CN113444417A - Antibacterial antistatic water-based acrylic coating and preparation method thereof - Google Patents
Antibacterial antistatic water-based acrylic coating and preparation method thereof Download PDFInfo
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- CN113444417A CN113444417A CN202110622244.3A CN202110622244A CN113444417A CN 113444417 A CN113444417 A CN 113444417A CN 202110622244 A CN202110622244 A CN 202110622244A CN 113444417 A CN113444417 A CN 113444417A
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- acrylic acid
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- methyl methacrylate
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000000576 coating method Methods 0.000 title claims abstract description 55
- 239000011248 coating agent Substances 0.000 title claims abstract description 46
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 27
- JADNEWQXDKBXRI-UHFFFAOYSA-M ethyl-dimethyl-(2-prop-2-enoyloxyethyl)azanium;bromide Chemical compound [Br-].CC[N+](C)(C)CCOC(=O)C=C JADNEWQXDKBXRI-UHFFFAOYSA-M 0.000 claims abstract description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 18
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 18
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000008367 deionised water Substances 0.000 claims abstract description 14
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 14
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000012874 anionic emulsifier Substances 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 8
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 4
- 229960002887 deanol Drugs 0.000 claims description 4
- 239000012972 dimethylethanolamine Substances 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 fatty alcohol ether sulfates Chemical class 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 230000001276 controlling effect Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000011256 inorganic filler Substances 0.000 abstract description 6
- 229910003475 inorganic filler Inorganic materials 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000523 sample Substances 0.000 description 10
- 239000003973 paint Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
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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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
-
- 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
- C09D5/24—Electrically-conducting paints
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plant Pathology (AREA)
- Paints Or Removers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an antibacterial antistatic water-based acrylic coating and a preparation method thereof, wherein the coating comprises the following raw material components: 8-10 parts of acrylic acid, 80-85 parts of methyl methacrylate, 100 parts of butyl acrylate, 4-6 parts of diacetone acrylamide, 8-10 parts of adipic dihydrazide, 20-25 parts of acryloyloxyethyl dimethyl ethyl ammonium bromide, 20-25 parts of an anionic emulsifier, a pH regulator and deionized water. The water-based acrylic coating can simultaneously obtain excellent antibacterial and antistatic effects under the condition of not adding inorganic filler.
Description
Technical Field
The invention relates to the technical field of acrylic coatings, in particular to an antibacterial and antistatic acrylic coating.
Background
The distribution of microorganisms in the environment is wide, the damage to various materials is ubiquitous, and various infectious diseases caused by the action of microorganisms cause great harm to human beings. After the coating is polluted by microorganisms, once the growth conditions are proper, the microorganisms can grow and propagate in the coating in a large quantity, so that the coating system shows an unstable sign, which is mainly shown in that the viscosity of the coating system is reduced, pigments are precipitated, gas is generated, the pH value is changed, and the like. Once a coating formed after the coating is coated by the paint is corroded by microorganisms, bacterial plaque is easily formed on the surface of the coating, so that the coating loses the adhesive capacity, the coating can seriously fall off, the protective function and the attractiveness and tidiness of the coating are directly influenced, and the practical value of the paint is reduced. In the world, a considerable amount of coatings lose practical value due to the putrefaction of microorganisms, causing huge economic loss, and the research on antibacterial coatings has great environmental protection and economic benefits, so the research and application of antibacterial coatings are greatly concerned.
In addition, with the development of high and new technologies and the wide application of polymer materials, the electrostatic problem is more and more regarded in various aspects. Most of high polymer materials are excellent electric insulating materials, and have high surface resistivity and volume resistivity, so that a large amount of static charges are easily accumulated, the production process is hindered and the product quality is reduced if the static charges are light, and accidents such as fire and explosion are caused if the static charges are heavy. The antistatic coating can eliminate the harm of static electricity, and is widely applied due to simple production equipment, convenient construction and low cost. An antistatic coating is a functional coating which has been rapidly developed in recent years, imparts conductivity to an object, and is widely used in the fields of electronics, construction, aviation, military, and the like.
In the prior art, a few researches are conducted on coatings with antibacterial and antistatic effects, and in a few technical means, the antibacterial and antistatic acrylic coatings are obtained by mainly adding a plurality of inorganic fillers with antibacterial and antistatic effects respectively, but on one hand, the fillers are slowly released or separated out from a coating base material, the antibacterial property and the antistatic property of the fillers are gradually weakened along with the lapse of the using time, and simultaneously separated heavy metals such as silver and copper ions cause certain pollution to the environment, on the other hand, the compatibility and other problems often exist between the inorganic fillers and matrix resin, and effect influence exists among the inorganic fillers, so that the antibacterial or antistatic property of the obtained coatings cannot meet the ideal requirements at the same time.
Disclosure of Invention
The invention aims to provide an environment-friendly multifunctional water-based acrylic coating with antibacterial and antistatic functions and a preparation method thereof.
The invention firstly discloses the following technical scheme:
an antibacterial antistatic water-based acrylic coating comprises the following raw material components: 8-10 parts of acrylic acid, 80-85 parts of methyl methacrylate, 100 parts of butyl acrylate, 4-6 parts of diacetone acrylamide, 8-10 parts of adipic dihydrazide, 20-25 parts of acryloyloxyethyl dimethyl ethyl ammonium bromide, 20-25 parts of an anionic emulsifier, a pH regulator and deionized water.
According to some preferred embodiments of the present invention, the acrylic coating comprises the following raw material components: 10 parts by mass of acrylic acid, 80 parts by mass of methyl methacrylate, 100 parts by mass of butyl acrylate, 5 parts by mass of diacetone acrylamide, 9 parts by mass of adipic dihydrazide, 20 parts by mass of acryloyloxyethyl dimethyl ethyl ammonium bromide, 20 parts by mass of an anionic emulsifier, 70 parts by mass of deionized water and a pH regulator.
According to some preferred embodiments of the invention, the anionic emulsifier is selected from fatty alcohol ether sulfates.
According to some preferred embodiments of the invention, the pH adjusting agent is selected from ammonia.
The present invention further provides a method for preparing the acrylic coating, which comprises:
mixing a first part of acrylic acid, methyl methacrylate, butyl acrylate, diacetone acrylamide and the emulsifier in the raw material components, adding the deionized water and the pH regulator, dissolving uniformly to obtain a pre-emulsion, and carrying out polymerization reaction for 1-3 hours at 80-90 ℃ to obtain a prepolymer;
adding a second part of acrylic acid, methyl methacrylate, butyl acrylate and diacetone acrylamide, the adipic acid dihydrazide, the acryloyloxyethyl dimethyl ethyl ammonium bromide and the pH regulator into the obtained prepolymer, continuously reacting at 80-90 ℃ for 1-3 hours, and discharging to obtain the antibacterial antistatic waterborne acrylic coating.
According to some preferred embodiments of the present invention, the mass ratio of the first portion of acrylic acid, methyl methacrylate, butyl acrylate, diacetone acrylamide to the second portion of acrylic acid, methyl methacrylate, butyl acrylate, diacetone acrylamide is 1-2: 1.
According to some preferred embodiments of the present invention, the pH adjusting agent adjusts the pH of the mixture system in which it is present to a range of 8 to 10.
According to some preferred embodiments of the present invention, the deionized water is added in an amount such that the oil-water ratio of the deionized water to the system is 1: (0.65-0.75).
According to some preferred embodiments of the present invention, the acryloyloxyethyldimethylethylammonium bromide is prepared by a preparation method comprising the following processes:
refluxing thionyl chloride, the first part of polymerization inhibitor and acrylic acid at 30-50 ℃ for 1-10h to obtain acryloyl chloride;
adding the acryloyl chloride into a mixture of the dimethylethanolamine, the organic solvent and the second part of polymerization inhibitor, controlling the reaction temperature to be 4-6 ℃, and reacting for 1-7h at a heat preservation degree to obtain dimethylaminoethyl acrylate;
and uniformly mixing the obtained dimethylaminoethyl acrylate and bromoethane, and reacting for 1-5h at the temperature of 50-80 ℃ to obtain the acryloyloxyethyl dimethyl ethyl ammonium bromide.
According to some preferred embodiments of the invention, the organic solvent is selected from diethyl ether.
According to some preferred embodiments of the invention, the polymerization inhibitor is selected from hydroquinone.
The invention has the following beneficial effects:
(1) according to the preparation method, the quaternary ammonium salt is introduced into the polyacrylic acid skeleton through the acrylic acid modified quaternary ammonium salt, so that the coating can obtain antibacterial and antistatic capabilities simultaneously on the premise of not adding inorganic filler, and the antibacterial and antistatic capabilities are lasting and efficient;
(2) compared with the traditional inorganic filler modified antibacterial antistatic acrylic coating, the coating disclosed by the invention does not contain heavy metal ions, is green and environment-friendly, and has better antibacterial capability and higher durability;
(3) the coating disclosed by the invention belongs to a water-based acrylic coating, is low in organic matter volatilization, is more green and healthy than other types of coatings, and can be used for indoor decoration and the like;
(4) the preparation method is simple, has less working procedures, has non-strict reaction conditions, is easy for industrial production and has good prospect.
Detailed Description
The present invention is described in detail with reference to the following examples, but it should be understood that the examples are only for illustrative purposes and are not intended to limit the scope of the present invention. All reasonable variations and combinations that fall within the spirit of the invention are intended to be within the scope of the invention.
According to the technical scheme of the invention, some specific preparation method embodiments comprise the following steps:
(1) adding thionyl chloride into a three-neck flask provided with a condenser pipe, a dropping funnel and a thermometer, adding hydroquinone serving as a polymerization inhibitor, adding refined acrylic acid into the dropping funnel, stirring and dropping the acrylic acid, heating to 30-50 ℃ after dropping, carrying out reflux reaction for 1-10h, cooling to room temperature, and carrying out reduced pressure distillation on a product to obtain acryloyl chloride;
(2) adding dimethylethanolamine, solvent ether and polymerization inhibitor hydroquinone into a three-neck flask in sequence, controlling the reaction temperature to be 4-6 ℃, slowly dropwise adding acryloyl chloride under continuous stirring, keeping the temperature to react for 1-7h after dropwise adding is finished, and obtaining dimethylaminoethyl acrylate after the reaction is finished;
(3) adding dimethylaminoethyl acrylate and bromoethane serving as a solvent into a three-neck flask, stirring and mixing uniformly, slowly heating to 50-80 ℃, carrying out heat preservation reaction for 1-5h, carrying out reduced pressure distillation to remove micromolecule low-boiling-point substances, fully washing a product with diethyl ether, and drying to obtain acryloyloxyethyl dimethyl ethyl ammonium bromide;
(4) taking part of acrylic acid, methyl methacrylate, butyl acrylate and diacetone acrylamide as reaction monomers, taking Disponil FES 993 as an initiator and an emulsifier, mixing the two, and adding the mixture to ensure that the oil-water ratio of the system is 1: (0.65-0.75) stirring and dissolving the deionized water uniformly, adding ammonia water to adjust the pH value to 8-9 to obtain a pre-emulsion, and carrying out polymerization reaction for 1-3 hours at the temperature of 80-90 ℃ to obtain a prepolymer;
(5) and (3) adding the residual acrylic acid, methyl methacrylate, butyl acrylate, diacetone acrylamide, adipic dihydrazide and the acryloyloxyethyl dimethyl ethyl ammonium bromide obtained in the step (3) into the obtained prepolymer, adding ammonia water to adjust the pH value to 8-10, continuously reacting at 80-90 ℃ for 1-3 hours, and discharging to obtain the antibacterial antistatic waterborne acrylic coating.
Wherein the paint comprises the following raw materials in parts by weight: 8-10 parts of acrylic acid, 80-85 parts of methyl methacrylate, 100 parts of butyl acrylate, 4-6 parts of diacetone acrylamide, 8-10 parts of adipic dihydrazide, a proper amount of ammonia water (PH 10), 20-25 parts of acryloyloxyethyl dimethyl ethyl ammonium bromide, 99320-25 parts of Disponil FES and a proper amount of deionized water.
The coatings obtained in the examples were subjected to an antibacterial test by the following procedure:
1. preservation and activation of strains
Inoculating the strain on a culture medium plane, culturing at 37 deg.C for 24 hr, and preserving in refrigerator as slant preserving strain. The slant culture was transferred to a plate medium and cultured at 37 ℃ for 24 hours.
2. Preparation of the bacterial suspension
A small amount of bacteria was taken from the transfer plate medium with an inoculating loop, added to 50ml of Phosphate Buffered Saline (PBS), and sequentially made 10-foldThe dilution was increased incrementally. Counting viable bacteria according to the method in GB \ T4789.2-2008, and selecting the concentration of the bacteria liquid as (5.0-50.0) x 105cfu/ml。
3. Preparation of antibacterial sample plate
And dissolving the antibacterial high polymer in butyl acetate, and coating the solution on a tinplate to obtain the antibacterial sample plate. The size of the experimental sample plate is 50mm multiplied by 50mm, and the sample plate which is coated well needs to be sterilized for 30min under an ultraviolet lamp before the experiment.
4. Experiment of antibacterial Properties
0.2ml of the experimental bacterial liquid is respectively dripped on the blank control sample plate without the antibacterial component and the antibacterial sample plate. And clamping sterilized films by using sterile forceps, respectively covering the samples, paving to ensure that the bacteria liquid is uniformly contacted with the samples, placing in a sterilized plate, and culturing for 24 hours in a constant-temperature incubator with the relative humidity of more than 90 percent and the temperature of 37 ℃. Taking out the sample plate and the cover film after 24h of culture, respectively putting the sample plate and the cover film into sterilized beakers, respectively adding 50ml of PBS solution, clamping the film by sterilized tweezers to repeatedly wash the sample plate, fully shaking up the sample plate to obtain bacterial suspension with the dilution degree of 100, sequentially diluting the bacterial suspension by 10 times by using the PBS solution to obtain a series of bacterial suspensions, and measuring the viable count according to the method specified in GB \ T4789.2-2008.
5. Calculation of antibacterial ratio
The actual colony values after the blank control test and the antibacterial paint sample are cultured for 24 hours are respectively recorded as A and B (cfu/ml), and the antibacterial rate of the antibacterial paint is calculated according to the following formula:
the antibacterial rate R (%) < 100 × (a-B)/a.
The following examples were conducted in accordance with the method specified in GB/T1696-1997 (resistivity measurement method for petroleum tank conductive electrostatic coating), in which a copper plate was used in place of the polyester film in GB/T1696-1997.
Example 1
Acryloyloxyethyldimethylethylammonium bromide was prepared by the following procedure:
(1) adding thionyl chloride into a three-neck flask provided with a condenser pipe, a dropping funnel and a thermometer, adding hydroquinone serving as a polymerization inhibitor of acrylic acid, adding refined acrylic acid into the dropping funnel, stirring and dropping the acrylic acid, heating to 40 ℃ after dropping, carrying out reflux reaction for 5 hours, cooling to room temperature, and carrying out reduced pressure distillation on a product to obtain acryloyl chloride;
(2) adding 133 parts of dimethylethanolamine, 150 parts of solvent ether and polymerization inhibitor hydroquinone of acrylic acid into a three-neck flask in sequence, controlling the reaction temperature to be 5 ℃, slowly dripping 90 parts of acryloyl chloride under continuous stirring, keeping the temperature for reaction for 4 hours after dripping is finished, and obtaining dimethylaminoethyl acrylate after the reaction is finished;
(3) adding 60 parts of the obtained dimethylaminoethyl acrylate and 30 parts of bromoethane into a three-neck flask, stirring and mixing uniformly, slowly heating to 70 ℃, carrying out heat preservation reaction for 3 hours, carrying out reduced pressure distillation to remove micromolecular low-boiling-point substances, fully washing a product by diethyl ether, and drying to obtain the acryloyloxyethyl dimethyl ethyl ammonium bromide.
Example 2
The antibacterial antistatic water-based acrylic coating is prepared by the following steps:
(1) taking 5 parts of acrylic acid, 40 parts of methyl methacrylate, 60 parts of butyl acrylate and 2.5 parts of diacetone acrylamide as reaction monomers, taking 99310 parts of Disponil FES as an initiator and an emulsifier, mixing the two, adding 70 parts of deionized water, stirring and dissolving uniformly to obtain a pre-emulsion, adjusting the pH to 8.5 by ammonia water, and carrying out polymerization reaction for two hours at 85 ℃;
(2) and then adding 5 parts of the rest acrylic acid, 40 parts of methyl methacrylate, 40 parts of butyl acrylate, 2.5 parts of diacetone acrylamide, 9 parts of adipic acid dihydrazide and 20 parts of acryloyloxyethyl dimethyl ethyl ammonium bromide obtained in example 1, adding ammonia water to adjust the pH value to 8.5, continuously reacting for 2 hours, and discharging to obtain the antibacterial antistatic waterborne acrylic coating.
According to antibacterial property tests, the antibacterial and antioxidant water-based acrylic coating prepared by the embodiment has removal rates of 74.8%, 64.3%, 84.5% and 78.4% for aspergillus niger, staphylococcus aureus, escherichia coli (C83) and pseudomonas aeruginosa respectively; the antistatic property test shows that the surface resistivity of the coating film reaches 8.2 multiplied by 105Ω。
Example 3
An antibacterial and antistatic aqueous acrylic paint was prepared by the same procedure as in example 2 except that the amount of acryloyloxyethyldimethylethylammonium bromide used therein was 30 parts.
The antibacterial property test of the obtained acrylic paint shows that: the antibacterial and antioxidant water-based acrylic coating prepared by the embodiment has removal rates of 81.3%, 74.3%, 90.7% and 86.4% for aspergillus niger, staphylococcus aureus, escherichia coli (C83) and pseudomonas aeruginosa respectively; the antistatic property test shows that the surface resistivity of the coating film reaches 6.5 multiplied by 105Ω。
Example 4
An antibacterial and antistatic aqueous acrylic paint was prepared by the same procedure as in example 2 except that the amount of acryloyloxyethyldimethylethylammonium bromide used was 40 parts.
The antibacterial property test of the obtained acrylic paint shows that: the antibacterial and antioxidant water-based acrylic coating prepared by the embodiment has the removal rates of 90.6%, 85.2%, 96.3% and 98.5% for aspergillus niger, staphylococcus aureus, escherichia coli (C83) and pseudomonas aeruginosa respectively; the antistatic property test shows that the surface resistivity of the coating film reaches 1.3 multiplied by 105Ω。
The above examples are merely preferred embodiments of the present invention, and the scope of the present invention is not limited to the above examples. All technical schemes belonging to the idea of the invention belong to the protection scope of the invention. It should be noted that modifications and embellishments within the scope of the invention may be made by those skilled in the art without departing from the principle of the invention, and such modifications and embellishments should also be considered as within the scope of the invention.
Claims (10)
1. An antibacterial antistatic water-based acrylic coating is characterized in that: the material comprises the following raw material components: 8-10 parts of acrylic acid, 80-85 parts of methyl methacrylate, 100 parts of butyl acrylate, 4-6 parts of diacetone acrylamide, 8-10 parts of adipic dihydrazide, 20-25 parts of acryloyloxyethyl dimethyl ethyl ammonium bromide, 20-25 parts of an anionic emulsifier, a pH regulator and deionized water.
2. The acrylic coating according to claim 1, characterized in that: the material comprises the following raw material components: 10 parts by mass of acrylic acid, 80 parts by mass of methyl methacrylate, 100 parts by mass of butyl acrylate, 5 parts by mass of diacetone acrylamide, 9 parts by mass of adipic dihydrazide, 20 parts by mass of acryloyloxyethyl dimethyl ethyl ammonium bromide, 20 parts by mass of an anionic emulsifier, 70 parts by mass of deionized water and a pH regulator.
3. The acrylic coating according to claim 1 or 2, characterized in that: the anionic emulsifier is selected from fatty alcohol ether sulfates.
4. The acrylic coating according to claim 1 or 2, characterized in that: the pH regulator is selected from ammonia water.
5. The method for producing an acrylic coating material as set forth in any one of claims 1 to 4, characterized in that: it includes:
mixing a first part of acrylic acid, methyl methacrylate, butyl acrylate, diacetone acrylamide and the emulsifier in the raw material components, adding the deionized water and the pH regulator, dissolving uniformly to obtain a pre-emulsion, and carrying out polymerization reaction for 1-3 hours at 80-90 ℃ to obtain a prepolymer;
adding a second part of acrylic acid, methyl methacrylate, butyl acrylate and diacetone acrylamide, the adipic acid dihydrazide, the acryloyloxyethyl dimethyl ethyl ammonium bromide and the pH regulator into the obtained prepolymer, continuously reacting at 80-90 ℃ for 1-3 hours, and discharging to obtain the antibacterial antistatic waterborne acrylic coating.
6. The method of claim 5, wherein: the mass ratio of the first part of acrylic acid, methyl methacrylate, butyl acrylate and diacetone acrylamide to the second part of acrylic acid, methyl methacrylate, butyl acrylate and diacetone acrylamide is 1-2: 1.
7. The method of claim 5, wherein: the pH value of the mixture system in which the pH regulator is arranged is regulated to be 8-10 by the pH regulator.
8. The method of claim 5, wherein: the addition amount of the deionized water enables the oil-water ratio of the deionized water added into the system to be 1: (0.65-0.75).
9. The method of claim 5, wherein: the acryloyloxyethyl dimethyl ethyl ammonium bromide is prepared by a preparation method comprising the following steps of:
refluxing thionyl chloride, the first part of polymerization inhibitor and acrylic acid at 30-50 ℃ for 1-10h to obtain acryloyl chloride;
adding the acryloyl chloride into a mixture of the dimethylethanolamine, the organic solvent and the second part of polymerization inhibitor, controlling the reaction temperature to be 4-6 ℃, and reacting for 1-7h at a heat preservation degree to obtain dimethylaminoethyl acrylate;
and uniformly mixing the obtained dimethylaminoethyl acrylate and bromoethane, and reacting for 1-5h at the temperature of 50-80 ℃ to obtain the acryloyloxyethyl dimethyl ethyl ammonium bromide.
10. The method of claim 9, wherein: the organic solvent is selected from diethyl ether; and/or the polymerization inhibitor is selected from hydroquinone.
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