Fatty acids, linseed-oil, reaction products with bisphenol A-epichlorohydrin polymer and glycidyl neodecanoate

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

other: Adsorption estimated

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 limited documentation / justification

Justification for type of information:

See below under 'Overall remarks, attachments' for applicability domain.

Qualifier:

according to guideline

Guideline:

other: REACH guidance on QSARs: Chapter R.6. QSARs and grouping of chemicals

Principles of method if other than guideline:

Since the test substance is an UVCB with several constituents and not all of its constituents are defined, the Koc values were estimated for the major constituents, (which are approx. 90% of the composition) using the MCI (molecular connectivity index) approach of KOCWIN v2.00 program.

Specific details on test material used for the study:

Input data for the model: SMILES of the major constituents:
1. BADGE + 2 Linseed oil and derivatives: C(=C/C\C=C/C\C=C/CCCCCCCC(OCC(COc1ccc(cc1)C(c2ccc(cc2)OCC(COC(CCCCCCC/C=C\C/C=C\C/C=C\CC)=O)O)(C)C)O)=O)/CC (representative SMILES)
2. Neodecanoic acid, oxiranylmethyl ester + 1 Linseed oil: C(=C/C\C=C/C\C=C/CCCCCCCC(OCC(COC(C(C(CC(C)C)C)(C)C)=O)O)=O)/CC (representative SMILES)

Computational methods:

Since the test substance is an UVCB and not all of its constituents are defined, the Koc values were estimated for its two major constituents (which comprise 90% of the compostion) using the MCI (molecular connectivity index) method of KOCWIN v2.00. program. Estimation by MCI method was chosen over Kow based method, because it is relatively more accurate than Kow based method and also because no experimental Kow value could be determined.

Methodology:
The methodology as described in (Meylan et al, 1992) was used to develop the QSAR equations utilizing Molecular Connectivity Index (MCI). Two separate regressions were performed. The first regression related log Koc of non-polar compounds to the first-order MCI. For the current model development, the non-polar dataset is designated as compounds having "No Correction Factors" while the polar compounds are designated as compounds "Having Correction factors", which means the MCI descriptor alone can adequately predict the Koc for non-polar compounds.
Measured log Koc values were fit to a simple linear equation of the form:
log Koc = a MCI + b
where a and b are the coefficients fit by least-square analysis. The 69 compounds used for this regression are listed in Appendix E of EPISuite KOCWIN help manual. The second regression included the 447 compounds having correction factors; these compounds are listed in Appendix F of EPISuite KOCWIN help manual. The correction factors descriptors are listed in Appendix D.
Correction factors are specific chemical classes or structural fragments. The regression coefficients were derived via multiple linear regression of the correction descriptors to the residual error of the prediction from the non-polar equation.

The equation derived by the non-polar (no correction factor) regression is:
log Koc = 0.5213 MCI + 0.60
(n = 69, r2 = 0.967, std dev = 0.247, avg dev = 0.199)

Key result

Type:

Koc

Value:

>= 403 000 - <= 10 000 000 000 L/kg

Remarks on result:

other: estimated based on MCI method of KOCWIN v.2.00 for major constituents

Key result

Type:

log Koc

Remarks:

(estimated)

Value:

>= 5.61 - <= 10.5 dimensionless

Remarks on result:

other: estimated based on MCI method of KOCWIN v.2.00 for major constituents

Details on results

SMILES : C(=CCC=CCC=CCCCCCCCC(=O)(OCC(COC(=O)(C(C(CC(C)C)C)(C)C))O))CC

CHEM : neodecanoic acid, oxiranylmethyl ester + 1 linseed oil

MOL FOR: C31 H54 O5

MOL WT : 506.77

---------------------------  KOCWIN v2.00 Results  ---------------------------

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index  ........... : 17.106

        Non-Corrected Log Koc (0.5213 MCI + 0.60)  .......... :  9.5173

        Fragment Correction(s):

                 1   Aliphatic Alcohol  (-C-OH)  ...........  : -1.3179

                 2   Ester  (-C-CO-O-C-) or (HCO-O-C) ......  : -2.5939

        Corrected Log Koc  .................................. :  5.6055

                        Estimated Koc:  4.032e+005  L/kg   <===========

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow  (Kowwin estimate)  ......................... : 10.24

        Non-Corrected Log Koc (0.55313 logKow + 0.9251)  .... :  6.5892

        Fragment Correction(s):

                 1   Aliphatic Alcohol  (-C-OH)  ...........  : -0.4114

                 2   Ester  (-C-CO-O-C-) or (HCO-O-C) ......  : -0.1312

        Corrected Log Koc  .................................. :  6.0465

                        Estimated Koc:  1.113e+006  L/kg   <===========

SMILES : C(=CCC=CCC=CCCCCCCCC(=O)(OCC(COc1ccc(cc1)C(c2ccc(cc2)OCC(COC(=O)(CCCCCCCC=CCC=CCC=CCC))O)(C)C)O))CC

CHEM : BADGE + 2 linseed oil and derivatives

MOL FOR: C57 H84 O8

MOL WT : 897.30

---------------------------  KOCWIN v2.00 Results  ---------------------------

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index  ........... : 31.649

        Non-Corrected Log Koc (0.5213 MCI + 0.60)  .......... : 17.0987

        Fragment Correction(s):

                 2   Ether, aromatic  (-C-O-C-)  ...........  : -1.3582

                 2   Aliphatic Alcohol  (-C-OH)  ...........  : -2.6358

                 2   Ester  (-C-CO-O-C-) or (HCO-O-C) ......  : -2.5939

        Corrected Log Koc  .................................. : 10.5107

                        Estimated Koc:  1e+010  L/kg   <===========

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow  (Kowwin estimate)  ......................... : 17.57

        Non-Corrected Log Koc (0.55313 logKow + 0.9251)  .... : 10.6436

        Fragment Correction(s):

                 2   Ether, aromatic  (-C-O-C-)  ...........  :  0.1118

                 2   Aliphatic Alcohol  (-C-OH)  ...........  : -0.8229

                 2   Ester  (-C-CO-O-C-) or (HCO-O-C) ......  : -0.1312

        Corrected Log Koc  .................................. :  9.8014

                        Estimated Koc:  6.329e+009  L/kg   <===========

Conclusions:

Based on the estimated values for the major constituents using MCI method of KOCWIN v2.00 program (EPISuite v 4.1), the Koc of the test substance is considered to range from 4.03E5 to 10E9 L/kg (log Koc: 5.6 to 10.5).

Executive summary:

The Koc was estimated using the MCI method of KOCWIN v2.00 program (EPISuite v4.1). Since the test substance is an UVCB and not all of its constituents are defined, the Koc values were estimated for its two major constituents, which comprise 90% of the composition. Estimation by MCI method was chosen over Kow-based method, because it is relatively more accurate than Kow-based method, especially for very high lipophilic substances. Using SMILES codes as the input parameter, the Koc values were estimated to be 4.03E5 L/kg (log Koc = 5.61) for ‘neodecanoic acid, oxiranylmethyl ester+ 1 linseed oil’ and 10E9 L/kg (log Koc = 10.5) for ‘BADGE + 2 linseed oil and derivatives’ (US EPA, 2016). This indicates very high adsorption potential to organic matter or low mobility (White, 2009). The evaluation of the applicability domain indicated that the estimate for the neodecanoic acid, oxiranylmethyl ester constituent is relatively more accurate than the BADGE constituent. Therefore, as a conservative approach the lower and more accurate estimated Koc forneodecanoic acid, oxiranylmethyl ester+ 1 linseed oil constituent has been taken forward for risk assessment. Overall, based on this information, the Koc of the test substance can be considered to be ≥4.03E5 L/kg (log Koc ≥5.6).

Description of key information

Based on the estimated values for the major constituents using MCI method of KOCWIN v2.00 program (EPISuite v 4.1), the Koc of the test substance can be considered to be ≥4.03E5 L/kg (log Koc ≥5.6).

Key value for chemical safety assessment

Koc at 20 °C:

403 000

Additional information

The Koc was estimated using the MCI method of KOCWIN v2.00 program (EPISuite v4.1). Since the test substance is an UVCB and not all of its constituents are defined, the Koc values were estimated for its two major constituents, which comprise 90% of the composition. Estimation by MCI method was chosen over Kow-based method, because it is relatively more accurate than Kow-based method, especially for very high lipophilic substances. Using SMILES codes as the input parameter, the Koc values were estimated to be 4.03E5 L/kg (log Koc = 5.61) for ‘neodecanoic acid, oxiranylmethyl ester+ 1 linseed oil’ and 10E9 L/kg (log Koc = 10.5) for ‘BADGE + 2 linseed oil and derivatives’ (US EPA, 2016). This indicates very high adsorption potential to organic matter or low mobility (White, 2009). The evaluation of the applicability domain indicated that the estimate for the neodecanoic acid, oxiranylmethyl ester constituent is relatively more accurate than the BADGE constituent. Therefore, as a conservative approach the lower and more accurate estimated Koc forneodecanoic acid, oxiranylmethyl ester+ 1 linseed oil constituent has been taken forward for risk assessment. Overall, based on this information, the Koc of the test substance can be considered to be ≥4.03E5 L/kg (log Koc ≥5.6).

[LogKoc: 5.6]