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Trimethoxyvinylsilane presents as a limpid, volatile liquid with low viscosity and a distinctive ethereal odor reminiscent of sweet esters.
Its physical properties stem from a balance between the polar methoxysilane moiety and the unsaturated hydrocarbon chain.
The compound exhibits Newtonian flow characteristics with a viscosity of approximately 0.6-0.8 cP at 25°C, facilitating easy handling and mixing in industrial applications.
Surface tension measurements indicate values around 22-24 dyn/cm, contributing to excellent wetting properties on inorganic substrates.
Systematic Identification:
IUPAC Nomenclature: Ethenyltrimethoxysilane
Chemical Abstract Service Registry: 2768-02-7
Molecular Architecture: C₅H₁₂O₃Si
Structural Representation: CH₂=CH–Si(OCH₃)₃
Molecular Mass: 148.23 g/mol ± 0.02 g/mol
Melting Point: < -70°C (supercools readily)
Boiling Point: 123°C at 1013 hPa (with decomposition onset)
Vapor Pressure: 12.5 hPa at 20°C; 24 hPa at 30°C
Heat of Vaporization: ~38 kJ/mol
Critical Temperature: Estimated 310-320°C
Critical Pressure: Estimated 2.8-3.2 MPa
Detailed Chemical Behavior and Reactivity:
The molecular architecture of VTMS embodies a sophisticated duality of reactivity—a convergence of organic unsaturation and inorganic hydrolysable functionality. This bifunctionality enables the molecule to operate as a molecular bridge between disparate material phases.
Hydrolysis Kinetics: The methoxysilane group undergoes rapid solvolysis even at ambient humidity levels (30-50% RH). The hydrolysis mechanism proceeds through a nucleophilic substitution pathway (S_N2-Si) where water molecules attack the silicon center, displacing methoxy groups as methanol. This reaction exhibits pseudo-first-order kinetics with a half-life of approximately 2-4 hours at 25°C and 50% RH. The hydrolysis rate accelerates dramatically in acidic or basic environments, with optimum catalysis occurring at pH 4-5 (acid-catalyzed) or pH 9-10 (base-catalyzed).
Condensation Chemistry: Following hydrolysis, the generated silanol groups (Si–OH) undergo polycondensation through either:
Water-producing condensation: Si–OH + HO–Si → Si–O–Si + H₂O
Alcohol-producing condensation: Si–OH + RO–Si → Si–O–Si + ROH
The condensation kinetics are influenced by temperature, concentration, and catalyst presence, with gelation times ranging from hours to days depending on conditions.
Polymerization Pathways: The vinyl group participates in multiple polymerization mechanisms:
Free-radical polymerization (initiated by peroxides, azo-compounds, or radiation)
Cationic polymerization (with Lewis or Brønsted acids)
Coordination polymerization (with Ziegler-Natta or metallocene catalysts)
Thiol-ene click chemistry (with multifunctional thiols under UV initiation)
Surface Bonding Mechanism: When applied to hydroxylated surfaces (glass, metals, ceramics), VTMS forms covalent Si–O–M bonds (where M = Si, Al, Fe, Ti, etc.) through a condensation reaction with surface hydroxyl groups. This creates a permanent, hydrolytically stable interface with an areal density of approximately 3-5 molecules/nm² for monolayer coverage.
Industrial Applications – Expanded Analysis:
Composite Materials Engineering:
In fiberglass-reinforced plastics, VTMS serves as a critical sizing component applied during fiber manufacturing. The silane forms a durable interphase region approximately 50-200 nm thick that:
Transfers stress efficiently between matrix and reinforcement
Prevents microcrack propagation at the interface
Reduces water ingress along the fiber-matrix boundary
Improves fatigue resistance by up to 300% compared to untreated systems
Typical application involves a 0.1-0.5% aqueous or hydroalcoholic solution (pH adjusted to 4.5-5.5) applied to fibers at 80-120°C, followed by thermal curing at 110-130°C for 1-3 minutes.
Adhesive and Sealant Formulations:
VTMS functions as an adhesion promoter through multiple mechanisms:
Primary chemical bonding to substrates
In-situ formation of an interpenetrating network
Modification of rheological properties
Enhancement of cohesive strength through crosslinking
In one-component moisture-curing systems, VTMS concentrations of 0.5-2.0% provide optimal balance between shelf stability and cure performance. The methoxy groups offer rapid cure initiation, making VTMS particularly valuable in fast-assembly applications.
Advanced Coating Systems:
In corrosion protection coatings, VTMS-containing primers create a hybrid organic-inorganic interface that:
Reduces oxygen and electrolyte permeability
Provides self-healing functionality through continued crosslinking
Enhances mechanical interlocking with metal substrates
Improves resistance to cathodic delamination
Electrochemical impedance spectroscopy (EIS) studies demonstrate impedance modulus increases of 2-3 orders of magnitude for VTMS-treated steel substrates compared to untreated controls.
Nanotechnology Applications:
For nanoparticle functionalization, VTMS enables precise surface engineering of:
Silica nanoparticles (20-100 nm) for rubber reinforcement
TiO₂ photocatalysts for improved dispersion in polymers
Quantum dots for enhanced compatibility with organic matrices
Cellulose nanocrystals for thermoplastic composites
SAFETY INFORMATION ABOUT TRIMETHOXYVINYLSILANE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
