CN112831266B - N-alkyl-glycol-amine-based antibacterial and mildewproof polyurethane paint film and preparation method thereof - Google Patents
N-alkyl-glycol-amine-based antibacterial and mildewproof polyurethane paint film and preparation method thereof Download PDFInfo
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- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- 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
Abstract
The invention discloses a preparation method of a novel antibacterial and mildewproof polyurethane paint film based on N-alkyl glycol amine, which comprises the following steps: dissolving N-alkylglycol amine and alkyl halide in ethanol, reacting for 12-72 h at 20-80 ℃, precipitating with a precipitator, drying in vacuum to obtain dihydroxyquaternary ammonium salt, mixing the dihydroxyquaternary ammonium salt with 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate, ultrasonically stirring uniformly, and heating the obtained solution to 50-60 ℃ under the protection of inert gas; adding 1, 6-hexamethylene diisocyanate and butyl acetate into the solution, heating to 60-80 ℃, and reacting for 5-7 hours to obtain the antibacterial polyurethane coating; the obtained polyurethane coating is brushed on the surface of a base material and naturally dried to form a film. The preparation method is simple, convenient to operate, safe and environment-friendly, is suitable for industrial production, and has good antibacterial and mildew resistant performance.
Description
Technical Field
The invention belongs to the technical field of antibacterial coatings, and relates to a novel antibacterial and mildewproof polyurethane paint film based on N-alkyldialkanolamine and a preparation method thereof.
Background
The antibacterial coating is a coating with an antibacterial function, and the antibacterial coating is mainly divided into two types, namely an additive coating and a structural coating. The additive type antibacterial coating is prepared by adding an antibacterial agent as an antibacterial component to the coating, and by releasing the antibacterial agent to the paint surface, when bacteria contact the surface of the paint, the bacteria are killed. The structural antibacterial coating achieves the antibacterial effect by modifying a coating film of the coating. The existing commercial antibacterial products generally adopt additive antibacterial coatings, but the antibacterial products have the defects that the antibacterial performance of the paint is continuously reduced along with the release of the antibacterial agent, and the environmental pollution is caused by the release of the antibacterial agent to the environment.
Disclosure of Invention
In view of the above, the first objective of the present invention is to provide a novel antibacterial and mildewproof polyurethane paint film based on N-alkyldialkanolamine and a preparation method thereof. The invention specifically provides the following technical scheme:
1. a preparation method of a novel antibacterial and mildewproof polyurethane paint film based on N-alkyl glycol amine comprises the following steps:
1) dissolving N-alkyl glycol amine and alkyl halide in ethanol, reacting for 12-72 h at 20-80 ℃, precipitating with a precipitator, and drying in vacuum to obtain the dihydroxyl quaternary ammonium salt, wherein the molecular formula is as follows:
m is 0 to 18, n is 0 to 18, R1 is methyl-octadecyl, R2 is methyl-octadecyl, and X is a halogen element;
2) mixing the dihydroxyl quaternary ammonium salt obtained in the step 1) with 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate, and ultrasonically stirring uniformly;
3) heating the solution obtained in the step 2) to 50-60 ℃ under the protection of inert gas;
4) adding 1, 6-hexamethylene diisocyanate and butyl acetate into the solution obtained in the step 3), heating to 60-80 ℃, and reacting for 5-7 hours to obtain an antibacterial polyurethane coating;
5) brushing the polyurethane coating obtained in the step 4) on the surface of a base material, and naturally drying to form a film.
Further, the molar ratio of the N-alkyl glycol amine and the alkyl halide in the step 1) is 1: 3-3: 1.
Further, the precipitant in the step 1) is one or two of ethyl acetate, n-hexane and petroleum ether.
Further, by mass, 45-55 parts of dihydroxyl quaternary ammonium salt, 250-350 parts of 1, 6-hexamethylene diisocyanate, 120-220 parts of 2-ethyl-1, 3-hexanediol, 0.1-2 parts of dibutyltin dilaurate and 140-240 parts of butyl acetate.
Further, by mass, 45-50 parts of dihydroxyl quaternary ammonium salt, 300-340 parts of 1, 6-hexamethylene diisocyanate, 150-200 parts of 2-ethyl-1, 3-hexanediol, 0.1-1 part of dibutyltin dilaurate and 180-220 parts of butyl acetate.
Further, by mass, 46-48 parts of dihydroxyl quaternary ammonium salt, 275-285 parts of 1, 6-hexamethylene diisocyanate, 165-175 parts of 2-ethyl-1, 3-hexanediol, 0.1-0.4 part of dibutyltin dilaurate and 200-210 parts of butyl acetate.
Further, the alkyl halide is one or more of bromohexane, bromooctane, 1-bromododecane and 1-bromohexadecane.
2. The novel antibacterial and mildewproof polyurethane paint film based on the N-alkyl dialkanolamine is prepared according to the preparation method.
The principle of the invention for constructing the structural antibacterial polyurethane paint film is that the antibacterial agent is combined into the molecular structure of the polyurethane paint film through the reaction of the hydroxyl of the dihydroxyl quaternary ammonium salt and isocyanate to construct the structural antibacterial polyurethane paint film, thereby achieving good antibacterial and antifungal effects. The principle of the invention for antibiosis and mould prevention is that the cationic antimicrobial dihydroxyl quaternary ammonium salt is positively charged, so that the whole surface is positively charged when a polyurethane paint film is formed; when bacteria contact the surface, negatively charged bacteria can be adsorbed to the paint surface, destroy the fine membrane potential, destroy the biological electrical balance of a cell system, and simultaneously cause cell protein denaturation, thereby destroying the cell structure and achieving the aim of inactivating bacterial mould bodies. The invention can be used for indoor decoration products with sterilization and mildew prevention functions in high-cleanness places such as hospitals, sterile laboratories and the like, and reduces infection and secondary infection caused by unclean environment; and the coating can also be used for home interior decoration and provides a long-term antibacterial protection function for the interior.
The invention has the beneficial effects that: the coating is safe, environment-friendly and durable in action, and the antibacterial and mildewproof active components do not seep out, so that the coating has good antibacterial and mildewproof performance and does not pollute the surrounding environment; the preparation method is simple and is suitable for industrial production. The bacterial mould for HG/T3950 standard detection can be effectively killed. According to the detection basis of HG/T3950, the antibacterial and mildewproof functions of the technology are as follows: the antibacterial property is more than or equal to 99.9 percent; the anti-mould performance is 0 grade or 1 grade; the coating has the advantages of simple preparation method, less environmental pollution and more durable antibacterial effect.
Drawings
In order to make the purpose, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings:
FIG. 1 is a surface potential diagram of a polyurethane paint film without an antibacterial agent and an antibacterial and mildewproof polyurethane paint film of the present invention;
FIG. 2 is an antibacterial map of a polyurethane paint film without an antibacterial agent added and an antibacterial and mildewproof polyurethane paint film of the present invention;
fig. 3 is a diagram showing the mildew resistance of the polyurethane paint film without the addition of the antibacterial agent and the antibacterial and mildewproof polyurethane paint film of the present invention.
Detailed Description
Preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings.
Example 1
Dissolving 5.95g 5.95g N-methyldiethanolamine and 10.3g bromohexane in 15g ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitation with ethyl acetate and drying in vacuo gave a white solid, bromohexane quaternized N-methyldiethanolamine (QMDEA-C6).
Mixing 7.37g of quaternized N-methyldiethanolamine, 26.32g of 2-ethyl-1, 3-hexanediol, 15.57g of butyl acetate and 0.05g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; 43.73g of 1, 6-hexamethylene diisocyanate and 15.57g of butyl acetate are added into the solution, heated to 70 ℃, and reacted for 6 hours to obtain the antibacterial polyurethane coating. And (3) brushing the coating on the surface of the metal substrate by using a brush, and airing to obtain the antibacterial and mildewproof polyurethane paint film.
The raw material formula comprises 284 parts of 1, 6-hexamethylene diisocyanate, 171 parts of 2-ethyl-1, 3-hexanediol, 0.3 part of dibutyltin dilaurate, 202 parts of butyl acetate and 648 parts of QMDEA-C.
Applied to tinplate, the performance parameters are as follows: the antibacterial property is more than or equal to 99.9 percent; the anti-mould performance is grade I.
Example 2
Dissolving 5.25g 5.25g N-methyldiethanolamine and 8.11g octyl bromide in 15g ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitation with ethyl acetate and drying in vacuo gave white solid octyl bromide quaternized N-methyldiethanolamine (QMDEA-C8).
Mixing 7.37g of quaternized N-methyldiethanolamine, 26.32g of 2-ethyl-1, 3-hexanediol, 15.57g of butyl acetate and 0.05g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; 43.73g of 1, 6-hexamethylene diisocyanate and 15.57g of butyl acetate are added into the solution, heated to 70 ℃, and reacted for 6 hours to obtain the antibacterial polyurethane coating. And (3) brushing the coating on the surface of the metal substrate by using a brush, and airing to obtain the antibacterial and mildewproof polyurethane paint film.
The raw material formula comprises 284 parts of 1, 6-hexamethylene diisocyanate, 171 parts of 2-ethyl-1, 3-hexanediol, 0.3 part of dibutyltin dilaurate, 202 parts of butyl acetate and 848 parts of QMDEA-C.
Applied to tinplate, the performance parameters are as follows: the antibacterial property is more than or equal to 99.9 percent; the anti-mould performance is grade I.
Example 3
Dissolving 8.88g of 8.88g N-methyldiethanolamine and 15.56g of bromododecane in 15g of ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitation with ethyl acetate and drying in vacuo gave bromododecane quaternized N-methyldiethanolamine (QMDEA-C12) as a white solid powder.
Mixing 7.37g of quaternized N-methyldiethanolamine, 26.32g of 2-ethyl-1, 3-hexanediol, 15.57g of butyl acetate and 0.05g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; 43.73g of 1, 6-hexamethylene diisocyanate and 15.57g of butyl acetate are added into the solution, heated to 70 ℃, and reacted for 6 hours to obtain the antibacterial polyurethane coating. And brushing the film on the surface of a metal substrate by using a brush, and airing to obtain the antibacterial and mildewproof polyurethane paint film.
The raw material formula comprises 284 parts of 1, 6-hexamethylene diisocyanate, 171 parts of 2-ethyl-1, 3-hexanediol, 0.3 part of dibutyltin dilaurate, 202 parts of butyl acetate and 1248 parts of QMDEA-C.
Applied to tinplate, the performance parameters are as follows: the antibacterial property is more than or equal to 99.9 percent; the anti-mould performance is grade I.
Example 4
Dissolving 15g N-methyldiethanolamine and 10.62g bromohexadecane in 15g ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitation with ethyl acetate and vacuum drying gave bromohexadecane quaternized N-methyldiethanolamine (QMDEA-C16) as a white solid powder.
Mixing 7.37g of quaternized N-methyldiethanolamine, 26.32g of 2-ethyl-1, 3-hexanediol, 15.57g of butyl acetate and 0.05g of dibutyltin dilaurate, and stirring uniformly by ultrasonic waves; introducing nitrogen into the obtained solution, and heating to 60 ℃; 43.73g of 1, 6-hexamethylene diisocyanate and 15.57g of butyl acetate are added into the solution, heated to 70 ℃, and reacted for 6 hours to obtain the antibacterial polyurethane coating. And (3) brushing the coating on the surface of the metal substrate by using a brush, and airing to obtain the antibacterial and mildewproof polyurethane paint film.
The raw material formula comprises 284 parts of 1, 6-hexamethylene diisocyanate, 171 parts of 2-ethyl-1, 3-hexanediol, 0.3 part of dibutyltin dilaurate, 202 parts of butyl acetate and 1648 parts of QMDEA-C.
Applied to tinplate, the performance parameters are as follows: the antibacterial property is more than or equal to 99.9 percent; the anti-mould performance is grade I.
Example 5
Mixing 26.32g of 2-ethyl-1, 3-hexanediol, 15.57g of butyl acetate and 0.05g of dibutyltin dilaurate, and uniformly stirring by ultrasonic waves; introducing nitrogen into the obtained solution, and heating to 60 ℃; 43.73g of 1, 6-hexamethylene diisocyanate and 15.57g of butyl acetate are added into the solution, heated to 70 ℃, and reacted for 6 hours to obtain the polyurethane coating without the antibacterial agent. And brushing the metal base material on the surface of the metal base material by using a brush, and airing to obtain the polyurethane paint film without the antibacterial agent.
The raw material formula comprises 284 parts of 1, 6-hexamethylene diisocyanate, 171 parts of 2-ethyl-1, 3-hexanediol, 0.3 part of dibutyltin dilaurate and 202 parts of butyl acetate.
Applied to tinplate, the performance parameters are as follows: it is not antibacterial and antifungal.
FIG. 1 is a surface potential diagram of the polyurethane paint film obtained in example 5 without the addition of the antibacterial agent and the antibacterial and antifungal polyurethane paint film obtained in example 3 according to the present invention; as can be seen from FIG. 1, the surface potential of the antibacterial and mildewproof polyurethane paint film of the invention is greatly improved relative to the surface potential of the polyurethane paint film without the antibacterial agent, and the positive surface charge is helpful for killing bacteria and mildew.
FIG. 2 is an antibacterial pattern of the polyurethane paint film of example 5 without the addition of an antibacterial agent and the antibacterial and antifungal polyurethane paint film of example 3 according to the present invention; in fig. 2, the control group is the colony growth conditions of staphylococcus aureus and escherichia coli under the optimal growth conditions, 1 is the antibacterial diagram of the polyurethane paint film without the antibacterial agent, and 2 and 3 are the antibacterial diagrams of the antibacterial and mildew-proof polyurethane paint film with 24 parts and 48 parts of the addition amount of the dihydroxyquaternary ammonium salt of the antibacterial agent respectively. As can be seen from FIG. 2, the antibacterial effect of the antibacterial and mildewproof polyurethane paint film reaches 99.9%.
FIG. 3(a) is a polyurethane paint film without an antibacterial agent in example 5, and FIG. 3(b) is a mold-resistant diagram of an antibacterial and mildewproof polyurethane paint film in example 3 of the present invention; as can be seen from FIG. 3, the antibacterial and mildewproof polyurethane paint film has good mildewproof performance, and reaches the I level.
From this it can be concluded that: compared with the polyurethane paint film without the antibacterial agent, the antibacterial and mildewproof polyurethane paint film has good antibacterial and mildewproof effects.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (8)
1. A preparation method of an antibacterial and mildewproof polyurethane paint film based on N-alkyl glycol amine is characterized by comprising the following steps:
1) dissolving N-alkyl glycol amine and alkyl halide in ethanol, reacting for 12-72 h at 20-80 ℃, precipitating with a precipitator, and drying in vacuum to obtain the dihydroxyl quaternary ammonium salt, wherein the molecular formula is as follows:
2) mixing the dihydroxyl quaternary ammonium salt obtained in the step 1) with 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate, and ultrasonically stirring uniformly;
3) heating the solution obtained in the step 2) to 50-60 ℃ under the protection of inert gas;
4) adding 1, 6-hexamethylene diisocyanate and butyl acetate into the solution obtained in the step 3), heating to 60-80 ℃, and reacting for 5-7 hours to obtain an antibacterial polyurethane coating;
5) brushing the polyurethane coating obtained in the step 4) on the surface of a base material, and naturally drying to form a film.
2. The preparation method of the N-alkyl dialkanol amine-based antibacterial and mildewproof polyurethane paint film as claimed in claim 1, wherein the molar ratio of the N-alkyl dialkanol amine and the alkyl halide in the step 1) is 1: 3-3: 1.
3. The method for preparing the N-alkyldialkanolamine-based antibacterial and mildewproof polyurethane paint film according to claim 1, wherein the precipitant in the step 1) is one or two of ethyl acetate, N-hexane and petroleum ether.
4. The method for preparing an N-alkyldialkanolamine-based antibacterial and mildewproof polyurethane paint film according to claim 1, wherein the weight parts of the dihydroxyquaternary ammonium salt are 45 to 55 parts, the weight parts of 1, 6-hexamethylene diisocyanate are 250 to 350 parts, the weight parts of 2-ethyl-1, 3-hexanediol are 120 to 220 parts, the weight parts of dibutyltin dilaurate are 0.1 to 2 parts, and the weight parts of butyl acetate are 140 to 240 parts.
5. The method for preparing an N-alkyldialkanolamine-based antibacterial and mildewproof polyurethane paint film according to claim 1, wherein the weight parts of the dihydroxyquaternary ammonium salt are 45 to 50 parts, the weight parts of 1, 6-hexamethylene diisocyanate are 300 to 340 parts, the weight parts of 2-ethyl-1, 3-hexanediol are 150 to 200 parts, the weight parts of dibutyltin dilaurate are 0.1 to 1 part, and the weight parts of butyl acetate are 180 to 220 parts.
6. The method for preparing the N-alkyldiol amine-based antibacterial and mildewproof polyurethane paint film according to claim 1, wherein the weight parts of the dihydroxyquaternary ammonium salt are 46-48 parts, the weight parts of 1, 6-hexamethylene diisocyanate are 275-285 parts, the weight parts of 2-ethyl-1, 3-hexanediol are 165-175 parts, the weight parts of dibutyltin dilaurate are 0.1-0.4 part, and the weight parts of butyl acetate are 200-210 parts.
7. The method for preparing an N-alkyldialkanolamine based antibacterial and mildewproof polyurethane paint film according to claim 1, wherein the alkyl halide is one or more of bromohexane, bromooctane, 1-bromododecane and 1-bromohexadecane.
8. An antibacterial and mildewproof polyurethane paint film based on N-alkyl dialkanolamine prepared by the preparation method according to any one of the claims 1 to 7.
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| WO2018102152A1 (en) * | 2016-11-30 | 2018-06-07 | Croda International Plc | An aqueous binder system, a coating composition & a coating |
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| CN111732874A (en) * | 2020-07-29 | 2020-10-02 | 北京化工大学 | Novel antibacterial and mildewproof paint film and preparation method thereof |
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| CN103304762A (en) * | 2013-07-01 | 2013-09-18 | 浙江大学 | Method for preparing organosilicon quaternary ammonium salt modified polyurethane resin for marine antifouling coating |
| CN105199070A (en) * | 2015-10-19 | 2015-12-30 | 浙江大学 | Amphipathic polyurethane with anti-bacterial and anti-protein function as well as preparation method and application of amphipathic polyurethane |
| CN108070067A (en) * | 2016-11-15 | 2018-05-25 | 中国科学院青岛生物能源与过程研究所 | A kind of preparation method of Cross-linkable coating antibacterial polyurethane |
| WO2018102152A1 (en) * | 2016-11-30 | 2018-06-07 | Croda International Plc | An aqueous binder system, a coating composition & a coating |
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| CN111732874A (en) * | 2020-07-29 | 2020-10-02 | 北京化工大学 | Novel antibacterial and mildewproof paint film and preparation method thereof |
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