CN114591466A - Preparation method and application of polymerizable eutectic solvent type antistatic agent - Google Patents
Preparation method and application of polymerizable eutectic solvent type antistatic agent Download PDFInfo
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- CN114591466A CN114591466A CN202210223572.0A CN202210223572A CN114591466A CN 114591466 A CN114591466 A CN 114591466A CN 202210223572 A CN202210223572 A CN 202210223572A CN 114591466 A CN114591466 A CN 114591466A
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- China
- Prior art keywords
- eutectic solvent
- antistatic agent
- hydrogen bond
- polymerizable
- type antistatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000005496 eutectics Effects 0.000 title claims abstract description 64
- 239000002904 solvent Substances 0.000 title claims abstract description 61
- 239000002216 antistatic agent Substances 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 21
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 6
- 235000019743 Choline chloride Nutrition 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 6
- 229960003178 choline chloride Drugs 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- 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 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- 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 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 229960001040 ammonium chloride Drugs 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- 238000003760 magnetic stirring Methods 0.000 claims description 2
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 238000003848 UV Light-Curing Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000004090 dissolution Methods 0.000 abstract description 3
- 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
- 229920000877 Melamine resin Polymers 0.000 description 22
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 21
- 239000002023 wood Substances 0.000 description 19
- 238000007598 dipping method Methods 0.000 description 18
- 239000003292 glue Substances 0.000 description 15
- 239000000123 paper Substances 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 238000006116 polymerization reaction 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
- 230000003068 static effect Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000007761 roller coating Methods 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
- 239000002131 composite material Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000011094 fiberboard 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
- 150000002739 metals Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 239000000843 powder 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
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-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
- 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
- 238000005034 decoration Methods 0.000 description 1
- 229940079593 drug Drugs 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
- 238000004880 explosion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920002521 macromolecule Polymers 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
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 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 ℃, and mixing the dried hydrogen bond donor compound and the hydrogen bond acceptor compound according to a molar ratio of 1: 0.5-3, heating at the constant temperature of 60-100 ℃, stirring for reaction for 30 min-4 h until a transparent clear liquid is formed, and cooling to room temperature to prepare a colorless transparent eutectic solvent; adding a cross-linking agent and an initiator into the eutectic solvent, and uniformly mixing to form a mixed solution, thus obtaining the eutectic solvent. The prepared polymerizable eutectic solvent type antistatic agent is applied to preparation of UV curing antistatic acrylic coating and antistatic decorative impregnated bond paper. The invention can stably polymerize without using additional liquid solvent for dissolution, avoids the use of toxic organic solvents with high boiling points, 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 cause many hazards, such as surface dust collection, electronic device breakdown, explosion and the like. Therefore, the market demand for the floor/wall board with antistatic function is increasing, especially in public places such as schools, hospitals, nursing homes, stadiums and the like.
The wood floor/wallboard is one of the preferred decorating materials of consumers at present, and the surface decoration/coating material commonly used for the wood floor/wallboard is paint or melamine impregnated bond paper, so in order to realize the wood floor/wallboard with the antistatic function, the paint or the melamine impregnated bond paper needs to be subjected to antistatic treatment, and the main method is to add a proper antistatic agent.
The antistatic agents commonly used at present mainly include two categories, i.e., 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 oxides thereof, conductive polymers, and the like; surfactants dissipate static charges by migrating to the surface and adsorbing moisture from the surrounding environment to form a conductive water film, typically quaternary ammonium salts. The main defects of applying the surfactant type antistatic agent to the wood floor/wallboard are that the antistatic durability is poor, the scrubbing resistance is not high, the dependence on the environmental humidity is large, and the use of the surfactant type antistatic agent is limited; the main disadvantages of the conductive materials, such as carbon materials, metals and oxides thereof, are their opacity, influence on the decorative color, and high cost, which limits their wide use.
The ionic liquid is a liquid plasma at room temperature, has the characteristics of conductivity, designable molecular structure and the like, and has good application prospect in the aspects of polymer antistatic and the like, wherein imidazole ionic liquid antistatic agents and the like are widely reported. However, the imidazole ionic liquid antistatic agent has high cost, and the application of the imidazole ionic liquid antistatic agent in wood floor/wallboard coating or impregnating glue is limited.
The eutectic solvent is a special ionic liquid, and has the advantages of low vapor pressure, chemical stability, non-inflammability, high dissolving capacity, low toxicity, environmental friendliness, 100% of atom utilization rate in the preparation process, low cost and the like. At present, eutectic solvents are mainly applied to the aspects of dissolving medicines, purifying, electrodepositing, material preparation, capturing carbon dioxide, processing biological macromolecules and the like, and relatively few reports are made on the application of polymerizable eutectic solvents to antistatic agents.
Therefore, a polymerizable eutectic solvent applied to the antistatic agent of the coating/melamine impregnated bond paper needs to be explored, so that the durability of the antistatic property can be improved, and the lower cost and the better environment friendliness can be realized.
Disclosure of Invention
In view of the defects in the prior art, the invention aims to provide a preparation method of a polymerizable eutectic solvent type antistatic agent.
A preparation method of a polymerizable eutectic solvent type antistatic agent comprises the following steps:
(1) drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃, and mixing the dried hydrogen bond donor compound and the hydrogen bond acceptor compound according to a molar ratio of 1: 0.5-3, heating at the constant temperature of 60-100 ℃, stirring for reaction for 30 min-4 h until a transparent clear liquid is formed, and cooling to room temperature to prepare a colorless and transparent eutectic solvent, wherein the hydrogen bond acceptor compound is 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) and 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 and accounts for 5-20% of the mass of the antistatic agent, and the initiator is a photoinitiator or a thermal initiator and 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, and 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, and 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 crosslinking agent in the 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 diphenylethanone, alpha-hydroxyalkyl benzophenone, bis-benzoylphenyl phosphine oxide and benzoin; the thermal initiator is any one of ammonium persulfate, potassium persulfate, lauroyl peroxide and azobisisobutyronitrile.
The prepared polymerizable eutectic solvent antistatic agent forms a conductive high polymer network in a matrix, has the characteristics of excellent antistatic performance, lasting electrostatic protection, small influence of 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.
Still another object of the present invention is 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 (ultraviolet) 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 on the surface and the sub-surface of a solid wood floor/wallboard or a solid wood composite floor/wallboard, preferably roller coating, and the total coating weight is not less than 16g/m2。
The third purpose of the 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 dipping glue to obtain the antistatic melamine dipping glue, wherein the mass ratio of the polymerizable eutectic solvent type antistatic agent to the melamine dipping glue is 1: 4-1: 25;
(2) and (3) dipping the antistatic melamine dipping glue into the decorative paper to obtain antistatic decorative dipping glue film paper, and sticking the antistatic decorative dipping glue film paper on the fiber board/the block board to obtain the antistatic strengthened floor/ecological board.
Preferably, the antistatic melamine impregnated adhesive is used for impregnating decorative paper, a polymerizable eutectic solvent type antistatic agent and melamine impregnated adhesive are mixed and then impregnated into adhesive film paper, and the impregnation amount is 0.6-1.6 times of the weight of the original paper; after two times of drying (the first drying temperature is 100-120 ℃, the second drying temperature is 130-180 ℃), cooling to obtain the antistatic veneer impregnated bond paper; and (3) sticking the melamine impregnated bond paper veneer antistatic wood floor/wallboard on the surface of the base material.
Advantageous effects
The invention mixes and heats a hydrogen bond donor compound (solid powder/liquid) and a hydrogen bond acceptor compound (solid powder) to obtain a stable nontoxic polymerizable eutectic solvent, then uses the eutectic solvent as a monomer of front-end polymerization and acrylic resin/melamine resin to carry out self polymerization and cross-linking polymerization to form the polymerizable eutectic solvent type antistatic agent, and applies the polymerizable eutectic solvent type antistatic agent to the preparation of antistatic acrylic coating/melamine impregnated bond paper. The method can stably polymerize without using additional liquid solvent for dissolution, 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 below with reference to examples to provide those skilled in the art with a better understanding of the present invention, but the present invention is not limited to the following examples.
Example 1
A preparation method of a polymerizable eutectic solvent type 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 ℃, and magnetically stirring at 500rpm for 3 hours until a transparent and clear liquid is formed, thus obtaining a eutectic solvent;
(2) 5.055g of N-hydroxymethyl acrylamide and 0.134g of diphenylethanone are added into the eutectic solvent and stirred for dissolution to obtain the UV polymerization eutectic solvent type antistatic agent.
The prepared UV polymerization eutectic solvent type antistatic agent is added into 223.61g of UV curing acrylic coating to obtain the UV curing antistatic acrylic coating.
The UV-cured antistatic acrylic coating is coated at a coating weight of 14g/m2And (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 prepared antistatic wood floor/wallboard is 4 multiplied by 109Ω。
Example 2
A preparation method of a polymerizable eutectic solvent type antistatic agent comprises the following steps:
(1) weighing 13.963g of choline chloride and 13.01g of itaconic acid, drying in an 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-isopropylacrylamide and 0.10g of ammonium persulfate are added into the eutectic solvent and stirred and dissolved to obtain the heat-polymerizable eutectic solvent type antistatic agent.
The prepared thermal-polymerizable eutectic solvent type antistatic agent is added into 134.1g of melamine dipping glue to obtain the antistatic melamine dipping glue. Because the heat-polymerizable eutectic solvent type antistatic agent has the function of a curing agent of melamine impregnated glue, no additional curing agent is needed.
Dipping 80g of decorative paper by using 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 that the antistatic melamine decorative adhesive film paper is obtained; and (3) attaching the adhesive to the surface of the fiber board to obtain the antistatic strengthened floor/wallboard.
The surface resistance of the prepared antistatic wood floor/wallboard is 8 multiplied by 108Ω。
Example 3
A preparation method of a polymerizable eutectic solvent type antistatic agent comprises the following steps:
(1) weighing 11.715g of betaine and 14.412g of acrylic acid, drying the betaine in an 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 clear liquid is formed, thereby obtaining a eutectic solvent;
(2) 3.92g of acrylamide and 0.150g of alpha-hydroxyalkylphenone were added to the eutectic solvent and dissolved by stirring to obtain a UV polymerizable eutectic solvent type antistatic agent.
And adding the prepared UV polymerization eutectic solvent type antistatic agent into 180g of UV curing acrylic coating to obtain the UV curing antistatic acrylic coating.
The UV-cured antistatic acrylic coating is coated at the weight of 15g/m2And (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 prepared antistatic wood floor/wallboard is 9 multiplied by 108Ω。
Example 4
A preparation method of a polymerizable eutectic solvent type 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 liquid was formed, yielding a eutectic solvent.
(2) 6.82g N, N-dimethylacrylamide and 0.30g of potassium persulfate were added to the eutectic solvent and dissolved with stirring to obtain a heat-polymerizable eutectic solvent-based antistatic agent.
The prepared thermal-polymerizable eutectic solvent type antistatic agent is added into 600g of melamine dipping glue to obtain the antistatic melamine dipping glue. Because the heat-polymerizable eutectic solvent type antistatic agent is acidic and has the function of a curing agent of melamine dipping glue, no additional curing agent is needed.
Dipping 80g of decorative paper by using antistatic melamine dipping glue, wherein the dipping amount is 100g, the first drying temperature is 120 ℃, and the second drying temperature is 150 ℃, so that antistatic melamine decorative adhesive film paper is obtained; and (3) sticking the floor board to the surface of the joinery board to obtain the antistatic strengthened floor/wallboard.
The surface resistance of the prepared antistatic wood floor/wallboard is 3 multiplied by 109Ω。
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes performed by the present invention or directly or indirectly applied to other related technical fields are included in the scope of the present invention. It should be noted that the above-mentioned embodiments are only for explaining the present invention, and do not set any limit to the present invention. The present invention has been described with reference to exemplary embodiments, but the words which have been used herein are words of description and illustration, rather than words of limitation. The invention can be modified, as prescribed, within the scope of the claims and without departing from the scope and spirit of the invention. Although the invention has been described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, but rather extends to all other methods and applications having the same functionality.
Claims (10)
1. The preparation method of the polymerizable eutectic solvent type antistatic agent is characterized by comprising the following steps of:
(1) drying the hydrogen bond donor compound and the hydrogen bond acceptor compound at 60-80 ℃, and mixing the dried hydrogen bond donor compound and the hydrogen bond acceptor compound according to a molar ratio of 1: 0.5-3, heating at the constant temperature of 60-100 ℃, stirring for reaction for 30 min-4 h until a transparent clear liquid is formed, and cooling to room temperature to prepare a colorless and transparent eutectic solvent, wherein the hydrogen bond acceptor compound is 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) and 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 and accounts for 5-20% of the mass of the antistatic agent, and the initiator is a photoinitiator or a thermal initiator and accounts for 0.1-5% of the mass of the antistatic agent.
2. The method for preparing the polymerizable eutectic solvent-type antistatic agent according to claim 1, wherein: the hydrogen bond receptor compound in the step (1) is one or more of choline chloride, betaine, ammonium chloride and hexadecyl trimethyl ammonium bromide, and choline chloride is preferred.
3. The method for preparing the polymerizable eutectic solvent-type antistatic agent according to claim 1, wherein: 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, preferably maleic acid.
4. The method for preparing the polymerizable eutectic solvent-type antistatic agent according to claim 1, wherein: the stirring in the step (1) is magnetic stirring or mechanical stirring, and the stirring speed is 100-1000 rpm.
5. The method for preparing the polymerizable eutectic solvent type antistatic agent according to claim 1, characterized in that: the cross-linking agent in the step (2) is one or more of acrylamide, N-methylolacrylamide, N-isopropylacrylamide and N, N-dimethylacrylamide.
6. The method for preparing the polymerizable eutectic solvent-type antistatic agent according to claim 1, wherein: the photoinitiator in the step (2) is any one of diphenylethanone, alpha-hydroxyalkyl benzophenone, bis-benzoyl phenyl phosphine oxide and benzoin.
7. The method for preparing the polymerizable eutectic solvent-type antistatic agent according to claim 1, wherein: the thermal initiator in the step (2) is any one of ammonium persulfate, potassium persulfate, lauroyl peroxide and azobisisobutyronitrile.
8. A polymerizable eutectic solvent based antistatic agent prepared according to the method of any one of claims 1 to 7.
9. Use of the polymerizable eutectic solvent-based antistatic agent according to claim 8, wherein: the UV-curable antistatic acrylic coating is applied to the preparation of UV-curable antistatic acrylic coatings.
10. Use of the polymerizable eutectic solvent-based antistatic agent according to claim 8, wherein: the preparation method is applied to the preparation of the antistatic decorative impregnated bond paper.
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| 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 |
| CN108797153A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of function colouring method 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 |
| 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 |
| CN108797153A (en) * | 2018-06-21 | 2018-11-13 | 东华大学 | A kind of function colouring method 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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