Carbamic acid,N,N'-[1,3-phenylenebis[methyleneiminocarbonylimino(methyl-3,1-phenylene)]]bis-di-C11-14-isoalkylesters, C13-rich

Partition coefficient

Administrative data

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2014

Materials and methods

Test guideline

Qualifier:

according to guideline

Guideline:

OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Test material

Test material information

Constituent 1

Reference substance name:

bis(11-methyldodecyl) ((((1,3-phenylenebis(methylene)bis(azanediyl))bis(carbonyl) bis(azanediyl))bis(4-methyl-3,1-phenylene) dicarbamate

Cas Number:

865536-03-4

Molecular formula:

C52H80N6O6

IUPAC Name:

bis(11-methyldodecyl) ((((1,3-phenylenebis(methylene)bis(azanediyl))bis(carbonyl) bis(azanediyl))bis(4-methyl-3,1-phenylene) dicarbamate

Constituent 2

Reference substance name:

bis(11-methyldodecyl)(4-methyl-1,3-phenylene)dicarbamate

Molecular formula:

C35H62N2O4

IUPAC Name:

bis(11-methyldodecyl)(4-methyl-1,3-phenylene)dicarbamate

Constituent 3

Reference substance name:

11-methyldodecyl (3-(3-(3-(aminomethyl)benzyl)ureido)-4-methylphenyl)carbamate

Molecular formula:

C30H46N4O3

IUPAC Name:

11-methyldodecyl (3-(3-(3-(aminomethyl)benzyl)ureido)-4-methylphenyl)carbamate

Constituent 4

Reference substance name:

1,1'-(4-methyl-1,3-phenylene)bis(3-(3-(aminomethyl)benzyl)urea)

Molecular formula:

C25H30N6O2

IUPAC Name:

1,1'-(4-methyl-1,3-phenylene)bis(3-(3-(aminomethyl)benzyl)urea)

Test material form:

solid

Study design

Analytical method:

high-performance liquid chromatography

Results and discussion

Partition coefficient

Key result

Type:

log Pow

Partition coefficient:

>= 3.938 - <= 4.23

Temp.:

25 °C

pH:

ca. 6

Details on results:

As peak 1 showed a relative area < 5 %, it was considered as minor peak.
Although area is not necessarily correlated to absolute concentration if a UV detector is
used, it is assumed that the test item consists mainly of the peaks 2 and 3. Using the correlation
log K / log POW, the log POW of the major components of test item Addukt TI 65 -
MXDA was calculated as 3.938– 4.230 (mean ± standard deviation).

Applicant's summary and conclusion

Conclusions:

Variations in the retention times of reference items and test item are very small. Therefore,
a stable configuration of the HPLC-column can be assumed.
The correlation log K/log POW is good: the coefficient of determination r2 was calculated
with 0.9905. This value was considered as sufficiently high to use the calibration function
for the determination of the log POW of the test item Addukt TI 65 - MXDA.
As peak 1 showed a relative area < 5 %, it was considered as minor peak. Although area
is not necessarily correlated to absolute concentration if UV detection is used, it is assumed
that the test item Addukt TI 65 - MXDA consists mainly of peak 2 and 3, indicating
that the log POW of Addukt TI 65 - MXDA should be stated as range from 3.938 - 4.230.
No observations were made which might cause doubts concerning the validity of the study
outcome.

Executive summary:

The study was performed using a HPLC with a C18 column. Six reference items with different

retention times and thiourea for the determination of the dead time were used to

produce a calibration curve, since retention time on hydrophobic columns and POW are

correlated. The reference items were chosen on behalf of the pre-test.

One vial was filled with the reference item mix and one vial with the test item solution. The

vials were analysed using the HPLC with the program described above. First one injection

from the solvent blank methanol/water 75/25 (v/v) was made. Then three injections were

measured from the reference item mix, three injections from the test item and again three

injections from the reference item mix.

For each reference item, the capacity factor K was calculated from the retention time of

thiourea and the retention time of the respective reference item.

A calibration function (log K versus log POW, linear fit) was determined using the literature

values for POW of the reference items and the retention times in the six determinations.

The chromatogram of the test item gave two major and one minor peaks. With the calibration

function log K versus log POW, the corresponding log POWs of the peaks were determined

with:

Peak Mean Area

[mAU*min]

Rel. Area % Mean Retention

Time [min]

Log POW

± Stand. Dev

1 0.167 3.304 5.287 3.602 ± 0.002

2 1.987 39.346 6.571 3.938 ± 0.003

3 2.896 57.350 8.030 4.230 ± 0.002

These values are the means ± standard deviations of three independent determinations

As peak 1, showed a relative area < 5 %, it was considered as minor peak and was not

taken into account in the determination of log POW of the test item.

Although area is not necessarily correlated to the absolute concentration, if a UV detector

is used, it is assumed that the test item consists mainly of peaks 2 and 3, indicating that

the log POW of the test item Addukt TI 65 - MXDA lies in the range of 3.938 - 4.230.