Silicone release agent composition and laminate

Abstract

To provide a silicone release agent composition that suppresses bleed-out on a release layer surface, and to which anti-static capability is imparted without impairing peeling performance, and a laminate of the same.SOLUTION: A silicone release agent composition contains a silicone-based resin and an onium salt represented by formula (1): Q+.(R1SO2)2 N-, wherein Q+ represents pyridinium cation having an alkenyl group or imidazolium cation. R1 in the formula (1) represents a perfluoroalkyl group having 1 to 4 carbon chains or a fluoro group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a silicone release agent composition that contains an onium salt having an alkenyl group in the cation, and a laminate thereof. [Background technology]

[0002] It is known that a conductive polymer (PEDOT dispersion) can be used to impart an antistatic function to a silicone release agent composition (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2020-23690 A Summary of the Invention [Problem to be solved by the invention]

[0004] A release layer containing a silicone resin has a problem of bleeding out to the surface due to the low compatibility of the antistatic agent with the silicone resin. In addition, in order to compensate for the antistatic performance of the release layer, it is necessary to coat a separate antistatic primer layer containing a conductive polymer or the like. Therefore, the present invention provides a silicone release agent composition that has excellent release properties and does not lose its antistatic properties due to bleed-out, by incorporating an onium salt having an alkenyl group in the cation into a silicone resin as an antistatic agent. [Means for solving the problem]

[0005] Means for Solving the Problems The present inventors have conducted extensive research and have found that by incorporating a certain amount of an onium salt having an alkenyl group at the cation moiety into a silicone resin, it is possible to obtain a silicone release agent composition having sufficient antistatic ability and excellent release properties, thereby completing the present invention.

[0006] The present invention is described in the following [1] to [6].

[0007] [1] A silicone release agent composition comprising a silicone resin and an onium salt represented by formula (1). Formula (1):Q + ·(R 1 SO 2 ) 2 N - (1) (In the formula, Q + is formula (2) or formula (3) R in formula (1) 1 represents a perfluoroalkyl group having a carbon chain of 1 to 4 or a fluoro group. [ka] TIFF2024106777000002.tif1946 In formula (2), R 2 In formula (3), R may be the same or different and is an alkyl group having 1 to 4 carbon atoms or a hydrogen atom. 3 represents an alkyl group having 1 to 4 carbon atoms. n represents 1 to 4. [2] R in Equation (1) 1 The silicone release agent composition according to [1], wherein [3] The silicone release agent composition according to [1] or [2], comprising 0.1 to 10 parts by mass of an onium salt represented by formula (1) per 100 parts by mass of the silicone resin. [4] The silicone release agent composition according to any one of [1] to [3], wherein the silicone resin is an addition reaction type silicone resin. [5] A laminate comprising a release layer comprising the silicone release agent composition according to any one of [1] to [4] formed on a substrate. [6] A method for producing a laminate, comprising the step of forming a release layer comprising the silicone release agent composition according to any one of [1] to [4] on a substrate. Effect of the Invention

[0008] According to the present invention, it is possible to provide a silicone release agent composition containing a silicone resin to which antistatic properties are imparted without impairing release performance. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present invention will be described below.

[0010] [Alkenyl-containing onium salts] The silicone release agent composition of the present invention contains an onium salt represented by formula (1). Formula (1): Q + ·(R 1 SO 2 ) 2 N - (1) (In the formula, Q + is formula (2) or formula (3) [ka] TIFF2024106777000004.tif1946

[0011] R in formula (1) 1 is a perfluoroalkyl group having a carbon chain of 1 to 4 or a fluoro group, and examples thereof include a fluoro group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group, and is preferably a trifluoromethyl group.

[0012] In formula (2), R 2 R is an alkyl group having 1 to 4 carbon atoms or a hydrogen atom, and this alkyl group may be either linear or branched. A linear alkyl group or a hydrogen atom is preferred. Specific examples include a methyl group, an ethyl group, a propyl group, and a butyl group, and a linear alkyl group having 1 to 2 carbon atoms or a hydrogen atom is particularly preferred. 3is an alkyl group having 1 to 4 carbon atoms. This alkyl group may be either linear or branched, and is preferably a linear alkyl group. Specific examples include a methyl group, an ethyl group, a propyl group, and a butyl group, and is preferably a methyl group. In formula (2) and formula (3), n represents 1 to 4, and is preferably 1.

[0013] The onium salt represented by formula (1) of the present invention can be produced by various methods, a typical method being to react an amine with an alkyl halide having an alkenyl group to synthesize an onium halide, and then synthesize an onium salt by a double decomposition reaction with an alkali metal salt of imidic acid.

[0014] Examples of amines suitable for this synthesis include 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 3-ethylpyridine, 4-ethylpyridine, 2-propylpyridine, 3-propylpyridine, 4-propylpyridine, 2-butylpyridine, 3-butylpyridine, 4-butylpyridine, 2,3-dimethylpyridine, 3,4-dimethylpyridine, 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, and 1-butylimidazole.

[0015] Examples of alkyl halides include allyl chloride, allyl bromide, allyl iodide, 4-chloro-1-butene, 4-bromo-1-butene, 4-iodo-1-butene, 5-chloro-1-pentene, 5-bromo-1-pentene, 5-iodo-1-pentene, 6-chloro-1-hexene, 6-bromo-1-hexene, and 6-iodo-1-hexene.

[0016] The quaternization reaction of amines with alkyl halides may or may not be carried out in the presence of a solvent, and examples of the solvent include alcohols such as methanol, ethanol, and 2-propanol, acetonitrile, ethyl acetate, tetrahydrofuran, and dimethylformamide.

[0017] The amount of the alkyl halides used may be 0.7 mol or more, and preferably 0.9 to 1.5 mol, per mol of the amines.

[0018] Examples of the alkali metal salt of imidic acid include lithium bis(trifluoromethanesulfonyl)imide, sodium bis(trifluoromethanesulfonyl)imide, potassium bis(trifluoromethanesulfonyl)imide, lithium bis(fluoromethanesulfonyl)imide, sodium bis(fluoromethanesulfonyl)imide, and potassium bis(fluoromethanesulfonyl)imide.

[0019] The amount of the imidic acid alkali metal salt used in the metathesis reaction is usually 0.8 mol or more, preferably 0.9 to 1.2 mol, and more preferably 1 to 1.05 mol, per mol of the onium halide.

[0020] The metathesis reaction is usually carried out in a solvent, such as ketones (e.g., acetone, methyl ethyl ketone (MEK) and the like), alcohols (e.g., methanol, ethanol, 2-propanol and the like), acetonitrile, ethyl acetate, tetrahydrofuran, dimethylformamide and the like.

[0021] The order of mixing the onium halide, the alkali metal imidate, and the solvent is not particularly limited. The onium halide and the solvent may be mixed and then the alkali metal imidate may be added, or the onium halide may be mixed and then the alkali metal imidate may be added.

[0022] The reaction temperature in the metathesis reaction is usually 10°C or higher, preferably 10 to 60°C, and particularly preferably 10 to 30°C.

[0023] To isolate the onium salt from the reaction solution after the completion of the metathesis reaction, the solvent and the inorganic salt produced are removed from the reaction solution. If the inorganic salt precipitates in the reaction solution, the reaction solution is filtered to remove the precipitated inorganic salt, and then the onium salt is isolated by an appropriate combination of unit operations such as concentration, filtration, and extraction.

[0024] It is known that amine compounds and ammonium cations can be catalytic poisons for platinum catalysts. Therefore, ammonium-based onium salts tend to inhibit the curing of silicone-based resins, and poor curing leads to a decrease in solvent resistance, which causes the release layer to dissolve into the adherend (adhesive layer, etc.). In addition, ammonium-based onium salts have poor compatibility with silicone-based resins, so they bleed out onto the surface, causing the problem of contaminating the adherend. The cations represented by formulas (2) and (3) do not act as catalytic poisons to the platinum catalyst, and therefore do not inhibit the curing of the silicone resin. Furthermore, there is no deterioration in solvent resistance due to poor curing, and therefore the release layer is prevented from falling off from the substrate. In addition, since the onium salt represented by formula (1) has a reactive alkenyl group, it reacts and is fixed in the silicone resin during the curing reaction in forming the release layer, so that the onium salt is prevented from leaching out, and contamination of the adherend and changes in electrostatic performance over time are less likely to occur.

[0025] [Silicone release agent composition] The silicone release agent composition of the present invention contains at least an onium salt and a silicone resin. As the silicone resin, a mixture of an organic resin and a silicone resin or a copolymer resin may be used. In view of excellent releasability and heat resistance, it is particularly preferable to contain a curable silicone resin.

[0026] Curable silicone resins include an "addition reaction type" in which an organohydrogenpolysiloxane and an organopolysiloxane containing an alkenyl group are heat-cured in the presence of a platinum catalyst, a "condensation polymerization reaction type" in which an organohydrogenpolysiloxane and an organopolysiloxane containing a terminal hydroxyl group are heat-cured using an organotin catalyst, a "radical addition type" in which an organopolysiloxane containing an alkenyl group and an organopolysiloxane containing a mercapto group are cured using a photopolymerization catalyst, and a "cationic polymerization type" in which an epoxy group is photo-ring-opened with an onium salt initiator and cured. From the viewpoint of the reactivity of the alkenyl group, the addition reaction type in which an organohydrogenpolysiloxane and an organopolysiloxane containing an alkenyl group are heat-cured in the presence of a platinum catalyst is preferred. The silicone release agent composition of the present invention is formed by removing the solvent from the coating composition, if necessary, in a drying step, and then curing the composition.

[0027] [Paint composition] The coating composition described above is a mixture that exhibits liquid properties at room temperature, and contains a material capable of forming a silicone release agent composition, a polymerization initiator, a curing agent, and a curing catalyst, and may further contain various additives such as a solvent, particles, a crosslinking agent, and an antistatic agent. The coating composition is not particularly limited in its composition, but from the viewpoints of releasability and heat resistance as described above, a resin precursor capable of forming a curable silicone-based resin is preferred, and a coating composition containing an "addition reaction type" resin precursor, a polymerization initiator, a curing agent, and a curing catalyst is more preferred.

[0028] The addition reaction type silicone resin preferably contains polydimethylsiloxane containing vinyl groups at its terminals and hydrogensiloxane. Specific examples include KS-3650, KS843, KS847, KS847H, KS847T, X62-2829, and KS838 manufactured by Shin-Etsu Chemical Co., Ltd., and SD7333, SRX357, SRX345, LTC310, LTC303E, LTC300B, LTC350G, LTC750A, LTC851, LTC759, LTC755, LTC761, and LTC856 manufactured by Dow Corning Toray Co., Ltd.

[0029] Examples of the curing catalyst include platinum-based catalysts, that is, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a reaction product of chloroplatinic acid and an alcohol solution, a reaction product of chloroplatinic acid and an olefin compound, a reaction product of chloroplatinic acid and a vinyl group-containing siloxane compound, a platinum-olefin complex, a platinum-vinyl group-containing siloxane complex, a platinum-phosphorus complex, etc. More specifically, examples of the above-mentioned curing catalyst include CAT-PL-50T manufactured by Shin-Etsu Chemical Co., Ltd. and SRX-212 manufactured by Dow Corning Toray Co., Ltd.

[0030] The amount of the curing catalyst is usually 0.1 to 1 part by mass, preferably 0.3 to 0.6 parts by mass, based on the silicone resin component in terms of platinum element amount. If it is less than 0.1 part by mass, the curability decreases and the cohesive force (retentive force) of the release layer decreases, whereas if it is 1 part by mass or more, the platinum content is high, which increases the cost and decreases the stability of the release layer. Here, the release layer refers to a layer formed by curing the coating composition applied on the support substrate after the solvent is removed by a drying process.

[0031] Since it is necessary to impart sufficient antistatic properties while maintaining the release properties, the content of the onium salt in the silicone release agent composition of the present invention is usually preferably 0.1 to 10 parts by mass, and more preferably 1 to 6 parts by mass, based on 100 parts by mass of the silicone resin solid content.

[0032] The solids concentration of the coating composition of the present invention is not particularly limited, but when the coating composition contains a solvent, it is usually 10 parts by mass or less, and more preferably 0.5 to 5 parts by mass.

[0033] The coating composition of the present invention does not need to be divided into two layers, a release layer to be applied to the supporting substrate and a primer layer having an antistatic layer, as in the conventional method, in order to avoid impairing the peelability, and can be applied in a single layer to the supporting substrate.

[0034] [Other paint composition additives] The coating composition preferably contains a solvent from the viewpoint of manufacturability. Here, the solvent refers to a substance that is liquid at room temperature and normal pressure and can be evaporated in almost its entirety in a drying process after application. The coating composition suitable for the laminate of the present invention may contain a solvent. The number of types of solvents is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. By drying the coating composition, it becomes a silicone release agent composition and can form a release layer.

[0035] Examples of the solvent that can be used include aromatic hydrocarbons such as toluene, aliphatic hydrocarbons such as hexane, ketones such as methyl ethyl ketone (MEK) and isobutyl methyl ketone, esters such as ethyl acetate and butyl acetate, alcohols such as ethanol and 2-propanol, and ethers such as diisopropyl ether and dibutyl ether. Taking into consideration the solubility, coatability, boiling point, etc., it is preferable to use these alone or in combination.

[0036] Since aqueous solvents can act as a catalyst poison for the platinum catalyst necessary for curing silicone resins, it is preferable to use an organic solvent as the solvent for the coating composition of the present invention.

[0037] The laminate in the present invention refers to a support substrate on which a release layer containing a silicone release agent composition is formed. The laminate referred to here is a release film or the like.

[0038] [Supporting base material] Examples of the supporting substrate in the present invention include polyester films such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate, polyethylene films, polypropylene films, polyvinyl chloride films, polyvinylidene chloride films, polyvinyl alcohol films, ethylene-vinyl acetate copolymer films, polystyrene films, polycarbonate films, polymethylpentene films, polysulfone films, polyether ether ketone films, polyether sulfone films, polyphenylene sulfide films, polyetherimide films, polyimide films, fluororesin films, polyamide films, acrylic resin films, norbornene-based resin films, and cycloolefin resin films. In particular, when used as a release film, polyethylene terephthalate films are preferred.

[0039] The thickness of the substrate is preferably 10 to 100 μm, more preferably 15 to 80 μm, and even more preferably about 20 to 50 μm for ease of handling.

[0040] [Method of manufacturing laminate] Although the method of applying the coating composition onto the supporting substrate is not particularly limited, it is preferable to apply the coating composition to the supporting substrate or the like by a dip coating method, a roller coating method, a wire bar coating method, a gravure coating method, or the like to form a layer. Furthermore, among these coating methods, the wire bar coating method is more preferable. Next, the liquid film applied onto the supporting substrate or the like is dried. In addition to completely removing the solvent from the obtained laminate, it is preferable that the liquid film is heated in the drying process from the viewpoint of promoting the curing of the coating film. In the drying process, when the curing is performed by heat, the temperature is preferably from room temperature to 200°C or less, and more preferably from the viewpoint of the activation energy of the curing reaction, it is more preferably from 80°C to 200°C, and further preferably from 80°C to 150°C. EXAMPLES

[0041] The present invention will now be described with reference to examples, but the present invention is not necessarily limited to these. Note that the same compounds were used in the same products unless otherwise specified.

[0042] (Synthesis Example 1) A mixture of 13.0 g (140 mmol) of 3-methylpyridine and 18.6 g (154 mmol) of allyl bromide was stirred and reacted at 80° C. for 3 hours. After completion of the reaction, the mixture was dried under reduced pressure to obtain 29.1 g (yield 97%) of 1-allyl-3-methylpyridinium bromide. 15.0 g (70 mmol) of the obtained 1-allyl-3-methylpyridinium bromide was dissolved in 30 g of pure water, and 22.1 g (77 mmol) of lithium bis(trifluoromethanesulfonyl)imide was added, followed by stirring at room temperature for 1 hour. The reaction solution was filtered and then washed with pure water to remove inorganic salts. After concentration, 25.2 g (91% yield) of liquid 1-allyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide was obtained.

[0043] (Synthesis Example 2) The synthesis was performed without any changes except that lithium bis(fluorosulfonyl)imide was used instead of lithium bis(trifluoromethanesulfonyl)imide described in Synthesis Example 1, and 20.7 g (yield 94%) of liquid 1-allyl-3-methylpyridinium bis(fluorosulfonyl)imide was obtained.

[0044] (Synthesis Example 3) A mixture of 11.5 g (140 mmol) of 1-methylimidazolium and 18.6 g (154 mmol) of allyl bromide was stirred and reacted at 80° C. for 3 hours. After the reaction was completed, the mixture was dried under reduced pressure to obtain 28.4 g (yield 99%) of 1-methyl-3-allylimidazolium bromide. 12.8g (63mmol) of the obtained 1-methyl-3-allylimidazolium bromide was dissolved in 30g of pure water, 20.1g (70mmol) of lithium bis(trifluoromethanesulfonyl)imide was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was filtered, and then washed with pure water to remove inorganic salts. After concentration, 24.0g (99% yield) of liquid 1-methyl-3-allylimidazolium bis(trifluoromethanesulfonyl)imide was obtained.

[0045] (Synthesis Example 4) The synthesis was performed without any changes except that lithium bis(fluorosulfonyl)imide was used instead of lithium bis(trifluoromethanesulfonyl)imide described in the synthesis conditions of Synthesis Example 1, and 17.9 g (yield 93%) of liquid 1-methyl-3-allylimidazolium bis(fluorosulfonyl)imide was obtained.

[0046] (Synthesis Example 5) A mixture of 13.0 g (140 mmol) of 3-methylpyridine and 23.0 g (154 mmol) of 5-bromo-1-pentene was stirred and reacted at 80° C. for 4 hours. After completion of the reaction, the mixture was dried under reduced pressure to obtain 30.5 g (yield 90%) of 1-pentenyl-3-methylpyridinium bromide. 15.0 g (70 mmol) of the obtained 1-pentenyl-3-methylpyridinium bromide was dissolved in pure water, and 22.1 g (77 mmol) of lithium bis(trifluoromethanesulfonyl)imide was added, followed by stirring at room temperature for 1 hour. The reaction solution was filtered, and then washed with pure water to remove inorganic salts. After concentration, 29.4 g (95% yield) of liquid 1-pentenyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide was obtained.

[0047] (Synthesis Example 6) The synthesis was carried out in the same manner as in Synthesis Example 5, except that lithium bis(fluorosulfonyl)imide was used instead of lithium bis(trifluoromethanesulfonyl)imide, and 23.0 g (yield 96%) of liquid 1-pentenyl-3-methylpyridinium bis(fluorosulfonyl)imide was obtained.

[0048] (Synthesis Example 7) A mixture of 11.5 g (140 mmol) of 1-methylimidazole and 23.0 g (154 mmol) of 5-bromo-1-pentene was stirred and reacted at 80° C. for 4 hours. After the reaction was completed, the mixture was dried under reduced pressure to obtain 30.4 g (yield 94%) of 1-methyl-3-pentenylimidazolium bromide. The obtained 1-methyl-3-pentenylimidazolium bromide 15.0g (70mmol) was dissolved in pure water, and 22.1g (77mmol) of lithium bis(trifluoromethanesulfonyl)imide was added, followed by stirring at room temperature for 1 hour. The reaction solution was filtered, and then washed with pure water to remove inorganic salts. After concentration, 27.5g (yield 91%) of liquid 1-methyl-3-pentenylimidazolium bis(trifluorosulfonyl)imide was obtained.

[0049] (Synthesis Example 8) The synthesis was performed without any changes except that lithium bis(fluorosulfonyl)imide was used instead of lithium bis(trifluoromethanesulfonyl)imide described in Synthesis Example 7, and 20.9 g (yield 90%) of liquid 1-methyl-3-pentenylimidazolium bis(fluorosulfonyl)imide was obtained.

[0050] Example 1 [Preparation of coating composition] Methylvinylpolysiloxane and methylhydrogenated polysiloxane (solid content of silicone resin precursor): 100 parts by mass (KS847, Shin-Etsu Chemical Co., Ltd., solid content 30 parts by mass) Methylvinylpolysiloxane and platinum complex solution: 2 parts by weight (CAT_PL-50T manufactured by Shin-Etsu Chemical Co., Ltd.) Onium salt of Synthesis Example 1: 4 parts by mass The above composition was diluted with toluene and MEK at a ratio of 1:1 to prepare a coating material having a solid content of 5 parts by mass.

[0051] Example 2 A coating composition was prepared without making any changes to Example 1 except that the onium salt in Synthesis Example 2 was used.

[0052] Example 3 A coating composition was prepared without making any changes to Example 1, except that the onium salt in Synthesis Example 3 was used.

[0053] Example 4 A coating composition was prepared without making any changes to Example 1 except that the onium salt in Synthesis Example 4 was used.

[0054] Example 5 A coating composition was prepared without making any changes to Example 1, except that the onium salt of Synthesis Example 5 was used.

[0055] Example 6 A coating composition was prepared without making any changes to Example 1, except that the onium salt of Synthesis Example 6 was used.

[0056] Example 7 A coating composition was prepared without making any changes to Example 1, except that the onium salt of Synthesis Example 7 was used.

[0057] Example 8 A coating composition was prepared without making any changes to Example 1, except that the onium salt of Synthesis Example 8 was used.

[0058] Comparative Example 1 A coating composition was prepared without changing the conditions of Example 1 except that the onium salt was not added.

[0059] Comparative Example 2 A coating composition was prepared without making any changes to Example 1, except that 1-butylpyridinium bis(trifluoromethanesulfonyl)imide was used as the onium salt.

[0060] Comparative Example 3 A coating composition was prepared without making any changes to Example 1, except that 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide was used as the onium salt.

[0061] Comparative Example 4 A coating composition was prepared without making any changes to Example 1, except that 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide was used as the onium salt.

[0062] Comparative Example 5 A coating composition was prepared without making any changes to Example 1, except that diallyldimethylammonium bis(trifluoromethanesulfonyl)imide was used as the onium salt.

[0063] Comparative Example 6 A coating composition was prepared without making any changes to Example 1, except that diallyldimethylammonium bis(fluorosulfonyl)imide was used as the onium salt.

[0064] [Coating conditions] The coating composition was coated onto a PET film using a bar coater to give a film thickness of about 500 nm after drying, and heated at 150° C. for 2 minutes to prepare a test piece (release film).

[0065] [Surface resistivity measurement] Using a Simco-Ion surface resistivity meter ST-4, the surface resistivity of the test pieces was measured at room temperature, 50% RH, and an applied voltage of 100 V initially and after 7 days of storage at room temperature.

[0066] [Peel test] Nitto Denko No. 31 tape was applied to the coating surface and after curing for 1 hour, the peel strength was measured at 180° peeling speed of 0.3 m / min.

[0067] [Evaluation of adhesion to substrate] A cross-shaped cut (50 mm x 50 mm) was made with a cutter knife on the release layers produced in the examples and comparative examples. The release layers at the cut sites were then rubbed with the pads of fingers to check the degree of removal of the release layers, and the adhesion to the substrate was evaluated. ○ The release layer does not fall off from the substrate and maintains good adhesion △: Part of the release layer becomes cloudy, but it does not fall off and maintains adhesion. × The entire release layer falls off from the substrate, resulting in insufficient adhesion

[0068] The results of Examples 1 to 8 and Comparative Examples 1 to 6 are shown in Table 1. [Table 1]

[0069] As described above, the silicone release agent compositions of Examples 1 to 8 of the present invention can provide a surface resistivity (10 13 The peel strength of each of the Examples was equal to that of the blank of Comparative Example 1, which indicates that the alkenyl-containing onium salt does not adversely affect the peeling properties. Furthermore, even after 7 days of storage, the increase or decrease in surface resistivity was suppressed to within an index change of 1, and the peel strength was also maintained, which indicates that the onium salt has an effect of suppressing bleeding out onto the release layer surface. On the other hand, Comparative Examples 1 and 5 to 6 had no change over time but high surface resistivity, and Comparative Examples 2 to 4 had insufficient adhesion and large changes over time in surface resistivity and peel strength, which is thought to be the cause of bleeding out. All of the Comparative Examples lacked the performance required for an antistatic silicone release agent. [Industrial Applicability]

[0070] According to the present invention, it is possible to provide a silicone release agent composition containing a silicone resin to which antistatic properties are imparted without impairing release performance, and a laminate thereof.

Claims

1. A silicone release agent composition comprising a silicone resin and an onium salt represented by formula (1): Formula (1): Q ＋ · (R 1 SO 2 ) 2 N － (1) (In the formula, Q ＋ is the formula (2) or the formula (3) [Chemistry 2-3] 【change】 R in formula (1) 1 represents a perfluoroalkyl group having a carbon chain of 1 to 4 or a fluoro group. 2 are the same or different alkyl groups having 1 to 4 carbon atoms or hydrogen atoms. 3 represents an alkyl group having 1 to 4 carbon atoms, and n represents 1 to 4.

2. R in formula (1) 1 2. The silicone release agent composition according to claim 1, wherein is a trifluoromethyl group or a fluoro group.

3. 2. The silicone release agent composition according to claim 1, comprising 0.1 to 10 parts by mass of the onium salt represented by formula (1) relative to 100 parts by mass of the silicone resin.

4. 2. The silicone release agent composition according to claim 1, wherein the silicone resin is an addition reaction type silicone resin.

5. A laminate comprising a substrate and a release layer formed on the substrate, the release layer comprising the silicone release agent composition according to any one of claims 1 to 4.

6. A method for producing a laminate, comprising the step of forming a release layer comprising the silicone release agent composition according to any one of claims 1 to 4 on a substrate.

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