2,3-Dihydroxypropyl Methacrylate

• CAS: 5919-74-4
• Catalog Number: ACM5919744
• Category: Main Products
• Molecular Weight: 160.17
• Molecular Formula: C7H12O4
• Synonyms: 2,3-dihydroxypropyl 2-methylprop-2-enoate
• Appearance: Yellowish to colorless oily; liquid

Case Study

2,3-Dihydroxypropyl Methacrylate Hydrogel Studies

Gates, G., et al. Polymer 44.1 (2003): 215-222.

The drying kinetics of four crosslinked polymers forming hydrogels were studied: 2,3-dihydroxypropyl methacrylate (DHPMA) and 2-hydroxyethyl methacrylate (HEMA) and two random copolymers in which HEMA was present in one-to-one and three-to-one molar ratios to DHPMA. The hydrogels were saturated with buffered isotonic saline solution and deionized water; the weight loss kinetics were monitored at temperatures ranging from 16 to 37 8°C, at 30% and 60% relative humidity, with air flow. While there are many studies on hydrogel diffusion, this is one of the few that examined the initial evaporative drying period. Analysis of these short-term data indicates that increasing DHPMA content decreases water volatility; the percent water loss decreases with increasing DHPMA content. Long-term desorption data combined with differential scanning calorimetry (DSC) results indicate that the departure from Fickian desorption kinetics is consistent with the onset of nonfreezing water desorption. Dynamic mechanical analysis (DMA) showed that the change in stiffness accompanying desorption was more pronounced in the polymers containing HEMA. Preliminary results indicate that the ion transport rate of the hydrogels containing DMPMA is greater.
Four different polymers were provided in standard sizes (12.8 mm diameter, 6.0 mm thick): HEMA and DHPMA homopolymers, and two HEMA/DHPMA random copolymers. Table 1 provides the copolymer name and composition, batch number, linear expansion coefficient, and weight percent of water at equilibrium swelling for all materials in this study. Water or ethylene glycol was used as the diluent during the polymerization process; for all materials, the crosslinker concentration was approximately 0.2% (by weight of EGDMA). 0.50 mm thick samples were cut from the hydrogels using a diamond cutting blade lubricated with silicone oil and rinsed in hexane. The samples were dried under vacuum at 120 ± 8 °C. The drying time for DHPMA was approximately twice that required for HEMA.

Polymerization kinetics of 2,3-dihydroxypropyl methacrylate

García, F., et al. Journal of Polymer Science Part A: Polymer Chemistry 39.11 (2001): 1843-1853.

The free radical polymerization of 2,3-dihydroxypropyl acrylate (GA) and 2,3-dihydroxypropyl methacrylate (GM) was studied in water-dioxane solutions at several temperatures. The kinetic constants were determined by UV spectroscopic techniques and the results were compared with those obtained for methyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate under the same conditions. The k/k ratios for the methacrylic monomer GM were higher than 0.5 Lmols at temperatures between 50 °C and 65 °C. For the acrylic monomer GA, these values exceeded 2 Lmol, which is probably the highest reported for this type of monomer. Electron paramagnetic resonance spectroscopy was also used to study the polymerization of GM. All polymers dissolved in the reaction mixture until very high conversions were achieved and gel effects were never detected at monomer concentrations equal to or below 1 mol·L.
2,3-Dihydroxypropyl acrylate (GA) and 2,3-dihydroxypropyl methacrylate (GM) were obtained by acid hydrolysis of their intermediate compounds isopropyl acrylate and methacrylate, respectively, to avoid separation from other compounds. Isopropyl acrylate and isopropyl methacrylate were prepared by reacting acryloyl chloride and methacryloyl chloride (1/1) with 1,2-isopropylidene glycerol (IPG) in chloroform under nitrogen atmosphere and neutralizing the hydrogen chloride produced during the reaction with triethylamine. Acryloyl and methacryloyl chloride were added dropwise to the IPG solution within 30 minutes, and the reaction medium was kept cool with an ice-water bath. The triethyl-amine salts were removed by filtration, and the reaction mixture was washed several times with distilled water. Finally, the crude product was distilled under vacuum to obtain the monomers GA and GM. IPG was easily prepared from glycerol and acetone in the presence of trace amounts of hydrogen chloride, and the purity of all compounds was checked by HPLC and NMR.

Custom Q&A

What is the molecular formula of 2,3-Dihydroxypropyl Methacrylate?

The molecular formula of 2,3-Dihydroxypropyl Methacrylate is C7H12O4.

What is the molecular weight of 2,3-Dihydroxypropyl Methacrylate?

The molecular weight of 2,3-Dihydroxypropyl Methacrylate is 160.17 g/mol.

What are the synonyms of 2,3-Dihydroxypropyl Methacrylate?

The synonyms of 2,3-Dihydroxypropyl Methacrylate are Glyceryl methacrylate and 2,3-dihydroxypropyl 2-methylprop-2-enoate.

What is the IUPAC name of 2,3-Dihydroxypropyl Methacrylate?

The IUPAC name of 2,3-Dihydroxypropyl Methacrylate is 2,3-dihydroxypropyl 2-methylprop-2-enoate.

What is the InChI of 2,3-Dihydroxypropyl Methacrylate?

The InChI of 2,3-Dihydroxypropyl Methacrylate is InChI=1S/C7H12O4/c1-5(2)7(10)11-4-6(9)3-8/h6,8-9H,1,3-4H2,2H3.

What is the InChIKey of 2,3-Dihydroxypropyl Methacrylate?

The InChIKey of 2,3-Dihydroxypropyl Methacrylate is QRIMLDXJAPZHJE-UHFFFAOYSA-N.

What is the canonical SMILES of 2,3-Dihydroxypropyl Methacrylate?

The canonical SMILES of 2,3-Dihydroxypropyl Methacrylate is CC(=C)C(=O)OCC(CO)O.

What is the CAS number of 2,3-Dihydroxypropyl Methacrylate?

The CAS number of 2,3-Dihydroxypropyl Methacrylate is 5919-74-4.

What is the physical description of 2,3-Dihydroxypropyl Methacrylate?

2,3-Dihydroxypropyl Methacrylate is a liquid.

What is the hydrogen bond donor count of 2,3-Dihydroxypropyl Methacrylate?

The hydrogen bond donor count of 2,3-Dihydroxypropyl Methacrylate is 2.