Reaction mass of 4,4'-Isopropylidenediphenol, 1-chloro-2,3-epoxypropane and ethylenediamine

Partition coefficient

Link to relevant study record(s)

Reference

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Study period:

This study was conducted between 19 December 2016 and 25 May 2017

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: The study is considered to be a reliability 1 as it has been conducted according to OECD TG 117 and in compliance with GLP.

Justification for type of information:

See attached justification in Section 13

Reason / purpose for cross-reference:

data waiving: supporting information

Qualifier:

according to guideline

Guideline:

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

Version / remarks:

13 April 2004

Deviations:

no

Qualifier:

according to guideline

Guideline:

EU Method A.8 (Partition Coefficient - HPLC Method)

Version / remarks:

EC No. 440/2008 of 30 May 2008

Deviations:

no

GLP compliance:

yes

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Specific details on test material used for the study:

Identification : 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, reaction products with ethylenediamine
Appearance/Physical state: Yellow/brown extremely viscous liquid
Batch : BBF01102V1
Purity : 100% UVCB
Expiry date : 01 January 2021
Storage conditions*: Room temperature in the dark

* Test item was held at room temperature in the dark, heated to approximately 50 or 80 °C for subsampling, as per sponsor’s communications.

Analytical method:

high-performance liquid chromatography

Key result

Type:

log Pow

Partition coefficient:

> 3.9 - < 5.4

Remarks on result:

other: 95% of test item at 5.4

Key result

Type:

Pow

Partition coefficient:

> 7 860 - < 257 000

Remarks on result:

other: 95% of test item at 257000

Details on results:

Preliminary Estimate
The log10 Pow was calculated to be: 0.09 to 1.39 (major 3 components)

Discussion
The result from the preliminary test indicated that the HPLC method was suitable for determination of partition coefficient for this test item.
The mobile phase was adjusted to pH 12.0 to ensure the test item was tested in its non-ionized form.The test item has a predicted dissociation constant of between 9.63 and 13.57 for the major constituents (ACD/Labs I-Lab 2.0 - ilab.acdlabs.com, algorithm version: v12.1.0.50374). Therefore, testing was performed at pH 12.0 to obtain the test item in its non-ionized form

 

DefinitiveTest

Calibration

The retention times of the dead time and the retention times, capacity factors (k') and log₁₀P_owvalues for the reference standards are shown in the following tables:

Table 13

Dead time	Retention Time (mins)		Mean retention time (mins)
	Injection 1	Injection 2
Thiourea	3.105	3.105	3.105

Table 14

Standard	Retention time (mins)			Capacity factor (k')	Log10k'	Log10Pow
	Injection 1	Injection 2	Mean
2-Butanone	3.557	3.557	3.557	0.146	-0.837	0.3
Benzene	4.956	4.947	4.952	0.595	-0.226	2.1
Toluene	5.991	5.977	5.984	0.927	-3.28 x 10^-2	2.7
Naphthalene	6.983	6.963	6.973	1.25	9.54 x 10^-2	3.6
Phenanthrene	11.322	11.273	11.298	2.64	0.421	4.5
Triphenylamine	20.214	20.136	20.175	5.50	0.740	5.7
DDT	24.752	24.674	24.713	6.96	0.843	6.5

Partition coefficient of sample

The retention times, capacity factor and log₁₀P_owvalue determined for the sample are shown in the following table:

Table 15

Peak ID	Injection	Retention time (mins)	Capacity factor (k′)	Log10k'	Log10Pow	% Area
1	1	8.186	1.64	0.214	3.89	2.52
	2	8.230	1.65	0.218	3.90
2	1	15.098	3.86	0.587	5.26	1.61
	2	15.192	3.89	0.590	5.28
3	1	16.150	4.20	0.623	5.40	95.9
	2	16.351	4.27	0.630	5.42

Mean log₁₀P_ow:         Between 3.9 and 5.4 (95.9% of test item at 5.4)
Partition coefficient:  Between 7.86 x 10³and 2.57 x 10⁵(95.9% of test item at 2.57 x 10⁵)

Conclusions:

The partition coefficient of the test item has been determined to be between 7.86 x 10^3 and 2.57 x 10^5 (95.9% of test item at 2.57 x 10^5), log10 Pow between 3.9 and 5.4 (95.9% of test item at 5.4).

Executive summary:

The general physico-chemical properties of 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, reaction products with ethylene diamine have been determined.

Partition Coefficient Between 7.86 x 10³and 2.57 x 10⁵(95.9% of test item at 2.57 x 10⁵), log₁₀P_ow between 3.9 and 5.4 (95.9% of test item at 5.4),using the HPLC method, designed to be compatible with Method A.8 Partition Coefficient of Commission Regulation (EC) No 440/2008 of 30 May 2008 and Method 117 of the OECD Guidelines for Testing of Chemicals, 13 April 2004.

Key value for chemical safety assessment

Log Kow (Log Pow):

1.97

at the temperature of:

20 °C

Additional information

Using a combined weight of evidence approach to compare the following points:

 

1)     preliminary Logkow assessments for BADGE-EDA, DETA and TETA (i.e. cumulative assessment of components A-C)

2)     experimental data (HPLC and Shake Flask)

3)     experimental data for each amine and BADGE

4)     In-silico methods (QSAR toolbox, ECOSAR and US-EPA T.E.S.T)

5)     The HPLC method (OECD 117) was not appropriate to differentiate the components or sensitive enough for determination of the LogPow for BADGE-EDA

6)     BADGE-EDA is not a mixture of homologues

7)     The OECD 117 test provides a qualitative estimate but the OECD 107 provides and definitive quantitative value. For, BADGE-EDA and OECD 107 test design should have been used

It is concluded that the LogKow derived using the OECD 117 HPLC method is likely to be an anomalous poor estimate and is not supported by the experimental/in-silico data presented within this document. It is concluded that the determined LogKow range of 3.9 - 5.4 for BADGE-EDA should not be considered. It is proposed that the experimentally derived LogKow of 1.97 determined for BADGE-TETA is used as a conservative estimate for regulatory purposes.