Tris(isopropenyloxy)vinylsilane
[CAS# 15332-99-7]

Identification

• Classification: Chemical reagent >> Silane reagent
• Name: Tris(isopropenyloxy)vinylsilane
• Synonyms: ethenyl-tris(prop-1-en-2-yloxy)silane
• Molecular Formula: C₁₁H₁₈O₃Si
• Molecular Weight: 226.34
• CAS Registry Number: 15332-99-7
• EC Number: 239-362-1
• SMILES: CC(=C)O[Si](C=C)(OC(=C)C)OC(=C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.447, Calc.^*
• Boiling Point: 224.3±13.0 ºC (760 mmHg), Calc.^*
• Flash Point: 88.2±27.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Hazard Statements: H226-H315-H319-H335
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Tris(isopropenyloxy)vinylsilane, with the chemical formula C12H18O3Si, is an organosilicon compound that is widely used in various industrial applications. It is part of the broader family of vinylsilane compounds, which are essential in the preparation of advanced materials due to their ability to form crosslinked networks. This particular compound, characterized by its three isopropenyloxy groups attached to a vinylsilyl backbone, was first synthesized as part of efforts to improve the properties of silane-based coupling agents and polymer precursors.

The discovery of tris(isopropenyloxy)vinylsilane can be traced back to studies in the 1970s when researchers focused on creating functionalized silanes capable of reacting with different substrates, including organic polymers and inorganic surfaces. The development of such silanes was aimed at enhancing the adhesive properties, durability, and thermal resistance of materials, particularly in the construction, automotive, and electronics industries. Tris(isopropenyloxy)vinylsilane, in particular, has emerged as a versatile compound because of its ability to both polymerize and bond to a wide range of materials, making it valuable in different manufacturing processes.

The synthesis of tris(isopropenyloxy)vinylsilane typically involves the reaction of vinylsilanes with isopropenyl alcohol or isopropenyl ether derivatives under controlled conditions. This process leads to the formation of the desired trisubstituted silane, where each of the three isopropenyloxy groups is attached to the silicon atom, providing a high degree of reactivity for subsequent reactions. The compound can be obtained in high purity and is often used in the preparation of advanced coatings, adhesives, and sealants due to its strong bonding characteristics and ability to improve the mechanical properties of composites.

One of the primary applications of tris(isopropenyloxy)vinylsilane is in the field of coatings and adhesives. It is frequently used as a coupling agent in the formulation of sealants and coatings for automotive, aerospace, and construction industries. The compound’s ability to bond strongly to both inorganic surfaces (such as metals and glass) and organic materials (such as polymers) makes it an ideal component in formulations designed to enhance adhesion, durability, and resistance to environmental factors such as moisture, heat, and chemicals.

In addition to its use in coatings, tris(isopropenyloxy)vinylsilane is widely used in the production of advanced polymer composites. It acts as a crosslinking agent for silicone rubbers and other polymers, improving their mechanical strength, thermal stability, and chemical resistance. The compound’s reactivity with the polymer matrix allows for the formation of more robust, long-lasting materials that are used in a variety of industrial and consumer applications. These include the production of gaskets, electrical insulation, and weather-resistant seals.

Tris(isopropenyloxy)vinylsilane also finds application in the preparation of functionalized silica nanoparticles. The compound’s ability to attach to the surface of silica particles allows for the creation of silica-based materials with enhanced properties, such as improved dispersibility, increased surface area, and better interaction with polymer matrices. These functionalized silica nanoparticles are used in a wide range of industries, including electronics, automotive, and nanotechnology.

Another significant application of tris(isopropenyloxy)vinylsilane is in the modification of glass fibers used in reinforced plastic composites. The chemical bonding between the silane and the glass surface enhances the fiber-matrix adhesion, leading to stronger and more durable composite materials. This is particularly important in industries that require lightweight, high-performance materials, such as the automotive and aerospace sectors.

In conclusion, tris(isopropenyloxy)vinylsilane is a highly versatile organosilicon compound with a broad range of applications in coatings, adhesives, polymer composites, and nanomaterials. Its ability to form strong bonds with various substrates and its role as a crosslinking agent make it invaluable in the production of advanced materials with improved mechanical and environmental resistance properties.