CN112047976B - Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof - Google Patents
Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof Download PDFInfo
- Publication number
- CN112047976B CN112047976B CN202010950867.9A CN202010950867A CN112047976B CN 112047976 B CN112047976 B CN 112047976B CN 202010950867 A CN202010950867 A CN 202010950867A CN 112047976 B CN112047976 B CN 112047976B
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- fluorine
- intermediate product
- containing organosilicon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
- C07F7/18—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
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
- C07F7/18—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
-
- 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
Abstract
The invention relates to a fluorine-containing organosilicon quaternary ammonium salt and a preparation method and application thereof, wherein the chemical structural formula of the organosilicon quaternary ammonium salt is as follows:
wherein R is 1 Is CH 3 、CH 2 CH 3 、CH(CH 3 ) 2 Or CH 2 CH 2 CH 3 (ii) a Y is a chain segment containing alkyl, ether, thioether, amide, carbonyl, ester, alkenyl or alkynyl; rf has the formula: f- (CF) 2 ) a ‑(OC 3 F 6 ) b ‑(OC 2 F 4 ) c ‑(OCF 2 ) d ‑(CH 2 ) e -, a is any integer of 1 to 3, b, c, d are each 1 to 100Any integer, e is 1 or 2; x is Cl, br or I. The fluorine-containing organosilicon quaternary ammonium salt is used for spraying and coating a film on the surface of glass, so that the surface of the glass has the performances of antibiosis, hydrophobicity, oleophobicity, wear resistance and the like.
Description
Technical Field
The invention relates to the technical field of glass surface modification, in particular to a fluorine-containing organosilicon quaternary ammonium salt and a preparation method and application thereof.
Background
With the continuous improvement of living standard and the development of science and technology, people have increasingly strengthened health care consciousness, and health becomes an important factor for measuring quality of life. And the germs seriously harm the life and health of the masses in the actual life. In order to reduce these hazards, research on antibacterial materials has become a focus of research.
Glass uses very extensively in daily life, and from the smart mobile phone screen of private application to the various intelligent touch equipment of public place, mostly be the glass material at present, these equipment are attached to by the sweat on the fingerprint very easily in the use, leave the fingerprint trace, influence visual effect. In recent years, in order to improve user experience, most touch screens are coated with an anti-fingerprint film layer, and the film layer has a hydrophobic and oleophobic function and can effectively prevent the residue of fingerprint prints. But the anti-fingerprint film layer does not have obvious antibacterial property and can not meet the antibacterial requirement of customers at the same time. Most of the currently reported antibacterial glass is prepared by adding nano-silver into a matching material, and the product has the defects of low light transmittance, low strength, high cost, non-lasting sterilization, single function and the like. Therefore, a new solution is needed to be found, and the dual requirements of antifouling and antibacterial properties are met on the premise of not influencing the inherent characteristics of glass products.
Disclosure of Invention
The technical problem to be solved is as follows: aiming at the defect that the existing glass surface coating does not have antifouling and antibacterial properties at the same time, the invention provides the fluorine-containing organosilicon quaternary ammonium salt and the preparation method and application thereof.
The technical scheme is as follows: a fluorine-containing organosilicon quaternary ammonium salt has a chemical structural formula as follows:
wherein R is 1 Is CH 3 、CH 2 CH 3 、CH(CH 3 ) 2 Or CH 2 CH 2 CH 3 ；
Y is a chain segment containing alkyl, ether, thioether, amide, carbonyl, ester, alkenyl or alkynyl;
rf has the formula: f- (CF) 2 ) a -(OC 3 F 6 ) b -(OC 2 F 4 ) c -(OCF 2 ) d -(CH 2 ) e A is any integer from 1 to 3, b, c, d are each any integer from 1 to 100, e is 1 or 2;
x is Cl, br or I.
Rf is C 14 ~C 20 Y is a segment comprising an ester group or an alkane chain.
The preparation method of the fluorine-containing organosilicon quaternary ammonium salt comprises the following steps:
step 1: mixing a monomer and an acyl chlorination reagent in a reaction container, heating to 50-100 ℃ under the protection of inert gas, then dropwise adding dimethylformamide into the reaction container, and reacting for 2-4 hours under the condition of 50-100 ℃ to obtain an intermediate product a, wherein the structural formula of the monomer is Rf-COOH, the molar ratio of the monomer to the acyl chlorination reagent is (1-2): 1, and the weight of the dimethylformamide is 0.1-1% of the weight of the acyl chlorination reagent;
and 2, step: mixing dimethylethanolamine, an acid-binding agent and perfluorohexane, and cooling to 0 to 10 ℃ to obtain a reaction system, wherein the molar ratio of the dimethylethanolamine to the intermediate product a obtained in the step (1 to 1.2) to 1, the molar ratio of the acid-binding agent to the intermediate product a obtained in the step (1 to 3) to 1, and the volume ratio of the perfluorohexane to the dimethylethanolamine is 50;
and step 3: slowly dropwise adding the intermediate product a obtained in the step 1 into the reaction system obtained in the step 2, and reacting at room temperature for 1-2h;
and 4, step 4: after the reaction in the step 3 is finished, extracting with methanol, and then purifying to obtain an intermediate product b;
and 5: heating gamma-chloropropyltrimethoxysiloxane, an intermediate product b, potassium iodide and a solvent to 50-150 ℃ under the protection of inert gas, reacting for 12-48h, and purifying after the reaction is finished to obtain the fluorine-containing organosilicon quaternary ammonium salt, wherein the molar ratio of the intermediate product b to the gamma-chloropropyltrimethoxysiloxane is 1 (1-1.5), the weight of potassium iodide is 0.5-1% of that of the gamma-chloropropyltrimethoxysiloxane, the solvent is a mixed solution of m-benzotrifluoride and dimethylformamide, the volume ratio of the m-benzotrifluoride to the dimethylformamide is 1 (0.5-1), and the volume of the solvent to the intermediate product b is 50.
The acyl chloride reagent in the step 1 is oxalyl chloride or thionyl chloride.
The acid-binding agent in the step 2 is triethylamine or diisopropylethylamine.
The purification methods in step 4 and step 5 are both decompression rotary evaporation of solvent.
The fluorine-containing organosilicon quaternary ammonium salt is applied to the preparation of glass coatings.
Has the advantages that: the fluorine-containing organosilicon quaternary ammonium salt and the preparation method and the application thereof have the following beneficial effects: the silicon-oxygen radical of the organic silicon quaternary ammonium salt can be chemically bonded with the hydroxyl on the surface of the glass, so that the glass has excellent water and oil repellency and antibacterial performance, and the functional coating formed on the surface of the glass has excellent wear resistance. In addition, the coating can be formed only by adopting a heating and curing mode, the operation is simple, the feasibility is high, and the formed coating is a transparent coating layer and does not influence the attractiveness of the glass.
Detailed Description
For a further understanding of the invention, reference will now be made to the following examples, but it will be understood that these examples are intended to illustrate further features and advantages of the invention, and are not intended to limit the scope of the claims. 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 scope of protection of the present invention.
Example 1
A preparation method of fluorine-containing organosilicon quaternary ammonium salt comprises the following steps:
step 1: mixing a monomer and oxalyl chloride in a reaction vessel, heating to 50-60 ℃ under the protection of inert gas, then dropwise adding dimethylformamide into the reaction vessel, and reacting for 2h at 50-60 ℃ to obtain a light green solution intermediate product a, wherein the monomer is perfluoropolyether acid with the average molecular weight of 1500, and the structural formula of the intermediate product is CF 3 CF 2 CF 2 -(OCF 2 CF 2 CF 2 )n-O-CF 2 CF 2 -COOH, the molar ratio of monomer to oxalyl chloride is 1, the weight of dimethylformamide is 0.1% of the weight of oxalyl chloride;
step 2: mixing dimethylethanolamine, triethylamine and perfluorohexane, and cooling to 0-10 ℃ to obtain a reaction system, wherein the molar ratio of the dimethylethanolamine to the intermediate product a obtained in the step 1 to the triethylamine is 1;
and step 3: slowly dropwise adding the intermediate product a obtained by the reaction in the step 1 into the reaction system obtained in the step 2, and then reacting for 1h at room temperature;
and 4, step 4: after the reaction in the step 3 is finished, adding methanol for extraction and purification, and then carrying out reduced pressure rotary evaporation at 70 ℃ to remove the solvent to obtain a colorless transparent viscous liquid intermediate product b;
and 5: heating gamma-chloropropyltrimethoxysiloxane, an intermediate product b, potassium iodide and a solvent to 50-60 ℃ under the protection of inert gas, reacting for 18h, and performing reduced pressure rotary evaporation to remove the solvent after the reaction is finished to obtain a light yellow viscous liquid, namely the fluorine-containing organosilicon quaternary ammonium salt, wherein the molar ratio of the intermediate product b to the gamma-chloropropyltrimethoxysiloxane is 1:1, the weight of potassium iodide is 0.5% of the weight of the gamma-chloropropyltrimethoxysiloxane, the solvent is a mixed solution of m-ditrifluoromethane and dimethylformamide, the volume ratio of the m-ditrifluoromethane to dimethylformamide is 1:1, and the volume of the solvent to the intermediate product b is 50.
Example 2
A preparation method of fluorine-containing organosilicon quaternary ammonium salt comprises the following steps:
step 1: mixing a monomer and thionyl chloride in a reaction vessel, heating to 60-70 ℃ under the protection of inert gas, then dropwise adding dimethylformamide into the reaction vessel, and reacting for 3 hours at 60-70 ℃ to obtain a light green solution intermediate product a, wherein the monomer is perfluoropolyether acid with the average molecular weight of 3000, the structural formula of the perfluoropolyether acid is CF3CF2CF2- (OCF 2CF2CF 2) n-O-CF2CF2-COOH, the molar ratio of the monomer to oxalyl chloride is 1.2, and the weight of the dimethylformamide is 0.1 percent of the weight of the thionyl chloride;
step 2: mixing dimethylethanolamine, triethylamine and perfluorohexane, and cooling to 0-10 ℃ to obtain a reaction system, wherein the molar ratio of the dimethylethanolamine to the intermediate product a obtained in the step (1) to the triethylamine is 1.1;
and step 3: slowly dropwise adding the intermediate product a obtained in the step 1 into the reaction system obtained in the step 2, and reacting at room temperature for 1.5h;
and 4, step 4: after the reaction in the step 3 is finished, adding methanol for extraction and purification, and then carrying out reduced pressure rotary evaporation at 70 ℃ to remove the solvent to obtain a colorless transparent viscous liquid intermediate product b;
and 5: heating gamma-chloropropyltrimethoxysiloxane, an intermediate product b, potassium iodide and a solvent to 85-95 ℃ under the protection of inert gas, reacting for 24h, and performing reduced pressure rotary evaporation to remove the solvent after the reaction is finished to obtain a yellow viscous liquid, namely the fluorine-containing organosilicon quaternary ammonium salt, wherein the molar ratio of the intermediate product b to the gamma-chloropropyltrimethoxysiloxane is 1:1.2, the weight of potassium iodide is 0.5 percent of the weight of the gamma-chloropropyltrimethoxysiloxane, the solvent is a mixed solution of m-ditrifluoromethane and dimethylformamide, the volume ratio of the m-ditrifluoromethane to the dimethylformamide is 1: 0.5, and the volume of the solvent to the intermediate product b is 50.
Example 3
A preparation method of fluorine-containing organosilicon quaternary ammonium salt comprises the following steps:
step 1: mixing a monomer and thionyl chloride in a reaction vessel, heating to 70-80 ℃ under the protection of inert gas, then dropwise adding dimethylformamide into the reaction vessel, and reacting for 2 hours at 70-80 ℃ to obtain a light green solution intermediate product a, wherein the monomer is perfluorinated polyether acid with the average molecular weight of 4000, the structural formula of which is CF3CF2CF2- (OCF 2CF2CF 2) n-O-CF2CF2-COOH, the molar ratio of the monomer to oxalyl chloride is 1.5, and the weight of the dimethylformamide is 0.1% of the weight of the thionyl chloride;
step 2: mixing dimethylethanolamine, triethylamine and perfluorohexane, and cooling to 0-10 ℃ to obtain a reaction system, wherein the molar ratio of the dimethylethanolamine to the intermediate product a obtained in the step 1 to the triethylamine is 1.2;
and step 3: slowly dropwise adding the intermediate product a obtained by the reaction in the step 1 into the reaction system obtained in the step 2, and then reacting for 2 hours at room temperature;
and 4, step 4: after the reaction in the step 3 is finished, adding methanol for extraction and purification, and then carrying out reduced pressure rotary evaporation at 70 ℃ to remove the solvent to obtain a colorless transparent viscous liquid intermediate product b;
and 5: heating gamma-chloropropyltrimethoxysiloxane, an intermediate product b and a solvent to 100-120 ℃ under the protection of inert gas, reacting for 36h, and removing the solvent through reduced pressure rotary evaporation after the reaction is finished to obtain a reddish brown viscous liquid, namely the fluorine-containing organosilicon quaternary ammonium salt, wherein the molar ratio of the intermediate product b to the gamma-chloropropyltrimethoxysiloxane is 1:1.2, the solvent is a mixed solution of m-ditrifluoromethane and dimethylformamide, the volume ratio of the m-ditrifluoromethane to the dimethylformamide is 1:1, and the volume ratio of the solvent to the intermediate product b is 50.
The chemical structural formulas of the fluorine-containing organosilicon quaternary ammonium salts prepared in examples 1 to 3 are as follows:
wherein n is any integer from 7 to 22.
The method for plating the film on the surface of the glass by adopting the fluorine-containing organosilicon quaternary ammonium salt comprises the following steps: preparing a 0.1% solution of fluorine-containing organosilicon quaternary ammonium salt by using a fluorine-containing solvent, spraying the solution on the surface of glass in a spraying manner, and drying and curing the solution for 30 minutes at 120 ℃; the fluorine-containing solvent is perfluorohexane or m-ditrifluorotoluene.
The fluorine-containing organosilicon quaternary ammonium salts obtained in the embodiments 1 to 3 are respectively coated on the surfaces of glass, the surfaces are respectively marked as modified glass 1, modified glass 2 and modified glass 3, then blank glass without being coated, the modified glass 1, the modified glass 2 and the modified glass 3 are subjected to performance test, and the antibacterial test method refers to a method in appendix A (a film pasting method) of GB 21551.2-2010 (Special requirements for antibacterial, degerming and purifying functional antibacterial materials of household and similar-purpose electric appliances) issued by the Ministry of public health of the people's republic of China. The test strains selected for the experiment were: e.coli (AS 1.90) and Staphylococcus aureus (ATCC 6538). The test results are given in table 1 below.
TABLE 1
As can be seen from Table 1, when the fluorine-containing organosilicon quaternary ammonium salt is used for coating, the coating is bonded with the glass surface through chemical bonds, the coated glass surface has high antibacterial performance and antifouling performance, and the steel wool friction resistance of the coated glass surface is more than 2000 times.
While the embodiments of the present invention have been described in detail, those skilled in the art will recognize that the embodiments of the present invention can be practiced without departing from the spirit and scope of the claims.
Claims (6)
1. A fluorine-containing organosilicon quaternary ammonium salt is characterized in that the chemical structural formula of the organosilicon quaternary ammonium salt is as follows:
wherein n is any integer from 7 to 22.
2. The method for preparing the fluorine-containing organosilicon quaternary ammonium salt according to claim 1, characterized by comprising the following steps:
step 1: mixing a monomer and an acyl chlorination reagent in a reaction container, heating to 50-100 ℃ under the protection of inert gas, then dropwise adding dimethylformamide into the reaction container, and reacting for 2-4 hours under the condition of 50-100 ℃ to obtain an intermediate product a, wherein the structural formula of the monomer is CF3CF2CF2- (OCF 2CF2CF 2) n-O-CF2CF2-COOH, n is any integer from 7 to 22, the molar ratio of the monomer to the acyl chlorination reagent is (1-2): 1, and the weight of the dimethylformamide is 0.1-1% of the weight of the acyl chlorination reagent;
step 2: mixing dimethylethanolamine, an acid-binding agent and perfluorohexane, and cooling to 0-10 ℃ to obtain a reaction system, wherein the molar ratio of the dimethylethanolamine to the intermediate product a obtained in the step (1-1.2) to 1, the molar ratio of the acid-binding agent to the intermediate product a obtained in the step (1-3) to 1, and the volume ratio of the perfluorohexane to the dimethylethanolamine (25-50) to 1;
and step 3: slowly dropwise adding the intermediate product a obtained by the reaction in the step 1 into the reaction system obtained in the step 2, and then reacting for 1-2h at room temperature;
and 4, step 4: after the reaction in the step 3 is finished, adding methanol for extraction, and then purifying to obtain an intermediate product b;
and 5: heating gamma-chloropropyltrimethoxysiloxane, an intermediate product b, potassium iodide and a solvent to 50-150 ℃ under the protection of inert gas, reacting for 12-48h, and purifying after the reaction is finished to obtain the fluorine-containing organosilicon quaternary ammonium salt, wherein the molar ratio of the intermediate product b to the gamma-chloropropyltrimethoxysiloxane is 1 (1-1.5), the weight of potassium iodide is 0.5-1% of that of the gamma-chloropropyltrimethoxysiloxane, the solvent is a mixed solution of m-benzotrifluoride and dimethylformamide, the volume ratio of the m-benzotrifluoride to the dimethylformamide is 1 (0.5-1), and the volume of the solvent to the intermediate product b is 50.
3. The method for preparing fluorine-containing organosilicon quaternary ammonium salt according to claim 2, characterized in that: the acyl chlorination reagent in the step 1 is oxalyl chloride or thionyl chloride.
4. The method for preparing the fluorine-containing organosilicon quaternary ammonium salt according to claim 2, characterized in that: and the acid-binding agent in the step 2 is triethylamine or diisopropylethylamine.
5. The method for preparing fluorine-containing organosilicon quaternary ammonium salt according to claim 2, characterized in that: the purification method in the step 4 and the purification method in the step 5 are decompression rotary evaporation of the solvent.
6. The use of the quaternary ammonium salt of fluorine-containing organosilicon according to claim 1 for preparing glass coatings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010950867.9A CN112047976B (en) | 2020-09-11 | 2020-09-11 | Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010950867.9A CN112047976B (en) | 2020-09-11 | 2020-09-11 | Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112047976A CN112047976A (en) | 2020-12-08 |
| CN112047976B true CN112047976B (en) | 2022-12-27 |
Family
ID=73610042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010950867.9A Active CN112047976B (en) | 2020-09-11 | 2020-09-11 | Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112047976B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112691607B (en) * | 2020-12-26 | 2022-05-03 | 张家港邦力材料科技有限公司 | Gemini type fluorine-containing surfactant and preparation method and application thereof |
| CN114479474B (en) * | 2022-01-26 | 2024-03-01 | 广州万乐实业有限公司 | Preparation method of antibacterial silicone rubber product and antibacterial silicone rubber product |
| CN114736551B (en) * | 2022-04-13 | 2022-10-14 | 深圳德诚达光电材料有限公司 | Fluorine-containing organic silicon coating agent with excellent adhesion performance and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798324A (en) * | 2010-03-11 | 2010-08-11 | 杭州奥坦斯布艺有限公司 | Method for preparing antibacterial agent achieving antibacterial effect on decorative textile fabric |
| CN103572594A (en) * | 2013-11-20 | 2014-02-12 | 苏州大学 | Antibacterial agent containing fluorinated alkyl quaternary ammonium salt, and preparation method and application of antibacterial agent |
| EP3312242A1 (en) * | 2016-10-24 | 2018-04-25 | 3M Innovative Properties Company | Protective coating composition with mixed functionalities |
| CN109651941A (en) * | 2018-12-13 | 2019-04-19 | 苏州东杏表面技术有限公司 | One kind is based on double open coats of organic-silicon-modified wear-resisting type and preparation method thereof |
| CN107987722B (en) * | 2017-11-30 | 2019-11-05 | 深圳南玻应用技术有限公司 | Organosilicon bactericidal liquid, organosilicon fungicide, antibiotic glass, preparation method and application |
| CN110627828A (en) * | 2019-09-29 | 2019-12-31 | 清远市宏图助剂有限公司 | Organosilicon quaternary ammonium salt for improving antibacterial performance and preparation method and application thereof |
| CN111138652A (en) * | 2018-05-16 | 2020-05-12 | 广州优尔材料科技有限公司 | Perfluoropolyether group-containing silane compound, method for producing same, surface treatment agent, and article |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130264276A1 (en) * | 2010-12-21 | 2013-10-10 | 3M Innovative Properties Company | Filter Media Treated with Cationic Fluorinated Ether Silane Compositions |
-
2020
- 2020-09-11 CN CN202010950867.9A patent/CN112047976B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798324A (en) * | 2010-03-11 | 2010-08-11 | 杭州奥坦斯布艺有限公司 | Method for preparing antibacterial agent achieving antibacterial effect on decorative textile fabric |
| CN103572594A (en) * | 2013-11-20 | 2014-02-12 | 苏州大学 | Antibacterial agent containing fluorinated alkyl quaternary ammonium salt, and preparation method and application of antibacterial agent |
| EP3312242A1 (en) * | 2016-10-24 | 2018-04-25 | 3M Innovative Properties Company | Protective coating composition with mixed functionalities |
| CN107987722B (en) * | 2017-11-30 | 2019-11-05 | 深圳南玻应用技术有限公司 | Organosilicon bactericidal liquid, organosilicon fungicide, antibiotic glass, preparation method and application |
| CN111138652A (en) * | 2018-05-16 | 2020-05-12 | 广州优尔材料科技有限公司 | Perfluoropolyether group-containing silane compound, method for producing same, surface treatment agent, and article |
| CN109651941A (en) * | 2018-12-13 | 2019-04-19 | 苏州东杏表面技术有限公司 | One kind is based on double open coats of organic-silicon-modified wear-resisting type and preparation method thereof |
| CN110627828A (en) * | 2019-09-29 | 2019-12-31 | 清远市宏图助剂有限公司 | Organosilicon quaternary ammonium salt for improving antibacterial performance and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 单端Z型全氟聚醚硅氧烷的制备与性能;冯裕智等;《有机硅材料》;20160925;第30卷(第05期);第385-389页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112047976A (en) | 2020-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112047976B (en) | Fluorine-containing organosilicon quaternary ammonium salt and preparation method and application thereof | |
| JP7067562B2 (en) | Fluorine-containing ether compounds, compositions and articles | |
| US11926756B2 (en) | Fluorine-containing ether compound, fluorine-containing ether composition, coating liquid, article, method for producing article, and method for producing fluorine-containing compound | |
| KR102268922B1 (en) | Perfluoropolyether group-containing silane compound, manufacturing method thereof, surface treatment agent and article | |
| JP7031689B2 (en) | Fluorine-containing ether compositions, coating liquids and articles | |
| KR20160129829A (en) | Fluorine-containing ether composition, method for producing same, coating liquid, base material having surface treatment layter, and method for producing same | |
| WO2019039226A1 (en) | Fluorine-containing ether compound, fluorine-containing ether composition, coating solution, article, and production method thereof | |
| WO2018168497A1 (en) | Fluorinated ether composition, coating liquid, and article | |
| JP7180665B2 (en) | Fluorine-containing ether compound, fluorine-containing ether composition, coating liquid, article, and method for producing the same | |
| JP6690675B2 (en) | Compound, composition, surface treatment agent, article and method for producing compound | |
| US20200165273A1 (en) | Fluorinated ether compound, fluorinated ether composition, coating liquid, article and its production method | |
| WO2019208503A1 (en) | Fluorine-containing ether compound, composition containing same, coating solution, and product | |
| US20210269592A1 (en) | Fluorinated compound, fluorinated compound-containing composition, coating liquid, article, and method of producing the same | |
| JP4016428B2 (en) | Fluorine-containing polymer and its production and use | |
| JP6993894B2 (en) | Composition | |
| JP3758247B2 (en) | Antifouling substrate | |
| WO2018203491A2 (en) | Manufacturing method for fluorine-containing ether compound, and fluorine-containing ether compound | |
| WO2020241750A1 (en) | Base material with water repellent oil repellent layer | |
| JPWO2019035288A1 (en) | Method for producing fluorine-containing ether compound and method for producing article | |
| JP2022036343A (en) | Fluorine-containing ether compound and article | |
| JP5731038B1 (en) | Fluorine-containing silane compound | |
| JP6741170B2 (en) | Method for producing fluorine-containing ether compound, method for producing article | |
| WO2022059623A1 (en) | Composition, substrate with surface layer, method for producing substrate with surface layer, compound, and method for producing compound | |
| WO2021117687A1 (en) | Fluorine-containing ether compound, composition, and article having water- and oil-repellent layer | |
| WO2021235319A1 (en) | Fluorine-containing ether compound, fluorine-containing ether composition, coating solution, high oxygen solubility liquid, and article |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |