Curable perfluoropolyether pressure-sensitive adhesive composition, pressure-sensitive adhesive using cured product of composition, and pressure-sensitive adhesive tape

Abstract

The present invention is a curable perfluoropolyether pressure-sensitive adhesive composition containing: (A) 100 parts by mass of a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and having a perfluoropolyether structure containing a repeating unit represented by-CaF2aO-in the main chain (where a represents an integer of 1-6); (B) an organosilicon compound having at least two hydrogen atoms bonded to a silicon atom in one molecule, the organosilicon compound being a curing effective amount; (C) a hydrosilylation reaction catalyst in a catalytic amount; and (D) an antistatic agent in an effective amount. As a result, it is possible to provide a curable perfluoropolyether pressure-sensitive adhesive composition, and a pressure-sensitive adhesive and a pressure-sensitive adhesive tape using a cured product of the composition. The curable perfluoropolyether pressure-sensitive adhesive composition forms a cured product which has excellent heat resistance, weather resistance, hydrophobicity, oleophobicity, chemical resistance, solvent resistance and the like, and particularly can prevent static electricity when an adherend attached to the pressure-sensitive adhesive or an adhesive tape with the pressure-sensitive adhesive is peeled off.

Description

Technical Field

[0001] The present invention relates to a curable perfluoropolyether pressure-sensitive adhesive composition (hereinafter also referred to as a perfluoropolyether pressure-sensitive adhesive composition), and a pressure-sensitive adhesive and a pressure-sensitive adhesive tape using a cured product of the composition. The curable perfluoropolyether pressure-sensitive adhesive composition forms a pressure-sensitive adhesive (cured perfluoropolyether rubber or cured perfluoropolyether gel) that is excellent in heat resistance, oil resistance, chemical resistance, solvent resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and is particularly capable of resisting static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive. Background Art

[0002] In the past, it has been proposed to obtain a cured product having well-balanced and excellent properties such as heat resistance, chemical resistance, solvent resistance, hydrophobicity, oleophobicity, and weather resistance by using a composition consisting of a straight-chain perfluoropolyether compound having at least two alkenyl groups in one molecule and a perfluoropolyether structure in the main chain, an organosilicon compound having two or more H-SiOSiO structures in one molecule, and a hydrosilylation reaction catalyst (Patent Documents 1 and 2).

[0003] On the other hand, pressure-sensitive adhesives are used in various occasions, mainly in labels or pressure-sensitive tapes attached to products. Recently, with the advancement of electronic terminal-related technologies such as pressure-sensitive adhesive films for protecting displays and protective films in product manufacturing processes, the above applications are also expanding. In addition, not only surface protection, but also the use of the transparency of the material to apply it to optical components, such as optical clear adhesive tape (OCA tape) for use inside products, is also being developed.

[0004] As the main classification of pressure-sensitive adhesives, there are acrylic, rubber, silicone, etc., each of which has its own advantages and disadvantages. Silicone pressure-sensitive adhesives are less costly than acrylic and rubber, but their heat resistance, cold resistance, weather resistance, chemical resistance, and electrical insulation properties are superior to the other two pressure-sensitive adhesives.

[0005] Recently, terminals such as mobile phones have become widely popular, but most of the pressure-sensitive adhesive films for protecting these displays use silicone pressure-sensitive adhesives. Silicone has good wettability to the adherend due to its characteristics, so it will not be involved in bubbles during lamination, will not automatically shift or peel off, and can be re-attached due to its good reprocessability (Patent Document 3). In addition, since the protective film used in the product manufacturing process is also in the same situation, and further requires heat resistance, etc., a large number of pressure-sensitive adhesive films using silicone pressure-sensitive adhesives are used.

[0006] In addition, mobile phones, which are called smart phones, are rapidly gaining popularity. Most of them can be operated by touching a display called a touch panel instead of the traditional key operation. Similarly, there are tablet terminals, which are easy-to-carry computers with touch panels. As these become popular, the demand for pressure-sensitive adhesive films for protecting screens tends to increase as the area of ​​the display increases.

[0007] However, although such silicone pressure-sensitive adhesives have sufficient performance in most applications, there is a strong demand for a pressure-sensitive adhesive composition having excellent chemical resistance and solvent resistance, such as in applications around automobile engines and barcode labels used in clinical examinations and pathological examinations, where chemical resistance and solvent resistance are further required.

[0008] Among them, a curable perfluoropolyether pressure-sensitive adhesive composition is proposed (Patent Document 4). The composition shows that a cured product with excellent heat resistance, weather resistance, hydrophobicity, oleophobicity, etc., as well as excellent chemical resistance and solvent resistance can be obtained. However, the exemplified compositions all have a volume resistivity of 1×10 cm 9 Non-conductive pressure-sensitive adhesives with a resistance of Ω·m or more may cause electrostatic discharge due to static electricity generated during peeling, especially when electronic parts are used as adherends.

[0009] Prior art literature

[0010] Patent Literature

[0011] Patent Document 1: Japanese Patent No. 2990646

[0012] Patent Document 2: Japanese Patent Application Publication No. 2000-248166

[0013] Patent Document 3: Japanese Patent Application Laid-Open No. 07-197008

[0014] Patent Document 4: Japanese Patent Application Publication No. 2019-38904 Summary of the invention

[0015] 1. Technical issues to be resolved

[0016] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a curable perfluoropolyether pressure-sensitive adhesive composition (hereinafter also referred to as a perfluoropolyether pressure-sensitive adhesive composition), a pressure-sensitive adhesive and a pressure-sensitive adhesive tape using a cured product of the composition, wherein the curable perfluoropolyether pressure-sensitive adhesive composition forms a cured product having excellent heat resistance, weather resistance, hydrophobicity, oleophobicity, chemical resistance and solvent resistance, and the cured product is a pressure-sensitive adhesive (cured perfluoropolyether rubber or cured perfluoropolyether gel) that can prevent static electricity when an adherend or a tape with the pressure-sensitive adhesive attached to the pressure-sensitive adhesive is peeled off.

[0017] (II) Technical solution

[0018] In order to solve the above technical problems, the first embodiment of the present invention provides a curable perfluoropolyether pressure-sensitive adhesive composition, which contains:

[0019] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 parts by mass;

[0020] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount;

[0021] (C) a hydrosilylation reaction catalyst in a catalytic amount; and

[0022] (D) an antistatic agent in an effective amount.

[0023] If the curable perfluoropolyether pressure-sensitive adhesive composition containing components (A) to (D) according to the first embodiment of the present invention is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, oil resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and can prevent static electricity when peeling off the adherend attached to the pressure-sensitive adhesive or the tape with the pressure-sensitive adhesive. In addition, if the curable perfluoropolyether pressure-sensitive adhesive composition containing components (A) to (D) of the present invention and containing no organic solvent in the composition is used, a rubber cured product (perfluoropolyether rubber cured product) can be obtained.

[0024] In addition, in a first embodiment of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, wherein the component (A) is a linear perfluoropolyether compound represented by the following general formula (1):

[0025] [Chemical formula 1]

[0026]

[0027] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z) (i.e., dimethylphenylsilylene represented at the ortho, meta or para position), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z') (i.e., a dimethylphenylsilylene group represented at the ortho, meta or para position), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0028] [Chemical formula 2]

[0029]

[0030] [Chemical formula 3]

[0031] .

[0032] A composition containing the component (A) can provide a cured product (pressure-sensitive adhesive) having superior chemical resistance and solvent resistance and can also provide a curable perfluoropolyether pressure-sensitive adhesive composition having high pressure-sensitive adhesive strength.

[0033] In addition, in a first aspect of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, wherein the antistatic agent of the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides and carbon materials.

[0034] In the present invention, such an antistatic agent can be used as the component (D).

[0035] Furthermore, in a first aspect of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, which further contains 0.01 to 5 parts by mass of (E) an addition reaction control agent based on 100 parts by mass of the component (A).

[0036] The curable perfluoropolyether pressure-sensitive adhesive composition containing the component (E) of the present invention does not increase viscosity or gel when the composition is prepared or applied to a substrate, thereby improving workability. The curable perfluoropolyether pressure-sensitive adhesive composition is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, oil resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive.

[0037] In addition, in the first embodiment of the present invention, a perfluoropolyether pressure-sensitive adhesive composition is provided, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0038] When the antistatic agent (D) component is contained and the volume resistivity is within the above range as in the present invention, the curable perfluoropolyether pressure-sensitive adhesive composition has sufficient antistatic performance, particularly when peeling an adherend or a pressure-sensitive adhesive tape attached to the pressure-sensitive adhesive.

[0039] In addition, in a first embodiment of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, which is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0040] If the composition can provide a cured product having such pressure-sensitive adhesive strength, it will be a curable perfluoropolyether pressure-sensitive adhesive composition having excellent pressure-sensitive adhesive strength with an adherend.

[0041] In addition, in a second embodiment of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition comprising:

[0042] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 to 40 parts by mass;

[0043] (F) a polyfluoromonoalkenyl compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain, wherein the polyfluoromonoalkenyl compound (F) is present in an amount of 0 to 60 parts by mass, and the total amount of the component (A) and the component (F) is 100 parts by mass;

[0044] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount;

[0045] (C) a hydrosilylation reaction catalyst in a catalytic amount; and

[0046] (D) an antistatic agent in an effective amount.

[0047] If it is a curable perfluoropolyether pressure-sensitive adhesive composition containing components (A) to (D) and (F) as in the second embodiment of the present invention and preferably containing no organic solvent in the composition, it will be a curable perfluoropolyether pressure-sensitive adhesive composition that is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, oil resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with a pressure-sensitive adhesive. In addition, if it is a curable perfluoropolyether pressure-sensitive adhesive composition containing components (A) to (D) and (F) of the present invention as described above, a rubber cured product or a gel cured product (perfluoropolyether rubber cured product or gel cured product) can be obtained.

[0048] In addition, in a second embodiment of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, wherein the component (A) is a linear perfluoropolyether compound represented by the following general formula (1):

[0049] [Chemical formula 4]

[0050]

[0051] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z) (i.e., dimethylphenylsilylene represented at the ortho, meta or para position), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z') (i.e., a dimethylphenylsilylene group represented at the ortho, meta or para position), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0052] [Chemical formula 5]

[0053]

[0054] [Chemical formula 6]

[0055] .

[0056] A composition containing such a component (A) can provide a cured product (pressure-sensitive adhesive) having more excellent chemical resistance and solvent resistance and can also provide a curable perfluoropolyether pressure-sensitive adhesive composition having high pressure-sensitive adhesive strength.

[0057] In addition, in a second embodiment of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, wherein the component (F) is a polyfluoromonoolefin compound represented by the following general formula (2):

[0058] R 1 -(X') p -CH=CH2(2)

[0059] In formula (2), X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z') (i.e., a dimethylphenylsilylene group represented at the ortho, meta or para position), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is 0 or 1; Rf 1 The general formula is F-[CF(CF3)CF2O] w -CF(CF3)-, wherein w in the general formula represents an integer of 1 to 500,

[0060] [Chemical formula 7]

[0061] .

[0062] A composition containing such a component (F) can provide a curable perfluoropolyether pressure-sensitive adhesive composition capable of obtaining a cured product (pressure-sensitive adhesive) having further excellent chemical resistance and solvent resistance.

[0063] In a second aspect of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition, wherein the antistatic agent of the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides and carbon materials.

[0064] In the present invention, such an antistatic agent can be used as the component (D).

[0065] Furthermore, in a second aspect of the present invention, there is provided a curable perfluoropolyether pressure-sensitive adhesive composition further comprising 0.01 to 5 parts by mass of (E) an addition reaction control agent based on 100 parts by mass of the total of the component (A) and the component (F).

[0066] If the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention contains such a component (E), the pressure-sensitive adhesive composition does not increase in viscosity or gel when the composition is prepared or applied to a substrate, so the workability is improved, and it becomes a curable perfluoropolyether pressure-sensitive adhesive composition that is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, oil resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and can prevent static electricity when peeling off a to-be-adhered object attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive.

[0067] In addition, in the second embodiment of the present invention, a perfluoropolyether pressure-sensitive adhesive composition is provided, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0068] When the antistatic agent (D) component of the present invention is contained and the volume resistivity is within the above range, the curable perfluoropolyether pressure-sensitive adhesive composition can have sufficient antistatic performance, especially when peeling an adherend or a pressure-sensitive adhesive tape attached to the pressure-sensitive adhesive.

[0069] In addition, in a second embodiment of the present invention, a curable perfluoropolyether pressure-sensitive adhesive composition is provided, wherein the composition is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0070] If the composition can provide a cured product having such pressure-sensitive adhesive strength, it will be a curable perfluoropolyether pressure-sensitive adhesive composition having excellent pressure-sensitive adhesive strength with an adherend.

[0071] Furthermore, in the first aspect or the second aspect of the present invention, there is provided a pressure-sensitive adhesive comprising a cured product of the curable perfluoropolyether pressure-sensitive adhesive composition.

[0072] Thus, the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive capable of obtaining a perfluoropolyether rubber cured product or a perfluoropolyether gel cured product having excellent pressure-sensitive adhesiveness to various substrates.

[0073] In the first aspect or the second aspect of the present invention, there is provided a pressure-sensitive adhesive tape comprising a substrate and a cured layer of the curable perfluoropolyether pressure-sensitive adhesive composition laminated thereon.

[0074] Thus, a pressure-sensitive adhesive tape having a conductive pressure-sensitive adhesive layer can be used by laminating a cured layer of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention (a pressure-sensitive adhesive layer composed of a cured perfluoropolyether rubber or a cured perfluoropolyether gel) on a substrate.

[0075] (III) Beneficial effects

[0076] As described above, the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention can provide a rubber-like or gel-like cured product (pressure-sensitive adhesive) that is excellent in heat resistance, weather resistance, oil resistance, low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, chemical resistance, solvent resistance, etc., and that can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive. DETAILED DESCRIPTION

[0077] As described above, it is sought to develop a curable perfluoropolyether pressure-sensitive adhesive composition that can obtain a cured product (pressure-sensitive adhesive) that is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, etc. and that can prevent static electricity when peeling an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive, as well as a pressure-sensitive adhesive and a pressure-sensitive adhesive tape containing the cured product of the curable perfluoropolyether pressure-sensitive adhesive composition.

[0078] The inventors of the present application have conducted intensive studies to achieve the above-mentioned purpose, and as a result, have found that according to the specific curable perfluoropolyether pressure-sensitive adhesive composition of the present invention, it is possible to obtain a rubber-like or gel-like cured product (perfluoropolyether rubber cured product or perfluoropolyether gel cured product) having better chemical resistance and solvent resistance than conventional silicone pressure-sensitive adhesives, and in particular, a cured product (pressure-sensitive adhesive) that can prevent static electricity when an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive is peeled off, thereby completing the present invention.

[0079] <First option>

[0080] That is, the first embodiment of the present invention is a curable perfluoropolyether pressure-sensitive adhesive composition which is a curable perfluoropolyether pressure-sensitive adhesive composition capable of obtaining a rubber-like cured product (perfluoropolyether rubber cured product), comprising:

[0081] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 parts by mass;

[0082] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount;

[0083] (C) a hydrosilylation reaction catalyst in a catalytic amount; and

[0084] (D) an antistatic agent in an effective amount.

[0085] Hereinafter, the first aspect of the present invention will be described in detail, but the present invention is not limited thereto.

[0086] [(A) ingredient]

[0087] In the first embodiment of the present invention, the component (A) contained in the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention is a component that functions as a main agent (base polymer) of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention, and is a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a perfluoropolyether structure (perfluorooxyalkylene structure) in the main chain, preferably a divalent perfluorooxyalkylene structure.

[0088] Here, as the perfluorooxyalkylene structure, it contains -C a F 2a The multiple repeating structures of the oxyalkylene units represented by O-, wherein a in each unit is independently an integer of 1 to 6, include, for example, the structure represented by the following general formula (3).

[0089] (C a F 2a O) q (3)

[0090] In formula (3), q is an integer of 50 to 600, preferably an integer of 50 to 400, and more preferably an integer of 50 to 200.

[0091] As each repeating structure constituting the perfluorooxyalkylene structure represented by the above formula (3), a F 2a O- (that is, oxyalkylene unit) includes, for example, the following structures. The perfluoroalkyl ether structure may be composed of a single type of these repeating structures or a combination of two or more types.

[0092] -CF2O-

[0093] -CF2CF2O-

[0094] -CF2CF2CF2O-

[0095] -CF(CF3)CF2O-

[0096] -CF2CF2CF2CF2O-

[0097] -CF2CF2CF2CF2CF2CF2O-

[0098] -C(CF3)2O-

[0099] Among these, the following structures are particularly suitable.

[0100] -CF2O-

[0101] -CF2CF2O-

[0102] -CF2CF2CF2O-

[0103] -CF(CF3)CF2O-

[0104] In the present invention, "linear" means that each repeating unit -C a F 2a O-(units) are bonded to each other to form a straight chain, and each repeating unit (oxyalkylene unit) itself can be a straight chain oxyalkylene unit or a branched chain oxyalkylene unit (for example, -CF(CF3)CF2O-, -C(CF3)2O-, etc.).

[0105] As the alkenyl group in the linear perfluoropolyether compound of the component (A), a group having 2 to 8 carbon atoms, particularly 2 to 6 carbon atoms, and a CH2=CH- structure at the end is preferably a vinyl, allyl, propenyl, isopropenyl, butenyl, hexenyl, etc., and a group having a CH2=CH- structure at the end is preferably a vinyl, allyl, propenyl, isopropenyl, butenyl, hexenyl, etc., and a vinyl, allyl, etc. are particularly preferred. The alkenyl group can be directly bonded to the perfluoropolyether structure constituting the main chain of the linear perfluoropolyether compound, especially directly bonded to both ends of the divalent perfluorooxyalkylene structure, or can be bonded via a divalent linking group, such as -CH2-, -CH2O-, -CH2OCH2- or -Y-NR-CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z) (dimethylphenylsilyl represented by ortho, meta or para), and R is a hydrogen atom, a methyl, a phenyl or an allyl group. In addition, one molecule of the component (A) has at least two alkenyl groups.

[0106] [Chemical formula 8]

[0107]

[0108] As the component (A), for example, a polyfluorodiene compound represented by the following general formula (4) or (5) can be mentioned.

[0109] CH2=CH-(X) p -Rf 2 -(X') p -CH=CH2(4)

[0110] CH2=CH-(X) p -Q-Rf 2 -Q-(X') p-CH=CH2(5)

[0111] In formula (4) and (5), X is independently -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 It is a hydrogen atom, a methyl group, a phenyl group or an allyl group.

[0112] [Chemical formula 9]

[0113]

[0114] (dimethylphenylsilylene represented in the o-, m- or p-position)

[0115] [Chemical formula 10]

[0116]

[0117] (dimethylphenylsilylene represented in the o-, m- or p-position)

[0118] R 2 is a divalent perfluoropolyether structure (perfluorooxyalkylene structure), preferably the above formula (3), i.e. (C a F 2a O) q Q is a divalent hydrocarbon group having 1 to 15 carbon atoms, optionally containing an ether bond, specifically, an alkylene group, or an alkylene group optionally containing an ether bond. p is independently 0 or 1.

[0119] As such a linear perfluoropolyether compound of the component (A), a compound represented by the following general formula (1) is suitable.

[0120] [Chemical formula 11]

[0121]

[0122] In formula (1), X, X' and p are the same as those described above, r is an integer of 2 to 6, m and n are integers of 0 to 600, respectively, and the sum of m and n is 50 to 600.

[0123] The linear perfluoropolyether compound represented by the general formula (1) has a polyethylene-converted weight average molecular weight of 3,000 to 100,000, preferably 4,000 to 50,000, in a molecular weight distribution measurement obtained by gel permeation chromatography (GPC) analysis using a fluorine-based solvent as a developing solvent. If the weight average molecular weight is 3,000 or more, the swelling to gasoline or various solvents becomes small. In particular, the swelling to gasoline is 6% or less, which can meet the characteristics of a component requiring gasoline resistance. In addition, if the weight average molecular weight is 100,000 or less, the viscosity will not be too high, and the operability is excellent, so it has practicality. In addition, the value of the degree of polymerization (m+n) of the linear perfluoropolyether compound of the general formula (1) can also be obtained by the polyethylene-converted number average degree of polymerization or weight average degree of polymerization in a molecular weight distribution measurement obtained by gel permeation chromatography (GPC) analysis using a fluorine-based solvent as a developing solvent. In addition, these number average degree of polymerization and weight average degree of polymerization can also be calculated according to 19 The ratio of the terminal structure to the repeating unit structure obtained by F-NMR spectrum was calculated.

[0124] Specific examples of the linear perfluoropolyether compound represented by the general formula (1) include compounds represented by the following formulas.

[0125] [Chemical formula 12]

[0126]

[0127] [Chemical formula 13]

[0128]

[0129] [Chemical formula 14]

[0130]

[0131] In the chemical formula, m and n each represent an integer of 0 to 600, preferably an integer of 0 to 200, and are integers satisfying m+n=50 to 600, preferably m+n=50 to 200.

[0132] Furthermore, in the present invention, in order to adjust the linear perfluoropolyether compound of the above formula (1) to a desired weight average molecular weight according to the purpose, the linear perfluoropolyether compound as described above can be subjected to a hydrosilylation reaction with an organosilicon compound containing two SiH groups in the molecule by a common method and conditions, and the product after the chain length is extended can be used as the (A) component. In addition, the linear perfluoropolyether compound of the (A) component can be used alone or in combination of two or more.

[0133] [(B) ingredient]

[0134] In the first embodiment of the present invention, the component (B) is a component that functions as a crosslinking agent and / or chain extender for the component (A). The component (B) is an organosilicon compound such as an organohydrogenpolysiloxane having at least two, preferably three or more hydrogen atoms (hydrosilyl groups represented by SiH) bonded to silicon atoms in one molecule. As the component (B), for example, known organosilicon compounds described in the above-mentioned Patent Documents 1, 2, and 4 can be cited, but there is no particular limitation.

[0135] In addition, from the viewpoints of compatibility with component (A) or between component (A) in the second embodiment of the present invention described later and component (F) described later, dispersibility, uniformity of the rubber or gel cured product (pressure-sensitive adhesive) after curing, etc., the organosilicon compound of component (B) is preferably a fluorinated organohydrogenpolysiloxane having one or more monovalent perfluoroalkyl groups, monovalent perfluorooxyalkyl groups, divalent perfluoroalkylene groups and / or divalent perfluorooxyalkylene groups in one molecule.

[0136] Examples of the monovalent or divalent fluorine-containing organic group include a perfluoroalkyl group, a perfluorooxyalkyl group, a perfluoroalkylene group, and a perfluorooxyalkylene group represented by the following formula.

[0137] C g F 2g+1 -

[0138] -C g F 2g -

[0139] In the general formula, g is an integer of 1-20, preferably an integer of 2-10.

[0140] [Chemical formula 15]

[0141]

[0142] In the chemical formula, f is an integer of 1-200, preferably an integer of 1-100, and h is an integer of 1-3.

[0143] [Chemical formula 16]

[0144]

[0145] In the chemical formula, i and j are each an integer greater than or equal to 1, preferably an integer from 1 to 100, and the average of i+j is 2 to 200, preferably 2 to 100.

[0146] -(CF2O) d -(CF2CF2O) e -CF2-

[0147] In the general formula, d and e are each an integer of 1 to 50, preferably an integer of 1 to 40.

[0148] In addition, it is preferred that these perfluoroalkyl groups, perfluorooxyalkyl groups, perfluoroalkylene groups or perfluorooxyalkylene groups are connected to the silicon atom via a divalent linking group. The divalent linking group may be an alkylene group, an arylene group, and a combination thereof, or may be a group in which an ether bond oxygen atom, an amide bond, a carbonyl bond, an ester bond, a diorganosiliconyl group, etc. are interspersed in these groups. For example, the following divalent linking groups having 2 to 12 carbon atoms may be listed, but are not limited to these.

[0149] -CH2CH2-,

[0150] -CH2CH2CH2-,

[0151] -CH2CH2CH2OCH2-,

[0152] -CH2CH2CH2-NH-CO-,

[0153] -CH2CH2CH2-N(Ph)-CO-,

[0154] -CH2CH2CH2-N(CH3)-CO-,

[0155] -CH2CH2CH2-N(CH2CH3)-CO-,

[0156] -CH2CH2-Si(CH3)2-Ph'-N(CH3)-CO-、

[0157] -CH2CH2CH2-Si(CH3)2-Ph'-N(CH3)-CO-,

[0158] -CH2CH2CH2-O-CO-

[0159] In the general formula, Ph is a phenyl group, and Ph' is a phenylene group.

[0160] In addition, examples of the monovalent substituents bonded to silicon atoms other than the monovalent or divalent fluorinated organic groups and hydrogen atoms bonded to silicon atoms in the fluorinated organohydrogenpolysiloxane of the component (B) include alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, cyclohexyl, octyl, and decyl; alkenyl groups such as vinyl and allyl; aryl groups such as phenyl, tolyl, and naphthyl; aralkyl groups such as benzyl and phenethyl; and unsubstituted or substituted monovalent hydrocarbon groups having 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, such as chloromethyl, chloropropyl, and cyanoethyl, in which a part or all of the hydrogen atoms in these groups are substituted with chlorine atoms, cyano groups, or the like.

[0161] The fluorinated organohydrogen polysiloxane as component (B) may be cyclic, linear, branched, three-dimensional network, or a combination thereof. The number of silicon atoms in the fluorinated organohydrogen polysiloxane is not particularly limited, but is generally 2 to 60, preferably about 3 to 30.

[0162] As component (B) having such a monovalent or divalent fluorine-containing organic group and a hydrogen atom bonded to a silicon atom, for example, the following compounds can be cited. These compounds can be used alone or in combination of two or more. In the following chemical formula, Me represents a methyl group, and Ph represents a phenyl group.

[0163] [Chemical formula 17]

[0164]

[0165] [Chemical formula 18]

[0166]

[0167] [Chemical formula 19]

[0168]

[0169] [Chemical formula 20]

[0170]

[0171] [Chemical formula 21]

[0172]

[0173] [Chemical formula 22]

[0174]

[0175] [Chemical formula 23]

[0176]

[0177] [Chemical formula 24]

[0178]

[0179] [Chemical formula 25]

[0180]

[0181] [Chemical formula 26]

[0182]

[0183] [Chemical formula 27]

[0184]

[0185] [Chemical formula 28]

[0186]

[0187] [Chemical formula 29]

[0188]

[0189] The amount of the above-mentioned (B) component is an effective amount for curing the (A) component and the (F) component described later, i.e., a curing effective amount. In particular, the amount of the hydrosilyl group (Si-H) in the (B) component is preferably 0.2 to 4 moles, more preferably 0.5 to 3 moles, relative to 1 mole of the alkenyl group possessed by the above-mentioned (A) component in the present composition, or relative to 1 mole of the total of the alkenyl groups possessed by the (A) component and the (F) component in the second embodiment of the present invention described later. If the amount of the hydrosilyl group (Si-H) is 0.2 moles or more, the degree of crosslinking is sufficient and a cured product can be obtained reliably. In addition, if the amount of the hydrosilyl group (Si-H) is 4 moles or less, no foaming will occur during curing.

[0190] (B) The component may be used alone or in combination of two or more.

[0191] [(C) ingredient]

[0192] In the first embodiment of the present invention, the hydrosilylation reaction catalyst (addition reaction catalyst) of the component (C) of the present invention is a catalyst for promoting the addition reaction of the alkenyl group in the component (A), or the alkenyl group in the component (A) and the component (F) described later in the second embodiment of the present invention, with the hydrosilyl group in the component (B). The hydrosilylation reaction catalyst is usually a compound of a noble metal (platinum group metal), and platinum or a platinum compound that is relatively easy to obtain is often used due to its high price.

[0193] Examples of platinum compounds include chloroplatinic acid or a complex of chloroplatinic acid and an olefin such as ethylene, a complex of chloroplatinic acid and vinylsiloxane, and metal platinum supported on silica, alumina, carbon, and the like. Rhodium, ruthenium, iridium, and palladium compounds are also known as platinum group metal catalysts other than platinum compounds, and examples thereof include RhCl(PPh3)3, RhCl(CO)(PPh3)2, Ru3(CO) 12 , IrCl(CO)(PPh3)2, Pd(PPh3)4, etc.

[0194] The amount of the hydrosilylation reaction catalyst added can be a catalytic amount, and is usually preferably added at a ratio of 0.1 to 500 ppm (calculated as the mass of the platinum group metal) relative to the total mass of the components (A), (B) and (F), and more preferably at a ratio of 0.1 to 100 ppm. The hydrosilylation reaction catalyst of the component (C) may be used alone or in combination of two or more.

[0195] The hydrosilylation reaction catalyst (addition reaction catalyst) of the component (C) of the present invention preferably does not contain an organic solvent (for example, the platinum group metal catalyst is not diluted, dissolved or dispersed in an organic solvent).

[0196] [(D) ingredient]

[0197] In the first embodiment of the present invention, the antistatic agent as the component (D) of the present invention is not particularly limited as long as it has conductivity, and examples thereof include conductive polymers, surfactants, metals, metal oxides, and carbon materials. One of these antistatic agents may be used alone, or two or more thereof may be used in combination.

[0198] As conductive polymers in these antistatic agents, for example, polythiophene, polyaniline, polypyrrole, polyacetylene, polyethylenedioxythiophene (PEDOT), polyethylenedioxythiophene / polystyrene sulfonic acid (PEDOT / PSS), polyparaphenylene, polyfluorene, polycarbazole, polysilane or their derivatives can be listed. One of these conductive polymers can be used, or two or more of them can be used in combination.

[0199] Moreover, as a surfactant, an anionic surfactant, a cationic surfactant, a nonionic surfactant, a zwitterionic surfactant etc. are mentioned, for example.

[0200] Furthermore, examples of the metal include gold, silver, copper, silver-coated copper, nickel, and the like, and metal powders thereof are preferably used.

[0201] Examples of the metal oxide include indium tin oxide (ITO), indium oxide (IO), and indium zinc oxide (IZO), and metal oxide powders thereof are preferably used.

[0202] In addition, examples of carbon materials include carbon black such as acetylene black and furnace black; carbon nanotubes such as single-walled carbon nanotubes and multi-walled carbon nanotubes; carbon nanofibers, CN nanotubes, CN nanofibers, BCN nanotubes, BCN nanofibers, and graphene.

[0203] Among them, carbon black is preferred as the conductive material because it has a small temperature dependence of resistivity, high heat resistance, and can exhibit conductivity even when added in a small amount.

[0204] The amount of component (D) to be added varies depending on its type, but is preferably in the range of 0.5 to 20 parts by mass, more preferably 1 to 15 parts by mass, relative to 100 parts by mass of component (A), or relative to 100 parts by mass of the total of component (A) and component (F) in the second embodiment of the present invention described later. If it is 0.5 parts by mass or more, sufficient antistatic properties can be obtained, and if it is 20 parts by mass or less, significant viscosity increase of the composition can be suppressed.

[0205] In the pressure-sensitive adhesive and pressure-sensitive tape of the present invention described below, the volume resistivity measured on the surface of the pressure-sensitive adhesive is preferably 1.0×10 2 ~1.0×10 8 Ω·m, and more preferably 1.0×10 3 ~1.0×10 7 Ω·m.

[0206] In addition, surface resistivity may be required in some cases. In this case, the surface resistivity of the pressure-sensitive adhesive and the pressure-sensitive tape of the present invention is preferably 1.0×10 3 ~1.0×10 9 Ω / □, more preferably 1.0×10 4 ~1.0×10 8 Ω / □. In addition, the volume resistivity and surface resistivity in this specification are values ​​measured in accordance with JIS K6911.

[0207] [Other ingredients]

[0208] In the first aspect of the present invention (or in the second aspect described below), various additives may be arbitrarily added in addition to the above-mentioned components (A) to (C).

[0209] [(E) ingredient]

[0210] In the first aspect of the present invention (or in the second aspect described below), a control agent for the hydrosilylation reaction catalyst (addition reaction control agent) as the component (E) may be optionally blended.

[0211] Before heat curing, for example, when a curable perfluoropolyether pressure-sensitive adhesive composition is blended or when the pressure-sensitive adhesive composition is applied to a substrate, in order to prevent the pressure-sensitive adhesive composition from being tackified or gelled, component (E) may be added. For example, acetylene alcohols such as 1-ethynyl-1-hydroxycyclohexane, 3-methyl-1-butyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3-methyl-1-pentene-3-ol, and phenylbutynol may be listed; or 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, etc.; or polymethylvinylsiloxane cyclic compounds, organic phosphorus compounds, etc., can be added to keep the curing reactivity and storage stability to a moderate level. In addition, component (E) may be used alone or in combination of two or more.

[0212] The amount of the component (E) is in the range of 0 to 5 parts by mass relative to 100 parts by mass of the component (A) or in the second embodiment of the present invention described later, the total amount of the component (A) and the component (F) is in the range of 0 to 5 parts by mass. When the amount is 5 parts by mass or less, the curability of the obtained composition will not be reduced.

[0213] [(G) ingredient]

[0214] In the first embodiment of the present invention (or the second embodiment described later), the hydrophobic silica powder as the component (G) can be arbitrarily blended as needed. The hydrophobic silica powder of the component (G) is a substance that imparts appropriate physical strength to the cured product obtained by the curable perfluoropolyether pressure-sensitive adhesive composition. The hydrophobic silica powder as the component (G) is suitable for a BET specific surface area of ​​50 m2 that is known as a filler for silicone rubber. 2 / g or more, especially 50~400m 2 / g of fine powdered silicon dioxide subjected to a hydrophobic treatment.

[0215] Examples of fine powder silica include fumed silica (gas-phase silica or dry silica), precipitated silica (wet silica), and colloidal silica. Among them, fumed silica is most preferred.

[0216] If the BET specific surface area is 50 m 2 / g or more, the physical strength of the obtained cured product is sufficient. 2 / g or less, the kneading operation becomes easy and the (G) component itself is evenly dispersed. In addition, the BET specific surface area in the present invention can be measured in accordance with DIN 66131.

[0217] Examples of the hydrophobic treatment agent for the fine powder silica include organochlorosilane, organodisilazane, cyclic organopolysilazane, linear organopolysiloxane, and the like. Among these, organochlorosilane, organodisilazane, and cyclic organopolysiloxane are preferred.

[0218] When the (G) component is blended in the composition of the present invention, the blending amount is preferably 0.4 to 20 parts by mass, more preferably 0.5 to 18 parts by mass, relative to 100 parts by mass of the (A) component or relative to 100 parts by mass of the total of the (A) component and the (F) component described later. If the blending amount is 0.4 parts by mass or more, the effect of blending the component can be obtained reliably. On the other hand, if it is 20 parts by mass or less, the fluidity of the composition will not be reduced, and the coating property on the substrate becomes good.

[0219] <Second Option>

[0220] The second embodiment of the present invention is a curable perfluoropolyether pressure-sensitive adhesive composition, which is a curable perfluoropolyether pressure-sensitive adhesive composition that can be obtained as a rubber-like cured product (perfluoropolyether rubber cured product) or a gel-like cured product (perfluoropolyether gel cured product), and contains:

[0221] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 to 40 parts by mass;

[0222] (F) a polyfluoromonoalkenyl compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain, wherein the polyfluoromonoalkenyl compound (F) is present in an amount of 0 to 60 parts by mass, and the total amount of the component (A) and the component (F) is 100 parts by mass;

[0223] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount;

[0224] (C) a hydrosilylation reaction catalyst in a catalytic amount; and

[0225] (D) an antistatic agent in an effective amount.

[0226] In the second aspect of the present invention, as components (A) to (D), the same components as those described above can be used.

[0227] [(F)INGREDIENT]

[0228] The component (F) is a component used in the specific second embodiment (i.e., a composition that can obtain a gel cured product) of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention relative to the first embodiment of the present invention (i.e., a composition that can obtain a rubber cured product), and is a polyfluoromonoolefin compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain. The polyfluoromonoolefin compound represented by the following general formula (2) is particularly preferred.

[0229] R 1 -(X') p -CH=CH2(2)

[0230] In formula (2), X' and p are the same as X' and p described in the above general formula (1), and Rf 1 It is a perfluoropolyether structure (monovalent perfluoropolyether group) represented by the following general formula.

[0231] F-[CF(CF3)CF2O] w -CF(CF3)-

[0232] In the general formula, w represents an integer of 1 to 500, preferably an integer of 2 to 200.

[0233] Specific examples of the polyfluoromonoalkenyl compound represented by the general formula (2) include the following compounds.

[0234] [Chemical formula 30]

[0235]

[0236] [Chemical formula 31]

[0237]

[0238] In the above chemical formula, m is an integer of 1-200, particularly an integer of 2-100.

[0239] When the polyfluoromonoolefin compound of component (F) is blended, the blending amount thereof is determined as follows: in the curable perfluoropolyether pressure-sensitive adhesive composition, the ratio of the linear perfluoropolyether diene compound of component (A) to component (F) in the present composition is 100 to 40 parts by mass of component (A) and 0 to 60 parts by mass of component (F), and the total of components (A) and (F) is 100 parts by mass.

[0240] For example, the curable perfluoropolyether pressure-sensitive adhesive composition of the second embodiment of the present invention can contain the (F) component in the following manner: relative to 99 to 40 parts by mass, particularly 95 to 50 parts by mass, and further 92 to 60 parts by mass of the (A) component, the (F) component is 1 to 60 parts by mass, particularly 5 to 50 parts by mass, and further 8 to 40 parts by mass, and the total of the (A) component and the (F) component is 100 parts by mass. In addition, the polyfluoromonoolefin compound of the (F) component can be used alone or in combination of two or more.

[0241] [Other ingredients]

[0242] In the second embodiment of the present invention, in addition to the above-mentioned (A) to (D) and (F) components, various admixtures can be added arbitrarily in the same manner as in the first embodiment. The control agent (E) component of the hydrosilylation reaction catalyst and the hydrophobic silica powder (G) component can also be exemplified by the same substances as those described above.

[0243] [cured material]

[0244] The perfluoropolyether pressure-sensitive adhesive composition of the present invention is formed into a pressure-sensitive adhesive composed of a cured product of perfluoropolyether rubber or gel having a surface pressure-sensitive adhesive force of 0.001 to 10.0 N / 25 mm, preferably 0.002 to 8.0 N / 25 mm, and more preferably 0.003 to 6.0 N / 25 mm by curing the above-mentioned composition. The cured product (pressure-sensitive adhesive) having excellent heat resistance, hydrophobicity, oleophobicity, weather resistance, chemical resistance, solvent resistance, etc. and further excellent antistatic performance can be formed, and can be used in various applications.

[0245] For example, in the first embodiment of the present invention, the perfluoropolyether pressure-sensitive adhesive composition can be formed by adding the components in the following manner and curing them: relative to 100 parts by mass of the component (A), the component (B) is added in an amount such that the number of hydrosilyl groups of the component (B) is 0.2 to 3.0 mol relative to the total mole number of alkenyl groups possessed by the component (A) is 1, the component (C) is added in an amount of 0.1 to 100 ppm in terms of platinum relative to the total amount of the components (A) and (B), and the component (D) is added in an amount of 0.5 to 20 parts by mass relative to 100 parts by mass of the component (A).

[0246] In addition, for example, in the second embodiment of the present invention, the perfluoropolyether pressure-sensitive adhesive composition can be formed by adding the components and curing them in the following manner: the component (F) is 20 to 60 parts by mass relative to 40 to 80 parts by mass of the component (A), and the total of the components (A) and (F) is 100 parts by mass; the component (B) is an amount such that the hydrosilyl group of the component (B) is 0.2 to 3.0 moles relative to the total mole number of alkenyl groups possessed by the components (A) and (F); the component (C) is 0.1 to 100 ppm in terms of platinum relative to the total amount of the components (A), (B), and (F); and the component (D) is 0.5 to 20 parts by mass relative to 100 parts by mass of the total of the components (A) and (F).

[0247] The formation of the cured product of the above-mentioned perfluoropolyether pressure-sensitive adhesive composition is carried out by applying each composition of the present invention on a suitable substrate and then curing it, or by laminating it, etc. Curing can usually be easily carried out by heating at a temperature of 60 to 150° C. for about 1 to 60 minutes.

[0248] The pressure-sensitive adhesive using the cured product of the perfluoropolyether pressure-sensitive adhesive composition of the present invention can be used as a member for automobiles, chemical plants, semiconductor production lines, analytical / physical and chemical instruments, medical equipment, aircraft, optics, and the like.

[0249] In addition, for example, a pressure-sensitive adhesive tape in which a cured product (cured perfluoropolyether rubber or cured perfluoropolyether gel) of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention is laminated on a substrate composed of an organic resin film such as a polyethylene terephthalate (PET) film can be used as a pressure-sensitive adhesive tape having a conductive pressure-sensitive adhesive layer having excellent heat resistance, oil resistance, low temperature characteristics, moisture resistance, low air permeability, etc., and particularly excellent chemical resistance and solvent resistance.

[0250] In addition, when applying the pressure-sensitive adhesive composition of the present invention, in order to improve the adhesion or adhesion between the substrate, it is more useful to carry out known primer at the same time. Through primer, chemicals and solvents can be prevented from penetrating from the substrate surface, and the acid resistance, chemical resistance and solvent resistance of the entire component can be improved.

[0251] As the primer, a silane-based primer mainly composed of a silane coupling agent, a primer mainly composed of an organohydrogenpolysiloxane, a primer mainly composed of a synthetic rubber, or a primer mainly composed of an acrylic resin, a primer mainly composed of a urethane resin, or a primer mainly composed of an epoxy resin can be used. In addition, a composition obtained by adding a tackifier to the perfluoropolyether pressure-sensitive adhesive composition of the present invention can also be used as a primer.

[0252] Such a perfluoropolyether pressure-sensitive adhesive composition of the present invention is a curable perfluoropolyether pressure-sensitive adhesive composition that can obtain a cured product (pressure-sensitive adhesive) that is excellent in heat resistance, weather resistance, oil resistance, low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive.

[0253] Furthermore, a third aspect of the present invention is a pressure-sensitive adhesive comprising a cured product (a cured perfluoropolyether rubber or a cured perfluoropolyether gel) of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention described above.

[0254] As described above, the perfluoropolyether pressure-sensitive adhesive composition of the present invention can obtain a cured product (pressure-sensitive adhesive) having excellent heat resistance, weather resistance, oil resistance, chemical resistance, solvent resistance (solvent resistance), low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with a pressure-sensitive adhesive. Therefore, the pressure-sensitive adhesive of the present invention can be a coating film having excellent heat resistance, weather resistance, oil resistance, chemical resistance, solvent resistance (solvent resistance), low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with a pressure-sensitive adhesive.

[0255] Furthermore, a fourth aspect of the present invention is a pressure-sensitive adhesive tape including a laminate of a cured product layer of the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention described above.

[0256] As described above, the perfluoropolyether pressure-sensitive adhesive composition of the present invention can obtain a cured product (pressure-sensitive adhesive) having excellent heat resistance, weather resistance, oil resistance, chemical resistance, solvent resistance (solvent resistance), low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with a pressure-sensitive adhesive. Therefore, the pressure-sensitive adhesive tape of the present invention can be a coating film having excellent heat resistance, weather resistance, oil resistance, chemical resistance, solvent resistance (solvent resistance), low temperature characteristics, moisture resistance, low air permeability, hydrophobicity, oleophobicity, etc., and can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with a pressure-sensitive adhesive.

[0257] Furthermore, in order to enhance the effect of surface modification, the surface of the substrate may be subjected to a degreasing treatment or a pre-baking treatment using an organic solvent or the like before plasma irradiation.

[0258] Example

[0259] The present invention will be described in detail below with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples. In the following examples, % means mass %.

[0260] [Examples 1 to 4, Comparative Examples 1 to 4]

[0261] The following raw materials were used to prepare the curable perfluoropolyether pressure-sensitive adhesive compositions shown in Table 1. These pressure-sensitive adhesive compositions were cured under the curing conditions of 130° C. and 5 minutes, and the surface pressure-sensitive adhesive strength of each cured product was measured, and the solvent resistance test and volume resistivity were measured by the following methods. The results are collectively recorded in Table 1.

[0262] raw material

[0263] (A) Linear perfluoropolyether compounds

[0264] (a-1) Difunctional perfluoropolyether (perfluoropolyether 1)

[0265] [Chemical formula 32]

[0266]

[0267] (a-2) Difunctional perfluoropolyether (perfluoropolyether 2)

[0268] CH2=CH-CH2-O-CH2-Rf-CH2-O-CH2-CH=CH2

[0269] Rf: -CF2O(CF2CF2O) 20.8 (CF2O) 22.1 CF2-,

[0270] The arrangement of the repeating units CF2CF2O and CF2O is random.

[0271] (B) Organohydrogenpolysiloxane

[0272] (b-1) Organohydrogensiloxane 1

[0273] [Chemical formula 33]

[0274]

[0275] (b-2) Organohydrogensiloxane 2

[0276] [Chemical formula 34]

[0277]

[0278] (C) Addition reaction catalyst (platinum compound)

[0279] CAT-PL-56 (trade name manufactured by Shin-Etsu Chemical Co., Ltd.)

[0280] (D) Antistatic agent

[0281] (d-1) DENKA BLACK Li-100 (acetylene black manufactured by Denka Company Limited., antistatic agent 1)

[0282] (d-2) ENSACO260G (conductive carbon black dispersion manufactured by IMERYS, antistatic agent 2)

[0283] (D) Antistatic agent (blended with the following base composites d-1, d-2, d-3)

[0284] [Preparation of substrate complex d-1]

[0285] 100 parts of the polymer represented by the above formula (a-1) were added to a planetary mixer, and 12 parts of DENKA BLACK Li-100 (manufactured by DENKA COMPANY LIMITED.) were added in portions. Then, the internal temperature was maintained at 100 to 130° C., and heat treatment was performed under reduced pressure (gauge pressure; -0.093 MPa) for 1 hour. Then, the contents were cooled to below 40° C., and then the contents were taken out and passed through a three-roll mill once to obtain a base composite d-1 (base composite 1).

[0286] [Preparation of substrate complex d-2]

[0287] 100 parts of the polymer represented by the above formula (a-1) were added to a planetary mixer, and 15 parts of ENSACO260G (manufactured by IMERYS) were added in portions. Then, the mixture was heat treated for 1 hour under reduced pressure (gauge pressure; -0.093 MPa) while the internal temperature was maintained at 100 to 130°C. Then, the contents were cooled to below 40°C, and then the contents were taken out and passed through a three-roll mill once to obtain a base composite d-2 (base composite 2).

[0288] [Preparation of substrate complex d-3]

[0289] 100 parts of the polymer represented by the above formula (a-2) are added to a planetary mixer, and 12 parts of DENKA BLACK Li-100 (manufactured by DENKA COMPANY LIMITED.) are added in portions. Then, the internal temperature is maintained at 100-130°C, and heat treatment is performed for 1 hour under reduced pressure (gauge pressure; -0.093MPa). Then, the contents are cooled to below 40°C, and then the contents are taken out and passed through a three-roll mill once to obtain a base composite d-3 (base composite 3).

[0290] (F) Monofunctional perfluoropolyether compound (perfluoropolyether 3)

[0291] [Chemical formula 35]

[0292]

[0293] (E) Curing control agent: ethynyl cyclohexanol

[0294] Pressure sensitive adhesive strength test

[0295] Using an applicator, each composition of the embodiment and comparative example was applied to a PET (polyethylene terephthalate) film with a thickness of 50 μm and a width of 25 mm in a manner of 30 μm, and then heated at 130°C for 5 minutes to cure it into a rubber or gel state, thereby preparing a pressure-sensitive tape having a pressure-sensitive adhesive layer (rubber or gel cured material layer) with a thickness of 30 μm laminated on a PET film with a thickness of 50 μm. The pressure-sensitive tape was pasted on a metal plate (polished stainless steel plate), and a roller covered with a rubber layer weighing 2 kg was moved back and forth once on the tape substrate, thereby pressing the pressure-sensitive tape. After being left at room temperature for 20 hours, the force (N / 25 mm) required to peel the pressure-sensitive tape from the stainless steel plate at an angle of 180° at a tensile speed of 300 mm / min was measured using a tensile tester at 25°C, and it was used as the pressure-sensitive adhesive force of each pressure-sensitive adhesive layer (rubber or gel cured material layer).

[0296] Solvent resistance test (weight change)

[0297] 3 g of the composition of the example and comparative example was filled in a 32φ×15 mm glass container and then cured at 130°C for 5 minutes to prepare a sample. The sample was immersed in xylene at 25°C for 7 days and the weight change rate before and after the immersion was measured.

[0298] Volume resistivity measurement

[0299] Each composition of the examples and comparative examples was applied to a stainless steel plate (thickness 0.5 mm) in a thickness of 30 μm using an applicator, and then heated at 130° C. for 5 minutes to cure it into a rubber or gel state. Then, the stainless steel plate after curing each composition of the examples and comparative examples was placed between a ring probe (manufactured by Mitsubishi Chemical Corporation, trade name: URS PROBE) and a measuring table (manufactured by Mitsubishi Chemical Corporation, trade name: Resitable UFL) in a manner that the stainless steel plate and the measuring table were in contact, and a voltage of 100 V was applied between the inner electrode of the probe and the measuring table while the ring probe was pressed against the pressure-sensitive adhesive side, and then the resistivity was measured using a resistivity measuring device (manufactured by Mitsubishi Chemical Corporation, trade name: Hiresta UX).

[0300] [Table 1]

[0301]

[0302] As shown in Table 1, the pressure-sensitive adhesives of Examples 1 to 4 using the curable perfluoropolyether pressure-sensitive adhesive composition of the present invention not only have good pressure-sensitive adhesive strength and solvent resistance, but also have conductivity as confirmed by the volume resistivity after curing. In contrast, Comparative Examples 1 and 2, which do not contain the component (B) or the component (C) which are essential components of the present invention, are not cured, and Comparative Examples 3 to 4, which do not contain the component (D), have high volume resistivity and are known to be non-conductive.

[0303] As can be seen from the above, according to the present invention, it is possible to obtain a curable perfluoropolyether pressure-sensitive adhesive composition which is excellent in heat resistance, weather resistance, hydrophobicity, oleophobicity, chemical resistance, solvent resistance, etc., and which can prevent static electricity when peeling off an adherend attached to the pressure-sensitive adhesive or a tape with the pressure-sensitive adhesive.

[0304] This specification includes the following inventions.

[0305] [1]: A curable perfluoropolyether pressure-sensitive adhesive composition comprising:

[0306] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2aO-represented perfluoropolyether structure of repeating units, wherein a represents an integer of 1 to 6, the (A) linear perfluoropolyether compound is 100 parts by mass; (B) an organosilicon compound having at least 2 hydrogen atoms bonded to silicon atoms in one molecule, the (B) organosilicon compound is a curing effective amount; (C) a hydrosilylation reaction catalyst is a catalytic amount; and (D) an antistatic agent is an effective amount.

[0307] [2]: The curable perfluoropolyether pressure-sensitive adhesive composition as described in [1] above,

[0308] The component (A) is a linear perfluoropolyether compound represented by the following general formula (1):

[0309] [Chemical formula 36]

[0310]

[0311] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0312] [Chemical formula 37]

[0313]

[0314] [Chemical formula 38]

[0315] .

[0316] [3]: The curable perfluoropolyether pressure-sensitive adhesive composition as described in [1] or [2] above, wherein the antistatic agent of the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides and carbon materials.

[0317] [4]: The curable perfluoropolyether pressure-sensitive adhesive composition according to [1], [2] or [3], further comprising 0.01 to 5 parts by mass of (E) an addition reaction control agent based on 100 parts by mass of the component (A).

[0318] [5]: The curable perfluoropolyether pressure-sensitive adhesive composition as described in [1], [2], [3] or [4] above, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0319] [6]: The curable perfluoropolyether pressure-sensitive adhesive composition as described in [1], [2], [3], [4] or [5] above, which is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0320] [7]: A curable perfluoropolyether pressure-sensitive adhesive composition comprising:

[0321] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a O-repeating units represented by a perfluoropolyether structure, wherein a represents an integer of 1 to 6, the (A) linear perfluoropolyether compound is 100 to 40 parts by mass; (F) a polyfluoromonoolefin compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain, the (F) polyfluoromonoolefin compound is 0 to 60 parts by mass, and the total amount of the (A) component and the (F) component is 100 parts by mass; (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, the (B) organosilicon compound is a curing effective amount; (C) a hydrosilylation reaction catalyst, which is a catalytic amount; and (D) an antistatic agent, which is an effective amount.

[0322] [8]: The curable perfluoropolyether pressure-sensitive adhesive composition according to [7] above, wherein the component (A) is a linear perfluoropolyether compound represented by the following general formula (1):

[0323] [Chemical formula 39]

[0324]

[0325] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0326] [Chemical formula 40]

[0327]

[0328] [Chemical formula 41]

[0329] .

[0330] [9]: The curable perfluoropolyether pressure-sensitive adhesive composition as described in [7] or [8] above, wherein the component (F) is a polyfluoromonoolefin compound represented by the following general formula (2):

[0331] R 1 -(X') p -CH=CH2(2)

[0332] In formula (2), X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group, p is 0 or 1, Rf 1 The general formula is F-[CF(CF3)CF2O] w -CF(CF3)-, wherein w in the general formula represents an integer of 1 to 500,

[0333] [Chemical formula 42]

[0334] .

[0335]

[10] : The curable perfluoropolyether pressure-sensitive adhesive composition as described in [7], [8] or [9] above, wherein the antistatic agent of the component (D) is at least one selected from a conductive polymer, a surfactant, a metal, a metal oxide and a carbon material.

[0336]

[11] : The curable perfluoropolyether pressure-sensitive adhesive composition as described in [7], [8], [9] or

[10] , further comprising 0.01 to 5 parts by mass of (E) an addition reaction control agent, based on 100 parts by mass of the total of the component (A) and the component (F).

[0337]

[12] : The curable perfluoropolyether pressure-sensitive adhesive composition as described in [7], [8], [9],

[10] or

[11] above, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0338]

[13] : The curable perfluoropolyether pressure-sensitive adhesive composition as described in [7], [8], [9],

[10] ,

[11] or

[12] above, which is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0339]

[14] : A pressure-sensitive adhesive comprising a cured product of the curable perfluoropolyether pressure-sensitive adhesive composition described in [1], [2], [3], [4], [5], [6], [7], [8], [9],

[10] ,

[11] ,

[12] or

[13] .

[0340]

[15] : A pressure-sensitive adhesive tape comprising a substrate on which is laminated a cured layer of the curable perfluoropolyether pressure-sensitive adhesive composition described in [1], [2], [3], [4], [5], [6], [7], [8], [9],

[10] ,

[11] ,

[12] or

[13] .

[0341] Furthermore, when the present invention is described from a different perspective, it will be as described in the following <1> to <15>.

[0342] <1> A curable perfluoropolyether pressure-sensitive adhesive composition comprising:

[0343] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6;

[0344] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule;

[0345] (C) a hydrosilylation reaction catalyst; and

[0346] (D) Antistatic agent.

[0347] <2> The curable perfluoropolyether pressure-sensitive adhesive composition according to <1>, wherein the component (A) is a linear perfluoropolyether compound represented by the following general formula (1),

[0348] [Chemical formula 43]

[0349]

[0350] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0351] [Chemical formula 44]

[0352]

[0353] [Chemical formula 45]

[0354] .

[0355] <3> The curable perfluoropolyether pressure-sensitive adhesive composition according to <1>, wherein the antistatic agent as the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides, and carbon materials.

[0356] <4> The curable perfluoropolyether pressure-sensitive adhesive composition according to <1>, further comprising (E) an addition reaction control agent.

[0357] <5> The curable perfluoropolyether pressure-sensitive adhesive composition according to <1>, wherein the volume resistivity is 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0358] <6> The curable perfluoropolyether pressure-sensitive adhesive composition according to <1>, which forms a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0359] <7> A curable perfluoropolyether pressure-sensitive adhesive composition comprising:

[0360] (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -Ca F 2a A perfluoropolyether structure of a repeating unit represented by O-, wherein a represents an integer of 1 to 6;

[0361] (F) a polyfluoromonoalkenyl compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain;

[0362] (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule;

[0363] (C) a hydrosilylation reaction catalyst; and

[0364] (D) Antistatic agent.

[0365] <8> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, wherein the component (A) is a linear perfluoropolyether compound represented by the following general formula (1),

[0366] [Chemical formula 46]

[0367]

[0368] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600,

[0369] [Chemical formula 47]

[0370]

[0371] [Chemical formula 48]

[0372] .

[0373] <9> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, wherein the component (F) is a polyfluoromonoolefin compound represented by the following general formula (2):

[0374] R 1 -(X') p -CH=CH2(2)

[0375] In formula (2), X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group, p is 0 or 1, Rf 1 The general formula is F-[CF(CF3)CF2O] w -CF(CF3)-, wherein w in the general formula represents an integer of 1 to 500,

[0376] [Chemical formula 49]

[0377] .

[0378] <10> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, wherein the antistatic agent as the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides, and carbon materials.

[0379] <11> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, further comprising (E) an addition reaction control agent.

[0380] <12> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product.

[0381] <13> The curable perfluoropolyether pressure-sensitive adhesive composition according to <7>, which forms a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

[0382] <14> A pressure-sensitive adhesive comprising a cured product of the curable perfluoropolyether pressure-sensitive adhesive composition according to any one of <1> to <13>.

[0383] <15> A pressure-sensitive adhesive tape comprising a substrate and a cured product layer of the curable perfluoropolyether pressure-sensitive adhesive composition according to any one of <1> to <13> laminated on the substrate.

[0384] In the above <1> to <15>, the balance of various properties may be changed by changing the blending ratio of each component. In such a case, some properties may become unstable or deteriorate, but the desired properties vary depending on the application, so they can be applied in practice according to the application.

[0385] The present invention is not limited to the above-mentioned embodiments. The above-mentioned embodiments are examples, and all technical solutions having substantially the same structure and achieving the same technical effects as the technical concept described in the claims of the present invention are included in the technical scope of the present invention.

Claims

1. A curable perfluoropolyether pressure-sensitive adhesive composition comprising: (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a O-repeating unit represented by a perfluoropolyether structure, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 parts by mass; (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount; (C) a hydrosilylation reaction catalyst in a catalytic amount; and (D) an antistatic agent in an effective amount.

2. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1, wherein The component (A) is a linear perfluoropolyether compound represented by the following general formula (1): [Chemical formula 1] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600, [Chemical formula 2] [Chemical formula 3] 。 3. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1, wherein The antistatic agent of the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides and carbon materials.

4. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1, wherein The (E) addition reaction control agent is further contained in an amount of 0.01 to 5 parts by mass based on 100 parts by mass of the (A) component.

5. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1, which can obtain a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product. 6 . The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1 , which is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm.

7. A curable perfluoropolyether pressure-sensitive adhesive composition comprising: (A) a linear perfluoropolyether compound having at least two alkenyl groups in one molecule and a main chain containing -C a F 2a O-repeating unit represented by a perfluoropolyether structure, wherein a represents an integer of 1 to 6, and the (A) linear perfluoropolyether compound is 100 to 40 parts by mass; (F) a polyfluoromonoalkenyl compound having one alkenyl group in one molecule and a perfluoropolyether structure in the main chain, wherein the polyfluoromonoalkenyl compound (F) is present in an amount of 0 to 60 parts by mass, and the total amount of the component (A) and the component (F) is 100 parts by mass; (B) an organosilicon compound having at least two hydrogen atoms bonded to silicon atoms in one molecule, wherein the organosilicon compound (B) is in a curing effective amount; (C) a hydrosilylation reaction catalyst in a catalytic amount; and (D) an antistatic agent in an effective amount.

8. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7, wherein: The component (A) is a linear perfluoropolyether compound represented by the following general formula (1): [Chemical formula 4] In formula (1), X is -CH2-, -CH2O-, -CH2OCH2- or -Y-NR 1 -CO-, wherein Y is -CH2- or a group represented by the following structural formula (Z), R 1 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is independently 0 or 1, r is an integer of 2 to 6, m and n are integers of 0 to 600, and the sum of m and n is 50 to 600, [Chemical formula 5] [Chemical formula 6] 。 9. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7, wherein: The component (F) is a polyfluoromonoolefin compound represented by the following general formula (2): Rf 1 -(X’) p -CH=CH2(2) In formula (2), X' is -CH2-, -OCH2-, -CH2OCH2- or -CO-NR 2 -Y'-, wherein Y' is -CH2- or a group represented by the following structural formula (Z'), R 2 is a hydrogen atom, a methyl group, a phenyl group or an allyl group; p is 0 or 1; Rf 1 The general formula is F-[CF(CF3)CF2O] w -CF(CF3)-, wherein w in the general formula represents an integer of 1 to 500, [Chemical formula 7] 。 10. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7, wherein The antistatic agent of the component (D) is at least one selected from the group consisting of conductive polymers, surfactants, metals, metal oxides and carbon materials.

11. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7, wherein: The (E) addition reaction control agent is further contained in an amount of 0.01 to 5 parts by mass based on 100 parts by mass of the total of the (A) component and the (F) component.

12. The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7, which has a volume resistivity of 1.0×10 2 ~1.0×10 8 Ω·m solidified product. 13 . The curable perfluoropolyether pressure-sensitive adhesive composition according to claim 7 , which is cured to form a pressure-sensitive adhesive having a pressure-sensitive adhesive force of 0.001 N / 25 mm to 10.0 N / 25 mm. 14 . A pressure-sensitive adhesive comprising a cured product of the curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1 . 15 . A pressure-sensitive adhesive tape comprising a substrate and a cured product layer of the curable perfluoropolyether pressure-sensitive adhesive composition according to claim 1 laminated thereon.

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