Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/068—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
  • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/10—Esters
  • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
  • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
  • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09D133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09D133/10—Homopolymers or copolymers of methacrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D135/02—Homopolymers or copolymers of esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
  • C09D183/04—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
  • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
• • 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
  • C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J135/02—Homopolymers or copolymers of esters
• • 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
• • 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
  • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Definitions

• the present invention relates to ultraviolet latitude-curable compositions curable by actinic rays, such as ultraviolet or electron beams, in particular ultraviolet curable compositions comprising organosilicon compounds, preferably organopolysiloxanes, and in particular obtainable therefrom.
• the present invention relates to an ultraviolet curable composition whose cured product has high viscosity adjustment ability and excellent coating properties.
• the curable composition of the invention is suitable as an insulating material for electronic and electrical devices, especially as a material for use as a coating agent. Furthermore, since it has excellent coating properties, excellent wettability to substrates, and viscosity adjustment ability, it is useful as an injection molding material and an inkjet printing material.
• silicone resins Due to its high heat resistance and excellent chemical stability, silicone resins have been used as coating agents, potting agents, insulating materials, etc. for electronic and electrical devices. Among silicone resins, ultraviolet curable silicone compositions have also been reported.
• Touch panels are used in various display devices such as mobile devices, industrial equipment, and car navigation systems. In order to improve the detection sensitivity, it is necessary to suppress the electrical influence from light emitting parts such as light emitting diodes (LEDs) and organic EL devices (OLEDs), and an insulating layer is usually placed between the light emitting part and the touch screen. Placed.
• LEDs light emitting diodes
• OLEDs organic EL devices
• thin display devices such as OLEDs have a structure in which many functional thin layers are laminated.
• studies have begun to improve the reliability of display devices, particularly flexible display devices, as a whole by laminating a highly flexible insulating layer on a touch screen layer.
• an inkjet printing method has been adopted as a processing method for the organic layer. Therefore, for the above-mentioned insulating layer as well, there is a demand for materials that can be processed by inkjet printing.
• JP 2016-56330A discloses an ultraviolet curable organopolysiloxane composition consisting of a polysiloxane having a methacryloxy functional group, a polysiloxane having two or more acryloxy functional groups in one molecule, and a polysiloxane containing an alkenyl group at both ends.
• a silicone gel cured product obtained from the composition is disclosed.
• WO2018-3381 discloses an ultraviolet curable silicone composition comprising a polysiloxane having two (meth)acryloxy functional groups in one molecule and an acrylate compound containing no silicon atom.
• An inkjet ink composition is disclosed.
• the composition disclosed herein cannot be said to have a sufficiently high viscosity adjustment ability, and it is difficult to provide a low-viscosity composition that can be used in an inkjet method.
• UV-curable compositions containing organopolysiloxanes having an acryloxy functional group are known, but the mechanical properties of the cured product can be easily adjusted and the compositions are excellent for coating on substrates.
• the present invention provides a curable composition containing silicon atoms that has both high controllability of the mechanical properties of the product obtained by curing and excellent workability when applied to a substrate even if it is a solvent-free type.
• the total mass of the composition is 100 parts by mass, (A) 1 to 99 parts by mass of a compound having one or more (meth)acryloxy groups in one molecule, and (B) a compound having two or more alkenyl groups and at least one carbon number of 6 to 20 in one molecule.
• 99 to 1 part by mass of an organopolysiloxane having an aromatic hydrocarbon group and having no ultraviolet curable functional group The composition containing the composition exhibits a viscosity that allows coating even when substantially no organic solvent is used, and the cured product thereof has excellent mechanical properties, and the viscosity of the composition and the cured product have excellent mechanical properties. This was completed by discovering that the mechanical properties of the can be easily adjusted.
• the present invention relates to an ultraviolet curable composition
• an ultraviolet curable composition comprising an organosilicon compound, particularly an ultraviolet curable organopolysiloxane composition, which is cured by the formation of bonds by ultraviolet curable functional groups.
• the curing method is not limited to ultraviolet irradiation, and any method by which the ultraviolet curable functional group can undergo a curing reaction can be used, for example, by curing the composition of the invention using electron beam irradiation. It's okay.
• the ultraviolet curable composition of the present invention has the following properties when the total mass of the composition is 100 parts by mass: (A) 1 to 99 parts by mass of a compound having one or more (meth)acryloxy groups in one molecule, (B) Organopolysiloxane having two or more alkenyl groups and at least one aromatic hydrocarbon group having 6 to 20 carbon atoms in one molecule and having no ultraviolet curable functional group 99 to 1 part by mass , The composition is characterized in that it contains substantially no organic solvent.
• the viscosity of a substance is a value measured using an E-type viscometer at 25°C.
• the viscosity of the entire composition measured at 25° C. using an E-type viscometer is preferably in the range of 500 mPa ⁇ s or less.
• the above component (B) has an average compositional formula: R a R' b SiO (4-ab)/2 (1) (wherein R is an alkenyl group, R' is a group selected from monovalent hydrocarbon groups excluding alkenyl groups, hydroxyl groups, and alkoxy groups, a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.05 ⁇ a/(a+b) ⁇ 1.0, and have at least 2 R in the molecule, and at least 1 of R' is an aromatic hydrocarbon group having 6 to 20 carbon atoms. )
• R is an alkenyl group
• R' is a group selected from monovalent hydrocarbon groups excluding alkenyl groups, hydroxyl groups, and alkoxy groups
• a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.05 ⁇ a/(a+b) ⁇ 1.0, and have at least 2 R in the molecule, and at least 1 of R' is an aromatic hydrocarbon group having 6 to 20 carbon atoms.
• the organopolysiloxane of the component (B) has the following formula (2): (2) (In the formula, among all R 1 to R 8 groups, at least two alkenyl groups exist in the molecule; at least one aromatic hydrocarbon group having 6 to 20 carbon atoms exists in the molecule; R 1 to R 8 are each independently an unsubstituted or fluorine-substituted monovalent hydrocarbon group, a hydroxyl group, and an alkoxy group; n is a numerical value of 0 to 1,000) organopolysiloxane, Average unit formula (3): (R 3 SiO 1/2 ) c (R 2 SiO 2/2 ) d (RSiO 3/2 ) e (SiO 4/2 ) f (3) (In the formula, R is each independently a group selected from an alkenyl group, an unsubstituted or fluorine-substituted monovalent hydrocarbon group, a hydroxyl group, and an alkoxy group, and at least two of all R's
• R is a group independently selected from an alkenyl group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group
• x is an integer from 3 to 10, and at least 2 alkenyl group and at least one aromatic hydrocarbon group having 6 to 20 carbon atoms
• one or more organopolysiloxanes having at least two alkenyl groups and one or more aromatic hydrocarbon groups having 6 to 20 carbon atoms in the molecule, selected from the group consisting of It is preferable that there be.
• the component (B) is a linear organopolysiloxane having two alkenyl groups and at least one aromatic hydrocarbon group having 6 to 20 carbon atoms in one molecule represented by the formula (2) above. It is preferable to include.
• the above component (A) may be a compound having one (meth)acryloxy group, or a mixture of a compound having one (meth)acryloxy group and a compound having two or more (meth)acryloxy groups.
• the compound having one (meth)acryloxy group in the component (A) is preferably the following (A1) or (A2).
• A1 One or more compounds having one (meth)acryloxy group and no silicon atom
• A2 A1 and one or more compounds having one (meth)acryloxy group and having a silicon atom mixture of
• the above component (A) contains a compound having at least one type of acryloxy group.
• the content of the aromatic hydrocarbon group having 6 to 20 carbon atoms in component (B) is preferably 10 mol% or more based on all substituents on the silicon atom.
• the viscosity of the entire composition measured at 25° C. using an E-type viscometer is preferably in the range of 5 to 60 mPa ⁇ s.
• the present invention further provides an insulating coating agent or an insulating adhesive containing the above-mentioned ultraviolet curable composition.
• the ultraviolet curable composition of the present invention is useful as an insulating coating or an insulating adhesive.
• the present invention further provides a cured product of the above ultraviolet curable composition. Furthermore, a method of using the cured product as an insulating coating layer or an insulating adhesive layer is provided.
• the present invention further provides a display device, such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer made of a cured product of the above-mentioned ultraviolet curable composition.
• a display device such as a liquid crystal display, an organic EL display, and an organic EL flexible display, including a layer made of a cured product of the above-mentioned ultraviolet curable composition.
• the ultraviolet curable composition of the present invention has the following properties when the total mass of the composition is 100 parts by mass: (A) 1 to 99 parts by mass of a compound having one or more (meth)acryloxy groups in one molecule, and (B) a compound having two or more alkenyl groups and at least one carbon number of 6 to 20 in one molecule. 99 to 1 part by mass of an organopolysiloxane having an aromatic hydrocarbon group and not having an ultraviolet curable functional group, as an essential curable component, and, if necessary, components selected from a photoradical polymerization initiator and various additives.
• the curable composition of the present invention is characterized in that it does not substantially contain an organic solvent.
• polysiloxane refers to a polysiloxane with a degree of polymerization of siloxane units (Si-O) of 2 or more, that is, an average of 2 or more Si-O bonds per molecule. It includes siloxane oligomers such as disiloxane, trisiloxane, and tetrasiloxane, as well as siloxane polymers with a higher degree of polymerization.
• Component (A) is a compound having one or more (meth)acryloxy groups in one molecule. As long as this purpose can be achieved, there is no limitation on the molecular structure, and it can be any one such as linear, branched, cyclic, cage-shaped, etc.
• (meth)acryloxy group means a group selected from methacryloxy groups and acryloxy groups, and can include both.
• the compound having a (meth)acryloxy group includes both methacrylate compounds and acrylate compounds.
• the above component (A) preferably has a viscosity of 1 to 1,000 mPa ⁇ s at 25°C, more preferably 1 to 500 mPa ⁇ s, and particularly preferably 1 to 20 mPa ⁇ s.
• the above component (A) contains on average 1 to 4 (meth)acryloxy groups, preferably 1 to 3, and more preferably 1 to 2 (meth)acryloxy groups per molecule.
• the position of the (meth)acryloxy groups in the molecule there is no restriction on the position of the (meth)acryloxy groups in the molecule, and they may be located close to each other or may be located apart.
• the above component (A) may be a compound having one (meth)acryloxy group, or a mixture of a compound having one (meth)acryloxy group and a compound having two or more (meth)acryloxy groups.
• the compound having one (meth)acryloxy group in the above component (A) may be (A1), one or more compounds having one (meth)acryloxy group and no silicon atom, or a mixture thereof, and is preferred.
• component (A) may be the following (A1) or (A2).
• (A1) One or more compounds having one (meth)acryloxy group and no silicon atoms
• (A2) A mixture of (A1) and one or more compounds having one (meth)acryloxy group and a silicon atom.
• the mixture (A2) is a mixture of a compound having one (meth)acryloxy group and a silicon atom (for example, a (meth)acryloxy-functional polydimethylsiloxane, a (meth)acryloxy-functional branched organopolysiloxane, etc.) and (A1) which has no silicon atoms.
• a silicon atom for example, a (meth)acryloxy-functional polydimethylsiloxane, a (meth)acryloxy-functional branched organopolysiloxane, etc.
• the component (A) may contain at least one type of compound having an acryloxy group, or may be a mixture of two or more types of compounds having an acryloxy group.
• compounds having one (meth)acryloxy group include isoamyl (meth)acrylate, octyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and diethylene glycol monoethyl ether.
• (meth)acrylate diethylene glycol monomethyl ether (meth)acrylate, 2-ethylhexyl (meth)acrylate, phenoxyethyl (meth)acrylate, diethylene glycol monophenyl ether (meth)acrylate, (meth)acrylic acid, 2-hydroxyethyl acrylate, 2 -Hydroxypropyl (meth)acrylate, 2-hydroxy-1-methylethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate Acrylate, 1-hydroxymethylpropyl (meth)acrylate, 4-(meth)acryloyloxyphenol, 6-hydroxyhexyl (meth)acrylate, Methyl-2-(2-hydroxy-1-methylethyl)(meth)acrylate, Tetrahydro Furfuryl (meth)acrylate, isobornyl (meth)acrylate, dicycl
• acryloxypropyltristrimethylsiloxysilane methacryloxypropyltristrimethylsiloxysilane, acryloxypropyltris(trimethylsilylethyldimethylsiloxy)silane, methacryloxypropyltris(trimethylsilylethyldimethylsiloxy) ) silane, acryloxypropyltris((tristrimethylsiloxysilyl)ethyldimethylsiloxy)silane, and methacryloxypropyltris((tristrimethylsiloxysilyl)ethyldimethylsiloxy)silane, which can be used alone or in combination of two or more. be able to.
• the compound having one (meth)acryloxy group can be used alone or in combination of two or more, taking into consideration the viscosity, curability, hardness after curing, and glass transition temperature of the compound.
• 2-ethylhexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, (meth)acryloxypropyltristrimethylsiloxysilane can be preferably used
• 2-ethylhexyl acrylate, isobornyl acrylate, Dicyclopentanyl acrylate and (meth)acryloxypropyltristrimethylsiloxysilane can be particularly preferably used.
• compounds having two or more (meth)acryloxy groups include diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,4-bis(acryloyloxy)butane, 1,6-bis((meth)acryloyloxy)hexane, 1,9-bis(acryloyloxy)nonane, tricyclodecane dimethanol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(2-acryloyloxy)ethyl isocyanurate, pentaerythritol tetraacrylate, 3-acryloyloxy-2-hydroxyethyl acrylate, and 1,2-dimethylphenyl ether.
• acrylates include acryloyloxypropyl methacrylate, 3-methacryloyloxy-2-hydroxypropyl methacrylate, 3-(meth)acryloyloxy-2-hydroxypropyl (meth)acrylate, glycerol di(meth)acrylate, glycerol-1,3-diglycerolate di(meth)acrylate, polydimethylsiloxane having (meth)acryloxy functionality at both ends, polydimethyldiphenylsiloxane copolymer having (meth)acryloxy functionality at both ends, polydimethyl((meth)acryloxyalkylmethyl)siloxane copolymer having trimethylsilyl functionality at both ends, and polydimethyl((meth)acryloxyalkylmethyl)siloxane copolymer having acryloxy functionality at both ends.
• Terminated (meth)acryloxy-functional polydimethylsiloxanes can preferably be used, but compounds without silicon atoms, namely diethylene glycol di(meth)acrylate, 1,6-bis((meth)acryloyloxy)hexane, tricyclodecane dimethanol More preferably, di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate is used.
• a compound having two or more of these (meth)acryloxy groups in combination with a compound having one (meth)acryloxy group.
• both can be combined in any ratio, but usually [compound having two or more (meth)acryloxy groups]/[compound having one (meth)acryloxy group] is 1/99 to 75/ 25 (mass ratio), which may range from 1/99 to 50/50, preferably from 1/99 to 30/70. This is because if the ratio of the compound having two or more (meth)acryloxy groups is too high, the cured product tends to have high hardness and become brittle.
• Component (B) is an organopolysiloxane having two or more alkenyl groups and at least one aromatic hydrocarbon group having 6 to 20 carbon atoms in one molecule and having no ultraviolet curable functional group.
• Such component (B) improves the viscosity and mechanical strength (particularly toughness and tensile elongation) of the cured product, as well as improves the molecular Since it contains an aromatic hydrocarbon group such as an aryl group, it has the advantage of not impairing the ultraviolet curability of the entire composition.
• the alkenyl group in component (B) is preferably a terminal alkenyl group in its molecular structure.
• the component (B) having alkenyl groups at both ends of the molecular chain functions as a crosslinking agent and/or a chain extender in the crosslinked structure, and contributes to improving the rubber physical properties of the cured product, especially elongation and tensile strength. be.
• the above component (B) has the following average composition formula: R a R' b SiO (4-ab)/2 (1)
• R is an alkenyl group
• R' is a group selected from monovalent hydrocarbon groups excluding alkenyl groups, hydroxyl groups, and alkoxy groups
• a and b are numbers satisfying the following conditions: 1 ⁇ a+b ⁇ 3 and 0.05 ⁇ a/(a+b) ⁇ 1.0, and have at least 2 R in the molecule
• at least 1 of R' is an aromatic hydrocarbon group having 6 to 20 carbon atoms.
• It can be a linear, branched, or cyclic organopolysiloxane represented by:
• the alkenyl group represented by R in formula (1) is exemplified by an alkenyl group having 2 to 8 carbon atoms, and specific examples thereof include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, and an octenyl group. Particularly preferred among these are a vinyl group and a hexenyl group.
• At least one R' is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and the rest are groups selected from monovalent hydrocarbon groups, hydroxyl groups, and alkoxy groups.
• the aromatic hydrocarbon group having 6 to 20 carbon atoms, which is R' includes groups such as phenyl group, tolyl group, xylyl group, and naphthyl group, with phenyl group being preferred. If R' does not contain an aromatic hydrocarbon group having 6 to 20 carbon atoms, even if an organopolysiloxane containing an alkenyl group is used in place of component (B), the composition as a whole will have significant UV curability. In some cases, it may not be possible to achieve improved mechanical strength and good UV curability of the cured product according to the present invention.
• R' include unsubstituted monovalent hydrocarbon groups and fluorine-substituted monovalent hydrocarbon groups.
• the unsubstituted or fluorine-substituted monovalent hydrocarbon group is preferably a group selected from unsubstituted or fluorine-substituted alkyl having 1 to 20 carbon atoms, and cycloalkyl.
• alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, hexyl, and octyl, with methyl and hexyl groups being particularly preferred. .
• Examples of the cycloalkyl group include cyclopentyl and cyclohexyl.
• Examples of monovalent hydrocarbon groups substituted with fluorine include 3,3,3-trifluoropropyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
• the fluorine-substituted monovalent hydrocarbon group is preferably 3,3,3-trifluoropropyl group.
• the organopolysiloxane represented by the above formula (1) has a viscosity at 25°C of 1 to 25,000 mPa. s, more preferably 1 to 5,000 mPa ⁇ s.
• the viscosity of the organopolysiloxane can be adjusted by changing the ratio of a and b in formula (1) and the molecular weight.
• the organopolysiloxane represented by formula (1) preferably has an average of 2 to 1,000 silicon atoms, more preferably 2 to 500 silicon atoms per molecule.
• the organopolysiloxane of component (B) is The following formula (2): (2) This is a compound represented by
• the organopolysiloxane represented by the formula (2) has at least two alkenyl groups in one molecule, and at least one having 6 to 20 carbon atoms. aromatic hydrocarbon group.
• the structure of the alkenyl group is not limited to a specific chemical structure as long as it has a carbon-carbon double bond.
• the alkenyl group is particularly preferably a terminal alkenyl group, such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, and 4-vinyl group.
• Examples include, but are not limited to, alkenyl groups having 2 to 20 carbon atoms such as phenyl, and particularly preferred are vinyl and hexenyl groups.
• Examples of the 6-20 aromatic hydrocarbon group include phenyl, tolyl, xylyl, and naphthyl groups, with phenyl being preferred.
• R 1 to R 8 other than the alkenyl group and the 6 to 20 aromatic hydrocarbon group are each independently an unsubstituted or fluorine-substituted monovalent hydrocarbon group, preferably having a carbon atom number.
• the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, pentyl, and octyl, with methyl being particularly preferred.
• Examples of the cycloalkyl group include cyclopentyl and cyclohexyl.
• Examples of monovalent hydrocarbon groups substituted with fluorine include 3,3,3-trifluoropropyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups. .
• the fluorine-substituted monovalent hydrocarbon group is preferably 3,3,3-trifluoropropyl group.
• n in formula (2) is a value such that the viscosity of the organopolysiloxane represented by formula (2) at 25°C is preferably 1 to 25,000 mPa ⁇ s, more preferably 1 to 5,000 mPa ⁇ s. .
• Those skilled in the art can easily determine the value of n without undue trial and error so that the viscosity of the organopolysiloxane of formula (2) falls within the above-mentioned viscosity range.
• the number of alkenyl groups in the organopolysiloxane of formula (2), which is component (B), is 2 or more per molecule, preferably 2 or more and 10 or less, and more preferably 2 or more and 8 or less.
• the organopolysiloxane of formula (2) can be used alone or as a mixture of two or more. When two or more organopolysiloxanes are used as a mixture, it is preferable that the viscosity of the mixture at 25°C is as described above.
• the compound of the above formula (1) may be a branched organopolysiloxane represented by the following average unit formula (3).
• Average unit formula (3) (R 3 SiO 1/2 ) c (R 2 SiO 2/2 ) d (RSiO 3/2 ) e (SiO 4/2 ) f (3)
• R is each independently a group selected from an alkenyl group, an unsubstituted or fluorine-substituted monovalent hydrocarbon group, a hydroxyl group, and an alkoxy group; is an alkenyl group, at least one is an aromatic hydrocarbon group having 6 to 20 carbon atoms, (e+f) is a positive number, c is 0 or a positive number, and d is in the range of 0 to 100. is the number within.
• alkenyl group and the 6-20 aromatic hydrocarbon group and monovalent hydrocarbon group are as defined above for formula (2).
• preferred viscosity of the organopolysiloxane represented by formula (3) is also as defined above for the organopolysiloxane represented by formula (2).
• alkoxy groups and silanol groups may remain in the molecule as long as the amount is small.
• the organopolysiloxane represented by formula (3) preferably has 4 to 30, particularly 6 to 20, silicon atoms per molecule.
• the number of alkenyl groups that the organopolysiloxane represented by formula (3) has is 2 or more per molecule on average, and preferably 2 or more and 10 or less.
• component (B), in particular the organopolysiloxane of formula (3) is a branched organopolysiloxane having (RSiO 3/2 ) units.
• linear organopolysiloxane represented by the above (1), especially formula (2) include dimethylvinylsilylpolymethylphenylsiloxane at both ends, dimethylvinylsilylpolydimethyl/methylphenylsiloxane copolymer at both ends.
• branched organopolysiloxane represented by the above (1) especially the formula (3), include polysiloxanes consisting of M Vi (dimethylvinylsiloxy) units and T Ph (phenylsiloxy) units, M Vi units and Polysiloxane consisting of M (trimethylsilyl) units and T Ph (phenylsiloxy) units, polysiloxane consisting of M Vi units, D (dimethylsiloxy) units and T Ph units, M Hex (dimethylhexenylsiloxy) units and T Ph units.
• polysiloxane consisting of M Hex units, M units and T Ph units, polysiloxanes consisting of M Hex units, D units and T Ph units, polysiloxanes consisting of M units, D Vi (methylvinylsiloxy) units and T Ph units.
• polysiloxane consisting of D Hex units, D units and T Ph units
• polysiloxanes consisting of D Hex units and T Ph units
• polysiloxanes consisting of T Hex units and T Ph units
• M units T Hex units and T Ph units.
• examples include, but are not limited to, polysiloxanes consisting of the following.
• the compound of the above formula (1) is the following formula (4): (4)
• R is a group independently selected from an alkenyl group and an unsubstituted or fluorine-substituted monovalent hydrocarbon group
• x is an integer from 3 to 10, and at least 2 and at least one aromatic hydrocarbon group having 6 to 20 carbon atoms.
• alkenyl group, aromatic hydrocarbon group having 6 to 20 carbon atoms, and unsubstituted or fluorine-substituted monovalent hydrocarbon group that R in formula (4) may represent are as defined for formula (1) above. .
• the preferred viscosity of the organopolysiloxane represented by formula (4) is also as defined above for the organopolysiloxane represented by formula (1).
• cyclic organopolysiloxane represented by formula (4) include cyclic trisiloxanes consisting of methylvinylsiloxy groups and methylphenylsiloxy groups, and cyclic tetrasiloxanes consisting of methylvinylsiloxy groups and methylphenylsiloxy groups. .
• organopolysiloxane represented by the above formula (1) more specifically, any one of formulas (2) to (4), can be used singly or in any combination of two or more to form the component ( It can be used as B).
• Component (B) is particularly one or more selected from the group consisting of organopolysiloxanes represented by the above formula (2), branched organopolysiloxanes represented by formula (3), and combinations thereof.
• an organopolysiloxane of Particularly preferred is an organopolysiloxane represented by the above formula (2), in which R 2 and R 7 at both ends of the molecular chain are alkenyl groups, and other substituents (R 1 , R 3 , R 4 , R 5 , R 6 and R 8 ) is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and n in formula (2) is 25 of the organopolysiloxane represented by formula (2).
• the organopolysiloxane has a viscosity of preferably 1 to 25,000 mPa ⁇ s, more preferably 1 to 5,000 mPa ⁇ s at °C.
• Compounds recommended as component (B) include polymethylphenylsiloxane having dimethylvinylsilyl at both ends, polydimethylphenylsiloxane having dimethylvinylsilyl at both ends/methylphenylsiloxane copolymer, polydimethylphenylsiloxane having dimethylvinylsilyl at both ends/diphenylsiloxane copolymer, polymethylphenylsiloxane having dimethylhexenylsilyl at both ends, polydimethylphenylsiloxane having dimethylhexenylsilyl at both ends/methylphenylsiloxane copolymer, polymethylphenylsiloxane having trimethylsilyl at both ends/methylvinylsiloxane copolymer, polymethylphenylvinylsilyl at both ends/methylhexenylsiloxane copolymer, polydimethylphenylsiloxane
• polymethylphenylsiloxanes having dimethylvinylsilyl at both ends polydimethyl/diphenylsiloxane copolymers having dimethylvinylsilyl at both ends, polysiloxanes consisting of M units, D Hex units and T Ph units, polysiloxanes consisting of D Hex units and T Ph units, and polysiloxanes consisting of T Hex units and T Ph units are particularly preferably used.
• the mixing ratio of component (A) and component (B) is 1 to 99% by mass of component (A) and 1 to 99% by mass of component (B) relative to the total amount of component (A) and component (B) (100% by mass). is in the range of 99 to 1% by mass.
• the ratio of components (A) and (B) is within this range, the viscosity of the curable composition is appropriate, good ultraviolet curability is maintained, and the mechanical properties of the resulting cured product are improved, especially the tensile elongation. Large materials can be designed.
• the preferred proportion of component (A) is 15% by mass or more and 85% by mass or less, more preferably 25% by mass or more and 75% by mass or less of the total amount of components (A) and (B).
• component (A) and component (B) in the ultraviolet curable composition of the present invention is within the above content range, but when the total mass of the composition is 100 parts by mass, component (A) ) and component (B) is preferably 90 parts by mass or more, particularly preferably in the range of 90 to 99.9 parts by mass, and particularly preferably in the range of 90 to 99 parts by mass. That is, most of the preferred UV-curable compositions are composed of component (A) and component (B). However, the present composition may also contain other components described below.
• the ultraviolet curable composition of the present invention can achieve a viscosity suitable for a coating agent without substantially using an organic solvent, and can achieve a viscosity suitable for a coating agent without substantially using an organic solvent. It does not include.
• substantially free of organic solvents means that the content of organic solvents is less than 0.1% by mass of the entire composition, and is preferably analyzed using an analytical method such as gas chromatography. It means that it is below the limit.
• a desired viscosity can be achieved without using an organic solvent.
• a photopolymerization initiator can be added to the ultraviolet curable composition of the present invention, if desired.
• a photoradical polymerization initiator can be used as the photopolymerization initiator.
• the photoradical polymerization initiator generates free radicals upon irradiation with ultraviolet rays or electron beams, which causes a radical polymerization reaction and can cure the composition of the present invention.
• a polymerization initiator is usually not necessary.
• Photoradical polymerization initiators are broadly divided into photocleavage type and hydrogen abstraction type, but the photoradical polymerization initiator used in the composition of the present invention can be arbitrarily selected from those known in the art and is not particularly limited to a specific one.
• photoradical polymerization initiators include acetophenone, p-anisil, benzyl, benzoin, benzophenone, 2-benzoylbenzoic acid, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, 4-benzoylbenzoic acid, 2,2'-bis(2-chlorophenyl)-4, 4',5,5'-Tetraphenyl-1,2'-biimidazole, Methyl 2-benzoylbenzoate, 2-(
• photoradical polymerization initiators include Omnirad (registered trademark) 651, 184, 1173, 2959, 127, 907, 369, 369E, and 379EG (alkylphenone-based photopolymerization initiators, IGM Resins B.V.), Omnirad (registered trademark) TPO H, TPO-L, and 819 (acylphosphine oxide-based photopolymerization initiators, IGM Resins B.V.), Omnirad (registered trademark) MBF and 754 (intramolecular hydrogen abstraction type photopolymerization initiators, IGM Resins B.V.), and Irgacure (registered trademark) OXE01 and OXE02 (oxime ester-based non-polymerization initiators, BASF).
• Omnirad registered trademark 651, 184, 1173, 2959, 127, 907, 369, 369E, and 379EG
• alkylphenone-based photopolymerization initiators IGM Resin
• the amount of the photoradical polymerization initiator to be added to the composition of the present invention is not particularly limited as long as the desired photopolymerization reaction or photocuring reaction occurs, but it is generally based on the total mass of the composition of the present invention. It is used in an amount of 0.01 to 5% by weight, preferably 0.05 to 1% by weight.
• a photosensitizer can also be used in combination with the above-mentioned radical photopolymerization initiator.
• the use of 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 a 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.
• Examples of sensitizers include anthracene compounds, phenothiazine compounds, perylene compounds, cyanine compounds, merocyanine compounds, coumarin compounds, benzylidene ketone compounds, (thio)xanthenes or (thio)xanthone compounds, such as isopropyl.
• Thioxanthone, 2,4-diethylthioxanthone, alkyl-substituted anthracenes, squalium-based compounds, (thia)pyrylium-based compounds, porphyrin-based compounds, etc. are known, and any photosensitizer, including but not limited to these, can be used in the curing process of the present invention. It can be used in sexual compositions.
• the cured product obtained from the curable composition of the present invention is characterized by the molecular chain length and molecular structure of component (A) and component (B), the number of (meth)acryloxy groups per molecule of component (A), and the composition of component (A) and component (B). Designed so that the desired physical properties of the cured product and the curing speed of the curable composition can be obtained depending on the number of alkenyl groups per molecule of (B), and the viscosity of the curable composition has the desired value. It is possible. Further, a cured product obtained by curing the curable composition of the present invention is also included within the scope of the present invention.
• the shape of the cured product obtained from the composition of the present invention is not particularly limited, and may be a thin coating layer or an adhesive layer, a molded product such as a sheet, or an uncured state. It may be injected into a specific site and cured to form a filler, or it may be used as a sealing material or intermediate layer for a laminate or a display device.
• the cured product obtained from the composition of the present invention is preferably in the form of an injection-molded protective/adhesive layer and a thin coating layer, particularly preferably a thin insulating coating layer or an adhesive layer. .
• the curable composition of the present invention is suitable for use as a coating or potting agent or adhesive, in particular as an insulating coating or insulating adhesive or potting agent for electronic and electrical devices.
• the cured product obtained by curing the curable composition of the present invention is characterized by excellent mechanical properties, particularly tensile properties.
• By optimizing the curable composition it is possible to achieve a tensile elongation of the cured product of 100% or more when evaluated at a tensile rate of 50 mm/min at 25°C using a test specimen with a thickness of 0.5 mm. , is useful as a layer forming material for flexible displays.
• the cured product obtained by curing the curable composition of the present invention can be designed to have a dielectric constant of less than 3.0, less than 2.8, etc.
• the dielectric compositions can also be used to form coating layers with low dielectric constants.
• the viscosity of the entire composition must be , measured using an E-type viscometer, is recommended to be 500 mPa ⁇ s or less at 25°C.
• the viscosity is preferably 200 mPa ⁇ s or less, particularly 80 mPa ⁇ s or less, although it depends on the gap in which it is injected.
• the viscosity range is preferably 5 to 60 mPa ⁇ s, more preferably 5 to 30 mPa ⁇ s, and particularly preferably 5 to 20 mPa ⁇ s, considering the application of inkjet printing methods, which are rapidly beginning to be put into practical use.
• ⁇ It is s.
• compounds having preferred viscosity can be used as each component so that the viscosity of the entire composition has the desired viscosity.
• additives In addition to the above components, further additives may be added to the compositions of the invention if desired. Examples of additives include, but are not limited to, those listed below.
• An adhesion promoter can be added to the composition of the present invention in order to improve adhesion or adhesion to a substrate that is in contact with the composition.
• an adhesion imparting agent may be added to the curable composition of the present invention. is preferred.
• any known adhesion promoter can be used as long as it does not inhibit the curing reaction of the composition of the present invention.
• adhesion promoters examples include trialkoxysiloxy groups (e.g., trimethoxysiloxy, triethoxysiloxy) or trialkoxysilylalkyl groups (e.g., trimethoxysilylethyl, triethoxysilylethyl).
• organosilane having a hydrosilyl group or alkenyl group e.g., vinyl group, allyl group
• organosiloxane oligomer with a linear structure, branched structure, or cyclic structure having about 4 to 20 silicon atoms trialkoxy
• An organosilane having a siloxy group or a trialkoxysilylalkyl group and a methacryloxyalkyl group for example, a 3-methacryloxypropyl group
• Siloxane oligomer trialkoxysiloxy group or trialkoxysilylalkyl group and epoxy group-bonded alkyl group (e.g., 3-glycidoxypropyl group, 4-glycidoxybutyl group, 2-(3,4-epoxycyclohexyl)ethyl group) , 3-(3,4-epoxycyclohexyl)propyl group) or an organosiloxane oligomer with a linear, branched or cyclic structure having about 4 to 20 silicon atoms; trialkoxysilyl group (e.g.
• the amount of the adhesion promoter added to the curable composition of the present invention is not particularly limited, but since it does not promote the curing properties of the curable composition or discoloration of the cured product, the total amount of the adhesion promoter added to the curable composition of the present invention is 100%. It is preferably within the range of 0.01 to 5 parts by mass, or within the range of 0.01 to 2 parts by mass.
• additives In addition to or in place of the above-mentioned adhesion-imparting agent, other additives may be added to the composition of the present invention, if desired.
• Additives that can be used include leveling agents, silane coupling agents not included in the adhesion imparting agents mentioned above, ultraviolet absorbers, antioxidants, polymerization inhibitors, fillers (reinforcing fillers, insulation functional fillers such as functional fillers and thermally conductive fillers). If necessary, suitable additives can be added to the compositions of the invention.
• a thixotropy imparting agent may be added to the composition of the present invention, if necessary, particularly when used as a potting agent or sealing material.
• Examples of usable high-energy rays include ultraviolet rays, gamma rays, X-rays, alpha rays, and electron beams. Particular examples include ultraviolet rays, X-rays, and electron beams irradiated from commercially available electron beam irradiation equipment. Among these, ultraviolet rays are preferable from the viewpoint of catalyst activation efficiency, and ultraviolet rays in the wavelength range of 280 to 405 nm are used for industrial purposes. preferred from the standpoint of practical use. Further, the amount of ultraviolet irradiation is preferably such that the cumulative amount of irradiation at a wavelength of 365 nm or 405 nm is within the range of 100 mJ/cm 2 to 10 J/cm 2 .
• the curable composition of the present invention has a high viscosity adjustment ability, it is particularly useful as a material for forming insulating layers constituting various articles, particularly electronic devices and electrical devices.
• the composition of the present invention can be prepared by applying ultraviolet rays or electron beams to the composition, or by sandwiching the composition between two substrates, at least one of which is made of a material that transmits ultraviolet rays or electron beams.
• the material can be cured to form an insulating layer. In that case, it is also possible to form a pattern when applying the composition of the present invention to a substrate and then cure the composition, or to apply ultraviolet rays or electron beams when applying the composition to a substrate and curing the composition.
• an insulating layer in a desired pattern by leaving a hardened part and an unhardened part by irradiation and then removing the unhardened part with a solvent.
• the cured layer according to the invention when it is an insulating layer, it can be designed to have a low dielectric constant of less than 3.0.
• the curable composition of the present invention is particularly suitable as a material for forming an insulating layer in a display device such as a touch panel or a display, since the cured product obtained from the composition has good transparency.
• the insulating layer may be formed into any desired pattern as described above, if necessary. Therefore, a display device such as a touch panel or a display, which includes an insulating layer obtained by curing the ultraviolet-curable organopolysiloxane composition of the present invention, is also an aspect of the present invention.
• the curable composition of the present invention can be used to coat an article and then cured to form an insulating coating layer (insulating film) or adhesive layer. Therefore, the composition of the present invention can be used as an insulating coating agent or insulating adhesive. In addition, the curable composition of the present invention can be cured to form a cured product, which can be used as an insulating coating layer or insulating adhesive layer.
• the insulating film formed from the curable composition of the present invention can be used for various purposes. In particular, it can be used as a component of electronic devices or as a material used in the process of manufacturing electronic devices. Electronic devices include electronic equipment such as semiconductor devices and magnetic recording heads.
• the curable composition of the present invention can be used for semiconductor devices such as LSI, system LSI, DRAM, SDRAM, RDRAM, D-RDRAM, and insulating films for multi-chip module multilayer wiring boards, interlayer insulating films for semiconductors, and etching stopper films. It can be used as a surface protective film, a buffer coat film, a passivation film in LSI, a cover coat for a flexible copper clad board, a solder resist film, and a surface protective film for optical devices.
• the UV-curable composition of the present invention is also suitable for use as a potting agent, particularly as an insulating potting agent for electronic and electrical devices.
• composition of the present invention can be coated on the surface of a substrate using an inkjet printing method, since it is possible to provide a low-viscosity composition by adjusting the mixing ratio of component (A) and component (B). It can be used as a material for forming layers.
• Viscosity of curable composition and each component The viscosity (mPa ⁇ s) of the composition at 25° C. was measured using a rotational viscometer (manufactured by Tokimec Corporation, E-type viscometer VISCONIC EMD).
• a 1 mm thick mold having a circular hole with an inner diameter of 40 mm was placed on a PET film coated with a fluoropolymer-based release agent, and about 1.3 g of a curable composition was poured into the hole.
• the composition was covered with the same PET film as above, and a 10 mm thick glass plate was placed on top of it.
• the composition was cured by irradiating the LED light with a wavelength of 405 nm with an energy amount of 2 J/ cm2 from above, to produce a disk-shaped organopolysiloxane cured product with a diameter of 40 mm and a thickness of 1 mm.
• the ultraviolet curable compositions of the present invention are solvent-free compositions, and the type and number of functional groups of component (A), ) and component (B), it is possible to easily adjust the viscosity and tensile elongation of the cured product.
• the composition contains a component (A) of low viscosity, the viscosity at 25°C is suitable for application to substrates as injection molding material and as a coating agent, in particular for application by inkjet printing.
• the resulting cured product had high transparency.
• the cured product obtained from the composition of the present invention exhibited low dielectric properties.
• the ultraviolet curable composition of the present invention is suitable for the above-mentioned uses, particularly as a material for forming an insulating layer of display devices such as touch panels and displays, especially flexible displays.

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