CN112778894B - Antibacterial and mildewproof polyurethane paint film based on triethanolamine and preparation method thereof - Google Patents
Antibacterial and mildewproof polyurethane paint film based on triethanolamine and preparation method thereof Download PDFInfo
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- CN112778894B CN112778894B CN202110013492.8A CN202110013492A CN112778894B CN 112778894 B CN112778894 B CN 112778894B CN 202110013492 A CN202110013492 A CN 202110013492A CN 112778894 B CN112778894 B CN 112778894B
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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
- C08G18/3278—Hydroxyamines containing at least three hydroxy groups
- C08G18/3281—Hydroxyamines containing at least three hydroxy groups containing three hydroxy groups
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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 triethanolamine, which comprises the following steps: dissolving triethanolamine and alkyl halide in ethanol, reacting for 12-72 h at 30-80 ℃, precipitating with a precipitator, vacuum drying to obtain quaternized triethanolamine, ultrasonically stirring the quaternized triethanolamine, 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate uniformly, and heating to 50-60 ℃ under the protection of inert gas; adding 1, 6-hexamethylene diisocyanate and butyl acetate into the solution, heating to 65-85 ℃, and reacting for 3-6 hours to obtain the antibacterial polyurethane coating; and (3) brushing the polyurethane on the surface of the base material, and naturally drying to form a film. The invention has good antibacterial and mildew resistance, better solvent resistance and mechanical property of the paint film, simple preparation method, convenient operation, safety and environmental protection, and is suitable for industrial production.
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 triethanolamine and a preparation method thereof.
Background
The existing commercially available antibacterial products generally adopt additive antibacterial coatings, most of the antibacterial additives are inorganic antibacterial agents and micromolecular organic antibacterial agents, and the coatings can kill bacteria contacting the surface of a paint film through the release of the antibacterial agents. However, such antibacterial products have disadvantages in that the antibacterial property of the paint is continuously lowered as the antibacterial agent is released, and the release of the antibacterial agent to the environment causes environmental pollution.
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 triethanolamine 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 triethanolamine comprises the following steps:
1) dissolving triethanolamine and alkyl halide in ethanol, mixing and stirring to obtain a uniform solution, reacting at 30-80 ℃ for 12-72 h, precipitating with a precipitator, and vacuum drying to obtain quaternized triethanolamine, wherein the molecular formula is as follows:
a ═ b ═ 0, c ═ 0, R1 is methyl to octadecyl, and X is a halogen element;
2) ultrasonically and uniformly stirring the quaternized triethanolamine obtained in the step 1) and 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate;
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 65-85 ℃, and reacting for 3-6 hours to obtain the antibacterial polyurethane coating;
5) brushing the polyurethane 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 triethanolamine to the alkyl halide in the step 1) is 1: 4-2: 1.
further, the precipitant in the step 1) is one or two of ethyl acetate, n-hexane and petroleum ether.
Furthermore, by mass, 52-62 parts of quaternized triethanolamine, 300-350 parts of 1, 6-hexamethylene diisocyanate, 180-220 parts of 2-ethyl-1, 3-hexanediol, 0-4 parts of dibutyltin dilaurate and 250-270 parts of butyl acetate.
Furthermore, by mass, 52-60 parts of quaternized triethanolamine, 310-330 parts of 1, 6-hexamethylene diisocyanate, 190-210 parts of 2-ethyl-1, 3-hexanediol, 0-2 parts of dibutyltin dilaurate and 250-260 parts of butyl acetate.
Further, by mass, 54-56 parts of quaternized triethanolamine, 320-330 parts of 1, 6-hexamethylene diisocyanate, 190-200 parts of 2-ethyl-1, 3-hexanediol, 0-1 part of dibutyltin dilaurate and 255-260 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 triethanolamine 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 hydroxyl of the polyhydroxy quaternary ammonium salt and isocyanate, and the structural reticular antibacterial polyurethane paint film is constructed through the crosslinking of the polyhydroxy quaternary ammonium salt and the isocyanate, so that a good antibacterial and antifungal effect is achieved, and meanwhile, the paint film has good stability. The principle of the invention for antibiosis and mould prevention is that the polyhydroxy quaternary ammonium salt of the cationic antimicrobial agent is positively charged, the bacterial cell membrane is negatively charged, when bacteria contact the surface of the paint film, the polyhydroxy quaternary ammonium salt can destroy the membrane potential balance of the bacteria, destroy the cell membrane and make the substances in the cell flow out, thereby achieving the purpose of killing the bacteria and the mould. The invention can be used on medical equipment, laboratories and wards which need high sterility, and can be used for coating indoor environment, thereby providing a long-term antibacterial environment for people.
The invention has the beneficial effects that: the coating is safe and environment-friendly, the paint film structure is stable, the effect is lasting, 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 antibacterial agent and the coating have the advantages of simple preparation method, more stable paint film structure, more lasting antibacterial effect and less environmental pollution.
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 4.5g triethanolamine and 12.5g bromohexane in 20g ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitating with ethyl acetate, and vacuum drying to obtain white solid powder of bromohexane quaternized triethanolamine (QTEA-C6).
Mixing 11.5g of quaternized triethanolamine, 39.5g of 2-ethyl-1, 3-hexanediol, 25.0g of butyl acetate and 0.1g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; adding 65.6g of 1, 6-hexamethylene diisocyanate and 25.0g of butyl acetate into the solution, heating to 75 ℃, and reacting for 5 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 328 parts of 1, 6-hexamethylene diisocyanate, 197 parts of 2-ethyl-1, 3-hexanediol, 0.4 part of dibutyltin dilaurate, 257 parts of butyl acetate and 655 parts of QTEA-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 5.95g of triethanolamine and 9.66g of octyl bromide in 15g of ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitating with ethyl acetate, and vacuum drying to obtain white solid powder of octyl bromide quaternized triethanolamine (QTEA-C8).
Mixing 12.5g of quaternized triethanolamine, 39.5g of 2-ethyl-1, 3-hexanediol, 25.0g of butyl acetate and 0.1g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; adding 65.6g of 1, 6-hexamethylene diisocyanate and 25.0g of butyl acetate into the solution, heating to 75 ℃, and reacting for 5 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 328 parts of 1, 6-hexamethylene diisocyanate, 197 parts of 2-ethyl-1, 3-hexanediol, 0.4 part of dibutyltin dilaurate, 257 parts of butyl acetate and 855 parts of QTEA-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 5.95g of triethanolamine and 12.46g 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; precipitating with ethyl acetate, and vacuum drying to obtain white solid powder of bromododecane quaternized triethanolamine (QTEA-C12).
Mixing 16.5g of quaternized triethanolamine, 39.5g of 2-ethyl-1, 3-hexanediol, 25.0g of butyl acetate and 0.1g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; adding 65.6g of 1, 6-hexamethylene diisocyanate and 25.0g of butyl acetate into the solution, heating to 75 ℃, and reacting for 5 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 328 parts of 1, 6-hexamethylene diisocyanate, 197 parts of 2-ethyl-1, 3-hexanediol, 0.4 part of dibutyltin dilaurate, 257 parts of butyl acetate and 5 parts of QTEA-C1055.
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 5.95g of triethanolamine and 15.27g of bromohexadecane in 15g of ethanol, stirring to obtain a uniform solution, heating the solution to 70 ℃, and carrying out condensation reflux reaction for 24 hours; precipitating with ethyl acetate, and vacuum drying to obtain white solid powder of bromohexadecane quaternized triethanolamine (QTEA-C16).
Mixing 18.5g of quaternized triethanolamine, 39.5g of 2-ethyl-1, 3-hexanediol, 25.0g of butyl acetate and 0.1g of dibutyltin dilaurate, and ultrasonically stirring uniformly; introducing nitrogen into the obtained solution, and heating to 60 ℃; adding 65.6g of 1, 6-hexamethylene diisocyanate and 25.0g of butyl acetate into the solution, heating to 75 ℃, and reacting for 5 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 328 parts of 1, 6-hexamethylene diisocyanate, 197 parts of 2-ethyl-1, 3-hexanediol, 0.4 part of dibutyltin dilaurate, 257 parts of butyl acetate and 1655 parts of QTEA-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 39.5g of 2-ethyl-1, 3-hexanediol, 25.0g of butyl acetate and 0.1g of dibutyltin dilaurate, and uniformly stirring by ultrasonic waves; introducing nitrogen into the obtained solution, and heating to 60 ℃; 65.6g of 1, 6-hexamethylene diisocyanate and 25.0g of butyl acetate are added into the solution, heated to 75 ℃ and reacted for 5 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 328 parts of 1, 6-hexamethylene diisocyanate, 197 parts of 2-ethyl-1, 3-hexanediol, 0.4 part of dibutyltin dilaurate and 257 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 without the addition of the antibacterial agent of example 5 and the antibacterial and antifungal polyurethane paint film of example 1 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 mildewproof polyurethane paint film of example 1 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, a is the antibacterial diagram of the polyurethane paint film without the antibacterial agent, and b and c are the antibacterial diagrams of the antibacterial and mildewproof polyurethane paint film with 27 parts and 55 parts of the addition amount of the polyhydroxy quaternary 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 of example 5, and FIG. 3(b) is an antifungal pattern of an antibacterial and antifungal polyurethane paint film of example 1 according to 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 triethanolamine is characterized by comprising the following steps:
1) dissolving triethanolamine and alkyl halide in ethanol, reacting for 12-72 h at 30-80 ℃, precipitating with a precipitator, and vacuum drying to obtain quaternized triethanolamine, wherein the molecular formula is as follows:
a＝0，b＝0,c＝0,R1is methyl-octadecyl, and X is halogen element;
2) ultrasonically and uniformly stirring the quaternized triethanolamine obtained in the step 1) and 2-ethyl-1, 3-hexanediol, butyl acetate and dibutyltin dilaurate;
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 65-85 ℃, and reacting for 3-6 hours to obtain the antibacterial polyurethane coating;
5) brushing the polyurethane obtained in the step 4) on the surface of a base material, and naturally drying to form a film.
2. The method for preparing the antibacterial and mildewproof polyurethane paint film based on the triethanolamine according to claim 1, wherein the molar ratio of the triethanolamine to the alkyl halide in the step 1) is 1: 4-2: 1.
3. the method for preparing the antibacterial and mildewproof polyurethane paint film based on the triethanolamine 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 preparation method of the antibacterial and mildewproof polyurethane paint film based on the triethanolamine as claimed in claim 1, wherein the quaternary ammonium triethanolamine is 52-62 parts, 1, 6-hexamethylene diisocyanate is 300-350 parts, 2-ethyl-1, 3-hexanediol is 180-220 parts, dibutyltin dilaurate is 0-4 parts, and butyl acetate is 250-270 parts by weight.
5. The preparation method of the antibacterial and mildewproof polyurethane paint film based on the triethanolamine as claimed in claim 1, wherein the quaternary ammonium triethanolamine comprises 52-60 parts by weight of 1, 6-hexamethylene diisocyanate 310-330 parts by weight of 2-ethyl-1, 3-hexanediol 190-210 parts by weight of dibutyl tin dilaurate and 250-260 parts by weight of butyl acetate.
6. The preparation method of the antibacterial and mildewproof polyurethane paint film based on the triethanolamine as claimed in claim 1, wherein the quaternary ammonium triethanolamine comprises 54 to 56 parts by weight of 1, 6-hexamethylene diisocyanate 320 to 330 parts by weight of 2-ethyl-1, 3-hexanediol 190 to 200 parts by weight of dibutyl tin dilaurate and 255 to 260 parts by weight of butyl acetate.
7. The method for preparing the antibacterial and mildewproof polyurethane paint film based on the triethanolamine as recited in 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 triethanolamine, which is prepared by the preparation method according to any one of claims 1 to 7.
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| US8299147B2 (en) * | 2009-12-11 | 2012-10-30 | Perfect Defense Technology Co., Ltd. | Chemical resistant ionomers and protective coverings |
| CN102604002B (en) * | 2012-01-10 | 2013-09-18 | 湖南工程学院 | Preparation method of multifunctional waterborne polyurethane and quaternary ammonium polymer |
| CN107141439A (en) * | 2017-06-05 | 2017-09-08 | 武汉理工大学 | A kind of antimicrobial form castor oil-base cation aqueous polyurethane emulsion and preparation method thereof |
| CN109694483B (en) * | 2017-10-23 | 2020-07-10 | 江南大学 | Antibacterial aqueous polyurethane emulsion and preparation method thereof |
| CN107936748A (en) * | 2017-12-15 | 2018-04-20 | 合众（佛山）化工有限公司 | A kind of acrylic acid aqueous coating of long-lasting antibacterial |
| CN108715664A (en) * | 2018-06-25 | 2018-10-30 | 合肥艾飞新材料有限公司 | A kind of preparation method of organic silicon hydrophobic film |
| CN110964205A (en) * | 2018-09-30 | 2020-04-07 | 天津大学 | Application of chitosan guanidine cation waterborne polyurethane in preparation of antibacterial coating |
| CN110964430A (en) * | 2018-09-30 | 2020-04-07 | 天津大学 | Chitosan guanidine cation waterborne polyurethane coating and preparation method thereof |
| CN109354706B (en) * | 2018-10-12 | 2021-03-26 | 淮海工学院 | Application of multifunctional polyurethane prepolymer in surface modification of medical catheter |
| CN111732926B (en) * | 2020-07-06 | 2022-04-05 | 河南功能高分子膜材料创新中心有限公司 | Preparation method of antibacterial sealant and antibacterial sealant product prepared by preparation method |
| CN111732874B (en) * | 2020-07-29 | 2022-09-27 | 北京化工大学 | Antibacterial and mildewproof paint film |
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| Title |
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| Enhancing the Fouling Resistance of Biocidal Urethane Coatings via Surface Chemistry Modulation;Peter N. Coneski等;《Langmuir》;20120405;第28卷(第17期);第7039-7048页 * |
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