WO2023042745A1 - 硬化性オルガノポリシロキサン組成物、その硬化により得られる微粘着性のオルガノポリシロキサン粘着剤層および積層体 - Google Patents
硬化性オルガノポリシロキサン組成物、その硬化により得られる微粘着性のオルガノポリシロキサン粘着剤層および積層体 Download PDFInfo
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- WO2023042745A1 WO2023042745A1 PCT/JP2022/033709 JP2022033709W WO2023042745A1 WO 2023042745 A1 WO2023042745 A1 WO 2023042745A1 JP 2022033709 W JP2022033709 W JP 2022033709W WO 2023042745 A1 WO2023042745 A1 WO 2023042745A1
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- Prior art keywords
- curing
- organopolysiloxane
- composition
- adhesive layer
- curable
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- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- VNJISVYSDHJQFR-UHFFFAOYSA-N tert-butyl 4,4-dimethylpentaneperoxoate Chemical compound CC(C)(C)CCC(=O)OOC(C)(C)C VNJISVYSDHJQFR-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/29—Laminated material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
Definitions
- the present invention can be solvent-free or low-solvent as required, and the radical polymerization curing reaction proceeds by heating or irradiation with high energy rays, etc., and has excellent transparency and slightly tacky organopoly
- the present invention relates to a curable organopolysiloxane composition forming a siloxane pressure-sensitive adhesive layer, a laminate having the organopolysiloxane pressure-sensitive adhesive layer, and a method for producing the same.
- a curable silicone composition that can form an adhesive layer by curing has excellent heat resistance, cold resistance, electrical insulation, and weather resistance compared to acrylic or rubber-based adhesives and pressure-sensitive adhesive compositions. It is used in a wide range of industrial fields because it forms a pressure-sensitive adhesive layer with water repellency and transparency.
- the silicone-based pressure-sensitive adhesive layer after curing has excellent heat resistance compared to other organic materials, does not easily discolor even at high temperatures, and has little deterioration in physical properties. It is suitable for use as an adhesive between members, a sealant or a temporary fixing agent in the manufacturing process of semiconductor devices, etc.
- Such a device has a structure in which a film consisting of multiple layers including an electrode layer and a display layer is sandwiched between transparent substrates. It is expected that the silicone pressure-sensitive adhesive layer, which is excellent in heat and cold resistance, will work effectively in articles and their manufacturing processes.
- cured silicone pressure-sensitive adhesives are classified into addition reaction curing type, condensation reaction curing type, peroxide curing type and the like according to the curing mechanism.
- Addition reaction curable silicone pressure-sensitive adhesive compositions are widely used because they cure quickly when left at room temperature or when heated, do not cause turbidity in the pressure-sensitive adhesive layer, are excellent in transparency, and do not generate by-products. From the standpoint of workability and handling workability, it is generally commercialized by dissolving it in an organic solvent, so its use has been limited. Especially in recent years, development of a solvent-free or low-solvent composition is strongly desired in view of the direction of environmental regulations in various countries around the world.
- Patent Document 1 (in particular, Preparation Example 1, etc.) describes a solvent-free silicone pressure-sensitive adhesive composition containing acrylic group-containing dimethylpolysiloxane, an MQ-type dimethylpolysiloxane resin, and a photopolymerization initiator, and the use thereof. A dicing tape and the like are disclosed.
- Patent Document 2 discloses a solvent-free addition-type silicone adhesive composition comprising an MQT OH -type resin component and a platinum-based catalyst.
- these silicone pressure-sensitive adhesive compositions are difficult to cure within a practical curing time unless the temperature is substantially higher than 100° C., and the pressure-sensitive adhesive layer contains a large amount of resin component. It has a problem that it is difficult to apply to applications that require slight adhesion and easy peelability.
- Patent Document 3 describes a solvent-free UV-curable silicone adhesive containing an organopolysiloxane having a (meth)acrylic functional group, a monofunctional or polyfunctional acrylate monomer, an MQ-type organopolysiloxane resin, and a photopolymerization initiator. Agent compositions and uses such as temporary fixation are disclosed. However, this document does not disclose a composition containing an alkenyl group as a main component, and the composition disclosed in Patent Document 3 only provides a relatively hard pressure-sensitive adhesive layer containing a large amount of resin. Therefore, there is a strong demand for a silicone pressure-sensitive adhesive that has a slightly sticky property derived from the rubber-like viscoelastic properties of the cured product.
- Patent Document 4 (unpublished at the time of filing), the applicants disclosed a solvent-free/low-solvent silicone containing an organopolysiloxane resin with a relatively small molecular weight and using a photoactive hydrosilylation reaction catalyst.
- a pressure-sensitive adhesive composition is proposed. However, it does not describe or suggest a radically polymerizable composition, and heating may be required in order to achieve a practical curing time.
- the present invention has been made to solve the above problems, and it is possible to design a composition having a viscosity that can be applied even if the solvent content is small, and depending on the industrial process, it is widely used for heat curing. It is a curable reactive organopolysiloxane composition that can be used not only for curing processes but also for high-energy ray curing processes such as ultraviolet rays, and that gives cured products with excellent transparency and slightly tackiness, and cured products thereof. It is an object of the present invention to provide an organopolysiloxane adhesive layer. A further object of the present invention is to provide a laminate comprising the organopolysiloxane pressure-sensitive adhesive layer and a method for producing a laminate comprising a step of bonding between substrates.
- the composition can be designed to have sufficient coatability even with no solvent to low solvent, and depending on the selection of the radical polymerization initiator, heat curing at high temperature or irradiation with high energy rays It is possible to realize room temperature to low temperature curing characteristics by curing or semi-curing, and it is possible to form an organopolysiloxane adhesive layer with excellent transparency and slight adhesiveness. Further, the above-mentioned problems are a laminate having an organopolysiloxane pressure-sensitive adhesive layer according to the present invention, and a method for producing a laminate including a step of applying the curable organopolysiloxane composition onto a substrate and curing or semi-curing it. resolved by
- the curable organopolysiloxane composition of the present invention can be designed to have a viscosity that allows coating even when the solvent content is low. It can be used not only for heat curing processes that are widely used in general, but also for curing processes by irradiation with high-energy rays such as ultraviolet rays. It is possible to form an organopolysiloxane pressure-sensitive adhesive layer with little haze. Furthermore, according to the present invention, it is possible to provide a method for manufacturing a laminate including a laminate including the organopolysiloxane pressure-sensitive adhesive layer and a step of bonding between substrates.
- the curable silicone composition of the present invention contains the above components (A) to (C).
- an organic solvent may be optionally contained, and a photosensitizer and other additives may be contained within a range not contrary to the purpose of the present invention. .
- a photosensitizer and other additives may be contained within a range not contrary to the purpose of the present invention. .
- Component (A) is a chain polysiloxane molecule having at least two alkenyl groups in the molecule, and is the main ingredient (base polymer) of this composition.
- the alkenyl group of the component (A) organopolysiloxane includes, for example, alkenyl groups having 2 to 10 carbon atoms such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group and heptenyl group, particularly vinyl group. or a hexenyl group.
- the bonding position of the alkenyl group of the component (A) includes, for example, the terminal of the molecular chain and/or the side chain of the molecular chain.
- component (A) preferably has an alkenyl group bonded to a silicon atom at a site other than the terminal of the molecular chain, and the alkenyl group is added to the side chain of the molecular chain.
- the use of a linear organopolysiloxane having is one of the preferred embodiments of the present invention.
- the (A) component may contain only a single component, or may be a mixture of two or more different components.
- the organic groups other than alkenyl groups bonded to silicon atoms include, for example, alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl and heptyl groups.
- alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl and heptyl groups.
- aryl groups such as phenyl group, tolyl group, xylyl group and naphthyl group; aralkyl groups such as benzyl group and phenethyl group; halogens such as chloromethyl group, 3-chloropropyl group and 3,3,3-trifluoropropyl group alkyl group, etc., and particularly preferably a methyl group or a phenyl group.
- Component (A) unlike component (B), has a chain polysiloxane molecular structure.
- the component (A) is preferably linear or partially branched linear (branched), and may partially contain a cyclic or three-dimensional network.
- it is a linear or branched diorganopolysiloxane whose main chain consists of repeating diorganosiloxane units and whose molecular chain ends are blocked with triorganosiloxy groups.
- the siloxane units that give the branched organopolysiloxane are the T units or Q units described later.
- the properties of component (A) at room temperature may be oily or gum-like. From the standpoint of the properties, it is preferable that the component (A) has an oily state at room temperature, and the viscosity of the component (A) at 25° C. is preferably 1 mPa ⁇ s or more and 100,000 mPa ⁇ s or less, which will be described later. It is particularly preferable that the viscosity is 10 mPa ⁇ s or more, 50,000 mPa ⁇ s or less, and 10,000 mPa ⁇ s or less in relation to the vinyl content.
- the curable organopolysiloxane composition according to the present invention is a solvent type
- at least part of component (A) has a viscosity exceeding 100,000 mPa ⁇ s at 25°C or Plasticity measured according to the specified method (25°C, 4.2 g spherical sample, 1 kgf load for 3 minutes, read thickness to 1/100 mm, multiply this value by 100) is in the range of 50-200, more preferably in the range of 80-180.
- the content of alkenyl groups in component (A) is preferably in the range of 0.001 to 10% by mass, preferably in the range of 0.005 to 5.0% by mass, based on the mass of component (A). A range of 01 to 3.0% by mass is more preferable.
- the content of the vinyl (CH 2 ⁇ CH—) moiety in the aliphatic unsaturated carbon-carbon bond-containing group (hereinafter referred to as “vinyl content”) is in the range of 0.005 to 10.0% by mass. It is particularly preferred to use organosiloxanes in the range of 0.005 to 5.0% by weight.
- Component (A) contains, as organic groups other than aliphatic unsaturated carbon-carbon bond-containing groups, alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and heptyl group; Aryl groups such as tolyl group, xylyl group and naphthyl group; Aralkyl groups such as benzyl group and phenethyl group; Halogenated alkyl groups such as chloromethyl group, 3-chloropropyl group and 3,3,3-trifluoropropyl group; may contain From an industrial point of view, it is particularly preferred to contain a methyl group.
- alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and heptyl group
- Aryl groups such as tolyl group, xylyl group and naphthyl group
- an organic group other than the aliphatic unsaturated carbon-carbon bond-containing group in the component (A) is preferably a methyl group, and the content of the aryl group or aralkyl group is less than 0.1 mol%, particularly 0.0 mol%, relative to the entire silicon-bonded groups, and substantially Preferably, it does not contain any aryl or aralkyl groups.
- Such component (A) may be used alone or as a mixture of a plurality of components.
- (A1) a linear or branched organopolysiloxane having at least two alkenyl groups only at both ends of the molecular chain, and (A2) having at least one or more alkenyl groups at sites other than the ends of the molecular chain and a linear or branched organopolysiloxane having at least 3 or more alkenyl groups in the molecule in a weight ratio of 30:70 to 70:30.
- These components (A1) and (A2) may also preferably be a mixture of two or more components having different viscosities, siloxane polymerization degrees, or alkenyl group contents.
- volatile or low-molecular-weight siloxane oligomers octamethyltetrasiloxane (D4), decamethylpentasiloxane (D5), etc.
- D4 octamethyltetrasiloxane
- D5 decamethylpentasiloxane
- the degree can be designed as desired, it may be less than 1% by mass of the entire component (A) and less than 0.1% by mass for each siloxane oligomer, and if necessary, may be reduced to near the detection limit.
- composition according to the present invention comprises (B1) a monofunctional or polyfunctional vinyl-based monomer, and (B2) an organopolysiloxane compound having an organic group containing at least one acrylic or methacrylic group in the molecule. It may also contain one or more selected radically reactive components.
- (meth)acrylic acid indicates that both acrylic acid and methacrylic acid are included.
- (meth)acrylate”, “(meth)acryloxy”, and “(meth)acrylamide” are each meant to include both acrylate and methacrylate, acryloxy and methacryloxy, acrylamide and methacrylamide.
- component (B) contains carbon-carbon unsaturated double bonds mainly derived from acrylic or methacrylic groups in the molecule, so it is a radical-reactive component. Participates in curing reaction by radical polymerization. Therefore, by using the component (B) in combination, it is possible to adjust the adhesion to the substrate, the crosslink density of the cured product, etc., and depending on the amount of the component used, the composition can be cured or semi-cured. It is possible to adjust the hardness and adhesion to the substrate of the organopolysiloxane pressure-sensitive adhesive layer to have a slightly adhesive property, especially the improvement of the curing speed, the adjustment of the cross-linking density and the adhesion to the substrate. Useful for force adjustment.
- the amount of the radical-reactive component (B) used is in the range of 0.1 to 49.9 parts by mass with respect to 50 to 99 parts by mass of component (A), and 0.1 to 25 parts by mass. A range is particularly preferred.
- the sum of components (A) and (B2) must be 50% by mass or more with respect to the total mass of solids, and the content of component (B) must be If the upper limit is exceeded, the organopolysiloxane pressure-sensitive adhesive layer formed by curing the present composition tends to be hard and brittle, and may not be sufficiently used as a slightly sticky pressure-sensitive adhesive layer. Transparency is impaired and turbidity (haze) tends to occur.
- the adjustment of the curing speed, crosslink density, etc. of the organopolysiloxane pressure-sensitive adhesive layer may be insufficient, and the purpose of a slightly tacky pressure-sensitive adhesive layer may not be achieved. be.
- the (B1) component is a vinyl-based monomer that is a starting material for an organic resin generally called a vinyl-based resin, and includes methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, lower alkyl (meth)acrylates such as isopropyl (meth)acrylate; glycidyl (meth)acrylate; n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, Cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isoamyl (meth)acrylate, octyl (meth)acrylate, dodecyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, dicyclopentanyl (
- polyfunctional vinyl monomers can also be used, such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate.
- polyethylene glycol di(meth)acrylate 1,4-bis((meth)acryloyloxy)butane, 1,6-bis((meth)acryloyloxy)hexane, 1,9-bis((meth)acryloyloxy)nonane , 1,12-bis((meth)acryloyloxy)dodecane, tris(2-acryloyloxy)ethylisosialate, pentaerythritol tetraacrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tri methylolpropane trioxyethyl (meth)acrylate, tris(2-hydroxyethyl)isocyanurate di(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethylene oxide or propylene oxide of bisphenol A (Meth)acryloyl group-containing mono
- the preferred component (B1) is an acrylate-based vinyl monomer having one acryloxy group.
- Two or more kinds can be used in combination.
- acrylate or methacrylate compounds having 8 or more carbon atoms in the molecule, preferably 8 to 30 carbon atoms provide low volatility, low viscosity of the composition, and high glass transition temperature of the cured product.
- a suitable (B1) component is an acrylate-based vinyl monomer having two acryloxy groups, and the viscosity, curability, compatibility with the compound having one acryloxy group, and after curing It can be used alone or in combination of two or more in consideration of the hardness and glass transition temperature of.
- Diethylene glycol diacrylate, 1,6-bis(acryloyloxy)hexane, trimethylolpropane triacrylate, polydimethylsiloxane with both ends acryloxy functional are preferably used.
- Component (B2) is an organopolysiloxane compound having an organic group containing at least one acryl or methacryl group in the molecule, and is resinous, chain (including linear and branched), cyclic and Any resin-linear block copolymer composed of resinous blocks and chain blocks can be used.
- the (B2) component has the general formula (1) at the terminal or side chain of the molecular chain:
- Z is a divalent organic group that may contain a hetero atom and is bonded to the silicon atom that constitutes the main chain of the polysiloxane *, and is a divalent organic group that may contain a silicon atom, an oxygen atom, a nitrogen atom, or a sulfur atom. may be a valent organic group.
- Z is an alkylene group having 2 to 22 carbon atoms
- Z 2 is * -[(CH 2 ) 2 O] m (C n H 2n )-(m is a number ranging from 0 to 3, n is 2 a number in the range of to 10) ⁇ , and -Z 1 -R 2 2 Si-OR 2 2 Si-Z 2 - described later. Any one group selected from divalent linking groups represented by is preferable.
- the silicon-bonded functional group (R A ) has the general formula (1): is represented by In the formula, each R 1 independently represents a hydrogen atom, a methyl group or a phenyl group, preferably a hydrogen atom or a methyl group. Each R 2 independently represents an alkyl group or an aryl group, and is industrially preferably an alkyl group having 1 to 20 carbon atoms or a phenyl group, particularly preferably a methyl group.
- Z 1 represents -O(CH 2 ) m - (m is a number ranging from 0 to 3), m is preferably 1 or 2.
- Z 2 is a divalent organic group represented by —C n H 2n — (where n is a number in the range of 2 to 10) bonded to a silicon atom constituting the main chain of polysiloxane *, and n is 2 to 6 are practically preferred.
- the silicon-bonded functional group (R A ) represented by the general formula (1) includes a silicon-bonded functional group (R Alk ) containing at least one alkenyl group, and a silicon-bonded hydrogen atom and a silicon-bonded hydrogen atom in the molecule.
- Method by reacting a hydrosilane compound having an acrylic functional group (e.g., 3-(1,1,3,3-tetramethyldisiloxanyl)propyl methacrylate, etc.) in the presence of a hydrosilylation reaction catalyst It can be introduced intramolecularly.
- a hydrosilylation reaction catalyst such as dibutylhydroxytoluene (BHT).
- the (B2) component may contain one or more linear organopolysiloxanes selected from the following components (B2-1-1) and (B2-1-2) below.
- Component (B2-1-1) is a linear organopolysiloxane having at least one functional group (R A ) in the molecule, represented by the following structural formula.
- R 1 is independently a C1-C6 alkyl group, C2-C20 alkenyl group, C6-C12 aryl group
- R A' is independently a C1-C6 alkyl group, C2-C20 alkenyl a C6-C12 aryl group, and a silicon atom-bonded functional group (R A ) including the aforementioned acryl or methacryl groups
- n1 is a positive number
- n2 is 0 or a positive number be.
- at least one of R A' is a silicon atom-bonded functional group (R A ) containing an acryl group or a methacryl group as described above.
- n1+n2 is a positive number of 0 or more and is not limited, it is preferably in the range of 10 to 5,000, more preferably 10 to 2,000, still more preferably 10 to 1,000.
- the value of n1+n2 is such that the viscosity of component (C'1) at 25° C. is in the range of 1 to 100,000 mPa ⁇ s, more preferably 10 to 50,000 mPa ⁇ s, and still more preferably 500 to 50,000 mPa ⁇ s. Any number that satisfies the viscosity range of s may be used and is preferred.
- Component (B2-1-2) is a branched-chain organopolysiloxane having at least one functional group (R A ) in the molecule and containing branched siloxane units, represented by the following average unit formula: be.
- Component (B2-1-2) is more specifically a branched organopolysiloxane represented by the following siloxane unit formula.
- R A' R 1 2 SiO 1/2 a (R 1 2 SiO 2/2 ) b1 (RA ' R 1 SiO 2/2 ) b2 (R 1 SiO 3/2 ) c1 (R A' SiO 3 /2 ) c2
- R 1 and R A′ are the same groups as above
- R 1 and R A′ are the same groups as above
- component (B2-1-2) may be a branched organopolysiloxane having methacryloyl group-containing organic groups only on terminal M units represented by the following siloxane unit formula.
- R A' R 1 2 SiO 1/2 a (R 1 2 SiO 2/2 ) b1 (R 1 SiO 3/2 ) c1
- R 1 and R A′ are the same groups as described above, and 0 ⁇ a ⁇ 10, 15 ⁇ b1 ⁇ 2000, 0 ⁇ c1 ⁇ 10, and at least one of R A′ is the above acrylic group. or a silicon atom-bonded functional group (R A ) containing a methacrylic group.
- the viscosity of component (B2-1-2) at 25° C. is preferably 10 to 50,000 mPa ⁇ s, more preferably 100 to 2,000 mPa ⁇ s.
- Examples of (B2) component widely available in the market include (branched or straight-chain) polydimethylsiloxane containing (meth)acrylic groups at one end; polydimethylsiloxane endblocked with methacryloxypropyl at both ends.
- the curable organopolysiloxane composition according to the present invention comprises component (A), which is a linear reactive siloxane component, and optionally (B2) an organic group containing at least one acrylic or methacrylic group in the molecule.
- the ratio of the sum of the weights of the components (A) and (B2) to the total weight of the solid content of the composition (components that form an organopolysiloxane pressure-sensitive adhesive layer upon curing, excluding the organic solvent) is It can be defined as "mass % siloxane of the composition", where the siloxane mass % is at least 50 wt %, preferably in the range of 55-99.5 wt %, more preferably in the range of 60-99.5 wt %
- the organopolysiloxane pressure-sensitive adhesive layer according to the present invention can be designed to have a transparent appearance, flexibility peculiar to silicone, and slight adhesiveness derived from the viscoelastic properties of the cured product. be.
- composition according to the present invention may contain an organopolysiloxane resin other than the components (A) and (B2) within the range where the slight tackiness, which is the technical effect of the present invention, can be achieved.
- organopolysiloxane resin is a component that adjusts adhesive strength, that is, adhesion to a substrate. can be adjusted.
- a siloxane unit (M unit) represented by R 3 SiO 1/2 (wherein R independently represents a monovalent organic group) in the molecule, and SiO Organopolysiloxane resins containing siloxane units represented by 4/2 (Q units) are exemplified.
- the molar ratio of M units to Q units may be from 0.5 to 2.0. If this molar ratio is less than 0.5, the adhesion of the cured product to the substrate may be reduced, and if it is greater than 2.0, the cohesive force of the substances constituting the adhesion layer will be reduced. is.
- the curable organopolysiloxane composition according to the present invention preferably contains little or substantially no organopolysiloxane resin as described above.
- the mass ratio of the organopolysiloxane resin to the sum of the linear reactive siloxane component (A) and the component (B2) described later is preferably in the range of 0 to 0.1, and the same mass ratio is in the range of 0 to 0.05.
- organopolysiloxane resin ie substantially free of organopolysiloxane resin. If the content of the organopolysiloxane resin exceeds the above upper limit, the adhesive strength and adhesive strength derived from the organopolysiloxane resin will increase in the cured organopolysiloxane pressure-sensitive adhesive layer, resulting in a slightly sticky pressure-sensitive adhesive layer. may not be.
- Component (C) is a radical polymerization initiator, which may be (C1) a photo-radical polymerization initiator, (C2) a thermal radical polymerization initiator, or a combination thereof.
- the type of component (C), the curing method, and the curing temperature may be appropriately selected according to the curing and adhesion processes of the base material, the heat resistance of the substrate, the need for low energy consumption, and the like. Since the composition according to the present invention has an alkenyl group in component (A), which is the main ingredient, good curability can be achieved by irradiation with high-energy rays and/or heating in the presence of component (C). can be done.
- the amount of component (C) to be used is 0.1 to 10 parts by mass, and particularly preferably 0.2 to 5 parts by mass, when the mass of component (A) is 30 to 99 parts by mass. .
- the amount of component (C) used depends on the process and curing time of the pressure-sensitive adhesive layer to which the present composition is applied, the content of alkenyl groups derived from component (A), the dose of high-energy radiation and/or heating. It can be appropriately designed within the above range depending on the conditions.
- Component (C1) is a photoradical polymerization initiator, and is a component that accelerates the photocuring reaction of the alkenyl groups in component (A) and optionally the thiol compound (E) by irradiation with high-energy rays such as ultraviolet rays.
- Radical photopolymerization initiators are roughly classified into photocleavage type and hydrogen abstraction type, but the photoradical polymerization initiator used in the composition of the present invention is arbitrarily selected from those known in the art. It can be selected and used, and is not particularly limited. Some photoradical polymerization initiators can accelerate the curing reaction not only under irradiation with high-energy rays such as ultraviolet rays but also under light irradiation in the visible light range.
- radical photopolymerization initiators include 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)ketone, ⁇ -hydroxy- ⁇ , ⁇ '-dimethylacetophenone, 2-methyl-2 ⁇ -ketol compounds such as hydroxypropiophenone and 1-hydroxycyclohexylphenyl ketone; methoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 2-methyl-1-[4 Acetophenone compounds such as -(methylthio)-phenyl]-2-morpholinopropane-1; benzoin ether compounds such as benzoin ethyl ether, benzoin isopropyl ether, and anisoin methyl ether; ketal compounds such as benzyl dimethyl ketal; aromatic sulfonyl chloride compounds such as naphthalenesulfonyl chloride; photoactive oxime compounds such as 1-phenone-1,1-
- photoradical polymerization initiators suitable as the component (C1) in the present invention include bis-(2,6-dichlorobenzoyl)phenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-2,5- Dimethylphenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl) )-2,4,4-trimethylpentylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine bisacylphosphine oxides such as oxide, bis-(2,6-dimethoxybenzoyl)-2,5-dimethylphenylpho
- acetophenone-based photopolymerization initiator suitable as the component (C1) in the present invention include Omnirad 907, 369, 369E, 379 manufactured by IGM Resins.
- Commercially available acylphosphine oxide-based photopolymerization initiators include Omnirad TPO, TPO-L, and 819 manufactured by IGM Resins.
- Commercially available oxime ester photopolymerization initiators include Irgacure OXE01 and OXE02 manufactured by BASF Japan Ltd., N-1919 manufactured by ADEKA Co., Ltd., Adeka Arcles NCI-831, NCI-831E manufactured by Changzhou Yutaka Electronic New Materials Co., Ltd. and TR-PBG-304.
- Component (C2) is a thermal radical polymerization initiator that generates radical species upon heating to accelerate the thermosetting reaction of the alkenyl groups in component (A) and optionally the thiol compound (E).
- thermal radical polymerization initiators include azo compounds and organic peroxides.
- azo compounds 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 1,1 '-Azobis-1-cyclohexanecarbonitrile, dimethyl-2,2'-azobisisobutyrate, dimethyl-2,2'-azobis (2-methylpropionate), dimethyl-1,1'-azobis (1 -cyclohexanecarboxylate), 4,4′-azobis(4-cyanovaleric acid), 2,2′-azobis(2-amidinopropane) dihydrochloride, 2-tert-butylazo-2-cyanopropane, 2,2 '-Azobis(2-methylpropionamide) dihydrate, 2,2'-azobis(2,4,4-trimethylpentane) and the like.
- organic peroxides include alkyl peroxides, diacyl peroxides, ester peroxides, and carbonate peroxides.
- the alkyl peroxides include dicumyl peroxide, di-tert-butyl peroxide, di-tert-butylcumyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy ) hexane, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3, tert-butylcumyl, 1,3-bis(tert-butylperoxyisopropyl)benzene, 3,6,9- Triethyl-3,6,9-trimethyl-1,4,7-triperoxonane is exemplified.
- diacyl peroxides include benzoyl peroxide, lauroyl peroxide, and decanoyl peroxide.
- peroxide esters include 1,1,3,3-tetramethyl butyl peroxy neodecanoate, ⁇ -cumyl peroxy neo decanoate, tert-butyl peroxy neo decanoate, tert-butyl peroxy neoheptanoate, tert-butyl peroxypivalate, tert-hexyl peroxypivalate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-amylperoxyl-2- Ethylhexanoate, tert-butylperoxy-2-ethylhexanoate, tert-butylperoxyisobutyrate, di-tert-butylperoxyhexahydroterephthalate, tert-
- Peroxycarbonates include di-3-methoxybutylperoxydicarbonate, di(2-ethylhexyl)peroxydicarbonate, diisopropylperoxycarbonate, tert-butylperoxyisopropylcarbonate, di(4-tert-butylcyclohexyl ) peroxydicarbonate, dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate.
- the present composition can also use (C') a photosensitizer in combination with (C1) a photoradical polymerization initiator.
- a sensitizer can increase the photon efficiency of the polymerization reaction, making longer wavelength light available for the polymerization reaction compared to the use of the photoinitiator alone. It is known to be particularly effective when the coating thickness is relatively thick or when relatively long wavelength LED light sources are used.
- Sensitizers include anthracene compounds, phenothiazine compounds, perylene compounds, cyanine compounds, merocyanine compounds, coumarin compounds, benzylidene ketone compounds, (thio)xanthene or (thio)xanthone compounds such as isopropyl Thioxanthone, 2,4-diethylthioxanthone, squalium-based compounds, (thia)pyrylium-based compounds, porphyrin-based compounds, and the like are known, and any photosensitizer may be used in the curable organopolysiloxane composition of the present invention. It can be used for products and adhesive compositions. The amount used is arbitrary, but the mass ratio of the component (C') to the component (C1) is in the range of 0 to 10, and when used, it is selected in the range of 0.01 to 5. is common.
- the present composition contains the above components (A) and (B), it forms a cured product through a radical polymerization reaction.
- the present composition when at least part of the component (C) is the photoradical polymerization initiator (C1), the present composition can be cured by irradiation with high-energy rays such as ultraviolet rays.
- the thermal radical polymerization initiator (C2) when at least part of the component (C) is the thermal radical polymerization initiator (C2), the composition can be cured by heating.
- heating and high-energy ray irradiation can be selected or combined for curing, and can be appropriately selected according to the desired curing method and sealing process.
- the composition according to the present invention is a solvent-free to low-solvent type, and at least part of the component (C) is (C1) a photoradical polymerization initiator, and optionally further (C') photosensitizer
- the agent By including the agent, the environmental load is small, and even for base materials and members with poor heat resistance, rapid curing is possible even at low temperatures including room temperature, and it is compatible with low energy consumption in the field of semiconductors. There are advantages that are also suitable for industrial production processes.
- at least part of the component (C) is the thermal radical polymerization initiator (C2)
- C2 thermal radical polymerization initiator
- the curable organopolysiloxane composition according to the present invention can be designed as a low-solvent or solvent-free composition by selecting its constituent components (especially by selecting a low-viscosity component as component (A) as a whole).
- component (A) a low-viscosity component
- (D) It is possible to design a composition that has practically sufficient coatability even for a composition containing a small amount of organic solvent or substantially no organic solvent.
- the content of the organic solvent is 0 to less than 60% by mass, less than 50% by mass, and substantially within the range of 0 to 30% by mass with respect to 100 parts by mass of the entire composition. is particularly preferred.
- an organic solvent is permissible in order to improve the wettability of the present composition to a substrate or to be included as a solvent incidental to other components.
- the type and blending amount of the organic solvent are adjusted in consideration of coating workability and the like, but from the standpoint of solvent-free composition design, it is preferable to use the amount as small as possible.
- the total amount of component (D), which is a diluent is in the range of 0 to 100 parts by mass, preferably in the range of 0 to 25 parts by mass.
- the (D) organic solvent includes, for example, aromatic hydrocarbon solvents such as toluene, xylene, and benzene; aliphatic hydrocarbon solvents such as heptane, hexane, octane, and isoparaffin; Ester solvents, diisopropyl ether, ether solvents such as 1,4-dioxane, trichlorethylene, perchlorethylene, chlorinated aliphatic hydrocarbon solvents such as methylene chloride, solvent volatile oils, etc. You may combine two or more types according to wettability etc. to material.
- aromatic hydrocarbon solvents such as toluene, xylene, and benzene
- aliphatic hydrocarbon solvents such as heptane, hexane, octane, and isoparaffin
- Ester solvents diisopropyl ether, ether solvents such as 1,4-dioxane, trichlorethylene, perchlor
- the composition according to the present invention may further contain (E) a polyfunctional thiol compound having at least two thiol groups (--SH) in the molecule. Since the polyfunctional thiol compound functions as a chain transfer agent to promote radical polymerization, a part of the component (C) according to the present invention is a radical photopolymerization initiator, and the composition is exposed to high energy such as ultraviolet rays. In the case of curing by radiation irradiation, the curing speed and the deep-part curability of the cured product can be improved even when the irradiation dose of high-energy radiation is small.
- polyfunctional thiol compounds examples include pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(2-(3 sulfanylbutanoyloxy)ethyl)-1,3,5-triazinane-2,4,6-trione, trimethylolpropane tris(3-mercaptobutyrate) and the like.
- component (E) may be an organopolysiloxane compound having an organic group containing at least two thiol groups in the molecule, and may be a resinous, chain (including linear and branched), cyclic and resin-linear type block copolymers composed of resin blocks and chain blocks.
- the binding site of the thiol modified group is not particularly limited, and may be either the terminal of the molecular chain or the side chain.
- linear organopolysiloxane having a thiol modifying group at the side chain site, such as a dimethylsiloxane/2-thiolpropylmethylsiloxane copolymer whose molecular chain end is blocked with a trimethylsiloxy group.
- component (E) is a thiol group-containing organopolysiloxane compound
- the compatibility with other constituent components and the uniformity and viscosity of the composition as a whole can be improved, and the intramolecular crosslink density and the like can be adjusted.
- Component (E) can be used arbitrarily, but the amount used is 0 to 20 parts by mass, and 0 to 10 parts by mass, based on 50 to 99 parts by mass of component (A). Amounts of 0 to 5 parts by weight are particularly preferred.
- the curable organopolysiloxane composition according to the present invention includes a non-reactive polydimethylsiloxane or polydimethyldiphenylsiloxane that does not contain a carbon-carbon double bond-containing reactive group such as an alkenyl group, an acrylic group, or a methacrylic group. of the organopolysiloxane can be blended, thereby improving the loss coefficient (tan ⁇ ), storage modulus (G') and loss modulus (G'') of the organopolysiloxane pressure-sensitive adhesive layer.
- the use of hydroxyl-terminated polydimethylsiloxane or polydimethyldiphenylsiloxane can increase the loss factor of the cured layer, and such compositions are within the scope of the present invention.
- the curable organopolysiloxane composition according to the present invention can optionally contain components other than the above components within a range that does not impair the technical effects of the present invention.
- adhesion promoters such as phenol, quinone, amine, phosphorus, phosphite, sulfur, or thioether
- light stabilizers such as triazoles or benzophenones
- one or more antistatic agents such as cationic surfactants, anionic surfactants, or nonionic surfactants, polymerization inhibitors, and UV absorbers agents and the like.
- pigments, dyes, and optionally surface-treated inorganic fine particles can also be arbitrarily blended. .
- the method for preparing the curable organopolysiloxane composition of the present invention is not particularly limited, and is carried out by homogeneously mixing each component.
- An organic solvent may be added as necessary, and a known stirrer or kneader may be used to mix and prepare.
- the present composition may have radical polymerizability when heated. is preferred.
- the curable organopolysiloxane composition of the present invention has a viscosity of 1,000 to 300 at 25° C. in terms of coatability and handling workability as an adhesive or an adhesive-forming composition. ,000 mPa ⁇ s, and the viscosity of the entire composition is preferably in the range of 5,000 to 50,000 mPa ⁇ s. In particular, when the content of the organic solvent is 30% by mass or less based on 100 parts by mass of the composition, the viscosity of the entire composition is preferably in the range of 5,000 to 300,000 mPa s. . Such a composition can realize practically sufficient coatability even if it is a low-solvent type or a solvent-free type.
- the curable organopolysiloxane composition according to the present invention contains the components (A), (B) and (C), (i) the heat curing reaction and (ii) the light from high energy ray irradiation It can be cured by one or more radical polymerization reactions selected from curing reactions.
- the state in which the radical polymerization reaction is completed in the organopolysiloxane pressure-sensitive adhesive layer is "cured"
- the solid state Although an organopolysiloxane adhesive layer is formed, the adhesive layer retains radical polymerization reactivity, and the state in which the curing reaction can proceed further by heating and irradiation with high-energy rays is called “semi-cured.” do.
- the reaction for forming the semi-cured organopolysiloxane pressure-sensitive adhesive layer and the subsequent reaction for forming the cured organopolysiloxane pressure-sensitive adhesive layer may be the same radical polymerization reaction or different radical polymerization reactions. Two or more radical polymerization reactions may be carried out simultaneously.
- a semi-cured organopolysiloxane pressure-sensitive adhesive layer may be formed by a heat curing reaction, and then a completely cured organopolysiloxane pressure-sensitive adhesive layer may be formed by irradiation with high-energy rays.
- the same curing reaction may be stepped to form a semi-cured/cured organopolysiloxane adhesive layer by temporarily interrupting and resuming the radiation.
- one or more radical polymerization reactions selected from (i) heat-curing reaction and (ii) photo-curing reaction by irradiation with high-energy rays further proceed.
- the crosslink density of the adhesive layer changes when changing to the "cured" state, and the adhesive force to the substrate can be changed.
- the "semi-cured" organopolysiloxane pressure-sensitive adhesive layer is brought into contact with a substrate, and cured by allowing the above-mentioned radical polymerization reaction to proceed, so that the completely cured pressure-sensitive adhesive layer becomes It may exhibit stronger adhesion to the substrate and form a stronger bond.
- the curable organopolysiloxane composition according to the present invention forms a coating film by coating on a substrate, and is selected from (i) heat-curing reaction and (ii) photo-curing reaction by irradiation with high-energy rays.
- a cured or semi-cured organopolysiloxane pressure-sensitive adhesive layer is formed by one or more radical polymerization reactions.
- Coating methods include gravure coating, offset coating, offset gravure, roll coating, reverse roll coating, air knife coating, curtain coating, and comma coating.
- the coating amount can be designed to have a desired thickness according to the application of the adhesive layer and the display device. It may be 900 ⁇ m, and may be 10-800 ⁇ m, but is not limited to these.
- the temperature is 80 to 200°C, preferably 100°C or higher, and more preferably 100 to 180°C.
- a slightly sticky cured or semi-cured adhesive layer is obtained by a thermal radical polymerization reaction.
- the heating time required for curing can be appropriately selected according to the degree of curing, the thickness of the pressure-sensitive adhesive layer and the amount of catalyst used, but it is generally in the range of 0.5 to 90 minutes. may be interrupted or performed step by step to obtain an organopolysiloxane pressure-sensitive adhesive layer in the form of a semi-cured material that retains heat curing reactivity.
- the heating temperature and heating time may be appropriately selected depending on the heat resistance of the substrate, the sealing process, and the like.
- the curable organopolysiloxane composition according to the present invention is cured by (ii) a photo-curing reaction by irradiation with high-energy rays
- usable high-energy rays include ultraviolet rays, gamma rays, X-rays, ⁇ -rays, and electron rays. etc., but ultraviolet rays are preferable from the viewpoint of practicality.
- High-pressure mercury lamps, medium-pressure mercury lamps, Xe—Hg lamps, deep UV lamps, and the like are suitable as the ultraviolet light source, and ultraviolet irradiation with a wavelength of 280 to 400 nm, preferably 300 to 400 nm, is preferred.
- Light sources with emission bands may also be used.
- the irradiation dose of high-energy rays varies depending on the type and amount of (C1) photoradical polymerization initiator and the degree of curing reaction. It is preferably within the range of 2 .
- Irradiation with high-energy rays may be performed with a substrate interposed therebetween as long as the substrate carrying the pressure-sensitive adhesive layer according to the present invention does not absorb electromagnetic waves in the above wavelength range. That is, if a certain amount of irradiation can be realized, high-energy rays may be irradiated through a base material or a cover material such as a protective film.
- low temperature means, for example, 100° C. or lower, specifically a temperature range of 15° C. to 100° C., and a temperature of 80° C. or lower can be selected.
- reaction of the composition of the present invention proceeds in a temperature range of 15 to 100 ° C., it is preferably around room temperature (a temperature range that can be reached without heating or cooling, and 20 to In particular, the temperature range of 25° C. is included), the composition may be left standing, may be cooled to room temperature or lower and 15° C.
- the time required for the curing reaction can be appropriately designed according to the irradiation dose of high-energy rays such as ultraviolet rays and the temperature. Furthermore, by interrupting the irradiation before reaching a predetermined cumulative irradiation dose, a semi-cured organopolysiloxane pressure-sensitive adhesive layer that retains photocuring reactivity may be obtained.
- the organopolysiloxane pressure-sensitive adhesive layer obtained by the above curing reaction is slightly sticky, for example, a 180° peeling test method according to JIS Z 0237 for a 2 mm-thick polymethyl methacrylate sheet of a 55 ⁇ m-thick cured product layer. It is possible to design an adhesive layer having an adhesive strength in the range of 5 to 50 gf/25 mm, preferably in the range of 5 to 40 gf/25 mm, measured at a tensile speed of 300 mm/min.
- the above thickness (55 ⁇ m) is the thickness of the cured layer itself, which serves as a reference for objectively defining the adhesive strength of the cured layer according to the present invention. Needless to say, the thickness is not limited to 55 ⁇ m, and any thickness can be used as a cured layer or pressure-sensitive adhesive layer.
- the cured product or semi-cured product of the present invention is slightly adhesive and can be used as an organopolysiloxane pressure-sensitive adhesive layer or an elastic pressure-sensitive adhesive member.
- the surface of the pressure-sensitive adhesive layer or substrate may be subjected to surface treatment such as primer treatment, corona treatment, etching treatment, plasma treatment, or the like. good.
- the curable organopolysiloxane composition according to the present invention is coated on a release liner, it is cured by heating under the temperature conditions described above, and the release liner is peeled off to form a film-like substrate, tape-like substrate, or After bonding with a sheet-like substrate (hereinafter referred to as "film-like substrate") or coating on a film-like substrate, it is cured by heating under the above temperature conditions, and adheres to the surface of the substrate. agent layer can be formed.
- Laminates comprising a cured layer obtained by curing the organopolysiloxane composition of the present invention on these film-like substrates, particularly a film-like pressure-sensitive adhesive layer, can be used as adhesive tapes, bandages, low-temperature supports, May be used for transfer films, labels, emblems and decorative or instructional markings.
- the cured layer formed by curing the organopolysiloxane composition of the present invention may be used in the construction of automobile parts, toys, electronic circuits, or keyboards.
- cured layers, especially film adhesive layers, formed by curing the organopolysiloxane compositions of the present invention may be used in the construction and application of laminated touch screens or flat panel displays.
- substrate types include paperboard, cardboard, clay-coated paper, polyolefin-laminated paper, especially polyethylene-laminated paper, synthetic resin film/sheet, natural fiber cloth, synthetic fiber cloth, artificial leather cloth, and metal foil.
- synthetic resin films and sheets are preferred, and examples of synthetic resins include polyimide, polyethylene, polypropylene, polystyrene, polyvinyl chloride, polyvinylidene chloride, polycarbonate, polyethylene terephthalate, cyclopolyolefin, and nylon.
- heat-resistant synthetic resin films such as polyimide, polyetheretherketone, polyethylenenaphthalate (PEN), liquid crystal polyarylate, polyamideimide, and polyethersulfone are suitable.
- transparent substrates specifically transparent materials such as polypropylene, polystyrene, polyvinylidene chloride, polycarbonate, polyethylene terephthalate, and PEN, are suitable.
- the base material is preferably film-like or sheet-like.
- the thickness is not particularly limited, and can be designed to have a desired thickness depending on the application.
- a support film that has been subjected to primer treatment, corona treatment, etching treatment, or plasma treatment may be used.
- the surface opposite to the surface of the pressure-sensitive adhesive layer of the film-like substrate may be subjected to surface treatment such as anti-scratch, anti-fouling, anti-fingerprint, anti-glare, anti-reflection and anti-static treatments. .
- the pressure-sensitive adhesive layer according to the present invention may be a single layer or a multiple layer formed by laminating two or more pressure-sensitive adhesive layers depending on the required properties.
- the multi-layer pressure-sensitive adhesive layer may be formed by laminating pressure-sensitive adhesive films prepared one by one, or by coating the curable organopolysiloxane composition according to the present invention on a film substrate having a release layer or the like. The curing step may be performed multiple times.
- the pressure-sensitive adhesive layer according to the present invention is expected to function as an elastic pressure-sensitive adhesive member because it has a function of bonding or sticking between members. Furthermore, the pressure-sensitive adhesive layer may be given a role as another functional layer selected from a dielectric layer, a conductive layer, a heat dissipation layer, an insulating layer, a reinforcing layer, and the like. In addition, by performing the above-described curing reaction in multiple stages, when utilizing the change in adhesive force accompanying the change from a semi-cured product to a cured product, it may be used as an easily peelable adhesive layer for temporary fixing. .
- the cured layer formed by curing the curable organopolysiloxane composition of the present invention is an adhesive layer, particularly an adhesive/pressure-sensitive adhesive film
- the cured layer is provided with a release layer having release coating capability. It is preferable to handle it as a laminate film adhered to a film substrate in a peelable state.
- the release layer is sometimes called a release liner, separator, release layer, or release coating layer, and is preferably a release coating such as a silicone-based release agent, a fluorine-based release agent, an alkyd-based release agent, or a fluorosilicone-based release agent.
- the release layer may be a release layer having an ability, a base material that physically forms fine irregularities on the surface of the base material, or a base material itself that is difficult to adhere to the pressure-sensitive adhesive layer of the present invention.
- a release layer obtained by curing a fluorosilicone release agent may be used as the release layer.
- the release layer may be a differential release layer, which is a first release layer and a second release layer having different types of release agents constituting the release layer and different release strengths, and a fluorosilicone-based release agent.
- a cured product obtained by curing the curable organopolysiloxane composition of the present invention has both viscoelasticity and slight adhesiveness as described above, and is therefore useful as an elastic adhesive member for various electronic devices or electrical devices.
- it is useful as an electronic material, display device member, or transducer member (including sensors, speakers, actuators, and generators), and the cured product is preferably used as an electronic component or display device member.
- the film-shaped cured product particularly the substantially transparent pressure-sensitive adhesive film, is suitable as a member for a display panel or a display. It is particularly useful for a so-called touch panel application that can operate a device, particularly an electronic device, by touching with a touch panel.
- the elastic adhesive layer is particularly useful for film-like or sheet-like members used in sensors, speakers, actuators, etc., where transparency is not required and the adhesive layer itself is required to have a certain degree of stretchability or flexibility. be.
- the pressure-sensitive adhesive layer obtained by curing the curable organopolysiloxane composition can be designed with low solvent or no solvent, and can realize pressure-sensitive adhesive properties such as slight stickiness or easy peeling. Therefore, it is possible to improve the adhesion to substrates such as display devices. Furthermore, if desired, by using a semi-cured product or a multi-stage curing reaction, for display devices, semiconductors, etc., temporarily used as a functional film (e.g., protective film) on the premise of detachment. There is an advantage that it can be used as an easily peelable adhesive layer.
- Articles containing an adhesive layer obtained by curing the curable organopolysiloxane composition of the present invention may be adhesive tapes, particularly protective tapes intended for attachment and detachment. , a sheet-like member made of a fiber product such as a woven fabric, a non-woven fabric, or paper, and the adhesion layer.
- the types of such adhesive tapes are not particularly limited, and include insulating tapes, heat-resistant tapes, solder masking tapes, mica tape binders, temporary fixing tapes (particularly including temporary fixing tapes for silicone rubber parts, etc.), and splicing tapes. (particularly including splicing tapes for silicone release papers).
- a laminate having a pressure-sensitive adhesive layer obtained by curing the curable organopolysiloxane composition of the present invention may be formed on the film-like substrate described above.
- a release layer may be provided for the cured adhesion layer.
- the sheet-like substrate has at least one release layer, and the release layer is in contact with the cured adhesion layer.
- the pressure-sensitive adhesive layer according to the present invention can be easily peeled off from the sheet-like substrate.
- the release agent contained in the release layer is not particularly limited, and includes the same release agents as described above.
- the above-mentioned laminate may be able to handle the pressure-sensitive adhesive layer separated from the film-like substrate alone, or may have two film-like substrates.
- film substrate a first release layer formed on the film-like substrate; It may comprise a pressure-sensitive adhesive layer formed by coating and curing the curable organopolysiloxane composition on the release layer, and a second release layer laminated on the pressure-sensitive adhesive layer.
- the laminate of the above embodiment can be obtained, for example, by coating the curable organopolysiloxane composition on one of the release layers formed on the film-like substrate and curing the pressure-sensitive adhesive layer. may be formed, and another release layer may be laminated and formed on the adhesion layer.
- a step of curing or semi-curing by a curing reaction can be produced by a production method including a step of laminating another substrate on the organopolysiloxane pressure-sensitive adhesive layer formed in step (L1-II).
- the first substrate used in step (L1-I) is preferably a film-like substrate having a first release layer on its surface
- the other substrates used in step (L2-III) are A film-like substrate having a second release layer on its surface is preferred.
- the laminate having the above configuration can be obtained, for example, by sandwiching the above curable silicone composition between the first film-like substrate and the second film-like substrate, heating the composition, and pressing or rolling it to a certain thickness. It may be produced by curing the composition after molding.
- the first sheet base material may have a first release layer, or the first sheet base material itself may have releasability.
- the second sheet substrate may have a second release layer, or the second sheet substrate itself may have peelability.
- the cured adhesion layer is the first release layer and/or the second release layer. It is preferred to contact the layer.
- the sheet substrate having releasability examples include a sheet substrate made of a material having releasability such as a fluororesin film, or a material having no or low releasability such as a polyolefin film and a material such as silicone or fluororesin.
- a sheet substrate made of one to which a release agent is added may be mentioned.
- examples of sheet substrates having a release layer include polyolefin films coated with a release agent such as silicone and fluororesin.
- the laminate can be used, for example, by peeling off the adhesive layer from the film-like substrate after applying the cured adhesive layer to the adherend.
- the thickness of the adhesive layer is preferably 5 to 10000 ⁇ m, more preferably 10 ⁇ m or more or 8000 ⁇ m or less, and particularly preferably 20 ⁇ m or more or 5000 ⁇ m.
- the organopolysiloxane pressure-sensitive adhesive layer obtained by semi-curing the curable organopolysiloxane composition of the present invention can be used as a slightly tacky adhesive layer for producing laminates other than the peelable laminate described above.
- the organopolysiloxane adhesive layer according to the present invention is a semiconductor (including semiconductor precursors and integrated semiconductor devices such as LSI and MEMS), semiconductor substrates (flexible substrates and stretchable substrates such as wearable devices). including), etc., batteries such as secondary batteries, display panels or displays such as laminated touch screens or flat panel displays, etc.
- Known methods of using layers such as silicone PSAs, silicone adhesives, and silicone sealants can be used without particular limitation.
- the method for producing a laminated body such as a semiconductor is not particularly limited as long as an organopolysiloxane adhesive layer is used for adhesion between members, and an already cured or semi-cured organopolysiloxane adhesive layer may be used.
- an already cured or semi-cured organopolysiloxane adhesive layer may be used.
- the above-described laminate containing the organopolysiloxane adhesive layer for example, single-sided or double-sided adhesive film
- the substrate that forms a laminate such as a semiconductor is adhered to the exposed organopolysiloxane adhesive layer, and the laminate such as a semiconductor (precursor for the purpose of protection in the process, including temporary fixing) may be formed.
- the laminate of semiconductors and the like according to the present invention can be obtained by coating an uncured curable organopolysiloxane composition on or between substrates and curing or semi-curing the composition to obtain organopolysiloxane adhesion.
- An agent layer may be formed.
- the laminate according to the present invention is Step (L2A-I): a step of applying the curable organopolysiloxane composition of the present invention onto a first substrate;
- an organopolysiloxane pressure-sensitive adhesive layer is formed between one base material, and another base material is laminated thereon.
- the laminate according to the invention is Step (L2B-I): a step of applying the curable organopolysiloxane composition of the present invention onto a first substrate; Step (L2B-II): Step of further laminating another substrate on the curable organopolysiloxane composition applied in Step (L2B-I), and Step (L2B-III): Step (L2B-II ), the uncured curable organopoly between the substrates by one or more curing reactions selected from (i) a heat curing reaction and (ii) a photocuring reaction by irradiation with high energy rays.
- a laminate manufacturing method comprising a step of curing or semi-curing a siloxane composition.
- an uncured curable organopolysiloxane composition is placed between the substrates to be laminated, and the curable organopolysiloxane composition is subjected to a curing reaction to form an organopolysiloxane between the substrates. It takes a form in which a polysiloxane adhesive layer is formed.
- the substrates forming the laminate is a translucent substrate
- the curable organopolysiloxane composition according to the present invention contains (C1) a photoradical polymerization initiator and is irradiated with high-energy rays.
- the laminate may be formed by irradiating a high-energy ray that passes through the translucent member base material.
- the laminate according to the present invention is Step (L3-I): a step of applying the curable organopolysiloxane composition of the present invention, which has photo-curing properties when irradiated with high-energy rays, onto a substrate; Step (L3-II): a step of further laminating another substrate on the curable organopolysiloxane composition applied in step (L3-I); Step (L3-III): The laminate precursor formed in the step (L3-II) is irradiated with high-energy rays passing through the translucent substrate, thereby forming an uncured curable organoleptic layer between the substrates.
- a laminate manufacturing method comprising a step of curing or semi-curing a polysiloxane composition.
- this method since high-energy rays can be irradiated through a light-transmitting substrate, it is suitable for the process of forming an organopolysiloxane adhesive layer between substrates with particularly low heat resistance.
- After laminating to form a laminate precursor by irradiating with high energy rays at a low temperature, it is possible to form a large number of laminates at low energy When it is excellent in industrial production efficiency There is
- the curing method is appropriately selected from a heat curing reaction and a photocuring reaction according to the curing reactivity of the curable organopolysiloxane, the purpose of use of the laminate, heat resistance, and process requirements. and the two curing reactions may be carried out simultaneously or stepwise.
- the organopolysiloxane adhesive layer in the laminate is in a semi-cured state
- the laminate is subjected to the same or different curing reaction to complete the curing reaction, and the organopolysiloxane in the laminate is cured.
- the pressure-sensitive adhesive layer may be converted into a completely cured state.
- the method for producing the laminate according to the present invention optionally includes (i) a heat curing reaction and (ii) a high-energy beam. may further include a step of curing the semi-cured organopolysiloxane pressure-sensitive adhesive layer by one or more curing reactions selected from photocuring reactions by irradiation of .
- the organopolysiloxane pressure-sensitive adhesive layer obtained by curing or semi-curing the curable organopolysiloxane composition of the present invention can be used for construction and utilization of laminated touch screens or flat panel displays, as described above.
- the cured product obtained by curing the curable organopolysiloxane composition of the present invention is an optically transparent silicone-based pressure-sensitive adhesive disclosed in JP-A-2014-522436 or JP-A-2013-512326. It can be used as an agent film or an adhesive layer for manufacturing a display device such as a touch panel.
- the organopolysiloxane pressure-sensitive adhesive layer according to the present invention can be used without particular limitation as the pressure-sensitive adhesive layer or pressure-sensitive adhesive film described in JP-T-2013-512326.
- the touch panel according to the present invention includes a base material such as a conductive plastic film having a conductive layer formed on one surface, and the conductive layer formed on the side or the opposite side thereof. It may be a touch panel comprising a cured layer obtained by curing the curable organopolysiloxane composition.
- the substrate is preferably a sheet-like or film-like substrate, exemplified by a resin film or a glass plate.
- the conductive plastic film may be a resin film or a glass plate, especially a polyethylene terephthalate film, having an ITO layer formed on one surface thereof.
- organopolysiloxane pressure-sensitive adhesive layer according to the present invention may be used as an adhesive film for polarizing plates used in the production of display devices such as touch panels, and between the touch panel and the display module described in JP-A-2013-065009. It may be used as a pressure-sensitive adhesive layer for lamination.
- the use of the curable reactive organopolysiloxane composition of the present invention and the cured product obtained by curing the composition are not limited to those disclosed above, and the cured product obtained by curing the composition is not limited.
- the organopolysiloxane pressure-sensitive adhesive layer is used for television receivers, computer monitors, personal digital assistant monitors, surveillance monitors, video cameras, digital cameras, mobile phones, personal digital assistants, instrument panel displays for automobiles, and various equipment. ⁇ It can be used for a variety of display devices for displaying characters, symbols, and images, such as instrument panel displays for devices and equipment, automatic ticket vending machines, automatic teller machines, vehicle-mounted display devices, and vehicle-mounted transmissive screens. be.
- the surface shape of such a display device may be a curved or curved shape instead of a flat surface, and in addition to various flat panel displays (FPD), curved displays used in automobiles (including electric vehicles), aircraft, etc.
- FPD flat panel displays
- curved displays used in automobiles (including electric vehicles), aircraft, etc.
- a curved transmissive screen is exemplified.
- these display devices display icons for executing functions or programs on screens and displays, notification displays such as e-mail programs, and operation buttons for various devices such as car navigation devices, audio devices, and air conditioners.
- a touch panel function may be added to enable input operations by touching the icons, notification displays, and operation buttons with a finger.
- the cured product obtained by curing the composition has excellent adhesiveness and viscoelastic properties, it is a film that is a member for transducers such as membranes for speakers (including for sensors, speakers, actuators, and generators). Alternatively, it can be used as a sheet-like member, and further, it can be used as a sealing layer or an adhesive layer for use in secondary batteries, fuel cells, or solar cell modules.
- the organopolysiloxane pressure-sensitive adhesive layer according to the present invention has excellent transparency and excellent adhesion to substrates such as various display devices.
- Apparatuses in particular, display apparatuses for vehicles with a curved screen or curved display, optionally with a touch panel function.
- JP-A-2017-047767, JP-A-2014-182335, JP-A-2014-063064, JP-A-2013-233852, etc. disclose a vehicle display device having a curved display surface.
- the pressure-sensitive adhesive layer according to the present invention can be suitably applied or replaced as part or all of the adhesive layer or pressure-sensitive adhesive layer that requires transparency in these documents.
- the curable organopolysiloxane composition of the present invention and its cured product can be used in other known curved display devices by replacing the currently used adhesive layer or adhesive layer that requires transparency.
- the transparent film-like substrate provided with the organopolysiloxane pressure-sensitive adhesive layer according to the present invention is used to prevent scratches on the surface of the display, stain prevention, fingerprint adhesion prevention, static electricity prevention, anti-reflection, anti-peeping, etc. may be used for the purpose.
- composition Solid content of each composition (components forming a cured product excluding (D) organic solvent) relative to the total mass, when the total mass% of the A component is a, and the synthetic mass% of the B2 component is b, the The siloxane weight percent of the composition is defined as a+b2.
- the composition according to this example does not contain an organopolysiloxane resin component.
- Viscosity of curable composition Using a rotational viscometer (E-type viscometer VISCONIC EMD manufactured by Tokimec Co., Ltd.), the viscosity (Pa ⁇ s) of the composition and each component at 25° C. was measured.
- Each composition is coated on a PET film (manufactured by Toray, Lumirror (registered trademark) S10, thickness 50 ⁇ m) so that the thickness after curing is 55 ⁇ m, and a release film (manufactured by Nippa, FSC-6, thickness 50 ⁇ m) on the composition, and then using a UV-LED ultraviolet irradiation device (manufactured by JATEC), from the PET film side, the ultraviolet irradiation amount (illuminance) is 4,000 mJ / cm as an integrated light amount .
- the composition was cured by irradiation with ultraviolet rays of 365 nm.
- Table 1 shows the adhesive strength (gf/25 mm) of the test piece measured at a tensile speed of 300 mm/min using the 180° peeling test method according to JIS Z 0237.
- the compositions of the present invention according to Examples 1 to 4 have viscosities that allow coating without using an organic solvent, and can be easily cured with ultraviolet rays.
- the composition of the present invention according to Example 5 has a viscosity that enables coating and can be heat-cured in the same manner as in the conventional method by using an organic solvent.
- the cured product obtained by curing the composition had no turbidity, had a transparent appearance, and had practically low adhesiveness.
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Abstract
Description
(A)成分は、分子内に少なくとも2個のアルケニル基を有する鎖状のポリシロキサン分子であり、この組成物の主剤(ベースポリマー)である。(A)成分のオルガノポリシロキサンのアルケニル基としては、例えば、ビニル基、アリル基、ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基などの炭素数2~10のアルケニル基が挙げられ、特にビニル基またはヘキセニル基であることが好ましい。(A)成分のアルケニル基の結合位置としては、例えば、分子鎖末端及び/又は分子鎖側鎖が挙げられる。本発明の技術的効果の見地から、(A)成分の少なくとも一部または全部が、分子鎖末端以外の部位のケイ素原子に結合したアルケニル基を有することが好ましく、分子鎖側鎖にアルケニル基を有する鎖状オルガノポリシロキサンの使用は、本発明の好適な実施形態の一つである。なお、(A)成分は、単一の成分のみを含んでいてもよく、2種以上の異なった成分の混合物であってもよい。
(A1)分子鎖両末端にのみ少なくとも2個のアルケニル基を有し、直鎖状又は分岐鎖状オルガノポリシロキサン、および
(A2)分子鎖末端以外の部位に少なくとも1個以上のアルケニル基を有し、かつ、分子内に少なくとも3個以上のアルケニル基を有する、直鎖状又は分岐鎖状オルガノポリシロキサン
を30:70~70:30の質量比で含む混合物であってよい。また、これらの(A1)成分および(A2)成分は、さらに、粘度、シロキサン重合度またはアルケニル基の含有量が異なる2種類以上の成分の混合物であってもよく、かつ、好ましい。
本発明にかかる組成物は、(B1)単官能または多官能のビニル系単量体、および(B2)分子内に少なくとも1個のアクリル基またはメタクリル基を含む有機基を有するオルガノポリシロキサン化合物から選ばれる1種類以上のラジカル反応性成分を含んでもよい。なお、以下、「(メタ)アクリル酸」とは、アクリル酸およびメタクリル酸の双方を含むことを示す。同様に、「(メタ)アクリレート」、「(メタ)アクリロキシ」、「(メタ)アクリルアミド」もそれぞれ、アクリレート及びメタアクリレート、アクリロキシ及びメタアクリロキシ、アクリルアミド及びメタアクリルアミドの双方を含むことを示す。
一般式(1):
-R3-C(=O)-O-R4-で示される2価の有機基{式中、R3は炭素原子数2~22のアルキレン基であり、R4はエチレン基、プロピレン基、メチルエチレン基又はヘキシレン基から選択される基である}、
-Z1-X-C(=O)-X-Z2-で示される2価の有機基{式中、Z1は-O(CH2)k-(kは0~3の範囲の数)を表し、Xは酸素原子、窒素原子、または硫黄原子をあらわす。Z2は*であるポリシロキサンの主鎖を構成するケイ素原子に結合する-[(CH2)2O]m(CnH2n)-(mは0~3の範囲の数、nは2~10の範囲の数)で表される2価の有機基である}、および
後述する ―Z1-R2 2Si-O-R2 2Si―Z2-
で表される2価の連結基
から選ばれるいずれか1種類の基であることが好ましい。
(RA’R1 2SiO1/2)x(R1 2SiO2/2)y1(RA’R1SiO2/2)y2(R1SiO3/2)z1(RA’SiO3/2)z2 (I-2)
(RA’R1 2SiO1/2)a(R1 2SiO2/2)b1(RA’R1SiO2/2)b2(R1SiO3/2)c1(RA’SiO3/2)c2
(式中、R1,RA’は前記同様の基)
で表した場合、0<a≦10、15≦b1+b2<2000、0<c1+c2≦10であり、b2+c2=0の場合、RA’の少なくとも一つは、前記のアクリル基またはメタクリル基を含むケイ素原子結合官能基(RA)である。
(RA’R1 2SiO1/2)a(R1 2SiO2/2)b1(R1SiO3/2)c1
式中、R1,RA’は前記同様の基であり、0<a≦10、15≦b1<2000、0<c1≦10であり、RA’の少なくとも一つは、前記のアクリル基またはメタクリル基を含むケイ素原子結合官能基(RA)である。
本発明に係る硬化性オルガノポリシロキサン組成物は、鎖状の反応性シロキサン成分である(A)成分、および任意で(B2)分子内に少なくとも1個のアクリル基またはメタクリル基を含む有機基を有するオルガノポリシロキサン化合物を含む。このとき、組成物の固形分(有機溶媒を除く、硬化によりオルガノポリシロキサン粘着剤層を形成する成分)全体質量に占める前記の(A)成分および(B2)成分の質量の和の比率を、「組成物のシロキサン質量%」と定義することができ、当該シロキサン質量%が50質量%以上、好ましくは55~99.5質量%、より好ましくは60~99.5質量%の範囲内にある場合、本発明にかかるオルガノポリシロキサン粘着剤層は、透明な外観を有し、かつ、シリコーン特有の柔軟性を備え、硬化物の粘弾特性に由来する微粘着性を有するように設計可能である。
本発明にかかる組成物は、本発明の技術的効果である微粘着性を達成できる範囲で、(A)成分、(B2)成分以外のオルガノポリシロキサン樹脂を含んでもよい。このようなオルガノポリシロキサン樹脂は、接着力、すなわち、基材への密着力を調整する成分であり、当該成分の使用量応じて、本組成物の硬化物の硬さおよび基材に対する密着性を調整することが可能である。
(C)成分はラジカル重合開始剤であり、(C1)光ラジカル重合開始剤、(C2)熱ラジカル重合開始剤、およびこれらの組み合わせであってよく、本発明にかかる硬化性オルガノポリシロキサン組成物の硬化および接着プロセス、基材の耐熱性や低エネルギー化の要求などに応じて、(C)成分の種類および硬化方法、硬化温度を適宜選択してよい。本発明にかかる組成物は、主剤である(A)成分中にアルケニル基を有するので、(C)成分の存在下、高エネルギー線の照射および/または加熱により、良好な硬化性を実現することができる。
過酸化ジアシル類としては、ベンゾイルパーオキサイド、ラウロイルパーオキサイド、デカノイルパーオキサイドが例示される。過酸化エステル類としては、1,1,3,3-テトラメチルブチルパーオキシネオデカノエート、α-クミルパーオキシネオデカノエート、tert-ブチルパーオキシネオデカノエート、tert-ブチルパーオキシネオヘプタノエート、tert-ブチルパーオキシピバレート、tert-ヘキシルパーオキシピバレート、1,1,3,3-テトラメチルブチルパーオキシ-2-エチルヘキサノエート、tert-アミルパーオキシル-2-エチルヘキサノエート、tert-ブチルパーオキシ-2-エチルヘキサノエート、tert-ブチルパーオキシイソブチレート、ジ-tert-ブチルパーオキシヘキサヒドロテレフタレート、tert-アミルパーオキシ-3,5,5―トリメチルヘキサノエート、tert-ブチルパーオキシ-3,5,5―トリメチルヘキサノエート、tert-ブチルパーオキシアセテート、tert-ブチルパーオキシベンゾエート、ジ-ブチルパーオキシトリメチルアディペートが例示される。過酸化カーボネート類としては、ジ-3-メトキシブチルパーオキシジカーボネート、ジ(2-エチルヘキシル)パーオキシジカーボネート、ジイソプロピルパーオキシカーボネート、tert-ブチルパーオキシイソプロピルカーボネート、ジ(4-tert-ブチルシクロヘキシル)パーオキシジカーボネート、ジセチルパーオキシジカーボネート、ジミリスチルパーオキシジカーボネートが例示される。
本組成物は、任意選択により、(C1)光ラジカル重合開始剤と組み合わせて(C´)光増感剤を用いることもできる。増感剤の使用は、重合反応の光量子効率を高めることができ、光開始剤のみを用いた場合と比べて、より長波長の光を重合反応に利用できるようになるために、組成物のコーティング厚さが比較的厚い場合、又は比較的長波長のLED光源を使用する場合に特に有効であることが知られている。増感剤としては、アントラセン系化合物、フェノチアジン系化合物、ペリレン系化合物、シアニン系化合物、メロシアニン系化合物、クマリン系化合物、ベンジリデンケトン系化合物、(チオ)キサンテンあるいは(チオ)キサントン系化合物、例えば、イソプロピルチオキサントン、2,4-ジエチルチオキサントン、スクアリウム系化合物、(チア)ピリリウム系化合物、ポルフィリン系化合物などが知られており、これらに限らず任意の光増感剤を本発明の硬化性オルガノポリシロキサン組成物および粘着剤組成物に用いることができる。その使用量は任意であるが、(C1)成分に対する(C´)の成分の質量比が0~10となる範囲であり、使用する場合には0.01~5となる範囲で選択するのが一般的である。
本組成物は、上記の(A)成分および(B)成分を含むため、ラジカル重合反応により、硬化生成物を形成する。ここで、(C)成分の少なくとも一部が(C1)光ラジカル重合開始剤である場合、本組成物は紫外線等の高エネルギー線を照射することで硬化させることができる。同様に、(C)成分の少なくとも一部が(C2)熱ラジカル重合開始剤である場合、本組成物は加熱により硬化させることができる。さらに、両者を組み合わせることで、加熱および高エネルギー線照射を選択または組み合わせて硬化させることが可能であり、所望とする硬化方法および封止プロセスにより、適宜選択することができる。
本発明にかかる硬化性オルガノポリシロキサン組成物は、その構成成分の選択(特に(A)成分全体として低粘度の成分を選択すること)により、低溶剤型乃至無溶剤型の組成物が設計可能であり、(D)有機溶剤の含有量が少量乃至実質的に有機溶剤を含有しない組成であっても、実用上十分な塗工性を有する組成上の設計が可能である。具体的には、有機溶媒の含有量が組成物全体100質量部に対しての0~60質量%未満であり、50質量%未満であり、実質的に0~30質量%の範囲内であることが特に好ましい。一方、本組成物の基材への濡れ性改良や、その他の成分に付随する溶媒として不可避的に含まれる場合、有機溶剤を少量含むことは許容される。有機溶剤は、塗工作業性などを考慮してその種類及び配合量を調整するが、無溶剤型の組成設計の見地から、極力少量とすることが好ましい。
本発明に係る組成物は、さらに、(E)分子内に少なくとも2個以上のチオール基(-SH)を有する多官能チオール化合物を含んでもよい。多官能のチオール化合物は連鎖移動剤として、ラジカル重合反応を促進するため、特に、本発明にかかる(C)成分の一部が光ラジカル重合開始剤であり、本組成物を紫外線等の高エネルギー線照射によって硬化させる場合、高エネルギー線の照射量が少ない場合でも硬化速度および硬化物の深部硬化性を改善できるほか、本組成物における架橋点としても機能する。
本発明にかかる硬化性オルガノポリシロキサン組成物には、アルケニル基、アクリル基、メタクリル基等の炭素-炭素二重結合含有反応性基を含まないポリジメチルシロキサンまたはポリジメチルジフェニルシロキサンなどの非反応性のオルガノポリシロキサンを配合することができ、これにより、オルガノポリシロキサン粘着剤層の損失係数(tanδ)、貯蔵弾性率(G’)および損失弾性率(G’’)を改善することができる場合がある。例えば、水酸基末端を有するポリジメチルシロキサンまたはポリジメチルジフェニルシロキサンの使用により、硬化物層の損失係数を増加させることができ、そのような組成物は、本発明の範囲に包含される。
本発明の硬化性オルガノポリシロキサン組成物は、粘着剤として、または粘着剤形成性組成物としての塗工性および取り扱い作業性の見地から、25℃における組成物全体の粘度が1,000~300,000mPa・sの範囲であり、組成物全体の粘度が5,000~50,000mPa・sの範囲であることが好ましい。特に、有機溶媒の含有量を組成物100質量部に対して、全体の30質量%以下とした場合に、組成物全体の粘度が5,000~300,000mPa・sの範囲であることが好ましい。このような組成物は、低溶剤型乃至無溶剤型であっても、実用上十分な塗工性を実現することができる。
本発明にかかる硬化性オルガノポリシロキサン組成物は、前記の(A)成分、(B)成分および(C)成分を含むため、(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上のラジカル重合反応により硬化することができる。ここで、硬化反応が完結した硬化物および組成物として硬化反応性を残した半硬化物のいずれの形態であっても、基材に対する粘着力を有するオルガノポリシロキサン粘着剤層を形成することができ、本発明において「硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させる」という表現を用いる場合には、オルガノポリシロキサン粘着剤層においてラジカル重合反応が完結した状態を「硬化」、固体状のオルガノポリシロキサン粘着剤層を形成しているが、当該粘着剤層がラジカル重合反応性を残しており、加熱および高エネルギー線の照射によりさらに硬化反応が進行可能である状態を「半硬化」とする。なお、半硬化状態のオルガノポリシロキサン粘着剤層を形成させる反応と、その後の硬化状態のオルガノポリシロキサン粘着剤層を形成させる反応は、同一のラジカル重合反応でも異なるラジカル重合反応であってよく、2種類以上のラジカル重合反応を同時に行ってもよい。一例として、加熱硬化反応により半硬化状態のオルガノポリシロキサン粘着剤層を形成させ、その後に高エネルギー線の照射により完全に硬化したオルガノポリシロキサン粘着剤層を形成させてもよく、加熱または高エネルギー線の照射を一時的に中断乃至再開することにより、同一の硬化反応を段階的に行って半硬化/硬化状態のオルガノポリシロキサン粘着剤層を形成してもよい。
本発明にかかる硬化性オルガノポリシロキサン組成物は、基材上に塗工することによって塗膜を形成し、(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上のラジカル重合反応により、硬化物または半硬化物であるオルガノポリシロキサン粘着剤層を形成する。
本発明の硬化物または半硬化物は微粘着性であり、オルガノポリシロキサン粘着剤層または弾性粘着部材としてとして使用することができる。ここで、被着体と当該粘着剤層の密着性を向上させるために、粘着剤層または基材の表面に対してプライマー処理、コロナ処理、エッチング処理、プラズマ処理等の表面処理を行ってもよい。
本発明の硬化性オルガノポリシロキサン組成物を硬化させてなる粘着剤層を含む物品は、粘着テープ、特に、着脱を前提とする保護テープであってよく、上記の合成樹脂フィルム・シート、金属箔、織布、不織布、紙等の繊維製品からなるシート状部材と上記の密着層を備えることを特徴とする。このような密着テープの種類は、特に制限されるものではなく、絶縁テープ、耐熱テープ、ハンダマスキングテープ、マイカテープバインダー、仮止めテープ(シリコーンゴム部品等の仮止めテープを特に含む)、スプライシングテープ(シリコーン剥離紙用スプライシングテープを特に含む)があげられる。
上記のフィルム状基材上に、本発明にかかる硬化性オルガノポリシロキサン組成物を硬化させてなる粘着剤層を備えた積層体を形成させて良く、好適には、これらのフィルム状基材に当該硬化密着層に対する剥離層が設けられていてもよい。
具体的には、
フィルム状基材、
該フィルム状基材上に形成された第1剥離層、
該剥離層上に上記の硬化性オルガノポリシロキサン組成物を塗工し硬化させて形成された粘着剤層、及び該粘着剤層上に積層された第2剥離層
を備えるものであってよい。
工程(L1-I):任意で剥離層を有してもよいフィルム状基材上に、本発明にかかる硬化性オルガノポリシロキサン組成物を塗布する工程、
工程(L1-II):工程(L1-I)で塗布した硬化性オルガノポリシロキサン組成物を(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により硬化ないし半硬化させる工程であり、さらに、任意で、
工程(L1-III):工程(L1-II)で形成したオルガノポリシロキサン粘着剤層上にその他の基材を積層する工程
を含む製造法により製造することができる。ここで、工程(L1-I)で使用する第一の基材は好ましくは第1剥離層を表面に備えたフィルム状基材であり、工程(L2-III)で使用するその他の基材は好ましくは第2剥離層を表面に備えたフィルム状基材である。
本発明の硬化性オルガノポリシロキサン組成物をないし半硬化させてなるオルガノポリシロキサン粘着剤層は、上記の剥離性積層体以外の積層体の製造にかかる、微粘着性の密着層として用いることができる。具体的には、本発明にかかるオルガノポリシロキサン粘着剤層は、半導体(半導体前駆体や、LSI,MEMSなどの集積型半導体デバイスを含む)、半導体基板(フレキシブル基板およびウェアラブルデバイス等の伸縮性基板を含む)等の電子部品、二次電池等の電池、積層タッチスクリーン又はフラットパネルディスプレイ等の表示パネルまたはディスプレイの保護、構築及び利用に使用することができ、その具体的な使用方法は、密着層(例えば、シリコーンPSA、シリコーン接着剤、およびシリコーン封止剤)の公知の使用方法を特に制限なく用いることができる。
工程(L2A-I):本発明にかかる硬化性オルガノポリシロキサン組成物を第一の基材上に塗布する工程、
工程(L2A-II):工程(L2A-I)で塗布した硬化性オルガノポリシロキサン組成物を(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により硬化ないし半硬化させる工程、および
工程(L2A-III):工程(L2A-II)で形成したオルガノポリシロキサン粘着剤層上にその他の基材を積層する工程
を有する、積層体の製造方法により得ることができる。本方法においては、一方の基材間上にオルガノポリシロキサン粘着剤層上を形成させ、その上に他の基材を積層する形態をとる。
工程(L2B-I):本発明にかかる硬化性オルガノポリシロキサン組成物を第一の基材上に塗布する工程、
工程(L2B-II):工程(L2B-I)で塗布した硬化性オルガノポリシロキサン組成物上に、さらに、その他の基材を積層する工程、および
工程(L2B-III):工程(L2B-II)で形成した積層体前駆体について、(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により基材間の未硬化の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させる工程
を有する、積層体の製造方法により得ることができる。本方法においては、積層される基材間上に未硬化の硬化性オルガノポリシロキサン組成物を配置し、当該硬化性オルガノポリシロキサン組成物に対して硬化反応を行うことで、基材間にオルガノポリシロキサン粘着剤層が形成される形態をとる。
工程(L3-I):高エネルギー線の照射による光硬化性を有する、本発明の硬化性オルガノポリシロキサン組成物を基材上に塗布する工程、
工程(L3-II):工程(L3-I)で塗布した硬化性オルガノポリシロキサン組成物上に、さらに、その他の基材を積層する工程、
工程(L3-III):工程(L3-II)で形成した積層体前駆体について、透光性基材を透過して高エネルギー線を照射することにより、基材間の未硬化の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させる工程
を有する、積層体の製造方法により得ることができる。本方法においては、透光性基材を透過して高エネルギー線を照射できるため、特に耐熱性の低い基材間にオルガノポリシロキサン粘着剤層を形成する工程に適する他、事前に基材間の貼り合わせを行って積層体前駆体を形成した後、低温下で高エネルギー線の照射を行うことで、低エネルギーに多数の積層体を形成することができる点で工業的生産効率に優れる場合がある。
本発明にかかる硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させてなるオルガノポリシロキサン粘着剤層は、上記の通り、積層タッチスクリーン又はフラットパネルディスプレイの構築及び利用に使用することができる。例えば、本発明の硬化性オルガノポリシロキサン組成物を硬化してなる硬化物は、前記の特表2014-522436号または特表2013-512326等で開示された光学的に透明なシリコーン系感圧接着剤フィルムあるいは粘着剤層として、タッチパネル等の表示デバイスの製造に用いることができる。具体的には、本発明にかかるオルガノポリシロキサン粘着剤層は、特表2013-512326に記載の粘着層または粘着フィルムとして、特に制限なく用いることができる。
以下に、本発明の実施例及び比較例を記す。なお、各実施例・比較例・参考例において「硬化させた」とは、各々の硬化条件により、各組成物が完全に硬化したことを意味するものである。
表1に示す各成分を用いて、各実施例、比較例に示す硬化反応性のオルガノポリシロキサン組成物からなる粘着剤組成物を調製した。なお、同表における%は全て質量%である。また、各成分の粘度および可塑度は25℃における測定値である。
(A1)粘度45Pa・sの両末端トリメチルシロキシ基封鎖ジメチルシロキサン・(5-ヘキセニル)メチルシロキサン共重合物(ビニル基含有量:0.83質量%)
(A2)可塑度が120の両末端トリメチルシロキシ基封鎖ジメチルシロキサン・メチルビニルシロキサン共重合物生ゴム(ビニル基含有量:0.84質量%)
(A3)粘度40Pa・sの両末端ジメチルビニルシロキシ基封鎖フェニルメチルシロキサン重合物(ビニル基含有量:1.50質量%)
(B1-1)イソボルニルアクリレート(東京化成工業製)
(B1-2)アクリル酸ドデシル(=ドデシルアクリレート)(東京化成工業製)
(B1-3)トリメチロールプロパントリアクリレート(東京化成工業製)
(B2-1)両末端ジメチル(アクリロイルオキシオクチル)シロキシ基封鎖ジメチルシロキサン重合物(C3H3O2基含有量:8.43質量%)
(C1-1)2,4,6-トリメチルベンゾイルジフェニルフォスフィンオキサイド(製品名Omnirad TPO-L、IGM Resins社製)
(C1-2)2-ヒドロキシ-2-メチルプロピオフェノン(東京化成工業製)
(C2-1)ジベンゾイルパーオキサイド、ベンゾイル-メタ-メチルベンゾイルパーオキサイド、及び、メタ-トリルパーオキサイドをキシレンで希釈した混合物(ナイパーBMT-K40、日本油脂製社製)
(D)キシレン
各組成物の固形分((D)有機溶媒を除く、硬化物を形成する成分)全体質量に対して、A成分の合計質量%をa、B2成分の合成質量%をbとしたとき、当該組成物のシロキサン質量%はa+b2で定義される。なお、本件実施例にかかる組成物は、オルガノポリシロキサン樹脂成分を含まない。
回転粘度計(トキメック株式会社製、E型粘度計VISCONIC EMD)を使用して、25℃における組成物および各成分の粘度(Pa・s)を測定した。
各組成物を、PETフィルム(東レ製、ルミラー(登録商標)S10、厚さ50μm)に硬化後の厚みが55μmとなるように塗工し、離型フィルム(ニッパ製、FSC-6、厚さ50μm)を組成物に被せた後、UV-LED紫外線照射装置(JATEC製)を用いて、PETフィルム側から、紫外線照射量(照度)が積算光量として4,000mJ/cm2となるように波長365nmの紫外線を照射し、組成物を硬化させた。1時間放置後、同試料を幅25mmに切断し、粘着層面をSUS304BA板(パルテック製)およびPMMA板(パルテック製、アクリライトL001,50x120x2mm)にローラーを用いて貼り合せて試験片とした。同試験片に対し、JIS Z 0237に従う180°引き剥がし試験方法を用いて引張速度300mm/minにより測定された粘着力(gf/25mm)を表1に示した。
各組成物を、PETフィルム(東レ製、ルミラー(登録商標)S10、厚さ50μm)に硬化後の厚みが55μmとなるように塗工し、130℃で5分間硬化させた。1時間放置後、同試料を幅25mmに切断し、粘着層面をSUS304BA板(パルテック製)およびPMMA板(パルテック製、アクリライトL001,50x120x2mm)にローラーを用いて貼り合せて試験片とした。同試験片に対し、JIS Z 0237に従う180°引き剥がし試験方法を用いて引張速度300mm/minにより測定された粘着力(gf/25mm)を表1に示した。
各組成物の硬化後の厚みが200μmとなるように、2枚の無アルカリガラス板(コーニング製)を同組成物で貼り合わたせ、未硬化であれば貼り合わせ後に硬化し、試験片を作製した。該試験片のヘイズ値を分光側色計CM-5(コニカミノルタ製)で測定した。ヘイズ値が1未満を「〇」、1以上を「×」に分類した。
Claims (22)
- (A)分子内に2以上のアルケニル基を有する鎖状オルガノポリシロキサン 50~99質量部、
(B)以下の(B1)成分および(B2)成分から選ばれる1種類以上のラジカル反応性成分 0.1~49.9質量部、
(B1)単官能または多官能のビニル系単量体、および
(B2)分子内に少なくとも1個のアクリル基またはメタクリル基を含む有機基を有するオルガノポリシロキサン化合物
(C)ラジカル重合開始剤 0.1~10質量部
を含有し、組成物の固形分の全体質量に対して、(A)成分および(B2)成分の和が50質量%以上である、硬化性オルガノポリシロキサン組成物。 - 組成物の固形分の全体質量に対して、(A)成分および(B2)成分の和が60~99.5質量%の範囲であり、かつ、(A)成分および(B2)成分の質量の和に対するオルガノポリシロキサン樹脂成分の質量比が0~0.1の範囲にある、請求項1に記載の硬化性オルガノポリシロキサン組成物。
- (B)成分の少なくとも一部が、(B1-1)炭素原子数8~30の範囲にある(メタ)アクリレート化合物から選ばれるビニル系単量体である、請求項1に記載の硬化性オルガノポリシロキサン組成物。
- (B)成分の少なくとも一部が、(B1-1―1)ドデシルアクリレート、イソボルニルアクリレートおよび2-エチルヘキシルアクリレートから選ばれるビニル系単量体である、請求項1に記載の硬化性オルガノポリシロキサン組成物。
- 当該組成物の硬化により得られる厚み55μmの硬化物層の、厚み2mmのポリメチルメタクリレートシートに対する、JIS Z 0237に従う180°引き剥がし試験方法を用いて引張速度300mm/minにより測定された粘着力が5~50gf/25mmの範囲であることを特徴とする、請求項1~請求項5のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- 無溶剤型または低溶剤型である、請求項1~請求項6のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- さらに、(D)有機溶媒を0~100質量部の範囲で含有する、請求項1~請求項6のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- 25℃における組成物全体の粘度が500~100,000mPa・sの範囲内である、請求項1~請求項8のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- (C)成分の少なくとも一部が(C1)光ラジカル重合開始剤であり、高エネルギー線の照射による光硬化性を有することを特徴とする、請求項1~請求項9のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- (C)成分の少なくとも一部が(C2)熱ラジカル重合開始剤であり、加熱硬化性を有することを特徴とする、請求項1~請求項9のいずれか1項に記載の硬化性オルガノポリシロキサン組成物。
- 請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させてなる、オルガノポリシロキサン粘着剤層。
- 請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を硬化させてなる、弾性粘着部材。
- フィルム状基材上に、請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させてなる、オルガノポリシロキサン粘着剤層を備えた積層体。
- 1または2以上のフィルム状基材に当該オルガノポリシロキサン粘着剤層に対する剥離層が設けられている、請求項14に記載の積層体。
- 少なくとも2つの基材間に請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させてなる、オルガノポリシロキサン粘着剤層を有する、積層体。
- 工程(L1-I):任意で剥離層を有してもよいフィルム状基材上に、請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を塗布する工程、
工程(L1-II):工程(L1-I)で塗布した硬化性オルガノポリシロキサン組成物を(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により硬化ないし半硬化させる工程
を少なくとも有する、請求項14または請求項15に記載の積層体の製造方法。 - 工程(L2A-I):請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を第一の基材上に塗布する工程、
工程(L2A-II):工程(L2A-I)で塗布した硬化性オルガノポリシロキサン組成物を(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により硬化ないし半硬化させる工程、および
工程(L2A-III):工程(L2A-2)で形成したオルガノポリシロキサン粘着剤層上にその他の基材を積層する工程
を有する、請求項16に記載の積層体の製造方法。 - 工程(L2B-I):請求項1~請求項11のいずれか1項に記載の硬化性オルガノポリシロキサン組成物を第一の基材上に塗布する工程、
工程(L2B-II):工程(L2B-I)で塗布した硬化性オルガノポリシロキサン組成物上に、さらに、その他の基材を積層する工程、および
工程(L2B-III):工程(L2B-II)で形成した積層体前駆体について、(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により基材間の未硬化の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させる工程
を有する、請求項16に記載の積層体の製造方法。 - 積層体を形成する基材の少なくとも一方が透光性基材であり、
工程(L3-I):請求項10に記載の高エネルギー線の照射による光硬化性を有する硬化性オルガノポリシロキサン組成物を基材上に塗布する工程、
工程(L3-II):工程(L3-I)で塗布した硬化性オルガノポリシロキサン組成物上に、さらに、その他の基材を積層する工程、
工程(L3-III):工程(L3-II)で形成した積層体前駆体について、透光性基材を透過して高エネルギー線を照射することにより、基材間の未硬化の硬化性オルガノポリシロキサン組成物を硬化ないし半硬化させる工程
を有する、請求項16に記載の積層体の製造方法。 - 積層体中に半硬化の状態にあるオルガノポリシロキサン粘着剤層が存在する場合に、さらに、(i)加熱硬化反応および(ii)高エネルギー線の照射による光硬化反応から選ばれる1種類以上の硬化反応により当該半硬化の状態にあるオルガノポリシロキサン粘着剤層を硬化させる工程を有する、請求項18~請求項20のいずれか1項に記載の積層体の製造方法。
- 半硬化の状態にあるオルガノポリシロキサン粘着剤層を硬化させる工程により、オルガノポリシロキサン粘着剤層の基材に対する粘着力が変化することを特徴とする、請求項21に記載の積層体の製造方法。
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JP2019085489A (ja) * | 2017-11-07 | 2019-06-06 | 信越化学工業株式会社 | 基板の接着方法 |
JP2019085488A (ja) * | 2017-11-07 | 2019-06-06 | 信越化学工業株式会社 | 基板の接着方法 |
WO2019159611A1 (ja) * | 2018-02-19 | 2019-08-22 | 東レ・ダウコーニング株式会社 | シリコーン感圧接着剤組成物および積層体 |
WO2020116126A1 (ja) * | 2018-12-04 | 2020-06-11 | 信越化学工業株式会社 | 紫外線硬化型シリコーン粘着剤組成物およびその硬化物 |
JP2021501813A (ja) * | 2017-10-27 | 2021-01-21 | ダウ シリコーンズ コーポレーション | 硬化性ポリオルガノシロキサン組成物、当該組成物を硬化することにより得られる硬化体、およびそれを含む電子デバイス |
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JP4171898B2 (ja) | 2003-04-25 | 2008-10-29 | 信越化学工業株式会社 | ダイシング・ダイボンド用接着テープ |
JP5234064B2 (ja) | 2010-08-23 | 2013-07-10 | 信越化学工業株式会社 | 無溶剤型付加型シリコーン粘着剤組成物及び粘着性物品 |
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JP2021501813A (ja) * | 2017-10-27 | 2021-01-21 | ダウ シリコーンズ コーポレーション | 硬化性ポリオルガノシロキサン組成物、当該組成物を硬化することにより得られる硬化体、およびそれを含む電子デバイス |
JP2019085489A (ja) * | 2017-11-07 | 2019-06-06 | 信越化学工業株式会社 | 基板の接着方法 |
JP2019085488A (ja) * | 2017-11-07 | 2019-06-06 | 信越化学工業株式会社 | 基板の接着方法 |
WO2019159611A1 (ja) * | 2018-02-19 | 2019-08-22 | 東レ・ダウコーニング株式会社 | シリコーン感圧接着剤組成物および積層体 |
WO2020116126A1 (ja) * | 2018-12-04 | 2020-06-11 | 信越化学工業株式会社 | 紫外線硬化型シリコーン粘着剤組成物およびその硬化物 |
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