Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
  • C09K3/16—Anti-static materials
• • 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
  • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
  • C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or 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
  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
  • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
  • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L2201/00—Properties
  • C08L2201/04—Antistatic

Definitions

• the present invention relates to a solventless liquid composition, and more particularly, to a solventless liquid composition containing a polymerizable group-containing ionic liquid as a reactive diluent.
• solvent-based adhesives and solvent-based paints have been widely used not only industrially but also at home in various fields such as packaging 'bookbinding, civil engineering' architecture, electronic and electrical equipment, automotive materials, and optical components. It is used.
• adhesives and paints are generally applied to the surface to be adhered or painted as a composition in which an adhesive component or a paint component is dissolved in an organic solvent or the like, and then the solvent is removed and solidified. What is used.
• Patent Document 1 JP-A-9-20878
• Patent Document 2 JP-A-10 -71664
• Patent Document 3 Japanese Patent Application Laid-Open No. 11-302621
• Patent Document 4 Japanese Patent Application Laid-Open No. 2001-164229
• Patent Document 5 Japanese Patent Application Laid-Open No. 2001-172602
• Patent Document 6 Japanese Patent Application Laid-Open No. 2001- No.
• Patent Document 7 JP-A-2002-146284
• Patent Document 8 JP-A-2002-146285
• Patent Document 9 JP-A-2002-322419
• solvent-free adhesives and paints it is possible to work without using an organic solvent such as toluene by devising the material used as the main agent to lower the viscosity, etc. It also demonstrates the basic performance required for paints and paints.
• the reactive diluent itself reacts with the functional group of the resin and contributes to the formation of a coating film, there is an advantage that a problem such as evaporation of the residual organic solvent does not occur.
• Patent Document 10 the reactive diluent used in Patent Document 10 is still inadequate in view of the solubility of the main agent such as resin and inorganic substance and the like.
• Patent Document 1 JP-A-920878
• Patent Document 2 JP-A-10-71664
• Patent Document 3 JP-A-11-302621
• Patent Document 4 JP 2001-164229 A
• Patent Document 5 JP 2001-172602 A
• Patent Document 6 JP 2001-214144 A
• Patent Document 7 JP-A-2002-146284
• Patent Document 8 JP-A-2002-146285
• Patent Document 9 JP-A-2002-322419
• Patent Document 10 JP-A-6-299119
• the present invention has been made in view of such circumstances, and has high versatility that is excellent in safety without volatilization of an organic solvent and can reduce an environmental load! And a solvent-free liquid composition, a solvent-free adhesive, a solvent-free paint, and an antistatic agent. Means for solving the problem
• the present inventors have conducted intensive studies to achieve the above object, and as a result, obtained a solvent-free liquid composition using an ionic liquid into which a polymerizable group was introduced as a reactive diluent, using an adhesive.
• the ionic liquid stays in the adhesive layer or coating film due to the polymerization reaction, which can solve various problems caused by solvent-based adhesives, etc., safety, environmental compatibility
• the present inventors have found that a composition having excellent versatility can be obtained, and that a small polymerizable group-containing ionic liquid is also suitable as an antistatic agent, thereby completing the present invention.
• the present invention provides:
• At least one reactive group-containing low molecular organic compound (excluding polymerizable group-containing ionic liquid) and Z or at least one polymer compound, and at least one polymerizable group-containing ionic compound A reactive diluent comprising a liquid, and a solvent-free liquid composition, comprising:
• X represents a polymerizable functional group
• A represents a linear or branched hydrocarbon group having 11 to 15 carbon atoms which may contain an alkylene oxide unit
• R 1 to R 3 are each other The same or different alkyl groups having 1 to 10 carbon atoms, alkoxy groups, aryl groups or polymerizable group-containing alkyl groups. Of these R 1 to R 3 , two or more groups form a ring. ! /, You can! / ⁇ o Y indicates a monovalent key.
• X represents a polymerizable functional group
• B represents a linear hydrocarbon group having 114 carbon atoms which may contain an ethylene oxide unit
• R 1 — R 3 are the same or different. It represents an alkyl group, an alkoxy group, an aryl group, or a polymerizable group-containing alkyl group having 11 to 10 carbon atoms, and any two of R 1 to R 3 may form a ring.
• Y indicates a monovalent aeon.
• a reactive diluent comprising a polymerizable group-containing ionic liquid
• X represents a polymerizable functional group
• A represents a linear or branched hydrocarbon group having 11 to 15 carbon atoms which may contain an alkylene oxide unit
• R 1 to R 3 are each other The same or different alkyl groups having 1 to 10 carbon atoms, alkoxy groups, aryl groups or polymerizable group-containing alkyl groups. Of these R 1 to R 3 , two or more groups form a ring. ! /, You can! / ⁇ .
• R 4 represents an alkyl group, an alkoxy group, an aryl group or a polymerizable group-containing alkyl group having 110 carbon atoms.
• Y indicates a monovalent ion.
• the polymerizable group-containing ionic liquid is represented by the following general formula (2). 5 reactive diluents,
• X represents a polymerizable functional group
• B represents a linear hydrocarbon group having 114 carbon atoms which may contain an ethylene oxide unit
• R 1 — R 3 are the same or different. It represents an alkyl group, an alkoxy group, an aryl group, or a polymerizable group-containing alkyl group having 11 to 10 carbon atoms, and any two of R 1 to R 3 may form a ring.
• Y indicates a monovalent aeon.
• Solvent-free paints characterized by using any of the reactive diluents of 5-7.
• An antistatic agent comprising a polymerizable group-containing ionic liquid
• the ionic liquid containing a polymerizable group is at least one kind selected from quaternary amo-pium salt ionic liquids represented by the following general formulas (1), (3) and (4).
• Antistatic agent is at least one kind selected from quaternary amo-pium salt ionic liquids represented by the following general formulas (1), (3) and (4).
• X represents a polymerizable functional group
• A represents a linear or branched hydrocarbon group having 11 to 15 carbon atoms which may contain an alkylene oxide unit
• R 1 to R 3 are each other The same or different alkyl groups having 1 to 10 carbon atoms, alkoxy groups, aryl groups or polymerizable group-containing alkyl groups. Of these R 1 to R 3 , two or more groups form a ring. ! / .
• R 4 represents an alkyl group, an alkoxy group, an aryl group or a polymerizable group-containing alkyl group having 110 carbon atoms.
• Y indicates a monovalent ion.
• X represents a polymerizable functional group
• B represents a linear hydrocarbon group having 114 carbon atoms which may contain an ethylene oxide unit
• R 1 — R 3 are the same or different. It represents an alkyl group, an alkoxy group, an aryl group, or a polymerizable group-containing alkyl group having 11 to 10 carbon atoms, and any two of R 1 to R 3 may form a ring.
• Y indicates a monovalent aeon.
• the solvent-free liquid composition of the present invention at least one reactive group-containing low molecular weight organic compound (excluding a polymerizable group-containing ionic liquid) and Z or at least one high molecular weight compound Since it contains a molecular compound and a reactive diluent comprising at least one ionic liquid containing a polymerizable group, it is excellent in safety and environmental adaptability.
• this solvent-free liquid composition when this solvent-free liquid composition is used as an adhesive or paint, it does not contain a volatile solvent generally used for solvent-based paints and adhesives. Since the reactive liquid stays in the adhesive layer or the coating film due to the polymerization reaction, adverse effects on the human body and the environment due to solvent volatilization and the like can be prevented as much as possible.
• a reactive diluent consisting of a polymerizable group-containing ionic liquid is not only compatible with many organic compounds but also insoluble or difficult to dissolve in organic solvents, and also dissolves inorganic compounds. And various functions can be imparted to the liquid composition.
• the polymerizable group-containing ionic liquid used as a reactive diluent changes into an adhesive or a coating film component by a polymerization reaction, a drying step for removing the solvent after polymerization is not required. Yes. For this reason, the entire process of bonding and painting can be simplified, and productivity can be improved.
• the polymerizable group-containing ionic liquid used in the solvent-free liquid composition of the present invention is a compound having a cation and an ion in a molecule, and also functions as an antistatic agent. is there.
• the objects to be coated, the objects to be bonded, and the like have the same antistatic properties, although the degree differs depending on the content of the ionic liquid containing a polymerizable group.
• the adhesive layer when a polymerizable group-containing ionic liquid is used as a reactive diluent, the adhesive layer is more effective than when a quaternary ammonium salt compound having no polymerizable group is used as an antistatic agent. And the charge ratio present in the coating film can be increased, so that excellent antistatic properties are imparted.
• the antistatic agent stays in the adhesive layer or the like due to the polymerization reaction, and does not cause problems such as bleed-out.
• the solvent-free liquid composition according to the present invention comprises at least one reactive group-containing low molecular organic compound (excluding a polymerizable group-containing ionic liquid) and Z or at least one high molecular compound. And a reactive diluent comprising one kind of ionic liquid containing a polymerizable group.
• the polymerizable group-containing ionic liquid used as the reactive diluent is not particularly limited as long as it is an ionic liquid into which a polymerizable group has been introduced, but the above general formulas (1), (3) and It is preferably at least one selected from quaternary salt type ionic liquids represented by (4). Above all, considering the production cost, the raw material is inexpensive and relatively easy to synthesize, and the polymerizable group-containing ionic liquid represented by the general formula (1), particularly It is preferable to use an ionic liquid.
• the polymerizable group-containing ionic liquid can be used in combination of two or more. In this case, it is easy to adjust the viscosity of the adhesive or the coating film component to the intended use, and It is possible to improve the toughness of the adhesive layer and the coating film.
• the polymerizable functional group X is not particularly limited as long as it is a group that can participate in a polymerization reaction.
• a, j8-unsaturated carbonyl group such as (meth) acryl group, ⁇ , ⁇ Unsaturated-tolyl group, conjugated group, group having reactive unsaturated bond such as vinyl carboxylate, carboxyl group, carboxyl group, epoxy group, isocyanate group, hydroxy group, amide group, cyano group, amino group Chloromethyl group, glycidyl ether group, litho group, ester group, formyl group, nitrile group, nitro group, carbodiimide group, oxazoline group and the like.
• Examples of the linear or branched divalent hydrocarbon group having 1 to 15 carbon atoms which may contain an alkylene oxide unit include divalent carbon such as methylene, ethylene, propylene, butylene and pentylene. Examples include a hydrogen group and a group obtained by adding an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide to these groups.
• linear hydrocarbon group B having 114 carbon atoms may contain methylene, ethylene, propylene and butylene groups, and ethylene oxide may be added to these groups. Groups.
• the number of moles of alkylene (ethylene) oxide added is preferably 117.
• alkyl group having 1 to 10 carbon atoms of R 1 to R 4 , an alkoxy group, an aryl group, and a polymerizable group-containing alkyl group examples include, for example, methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, Examples include methoxy, ethoxy, propoxy, isopropoxy, s-butoxy, t-butoxy, phenyl, and benzyl groups, and groups in which the hydrogen atoms of these groups have been substituted with the above-described polymerizable groups.
• a compound in which any two groups of R 1 to R 3 form a ring refers to a compound having an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring, etc. in formulas (1) and (2).
• An ionic liquid containing a polymerizable group is exemplified.
• CF CF SO- CF CH SO-, CH CH SO-, (CF SO) N-, (CF SO) (CF (SO) N-, (CF SO) N-, etc.
• (CF SO) N— is particularly preferable.
• polymerizable group-containing ionic liquid examples include a compound represented by the following formula. These compounds can be obtained, for example, by reacting an alkyl tertiary amine having a polymerizable group with an alkyl halide and the like to quaternize, and then performing an exchange reaction with a desired aone. . It is also possible to introduce a desired anion at the same time as quaternization, for example, by reacting tert-amine with methyl paratosylate.
• polymerizable group-containing ionic liquid examples include a compound represented by the following formula. These compounds are prepared, for example, by reacting N-alkyl imidazole / pyridine with imidazolium salt / pyridi-dim salt obtained by reacting 2-methyl ethanol or the like with (meth) atari-original chloride. Can be obtained by performing an exchange reaction with the anion. Also, 2-((meth) atalyloylethyl) is added to N-alkylimidazole-pyridine. B) After the reaction with chloride, the compound can be obtained by performing an exchange reaction with a desired arnone.
• the content of the polymerizable group-containing ionic liquid in the solventless liquid composition of the present invention is not particularly limited, but the solventless liquid composition has an appropriate viscosity. In order to facilitate work such as coating and application, the content is preferably 30 to 90% by mass, more preferably 50 to 80% by mass.
• the present invention is characterized in that a polymerizable group-containing ionic liquid is used as a reactive diluent for a solventless liquid composition, and the reactive group contained in the solventless liquid composition is used as a reactive diluent.
• the low molecular weight organic compound and the high molecular weight compound are not particularly limited. Specific examples of these compounds include various conjugates commonly used as base agents, curing agents and the like in the field of adhesives and coatings.
• the reactive group-containing low molecular weight organic compound for example, a,
• a compound having at least one selected group can be used.
• the low-molecular organic compound examples include (meth) acrylic acid, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl acrylate, methyl (meth) acrylate and the like. (Meth) acrylic acid-based low molecular weight compounds, acrylonitrile, metharylic-tolyl, etalaritic-tolyl, maleo-tolyl, fumaro-tolyl, etc.
• -tolyl-based low molecular weight compounds (meth) acrylamide, ⁇ — Amide-based low-molecular compounds such as methyl (meth) acrylamide and methylol acrylamide; isocyanate-based low-molecular compounds such as toluenediisocyanate and hexamethylenediisocyanate; styrene, butadiene, vinyl chloride, and vinyl acetate; Low-molecular-weight compounds containing a carbon-carbon triple bond, such as carbon-carbon double bond-containing low-molecular weight compounds, 1-butyn-1-ol, and 1,6-heptadiyne.
• the high molecular compound for example, at least one selected from the group consisting of fluorine resin, acrylic resin, polyester resin, epoxy resin, melamine resin, silicone resin, polyurethane resin, and the like. Can be used.
• fluorinated resin examples include a terpolymer of a fluorinated vinyl monomer and a functional group-containing vinyl monomer, a terpolymer of a fluorinated vinyl monomer, a functional group-containing vinyl monomer, and other copolymerizable vinyl monomers. Polymers.
• fluorinated vinyl monomer examples include, for example, butyl fluoride, bilidene fluoride, trifluoroethylene, tetrafluoroethylene, bromotrifluorophenol, ethylene, chlorotrifluorophenol, ethylene, pentafluorophenol, hexafenole. Mouth propylene, (per) funoleoloalkyl trifluorofluoroether and the like.
• Examples of the functional group-containing monomer include hydroxyalkyl vinyl ether, hydroxypropyl vinyl ether, hydroxybutyl vinyl ether, and other hydroxyalkyl ethers, 2-hydroxyethyl (meth) acrylate, 2-hydroxyethyl ether, and the like.
• Hydroxyalkyl (meth) acrylates and other hydroxyalkyl (meth) acrylates and other hydroxyl-containing butyl monomers acrylic acid, methacrylic acid, maleic acid, anhydrous maleic acid, itaconic acid, itaconic anhydride, fumaric acid Carboxyl group-containing monomer such as acid; dimethylaminoethyl vinyl ether, dimethylaminopropyl butyl ether, N, N-dimethylaminopropyl (meth) acrylamide, dimethylaminoethyl (meth) phthalate Amino group-containing Bulle monomers such like.
• Examples of other copolymerizable vul monomers include alkyl butyl ether, aliphatic carboxylic acid butyl ester, aromatic carboxylic acid butyl ester, epoxy group-containing butyl monomer, carboxyl group-containing butyl monomer, and halogenated butyl monomer. , Aromatic vinyl monomers, (meth) acrylic acid derivatives and the like.
• Each of the above-mentioned fluorine-containing vinyl monomer, functional group-containing monomer, and copolymerizable monomer can be used alone or in combination of two or more.
• acrylic resin examples include, for example, a polymer obtained by polymerization and copolymerization of an acrylic or methacrylic monomer, or a copolymer of an acrylic or methacrylic monomer and a monomer copolymerizable with them. And the like.
• acrylic and methacrylic monomers examples include acrylic acid, methacrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, and i- (meth) acrylic acid.
• methoxydiethylene glycol (meth) atalylate methoxy nona ethylene glycol (meth) atalylate
• NK ester 2G manufactured by Shin-Nakamura-Danigaku Co., Ltd.
• NK ester 9G manufactured by Shin-Nakamura-danigaku Co., Ltd.
• (Meth) acrylic acid monoesters or (meth) acrylic acid diesters having an alkylene oxide as a repeating unit such as NK ester 23G (manufactured by Shin-Nakamura-Danigaku Co., Ltd.)
• TMPT Shin-Nakamura Chemical And polyfunctional (meth) acrylic acid derivatives having a plurality of (meth) acryl groups in the molecule.
• the copolymerizable monomer is not particularly limited as long as it is a monomer having a functional group copolymerizable with an acrylic or methacrylic monomer. Chlorotolyl, vinyl chloride, bilidene chloride, vinyl acetate, dimethyl itaconate, getyl maleate, ethyl vinyl ether, styrene, vinyltoluene, ⁇ -methylstyrene, butylpyridine, dibutylbenzene, dibutyl adipate, etc. No.
• polyester resin examples include polybasic acids such as phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, succinic acid, adipic acid, sebacic acid, azelaic acid, trimellitic acid, and ethylene glycol.
• polybasic acids such as phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, succinic acid, adipic acid, sebacic acid, azelaic acid, trimellitic acid, and ethylene glycol.
• the melamine resin examples include a resin obtained by reacting melamine with formalin and modifying an initial condensate of methylolated melamine with butanol or the like, and a resin soluble in an organic solvent is preferable.
• epoxy resin examples include bisphenol A type epoxy resin, brominated bisphenol A type epoxy resin, other polyphenol type, polyglycidylamine type, alcohol type, and ester type.
• the silicone resin is, for example, a resin based on a polysiloxane obtained by polycondensation of silanol by hydrolysis of dimethyldichlorosilane, methylphenyldichlorosilane or the like, and is a dimethylsiloxane or methylphenolsiloxane unit.
• a silicone resin of a silicone type a part of which is substituted with a butyl group
• a silicone resin of a ferrule silicone type for example, a resin based on a polysiloxane obtained by polycondensation of silanol by hydrolysis of dimethyldichlorosilane, methylphenyldichlorosilane or the like.
• examples thereof include a silicone resin of a silicone type, a part of which is substituted with a butyl group, and a silicone resin of a ferrule silicone type.
• polyurethane resins examples include isocyanates such as 2,4-tolylene diisocyanate, 2,4-tolylene diisocyanate, hexamethylene diisocyanate, and ethylene oxide, propylene oxide, propylene glycol, Examples thereof include polyurethane resins and the like obtained by subjecting at least one kind of glycolca such as butanediol to an addition reaction.
• the above-described polymer compound has a reactive group! /, Or has or does not have to have a reactive group.
• the reactive dilution is used.
• a polymer compound containing a reactive group include fluorine resin, acrylic resin, polyester resin, epoxy resin, melamine resin, silicone resin, polyurethane resin and the like containing a reactive group.
• the solvent-free liquid composition of the present invention comprises a reactive dilution comprising various reactive group-containing low molecular weight organic compounds and Z or high molecular weight compounds, and a polymerizable group-containing ionic liquid.
• the ratio of the reactive group-containing low molecular weight organic compound and Z or the high molecular weight compound to the polymerizable group-containing ionic liquid in the composition is, for example, the mass ratio 70: 30-1: 99, preferably 60: 40-10: 90, more preferably 50: 50-20: 80.
• the solvent-free liquid composition of the present invention includes, in addition to the reactive group-containing low molecular weight organic compound, the high molecular weight compound, and the reactive diluent, optional components used in adhesives, paints, and the like, if necessary. Included.
• Specific optional components include an antifoaming agent, an antioxidant, an ultraviolet absorber, a plasticizer, a surfactant, a dye, a pigment, organic or inorganic fine particles, and the like.
• the solvent-free liquid composition of the present invention may be prepared by any method, including a reactive group-containing low molecular weight organic compound and Z or a high molecular weight compound, a reactive diluent comprising a polymerizable group-containing ionic liquid, and others. Can be prepared by mixing the above optional components in an appropriate order and stirring the mixture.
• the liquid is a concept including various forms such as a uniform solution, an emulsion, and a suspension.
• the solvent-free liquid composition of the present invention is suitable as a composition for an adhesive or a composition for a coating.
• the adhesive is not particularly limited.
• epoxy-based adhesives such as epoxy-phenolic, epoxy polyamide-based, epoxy-tolyl rubber-based, and epoxy vulcanized acrylic rubber-based adhesives, nitrile-phenolic-based adhesives
• Phenol-based adhesives such as butyl-phenolic adhesives, acrylic resin-based adhesives, urethane resin-based adhesives, silicone-based adhesives, rubber-based adhesives, etc., in solvent-free liquid compositions.
• the required adhesive composition can be prepared by appropriately selecting the reactive group-containing low molecular weight organic compound and the high molecular compound contained therein.
• the solvent-free liquid composition of the present invention can be used as a functional adhesive such as an ultraviolet-curable adhesive, a visible-curable adhesive, an elastic adhesive, a heat-resistant adhesive, a pressure-sensitive adhesive, and a conductive adhesive. Can also be applied.
• a functional adhesive such as an ultraviolet-curable adhesive, a visible-curable adhesive, an elastic adhesive, a heat-resistant adhesive, a pressure-sensitive adhesive, and a conductive adhesive. Can also be applied.
• the coating material is not particularly limited. Examples thereof include nitrocellulose, alkyd resin, amino alkyd resin, vinyl resin, acrylic resin, epoxy resin, and urethane. Resin-based, polyester resin-based, salt-based rubber-based, paint silicone resin-based, fluorine resin-based paint, etc., also in this case containing a reactive group contained in the solventless liquid composition. By appropriately selecting the low molecular weight organic compound and the high molecular weight compound, the required coating composition can be prepared.
• the solvent-free liquid composition of the present invention When used as a composition for an adhesive, for example, the solvent-free liquid composition prepared by an appropriate method as described above may be used to prepare one of the adherends. After applying to the adhesion surface, laminating and fixing the other adherend on this, depending on the type of the reactive group in the solventless liquid composition, heating, ultraviolet irradiation, electron beam irradiation, etc. It should be cured and bonded in a suitable way.
• the type of the reactive group in the composition is determined in the same manner as the adhesive composition. May be cured by a curing method according to the above to form a coating film.
• the polymerizable group-containing ionic liquid of the present invention has a cation and an ion in the molecule, it can be suitably used as an antistatic agent.
• an antistatic agent regardless of whether it is a solvent type or a non-solvent type, it can be used by adding it to a liquid composition or by adding it to a composition for obtaining a resin molded article. ⁇ ⁇ ⁇ Can be kneaded into fat.
• the compounding amount of the antistatic agent in each composition is not particularly limited as long as the composition contains about 0.01 to 30% by mass in the composition.
• an antistatic film may be produced by polymerizing the above-mentioned antistatic agent having a polymerizable group-containing ionic liquid alone, or an antistatic agent comprising a polymerizable group-containing ionic liquid. May be applied to an object to be coated such as a resin molded product, and then polymerized alone to form an antistatic coating.
• the polymerization conditions as described above, heating, ultraviolet light
• An appropriate method depending on the polymerizable group, such as irradiation or electron beam irradiation, may be used.
• the polymerizable group-containing ionic liquid stays inside the film or coating due to its polymerization reaction, so that adverse effects on the human body and environment due to solvent volatilization, etc. can be prevented as much as possible after polymerization. No drying step is required for removing the solvent.
• the polymerizable group-containing ionic liquid When the polymerizable group-containing ionic liquid is used as an antistatic agent, only the polymerizable group-containing ionic liquid may be used, but the defoaming agent is contained in the polymerizable group-containing ionic liquid.
• Optional components such as an antioxidant, an ultraviolet absorber, a plasticizer, a surfactant, a dye, a pigment, and organic or inorganic fine particles can also be added.
• the separated organic layer was washed by adding an appropriate amount of ion-exchanged water to remove impurities in the organic layer.
• the organic layer after washing was removed with a vacuum pump to remove water, and 16.27 g of a polymerizable group-containing ionic liquid (9) was obtained.
• the separated organic layer was washed by adding an appropriate amount of ion-exchanged water to remove impurities in the organic layer.
• the organic layer after washing was removed with a vacuum pump to remove water, and 13.28 g of a polymerizable group-containing ionic liquid (10) was obtained.
• reaction solution was extracted with tetrahydrofuran, dried over potassium carbonate (manufactured by Wako Pure Chemical Industries, Ltd.), filtered, and the filtrate was separated with a silica gel column to give N-methyl-N- (2-methoxyethyl) amino. 5.14 g of ethyl methacrylate was obtained.
• the separated organic layer was washed by adding an appropriate amount of ion-exchanged water to remove impurities in the organic layer.
• the organic layer after washing was removed with a vacuum pump to remove water, and 5.20 g of a polymerizable group-containing ionic liquid (12) was obtained.
• Polymerizable group-containing ionic liquid (6) prepared in Synthesis Example 1 (Examples 1, 2, 6), Prepared polymerizable group-containing ionic liquid (9) (Examples 3-6), polymerizable group-containing ionic liquid (10) prepared in Synthesis Example 3 (Examples 7, 8), prepared in Synthesis Example 4 Polymerizable group-containing ionic liquid (11) (Examples 9 and 10), polymerizable group-containing ionic liquid (12) prepared in Synthesis Example 5 (Example 11), 2-hydroxyethyl methacrylate (Mitsubishi Gas Chemical Co., Ltd., called 2-HEMA), trimethylolpropane trimethacrylate (TMP, manufactured by Shin-Nakamura-Danigaku Co., Ltd.) 2,2'-Dimethylphenolacetone (Tokyo (Manufactured by Kasei Co., Ltd.) at the ratios shown in Table 1 to prepare a liquid ultraviolet-curable adhesive composition.
• Example 6 the polymerizable group
• EXAMPLE 1 one 11 adhesive composition obtained, in size 3. OCM X 4. Poryechi terephthalate film on the OCM, was applied in an amount of 5. 0 X 10- 3 g / cm 2 Then, another polyethylene terephthalate film of the same size was laminated thereon, and then cured by irradiating ultraviolet rays (160 W / cm 2 ) for 10 seconds to bond the two films together. The two bonded films were peeled off, and the adhesion was evaluated according to the following criteria.
• Polymerizable group-containing ionic liquid (6) 80 parts by mass, 2-hydroxyethyl methacrylate (Mitsubishi Gas Chemical Co., Ltd.) 20 parts by mass, Macrolex Blue 3R Gran (Bayer Yakuhin Ltd.) 2 parts by mass Then, 0.5 parts by mass of 2,2′-dimethoxyphenylacetone as a photopolymerization initiator was mixed to prepare a liquid ultraviolet-curable coating composition.
• the obtained coating composition was applied to a solvent-washed 100 ⁇ m-thick polyethylene-terephthalate film to a thickness of 5.0 m with a bar coater, and irradiated with ultraviolet rays (160 WZcm 2 ) for 10 seconds. It was cured to form a coating film.
• An ultraviolet-curable coating composition was prepared in the same manner as in Example 12, except that the polymerizable group-containing ionic liquid (9) was used. A coating film was formed on the obtained coating composition in the same manner as in Example 12.
• the polymerizable group-containing ionic liquid (9) is applied to a solvent-washed 100- ⁇ m-thick polyethylene-terephthalate film with a bar coater so that the thickness becomes 5.0 m, and ultraviolet rays (160 W / cm ) For 15 minutes to cure.
• the pencil hardness, adhesion, and surface resistance of the obtained coating film were measured in the same manner as in Example 12. As a result, the pencil hardness was 4H, the adhesion was OZ36, and the surface resistance was 3.2 ⁇ 10 9 ( ⁇ ).

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