CN118909228B - Solid cation etherifying agent and preparation method thereof - Google Patents
Solid cation etherifying agent and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of etherifying agents, and discloses a solid cationic etherifying agent and a preparation method thereof. The invention adds organosilicon modified gemini quaternary ammonium salt, pyridine modified epoxy resin modified quaternary ammonium salt and 3-chloro-2-hydroxypropyl trimethyl ammonium chloride into a reactor for reaction, and then vacuum-dries after the reaction is finished to obtain the solid cationic etherifying agent. In the organosilicon modified gemini quaternary ammonium salt, imidazolyl plays an antibacterial role by inhibiting synthesis of ergosterol in fungal cell membranes to cause fungal death, the gemini quaternary ammonium salt has a better bactericidal effect compared with single-chain quaternary ammonium salt, in the pyridine modified epoxy resin modified quaternary ammonium salt, pyridyl can interact with bacterial cell membranes to influence metabolism and cell structures of bacteria to play an antibacterial role, sulfur element can be combined with protein and DNA in bacteria to inhibit enzyme activity and protein synthesis to play a bactericidal role, and sulfur element can also damage cell walls and cell membranes of bacteria to accelerate cell death.
Description
Technical Field
The invention relates to the technical field of etherifying agents, in particular to a solid cationic etherifying agent and a preparation method thereof.
Background
The solid cationic etherifying agent is a solid etherifying agent with a quaternary ammonium salt structure, can react with starch, cellulose and the like to prepare cationic biodegradable high molecular compound substances such as starch, cellulose and the like, and has wide application in the fields of salt-free printing and dyeing, papermaking auxiliary agents, cotton fiber spinning, petroleum exploitation, daily chemical industry and the like. However, most of the solid cationic etherifying agents have poor antibacterial effect, so that the further application and development of the solid cationic etherifying agents are limited, as a fast-reaction solid etherifying agent is disclosed in patent CN108102000A, the reaction time for preparing the etherifying agent is shortened, the environment friendliness is better, the production efficiency is high, and the antibacterial effect of the solid cationic etherifying agent is still to be improved.
Disclosure of Invention
(One) solving the technical problems
Aiming at the defects of the prior art, the invention provides a solid cationic etherifying agent and a preparation method thereof, and the solid cationic etherifying agent has a good antibacterial effect.
(II) technical scheme
The solid cationic etherifying agent comprises, by weight, 15-20 parts of organosilicon modified gemini quaternary ammonium salt, 16-18 parts of pyridine modified epoxy resin modified quaternary ammonium salt and 5-7 parts of 3-chloro-2-hydroxypropyl trimethyl ammonium chloride.
Preferably, the preparation method of the organosilicon modified gemini quaternary ammonium salt comprises the following steps:
(1) Adding methyl epoxypropanol, dichloromethyltriethoxysilane and potassium hydroxide catalyst into tetrahydrofuran solvent, stirring and mixing, reacting for 3-5h at 35-45 ℃, filtering, washing and drying after the reaction is finished to obtain an intermediate 1;
(2) Adding N-methylimidazole, 4-bromo-N, N-dimethylaniline and a potassium carbonate catalyst into an N, N-dimethylformamide solvent under the nitrogen atmosphere, reacting for 5-8 hours at 75-90 ℃, and performing reduced pressure distillation, washing and drying after the completion to obtain an intermediate 2;
(3) Adding the intermediate 1, the intermediate 2 and acetic acid into a three-neck flask, adding isopropanol with the same solute volume, stirring and heating to 78-82 ℃ under the condition of nitrogen replacement, carrying out reflux reaction for 6-8h, standing and cooling after the reaction is finished, and carrying out rotary evaporation to obtain the organosilicon modified gemini quaternary ammonium salt.
Preferably, in the step (1), the mass ratio of the methyl epoxypropanol, the dichloromethyltriethoxysilane and the potassium hydroxide is 1:0.4-0.6:0.04-0.05.
Preferably, in the step (2), the mass ratio of the N-methylimidazole to the 4-bromo-N, N-dimethylaniline to the potassium carbonate is 1:1.2-1.4:0.04-0.08.
Preferably, in the step (3), the mass ratio of the intermediate 1 to the intermediate 2 to the acetic acid is 1:1.8-2:1.5-1.7.
Preferably, the preparation method of the pyridine modified epoxy resin modified quaternary ammonium salt comprises the following steps:
S1, adding 3-5 parts by weight of bisphenol A epoxy resin into a constant temperature reaction kettle, stirring and heating to control the system temperature to be 45-55 ℃, fully mixing 7-11 parts by weight of 2, 3-pyridine dicarboxylic acid and 0.2-0.5 part by weight of triethylamine catalyst, adding the mixture into the constant temperature reaction kettle, heating to the reaction temperature at the rotating speed of 300-500rmp, controlling the temperature to react for 3-4 hours, filtering and distilling under reduced pressure after the reaction is finished to obtain pyridine modified epoxy resin;
S2, adding 4- ((ethylaniline) methyl) benzenesulfonic acid and pyridine modified epoxy resin into an acetonitrile solvent, stirring and mixing, reacting for 1.5-2h at 30-40 ℃, and washing and drying after the reaction is finished to obtain an intermediate 3;
S3, adding 10-12 parts by weight of epichlorohydrin into a reactor under ice water bath, stirring for 20-30min, dropwise adding 5-8 parts by weight of intermediate 3, reacting for 3-4.5h at 25-28 ℃ after the dropwise adding is finished, filtering, washing and vacuum drying to obtain the pyridine modified epoxy resin modified quaternary ammonium salt.
Preferably, the temperature of the temperature-controlled reaction in S1 is 90-95 ℃.
Preferably, the mass ratio of the 4- ((ethylaniline) methyl) benzenesulfonic acid to the pyridine modified epoxy resin in the S2 is 1:0.75-0.8.
Preferably, the dripping time in the step S3 is 1.5-2h.
Preferably, the preparation method of the solid cationic etherifying agent comprises the steps of adding organosilicon modified gemini quaternary ammonium salt, pyridine modified epoxy resin modified quaternary ammonium salt and 3-chloro-2-hydroxypropyl trimethyl ammonium chloride into a reactor, reacting for 5-10min at the rotating speed of 800-1000rmp, and vacuum drying after the reaction is finished to obtain the solid cationic etherifying agent.
(III) beneficial technical effects
The invention adds organosilicon modified gemini quaternary ammonium salt, pyridine modified epoxy resin modified quaternary ammonium salt and 3-chloro-2-hydroxypropyl trimethyl ammonium chloride into a reactor for reaction, and then vacuum-dries after the reaction is finished to obtain the solid cationic etherifying agent.
Hydroxyl in methyl epoxy propanol and chlorine in dichloromethyl triethoxysilane react, a siloxane bond and a bisepoxy group are introduced to obtain an intermediate 1, 4-bromo-N, N-dimethylaniline, bromine in N-methylimidazole reacts with imidazole groups in N-methylimidazole, imidazole groups are introduced to obtain an intermediate 2, tertiary amine in the intermediate 2 reacts with acetic acid to obtain quaternary ammonium salt, and the quaternary ammonium salt attacks the bisepoxy group in the intermediate 1 to perform a ring-opening reaction to obtain the organosilicon modified gemini quaternary ammonium salt. The epoxy group in bisphenol A epoxy resin and 2, 3-pyridine dicarboxylic acid are subjected to ring-opening esterification reaction, pyridyl is introduced to obtain pyridine modified epoxy resin, hydroxyl in the pyridine modified epoxy resin and sulfonic group in 4- ((ethylaniline) methyl) benzenesulfonic acid are subjected to reaction, tertiary amine is introduced to obtain intermediate 3, and tertiary amine in the intermediate 3 and epoxy chloropropane are subjected to quaternization reaction to obtain pyridine modified epoxy resin modified quaternary ammonium salt.
In the organosilicon modified gemini quaternary ammonium salt, imidazolyl plays an antibacterial role by inhibiting biosynthesis of ergosterol in fungal cell membranes, so that cell membrane permeability is changed, intracellular important substances are lost, and fungi are killed; compared with the traditional single-chain quaternary ammonium salt, the gemini quaternary ammonium salt has stronger positive charge and better sterilization effect, in the pyridine modified epoxy resin modified quaternary ammonium salt, the pyridyl group contains an azacyclic structure and has higher electron density and anti-nucleophilicity, so that the pyridine derivative has certain lipophilicity and electrophilicity and can interact with biological molecules such as bacterial cell membranes and enzymes, thereby influencing the physiological metabolic process and the cell structure of bacteria to play a role in resisting bacteria, the sulfur element can be combined with proteins and DNA in bacteria to interfere the metabolic activity of the bacteria, inhibit the enzyme activity and protein synthesis in bacterial cells, achieve the sterilization effect, and the sulfur element can also damage the cell walls and the cell membranes of the bacteria and accelerate the death of the cells.
Detailed Description
Example 1
(1) Adding methyl epoxy propanol, dichloromethyl triethoxysilane and a potassium hydroxide catalyst into a tetrahydrofuran solvent, stirring and mixing, wherein the mass ratio of the methyl epoxy propanol to the dichloromethyl triethoxysilane to the potassium hydroxide is 1:0.4:0.04, reacting for 3 hours at 35 ℃, filtering, washing and drying after the reaction is finished to obtain an intermediate 1;
(2) Adding N-methylimidazole, 4-bromo-N, N-dimethylaniline and a potassium carbonate catalyst into an N, N-dimethylformamide solvent under the nitrogen atmosphere, wherein the mass ratio of the N-methylimidazole to the 4-bromo-N, N-dimethylaniline to the potassium carbonate is 1:1.2:0.04, reacting for 5 hours at 75 ℃, distilling under reduced pressure after the completion, washing and drying to obtain an intermediate 2;
(3) Adding the intermediate 1, the intermediate 2 and acetic acid into a three-neck flask, wherein the mass ratio of the intermediate 1 to the intermediate 2 to the acetic acid is 1:1.8:1.5, adding isopropanol with the same solute volume, stirring and heating to 78 ℃ under the condition of nitrogen replacement, carrying out reflux reaction for 6h, standing and cooling after the reaction is finished, and carrying out rotary evaporation to obtain the organosilicon modified gemini quaternary ammonium salt;
(4) Adding 3 parts by weight of bisphenol A epoxy resin into a constant temperature reaction kettle, stirring and heating to control the system temperature to 45 ℃, fully mixing 7 parts by weight of 2, 3-pyridine dicarboxylic acid and 0.2 part by weight of triethylamine catalyst, adding into the constant temperature reaction kettle, heating to the reaction temperature at a rotating speed of 300rmp, and controlling the temperature to react for 3 hours, wherein the temperature of the temperature-controlled reaction is 90 ℃, filtering and distilling under reduced pressure after the reaction is finished to obtain pyridine modified epoxy resin;
(5) Adding 4- ((ethylaniline) methyl) benzenesulfonic acid and pyridine modified epoxy resin into an acetonitrile solvent, wherein the mass ratio of the 4- ((ethylaniline) methyl) benzenesulfonic acid to the pyridine modified epoxy resin is 1:0.75, stirring and mixing, reacting for 1.5h at 30 ℃, washing and drying after the reaction is finished to obtain an intermediate 3;
(6) Adding 10 parts by weight of epichlorohydrin into a reactor under ice water bath, stirring for 20min, dropwise adding 5 parts by weight of intermediate 3 into the reactor, wherein the dropwise adding time is 1.5h, reacting for 3h at 25 ℃ after the dropwise adding is finished, filtering, washing and vacuum drying to obtain pyridine modified epoxy resin modified quaternary ammonium salt;
(7) 15 parts by weight of organosilicon modified gemini quaternary ammonium salt, 16 parts by weight of pyridine modified epoxy resin modified quaternary ammonium salt and 5 parts by weight of 3-chloro-2-hydroxypropyl trimethyl ammonium chloride are added into a reactor to react for 5min at the rotation speed of 800rmp, and the solid cationic etherifying agent is obtained after the reaction is finished and is dried in vacuum.
Example 2
(1) Adding methyl epoxy propanol, dichloromethyl triethoxysilane and a potassium hydroxide catalyst into a tetrahydrofuran solvent, stirring and mixing, wherein the mass ratio of the methyl epoxy propanol to the dichloromethyl triethoxysilane to the potassium hydroxide is 1:0.6:0.05, reacting for 5 hours at 45 ℃, filtering, washing and drying after the reaction is finished to obtain an intermediate 1;
(2) Adding N-methylimidazole, 4-bromo-N, N-dimethylaniline and a potassium carbonate catalyst into an N, N-dimethylformamide solvent under the nitrogen atmosphere, wherein the mass ratio of the N-methylimidazole to the 4-bromo-N, N-dimethylaniline to the potassium carbonate is 1:1.4:0.08, reacting for 8 hours at 90 ℃, distilling under reduced pressure after the completion, washing and drying to obtain an intermediate 2;
(3) Adding the intermediate 1, the intermediate 2 and acetic acid into a three-neck flask, wherein the mass ratio of the intermediate 1 to the intermediate 2 to the acetic acid is 1:2:1.7, adding isopropanol with the same solute volume, stirring and heating to 82 ℃ under the condition of nitrogen replacement, carrying out reflux reaction for 8 hours, standing and cooling after the reaction is finished, and carrying out rotary evaporation to obtain the organosilicon modified gemini quaternary ammonium salt;
(4) Adding 5 parts by weight of bisphenol A epoxy resin into a constant temperature reaction kettle, stirring and heating to control the system temperature to 55 ℃, fully mixing 11 parts by weight of 2, 3-pyridine dicarboxylic acid and 0.5 part by weight of triethylamine catalyst, adding into the constant temperature reaction kettle, heating to the reaction temperature at a rotating speed of 500rmp, and controlling the temperature to react for 4 hours, wherein the temperature of the temperature-controlled reaction is 95 ℃, filtering and distilling under reduced pressure after the reaction is finished to obtain pyridine modified epoxy resin;
(5) Adding 4- ((ethylaniline) methyl) benzenesulfonic acid and pyridine modified epoxy resin into an acetonitrile solvent, wherein the mass ratio of the 4- ((ethylaniline) methyl) benzenesulfonic acid to the pyridine modified epoxy resin is 1:0.8, stirring and mixing, reacting for 2h at 40 ℃, washing and drying after the reaction is finished to obtain an intermediate 3;
(6) Adding 12 parts by weight of epichlorohydrin into a reactor under ice water bath, stirring for 30min, dropwise adding 8 parts by weight of intermediate 3 into the reactor, wherein the dropwise adding time is 2h, reacting for 4.5h at 28 ℃ after the dropwise adding is finished, filtering, washing and vacuum drying to obtain pyridine modified epoxy resin modified quaternary ammonium salt;
(7) Adding 20 parts by weight of organosilicon modified gemini quaternary ammonium salt, 18 parts by weight of pyridine modified epoxy resin modified quaternary ammonium salt and 7 parts by weight of 3-chloro-2-hydroxypropyl trimethyl ammonium chloride into a reactor, reacting for 10min at a rotating speed of 1000rmp, and vacuum drying after the reaction is finished to obtain the solid cationic etherifying agent.
Example 3
(1) Adding methyl epoxy propanol, dichloromethyl triethoxysilane and a potassium hydroxide catalyst into a tetrahydrofuran solvent, stirring and mixing, wherein the mass ratio of the methyl epoxy propanol to the dichloromethyl triethoxysilane to the potassium hydroxide is 1:0.5:0.045, reacting for 4 hours at 40 ℃, filtering, washing and drying after the reaction is finished to obtain an intermediate 1;
(2) Adding N-methylimidazole, 4-bromo-N, N-dimethylaniline and a potassium carbonate catalyst into an N, N-dimethylformamide solvent under the nitrogen atmosphere, wherein the mass ratio of the N-methylimidazole to the 4-bromo-N, N-dimethylaniline to the potassium carbonate is 1:1.3:0.06, reacting for 6.5 hours at 82 ℃, distilling under reduced pressure after the completion, washing and drying to obtain an intermediate 2;
(3) Adding the intermediate 1, the intermediate 2 and acetic acid into a three-neck flask, wherein the mass ratio of the intermediate 1 to the intermediate 2 to the acetic acid is 1:1.9:1.6, adding isopropanol with the same solute volume, stirring and heating to 80 ℃ under the condition of nitrogen replacement, carrying out reflux reaction for 7h, standing and cooling after the reaction is finished, and carrying out rotary evaporation to obtain the organosilicon modified gemini quaternary ammonium salt;
(4) Adding 4 parts by weight of bisphenol A epoxy resin into a constant temperature reaction kettle, stirring and heating to control the system temperature to be 50 ℃, fully mixing 9 parts by weight of 2, 3-pyridine dicarboxylic acid and 0.3 part by weight of triethylamine catalyst, adding into the constant temperature reaction kettle, heating to the reaction temperature at 400rmp, controlling the temperature to react for 3.5 hours, wherein the temperature of the temperature-controlled reaction is 90-95 ℃, filtering and distilling under reduced pressure after the reaction is finished to obtain pyridine modified epoxy resin;
(5) Adding 4- ((ethylaniline) methyl) benzenesulfonic acid and pyridine modified epoxy resin into an acetonitrile solvent, wherein the mass ratio of the 4- ((ethylaniline) methyl) benzenesulfonic acid to the pyridine modified epoxy resin is 1:0.78, stirring and mixing, reacting for 1.8h at 35 ℃, washing and drying after the reaction is finished to obtain an intermediate 3;
(6) Adding 11 parts by weight of epichlorohydrin into a reactor under ice water bath, stirring for 25min, dropwise adding 6 parts by weight of intermediate 3 into the reactor, wherein the dropwise adding time is 1.8h, reacting for 3.5h at 26 ℃ after the dropwise adding is finished, filtering, washing and vacuum drying to obtain pyridine modified epoxy resin modified quaternary ammonium salt;
(7) 18 parts by weight of organosilicon modified gemini quaternary ammonium salt, 17 parts by weight of pyridine modified epoxy resin modified quaternary ammonium salt and 6 parts by weight of 3-chloro-2-hydroxypropyl trimethyl ammonium chloride are added into a reactor to react for 8min at 900rmp, and after the reaction is finished, the solid cationic etherifying agent is obtained by vacuum drying.
Example 4
(1) Adding methyl epoxy propanol, dichloromethyl triethoxysilane and a potassium hydroxide catalyst into a tetrahydrofuran solvent, stirring and mixing, wherein the mass ratio of the methyl epoxy propanol to the dichloromethyl triethoxysilane to the potassium hydroxide is 1:0.4:0.04, reacting for 3 hours at 35 ℃, filtering, washing and drying after the reaction is finished to obtain an intermediate 1;
(2) Adding N-methylimidazole, 4-bromo-N, N-dimethylaniline and a potassium carbonate catalyst into an N, N-dimethylformamide solvent under the nitrogen atmosphere, wherein the mass ratio of the N-methylimidazole to the 4-bromo-N, N-dimethylaniline to the potassium carbonate is 1:1.2:0.04, reacting for 5 hours at 75 ℃, distilling under reduced pressure after the completion, washing and drying to obtain an intermediate 2;
(3) Adding the intermediate 1, the intermediate 2 and acetic acid into a three-neck flask, wherein the mass ratio of the intermediate 1 to the intermediate 2 to the acetic acid is 1:2:1.7, adding isopropanol with the same solute volume, stirring and heating to 82 ℃ under the condition of nitrogen replacement, carrying out reflux reaction for 8 hours, standing and cooling after the reaction is finished, and carrying out rotary evaporation to obtain the organosilicon modified gemini quaternary ammonium salt;
(4) Adding 5 parts by weight of bisphenol A epoxy resin into a constant temperature reaction kettle, stirring and heating to control the system temperature to 55 ℃, fully mixing 11 parts by weight of 2, 3-pyridine dicarboxylic acid and 0.5 part by weight of triethylamine catalyst, adding into the constant temperature reaction kettle, heating to the reaction temperature at a rotating speed of 500rmp, and controlling the temperature to react for 4 hours, wherein the temperature of the temperature-controlled reaction is 95 ℃, filtering and distilling under reduced pressure after the reaction is finished to obtain pyridine modified epoxy resin;
(5) Adding 4- ((ethylaniline) methyl) benzenesulfonic acid and pyridine modified epoxy resin into an acetonitrile solvent, wherein the mass ratio of the 4- ((ethylaniline) methyl) benzenesulfonic acid to the pyridine modified epoxy resin is 1:0.78, stirring and mixing, reacting for 1.8h at 35 ℃, washing and drying after the reaction is finished to obtain an intermediate 3;
(6) Adding 11 parts by weight of epichlorohydrin into a reactor under ice water bath, stirring for 25min, dropwise adding 6 parts by weight of intermediate 3 into the reactor, wherein the dropwise adding time is 1.8h, reacting for 3.5h at 26 ℃ after the dropwise adding is finished, filtering, washing and vacuum drying to obtain pyridine modified epoxy resin modified quaternary ammonium salt;
(7) 18 parts by weight of organosilicon modified gemini quaternary ammonium salt, 17 parts by weight of pyridine modified epoxy resin modified quaternary ammonium salt and 6 parts by weight of 3-chloro-2-hydroxypropyl trimethyl ammonium chloride are added into a reactor to react for 8min at 900rmp, and after the reaction is finished, the solid cationic etherifying agent is obtained by vacuum drying.
Comparative example 1
This comparative example is different from example 4 in that no silicone modified gemini quaternary ammonium salt was added.
Comparative example 2
This comparative example is different from example 4 in that no pyridine-modified epoxy resin-modified quaternary ammonium salt was added.
Taking streptococcus aureus, escherichia coli and candida krusei as test strains, transferring 1.5mL of bacterial suspension (with the concentration of 1 multiplied by 105 CFU/mL) of the test strains into a sterilization culture dish containing MH broth culture medium, attaching a solid cationic etherifying agent sample to the surface of the culture medium, culturing for 14 hours at 40 ℃ in a constant temperature incubator, and measuring the diameter of a bacteriostasis ring after culturing.
Table 1 antibacterial test.
As can be seen from Table 1, examples 1-4 of the present invention have a better antibacterial effect than comparative examples 1-2.
The preferred embodiments of the invention disclosed above are intended only to assist in the explanation of the invention. The preferred embodiments are not exhaustive or to limit the invention to the precise form disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best understand and utilize the invention. The invention is limited only by the claims and the full scope and equivalents thereof.
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| CN105503777A (en) * | 2015-12-09 | 2016-04-20 | 九江天赐高新材料有限公司 | Preparation method of quaternary ammonium salt GTMAC |
| CN109575148A (en) * | 2018-11-30 | 2019-04-05 | 河南华丽纸业包装股份有限公司 | A kind of quaternary ammonium salt cationic starch and preparation method thereof |
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| CN111978186A (en) * | 2020-08-24 | 2020-11-24 | 上海东升新材料有限公司 | Preparation method of solid cationic etherifying agent |
| CN113698444B (en) * | 2021-08-25 | 2024-05-03 | 东莞市妮特洗涤用品有限公司 | Cationic alkyl glycoside quaternary ammonium salt surfactant and preparation process thereof |
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| CN105503777A (en) * | 2015-12-09 | 2016-04-20 | 九江天赐高新材料有限公司 | Preparation method of quaternary ammonium salt GTMAC |
| CN109575148A (en) * | 2018-11-30 | 2019-04-05 | 河南华丽纸业包装股份有限公司 | A kind of quaternary ammonium salt cationic starch and preparation method thereof |
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