Tripropylene glycol diacrylate
Basic information
- CAS
42978-66-5- Standard SMILES
C=CC(=O)OCC(C)OCC(C)OCC(C)OC(=O)C=C- InChIKey
LJRSZGKUUZPHEB-UHFFFAOYSA-N- Molecular formula
- C15H24O6
- Average molar mass
- 300.35 g/mol
- Monoisotopic mass
- 300.15728848
Overview
a component of UV-Cured Lacquer; structure given in first source
Names & identifiers
- Preferred name
- Tripropylene glycol diacrylate
- IUPAC
- 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate
- English name
- Tri(propylene glycol) diacrylate
- Molecular formula
- C15H24O6
- Molecular weight
- 300.35
Names & synonyms
Tripropylene glycol diacrylate42978-66-5DTXSID7028015DTXCID108015(1-Methyl-1,2-ethanediyl)bis(oxy(methyl-2,1-ethanediyl)) diacrylateAcrylic acid, propylenebis(oxypropylene) esterRefChem:900078256-032-2272-647-92-Propenoic acid, (1-methyl-1,2-ethanediyl)bis(oxy(methyl-2,1-ethanediyl)) ester2-Propenoic acid, 1,3-propanediylbis(oxy-3,1-propanediyl) ester23WVB80NSU
Show more names
TPGDATRPGDA2-{2-[2-(Acryloyloxy)-1-methylethoxy]-1-methylethoxy}-1-methylethyl acrylate(1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)] diacrylatePhotomer 4061Photomer 4061GPhotomer 3016 TFPhotomer 4061 G TFCHLUMICRYL TPGDA Monomer
Tri(propylene glycol) diacrylate94120-00-0tri(propyleneglycol)diacrylate2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate1,4,7-Trimethyl-3,6-dioxaoctamethylene diacrylateMFCD00064598VFM08CHC4DTRIPROPLYLENEGLYCOL DIACRYLATE
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 71.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 352
Experimental & physicochemical properties
PolymersPlastics & Rubber -> (Meth)acrylates
Physical Description
Dry Powder; CBI; Liquid
Pale yellow to amber liquid with an ester odor; Hygroscopic; [IUCLID] Light yellow liquid; [Aldrich MSDS]
Collision Cross Section169.9 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7028015]
Physicochemical properties
- Boiling point
- 361.58 °C · 361.58°C (rough estimate)
- Density
- 1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.01 mm · <0.01 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.45(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Amber Vial, Refrigerator, Under inert atmosphere
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315: Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3100) of reports.
Warning
H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, (1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)] ester
2-Propenoic acid, 1,1'-[(1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)]] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 1,1'-[(1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)]] ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: (1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)] diacrylate (EC: 256-032-2)
Tripropylene glycol diacrylate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Propenoic acid, (1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)] ester: Human health tier II assessment
Hazards Summary
Allergic contact dermatitis reported in workers handling dental resins, inks, and nail products; [Kanerva, p. 1745] May polymerize on light exposure; Heat may cause rapid and violent polymerization; A skin, eye, and respiratory tract irritant; May cause skin sensitization; One report of occupational skin sensitization in a print worker; Highly irritating to rabbit eyes; Equivocal results in guinea pig skin sensitization studies; [IUCLID] May polymerize on light exposure; A skin, respiratory tract, and strong eye irritant; May cause skin sensitization; [Aldrich MSDS]
Chemistry & industry
Uses & manufacturing
Uses
Used in UV-cured inks and resins for dentistry and artificial nails; [Kanerva, p. 1745] Used for synthesis in the chemical industry and in the paint/lacquer/varnish industry; [IUCLID]
Plastic Composites Manufacturing [Category: Industry]
U.S. Production2023: 7,000,000 - <8,500,000 lb
Consumer UsesHardener
Industry UsesPigment
General Manufacturing Information
Printing and Related Support Activities
2-Propenoic acid, 1,1'-[(1-methyl-1,2-ethanediyl)bis[oxy(methyl-2,1-ethanediyl)]] ester: ACTIVE
Applications
DescriptionAs a cause of occupational contact dermatitis, tripropylene glycol diacrylate (TPGDA) was contained in dental resins, in UV-cured inks and in nail eosmetics.
UsesTripropylene glycol diacrylate is a diacrylate monomer for use in UV-curable flexographic and silk-screen inks, wood-finish varnishes, coatings on plastics, etc.
UsesTripropylene Glycol Diacrylate is a microparticle used to study continuous-flow lithography of high-throughput microparticle synthesis.
Preparation methods
PreparationA direct esterification method for Tri(propylene glycol) diacrylate was employed to synthesize the product. Specifically, dipropylene glycol and C3H4O2 were reacted in a specific molar ratio with an acidic catalyst, a polymerization inhibitor, and a solvent at a controlled temperature. During the reaction, water generated was continuously removed from the reaction system through azeotropic extraction of the solvent and water. After the esterification reaction was complete, the acidic catalyst and residual C3H4O2 were removed from the reaction system by neutralization, and then the solvent was removed under vacuum to obtain the product.
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