CN111892619A - Synthetic method of double-long-chain organosilicon quaternary ammonium salt - Google Patents
Synthetic method of double-long-chain organosilicon quaternary ammonium salt Download PDFInfo
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 82
- 238000010189 synthetic method Methods 0.000 title claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 methyl tertiary amine Chemical class 0.000 claims abstract description 23
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 72
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 24
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical group [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- LLROOTQECVJATI-UHFFFAOYSA-N triethoxy(isocyanato)silane Chemical compound CCO[Si](OCC)(OCC)N=C=O LLROOTQECVJATI-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 2
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical group [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
Abstract
The invention discloses a method for synthesizing double-long-chain organosilicon quaternary ammonium salt, which comprises the steps of firstly synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt by using double-long-chain methyl tertiary amine and chloroethanol as raw materials under the action of a catalyst, and then reacting the hydroxyl-containing double-long-chain quaternary ammonium salt with isocyanatosilane to generate carbamate triethoxysilane quaternary ammonium salt containing double long chains. Simple process, short synthesis time and stronger antibacterial property than single long-chain organosilicon quaternary ammonium salt.
Description
Technical Field
The invention relates to a method for synthesizing double-long-chain organosilicon quaternary ammonium salt.
Background
The quaternary ammonium salt can adsorb bacteria with negative charges and has good bactericidal effect. However, the chemical activity of the common quaternary ammonium salt is low, the quaternary ammonium salt exists in a basically free state during application, the toxicity is relatively high, and the irritation is strong. Researches find that the performance of the organosilicon quaternary ammonium salt prepared by introducing siloxane into a quaternary ammonium salt structure is greatly changed, and the organosilicon quaternary ammonium salt has excellent antibacterial and bacteriostatic properties, and has no stimulation and carcinogenic effect on human skin. The formula of the organosilicon quaternary ammonium salt is RnSiX4-n (n is a positive integer from 0 to 3; R is a non-hydrolyzable alkyl group; X is a group capable of being hydrolyzed, such as hydroxyl and alkoxy), wherein the X group is easy to hydrolyze, so that the organosilicon quaternary ammonium salt can form oligomers and polymers in aqueous solution, and the antibacterial and mildewproof effects of the organosilicon quaternary ammonium salt are lost.
On the market, antibacterial agent developed by Dow Corning company (Dow Corning) of America under the trade name DC-5700 (dimethyloctadecyl [3- (trimethoxysilyl) propyl ] ammonium chloride) is one of representative organosilicon quaternary ammonium salt products. As the quaternary ammonium salt is positively charged, the surface of the bacteria is negatively charged, and the interaction of the charges enables the DC-5700 to be close to the bacteria, so that an alkyl chain is inserted into a cell membrane of the bacteria, the integrity of the alkyl chain is damaged, and the aim of durable sterilization is fulfilled. As mentioned above, the methoxyl group in the quaternary ammonium salt is easily activated in water, so the real active component is dimethyl octadecyl [3- (trihydroxy) propyl ] ammonium chloride obtained after activation, and the dimethyl octadecyl [3- (trihydroxy) propyl ] ammonium chloride can dehydrate with hydroxyl on various natural or synthetic surfaces to form covalent bonds, so that the covalent bonds are attached on the surfaces to form a firm film capable of sterilizing and inhibiting bacteria, and the effect of lasting antibiosis and mildew prevention is achieved.
However, dimethyloctadecyl [3- (trimethoxysilyl) propyl ] ammonium chloride is obtained by reacting octadecyl dimethyl tertiary amine with chloropropyltrimethoxysilane at 80-120 ℃ for 30-80 hours. The reaction time is long, the utilization rate of equipment is low, and the antibacterial property needs to be further improved.
Therefore, the existing synthetic method of the organic silicon quaternary ammonium salt is to be further perfected.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a method for synthesizing double-long-chain organosilicon quaternary ammonium salt with simple process, short synthesis time and stronger antibacterial property than single-long-chain organosilicon quaternary ammonium salt
In order to achieve the purpose, the invention adopts the following scheme: a synthetic method of double-long-chain organosilicon quaternary ammonium salt is characterized by comprising the following steps: s1, synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt, namely putting double-long-chain methyl tertiary amine, chloroethanol, a first solvent and a catalyst into a reaction container, and reacting to obtain hydroxyl-containing double-long-chain quaternary ammonium salt; s2, synthesis of organosilicon quaternary ammonium salt: and (4) adding a second solvent and the hydroxyl-containing double-long-chain quaternary ammonium salt obtained in the step S1 into a reaction container, dropwise adding an acetone solution of isocyanate-based triethoxy silane, and reacting to generate the double-long-chain carbamate triethoxy silane quaternary ammonium salt.
As the synthetic method of the double-long-chain organosilicon quaternary ammonium salt, the molar ratio of the double-long-chain methyl tertiary amine to the chloroethanol in the step S1 is 1: 1.1-1.4.
As the method for synthesizing the double-long-chain organosilicon quaternary ammonium salt, the first solvent in the step S1 is one of acetone, methanol, ethanol or isopropanol.
As the synthesis method of the double-long-chain organosilicon quaternary ammonium salt, the addition amount of the solvent is 28-34% of the total reaction liquid.
As the synthetic method of the double-long-chain organosilicon quaternary ammonium salt, the catalyst is potassium iodide.
As the synthetic method of the double-long-chain organosilicon quaternary ammonium salt, the dosage of the catalyst is 0.1-0.3% of the total reaction liquid.
As the synthetic method of the double-long-chain organosilicon quaternary ammonium salt, the reaction process in the step S1 is heated to the boiling reflux of the solvent, the reaction is carried out for 8 to 16 hours, when the tertiary amine conversion rate reaches more than 95 percent, isopropanol and chloroethanol are evaporated out under reduced pressure, and the product is dissolved by acetone.
As the method for synthesizing the double-long-chain organosilicon quaternary ammonium salt, the second solvent in the step S2 is acetone.
As the synthetic method of the double-long-chain organosilicon quaternary ammonium salt, the mass concentration of the acetone solution of the isocyanate group triethoxy silane in the step S2 is 45-55%.
As the synthesis method of the double-long-chain organosilicon quaternary ammonium salt, in step S2, an acetone solution of isocyanate group triethoxy silane is dripped at the temperature of 25-32 ℃, the dripping speed is controlled at the internal temperature of not more than 50 ℃, then the temperature is raised to boiling reflux for 3-6 hours, when the hydroxyl content is detected to be 0, the reaction is stopped, and the acetone is evaporated under reduced pressure.
In summary, compared with the prior art, the invention has the beneficial effects that: the invention takes double-long-chain methyl tertiary amine and chloroethanol as raw materials, under the action of a catalyst, firstly synthesizes double-long-chain quaternary ammonium salt containing hydroxyl, and then reacts with isocyanatosilane to generate carbamate triethoxysilane quaternary ammonium salt containing double long chains. Simple process, short synthesis time and stronger antibacterial property than single long-chain organosilicon quaternary ammonium salt.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A synthetic method of double-long-chain organosilicon quaternary ammonium salt comprises the following steps: s1, synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt, namely adding didecyl methyl tertiary amine and chloroethanol into a three-neck flask with a nitrogen-attached connecting pipe, a thermometer and an electric stirrer, wherein the molar ratio of the didecyl methyl tertiary amine to the chloroethanol is 1:1.1, acetone is used as a solvent, the addition amount of the isopropanol is 28 percent of the total reaction liquid, 0.1 percent of potassium iodide is added as a catalyst, heating is carried out until the isopropanol boils and refluxes, the reaction is carried out for 8 hours, when the conversion rate of the tertiary amine is more than 95 percent, the isopropanol and the chloroethanol are evaporated under reduced pressure, and the product is dissolved by the acetone.
S2, synthesis of organosilicon quaternary ammonium salt: adding acetone and the hydroxy-containing double-long-chain quaternary ammonium salt synthesized in the above case into a three-mouth bottle by taking acetone as a solvent, dripping an acetone solution of isocyanate group triethoxy silane with the mass concentration of 45% at 25 ℃, controlling the dripping speed to ensure that the internal temperature is not more than 50 ℃, heating to boil and refluxing for 3 hours, stopping the reaction when the hydroxy content is detected to be 0, evaporating the acetone under reduced pressure to obtain a double-long-chain-containing organosilicon quaternary ammonium salt solid, and dissolving the double-long-chain-containing organosilicon quaternary ammonium salt solid by using a proper solvent to prepare the double-long-chain organosilicon quaternary ammonium salts with different concentrations.
Example 2
A synthetic method of double-long-chain organosilicon quaternary ammonium salt comprises the following steps: s1, synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt, namely adding didecyl methyl tertiary amine and chloroethanol into a three-neck flask with a nitrogen-attached connecting pipe, a thermometer and an electric stirrer, wherein the molar ratio of the didecyl methyl tertiary amine to the chloroethanol is 1:1.2, methanol is used as a solvent, the addition amount of isopropanol is 34% of the total reaction liquid, 0.3% of potassium iodide is added as a catalyst, heating is carried out until the isopropanol boils and refluxes, the reaction is carried out for 16 hours, when the conversion rate of the tertiary amine is more than 95%, the isopropanol and the chloroethanol are evaporated under reduced pressure, and the product is dissolved by acetone.
S2, synthesis of organosilicon quaternary ammonium salt: adding acetone and the hydroxy-containing double-long-chain quaternary ammonium salt synthesized in the above case into a three-mouth bottle by taking acetone as a solvent, dripping an acetone solution of isocyanate group triethoxy silane with the mass concentration of 55% at 32 ℃, controlling the dripping speed to ensure that the internal temperature is not more than 50 ℃, then heating to boil back for 6 hours, stopping the reaction when the hydroxy content is detected to be 0, decompressing and distilling out the acetone to obtain a double-long-chain-containing organosilicon quaternary ammonium salt solid, and dissolving the double-long-chain-containing organosilicon quaternary ammonium salt solid by using a proper solvent to prepare the double-long-chain organosilicon quaternary ammonium salts with different concentrations.
Example 3
A synthetic method of double-long-chain organosilicon quaternary ammonium salt comprises the following steps: s1, synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt, namely adding didecyl methyl tertiary amine and chloroethanol into a three-neck flask with a nitrogen-attached connecting pipe, a thermometer and an electric stirrer, wherein the molar ratio of the didecyl methyl tertiary amine to the chloroethanol is 1:1.3, isopropanol is used as a solvent, the addition amount of the isopropanol is 28-34% of the total reaction liquid, 0.2% of potassium iodide is added as a catalyst, heating is carried out until the isopropanol boils and refluxes, the reaction is carried out for 12 hours, when the conversion rate of the tertiary amine is more than 95%, the isopropanol and the chloroethanol are evaporated under reduced pressure, and the product is dissolved by acetone.
S2, synthesis of organosilicon quaternary ammonium salt: adding acetone and the hydroxy-containing double-long-chain quaternary ammonium salt synthesized in the above case into a three-mouth bottle by taking acetone as a solvent, dripping an acetone solution of isocyanate group triethoxy silane with the mass concentration of 50% at the temperature of 30 ℃, controlling the dripping speed to ensure that the internal temperature is not more than 50 ℃, then heating to boil and refluxing for 4 hours, stopping the reaction when the hydroxy content is detected to be 0, evaporating the acetone under reduced pressure to obtain the double-long-chain-containing organosilicon quaternary ammonium salt solid, and dissolving the double-long-chain-containing organosilicon quaternary ammonium salt solid by using a proper solvent to prepare the double-long-chain organosilicon quaternary ammonium salt with different.
Example 4
A synthetic method of double-long-chain organosilicon quaternary ammonium salt comprises the following steps: s1, synthesizing hydroxyl-containing double-long-chain quaternary ammonium salt, namely adding didecyl methyl tertiary amine and chloroethanol into a three-neck flask with a nitrogen-attached connecting pipe, a thermometer and an electric stirrer, wherein the molar ratio of the didecyl methyl tertiary amine to the chloroethanol is 1:1.4, ethanol is used as a solvent, the addition amount of the isopropanol is 32 percent of the total reaction liquid, 0.1 percent of potassium iodide is added as a catalyst, heating is carried out until the isopropanol boils and refluxes, the reaction is carried out for 10 hours, when the conversion rate of the tertiary amine is more than 95 percent, the isopropanol and the chloroethanol are evaporated under reduced pressure, and the product is dissolved by acetone.
S2, synthesis of organosilicon quaternary ammonium salt: adding acetone and the hydroxy-containing double-long-chain quaternary ammonium salt synthesized in the above case into a three-mouth bottle by taking acetone as a solvent, dripping an acetone solution of isocyanate group triethoxy silane with the mass concentration of 48% at 25-32 ℃, controlling the dripping speed to ensure that the internal temperature is not more than 50 ℃, then heating to boil and refluxing for 5 hours, stopping the reaction when the hydroxy content is detected to be 0, decompressing and evaporating the acetone to obtain the double-long-chain-containing organosilicon quaternary ammonium salt solid, and dissolving the double-long-chain-containing organosilicon quaternary ammonium salt solid by using a proper solvent to prepare the double-long-chain organosilicon quaternary ammonium salts with different concentrations.
In order to further prove the proper proportion of the components in the synthetic process of the invention and achieve the beneficial effects, the invention carries out the following comparative tests: the conversion of tertiary amine in the resulting product was shown in the following table by varying the molar ratio of didecyl tertiary amine to chlorohydrin.
TABLE 1 conversion of tertiary amines obtained by different molar ratios of reactants
As can be seen from the above table, when the molar ratio of the tertiary amine to the chlorohydrin is increased from 1:1.0 to 1:1.3, the conversion of the tertiary amine is increased from 82.8% to 98.5%, and the conversion is not increased by further increasing the amount of the chlorohydrin.
In order to illustrate the bacteriostatic effect of the double-long-chain organosilicon quaternary ammonium salt, the following tests are carried out.
The minimum inhibitory concentration of the product to various bacteria is detected by a third-party detection unit for product inspection, and compared with the existing single-long-chain organosilicon quaternary ammonium salt, the minimum inhibitory concentration is as follows:
TABLE 2 minimum inhibitory concentrations for various bacteria and comparison with existing mono-long chain organosilicon quaternary ammonium salts
The foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. A synthetic method of double-long-chain organosilicon quaternary ammonium salt is characterized by comprising the following steps:
s1 synthesis of hydroxyl-containing double-long-chain quaternary ammonium salt
Putting double-long-chain methyl tertiary amine, chloroethanol, a first solvent and a catalyst into a reaction container, and reacting to prepare hydroxyl-containing double-long-chain quaternary ammonium salt;
s2 synthesis of organosilicon quaternary ammonium salt
And (4) adding a second solvent and the hydroxyl-containing double-long-chain quaternary ammonium salt obtained in the step S1 into a reaction container, dropwise adding an acetone solution of isocyanate-based triethoxy silane, and reacting to generate the double-long-chain carbamate triethoxy silane quaternary ammonium salt.
2. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: in the step S1, the molar ratio of the double-long-chain methyl tertiary amine to the chloroethanol is 1: 1.1-1.4.
3. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: in step S1, the first solvent is one of acetone, methanol, ethanol, and isopropanol.
4. The method for synthesizing a double-long-chain organosilicon quaternary ammonium salt according to claim 1 or 3, wherein: the addition amount of the solvent is 28-34% of the total reaction solution.
5. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: the catalyst is potassium iodide.
6. The method for synthesizing a double-long-chain organosilicon quaternary ammonium salt according to claim 1 or 5, wherein: the dosage of the catalyst is 0.1-0.3% of the total reaction liquid.
7. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: and (S1) heating the reaction process until the solvent is boiled and refluxed, reacting for 8-16 hours, when the tertiary amine conversion rate reaches more than 95%, decompressing and distilling to remove isopropanol and chloroethanol, and dissolving the product by using acetone.
8. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: the second solvent in step S2 is acetone.
9. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: the mass concentration of the acetone solution of the isocyanatotriethoxysilane in the step S2 is 45-55%.
10. The method for synthesizing the double-long-chain organosilicon quaternary ammonium salt according to claim 1, wherein the method comprises the following steps: and step S2, dropwise adding an acetone solution of isocyanate group triethoxy silane at 25-32 ℃, controlling the dropping speed to ensure that the internal temperature is not more than 50 ℃, then heating to boiling and refluxing for 3-6 hours, stopping the reaction when detecting that the hydroxyl content is 0, and distilling out the acetone under reduced pressure.
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| CN (1) | CN111892619A (en) |
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| CN113278029A (en) * | 2021-05-31 | 2021-08-20 | 杭州昕洋生物科技有限公司 | Double-branched-chain organosilicon quaternary ammonium salt and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024868A (en) * | 2021-03-04 | 2021-06-25 | 浙江伟星光学有限公司 | Antibacterial resin lens and preparation method thereof |
| CN113278029A (en) * | 2021-05-31 | 2021-08-20 | 杭州昕洋生物科技有限公司 | Double-branched-chain organosilicon quaternary ammonium salt and preparation method and application thereof |
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Application publication date: 20201106 |