735094

Bis(2-methacryloyl)oxyethyl disulfide

contains ≤6000 ppm hydroquinone as stabilizer

• Synonym(s): DSDMA, Disulfide-based dimethacrylate
• Empirical Formula (Hill Notation): C₁₂H₁₈O₄S₂
• CAS Number: 36837-97-5
• Molecular Weight: 290.40
• MDL number: MFCD18785736
• UNSPSC Code: 12162002
• PubChem Substance ID: 329763793
• NACRES: NA.23

Properties

• form: liquid
• contains: ≤6000 ppm hydroquinone as stabilizer
• refractive index: n20/D 1.517
• density: 1.141 g/mL at 25 °C
• storage temp.: 2-8°C
• SMILES string: CC(=C)C(=O)OCCSSCCOC(=O)C(C)=C
• InChI: 1S/C12H18O4S2/c1-9(2)11(13)15-5-7-17-18-8-6-16-12(14)10(3)4/h1,3,5-8H2,2,4H3
• InChI key: CGDNFXSLPGLMHK-UHFFFAOYSA-N

Description

General description

Bis(2-methacryloyl)oxyethyl disulfide (DSDMA) belongs to the class of monomers known as disulfide-based dimethacrylates. It is widely employed as a crosslinker in the synthesis of various polymers with specific properties such as redox sensitivity and self-healing properties. DSDMA contains a disulfide bond, which can be cleaved under specific conditions, making it useful for drug delivery systems. It also undergoes thiol-disulfide exchange reactions, allowing it to react with thiols in polymers and form covalent crosslinks. This property enables the formation of networks and gels in polymer systems. Additionally, DSDMA is employed in the development of biomedical materials, such as tissue engineering scaffolds. Its ability to form stable crosslinks in biological environments makes it suitable for these applications.

Application

Bis(2-methacryloyl)oxyethyl disulfide (DSDMA) can be used in the following applications:

• Used as a crosslinker in the synthesis of reduction-responsive molecularly imprinted polymer (MIPs) nanogels for drug delivery applications. This reduction-responsive property allows for control over drug delivery and modulation of the release properties of the MIPs.
• Used as a crosslinker in the synthesis of self-healing polymer nanocomposites via dynamic disulfide exchange reaction and crosslinking properties. These self-healing polymer nanocomposites can be used in coatings, electronics, and packaging applications.
• Used as a redox-responsive cross-linker in the synthesis of zwitterionic hydrogels for effective drug delivery. DSDMA provides structural stability, redox-responsiveness, and self-healing properties, which are essential for effective drug delivery.

Safety Information

• Pictograms: GHS09
• Hazard Statements: H411
• Precautionary Statements: P273 - P391 - P501
• Hazard Classifications: Aquatic Chronic 2
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable