Reaction product of m-tolylidene diisocyanate and cyclohexylamine and cyclohex-1,2-ylenediamine and (Z)-octadec-9-enylamine

Water solubility

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

24 November 2009 - 15 December 2009

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

OECD Guideline 105 (Water Solubility)

Version / remarks:

Adopted July 1995

Deviations:

no

Qualifier:

according to guideline

Guideline:

EU Method A.6 (Water Solubility)

Version / remarks:

May 2008

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Other quality assurance:

other: Chemikaliengesetz ('Chemicals Act') der Bundesrepublik Deutschland (ChemG), Anhang 1 ('Annex 1'), 2008 and Directive 2004/10/EC of 11 February 2004 (Official Journal No. L 50/44)

Type of method:

column elution method

Water solubility:

1.5 mg/L

Conc. based on:

test mat.

Temp.:

20 °C

pH:

>= 7 - <= 7.3

Remarks on result:

other: Mean of 8 results. SD: 0.2

Details on results:

The determined IC values used in the calculation of the TOC values, and therefore, test item concentrations for all samples were below the limit of quantification of 3.971 mg Carbon/L (Table 1), however the calculated values were used for the results evaluation.

Table 1: Results for the Determination of the Water Solubility of the Test Item

Sample Description	Time (h)	TC^1 found (mg C/L)	IC^1 found (mg C/L)	TOC^1 calculated (mg C/L)	TOC^2 corrected (mg C/L)	Test Item Conc.^3 calculated (mg test item/L)	Measured pH^4 after Incubation
Blank Pure Water		1.365	0.368	0.997
Flow rate 0.4 mL/min
50574185	0	4.798	2.686	2.112	1.115	1.564	7.3
50574185	1	4.820	2.621	2.199	1.202	1.686	7.2
50574185	2	4.681	2.606	2.075	1.078	1.512	7.2
50574185	3	4.801	2.678	2.123	1.126	1.579	7.1
50574185	4	4.954	2.645	2.309	1.312	1.840	7.0
Flow rate 0.2 mL/min
50574185	0	4.760	2.608	2.152	1.155	1.620	7.0
50574185	1	4.634	2.642	1.992	0.995	1.395	7.1
50574185	2	4.752	2.608	2.144	1.147	1.608	7.1
50574185	3	4.610	2.626	1.983	0.986	1.383	7.1
50574185	4	4.544	2.639	1.908	0.908	1.273	7.0
Mean value (n = 8):						1.5
SD (n = 8):						0.2

¹rounded value calculated from exact raw data

²value corrected for the blank value of 0.997 mg Carbon/L

³calculated using carbon content of 71.31 %

⁴measured with pH electrode

italic values are below the limit of quantification, however, they were used for the calculation of TOC

TC: Total Carbon

IC: Inorganic Carbon

Limit of Detection: LOD_TC: 0.349 mg Carbon/L and LOD_IC: 1.128 mg Carbon/L

Limit of Quantification: LOQ_TC: 1.245 mg Carbon/L and LOQ_IC: 3.971 mg Carbon/L

Conclusions:

The water solubility of the test item was determined using the column elution method and TOC analysis and was determined to be 1.5 ± 0.2 mg test item/L.

Executive summary:

The water solubility of the test item was determined in an OECD 105 and EC A.6 guideline study using the column elution method, with the samples analysed by TOC analysis with an infrared gas analyser detector. The limits of detection of the analysis were determined to be 0.349 mg Carbon/L and 1.128 mg Carbon/L for total and inorganic carbon, respectively. The limits of detection of the analysis were determined to be 1.245 mg Carbon/L and 3.971 mg Carbon/L for total and inorganic carbon, respectively. The measurements were performed on 5 occasions over 4 hours in two experiments; the initial experiment utilised a flow rate 0.4 mL/min and the second experiment at 0.2 mL/min. The determined IC values used in the calculation of the TOC values, and therefore, test item concentrations for all samples were below the limit of quantification, however the calculated values were used for the results evaluation. The water solubility of the test item was estimated to be 1.5 ± 0.2 mg test item/L.

 

Water solubility was investigated in a GLP compliant guideline experimental study and is adequate for assessment of this endpoint with some restrictions due to the determined inorganic carbon values being below the limit of quantification.

Reference 2

Endpoint:

water solubility

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification

Justification for type of information:

Dissolution of PU substances from grease into water is very unlikely as the thickeners are poorly water soluble and are embedded in the hydrophobic grease matrix. Additionally, extensive method development on PU grease thickeners have shown that the measurable concentrations of PU grease thickeners in water are at, or below, the limit of quantification. Therefore, (Q)SAR modelling has been used to fulfil this endpoint. Further details on the (Q)SAR modelling is available in the attached QPRF and QMRFs.

Principles of method if other than guideline:

- Software tool(s) used including version: EPISuite v.4.11, SPARC v6.0, ALOGPS
- Model(s) used: WSKOWWIN v1.42, WATERNT v1.01, SPARC v6.0 and ALOGPS 2.1
- Model description: see fields 'Justification for non-standard information' and 'Attached justification'
- Justification of QSAR prediction: see field 'Justification for non-standard information' and 'Attached justification'

Type of method:

other: QSAR

Water solubility:

0 mg/L

Conc. based on:

test mat.

Remarks:

Mean geometric for two structures

Remarks on result:

not determinable because of methodological limitations

Remarks:

QSAR predictions reported

Details on results:

The water solubility of the substance has been predicted using EPISuite (WSKOWWIN and WATERNT), SPARC and ALOGPS, well established and validated model programmes. The substance is of uncertain and variable composition which cannot be measured directly due to dispersion in a base oil medium. The constituents present are assumed based on the reactants, and detected analytically only when isolated from the base oil. Predicted average geomean water solubility for the structures present in the test item is 6.75e-10 mg/L.

Table 1: Water solubility (mg/L)

Chemical Formula	SMILES	Model	Sub-Model	Water Solubility (mg/L)	Geomean (mg/L)
C34H58N4O2	CCCCCCCCCC=CCCCCCCCCNC(=O)Nc2ccc(C)c(NC(=O)NC1CCCCC1)c2	EPISuite v4.11	WSKOWWIN v1.42	7.92e-8	1.19e-06
		EPISuite v4.11	WATERNT v1.01	5.55e-7
		SPARC v6.0	-	5.53e-10
		ALOGPS 2.1	ALOGPS	8.34e-2
C47H74N8O4	CCCCCCCCCC=CCCCCCCNC(=O)Nc4ccc(C)c(NC(=O)NC1CCCCC1NC(=O)Nc3cccc(NC(=O)NC2CCCCC2)c3C)c4	EPISuite v4.11	WSKOWWIN v1.42	3.52e-10	1.57e-7
		EPISuite v4.11	WATERNT v1.01	8.15e-7
		SPARC v6.0	-	1.52e-12
		ALOGPS 2.1	ALOGPS	1.38
MEAN					6.75e-10

Conclusions:

The water solubility of the test item was determined using the SPARC (v6.0), ALOGPS, WSKOWWIN (v1.42) and WATERNT (v1.01) QSAR models and the average of the geometric mean water solubilites of the constituents was 6.75E-10 mg/L.

Executive summary:

The water solubility of the test item was determined using the SPARC (v6.0), ALOGPS, WSKOWWIN (v1.42) and WATERNT (v1.01) QSAR models. The substance is of uncertain and variable composition which cannot be measured directly due to dispersion in a base oil medium. The constituents present are assumed based on the reactants, and detected analytically only when isolated from the base oil and the average of the geometric mean water solubilites of the constituents was 6.75 x10 ^-10 mg/L.

Description of key information

The water solubility of the test item was determined using the SPARC (v6.0), ALOGPS, WSKOWWIN (v1.42) and WATERNT (v1.01) QSAR models and the average of the geometric mean water solubilites of the constituents was 6.75E-10 mg/L.

In the supporting study, the water solubility of the test item was determined in a GLP compliant OECD 105 and EC A.6 guideline study using the column elution method, with the samples analysed by TOC analysis with an infrared gas analyser detector (Mollandin 2010). The limits of detection of the analysis were determined to be 0.349 mg Carbon/L and 1.128 mg Carbon/L for total and inorganic carbon, respectively. The limits of quantification of the analysis were determined to be 1.245 mg Carbon/L and 3.971 mg Carbon/L for total and inorganic carbon, respectively. The determined IC values used in the calculation of the TOC values, and therefore test item concentrations for all samples, were below the limit of quantification. However, the calculated values were used for the results evaluation. The water solubility of the test item was estimated to be 1.5 ± 0.2 mg test item/L. Due to the results being calculated using data below the instrumental LoQ, the study is used as a supporting study only.

Key value for chemical safety assessment

Water solubility:

0 mg/L

at the temperature of:

25 °C

Additional information

Polyurea greases thickeners are not synthesized as “pure” compounds and do not exist except in the presence of base oil grease matrix. High temperature stability indicates that the structures of PU substances are robust and resistant to diffusion out of the grease matrix. Therefore, dissolution of PU substances from grease into water is very unlikely as the thickeners are poorly water soluble and are embedded in the hydrophobic grease matrix. PU substances are expected to reside within the grease base oil matrix and is not expected to favourably partition to water. Additionally, due to the low water solubilities of these substances, below the limit of detection (LoD) or Limit of Quantification (LoQ) for standard methods the water solubility was predicted by QSAR modelling.