• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    PURPOSE: Provided is a method for preparing a surfactant which is excellent in disinfection even if used in extremely small quantities, and which has low toxicity, and thus can be used for infection of home cooker, medical implement, pen, and so on. CONSTITUTION: The method comprises the steps of (S10) dissolving 2-chloro-1-(4-chlorophenyl)ethanone(ClC6H4COCH2Cl) in predetermined reaction solvent; (S20) adding a linear dimethyldodecylamine to 2-chloro-1-(4-chlorophenyl)ethanone dissolved in the reaction solvent, and reacting the amine and the solution for predetermined hours with heating; (S30) removing the reaction solvent after the reaction, and cooling the remaining reactant; (S40) adding hexane to the cooled reactant to solidify the reactant; (S50) aging the solidified reactant at room temperature with stirring; (S60) filtrating the aged material; and (S70) pulverizing the filtrates.
    公开号:KR20020086036A
    申请号:KR1020010025675
    申请日:2001-05-11
    公开日:2002-11-18
    发明作者:배선건
    申请人:주식회사 코씰；배선건；
    IPC主号:
    专利说明:

    Method for preparing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride {Synthesis method of 2- (4-Chlorophenyl) -2-oxo-ethyl-dodecyldimethyl Ammonium Chloride}
    [2] The present invention relates to a method for preparing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride salt, and particularly, even with a small amount, excellent sterilization power and low toxicity, such as household kitchen appliances, clothing appliances, barns, etc. It relates to a method for producing a surfactant that exhibits strong antimicrobial properties that can be used for disinfection and sterilization of agricultural and industrial applications.
    [3] Due to the excessive use of surfactants used in detergents and industrial use today, the environmental pollution is getting serious and there is a demand for the development of surfactants with high antibacterial activity while using as little as possible.
    [4] Most conventional surfactants are quaternary ammonium salts prepared by the reaction of fatty acid alkylamines, dimethylamines, and alkyl chlorides. For example, benzyl chloride and dimethylamine are used to prepare benzalkonium, a quaternary ammonium salt, followed by an exothermic reaction of 100 ° C. or higher during the reaction. In addition, among the surfactants prepared in this way, the antibacterial activity may be low, so that a large amount of the surfactant may be used, causing environmental pollution.
    [5] In addition, cationic surfactants dissociate hydrophilic groups into cations when dissolved in water, and are widely used in detergents, agriculture, and industrial applications, and require environmental friendliness such as economical efficiency and low irritation while using a small amount.
    [6] Representative examples of the cationic surfactants include dimethyl dialkyl ammonium chloride, but these surfactants have a low biodegradability.
    [7] In an effort to make up for such drawbacks, introduction of degradable functional groups such as esters and amides into alkyl groups has been attempted. As an example, Japanese Patent No. Hei 6-345704 discloses an amidoamine compound and a method of preparing a cationic surfactant using the same, and Japanese Patent Hei 6-336466 discloses an amidoesteramine compound and a cationic interface using the same. Japanese Patent No. Hei 4-257372 discloses a softener composition containing an imidazoline ester, and Japanese Patent Hei 2-1479 discloses a compound for conditioning comprising imidazoline. A manufacturing method is disclosed.
    [8] However, these cationic surfactants do not obtain satisfactory levels of biodegradability, and efforts have been made to include highly degradable functional groups such as ester groups in alkyl groups, which are lipophilic moieties in cationic surfactant molecules.
    [9] As a result of these efforts, various derivatives of quaternary ammonium salts have been developed, for example WO 94/07978 discloses quaternized cationic surfactants derived from triethanol amines, and WO 93/23510 discloses two hydrophobic Cationic surfactants having ester bonds to the groups).
    [10] The development of such cationic surfactants has led to the development of cationic surfactants having excellent sterilization and antimicrobial function but no toxicity with improvement in biodegradation properties.
    [11] It is an object of the present invention to provide a method for producing a surfactant having a strong antibacterial property, which can be used for disinfecting and disinfecting household kitchen utensils, clothing utensils, barns and the like, and for agricultural and industrial use, even if a trace amount is used.
    [12] Another object of the present invention is to provide a quaternary ammonium salt manufacturing method excellent in antibacterial activity as well as the function of a surfactant even when a small amount is used to minimize environmental pollution. In other words, the present invention reacts 2-chloro-1- (4-chlorophenyl) ethanone (ClC 6 H 4 COCH 2 Cl) with dimethyldodecylamine at low temperature in a low alcohol (methanol, ethanol and isopropanol) solvent. To provide a method of synthesizing quaternary ammonium salt (melting point: 114 to 116 ° C.) at a high yield of 95%, resulting in surface tension and bubble test results, as well as the function of surfactants and minimum inhibitory concentration (MIC). A new antimicrobial surfactant preparation method up to 3.9 ppm is provided.
    [13] Other objects and advantages of the present invention will become more apparent from the following detailed description of the invention and the accompanying drawings.
    [1] 1 is a flow chart showing a method for preparing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride according to the present invention.
    [14] In order to achieve the above object, the present invention dissolves 2-chloro-1- (4-chlorophenyl) ethanone in the reaction solvent and then adds dimethyldodecylamine to warm it for 12 to 24 hours at a low temperature of 40 to 60 ℃. The reaction is carried out to remove the solvent, solidified with a nucleic acid, and stirred at room temperature while aging. The method provides a method for preparing a cationic surfactant of Formula 1 prepared after filtration in powder form.
    [15]
    [16] Hereinafter, the present invention will be described in detail through various embodiments. The examples presented below are provided to aid the understanding of the present invention, and the present invention is not limited to the following examples.
    [17] <Example 1>
    [18] 3.78 g (0.02 mol) of 2-chloro-1- (4-chlorophenyl) ethanone (ClC 6 H 4 COCH 2 Cl) was added to a 250 mL round bottom flask equipped with a stirrer, a reflux condenser, and a thermometer. 50 mL of isopropanol was added to dissolve (s10), and then 4.27 g (0.02 mol) of linearized dimethyldodecylamine was added and reacted at 40 to 60 ° C. for 12 to 24 hours (s20). After completion of the reaction, the reaction solvent is removed and cooled (s30), the nucleic acid is added to solidify (s40), stirred at room temperature and aged (s50), and filtered (s60) to form a quaternary ammonium chloride salt in powder form ( s70).
    [19] <Example 2>
    [20] Example 2 uses methanol instead of the isopropanol solvent in Example 1, and the rest is the same as Example 1. Example 2 gives a quaternary ammonium chloride salt in powder form.
    [21] <Example 3>
    [22] Example 3 uses ethanol instead of the isopropanol solvent in Example 1, and the rest is the same as Example 1. Example 2 gives a quaternary ammonium chloride salt in powder form.
    [23] Physical properties of the cationic surfactants prepared in Examples 1 to 3 were measured and shown in Table 1. At this time, the surface tension is the value measured at 20 ℃, and the bubble force is the value measured by foaming 0.1% aqueous solution into 100 mL cylinder, shaking it 20 times, reading the bubble height within 10 seconds, and measuring the bubble height after 5 minutes. Inhibitory concentrations were measured against four strains (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis).
    [24]
    [25] As shown in Table 1, the amount of 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride as surface active agent and foaming force as a surfactant, as well as a minimum inhibitory concentration of 3.9 ppm, very high bactericidal activity It can also be used to minimize environmental pollution, and can also be used in many applications because it is well soluble in water and alcohol.
    [26] The present invention can be variously modified and can take various forms and only the specific embodiments thereof are described in the detailed description of the invention. It is to be understood, however, that the present invention is not limited to the specific forms mentioned in the detailed description of the invention, but rather includes all modifications, equivalents, and substitutions within the spirit and scope of the invention as defined by the appended claims. It should be understood to do.
    [27] According to the present invention, quaternary ammonium chloride salt ([2- (4-chlorophenyl) is prepared by simply heating and stirring the reaction of 2-chloro-1- (4-chlorophenyl) ethanone and dimethyldodecylamine in a low boiling point solvent. ) -2-oxo-ethyl] dodecyldimethyl) up to 95%. [2- (4-Chlorophenyl) -2-oxo-ethyl] dodecyldimethyl ammonium chloride prepared according to the present invention has a very high disinfectant with surface tension and foaming force as a surfactant and a minimum inhibitory concentration of 3.9 ppm. Even if a small amount is used, a high effect can be obtained to minimize environmental pollution, and it can also be used in various applications because it is well soluble in water and alcohol.
    权利要求:
    Claims (5)
    [1" claim-type="Currently amended] Formula is
    In the method for preparing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride represented by
    Dissolving 2 -chloro-1- (4-chlorophenyl) ethanone (ClC 6 H 4 COCH 2 Cl) in a predetermined reaction solvent;
    Reacting by adding dimethyldodecylamine linearized to 2-chloro-1- (4-chlorophenyl) ethanone dissolved in the reaction solvent and heating for a predetermined time;
    Removing the reaction solvent and cooling the reaction after completion of the reaction;
    Solidifying by adding nucleic acid to the cooled reactant;
    Aging the solidified material with stirring at room temperature;
    Filtering the aged material; And
    A method for preparing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride salt comprising the step of making the filtered material into powder form.
    [2" claim-type="Currently amended] The method for producing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride according to claim 1, wherein the predetermined time is 12 to 24 hours.
    [3" claim-type="Currently amended] The method of claim 2, wherein the heating is performed between 40 and 60 ° C. 4.
    [4" claim-type="Currently amended] 4. The reaction solvent according to claim 3, wherein when the 2-chloro-1- (4-chlorophenyl) ethanone is dissolved in the reaction solvent, the reaction solvent is reacted with respect to 0.02 mol of 2-chloro-1- (4-chlorophenyl) ethanone. A method for producing 2- (4-chlorophenyl) -2-oxo-ethyl dodecyldimethyl ammonium chloride, characterized in that it is dissolved in a ratio of mL.
    [5" claim-type="Currently amended] The 2- (4-chlorophenyl) -2-oxo-ethyl dode according to any one of claims 1 to 4, wherein the predetermined reaction solvent is selected from isopropanol, methanol and ethanol. Process for preparing sildimethylmethyl ammonium chloride salt.
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    同族专利:
    公开号 | 公开日
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    2001-05-11|Application filed by 주식회사 코씰, 배선건
    2001-05-11|Priority to KR1020010025675A
    2002-11-18|Publication of KR20020086036A
    优先权:
    申请号 | 申请日 | 专利标题
    KR1020010025675A|KR20020086036A|2001-05-11|2001-05-11|Synthesis method of 2--2-oxo-ethyl-dodecyldimethyl Ammonium Chloride|
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