DISCLAIMER 

This report is the property of Clariant. 

Its content is confidential and not for general 

release. It is not allowed to cite and reveal the report or its 

content to a third party without prior written approval of 

Clariant. 

REPORT 

Leuco Sulfur Black 1 

Determination of the Boiling Point /Boiling Range 

harlanTM 

... 

Data Requirements I 

Test Guidelines: 

EEC Directive 92/69, A.2, December 1992 

OECD No. 103, July 1995 

Study Director: 

Test Facility: 

Sponsor: 

Study Identification: 

Version: 

Study Completion Date: 

Council Regulation (EC) No. 440/2008, A.2 

Dr Jens Franke 

Harlan Laboratories Ltd. 

Zelgliweg 1 

4452 Itingen I Switzerland 

Clariant Products (Switzerland) Ltd. 

Rothausstrasse 61 

4132 Muttenz I/ Switzerland 

Harlan Laboratories Study C30931 

Final 

February 24, 2009 

Page 1 of 18 

188 ON SNIV1N08 

p ~ 6J;)_7/ ).=<_ 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

CONTENTS 

Report Page2 

CONTENTS .................................................................................................................................... 2 

LIST OF TABLES .......................................................................................................................... 2 

LIST OF FIGURES ......................................................................................................................... 2 

GLP CERTIFICATE ....................................................................................................................... 3 

SIGNATURES ................................................................................................................................ 4 

STATEMENT OF COMPLIANCE ................................................................................................ 5 

QUALITY ASSURANCE GLP STATEMENT ............................................................................. 6 

PREFACE ....................................................................................................................................... 7 

General Information ............................................................................................................... 7 

Responsibilities ...................................................................................................................... 7 

Schedule ................................................................................................................................. 7 

Data Requirements I Test Guidelines .................................................................................... 8 

Archiving ............................................................................................................................... 8 

Summary of Study Plan Amendments ................................................................................... 8 

1 SUMMARY ........................................................................................................................... 9 

2 PURPOSE ..... : ...................................................................................................................... 10 

3 MATERIALS AND METHODS ......................................................................................... 11 

3.1 Test Item ................................................................................................................ ll 

3.2 Test System ............................................................................................................ 11 

3.3 Principle of the Test ............................................................................................... 11 

3.4 Performance of the Test ......................................................................................... 12 

3.4.1 Test System ............................................................................................. 12 

3.4.2 Preliminary Test ...................................................................................... 12 

3.4.3 Main Test ................................................................................................. 12 

3.5 Data Handling ........................................................................................................ 13 

4 RESULTS AND DISCUSSION .......................................................................................... 14 

4.1 Preliminary Test .................................................................................................... 14 

4.2 Main Test ............................................................................................................... 14 

5 CONCLUSION .................................................................................................................... 15 

6 TABLES .............................................................................................................................. 16 

7 FIGURES ............................................................................................................................. 17 

LIST OF TABLES 

Table 1 Determination ofthe Boiling Point ofLeuco Sulfur Black 1 (Summary) .................. 16 

LIST OF FIGURES 

Figure 1 DSC-curve of Leuco Sulfur Black 1 (Preliminary Test) ............................................ 17 

Figure 2 DSC-curve ofLeuco Sulfur Black 1 (1st Main Test) .................................................. 18 

t. \ •. '•. 
\ 

Harlan Laboratories Study C30931 

Leuco Sulfur Black I 

GLP CERTIFICATE 

..... 5chwelretisc:he EidgtftOssenschlft V Conf6diltatloo sul111 

ConfedHIZIOnt Svii'Zifl 

Conftdernlun IYizra 

Swlu CDnftderatlon 

Report 

fedt11l Deptrtment of Home Affairs DHA 

- Ollbof ..... _POPII 

Fedtfll DoptrlmtM of tilt I<Mtonmenl. 

Tronspotl. Enerp and CommuniCitlorll OETEC 

---.... ·--

SWlSSme ~ d" lC 

Statement of GLP Compliance 

According to Article 14 paragraph 3 Ordinance on Good Laboratoly Practice (OGLP, SR 813.112.1] 

The notification authority for chemicals confirms that the foHowing test facility was inspected with 

respect to the compliance with the SWiss Ordinance on Good Laboratory PractiCe, adopted on 18th 

May 2005 (OGLP, SR 813.112.1). This Ordinance is baaed on the OECD Principles of Good 

Laboratory Practice, as revised In 1997 and adopted on 26th November 1997 by decision of the 

OECD Council [C(97)1861Finaq. 

Unequivocal name and address 

of the test facility: 

Areas of expertise according to 

article 3 paragraph 1 letter d OGI..P: 

Harlan Laboratories Ltd. 

lelglweg 1 

44521tingen,~erland. 

1 J Physical-chemical testing, 

2J Toxicity studies, 

4.1 Environmental toxicity studies on aquatic 

and terrestrial organisms, 

5J Studies on behaviour In water, soil and air; 

bloaocumulation, 

6.1 Residue studies, 

1.1 Studies on etrects on mesocosms and 

natural ecosystems, 

8J Analytical and clinical chemistry testing, 

9.1 Other studies (safely pharmacology and 

anlmel melabollam). 

Inspection authority: Federal Office for the Environment (FOEN) I Federal Office of PubUc Health 

(FOPH) I Swiss Agency for Therapeutic Producls (SwissmecfiC) 

Date of inspection: 05th to D9th and 26th to 30th Novamber 2007 

Date of decision: 30th Aprft 2008 

Based on the above mentioned decision It can be confirmed that the above mentioned last facUlty 

Is able to conduct studies acc:ordlng to the aforementioned areas of expertise In compliance with 

the principles of GLP. The above mentioned test facility Is listed In the register and GLP 1st 

according to the Article 14 OGLP and is inspected on a regular basis according lo Article 6 

paragraph 2 OGLP. 

Swiss Fed8f1!1.011ice of Public Health 

Consumer P.fO(ectlon directorate 

,. __ .. __ .... _..,_....., .... _ _...,_,CIU'JIOr .. ,_, ... _ .... _ _ ,_OIIotaiP ... Ic __ or ____ .., ___ _ 

•• .,.. • .,_ . ...,••mnoa.r.t...,(CI!1IZIICM 

Page 3 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

SIGNATURES 

Study Director: 

Management: 

Report Page4 

Dr Jens Franke 

~ Dr Jom Schreitmiiller 

Date: ~7VotLf Zf;-t( lfl.O'\ 
Harlan Laboratories Study C30931 

Leuco Sulfur Black l 

GOOD LABORATORY PRACTICE 

Report 

STATEMENT OF COMPLIANCE 

Harlan Laboratories Study: 

Test Item: 

Study Director: 

C30931 

Leuco Sulfur Black 1 

Dr Jens Franke 

PageS 

Study Title: Determination of the Boiling Point I Boiling Range 

This study has been performed in compliance with the: 

Swiss Ordinance relating to Good Laboratory Practice adopted May 18th, 2005 [RS 813.112.1]. 

This Ordinance is based on the OECD Principles of Good Laboratory Practice, as revised in 

1997 and adopted on November 26th, 1997 by decision ofthe OECD Council [C (97)186/Final]. 

There were no circumstances that may have affected the quality or integrity of the data. 

Study Director: Dr Jens Franke 
Harlan Laboratories Study C30931 

Leuco Sulfur Black I 

Report Page 6 

QUALITY ASSURANCE GLP STATEMENT 

Harlan Laboratories Ltd., Zelgliweg I, 4452 Itingen I Switzerland 

Harlan Laboratories Study: 

Test Item: 

Study Director: 

Study Title: 

C30931 

Leuco Sulfur Black 1 

Dr Jens Franke 

Detennination of the Boiling Point I Boiling Range 

The general facilities and activities are inspected at least once a year and the results are reported 

to the responsible person and the management. 

Study procedures were periodically inspected. The study plan and this report were audited by the 

Quality Assurance. The dates are given below. 

Dates of Reports to the Study 

Dates and Types ofQA Inspections Director and Test Facility 

Management 

December 16, 2008 Study plan December 16, 2008 

January 06, 2009 Process based January 06, 2009 (Test perfonnance) 

February 18, 2009 Report February 18, 2009 

This statement also confinns that this final report reflects the raw data. 

Quality Assurance: Mr Ulrich Kofink 
Harlan Laboratories Study C30931 

Leuco Sulfur Black I 

PREFACE 

General Information 

Test Item: 

Study Title: 

Sponsor: 

Study Monitor: 

Test Facility: 

QA: 

Responsibilities 

Study Director: 

Deputy Study Director: 

Reporting: 

Technical Coordinator: 

HeadofQA: 

Schedule 

Experimental Starting Date: 

Experimental Completion Date: 

Study Completion Date: 

Report Page 7 

Leuco Sulfur Black I 

Determination of the Boiling Point I Boiling Range 

Clariant Products (Switzerland) Ltd. 

Rothausstrasse 6I 

4132 Muttenz I I Switzerland 

Dr Bruno Kunz 

Harlan Laboratories Ltd. 

Zelgliweg 1 

4452 Itingen I Switzerland 

Harlan Laboratories Ltd. 

Quality Assurance GLP 

Zelgliweg 1 

4452 Itingen I Switzerland 

Dr Jens Franke 

Ms Mirjam Weissenfeld 

Ms Sabine Affolter 

Mr Gregor Czichy 

Mr Tobias Fink 

January 12, 2009 

January 13,2009 

February 24, 2009 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

Report 

Data Requirements I Test Guidelines 

Page 8 

This study followed the procedures indicated by the following internationally accepted 

guidelines and recommendations: 

• EEC Directive 92/69, Part A, Methods for the determination of physico-chemical 

properties, A.2 "Boiling temperature", EEC Publication No. L383, December 1992. 

• OECD Guideline for Testing of Chemicals No. 103, "Boiling Point", adopted July 27, 

1995. 

• Council Regulation (EC) No. 440/2008, 30 May 2008, Part A, Methods for the 

determination of physico-chemical properties, A.2 "Boiling temperature" 

Archiving 

Harlan Laboratories Ltd., 4452 Itingen/Switzerland will retain the study plan, raw data, a sample 

of test item and the final report of the present study for at least ten years. 

No data will be discarded without the Sponsor's consent. 

Summary of Study Plan Amendments 

There were no amendments to the study plan. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

1 SUMMARY 

Report 

The boiling point of Leuco Sulfur Black 1 was determined to be 

which is equal to 

99.9 oc ± 0.1 oc 

373.1 K ± 0.1 K. 

Page 9 

This result was obtained using Differential Scanning Calorimetry (Thermal Analysis) method. 

The atmospheric pressure during the measurements was 100.4 kPa (preliminary test) and 

99.8 kPa (main tests). 

The boiling point of Leuco Sulfur Black 1 is influenced by its high water content. It can be 

assumed that the measured value corresponds to water only. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

2 PURPOSE 

Report 

The purpose of the study was to evaluate the boiling point I boiling range of the test item. 

Page 10 
Harlan Laboratories Study C30931 

Leuco Sulfur Black I 

Report 

3 MATERIALS AND METHODS 

3.1 Test Item 

Data of test item as supplied by the Sponsor. 

Identification: 

Batch Number: 

Purity: 

Appearance: 

Expiry Date: 

Storage Conditions: 

3.2 Test System 

See detailed description in Section 3 .4.1. 

Leuco Sulfur Black 1 

ESA0007595 

45.5% 

Paste Liquid 

July 11,2011 

At room temperature at about 20 oc 

Page 11 

Rationale: The test system(s) and test method(s) are recommended by international guidelines. 

3.3 Principle of the Test 

The above-mentioned guidelines contain several different methods for the determination of the 

boiling point I boiling range. These methods include thermal analysis using a calorimeter and 

visual tests (e.g. capillary test). During the present study the thermal analysis was used. 

A phase transformation, e.g. melting or evaporation, or a reaction, e.g. dissociation, usually is 

associated with a heat effect. In the calorimeter, two identical aluminium sample containers, one 

filled with the test item and the other empty (used as a reference), are heated at a constant rate. 

During the experiment, the heat effect, i.e. the difference in heat flow, between the sample 

container and the reference container is registered. 
Harlan Laboratories Study C3093 I 

Leuco Sulfur Black I 

3.4 Performance of the Test 

3.4.1 Test System 

Report Page 12 

Differential Scanning Calorimeter (Preliminary Test and Main Tests) 

Instrument: 

Sample cups: 

Reference cup: 

Test conditions: 

3.4.2 Preliminary Test 

Differential Scanning Calorimeter 

DSC 821, Mettler Toledo 

Aluminium cups. A lid with a defined perforation was 

used. 

Empty aluminium cup. 

The test was performed in an air atmosphere 

A test item amount of 13.76 mg was heated up from 25 °C to 400 °C at a rate of20 °C/min. The 

quantities of heat absorbed or released were measured and recorded. Before and after the test, the 

weight and the appearance of the sample were determined. 

3.4.3 Main Test 

As in the temperature range investigated, peaks were observed from which boiling of the sample 

could be deduced, the thermal analysis was repeated with 21.74 mg and 7.31 mg, respectively, in 

the immediate vicinity of the peak temperature (25 °C - 215 °C). For the actual determination of 

the boiling point, the temperature rise was adjusted to 10 °C/min. Before and after the tests, the 

weight and the appearance of the sample were determined. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

3.5 Data Handling 

Report Page 13 

The standard boiling point is defined as the temperature at which the vapour pressure of a liquid 

is the same as the standard pressure (101.325 KPa). The measured boiling point depends on the 

atmospheric pressure. 

During thermal analysis the peak width of an endothermic reaction also depends on sample 

amount. Therefore, the onset point of the relevant endothermic peak will usually be stated as 

boiling point. For poorly defined endothermic peaks/effects the range will be stated in the result 

section. 

The temperature at the boiling point I range is stated in degrees centigrade [

0

C] and Kelvin [K] , 

with regard to the ambient pressure during the measurement. 

Results are given in degrees centigrade and in Kelvin. 

Conversion of units ec to K): 

t = T- 273.2 

with 

t = Celsius temperature, degrees Centigrade [

0

C] 

T Thermodynamic temperature, Kelvin [K] 

The boiling point depends on the atmospheric pressure. A correction to normalized pressure can 

be made. Because the correction factor for the boiling point is a specific parameter for each test 

item, the correction factor had to be determined. The determination of this correction factor is 

beyond the scope of this study, therefore no correction will be applied to the boiling point 

observed. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

Report 

4 RESULTS AND DISCUSSION 

Page 14 

The determination of the boiling point I boiling range of the test item was performed according 

to the EEC Directive 92/69 and Council Regulation (EC) No. 440/2008, A.2 "Boiling 

temperature" and to the OECD Guideline No. 103: "Boiling point", adopted July 27, 1995. 

4.1 Preliminary Test 

The DSC-curve of the preliminary test (heating rate of 20 °C/min from 25 oc to 400 oq is 

shown in Figure 1. An endothermic heat effect, the boiling, was observed at 99.8 °C. After the 

experiment, the sample had lost 55% of its mass and the colour ofthe sample was black. 

4.2 Main Test 

In order to determine the boiling point more precisely, further DSC-runs were recorded between 

25 oc and 215 °C with a heating rate of 10 °C/min. During these runs, the boiling point was 

determined to be 100.0 °C and 99.8 °C. The samples lost 51% and 50% of their mass, 

respectively. After the measurements the sample was a black powder. The DSC curve of the first 

main test is given in Figure 2. The results of the thermal analysis are summarized in Table 1. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black I 

5 CONCLUSION 

Report 

The aim of this study was to determine the boiling point/range ofLeuco Sulfur Black I. 

The boiling point of Leuco Sulfur Black 1 is determined to be 

which is equal to 

99.9 oc ± 0.1 oc 

373.1 K ± 0.1 K. 

Page 15 

The atmospheric pressure during the measurements was 100.4 kPa (preliminary test) and 

99.8 kPa (main tests). 

The boiling point of Leuco Sulfur Black 1 is influenced by its high water content. It can be 

assumed that the measured value corresponds to water only. 
Harlan Laboratories Study C30931 

Leuco Sulfur Black 1 

6 TABLES 

Report Page 16 

Table 1 Determination of the Boiling Point of Leuco Sulfur Black 1 (Summary) 

Heating Range Heating Rate Boiling Point Boiling Point 

[oC] [°C/min] [OC] [K] 

Preliminary 25-400 20 99.8 373.0 Test 

1st Main Test 25-215 10 100.0 373.2 

2nd Main Test 25-215 10 99.8 373.0 

Mean of boiling point: 99.9 373.1 

Standard deviation(±): 0.1 0.1 

The mean boiling point was calculated from the bold values (onset point of the endothermic 

reaction). 

The tabulated values represent rounded results obtained by calculation using the exact raw data. 
i-C: 

"'eXO 

mw Experiment: C30931/VT/LSB1/CZG/12.1.09, 12.01.2009 14:21:53 

Methodenname: Vortest 25-400/20°C/min/AirMethode: Vortest 25-400/20°C/min/Air 

25.0-400.0°C 20.00°C/min 

0 

-so 

Integral -13.55e+03 mJ 

Onset 99.75 oc 

-100 Peak 122.14 oc 

Endset 146.14 °C 

Heizrate 20.00 

&C30931/VT/LSB1/CZG/12.1.09 

C30931/VT/LSBl/CZG/12.1.09, 13.7600 

so l.OO l.SO 200 250 300 350 

Harlan Laboratories ltd.: PhysChem METTLER TOLEDO STARe Sy
-o 

r 

$U 

-

(') 

0 

z 

z 

en 

z 

0 

(') 

. 22-

Aexo 

mW Experiment: C30931IHT1ILSB1ICZGI13.1.09, 13.01.2009 12:01:11 

0 

Methodenname: Maintest 25-215°CI10°C I Air 

1\... 

.. \ 1.. 

-20-

. .., 

-40-

-60-

-80-

-100-

Methode: Maintest 25-215°CI10°C I Air 

25.0-215.0°C 10.00°Cimin 

-120- Integral -20.84e+03 

Onset 100.03 °

&$C30931IHT1ILSB1ICZGI13.l.09 Peak l.l.7.9l. °

-l.40- C30931IHTl.ILSBl.ICZG/13.l..09, 21.7400 mg Endset l.38.2l. °

v 

Heizrate 10.00 °C

I I 

120 II 

T I I 

40 60 80 l.OO l.40 l.60 l.SO 2

-----

Harlan Laboratories Ltd.: PhysChem METTLER TOLEDO STAR