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PBT assessment

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PBT assessment: overall result

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Name:
Tripropylene glycol diacrylate
Type of composition:
boundary composition of the substance
State / form:
liquid
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Name:
Tripropylene glycol diacrylate
Type of composition:
legal entity composition of the substance
State / form:
liquid
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
Reference substance:
Composition 1
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.