattoo inks is low. Thus, it
remains unclear whether this substance can cause health
problems when tattooed into skin.
Hexamethylenetetramine
HET is used as a preservative in citrus washing solutions
and in the manufacture of rubber, resins, and coatings,
as well as in pharmaceuticals and cosmetics.
It is well known that preservatives used in cosmetics
constitute an important source of allergic contact dermati- Fig. 3. Example of a simple flask containing black tattoo ink with
tis (29). Some of the most problematic preservatives are no listing of ingredients.
and even cases of contact anaphylaxis (33). BP showed About 10% of the population are tattooed in Ger-
phototoxic reactions and caused photosensitization in the many. If we extrapolate this percentage to all tattooed
skin of guinea pigs under UV irradiation (34). individuals, we tentatively assume that about 0.5 million
Previous studies in humans have indicated that the people might have persistent skin problems with tattoos.
dermal absorption of organic UV filters during the appli- The investigated black inks are from different countries,
cation of sunscreens is very limited; in fact, only very low including the United States, where about 80 million peo-
concentrations of these UV filters were detected in the ple are tattooed (41). If the frequency of skin problems
blood after repeated, intensive application (35). However, is the same in the United States, we tentatively calculate
dermal penetration is maximal for such substances during a number of about 5 million people with persistent skin
tattooing, and many of the black ink samples contained problems at the tattooed site.
high concentrations of BP of up to 557 μg/g. Carbon black in the inks is not suspected of causing
allergic or irritant skin reactions. Thus, the described
health problems are more likely to be caused by some of
9-Fluorenone
the ingredients listed in this investigation, although the
9F is not commercially synthesized, but is obtained from listing might still be incomplete. Many of the 14 inks con-
the middle oil fraction of coal tar. It is used in the manu- tain more than one ingredient that might lead to complex
facture of antimalaria drugs and other pharmaceuticals. skin reactions. However, reports on adverse reactions in
9F may cause phototoxic reactions in vitro and in vivo, tattoos to the substances detected in this investigation are
in particular in the oral mucosa (36, 37). Beyond that, lacking so far. This first, but probably incomplete, list of
little is known about adverse reactions to 9F, in particu- tattoo ink ingredients may help physicians to search for
lar regarding skin. 9F was found in 10 of the black ink the chemical trigger of adverse skin reactions.
samples at low concentrations (up to 3.04 μg/g), and it In light of these results, we urgently recommend reg-
remains unclear to what extent 9F can harm the skin ulation of tattoo inks, so that only those inks without
after tattooing. hazardous substances may be used. This could be started
with a first step: substances that are not permitted to
be used in cosmetics should be prohibited from being
Conclusion punctured into skin. Moreover, lack of knowledge (Fig. 3)
The medical literature contains numerous case reports should be remedied by requiring complete listing of the
on dermatological diseases caused by tattoos, including ingredients, as for cosmetics.
pseudolymphoma, and allergic or granulomatous skin
reactions (38–40). Considering the results of the survey
in German-speaking countries, approximately 7.3% of Acknowledgement
tattooed people describe persistent skin reactions at the This study was supported by the Deutsche Forschungs-
site of tattooing, including light sensitivity (2). geneinschaft (DFG, grant BA 1741/3-2).
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Contact Dermatitis Lehner Are A Source of Problematic Substances Such As Dibutyl Phthalate

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Contact Dermatitis • Original Article COD

Black tattoo inks are a source of problematic substances

Key words: black inks; dibenzofuran; gas chromatography; health problems;

Materials and Methods Analysis was performed with an Agilent Technologies

Table 2. Chemical structures of identified and quantified ingredients

Fig. 1. Chromatography of the quantified substances. The

detected in a first GC run, were measured with the ISTD

Retention time (min) Reference substance

Hexachloro-1,3-butadiene formaldehyde and formaldehyde-releasing agents (30).

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