In recent years, Organosilicon Surfactant has gradually become a research hotspot, mainly because its molecular structure is different from general hydrocarbon surfactants, and it has both inorganic properties and organic functions. On the one hand, Organosilicon Surfactant has relatively stable properties, such as heat resistance, low temperature adaptability, antistatic properties, hydrophobicity and biochemical inertness, etc., and can be widely used in the production of medical devices. On the other hand, because silicone also has low surface properties, low toxicity and antibacterial properties, it can be used in fabric finishing and pesticides. Therefore, Organosilicon Surfactant surfactants have broad application prospects and huge development potential, and the prospects are bright.
The hydrophobic group of the surface active material is composed of alkyl siloxane main chain, its hydrophobic performance is stronger than that of traditional carbon chain hydrocarbon surfactants, and it shows lower surface tension in the solution of the same concentration, and The higher bond energy (105kcal/mol) of the hydrophobic group Si-O makes it more stable, and it is a kind of high-efficiency surfactant. Surfactants currently on the market are elution-type, easy to wash off, and easy to gradually accumulate on the surface of the human body when used on textiles. Long-term use is prone to lesions. If the alkyl groups of ordinary silanes are replaced by methoxy silanes, the properties can be greatly changed. First, methoxysilane has silane coupling properties, and when diluted with water, silanol and methanol will be formed due to the hydrolysis of the methoxy group. The hydrolyzed organosilicon compound can be combined with the fiber through a covalent bond, that is, the hydroxyl group in the silanol and the fiber surface undergo a dehydration condensation reaction, and they are closely combined to form a firm film with each other; secondly, the toxicity and irritation of the Organosilicon Surfactant surfactant Sex is greatly reduced.
Application of Organosilicon Surfactant
1 Antibacterial finishing agent In 1967, Dow Corning of the United States successfully developed Organosilicon Surfactant antibacterial finishing agent DC-5700. This substance improved the binding ability of quaternary ammonium salts and fibers. Because of its good safety, it was known as “BIOSIL” antibacterial finishing with excellent durability. agent, and widely used in textiles. In 1975, when the U.S. Environmental Protection Agency (EPA) approved the application of this type of antimicrobial agent, it noticed that the added product would be in contact with the human body, so it conducted a safety appraisal from various aspects, and the result was recognized by the EPA. Therefore, silicone surfactant is an excellent antibacterial finishing agent, which has both antibacterial and fabric finishing functions.
2 Fabric softener Organosilicon Surfactant is a kind of fabric auxiliaries with excellent performance and wide application. It can treat natural fibers as well as synthetic fibers such as polyester and nylon. The treated fabrics are anti-wrinkle, anti-static, anti-pilling, soft and plump. Rich in elasticity and luster, it has the characteristics of cool, smooth and stiff, and can also improve the strength of fabric fibers and reduce wear and tear. Methoxy silicone has a highly hydrolyzable methoxy group in the molecule. When the methoxy group meets water, it can be hydrolyzed into a hydroxyl group. It can form a very strong adsorption and orientation with the fabric fibers; the Si-O bond is mainly The flexibility of the chain reduces the coefficient of static friction between fabric fibers, and the fibers can start to slide with a small force; at the same time, due to the condensation of siloxane itself, an elastic network structure is produced on the surface and inside of the fabric fibers, thereby Gives fabrics good softness and strong washability.
3 Emulsifiers Domestic research on Organosilicon Surfactant began in the middle of the 20th century, and research on organosilicon surfactants was later. The earliest silicon-containing cationic surfactants appeared as emulsifiers in the 1940s. Many varieties have been developed in developed countries, but the research in this area in my country started relatively late, with fewer varieties, and there is still a lot of room for development. Li Junying and others synthesized diethylbenzyl-3-(methyldimethoxysilyl)propylammonium chloride, and investigated the product and n-butanol, water, octamethylcyclotetrasiloxane (D4) system According to the pseudo-ternary phase diagram of the microemulsion, the relationship between the water content and the electrical conductivity of the microemulsion was determined, and the structure of the microemulsion was preliminarily determined to be in two forms: W/O and O/W.
Preparation of Organosilicon Surfactant
Organosilicon Surfactant can be divided into four types of surfactants: cationic, anionic, nonionic and amphoteric according to the ionization situation in water.
1. Synthesis of anionic silicone surfactants Anionic silicone surfactants include sulfonic acid type, carboxylic acid type, succinate type and phosphate ester type, etc., which can be obtained by the hydrosilicon addition reaction of the corresponding ester with unsaturated bonds and hydrogen-containing silicone oil, or by Epoxy intermediate conversion. Phosphate ester organosilicon surfactants are the most common. The products are phosphorylated by siloxane alcohols, and then neutralized and refined as required. Huang Liangxian et al. used platinum as a catalyst to obtain a polyether-modified silicone oil intermediate through the hydrosilylation addition reaction of hydrogen silicone oil and terminal alkenyl polyether, and then carried out esterification with phosphorus pentoxide to obtain a phosphate ester silicone Surfactant; Wang Xuechuan et al. synthesized a new type of organosilicon succinate surfactant by ring-opening reaction using alcohol amine silicone oil and maleic anhydride as starting materials and p-toluenesulfonic acid as a catalyst.
2 Synthesis of Cationic Silicone Surfactant Amino silicone oil and amino silane are the most typical, largest and most widely used organosilicon cationic surfactants. The addition reaction of epoxy silane and tertiary amine, the substitution reaction of halohydrocarbyl silane and tertiary amine, the quaternization reaction of aminosilane and the ring-opening reaction of aminosilane and epoxy compound are all commonly used methods. Lv Yanping, Li Linsheng et al. used aminoethylaminopropyldimethoxysilane (DL-602) as a raw material at 100°C for amidation reaction with methyl oleate for 6 h to obtain the intermediate of oleamideethylaminopropylsilane , and then the organosilicon quaternary ammonium salt antibacterial finishing agent ASQA was prepared by the quaternization reaction of dimethyl sulfate. Cheng Jianhua et al.  synthesized a cationic polyether-modified silicone surfactant through addition, ring-opening and quaternization reactions starting from low hydrogen-containing silicone oil. Zhu Xinhai et al. used tertiary amine and chloropropyl siloxane as raw materials, methanol or ethanol as solvent, and under the condition of microwave radiation, only need to react for 1.5 h at 150 ℃ (triethyldiamine, 65 ℃), and then A high yield of 84%~96% of the target product can be obtained.
3 Synthesis of amphoteric silicone surfactants The synthesis of amphoteric silicone surfactants adopts the reaction of epoxy-modified silicone oil and secondary amines to obtain intermediates, which are then reacted with haloacetates for quaternization. Josef Bauerb et al. reacted octamethylcyclotetrasiloxane with Si(CH3)3CHLi to obtain an intermediate, reacted with hexamethylcyclotrisiloxane and trimethylsilyl chloride to obtain vinyl silicone oil, and then Under the action of the silicon atom, it is converted into a silicone oil with an oxirane group attached to the silicon atom, and then reacted with a substance with a secondary amino functional group to obtain a betaine-type silicon surfactant.
4 Synthesis of nonionic silicone surfactants Nonionic silicone surfactants are widely prepared by the addition reaction of hydrosilane and unsaturated bond-containing compounds under certain conditions. He Ting et al. used hydrogen-containing silicone oil and allyl-terminated polyether as raw materials, and catalyzed by chloroplatinic acid Under the action of polyether modified silicone emulsifier was synthesized by hydrosilylation reaction. The results show that the surfactant can effectively reduce the surface tension and has excellent emulsifying properties. In addition to the silane addition synthesis method, the condensation method is also a relatively common method for synthesizing non-ionic silicone surfactants. The hydroxyl-containing polyether is reacted with a silicon-hydrogen bond to remove a molecule of hydrogen to obtain the target product.
Organosilicon Surfactant Research Status and Trends at Home and Abroad
There are many synthetic methods of Organosilicon Surfactant, such as the addition reaction of epoxy silane and octadecyl dimethyl tertiary amine, the substitution reaction of haloalkyl silane and octadecyl dimethyl tertiary amine, the synthesis of aminosilane Quaternization reaction and ring-opening reaction of aminosilane and epoxy compound, etc. Among them, the substitution reaction between haloalkylsilane and octadecyldimethyl tertiary amine is the most convenient way to prepare organosilicon quaternary salt. Such as: the substitution reaction of long carbon chain octadecyl dimethyl tertiary amine and γ-chloropropyl trimethoxysilane is a convenient way to prepare the target product.
In 1967, Dowcorning Corporation of the United States developed the silicone surfactant DC-5700 and applied for a patent. It was loved by users as soon as it went on the market, and it is still one of the most popular fabric antibacterial agents so far. Silicone surfactants have been used in various industrial fields since the 1960s, but large-scale, rapid and comprehensive development began in the 1980s.
In the late 1980s, Silicon Crown Company of Shandong University developed a silicone surfactant product similar in structure to DC-5700, namely STU-AM101, whose molecular structure is:
Shao Hui and others synthesized a new type of fluorine-containing alkyl quaternary salt, which was used as a finishing agent to treat cotton fabrics showing durable antibacterial activity and extremely low critical surface energy. The synthetic route is as follows:
Such products abroad emerge in endlessly, and most of them appear in the form of patents. The US patent uses allyl glycidyl ether hydrogen-containing silicone oil and under the action of acid catalysis to prepare polysiloxane containing epoxy groups, and then utilizes epoxy groups to react with organic amines to synthesize compounds with a quaternary ammonium salt structure. This route can change the content of epoxy groups in polysiloxane and polymer arbitrarily, and can also choose different organic amines and quaternizing reagents to react to synthesize a series of Organosilicon Surfactant surfactants.
Burow et al. used long-chain octadecyldimethyl tertiary amine and haloalkylsilane as reaction raw materials, inorganic iodide as catalyst, and ether compound as solvent to synthesize this type of compound, and the conversion rate exceeded 90%. It was found that Nal’s The catalytic effect is the best. Kang et al. used low-hydrogen-containing silicone oil as a raw material to graft quaternary ammonium groups on polysiloxane chains through addition and quaternization reactions, and optimized and established the best reaction conditions. Unfortunately, most of the existing reports on the synthesis of Organosilicon Surfactant compounds are technological studies, and no detailed investigation has been carried out on the factors (solvent, temperature, catalyst, etc.) that affect this type of reaction. The ability of siloxane surfactants to reduce surface tension is significantly greater than that of hydrocarbon-based surfactants, and they are favored for their excellent wetting properties, defoaming and foam stabilization, and physiological inertness. In recent years, siloxane surfactants have been widely used in industrial fields such as plastics, coatings, fibers, cosmetics, pesticides and oil field exploitation.
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