(1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)] diacrylate

PBT assessment

PBT assessment: overall result

Reference

Reference 1

Name:

Tripropylene glycol diacrylate

Type of composition:

boundary composition of the substance

State / form:

liquid

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference 2

Name:

Tripropylene glycol diacrylate

Type of composition:

legal entity composition of the substance

State / form:

liquid

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

Reference substance:

Tripropylene glycol diacrylate

PBT status:

the substance is not PBT / vPvB

Justification:

Parent compound:

 The substance is an UVCB substance. The following four main constituents which concentrations at or above 0.1 % (w/w) were analytically determined:

1.   Constituent 1 (2-{2-[2-(acryloyloxy)-1-methylethoxy]-1-methylethoxy}-1-methylethyl acrylate), ca. 85% (w/w)

2.   Constituent 2 (2-Propenoic acid, 2-[2-(2-hydroxymethylethoxy)methylethoxy]methylethyl ester), ca. 4% (w/w)

3.   Constituent 3 (2-Propenoic acid (1 or 2), (4 or 5), (7 or 8)-trimethyl-10,14-dioxo-3,6,9,13-tetraoxahexadec-15-en-1-yl ester), ca. 3% (w/)

4.   Constituent 4 ((1 or 2)-methyl-2-{(1 or 2)-methyl-2-[(1 or 2)-methyl-2-(2-propenoyloxy)ethoxy]ethoxy}ethyl (5 or 6), (8 or 9), (11 or 12)-trimethyl-14-oxo-4,7,10,13-tetraoxahexadec-15-en-1-oate), ca. 2% (w/w)

In accordance with Annex IX, Section 9.3.2 and Section 9.2.1.2 the assessment of bioaccumulation or bioconcentration and biodegradation of each constituent and impurity present in concentrations at or above 0.1% (w/w) must be performed.

The substance meets the criteria for classification as persistance (P) or very persistance (vP). As the substance is concluded to be not readily biodegradable (according to OECD criteria), it should be considered as potentially P/vP from a worst-case point of view.

However, the substance is not B/vB based on a measured log Kow of 2.7 (BASF SE, rep. no.:19L00100, 2019).

In order to assess the bioaccumulation potential of the test substance, a WoE approach with several estimation models for each main constituent was conducted. Overall, considering all models applied constituents of the registration item are estimated to have BCF values range between 0.947 and 59.29 L/kg.

The substance is also not T since the lowest available chronic value is >> 0.01 mg/L and the substance holds no relevant classification.

The remaining “non-specified constituents” sum up to a typical concentration of approximately 6.0 % (w/w). According to GC analytics, more than 45 peaks contribute to this part of the composition of the registration item. Though it is virtually not possible to identify each single peak and assess the respective substance(s) individually, a generic assessment of the environmentally relevant properties of these ingredients may be applied. Multifunctional acrylates are synthesized from alcohols and acrylic acid. As a consequence, the resulting products – including the “non-specified constituents” – are made of the same, similar chemistry. As shown by the evidence provided above, this chemistry basically is subject to ultimate biotic degradation: in none of the four main constituents, a potential metabolite that may be generated from the degradation of these compounds was identified. Therefore, from a scientific perspective, it is extremely likely that also the degradation of the chemically similar “non-specified constituents” of the registration item will not lead to the formation of a persistent metabolite. The raw materials used as well as the conditions of the reaction chosen during manufacture are targeted to produce 2-{2-[2-(acryloyloxy)-1-methylethoxy]-1-methylethoxy}-1-methylethyl acrylate. Side-products beyond the main constituents discussed above are expected to slightly vary in chain lengths and/or branching, but are not anticipated to significantly differ in terms of structural elements – if at all. Therefore, also these structures are deemed degradable by the same metabolic pathways. Consequently, there is no concern that (part of) the UVCB may persist in the environment.

 

PBT / vPvB – Assessment for modelled metabolites of TPGDA (CAS 42978-66-5):

ECHA Guidance on information requirements and chemical safety assessment (v3.0, June 2017), Chapter R.11.4.1 specifies that “Constituents, impurities and additives should normally be considered relevant for the PBT/vPvB assessment when they are present in concentration of ≥ 0.1% (w/w)” […] “Similar arguments apply to relevant transformation/degradation products”.

In order to identify the relevant degradation products of the main constituents of TPGDA as a standard information requirement according to Column 1, Section 9.2.3. of Annex IX to REACH and for purposes of an assessment of potential PBT/vPvB properties, the metabolites were modelled using CATALOGIC 301C v11.15 – July 2018 and CATALOGIC 301F (OASIS CATALOGIC v5.13.1.156).

Overall, the CATALOGIC 301C v11.15 calculated 212 metabolites (Table 1) identifying 133 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥0.1% (equivalent to quantity setting in OASIS CATALOGIC: ≥ 0.001 [mol/mol parent]).

Table 1: QSAR prediction for CAS-#42978-66-5 (TPGDA) using CATALOGIC 301C v11.15 – July 2018 the predicted metabolites from the CATALOGIC 301C v11.15 estimation model with an estimated quantity of ≥ 0.1%.

#	Smiles	Quantity [mol/mol parent]	log Kow
	Constituent 1
1	CC(COC(C)COC(C)COC(=O)C=C)OC(=O)C=C	0.1138	1.8182	42
2	CC(O)COC(C)COC(C)COC(=O)C=C	0.134	0.4581	48
3	CC(COC(C)COC(=O)C=C)OCOC(C)=O	0.03356	0.5548	58
4	CC(O)COC(C)COC(=O)C=C	0.08252	0.3149	55
5	CC(COC(=O)C=C)OCOC(C)=O	0.02067	0.4116	66
6	CC(O)COC(=O)C=C	0.05084	0.1717	61
7	CC(=O)OCOC(=O)C=C	0.04302	0.2684	49
8	CC(=O)OCO	0.03591	-1.0917	50
9	CC(COC(C)COC(C)C(O)=O)OC(=O)C=C	0.1399	0.6861	50
10	CCOCC(C)OCC(C)OC(=O)C=C	0.1111	1.5053	56
11	CC(O)C(O)=O	0.06854	-0.649	68
12	CCOCOC(C)=O	0.01028	0.0987	89
13	CC(O)COC(C)C(O)=O	0.01422	-0.8172	75
14	CC(C(O)=O)OCOC(C)=O	0.003561	-0.7205	84
15	CC(COC(C)COC(C)COC(=O)C=C)OC(=O)C(O)CO	0.006802	0.5579	44
16	OC(C(O)=O)C(O)=O	0.01121	-2.4723	90
17	CC(COC(C)COC(C)COC(=O)C1CO1)OC(=O)C=C	0.006802	1.5121	51
	Constituent 2
1	CC(COCC(C)OCC(C)O)OC(=O)C=C	0.1036	0.4581	56
2	CC(COCC(C)OCOC(C)=O)OC(=O)C=C	0.04861	0.5548	52
3	CC(COCC(C)O)OC(=O)C=C	0.1196	0.3149	45
4	CC(COCOC(C)=O)OC(=O)C=C	0.02995	0.4116	74
5	CC(CO)OC(=O)C=C	0.08994	0.1717	57
6	CC(O)C(O)=O	0.28	-0.649	68
7	CC(O)COCC(C)O	0.08987	-0.6388	0
8	CC(O)COC(C)C(O)=O	0.05544	-0.8172	75
9	CC(C(O)=O)OCOC(C)=O	0.01389	-0.7205	84
10	CC(O)COCOC(C)=O	0.02004	-0.9485	80
11	CC(COCC(C)OCC(C)O)OC(=O)C(O)CO	0.007037	-0.8022	55
12	OC(C(O)=O)C(O)=O	0.005799	-2.4723	90
	Constituent 3
1	CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C=C)OC(=O)C=C	0.01263	1.8499	50
2	CC(COCC(C)OCC(C)OC(=O)C=C)OC(=O)C=C	0.05805	1.8182	43
3	CC(COCC(C)O)OCC(C)OC(=O)C=C	0.1367	0.4581	56
4	CC(COCOC(C)=O)OCC(C)OC(=O)C=C	0.03425	0.5548	62
5	CC(COC(C)C(O)=O)OC(=O)C=C	0.08799	0.5429	57
6	CCOCC(C)OC(=O)C=C	0.06987	1.3621	60
7	CC(O)C(O)=O	0.06865	-0.649	68
8	CC(COCC(C)OCC(C)O)OC(=O)C=C	0.1265	0.4581	56
9	CC(COCC(C)OCOC(C)=O)OC(=O)C=C	0.03168	0.5548	52
10	CC(COCC(C)O)OC(=O)C=C	0.0779	0.3149	45
11	CC(COCOC(C)=O)OC(=O)C=C	0.01951	0.4116	74
12	CC(CO)OC(=O)C=C	0.05861	0.1717	57
13	CC(COCC(C)O)OCC(C)OC(=O)CCOC(=O)C=C	0.02928	0.4898	55
14	CC(COCC(C)OCC(C)OC(=O)CC(O)=O)OC(=O)C=C	0.02928	0.7178	51
15	CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C=C)OC (=O)C(O)CO	0.004699	0.5896	52
16	CC(COCC(C)OCC(C)OC(=O)C=C)OC(=O)C(O)CO	0.004177	0.5579	50
17	OC(C(O)=O)C(O)=O	0.007314	-2.4723	90
18	CC(COCC(C)OCC(C)OC(=O)CCOC(=O)C1CO1) OC(=O)C=C	0.004699	1.5438	47
	Constituent 4
1	CC(COCC(C)OCC(C)OCCC(=O)OC(C)COC(C)COCC (C)OC(=O)C=C)OC(=O)C=C	0.01263	2.2795	37
2	CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C=C	0.2082	0.9028	38
3	CCOC(C)COC(C)COCC(C)OC(=O)C=C	0.1653	1.6485	38
4	CCOC(C)COC(C)C(O)=O	0.05354	0.3732	45
5	CCOCC(C)OCC	0.001786	1.1924	66
6	CCOCC(C)OC(C)O	0.001005	-0.3459	91
7	CC(O)C(O)=O	0.2925	-0.649	68
8	CC=O	0.00517	-0.1659	100
9	CCOC(C)COC(C)O	0.001005	-0.3459	42
10	CCOC(C)C(O)=O	0.06995	0.23	8
11	CCOCC	0.1376	1.0492	7
12	CCOCCO	0.01054	-0.4156	92
13	CC(O)COCOC(C)=O	0.02417	-0.9485	80
14	CC(O)COCC(C)O	0.1084	-0.6388	0
15	CC(O)COC(C)C(O)=O	0.03866	-0.8172	75
16	CC(C(O)=O)OCOC(C)=O	0.009684	-0.7205	84
17	CC(O)COCC(C)(O)OCC(C)O	0.001119	-1.2933	79
18	CC(COCC(C)OCC(C)O)OC(=O)C=C	0.1993	0.4581	56
19	CC(COCC(C)OCOC(C)=O)OC(=O)C=C	0.04993	0.5548	52
20	CC(COCC(C)O)OC(=O)C=C	0.1228	0.3149	45
21	CC(COCOC(C)=O)OC(=O)C=C	0.03076	0.4116	74
22	CC(CO)OC(=O)C=C	0.09238	0.1717	57
23	CC(COCC(C)O)OCC(C)OCCC(=O) OC(C)COC(C)COCC(C)OC(=O)C=C	0.0316	0.9194	44
24	CC(COCC(C)O)OCC(C)OCCC(O)=O	0.08341	-0.4573	47
25	CC(COCOC(C)=O)OCC(C)OCCC(O)=O	0.02089	-0.3606	56
26	CC(COC(C)C(O)=O)OCCC(O)=O	0.01722	-0.959	42
27	CCOCC(C)OCCC(O)=O	0.02408	0.4467	46
28	CC(COCC(C)O)OCC(C)OC(=O) CCOC(C)COC(C)COCC(C)OC(=O)C=C	0.0316	0.9194	43
29	OC(C(O)=O)C(O)=O	0.008126	-2.4723	90
30	CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C(O)CO	0.00232	-0.3575	44
31	CC(COCC(C)OCC(C)O)OC(=O)C(O)CO	0.00232	-0.8022	55

 

Another estimation model CATALOGIC 301F v13.16 calculated 119 metabolites (Table 2) identifying 24 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥0.1% (equivalent to quantity setting in OASIS CATALOGIC: ≥ 0.001 [mol/mol parent]).

Table 2: QSAR prediction for CAS-#42978-66-5 (TPGDA) using CATALOGIC 301C v11.15 – July 2018 (OASIS CATALOGIC v5.13.1.156; metabolites with a quantity > 0.001 mol/mol parent after 28 d metabolite no: according to (Q)SAR model Catalogic v11.15 – July 2018 (OASIS CATALOGIC v5.13.156))

#	Smiles	Quantity [mol/mol parent]	log Kow	BOD (%)
	Constituent 1	>=0,001	>4,5
1	CC(COC(C)COC(C)C(O)=O)OC(=O)C=C	0.173	0.6861	60
2	CC(O)COC(C)COC(C)C(O)=O	0.09475	-0.674	72
3	CC(O)COC(C)C(O)=O	0.08389	-0.8172	77
4	CC(O)=O	1.06	0.0868	73
	Constituent 2
1	CC(COCC(C)OCC(O)=O)OC(=O)C=C	0.09455	0.2685	73
2	CC(O)COCC(C)=O	0.001575	-1.0566	89
3	OC(=O)C(O)=O	0.3008	-1.7365	81
4	CC(O)=O	0.5445	0.0868	73
5	CC(C(O)=O)OCC(C)=O	0.02588	-0.8286	85
	Constituent 3
1	CC(COCC(C)OCC(C)O)OC(=O)C=C	0.001904	0.4581	80
2	CC(COCC(C)OCC(O)=O)OC(=O)C=C	0.1698	0.2685	73
3	CC(O)COCC(C)=O	0.001886	-1.0566	89
4	OC(=O)C(O)=O	0.3087	-1.7365	81
5	CC(O)=O	0.9953	0.0868	73
6	CC(COCC(C)OCC(O)C(O)=O)OC(=O)C=C	0.01641	-0.4673	78
	Constituent 4
1	CC(COCC(C)OCC(C)OCCC(O)=O)OC(=O)C=C	0.1267	0.9028	70
2	CC(O)COCC(C)=O	0.002698	-1.0566	89
3	OC(=O)C(O)=O	0.5498	-1.7365	81
4	CC(O)=O	1.311	0.0868	73
5	CC(C(O)=O)OCC(C)=O	0.06505	-0.8286	85
6	CC(COCC(C)=O)OCC(C)O	0.001942	-0.9134	84
7	CC(COCC(C)OCC(C)O)OC(=O)C=C	0.00137	0.4581	80
8	CC(COCC(C)OCC(O)=O)OC(=O)C=C	0.1242	0.2685	73
9	CC(COCC(C)OCC(O)C(O)=O)OC(=O)C=C	0.01294	-0.4673	78

 

Persistence (“P/vP”):

In order to assess the biodegradation potential of the relevant degradation products, the (Q)SAR models CATALOGIC 301C v11.15, CATALOGIC 301F v5.13.1 July 2018 (OASIS CATALOGIC v5.13.1.156), were applied.    

- CATALOGIC 301C v11.15 (OASIS Catalogic v5.13.1) predicted for the constituents 212 metabolites, identifying 133 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record). Thirty of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD). The other relevant metabolites were estimated to be not readily biodegradable (0 to 56% after 28 days, based on BOD). In conclusion, the majority of the predicted metabolites present in a concentration of ≥ 0.1% (equivalent to >=0.001 mol/mol parent) are estimated to be not readily biodegradable.

- CATALOGIC 301F v13.16 (OASIS Catalogic v5.13.1) predicted for the constituents 119 metabolites, identifying 24 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record). All of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD).

In conclusion, the majority of the predicted metabolites present in concentration of ≥0.1% (equivalent to quantity setting in OASIS CATALOGIC: 0.001 [mol/mol parent]) are estimated to be not readily biodegradable.

The degradation products of TPGDA (CAS42978-66-5) which are predicted to be not readily biodegradable should be considered as potentially P/vP from a precautionary point of view, until further data become available.

 

Bioaccumulation (“B/vB”):

Without exception, all of the modelled degradation products of TPGDA were estimated to exhibit log Kow values of clearly ≤4.5 (see Table 1), thereby not fulfilling the screening criteria for bioaccumulation (B/vB) as laid down in Section 3.1 of REACH Annex XIII.

In addition, several QSAR calculations (calculated BCF values range between 0.95 L/kg and 59.3 L/kg, BASF SE 2016, 2017) indicate no potential for bioaccumulation.

Based on the estimation data available for the modelled metabolites, all (relevant) metabolites of TPGDA are concluded to be “not B” and “not vB”.

 

Toxicity (“T”):

As the predicted degradation products are not likely to fulfill both the P/vP and B/vB criteria, no information was collected on their toxicity properties.

 

Overall conclusion:

1.  Sufficient test data are available to assess the PBT/vPvB properties of TPGDA.

2.  Potentially relevant degradation products were modeled using (Q)SARmodel CATALOGIC 301C v11.15 and CATALOGIC 301F v5.13.1 – July 2018 (OASIS CATALOGIC v5.13.1.156):

2a. Based on modeled data relevant degradation products present in concentration of ≥ 0.1% (equivalent to quantity setting in OASIS CATALOGIC: ≥0.001 [mol/mol parent]) do neither fulfill the PBT criteria (not PBT) nor the vPvB criteria (not vPvB).

2b. However, 103 predicted relevant metabolites present in concentration of ≥0.1% (equivalent to quantity setting in OASIS CATALOGIC: ≥0.001 [mol/mol parent]) should be considered as potentially P/vP from a precautionary point of view.