CN114591466B - Preparation method and application of polymerizable eutectic solvent antistatic agent - Google Patents
Preparation method and application of polymerizable eutectic solvent antistatic agent Download PDFInfo
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- CN114591466B CN114591466B CN202210223572.0A CN202210223572A CN114591466B CN 114591466 B CN114591466 B CN 114591466B CN 202210223572 A CN202210223572 A CN 202210223572A CN 114591466 B CN114591466 B CN 114591466B
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- eutectic solvent
- antistatic agent
- polymerizable
- antistatic
- polymerizable eutectic
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- 239000002904 solvent Substances 0.000 title claims abstract description 88
- 230000005496 eutectics Effects 0.000 title claims abstract description 86
- 239000002216 antistatic agent Substances 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 239000011248 coating agent Substances 0.000 claims abstract description 25
- 238000000576 coating method Methods 0.000 claims abstract description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 18
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 238000003848 UV Light-Curing Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims abstract description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 28
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000123 paper Substances 0.000 claims description 27
- 239000002023 wood Substances 0.000 claims description 25
- 239000000853 adhesive Substances 0.000 claims description 17
- 230000001070 adhesive effect Effects 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 12
- 239000002313 adhesive film Substances 0.000 claims description 9
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 8
- 235000019743 Choline chloride Nutrition 0.000 claims description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 8
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 8
- 229960003178 choline chloride Drugs 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 6
- 229960003237 betaine Drugs 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 239000011094 fiberboard Substances 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 4
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 4
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 244000028419 Styrax benzoin Species 0.000 claims description 3
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 3
- RAWPGIYPSZIIIU-UHFFFAOYSA-N [benzoyl(phenyl)phosphoryl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 RAWPGIYPSZIIIU-UHFFFAOYSA-N 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 229960001040 ammonium chloride Drugs 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 229960002130 benzoin Drugs 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 235000019382 gum benzoic Nutrition 0.000 claims description 3
- 238000003760 magnetic stirring Methods 0.000 claims description 3
- 238000010907 mechanical stirring Methods 0.000 claims description 3
- 238000007761 roller coating Methods 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 6
- 239000002608 ionic liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000003575 carbonaceous material Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- STGNLGBPLOVYMA-TZKOHIRVSA-N (z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O STGNLGBPLOVYMA-TZKOHIRVSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
-
- 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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/52—Amides or imides
- C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/47—Condensation polymers of aldehydes or ketones
- D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
- D21H17/51—Triazines, e.g. melamine
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
Abstract
The invention belongs to the technical field of antistatic agents, and particularly relates to a preparation method of a polymerizable eutectic solvent type antistatic agent, which comprises the following steps: drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃ according to the mole ratio of 1: mixing 0.5-3, heating at the constant temperature of 60-100 ℃, stirring and reacting for 30 min-4 h until transparent and clear liquid is formed, and cooling to room temperature to obtain colorless and transparent eutectic solvent; adding a cross-linking agent and an initiator into the eutectic solvent, and uniformly mixing to form a mixed solution. The prepared polymerizable eutectic solvent type antistatic agent is applied to the preparation of UV curing antistatic acrylic coating and antistatic decorative impregnated bond paper. The invention can stably polymerize without using extra liquid solvent to dissolve, avoids using high boiling point toxic organic solvent, and has simple and standard synthesis process, easily mastered production process and production flow, and relatively low production cost and raw material cost.
Description
Technical Field
The invention belongs to the technical field of antistatic agents, and particularly relates to a preparation method and application of a polymerizable eutectic solvent type antistatic agent.
Background
In daily life, static electricity is a common phenomenon, and particularly in a low-humidity environment, the existence of the static electricity can generate a plurality of hazards, such as dust collection on the surface, breakdown of electronic devices, explosion and the like. Therefore, there is an increasing demand for floors/wallboards with antistatic function in the market, especially in public places such as schools, hospitals, nursing homes, stadiums, etc.
The wood floor/wallboard is one of the preferred decorative materials of the current consumers, and the surface decorative/coating materials commonly used for the wood floor/wallboard are paint or melamine impregnated bond paper, so that to realize the antistatic function of the wood floor/wallboard, the paint or melamine impregnated bond paper needs to be subjected to antistatic treatment, and the main method is to add a proper antistatic agent.
Antistatic agents currently in common use are mainly classified into conductive materials and surfactants, wherein the conductive materials dissipate static charges by forming a conductive network in a polymer matrix, typically carbon materials, metals and their oxides, conductive polymers, and the like; surfactants are typically quaternary ammonium salts by which they migrate to the surface and adsorb moisture from the surrounding environment to form a conductive water film to dissipate static charge. The main disadvantages of the application of the surface active antistatic agent to the wood floor/wallboard are that the antistatic durability is poor, the antistatic agent is not scrubbing-resistant, the dependence on the environment humidity is large, and the use of the antistatic agent is limited; the carbon material, metal and oxide in the conductive material have the main defects of opaqueness, influence on decorative color and high cost, and limit the wide use of the conductive material.
The ionic liquid is a liquid ion body at room temperature, has the characteristics of conductivity, designable molecular structure and the like, and has good application prospect in the aspects of high polymer antistatic and the like, wherein imidazole ionic liquid antistatic agents and the like are reported. However, the imidazole ionic liquid antistatic agent has high cost and limits the application of the imidazole ionic liquid antistatic agent in wood floor/wallboard paint or impregnating adhesive.
The eutectic solvent is a special ionic liquid and has the advantages of low vapor pressure, chemical stability, incombustibility, high dissolving capacity, low toxicity, environmental friendliness, 100% of atomic utilization rate in the preparation process, low cost and the like. At present, the eutectic solvent is mainly applied to aspects of medicine dissolution, purification, electrodeposition, material preparation, carbon dioxide capture, biopolymer treatment and the like, and reports on application of the polymerizable eutectic solvent to antistatic agents are relatively few.
Therefore, it is necessary to explore a polymerizable eutectic solvent applied to a coating/melamine impregnated bond paper antistatic agent, which can improve the antistatic durability, and realize lower cost and better environmental friendliness.
Disclosure of Invention
In view of the above-mentioned shortcomings in the prior art, the present invention aims to provide a method for preparing a polymerizable eutectic solvent-based antistatic agent.
The preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃ according to the mole ratio of 1:0.5 to 3, heating at a constant temperature of 60 to 100 ℃, stirring and reacting for 30 minutes to 4 hours until transparent and clear liquid is formed, and cooling to room temperature to obtain a colorless and transparent eutectic solvent, wherein the hydrogen bond acceptor compound is any one or more of halogen-containing ammonium salt and halogen-containing quaternary ammonium salt; the hydrogen bond donor compound is any one or more of polymerizable carboxylic acid monomers;
(2) Adding a cross-linking agent and an initiator into the eutectic solvent, and uniformly mixing to form a mixed solution to prepare the polymerizable eutectic solvent type antistatic agent, wherein the cross-linking agent is an acrylamide monomer, the mass of the cross-linking agent accounts for 5-20% of the mass of the antistatic agent, and the initiator is a photoinitiator or a thermal initiator, and the mass of the initiator accounts for 0.1-5% of the mass of the antistatic agent.
Preferably, the hydrogen bond acceptor compound in step (1) is one or more of choline chloride, betaine, ammonium chloride, cetyltrimethylammonium bromide, preferably choline chloride.
Preferably, the hydrogen bond donor compound in step (1) is one or more of maleic acid (maleic acid), itaconic acid, acrylic acid, methacrylic acid, lactic acid, preferably maleic acid.
Preferably, the stirring in the step (1) is magnetic stirring or mechanical stirring, and the stirring speed is 100-1000 rpm.
Preferably, the cross-linking agent in step (2) is one or more of acrylamide, N-methylolacrylamide, N-isopropylacrylamide and N, N-dimethylacrylamide.
Preferably, the photoinitiator in the step (2) is any one of diphenyl ethanone, alpha-hydroxyalkyl benzophenone, dibenzoyl phenyl phosphine oxide and benzoin; the thermal initiator is any one of ammonium persulfate, potassium persulfate, lauroyl peroxide and azodiisobutyronitrile.
The polymerizable eutectic solvent antistatic agent prepared by the invention forms a conductive high polymer network in a matrix, has the characteristics of excellent antistatic property, lasting electrostatic protection, less influence by environmental humidity and the like, can be directly used for edge sealing of floors/wallboards, realizes low-resistance connection between boards, and reduces the use of conductive strips.
It is still another object of the present invention to apply the prepared polymerizable eutectic solvent type antistatic agent to the preparation of UV-curable antistatic acrylic coating.
The method comprises the following specific steps:
(1) Adding the prepared polymerizable eutectic solvent type antistatic agent into a UV curing acrylic coating to obtain the UV curing antistatic acrylic coating, wherein the mass ratio of the polymerizable eutectic solvent type antistatic agent to the UV acrylic coating is 1:4-1:20;
(2) The UV-cured antistatic acrylic coating is applied to solid wood floors/wallboards and solid wood composite floors/wallboards, and the antistatic wood floors/wallboards are obtained after UV curing.
Preferably, the UV-cured antistatic acrylic coating is used for the surface and the subsurface of a solid wood floor/wallboard or a solid wood composite floor/wallboard, preferably roll coating, and the total coating weight is not less than 16g/m 2 。
The third object of the present invention is to apply the prepared polymerizable eutectic solvent type antistatic agent to the preparation of antistatic decorative impregnated bond paper.
The method comprises the following specific steps:
(1) Adding the prepared polymerizable eutectic solvent type antistatic agent into melamine impregnating adhesive to obtain antistatic melamine impregnating adhesive, wherein the mass ratio of the polymerizable eutectic solvent type antistatic agent to the melamine impregnating adhesive is 1:4-1:25;
(2) And (3) impregnating the decorative paper with the antistatic melamine impregnated adhesive to obtain antistatic decorative impregnated adhesive film paper, and attaching the antistatic decorative impregnated adhesive film paper to a fiber board/blockboard to obtain the antistatic reinforced floor/ecological board.
Preferably, the antistatic melamine impregnated paper is impregnated with the decorative paper, and the polymerizable eutectic solvent type antistatic agent is mixed with the melamine impregnated paper to impregnate the adhesive film paper, wherein the impregnation amount is 0.6-1.6 times of the weight of the base paper; after twice drying (the first drying temperature is 100-120 ℃ and the second drying temperature is 130-180 ℃), cooling to obtain the antistatic decorative impregnated adhesive film paper; and (3) sticking the surface of the base material to obtain the melamine impregnated bond paper facing antistatic wood floor/wallboard.
Advantageous effects
The invention mixes and heats the hydrogen bond donor compound (solid powder/liquid) and the hydrogen bond acceptor compound (solid powder) to obtain a stable nontoxic polymerizable eutectic solvent, then uses the eutectic solvent as a monomer polymerized at the front end and acrylic resin/melamine resin to carry out self-polymerization and cross-linking polymerization to form a polymerizable eutectic solvent antistatic agent, and applies the polymerizable eutectic solvent antistatic agent to the preparation of antistatic acrylic coating/melamine impregnated bond paper. The method can stably polymerize without using extra liquid solvent to dissolve, and avoids the use of toxic organic solvents with high boiling points. Meanwhile, the synthesis process is simple and standard, the production process and the production flow are easy to master, and the production cost and the raw material cost are relatively low.
Detailed Description
The present invention will be described in detail with reference to the following examples, so that those skilled in the art can better understand the present invention, but the present invention is not limited to the following examples.
Example 1
The preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Weighing 27.926g of choline chloride and 11.607g of maleic acid, drying in an oven at 80 ℃, putting into a round bottom flask, mixing at 70 ℃, magnetically stirring at 500rpm for 3 hours until a transparent and clear liquid is formed, and obtaining a eutectic solvent;
(2) 5.055g of N-methylolacrylamide and 0.134g of diphenylethanone were added to the eutectic solvent and stirred to dissolve to obtain the UV polymerizable eutectic solvent type antistatic agent.
And adding the prepared Ultraviolet (UV) polymerizable eutectic solvent type antistatic agent into 223.61g of UV-curable acrylic coating to obtain the UV-curable antistatic acrylic coating.
The UV curing antistatic acrylic coating is coated according to the coating weight of 14g/m 2 And (3) roller coating the surface and the side surface of the solid wood/plywood, and curing after passing through a UV lamp to obtain the antistatic wood floor/wallboard.
The surface resistance of the obtained antistatic wood floor/wallboard is 4 multiplied by 10 9 Ω。
Example 2
The preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Weighing 13.963g of choline chloride and 13.01g of itaconic acid, drying in a baking oven at 70 ℃, putting into a round bottom flask, mixing at 80 ℃ and magnetically stirring at 600rpm for 2 hours until a transparent and clear liquid is formed, thus obtaining a eutectic solvent;
(2) 2.70g of N-isopropyl acrylamide and 0.10g of ammonium persulfate were added to the eutectic solvent and stirred for dissolution to obtain a heat polymerizable eutectic solvent type antistatic agent.
And adding the prepared thermal polymerization eutectic solvent type antistatic agent into 134.1g of melamine impregnating adhesive to obtain the antistatic melamine impregnating adhesive. Since the thermally polymerizable eutectic solvent type antistatic agent has the function of a melamine impregnated adhesive curing agent, no additional curing agent is required.
Dipping 80g of decorative paper with the antistatic melamine dipping glue, wherein the dipping amount is 80g, the first drying temperature is 110 ℃, and the second drying temperature is 160 ℃, so as to obtain the antistatic melamine decorative adhesive film paper; and (3) attaching the fiber board to the surface of the fiber board to obtain the antistatic reinforced floor/wallboard.
The surface resistance of the obtained antistatic wood floor/wallboard is 8 multiplied by 10 8 Ω。
Example 3
The preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Weighing 11.715g of betaine and 14.412g of acrylic acid, drying the betaine in a baking oven at 60 ℃, putting the betaine into a round bottom flask, mixing at 65 ℃ and mechanically stirring at 200rpm for 1.5 hours until a transparent and clear liquid is formed, thus obtaining a eutectic solvent;
(2) 3.92g of acrylamide and 0.150g of alpha-hydroxyalkyl benzophenone are added into the eutectic solvent, and stirred and dissolved to obtain the UV polymerizable eutectic solvent type antistatic agent.
And adding the prepared Ultraviolet (UV) polymerizable eutectic solvent type antistatic agent into 180g of Ultraviolet (UV) curable acrylic coating to obtain the Ultraviolet (UV) curable antistatic acrylic coating.
The UV-cured antistatic acrylic coating is coated according to the coating weight of 15g/m 2 And (3) roller coating the surface and the side surface of the solid wood/plywood, and curing after passing through a UV lamp to obtain the antistatic wood floor/wallboard.
The surface resistance of the obtained antistatic wood floor/wallboard is 9 multiplied by 10 8 Ω。
Example 4
The preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) 36.446g of cetyltrimethylammonium bromide and 9.008g of lactic acid were weighed into a round bottom flask, mixed at 60℃and mechanically stirred at 150rpm for 2h until a clear transparent liquid formed, yielding a eutectic solvent.
(2) 6.82g of N, N-dimethylacrylamide and 0.30g of potassium persulfate were added to the eutectic solvent and stirred to dissolve to obtain the heat-polymerizable eutectic solvent type antistatic agent.
And adding the prepared heat-polymerizable eutectic solvent type antistatic agent into 600g of melamine impregnating adhesive to obtain the antistatic melamine impregnating adhesive. Because the heat-polymerizable eutectic solvent type antistatic agent is acidic and has the function of a melamine impregnated adhesive curing agent, the curing agent is not additionally reinforced.
Dipping 80g of decorative paper with antistatic melamine dipping glue, wherein the dipping amount is 100g, the first drying temperature is 120 ℃, and the second drying temperature is 150 ℃, so as to obtain antistatic melamine decorative adhesive film paper; and (3) attaching the surface of the laminated wood board to obtain the antistatic reinforced floor/wallboard.
The surface resistance of the prepared antistatic wood floor/wallboard is 3 multiplied by 10 9 Ω。
The foregoing description is only illustrative of the present invention and is not intended to limit the scope of the invention, and all equivalent structures or equivalent processes or direct or indirect application in other related technical fields are included in the scope of the present invention. It should be noted that the above-described embodiments are only for explaining the present invention and do not limit the present invention in any way. The invention has been described with reference to exemplary embodiments, but it is understood that the words which have been used are words of description and illustration, rather than words of limitation. Modifications may be made to the invention as defined in the appended claims, and the invention may be modified without departing from the scope and spirit of the invention. Although the invention is described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, as the invention extends to all other means and applications which perform the same function.
Claims (21)
1. The application of a polymerizable eutectic solvent type antistatic agent is characterized in that the application of the polymerizable eutectic solvent type antistatic agent to the preparation of UV-cured antistatic acrylic paint comprises the following steps:
(A) Adding the prepared polymerizable eutectic solvent type antistatic agent into a UV curing acrylic coating to obtain the UV curing antistatic acrylic coating, wherein the mass ratio of the polymerizable eutectic solvent type antistatic agent to the UV acrylic coating is 1:4-1:20;
(B) The UV curing antistatic acrylic coating is applied to a solid wood floor/wallboard and a solid wood composite floor/wallboard, and the antistatic wood floor/wallboard is obtained after UV curing;
wherein, the preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃ according to the mole ratio of 1:0.5 to 3, heating at a constant temperature of 60 to 100 ℃, stirring and reacting for 30 minutes to 4 hours until transparent and clear liquid is formed, and cooling to room temperature to obtain a colorless and transparent eutectic solvent, wherein the hydrogen bond acceptor compound is any one or more of halogen-containing ammonium salt and halogen-containing quaternary ammonium salt; the hydrogen bond donor compound is any one or more of polymerizable carboxylic acid monomers;
(2) Adding a cross-linking agent and an initiator into the eutectic solvent, and uniformly mixing to form a mixed solution to prepare the polymerizable eutectic solvent type antistatic agent, wherein the cross-linking agent is an acrylamide monomer, the mass of the cross-linking agent accounts for 5-20% of the mass of the antistatic agent, and the initiator is a photoinitiator or a thermal initiator, and the mass of the initiator accounts for 0.1-5% of the mass of the antistatic agent.
2. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the UV cured antistatic acrylic coating in the step (B) is used for the surface and the subsurface of a solid wood floor/wallboard or a solid wood composite floor/wallboard, and is coated by roller coating and total coatingThe cloth amount is not less than 16g/m 2 。
3. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the hydrogen bond acceptor compound in the step (1) is one or more of choline chloride, betaine, ammonium chloride and hexadecyl trimethyl ammonium bromide.
4. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the hydrogen bond acceptor compound in the step (1) is choline chloride.
5. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the hydrogen bond donor compound in the step (1) is one or more of maleic acid, itaconic acid, acrylic acid, methacrylic acid and lactic acid.
6. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the hydrogen bond donor compound in the step (1) is maleic acid.
7. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the stirring in the step (1) is magnetic stirring or mechanical stirring, and the stirring speed is 100-1000 rpm.
8. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the cross-linking agent in the step (2) is one or more of acrylamide, N-methylol acrylamide, N-isopropyl acrylamide and N, N-dimethyl acrylamide.
9. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the photoinitiator in the step (2) is any one of diphenyl ethanone, a-hydroxyalkyl benzophenone, dibenzoyl phenyl phosphine oxide and benzoin.
10. Use of a polymerizable eutectic solvent based antistatic agent according to claim 1, characterized in that: the thermal initiator in the step (2) is any one of ammonium persulfate, potassium persulfate, lauroyl peroxide and azodiisobutyronitrile.
11. The application of the polymerizable eutectic solvent type antistatic agent is characterized in that the polymerizable eutectic solvent type antistatic agent is applied to the preparation of antistatic decorative impregnated bond paper, and comprises the following steps:
(a) Adding the prepared polymerizable eutectic solvent type antistatic agent into melamine impregnating adhesive to obtain antistatic melamine impregnating adhesive, wherein the mass ratio of the polymerizable eutectic solvent type antistatic agent to the melamine impregnating adhesive is 1:4-1:25;
(b) Impregnating decorative paper with antistatic melamine impregnated adhesive to obtain antistatic decorative impregnated adhesive film paper, and attaching the antistatic decorative impregnated adhesive film paper to a fiber board/blockboard to obtain an antistatic reinforced floor/ecological board;
wherein, the preparation method of the polymerizable eutectic solvent antistatic agent comprises the following steps:
(1) Drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃ according to the mole ratio of 1:0.5 to 3, heating at a constant temperature of 60 to 100 ℃, stirring and reacting for 30 minutes to 4 hours until transparent and clear liquid is formed, and cooling to room temperature to obtain a colorless and transparent eutectic solvent, wherein the hydrogen bond acceptor compound is any one or more of halogen-containing ammonium salt and halogen-containing quaternary ammonium salt; the hydrogen bond donor compound is any one or more of polymerizable carboxylic acid monomers;
(2) Adding a cross-linking agent and an initiator into the eutectic solvent, and uniformly mixing to form a mixed solution to prepare the polymerizable eutectic solvent type antistatic agent, wherein the cross-linking agent is an acrylamide monomer, the mass of the cross-linking agent accounts for 5-20% of the mass of the antistatic agent, and the initiator is a photoinitiator or a thermal initiator, and the mass of the initiator accounts for 0.1-5% of the mass of the antistatic agent.
12. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the antistatic melamine impregnated adhesive impregnated decorative paper in the step (b), wherein the polymerizable eutectic solvent type antistatic agent is mixed with the melamine impregnated adhesive to impregnate the adhesive film paper, and the impregnation amount is 0.6-1.6 times of the weight of the base paper; and (3) after twice drying, cooling to obtain the antistatic finish impregnated bond paper.
13. Use of a polymerizable eutectic solvent based antistatic agent according to claim 12, characterized in that: and (b) performing secondary drying, namely, performing primary drying at 100-120 ℃ and performing secondary drying at 130-180 ℃.
14. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the hydrogen bond acceptor compound in the step (1) is one or more of choline chloride, betaine, ammonium chloride and hexadecyl trimethyl ammonium bromide.
15. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the hydrogen bond acceptor compound in the step (1) is choline chloride.
16. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the hydrogen bond donor compound in the step (1) is one or more of maleic acid, itaconic acid, acrylic acid, methacrylic acid and lactic acid.
17. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the hydrogen bond donor compound in the step (1) is maleic acid.
18. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the stirring in the step (1) is magnetic stirring or mechanical stirring, and the stirring speed is 100-1000 rpm.
19. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the cross-linking agent in the step (2) is one or more of acrylamide, N-methylol acrylamide, N-isopropyl acrylamide and N, N-dimethyl acrylamide.
20. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the photoinitiator in the step (2) is any one of diphenyl ethanone, a-hydroxyalkyl benzophenone, dibenzoyl phenyl phosphine oxide and benzoin.
21. Use of a polymerizable eutectic solvent based antistatic agent according to claim 11, characterized in that: the thermal initiator in the step (2) is any one of ammonium persulfate, potassium persulfate, lauroyl peroxide and azodiisobutyronitrile.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108797153A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of function colouring method based on eutectic solvent |
| CN108797115A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of durable afterfinish method of fabric multifunctional based on eutectic solvent |
| WO2020031150A1 (en) * | 2018-08-09 | 2020-02-13 | Universidade Do Minho | Hair treatment composition, methods and uses thereof |
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| CN107177024A (en) * | 2017-05-23 | 2017-09-19 | 广州纽楷美新材料科技有限公司 | Application of the polymerizable eutectic solvent in electrically conducting transparent elastomer is prepared |
| CN108797153A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of function colouring method based on eutectic solvent |
| CN108797115A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of durable afterfinish method of fabric multifunctional based on eutectic solvent |
| WO2020031150A1 (en) * | 2018-08-09 | 2020-02-13 | Universidade Do Minho | Hair treatment composition, methods and uses thereof |
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