STUDY REPORT 

Sponsor: 

Monitor: 

Order no.: 

Test Faciity: 

Date: 

Page 1 of 24 
3 MATERIALS ... ............................................................................................................................................. 4 

3.1 Reference and Calibration Items ...................................................................................................... 4 

3.2 Chemicals and Materials ................................................................................................................... 4 

3.3 Instruments ........................................................................................................................................ 5 

4 METHODS .................................................................................................................................................... 5 

4.1 NMR Spectroscopy ............................................................................................................................ 5 

4.2 Mass Spectroscopy ............................................................................................................................ 5 

5 RESULTS AND DISCUSSION ...................................................................................................................... ? 

6 SUMMARY ........................................................................................................................................................ 24 

7 PERSONNEL .............................................................................................................................................. 24 

8 CONFIRMATION OFTHESTUDY REPORT ............................................................................................ 24 

page2 of24 
Fig. 6 Suggested reaction of

at high pH values ............................................................................... 9 

Fig. 7 Base Peak ( +ESI/MS), detail: V1 to V7 ............................................................................................. 1 0 

Fig. 8 Base Peak (-ESIIMS), detaii:V1 to V7 .............................................................................................. 11 

Fig. 9 Detail: (1) Base Peak and (2) +ESIIMS at RT 9.5 min of main peak (V4) ...................................... 12 

Fig. 10 Detail: (1) Base Peak and (2) -ESI/MS at RT 9.5 min of main peak (V4) ................................... 12 

Fig. 11 Detail:{1) Base Peak and (2) +ESIIMS at RT 14.6 min (V4) ........................................................... 13 

Fig. 12 Detail: (1) Base Peak, (2) lon trace at m/z 471 and (3) -ESIIMS at RT 14.6 min (V4) ................... 13 

Fig. 13 Suggested chemi:::al structure at RT 14.6 min ................................................................................. 14 

Fig. 14 Comparison of 13C-NMR spectra, detailed carbonyl region, bottom blue( .. in ~0. pH 4). XTAN reaction ... 14 

Fg. 15 1H-NMR spectrum of test item 

Fig. 16 I.~C-NMR spectrum of test item 

Fig. 17 ':C-NMR spectrum of test item 

Fig. 18 ':C-NMR spectrum of test item 

Fig.19 't-NMR spectrum of test item 

Fig. 20 ':C-NMR spectrum of test item 

1"1 Fig. 21 ·c-NMR spectrum of test item 

Fig. 22 L'c-NMR spectrum of test item 

Fig. 23 1H-NMR spectrum of test item 

Fig. 24 1H-NMR spectrum of test item 

Fig. 25 1H-NMR spectrum of test item 

Fig. 26 1H-NMR spectrum of test item 

Fig.27 1H-NMR spectrum of test item 

Fig.28 1H-NMR spectrum of test 

Fig. 29 1H-NMR spectrum attest item 

Fig. 30 1H-NMR spectrum of test i:em 

in D20 ................................................................... 15 

D20 ....................................................................... 15 

after 1000 I additbn,0.5h ................................. 16 

I additbn, 24h .................................. 16 

after 2000 I additbn, 1h .................................... 17 

I addition, 24h .................................. 17 

I addition, 1h .................................... 18 

after 2600 I addition, 24h ................................. 18 

after 1000 I addition, 30 min .................................. 19 

after 1000 I addition, 16h ................................... 20 

after 1000 I addition,24h .................................... 20 

after 2000 I addition, 30 min .............................. 21 

after 2000 I addition,24h ........................... 21 

2600 I add.,30 min (pH shift2.9 ppm!) ............. 22 

2600 I additbn, 24h ................................... 22 

Fig. 31 HMBC spectrum of test item ,~~~~after 1000 I addition, 24h ......................................... 23 

Fig. 32 HMBC spectrum of test item I after 2000 I addition, 24h ......................................... 23 

TABLES 

Tab.1 

Tab.2 

Tab.3 

Tab.4 

Tab.5 

Test item data ...................................................................................................................................... 4 

Chemicals actually used as reference and calibration items ........................................................... 4 

Chemicals and materials used in the study ....................................................................................... 4 

HPLC and MS parameters .................................................................................................................. 6 

Physical properties pH and temperature during titration ................................................................... 7 

page 3of24 
Tab.1 Test item data 

3 MATERIALS 

3.1 Reference and Calbration Items 

Tab.2 Chemicals actually used as reference and calibration items 

• 

3.2 Chemicals and Materials 

Tab. 3 Chemicals and materials used in the study 

page4of24 
Mass spectrometer Finnigan LTQ {Thermo Electron Corp., San Jose, CA) 

±ESI modus, introduction via LC 

Gradient pump Rheas2000 (Flux Instruments, Basei,CH) 

Degassing unit Online-DEGASSER ERC-3415 a (ERC GmbH, Riemerling , D) 

Autosampler HTC PAL System (CTCAnalytics AG, Zwingen, CH) 

Column oven L-5025 (Merck, Darmstadt, D) 

Diode array detector UV6000LP (ThermoFinnigan, San Jose, CA) 

Computer PIV 2B GHz under Windows XP and Software Xcaibur2.0. 

Standard operation procedures SAA-GMR011-02, -GMR012-03 and -GMR016-02 

Electronic semi-micro balance Sartorius R 180 D-"•D1 (Gottingen, D) 

Standard operation procedure SAA-G MR005-04 

4 METHODS 

4.1 NMRSpectroscopy 

1H-NMR and 13C-NMR spectra were recorded directly after sample preparation during the titration 

process and after different reaction times. 

The actually used NMR parameters appear on the spectrum plot. 

4.2 MassSpectroscopy 

HPLC/MS analyses (±ESI) were recorded from a second titration trial of several addition steps 

(adding of 50 ul , 100 ul, 150 ul, 200 I-ll and 400 ul, equivalent to V1 to V5). The last titration samples 

were additionally heated (equivalent to V6 and V7). 

The sample solutions were diluted and introduced by LC/MS coupling with column. 

page 5of24 
40 90 10 

45 90 10 

45.1 10 90 

50 10 90 

Flow: 230 IJI!min 

Injection Volume: 10 IJI 

Column Temperature: 40°C 

Detection Wavelength: 200-600 nm (PDA) 

Split: -

Scan Parameter: 50-2000 amu 

Number Micro Scans in Time: 5 in 200 ms 

Polarity and Source Type: +ESI -ESI 

Capillary Temperature: 275°C 275°C 

Sheath Gas Flow: 40 40 

Aux Gas Flow: 0 0 

Sweep Gas Flow: 0 0 

Spray Voltage: 5kV 4.9kV 

Capillary Voltage: 38V -34V 

Tube Lens: 125V -100V 

page 6 of24 
Tab.5 Physical properties pH and temperature during titration 

Comments : Samples taken at yellow highlighted titration steps 

The titration curves are shown in Fig. 2 and Fig. 3. The step by step addition of - solution 

changes the pH only slightly until approx. 2300 IJI were added. The buffer capacity was reached at 

2500 IJI. At 2600 IJI addition the pH dropped down comparable to a titration point. Further addition of 

- solution shows linear strong decrease of the pH value. After this titration point the reaction 

mixture became cloudy which is an indicator of intermolecular polymerisation. The reaction mixtures 

taken before stayed clear even after 24h. 

The temperature increases nearly linear indicating an exothermic reaction . At the titration point the 

temperature dropped down and rises up in the same linear way after further adding of -

solution. 

The NMR spectra ndicate a first and fast chemical reaction of-with NaOD at high pH values, 

the splitting of sulfonic acid and the formation of the carbaminic acid. This molecule dominants the 

NMR spectra after short reaction times. The further degradation to the amine is a slower reactbn 

and can be observed over hours and days at these high pH values (see comparison e.g. of Fig. 17 

and Fig. 18). 

page 7 of24 
Fig, 3 

10,.50 

10,1.10 

27 26,~ 26 

2S..S 

p 25 .s ,l4,5 

#! ~ ~.s 23 

u.s 

22 

·--.. ...... 

..... 

.. 

·~ 

0 

Temp. Variation during Titration 

..... 

........ ....... 

....... y 

......... 

...... 

...... 

.... 

!• 

0 500 

Altar the caneu.mption of the ~ NaOO the 9H dropped down and the eeconcfary lll8diorl etarta 

fcrmJnQ the emlno fllnction by loss of ~ followed by 1t1e tttltd ructiOn atep of forming the utea 

811uctln$. .. 

The tnttamalar:ular reac:ttan d is e GOmpetltlve reaction 10 the lnlemlolec:Uiat ~~. 

The end producta are molecules or partial cyclic a~ructum (d. Ag. 4 and Fig. 5). The Sll\letuMA 

were confirmed by the HPLCIMS anal~ of se~ reac1ton mblt.na. 

page 8 of24 

i I J a i ; a ~ a ~ a ~ I 1l .. .. a '! .. I • I i 8 I I f .. ., ... I I - I .. • • • • • ... fi t ~ B J rr ~ .., • s > ,. #i ~ I:S .. d ft ·- ;; ! .. I I ~ ""' e! " "' e ..: ... 

; .. ~ I '1 

- • .. ~ ! D i N 

.. ~ .. . '

· 

..,- 0 -· .. I 

... ... • 

0 

!· s 

... ~ 5 

9: H 

0 a" i"Tf .. .. .. .. 

Pnll.(~dl*al V1 to V1 

page 10 of 24 
"C 

fl) 

<0 

CD 

....\ 

....\ 

a 

~ 

'"T1 <P' 

():) 

i 

m 

~ 

I' 

rn 

~ (/) 

':::'-" 

0. 

! 

< -" 

6' 

!l 

0 :\Dato · 

(V.2.0) Slllile 86; E!SI neg. (LNX3n) 

V2.0 dEVG 

RT: 0 .00 - 29.96 SM: 78 

+50 IJL 

RT:9.48 

6 .40 8 .2"l MA: 1890319 

3.5 ~ 

13.22 14.86 17.25 20.78 

10~~_'I _L~~ ~=:::=:::~:: ;;;; --------------------------------~~~~~:-------~----- , 

n 

NL.... · 50c; , -· + 1 00 "L e.M Paak RT: 9.48 MS 

MA: 7259378 25.09 27.37 tnx33021v2n 

1003 

- 4 62 6.0_1 50~ 1 41 3 ·

7

~ 9 · 

RT: 9.48 

100~ MA:5069500 

50~ 1.86 3.88 4.8_8 6.14 8.68 8."Z6 A 

V3: + 150 fJL 

NL: 

5.87E5 

Base Peak 

~ MS 

3.~~ tnx33021v3n 

15.0..7 "\6;.._3~ ~Z..:.58 __ 1~.5"!..___20.30 12.16 "-,/ .,. V><" ~ V--....rv""~ 

RT:9.48 NL 

MA: 7536628 

1.~5 5.:11 6.08 6.95 8.77 l 13.58 14.18 

100-. V4: + 200 fJL 6.71E5 

Btleo Peak 

MS 

so . lmc33021V4n _,....,....J'"\,~-----"::;~""-._."" -~ ~ f''v'-..-

16.17 17.:.57 .. 1...8.84 21_.10 23.19 2~ .33 25~29 28.01 ---- ---------~-~ ..... 

RT:9.48 

100-:J MA: 22290265 

_J 

V5: +400J,JL 

NL: 

1.25E6 

Base Peak _ MS 

5 0-=j lnx330:?1 v5n 

~o 7.49 8.55 12 .. 7..5 13.47 16.19 18.92 21.36 23.34 24.75 2~.24 2_7 .97 

RT: 9.48 Nl..: 

100-:::; 

MA: 10695023 7 ,74E5 

V6: warm titr. 1 Baaa Peak _J 

MS 

50 2.6_6_ 3 .58_ 5.25_ 7.0.3. 11 .9.§. 12.96 15.82 17.96 20.49 ~_1_.42 24.33 25_.61 2§.98 lnx33021 vf)n 

RT:9~48 ___ --- -

1 00~ MA: 2360566 NL: 

4.0S 5.69 5.88 8.02_ ~1§. .· 12.~.9 13.46 17.15 18.46 20.48 3.08E5 

50 1.7..? . - ~ -~I"V-~ · """'-~ 26 59 Base Peak ,..,..,vv-- ~·~y- · ·· ...;_ 28.39 MS r ~~lnx33021v7n 

r-r-r-r-r-r-r-r-.,...-.,.--~-r--r---r-,---r-r--r- ---. --r-. -,--T-,r--r ,- -~- r· 1 r 1 r'" ,--r-·r- r -T-T--,--, -r·--T·--r--T T-T--T 1 ,---1--r- 1 r· -~--, 1 1 

0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 

Time (min) 

en 

c 

c.. 

'< 

~ 

'8 

;:+ 
- -

J 

I 

1' t:l • • • ·---··· ••• • 

285.2 

28e.2 

300 

(M+HJ+ 

330.2 3158..2 301.2 410.0 

""" mJz

830. 1 

..... 3 

01U• 

.. = 284 

Fig. 9 Detail: (1) Base Peak and (2) +ESI/MS at RT 9.5 min of main peak (V4) 

--(\-) 

RT· G.C:0•3000 SM )8 

! 

I 

• 0 0 10 12 1. 18 

nm•(mln) 

~1WVI~ Rl': ez A.V· 14 SB: 07 e...,oe.e,oa . e.-.. o. ~ HL; 6.tleE~ T: nus . o Ea• ~ ,.,. 1 :"JO.oo-.:lOOO 001 

32G.2 

(M+CI)· 

(.M-HJ· 

140.1 170.0 207.0 

1<50 200 230 

V4: +200 ~ 18 .. 30 

M=21W 

811 .0 537.2 

300 oOo 

S$0.0 &13f I l "P'11 I ~~·.3, 733.0 7<48.2 

eoo OSJ 100 ~ Fig.10 Detail: ( 1) Base Peak and (2) -ESIIMS at RT 9.5 min of main peak (V4) 

page 12 of 24 
\ 

10 12 14 

11me(tr.1n) :r,x:~:·J:)7,:. ·1·..:~-;~_;.l! .. (i~}t~ RT:1.t!~~4·1~.•:?.S AV:.l:~ SO:~? 1..-!.?; ! 1• U1 Nl:"!4H~·· 1": l n·.o~s . t: f. ... ·:·; I F~·li m1;· : ·.X}·~:m}·~- ~>)} I 

j 

111.J 1<1.11 -~27 . ."l. " 259.3 28$. 311 2 302 .3 47:!, SQO .t ~7<2 ~~4.1 mtr. 

1~.1-~ 7!tH5 21.J·l .~2.<)(.' '" 

Fig. 11 Detail: (1) Base Peak and (2) +ESI/MS at RT 14.6 min (V4) 

.. 2\.rO J.il 

a ... 

L 

V4; ·• 200 1 

2A 28 ]0 

M::::420 

tntl!\ .:1 11£ ~ 1 no .. l l•l-l.7 

I I t I I 1 I I I I I r~ ~· '··' .. ., ...... oo .... · j --------------------------------- ::n lt..os 21.10 :Z4.:U l.:S.t,9 7.ot !'~ >. 17 2.34 

4 8 10 12 

4.59--------------------------------------. 

1·1 

Tlme(min) 

17.22 IK.6J ln.54 

18 20 22 2·1 

·'-"'·· 

.-. i\o~l• ln -1 l'll•n 

26 28 3(l 

ltt:\.:~]lJL.i"\"·' XE-¥· '-~(. •. ~-... RT:l·•·+l.·l~-1:: AV:$8 SB:I.:>~ >·">··1 ~(}7 '1•)1'"!··1~10 NJ..:.l- 0<1 1.~ "l"·iTM~ '"'"· ~I Fu. rr..a. ( {l(/ .. 200(1 ():)J 

471.3 

IM+HCOO)· 

(M-H)· 

472.1 

461.:."' S:-\93 

tu

1:1.01 2%7.0 ' """")83flr'll1,_s, ... 2-·· 14""1"" ·t-Sjo.,. ""~.·2, .. :SOQ:;:;;·;;:.o .. , ... ~J1;.;· ' ... .eos;:.:- Q .•. ; ·- .. ~i;;3, ... , ... ::;Q 83:;;:;·;.2-t 10272 m• 9 u2o.o;; 

100 200 JOO 400 :500 000 700 600 goo J 000 1100 1200 

rnhr. 

Ftg. 12 Detail :(1) Base Peak,(2) lontrace at m/z471 and (3)-ESI/MSat RT 14.6 min (V4) 

page 13of 24 
I 

Fig.13 Suggested chemical structure at AT 14.6 min 

......... . 

... 

..... 

I 

uu• • ..-.. a 

page 14of 24 
10 

. .-.~"'\!.a.uc ..,_ 

~01"; 

ttX'JO(t)(IIJOs .... 

1 

lftA.,..~tH• .. ,. 

IH 

1.:0CIU"AC. 

....... 

11'01t~m1U\V 

t.OC!.7:!10Sif.H.-

"""'"' t't.O~.W7l"'r.tlt' FU 

0 

(130>1.- • 100 

Fig.15 1H-NMR spectrum of test item -in 0 20 

• D• 

--

. -· 

" ·-. --. --

~.' -· 

. . 

··-

'A~ 

Fig.16 

•• II 

page 15 of 24 
l·'~ ~r" ' ' ... - -- l'- ··• "'---l'-·· - ... l · · t----r---·-- - - - - --r----........... , ...... ----r--

l}u 1~1) 110 h)( I !50 I '\) t ';\! 12•) 110 Inc'~ eo t!J "'O ..to 3n 2•l 

Fig. 17 13C-NMR spectrum of test item-after 1000 1-11 addition, O.Sh 

-ml.l!-4h 

•••• '\I' 

.. 

-· ·-------······--·· ...... - -·-··r··-·· .. ··· · ······ .. .- .. --·· .. ... , -· 

IQ(• I~(• I ":"() W.• l41i !N 120 !H) I•Xi ItO ·•· 

Fig. 18 13C-NMR spectrum of test item -after 1000 1-11 addition, 24h 

page 16of24 
..... ·-· 

. , . 

.... 

Fig.19 

.... , .. ~.. ..... . 

...... -· ,""" ·-u• 

'1) ''"'"' .. 

_.,,,. .. , .... 

. 

~..: ... 

~:lll'··~···· 

'","i,~l,.""·::: ·.-. 

···:--r_: .... 

Fig. 20 

13C-NMR spectrum of test item -after 2000 IJI addition, 1 h 

........ 

13C-NMR spectrum of test item--after 2000 JJI addition, 24h 

page 17 of24 
Fig. 21 

. . 

' 

. ,. .. ···" 

13C-NMR spectrum of test item-after 2600 ~I addition, 1 h 

-. ..... 

page 18 of24 
11.0 

40.5J.iUWw." 

C.~~Atr<. 7..6a,... 

1flO((W\O(,I(.tM'\-

1 

(.;if,l,.H"4! I 11 •4~ ...... 

"' I..:IX'uwr. 1.;()CD 

1~"1'ilt/Cl(.o'(: 

i.(YJ ~73'1flr!I;U UH1 

f..Mo3t 

tAJCI~tZ11Jicr 

Ft.t 

0 

1'3f.liV 

0 

,.,. 

L-----"'-

Fig.~ 

111·NMRspectrum of test 

..,r,.,.. 

12.!17 

..... 

!lmmcPtn«r 11-! 

... ~ ..... 

,. 020 

t~!~tt.c 

01(1:8z:'SH: :'650t-4::>l\tM 

... 

.;O.bllm«" .,._ 

..... 

I 

(X'JOO(l(lU(iS~f: 

I 

CtU.UNII tt• • 

t:Wuc.c "' 

1!.,U47rtti<N '"""" 

OUO!.U'i"CWJ.fb: 

"""" roo 50'01W r.tn: lLI 

U'Jlllt: • 

0 

100 

· --A 

Fig:·24--·- rt-NMR~ of test item 

.0 

___ .A 

after 1000 !JI addition, 30 min 

page 19 of 24 
•• .:V!-D•r:.« 

Ci!IO uMIC 

r~t'l-:: ~ MO'XlDOO de; 

I 

C1Wlf,!EJ,.!1r ... 

"' :-10').-,c 

,..,.., 

1:-iliftl(.lfJtf( 

lOl !i731QI.t f .• u rM.Y. 

(,(J( !1:111.1::. l,:tv 

,,. 

v 

OXIIt.· 

0 

:& 

Fig. 25 1H-NMR spectrum oftest item -after 1000 ~I addition, 16h ~"• Ctu.HHf.l t1 

'" 1.4 aCJutae 

.... .., 1i'01007C10W 

(Q)61JI'OI:aa.""' 

, .. 

cor.~t61J.'.It 

Eu 

0 

v,.,H: 

0 

"'' .::~; ;:. : • v i i i 

l 

__ L ____ ._ -----·---· 

Fig. 26 1 H-NMR spectrum of test item •••• after 1000 ~I addition, 24h 

page20 of24 
C 

1.12 

.. .,...., 

C!;(lu:lilf": 

:'!"JOC.illf 

\UI(.(JCJI)"i()~ 

' 

O~ff 

1-tOOo.~sa ·~ ...... 

1'fl*el7(.lDW fAJ05rJ1'0llllt.OI.· 

<1630 

tti:J!..fN'I'13•1.-t.; 

'" 0 O>O>V 

. 

"'" 

Fig. 27 1H-NMR spectrum of test item-after 2000 lJI addition, 30 min 

·-•CIJ.Utlet,!l.-.. ,. ..... ._. 

1H 

1 .. 00'\IM(. 

.... 

l291tffttOVI 

GOD 572'JON.Mt17 

..... 

OQCI!«lllr.'M~tl% 

w 

031)1-1.· " 

0 

"" 

_______ L _______ _ 

XTANV~Ne0H

2ni~ 

... 

\7 

Fig.28 1H-NMR spectrum of test item ~fter 2000 IJI addition, 24h 

•• 

page 21 of 24 
12i 

.:ow~ .,.,_ 

..... 

100000000-

, 

~·Ct\.&JMI f1••••••-.oo 

Ill 

1.:QOw.«. 

........ 

~7$U~1t1.0W 

O(il)~-;:r.mr.J.Ifi.· 

r.~ f«• •A¥.00."17 WI C:. 

IU 

O:IOtf: • 

• "'' 

Fig.29 1H-NMR spectrum of test item-after 2600 !JI add., 30 min (pH shift 2.9 ppm!) 

CHI. .. Hlln ••• •·-

1 ~ "'"' "' UC;f.t. ....... 

12 91911610 Ill 

liOO.J7.11CitaT.Wir r;<>)!l 

tcn:.oo')1Atii.JIV 

Ul 

il:.JII.; • 

0 

'"" 

1------ -·---·- -J.._ - ---

- - ---.---·--- •• 

Fig. 30 

~2

tm124t\ 

·~ i \7 

page 22 of 24 
Fig. 31 

Fig.32 

. . ~ 1 

;

.; ... 

• ' 

·; -~ ; -~ - ----t-. 

:· 

.... ~ 1 r 

I 

2.5 2.0 

!·-t

l . 

=----1. 

f'"" ~ 

-r ~ ---......,..=---

1.5 1.0 

· 60 

I 

!L: 

: rl 120 

: · 140 

:' 

1r60 

.. ;l: 

HMBC spectrum of test item --after 1000 JJI addition, 24h 

ai 

.;,--. j• ~ "! . , ..... 

.. 

. ;. 

--+- .... ----~----- 4.0 3.5 3.0 2.5 2.0 1.5 

~ 

' 

! 

.j 

! 1------· 

1.0 

• 80 

l ,oo :I 

;·c 120 

• 140 

160 

180 

.j f 200 \J 

0.5 

HMBC spectrum of test item-after 2000 JJI addition, 24h 

.. ....,, -~·~--- .. .... _ .. .._.._ "'' ,.,, ... ,, , ....... ..... .. . WoOl • 

.,~ .... 

--~

n-- '"'" ...,. w•- .. " ""' ··-uoa "LfW t2..11t1H•w 

POt Mel PU1t1 Mel 

-~o- -· '""' "" .., 11-- "-2 ..... ••uw .. ,......, ., lfO: llfi::IIC."» .... 

~~ 

---~HTC:

.....,... •- ~ IIIC 1:-

...,.... 

..

.... 

. 

,

. 

. 

CJI'n ..... ... OI'J2 .. .. 

~ ... .. 

.... 

- --

, 

-

"' "' .01 ,.,..,""' 

~~ tMMmHI ::.0... =--:,.-

. .. -~

- Mkl ..... 

......

... 

-

. 

... 

.. . " .... 

. ""' 

-

., • 1\l.IDr» ... 

-

u 

-

... 

-

. ..,_ .. . 

page 23of24 
7 PERSONNEL 

Study director: 

Co-worker: 

Qually assurance: 

All are staff members of the test facility. 

8 CONFIRMATON OF THE STUDY REPORT 

Date: 

Study director 

Chemist 

Chemist 

Food chemist 

Biological technical assistant 

Company stamp: 

Page 1 of the original report is printed on paper; the report is authorised 

by original signature and company's stamp. Use or publication in parts is not authorised on principle 

and is not allowed to be connected with the company's name or a signature of a staff member. 

Misuse will be prosecuted. 

page 24 of24