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The new ECHA CHEM database has been released by ECHA, and it now contains all REACH registration data. There are more details on the transition of ECHA's published data to ECHA CHEM here.
Diss Factsheets
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EC number: - | CAS number: -
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Hydrolysis
Some information in this page has been claimed confidential.
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- other information
- Study period:
- 2010
- Reliability:
- 3 (not reliable)
- Rationale for reliability incl. deficiencies:
- unsuitable test system
Data source
Reference
- Reference Type:
- publication
- Title:
- Degradation of 10-Methacryloyldecyl dihydrogen phosphate
- Author:
- Teshima I
- Year:
- 2 010
- Bibliographic source:
- J Dental Res Vol. 89 No.11 pp. 1281-1286
- Report date:
- 2010
Materials and methods
Test guideline
- Qualifier:
- no guideline followed
- Principles of method if other than guideline:
- - Principle of test:
0.5 mmol of 10-methacryloyloxydecyl dihydrogen phosphate or 2-methacryloyloxyethyl dihydrogen phosphate were dissolved in a 5 mol% aqueous solution of N-methacryloyl glycine or hydroxyethyl methacrylate and stored. Period samples were analyzed by 13C-NMR
- Short description of test conditions: After formulation of reaction mixtures, they were incubated at 40 ± 0.5 °C for 1, 3, 6, 10, and 14 weeks. NMR scans were done immediately after formulation and after each of the storage periods. Solution pH was measured by pH meter after formulation and at weeks 6 and 14.
- Parameters analysed / observed: relative peak intensity of specific peaks were used to identify parent and hydrolysis products. Hydrolytic rates were determined relative to the other methacrylate-phosphate material and were not reported as absolute rate constants. Rate data is thus not reported. - GLP compliance:
- no
- Remarks:
- published study
Test material
- Reference substance name:
- 10-(phosphonooxy)decyl methacrylate
- Molecular formula:
- C14H27O6P
- IUPAC Name:
- 10-(phosphonooxy)decyl methacrylate
Constituent 1
Study design
- Analytical monitoring:
- yes
Duration of test
- Duration:
- 14 wk
- pH:
- 2
- Temp.:
- 40 °C
- Initial conc. measured:
- 0.5 mmol/L
Results and discussion
- Transformation products:
- yes
Identity of transformation productsopen allclose all
- No.:
- #2
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- methacrylic acid
- Inventory number:
- InventoryMultipleMappingImpl [inventoryEntryValue=EC 201-204-4]
- CAS number:
- 79-41-4
- Identity:
- 2-Propenoic acid, 2-methyl-
- Molecular formula:
- C4H6O2
- Molecular weight:
- 86.089
- SMILES notation:
- CC(=C)C(=O)O
- InChl:
- InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
- No.:
- #3
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- decane-1,10-diol
- Inventory number:
- InventoryMultipleMappingImpl [inventoryEntryValue=EC 203-975-2]
- CAS number:
- 112-47-0
- Identity:
- 1,10-Decanediol
- Molecular formula:
- C10H22O2
- Molecular weight:
- 174.28
- SMILES notation:
- OCCCCCCCCCCO
- InChl:
- InChI=1/C10H22O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,1-10H2
- Details on hydrolysis and appearance of transformation product(s):
- The carbon shifts followed for 10-methacryloyloxydecyl dihydrogen phosphate are depicted in the illustration. Specific 13C NMR shifts followed included the methacrylate carbonyl (d) and methylene (a) carbons, the terminal and subterminal carbons on either side of decane-1,10-diol (e, g, zeta). Neither the central 8 carbons of decane-1,10-diol (f) nor the remaining methacrylate carbons provided useful information. Differential results were found when 10-methacryloyloxydecyl dihydrogen phosphate was co-incubated with N-methacryloyl glycine (NMG) v. 2-hydroxyethyl methacrylate (HEMA). In particular, a small peak for the d- and a- carbons (methacrylate carbonyl and methylene) developed in the HEMA co-incubation but not in the NMG co-incubation. The new peaks were attributed to hydrolysis of the phosphate ester on the opposite side of the structure. No such difference was found in the e- or g-carbons adjacent to the acrylate and phosphate, respectively, for hydrolysis of the opposite moiety. Also, while the decane-1,10-diyl terminal carbons could be distinguished between intact and hydrolyzed forms, the hydrolyzed 1- and 10-carbons could not be distinguished: these carbons appeared identical whether in 10-hydroxydecyl dihydrogen phosphate, 10-hydroxyoxydecyl methacrylate, or decan-1,10-diol. Similar behavior was found for the subterminal carbon (labeled zeta after hydrolysis). Initial hydrolysis of the phosphate group in the HEMA co-incubation was concluded, but hydrolysis of the phosphate ester could not be demonstrated by the NMR results. The authors concluded that they phosphate ester hydrolyzed due to acidification of the test solution over the course of the experiment (initial pH 1.90 and 1.84, final pH 1.67 and 1.58 for the NMG and HEMA experiments, respectively).
- Results with reference substance:
- 2-methacryloxyethyl dihydrogen phosphate was also tested. In this case, the three hydrolysis products could clearly be distinguished on the NMR spectra, indicating complete hydrolysis of the molecule.
Applicant's summary and conclusion
- Validity criteria fulfilled:
- not applicable
- Conclusions:
- 10-methacryloyloxydecyl dihydrogen phosphate, a constituent of MDP, hydrolyzes to form decane-1,10-diol under acidic conditions (pH <2)
- Executive summary:
Hydrolytic behavior of the 10-methacryloyloxydecyl dihydrogen phosphate of MDP was studied in acidic conditions using 13C NMR. The test material was co-incubated with 5 mole percent of N-methacryloyl glycine or 2-hydroxyethyl methacrylate for 14 weeks. Acidity of the solutions increased during the incubation. Chemical shift data indicated hydrolysis of the molecule, and decrease in solution pH was taken as evidence that hydrolysis led to 1,10-decanediol. Hydrolysis rate was expressed relative to 2-methacryloyloxydecyl dihydrogen phosphate. The experiment appears to have been conducted well. However, given the extreme reaction conditions the test system is considerable unsuitable and the result is not considered reliable.
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