Trimethoxysilylpropanethiol

Silane coupling agent KH-590

Silane coupling agent KH-590 is the earliest widely applied coupling agent and so far has a history of more than 40 years. One end of its structure contains active groups such as amino group and vinyl group which are capable of having reaction with various kinds of synthetic resin molecules including epoxy, phenolic, and polyester. The other end includes either alkoxy group (e.g. methoxy, ethoxy, etc.) or a chlorine atom which are connected to silicon. These groups, in the presence of an aqueous solution or moisture in the air, can be hydrolyzed to be able to react with glass, minerals, and the surface hydroxyl group of inorganic filler to generate reactive silanols. Accordingly, the silane coupling agent is commonly used in the silicate-filled epoxy, phenolic and polyester resin systems. In addition, it can also be used for the production of the glass steel in order to improve their mechanical strength and resistance to humid environments. The organic groups of the silane coupling agent have selectivity on the reaction of the synthetic resin. In general, these organic groups don’t have enough reactivity with synthetic resin such as polyethylene, polypropylene and polystyrene, and thus having poor coupling effects. In recent years, it has been developed of new variety of silane coupling agent with better coupling effect with polyolefin. However, limited by the cost and other performance, its application is still not wide enough.
Silane coupling agent is also known as silane treatment agent or primer. Its general chemical formula is Y (CH2) nSiX3 which contains organosilicon monomers with two or more different reactive groups in the molecule. It can have chemical coupling reaction with both inorganic and organic materials to increase the adhesion between the two kinds of materials. The n in the general chemical formula is an integer of 0 to 3; X is a hydrolyzable group such as chloro, methoxy, ethoxy, acetoxy, etc., It is easily to be hydrolyzed into silanols and can have reaction with inorganic materials and further bind to them; the Y is organic functional groups, such as vinyl, amino, epoxy, methacryloxy group, and mercapto group, etc., it can react with organic materials and bind to them. The performance of typical silane coupling agent is as follows: can be used for the treatment of glass fiber and inorganic filler surface; can be used as sealants, adhesives and coatings thickener; also can be applied to ensure the immobilize enzyme be attached to the glass substrate surface, sand prevention for oil well drilling, making masonry surfaces be water-repellent, endowing the coating of fluorescent lamp with a high surface resistance, and also improving the hygroscopic effect of the surface of the organic glass in the liquid chromatography. It is prepared from the adduct reaction between silicon chloroform and active group containing olefin in the catalysis of platinum and further alcoholysis.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Uses

Trimethoxysilylpropanethiol is a bifunctional organosilane possessing a reactive organic mercapto and a hydrolyzable inorganic methoxysilyl group. Trimethoxysilylpropanethiol is a clear, colorless to light yellow liquid with a slightly mercaptan odor. It is soluble in alcohols, ketones and aliphatic or aromatic hydrocarbons.
Applications:

• Trimethoxysilylpropanethiol can be used as coupling agent to improve the adhesion of sulfur cured elastomers (polysulfide, polyurethane sealants) to inorganic fillers (such as silica, clay, glass, mica and talc etc.), fiberglass and surfaces. Mineral-reinforced articles such as shoe soles, rubber rollers and wheels, white sidewalls, and wire and cable insulation also can be produced with lower silane loadings.
• Used to improve properties of mineral filled elastomer, including modulus, tensile and tear strength, heat buildup, abrasion resistance, resilience, compression set and cure time.
• Used as a pretreatment on minerals or added at the time of compounding.
• Used to improve low-rolling resistance in silica-reinforced tire tread compounds.

Chemical Properties

Water white to light straw liquid clear liquid with an unpleasant odour of sulphide.

Uses

(3-Mercaptopropyl)trimethoxysilane is used as a capping molecule for cadmium sulphide nanocrystals. It is used in the preparation of multi-walled carbon nanotubes and bilayer modified gold electrode. It acts as a linker molecule used in the preparation of gold multilayers and as a molecular adhesive in the fabrication of vapor-deposited gold electrodes on glass substrates. It is also used as a precursor for silica.

Application

MPTMS can be coated with TiO₂, CeO₂ and La₂O₃ for protection against corrosion on quaternary bronze in urban atmosphere. It can also be used as a silica nanofluid (NF) to modify the surface of berea sandstone to improve the enhanced oil recovery (EOR) area in the petroleum industry. MPTMS forms composites with kaolin, that can be used as an absorbent for the removal of heavy metals from wastewater. MPTMS can form a bilayer with multiwalled carbon nanotubes (MWNTs) on gold electrodes which can be used to study the electrochemical properties of fluphenazine.

Preparation

(3-Mercaptopropyl)trimethoxysilane was prepared by using thiourea and 3-chloropropyltrimethoxysilane as raw materials, petroleum ether as solvent, KI as catalyst, and ethylenediamine as neutraliser.

General Description

(3-mercaptopropyl)trimethoxysilane (MPTMS) is an organosilane with a thiol group, which can be used as a self-assembled monolayer (SAM). It can be used as a conjunction reagent to immobilize a variety of nanoparticles.