Background and overview

3-(2,3-glycidoxy)propyltrimethoxysilane is a colorless and transparent liquid, easily soluble in various organic solvents, and easily hydrolyzed and condensed to form polysiloxane. Or easily polymerized in the presence of peroxides. As a silane coupling agent, KH-560 is the earliest widely used coupling agent with a history of more than 40 years. One end of its structure has an active group, which can react with synthetic resin molecules such as epoxy, phenolic, and polyester. The other end is an alkoxy group (such as methoxy, ethoxy, etc.) or chlorine atom attached to silicon. These groups hydrolyze with water in aqueous solution or in air to form compounds that can interact with glass, minerals and inorganic fillers. The hydroxyl groups on the surface react to form reactive silanols. Therefore, silane coupling agents are often used in silicate-filled epoxy resins, phenolic resins, polyester resins and other systems. In addition, it can also be used in FRP production to improve its mechanical strength and resistance to humid environments. The organic groups of silane coupling agents have selectivity for the reaction of synthetic resins. Generally, these organic groups lack sufficient reactivity with synthetic resins such as polyethylene, polypropylene, and polystyrene, so the coupling effect is poor.

Preparation

A three-necked flask equipped with a reflux condenser, stir bar and thermometer was purged with nitrogen three times, followed by the addition of allyl glycidyl ether (11.4 g, 0.1 mol) followed by 1 cm³ of catalyst (10^-5 mol based on platinum). The temperature was raised to about 50 °C with stirring, and trimethoxysilane (13.4 g, 0.11 mol) was added dropwise from the dropping funnel within 1 hour, the reaction temperature was maintained at 50 °C, and the reaction was further stirred for 30 minutes. Gas chromatographic analysis showed that the yield of γ-glycidyloxypropyltrimethoxysilane based on allyl glycidyl ether was 80%, and the crude product was rectified under reduced pressure in an anhydrous and oxygen-free environment to obtain the final product.

Use

Can be used to prepare 4-[[3-(trimethoxysilyl)propoxy]methyl]-1,3-dioxolan-2-one

Take 23.6g (0.1mol) of 3-(2,3-glycidoxy)propyltrimethoxysilane and 2.36g of tetrabutylammonium bromide, add them to 120mL of ethyl acetate and stir to dissolve them, then pass in carbon dioxide to exhaust the air, When the carbon dioxide pressure is 1.7 MPa, the temperature is increased to 90 ℃ , and the stirring is maintained at 90 ℃and 1.7 MPa. When stirring, first stir clockwise for 2 hours and counterclockwise for 2 hours alternately. Stirring for a total of 45 hours for rearrangement reaction. After the reaction is completed, reduce To room temperature and normal pressure, take out the obtained system and lower the temperature to 3°C again, add saturated brine to wash (60mL×2), separate the phases, the obtained organic phase is dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 26.91g of 4- [[3-(Trimethoxysilyl)propoxy]methyl]-1,3-dioxolane-2-one, the yield was 95.99%, and the purity was 99.6%.

Industrial use

It is used to improve the bonding properties of organic materials and inorganic materials, such as the treatment of glass fibers in FRP and siliceous fillers in plastics, rubber, paints, coatings, etc. It is also used in adhesives to increase Adhesive performance, it is suitable for resins including epoxy, phenolic, melamine, polysulfide polyurethane, polystyrene, etc. Improve the adhesion of inorganic fillers, substrates and resins, so that Chemicalbook improves the mechanical strength, electrical properties of composites, and has a higher retention rate in the wet state. As a surface treatment agent for inorganic fillers, this product is widely used in clay, glass beads, talc, wollastonite, silica, quartz, aluminum powder, iron powder. This product is suitable for use with quartz-filled epoxy sealants, grit-filled epoxy concrete repair materials or coatings, and metal-filled epoxy molds.

References

【1】EP277023,1990, A3

【2】CN113698428,2021, A