3-[Tris(trimethylsiloxy)silyl]propyl methacrylate
[CAS# 17096-07-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: 3-[Tris(trimethylsiloxy)silyl]propyl methacrylate
• Synonyms: 3-(Methacryloyloxy)propyltris(trimethylsiloxy)silane
• Molecular Formula: C₁₆H₃₈O₅Si₄
• Molecular Weight: 422.81
• CAS Registry Number: 17096-07-0
• EC Number: 241-165-0
• SMILES: CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C

Properties

• Solubility: 3.094e-005 mg/L (25 °C water)
• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.432, Calc.^*
• Melting point: 38.82 °C
• Boiling Point: 368.6±44.0 °C (760 mmHg), Calc.^*, 319.29 °C
• Flash Point: 146.9±24.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

3-[Tris(trimethylsiloxy)silyl]propyl methacrylate, commonly known as TMSPMA, is a silane coupling agent. Silane coupling agents are molecules that contain both organic and inorganic functional groups, allowing them to chemically bond with organic polymers and inorganic substrates. TMSPMA was developed as a multifunctional monomer and coupling agent with specific chemical properties.

One of the primary applications of TMSPMA is as an adhesion promoter or coupling agent in adhesive formulations and surface coatings. Due to its unique chemical structure, TMSPMA can form strong covalent bonds with organic substrates such as polymers and inorganic surfaces such as glass, metal, or ceramics. TMSPMA is commonly used in adhesive formulations for automotive, aerospace, construction and electronics applications. TMSPMA is also used for surface modification and functionalization of a variety of substrates to impart desired properties or enhance surface properties. When applied to a surface, TMSPMA can react with hydroxyl groups (-OH) present on the surface of the substrate to form strong siloxane bonds (-Si-O-Si-) that anchor the molecule to the surface. This surface modification can improve surface wetting, reduce surface energy, enhance water resistance, and promote paint adhesion. As a methacrylate monomer, TMSPMA can be copolymerized with other monomers to produce functional polymers with customized properties. Polymers containing TMSPMA find applications in coatings, adhesives, sealants, composites and surface modification technologies. TMSPMA can also be used as a cross-linking agent in polymerization reactions, reacting with other functional monomers or polymers to form a cross-linked network. Cross-linking gives polymer materials dimensional stability, chemical resistance and mechanical strength, making them suitable for demanding applications such as coatings, sealants and encapsulants. In biomedical and healthcare applications, TMSPMA is used for surface modification of medical devices, implants, and biomaterials to improve biocompatibility, reduce fouling, and enhance tissue integration. TMSPMA can also be used as a reactive diluent or cross-linker in photopolymerization processes, where rapid polymerization occurs upon exposure to ultraviolet (UV) or visible light with the advantages of rapid cure, low VOC emissions, and high yields.

References

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DOI: 10.1007/s10965-019-1813-6