CN113698444A - Cationic alkyl glycoside quaternary ammonium salt surfactant and preparation process thereof - Google Patents
Cationic alkyl glycoside quaternary ammonium salt surfactant and preparation process thereof Download PDFInfo
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- CN113698444A CN113698444A CN202110979164.3A CN202110979164A CN113698444A CN 113698444 A CN113698444 A CN 113698444A CN 202110979164 A CN202110979164 A CN 202110979164A CN 113698444 A CN113698444 A CN 113698444A
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- 229930182470 glycoside Natural products 0.000 title claims abstract description 59
- -1 Cationic alkyl glycoside quaternary ammonium salt Chemical class 0.000 title claims abstract description 55
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims abstract description 16
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 16
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 16
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 16
- FHLZUEPKLGQEQP-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCC[Si](C)(OC)OC FHLZUEPKLGQEQP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000012043 crude product Substances 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000010410 layer Substances 0.000 claims description 12
- 238000002390 rotary evaporation Methods 0.000 claims description 12
- 229910000474 mercury oxide Inorganic materials 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000005457 ice water Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000003760 magnetic stirring Methods 0.000 claims 1
- 238000004321 preservation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003093 cationic surfactant Substances 0.000 abstract description 3
- 238000004945 emulsification Methods 0.000 abstract description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 3
- 230000007928 solubilization Effects 0.000 abstract description 3
- 238000005063 solubilization Methods 0.000 abstract description 3
- 229910052710 silicon Inorganic materials 0.000 abstract description 2
- 239000010703 silicon Substances 0.000 abstract description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940101209 mercuric oxide Drugs 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a cationic alkyl glycoside quaternary ammonium salt surfactant and a preparation process thereof, wherein 3-chloro-2-methylpropene reacts with hypochlorous acid, hydrogen chloride is removed to prepare an intermediate 1, the intermediate 2 is reacted with N, N-diethylaminopropyl methyl dimethoxysilane to prepare an intermediate 2, the intermediate 2 reacts with dodecyl dimethyl tertiary amine hydrochloride to generate an intermediate 3, the intermediate 3 reacts with chloroacetyl chloride to prepare an intermediate 4, and finally the intermediate 4 reacts with alkyl glycoside to generate the cationic alkyl glycoside quaternary ammonium salt surfactant; in addition, the surfactant disclosed by the invention has an organic silicon structure, has the characteristics of both organic matters and inorganic matters, is endowed with excellent high-temperature resistance, and can play a role of an organic silicon cationic surfactant and a role of solubilization and emulsification.
Description
Technical Field
The invention belongs to the technical field of surfactant preparation, and particularly relates to a cationic alkyl glycoside quaternary ammonium salt surfactant and a preparation process thereof.
Background
The alkyl glycoside is a compound obtained by dehydration of glucose and fatty alcohol through acetal under the action of an acid catalyst. The general composition is a mixture of single glycoside, two glycosides, three glycosides and multiple glycosides, so the composition is also called alkyl polyglycoside, and the alkyl polyglycoside belongs to a novel high-efficiency, nontoxic and biodegradable nonionic surfactant.
In recent years, the green safety of APG is well known, the irritation is extremely low, the biocompatibility is good, and hydroxyl on a sugar ring in alkyl glycoside can react with various active groups to generate various APG derivatives. Meanwhile, the synthesis development of the alkyl glycoside derivatives is promoted by the industrial mature production of the alkyl glycoside, the alkyl glycoside derivatives not only retain the advantages of the alkyl glycoside, but also remarkably improve the water solubility, the hard water resistance, the foam stability, the surface activity, the antistatic performance and the like of the alkyl glycoside derivatives through the modification of the alkyl glycoside, wherein the cation alkyl glycoside quaternary ammonium salt is one of the alkyl glycoside derivatives. The cationic alkyl glycoside quaternary ammonium salt not only has the excellent performance of the cationic surfactant, but also has the characteristics of no toxicity, small irritation and easy degradation, increases the synergistic effect of compounding with the anionic surfactant, and is widely applied to the fields of cleaning agents, textile printing and dyeing, personal care, pesticides, antistatic agents, bactericides, industrial water treatment, drilling fluid treatment agents, foaming agents and the like.
However, in the prior art, the surfactant based on the alkyl glycoside quaternary ammonium salt only has excellent antibacterial performance, and does not have the excellent performances of high temperature resistance, solubilization and emulsification of organosilicon and the like.
Disclosure of Invention
In order to overcome the technical problems, the invention provides a cationic alkyl glycoside quaternary ammonium salt surfactant and a preparation process thereof.
The purpose of the invention can be realized by the following technical scheme:
a cationic alkyl glycoside quaternary ammonium salt surfactant comprises the following steps:
adding mercury oxide into deionized water, controlling the temperature of the system to be not more than 30 ℃, introducing chlorine until the water solution of the system becomes light brown, magnetically stirring and dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, stirring at constant speed until the water solution of the system is colorless, introducing chlorine and controlling the system to be not more than 50 ℃, preserving heat for 1h at the temperature, then cooling to 25-30 ℃, dropwise adding a sodium hydroxide water solution with the mass fraction of 35% to adjust the system to be neutral, continuously stirring at constant speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer with diethyl ether for three times, combining and collecting obtained organic phases, drying, and distilling under reduced pressure to prepare an intermediate 1;
in the first step, under the participation of mercuric oxide, chlorine is introduced into deionized water to form hypochlorous acid, then 3-chloro-2-methyl propylene is added, the 3-chloro-2-methyl propylene reacts with the hypochlorous acid, and then sodium hydroxide is added to remove hydrogen chloride, so that an intermediate 1 is prepared, wherein the process is as follows:
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyl dimethoxysilane and anhydrous methanol, heating in a water bath at 45-55 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then performing rotary evaporation to remove the methanol to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then performing vacuum drying for 5 hours to obtain an intermediate 2;
in the second step, N-diethylaminopropyl methyl dimethoxy silane and the intermediate 1 are mixed in a nitrogen atmosphere by using anhydrous methanol as a solvent to prepare an intermediate 2, and the reaction process is as follows:
thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 20-25 ℃ in the adding process, stirring at a constant speed and reacting for 6 hours to obtain a crude product, and carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3;
in the third step, dodecyl dimethyl tertiary amine hydrochloride and the intermediate 2 are mixed in absolute ethyl alcohol, and the dodecyl dimethyl tertiary amine hydrochloride and the intermediate 2 react to generate an intermediate 3, wherein the reaction process is as follows:
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 4-6 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.03-0.05;
in the fourth step, the intermediate 3 and chloroacetyl chloride are mixed in tetrahydrofuran, pyridine is added as organic base, and the intermediate 3 and chloroacetyl chloride react, wherein the reaction process is as follows:
and fifthly, adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 70-80 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, and performing rotary evaporation on the crude product under the conditions that the temperature is 65-70 ℃ and the pressure is 80kPa until the solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4, the isopropanol and the alkyl glycoside is 20.20-20.50 g: 30 mL: 105-.
In the fifth step, the intermediate 4 and alkyl glycoside are mixed in isopropanol, and the intermediate 4 and alkyl glycoside react to generate cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the reaction process is as follows:
further, in the second step, the mixture a is formed by mixing the intermediate 1 and anhydrous methanol according to the weight ratio of 1: 10.
Furthermore, the dosage ratio of the mercuric oxide, the deionized water and the 3-chloro-2-methyl propylene in the first step is 0.5-1g, 40mL and 50 mL.
Further, in the second step, the weight ratio of N, N-diethylaminopropylmethyldimethoxysilane to the mixture a is 1: 10-15.
Furthermore, the dosage ratio of the dodecyl dimethyl tertiary amine hydrochloride, the intermediate 2 and the absolute ethyl alcohol in the third step is 17.00-17.25 g: 6.25-6.30 g: 50-75 mL.
The invention has the beneficial effects that:
the invention relates to a cationic alkyl glycoside quaternary ammonium salt surfactant which is prepared by reacting 3-chloro-2-methylpropene with hypochlorous acid, removing hydrogen chloride to prepare an intermediate 1, reacting with N, N-diethylaminopropyl methyl dimethoxysilane to prepare an intermediate 2, reacting the intermediate 2 with dodecyl dimethyl tertiary amine hydrochloride to generate an intermediate 3, reacting the intermediate 3 with chloroacetyl chloride to prepare an intermediate 4, and reacting the intermediate 4 with alkyl glycoside to generate the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the surfactant has a quaternary ammonium salt structure, quaternary ammonium salt molecules are positively charged, relative molecular weight is increased after high molecular weight, charge density is increased, and as the surfaces of microbial cells are negatively charged, phospholipids and a plurality of membrane protein hydrolysates contained in cell membranes are also negatively charged, so that the sterilization can be carried out with high efficiency and the antibacterial effect can be achieved; in addition, the surfactant disclosed by the invention has an organic silicon structure, has the characteristics of both organic matters and inorganic matters, is endowed with excellent high-temperature resistance, and can play a role of an organic silicon cationic surfactant and a role of solubilization and emulsification.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the 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 cationic alkyl glycoside quaternary ammonium salt surfactant comprises the following steps:
adding mercury oxide into deionized water, controlling the temperature of the system to be not more than 30 ℃, introducing chlorine until the water solution of the system becomes light brown, magnetically stirring and dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, stirring at constant speed until the water solution of the system is colorless, introducing chlorine and controlling the temperature of the system to be not more than 50 ℃, preserving heat for 1h at the temperature, then cooling to 25 ℃, dropwise adding a sodium hydroxide water solution with the mass fraction of 35% to adjust the system to be neutral, continuously stirring at constant speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer with diethyl ether for three times, combining the collected organic phases, drying and distilling under reduced pressure to prepare an intermediate 1, wherein the dosage ratio of the mercury oxide, the deionized water and the 3-chloro-2-methylpropene is 0.5 g: 40 mL: 50 mL;
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyldimethoxysilane and anhydrous methanol, heating in a water bath at 45 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then removing the methanol by rotary evaporation to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then drying in vacuum for 5 hours to obtain an intermediate 2, N, N-diethylaminopropyl methyldimethoxysilane and the mixture a with the weight ratio of 1: 10;
the mixture a is formed by mixing the intermediate 1 and anhydrous methanol according to the weight ratio of 1: 10.
Thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 20 ℃ in the adding process, stirring at a constant speed, reacting for 6 hours to obtain a crude product, carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3, wherein the dosage ratio of the dodecyl dimethyl tertiary amine hydrochloride to the intermediate 2 to the absolute ethyl alcohol is 17.00 g: 6.25 g: 50 mL;
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 4 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.03;
adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 70 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, performing rotary evaporation on the crude product under the conditions that the temperature is 65 ℃ and the pressure is 80kPa until the solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4, the isopropanol and the alkyl glycoside is 20.20 g: 30 mL: 105 g.
Example 2
A cationic alkyl glycoside quaternary ammonium salt surfactant comprises the following steps:
adding mercury oxide into deionized water, controlling the temperature of the system to be not more than 30 ℃, introducing chlorine until the water solution of the system becomes light brown, magnetically stirring and dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, stirring at constant speed until the water solution of the system is colorless, introducing chlorine and controlling the temperature of the system to be not more than 50 ℃, preserving heat for 1h at the temperature, then cooling to 25 ℃, dropwise adding a sodium hydroxide water solution with the mass fraction of 35% to adjust the system to be neutral, continuously stirring at constant speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer with diethyl ether for three times, combining the collected organic phases, drying and distilling under reduced pressure to prepare an intermediate 1, wherein the dosage ratio of the mercury oxide, the deionized water and the 3-chloro-2-methylpropene is 0.81 g: 40 mL: 50 mL;
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyldimethoxysilane and anhydrous methanol, heating in a water bath at 45 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then removing the methanol by rotary evaporation to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then drying in vacuum for 5 hours to obtain an intermediate 2, N, N-diethylaminopropyl methyldimethoxysilane and the mixture a with the weight ratio of 1: 10;
the mixture a is formed by mixing the intermediate 1 and anhydrous methanol according to the weight ratio of 1: 10.
Thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 20 ℃ in the adding process, stirring at a constant speed, reacting for 6 hours to obtain a crude product, carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3, wherein the dosage ratio of the dodecyl dimethyl tertiary amine hydrochloride to the intermediate 2 to the absolute ethyl alcohol is 17.05 g: 6.28 g: 60 mL;
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 4 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.03;
adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 70 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, performing rotary evaporation on the crude product under the conditions that the temperature is 65 ℃ and the pressure is 80kPa until the solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4, the isopropanol and the alkyl glycoside is 20.30 g: 30 mL: 105 g.
Example 3
A cationic alkyl glycoside quaternary ammonium salt surfactant comprises the following steps:
adding mercury oxide into deionized water, controlling the temperature of the system to be not more than 30 ℃, introducing chlorine until the water solution of the system becomes light brown, magnetically stirring and dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, stirring at constant speed until the water solution of the system is colorless, introducing chlorine and controlling the temperature of the system to be not more than 50 ℃, preserving heat for 1h at the temperature, then cooling to 30 ℃, dropwise adding a sodium hydroxide water solution with the mass fraction of 35% to adjust the system to be neutral, continuously stirring at constant speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer with diethyl ether for three times, combining the collected organic phases, drying and distilling under reduced pressure to prepare an intermediate 1, wherein the dosage ratio of the mercury oxide, the deionized water and the 3-chloro-2-methylpropene is 0.8 g: 40 mL: 50 mL;
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyldimethoxysilane and anhydrous methanol, heating in a water bath at 55 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then removing the methanol by rotary evaporation to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then drying in vacuum for 5 hours to obtain an intermediate 2, N, N-diethylaminopropyl methyldimethoxysilane and the mixture a with the weight ratio of 1: 15;
the mixture a is formed by mixing the intermediate 1 and anhydrous methanol according to the weight ratio of 1: 10.
Thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 25 ℃ in the adding process, stirring at a constant speed and reacting for 6 hours to obtain a crude product, carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3, wherein the dosage ratio of the dodecyl dimethyl tertiary amine hydrochloride to the intermediate 2 to the absolute ethyl alcohol is 17.25 g: 6.28 g: 70 mL;
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 6 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.04;
adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 80 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, performing rotary evaporation on the crude product at a temperature of 70 ℃ and a pressure of 80kPa until a solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4 to the isopropanol to the alkyl glycoside is 20.40g to 30mL to 1110 g.
Example 4
A cationic alkyl glycoside quaternary ammonium salt surfactant comprises the following steps:
adding mercury oxide into deionized water, controlling the temperature of the system to be not more than 30 ℃, introducing chlorine until the water solution of the system becomes light brown, magnetically stirring and dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, stirring at constant speed until the water solution of the system is colorless, introducing chlorine and controlling the temperature of the system to be not more than 50 ℃, preserving heat for 1h at the temperature, then cooling to 30 ℃, dropwise adding a sodium hydroxide water solution with the mass fraction of 35% to adjust the system to be neutral, continuously stirring at constant speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer with diethyl ether for three times, combining the collected organic phases, drying and distilling under reduced pressure to prepare an intermediate 1, wherein the dosage ratio of the mercury oxide, the deionized water and the 3-chloro-2-methylpropene is 1 g: 40 mL: 50 mL;
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyldimethoxysilane and anhydrous methanol, heating in a water bath at 55 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then removing the methanol by rotary evaporation to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then drying in vacuum for 5 hours to obtain an intermediate 2, N, N-diethylaminopropyl methyldimethoxysilane and the mixture a with the weight ratio of 1: 15;
the mixture a is formed by mixing the intermediate 1 and anhydrous methanol according to the weight ratio of 1: 10.
Thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 25 ℃ in the adding process, stirring at a constant speed and reacting for 6 hours to obtain a crude product, carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3, wherein the dosage ratio of the dodecyl dimethyl tertiary amine hydrochloride to the intermediate 2 to the absolute ethyl alcohol is 17.25 g: 6.30 g: 75 mL;
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 6 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.05;
adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 80 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, performing rotary evaporation on the crude product at a temperature of 70 ℃ and a pressure of 80kPa until a solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4 to the isopropanol to the alkyl glycoside is 20.50g to 30mL to 110 g.
Comparative example 1
The comparative example is alkyl glycoside quaternary ammonium salt surfactant synthesized by alkyl glycoside and cationic etherifying agent in the prior art.
Antibacterial performance against examples 1 to 4 and comparative example 1 and
as can be seen from the above table, the bacteriostatic ratio of the examples 1-4 to Escherichia coli is 99.5-99.7%, the bacteriostatic ratio to Staphylococcus aureus is 96.3-97.5%, and the critical micelle concentration is 2.0-2.2 mmol/L; comparative example 1 has an inhibition rate of 98.5% for escherichia coli, an inhibition rate of 95.2% for staphylococcus aureus, and a critical micelle concentration of 2.5 mmol/L.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (6)
1. A preparation process of a cationic alkyl glycoside quaternary ammonium salt surfactant is characterized by comprising the following steps:
adding mercury oxide into deionized water, controlling the temperature of a system to be not more than 30 ℃, introducing chlorine gas, carrying out magnetic stirring, dropwise adding 3-chloro-2-methylpropene, controlling the dropwise adding time to be 1h, carrying out uniform stirring until an aqueous solution of the system is colorless, introducing chlorine gas, controlling the temperature of the system to be not more than 50 ℃, carrying out heat preservation for 1h at the temperature, then cooling to 25-30 ℃, dropwise adding a sodium hydroxide aqueous solution with the mass fraction of 35% to adjust the system to be neutral, continuing to stir at the uniform speed for 1h to prepare a reaction solution, separating an organic layer and a water layer, extracting the water layer for three times, combining and collecting obtained organic phases, drying, and carrying out reduced pressure distillation to prepare an intermediate 1;
secondly, introducing nitrogen into a three-neck flask to exhaust air, then adding N, N-diethylaminopropyl methyl dimethoxysilane and anhydrous methanol, heating in a water bath at 45-55 ℃ and magnetically stirring, slowly adding the mixture a, stirring at a constant speed at the temperature and reacting for 6 hours, then performing rotary evaporation to remove the methanol to obtain a crude product, eluting the crude product with anhydrous ether for 4 times, and then performing vacuum drying for 5 hours to obtain an intermediate 2;
thirdly, adding dodecyl dimethyl tertiary amine hydrochloride and absolute ethyl alcohol into a four-neck flask, slowly adding the intermediate 2, controlling the system temperature to be 20-25 ℃ in the adding process, stirring at a constant speed and reacting for 6 hours to obtain a crude product, and carrying out reduced pressure distillation, cooling and suction filtration on the crude product to obtain an intermediate 3;
fourthly, adding the intermediate 3 prepared in the third step into tetrahydrofuran, stirring at a constant speed at room temperature, adding pyridine, transferring to an ice water bath, adding chloroacetyl chloride, stirring at a constant speed, reacting for 4-6 hours to obtain an intermediate 4, and controlling the weight ratio of the intermediate 3 to the chloroacetyl chloride to the pyridine to be 1: 0.03-0.05;
and fifthly, adding the intermediate 4 prepared in the fourth step and isopropanol into a four-neck flask, stirring at a constant speed, heating to 70-80 ℃, adding alkyl glycoside, stirring at a constant speed, reacting for 6 hours to obtain a crude product, and performing rotary evaporation on the crude product under the conditions that the temperature is 65-70 ℃ and the pressure is 80kPa until the solvent is removed to obtain the cationic alkyl glycoside quaternary ammonium salt surfactant, wherein the dosage ratio of the intermediate 4, the isopropanol and the alkyl glycoside is 20.20-20.50 g: 30 mL: 105-.
2. The process according to claim 1, wherein the mixture a in the second step is obtained by mixing the intermediate 1 and anhydrous methanol in a weight ratio of 1: 10.
3. The process of claim 1, wherein the ratio of the mercury oxide to the deionized water to the 3-chloro-2-methylpropene in the first step is 0.5-1g to 40mL to 50 mL.
4. The process for preparing the cationic alkyl glycoside quaternary ammonium salt surfactant according to claim 1, wherein the weight ratio of the N, N-diethylaminopropylmethyldimethoxysilane to the mixture a in the second step is 1: 10-15.
5. The process for preparing a cationic alkyl glycoside quaternary ammonium salt surfactant according to claim 1, wherein the dosage ratio of dodecyl dimethyl tertiary amine hydrochloride, intermediate 2 and absolute ethyl alcohol in the third step is 17.00-17.25 g: 6.25-6.30 g: 50-75 mL.
6. The cationic alkyl glycoside quaternary ammonium salt surfactant is characterized by being prepared according to the preparation process of the cationic alkyl glycoside quaternary ammonium salt surfactant in claim 1.
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