CN115124563B - Seven-methyl siloxane polyoxyethylene ether gallate and preparation method and application thereof - Google Patents

Seven-methyl siloxane polyoxyethylene ether gallate and preparation method and application thereof Download PDF

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Publication number
CN115124563B
CN115124563B CN202210897646.9A CN202210897646A CN115124563B CN 115124563 B CN115124563 B CN 115124563B CN 202210897646 A CN202210897646 A CN 202210897646A CN 115124563 B CN115124563 B CN 115124563B
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gallate
polyoxyethylene ether
preparation
heptamethyl
reaction
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CN115124563A (en
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陈洪龄
赵雨萌
林勇强
梁齐波
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Guangdong Micro Control Biotechnology Co ltd
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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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • 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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0889—Reactions not involving the Si atom of the Si-O-Si sequence
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/54—Silicon compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention discloses a heptamethyl siloxane polyoxyethylene ether gallate and a preparation method and application thereof, wherein the preparation method is as follows: dissolving heptamethyltrisiloxane polyoxyethylene ether and sodium methoxide in an organic solvent to obtain a mixed solution; dissolving methyl gallate in an organic solvent, heating, and then adding the mixed solution for reaction; cooling after the reaction is finished, separating solid from liquid, and taking a liquid part for rotary evaporation to obtain the catalyst. According to the invention, the heptamethyl trisiloxane polyoxyethylene ether and the methyl gallate are subjected to transesterification reaction to prepare the heptamethyl trisiloxane polyoxyethylene ether gallate, which has good surfactant function and sterilization effect.

Description

Seven-methyl siloxane polyoxyethylene ether gallate and preparation method and application thereof
Technical Field
The invention belongs to the fields of surfactants, emulsifiers and antibacterial agents, and relates to heptamethyl siloxane polyoxyethylene ether gallate, a preparation method and application thereof.
Background
The surfactant consists of a hydrophilic end and a hydrophobic end, the amphiphilic structure property of the surfactant enables the aqueous solution to contact air at the hydrophobic end in an air-water interface, the hydrophilic end stretches into the liquid, the hydrophilic end is closely distributed at the air-liquid interface, the interfacial tension is obviously reduced, and the surfactant has the functions of emulsification, wetting, lotion and the like. Because of its special amphiphilic structure, surfactants are widely used in both industry and civilian industries, and are closely related to our lives.
The surfactant has a certain sterilization function, particularly the sterilization function of the cationic surfactant is more remarkable, and the widely used cationic surfactant benzalkonium chloride is one of the well-known representative varieties of the surfactant which is widely used as sterilization. However, such bactericides have a positive charge and have limited application to some extent, such as where anionic surfactants are present. Anionic and nonionic surfactants are widely used as detergents, emulsifiers, wetting spreaders, etc. in the life and industrial fields of people, and in order to ensure a long shelf life of finished detergents, emulsions, etc. products, it is necessary to add antibacterial and bacteriostatic agents to prevent the products from spoiling due to bacteria growth during storage and use.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the heptamethyl siloxane polyoxyethylene ether gallate, which is prepared from the heptamethyl trisiloxane polyoxyethylene ether and the methyl gallate serving as raw materials, has the functions of obviously reducing the surface tension and emulsifying, and has good antibacterial and bactericidal effects.
In order to solve the technical problems, the invention discloses a heptamethyl siloxane polyoxyethylene ether gallate, and a preparation method and application thereof.
In particular to a heptamethyl siloxane polyoxyethylene ether gallate with a structure shown in a formula I,
wherein n=5-7.
Wherein, the chemical reaction equation for preparing the compound of formula I is as follows:
wherein n=5-7.
Specifically, according to the preparation method of the heptamethyl siloxane polyoxyethylene ether gallate, heptamethyl trisiloxane polyoxyethylene ether and sodium methoxide are dissolved in an organic solvent (preferably, the mass ratio of the heptamethyl trisiloxane polyoxyethylene ether to the organic solvent is 1:2-4) to obtain a mixed solution; dissolving methyl gallate in an organic solvent, heating (preferably, the mass ratio of the methyl gallate to the organic solvent is 1:4-6), and then adding the mixed solution for reaction; cooling after the reaction is finished, separating solid from liquid, and taking a liquid part for rotary evaporation to obtain the catalyst.
Specifically, the organic solvent is any one or a combination of two of dioxane and tetrahydrofuran, and preferably dioxane.
Specifically, the molar ratio of the heptamethyltrisiloxane polyoxyethylene ether to the methyl gallate is 1:1.05 to 1.20.
Specifically, the molar ratio of the sodium methoxide to the methyl gallate is 0.0001-0.3: 1.
specifically, the heating temperature is 60-90 ℃ and the heating time is 0.1-2 h.
Specifically, the reaction temperature is 60-90 ℃ and the reaction time is 3-12 h.
Specifically, the rotary steaming temperature is 50-100 ℃, and the rotary steaming vacuum degree is 650-700 mmHg.
The application of the heptamethyl siloxane polyoxyethylene ether gallate as a surfactant is also within the protection scope of the invention.
The application of the heptamethyl siloxane polyoxyethylene ether gallate as a bactericide is also within the protection scope of the invention.
The beneficial effects are that:
according to the invention, methyl gallate is subjected to transesterification reaction by using polyoxyethylene ether modified heptamethyltrisiloxane to prepare the heptamethylsiloxane polyoxyethylene ether gallate bactericide, and the polyoxyethylene ether modified heptamethyltrisiloxane is combined with gallic acid, and organic silicon is introduced by using ester groups, so that the prepared bactericide has good surface spreadability and good surface tension reducing capability and bactericidal effect.
Drawings
The foregoing and/or other advantages of the invention will become more apparent from the following detailed description of the invention when taken in conjunction with the accompanying drawings and detailed description.
FIG. 1 is a graph showing the surface tension of heptamethylsiloxane polyoxyethylene ether gallate in example 1;
FIG. 2 is a graph showing the surface tension of heptamethylsiloxane polyoxyethylene ether gallate in example 2;
FIG. 3 is an infrared spectrum of methyl gallate, heptamethyltrisiloxane polyoxyethylene ether and heptamethyltrisiloxane polyoxyethylene ether gallate in example 2;
FIG. 4 is a graph showing the emulsifying ability of the heptamethylsiloxane polyoxyethylene ether gallate in example 2;
FIG. 5 is a graph showing the surface tension of heptamethylsiloxane polyoxyethylene ether gallate in example 3;
FIG. 6 is a graph showing the surface tension of heptamethylsiloxane polyoxyethylene ether gallate in example 4.
Detailed Description
The invention will be better understood from the following examples.
Example 1
2.024g (0.011 mol) of gallic acid methyl ester is dissolved in 10g of dioxane, the mixture is preheated for 0.5h to 60 ℃, then 0.0054g (0.0001 mol) of sodium methoxide and 5.44g of heptamethyltrisiloxane polyoxyethylene ether (n=5) are dissolved in 15g of dioxane, the mixture is slowly added dropwise into the solution of gallic acid methyl ester dioxane, the mixture is heated to 90 ℃ for reaction for 5h, after the solution is cooled, the solid is removed by suction filtration, and the mixture is distilled under the vacuum degree of 700mmHg in a rotary way at 80 ℃ to obtain the product, and the yield is 68.5%.
Surface tension test: the surface tension test of the heptamethylsiloxane polyoxyethylene ether gallate in example 1 is shown in fig. 1. As the concentration of surfactant in water increases, the surface tension of the solution begins to drop sharply at a concentration of 5X 10 -5 When the mass fraction is in%, the surface tension of the solution is reduced to 20.718mN/m, and the heptamethyl siloxane polyoxyethylene ether gallate has good capability of reducing the surface tension.
Example 2
19.32g (0.105 mol) of methyl gallate is dissolved in 100g of dioxane, the mixture is preheated for 0.5h to 65 ℃, then 0.054g (0.001 mol) of sodium methoxide and 58.8g (0.1 mol) of heptamethyltrisiloxane polyoxyethylene ether (n=6) are dissolved in 150g of dioxane and slowly added dropwise into the solution of methyl gallate dioxane, the mixture is heated to 80 ℃ for reaction for 6h, solids are removed by suction filtration after the solution is cooled, and the product is obtained by rotary evaporation under the conditions of 85 ℃ and 680mmHg in vacuum degree, and the yield is 66.5%.
Surface tension test: the surface tension test of the heptamethylsiloxane polyoxyethylene ether gallate in example 2 is shown in fig. 2. As the concentration of surfactant in water increases, the surface tension of the solution begins to drop sharply at a concentration of 5X 10 -5 When the mass fraction is in%, the surface tension of the solution is reduced to 22.242mN/m, and the heptamethyl siloxane polyoxyethylene ether gallate has good capability of reducing the surface tension.
And (3) infrared spectrum analysis: the infrared spectra of methyl gallate, heptamethyltrisiloxane polyoxyethylene ether and heptamethyltrisiloxane polyoxyethylene ether gallate in example 2 are shown in FIG. 3, for methyl gallate at 1716cm -1 An infrared characteristic absorption peak of carbon-oxygen double bond appears at 1254cm -1 An infrared characteristic absorption peak of ether bond appears at the position, and for heptamethyltrisiloxane polyoxyethylene ether, the infrared characteristic absorption peak is 1254cm -1 An infrared characteristic absorption peak of ether bond appears at 1200cm -1 An infrared characteristic absorption peak of a silicon-carbon bond appears at 950cm -1 The infrared characteristic absorption peak of the silicon oxide appears at the position, and the infrared characteristic absorption peak of the silicon oxide appears at 1716cm for heptamethyltrisiloxane polyoxyethylene ether gallate -1 Characteristic absorption peaks of carbon-oxygen double bonds appear at 1254cm -1 An infrared characteristic absorption peak of ether bond appears at 950cm -1 An infrared characteristic absorption peak of a siloxane bond appears at the position, and the successful synthesis of the heptamethyltrisiloxane polyoxyethylene ether gallate is proved.
Emulsification capability test: the emulsification capacity test of the heptamethylsiloxane polyoxyethylene ether gallate in example 2 is shown in fig. 4. The emulsifying capacity of the solution becomes stronger as the concentration of the surfactant in the water increases, the 20mL of surfactant with different concentrations is emulsified for 20mL of oil phase with a homogenizer at 10000rad/s for three minutes and then timing is started, the timing is stopped when 10mL of water phase is separated out, and the longer the time is, the stronger the emulsifying capacity is. The seven-methyl siloxane polyoxyethylene ether gallate has good emulsifying property.
Example 3
19.32g (0.115 mol) of methyl gallate is dissolved in 100g of dioxane, the mixture is preheated for 0.5h to 75 ℃, then 0.054g (0.001 mol) of sodium methoxide and 63.2g (0.1 mol) of heptamethyltrisiloxane polyoxyethylene ether (n=7) are dissolved in 150g of dioxane and slowly added dropwise into the solution of methyl gallate dioxane, the mixture is heated to 85 ℃ for reaction for 8h, solids are removed by suction filtration after the solution is cooled, and the product is obtained by rotary evaporation under the conditions of 90 ℃ and 660mmHg in vacuum degree, wherein the yield is 65.9%.
Surface tension test: the surface tension test of the heptamethylsiloxane polyoxyethylene ether gallate in example 3 is shown in fig. 5. As the concentration of surfactant in water increases, the surface tension of the solution begins to drop sharply at a concentration of 5X 10 -5 When the mass fraction is in%, the surface tension of the solution is reduced to 23.455mN/m, and the heptamethyl siloxane polyoxyethylene ether gallate has good capability of reducing the surface tension.
Sterilization capability test: the sterilization performance of the heptamethyl siloxane polyoxyethylene ether gallate bactericide is shown in table 1, a certain amount of bacterial culture solution is added into a sample, and after a certain period of time, the microbial detection is carried out. A proper amount of sample is sucked by a sterile straw and uniformly mixed in a tryptone agar medium, then the peptone agar medium is cultured for 48 hours at 35 ℃, and the peptone agar medium is taken out to observe the growth condition of microorganisms on an agar plate for reading. The sterilization rate of the heptamethyl siloxane polyoxyethylene ether gallate bactericide on escherichia coli, staphylococcus aureus and candida albicans is more than or equal to 90 percent, and the heptamethyl siloxane polyoxyethylene ether gallate bactericide has a sterilization effect.
TABLE 1 sterilizing Properties of heptamethyl siloxane polyoxyethylene ether gallate
Example 4
22.08g (0.12 mol) of methyl gallate is dissolved in 100g of dioxane, the mixture is preheated for 1h to 70 ℃, then 0.054g (0.001 mol) of sodium methoxide and 58.8g (0.1 mol) of heptamethyltrisiloxane polyoxyethylene ether (n=6) are dissolved in 150g of dioxane, slowly and dropwise added into the solution of methyl gallate dioxane, the mixture is heated to 90 ℃ for reaction for 9h, after the solution is cooled, the solid is removed by suction filtration, and the product is obtained by rotary evaporation under the conditions of 85 ℃ and 680mmHg of vacuum degree, and the yield is 68.7%.
Surface tension test: the surface tension test of heptamethylsiloxane polyoxyethylene ether gallate in example 4 is shown in fig. 6. As the concentration of surfactant in water increases, the surface tension of the solution begins to drop sharply at a concentration of 5X 10 -5 When the mass fraction is in%, the surface tension of the solution is reduced to 21.325mN/m, and the heptamethyl siloxane polyoxyethylene ether gallate has good capability of reducing the surface tension.
Foam performance test: the 4 surfactant samples (surfactant samples prepared in example 1, example 2, example 3 and example 4, respectively) were prepared as surfactant solutions with a mass fraction of 0.1%, and equilibrated in a thermostatic water bath at 25.+ -. 0.2 ℃ for 12 hours (eliminating the influence of temperature on foam properties). To a 100mL stoppered cylinder was added 10mL of a 0.1% mass fraction aqueous solution of the sample to be measured, shaken largely 30 times at 25℃and then allowed to stand horizontally, and the foam volumes after the shaking was completed for 0min and 5min were recorded.
Table 2 foam properties
The invention provides a heptamethyl siloxane polyoxyethylene ether gallate, a preparation method and an application thought and a method thereof, and particularly the method and the method for realizing the technical scheme are numerous, the above is only a preferred embodiment of the invention, and it should be pointed out that a plurality of improvements and modifications can be made to those skilled in the art without departing from the principle of the invention, and the improvements and modifications are also regarded as the protection scope of the invention. The components not explicitly described in this embodiment can be implemented by using the prior art.

Claims (9)

1. A heptamethyl siloxane polyoxyethylene ether gallate is characterized by having a structure shown in a formula I,
wherein n=5-7.
2. The method for preparing the heptamethyl siloxane polyoxyethylene ether gallate according to claim 1, which is characterized in that heptamethyl trisiloxane polyoxyethylene ether and sodium methoxide are dissolved in an organic solvent to obtain a mixed solution; dissolving methyl gallate in an organic solvent, heating, and then adding the mixed solution for reaction; cooling after the reaction is finished, separating solid from liquid, and taking a liquid part for rotary evaporation to obtain the catalyst.
3. The preparation method according to claim 2, wherein the organic solvent is any one or a combination of two of dioxane and tetrahydrofuran.
4. The preparation method of claim 2, wherein the molar ratio of the heptamethyltrisiloxane polyoxyethylene ether to the methyl gallate is 1:1.05 to 1.20.
5. The preparation method of claim 2, wherein the molar ratio of sodium methoxide to methyl gallate is 0.0001-0.3: 1.
6. the method according to claim 2, wherein the heating is performed at a temperature of 60 to 90 ℃ for a time of 0.1 to 2h.
7. The preparation method according to claim 2, wherein the reaction temperature is 60-90 ℃ and the reaction time is 3-12 h.
8. The preparation method according to claim 2, wherein the rotary steaming temperature is 50-100 ℃, and the rotary steaming vacuum degree is 650-700 mmHg.
9. The use of the heptamethylsiloxane polyoxyethylene ether gallate as defined in claim 1 as a surfactant.
CN202210897646.9A 2022-07-28 2022-07-28 Seven-methyl siloxane polyoxyethylene ether gallate and preparation method and application thereof Active CN115124563B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102936333A (en) * 2012-11-02 2013-02-20 陕西科技大学 Aromatic hyperbranched polymer surfactant and preparation method thereof
CN103638872A (en) * 2013-12-16 2014-03-19 南京美思德新材料有限公司 Trisiloxane polyether-ester surfactant as well as preparation method thereof
CN105669968A (en) * 2015-12-30 2016-06-15 中山大学惠州研究院 Preparation method of polyether grafted trisiloxane surfactant
CN107501531A (en) * 2017-08-23 2017-12-22 大连大学 A kind of double block stabilizer HMTS PCL synthetic method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102936333A (en) * 2012-11-02 2013-02-20 陕西科技大学 Aromatic hyperbranched polymer surfactant and preparation method thereof
CN103638872A (en) * 2013-12-16 2014-03-19 南京美思德新材料有限公司 Trisiloxane polyether-ester surfactant as well as preparation method thereof
CN105669968A (en) * 2015-12-30 2016-06-15 中山大学惠州研究院 Preparation method of polyether grafted trisiloxane surfactant
CN107501531A (en) * 2017-08-23 2017-12-22 大连大学 A kind of double block stabilizer HMTS PCL synthetic method

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