Irish Standard

1.5 EN ISO 163 73 -3:2014

Textiles - Dyestuffs - Part 3: Method for

determination of certain carcinogenic
dyestuffs (method using
triethylamine/methanol) (ISO 16373-
3:2014)

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1.5 . EN ISO 16373-3,2014

Incorpora ting amendments/corrigendalNaUonal Annexes issued since publication:

The National Standards Authority of Ireland (NSAI) produces the following categories of formal documents;

1.5. xxx : Iri sh Stan dard - national specification based on th e consensus of an expert panel and subject to public consultation .

S.R. xxx: Standard Recommendation - recommendation based on the consensus of an expert panel and subject to public consultation .

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This document Is based on: Published:

EN ISO 16373-3,2014 2014-06-04

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unde r the autho rity of the NSAI
and comes into effect on: 59.080 .01

2014-06-21

NOTE: If blank see CEN/CENELEC cover page

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 I.S. EN ISO 16373-3:2014

EUROPEAN STANDARD EN ISO 16373-3

NORME EUROPEENNE
EUROpAISCHE NORM June 2014

ICS 59080.01

English Version

Textiles - Dyestuffs - Part 3: Method for determination of certain

carcinogenic dyestuffs (method using triethylamine/methanol)
(ISO 16373-3:2014)

Texti!es - Colorants - Partie 3: Methode de determination de Textilien - Farbstoffe - Teil 3: Verfahren zur Beslimmung
certains colorants cancerigElOes (methode a 13 triethylamine von bestimmten karzinogenen Farbstoffen
et au methanol) (ISO 16373-3:2014) (Triethylamin/Methanol-Veriahren) (ISO 16373-3:2014)

This European Standard was approved by CEN on 17 April 2014.

CE N members are bound to comply with the CEN/CENELEC Internal Regulations which stipulate the conditions for giving this European
Standard the status of a national standard without any alteration. Up-to-date lists and bibliographical references concerning such national
standards may be obtained on application to the CE N-CE NELEC Management Centre or to any CEN member.

This European Standard exists in three official versions (English, French, German). A version in any other language made by translation
under the responsibility of a CEN member into its own language and notified to the CEN-CENELEC Management Centre has the same
status as the official versions

CE N members are the national standards bodies of Austria , Belgium, Bulgaria , Croatia, Cyprus, Czech Republic, Denmark, Estonia,
Finland, Former Yugoslav Republic of Macedonia, France, Germany, Greece, Hungary, Iceland, Ireland, Italy, Latvia , Lithuania,
Luxembourg, Malta, Netherlands, Norway , Poland , Portugal , Romania, Slovakia , Slovenia, Spain, Sweden, Switzerland , Turkey and United
Kingdom .

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© 2014 CEN All rights of exploitation in any form and by any means reserved Ref. No. EN ISO 16373-3:2014 E
worldwide for CE N national Members .
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 loS. EN ISO 16373-3:2014
EN ISO 16373-3:2014 (E)

Foreword

This document (EN ISO 16373·3:2014) has been prepared by Technical Committee ISOITC 38 "Textiles" in
collaboration with Technical Committee CENITC 248 "Textiles and textile products" the secretariat of which is
held by BSI.

This European Standard shall be given the status of a national standard , either by publication of an identical
text or by endorsement, at the latest by December 2014 , and conflicting national standards shall be withdrawn
at the latest by December 2014 .

Attention is drawn to the possibility that some of the elements of this document may be the subject of patent
rights . CEN [and/or CENELEC) shall not be held responsible for identifying any or all such patent rights.

According to the CEN-CENELEC Internal Regulations, the national standards organizations of the following
countries are bound to implement this European Standard: Austria, Belgium , Bulgaria, Croatia , Cyprus , Czech
Republic, Denmark, Estonia, Finland , Former Yugoslav Republic of Macedonia, France, Germany, Greece,
Hungary, Iceland , Ireland , Italy, Latvia, Lithuania, Luxembourg, Malta , Netherlands, Norway, Poland, Portugal ,
Romania, Slovakia , Slovenia, Spain , Sweden, Switzerland, Turkey and the United Kingdom.

Endorsement notice

The text of ISO 16373-3:2014 has been approved by CEN as EN ISO 16373-3:2014 without any modification.

3
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Get permission to copy from or network this publication www.saiglobal.com/licensing

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1.5. EN ISO 16373-3:2014

INTERNATIONAL ISO
STANDARD 16373-3

First edition
2014·06·01

Textiles - Dyestuffs -
Part 3:
Method for determination of certain
carcinogenic dyestuffs (method using
triethylamine/methanol)
Textiles· Colorants-
Partie 3: Methode de determination de certains colorants
cancerigenes (methode ala triethylamine et au methanol)

Reference number
ISO 16373·3:2014(E)

© ISO 2014
 I.S. EN ISO 16373-3:2014
ISO 16373-3 :2014(E)

COPYRIGHT PROTECTED DOCUMENT

© ISO 2014
All r ights rese rved. Unless othe rw ise specified, no part of t hi s publicatio n may be re produced or utilized otherwise in any form
or by any means, electro nic or mechan ical, including photocopying, or posti ng on the interne t or an intra net. without prior
wr itten per miss ion. Permissio n can be reqllested from either ISO at the address be low or ISO's member body in the country of
the requester.
ISO copyright office
Case postale 56 · CH-12 11 Geneva 20
Tel.+4 1 227490 1 11
Fax + 4 1227490947
E-mail copyr ight@iso.org
Web www.iso.o rg
Published in Switzerla nd

ii © [SO 2014 - All fig hts rese rved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Contents Page

Foreword .... iv
Introduction .... .V
1 Scope . 1
2 Terms and definitions 1
3 Principle .. . ...... 1
4 Safety precautions .. ... ..... .... ..... .. ..... . .......... .... .... .2
4.1 General... .. ........ 2
4.2 Handli ng. ... 2
5 Apparatus ... 2
6 Reagents .. 3
7 Test specimen sampling and preparation ...................................................................................................................... 3
7.1 General ............. 3
8 Procedure ... .... 3
8.1 Extracti on ... .. ... 3
8.2 Detectio n, ide ntifica tion and q ua ntifi catio n of carcinoge nic dyes tuffs . .. ......... 4
9 TestreporL 4
Annex A (in formative) Chromatographic analysis .... 5
Annex 8 (in formative) Round robin test results .. ....... 22
Bibliography ... 27

© 1$0 2014 - All rights reserved ii i

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Foreword
ISO (the International Organization for Sta nda rdi zation) is a worldwide federation of nationa l standards
bodies (ISO member bodies). The work of preparing International Standards is normally carried out
through ISO technica l committees. Each member body interested in a subject for which a technical
committee has been established has th e ri ght to be represented on that comm ittee. Internat io nal
orga nizations, governmenta l and non-governmental, in liaison with ISO, also take part in the work.
ISO col laborates closely with the Internationa l Electrotechnica l Commission (IEC) on a ll matters of
electrotechni ca l sta ndardization.
The procedures used to develop this docu ment and those intended for its furth er maintenance are
described in the ISO/ IEC Directives, Part 1. In particular the different approva l criteria needed for the
different types of ISO doc uments should be noted. This document was drafted in accordance with the
editoria l rules of the ISO/IEC Directives, Part 2. www.i so.org/directives

Attention is drawn to t he possibility t hat some of the elements of this document may be the subject of
patent rig hts. ISO shall not be held responsible for identifying any or all s uch patent rights. Detail s of
any patent ri ghts identified during the development of the document will be in the Introdu ction a nd /or
on the ISO list of patent declaration s received. www.iso.org/patents

Any trade name used in this document is information given for th e convenience of users and does not
constitute an endorsement.

For an explanation on the meaning of ISO specific terms and express ions related to conformity
assessme nt, as well as information about ISO's adherence to the WTO pr inciples in the Technica l Barriers
to Trad e (TBT) see the follow in g URL: Foreword - Supp lementa ry information

The committee responsible for this document is ISO/TC 38.

ISO 16373 consists of the following parts, under the genera l title Textiles - Dyestuffs:

Part 1: General principles of testing coloured textiles for dyestuff identification

Part 2: General method for the determination of extractable dyestuffs including allergeniC and
carcinogenic dyestuffs (method using pyridine-water)
Part3:Methodfordeterminotionofcertoincorcinogenicdyest,iffs(methodusingtriethylomine/methonol)

iv © ISO 20 14 - All righls reserved

 loS. EN ISO 16373-3:2014
[SO 16373-3:2014(E)

Introduction
Due to concerns of consumers over safety and hygiene, many countries have introduced regulations
regarding carcinogenic dyestuffs in textile articles. To support international and national regulations
the development of a test method is very important and this part of ISO 16373 does just that.

The ISO 16373 series deal with dyestuffs used in textile for qualification and quantification.

ISO 16373-1 1) includes the definition of the dyestuff, and classes the description of some procedures
to identify qualitatively the dyestuff class used in text ile material. The other parts of ISO 16373 are
related to the quantification of some dyestuffs.

In ISO 16373-2, the principle of the test method is based on extraction using pyridine-water solution,
which has been found to be the most efficient solution to extract a large range of dyestuffs, including
allergenic and carcinogenic dyestuffs.

In this part of ISO 16373, the principle of the test method is based on extraction using triethylam ine-
methanol solutio n. This solut ion has been found to be efficient at extract in g some dyestuffs in some
cases.

Additional information related to the recovery rate (to characterize the extraction efficiency) obtained
from th e application of ISO 16373-2 and th is part of ISO 16373 is summarized in ISO 16373-1:-, Annex B.

It is important to note that there are other test methods related to aza dyes, for which a reduction of th e
extracted aza dyes leads to the release of some aromatic amines to be detected and determined using
chromatography.16] ll ]

1) To be published.

© ISO 2014 - All rights rese rved v

Licensed to Ms. Dawn Burnett on 9 September 2016. 1 user personal license only. Copying, copy/pasting , storage & distribution or use on network prohibited . (10625080).
Gel permission to copy from or network this publication www.saiglobal.comlficensing

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 I.S. EN ISO 16373-3:2014

INTERNATIONAL STANDARD ISO 16373-3:2014(E)

Textiles - Dyestuffs -
Part 3:
Method for determination of certain carcinogenic dyestuffs
(method using triethylamine/methanol)

1 Scope
This part of ISO 16373 specifies a method for the detection and quantitative determination of the
presence of carcinogenic dyestuffs as listed in Table 1 in dyed. printed or coated textile products by
chromatographic analysis of their ex tracts.

2 Tel'ms and definitions

For the purposes of this document, the following terms and definitions app ly.
2.1
textile
woven fabric, knitted fabric, etc., formed by the interlocking of fibres and yarns having a certain cohesion
and which is generally intended for clothing or furniture applicatio ns
Note 1 to entry: Textiles often include certain types of non-woven fabrics.

2.2
carcinogenic dyestuff
substance yielding a dye that is a s ubs tance known to be or suspected of being a human carcinogen

3 Principle
The dyes tuff of a coloured tes t specimen is extracted by means of a solvent in an ultrasonic bath under
specified conditions. The ex tract is analysed using either a high·performance liquid chromatography
photodiode array detector ( HPLC-DA D) or a high-performance Iiqu id chromatography mass spect rometer
(HPLC·M5D).
The carcinogeni c dyestuffs are li sted in:Ial:!k..l.

Table 1 - List of carcinogenic dyestuffs

C.I. Constitution
C.I. Generic name CAS number
number
c.1. Basic Red 9 569-61-9 42500
c.1. Disperse Orange 11 82- 28-0 60700
c.l. Dispers e Yellow 3 2832-40-8 11855
c.1. Acid Red 114
c.1. Acid Red 26
6459 - 94-5
3761-53-3
23635
16150 \
c.1. Direc t Black 38 1937-37-7 302 35
c.1. Direct Red 28 573-58-0 22120
c.!. Dispe rs e Blue 1 2475 - 45-8 64500

© ISO 2014 - All rights reserved 1

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table 1 (continued)
C.I . Constitution
c.1. Generic name CAS number
number
c.!. Basic Vio let 14 632-99-5 42510
c.1. Direct Blue 6 2602 -46- 2 22610
c. 1. Direct Brown 95 16071- 86- 6 301 45

4 Safety precautions

4.1 General
Warning - The dyestuffs targeted in this part of ISO 16373 are classified as substances known
to be or suspected of being human carcinogens.

4.2 Handling
It is the user's responsibility to ensure any handling and disposal of these substances are in strict
accordance with the appropriate national health and safety regulations.
It is the user's responsibility to use safe and proper techniques in handling materials in this test
method. Consult manufacturers for specific details, such as material safety data sheets and other
recommendations.
Good laboratory practice should be followed. Wear safety glasses in all laboratory areas and
single-use dust respirator while handling the dyestuffpowder.

5 Apparatus

5.1 Ultrasonic hath, capabl e of heating to and main ta ining at (5 0 ± 5) °C and output power of 40 W,
oscillating frequency, 4 2 kH z, or equivalent.

5.2 Coil condenser, for chemica l testing use.

5.3 Vacuum rotary evaporator, ca pable of operating at water evaporation capa city of a maximum of
25 ml/min, or equivalent.

5.4 Round hottom flask, of 2001111 in capacity.

5.5 Pipettes, of 1 ml and 10 ml in capacity.

5.6 Volumetric flask, of 10 ml, 100 011 and 1 1 in capa city.

5.7 High'performance liquid chromatography (HPLC) system and diode array detector (DAD) or
mass spectroscope (MSDj.

5.8 Test tube, of 100 ml in ca pacity, with a silicone plu g.

NOT E For detai ls of t he hi gh -perfo r mance liqui d ch roma tog ra phy e quipm e nt, see Annex A.

5.9 Analytical balance, of 0,001 g in resolution.

2 © ISO 2014 - All rights reserved

 1.5 . EN ISO 16373-3:2014
ISO 16373-3:2014(E)

6 Reagents
Unless otherwise speci fied, use only reagents of recognized analytical grade.

6.1 Acetonitrile.

6.2 Methanol.

6.3 Hexane.

6.4 0,25 % tri-ethylamine methanol solution, 2,5 ml triethylamine is dissolved in methanol and
made up to 1 I.

6.5 10 mmol/l ammonium acetate aqueous solution, 0,77 g ammonium acetate is dissolved in water
and made up to 1 I.

6.6 Carcinogenic dyestuffs. Use only carcinogenic dyestuffs of reagent grade of the highest purity
ava ilable on the market, or dyestuffs of wh ich quantities of the dye are manufactured in controlled
e nvironments within Europe under the control of the EU creating standard dyestuffs.

6.7 Standard solution of carcinogenic dyestuffs.

An amount of each carcinogenic dyestuff is weighed accu r ately in the range of 1 mg to 10 mg and
transferred quantitatively to a 10 ml volumetric flask, and then made up to volume with methanol (62)
to prepare a standard solution in the range of 100 ug/ml to 1 000 ug/ml.
The standard solut ion may be diluted properly and four solutions with known concentrations may be
made to draw the ca libration curve. As an example, the range of concentration of standa rd solutions for
the calibration curve can be recommended to be from 1 ~g/ml to 100 pg/ml.

7 Test specimen sampling and preparation

7.1 General

The test specimen sha ll be selected based on th e following criteria:

parts of the text il e article;

nature of th e fibre component (fibre composition);

colours.
Prepare a test specimen of maximum 1,0 g (~1,0 g) by cutting the labora tory sample up into small pieces
no larger than 1 cm z, Determine the mass of the test specimen to the nearest 0,01 g and record it as mE
(see lU).

8 Procedure

8.1 Extraction

8.1.1 Cleansing

If required, remove oil, grease or other fatty matter from the s urface of the test specimen by soa king it
in 100 ml hexane (63) for 5 min in an ultrasonic bath (S,l) at ambient temperature.

© ISO 20 }4 - All rights reserved 3

 loS. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Remove and drain the test specimen.

8.1.2 Extraction of dyestuff

Place 1,0 g of the test specimen in a 100 ml test tube. Add 100 ml of th e 0,25 % tri-ethylamine me thanol
solution (6.1) and seal the test tub e using a silicone plug. Heat the tube in an ultrasonic bath until a
temperature of 50 °C ± 2 °C is r eached and maintained th is temperature for 3 h.

8.1.3 Concentration of extract and preparation of analysis solution

Tran sfer the ex tract obtained according to 8.1..2. to a 200 ml round bottolll flask (SA) and place it in a
vacuum rotary eva porator (53) in the water bath at 40 °C ± 2 °C until all the liquid has eva porated.

Di ssolve th e residue in 1 ml of methanol. Filter the solution through a 0,45 pm PTFE filter. If the resultant
measuremen t is higher than the calibrated range of the chromatograph, dilute the solution further with
methanol.

8.2 Detection, identification and quantification of carcinogenic dyestuffs

Detec tion of carcinogenic dyestuffs is performed by the chromatographic analys is using th e apparatus
described in 52. When the carcinogenic dyestu ffs are identified by comparing with peaks of reference
carcinogenic dyestuffs, qu an tifica tion is performed using a calibration curve, which is drawn by using a
minimulll offour points obtained from an HPLC analysis of the s ta ndard solution (.6.2) a nd the correlation
coefficient of the linear curve should be 0,99 in the range of concentration of 1 pg/ml to 100 pg/ ml.
Quantification is executed by th e met hod of HPLC/DAD. When a large amount of for eign s ubsta nces are
detected, HPLC/MSD is recommended for identifi cation and quantification.

The concentration of carcinogenic dyestuff in the s peci men is ca lculated as a ma ss fraction of the
s pecim en, w (pg/g), as given by Formula (1):

P xV
s -
w ;- (1 )
mE

where
Ps is the interpolated concentration of carcinogen ic dyes tuff, in microgram s per millilitre (~Ig/
ml);

V is the final sol ution volume made up to acco rdin g to ll.1.2.. in millilitres (01 1);

m E is the mass of th e test specimen, in millilitres (ml);

9 Test report
The test report s hall include the fo ll owing:

i a) reference to this part of ISO 16373, i.e. ISO 16373-3;

8
~ b) kind, origin and designation of th e s pecimen (pa rtial s peci men, if applicable);

c) detection method and quantification method;

d) res ults reported as level and detection limit for each of the carcinogenic dyestuffs (~Ig/g);

e) any deviation from the procedure.

4 © ISO 2014 - All rights reserved

 I.S. EN ISO 16373-3:2014
ISO 16373·3:2014(E)

AnnexA
(inform ative)

Chromatographic analysis

A.1 Chromatographic analysis - General

As t he instrumenta l equ ipment of laborator ies might va ry, no genera lly app licab le instructio ns can
be provided for ch romatograph ana lysis. Therefore, t he fo llow ing para mete rs have been successfu ll y
tested and used. See figures A 1 to A.ll and Ta ble A 1.

A.2 High-performance liquid chromatography/diode array detector (HPLC/DAD)

See Ta ble A.J.

Ta ble A.I - Co ndit ion of HPLC/DAD

Eluent 1: 10 mmoljl am mon ium acetate

Eluent 2: Acetonitrile
Colum n Ine rtsil 00S -3, 150 mm x 3,0 mm, 5 pm
Flow rate: O,8mlfmin
Gra d ient Time (min) Eluent 2 concentrations
Time programme Initial 5%
30 60%
40 60%
40.1 5%
50 S%
Column temperature: 45 '(
Inject ion volume: 5.0 "I
Determination: DAD
Qua ntification: 540 nm (for Basic Red 9)
480 nm (for Disperse Orange 11)
350 nm (for Di s perse Ye ll ow 3)
510 nm (for Acid Red 114)
510 nm (fo r Acid Red 26)
600 nm (for Dire ct Bl ac k 38)
500 nm (for Direct Red 28)
Remark Columns of equivalent quality may be used .

© ISO 20 14 - All rights rese rved 5

 1.5_ EN ISO 16373-3:2014
ISO 16373-3:2014(E)

mAU
.-------------<rrrr---------~

20

"
266.87

200 300 ' 00 500 600 700

om

Figure A_I - UV spectrum of Basic Red 9

mAU
30,-------- -- - - ---------------- -- -------,

20

"

o 30 35
" " 20 25
"
min

Figure A.2 - HPLC/DAD Chromatogram at 540 nm detection

mAUr - - o_ _ _ _ _ _ _ _ _ __ _ _ __ ______- ,

247,83
20

"
"
5
,
477.32

!lm

Figure A.3 - UV spectrum of Disperse Orange 11

6 © ISO 20 14 - All rights reserved

 1.5. EN ISO 16373-3:2014
[SO 16373-3:2014(E)

mAU
10 , O r - - - - - - - - - - - - - - - - - - - - ,

7 ,5

5,0

2 ,5

Figure A.4 - HPLC/DAD Chromatogram at 480 nm detection

mAUo-_ _ __ _ _ _ _ _ _ _ __ _ _ _ _ _--,

354 .40

200 300 400 600 700

om

Figure A.S - UV spectrum of Disperse Yellow 3

mAU
10,0

7,5
Disperse Yellow 3
5,0
/
2,5

0,0

10 20 25 3D 35
0
"
min

Figure A.6 - HPLC/DAD Chromatogram at 350 nm detection

mAU
35

30

25
511,92
2Q

15
,
364.27

10

200 300 "0 soo 600 700

om

Figure A .7 - UV spectrum of Acid Red 114

© ISO 2014 - All rights reserved 7

 1.5. EN ISO 16373-3:2014
ISO 16373-3:Z014(E)

". , - - - -- - - - - - - - -- - - ---,
mAU
.

/ ACOd Red 114

20 25 30 35 <0
min

Figure A.8 - HPLC/DAD Chromatogram at 510 nm detection

mAU

30
50~.93
25

20

15

!O

,m

Figure A.9 - UV spectrum of Acid Red 26

mAU
'5~--------------------_.

5 15 20 25 30 35 <0
min

Figure A.10 - HPLC/DAD Chromatogram at 510 nm detection

mAU

om

Figure A.ll - UV spectrum of Direct Black 38

8 © [SO 2014 - All rights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

mAU
10.5-r------------------,

7.' Direct Black 38

,/
'.0
2.'

o.oc:::::::::;::::~.lI::;::::::::;:;::;;::;:;:;::;:d
o 10 15 2{) 25 30 35

Figure A.12 - HPLC/DAD Chromatogram at 600 nm detection

mAU
,------------------------,

2S
20
1S
10

•
o~~~~~~~~~~~~
300 ' 00 soo 600 700
om

Figure A.13 - UV spectrum of Direct Red 28

mAU
. O~------~---------_,

30 Direct Red 28

20 /

10 1S 20 2S 30 35 40
m.

Figure A.14 - HPLC/ DAD Chromatogram at 500 nm detection

A.3 High-performance liquid chromatography/mass analysis detector

(HPLC/MSD)

A.3.t LC/MS SIM (selected ion monitoring) method

See Fi gures A.1S to A,2ll and Table A.2.

Table A.2 - Condition of the HPLC/ MSD

Eluent 1 10 mmol/l a mmonium aceta te
Eluent 2 Acetonitrile
Colu mn In ertsil 00S-3, 150 mill x 3,0 m Ol, 5 ~lIn

Flow ra te 0,8 ml/min

© ISO 2014 - All rights reserved 9

 I.S. EN ISO 16373-3:2014
ISO 163 7 3 ·3:2 0 14(E)

Table A.2 (continued)

Gradient Time (min) Eluent 2 concentrations
Time programme Init ial 5%
30 60 %
40 60 %
40,1 5%
50 5%
Column temperature: 45 · C
In jection volume: 5,0 ~I

Detection: Four pile pole or ion trap ma ss detector

SIM(selected ion monitoring) method
Ma ss spectrum
Ionization: ES I electro spray ionizing metho d and positive/negative
ion dete c tion
Monitor chan nel: pos itive QI m/z 288 (for Bas ic Red 9)
pos itive QI m/z 238 (for Di sperse Orange II)
positive Ql Ill/z 270 (for Di s perse Yellow 3)
negative QI m/z 785 (for Acid Red 114)
negative Ql Ill/z 435 (for Acid Red 26)
posit ive QI Ill/z 738 (for Dire ct Black 38)
positive Ql m/z 653 (for Direct Red 28)
Impre ssed voltage: 5000 V
Temperature of spray: 500 · C
Remark Columns of equivale nt quality Illay be use d.
28
6,0e7
Basic Red 9
5.0e7 m/z 288

<l ,Oe7

3,De7

2.0e7

1,0e7
5,0e6

200 300 400 500 600 700 800 900 1000 1100 1200
mlz. amu

Figure A.I S - Mass spectrum of Basic Red 9

10 © ISO 2014 - All rights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

18,1
9,0e5

8,De5

7.005

6,005

5,005

4.005

3,OeS

2.DeS

246810121416'8Mn~~a3032~~~404244%~~
Time, min

Figure A.16 - SIM Chromatogram of Basic Red 9

238
2.0e7
I,Be? Disperse Orange 11
1,6el mlz 238

1,4e7

1.2e7
I,De7

B,Qe6
6,De6
4.0e6

".De6

200 300 400 500 600 700 800 900 1000 1100 1200
mlz. amu

Figure A.17 - Mass spectrum of Disperse Orange 11

2.8e5
25.9

2,4e5

2,DeS
Disperse Orange 11

I.GeS
/
l,2eS

6,004

4 ,Oe4

10 14 16 22 ~ ~ ~ ~ 42 % ~
Time, min

Figure A.18 - SIM chromatogram of Disperse Orange 11

© ISO 2014 - All rights reserved 11

 1.5_ EN ISO 16373-3:2014
ISO 16373-3:2014(E)

270
J,Oe7

2.Se7 Disperse Yellow 3

mJz 270
2.2e7

I,Sel

l,4e7

I,Ge7

6 ,De6

2.oeS

200 300 <00 500 600 700 600 900 1000 1100 1200
mil, emu

Figure A.19 - Mass spectrum of Disperse Yellow 3

26,4
a,De4

1,0e4

6.'" Disperse Yenow 3

5,oe4 /
4,0e4 .

3,{)e4

2.004

1'0e4l:;:;::;:;:;:::;::::::~~~~~~~~~~~:;:;:;:::;:;;
2 6 n 10 14 18 ~ ~ ~ ~ Q ~ ~
Time, min

Figure A.20 - SIM chromatogram of Disperse Yellow 3

I,Sel
Acid Red 11 4
I.Gel
m!z 785
J92
1.4el

1.2eI

I,Oel

a,0e6

6.0.6

<.0.6

2,De6

~ ~ ~ ~ _ ~ _ m ,_ , . ,_
mil, amu

Figure A.21 - Mass spectrum of Acid Red 114

12 © ISO 20 14 - All r ights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

23.6
2,Oe4
I.8e4
1.6e4 Acid Red 114
1,4e4
1,2e4
I ,Oe4
/
8000
6000
4000
2000

2 6 10 14 18 22 26 30 34 38 42 46 50
Tome , min

Figure A.22 - SIM chromatogram of Acid Red 114

I,Sel '" Acid Red 26

1,6el mlz 435

!,4e7

1.2e7

I.Oel

B.De6 '"
'.0.< 2<'
4,De6

2.0e6

200 300 400 500 600 700 800 900 1000 1100 1200
mlz. amu

Figure A.23 - Mass spectrum of Acid Red 26

11.2
1,6eS

1,4aS
Acid Red 26

/
1.2a5

I.GeS

8.0e4

6,0e4

4,Oe4

2,0e4

10 14 18 n ~ ~ ~ ~ 46 50
Tome. min

Figure A.24 - SIM chromatogram of Acid Red 26

© ISO 2014 - All rights reserved 13

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

738
' ,6e6
4,2e6 Oirect Black 38
3.Be6 mlz 738
3,4e6
3,_
2,6e6
2.2e 6 370
I .Se6
1,4e6

I ,DeS
6,0e5
2.OeS
'"
200 300 400 500 600 700 800 900
mlz. arnu

Figur e A.2S - Mass spectrum of Direct Black 38

19,3
3.884

3,4 e4

3,De4

2.6e4 Direct Black 38

2,2e4 /
1.8e4

l,4 e 4

l ,0e4

6000

2000

6 10 14 18 U ~ ~ U ~ 42 46 ~
Time. min

Figure A.26 - SIM chromatogram of Direct Black 38

653
1.2e6
l ,le6 Direct Red 28
I ,De6 mlz 653
9,DaS
B,OeS
7,065
6,0e5
5,0e5
4,DeS
3,0e5
2.OeS
I ,OeS

200 JOO .00 500 600 700 800

mlZ.3mu

Figure A.27 - Mass spectrum of Direct Red 28

14 © ISO 2014 - All rights reserved

 I.S. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

15.2
7.OeS

6,OeS

5.0e5 Direct Red 28

4,0e5 /
J,0e5

2.0e5

I,OeS

a ,. •• • • • M • U A ~
TIme, mIn

Figure A.28 - SIM chromatogram of Direct Red 28

A.4 LCjMSjMS SRM (selected reaction monitoring) method

See Fig","es A.29 to A.42 and Table A 3.

Table A.3 - Cond ition of LCjMSjMS SRM

Eluent L ]0 ml110lfl ammonium acetate

Eluent 2 Acetonitrile
Column In e rtsil ODS·3, 150 111m x 3,0 mOl,S pm
Flow rate 0,8 mljrnin
Gradient Tim e(min) Eluent 2 concentrations
Time programme In itial S%
30 60 %
40 60 %
40.1 S%
50 S%
Column temperature: 45 · C
Injection volume: 5.0 "I
Detection : Four tandem type pile pole or ion trap mass detector
SRM(selecteci reaction monitoring) method
Product ion ma ss spect rum
Ionizing: E51 electro s pray ionizing method and positive/negative
ion detection

© ISO 2014 - All fights reserved 15

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table A.3 (continued)

Monitor channel positive Ql m/z 288 ~ Q3 m/z 195 for Basic Red 9
(collision energy: 43 eV)
pos itive Ql m/z 238 ~ Q3 m/z 167 for Di spe rse Orang e
11
(colli sion energy: 49 eV)
po s itive Ql m/z 270 ~ Q3 m/z 150 for Disperse Yellow 3
(colli sion energy: 23 eV)
negative Ql m/z 435 ~ Q3 m/z 355 for Acid Red 26
(collision energy: -36 eV)
negative Qlm/z 785 ~ Q3 m/z 302 for Acid Red 114
(collision energy: -36 eV)
positive Ql m/z 738 ~ Q3 m/z 274 for Dire ct Black 38
(collision energy: 65 eV)
positive Ql m/z 653 ~ Q3 m/z 353 for Direct Red 28
(collision energy: 4S eV)
Impressed voltage: 5000 V
Temperature of spray: 500 0 (
Spray gas: Nitrogen
Spray energy: 30 eV
Rem ark Columns of equivalent quality may be used.
3.6e6

3.4e6
Basic Red 9 '" mlz 195

~
3,Oe6

2,6e6

2.2e6 mlz 288

288
1,Se6

l Ae6

l,0e6

6.lleS

2.Oc5
60 80 "0 120 140 160 180 200 220 240 260 260 300 320 320
mlz. amu

Figure A.29 - Product ion mass spectrum of Basic Red 9

16 © ISO 2014 - All rights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

18,1
8,Oe 4

1.0e4

6,0e4 Basic Red 9

S.0e4
/
4.0e4

3,Oe4

2 ,Oe4

l,0e4

6 10 14 18 2'2 26 30 34 38 41 44 50
Time, min

Figure A.30 - SRM chromatogram of Basic Red 9

Disperse Orange 11
'"
2,SeS
2.4e5
'67
, mlz 167

~ml'238
2,2eS
2.0eS
I,SeS
1,6eS
1,4e5

1.2eS 223

1.OeS
8.0e4 '"
6,0e4

:r ~r
4,0e4
2.0e4

60
Y l'
80
T
100 120
J. ,
140
',II'60 \80
III
200
,l
220 240
mlz. amu

Figure A.31 - Product ion mass spectrum of Disperse Orange 11

26,0
4600
4200
3800
Disperse Orange 11
3400
3000
2600
/
2200
\800
"00
1000
600
200

6 10 ,'e' 22 26 30 34 38 42 46 50
" Time , min

Figure A.32 - SRM chromatogram of Disperse Orange 11

© ISO 2014 - All rights rese rved 17

 1.5. EN 150 16373·3:2014
ISO 16373·3 :2014(E)

1,266 "0
1,166
mlz 150 Disperse Yellow 3
'.""
9,0e5
6.OeS '07
7,DeS
6,DeS
mlz 270
5,OeS
4,Oe5
3,Oe5
2,OeS
270
I.DeS

50 70 90 110 130 150 110 190 210 230 250 270 290
mlz. amu

Figure A.33 - Product ion mass spectrum of Disperse Yellow 3

26.4

5,0e4

' .0.< Disperse Yellow 3

3,0e4
/
2.0e4

I,Oe4

6 '0 M '8 • • • M • a _ •
Time. min

Figure A.34 - SRM chromatogram of Disperse Yellow 3

3Ae6 302
mlz302 Acid Red 114
3.006

2....

2.266

1,Se6

1.4e6
mlz 785

6,Oe S

'00 200 300 400 500 600 700 800 900 1000 1100 1200
mlz. amu

Figure A.35 - Product ion mass spectrum of Acid Red 114

18 © ISO 2014 - All rights rese rved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

24 ,5

5000

/ A d d Red 114
'000

3000

2000

"00

'0 " ,. D • 30 M • U • 50
Time, min

Figure A.36 - SRM chromatogram of Acid Red 114

302 355
2,4e5

'\
Acid Red 26

2.0e5

l,SeS

1.2eS 207
435
m
2M
8,De4
m/z 435

<I,Oe.:!
'"
I 3r
200 240 280 320 360 "0 440
mlz, aml.l

Figure A.37 - Product ion mass spectrum of Acid Red 26

9000 11.2

.000
/ A ' ; d Red 26
7000

6000

5000

4000

3000

2000

"00

'0 " ,. D • 30 M • U • 50
Tome, mm

Figure A.38 - SRM chromatogram of Acid Red 26

© ISO 2014 - All rights reserved 19

 I.S. EN ISO 16373-3:2014
ISO 16373-3:Z014(E)

288
'200
3800 Direct Black 38
3<00
'"
3000
mh274

2600 .68

2200
152 ".
1800 mlz 738
.. 00 135 565
183 502
.000
600
200
. 00 200 300 '00 500 600 700 600
mlz. arnu

Figure A.39 - Product ion mass spectrum of Direct Black 38

19,3
600

500

"0 Direct Black 38

,/
300

200

' 00

o~~~~~~~~~~~~~~~~~
6 .0 •• '6 ~ ~ • M • q • 50
nme,miro

Figure A.40 - SRM chromatogram of Direct Black 38

353
MOO

3000 325

~OO

2200

1800

1400
222

"00 306

T
600

200 II, I, III I I

200
'" 280 320 360 '00 "0 ..0 520 560 600 .. 0 680
mil. amu

Figure A.41 - Product ion mass s pectrum of Direct Red 28

20 © ISO 2014 - All rights reser ved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

15,2

"000
9000
.000 Direcl Red 28
7000
6000
/
5000

""
3000
2000
'000
0
6 '0 M U • U ~ • • a ~ ~
TIme. min

Figure A.42 - SRM chromatogram of Direct Red 28

© ISO 20 14 - All rights reserved 21

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

AnnexB
(informative)

Round robin test results

B.l Sample preparation

Samples pre pa r ed with the carcinogenic dyes tuffs for the round robin tes t are shown in Table B.l .

Table B.l - Round robin test samples prepared

Dye concentration
No. Kind of dyestuff Textile material Kind oftextile
%
1 Acid Red 114 Wool woven 0.2
2 Acid Red 114 Polyami de w oven 1.0
3 Acid Red 26 Wool w oven 0.2
4 Acid Red 26 Polyam id e w oven 1,0
5 Dis per se Yellow 3 Polyam ide woven 1,0
6 Dispe r se Orange 11 Polyes ter woven 1,0
7 Basic Red 9 Acry li c woven 1,0

B.2 Participants
The tes t par ticipa nts were from Ja pa n, China, Ge rmany, Ita ly, Portugal, UK a nd Turkey. The number of
la bora tori es we re Ja pan : 5, Ch ina: 1, Ge rm a ny: 1, Italy: 1, Portuga l: 1, UK : 1 a nd Turkey: 1.

B.3 Test results

The da ta show ex tracts by mill ig r a m pe r kilogra m (mg/ kg). The re pea ta bility a nd r epro du cibility a r e
s hown in eac h table (see Tables B 2 to liJl).

Table B.2 - Round robin tes t result on Acid Red 114, 0,2 % (wool)

Data (Il = 3)
Standard
Testing facility mg/ kg Average Variance
deviation
1 2 3
A 124 117,8 121 120,9 3,1 9,6
B 123 122 191 145,3 39,6 1564,3
C 43,7 33,7 43,3 40, 2 5,7 32,1
D 140,8 146 131,2 139,3 7,5 56,4
A 124 117,8 121 120,9 3,1 9,6
B 123 122 191 145,3 39,6 1 564,3
C 43,7 33,7 43,3 40,2 5,7 32,1
D 140,8 146 131,2 139,3 7,5 56,4
G 143 146 151 146,7 4,0 16,3

22 © ISO 2014 - All rights reserved

 I.S. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table B.2 (cont inued)

Da ta (n = 3)
St a nd a rd
Testin g fa cility mg/kg Ave rage Va rian ce
de vi ati o n
1 2 3
Ii 102,6 110 107,1 106,6 3,7 13,9
Average 146,8 8,3 180,0
Within laboratory variance - - 1 800,0
Reproducibility variance - - 180,0
Between laboratory variance - - 5 529,3
Reproducibility variance - - 5 709,2
Repeatability standa rd deviation 13,4
Reproducibility sta ndard deviation 75,6
Coefficient of variat ion of repeatabil ity 9,1 %
Coefficient of variation of reproducibility 51,5%

Ta ble B.3 - Round robin tes t r esult on Acid Red 114, 1,0 % (polyamide)

Da t a (n = 3) mg/kg St a nd a rd
Testing facility Average Var ia nce
1 2 3 de viation
A 2774,6 2136 2377,2 2429,3 263,3 103985,7
B 23 15 2507 2221 2347,7 119,0 21 249,3
C 1568,9 1 341,5 1 611,2 1 507,2 118,4 21039,7
D 3265,9 3832,7 3488,7 3529,1 233,1 81539,7
E 4820,4 40 19,2 4231 4356,9 339,0 172 362,2
F 10500 10400 10 500 10466,7 47,1 3333,3
E 3720 3883,2 3775,2 3792,8 67,8 6890,9
F 2962,3 3098,5 2870,6 2977,1 93,6 13 149,6
G 3136 3018 3242 3132,0 91,5 12556,0
H 1 007,6 1024,3 909,1 980,3 50,8 3875,4
Average 3551,9 142,4 43998,2
Within laboratory variance - - 43998 1,8
Reproducibility va ria nce - - 43998,2
Between laboratory variance - - 6947936,8
Reproduc ibil ity va riance - - 6991935,0
Repeatability sta ndard deviation 209,8
Reproducib ility standard deviation 2644,2
Coeffic ient of variation of repeatability 5,9 0/0
Coefficient of var iatio n of reproducibility 74,4 %

Table B.4 - Round robin tes t result on Acid Red 26, 0,2 % (wool)

Da ta (n = 3) mg/kg St a nd a rd
Testing facility Average Variance
1 2 3 deviation
A 49 54,8 50 51,3 2,53 9,6
B 72 59 87 72,7 11,44 196,3

© ISO 2014 - All rights reserved 23

 I.S. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table 8.4 (continued)

Data (n ; 3) mgjkg Standard
Testing facility Average Variance
1 2 3 deviation

C 62,4 66,2 68,6 65,7 2,55 9,8

D 64,5 64,1 62,3 63,6 0,96 1,4
E 65,6 65,7 70,7 67,3 2,38 8,5
F 105 105 105 105,0 0,00 0,0
E 70,2 76 71,8 72,7 2,45 9,0
F 57 61,1 63,9 60,7 2,83 12,0
G 82 81 90 84,3 4,03 24,3
H 106,9 111.1 100,7 106,2 4,27 27,4
Average 75,0 3,3 29,8
Within laboratory variance - - 298,3
Reproducibility variance - - 29,8
Between laboratory variance - - 335,1
Reproducibility variance - - 365,0
Repeatability standard deviation 5,5
Reproducibility standard deviation 19,1
Coefficient of variation of repeatability 7,3 %
Coefficient of variation of reproducibility 25,5 %

Table 8.5 - Round robin test result on Acid Red 26, 1,0 % (polyamide)

Data (n ; 3) mgjkg Standard

Testing facility Average Variance
1 2 3 deviation
A 5515,3 5295,7 5876,2 5562,4 239,3 85908,9
B 5028 3994 4059 4360,3 472,86 335390,3
C 6826,2 5294,7 5908,7 6009,9 629,31 594049,1
D 6349,8 6400,1 6488,3 6412,7 57,24 4915,3
E 4992,1 5006,8 5 064,1 5021,0 31,06 1447,2
F 6950 6940 6870 6920,0 35,59 1900,0
E 6433,5 6489,3 6457,4 6460,1 22,86 783,7
F 6409,9 6498,7 6317,6 6408,7 73,94 8200,3
G 8134 7405 7382 7640,3 349,20 182912,3
H 4630,6 4497,9 4826,4 4651,6 134,93 27309,9
Average 5944,7 204,6 124281,7
Within laboratory variance - - 1242817,0
Reproducibility variance - - 124281,7
Between laboratory variance - - 1079136,5
Reproducibility variance - - 1203418,2
Repeatability standard deviation 352,5
Reproducibility sta nd ard deviation 1097.0
Coefficient of variation of repeatability 5,9 %
Coefficient of variation of reproducibility 18,5 %

24 © ISO 2014 - All rights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table B.6 - Round robin result on Disperse Yellow 3, 1,0 % (polyamide)

Data (n = 3) mg/kg Standard
Testing facility Average Variance
1 2 3 deviation
A 2362 3814 2861 3012 738 544252,3
B 4900 4400 4300 4533 321 103 333,3
F 2070 1930 1930 1 977 81 6533,3
K 776 706 - 741 49 2450,0
L 2012 1784 1 795 1864 129 16532,3
M 3848 3530 - 3689 225 SO 562.0
Average 2636,0 257,2 120610,6
Within laboratory variance - - 723663,3
Reproducibility variance - - 120610,6
Between laboratory var iance - - 1894510,8
Rep roducibi lity var iance - - 2015121,3
Repeatability s tandard deviation 347,3
Reproducibility sta ndard deviation 1419,S
Coefficient of va ri at ion of repeatability 13,2 %
Coefficient of var iat ion of reproducibility 53,9 %

Table B.7 - Round robin test result on Disperse Orange 11, 1,0 % (polyester)
Data (n = 3) mg/ kg Standard
Testing facility Average Variance
1 2 3 deviation
A 356 1440 354 716,7 626,4 392 409,3
B 754 754 756 754,7 1,2 1,3
F 173 164 102 146,3 38,7 1 494,3
K 316 293 327 312,0 17,4 301,0
L 222 248 203 224,3 22,6 510,3
M 160 172 - 166,0 8.5 72,0
Average 386,7 119,1 65798,1
Within laboratory va ria nce - - 394788,3
Reproducibility varia nce - - 65 798,1
Between laboratory varian ce - - 76541,0
Reproducibility variance - - 142339,1
Repeatability standard devi ation 256.5
Reproducibility standard deviation 377,3
Coefficient of variation of repeatability 66,3 %
Coefficient of variation of reproducib il ity 97,6 %

Table B.8 - Round robin result on Basic Red 9, 1,0 % (acrylic)

Data (Il = 3) mg/kg Standard

Testing facility Average Variance
1 2 3 deviation

A 3,6 33,0 3,8 13,5 16,9 286,6

© ISO 2014 - All rights reserved 25

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Table B.8 (continued)

Data (n = 3) mg/kg Standard
Testing facility Average Variance
1 2 3 deviation
B 9,6 8,1 7,0 8.2 1,3 1,8
F 1,0 1,5 1,3 1,3 0,3 0,1
K 1,5 6,8 4,7 4,3 2.7 7,1
L 10,2 12,6 16,6 13,1 3,2 10,5
M 2,4 2,8 - 2,6 0,3 0,1
Ave rage 7,2 52,6 51,0
Within laboratory variance - - 307,5
Reproducibility variance - - 44,8
Between laboratory variance - - 7380,8
Reproducibility var iance - - 7425,6
Repeatability standard deviation 6,7
Reproducibility sta ndard devi atio n 86,2
Coefficient of variation of repeatability 93,4 %
Coefficient of variation of reproducibility 1201,9 %

26 © ISO 2014 - All rights reserved

 1.5. EN ISO 16373-3:2014
ISO 16373-3:2014(E)

Bibliography

[1] ISO 3696, Water for analytical laboratory use - Specification and test methods

[Z] ISO 4787, Laboratory glassware - Volumetric instruments - Methods for testing of capacity and
for use
[3] ISO 5725-2, Accuracy (trueness and precision) of measurement methods and results - Part 2:
Basic method for the determination of repeatability and reproducibility of a standard measurement
method
[4] EN 14362-1, Textiles - Methods for determination of certain aromatic amines derived from azo
colorants - Part 1: Detection of the use of certain azo colorants accessible with and without
extracting the fibres
[5] EN 14362-3, Textiles - Methods for determination of certain aromatic amines derived from
azo colorants - Part 3: Detection of the use of certain azo colorants, which may release
4-aminoazobenzene

[6] EN 17234-1, Leather - Chemical tests for the determ ination of certain azo colorants in dyed
leathers - Part 1: Determination of certain aromatic amines derived from azo colorants
[7] EN 17234-2, Leather - Chemical testsfor the determination of certain azo colorants in dyed leathers
- Part 2: Determination of 4-aminoazobenzene

© ISO 2014 - All rights reserved 27

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Get permission to copy from or network this publication W'NW.saiglobal.com/licensing

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