CN106398581A - Antistatic agent for adhesive - Google Patents

Antistatic agent for adhesive Download PDF

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Publication number
CN106398581A
CN106398581A CN201610605489.4A CN201610605489A CN106398581A CN 106398581 A CN106398581 A CN 106398581A CN 201610605489 A CN201610605489 A CN 201610605489A CN 106398581 A CN106398581 A CN 106398581A
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Prior art keywords
methyl
double
ammonium
ethoxy
imines
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Granted
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CN201610605489.4A
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Chinese (zh)
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CN106398581B (en
Inventor
村上贤志
齐藤恭辉
三浦佑嗣
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DKS Co Ltd
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Dai Ichi Kogyo Seiyaku Co Ltd
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    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • 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
    • C09J133/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

The object of the invention is to provide an antistatic agent for an adhesive, and the antistatic agent has excellent durability under high-temperature high-humidity conditions. The antistatic agent for the adhesive contains an ionic compound, and the positive ion part of the ionic compound is represented by any one of the formula 1 to the formula 3, wherein R1 represents an alkyl group which is provided with 1-18 carbon atoms and can contain hetero atoms, R2 represents an alkyl group which is provided with 2-4 carbon atoms, and a plurality of R1s/R2s can be the same or different.

Description

Binding agent antistatic additive
Technical field
The present invention relates to a kind of binding agent antistatic additive.
Background technology
As a rule, electrostatic refers in object storage electric charge and powered phenomenon or refer to powered electric charge itself.Quiet Electricity, in addition to the accumulation of the electric charge that 2 kinds of dielectric substance frictions produce, also refers to produce and accumulate because of contact with charged object etc. Surface in object.Above-mentioned electrostatic can cause the suction of the foreign bodies such as dust, the electrostatic breakdown of equipment, the maloperation of mensuration machine or Person's fire etc..Additionally, the probability that present calutron is temporarily or permanently damaged due to the release of electrostatic is very high.
For example, in liquid crystal panel, in order that the bonding such as glass baseplate of Polarizer, polarizer and liquid crystal cell, many Using the adhesive phase being formed by adhesive composition.The opticses such as this Polarizer, polarizer are generally by plastic material structure Become, therefore electrical insulating property is high, in release adhesive layer when easily produce electrostatic.Therefore, remaining such generation Electrostatic in the state of, if Polarizer, polarizer are fitted to liquid crystal cell it is likely that taking of liquid crystal molecule can be caused Chaotic to occurring.
Additionally, in order to manufacture Polarizer at high speed, carrying out when polarization board protective film is peeled off it is possible to cause because of existing work The electrostatic that do not produce in sequence and the breakoff phenomenon of TFT, IC element that leads to, the product defects of induction display panels.
Therefore, in order to suppress to produce electrostatic, seek to give anti-static function to adhesive phase, give as to adhesive phase The method of anti-static function, proposes there is cooperation ionic compound (patent documentation in the adhesive composition forming adhesive phase 1).
Additionally, in semiconductor processing procedures (for example, cutting action, back grinding procedure), due to binding agent stripping, Rub, contact etc. and producing electrostatic, the method accordingly, as producing with aforementioned same suppression electrostatic, proposition has viscous in formation Cooperation ionic compound (patent documentation 2) in the adhesive composition of mixture layer.
But, for the binding agent having coordinated ionic compound, if keeping under the conditions of hot and humid, due to ionizing The diffusion of compound mobile it may appear that sheet resistance value through when raise or ionic compound oozes out such problem to surface.
Citation
Patent documentation 1：Japanese Unexamined Patent Publication 2011-037927 publication
Patent documentation 2：Japanese Unexamined Patent Publication 2015-003988 publication
Content of the invention
Invention technical problem to be solved
Even if it is an object of the invention to provide a kind of binding agent that durability is also excellent under the conditions of hot and humid is with resisting Electrostatic agent.
Technological means for solve problem
The present inventor is concentrated on studies to solve above-mentioned problem, it was found that by using the sun with regulation The ionic compound of ionic portions, can reach above-mentioned problem, so far complete the present invention.
The present invention relates to the content of following [1] to [3].
[1] a kind of binding agent antistatic additive is it is characterised in that described adhesive antistatic additive contains ion combination Thing, and the cationic moiety of described ionic compound is the cation represented by any one of following formula (1) to (3),
[changing 1]
[changing 2]
[changing 3]
Wherein, in above-mentioned formula (1) to (3), R1Represent the alkyl of carbon number more than 1, less than 18, can contain miscellaneous former Son；R2Represent the alkyl of carbon number more than 2, less than 4, multiple R1Or R2Can distinguish identical or different.
[2] the binding agent antistatic additive as described in above-mentioned [1], it is former that described ionic compound is that anionicsite contains fluorine The compound of son.
[3] the binding agent antistatic additive as described in above-mentioned [1] or [2], the anionicsite of described ionic compound is At least one selected from the group being made up of double (fluorosulfonyl) imines and double (trifyl) imines.
Invention effect
According to the present invention, even if being provided that the also excellent binding agent antistatic additive of durability under the conditions of hot and humid.
Specific embodiment
Hereinafter, embodiments of the present invention are illustrated.
Ionic compound (イ オ Application compound, the ionic contained by binding agent antistatic additive of the present invention Compound) comprise cationic moiety (Japanese：カ チ オ Application position) and anionicsite (Japanese：ア ニ オ Application position), Under room temperature, (23 DEG C/50%RH) can be solid, shaped and liquid any.
The cationic moiety of described ionic compound is represented by any one of above-mentioned formula (1) to (3).
In above-mentioned formula (1) to (3), R1The alkyl representing carbon number more than 1, less than 18 is it is also possible to contain hetero atom.R2 Represent the alkyl of carbon number more than 2, less than 4, the preferably alkyl of carbon number more than 2, less than 3, more preferably carbon atom The alkyl of number 2.Multiple R1Or R2Can be identical or different respectively.
The cation that formula (1) represents is not particularly limited, and specifically, can include：2- ethoxy trimethyl ammonium sun Ion, 2- hydroxyethyl dimethyl ethyl ammonium cations, 2- hydroxyethyl dimethyl propyl group ammonium cation, 2- hydroxyethyl dimethyl butyl Ammonium cation, 2- hydroxyethyl dimethyl hexyl ammonium cation, 2- hydroxyethyl dimethyl octyl group ammonium cation, 2- hydroxyethyl dimethyl Decyl ammonium cation, 2- hydroxyethyl dimethyl lauryl ammonium cation, 2- hydroxyethyl dimethyl benzyl ammonium cation, 2- ethoxy Diethylmethyl ammonium cation, 2- ethoxy triethyl ammonium cation, 2- ethoxy diethylpropyl ammonium cation, 2- ethoxy Diethyl butyl ammonium cation, 2- ethoxy diethylhexyl ammonium cation, 2- ethoxy diethyl octyl group ammonium cation, 2- hydroxyl Ethyl diethyl decyl ammonium cation, 2- ethoxy diethyl lauryl ammonium cation, 2- ethoxy diethylbenzyl ammonium sun from Son, 2- ethoxy dibutylmethyl ammonium cation, 2- ethoxy dibutylethyl ammonium cation, 2- ethoxy dibutyl propyl ammonium Cation, 2- ethoxy tributyl ammonium cation, 2- ethoxy dibutyl hexyl ammonium cation, 2- ethoxy dibutyl octyl group ammonium Cation, 2- ethoxy dibutyl decyl ammonium cation, 2- ethoxy dibutyl lauryl ammonium cation, 2- ethoxy dibutyl Benzyl ammonium cation, 2- Hydroxyproyl Trimethyl ammonium cation, 4- hydroxyl butyl trimethyl ammonium cation, 2- hydroxypropyl triethyl ammonium sun Ion, 4- hydroxyl butyl triethyl ammonium cation, 2- hydroxypropyl tributyl ammonium cation, 4- hydroxyl butyl tributyl ammonium cation, 2- Hydroxypropyl diethylmethyl ammonium cation, 2- hydroxypropyl diethylpropyl ammonium cation, 2- hydroxypropyl diethyl butyl ammonium sun from Son, 2- hydroxypropyl diethylhexyl ammonium cation, 2- hydroxypropyl diethyl octyl group ammonium cation, 2- hydroxypropyl diethyl decyl ammonium Cation, 2- hydroxypropyl diethyl lauryl ammonium cation, 2- hydroxypropyl diethylbenzyl ammonium cation etc..These can be independent Using a kind, it is possible to use two or more.
The cation that formula (2) represents is not particularly limited, and specifically, can include：Double (2- ethoxy) dimethyl Ammonium cation, double (2- ethoxy) ethyl-methyl ammonium cation, double (2- ethoxy) hydroxypropyl methyl ammonium cation, double (2- hydroxyl second Base) butyl methyl ammonium cation, double (2- ethoxy) hexyl methyl ammonium cation, double (2- ethoxy) octyl methyl ammonium sun from Sub, double (2- ethoxy) decyl methyl ammonium cation, double (2- ethoxy) lauryl methyl ammonium cation, double (2- ethoxy) oil Ylmethyl ammonium cation, double (2- ethoxy) benzyl methyl ammonium cation, double (2- ethoxy) diethyl ammonium cation, double (2- Ethoxy) ethyl propyl ammonium cation, double (2- ethoxy) ethyl-butyl ammonium cation, double (2- ethoxy) ethylhexyl ammonium sun Ion, double (2- ethoxy) ethyloctanyl ammonium cation, double (2- ethoxy) ethyl decyl ammonium cation, double (2- ethoxy) second Base lauryl ammonium cation, double (2- ethoxy) Ethylbenzyl ammonium cation, double (2- ethoxy) butyl propyl group ammonium cation, double (2- ethoxy) dibutyl ammonium cation, double (2- ethoxy) butyl hexyl ammonium cation, double (2- ethoxy) butyl octyl ammonium Cation, double (2- ethoxy) butyl decyl ammonium cation, double (2- ethoxy) butyl lauryl ammonium cation, double (2- hydroxyl second Base) butyl benzyl ammonium cation, double (2- hydroxypropyl) Dimethyl Ammonium cation, double (2- hydroxypropyl) diethyl ammonium cation, double (2- hydroxypropyl) dibutyl ammonium cation, double (2- hydroxypropyl) oleyl methyl ammonium cation, double (4- hydroxyl butyl) Dimethyl Ammonium sun Ion, double (4- hydroxyl butyl) diethyl ammonium cation, double (4- hydroxyl butyl) dibutyl ammonium cation, double (2- hydroxyl butyl) oil base first Base ammonium cation, polyoxyethylene laural ylmethyl ammonium cation (Port リ オ キ シ エ チ レ Application ラ ウ リ Le メ チ Le ア Application モ ニ ウ system カ チ オ Application), polyoxyethylene laural base ethyl ammonium cations, polyoxyethylene laural base butyl ammonium cation, polyoxyethylene Lauryl hexyl ammonium cation, polyoxyethylene laural Ji Xinji ammonium cation, polyoxyethylene oleyl methyl ammonium cation, polyoxy second Alkene oil base ethyl ammonium cations, polyoxyethylene oil base butyl ammonium cation, polyoxyethylene oil base hexyl ammonium cation, polyoxyethylene Oil base octyl group ammonium cation, polyoxyethylene stearyl ylmethyl ammonium cation, polyoxyethylene stearyl base ethyl ammonium cations, polyoxy second Alkene stearyl butyl ammonium cation, polyoxyethylene stearyl base hexyl ammonium cation, polyoxyethylene stearyl Ji Xinji ammonium cation etc.. These can be used alone a kind, it is possible to use two or more.
The cation that formula (3) represents is not particularly limited, and specifically, can include：Three (2- ethoxy) ammonium methyl Cation, three (2- ethoxy) ethyl ammonium cations, three (2- ethoxy) propyl group ammonium cation, three (2- ethoxy) butyl ammonium sun Ion, three (2- ethoxy) hexyl ammonium cation, three (2- ethoxy) octyl group ammonium cation, three (2- ethoxy) decyl ammonium sun from Son, three (2- ethoxy) lauryl ammonium cation, three (2- ethoxy) stearyl ammonium cation, three (2- ethoxy) oil base ammonium sun Ion, three (2- ethoxy) benzyl ammonium cation, three (2- hydroxypropyl) methyl ammonium cation, three (2- hydroxypropyl) ethyl ammonium sun from Son, three (2- hydroxypropyl) propyl group ammonium cation, three (2- hydroxypropyl) butyl ammonium cation, three (2- hydroxypropyl) hexyl ammonium sun from Son, three (2- hydroxypropyl) octyl group ammonium cation, three (2- hydroxypropyl) decyl ammonium cation, three (2- hydroxypropyl) lauryl ammonium sun from Son, three (2- hydroxypropyl) stearyl ammonium cation, three (2- hydroxypropyl) oil base ammonium cation, three (2- hydroxypropyl) hexadecyldimethyl benzyl ammonium sun from Son, three (4- hydroxyl butyl) methyl ammonium cation, three (4- hydroxyl butyl) ethyl ammonium cations, three (4- hydroxyl butyl) propyl ammonium sun from Son, three (4- hydroxyl butyl) butyl ammonium cation, three (4- hydroxyl butyl) hexyl ammonium cation, three (4- hydroxyl butyl) octyl group ammonium sun from Son, three (4- hydroxyl butyl) decyl ammonium cation, three (4- hydroxyl butyl) lauryl ammonium cation, three (4- hydroxyl butyl) stearyl ammonium sun Double (2- ethoxy)-N- (the 2- hydroxyl of ion, three (4- hydroxyl butyl) oil base ammonium cation, three (4- hydroxyl butyl) benzyl ammonium cation, N- Propyl group) methyl ammonium cation, double (2- ethoxy)-N- (the 2- hydroxyl butyl) methyl ammonium cation of N-, double (2- the hydroxypropyl)-N- of N- (2- hydroxyl butyl) methyl ammonium cation, N- (2- methylol)-N- (2- hydroxypropyl)-N- (2- hydroxyl butyl) methyl ammonium cation etc.. These can be used alone a kind, it is possible to use two or more.
As long as the anionicsite of ionic compound meets becomes ionic compound, it is not particularly limited, for example permissible Use：F-、Cl-、Br-、I-、AlCl4 -、Al2Cl7 -、BF4 -、PF6 -、SCN-、ClO4 -、NO3 -、CH3COO-、CF3COO-、CH3SO3 -、 CF3SO3 -、(CF3SO2)2N-、(F2SO2)2N-、(CF3SO2)3C-、AsF6 -、SbF6 -、NbF6 -、TaF6 -、F(HF)n -、(CN)2N-、 C4F9SO3 -、(C2F5SO2)2N-、C3F7COO-(CF3SO2)(CF3CO)N-Deng.These can be used alone a kind, it is possible to use Two or more.
Wherein, the anion component containing fluorine atom can obtain the ionic compound of low melting point, therefore preferably, more preferably Use (F2SO2)2N-(double (fluorosulfonyl) imines) and (CF3SO2)2N-(double (trifyl) imines).
The concrete example of ionic compound used in binding agent antistatic additive as the present invention, can from above-mentioned sun from Suitably select to use in the combining of subdivision and anionicsite, can include：2- ethoxy trimethyl ammonium=hexafluorophosphoric acid Salt, 2- ethoxy trimethyl ammonium=tetrafluoroborate, 2- ethoxy trimethyl ammonium=fluoroform sulphonate, 2- ethoxy trimethyl Ammonium=bis- (trifyl) imines, 2- ethoxy trimethyl ammonium=bis- (fluorosulfonyl) imines, 2- hydroxyethyl dimethyl second Base ammonium=bis- (trifyl) imines, 2- hydroxyethyl dimethyl ethyl ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy two Methyl butyl ammonium=bis- (trifyl) imines, 2- hydroxyethyl dimethyl butyl ammonium=bis- (fluorosulfonyl) imines, 2- hydroxyl Ethyl dimethyl octyl group ammonium=bis- (trifyl) imines, 2- hydroxyethyl dimethyl octyl group ammonium=bis- (fluorosulfonyl) are sub- Amine, 2- hydroxyethyl dimethyl lauryl ammonium=bis- (trifyl) imines, 2- hydroxyethyl dimethyl lauryl ammonium=bis- (fluorine Sulfonyl) imines, 2- ethoxy diethylmethyl ammonium=hexafluorophosphate, 2- ethoxy diethylmethyl ammonium=Tetrafluoroboric acid Salt, 2- ethoxy diethylmethyl ammonium=fluoroform sulphonate, 2- ethoxy diethylmethyl ammonium=bis- (trifyls) Imines, 2- ethoxy diethylmethyl ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy diethyl butyl ammonium=bis- (fluoroform sulphurs Acyl group) imines, 2- ethoxy diethyl butyl ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy diethyl octyl group ammonium=bis- (three Fluorine mesyl) imines, 2- ethoxy diethyl octyl group ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy dibutylmethyl ammonium= Double (trifyl) imines, 2- ethoxy dibutylmethyl ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy tributyl ammonium =bis- (trifyl) imines, 2- ethoxy tributyl ammonium=bis- (fluorosulfonyl) imines, 2- ethoxy dibutyl octyl group Ammonium=bis- (trifyl) imines, 2- ethoxy dibutyl octyl group ammonium=bis- (fluorosulfonyl) imines, 2- hydroxypropyl trimethylammonium Base ammonium=bis- (trifyl) imines, 2- Hydroxyproyl Trimethyl ammonium=bis- (fluorosulfonyl) imines, 4- hydroxyl butyl trimethyl Ammonium=bis- (trifyl) imines, 4- hydroxyl butyl trimethyl ammonium=bis- (fluorosulfonyl) imines, double (2- ethoxy) diformazan Base ammonium=hexafluorophosphate, double (2- ethoxy) Dimethyl Ammonium=tetrafluoroborate, double (2- ethoxy) Dimethyl Ammonium=trifluoro Mesylate, double (2- ethoxy) Dimethyl Ammonium=bis- (trifyl) imines, Dimethyl Ammonium=bis- (fluorosulfonyl) are sub- Amine, double (2- ethoxy) butyl methyl ammonium=bis- (trifyl) imines, double (2- ethoxy) butyl methyl ammonium=bis- (fluorine Sulfonyl) imines, double (2- ethoxy) octyl methyl ammonium=bis- (trifyl) imines, double (2- ethoxy) octyl methyl Ammonium=bis- (fluorosulfonyl) imines, double (2- ethoxy) oleyl methyl ammonium=bis- (trifyl) imines, double (2- hydroxyl second Base) oleyl methyl ammonium=bis- (fluorosulfonyl) imines, double (2- ethoxy) butyl octyl ammonium=bis- (trifyl) imines, Double (2- ethoxy) butyl octyl ammonium=bis- (fluorosulfonyl) imines, double (2- hydroxypropyl) Dimethyl Ammonium=bis- (trifluoro methylsulfonyl Base) imines, double (2- hydroxypropyl) Dimethyl Ammonium=bis- (fluorosulfonyl) imines, double (4- hydroxyl butyl) Dimethyl Ammonium=bis- (trifluoros Mesyl) imines, double (4- hydroxyl butyl) Dimethyl Ammonium=bis- (fluorosulfonyl) imines, polyoxyethylene laural ylmethyl ammonium=bis- (trifyl) imines, polyoxyethylene laural ylmethyl ammonium=bis- (fluorosulfonyl) imines, polyoxyethylene oleyl methyl ammonium =bis- (trifyl) imines, polyoxyethylene oleyl methyl ammonium=bis- (fluorosulfonyl) imines, polyoxyethylene stearyl Ji Jia Base ammonium=bis- (trifyl) imines, polyoxyethylene stearyl ylmethyl ammonium=bis- (fluorosulfonyl) imines, three (2- hydroxyl second Base) ammonium methyl=hexafluorophosphate, three (2- ethoxy) ammonium methyl=tetrafluoroborate, three (2- ethoxy) ammonium methyl=trifluoro Mesylate, three (2- ethoxy) ammonium methyl=bis- (trifyl) imines, three (2- ethoxy) ammonium methyl=bis- (fluorine sulphur Acyl group) imines, three (2- hydroxypropyl) ammonium methyl=bis- (trifyl) imines, three (2- hydroxypropyl) ammonium methyl=bis- (fluorine Sulfonyl) imines, three (4- hydroxyl butyl) ammonium methyl=bis- (trifyl) imines, three (4- hydroxyl butyl) ammonium methyl=bis- (fluorosulfonyl) imines etc..These can be used alone a kind, it is possible to use two or more.
It should be noted that above-mentioned such ionic compound can be using commercially available product it is also possible to be carried out as follows synthesis.Make For the synthetic method of ionic compound etc., as long as obtaining object ion compound etc., it is not particularly limited, can be as document As described in " forefront of ionic liquid-exploitation and future-" (Co., Ltd. C MC publication and distribution), using halide, Hydroxide process, acid esters method, complexation form method and neutralisation etc..
The binding agent antistatic additive of the present invention be containing the sun having shown in any one of above-mentioned formula (1)～(3) from The ionic compound of subdivision, as the antistatic additive of effective ingredient, can be used alone it is also possible to mix steady as needed Determine the additives such as agent or solvent etc. and use.
The addition of the binding agent antistatic additive of the present invention, with respect to binder polymer 100 mass parts, is 0.01 matter More than amount part, more than preferably 0.05 mass parts, more than more preferably 0.1 mass parts, and, below 40 mass parts, preferably 20 Below mass parts, below more preferably 10 mass parts.
The binding agent antistatic additive of the present invention extensively can make in the binder polymer that this technical field is used With.As above-mentioned binder polymer, can include：(methyl) acrylic acid series polymeric compounds, rubber-based polymeric thing, silicone (シ リ U Application) based polymer, polyurethane series polymer etc..In these, (methyl) acrylic acid series polymeric compounds can be preferably used.
Above-mentioned (methyl) acrylic acid series polymeric compounds e.g. contain (methyl) alkyl acrylate and (become as monomeric unit Point) polymer, should (methyl) alkyl acrylate have carbon number 1～20 straight or branched alkyl.Additionally, on State (methyl) acrylic acid series polymeric compounds can be the alkyl with carbon number 1～20 (methyl) alkyl acrylate individually or The structure of two or more combination.
As (methyl) alkyl acrylate of the alkyl with above-mentioned carbon number 1～20, for example, can include： (methyl) acrylic acid methyl ester., (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) Butyl acrylate, (methyl) Isobutyl 2-propenoate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate, (methyl) third Olefin(e) acid pentyl ester, (methyl) isoamyl acrylate, (methyl) Hexyl 2-propenoate, (methyl) heptylacrylate, (methyl) propylene are misery Ester, (methyl) 2-EHA, (methyl) Isooctyl acrylate monomer, (methyl) acrylic acid nonyl ester, (methyl) acrylic acid are different Nonyl ester, (methyl) decyl acrylate, (methyl) isodecyl acrylate, (methyl) acrylic acid hendecane base ester, (methyl) acrylic acid Dodecyl ester, (methyl) tridecyl acrylate, (methyl) acrylic acid tetradecane base ester, (methyl) acrylic acid pentadecyl Ester, (methyl) aliphatic acrylate, (methyl) acrylic acid heptadecane base ester, (methyl) octadecyl acrylate, (first Base) (methyl) acrylic acid C1-20 Arrcostab (preferably (first such as acrylic acid nonadecane base ester, (methyl) acrylic acid eicosane base ester Base) acrylic acid C2-14 Arrcostab, further preferably (methyl) acrylic acid C2-10 Arrcostab) etc..Wherein, (methyl) alkyl acrylate Base ester refers to alkyl acrylate and/or alkyl methacrylate, and " (methyl) ... " is all the same meaning.
The ratio of (methyl) alkyl acrylate with the alkyl of above-mentioned carbon number 1～20 is with respect to for preparing Monomeric unit (composition) total amount 100 mass parts of (methyl) acrylic acid series polymeric compounds, are more than 50 mass parts, more preferably 60 mass More than part, more than further preferred 70 mass parts.On the other hand, aforementioned proportion is below 99.9 mass parts, preferably 98 mass Below part, more preferably 96 mass parts are once.If within the above range, can obtain peeling off in purposes again for can be used on Bonding sheet for preferred adhesion characteristic, therefore for optimal way.
It should be noted that in above-mentioned (methyl) acrylic acid series polymeric compounds to improve cohesiveness, thermostability, bridging property etc. being Purpose, can also contain as needed can be with the other monomers unit (composition) of above-mentioned (methyl) alkyl acrylate copolymer (co-polymerized monomer).Therefore, (methyl) acrylic acid series polymeric compounds can also be with above-mentioned (methyl) acrylic acid as main component Ester alkyl ester contains co-polymerized monomer together.As co-polymerized monomer, can be suitably using the monomer with polar group.Need Illustrate, main component refers to mixing ratio highest monomer in monomer component total amount.
As the specific example of above-mentioned co-polymerized monomer, can include：Acrylic acid, methacrylic acid, carboxyethyl propylene The carboxylic monomers such as acid esters, carboxylic acrylate, itaconic acid, maleic acid, fumaric acid, butenoic acid, methacrylate；(methyl) Acrylic acid 2- hydroxyl ethyl ester, (methyl) acrylic acid 3- hydroxypropyl acrylate, (methyl) acrylic acid 4- hydroxy butyl ester, (methyl) acrylic acid 6- hydroxyl are own Ester, (methyl) acrylic acid 8- hydroxyl monooctyl ester, (methyl) acrylic acid 10- hydroxyl last of the ten Heavenly stems ester, (methyl) acrylic acid 12- hydroxyl lauryl, methyl-prop The monomer of the hydroxyls such as (methyl) acrylic acid hydroxy alkyl ester of olefin(e) acid (4- hydroxymethylcyclohexyl) methyl ester etc.；Maleic anhydride, clothing health Anhydride etc. contains the monomer of anhydride；Styrene sulfonic acid, allyl sulphonic acid, 2- (methyl) acrylamide-2-methyl propane sulfonic, (methyl) Acrylamide propane sulfonic acid, sulfopropyl (methyl) acrylate, (methyl) acryloyl-oxy LOMAR PWA EINECS 246-676-2 etc. contain sulfonic monomer；2- hydroxyl The monomer of the phosphorous acidic group such as ethyl propylene acyl phosphate；(methyl) acrylamide, N, N- dimethyl (methyl) acrylamide, N, N- diethyl (methyl) acrylamide, N, N- dipropyl (methyl) acrylamide, N, N- diisopropyl (methyl) acrylamide, N, N- di-n-butyl (methyl) acrylamide, N, the N such as N- di-t-butyl (methyl) acrylamide, N- dialkyl group (methyl) acryloyl Amine, N- ethyl (methyl) acrylamide, N- isopropyl (methyl) acrylamide, N- butyl (methyl) acrylamide, N- normal-butyl (methyl) acrylamide, N- methylol (methyl) acrylamide, N- ethoxy (methyl) acrylamide, N- hydroxymethyl-propane (first Base) acrylamide, N- methoxy (methyl) acrylamide, N- methoxy ethyl (methyl) acrylamide, N- butoxy first Base (methyl) acrylamide, N- acryloyl morpholine etc. (N- replacement) amide system monomer；N- (methyl) acryloyl-oxy methylene Butanimide, N- (methyl) acryloyl group -6- oxygen hexa-methylene butanimide, N- (methyl) acryloyl group -8- oxygen six are sub- The butanimide such as methyl succinimide system monomer；N- N-cyclohexylmaleimide, N- isopropylmaleimide, N- Laurel The maleimide amine system monomer such as base maleimide, N-phenylmaleimide；N- methyl clothing health acid imide, N- ethyl clothing health acyl Imines, N- butyl clothing health acid imide, N- octyl group clothing health acid imide, N-2- ethylhexyl clothing health acid imide, N- cyclohexyl clothing health acyl The clothing health imide series monomers such as imines, N- lauryl clothing health acid imide；The vinyl esters such as vinyl acetate, propionate；N- Vinyl-2-pyrrolidone, N- methyl ethylene ketopyrrolidine, N- vinylpyridine, N- vinylpiperidone, N- vinyl are phonetic Pyridine, N- vinyl piperazine, N- vinylpyrazine, N- vinyl pyrrole, N- vinyl imidazole, N- vinyl azoles, N- (methyl) Acryloyl group -2-Pyrrolidone, N- (methyl) acryloylpiperidine, N- (methyl) acryloyl group pyrrolidine, N- polyvinyl morpholinone, N- vinyl -2- piperidones, N- vinyl -3- morpholone, N- vinyl -2- caprolactam, N- vinyl -1,3- piperazine -2- Ketone, N- vinyl -3,5- morpholine diketone, N- vinyl pyrazoles, N- vinyl isoxazole, N- vinylthiazole, the different thiophene of N- ethylene The nitrogen-containing hetero ring system monomers such as azoles, N- ethylene radical pyridazine；N- vinylcarboxylic acid amide type；The lactams such as N- caprolactam system Monomer；The cyanoacrylate monomers such as acrylonitrile, methacrylonitrile；(methyl) acrylic-amino ethyl ester, (methyl) acrylic acid (methyl) the acrylate systems such as N, N- dimethyl aminoethyl ester, (methyl) acrylic acid t-butylamino ethyl ester are single Body；(methyl) methoxyethyl ethyl ester, (methyl) ethioxy ethyl ester, (methyl) acrylic acid Among (methyl) the acrylic acid alkoxyalkyls such as ester, (methyl) butoxyethyl acrylate, (methyl) ethioxy propyl diester Ester system monomer；The styrenic monomers such as styrene, α-methyl styrene；(methyl) glycidyl acrylate etc. contains ethyoxyl Acrylic monomer；(methyl) acrylic acid tetrahydro furfuryl ester, fluorine-containing (methyl) acrylate, silicone (methyl) acrylate etc. Acrylic ester monomer containing heterocycle, halogen atom, silicon atom etc.；The olefinic monomers such as isoprene, butadiene, isobutene.；First The vinyl ethers such as base vinyl ethers, ethyl vinyl ether system monomer；The vinyl esters such as vinyl acetate, propionate；Second The aromatic ethenyl compounds such as alkene toluene, styrene；The alkene such as ethylene, butadiene, isoprene, isobutene. or dienes； The vinyl ethers such as vinyl alkyl ethers；Vinyl chloride；Sodium vinyl sulfonate etc. contains sulfonic monomer；Cyclohexyl maleimide Amine, isopropylmaleimide etc. contain dant monomer；2- isocyanate ethyl (methyl) acrylate etc. contains isocyanates The monomer of base；Acryloyl morpholine；Cyclopenta (methyl) acrylate, cyclohexyl (methyl) acrylate, isobornyl (first Base) acrylate, bicyclopentyl (methyl) acrylate etc. have (methyl) acrylate of ester ring type alkyl；Phenyl (methyl) Acrylate, Phenoxyethyl (methyl) acrylate etc. have (methyl) acrylate of aromatic hydrocarbyl；By terpenes chemical combination (methyl) acrylate that thing derivant alcohol obtains；Etc..These can be used alone a kind, it is possible to use two or more.
In above-mentioned (methyl) acrylic acid series polymeric compounds and above-mentioned (methyl) the acrylate Arrcostab one as main component And in the case that ground contains co-polymerized monomer, can be suitably using above-mentioned hydroxyl monomer or carboxyl group-containing monomer.Wherein, as upper State hydroxyl monomer, (methyl) HEA, (methyl) acrylic acid 4- hydroxyl butyl ester are suitable, contain as above-mentioned Carboxylic monomer, can be suitably using acrylic acid.
Even if the reasons why binding agent antistatic additive of present invention durability under the conditions of hot and humid is also excellent there is no fixed By, but can be presumed as follows.That is, the feelings in above-mentioned (methyl) acrylic acid series polymeric compounds with hydroxyl, carboxyl etc. can be speculated Under condition, the ionic compound contained by binding agent antistatic additive of the present invention due to there is hydroxyl in cationic moiety, therefore The ionic compound contained by binding agent antistatic additive of the present invention and the intermiscibility of above-mentioned (methyl) acrylic acid series polymeric compounds Improve, and the raising of durability can be presented.
In order to adjust the molecular weight of above-mentioned (methyl) acrylic acid series polymeric compounds, can be using chain-transferring agent in its polymerization. As the example of the chain-transferring agent being used, can include：Octyl mercaptan, lauryl mercaptan, tert-dodecylmercaotan, sulfydryl Ethanol, α-thioglycerol etc. have the compound of sulfydryl；TGA, methyl thioglycolate, ethyl thioglycolate, TGA Propyl ester, TGA butyl ester, the TGA tert-butyl ester, 2-ethylhexyl mercaptoacetate, TGA monooctyl ester, the TGA last of the ten Heavenly stems Ester, TGA dodecyl ester, the mercaptoacetate of ethylene glycol, the mercaptoacetate of neopentyl glycol, the sulfydryl of tetramethylolmethane The TGA esters such as acetass；α-methyl styrene dimer etc..These can be used alone a kind, it is possible to use 2 kinds with On.
When preparing above-mentioned (methyl) acrylic acid series polymeric compounds, employ thermal polymerization, (light draws Photoepolymerizationinitiater initiater Send out agent) etc. polymerization initiator, using the curing reaction that carries out based on heat, ultraviolet, be able to easily form (methyl) propylene Sour based polymer.Particularly, consider from advantage that can shorten polymerization time etc., can be suitably using thermal polymerization.Polymerization causes Agent can be used alone, or combines two or more use.
As thermal polymerization, for example, it is possible to include：(for example, 2,2 '-azo is double different for azo system polymerization initiator Double -2- the methylbutyronitrile of butyronitrile, 2,2 '-azo, double (2 Methylpropionic acid) dimethyl ester of 2,2 '-azo, the double -4- cyano group of 4,4 '-azo The double isobutyl cyanide of valeric acid, azo, double (2- amidine propane) dihydrochloride of 2,2 '-azo, the double [2- (5- methyl -2- miaow of 2,2 '-azo Oxazoline -2- base) propane] double (N, N '-two are sub- for dihydrochloride, double (the 2- methyl-prop amidine) dithionate of 2,2 '-azo, 2,2 '-azo Methyl-isobutyl amidine) dihydrochloride etc.)；Peroxide system polymerization initiator (for example, benzoyl peroxide, tert-butyl hydroperoxide Maleate (t- Block チ Le ペ Le オ キ シ De マ レ エ ト), lauroyl peroxide etc.)；Redox system polymerization initiator Deng.
As the use level of above-mentioned thermal polymerization, it is not particularly limited, for example, with respect to preparing above-mentioned (methyl) third Total amount 100 mass parts of the monomer unit (composition) of olefin(e) acid based polymer, preferably with 0.01～5 mass parts coordinate, more preferably with Amount cooperation in the range of 0.05～3 mass parts.
As above-mentioned Photoepolymerizationinitiater initiater, it is not particularly limited, for example, can use benzoin ether system Photoepolymerizationinitiater initiater, benzene Ethyl ketone system Photoepolymerizationinitiater initiater, α -one alcohol system Photoepolymerizationinitiater initiater, aromatic sulfonyl system Photoepolymerizationinitiater initiater, photolytic activity oxime system Photoepolymerizationinitiater initiater, benzoin system Photoepolymerizationinitiater initiater, benzyl system Photoepolymerizationinitiater initiater, diphenylmethanone system Photoepolymerizationinitiater initiater, Ketal system Photoepolymerizationinitiater initiater, thiaxanthone system Photoepolymerizationinitiater initiater, acylphosphine oxide system Photoepolymerizationinitiater initiater etc..
Specifically, as above-mentioned benzoin ether system Photoepolymerizationinitiater initiater, for example, can include：Benzoin methyl ether, Benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2- dimethoxy -1,2- hexichol Base ethane -1- ketone [trade name：IRGACURE651, BASF AG manufacture], methyl phenyl ethers anisole methyl ether (anisole methyl Ether) etc..As 1-Phenylethanone. system Photoepolymerizationinitiater initiater, for example, can include：1- hydroxycyclohexyl phenyl ketone [trade name： IRGACURE 184, BASF AG manufacture], 4- phenoxydichloroacetophenone, the 4- tert-butyl group-dichloroacetophenone, 1- [4- (2- hydroxyl Base oxethyl)-phenyl] -2- hydroxy-2-methyl -1- propane -1- ketone [trade name：IRGACURE 2959, BASF AG manufactures], 2- hydroxy-2-methyl -1- phenyl-propan -1- ketone [trade name：DAROCUR 1173, BASF AG manufacture], methoxyacetophenone Deng.As α -one alcohol system Photoepolymerizationinitiater initiater, for example, can include：2- methyl -2- hydroxypropiophenonepreparation, 1- [4- (2- hydroxyl second Base)-phenyl] -2- hydroxy-2-methyl propane -1- ketone etc..As aromatic sulfonyl system Photoepolymerizationinitiater initiater, for example, can arrange Enumerate：2- naphthalene sulfonyl chloride etc..As photolytic activity oxime system Photoepolymerizationinitiater initiater, for example, can include：1- phenyl -1,1- the third two Alcohol -2- (adjacent carbethoxyl group)-oxime etc..
Additionally, above-mentioned benzoin system Photoepolymerizationinitiater initiater for example comprises benzoin etc..Benzyl system Photoepolymerizationinitiater initiater is for example Comprise benzyl etc..Diphenylmethanone system Photoepolymerizationinitiater initiater for example comprise diphenylmethanone, benzoyl benzoic acid, 3,3 '-two Methyl -4- methoxyl group diphenylmethanone, polyvinyl diphenylmethanone, Alpha-hydroxy cyclohexyl benzophenone etc..The photopolymerization of ketal system is drawn Send out agent and for example comprise benzyl dimethyl ketal etc..Thiaxanthone system Photoepolymerizationinitiater initiater for example comprises thiaxanthone, CTX, 2- Methyl thiaxanthone, 2,4- dimethyl thioxanthone, isopropyl thioxanthone, 2,4- bis- clopenthixal ketone, 2,4- diethyl thioxanthone, isopropyl Base thiaxanthone, 2,4- diisopropylthioxanthone, dodecyl thiaxanthone etc..
As above-mentioned acylphosphine oxide system Photoepolymerizationinitiater initiater, for example, can include：Double (2,6- dimethoxy benzene first Acyl) phenyl phosphine oxide, double (2,6- dimethoxybenzoyl) (2,4,4- tri-methyl-amyl) phosphine oxide, double (2,6- dimethoxy Benzoyl)-normal-butyl phosphine oxide, double (2,6- dimethoxybenzoyl)-(2- methylpropane -1- base) phosphine oxide, double (2,6- bis- Methoxybenzoyl)-(1- methylpropane -1- base) phosphine oxide, double (2,6- dimethoxybenzoyl)-tert-butyl group phosphine oxide, double (2,6- dimethoxybenzoyl) cyclohexyl phosphine oxide, double (2,6- dimethoxybenzoyl) octyl group phosphine oxide, double (2- methoxyl group Benzoyl) (2- methylpropane -1- base) phosphine oxide, double (2- methoxybenzoyl) (1- methylpropane -1- base) phosphine oxide, double (2,6- diethoxy benzoyl) (2- methylpropane -1- base) phosphine oxide, double (2,6- diethoxy benzoyl) (1- methyl-prop Alkane -1- base) phosphine oxide, double (2,6- dibutoxy benzoyl) (2- methylpropane -1- base) phosphine oxide, double (2,4- dimethoxy Benzoyl) (2- methylpropane -1- base) phosphine oxide, double (2,4,6- trimethylbenzoyl) (2,4- diamyl phenyl) oxidation Phosphine, double (2,6- dimethoxybenzoyl) benzyl phosphine oxide, double (2,6- dimethoxybenzoyl) -2- phenyl propyl phosphine oxide, Double (2,6- dimethoxybenzoyl) -2- phenylethyl phosphine oxide, the oxidation of double (2,6- dimethoxybenzoyl) -2- phenyl propyl Phosphine, double (2,6- dimethoxybenzoyl) -2- phenylethyl phosphine oxide, 2,6- dimethoxybenzoyl benzyl butyl phosphine oxide, 2,6- dimethoxybenzoyl octyl phosphine oxide, the oxidation of double (2,4,6- trimethylbenzoyl) -2,5- diisopropyl phenyl Phosphine, double (2,4,6- trimethylbenzoyl) -2- aminomethyl phenyl phosphine oxide, double (2,4,6- trimethylbenzoyl) -4- aminomethyl phenyl Phosphine oxide, double (2,4,6- trimethylbenzoyl) -2,5- diethyl phenyl phosphine oxide, double (2,4,6- trimethylbenzoyl) -2, 3,5,6- tetramethylphenyl phosphine oxide, double (2,4,6- trimethylbenzoyl) -2,4- two n-butoxyphenyl phosphine oxide, 2,4,6- Trimethylbenzoyl diphenyl phosphine oxide, double (2,6- dimethoxybenzoyl) -2,4,4- trimethylpentylphosphine oxide, double (2, 4,6- trimethylbenzoyl) isobutyl group phosphine oxide, 2,6- dimethoxybenzoyl -2,4,6- trimethylbenzoyl-normal-butyl oxygen Change phosphine, double (2,4,6- trimethylbenzoyl) phenyl phosphine oxide, double (2,4,6- trimethylbenzoyl) -2,4- dibutoxy phenyl Phosphine oxide, 1,10- double [double (2,4,6- trimethylbenzoyl) phosphine oxide] decane, three (2- toluyl) phosphine oxide etc..
The use level of above-mentioned Photoepolymerizationinitiater initiater is not particularly limited, for example, with respect to for preparing above-mentioned (methyl) third Monomer component total amount 100 mass parts of olefin(e) acid based polymer, preferably 0.01～5 mass parts, more preferably 0.05～3 mass parts In the range of amount.Herein, if the use level of Photoepolymerizationinitiater initiater is less than 0.01 mass parts, there is polyreaction insufficient Situation.If the use level of Photoepolymerizationinitiater initiater absorbs ultraviolet, accordingly, there are more than 5 mass parts, Photoepolymerizationinitiater initiater Ultraviolet cannot reach the situation within adhesive phase.In this case, aggregate rate is occurred to decline, the molecule of the polymer of generation Amount diminishes.
The method obtaining above-mentioned (methyl) acrylic acid series polymeric compounds is not particularly limited, and can be suitable for polymerisation in solution, emulsifying Polymerization, block polymerization, suspended polymerization, radiation-curing polymerization etc., the various polymerizations generally using as synthetic method, Obtain this polymer.
When above-mentioned (methyl) acrylic acid series polymeric compounds are used in bonding sheet, above-mentioned bonding sheet is being used as surface protection In the case of piece, from the viewpoint of the productivity of bonding sheet, can be suitably using polymerisation in solution, emulsion polymerization.Additionally, gained To polymer can be any of random copolymerization, block copolymerization, alternate copolymer, graft copolymer etc..
Preferably above-mentioned (methyl) acrylic acid series polymeric compounds contain firming agent.It is not particularly limited as above-mentioned firming agent, tool For body, preferably comprise from isocyanates system solidfied material, epoxy, aziridine (ethyleneimine) system, metallo-chelate That selects in system and amine system firming agent is one kind or two or more.
For (methyl) acrylic acid series polymeric compounds employing above-mentioned cross-linking agent, the binding agent antistatic additive warp of the present invention By cross-linking agent, be combined with (methyl) acrylic acid series polymeric compounds by covalent bond, therefore, it is possible to speculate under super-humid conditions at higher temperature Durability improve.
As above-mentioned isocyanates system solidfied material, specifically, preferably intramolecular contains the isocyanates of more than 2 functional groups The compound of base, the compound of NCOs more than further preferably 3 functional groups.
As the above-mentioned compound containing NCO, can include：Toluene di-isocyanate(TDI), hexa-methylene two are different Cyanate, isophorone diisocyanate, xylylene diisocyanate (キ シ リ レ Application ジ イ ソ シ ア ネ ト), hydrogenation of benzene Diformazan group diisocyanate, methyl diphenylene diisocyanate, hydrogenated diphenyl methane diisocyanate, durol dimethyl The polyisocyanates such as diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, polymethylene polyphenyl isocyanate Ester compounds and their isocyanate compound and the adduct of polyol compound or the biurets such as trimethylolpropane Body or isocyanuric acid body, further, their isocyanate compound and known polyether polyol, PEPA, Adduct of acrylic polyol (ア Network リ Le Port リ オ Le), polybutadiene polyol, polyisoprene polyol etc. etc..This Can be used alone a kind, it is possible to use two or more.
As the isocyanate curing agent being used as above-mentioned firming agent, the preferably trimethylolpropane of toluene di-isocyanate(TDI) Adduct, the isocyanuric acid ester body of toluene di-isocyanate(TDI), the isocyanuric acid ester body of isophorone diisocyanate, particularly preferably The trimethylolpropane adduct of toluene di-isocyanate(TDI).These can be used alone a kind, it is possible to use two or more.
As the example of aziridine system firming agent, can include：N, N '-diphenyl methane -4,4 '-bis- (1- nitrogen third Pyridine carbonyl compound) (N, N '-ジ Off ェ ニ Le メ タ Application -4,4'- PVC ス (1- ア ジ リ ジ Application カ Le ボ キ サ イ ト)), N- N '-Toluene-2,4-diisocyanate, 4- double (1- aziridinecarboxide), double different phthalyl -1- (2- methylaziridine), three -1- nitrogen third Piperidinyl phosphine oxide, N, double methylol butanol-three [3- (1- of N'- hexa-methylene -1,6- double (1- aziridinecarboxide), 2,2'- '-aziridino) propionic ester], trimethylolpropane tris-β-'-aziridino propionic ester, tetramethylol methane three-β-'-aziridino third Acid esters, three -2,4,6- (l- '-aziridino) -1,3,5- triazine etc..
As the example of epoxy firming agent, can include：The epoxy system resin of bisphenolA-epichlorohydrin type, second two Alcohol diglycidyl ether, polyethylene glycol diglycidyl base ether, glycerol diglycidyl ether, glycerol triglycidyl group Ether, 1,6-HD diglycidyl ether, trimethylolpropane tris glycidyl ether, diglycidylaniline, N, N, N ', N '-four glycidyl group-MXDP, 1,3- double (N, N '-diglycidyl amino methyl) hexamethylene, N, N, N ', N '-four glycidyl group aminophenyl methane, three-glycidyl etc..These can be used alone a kind, it is possible to use 2 More than kind.
As the example of metal-chelator firming agent, can include：Aluminum, ferrum, copper, zinc, stannum, titanium, nickel, antimony, magnesium, vanadium, Coordination compound of the polyvalent metal such as chromium and zirconium and acetylacetone,2,4-pentanedione or ethyl acetoacetate etc..These can be used alone a kind, Can be used two or more.
As the example of amine system firming agent, can include：Hexamethylene diamine, triethyl group diamidogen, polyethyleneimine, six Methenamine, diethylenetriamines, trientine, isophorone diamine, ammonia resin and methylene resin etc..These are permissible It is used alone a kind, it is possible to use two or more.
These firming agent, with respect to (methyl) acrylic acid series polymeric compounds 100 mass parts, preferably use 0.01～10 mass parts, More preferably 0.03～5 mass parts, further preferred 0.05～3 mass parts.
In above-mentioned binder polymer, in addition to mentioned component, do not damaging in the range of effect of the present invention, also may be used With containing from anti-polymerizer, viscosifier, plasticizer, crosslinking accelerator, antioxidant, light stabilizer, anticorrosive metal agent, except upper State a kind or 2 kinds selecting in (methyl) acrylic acid series polymeric compounds beyond binder polymer and reprocessing agent (リ ワ Network) More than.
In order to prepare its coating, preferably in above-mentioned binder polymer, contain organic solvent.As organic solvent, do not have It is particularly limited to, specifically, can include：Benzene,toluene,xylene etc. is aromatic hydrocarbon；Pentane, normal hexane, positive heptan The aliphatic hydrocarbons such as alkane, normal octane；The ester ring type hydro carbons such as Pentamethylene., hexamethylene, cycloheptane, cyclooctane；Anaesthetie Ether, diisopropyl The ethers such as base ether, 1,2- dimethoxy-ethane, dibutyl ethers, oxolane, dioxane, methyl phenyl ethers anisole, phenylethyl ether, diphenyl ether Class；The halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1,2- dichloroethanes, chlorobenzene；Ethyl acetate, propyl acetate, butyl acetate, propanoic acid The esters such as methyl ester；The ketones such as acetone, methyl ethyl ketone, metacetone, methyl iso-butyl ketone (MIBK), Ketohexamethylene；N, N- dimethyl formyl The amide-types such as amine, N-N- dimethyl acetylamide, N-Methyl pyrrolidone；The nitriles such as acetonitrile, benzonitrile；And dimethyl sulfoxide, Sulfoxide types such as sulfolane etc..These polymer solvents can be used alone a kind, it is possible to use two or more.
In above-mentioned binder polymer, the content of organic solvent is usually 50～90 mass %, preferably 60～85 matter Amount %.
Adhesive composition using the binding agent antistatic additive of the present invention is will by using existing known method Binding agent to be prepared with antistatic additive, binder polymer and cross-linking agent as needed, other compositions mixing.For example, Can enumerate to the polymerization containing this copolymer obtaining in i.e. (methyl) acrylic acid series polymeric compounds of composite adhesiveses polymer The method of cooperation ionic compound and cross-linking agent as needed, other composition in thing solution.
【Embodiment】
Then, based on embodiment, the present invention is specifically described, but the present invention is not limited by these embodiments.Following In the record of embodiment etc., unless otherwise noted, " part " expression " mass parts ".
[evaluation of measuring method]
In following embodiments and comparative example, the assay method of various character and evaluation methodology are as follows.
<Molecular weight：Weight average molecular weight (Mw)>
The molecular weight of (methyl) acrylic acid series copolymer is GPC device, the HLC- being manufactured using Tosoh Co., Ltd. 8220GPC is measured, and is obtained by polystyrene conversion value.
Condition determination is as follows.Sample concentration：0.2wt% (THF solution), sample injection rate：10 μ l, eluent：THF, stream Speed：0.6ml/min, temperature of the measurement：40 DEG C, post：Sample column：TSKguardcolumn SuperHZ-H 1+ TSKgelSuperHZM-H 2, reference column：TSKgel SuperH-RC 1, detector：Differential refractometer.
<Durability evaluation>
For the evaluation bonding sheet obtaining in embodiment and comparative example, measure surface electricity under 20 DEG C/65%RH environment Resistance.Sheet resistance value uses the R8340A that Advantest company manufactures, and measures under applied voltage 500V.In this, as first Phase sheet resistance value (Ω/).
Additionally, after placing 500 hours this evaluation bonding sheet under 60 DEG C/90%RH environment, similarly measuring surface Resistance value.In this, as the sheet resistance value after long duration test.
<The preparation of (methyl) acrylic acid series copolymer>
((methyl) acrylic acid series copolymer A)
After there is blender, thermometer, reflux condenser, dripping device, enclose nitrogen in the reaction unit of nitrogen conduit, Add 70 parts of ethyl acetate, 15 parts of acetone, 62.5 parts of butyl acrylate, 19.0 parts of phenoxyethyl acrylate, 16.0 part third E pioic acid methyl ester, 1.5 parts of acrylic acid, 1.0 parts of 2- hydroxy ethyl methacrylates and 0.1 part as azo system polymerization initiator 2,2 '- Azobis isobutyronitrile (and Wako Pure Chemical Industries (strain), trade name V-60).While stirring, in nitrogen stream, returning with solvent Stream thermotonuses 8 hours.After reaction terminates, add 315 parts of toluene, be cooled to room temperature, prepare the poly- of solid constituent 20 weight % Polymer solution.The viscosity of (methyl) the acrylic acid series copolymer A obtaining is 7000mPa s, and weight average molecular weight (Mw) is 1,350,000.
<The preparation of ionic compound>
(ionic compound C-1)
In the four-hole boiling flask with blender, thermometer and cooler, weigh and add the 2- ethoxy three of 139.6g Ammonio methacrylate, double (fluorosulfonyl) imines potassium of 219.2g and 359g acetonitrile, are stirred at room temperature 2 hours.
After the reactant liquor obtaining is filtered, filtrate is carried out concentrating/being dried, obtain the 2- ethoxy front three of 262g Base ammonium=bis- (fluorosulfonyl) imines (yield 92%).
By NMR (1H、13C) measure, FT-IR measures, sub- to the 2- ethoxy trimethyl ammonium obtaining=bis- (fluorosulfonyl) Amine is recognized (Japanese：With fixed)/confirm.
(ionic compound C-2)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add double (the 2- ethoxy) of 169.6g Double (fluorosulfonyl) imines of alkyl dimethyl ammonium chloride, 219.2g and the acetonitrile of 389g, are stirred at room temperature 2 hours.To obtaining After reactant liquor is filtered, filtrate is carried out concentrating/being dried, obtain double (2- ethoxy) Dimethyl Ammonium=bis- (fluorine sulphurs of 292g Acyl group) imines potassium (yield 93%).
By NMR (1H、13C) measure, FT-IR measures, to double (2- ethoxy) Dimethyl Ammonium=bis- (the fluorine sulphonyl obtaining Base) imines carries out recognizing/confirming.
(ionic compound C-3)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add double (the 2- ethoxy) of 267.8g Double (fluorosulfonyl) the imines potassium of octylmethylammonium chloride, 219.2g and 595g acetonitrile, are stirred at room temperature 2 hours.
After the reactant liquor obtaining is filtered, filtrate is carried out concentrating/being dried, double (the 2- ethoxy) that obtain 375g is pungent Ylmethyl ammonium=bis- (fluorosulfonyl) imines (yield 91%).
By NMR (1H、13C) measure, FT-IR measures, to double (2- ethoxy) octyl methyl ammonium=bis- (the fluorine sulphurs obtaining Acyl group) imines carries out recognizing/confirming.
(ionic compound C-4)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add double (2- ethoxy) oil of 406g Double (fluorosulfonyl) the imines potassium of methyl ammonium, 219.2g and 938g acetonitrile, are stirred at room temperature 2 hours.
After the reactant liquor obtaining is filtered, filtrate is carried out concentrating/being dried, obtain double (2- ethoxy) oil of 496g Ylmethyl ammonium=bis- (fluorosulfonyl) imines (yield 90%).
By NMR (1H、13C) measure, FT-IR measures, to double (2- ethoxy) oleyl methyl ammonium=bis- (the fluorine sulphurs obtaining Acyl group) imines carries out recognizing/confirming.
(ionic compound C-5)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add three (2- ethoxy) first of 200g Double (fluorosulfonyl) the imines potassium of ammonium chloride, 219.2g and 420g acetonitrile, are stirred at room temperature 2 hours.
After the reactant liquor obtaining is filtered, filtrate is carried out concentrating/being dried, obtain three (2- ethoxy) first of 310g Base ammonium=bis- (fluorosulfonyl) imines (yield 90%).
By NMR (1H、13C) measure, FT-IR measures, to three (2- ethoxy) ammonium methyl=bis- (fluorosulfonyl) obtaining Imines carries out recognizing/confirming.
(ionic compound C-6)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add double (the 2- ethoxy) of 169.6g Double (trifyl) imine lithium of alkyl dimethyl ammonium chloride, 287.1g and 457g acetonitrile, are stirred at room temperature 2 hours.
After the reactant liquor obtaining is filtered, filtrate is carried out concentrating/being dried, obtain double (2- ethoxys) two of 385g Ammonium methyl=bis- (trifyl) imines (yield 93%).
By NMR (1H、13C) measure, FT-IR measures, to double (2- ethoxy) Dimethyl Ammonium=bis- (fluoroforms obtaining Sulfonyl) imines carries out recognizing/confirming.
(ionic compound C-7)
To the four-hole boiling flask with blender, thermometer, cooler, weigh and the middle 1- octyl group -4- methyl adding 286g Double (fluorosulfonyl) the imines potassium of pyridinium bromide, 219.2g and 505g distilled water, are stirred at room temperature 2 hours, stand 3 hours.Go Except the supernatant of obtained reactant liquor, obtain liquid product (product).
Using 200g distilled water, the liquid product obtaining is carried out with 3 washings, concentrates/be dried, obtain the 1- octyl group of 348g- 4- picoline (1-Octyl-4-methylpyridinium)=bis- (fluorosulfonyl) imines (yield 90%).
By NMR (1H、13C) measure, FT-IR measures, to 1- octyl group -4- picoline=bis- (the fluorine sulphonyl obtaining Base) imines carries out recognizing/confirming.
(ionic compound C-8)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add the 1- ethyl -3- methyl of 236g Imidazole ethyl sulfate (Japanese：1- エ チ Le -3- メ チ Le イ ミ ダ ゾ リ ウ system エ チ Le sulphuric acid), 219.2g double (fluorosulfonyl) imines potassium and 455g distilled water, are stirred at room temperature 2 hours, stand 3 hours.Reactant liquor obtained by removing Supernatant, obtains liquid product.
Using 140g distilled water, the liquid product obtaining is carried out with 3 washings, concentrates/be dried, obtain the 1- ethyl of 233g- 3- Methylimidazole .=bis- (fluorosulfonyl) imines (yield 80%).
By NMR (1H、13C) measure, FT-IR measures, to the 1- ethyl-3-methylimidazole obtaining=bis- (fluorine sulphonyl Base) imines carries out recognizing/confirming.
(ionic compound C-9)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add the octyl trimethyl chlorine of 207.8g Change ammonium, double (fluorosulfonyl) the imines potassium of 219.2g and 427g distilled water, be stirred at room temperature 2 hours, stand 3 hours.Remove institute The supernatant of the reactant liquor obtaining, obtains liquid product.
Using 176g distilled water, the liquid product obtaining is carried out with 3 washings, concentrate/be dried, obtain 324g octyl group front three Base ammonium=bis- (fluorosulfonyl) imines (yield 92%).
By NMR (1H、13C) measure, FT-IR measures, the octyl trimethyl ammonium obtaining=bis- (fluorosulfonyl) imines is entered Row identification/confirm.
(ionic compound C-10)
To in the four-hole boiling flask with blender, thermometer, cooler, weigh and add the 1- ethyl -3- methyl of 236g Double (trifyl) imine lithium of imidazole ethyl sulfate, 287.1g and 523g distilled water, are stirred at room temperature 2 hours, Standing 3 hours.The supernatant of the reactant liquor obtained by removing, obtains liquid product.
Using 196g distilled water, the liquid product obtaining is carried out with 3 washings, concentrates/be dried, obtain the 1- ethyl of 329g- 3- Methylimidazole .=bis- (trifyl) imines (yield 84%).
By NMR (1H、13C) measure, FT-IR measures, to the 1- ethyl-3-methylimidazole obtaining=bis- (fluoroform sulphurs Acyl group) imines carries out recognizing/confirming.
[embodiment 1]
<The preparation of evaluation adhesive composition>
With respect to above-mentioned (methyl) acrylic acid series copolymer solution A 100 weight portion (solid constituent scaled value), add 1.5 The above-mentioned ionic compound C-1 of weight portion (solid constituent scaled value), is stirred.And mix 0.08 weight portion (solid constituent Scaled value) [(Asahi Chemical Industry Co., Ltd manufactures the biuret form of hexamethylene diisocyanate crosslinking agent B, trade name Duranate24A-100)], obtain evaluation adhesive composition.
<The making of evaluation bonding sheet>
The upper evaluation binding agent coating above-mentioned preparation of polyethylene terephthalate film (PET film) crossed in lift-off processing Compositionss, make dry coating thickness be 20 μm, are dried 4 minutes, and are transferred to tri acetyl cellulose membrane (TAC film) at 90 DEG C On, maintain 7 days under 20 DEG C, the atmosphere of 65%RH, obtain evaluation bonding sheet.
Using obtained evaluation bonding sheet, carry out durability evaluation, show the result in table 1.
[embodiment 2～6, comparative example 1～4]
The species of the ionic compound in embodiment 1 is changed according to the content that table 1 is recorded, in addition, with reality Apply example 1 same, preparation, making evaluation adhesive composition, evaluation bonding sheet, carry out durability evaluation.Show the result in Table 1.
[embodiment 7]
<The preparation of evaluation adhesive composition>
With respect to above-mentioned (methyl) acrylic acid series copolymer solution A 100 weight portion (solid constituent scaled value), add 1.5 The above-mentioned ionic compound C-1 of weight portion (solid constituent scaled value), is stirred, obtains evaluation adhesive composition.
<The making of evaluation bonding sheet>
The upper evaluation binding agent coating above-mentioned preparation of polyethylene terephthalate film (PET film) crossed in lift-off processing Compositionss, make dry coating thickness be 20 μm, are dried 4 minutes, are transferred on tri acetyl cellulose membrane (TAC film) at 90 DEG C, Maintain 1 day under 20 DEG C, the atmosphere of 65%RH, obtain evaluation bonding sheet.
Using the evaluation bonding sheet obtaining, carry out durability evaluation.Show the result in table 1.
[embodiment 8～11, comparative example 5～7]
The species of the ionic compound in embodiment 7 is changed according to the content that table 1 is recorded, in addition, with reality Apply example 7 same, preparation, making evaluation adhesive composition, evaluation bonding sheet, carry out durability evaluation.Show the result in Table 1.
[embodiment 12]
<The making of evaluation adhesive composition>
With respect to above-mentioned (methyl) acrylic acid series copolymer solution A 100 weight portion (solid constituent scaled value), add 1.5 The above-mentioned ionic compound C-1 of weight portion (solid constituent scaled value), is stirred.Further, (solid becomes mixing 0.08 weight portion Divide scaled value) [(Asahi Chemical Industry Co., Ltd manufactures the biuret form of hexamethylene diisocyanate crosslinking agent B, trade name Duranate24A-100)], obtain evaluation adhesive composition.
<The making of evaluation bonding sheet>
The upper evaluation binding agent coating above-mentioned preparation of polyethylene terephthalate film (PET film) crossed in lift-off processing Compositionss, make dry coating thickness be 20 μm, are dried 4 minutes, and are transferred to the PET film not carrying out lift-off processing at 90 DEG C On, maintain 7 days under 20 DEG C, the atmosphere of 65%RH, obtain evaluation bonding sheet.
In the state of after the PET film crossing the lift-off processing of obtained evaluation bonding sheet is peeled off, carry out durable Property evaluate.Show the result in table 1.
[embodiment 13～17, comparative example 8～11]
The species of the ionic compound in embodiment 12 is changed according to the content that table 1 is recorded, in addition, with reality Apply example 12 same, preparation, making evaluation adhesive composition, evaluation bonding sheet, carry out durability evaluation.Show the result in Table 1.
[embodiment 18]
<The preparation of evaluation adhesive composition>
With respect to above-mentioned (methyl) acrylic acid series copolymer solution A 100 weight portion (solid constituent scaled value), add 1.5 The above-mentioned ionic compound C-1 of weight portion (solid constituent scaled value), is stirred, obtains evaluation adhesive composition.
<The making of evaluation bonding sheet>
The upper evaluation binding agent coating above-mentioned preparation of polyethylene terephthalate film (PET film) crossed in lift-off processing Compositionss, make dry coating thickness be 20 μm, are dried 4 minutes, and are transferred to the PET film not carrying out lift-off processing at 90 DEG C On, maintain 1 day under 20 DEG C, the atmosphere of 65%RH, obtain evaluation bonding sheet.
In the state of after the PET film crossing the lift-off processing of obtained evaluation bonding sheet is peeled off, carry out durable Property evaluate.Show the result in table 1.
[embodiment 19～22, comparative example 12～14]
The species of the ionic compound in embodiment 18 is changed according to the content that table 1 is recorded, in addition, with reality Apply example 18 same, preparation, making evaluation adhesive composition, evaluation bonding sheet, carry out durability evaluation.Show the result in Table 1.
[evaluation result]
Table 1
According to above-described embodiment and comparative example, in the case of employing the binding agent antistatic additive of the present invention, The variation of sheet resistance value even if after long duration test, is also not observed, even if being durability under the conditions of hot and humid Also excellent binding agent antistatic additive.
Industrial applicability
According to the present invention, even if as the also excellent binding agent antistatic additive of durability under the conditions of hot and humid, being Useful.
Although in detail or with reference to specific embodiment, the present invention will be described, and those skilled in the art should Understand without departing from the spirit and scope of the present invention, various changes can be carried out and revise.
The Japanese patent application 2015-148214 that the present invention was proposed based on July 28th, 2015, and entire contents are tied Together in this as reference.

Claims (3)

1. a kind of binding agent antistatic additive it is characterised in that
Described adhesive antistatic additive contains ionic compound, and the cationic moiety of described ionic compound is by following formula (1) to the cation represented by any one of (3),
[changing 1]
[changing 2]
[changing 3]
Wherein, in above-mentioned formula (1) to (3), R1Represent the alkyl of carbon number more than 1, less than 18, hetero atom can be contained；R2 Represent the alkyl of carbon number more than 2, less than 4, multiple R1Or R2Can distinguish identical or different.
2. binding agent antistatic additive according to claim 1 it is characterised in that
Described ionic compound is the compound that anionicsite contains fluorine atom.
3. binding agent antistatic additive according to claim 1 and 2 it is characterised in that
The anionicsite of described ionic compound is from by double (fluorosulfonyl) imines and double (trifyl) imines group At least one selected in the group becoming.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111566210A (en) * 2018-01-12 2020-08-21 安捷伦科技有限公司 Use of trihydroxy and tetrahydroxy quaternary ammonium compounds as resolving agents for electrophoretic separations

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2017018125A1 (en) * 2015-07-28 2018-06-14 綜研化学株式会社 Adhesive composition for polarizing plate, adhesive layer and polarizing plate with adhesive layer

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1561364A (en) * 2001-08-02 2005-01-05 3M创新有限公司 Optically clear and antistatic pressure sensitive adhesives
CN102965057A (en) * 2011-08-29 2013-03-13 藤森工业株式会社 Adhesive composition containing antistaic agent and adhesive film
CN104105769A (en) * 2012-02-10 2014-10-15 住友化学株式会社 Adhesive sheet, optical film with adhesive, optical laminate, and method for producing adhesive sheet
CN104672715A (en) * 2015-03-06 2015-06-03 苏州市景荣科技有限公司 Environment-friendly antistatic agent for PVC (polyvinyl chloride) sole and preparation method of antistatic agent

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4904825A (en) * 1988-11-08 1990-02-27 Ppg Industries, Inc. Quaternary ammonium antistatic compounds
US20100136265A1 (en) * 2007-04-13 2010-06-03 Everaerts Albert I Antistatic optically clear pressure sensitive adhesive
JP2011032208A (en) * 2009-07-31 2011-02-17 Koei Chem Co Ltd New ammonium salt
JP5526645B2 (en) 2009-08-07 2014-06-18 東洋インキＳｃホールディングス株式会社 Optical pressure-sensitive adhesive and optical pressure-sensitive adhesive sheet using the optical pressure-sensitive adhesive
JP2012126877A (en) * 2010-11-24 2012-07-05 Toyo Ink Sc Holdings Co Ltd Pressure sensitive adhesive composition and pressure sensitive adhesive film using the same
JP5882667B2 (en) * 2011-10-19 2016-03-09 日東電工株式会社 Water-dispersed acrylic pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet
JP2013144777A (en) * 2011-12-15 2013-07-25 Canon Inc Antistatic polyester resin molded article
JP2015003988A (en) 2013-06-20 2015-01-08 古河電気工業株式会社 Adhesive tape for semiconductor processing

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1561364A (en) * 2001-08-02 2005-01-05 3M创新有限公司 Optically clear and antistatic pressure sensitive adhesives
CN102965057A (en) * 2011-08-29 2013-03-13 藤森工业株式会社 Adhesive composition containing antistaic agent and adhesive film
CN104105769A (en) * 2012-02-10 2014-10-15 住友化学株式会社 Adhesive sheet, optical film with adhesive, optical laminate, and method for producing adhesive sheet
CN104672715A (en) * 2015-03-06 2015-06-03 苏州市景荣科技有限公司 Environment-friendly antistatic agent for PVC (polyvinyl chloride) sole and preparation method of antistatic agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111566210A (en) * 2018-01-12 2020-08-21 安捷伦科技有限公司 Use of trihydroxy and tetrahydroxy quaternary ammonium compounds as resolving agents for electrophoretic separations
US11815488B2 (en) 2018-01-12 2023-11-14 Agilent Technologies, Inc. Use of tri- and tetra-hydroxyl quaternary ammonium compounds as resolving agents for electrophoretic separations

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