CN101898981A - Antistatic ionic compound, oligomer thereof, copolymer thereof and pressure-sensing agglutinant component thereof - Google Patents
Antistatic ionic compound, oligomer thereof, copolymer thereof and pressure-sensing agglutinant component thereof Download PDFInfo
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- CN101898981A CN101898981A CN2010102393238A CN201010239323A CN101898981A CN 101898981 A CN101898981 A CN 101898981A CN 2010102393238 A CN2010102393238 A CN 2010102393238A CN 201010239323 A CN201010239323 A CN 201010239323A CN 101898981 A CN101898981 A CN 101898981A
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Abstract
The invention relates to an antistatic ionic compound, an oligomer thereof, a copolymer thereof and a pressure-sensing agglutinant component thereof, wherein the pressure-sensing agglutinant component contains the ionic compound, the oligomer thereof, the copolymer thereof or the compound thereof containing (methyl) ammonium crylic esters cation and (CF3SO2)2N-anion, so the formed pressure-sensing adhering slice has an excellent antistatic property and a stable adhering property. The invention is suitable for being used in the plastics which easily generate static and the electronic products which have no static, such as a Polaroid, and the like.
Description
Technical field
The present invention relevant a kind of antistatic ionic compound, its oligomer, its multipolymer and contain its pressure-sensitive tackiness agent constituent, particularly relevant a kind of antistatic composition and contain its vinylformic acid pressure-sensing glue constituent, the tackiness of its tool excellence and static resistance.
Background technology
Pressure-sensitive tackiness agent (pressure-sensitive adhesives, PSAs) be to presser sensor, only the need contact pressure just can be with two kinds of tackiness agents that differing materials is glued together, use and extensively reach facility, be applied at present in the flat display apparatus, for example as the gum of the Polarizer of liquid-crystal display.
Known pressure-sensitive tackiness agent is made up of organic polymer material, generally has high-insulativity matter, so can produce static when rubbing or divesting.Therefore desire and display panels is done when sticking together when Polarizer; when on divesting pressure-sensitive adhesion sheet, being used for protecting the release film of pressure-sensitive adhesion sheet; can produce static because of friction makes pressure-sensitive adhesion sheet; cause dust absorption and pollute optical component; in addition also can the break disappearance of (electrostatic breakage) of static appear at the peripheral circuit element; cause because the undesired demonstration phenomenon that the liquid crystal orientation confusion is caused; so, need do antistatic treatment to the pressure-sensitive adhesive coating for fear of above-mentioned disappearance.
Desire solves the problem that buildup of static electricity produced, and the electroconductibility that increases material is general and efficient manner.The electrostatic charges accumulated method of control at present the most normal use be to utilize to increase aqueous vapor absorption to improve material electroconductibility, in general can increase the context moisture or use hygroscopic static inhibitor to reach, most static inhibitor is to be used to eliminate the cumulative static charge.
The chemical species that known antistatic kind contains comprises organic amine, acid amides, polyoxyethylene deriv, and organic substance such as polyvalent alcohol, or inorganic substance such as metal-powder, carbon dust, inorganic salts, even there have many interface promoting agents that can be, its character can be to be neutral or ionic.When adding metal-powder or carbon dust, easily cause the transparency not good, influence the optical property of pressure-sensitive tackiness agent.When adding polyoxyethylene deriv, therefore the class interfacial agent reduces the performance of pressure-sensitive tackiness agent to pressure-sensitive tackiness agent surface transport.Alkali metal cation (particularly lithium), because of it has good wettability power, so an alkali metal salt also often is used the usefulness as static inhibitor.In addition, room temperature melting salt such as ionic liquid also can be used as the static inhibitor use.But usually among the composition of polymkeric substance, to note the consistency of these static inhibitor and polymkeric substance especially, otherwise can produce unsuitable antistatic usefulness or tangible inapplicability be arranged in the physical properties or the outward appearance of final product or object.
Therefore, still need a kind of static inhibitor of novelty and contain the pressure-sensitive tackiness agent constituent of this kind static inhibitor, the two has good consistency, and makes the pressure-sensitive adhesion sheet of formation have good static resistance, and does not influence the adhesion function.
Summary of the invention
One of purpose of the present invention provides a kind of ionic compound, it has anti-static function, and provide a kind of pressure-sensitive tackiness agent constituent that contains this kind ionic compound as antistatic composition, this kind ionic compound and pressure-sensitive tackiness agent composition consistency are good, can make the pressure-sensitive adhesion sheet of formation have good static resistance, and do not influence the adhesion function, and have excellent adhesion confidence level.
According to ionic compound of the present invention, it has chemical formula (I):
Wherein, R is hydrogen base or methyl; R1, R2, and R3 independently be the alkyl of carbon number 1 to 6 separately; And n is 1 to 16 integer.
In another aspect of the present invention, according to oligomer of the present invention, be to close product as monomeric oligomerization by ionic compound as the aforementioned.
In another aspect of the present invention, according to multipolymer of the present invention, be by ionic compound as the aforementioned as monomer altogether and at least a can with the common monomeric copolymerization product of acryl reaction.
In another aspect of the present invention, according to pressure-sensitive tackiness agent constituent of the present invention, comprise be selected from aforesaid ionic compound, be monomeric oligomer, and multipolymer and make up one of them of formed cohort with ionic compound as the aforementioned; And pressure-sensing glue polymkeric substance.
As optional technical scheme, this pressure-sensitive tackiness agent constituent with the total amount of this composition (a) and this composition (b) be 100 weight percent meters it, this ionic compound accounts for 0.01 to 20 weight percent.
As optional technical scheme, this pressure-sensitive tackiness agent constituent further comprises solvent.
As optional technical scheme, this pressure-sensing glue polymkeric substance comprises that weight average molecular weight is 100,000 to 5,000,000 the polymkeric substance based on (methyl) propenyl.
As optional technical scheme, should comprise the product that forms as the copolymerization of common monomer institute by butyl acrylate, vinylformic acid, with methacrylic acid dihydroxyl ethyl ester based on polymkeric substance of (methyl) propenyl.
As optional technical scheme, with this amount based on the polymkeric substance of (methyl) propenyl is that 100 weight percents are as the criterion, and butyl acrylate, vinylformic acid, accounts for 80 to 99 weight percents, 0.1 to 15 weight percent, and 0.1 to 5 weight percent respectively with the amount of methacrylic acid dihydroxyl ethyl ester.
Pressure-sensitive tackiness agent constituent of the present invention contains a kind of ionic compound, its oligomer or multipolymer of novelty, this kind ionic compound is made of (methyl) ammonium acrylate alkane ester cationoid and (CF3SO2) 2N-negatively charged ion, make the pressure-sensitive adhesion sheet that forms have excellent static resistance, and tackiness can variation, be applicable to easy generation electrostatic plasthetics, and do not desire that electronic products such as electrostatic apparatus such as polaroid are arranged.
Can be further understood by following embodiment detailed description in the advantages and spirit of the present invention.
Embodiment
Can be used as the foundation ionic compound of the present invention of antistatic composition, it has general formula shown in following chemical formula (I):
Wherein, R can be hydrogen base or methyl; R1, R2, and R3 be alkyl, if consider steric barrier and reaction difficulty, preferable can be independent separately be carbon number 1 to 6, be preferably 1 to 4 alkyl; Reaching n is 1 to 16, is preferably 1 to 8, is more preferred from 1 to 6 integer.Make-(CH) the n-carbochain is long better than R1, R2, R3.
This ionic compound is made of (methyl) ammonium acrylate alkane ester cationoid and (CF3SO2) 2N-negatively charged ion." (methyl) vinylformic acid " expression " vinylformic acid " or " methacrylic acid ".Because cationic part has (methyl) acrylic acid groups, therefore can form with the pressure-sensing glue of acrylic acid or the like has good consistency.
In another aspect of the present invention, the oligomer of the ionic compound of above-mentioned chemical formula (I) expression also can be used as good antistatic composition.This kind oligomer obtains as monomer above-mentioned ionic compound via polyreaction.The polymeric position is the two keys on the propenyl.Employed polymerization methods is not limited to specific a kind of, but is good with solution polymerization, mass polymerization, suspension polymerization, letex polymerization and photopolymerization, especially with solution polymerization for better.Polymerization methods is to add a kind of initiator initiated polymerization, and initiator can be azo polymerization initiator, such as Diisopropyl azodicarboxylate and azo bicyclohexane nitrile, or superoxide such as benzoyl peroxide, acetyl peroxide and both mixtures.Under 50 to 100 ℃, carry out polyreaction with initiator.
In of the present invention again on the other hand; as above-mentioned polyreaction; but wherein polymerization single polymerization monomer does not exceed with the ionic compound of chemical formula (I) expression, and can be to make the ionic compound of representing with chemical formula (I) as being total to monomer and the multipolymer that can carry out the copolymerization gained with the common monomer of acryl reaction.Can with the common monomer of acryl reaction, for example can be (methyl) propenyl monomer, for example (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) n-butyl acrylate or (methyl) 2-EHA; Vinyl monomer, for example vinyl acetate, vinylbenzene or V-Pyrol RC; Or its combination.To be total to and carry out copolymerization after monomer mixes, the multipolymer that is obtained also has static resistance, and applicable in the pressure-sensitive tackiness agent constituent of the present invention.
According to pressure-sensitive tackiness agent constituent of the present invention, comprise that the pressure-sensing glue polymkeric substance is the ionic compound of composition and chemical formula (I) expression or is combined as another composition with it as monomeric oligomer or multipolymer or its.The amount of these two kinds of compositions is also without particular limitation, but in view of the tackiness and the static resistance of formed pressure-sensitive tackiness agent constituent are considered, the ionic compound of included chemical formula (I) expression is (if use its oligomer or multipolymer, also in ionic compound it) amount be preferably about 0.01 to 20 weight percent, with the gross weight of this binary be 100 weight percent meters it.The molecular weight that is applicable to the oligomer of pressure-sensitive tackiness agent constituent for example can be 1000 to 100000, be preferably 5000 to 50000, or ionic compound repeating unit number can be about 10 to 120.If consider monomeric wetting ability, then the n value of the ionic compound of chemical formula (I) expression is preferably 1 to 8, and is more preferred from 1 to 6.
Can further comprise solvent according to pressure-sensitive tackiness agent constituent of the present invention.This solvent for example can be the organic solvent of general solubilized acrylate, for example acetone, toluene, ethyl acetate etc., and consumption accounts for 30 to 85 weight percents of pressure-sensitive tackiness agent constituent, preferable about 50 to 80 weight percents.In the manufacturing of pressure-sensitive tackiness agent constituent of the present invention, can use the pressure-sensing glue polymkeric substance that makes as known techniques or its solution with the ionic compound of chemical formula (I) expression or the oligomer or the multipolymer of the ionic compound of chemical formula (I) expression mixes, and must pressure-sensitive tackiness agent constituent of the present invention.
The pressure-sensing glue polymkeric substance is preferably the polymkeric substance based on (methyl) propenyl, and itself and ionic compound consistency of the present invention are good, and can fully keep the bond property of pressure-sensitive tackiness agent.This kind based on the polymkeric substance of (methyl) propenyl preferable contain one or more alkyl carbon numbers be (methyl) alkyl acrylate of 1 to 14 as main component, be more preferred from and use that to have the alkyl carbon number be 2 to 13 the monomer based on (methyl) alkyl acrylate.The specific examples that has the alkyl carbon number and be (methyl) alkyl acrylate of 1 to 14 can comprise (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) n-butyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) isobutyl acrylate, (methyl) Ethyl acrylate, (methyl) 2-EHA, (methyl) vinylformic acid n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) vinylformic acid ester in the positive ninth of the ten Heavenly Stems, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, (methyl) vinylformic acid ester in the positive last of the ten Heavenly stems, (methyl) isodecyl acrylate, the positive 12 carbon esters of (methyl) vinylformic acid, the positive 13 carbon esters of (methyl) vinylformic acid, the positive 14 carbon esters of (methyl) vinylformic acid, or similar person.
Wherein, in the present invention, be preferably use (methyl) n-butyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) isobutyl acrylate, (methyl) Ethyl acrylate, (methyl) 2-EHA, (methyl) vinylformic acid n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) vinylformic acid ester in the positive ninth of the ten Heavenly Stems, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, (methyl) vinylformic acid ester in the positive last of the ten Heavenly stems, (methyl) isodecyl acrylate or similar person.
It is that 1 to 14 the monomer polymerization based on (methyl) alkyl acrylate forms that the pressure-sensing glue polymkeric substance can use single one or more to have the alkyl carbon number, and total content be preferably the total monomer composition 50 to 99.9 weight percents, be more preferred from 60 to 99 weight percents, good especially be 80 to 98 weight percents.Other tools functional group's monomer for example can be the Acrylic Acid Monomer that (methyl) vinylformic acid, (methyl) vinylformic acid 2-hydroxyl ethyl ester, (methyl) vinylformic acid 4-hydroxy butyl ester, (methyl) acrylic acid epoxy propyl ester etc. can carry out crosslinking reaction.Having the alkyl carbon number by use is 1 to 14 the monomer based on (methyl) alkyl acrylate, can appropriateness control and the better interaction of ionic compound, and obtain better adhesive pressure-sensitive tackiness agent.
The polymerization methods of (methyl) propenyl polymer is not limited to specific a kind ofly, but is good with solution polymerization, mass polymerization, suspension polymerization, letex polymerization and photopolymerization, especially with solution polymerization for better.Polymerization methods is to add a kind of initiator initiated polymerization, and initiator can be azo polymerization initiator, such as Diisopropyl azodicarboxylate and azo bicyclohexane nitrile, or superoxide such as benzoyl peroxide, acetyl peroxide and both mixtures.Temperature be set at 50 to 100 ℃.
The weight average molecular weight that is used in above-mentioned polymkeric substance based on (methyl) propenyl of the present invention is preferably 100,000 to 5,000,000, is more preferred from 200,000 to 4,000,000, and the best is 300,000 to 3,000,000.When weight average molecular weight is lower than at 100,000 o'clock, owing to the cohesive strength reduction of pressure sensitivity tackiness agent constituent tends to generate residual mashed prod (tackiness agent resistates).On the other hand, when weight average molecular weight surpasses at 5,000,000 o'clock, tend to moistening on polymer flow reduction, the Polarizer and become not enough, and between the pressure sensitivity tackiness agent constituent layer of Polarizer and surface protection film, have the tendency that generation is peeled off.Obtaining of weight average molecular weight is to get with GPC (gel permeation chromatography) tolerance.
In addition, usually employed above-mentioned polymkeric substance based on (methyl) propenyl has glass transition temperature (Tg) and is not less than-100 ℃, and is preferably glass transition temperature and is-90 ℃ to 0 ℃, and is more preferred from-80 ℃ to-10 ℃.When glass transition temperature is higher than 0 ℃, tends to moistening on polymer flow reduction, the Polarizer and become not enough, and between the pressure sensitivity tackiness agent constituent layer of Polarizer and surface protection film, have the tendency that generation is peeled off.In herein, can be based on the glass transition temperature (Tg) of the polymkeric substance of (methyl) propenyl by monomer component that appropriate change is used and constituent ratio, thereby be adjusted within the above-mentioned scope.
Specific embodiment based on the polymkeric substance of (methyl) propenyl is by butyl acrylate (butylacrylate, BA), vinylformic acid (acrylic acid, AA), with methacrylic acid dihydroxyl ethyl ester (2-hydroxyethylmethacrylate, HEMA) as being total to the product that the copolymerization of monomer institute forms, each monomeric amount, the product that forms with copolymerization be 100 weight percent meters it, for example can be respectively BA and account for that 80 to 99 weight percents, AA account for 0.1 to 15 weight percent, HEMA accounts for 0.1 to 5 weight percent.
In pressure-sensitive tackiness agent constituent of the present invention, can be by crosslinked polymkeric substance suitably based on (methyl) propenyl, and obtain the more pressure sensitivity adhesion sheet of excellent heat resistance.Can use known linking agent crosslinked to reach.For example add have can with based in the polymkeric substance of (methyl) propenyl as the compound of the group of the carboxyl of crosslinked fundamental point, hydroxyl reaction, for example isocyanate compound, epoxy compounds, based on the resin and the nitrogen heterocycle propane compound of trimeric cyanamide, to participate in reaction.Among them, by the viewpoint that obtains suitable cohesive strength, the preferably is for using isocyanate compound and epoxy compounds.These compounds can use separately, or mix two or the multiple class of using wherein.
On film, form the not restriction especially of method of pressure-sensitive bonding coat, but for example, the preparation of layer can be via the above-mentioned pressure-sensitive tackiness agent constituent of coating on carrier layer, and is dried employed solvent when removing polyreaction, and forms the pressure-sensitive bonding coat on carrier layer.In addition, when the preparation of pressure-sensitive adhesion sheet when coating pressure-sensitive tackiness agent constituent on the carrier film, one or more that can add employed solvent when being different from polyreaction are again planted solvents to constituent, and constituent can be coated on the carrier film equably.
Pressure-sensitive of the present invention adhesion sheet is above-mentioned pressure-sensitive shape bonding coat to be coated on the one or both sides of various different carriers and the form that forms sheet or band, this carrier comprises thickness and is generally 3 to 100 μ m, be preferably plastic film such as the polyester film of about 5 to 50 μ m, or the porous material such as the scraps of paper, and non-textile fiber.Particularly under the situation of surface protection film, preferable use plastic rubber substrate is as carrier.
Followingly enumerate some particular instances, wait example but the present invention is not limited thereto with explanation the present invention.
Test method
The test of glass tansition temperature:
The glass tansition temperature scans calorimeter (model: Q100 is by the TA instrument company manufacturing in Taiwan) by thermal different type to be judged.Rise (falling) warm speed: 10 ℃/min.
Tensile test:
The pressure-sensitive sheet of adhering is cut into 2.5 centimetres wide strip test piece, tear behind the release film, be affixed on two kilograms rubber rolls on the standard steel plate of SUS316, utilize puller system (model: Dachang is made by the wide rhenium instrument limited-liability company in Taiwan) to draw high the 180 degree peeling forces that speed 300mm/min measures pressure-sensitive adhesion sheet.
The confining force test:
The pressure-sensitive sheet of adhering is cut into 2.5 centimetres wide strip test piece, tearing, the rubber roll with two kilograms is affixed on the standard steel plate of SUS316 behind the release film, send in 70 ℃ the baking oven and left standstill 20 minutes, again with the test piece carry in holding viscous force tester (ChemInstruments HT-8, Ohio, USA ChemInstruments, Inc makes) go up and the counterweight of 1 kilogram of hanging in test piece, treat the distance of observing its time of dropping and moving after 40 minutes.
The antistatic surface property testing:
The antistatic surface property testing uses the device of model as Hiresta-Up Mcp-HT450 (Tokyo Mitsubishi chemical Co., Ltd (Mitsubishi Chemical Corporation) sells).This device applies by providing the surface impedance reading with 10 to 1000 volts of external voltages of two concentric annular electrodes of plane test materials and with ohm-sq unit.
Molecular weight measurement:
GPC device (600Controller, this Taiwan branch office of Internaional, Inc (Taibei) makes by US business's water) is used in the measurement of molecular weight.Measuring condition is as follows: sample concentration: 0.2 weight percent (THF solution); Sample injection quantity: 200 μ l; Towards extract: THF; Flow velocity: 1.0ml/min; Measure temperature: 40 ℃ of tubing strings; Sample tubing string: Shodex KF803 (tubing string 1)+Shodex KF804 (tubing string 2)+Shodex KF805 (tubing string 3)+Shodex KF806 (tubing string 4) that this Taiwan branch office of Internaional, Inc (Taibei) of US business's water makes; Detector: RI-detector (RI), estimating of molecular weight is a benchmark according to polystyrene standards inspection amount line.
The structural analysis of ionic compound:
The structural analysis of ionic compound utilizes FT-IR to measure and identifies.
FT-IR measures:
Use Infrared spectrophotometer (Spectrum One is made by U.S. Bo Jinaiermo limited-liability company (Perkin Elmer)), carry out with following measuring condition.Measuring method: ATR (weakening total reflection, attenuated total reflectance) method detector; DTGS (deuterate sulfuric acid three glycines, deuteratedtriglycine sulfate) resolution: 4.0cm-1; Cumulative frequency: 32.
Example
The preparation of preparation example methacrylate polymers (A)
Be equipped with paddle, thermometer, nitrogen ingress pipe, put into 189.4 parts by weight of acrylic butyl esters in the four neck flasks of condenser, 10 parts by weight of acrylic acid, 0.6 weight part hydroxyethyl methylacrylate, 0.16 weight part 2 as the polymerization initiator, 2 '-Diisopropyl azodicarboxylate, reach 466 weight part ethyl acetate as solvent, after under mild stirring, nitrogen being imported about 30 minutes, carried out polyreaction about 8 hours, and the fluid temperature in the flask is maintained about 60 ℃ therebetween, add the ethyl acetate dilution of 334 weight parts after being cooled to room temperature, so prepare polymkeric substance (A) (solid content 20%) based on acrylate.Polymkeric substance (A) obtains the glass tansition temperature through the examination of thermal different type scanning card instrumentation and is-44 ℃, and weight average molecular weight is 1,280,000.
Synthesizing of synthesis example ionic compound
Synthesizing of synthesis example 1 ionic compound (a)
In steel basin, add 45 weight part trimethyl ammonium chloride ethyl propylene acid esters ((2-(acryloyloxy) ethyl) trimethylammonium chloride) aqueous solution (80 weight percent), and dilute with 45 parts by weight of purified water, the MEHQ that adds 10 weight part acetone and 0.01 weight part again, temperature are controlled at 4 to 8 ℃.Two (trifluoromethane sulfonyl group) inferior acid amides lithiums (lithiumbis (trifluoromethane-sulfonyl) imide) of 60 weight parts are dissolved in the pure water of 60 weight parts; slowly splash in the steel basin again; add acetone simultaneously and keep clarity of solution, drip the back and continue stir about 3 hours.At room temperature extract acetone, add ethyl acetate again and extract 2 times, collect organic phase solution to rotate the mode of concentrating.In organic phase solution, add a little acetone, after dewatering with anhydrous magnesium sulfate again, with the sal epsom filtering, last solution with rotate concentrate drain get final product final product (a), be transparent liquid.Ionic compound (a) after FT-IR measures, is determined and turned out to be two (trifluoromethane sulfonyl group) the inferior acid amides QAE quaternary aminoethyl acrylate ((2-(acryloyloxy) ethyl) trimethylammonium bis (trifluoromethane-sulfonyl) imide) of trimethylammonium.
Synthesizing of synthesis example 2 ionic compounds (b)
In the double-neck flask that is equipped with nitrogen ingress pipe and condenser, put into magnetite, 100 weight part ionic compounds (a), as 400 weight part ethyl acetate of solvent, as 2 weight parts 2 of polymerization initiator, 2 '-Diisopropyl azodicarboxylate, under mild stirring, nitrogen was imported about 30 minutes, be heated to 70 ℃ and carried out polyreaction about 6 hours, obtain light yellow transparent liquid after being cooled to room temperature, be ionic compound (b) solution (solid content 20%), ionic compound (b) is the oligomer of ionic compound (a).The glass tansition temperature is 33 ℃ through the examination of thermal different type scanning card instrumentation.
Synthesizing of synthesis example 3 ionic compounds (c)
In the double-neck flask that is equipped with nitrogen ingress pipe and condenser, put into magnetite, 50 weight part ionic compounds (a), 50 parts by weight of acrylic acid butyl esters, as 400 weight part butanone of solvent, as 2 weight parts 2 of polymerization initiator, 2 '-Diisopropyl azodicarboxylate, under mild stirring, nitrogen was imported about 30 minutes, be heated to 80 ℃ and carried out polyreaction about 6 hours, be ionic compound (c) solution (solid content 20%) after being cooled to room temperature, ionic compound (c) is the multipolymer of ionic compound (a) and butyl acrylate.
Example 1
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The ionic compound (a) that in the solution (polymkeric substance (A) based on propenyl accounts for 20 weight percents) of the polymkeric substance based on propenyl (A) of the above-mentioned preparation example gained of 100 weight parts, adds above-mentioned synthesis example 1 gained of 0.1 weight part, also add following medicine in addition as linking agent and additive: 0.4 weight part polymeric polyisocyanate (polyisocyanate) affixture (toluene diisocyanate-trihydroxymethyl propaneadduct, Nippon Polyurethane Industry Co., Ltd.'s (being called for short NPU company) makes), 0.8 weight part aluminium acetylacetonate (aluminum acetylacetonate), and 0.04 weight part 3-glycidyl ether oxygen base propyl trimethoxy silicane (glycidoxypropyltrimethoxysilane, commercial disignation is Z-6040, Dow corning (Dow Corning) limited-liability company makes), at room temperature mixing and stir about are 5 minutes, make propenyl pressure-sensitive tackiness agent solution.
The preparation of pressure-sensitive adhesion sheet
On a polyethylene terephthalate (PET) film, it heats the pressure-sensitive adhesive coating that had thick 25 μ m in 3 minutes with formation down at 90 ℃ with above-mentioned propenyl pressure-sensitive tackiness agent solution coat.Then the release face of a polyethylene terephthalate release film is depressed into another surface of above-mentioned pressure-sensitive adhesive coating, therefore prepares pressure-sensitive adhesion sheet.At last this pressure-sensitive adhesion sheet is prepared the pressure-sensitive adhesion sheet that is used to measure pulling force, confining force, antistatic surface test with 90 ℃ of bakings in following 1 hour of baking oven.
Example 2
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 1, but adds the ionic compound (a) of 1 weight part but not 0.1 weight part.
The preparation of pressure-sensitive adhesion sheet
With example 1.
Example 3
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 1, but adds (b) (oligomer) solution of the ionic compound as synthesis example 2 gained of solid content 0.1 weight part and non-ionic compound (a).
The preparation of pressure-sensitive adhesion sheet
With example 1.
Example 4
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 3, but adds ionic compound (b) (oligomer) solution of solid content 1 weight part such as synthesis example 2 gained but not 0.1 weight part.
The preparation of pressure-sensitive adhesion sheet
With example 1.
Example 5
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 1, but adds (c) (multipolymer) solution of the ionic compound as synthesis example 3 gained of solid content 0.1 weight part and non-ionic compound (a).
The preparation of pressure-sensitive adhesion sheet
With example 1.
Example 6
Preparation according to pressure-sensitive tackiness agent constituent of the present invention
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 5, but adds ionic compound (c) (multipolymer) solution of solid content 1 weight part such as synthesis example 3 gained but not 0.1 weight part.
The preparation of pressure-sensitive adhesion sheet
With example 1.
Comparative example 1
The preparation of pressure-sensitive tackiness agent constituent
In the solution (polymkeric substance (A) based on propenyl accounts for 20 weight percents) of the polymkeric substance based on propenyl (A) of the above-mentioned preparation example gained of 100 weight parts, add following medicine as linking agent and additive: the silane coupling agent (commercial disignation Z-6040) of the polymeric polyisocyanate affixture as example 1 of 0.4 weight part, the aluminium acetylacetonate of 0.8 weight part, 0.04 weight part, at room temperature mixing and stir about are 5 minutes, make propenyl pressure-sensitive tackiness agent solution.
The preparation of pressure-sensitive adhesion sheet
With example 1.
Comparative example 2
The preparation of pressure-sensitive tackiness agent constituent
The preparation process of propenyl pressure-sensitive tackiness agent solution is with example 1; but two (trifluoromethane sulfonyl group) the inferior acid amides (1-propyl-3-methylimidazoliumbis (trifluoromethane-sulfonyl) imide) of the ionic liquid 1-propyl group-3-Methylimidazole that adds 0.1 weight part, and non-ionic compound (a).
The preparation of pressure-sensitive adhesion sheet
With example 1.
Comparative example 3
The preparation of pressure-sensitive tackiness agent constituent
The preparation process of propenyl pressure-sensitive tackiness agent solution is with comparative example 2, but adds two (trifluoromethane sulfonyl group) inferior acid amides of ionic liquid 1-propyl group-3-Methylimidazole of 1 weight part, but not 0.1 weight part.
The preparation of pressure-sensitive adhesion sheet
With example 1.
Test
Be shown in down for the test result of the resistance value of the propenyl pressure-sensitive of above-mentioned each example and comparative example adhesion sheet, pulling force, confining force and tabulate 1.As known from Table 1 along with the increase of the addition of ionic compound (a), resistance value has a declining tendency, similarly add ionic compound (b) (oligomer) or ionic compound (c) (multipolymer) also can be observed similar situation, resistance value has reduction slightly, and need only add the ionic compound of 0.1 weight part (is benchmark with the solid content), just square resistance can be reduced to 1011 Ω/ by 1014, represent this pressure-sensitive adhesion sheet that excellent antistatic is arranged.Aspect tensile test, when the addition of ionic compound (a) increased, value of thrust did not have considerable change, if be add ionic compound (b) or ionic compound (c) then pulling force a little increase is arranged, and confining force is all 0mm.Pulling force significantly decreases when adding ionic liquid with respect to comparative example 2 and 3, and showing to use according to the formed pressure-sensitive adhesion of pressure-sensitive tackiness agent constituent of the present invention sheet has excellent clinging power.
Square resistance, pulling force, the confining force table look-up of table 1 propenyl pressure-sensitive adhesion sheet
According to the detailed description of above embodiment, hope can be known description feature of the present invention and spirit more, and is not to come the present invention is limited with above-mentioned disclosed embodiment.
Claims (9)
2. an oligomer is to close product by ionic compound as claimed in claim 1 as monomeric oligomerization.
3. multipolymer, be by ionic compound as claimed in claim 1 as monomer altogether and at least a can with the common monomeric copolymerization product of acryl reaction.
4. pressure-sensitive tackiness agent constituent is characterized in that comprising:
Composition (a), it is selected from ionic compound as claimed in claim 1, be one of them of the cohort formed of monomeric oligomer, multipolymer and combination thereof with ionic compound as claimed in claim 1; And
Composition (b), its pressure-sensing glue polymkeric substance.
5. pressure-sensitive tackiness agent constituent according to claim 4 is characterized in that: this pressure-sensitive tackiness agent constituent with the total amount of this composition (a) and this composition (b) be 100 weight percent meters it, this ionic compound accounts for 0.01 to 20 weight percent.
6. pressure-sensitive tackiness agent constituent according to claim 4 is characterized in that: this pressure-sensitive tackiness agent constituent further comprises solvent.
7. pressure-sensitive tackiness agent constituent according to claim 4 is characterized in that: this pressure-sensing glue polymkeric substance comprises that weight average molecular weight is 100,000 to 5,000,000 the polymkeric substance based on (methyl) propenyl.
8. pressure-sensitive tackiness agent constituent according to claim 7 is characterized in that: should comprise the product that forms as the copolymerization of common monomer institute by butyl acrylate, vinylformic acid, with methacrylic acid dihydroxyl ethyl ester based on polymkeric substance of (methyl) propenyl.
9. pressure-sensitive tackiness agent constituent according to claim 8, it is characterized in that: with this amount based on the polymkeric substance of (methyl) propenyl is that 100 weight percents are as the criterion, and butyl acrylate, vinylformic acid, accounts for 80 to 99 weight percents, 0.1 to 15 weight percent, and 0.1 to 5 weight percent respectively with the amount of methacrylic acid dihydroxyl ethyl ester.
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Cited By (6)
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CN102352206A (en) * | 2011-09-06 | 2012-02-15 | 烟台德邦电子材料有限公司 | Pressure-sensitive adhesive for polaroid |
CN104736655A (en) * | 2012-09-04 | 2015-06-24 | 东友精细化工有限公司 | Adhesive composition |
US20170007464A1 (en) * | 2013-12-20 | 2017-01-12 | 3M Innovative Properties Company | Antimicrobial pressure-sensitive adhesive system |
CN107903355A (en) * | 2017-10-13 | 2018-04-13 | 住华科技股份有限公司 | Antistatic agent, adhesive composition using same, display device and polarizing plate |
CN109385236A (en) * | 2018-10-14 | 2019-02-26 | 佛山市顺德区永创翔亿电子材料有限公司 | Antistatic electrolyte resistance adhesive of lithium battery and preparation method thereof and terminal adhesive tape |
CN115368499A (en) * | 2022-09-28 | 2022-11-22 | 福州大学 | Underwater high-viscosity solid ionic elastomer and preparation method thereof |
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EP1724290A1 (en) * | 2004-03-11 | 2006-11-22 | Nisshinbo Industries, Inc. | Liquid composition containing no solvent |
JP2007009042A (en) * | 2005-06-30 | 2007-01-18 | Sanko Kagaku Kogyo Kk | Antistatic polymer composition, method for producing the same, molding using the same and polymerizable compound |
JP2007280912A (en) * | 2006-03-15 | 2007-10-25 | Institute Of National Colleges Of Technology Japan | Polymer electrolyte, and its manufacturing method |
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EP1724290A1 (en) * | 2004-03-11 | 2006-11-22 | Nisshinbo Industries, Inc. | Liquid composition containing no solvent |
JP2007009042A (en) * | 2005-06-30 | 2007-01-18 | Sanko Kagaku Kogyo Kk | Antistatic polymer composition, method for producing the same, molding using the same and polymerizable compound |
JP2007280912A (en) * | 2006-03-15 | 2007-10-25 | Institute Of National Colleges Of Technology Japan | Polymer electrolyte, and its manufacturing method |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102352206A (en) * | 2011-09-06 | 2012-02-15 | 烟台德邦电子材料有限公司 | Pressure-sensitive adhesive for polaroid |
CN104736655A (en) * | 2012-09-04 | 2015-06-24 | 东友精细化工有限公司 | Adhesive composition |
US20170007464A1 (en) * | 2013-12-20 | 2017-01-12 | 3M Innovative Properties Company | Antimicrobial pressure-sensitive adhesive system |
CN107903355A (en) * | 2017-10-13 | 2018-04-13 | 住华科技股份有限公司 | Antistatic agent, adhesive composition using same, display device and polarizing plate |
CN109385236A (en) * | 2018-10-14 | 2019-02-26 | 佛山市顺德区永创翔亿电子材料有限公司 | Antistatic electrolyte resistance adhesive of lithium battery and preparation method thereof and terminal adhesive tape |
CN115368499A (en) * | 2022-09-28 | 2022-11-22 | 福州大学 | Underwater high-viscosity solid ionic elastomer and preparation method thereof |
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