CN115433498A - Preparation method and application of waterproof antibacterial acrylic resin wood lacquer - Google Patents
Preparation method and application of waterproof antibacterial acrylic resin wood lacquer Download PDFInfo
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- CN115433498A CN115433498A CN202211099129.3A CN202211099129A CN115433498A CN 115433498 A CN115433498 A CN 115433498A CN 202211099129 A CN202211099129 A CN 202211099129A CN 115433498 A CN115433498 A CN 115433498A
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- 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
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- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
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- 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
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Abstract
The invention relates to the technical field of acrylic resin, and discloses a preparation method and application of waterproof antibacterial acrylic resin wood lacquer.
Description
Technical Field
The invention relates to the technical field of acrylic resin, in particular to waterproof and antibacterial acrylic resin wood lacquer and a preparation method thereof.
Background
The wood lacquer has important application in the fields of furniture building materials, ancient building wood structure protection and the like, wherein the acrylic resin has excellent mechanical property, solvent resistance and weather resistance, and is widely applied to the aspects of wood lacquer, adhesives, metal corrosion prevention and the like, for example, chinese patent CN113072852B, a preparation method of fluorine-containing silicon water-based polyurethane acrylate composite coating for wood lacquer, discloses that the fluorine-containing silicon water-based polyurethane acrylate composite coating is synthesized by taking monohydroxy terminated polydimethylsiloxane, fluorine-containing acrylate, acrylate and the like as raw materials, has the advantages of good adhesive force, high gloss, outstanding hydrophobic property and the like, and can play a role in the fields of wood lacquer and the like.
The antibacterial and mildew-proof performance of the acrylic resin is improved, the antibacterial, mildew-proof and corrosion-proof performance of the acrylic resin wood lacquer on furniture building materials and ancient building wood structures is favorably improved, chinese patent CN105199577B is an antibacterial low-surface-energy marine antifouling coating composition, and the polyhydroxy fluorine-containing acrylic resin modified by quaternary ammonium salt has the low surface energy of both organic fluorine and organic silicon polymer and the antibacterial performance of quaternary ammonium salt, and can be widely applied to the field of marine antifouling and building materials; the invention synthesizes the novel bi-full fluoroalkyl quaternary ammonium salt-based acrylate monomer and the waterproof antibacterial acrylic resin, and has wide application prospect in the fields of wood lacquer, antibacterial coating and the like.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a waterproof antibacterial acrylic resin wood lacquer, which solves the problems of poor waterproof property and low antibacterial property of the acrylic resin wood lacquer.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: a waterproof antibacterial acrylic resin wood lacquer is prepared by the following steps:
s1: adding an acrylate monomer, bi-perfluoroalkyl quaternary ammonium salt acrylate, sodium dodecyl sulfate and OP-10 into deionized water, and uniformly stirring to prepare a pre-polymerization monomer solution;
s2: dropwise adding an initiator into a 25-40% volume of prepolymer monomer solution, reacting for 30-60 min at the temperature of 65-75 ℃ in the nitrogen atmosphere, then adding the rest prepolymer monomer solution, supplementing the initiator, reacting for 2-4 h, cooling after reaction, adding an antifoaming agent accounting for 0.2-0.6% of the total mass of the acrylate monomer, a wetting dispersant accounting for 0.2-1% of the total mass of the acrylate monomer and a leveling agent accounting for 0.1-0.4%, and shearing and emulsifying at high speed to obtain the waterproof antibacterial acrylic resin wood lacquer.
Preferably, the acrylate monomer in S1 includes methyl acrylate, methyl methacrylate, n-butyl acrylate, n-butyl methacrylate, acrylic acid, methacrylic acid, and hydroxyethyl acrylate.
Preferably, the amount of the bi-perfluoroalkyl quaternary ammonium salt acrylate in the S1 is 2-12% of the total mass of the acrylate monomer.
Preferably, the initiator in S2 comprises potassium persulfate and ammonium persulfate; the total amount of the initiator is 0.7-1.2% of the total mass of the acrylate monomer.
Preferably, the preparation steps of the bi-per-fluoroalkyl quaternary ammonium salt-based acrylate in S1 are as follows:
s3, adding perfluoroalkyl sulfonyl chloride, 3-dimethylamino-1-propanol and triethylamine into a reaction solvent under ice bath, wherein the mass molar ratio of the substances is 1.1-1.4;
s4, adding 3-dimethylamino perfluoroalkyl sulfonate and 1,3-dichloropropanol into N, N-dimethylformamide, reacting at 70-110 ℃ for 24-72-h, adding deionized water and trichloromethane for extraction after reaction, adding anhydrous sodium sulfate into a trichloromethane organic layer for drying, filtering, adding trichloromethane and ethanol into filtrate, and recrystallizing a volatile solvent to obtain the bis-perfluoroalkyl quaternary ammonium salt base propanol;
s5, adding bi-perfluoroalkyl quaternary ammonium salt based propanol, acryloyl chloride and triethylamine into trichloromethane under ice bath, wherein the mass molar ratio of the materials is 1:1-1.3;
preferably, the reaction solvent in S3 comprises dichloromethane, 1,2-dichloroethane, trichloromethane and carbon tetrachloride.
Preferably, the molar ratio of the 3-dimethylamino perfluoroalkylsulfonate to the 1,3-dichloropropanol in S4 is 2-2.5.
(III) advantageous technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
the perfluoroalkyl sulfonyl chloride and the 3-dimethylamino-1-propanol are utilized to react to synthesize the 3-dimethylamino perfluoroalkyl sulfonate, and then the 3-dimethylamino perfluoroalkyl sulfonate sequentially reacts with 1,3-dichloropropanol and acryloyl chloride to synthesize a novel bi-perfluoroalkyl quaternary ammonium salt acrylate monomer which contains a bi-perfluoroalkyl quaternary ammonium salt group.
The bi-perfluoroalkyl quaternary ammonium salt acrylate and the acrylic monomer are polymerized to obtain the acrylic resin, the hydrophobic bi-perfluoroalkyl chain and the antibacterial bi-quaternary ammonium salt group are introduced into the main chain of the acrylic resin, so that the water resistance and the water resistance of the acrylic resin are improved, the acrylic resin is endowed with excellent antibacterial and mildewproof effects, the practical application of the acrylic resin in the aspects of furniture building materials, ancient building wood structure protection and the like is expanded, and the acrylic resin has wide application prospects in the fields of wood lacquer, antibacterial coating and the like.
Drawings
FIG. 1 is a reaction scheme for the preparation of bis-perfluorobutyl quaternary ammonium acrylate.
FIG. 2 is a FT-IR spectrum of the acrylic resin emulsion prepared in example 1.
Detailed Description
The present invention provides the following examples:
example 1
(1) Adding 2 g perfluorobutylsulfonyl chloride, 0.72 g 3-dimethylamino-1-propanol and 0.86 g triethylamine into trichloromethane under an ice bath, heating to 60 ℃, reacting for 12 h, concentrating under reduced pressure after reaction, and washing with petroleum ether to obtain 3-dimethylamino perfluorobutyl sulfonate;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.65-4.22 (t, 2H)，2.57-2.38(m, 2H)，2.78（s, 6 H），1.72-1.57(m, 2H)。
(2) Adding 3-dimethylamino perfluorobutyl sulfonate with the molar ratio of 3.1 g and 1,3-dichloropropanol with the molar ratio of 0.5 g into N, N-dimethylformamide, reacting at 110 ℃ for 72 h, adding deionized water and trichloromethane for extraction after the reaction, adding anhydrous sodium sulfate into a trichloromethane organic layer for drying, then filtering, adding trichloromethane and ethanol into the filtrate, volatilizing the solvent for recrystallization, and obtaining the bis-perfluorobutyl quaternary ammonium salt based propanol;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.58-4.30 (m, 1H)，3.60-3.52 (m, 1H)，3.50-3.32(m, 8H)，3.21（s, 12 H），3.18-3.06(m, 4H)，2.35-2.20(m, 4H)。
(3) Bis-perfluorobutyl quaternary ammonium salt based propanol, 0.2 g acryloyl chloride and 0.24 g triethylamine were added to chloroform while cooling on ice, followed by 24 h at 35 deg.CAfter reaction, decompressing and concentrating, washing with petroleum ether, adding the product into ethanol and trichloromethane, volatilizing the solvent for recrystallization, and obtaining the bis-per-fluoro butyl quaternary ammonium salt acrylate;
，1H NMR (CDCl 3 , 300 MHz) δ: 6.33-6.29 (m, 1H)，6.13-6.08 (m, 1H)，5.72-5.60(m, 1H)，5.32-5.16(m, 1H)，3.69-3.37 (m, 8H)，3.20（s, 12 H），3.15-3.02(m, 4H)，2.35-2.16(m, 4H)。
(4) Adding 2.5 g methyl acrylate, 10 g n-butyl methacrylate, 1 g acrylic acid, 0.6 g hydroxyethyl acrylate, 0.3 g bis-perfluorobutyl quaternary ammonium salt acrylate, 0.12 g sodium dodecyl sulfate and 0.2 g OP-10 into deionized water, and stirring uniformly to prepare a prepolymer monomer solution;
(5) Dropwise adding 0.03 g potassium persulfate into 30% volume of prepolymer monomer solution, heating to 75 ℃ in a nitrogen atmosphere for reaction for 30 min, then adding the rest prepolymer monomer solution, supplementing 0.08 g potassium persulfate, reacting 2 h, cooling after reaction to obtain acrylic resin emulsion, then adding 0.03 g defoamer BYK-A555, 0.07 g wetting dispersant BYK-190 and 0.04 g flatting agent TEGO-A115 based on the total mass of acrylate monomers, and carrying out high-speed shearing emulsification to obtain the waterproof and antibacterial acrylic resin wood lacquer.
Example 2
(1) Adding 2 g perfluorohexyl sulfonyl chloride, 1.22 g 3-dimethylamino-1-propanol and 1.58 g triethylamine into dichloromethane under ice bath, heating to 35 ℃ to react for 18 h, decompressing and concentrating after reaction, and washing with petroleum ether to obtain 3-dimethylamino perfluorohexyl sulfonate;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.62-4.21 (t, 2H)，2.59-2.41(m, 2H)，2.72（s, 6 H），1.72-1.56(m, 2H)。
(2) 3-dimethylamino perfluorohexyl sulfonate with a molar ratio of 4.5 g, 1,3-dichloropropanol of 0.5 g were added to N, N-dimethylformamide at 70 deg.CReacting 72 h, adding deionized water and trichloromethane for extraction after the reaction, adding anhydrous sodium sulfate into a trichloromethane organic layer for drying, then filtering, adding trichloromethane and ethanol into filtrate, volatilizing the solvent for recrystallization, and obtaining the bis-per-fluoro hexyl quaternary ammonium salt based propanol;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.52-4.28 (m, 1H)，3.65-3.54 (m, 1H)，3.50-3.34(m, 8H)，3.26（s, 12 H），3.23-3.07(m, 4H)，2.36-2.18(m, 4H)。
(3) Adding bis-perfluorobutyl quaternary ammonium salt based propanol, 0.3 g acryloyl chloride and 0.28 g triethylamine into trichloromethane under ice bath, then reacting at 48 h at 20 ℃, decompressing and concentrating after reacting, washing with petroleum ether, adding the product into ethanol and trichloromethane, volatilizing the solvent and recrystallizing to obtain bis-perfluorohexyl quaternary ammonium salt based acrylate;
1H NMR (CDCl 3 , 300 MHz) δ: 6.30-6.25 (m, 1H)，6.12-6.06 (m, 1H)，5.74-5.61(m, 1H)，5.33-5.15(m, 1H)，3.72-3.36 (m, 8H)，3.21（s, 12 H），3.15-3.01(m, 4H)，2.37-2.15(m, 4H)。
(4) Adding 4 g methyl methacrylate, 10 g n-butyl methacrylate, 1.3 g acrylic acid, 1 g methacrylic acid, 1.5 g hydroxyethyl acrylate, 1.2 g bis-per-fluorohexyl quaternary ammonium salt acrylate, 0.15 g sodium dodecyl sulfate, and 0.3 g OP-10 into deionized water, and stirring uniformly to prepare a prepolymer monomer solution;
(5) Dropwise adding 0.06 g ammonium persulfate into 30% volume of prepolymer monomer solution, reacting for 30 min at the temperature of 65 ℃ in a nitrogen atmosphere, then adding the rest prepolymer monomer solution, supplementing 0.12 g ammonium persulfate, reacting for 3 h, cooling after reaction, adding 0.03 g defoamer BYK-A555, 0.09 g wetting dispersant BYK-190, 0.03 g flatting agent TEGO-A115 in the total mass of acrylate monomers, and shearing and emulsifying at high speed to obtain the waterproof antibacterial acrylic resin wood paint.
Example 3
(1) Adding 2 g perfluorooctylsulfonyl chloride, 1.30 g 3-dimethylamino-1-propanol and 1.42 g triethylamine into carbon tetrachloride under an ice bath, heating to 50 ℃, reacting at 18 h, concentrating under reduced pressure after reaction, and washing with petroleum ether to obtain 3-dimethylamino perfluorooctylsulfonate;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.60-4.26 (t, 2H)，2.60-2.47(m, 2H)，2.74（s, 6 H），1.76-1.57(m, 2H)。
(2) Adding 3-dimethylamino perfluorooctyl sulfonate with the molar ratio of 5.8 g and 1,3-dichloropropanol with the molar ratio of 0.5 g into N, N-dimethylformamide, reacting at 100 ℃ for 48 h, adding deionized water and trichloromethane after the reaction for extraction, adding anhydrous sodium sulfate into a trichloromethane organic layer for drying, then filtering, adding trichloromethane and ethanol into the filtrate, volatilizing the solvent for recrystallization, and obtaining the bis-per-fluoro octyl quaternary ammonium salt based propanol;
，1H NMR (CDCl 3 , 300 MHz) δ: 4.50-4.27 (m, 1H)，3.69-3.58 (m, 1H)，3.46-3.32(m, 8H)，3.30（s, 12 H），3.18-3.06(m, 4H)，2.35-2.18(m, 4H)。
(3) Adding bis-perfluorobutyl quaternary ammonium salt based propanol, 0.34 g acryloyl chloride and 0.28 g triethylamine into trichloromethane under ice bath, then reacting at 35 ℃ for 36 h, decompressing and concentrating after reacting, washing with petroleum ether, adding the product into ethanol and trichloromethane, volatilizing the solvent and recrystallizing to obtain bis-perfluorooctyl quaternary ammonium salt based acrylate;
1H NMR (CDCl 3 , 300 MHz) δ: 6.31-6.26 (m, 1H)，6.14-6.07 (m, 1H)，5.73-5.62(m, 1H)，5.36-5.17(m, 1H)，3.65-3.33(m, 8H)，3.22（s, 12 H），3.13-3.03(m, 4H)，2.36-2.14(m, 4H)。
(4) Adding 3.2 g methyl acrylate, 10 g n-butyl methacrylate, 1.6 g methacrylic acid, 0.8 g hydroxyethyl acrylate, 1.8 g bis-per-fluoro octyl quaternary ammonium salt acrylate, 0.15 g sodium dodecyl sulfate, and 0.3 g OP-10 into deionized water, and stirring uniformly to prepare a prepolymer monomer solution;
(5) Dropwise adding 0.06 g potassium persulfate into 40% volume of prepolymer monomer solution, reacting for 30 min at the temperature of 65 ℃ in a nitrogen atmosphere, then adding the rest prepolymer monomer solution, supplementing 0.14 g potassium persulfate, reacting for 4 h, cooling after reaction, adding 0.08 g defoamer BYK-A555, 0.15 g wetting dispersant BYK-190 and 0.03 g flatting agent TEA 115 based on the total mass of acrylate monomers, and emulsifying at high speed to obtain the waterproof antibacterial GO wood paint.
Comparative example 1
(1) Adding 3.5 g methyl methacrylate, 10 g n-butyl methacrylate, 1.4 g acrylic acid, 0.8 g hydroxyethyl acrylate, 0.12 g sodium dodecyl sulfate, 0.25 g OP-10 into deionized water, and stirring uniformly to prepare a prepolymer monomer solution;
(2) Dropwise adding 0.06 g potassium persulfate into 30% volume of prepolymer monomer solution, heating to 70 ℃ in nitrogen atmosphere for reacting for 40 min, then adding the rest prepolymer monomer solution, supplementing 0.12 g potassium persulfate, reacting for 4 h, cooling after reaction, adding 0.06 g defoamer BYK-A555, 0.12 g wetting dispersant BYK-190 and 0.02 g leveling agent TEA 115 based on the total mass of acrylate monomers, and emulsifying at high speed to obtain the acrylic resin wood paint GO.
The zone of inhibition test: removing 1X 10 of 0.05 mL 7 Placing CFU/mL escherichia coli bacterial suspension into a culture dish, adding a beef extract peptone agar culture medium, uniformly shaking, placing the solidified waterproof antibacterial acrylic resin wood lacquer adhesive film (the radius is 0.5 cm, the thickness is 0.1 cm) on a solid culture medium, culturing in an incubator at constant temperature of 24 h, the culture temperature is 37 ℃, and measuring the diameter of a bacteriostatic zone after culturing.
| Sample(s) | Diameter of bacteriostatic circle (mm) |
| Example 1 | 10.4±0.1 |
| Example 2 | 16.7±0.1 |
| Example 3 | 15.2±0.1 |
| Comparative example 1 | - |
Water absorption test: weighing 1 g and adding the weighed 1 g into 100 mL deionized water, soaking and absorbing water 24 h, taking out the adhesive film, wiping residual water on the surface, weighing, and calculating the water absorption rate.
Water contact angle test: the water contact angle of the cured waterproof antibacterial acrylic resin woodenware paint adhesive film (10 cm X10 cm X0.2 cm) is measured by an optical contact angle tester
| Sample (I) | Water absorption (%) | Water contact Angle (°) |
| Example 1 | 4.9 | 93.4 |
| Example 2 | 4.2 | 106.8 |
| Example 3 | 4.0 | 112.7 |
| Comparative example 1 | 8.7 | 70.6 |
Water absorption = (M) After absorbing water -M Before water absorption ）/M Before water absorption ×100%。
Claims (7)
1. The waterproof antibacterial acrylic resin wood lacquer is characterized in that: the preparation steps of the waterproof antibacterial acrylic resin wood lacquer are as follows:
s1: adding an acrylate monomer, bi-perfluoroalkyl quaternary ammonium salt acrylate, sodium dodecyl sulfate and OP-10 into deionized water, and uniformly stirring to prepare a pre-polymerization monomer solution;
s2: dropwise adding an initiator into a 25-40% volume of prepolymer monomer solution, reacting for 30-60 min at the temperature of 65-75 ℃ in the nitrogen atmosphere, then adding the rest prepolymer monomer solution, supplementing the initiator, reacting for 2-4 h, cooling after reaction, adding an antifoaming agent accounting for 0.2-0.6% of the total mass of the acrylate monomer, a wetting dispersant accounting for 0.2-1% of the total mass of the acrylate monomer and a flatting agent accounting for 0.1-0.4%, and shearing and emulsifying at high speed to obtain the waterproof and antibacterial acrylic resin wood lacquer.
2. The waterproof antibacterial acrylic resin wood lacquer according to claim 1, characterized in that: the acrylate monomer in S1 comprises methyl acrylate, methyl methacrylate, n-butyl acrylate, n-butyl methacrylate, acrylic acid, methacrylic acid and hydroxyethyl acrylate.
3. The waterproof antibacterial acrylic resin wood lacquer according to claim 1, characterized in that: the dosage of the bi-perfluoroalkyl quaternary ammonium salt base acrylate in the S1 is 2-12% of the total mass of the acrylate monomer.
4. The waterproof antibacterial acrylic resin wood lacquer according to claim 1, characterized in that: the initiator in the S2 comprises potassium persulfate and ammonium persulfate; the total amount of the initiator is 0.7-1.2% of the total mass of the acrylate monomer.
5. The waterproof antibacterial acrylic resin wood lacquer according to claim 1, characterized in that: the preparation steps of the bi-perfluor alkyl quaternary ammonium salt base acrylate in the S1 are as follows:
s3, adding perfluoroalkyl sulfonyl chloride, 3-dimethylamino-1-propanol and triethylamine into a reaction solvent under ice bath, wherein the mass molar ratio of the substances is 1.1-1.4;
s4, adding 3-dimethylamino perfluoroalkyl sulfonate and 1,3-dichloropropanol into N, N-dimethylformamide, reacting at 70-110 ℃ for 24-72-h, and extracting, drying and recrystallizing after reaction to obtain bi-perfluoroalkyl quaternary ammonium salt base propanol;
s5, adding bis-perfluoroalkyl quaternary ammonium salt based propanol, acryloyl chloride and triethylamine into trichloromethane under ice bath, wherein the mass molar ratio of the materials is 1:1-1.3, reacting at 20-35 ℃ for 12-48 h, and after the reaction, decompressing, concentrating, washing and recrystallizing to obtain the bis-perfluoroalkyl quaternary ammonium salt based acrylate.
6. The waterproof antibacterial acrylic resin wood lacquer according to claim 5, characterized in that: the reaction solvent in S3 comprises dichloromethane, 1,2-dichloroethane, trichloromethane and carbon tetrachloride.
7. The waterproof antibacterial acrylic resin wood lacquer according to claim 5, characterized in that: the mass molar ratio of the 3-dimethylamino perfluoroalkyl sulfonate and 1,3-dichloropropanol in the S4 is 2-2.5.
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