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WO2009084651A1 - Composition adhésive, article adhésif, composition adhésive à usage optique et procédé d'adhésion - Google Patents

Composition adhésive, article adhésif, composition adhésive à usage optique et procédé d'adhésion Download PDF

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Publication number
WO2009084651A1
WO2009084651A1 PCT/JP2008/073776 JP2008073776W WO2009084651A1 WO 2009084651 A1 WO2009084651 A1 WO 2009084651A1 JP 2008073776 W JP2008073776 W JP 2008073776W WO 2009084651 A1 WO2009084651 A1 WO 2009084651A1
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WIPO (PCT)
Prior art keywords
cation
pressure
adhesive composition
sensitive adhesive
acrylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/JP2008/073776
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English (en)
Japanese (ja)
Inventor
Hiroyuki Ogawa
Manabu Kikuta
Masahiro Kitao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saiden Chemical Industry Co Ltd
DKS Co Ltd
Original Assignee
Saiden Chemical Industry Co Ltd
Dai Ichi Kogyo Seiyaku Co Ltd
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Application filed by Saiden Chemical Industry Co Ltd, Dai Ichi Kogyo Seiyaku Co Ltd filed Critical Saiden Chemical Industry Co Ltd
Priority to CN2008801197984A priority Critical patent/CN101889065A/zh
Priority to KR1020107009329A priority patent/KR101412889B1/ko
Publication of WO2009084651A1 publication Critical patent/WO2009084651A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • 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
    • 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
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C08K5/43—Compounds containing sulfur bound to nitrogen

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive article, an optical pressure-sensitive adhesive composition, and a pressure-sensitive adhesive method.
  • static electricity refers to a phenomenon in which electric charges are stored in an object and charged, or a charged electric charge itself. Static electricity is generated not only by the accumulation of electric charges generated by friction between two types of dielectrics, but also by contact with charged objects and is stored on the surface of the object.
  • Static electricity is a particular problem in the electronics industry because modern electronic devices are extremely susceptible to irreparable damage from electrostatic discharge. Accumulation of static electricity on an insulating object is a serious problem because it is very likely to occur when the humidity is low or when liquids or solids move while contacting each other (friction charging).
  • static electricity is generated on the surface of a display such as a CRT monitor.
  • a display such as a CRT monitor.
  • These static electricity can attract dust from the air.
  • it is an optically transparent antistatic pressure-sensitive adhesive, it can be applied to the surface of the CRT together with a display film such as a CRT permeation control film to release static electricity.
  • a display film such as a CRT permeation control film to release static electricity.
  • static electricity is generated on the surface of the pressure-sensitive adhesive when the release liner is removed. Such static electricity attracts dust, which can result in a product with poor performance.
  • Static electricity accumulation can be adjusted by increasing the conductivity of the material. This can be achieved by increasing the ionic or electronic conductivity.
  • Today, the most common means for regulating the accumulation of static electricity is to absorb moisture and increase conductivity.
  • optically transparent antistatic pressure-sensitive adhesives and the like have been proposed as applications of optical displays and other optical films using pressure-sensitive pressure-sensitive adhesives and release liners.
  • This invention is made
  • the first aspect of the present invention is: A pressure-sensitive adhesive composition containing bis (fluorosulfonyl) imide.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the second aspect of the present invention is Contains ion pairs,
  • the anion of the ion pair is bis (fluorosulfonyl) imide.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the third aspect of the present invention is 3.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the fourth aspect of the present invention is 3.
  • [R1 in the formula (A) represents a hydrocarbon group having 4 to 20 carbon atoms, and may contain a hetero atom, and R2 and R3 may be the same or different and represent hydrogen or a hydrocarbon group having 1 to 16 carbon atoms. Represents a hetero atom. However, when the nitrogen atom contains a double bond, there is no R3.
  • [R4 in the formula (B) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a heteroatom
  • R5, R6, and R7 may be the same or different, and may be hydrogen or 1 to 16 carbon atoms. It represents a hydrocarbon group and may contain a hetero atom.
  • [R8 in the formula (C) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a heteroatom
  • R9, R10, and R11 may be the same or different, and may be hydrogen or 1 to 16 carbon atoms. It represents a hydrocarbon group and may contain a hetero atom.
  • [X in the formula (D) represents a nitrogen, sulfur, or phosphorus atom, and R12, R13, R14, and R15 are the same or different and each represents a hydrocarbon group having 1 to 20 carbon atoms; May be included. However, when X is a sulfur atom, there is no R12. ] It is in.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • R1 in the formula (A) represents a hydrocarbon group having 4 to 20 carbon atoms and may contain a heteroatom
  • R2 and R3 may be the same or different and represent hydrogen or a hydrocarbon group having 1 to 6 carbon atoms. Represents a hetero atom. However, when the nitrogen atom contains a double bond, there is no R3. ]
  • R4 in the formula (B) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a hetero atom
  • R5, R6, and R7 may be the same or different, and may be hydrogen or 1 to 10 carbon atoms. It represents a hydrocarbon group and may contain a hetero atom.
  • R8 in the formula (C) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a heteroatom
  • R9, R10, and R11 may be the same or different, and may be hydrogen or 1 to 2 carbon atoms. It represents a hydrocarbon group and may contain a hetero atom.
  • X in the formula (D) represents a nitrogen, sulfur, or phosphorus atom; R12, R13, R14, and R15 are the same or different and each represents a hydrocarbon group having 1 to 10 carbon atoms; May be included. However, when X is a sulfur atom, there is no R12. ]
  • the fifth aspect of the present invention provides The cation of the ion pair is one selected from the group consisting of 1-octyl-2-methylpyridinium, 1-octyl-3-methylpyridinium, 1-octyl-4-methylpyridinium and 1-octylpyridinium.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the sixth aspect of the present invention provides 3.
  • the adhesive it is also possible to incorporate the excellent properties of the polymer into the adhesive.
  • an optical film based on a generally optically transparent acrylate polymer, silicone system, rubber resin system, block copolymer system, particularly those containing hydrogenated elastomer, or vinyl ether polymer system. .
  • the seventh aspect of the present invention provides 7.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the eighth aspect of the present invention is The polymer is composed of at least one selected from the group consisting of 2-ethylhexyl acrylate, butyl acrylate, methyl acrylate, phenoxyethyl acrylate, methoxypolyethylene glycol methacrylate, 2-hydroxyethyl acrylate, acrylic acid and acrylamide as a monomer composition.
  • the adhesive composition which is not inferior to the past adhesive composition or has the outstanding characteristic is obtained.
  • the ninth aspect of the present invention provides
  • the adhesive composition which can be used in the manufacturing process etc. which need to avoid the problem which arises by static electricity is obtained.
  • the tenth aspect of the present invention provides An adhesive article comprising bis (fluorosulfonyl) imide. It is in.
  • the adhesive article which is not inferior to the conventional adhesive composition or has an excellent characteristic is obtained.
  • the eleventh aspect of the present invention is An optical pressure-sensitive adhesive comprising bis (fluorosulfonyl) imide.
  • required to be optically transparent is obtained.
  • the twelfth aspect of the present invention is The object is to adhere an object with a composition containing bis (fluorosulfonyl) imide.
  • the adhesion method which is not inferior to the past adhesion method or has the outstanding characteristic is obtained.
  • a pressure-sensitive adhesive composition having excellent characteristics can be obtained.
  • the pressure-sensitive adhesive and pressure-sensitive adhesive composition of this embodiment comprise an ion pair such as an ionic liquid and a base polymer (base polymer).
  • the ionic liquid refers to, for example, a salt having a melting temperature of less than 100 ° C., a molten salt (ionic compound) that exhibits a liquid state at room temperature (25 ° C.), or a salt having good compatibility with a polymer.
  • the ionic liquid acts as an antistatic agent, and by using this, the antistatic agent bleed is suppressed, and the pressure-sensitive adhesive composition has low contamination to the adherend even over time or at high temperatures. Things are obtained.
  • the antistatic effect by the surfactant having a long chain alkyl group or the like is manifested by the surface of the surfactant bleed and the formation of a charge leakage layer with moisture in the air.
  • the ionic liquid since the ionic liquid is in a liquid state, the molecular movement is easier than that of the surfactant, and the rearrangement of molecules easily occurs due to the generation of electric charges. Therefore, in the case of an ionic liquid, since a charge neutralization mechanism by molecular rearrangement works, it is considered that an excellent antistatic effect can be obtained without bleed on the surface as compared with the surfactant.
  • the ionic liquid is preferably liquid at room temperature. Compared with a solid salt, addition to an adhesive and dispersion or dissolution can be easily performed. Furthermore, since the ionic liquid has no vapor pressure (nonvolatile), the antistatic property is continuously obtained without disappearing with time.
  • the acid value of the base polymer is preferably 10 or less, more preferably 1.0 or less. If the acid value is 10 or less, it has substantially no acid functional group that has a large interaction with the ionic liquid, and does not interfere with the charge neutralization mechanism by molecular rearrangement as described above, and thus is antistatic. The function can be suitably expressed. In addition, since a polymer having an alkyl group having a specific carbon number is used, the compatibility with the ionic liquid is good and the balance of the adhesive property is excellent.
  • the acid value means the number of mg of potassium hydroxide required to neutralize free fatty acid, resin acid, etc. contained in 1 g of a sample.
  • the acid value of the base polymer is preferably 10 or less, more preferably 1.0 or less, further preferably 0.8 or less, and most preferably 0.0.
  • Adjustment of the acid value of a polymer can be performed by making the usage-amount of the monomer which has a carboxyl group or a sulfonate group zero or less.
  • Tables 1A and 1B are measurement data of physical properties of various ionic liquids of the present embodiment. Thereby, the appropriateness etc. as an antistatic agent use can be investigated. Here, surface resistance, peeling voltage, adhesive strength, aluminum corrosion and substrate adhesion were measured. In the table, it is shown that as the background of the data is thinner, the physical property value is more preferable for use in antistatic or the like. In addition, the data with the underlined portion have particularly preferable physical property values when used for antistatic or the like.
  • Table 2 is a table showing a composition example of the base polymer.
  • Table 3 is a table showing the monomer structure.
  • Table 4 shows the ionic species structure. The compounds shown in these tables were used in the measurements. In addition, in this specification, each compound is shown by the abbreviation described in these tables.
  • the electrical conductivity is evaluated by measuring the surface resistance value based on the above-described “leakage amount”, that is, the measure of ease of leakage. This is because there are few errors due to the measurement environment and measurement method, and the measurement can be performed accurately. On the other hand, peeling band voltage is also measured. This is a technique for measuring the values corresponding to the “charge amount” and “generation amount”, both of which are values that change with time. In this way, it is possible to know the correctness more accurately by measuring the physical properties of the same sample from both viewpoints.
  • the ionic liquid of the present embodiment has the same physical properties as TFSI or much higher than TFSI.
  • Table 5 is data showing physical properties of the antistatic agent of this embodiment. For each combination of compounds, the melting point, surface resistance, electrical conductivity and adhesion were measured. Also in the measurement values of the sample of this embodiment, the antistatic agent of this embodiment has the same physical properties as the antistatic agent containing various compounds such as TFSI or the physical properties that greatly exceed the antistatic agent containing various compounds such as TFSI. You can see that
  • Table 6 shows data obtained by measuring changes in physical properties of the antistatic agent of the present embodiment while changing the content of each component.
  • FIG. 1 is a diagram showing a chemical formula and the like of a bis (fluorosulfonyl) imide anion.
  • compounds are indicated by abbreviations shown in this figure.
  • FIG. 2 is a diagram showing the molecular size of the FSI anion.
  • FSI has a minimum volume as an imide salt. This indicates that FSI can move freely in space and has high antistatic ability.
  • FIG. 3 is a diagram showing the properties of EMlm-FSI ionic liquid.
  • FIG. 4 is a diagram showing temperature dependence of viscosity. FSI has a lower viscosity than other compounds, indicating that it is easier to process.
  • FIG. 5 is a graph showing the temperature dependence of ion conductivity.
  • FIG. 6 is a diagram showing the properties of the FSI ionic liquid when the cation is changed.
  • FIG. 7 is a cyclic voltammetry (CV) curve.
  • FIG. 8 is a diagram comparing thermal stability.
  • FIG. 9 is a diagram for comparing the solubility.
  • FIG. 10 is a diagram showing the viscosity of a propylene carbonate (propylene carbonate) solution.
  • FIG. 11 is a diagram showing ionic conductivity as a propylene carbonate solution.
  • FIG. 12 is a diagram showing chemical stability in water.
  • FIG. 13 is a diagram showing the stability of anions in water.
  • FSI has excellent properties comparable to other compounds such as TFSI.
  • FSI has been found to be a very good compound for application as an adhesive with high conductivity, low viscosity, excellent solubility, good properties at low temperatures, and hydrophobic properties. .
  • the bis (chlorosulfonyl) imide anion compound obtained from sulfamic acid, chlorosulfonic acid and halogenating agent is fluorine-substituted using a base catalyst such as nitrogen-containing compound (for example, trimethylamine) to obtain the FSI compound. It is preferable to do.
  • This reaction may be in high yield, but in addition, the FSI compound obtained thereby has a high purity and is very good for applying the product as an adhesive.
  • the ion pair may be used alone or in combination of two or more. Moreover, the following may be sufficient as an ion pair, for example. Examples include ionic liquids that are at least one of nitrogen-containing onium salts, sulfur-containing onium salts, and phosphorus-containing onium salts. In particular, the ionic liquid preferably contains one or more cations represented by the following general formulas (A) to (D). An ionic liquid having these cations provides a further excellent antistatic ability.
  • R 1 in the formula (A) represents a hydrocarbon group having 4 to 20 carbon atoms and may contain a hetero atom
  • R 2 and R 3 may be the same or different and each may be hydrogen or 1 to 16 carbon atoms. It represents a hydrocarbon group and may contain a hetero atom. However, when the nitrogen atom contains a double bond, there is no R 3 .
  • [R 4 in the formula (B) represents a hydrocarbon group having 2 to 20 carbon atoms and may contain a hetero atom
  • R 5 , R 6 , and R 7 may be the same or different and each may represent hydrogen or carbon number. Represents 1 to 16 hydrocarbon groups and may contain heteroatoms.
  • [R8 in the formula (C) represents a hydrocarbon group having 2 to 20 carbon atoms, may contain a heteroatom
  • R 9, R 10 and R 11, are the same or different, hydrogen or C 1 -C To 16 hydrocarbon groups, which may contain heteroatoms.
  • [X in the formula (D) represents a nitrogen, sulfur, or phosphorus atom
  • R 12 , R 13 , R 14 , and R 15 are the same or different and represent a hydrocarbon group having 1 to 20 carbon atoms.
  • And may contain a heteroatom.
  • cations may be modified with an octyl group, an ethylhexyl group, an allyl group, or the like.
  • Examples of the cation represented by the formula (A) include a pyridinium cation, an octylpiperidinium cation, an allyl piperidinium cation, a pyrrolidinium cation, a cation having a pyrroline skeleton, and a cation having a pyrrole skeleton.
  • Examples of the cation represented by the formula (B) include an imidazolium cation, an octylimidazolium cation, a tetrahydropyrimidinium cation, and a dihydropyrimidinium cation.
  • Specific examples include 1,3-dimethylimidazolium cation, 1,3-diethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1-butyl-3-methylimidazolium cation, 1-hexyl- 3-methylimidazolium cation, 1-octyl-3-methylimidazolium cation, 1-decyl-3-methylimidazolium cation, 1-dodecyl-3-methylimidazolium cation, 1-tetradecyl-3-methylimidazolium cation 1,2-dimethyl-3-propylimidazolium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-butyl-2,3-dimethylimidazolium cation, 1-hexyl-2,3-dimethyl Imidazolium cation, 1,3-dimethyl-1,4 5,6-tetrahydro
  • Examples of the cation represented by the formula (C) include a pyrazolium cation and a virazolinium cation. Specific examples include 1-methylpyrazolium cation, 3-methylpyrazolium cation, 1-ethyl-2-methylpyrazolinium cation and the like.
  • Examples of the cation represented by the formula (D) include a tetraalkylammonium cation, a trialkylsulfonium cation, a tetraalkylphosphonium cation, and those in which a part of the alkyl group is substituted with an alkenyl group, an alkoxyl group, or an epoxy group. Is mentioned.
  • tetramethylammonium cation examples include tetramethylammonium cation, tetraethylammonium cation, tetrabutylammonium cation, tetrahexylammonium cation, triethylmethylammonium cation, tributylethylammonium cation, trimethyldecylammonium cation, N, N-diethyl-N-methyl-N -(2-methoxyethyl) ammonium cation, glycidyltrimethylammonium cation, N, N-dimethyl-N, N-dipropylammonium cation, N, N-dimethyl-N, N-dihexylammonium cation, N, N-dipropyl- N, N-dihexylammonium cation, trimethylsulfonium cation, triethylsulfon
  • ion pairs such as ionic liquids
  • commercially available ones may be used, but they can also be synthesized as follows.
  • the method of synthesizing the ionic liquid is not particularly limited as long as the desired ionic liquid can be obtained. However, it is described in the document “Ionic liquids—the forefront and future of development” [issued by CMC Publishing Co., Ltd.].
  • the halide method, hydroxide method, acid ester method, complex formation method, neutralization method and the like can be used.
  • the blending amount of the ionic liquid cannot be defined unconditionally because it varies depending on the compatibility of the acrylic polymer used and the ionic liquid, but is generally 0.01 to 40 weights with respect to 100 parts by weight of the base polymer. Parts, preferably 0.03 to 20 parts by weight, and most preferably 0.05 to 10 parts by weight. If it is less than 0.01 part by weight, sufficient antistatic properties cannot be obtained, and if it exceeds 40 parts by weight, the contamination of the adherend tends to increase.
  • the base polymer may be, for example:
  • the base polymer may be one containing an acrylic polymer having as a main component one or more of acrylates and / or methacrylates having an alkyl group having 1 to 14 carbon atoms.
  • the acrylic polymer preferably has a glass transition point Tg of 0 ° C. or lower (usually ⁇ 100 ° C. or higher) from the viewpoint of balance of adhesive performance.
  • the alkyl group preferably has 6 to 14 carbon atoms.
  • acrylic polymer mainly composed of one or more of acrylates and / or methacrylates having an alkyl group having 1 to 14 carbon atoms
  • examples of the acrylic polymer mainly composed of one or more of acrylates and / or methacrylates having an alkyl group having 1 to 14 carbon atoms include acrylates and / or methacrylates having an alkyl group having 1 to 14 carbon atoms ⁇ Hereinafter referred to as (meth) acrylate.
  • (meth) acrylate Acrylic polymer having a weight average molecular weight of 100,000 or more, the main component of which is a monomer containing 50 to 100% by weight of one or more of
  • the (meth) acrylate having an alkyl group having 1 to 14 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl ( (Meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl ( Examples include meth) acrylate, isodecyl (meth) acrylate, n-dodecyl (meth) acrylate, n-tridecyl (meth) acrylate, and n-tetradecyl (
  • a hydroxyl group-containing monomer is preferable because crosslinking can be easily controlled, and an acrylate and / or methacrylate having a hydroxyl group is particularly preferable.
  • Hydroxyl group-containing monomers include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate, (4-hydroxymethylcyclohexyl) methyl acrylate, N-methylol (meth) acrylamide, vinyl alcohol, allyl alcohol, 2-hydroxyethyl vinyl ether, 4 -Hydroxybutyl vinyl ether, diethylene glycol monovinyl ether and the like.
  • the amount of the hydroxyl group-containing monomer used is preferably 0.5 to 10% by weight, more preferably 1 to 8% by weight in the constituent monomer components.
  • Components other than the above hydroxyl group-containing monomers include cyano group-containing monomers such as acrylonitrile, vinyl esters such as vinyl acetate, aromatic vinyl compounds such as styrene, phenoxyethyl (meth) acrylate, and benzyl (meth) acrylate. Cohesive strength / heat resistance / refractive property improving component, amide group-containing monomer such as acrylamide, dimethylacrylamide, diethylacrylamide, N, N-dimethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, etc.
  • Amino group-containing monomers glycidyl (meth) acrylate, epoxy group-containing monomers such as allyl glycidyl ether, vinyl ethers such as N-acryloylmorpholine, vinyl ethyl ether, (meth) acrylic acid, Component having a functional group that acts as adhesion improvement and crosslinking base point, such as a carboxyl group-containing monomer such as carboxymethyl ethyl acrylate.
  • the above components can be used alone or in combination of two or more.
  • the pressure-sensitive adhesive of the present embodiment can obtain pressure-sensitive adhesive sheets that are further excellent in heat resistance by appropriately crosslinking an acrylic polymer.
  • a compound having a group capable of reacting with a hydroxyl group, an amino group, an amide group, or the like appropriately included as a crosslinking base point in an acrylic polymer such as a polyisocyanate compound, an epoxy compound, or an aziridine compound is added.
  • a so-called cross-linking agent that is reacted.
  • polyisocyanate compounds and epoxy compounds are particularly preferably used.
  • polyisocyanate compound examples include lower aliphatic polyisocyanates such as butylene diisocyanate and hexamethylene diisocyanate, alicyclic isocyanates such as cyclopentylene diisocyanate, cyclohexylene diisocyanate, and isophorone diisocyanate, 2,4-tolylene diisocyanate, Aromatic diisocyanates such as 4,4'-diphenylmethane diisocyanate and xylylene diisocyanate, trimethylolpropane / tolylene diisocyanate trimer adduct (trade name Coronate L), trimethylolpropane / hexamethylene diisocyanate trimer adduct ( Product name Coronate HL), isocyanurate of hexamethylene diisocyanate (Product name Coronate HX) Urethane Industry Co., Ltd.] and the like isocyanate adducts such as.
  • Epoxy compounds include N, N, N ′, N′-tetraglycidyl-m-xylenediamine (trade name TETRAD-X) and 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane (trade name TETRAD- C) [all manufactured by Mitsubishi Gas Chemical Co., Ltd.]. These crosslinking agents are used alone or in a mixture of two or more. The amount of the crosslinking agent to be used is appropriately selected depending on the balance with the acrylic polymer to be crosslinked and, further, depending on the intended use as the pressure-sensitive adhesive sheet.
  • the acrylic pressure-sensitive adhesive In order to obtain sufficient heat resistance by the cohesive strength of the acrylic pressure-sensitive adhesive, it is generally preferable to add 0.5 parts by weight or more with respect to 100 parts by weight of the acrylic polymer. Moreover, it is preferable to mix
  • MURA is better.
  • MURA is better when it contains low molecular weight components.
  • MURA is better if it contains a low molecular weight component with two aromatics.
  • the antistatic function is expressed by including an AS (antistatic) agent (antistatic agent), and the function is improved by including a low molecular weight component.
  • low molecular weight component examples include dimethyl adipate, diisobutyl adipate, dibutoxyethyl adipate, di- (2-ethylhexyl) adipate, diisooctyl adipate, diisodecyl adipate, octyldecyl adipate, di- (2-ethylhexyl) azelate, di- Dibasic fatty acid esters such as isooctyl azelate, diisobutyl azelate, dibutyl sebacate, di- (2-ethylhexyl) sebacate, diisooctyl sebacate; maleic acid ester; trimellitic acid isodecyl ester, trimellitic acid octyl ester , Trimellitic acid esters such as trimellitic acid n-octyl ester and isononyl trimellitic acid;
  • benzoic acid esters examples include diethylene glycol dibenzoate, dipropylene glycol dibenzoate, benzyl benzoate, and 1,4-cyclohexanedimethanol dibenzoate.
  • Tricresyl phosphate trixylenyl phosphate, cresyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate.
  • the usage fee for the low molecular weight component is usually 1 to 50 parts by weight per 100 parts by weight of the acrylic polymer.
  • polyfunctional monomer which has 2 or more of radiation reactive unsaturated bonds as a substantial crosslinking agent, and can also be bridge
  • the polyfunctional monomer having two or more radiation-reactive unsaturated bonds is one or more radiation reactions that can be crosslinked (cured) by irradiation with radiation such as vinyl, acryloyl, methacryloyl, and vinylbenzyl groups.
  • a polyfunctional monomer component having two or more properties is used. In general, those having 10 or less radiation-reactive unsaturated bonds are preferably used. Two or more polyfunctional monomers can be used in combination.
  • polyfunctional monomer examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6 hexanediol di ( And (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, divinylbenzene, and N, N′-methylenebisacrylamide.
  • the amount of the polyfunctional monomer used is appropriately selected depending on the balance with the acrylic polymer to be crosslinked and further depending on the intended use as an adhesive sheet. In order to obtain sufficient heat resistance by the cohesive strength of the acrylic pressure-sensitive adhesive, it is generally preferable to add 0.1 to 30 parts by weight with respect to 100 parts by weight of the acrylic polymer. Moreover, it is more preferable to mix
  • Examples of the radiation include ultraviolet rays, laser rays, ⁇ rays, ⁇ rays, ⁇ rays, x rays, electron rays, and the like, and ultraviolet rays are preferably used from the viewpoints of controllability, good handleability, and cost. More preferably, ultraviolet rays having a wavelength of 200 to 400 nm are used. Ultraviolet rays can be irradiated using an appropriate light source such as a high-pressure mercury lamp, a microwave excitation lamp, or a chemical lamp. In addition, when using an ultraviolet-ray as a radiation, a photoinitiator is added to an acrylic adhesive.
  • the photopolymerization initiator may be any substance that generates radicals or cations by irradiating ultraviolet rays having an appropriate wavelength that can trigger the polymerization reaction according to the type of the radiation-reactive component.
  • radical photopolymerization initiators include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, o-benzoyl benzoic acid methyl-p-benzoin ethyl ether, benzoin isopropyl ether, ⁇ -methylbenzoin, benzyldimethyl ketal, trichloroacetophenone Acetophenones such as 2,2-diethoxyacetophenone and 1-hydroxycyclohexyl phenyl ketone, propio such as 2-hydroxy-2-methylpropiophenone and 2-hydroxy-4'-isopropyl-2-methylpropiophenone Benzophenones such as phenones, benzophenone, methylbenzophenone, p-chlorobenzophenone, p-dimethylaminobenzofuninone, 2-chlorothioxanthone, 2-ethylthioxone Thioxanthones such as N,
  • Examples of the cationic photopolymerization initiator include onium salts such as aromatic diazonium salts, aromatic iodonium salts, and aromatic sulfonium salts, organometallic complexes such as iron-allene complexes, titanocene complexes, and arylsilanol-aluminum complexes, nitrobenzyl
  • examples thereof include esters, sulfonic acid derivatives, phosphoric acid esters, sulfonic acid derivatives, phosphoric acid esters, phenol sulfonic acid esters, diazonaphthoquinone, and N-hydroxyimide sulfonate.
  • the said photoinitiator it is also possible to use 2 or more types together.
  • the photopolymerization initiator is preferably blended in an amount of usually 0.1 to 10 parts by weight, preferably 0.2 to 7 parts by weight with respect to 100 parts by weight of the acrylic polymer.
  • a photoinitiated polymerization aid such as amines in combination.
  • the photoinitiator aid include 2-dimethylaminoethylbenzoate, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, p-dimethylaminobenzoic acid isoamyl ester, and the like.
  • Two or more photopolymerization initiation assistants can be used in combination.
  • the polymerization initiation assistant is preferably added in an amount of 0.05 to 10 parts by weight, more preferably 0.1 to 7 parts by weight, based on 100 parts by weight of the acrylic polymer.
  • Nitrogen gas was sealed in a reactor equipped with a stirrer, thermometer, reflux condenser and nitrogen inlet tube, and then 75 parts of ethyl acetate, 15 parts of acetone, 20 parts of butyl acrylate, 80 parts of 2-ethylhexyl acrylate, 4-hydroxyoxy Charge 3.5 parts of butyl acrylate and 0.2 part of a polymerization initiator (azobisisobutyronitrile). The reaction is carried out for 7 hours at the reflux temperature of the solvent with stirring.
  • a polymerization initiator azobisisobutyronitrile
  • a biuret type of hexamethylene diisocyanate (trade name Duranate 24A-100 manufactured by Asahi Kasei Kogyo Co., Ltd.) as a cross-linking agent is blended with 100 parts by weight of the solid content of the copolymer composition, and 2.0 parts by solid content. An adhesive was obtained.
  • FIG. 14 is a diagram showing a stripping voltage test method. At this time, the measurement is performed by fixing the polarizing plate attached to the glass plate on the aluminum plate. Various conditions at the time of measurement are as follows.
  • Electrostatic potential measuring device Keyence's high precision electrostatic sensor SK-200, SK-030 used
  • a copolymer A-1 having a viscosity of 7,000 mPa ⁇ s, a solid content of 20.0%, and a weight average molecular weight of 1.35 million was obtained.
  • polarizing plate general polarizing plate, thickness 100 ⁇ m.
  • the film was cured in an atmosphere of 23 ° C. and 65% RH for 7 days to obtain a polarizing plate sample.
  • the obtained polarizing plate sample was cut into 80 mm ⁇ 150 mm so that the absorption axis was 45 ° with respect to the long side of the polarizing plate, and a pressure of 5 kg / cm 2 was applied to one side of the glass plate at 50 ° C. for 18 minutes.
  • the test samples held and pasted were left in an atmosphere of 90 ° C., 60 ° C. and 90% RH for 500 hours, and as a result of examining the occurrence of foaming and peeling, both were good.
  • the obtained polarizing plate sample was placed on both surfaces of the glass plate so that the absorption axis was orthogonal, and a test sample was applied at 50 ° C. under a pressure of 5 kg / cm 2 and held for 18 minutes. As a result of examining the occurrence state of MURA (unevenness) by leaving it in the atmosphere for 500 hours, it was good.
  • MURA (unevenness) evaluation was performed visually.
  • the same sample after the 80 ° C. durability test using the adhesive sheet of the above-mentioned adhesive was bonded in a crossed Nicol state and placed on the backlight of the liquid crystal monitor, and the MURA (unevenness) state was changed. It observed visually and evaluated by the following reference
  • the adhesive sheet was peeled off 180 ° according to JIS Z-0237, and the adhesive strength was measured.
  • a glass plate is used as the adherend.
  • the amount of displacement of the pressure-sensitive adhesive pressure-sensitive adhesive sheet is measured according to the holding power measurement method of JIS Z-0237. That is, it is cut into 25 mm ⁇ 55 mm so that the absorption axis is 90 ° with respect to the long side of the polarizing plate, and a pressure of 5 kg / cm 2 is applied to the glass plate at 50 ° C. so that the adhesion area is 25 mm ⁇ 10 mm. Then, a test sample is prepared by holding for 18 minutes and affixed with a load of 9.8 N in an atmosphere of 90 ° C., and the deviation after 1 hour is measured.
  • the acid value is measured using an automatic titrator COM-550 manufactured by Hiranuma Sangyo Co., Ltd., and can be obtained from the following formula.
  • A Acid value
  • Y Titration volume of sample solution (ml)
  • X Titration volume of solution containing only 50 g of mixed solvent (ml)
  • f Factor of titration 30 solution
  • M Weight of polymer sample (g)
  • Titration solution 0.1N, 2-propanol potassium hydroxide solution (manufactured by Wako Pure Chemical Industries, Ltd., for petroleum product neutralization value test), electrode: glass electrode; GE-101, comparative electrode; RE-201 Measurement mode: Petroleum product neutralization number test 1.
  • the molecular weight is measured using a GPC apparatus manufactured by Tosoh Corporation, HLC-8220 GPC, and can be obtained as a converted value of polystyrene.
  • the measurement conditions are as follows. Sample concentration: 0.2 wt% (THF solution), sample injection amount: 10 ⁇ l, eluent: THF, flow rate: 0.6 ml / min, measurement temperature: 40 ° C., column: sample column; TSKguardcolumnSuperHZ-H1 + TSKgelSuperHZM-H2 Reference column; 1 TSKgel SuperH-RC; Detector: differential refractometer.
  • the glass transition temperature Tg (° C.) can be obtained from the following formula using the following literature values as the glass transition temperature Tgn (° C.) of the homopolymer of each monomer.
  • Tg (° C.) is the glass transition temperature of the copolymer
  • Wn ( ⁇ ) is the weight fraction of each monomer
  • Tgn (° C.) is the glass transition temperature of the homopolymer of each monomer
  • n is the type of each monomer Represents.
  • Isononyl acrylate -82 ° C
  • Acrylic acid 106 ° C
  • This embodiment can also be applied to pressure-sensitive adhesive sheets.
  • the pressure-sensitive adhesive sheets have a pressure-sensitive adhesive layer containing the pressure-sensitive adhesive composition as described above on one side or both sides of a support. According to the pressure-sensitive adhesive sheets of the present embodiment, since the pressure-sensitive adhesive composition of the present embodiment that exhibits the above-described effects is used, the adherend can be prevented from being charged when peeled, and the adherend is contaminated. The pressure-sensitive adhesive sheet can be reduced.
  • the said support body is equipped with the plastic film by which antistatic treatment was carried out.
  • the plastic film By subjecting the plastic film to an antistatic treatment, the withstand voltage to be peeled off from the adherend can be made within ⁇ 0.5 kV, for example, and the antistatic property is further improved.
  • the pressure-sensitive adhesive used for the pressure-sensitive adhesive sheet includes various tackifiers, surface lubricants, leveling agents, antioxidants, corrosion inhibitors, light stabilizers, ultraviolet absorbers, polymerization inhibitors, silane coupling agents, inorganic Or it can add suitably according to the use which uses various additives, such as powders, such as an organic filler, metal powder, and a pigment, and a particulate form and a foil-like thing.
  • the pressure-sensitive adhesive sheets are provided on one side of various supports made of a plastic film such as a polyester film or a porous material such as paper or nonwoven fabric so that the pressure-sensitive adhesive has a thickness of usually 3 to 100 ⁇ m, preferably about 5 to 50 ⁇ m. Alternatively, it is applied and formed on both sides to form a sheet or tape. Particularly in the case of a surface protective film, it is preferable to use a plastic substrate as a support.
  • the plastic substrate is not particularly limited as long as it can be formed into a sheet shape or a film shape.
  • the thickness of the film is usually about 5 to 200 ⁇ m, preferably about 10 to 100 ⁇ m.
  • an antistatic treated plastic film is more preferably used.
  • the antistatic treatment applied to the plastic film is not particularly limited, and a method of providing an antistatic layer on at least one surface of a generally used film or a method of kneading a kneading type antistatic agent into the plastic film is used.
  • a method of providing an antistatic layer on at least one surface of the film an antistatic resin comprising an antistatic agent and a resin component, a conductive polymer, a method of applying a conductive resin containing a conductive material, or a conductive material is deposited. Or the method of plating is mention
  • Antistatic agents contained in the antistatic resin include cationic antistatic agents having cationic functional groups such as quaternary ammonium salts, pyridinium salts, primary, secondary and tertiary amino groups, and sulfonates.
  • An anionic antistatic agent having an anionic functional group such as sulfate salt, phosphonate, phosphate ester salt, amphoteric antistatic agent such as alkylbetaine and its derivatives, imidazoline and its derivatives, alanine and its derivatives,
  • Nonionic antistatic agents such as aminoalcohol and derivatives thereof, glycerin and derivatives thereof, polyethylene glycol and derivatives thereof, and monomers having an ion conductive group of the above cation type, anion type and zwitterionic type are polymerized or Examples thereof include ionic conductive polymers obtained by copolymerization. These compounds may be used alone or in combination of two or more.
  • a cationic type antistatic agent for example, it has a quaternary ammonium group such as alkyltrimethylammonium salt, acyloylamidopropyltrimethylammonium methosulfate, alkylbenzylmethylammonium salt, acylcholine chloride, polydimethylaminoethyl methacrylate (meth) Examples thereof include acrylate copolymers, styrene copolymers having quaternary ammonium groups such as polyvinylbenzyltrimethylammonium chloride, and diallylamine copolymers having quaternary ammonium groups such as polydiallyldimethylammonium chloride. These compounds may be used alone or in combination of two or more.
  • anionic antistatic agent examples include alkyl sulfonate, alkyl benzene sulfonate, alkyl sulfate ester salt, alkyl ethoxy sulfate ester salt, alkyl phosphate ester salt, and sulfonic acid group-containing styrene copolymer. These compounds may be used alone or in combination of two or more.
  • zwitterionic antistatic agents examples include alkylbetaines, alkylimidazolium betaines, and carbobetaine graft copolymers. These compounds may be used alone or in combination of two or more.
  • Nonionic antistatic agents include, for example, fatty acid alkylolamide, di (2-hydroxyethyl) alkylamine, polyoxyethylene alkylamine, fatty acid glycerin ester, polyoxyethylene glycol fatty acid ester, sorbitan fatty acid ester, polyoxysorbitan fatty acid Examples thereof include esters, polyoxyethylene alkyl phenyl ethers, polyoxyethylene alkyl ethers, polyethylene glycols, polyoxyethylene diamines, copolymers composed of polyethers, polyesters and polyamides, and methoxypolyethylene glycol (meth) acrylates. These compounds may be used alone or in combination of two or more.
  • Examples of the conductive polymer include polyaniline, polypyrrole, polythiophene and the like.
  • Examples of the conductive material include tin oxide, antimony oxide, indium oxide, cadmium oxide, titanium oxide, zinc oxide, indium, tin, antimony, gold, silver, copper, aluminum, nickel, chromium, titanium, iron, cobalt, Examples include copper iodide, and alloys or mixtures thereof.
  • the resin component used for the antistatic resin and the conductive resin general-purpose resins such as polyester, acrylic, polyvinyl, urethane, melamine, and epoxy are used. In the case of a polymer type antistatic agent, it is not necessary to contain a resin component. Further, the antistatic resin component can contain a methylol- or alkylol-containing melamine-based, urea-based, glyoxal-based, acrylamide-based compound, epoxy compound, or isocyanate-based compound as a crosslinking agent.
  • the antistatic layer can be formed by, for example, diluting the antistatic resin, conductive polymer, or conductive resin with a solvent such as an organic solvent or water, and applying and drying the coating liquid on a plastic film. Is done.
  • organic solvent used for forming the antistatic layer examples include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexanone, n-hexane, toluene, xylene, methanol, ethanol, n-propanol, and isopropanol. can give. These solvents may be used alone or in combination of two or more.
  • coating method for forming the antistatic layer include roll coating, gravure coating, reverse coating, roll brush, spray coating, air knife coating, impregnation and curtain coating.
  • the thickness of the antistatic resin layer, conductive polymer, and conductive resin is usually about 0.01 to 5 ⁇ m, preferably about 0.03 to 1 ⁇ m.
  • Examples of the method for depositing or plating the conductive material include vacuum deposition, sputtering, ion plating, chemical vapor deposition, spray pyrolysis, chemical plating, and electroplating.
  • the thickness of the conductive material layer is usually 20 to 10,000 mm, preferably 50 to 5000 mm.
  • the above antistatic agent is appropriately used.
  • the amount of the kneading type antistatic agent is 20% by weight or less, preferably 0.05 to 10% by weight, based on the total weight of the plastic film.
  • the kneading method is not particularly limited as long as the antistatic agent can be uniformly mixed with the resin used for the plastic film. For example, a heating roll, a Banbury mixer, a pressure kneader, a biaxial kneader or the like is used. It is done.
  • silicone-based, fluorine-based, long-chain alkyl-based or fatty acid amide-based release agents release with silica powder, antifouling treatment, acid treatment, alkali treatment, primer treatment, corona Easy adhesion treatment such as treatment, plasma treatment, and ultraviolet treatment can also be performed.
  • a method used in the production of pressure-sensitive adhesive tapes can be used. Specific examples include roll coating, gravure coating, reverse coating, roll brushing, spray coating, and air knife coating.
  • the pressure-sensitive adhesive sheets can be bonded to the pressure-sensitive adhesive surface for the purpose of protecting the pressure-sensitive adhesive surface as necessary.
  • a base material constituting the separator there are paper and plastic film, but a plastic film is preferably used from the viewpoint of excellent surface smoothness.
  • the film is not particularly limited as long as it can protect the pressure-sensitive adhesive layer.
  • examples thereof include a film, a polyethylene terephthalate film, a polybutylene terephthalate film, a polyurethane film, and an ethylene-vinyl acetate copolymer film.
  • the thickness of the film is usually about 5 to 200 ⁇ m, preferably about 10 to 100 ⁇ m.
  • the adhesive layer bonding surface of the film is appropriately treated with a release agent such as a silicone, fluorine, long chain alkyl or fatty acid amide release agent, silica powder or the like.
  • the pressure-sensitive adhesive composition and the pressure-sensitive adhesive sheet of the present embodiment are used for plastic products that are particularly prone to generate static electricity, and in particular, polarizing plates, wave plates, optical compensation films, light diffusion materials used for liquid crystal displays and the like. It can also be used as a surface protective film used for the purpose of protecting the surface of an optical member such as a sheet or a reflective sheet.
  • the antistatic pressure-sensitive adhesive of the present invention on various surfaces that generate static charge at various temperatures and humidity ranges and require effective antistatic performance. Can receive.
  • flat panel displays such as liquid crystal displays, computer screens, and television screens can benefit.

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Abstract

L'invention porte sur une composition adhésive présentant d'excellentes propriétés, entre autres. De façon spécifique, l'invention porte sur une composition adhésive caractérisée en ce qu'elle renferme un bis(fluorosulfonyimide). La composition adhésive présente des propriétés équivalentes ou supérieures à celles de compositions adhésives classiques. De façon spécifique, l'invention porte également sur une composition adhésive caractérisée en ce qu'elle contient une paire d'ions, le bis(fluorosulfonylimide) étant un anion de la paire d'ions. La composition adhésive présente également des propriétés équivalentes ou supérieures à celles de compositions adhésives classiques.
PCT/JP2008/073776 2007-12-27 2008-12-26 Composition adhésive, article adhésif, composition adhésive à usage optique et procédé d'adhésion Ceased WO2009084651A1 (fr)

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CN2008801197984A CN101889065A (zh) 2007-12-27 2008-12-26 粘合剂组成物、粘合剂物品、光学用粘合剂组成物及粘合方法
KR1020107009329A KR101412889B1 (ko) 2007-12-27 2008-12-26 점착제 조성물, 점착제 물품, 광학용 점착제 조성물 및 점착 방법

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