2-Hydroxypropyl acrylate

• CAS: 32029-53-1
• Catalog Number: ACM32029531
• Category: Main Products
• Molecular Weight: 130.14
• Molecular Formula: C6H10O3
• Synonyms: Propylene glycol monoacrylate
• Appearance: Fused mass

Case Study

2-Hydroxypropyl Acrylate as a Model Water-Miscible Compound for Investigating Stratum Corneum Hydration Effects on Dermal Permeation

Frasch, H.F., et al. (2014). International Journal of Pharmaceutics, 460, 240-249.

2-Hydroxypropyl acrylate (HPA) functions as an ideal model water-miscible compound for studying how thermodynamic activity and skin hydration govern dermal permeation behavior, providing critical data for occupational risk assessment of acrylic monomers.
Experimental Protocol: In vitro permeation experiments employed heat-separated human epidermal membranes and silicone rubber membranes in static diffusion cells at 32-33 degrees C. Donor solutions spanned the full range of HPA-H₂O binary mixtures (volume fraction 0.10 to 1.00). Thermodynamic activities of HPA and H₂O were determined via static headspace gas chromatography and calibrated relative humidity sensing, respectively. Additional experiments held HPA activity constant while reducing H₂O activity using a high-molecular-weight polymer. Stratum corneum water uptake was measured gravimetrically after incubating desiccated SC discs with HPA-H₂O solutions.
Performance Evaluation: Steady-state HPA flux through silicone membranes was a linear function of HPA thermodynamic activity (r²=0.99), confirming activity as the true driving force. Through human epidermis, flux increased linearly up to an HPA activity of 0.35 but then declined sharply, with neat HPA flux being approximately one twenty-fifth of the extrapolated value. At constant HPA activity, flux decreased 4.5-fold as water activity dropped from 1.00 to 0.82. Stratum corneum water content diminished substantially with increasing HPA concentration, providing unequivocal evidence that SC dehydration substantially increases epidermal barrier function.

2-Hydroxypropyl Acrylate as a Thermo-Responsive Monomer for Tunable LCST Copolymers in Biomedical Applications

Savas, B., et al. (2025). Journal of Polymers and the Environment, doi: 10.21203/rs.3.rs-6958444/v1.

2-Hydroxypropyl acrylate (HPA) serves as the primary monomer for synthesizing thermo-responsive statistical copolymers whose lower critical solution temperature (LCST) can be precisely tuned by incorporating various acrylamide derivative comonomers, enabling applications in drug delivery and tissue engineering.
Experimental Protocol: A series of poly(2-hydroxypropyl acrylate)-based statistical copolymers were synthesized via free-radical polymerization at 70 degrees C for 16 hours in 1,4-dioxane using 2,2'-azoisobutyronitrile as initiator. Five acrylamide derivatives were copolymerized with HPA: N-isobutoxymethyl acrylamide, N-(3-methoxypropyl)acrylamide, acrylamide, N-(2-hydroxyethyl)acrylamide, and methacrylamide. Copolymer compositions were varied systematically. Structural characterization was performed by elemental analysis, FTIR, and ¹H-NMR. Thermal properties including glass transition temperature and LCST were determined by DSC and turbidimetry measurements.
Performance Evaluation: The LCST values of the statistical copolymers ranged from 7.5 to 48.2 degrees C, depending on the comonomer identity and its molar fraction in the copolymer. Increasing the comonomer content generally elevated the LCST. Among all comonomers, acrylamide and N-(2-hydroxyethyl)acrylamide were most effective at raising the cloud point due to their superior hydrophilicity and hydrogen-bonding capability. Conversely, copolymers containing the more hydrophobic N-isobutoxymethyl acrylamide exhibited LCST values even lower than the homopolymer value of 16 degrees C. The glass transition temperatures increased with comonomer incorporation, and all copolymers displayed multi-step thermal decomposition profiles with initial mass loss attributed to dehydration reactions.

2-Hydroxypropyl Acrylate as a Functional Comonomer for Improving Electro-Optical Properties and Stability of Polymer-Dispersed Liquid Crystal Films

Wang, L., et al. (2010). Molecular Crystals and Liquid Crystals, 518, 3-11.

2-Hydroxypropyl acrylate (HPA) acts as a critical comonomer in polymer-dispersed liquid crystal (PDLC) films, where its incorporation enhances polymer network elasticity, substrate adhesion strength, and the thermal and electro-optical stability of the films.
Experimental Protocol: Two PDLC films were fabricated via polymerization-induced phase separation between indium tin oxide (ITO) substrates using UV irradiation at 365 nm. The HPA-free formulation contained 1,4-butanediol diacrylate (BDDA) and butyl methacrylate (BMA) as monomers at 10 wt% each with 80 wt% nematic liquid crystal. The HPA-containing formulation used BDDA (3 wt%), BMA (3 wt%), and HPA (14 wt%) with the same liquid crystal loading. Electro-optical measurements were conducted at 632.8 nm with a 100 Hz square-wave electric field. Polymer morphologies were examined by scanning electron microscopy, and mechanical properties were evaluated by tensile testing.
Performance Evaluation: The HPA-containing PDLC film exhibited substantially lower threshold voltage (5.9 V vs. 10.3 V) and saturation voltage (18.5 V vs. 33.6 V) compared with the HPA-free counterpart, while maintaining a contrast ratio of 20. The polymer network holes were larger and more uniform in the HPA-containing film due to significant polymerization shrinkage (10.20% volume change vs. 0.19%). Adhesion strength to ITO substrates increased from 274 to 325 MPa. After 500 electric field switching cycles, the HPA-containing film showed negligible change in contrast and OFF-state response time, whereas the HPA-free film exhibited a 50% contrast reduction and threefold increase in response time.

Custom Q&A

What is the molecular formula of 2-Hydroxypropyl acrylate?

The molecular formula of 2-Hydroxypropyl acrylate is C6H10O3.

What are the synonyms of 2-Hydroxypropyl acrylate?

The synonyms of 2-Hydroxypropyl acrylate are 2-Hydroxypropyl prop-2-enoate, Propylene glycol monoacrylate, and 1,2-Propanediol, 1-acrylate.

What is the molecular weight of 2-Hydroxypropyl acrylate?

The molecular weight of 2-Hydroxypropyl acrylate is 130.14 g/mol.

When was 2-Hydroxypropyl acrylate created?

2-Hydroxypropyl acrylate was created on March 27, 2005.

What is the IUPAC name of 2-Hydroxypropyl acrylate?

The IUPAC name of 2-Hydroxypropyl acrylate is 2-hydroxypropyl prop-2-enoate.

What is the InChI of 2-Hydroxypropyl acrylate?

The InChI of 2-Hydroxypropyl acrylate is InChI=1S/C6H10O3/c1-3-6(8)9-4-5(2)7/h3,5,7H,1,4H2,2H3.

What is the InChIKey of 2-Hydroxypropyl acrylate?

The InChIKey of 2-Hydroxypropyl acrylate is GWZMWHWAWHPNHN-UHFFFAOYSA-N.

What are the other identifiers for 2-Hydroxypropyl acrylate?

The other identifiers for 2-Hydroxypropyl acrylate include CAS number 999-61-1, EC number 213-663-8, UN number 2927, and UNII F17T4R74K6.

What is the XLogP3 value of 2-Hydroxypropyl acrylate?

The XLogP3 value of 2-Hydroxypropyl acrylate is 0.3.

What is the topological polar surface area (TPSA) of 2-Hydroxypropyl acrylate?

The topological polar surface area (TPSA) of 2-Hydroxypropyl acrylate is 46.5Ų.