Oligomerisation products of 2,2'-[(1-methylethylidene)bis(4,1-phenyleneoxymethylene)]bisoxirane with acrylic acid and fatty acids, C18-unsatd., dimers and nonanoic acid

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

From October 12, 2011 to November 10, 2011

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test)

Deviations:

no

Qualifier:

according to guideline

Guideline:

EU Method C.4-C (Determination of the "Ready" Biodegradability - Carbon Dioxide Evolution Test)

Deviations:

no

Principles of method if other than guideline:

In addition, the procedures were designed to meet the test methods prescribed by the following guidelines:
- ISO Standard 9439 “Water Quality - Evaluation of ultimate aerobic biodegradability of organic compounds in aqueous medium - carbon dioxide evolution test (1999);
- ISO Standard 10634 "Water Quality - Guidance for the preparation and treatment of poorly water-soluble organic compounds for the subsequent evaluation of their biodegradability in an aqueous medium" (1995).

GLP compliance:

yes

Specific details on test material used for the study:

Ebecryl® 3702 radiation curing resin; Molecular weight: Mn is 950, Description: clear green to brown highly viscous liquid, Batch: HTIF11021, Purity: not indicated by the sponsor; treated as 100% pure, Test substance storage: at room temperature in the dark, Stability under storage conditions: stable, Solubility in water: no.

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge, domestic (adaptation not specified)

Remarks:

freshly obtained from a municipal sewage treatment plant

Details on inoculum:

The freshly obtained sludge was kept under continuous aeration until further treatment. The concentration of suspended solids was 4.6 g/l in the concentrated sludge. Before use, the sludge was allowed to settle (35 minutes) and the supernatant liquid was used as inoculum at the amount of 10 ml/l of mineral medium.

Duration of test (contact time):

28 d

Initial conc.:

15.5 mg/L

Based on:

other: TOC/L

Parameter followed for biodegradation estimation:

CO2 evolution

Details on study design:

Definitions:
-Readily biodegradable are those test substances giving a result of at least 60% biodegradation within 28 days. This pass level must be reached within the 10 days immediately following the attainment of 10% biodegradation (10-day window).
-Theoretical carbon dioxide (ThCO2) is the quantity of carbon dioxide calculated (mg) to be produced from the known or measured carbon content of the test substance when fully mineralized; also expressed as mg carbon dioxide evolved per mg test substance.
-Total Organic Carbon (TOC) of a sample is the sum of the organic carbon in solution and in suspension.

Reference substance:

acetic acid, sodium salt

Test performance:

- Temperatures recorded: 20.1 - 21.5°C.
- pH on Day 28: 7.5 - 7.8.

Key result

Parameter:

% degradation (CO2 evolution)

Value:

0

Sampling time:

29 d

Remarks on result:

other:

Remarks:

not readily biodegradable

Details on results:

The ThCO2 of the test substance was calculated to be 2.81 mg CO2/mg.

(In the toxicity control more than 25% biodegradation occurred within 14 days (35%, based on ThCO2). Therefore, the test substance was assumed not to inhibit microbial activity).

Results with reference substance:

The ThCO2 of sodium acetate was calculated to be 1.07 mg CO2/mg.

Because the theoretical calculation of the CO2 production was not possible a sample of the test substance was taken for TOC analysis.

ThCO2, expressed as mg CO2/mg test substance, was calculated from the results of carbon analysis. The first step in calculating the amount of CO2 produced is to correct for background (endogenous) CO2 production. Thus the amount of CO2 produced by a test substance is determined by the difference (in ml of titrant) between the experimental and blank Ba(OH)2 traps. The amount of 0.05 N HCl titrated is converted into mg of CO2 produced:

mg CO2 = (0.05 x delta ml HCL titrated)/2 x 44 = 1.1 x dela ml HCL titrated

Relative biodegradation values were calculated from the cumulative CO2 production relative to the total expected CO2 production based on the total carbon content of the amount of test substance present in the test bottles. A figure of more than 10% biodegradation was considered significant. The relative biodegradation values were plotted versus time together with the relative biodegradation of the positive control. If applicable, the number of days is calculated from the attainment of 10% biodegradation until 60% biodegradation. Should this period be ≤ 10 days (10-day window), then the test substance is designated as readily biodegradable. Toxicity control: if less than 25% biodegradation (based on ThCO2) occurred within 14 days, the test substance was assumed to be inhibitory. The total CO2 evolution in the inoculum blank was determined by the cumulative difference (in ml of titrant) between the blank Ba(OH)2 traps and fresh Ba(OH)2.

Validity criteria fulfilled:

yes

Interpretation of results:

not readily biodegradable

Conclusions:

Under the study conditions (modified Sturm test), the test substance was considered not readily biodegradable.

Executive summary:

A study was conducted to evaluate the ready biodegradability of the tests substance according to OECD Guideline 301B (CO2 evolution test), EU Method C.4 - C and ISO standards 9439 and 10634. Because the theoretical calculation of CO2 production was not possible, a sample of the test substance was taken for total organic carbon (TOC) analysis. The TOC content was determined to be 77%. The substance was tested in duplicate at 15.5 mg/L, i.e. 12 mg TOC/L. Based on TOC, the corresponding ThCO2 was calculated to be 2.81 mg CO2/mg. Due to low solubility in water, weighed amounts of substance on a glass plate were added to 2 L test bottles containing medium with microorganisms and mineral components. The relative biodegradation values calculated over a 28 d period revealed no significant biodegradation. In the toxicity control, the substance did not inhibit microbial activity. Under the study conditions (modified Sturm test), the test substance was considered not readily biodegradable (Desmares-Koopmans, 2011).

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

supporting study

Principles of method if other than guideline:

None

Test performance:

The purpose of this study was to determine the ready biode-gradability of the test item 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid. The test item was exposed to aerobic activated sludge from the aeration tank of a domestic waste water treatment plant for 28 days. The biodegradation was followed by the oxygen uptake of the micro organisms during exposure. As a reference item so-dium benzoate was tested simultaneously under the same conditions as the test item, and functioned as a procedure control.

Key result

Parameter:

% degradation (O2 consumption)

Value:

42

Sampling time:

28 d

Details on results:

After correction for the mean biochemical oxygen demand of the inoculum controls the mean percentage biodegrada-tion based on ThODNH4 at the end of the 28-day incubation period was 42% (mean value). The 10-day window criterion was not passed.
The degradation rate of 4,4’-Isopropylidenediphenol, oli-gomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid did not reach 60% within the 10-day window and after 28 days of incubation.
According to the test guideline, 4,4’-Isopropylidene-diphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid is considered not to be readily biodegradable, but an inherent potential was found.

Results with reference substance:

The reference substance sodium benzoate was sufficiently degraded to 85% after 14 days and to 88% after 28 days of incubation.

In the toxicity control containing both the test item and reference 44% biodegradation was noted within 14 days and 57% biodegradation was determined after 28 days of incubation. According to the test guidelines the test item can be assumed to be not inhibitory on theaerobic activatedsludge micro organisms because degradation was >25% within 14 days.

Validity criteria fulfilled:

yes

Interpretation of results:

inherently biodegradable

Conclusions:

Based on the results of the study, the test substance can be considered to be inherently biodegradable.

Executive summary:

A study was conducted to evaluate the ready biodegradability of the read across substance, 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid (i.e., BADGEDA), according to OECD Guideline 301F (CO2 evolution test), EU Method C.4 - D and in compliance with GLP.

The mean biodegradation after 28 days of the substance was 42% (ThODNH4). Therefore, the test substance is considered not to be readily biodegradable, but an inherent potential was found.

The reference substance, sodium benzoate, was sufficiently degraded to 85% after 14 days and to 88% after 28 days of incubation, thus confirming the suitability of theaerobic activatedsludge inoculum used.In the toxicity control containing both, the test substance and the reference substance, sodium benzoate, 44% biodegradation was noted within 14 days and 57% biodegradation after 28 days of incubation. Thus, the test substance can be assumed to be not inhibitory to theaerobic activated sludge microorganisms. (Feil, 2010).

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2010-05-05-2010-06-02

Reliability:

1 (reliable without restriction)

Reason / purpose for cross-reference:

reference to same study

Reason / purpose for cross-reference:

reference to other study

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 F (Ready Biodegradability: Manometric Respirometry Test)

Deviations:

no

Guideline:

EU Method C.4-D (Determination of the "Ready" Biodegradability - Manometric Respirometry Test)

Deviations:

no

Principles of method if other than guideline:

None

GLP compliance:

yes (incl. QA statement)

Specific details on test material used for the study:

Name: 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid
Product Name: CN104
CAS No.: 55818-57-0
Batch No.: 56728
Certificate of Analysis Date: March 16, 2010
Purity: Mixture of 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid (almost 100% purity of the whole substance according to comments of the customer).
Empirical Formula / Molecular Weight: C27H32O8 + n(C18H20O3) / 484.55 g/mol + 284.35 g/mol
Theoretical Oxygen Demand: ThODNH4: 2.289 mg oxygen per mg test item (calculated of total formula + n-homologous chain); n = 0.1
Physical Appearance / Colour: Liquid / colourless
Expiry Date: October 31, 2011
Storage: In original container, at room temperature (20 + 5ºC), in the dark
(stored for 7 days in refrigerator at 4 + 4ºC after receipt at the test facility)

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge, non-adapted

Details on inoculum:

Aerobic activated sludge, micro organisms from a domestic waste water treatment plant was supplied by the sewage plant Darmstadt, Germany.

Duration of test (contact time):

28 d

Initial conc.:

100 mg/L

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

The purpose of this study was to determine the ready biode-gradability of the test item 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid. The test item was exposed to aerobic activated sludge from the aeration tank of a domestic waste water treatment plant for 28 days. The biodegradation was followed by the oxygen uptake of the micro organisms during exposure. As a reference item so-dium benzoate was tested simultaneously under the same conditions as the test item, and functioned as a procedure control.

Reference substance:

benzoic acid, sodium salt

Test performance:

The purpose of this study was to determine the ready biode-gradability of the test item 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid. The test item was exposed to aerobic activated sludge from the aeration tank of a domestic waste water treatment plant for 28 days. The biodegradation was followed by the oxygen uptake of the micro organisms during exposure. As a reference item so-dium benzoate was tested simultaneously under the same conditions as the test item, and functioned as a procedure control.

Key result

Parameter:

% degradation (O2 consumption)

Value:

42

Sampling time:

28 d

Details on results:

After correction for the mean biochemical oxygen demand of the inoculum controls the mean percentage biodegrada-tion based on ThODNH4 at the end of the 28-day incubation period was 42% (mean value). The 10-day window criterion was not passed.
The degradation rate of 4,4’-Isopropylidenediphenol, oli-gomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid did not reach 60% within the 10-day window and after 28 days of incubation.
According to the test guideline, 4,4’-Isopropylidene-diphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid is considered not to be readily biodegradable, but an inherent potential was found.

Results with reference substance:

The reference item sodium benzoate was sufficiently degraded to 85% after 14 days and to 88% after 28 days of incubation.

In the toxicity control containing both the test item and reference 44% biodegradation was noted within 14 days and 57% biodegradation was determined after 28 days of incubation. According to the test guidelines the test item can be assumed to be not inhibitory on theaerobic activatedsludge micro organisms because degradation was >25% within 14 days.

Validity criteria fulfilled:

yes

Interpretation of results:

inherently biodegradable

Conclusions:

According to the test guideline, the test substance is considered not to be readily biodegradable, but an inherent potential was found.

Executive summary:

The test substance 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid contains no nitrogen, therefore the evaluation of biodegradation has to be based ThOD_NH4. The criterion for ready biodegradability under the conditions of a manometric respirometry test is the 10-day window, describing the period between reaching at least 10% degradation and 60% degradation. This period should not exceed 10 days.

The mean biodegradation after 28 days of 4,4’-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid was 42% (ThOD_NH4); the 10 day window criterion was not passed.

Therefore, the test substance is considered not to be readily biodegradable, but an inherent potential was found.

The reference substance, sodium benzoate, was sufficiently degraded to 85% after 14 days and to 88% after 28 days of incubation, thus confirming the suitability of the aerobic activated sludge inoculum used. In the toxicity control containing both, the test substance and the reference substance, sodium benzoate, 44% biodegradation was noted within 14 days and 57% biodegradation after 28 days of incubation. Thus, the test substance can be assumed to be not inhibitory to the aerobic activated sludge microorganisms.

Description of key information

Although the test substance is not readily biodegradable, based on the available weight of evidence it is not considered to be persistent in the environment.

Key value for chemical safety assessment

Biodegradation in water:

inherently biodegradable

Additional information

A study was conducted to evaluate the ready biodegradability of the test substance according to OECD Guideline 301B (CO2 evolution test), EU Method C.4 - C and ISO standards 9439 and 10634. Because the theoretical calculation of CO2 production was not possible, a sample of the test substance was taken for total organic carbon (TOC) analysis. The TOC content was determined to be 77%. The substance was tested in duplicate at 15.5 mg/L, i.e. 12 mg TOC/L. Based on TOC, the corresponding ThCO2 was calculated to be 2.81 mg CO2/mg. Due to low solubility in water, weighed amounts of substance on a glass plate were added to 2 L test bottles containing medium with microorganisms and mineral components. The relative biodegradation values calculated over a 28 d period revealed no significant biodegradation. In the toxicity control, the substance did not inhibit microbial activity. Under the study conditions (modified Sturm test), the test substance was considered not readily biodegradable (Desmares-Koopmans, 2011).

Although the above study with the test substance indicates it may have a potential to persist, however, considering the available weight of evidence on its major components, the substance can be expected to be inherently biodegradable and hence not likely to be persistent.

An OECD guideline compliant 301F study with 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane, esters with acrylic acid (i.e., BADGEDA), was found to be inherently biodegradable with 42% degradation in 28 days (Feil, 2010). Also, its experimental half-life value obtained (110 h at pH 7; EU method C7) in freshwater (Meinerling, 2010) was lower than the P (T1/2 > 40 days in freshwater) and vP (T1/2 > 60 days in freshwater) criteria.

Further, biodegradation modelling of 21% of the non-overlapping composition of the test substance (i.e., BADGEMA-monononanoate; containing C9 fatty acid instead of the second acrylate) via BioWin v.4.10 of US EPA EPISuite software (US EPA, 2016), did not fulfil the P and vP screening criteria as per Annex XIII.

Therefore, based on the above weight of evidence, the test substance is not expected to have a persistence potential in the environment.