Leather Determination of ethoxylated alkylphenols Part 1: Direct method
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1 DRAFT INTERNATIONAL STANDARD ISO/DIS IULTCS/IUC 28-1 Secretariat: IULTCS Voting begins on Voting terminates on INTERNATIONAL ORGANIZATION FOR STANDARDIZATION МЕЖДУНАРОДНАЯ ОРГАНИЗАЦИЯ ПО СТАНДАРТИЗАЦИИ ORGANISATION INTERNATIONALE DE NORMALISATION Leather Determination of ethoxylated alkylphenols Part 1: Direct method Cuir Détermination chimique des alkylphénols éthoxylés Partie 1: Méthode directe ICS ISO/CEN PARALLEL PROCESSING This draft has been developed within the European Committee for Standardization (CEN), and processed under the CEN-lead mode of collaboration as defined in the Vienna Agreement. This draft is hereby submitted to the ISO member bodies and to the CEN member bodies for a parallel five-month enquiry. Should this draft be accepted, a final draft, established on the basis of comments received, will be submitted to a parallel two-month approval vote in ISO and formal vote in CEN. This draft International Standard is submitted to all ISO member bodies for voting, as a standard prepared by an international standardizing body in accordance with Council Resolution 42/1999. The proposer, International Union of Leather Technologists and Chemists (Commission IUC, IULTCS), has been recognized by the ISO Council as an international standardizing body for the purpose of Council Resolution 42/1999. To expedite distribution, this document is circulated as received from the committee secretariat. ISO Central Secretariat work of editing and text composition will be undertaken at publication stage. Pour accélérer la distribution, le présent document est distribué tel qu'il est parvenu du secrétariat du comité. Le travail de rédaction et de composition de texte sera effectué au Secrétariat central de l'iso au stade de publication. THIS DOCUMENT IS A DRAFT CIRCULATED FOR COMMENT AND APPROVAL. IT IS THEREFORE SUBJECT TO CHANGE AND MAY NOT BE REFERRED TO AS AN INTERNATIONAL STANDARD UNTIL PUBLISHED AS SUCH. IN ADDITION TO THEIR EVALUATION AS BEING ACCEPTABLE FOR INDUSTRIAL, TECHNOLOGICAL, COMMERCIAL AND USER PURPOSES, DRAFT INTERNATIONAL STANDARDS MAY ON OCCASION HAVE TO BE CONSIDERED IN THE LIGHT OF THEIR POTENTIAL TO BECOME STANDARDS TO WHICH REFERENCE MAY BE MADE IN NATIONAL REGULATIONS. RECIPIENTS OF THIS DRAFT ARE INVITED TO SUBMIT, WITH THEIR COMMENTS, NOTIFICATION OF ANY RELEVANT PATENT RIGHTS OF WHICH THEY ARE AWARE AND TO PROVIDE SUPPORTING DOCUMENTATION. International Organization for Standardization, 2012
2 IULTCS/IUC 28-1 Copyright notice This ISO document is a Draft International Standard and is copyright-protected by ISO. Except as permitted under the applicable laws of the user s country, neither this ISO draft nor any extract from it may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, photocopying, recording or otherwise, without prior written permission being secured. Requests for permission to reproduce should be addressed to either ISO at the address below or ISO s member body in the country of the requester. ISO copyright office Case postale 56 CH-1211 Geneva 20 Tel Fax copyright@iso.org Web Reproduction may be subject to royalty payments or a licensing agreement. Violators may be prosecuted. ii ISO 2012 All rights reserved
3 Contents Page Foreword... iv Introduction... v 1 Scope Normative references Principle Apparatus and materials Chemicals Sampling Sample preparation and analysis Extraction Analysis Calculation Test reports... 3 Annex A (informative) Chromatographic analysis operating parameters... 4 A.1 Preliminary comment... 4 A.2 High Performance Liquid Chromatography (HPLC) and Triple Quadrupole Mass Spectrometer (MSMS) operating parameters... 4 A.3 Example of chromatogram and mass spectrum... 5 ISO 2012 All rights reserved iii
4 Foreword ISO (the International Organization for Standardization) is a worldwide federation of national standards bodies (ISO member bodies). The work of preparing International Standards is normally carried out through ISO technical committees. Each member body interested in a subject for which a technical committee has been established has the right to be represented on that committee. International organizations, governmental and non-governmental, in liaison with ISO, also take part in the work. ISO collaborates closely with the International Electrotechnical Commission (IEC) on all matters of electrotechnical standardization. International Standards are drafted in accordance with the rules given in the ISO/IEC Directives, Part 2. The main task of technical committees is to prepare International Standards. Draft International Standards adopted by the technical committees are circulated to the member bodies for voting. Publication as an International Standard requires approval by at least 75 % of the member bodies casting a vote. Attention is drawn to the possibility that some of the elements of this document may be the subject of patent rights. ISO shall not be held responsible for identifying any or all such patent rights. ISO /IUC 28-1 was prepared by the Chemical Test Commission of the International Union of Leather Technologists and Chemists Societies (IUC Commission, IULTCS) in collaboration with the European Committee for Standardisation (CEN) Technical Committee CEN/TC 289, Leather, the secretariat of which is held by UNI, in accordance with the agreement on technical co-operation between ISO and CEN (Vienna Agreement). IULTCS, originally formed in 1897, is a world-wide organisation of professional leather societies to further the advancement of leather science and technology. IULTCS has 3 Commissions, which are responsible for establishing international methods for sampling and the testing of leather. ISO recognises IULTCS as an International Standardising Body for the preparation of test methods for leather. ISO consists of the following parts, under the general title Leather Determination of ethoxylated alkylphenols: Part 1: Direct method Part 2: Indirect method iv ISO 2012 All rights reserved
5 Introduction Nonylphenol ethoxylate belongs to the non-ionic surfactants. The biodegradation of nonylphenol ethoxylate releases the difficult to biodegrade branched nonylphenol. Nonylphenol is a hormonal acting substance that is toxic for waterborne organisms and many other organisms. For this reason the release of nonylphenol ethoxylate into the environment should be avoided. In 2003 the European Directive 2003/53/EC restricted the sale and use of nonylphenol and nonylphenol ethoxylate in product preparations for industries with discharges to waste water. Preparations containing concentrations equal or higher than than 0,1 % of nonylphenol ethoxylate or nonylphenol were forbidden. This Directive is included as part of the EU Regulation 1907/2006 (REACH). In the leather industry the nonylphenol ethoxylate and octylphenol ethoxylate surfactants have been used. However, the water insoluble substances, nonylphenol and octylphenol, were not used. For this reason there have been 2 different analytical procedures prepared for analysing leather samples. Part 1 is a fast method that directly determines the ethoxylated alkylphenol. It is an efficient procedure for the analysing of a larger number of leather samples. This procedure requires HPLC with triple quadrupole mass spectrometer (MSMS) to identify the nonylphenol ethoxylate and octylphenol ethoxylate. Part 2 is a procedure for analysing the alkylphenol. The ethoxylated alkylphenol is cleaved to form the alkylphenol, which is identified using HPLC or GC-MS equipment. This method can also be used to indirectly determine the alkylphenol ethoxylate content in leather and process auxiliaries. ISO 2012 All rights reserved v
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7 DRAFT INTERNATIONAL STANDARD ISO/DIS Leather Determination of ethoxylated alkylphenols Part 1: Direct method 1 Scope This method is to determine alkylphenol ethoxylate (nonyphenol ethoxylate and octylphenol ethoxylate) in leather. This direct method is a suitable method where a larger number of leather samples are to be checked for the presence of alkylphenol ethoxylates. This method requires the use of HPLC with triple quadrupole mass spectrometer to identify the alkylphenol ethoxylate. Annex A of this standard is for information only. 2 Normative references The following referenced documents are indispensable for the application of this document. For dated references, only the edition cited applies. For undated references, the latest edition of the referenced document (including any amendments) applies. ISO 2418, Leather Chemical, physical and mechanical and fastness tests Sampling location ISO 4044, Leather Chemical tests Preparation of chemical test samples 3 Principle The leather sample is extracted in methanol using an ultrasonic bath. Subsequently an aliquot of the solution can be directly analysed without further reconditioning of the sample using High Performance Liquid Chromatography (HPLC) with a Triple Quadrupole Mass Spectrometer (MSMS). 4 Apparatus and materials Normal laboratory apparatus and, in particular, the following: 4.1 Ultrasonic bath, at least 160 Watt with controllable heating ml screw cap glass with lid. 4.3 Polypropylene or polyethylene syringe, 2 ml 4.4 Syringe membrane filters, 0,2 µm, for use with syringe (4.3). 4.5 Volumetric flasks, 10 ml and 100 ml 4.6 Analytical balance, weighing to 1 mg ISO 2012 All rights reserved 1
8 4.7 Pipettes, various sizes, 1mm to 5 ml 4.8 Instrumental equipment: High performance liquid chromatography with gradient elution and triple quadrupole mass spectrometer (HPLC-MSMS). 5 Chemicals If not otherwise defined, analytical reagent grade chemicals shall be used. 5.1 Methanol, CAS 1) No Nonylphenol ethoxylate, for example, 4-nonylphenol ethoxylate (technical), CAS No Octylphenol ethoxylate, for example, 4-nonylphenol ethoxylate (technical), CAS No Stock solution of nonylphenol ethoxylate and octylphenol ethoxylate, ρ = 250µg/ml 25 mg of the respective alkylphenol ethoxylate (5.2 and 5.3) are dissolved in different 100 ml volumetric flasks with methanol and filled up to the mark. 5.5 Calibration solutions of nonylphenol ethoxylate and octylphenol ethoxylate Four calibration solutions of ρ = 2,5 µg/ml, ρ = 5 µg/ml and ρ = 10 µg/ml and ρ = 50 µg/ml for each alkylphenol ethoxylate are prepared using the respective stock solution (5.4). 6 Sampling The sampling shall be made according to ISO If a sampling according to ISO 2418 is not possible (e.g. in case of leather from finished products like shoes, clothing, etc.) the details of the sampling must be stated in the test report. Glue residuals must be mechanically removed from leather samples. The leather samples shall be ground or cut into smaller pieces according to ISO Sample preparation and analysis 7.1 Extraction Approximately 1 g of the ground leather sample is weighed accurately to 10 mg in a 22 ml screw top glass bottle (4.2). 10 ml methanol (5.1) is added and the sample extracted for one hour in an ultrasonic bath (4.1) at 70 C. 7.2 Analysis An aliquot of the extraction solution is removed using a disposable syringe (4.3) and transferred into a HPLC sample vial using a syringe filter (4.4). The aliquot is now ready for the HPLC analysis. The detection of the alkylphenol ethoxylate is made using a HPLC with gradient elution and triple quadrupole mass spectrometer (4.8). Guidelines for suitable chromatographic conditions are given in Annex A. 1) CAS = Chemical Abstracts System 2 ISO 2012 All rights reserved
9 7.3 Calculation The determination of the alkylphenol ethoxylate in the extracted solution takes place using calibration graphs that will be defined through the peak areas of the four analysed calibration solutions (5.5). The content of alkylphenol ethoxylates is calculated as mass portion, w, in milligram per kilogram (mg/kg) of the leather sample according to the following equation: ( As b) V w a m E A s peak area of alkylphenolethoxlate in the extracted solution b a V intercept of the calibration graph slope of the calibration graph final volume used according to 7.1 in millilitre (ml); here 10ml m E weight of the leather sample in gram (g) 8 Test reports The test report shall include at least the following information: a) a reference to this international standard, ISO ; b) type, origin and denomination of the sample (aliquot, as far as relevant); c) date of receipt and date of examination; d) sampling method; e) detection method and method of the quantitative determination; f) results, stated as content of alkylphenol ethoxylates in milligram per kilogram (mg/kg) and limit of detection. ISO 2012 All rights reserved 3
10 Annex A (informative) Chromatographic analysis operating parameters A.1 Preliminary comment As the HPLC equipment (4.8) of the laboratories can vary, no general valid instructions can be provided for the chromatographic analysis. The following parameters have been successfully tested and used. A.2 High Performance Liquid Chromatography (HPLC) and Triple Quadrupole Mass Spectrometer (MSMS) operating parameters Eluent 1: 1 ml formic acid in 1000 ml water, 0,1 % Eluent 2: Stationary phase: Guard Column: Volume flow: Methanol Pursuit XRs C18 2) (3 µm); (150 x 2,0) mm MetaGuard 2.0 Pursuit XRs C18 (3 µm) 180 µl/min Gradient: See Table A.1 Table A.1 Gradient Program Time min Eluent 1 % Eluent 2 % Column temperature: 40 C Injection volume: 10,0 µl Detection: Spray-gas: Inert gas: Ionisation: Triple quadrupole mass spectrometer Nitrogen Argon API Electrospray positive, Fragmentor 100 V 2) Pursuit XRs C18 is an example for a suitable and commercially available product. This information serves to simplify the use of this document for the user and cannot be deemed as a recommendation by ISO for this product. 4 ISO 2012 All rights reserved
11 A.3 Example of chromatogram and mass spectrum Key X minutes Y kcounts Z m/z W kcounts 1 Std001.XMS Intensity of Base Peak Filtered 2 Spectrum 1A BP: 249,0 (45973=100%), std001.xms min, Scan: 955, Merged, RIC: 92588, BC Figure A.1 HPLC-MSMS Chromatogram and mass spectrum of nonylphenol ethoxylate ISO 2012 All rights reserved 5
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