Source: https://patents.google.com/patent/US7491758?oq=7222078
Timestamp: 2018-03-17 21:27:01
Document Index: 112165101

Matched Legal Cases: ['Application No. 05015766', 'Application No. 05004925', 'Application No. 05005660', 'Application No. 05009331', 'Application No. 05016102', 'Application No. 05020102', 'Application No. 2005']

US7491758B2 - Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and surface protecting film - Google Patents
US7491758B2
US7491758B2 US11141590 US14159005A US7491758B2 US 7491758 B2 US7491758 B2 US 7491758B2 US 11141590 US11141590 US 11141590 US 14159005 A US14159005 A US 14159005A US 7491758 B2 US7491758 B2 US 7491758B2
US11141590
US20050266238A1 (en )
The present invention provides a pressure-sensitive adhesive which can prevent electrification of a non-electrification-prevented adherend upon peeling, suppresses occurrence of peeling off even with time or via treatment under a high temperature, and is excellent in adhesion reliance, as well as an antistatic pressure-sensitive adhesive sheet, and surface protecting film using this. The pressure-sensitive adhesive composition of the present invention contains an ionic liquid, and a polymer having a glass transition temperature of Tg of 0° C. or lower as a base polymer, as well as an ethylene oxide group-containing compound and/or a surfactant.
That is, a pressure-sensitive adhesive composition of the present invention is characterized in that said composition contains an ionic liquid, and a polymer having a glass transition temperature Tg of 0° C. or lower as a base polymer, as well as an ethylene oxide group-containing compound and/or a surfactant. Herein, an ionic liquid refers to a melt salt (ionic compound) exhibiting liquid state at room temperature (25° C.).
Further, it is preferable that a polymer having a glass transition temperature Tg of 0° C. or lower is an acryl-based polymer containing, as a main component, one or more kinds of acrylate and/or methacylate having an alkyl group of a carbon number of 1 to 14. By these acryl-based polymers, balance between compatibilities with an ionic liquid and a base polymer becomes better, and pressure-sensitive adhesive property can be sufficiently maintained.
The pressure-sensitive adhesive composition of the present invention contains an ionic liquid, and a polymer having a glass transition temperature Tg of 0° C. or lower as a base polymer, as well as an ethylene oxide group-containing compound and/or a surfactant. An ionic liquid refers to as melt salt (ionic compound) exhibiting liquid state at room temperature (25° C.).
As the aforementioned ionic liquid, a commercially available ionic liquid may be used, and it may be also synthesized as described below. A method of synthesizing an ionic liquid is not particularly limited as far as an objective ionic liquid is obtained. Generally, a halide method, a hydroxide method, an acid ester method, a complex formation method, and a neutralization method described in reference “Ionic Liquid-Frontier Future of Development-” published by CMC Publisher are used.
R4NX+H2O→R4NOH+½H2+½X2 (X:Cl,Br,I) (4)
R4NX+P—OH→R4NOH+P—X(P—OH:OH-type ion exchange resin) (5)
In the present invention, as a base polymer, a polymer having a glass transition temperature Tg of 0° C. or lower is used. Tg is preferably −100 to −5° C., more preferably −80 to −10° C. When a glass transition temperature Tg is higher than 0° C., it becomes difficult to obtain a sufficient adhesive strength in some cases.
As other component, since balance of pressure-sensitive adhering performance can be taken, by rendering Tg 0° C. or lower (usually −100° C. or higher), a cohesive strength and heat resistance improving component such as a sulfonic acid group-containing monomer, a phosphoric acid group-containing monomer, a cyano group-containing monomer, vinyl esters, and an aromatic vinyl compound, and a component having a functional group which improves an adhering force or serves as a crosslinking point, such as a carboxyl group-containing monomer, an acid anhydride group-containing monomer, a hydroxyl group-containing monomer, an amido group-containing monomer, an amino group-containing monomer, an imido group-containing monomer, an epoxy group-containing monomer, and vinyl ethers can be appropriately used. Other components may be used alone, or may be used by mixing two or more kinds.
Y; titration amount (ml) of sample solution
X; titration amount (ml) of solution of only 50 g of mixed solvent
f; factor of titrating solution
M; weight (g) of polymer sample
Sample concentration: 0.2% by weight (THF solution)
Sample column; TSKguardcolumn SuperHZ-H (1)+TSKgel SuperHZM-H(2) Reference column; TSKgel SuperH-RC (1)
Regarding a glass transition temperature Tg (° C.), as a glass transition temperature Tgn (° C.) of a homopolymer for each monomer, the following reference value was used, and the temperature was obtained by the following equation.
[wherein, Tg (° C.) indicates a glass transition temperature of a copolymer, Wn(−) indicates a weight fraction of each monomer, Tgn (° C.) indicates a glass transition temperature of a homopolymer for each monomer, and n indicates a kind of each monomer]
Isononyl acrylate: −82° C.
Ethoxy-diethylene glycol acrylate: −70° C.
<Ionic Liquid Structural Analysis>
Measurement solvent: acetone-d6
First, Examples when an ethylene oxide group-containing compound is used will be explained.
Preparation Example 1 Acryl-based Polymer (A)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 200 parts by weight of 2-ethylhexyl acrylate, 8 parts by weight of 2-hydroxyethyl acrylate, 0.4 part by weight of 2,2′-azobisisobutyronitrile as a polymerization initiator, and 312 parts by weight of ethyl acetate, a nitrogen gas was introduced while mildly stirring, and a polymerization reaction was performed for 6 hours while maintaining a liquid temperature in a flask at around 65° C., to prepare a solution (40% by weight) of an acryl-based polymer (A). This acryl-based polymer (A) had Tg=−68° C., a weight average molecular weight of 500 thousands, and an acid value of 0.0.
Preparation Example 2 Acryl-based Polymer (B)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 200 parts by weight of isononyl acrylate, 8 parts by weight of 2-hydroxyethyl acrylate, 0.4 part by weight of 2,2′-azobisisobutyronitrile as a polymerization initiator, and 312 parts by weight of ethyl acetate, a nitrogen gas was introduced while mildly stirring, a polymerization reaction was performed for 6 hours while maintaining a liquid temperature in a flask at about 65° C., to prepare a solution (40% by weight) of an acryl-based polymer (B). This acryl-based polymer (B) had Tg=−80° C., a weight average molecular weight of 540 thousands, and an acid value of 0.0.
Preparation Example 3 Acryl-based Polymer (C)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 200 parts by weight of 2-ethylhexyl acrylate, 0.1 part by weight of 1-hydroxycyclohexyl phenyl ketone [Irgacure 184 manufactured by Ciba Specialty Chemicals], and 0.1 part by weight of benzyldimethylketal [Irgacure 651 manufactured by Ciba Specialty Chemicals], a nitrogen gas was introduced while mildly stirring, and a polymerization reaction was performed for about 3 minutes by irradiation with ultraviolet-ray with a high pressure mercury lamp (SHL-100UVQ-2 manufactured by Toshiba Lighting and Technology corporation), to prepare a solution of an acryl-based polymer (C) which is a partially polymerized polymer (syrup-like) of a polymerization ratio of 10%. This acryl-based polymer (C) had Tg=−70° C., a weight average molecular weight of 2200 thousands, and an acid value of 0.0.
Preparation Example 4 Acryl-based Polymer (D)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 140 parts by weight of 2-ethylhexyl acrylate, 60 parts by weight of ethoxy-diethylene glycol acrylate, 8 parts by weight of 2-hydroxyethyl acrylate, 0.4 part by weight of 2,2′-azobisisobutyronitrile as a polymerization initiator, 218 parts by weight of ethyl acetate, and 94 parts by weight of toluene, a nitrogen gas was introduced while mildly stirring, and a polymerization reaction was performed for about 6 hours while maintaining a liquid temperature in a flask at about 65° C., to prepare a solution (40% by weight) of an acryl-based polymer (D). This acryl-based polymer (D) had Tg=−68° C., a weight average molecular weight of 500 thousands, and an acid value of 0.0.
Preparation Example 5 Acryl-based Polymer (E)
To a four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser were added 120 parts by weight of toluene, and 10 parts by weight of 2,2′-azobisisobutyronitrile, a nitrogen gas was introduced while mildly stirring, and a liquid temperature was set to be 85° C. 50 parts by weight of 2-ethylhexyl acrylate, 50 parts by weight of ethoxy-diethylene glycol acrylate, 10 parts by weight of α-methylstyrene dimer were gradually added over 2 hours while maintaining a liquid temperature at 85° C., and a polymerization reaction was performed. After completion of addition, a polymerization reaction was performed for 1 hour while maintaining a liquid temperature at 85° C., to prepare a solution (42% by weight) of an acryl-based polymer (E). A solution (42% by weight) of an acryl-based polymer (E) was dried at 130° C. for 1 hour, to prepare an acryl-based polymer (E) (100% by weight) having an ethylene glycol group-containing acrylate rate of 50% by weight. A weight average molecular weight of this acryl-based polymer (E) was 3000.
Preparation Example 6 Antistatic Agent (A)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of N,N -diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), 5 parts by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 50% by weight) of polypropylene glycol-polyethylene glycol-polypropylene glycol, and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.) to prepare a solution (10% by weight) of an antistatic agent (A).
Preparation Example 7 Antistatic Agent (B)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of N,N -diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), 5 parts by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 10% by weight) of polyethylene glycol-polypropylene glycol-polyethylene glycol, and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare a solution (10% by weight) of an antistatic agent (B).
Preparation Example 8 Antistatic Agent (C)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of 1-butyl -3-methylpyridinium trifluoromethanesulfonate (liquid at 25° C.), 5 parts by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 50% by weight) of polypropylene glycol-polyethylene glycol-polypropylene glycol, and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare a solution (10% by weight) of an antistatic agent (C).
Preparation Example 9 Antistatic Agent (D)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of 1-butyl -3-methylpyridiniym bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), 5 parts by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 50% by weight) of polypropylene-glycol-polyethylene glycol-polypropylene glycol, and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare a solution (10% by weight) of an antistatic agent (D).
Preparation Example 10 Antistatic Agent (E)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of 1-butyl -3-methylpyridinium trifluoromethanesulfonate (liquid at 25° C.), 5 parts by weight of polypropylene glycol (number average molecular weight 700), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.) to prepare a solution (10% by weight) of an antistatic agent (E).
Preparation Example 11 Antistatic Agent (F)
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 0.2 part by weight of lithium perchlorate (melting point 236° C.), 9.8 parts by weight of polypropylene glycol (diol type, number average molecular weight 2,000), and 10 parts by weight of ethyl acetate, and mixing and stirring were performed for 2 hours while maintaining a liquid temperature in a flask at around 80° C., to prepare a solution (50% by weight) of an antistatic agent (F).
Preparation Example 12 Antistatic Agent (G)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of N,N -diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), 5 parts by weight of an acryl-based polymer (E), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare a solution (10% by weight) of an antistatic agent (G).
Preparation Example 13 Antistatic Agent (H)
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 5 parts by weight of an alicyclic amine-based ionic liquid (trade name: IL-A1, manufactured by KOEI CHEMICAL CO., LTD.; liquid at 25° C.), 5 parts by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 10% by weight) of polyethylene glycol-polypropylene glycol-polyethylene glycol, and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare a solution (10% by weight) of an antistatic agent (H).
Preparation Example 14 Antistatic-Treated Film
An antistatic agent solution was prepared by diluting 10 parts by weight of an antistatic agent [Microsolver RMd-142 manufactured by Solvex, a main component is tin oxide and polyester resin] with a mixed solvent consisting of 30 parts by weight of water and 70 parts by weight of methanol. The resulting antistatic agent solution was coated on a polyethylene terephthalate (PET) film (thickness 38 μm) using a Meyer bar, and this was dried at 130° C. for 1 minute to remove a solvent, to form an antistatic layer (thickness 0.2 μm), thereby, an antistatic-treated film was prepared.
A solution (40% by weight) of an acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1 part by weight of a solution (10% by weight) of an antistatic agent (A), 0.8 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (1).
The aforementioned acryl pressure-sensitive adhesive solution (1) was coated on a side opposite to an antistatic-treated side of the antistatic-treated film, and this was heated at 110° C. for 3 minutes to form a pressure-sensitive adhesive layer having a thickness of 20 μm. Then, a silicone-treated side of a polyethylene terephthalate film of a thickness of 25 μm, having a one silicone-treated side was applied on a surface of the pressure-sensitive adhesive layer to prepare a pressure-sensitive adhesive sheet.
To 100 parts by weight of a solution of an acryl-based polymer (C) were added 0.15 part by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), and 0.15 part by weight of a block copolymer (number average molecular weight 2,000, ethylene glycol rate 50% by weight) of polypropylene glycol-polyethylene glycol-polypropylene glycol, mixing and stirring were performed for about 1 hour under a room temperature (25° C.), 1.5 parts by weight of trimethylolpropane triacrylate as a polyfunctional monomer, and 0.1 part by weight of benzyldimethylketal [Irgacure 651 manufactured by Ciba Specialty Chemicals] as a polymerization initiator were added, mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (6).
A solution (40% by weight) of an acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 2 parts by weight of a solution (10% by weight) of an antistatic agent (G), 0.6 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1% by weight ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (7).
A solution (40% by weight) of an acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1.6 parts by weight of a solution (10% by weight) of an antistatic agent (H), 0.3 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1% by weight ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (8) was prepared.
According to the same manner as that of Example 1-1 except that 0.2 part by weight of 1-butyl-3-methylpyridinium trifluoromethanesulfonate (liquid at 25° C.) was used in place of 1 part by weight of a solution of an antistatic agent (A), an acryl pressure-sensitive adhesive solution (9) was prepared. According to the same manner as that of Example 1-1 except that this acryl pressure-sensitive adhesive solution (9) was used as an acryl pressure-sensitive adhesive solution, a pressure-sensitive adhesive sheet was prepared.
According to the same manner as that of Example 1-1 except that 0.05 part by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.) was used in place of 1 part by weight of a solution of an antistatic agent (A), an acryl pressure-sensitive adhesive solution (10) was prepared. According to the same manner as that of Example 1-1 except that this acryl pressure-sensitive adhesive solution (10) was used as an acryl pressure-sensitive adhesive solution, a pressure-sensitive adhesive sheet was prepared.
According to the same manner as that of Example 1-1 except that 0.2 part by weight of 1-butyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.) was used in place of 1 part by weight of a solution of an antistatic agent (A), an acryl pressure-sensitive adhesive solution (11) was prepared. According to the same manner as that of Example 1-1 except that this acryl pressure-sensitive adhesive solution (11) was used as an acryl pressure-sensitive adhesive solution, a pressure-sensitive adhesive sheet was prepared.
To 100 parts by weight of a solution obtained by diluting a solution (40% by weight) of an acryl-based polymer (A) to 20% by weight with ethyl acetate were added 4 parts by weight of a solution (50% by weight) of an antistatic agent (F), 0.53 part by weight of a trimethylolpropane/tolylene diisocyanate trimer adduct (Coronate L manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (13).
A solution (40% by weight) of an acryl-based polymer (D) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 0.2 part by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (liquid at 25° C.), 0.8 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (14).
A pressure-sensitive adhesive sheet is cut into a size of a width 70 mm and a length 130 mm, a separator is peeled, and this is adhered to a surface of a polarizing plate [SEG1224DUARC150T manufactured by Nitto Denko; width 70 mm, length 100 mm] having a surface treated with a fluorine compound, which has been applied to a pre-electricity-removed acryl plate of a thickness 1 mm, a width 70 mm, and a length 100 mm, with a hand roller, so that one end is protruded by 30 mm. After allowing to stand for one day under the environment of 23° C.×50% RH, a sample is set at a prescribed position as shown in FIG. 1. One end protruding by 30 mm is fixed to an automatic winding machine, and a sample is peeled at a peeling angle of 1500 and a peeling rate of 10 m/min. A voltage of a surface of a polarizing plate which is generated thereupon was measured with an electrostatic voltmeter [KSD-0103 manufactured by Kasuga Denki, Inc.] fixed at a prescribed position. Measurement was performed under the environment of 23° C.×50% RH.
A sample was obtained by laminating a pressure-sensitive adhesive sheet on a polarizing plate [SEG1224DUARC150T manufactured by Nitto Denko] having a surface treated with a fluorine resin at a pressure of 0.25 MPa, the sample was cut into a size of width 30 mm and a length 30 mm, and a separator applied to a polarizing plate side is peeled. This is adhered to a slide glass (Matsunami Glass Ind. Ltd., Suien polishing) having a size of thickness 1.3 mm, width 65 mm and length 165 mm with a hand roller to obtain a sample for assessment. After this is allowed to stand for one day under the environment of 23° C., autoclave treatment is performed for 40 minutes under the environment of 50° C.×5 atm. Thereafter, after allowing to stand for 2 hours under the environment of 80° C., whether a pressure-sensitive adhesive sheet is peeled off from a polarizing plate or not was confirmed with naked eyes. Assessment criteria was such that no perception of occurrence of peeling off was ∘, and perception of occurrence of peeling off was x.
A triacetylcellulose film [Fujitack manufactured by Fuji Photo Film Co., Ltd.] having a thickness of 90 μm was cut into a width 70 mm and a length 100 mm, and this was immersed in an aqueous sodium hydroxide solution (10% by weight) at 60° C. for 1 minute, and washed with distilled water to prepare an adherend. After the adherend was allowed to stand for one day under the environment of 23° C.×50% RH, a pressure-sensitive adhesive sheet which had been cut into a size of a width 25 mm and a length 100 mm was laminated thereon at a pressure of 0.25 MPa to prepare a sample for assessment. After lamination, the sample was allowed to stand for 30 minutes, and an adhesive strength when peeled at a peeling rate of 10 m/min and a peeling angle of 180° was measured with a universal tensile tester. Measurement was performed under the environment of 23° C.×50% RH.
electrification Occurrence of Adhesive strength
voltage [kV] peeling off [N/25 mm]
Example 1-1 −0.1 ∘ 0.6
Example 1-2 −0.3 ∘ 0.6
Example 1-3 0.0 ∘ 0.8
Example 1-4 0.0 ∘ 0.8
Example 1-5 0.0 ∘ 0.8
Example 1-6 0.0 ∘ 0.7
Example 1-7 −0.2 ∘ 0.5
Example 1-8 −0.1 ∘ 1.4
Comparative −1.4 ∘ 0.5
Comparative −0.8 ∘ 0.6
Comparative −1.1 ∘ 0.8
Comparative 0.0 x 0.5
Comparative −0.8 ∘ 0.4
A four-neck flask equipped with a stirring wing, a thermometer, a nitrogen gas introducing tube, and a condenser was charged with 200 parts by weight of 2-ethylhexyl acrylate, 8 parts by weight of 2-hydroxyethyl acrylate, 0.4 part by weight of 2,2′-azobisisobutyronitrile as a polymerization initiator, and 312 parts by weight of ethyl acetate, a nitrogen gas was introduced while mildly stirring, and a polymerization reaction was performed for 6 hours while maintaining a liquid temperature in a flask at around 65° C., to prepare a solution (40% by weight) of an acryl-based polymer (A). This acryl-based polymer (A) had Tg=−68° C., a weight average molecular weight of 550 thousands, and an acid value of 0.0.
After a solution obtained by diluting 10 parts by weight of 1-butyl-3-methylpyridinium chloride (manufactured by Wako Pure Chemical Industries, Ltd.) to 20% by weight with distilled water was added to a four-neck flask equipped with a stirring wing, a thermometer and a condenser, a solution obtained by diluting 19 parts by weight of lithium bis(trifluoromethanesulfonyl)imide (manufactured by Kishida Chemical Co., Ltd.) to 20% by weight with distilled water was gradually added while rotating a stirring wing. After addition, stirring was continued at 25° C. for 2 hours, then the system was allowed to stand for 12 hours, and the supernatant was removed to obtain a liquid product.
The resulting liquid product was washed with 200 parts by weight of distilled water three times, and dried for 2 hours under the environment of 110° C. to obtain 20 parts by weight of an ionic liquid (1) which is liquid under 25° C. NMR (1H, 13C) measurement, FT-IR measurement and XRF measurement of the resulting ionic liquid (1) were performed to identify and confirm that the product is 1-butyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide.
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of the ionic liquid (1), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP NE-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (a) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (manufactured by Kanto Kagaku; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP ER-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at a room temperature (25° C.), to prepare an antistatic agent solution (b) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 5 parts by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (manufactured by Kanto Kagaku; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (Emulgen 120 manufactured by Kao Corporation), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (c) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 5 parts by weight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (manufactured by Kanto Kagaku; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (Noigen EA130T manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (d) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 5 parts by weight of the ionic liquid (1), 5 parts by weight of a polypropylene glycol-polyethylene glycol-polypropylene glycol block copolymer (number average molecular weight 2000, ethylene glycol rate 50 wt %), and 90 parts by weight of ethyl acetate, mixing and stirring were performed for 30 minutes while maintaining a liquid temperature at around room temperature (25° C.), to prepare an antistatic agent solution (e) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 5 parts by eight of N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (manufactured by Kanto Kagaku; liquid at 25° C.), 5 parts by weight of a polypropylene glycol-polyethylene glycol-polypropylene glycol block copolymer (number average molecular weight 2000, ethylene glycol rate 50% by weight), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (f) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 0.1 part by weight of lithium iodide, 9.9 parts by weight of polypropylene glycol (number average molecular weight 2000, diol type) and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 2 hours while maintaining a liquid temperature in a flask at around 80° C., to prepare an antistatic agent solution (g) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of an alicyclic amine-based ionic liquid (IL-A1 manufactured by KOEI CHEMICAL CO., LTD.; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP ER-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (h) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of 1-ethyl-3-methylimidazolium (trifluoromethanesulfonyl)trifluoroacetamide (EMI-TSAC manufactured by Tokuyama corp.; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP ER-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for 30 minutes while maintaining a liquid temperature in a flask at around room temperature (25° C.), to prepare an antistatic agent solution (i) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer and a condenser was charged with 5 parts by weight an alicyclic ionic liquid (IL-C1 manufactured by KOEI CHEMICAL CO., LTD.; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP ER-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 1 hour under a liquid temperature in a flask of 25° C., to prepare an antistatic agent solution 0) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of an alicyclic ionic liquid (IL-C1 manufactured by KOEI CHEMICAL CO., LTD.; liquid at 25° C.), 5 parts by weight of a nonionic surfactant (Noigen XL-100 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 1 hour under a liquid temperature in a flask of 25° C., to prepare an antistatic agent solution (k) (10% by weight).
A four-neck flask equipped with a stirring wing, a thermometer, and a condenser was charged with 5 parts by weight of an alicyclic ionic liquid (IL-C3 manufactured by KOEI CHEMICAL CO., LTD.; liquid at 25° C.), 5 parts by weight of a nonionic reactive surfactant (ADEKA REASOAP ER-10 manufactured by Asahi Denka Co., Ltd.), and 90 parts by weight of ethyl acetate, and mixing and stirring were performed for about 1 hour under a liquid temperature in a flask of 25° C., to prepare an antistatic agent solution (1) (10% by weight).
An antistatic agent solution was prepared by diluting 10 parts by weight of an antistatic agent (Microsolver RMd-142 manufactured by Solvex; a main component is tin oxide and a polyester resin) with a mixed solvent consisting of 30 parts by weight of water and 70 parts by weight of methanol. The resulting antistatic agent solution was coated on a polyethylene terephthalate (PET) film (thickness 38 μm) using a Meyer bar, and this was dried at 130° C. for 1 minute to remove a solvent, to form an antistatic layer (thickness 0.2 μm), thereby, an antistatic-treated film was prepared.
A solution (40% by weight) of the acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1.4 parts by weight of the antistatic agent solution (a) (10% by weight), 0.6 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute at a room temperature (25° C.), to prepare an acryl pressure-sensitive adhesive solution (1).
The acryl pressure-sensitive adhesive solution (1) was coated on a side opposite to an antistatic-treated side of the antistatic-treated film, and this was heated at 110° C. for 3 minutes to form a pressure-sensitive adhesive layer of a thickness of 20 μm. Then, a silicone-treated side of a polyethylene terephthalate film of a thickness of 25 μm, having one silicone-treated side was applied to a surface of the pressure-sensitive adhesive layer to prepare a pressure-sensitive adhesive sheet.
A solution (40% by weight) of the acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1.6 parts by weight of the antistatic agent solution (h) (10% by weight), 0.3 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute at a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (6).
A solution (40% by weight) of the acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1.0 part by weight of the antistatic agent solution (i) (10% by weight), 0.3 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.) and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed for about 1 minute under a room temperature (25° C.) to prepare an acryl pressure-sensitive adhesive solution (7).
A solution (40% by weight) of the acryl-based polymer (A) was diluted to 20% by weight with ethyl acetate, to 100 parts by weight of this solution were added 1 part by weight of the antistatic agent solution (j) (10% by weight ethyl acetate solution), 0.35 part by weight of an isocyanurate entity of hexamethylene diisocyanate (Coronate HX manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.4 part by weight of dibutyltin dilaurate (1 weight % ethyl acetate solution) as a crosslinking catalyst, and mixing and stirring were performed at 25° C. for 1 minute to prepare an acryl pressure-sensitive adhesive solution (j).
After allowing to stand for one day under the environment of 23° C.×50% RH, a sample was set at a prescribed position as shown in FIG. 1. One end protruding by 30 mm was fixed at an automatic winding machine, and the sample was peeled at a peeling angle of 150° and a peeling rate of 10 m/min. A voltage of a polarizing plate surface which occurred thereupon was measured with an electrostatic voltmeter (KSD-0103 manufactured by Kasuga Denki, Inc.) fixed at a central position in a length direction of a sample. Measurement was performed under the environment of 23° C.×50% RH.
After allowing to stand for one day under the environment of 23° C.×50% RH, a sample was set at a prescribed position as shown in FIG. 1. One end protruding by 30 mm was fixed at an automatic winding machine, and the sample was peeled at a peeling angle of 150° and a peeling rate of 10 m/min. A voltage of a polarizing plate surface which occurred thereupon was measured with an electrostatic voltmeter (KSD-0103 manufactured by Kasuga Denki, Inc.) fixed at a prescribed position. Measurement was performed under the environment of 23° C.×50% RH.
A sample for assessment was allowed to stand for 24 hours under the environment of 50° C.×92% RH, and for 2 hours under the environment of 23° C.×50% RH, a pressure-sensitive adhesive sheet was peeled from an adherend with a hand, and the state of staining of an adherend surface was observed with naked eyes. Assessment criteria are as follows:
Case where stain was not perceived: ∘
Case where stain was perceived: x
<Assessment of Staining Property for Ex. 2-9 to 2-11>
This sample for assessment was allowed to stand for 1 month under the environment of 23° C.×50% RH, a pressure-sensitive adhesive sheet was peeled from an adherend with a hand, and the stain state of an adherend surface was observed with naked eyes. Assessment criteria are as follows:
<Adhesive Strength Measurement for Ex. 2-1 to 2-8 and Comp. Ex. 2-1 to 2-5>
After lamination, after allowing to stand for 30 minutes under the environment of 23° C.×50% RH, an adhesive strength when the sample was peeled at a peeling rate of 10 m/min and a peeling angle of 180° with a universal tensile tester was measured. Measurement was performed under the environment of 23° C.×50% RH.
A triacetylcellulose film [Fujitack manufactured by Fuji Photo Film Co., Ltd.] having a thickness of 90 μm was cut into a width 70 mm and a length 100 mm, and this was immersed in an aqueous sodium hydroxide solution (10% by weight) at 60° C. for 1 minute, and washed with distilled water to prepare an adherend.
After the adherend was allowed to stand for 24 hours under the environment of 23° C.×50% RH, a pressure-sensitive adhesive sheet which had been cut into a size of a width 25 mm and a length 100 mm was laminated thereon at a pressure of 0.25 MPa to prepare a sample for assessment. After lamination, the sample was allowed to stand for 30 minutes under the environment of 23° C.×50% RH, and an adhesive strength when peeled at a peeling rate of 10 m/min and a peeling angle of 180° was measured with a universal tensile tester. Measurement was performed under the environment of 23° C.×50% RH.
Peeling Staining
electrification property Adhesive strength
voltage [kV] [−] [N/25 mm]
Example 2-1 −0.4 ∘ 0.9
Example 2-2 −0.1 ∘ 1.1
Example 2-3 −0.1 ∘ 0.8
Example 2-4 −0.2 ∘ 0.9
Example 2-5 −0.1 ∘ 0.9
Example 2-6 0.0 ∘ 1.5
Example 2-7 0.0 ∘ 0.9
Example 2-8 0.0 ∘ 0.8
Comparative −0.2 x 0.6
Comparative −1.4 ∘ 1.0
Comparative −0.2 x 0.4
Peeling electrification Staining Adhesive
voltage [kV] property strength
SEG1425EWVAGS2B SEG1425EWV [−] [N/25 mm]
Example 2-9 0.0 −0.1 ∘ 1.0
Example 2-10 0.0 −0.2 ∘ 0.9
Example 2-11 0.0 0.0 ∘ 1.2
1. A pressure-sensitive adhesive composition, which comprises an ionic liquid, a polymer containing an acid functional group and having a glass transition temperature Tg of 0° C. or lower as a base polymer, and an ethylene oxide group-containing compound and/or a surfactant, wherein the acid value of the polymer is 1 or less.
3. A pressure-sensitive adhesive composition, which comprises an ionic liquid, a polymer having a glass transition temperature Tg of 0° C. or lower as a base polymer, and an ethylene oxide group-containing compound and/or a surfactant, wherein the acid value of the polymer is 1 or less, wherein the ionic liquid contains one or more kinds of cations represented by the following general formulas (A) to (D), wherein:
5. The pressure-sensitive adhesive composition according to claim 1, wherein the polymer having a glass transition temperature Tg of 0° C. or lower is an acryl-based polymer containing, as a main component, one or more kinds of acrylate and/or methacrylate having an alkyl group of a carbon number of 1 to 14.
6. A pressure-sensitive adhesive layer, wherein a pressure-sensitive adhesive composition , which comprises an ionic liquid, a polymer having a glass transition temperature Tg of 0° C. or lower as a base polymer, and an ethylene oxide group-containing compound and/or a surfactant, is crosslinked, wherein the acid value of the polymer is 1 or less.
US11141590 2004-06-01 2005-05-31 Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and surface protecting film Active 2025-06-24 US7491758B2 (en)
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US11141590 Active 2025-06-24 US7491758B2 (en) 2004-06-01 2005-05-31 Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and surface protecting film
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