CN116348556A - Ultraviolet curable polyorganosiloxane composition and use thereof - Google Patents
Ultraviolet curable polyorganosiloxane composition and use thereof Download PDFInfo
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- CN116348556A CN116348556A CN202180070730.7A CN202180070730A CN116348556A CN 116348556 A CN116348556 A CN 116348556A CN 202180070730 A CN202180070730 A CN 202180070730A CN 116348556 A CN116348556 A CN 116348556A
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- polyorganosiloxane
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- composition
- ultraviolet
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- WXIWSQBJNUSTTO-UHFFFAOYSA-N pentane-2,4-dione;platinum Chemical compound [Pt].CC(=O)CC(C)=O.CC(=O)CC(C)=O WXIWSQBJNUSTTO-UHFFFAOYSA-N 0.000 description 1
- VYKQKQNKTBJUFA-UHFFFAOYSA-N pentane-2,4-dione;platinum(2+) Chemical compound [Pt+2].CC(=O)CC(C)=O.CC(=O)CC(C)=O VYKQKQNKTBJUFA-UHFFFAOYSA-N 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- NRYWFNLVRORSCA-UHFFFAOYSA-N triethoxy(6-triethoxysilylhexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC[Si](OCC)(OCC)OCC NRYWFNLVRORSCA-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—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
- 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
- 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
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- 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
- C08G2150/00—Compositions for coatings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention provides a curable composition containing silicon atoms, particularly an ultraviolet curable composition, which has a low refractive index as a cured product and is excellent in workability when applied to a substrate. The ultraviolet curable composition of the present invention is characterized by comprising: (A) A polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule; (B) A polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule; and (C) a photoactive hydrosilylation catalyst, wherein the composition does not contain an organic solvent, the viscosity of the entire composition is 80 mPas or less as measured at 25 ℃ using an E-type viscometer, and the refractive index of the cured product after curing is 1.45 or less as measured at 25 ℃ and a wavelength of 589 nm.
Description
Technical Field
The present invention relates to an ultraviolet-curable polyorganosiloxane composition of a polyorganosiloxane curable by actinic rays (actinic rays) such as ultraviolet rays or electron beams, and particularly to an ultraviolet-curable polyorganosiloxane composition having a low refractive index and excellent coatability as a cured product obtained therefrom. The curable polyorganosiloxane composition of the present invention has a refractive index as low as 1.45 or less, and is suitable as an insulating material for electronic devices and electrical devices, particularly as a material for use as a coating agent. Further, the coating composition has excellent coating properties and excellent wettability to a substrate, and is useful as an inkjet printing material.
Background
Silicone resins have been used heretofore as coating agents, potting agents, insulating materials, and the like for electronic devices and electric devices because of their high heat resistance and excellent chemical stability. Heretofore, ultraviolet curable silicone compositions have also been reported for silicone resins.
Touch panels are used for various display devices such as mobile devices, industrial devices, and car navigation. In order to improve the sensing sensitivity, it is necessary to suppress the electrical influence from a light emitting portion such as a Light Emitting Diode (LED) or an organic EL device (OLED), and an insulating layer is generally disposed between the light emitting portion and the touch panel.
On the other hand, a thin display device such as an OLED has a structure in which a plurality of functional thin layers are stacked. In recent years, a study has been started to improve the brightness of the entire display device by laminating a layer having a high refractive index and a layer having a low refractive index on a touch panel layer. In addition, for the purpose of improving productivity, an inkjet printing method is used as a processing method of the organic layer. Therefore, the insulating layer is also required to be processable by an inkjet printing method.
JP-A2019-73588 discloses a photocurable resin composition comprising an aromatic compound having an unsaturated bond and a compound having a mercapto group, and JP-A2020-26515 discloses a photocurable resin composition comprising a naphthalene compound having an unsaturated bond as a main component. Any composition is characterized in that it can be applied by an inkjet method, and the cured product thereof has a refractive index of 1.60 or more and a high refractive index.
On the other hand, japanese patent No. 6200591 discloses a sealant for an electronic device for inkjet application comprising a polysiloxane silicone having an ultraviolet-curable functional group and a specific curable compound, and japanese patent application laid-open No. 2019-189844 discloses a photocurable resin composition for an electronic device comprising a multifunctional cationic polymerizable compound and a specific monofunctional cationic polymerizable compound. The refractive index of the composition after curing is not described in these patent documents, but in any case, the refractive index is a value of 1.48 or more when the refractive index is calculated based on the monomer structure in the curable composition.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2019-73588
Patent document 2: japanese patent laid-open No. 2020-26515
Patent document 3: japanese patent No. 6200591
Patent document 4: japanese patent laid-open No. 2019-189844
Disclosure of Invention
Problems to be solved by the invention
As described above, several ultraviolet-curable polyorganosiloxane compositions are known, but the cured products thereof are now further required to have a low refractive index of 1.45 or less and to have excellent workability for application to a substrate, particularly an ultraviolet-curable composition having a low viscosity. The purpose of the present invention is to provide a curable composition, particularly an ultraviolet-curable composition, which has a low refractive index as a cured product and is excellent in workability when applied to a substrate.
Solution for solving the problem
The present invention is based on the finding that the composition design of an ultraviolet-curable polyorganosiloxane composition which is excellent in workability such as coatability and has a refractive index of 1.45 or less as measured at 25 ℃ and a wavelength of 589nm of a cured product after curing can be performed, the ultraviolet-curable polyorganosiloxane composition comprising: (A) A polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule; (B) A polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule; and (C) a photoactive hydrosilylation catalyst, wherein the composition does not contain an organic solvent, and the viscosity of the entire composition, as measured at 25 ℃ using an E-type viscometer, is 80 mPas or less.
The ultraviolet-curable polyorganosiloxane composition of the present invention is characterized by comprising:
(A) A polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule;
(B) A polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule; and
(C) A photoactive hydrosilylation catalyst,
the composition does not contain an organic solvent, the viscosity of the entire composition is 80 mPas or less as measured at 25 ℃ using an E-type viscometer, and the refractive index of the cured product after curing is 1.45 or less as measured at 25 ℃ and a wavelength of 589 nm.
In the ultraviolet-curable composition of the present invention, it is preferable that the component (a) contains a polyorganosiloxane having a viscosity of 60mpa·s or less, two or more alkenyl group-containing groups per molecule, and three or more silicon atoms per molecule, as measured at 25 ℃ using an E-type viscometer.
In the ultraviolet-curable composition of the present invention, it is preferable that the composition (a) contains, as the component (a), a polyorganosiloxane having a viscosity of 10mpa·s or less, two or more alkenyl group-containing groups per molecule, and three silicon atoms per molecule, as measured at 25 ℃.
Preferably, the component (A) contains a polyorganosiloxane having alkenyl-containing groups at both ends.
Preferably, the polyorganosiloxane having an alkenyl group-containing group as the component (A) has an average of four or more silicon atoms per molecule.
Preferably, the organic groups bonded to silicon atoms other than the alkenyl group-containing groups of the polyorganosiloxane of the component (a) and the organic groups bonded to silicon atoms other than the silicon-bonded hydrogen atoms of the polyorganosiloxane of the component (B) are substantially all methyl groups. Substantially all of the organic groups bonded to silicon atoms are methyl groups, meaning that 95% or more, preferably 97% or more, more preferably 99% or more, and most preferably 100% of the organic groups bonded to silicon atoms in the polyorganosiloxane are methyl groups. The proportion of methyl groups in the organic groups bound to silicon atoms in all but alkenyl groups is, for example, by 1 The value obtained by H-NMR spectroscopy or the value calculated based on the amount of the organic group contained in the raw material used in the production of the polyorganosiloxane.
In the ultraviolet curable composition of the present invention, the viscosity of the entire composition is preferably 5 to 60mpa·s as measured at 25 ℃.
In the ultraviolet curable composition of the present invention, the viscosity of the entire composition is preferably 10 to 30mpa·s as measured at 25 ℃.
In the ultraviolet curable composition of the present invention, the content of the polyorganosiloxane having an alkenyl group-containing group and having a boiling point of not more than 200 ℃ at 1013.25 hundred pascals is preferably less than 1 mass%, preferably less than 0.1 mass% of the entire composition.
In the ultraviolet curable composition of the present invention, it is preferable that the photoactive hydrosilylation catalyst as component (C) is an unsubstituted or alkyl-substituted cyclopentadienyl trialkylplatinum complex.
The ultraviolet curable composition of the present invention is suitable for use as an insulating coating agent, and therefore, the present invention provides an insulating coating agent comprising the above ultraviolet curable polyorganosiloxane composition.
The present invention also provides a method for using the cured product of the ultraviolet-curable polyorganosiloxane composition as an insulating coating agent.
The present invention also provides a display device, such as a liquid crystal display or an organic EL display, comprising a layer composed of a cured product of the above ultraviolet-curable polyorganosiloxane composition.
Effects of the invention
The ultraviolet-curable polyorganosiloxane composition of the present invention has the following effects: the cured product obtained by curing the composition has a refractive index of 1.45 or less, and is low in viscosity, excellent in coating property on a substrate, and excellent in curability even when an organic solvent is not used.
Detailed Description
First, the ultraviolet-curable polyorganosiloxane composition (hereinafter also simply referred to as a curable composition or an ultraviolet-curable composition) of the present invention will be described in detail.
The curable composition of the present invention is characterized by comprising:
(A) A polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule;
(B) A polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule; and
(C) A photoactive hydrosilylation catalyst,
and contains no organic solvent as a constituent, the viscosity of the curable composition is 80 mPas or less as measured at 25 ℃ using an E-type viscometer, and the refractive index of the cured product obtained by curing the curable composition is 1.45 or less as measured at 25 ℃ at a wavelength of 589 nm.
The ultraviolet curable composition of the present invention contains a photo-active hydrosilylation catalyst, and when exposed to so-called actinic light (ultraviolet light), for example, the catalyst becomes active as a hydrosilylation catalyst, and as a result, crosslinking occurs by an addition reaction between the alkenyl group of component (a) and the silicon-bonded hydrogen atom (si—h) of component (B), i.e., a hydrosilane group, to cure the composition.
The components (a), (B), (C) and other optional components constituting the curable composition of the present invention will be described below.
< component (a): polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule)
The component (a) is a polyorganosiloxane having an alkenyl-containing group, that is, a curing-reactive group having a carbon-carbon double bond, and is not limited to an alkenyl-containing group of a specific chemical structure as long as its carbon-carbon double bond can react with an SiH group by hydrosilylation reaction. The alkenyl-containing group is particularly preferably a terminal alkenyl group, and examples thereof include: alkenyl groups having 2 to 20 carbon atoms such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and 4-vinylphenyl are not limited thereto. The alkenyl-containing group is particularly preferably a group selected from vinyl, allyl and hexenyl groups, and particularly preferably vinyl. The polyorganosiloxane of the component (a) preferably has an average of two or more alkenyl group-containing groups per molecule and three or more groups per molecule, and preferably has an average of four or more silicon atoms per molecule, and is particularly preferably a linear or branched polyorganosiloxane. One kind of such a polyorganosiloxane having an alkenyl group-containing group may be used, or two or more kinds selected from the group consisting of linear, branched, cyclic, and resinous (network-like) polyorganosiloxanes may be used in combination. It is particularly preferable to use only one or two or more kinds of linear polyorganosiloxanes or to use a linear polyorganosiloxane and a branched polyorganosiloxane in combination as the component (A).
The polyorganosiloxane of the component (a) is particularly preferably one or a combination of two or more selected from the group consisting of a linear polyorganosiloxane having alkenyl-containing groups at both molecular terminals and a branched polyorganosiloxane having alkenyl-containing groups at molecular terminals.
The polyorganosiloxane as the component (A) may contain, in addition to the group containing a carbon-carbon double bond, a group selected from monovalent hydrocarbon groups having no carbon-carbon double bond in the molecule, hydroxyl groups and alkoxy groups. Among the monovalent hydrocarbon groups are unsubstituted monovalent hydrocarbon groups and monovalent hydrocarbon groups substituted with fluorine. The monovalent hydrocarbon group which is unsubstituted or substituted with fluorine is preferably a group selected from the group consisting of an alkyl group, a cycloalkyl group, an arylalkyl group and an aryl group which are unsubstituted or substituted with fluorine having 1 to 20 carbon atoms. Examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, sec-butyl, pentyl, octyl and the like groups, particularly preferably methyl. Examples of the cycloalkyl group include: cyclopentyl, cyclohexyl, and the like. The arylalkyl groups include: benzyl, phenethyl, and the like. Examples of the aryl group include: phenyl, naphthyl, and the like. Examples of the monovalent hydrocarbon group substituted with fluorine include: 3, 3-trifluoropropyl group 3,4, 5, 6-nonafluorohexyl. As the monovalent hydrocarbon group substituted with fluorine, 3-trifluoropropyl group is preferable.
In the polyorganosiloxane of the component (a), it is preferable that the organic group bonded to the silicon atom other than the alkenyl group-containing group is substantially a methyl group. That is, the organic groups bonded to silicon atoms other than the alkenyl group-containing group are preferably 95% or more, preferably 97% or more, more preferably 99% or more, and most preferably 100% are methyl groups. Therefore, the most preferable embodiment of the component (a) is a polyorganosiloxane having a vinyl group as an alkenyl group-containing group and an organic group other than the vinyl group bonded to a silicon atom is substantially a methyl group, and is preferably a combination of one or two or more selected from the group consisting of linear polyorganosiloxanes and branched polyorganosiloxanes. In this case, the vinyl group is preferably located at the terminal end of the polyorganosiloxane molecule.
The polyorganosiloxane of the component (A) has the above alkenyl group-containing group and has three or more silicon atoms per molecule. The polyorganosiloxane of the component (A) preferably has an average of four or more silicon atoms per molecule. On the other hand, a silicone compound having a silicon atom number of less than three such as an organodisiloxane is a component having a boiling point of 1013.25 hundred pascals at 200 ℃ or less, and even if such a component has a low viscosity, hydrosilylation reaction between an alkenyl group-containing polyorganosiloxane and a silicon-bonded hydrogen atom (SiHH group) may be inhibited, and the ultraviolet curable composition of the present invention may not be achieved due to the inclusion of such a component.
In particular, in the polyorganosiloxane of the component (a) used in the curable composition of the present invention, the content of the polyorganosiloxane having a boiling point of not more than 200 ℃ at 1013.25 hundred pascals contained in the entire component (a) is preferably less than 1 mass%, preferably less than 0.1 mass%, particularly preferably not more than the detection limit of an analytical device such as a gas chromatograph. In order to achieve ultraviolet curability of the entire composition, it is particularly preferable that the polyorganosiloxane having a silicon atom number per molecule of less than three as in the organodisiloxane is substantially free of components having a boiling point of 1013.25 hundred pascals at 200 ℃. When such a component is contained, ultraviolet curability of the composition of the present invention may not be achieved.
From the viewpoint of achieving a low viscosity of the entire composition, the polyorganosiloxane of the component (a) has three or more silicon atoms per molecule, and the viscosity measured at 25 ℃ using an E-type viscometer is preferably 60mpa·s or less, more preferably 30mpa·s, and particularly preferably 10mpa·s or less. In this case, when two or more types of polyorganosiloxanes are used in combination as the component (a), the viscosity as a whole is preferably the above viscosity.
The component (a) may be preferably a polyorganosiloxane represented by the following average composition formula (1) or a mixture of two or more thereof.
R 11 a R 12 b SiO (4-a-b)/2 (1)
Wherein R is 11 Are the alkenyl-containing groups described above.
R 12 Is a group selected from the group consisting of monovalent hydrocarbon groups other than alkenyl-containing groups, hydroxyl groups, and alkoxy groups.
a and b are numbers satisfying the following conditions: 1.ltoreq.a+b.ltoreq.3 and 0.001.ltoreq.a/(a+b). Ltoreq.0.33, preferably a number satisfying the following condition: a+b is more than or equal to 1.5 and less than or equal to 2.5, and a/(a+b) is more than or equal to 0.005 and less than or equal to 0.2. The reason for this is that if a+b is not less than the lower limit of the above range, the flexibility of the cured product can be improved, while if a+b is not more than the upper limit of the above range, the toughness of the cured product can be improved, and if a/(a+b) is not less than the lower limit of the above range, the viscosity of the curable composition can be designed to be low, while if a/(a+b) is not more than the upper limit of the above range, the toughness of the cured product can be improved.
R 11 The alkenyl-containing group that can be represented is not limited to an alkenyl-containing group of a specific chemical structure as long as the carbon-carbon double bond thereof can react with an SiH group by hydrosilylation reaction. The alkenyl-containing group is particularly preferably a terminal alkenyl group, and examples thereof include: alkenyl groups having 2 to 20 carbon atoms such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and 4-vinylphenyl are not limited thereto. The alkenyl-containing group is particularly preferably a group selected from vinyl, allyl and hexenyl groups, and particularly preferably vinyl.
As R 12 Examples of monovalent hydrocarbon groups other than the alkenyl group-containing group that can be represented include: unsubstituted monovalent hydrocarbon groups and monovalent hydrocarbon groups substituted with fluorine. The monovalent hydrocarbon group which is unsubstituted or substituted with fluorine is preferably a group selected from the group consisting of an alkyl group, a cycloalkyl group, an arylalkyl group and an aryl group which are unsubstituted or substituted with fluorine having 1 to 20 carbon atoms. Examples of the alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, sec-butyl, pentyl, octyl and the like groups, particularly preferably methyl. Examples of the cycloalkyl group include: cyclopentyl, cyclohexyl, and the like. The arylalkyl groups include: benzyl, phenethyl, and the like. Examples of the aryl group include: phenyl, naphthyl, and the like. As examples of the monovalent hydrocarbon groups substituted with fluorine, there can be listedExamples are: 3, 3-trifluoropropyl group 3,4, 5, 6-nonafluorohexyl. As the monovalent hydrocarbon group substituted with fluorine, 3-trifluoropropyl group is preferable.
Thus, in formula (1), R is most preferred 11 Is vinyl, R 12 Is methyl.
Wherein the polyorganosiloxane represented by the average composition formula (1) has two or more alkenyl-containing groups in one molecule. The polyorganosiloxane represented by the average composition formula (1) is preferably one or a combination of two or more selected from the group consisting of linear polyorganosiloxanes and branched polyorganosiloxanes. In addition, the alkenyl-containing group is particularly preferably present at the molecular terminal.
The linear polyorganosiloxane having an alkenyl group-containing group which can be used as the component (A) includes a polyorganosiloxane represented by the following formula (2).
[ chemical formula 1]
Wherein R is 1 And R is 6 The same or different alkenyl groups having 2 to 12 carbon atoms (terminal alkenyl groups) are exemplified by: vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl are preferred, vinyl, allyl, 5-hexenyl, 7-octenyl are particularly preferred, from the viewpoint of high reactivity to hydrosilylation reaction.
R 2 、R 3 、R 4 R is as follows 5 The monovalent hydrocarbon groups other than alkenyl groups are each independently, for example, monovalent alkyl groups having 1 to 12 carbon atoms which are unsubstituted or substituted with fluorine, and are selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 3-chloropropyl and 3, 3-trifluoropropyl, and particularly preferably methyl.
Wherein m and n are numbers satisfying 0 < m < 50, 0.ltoreq.n < 5, 1.ltoreq.m+n < 50. In the case where m+n=1 or more, the polyorganosiloxane represented by the above formula has three or more silicon atoms per molecule.
Examples of such a particularly preferable component (a) include one or a mixture of two or more kinds of polyorganosiloxanes represented by the following general formula (3).
Me 2 ViSiO(Me 2 SiO) a SiMe 2 Vi (3)
In the formula, me and Vi each represent a methyl group and a represents a vinyl group, and a represents an integer of 1 or more in which the viscosity of the polyorganosiloxane of the formula (3) at 25℃is 1000 mPas or less, preferably 500 mPas or less, more preferably 100 mPas or less, particularly preferably 60 mPas or less, and most preferably 10 mPas or less. The lower limit of the viscosity is not limited, but is usually 2 mPas or more.
The branched polyorganosiloxane having an alkenyl group-containing group which can be used as the component (A) is preferably a polyorganosiloxane represented by the following average unit formula (4).
(R 21 SiO 3/2 ) o (R 22 2 SiO 2/2 ) p (R 23 3 SiO 1/2 ) q (SiO 4/2 ) r (KO 1/2 ) s (4)
In the above, R 21 、R 22 R is as follows 23 X is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and is a group selected from the group consisting of alkenyl groups and monovalent hydrocarbon groups having no carbon-carbon double bond. R is R 21 、R 22 R is as follows 23 Part of (2) is alkenyl, R being particularly preferred 23 3 SiO 1/2 R on the siloxane units shown 23 At least a portion of (2) is alkenyl.
In the above formula, (o+r) is a positive number, p is 0 or a positive number, q is a positive number, s is 0 or a positive number, p/(o+r) is a number in the range of 0 to 500, q/(o+r) is a number in the range of 2 to 5, (o+r)/(o+p+q+r) is a number in the range of 0.001 to 0.7, and s/(o+p+q+r) is a number in the range of 0 to 0.4.
As an upper partThe branched polyorganosiloxane having an alkenyl group-containing group is particularly preferably selected from the group consisting of a terminal dimethylvinylsilyl-terminated branched trifunctional polydimethylsiloxane and a terminal dimethylvinylsilyl-terminated branched tetrafunctional polydimethylsiloxane, and preferably a terminal dimethylvinylsilyl-terminated branched tetrafunctional polydimethylsiloxane. Examples of these trifunctional polydimethylsiloxanes include: having on average one T unit in the molecule, i.e. one R of formula (4) above 21 SiO 3/2 Units, other units being represented by M, i.e. R in formula (4) 23 3 SiO 1/2 A unit; or from M and D units, i.e. R for formula (4) 22 2 SiO 2/2 Polyorganosiloxane of unit constitution. Examples of the tetrafunctional polydimethylsiloxane include: having on average one Q unit in the molecule, i.e. one SiO with the above formula (4) 4/2 Units, other polyorganosiloxanes composed of M units, or of M units and D units.
The branched polyorganosiloxane used as component (A) particularly preferably has an average of 3 to 500, preferably 3 to 100, further preferably 3 to 50, particularly preferably 3 to 10 silicon atoms per molecule.
The viscosity of the branched polyorganosiloxane having an alkenyl group-containing group at 25℃is preferably 1000 mPas or less, more preferably 500 mPas or less, particularly preferably 300 mPas or less. The lower limit of the viscosity is not limited, but is usually 5 mPas or more.
In the curable composition of the present invention, the component (a) is preferably a linear polyorganosiloxane having alkenyl group-containing groups only at both ends of the molecular chain, a branched polyorganosiloxane having alkenyl group-containing groups only at the ends of the molecular chain, or a combination of both of them. It is particularly preferable to contain a linear polyorganosiloxane having alkenyl group-containing groups at both ends as the component (A).
The polyorganosiloxane used as the component (A) preferably has a viscosity of 60 mPas or less, more preferably 10 mPas or less, as measured at 25 ℃. When two or more types of the polyorganosiloxane are used in combination as the component (a), each component may be a component having a viscosity of 60mpa·s at 25 ℃, but even when the viscosity of a part of the components is larger than this value, the polyorganosiloxane having a lower viscosity may be contained as the whole component (a), and the viscosity is 60mpa·s or less, preferably 10mpa·s or less. For example, even if the component (a) contains a component having a viscosity exceeding 1000mpa·s as a part thereof, the viscosity of the other component as a whole can be set to a desired viscosity if the viscosity of the other component is sufficiently low.
Specific examples of the polyorganosiloxane used as the component (a) include, but are not limited to, the following.
Dimethylvinylsilyl-terminated polydimethylsiloxane (a substance having a viscosity of 2 to 1000 mPas at 25 ℃).
Terminal dimethylvinylsilyl-terminated branched trifunctional polydimethylsiloxane (a substance having a viscosity of 2 to 1000 mPas at 25 ℃).
Terminal dimethylvinylsilyl-terminated branched tetrafunctional polydimethylsiloxane (a substance having a viscosity of 2 to 1000 mPas at 25 ℃).
< component (B): polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule
The component (B) is a polyorganosiloxane having, on average, two or more silicon-bonded hydrogen atoms (Si-H) capable of bonding with the component (A) by hydrosilylation reaction in one molecule.
The polyorganosiloxane having a silicon-bonded hydrogen atom (hereinafter also referred to as organohydrogen polysiloxane) of the component (B) has an average of two or more silicon-bonded hydrogen atoms in one molecule, and functions as a crosslinking agent that forms a crosslink with the component (a) having an alkenyl group-containing group by hydrosilylation reaction.
As the component (B), one selected from the group consisting of linear organohydrogen polysiloxane and branched or resinous organohydrogen siloxane, or two or more kinds of them may be used in combination. Such organohydrogen polysiloxanes are compounds well known in the art.
Examples of the linear organohydrogen polysiloxane which can be used as the component (B) include: 1, 3-tetramethyldisiloxane, 1,3,5, 7-tetramethylcyclotetrasiloxane, tris (dimethylhydrosiloxy) methylsilane, tris (dimethylhydrosiloxy) phenylsilane, tetrakis (dimethylhydrosiloxy) silane, trimethylsiloxy-terminated methylhydrogen polysiloxane at both ends of the molecular chain, trimethylsiloxy-terminated dimethylsiloxane/methylhydrosiloxane copolymer at both ends of the molecular chain, dimethylhydrosiloxy-terminated dimethylsiloxane/methylhydrosiloxane copolymer at both ends of the molecular chain, trimethylsiloxy-terminated methylhydrosiloxane/diphenylsiloxane copolymer at both ends of the molecular chain, but are not limited thereto. They may be used singly or in combination of two or more. The compound used as the component (B) of the present invention is preferably an organohydrogen polysiloxane in which the proportion of methyl groups in the organic groups bonded to silicon atoms is 80% or more, preferably 90% or more. Most preferred are organohydrogen polysiloxanes wherein substantially all of the silicon-bonded organic groups are methyl groups.
Examples of the branched or resin (resin) organohydrogen polysiloxane which can be used as the component (B) include: hydrolysis condensate of trimethoxysilane, consisting of (CH) 3 ) 2 HSiO 1/2 Unit and SiO 4/2 Copolymers of units Composed of (CH) 3 ) 2 HSiO 1/2 Unit and (CH) 3 ) 3 SiO 1/2 Unit and SiO 4/2 Copolymers of units Composed of (CH) 3 ) 2 HSiO 1/2 Unit AND (C) 6 H 5 )SiO 3/2 Copolymers of units Composed of (CH) 3 ) 2 HSiO 1/2 Unit and SiO 4/2 Unit AND (C) 6 H 5 )SiO 3/2 Copolymers of units and mixtures of two or more selected from the group consisting of these. As a resinAs yet another example of the organohydrogen polysiloxane of (2), there may be mentioned: at least comprises a material selected from SiO 4/2 Units (Q units) and R 31 SiO 3/2 Branched siloxane units in the group consisting of units (T units) comprising R 31 3 SiO 1/2 Units (M units), R 31 2 HSiO 1/2 Unit (M) H Unit), optionally containing R 31 2 SiO 2/2 Unit (D unit), R 31 HSiO 1/2 Unit (D) H Unit) selected from M H MQ, M H Q, M H MT, M H T-shaped M H MQT, M H QT, M H MDQ type, M H MDD H Q, M H DQ, M H DD H Q, M H MDT type, M H MDD H T-shaped M H DT, M H DD H T-shaped M H MDQT type, M H MDD H QT, M H DQT type, M H DD H More than one organohydrogen polysiloxane resin in QT type. They may be used singly or in combination of two or more.
In the above formulae, R 31 Independently methyl or phenyl. R is R 31 Preferably methyl.
The organohydrogen polysiloxane which can be used as the component (B) in a branched or resin (resin) form may contain a small amount of silanol groups and alkoxysilane groups which do not affect the degree of hydrosilylation reaction. Herein, a small amount refers to an amount of less than 5% relative to the total number of substituents containing hydrogen atoms on silicon atoms.
The linear, branched, and resinous organohydrogen polysiloxanes described above may be used either singly or in any combination of two or more as component (B).
As component (B) of the present invention, an organohydrogen polysiloxane having a hydrogen group concentration of SiH groups of 0.1 to 10% by mass, preferably 0.1 to 5% by mass, and particularly preferably 0.1 to 3% by mass is particularly preferably used.
The viscosity of the component (B) is preferably 2 mPas to 100 mPas at 25 ℃, but any viscosity of the organohydrogen polysiloxane can be used as long as the viscosity of the curable composition of the invention when combined with the component (A) and the component (C) is 80 mPas or less as measured at 25 ℃ using an E-type viscometer.
In the curable composition of the present invention, the content of the component (B) is preferably an amount in the range of 0.1 to 5.0 mol, preferably an amount in the range of 0.2 to 5.0 mol, and particularly preferably an amount in the range of 0.5 to 2 mol, relative to 1 mol of the carbon-carbon double bond in the component (a) in the composition. By setting the amount of the silicon-bonded hydrogen atom contained in the component (B) within the above range, a curable composition excellent in curability and physical properties of a cured product after curing can be obtained. In the curable composition, the amount of the component (B) used is not hindered so that the silicon-bonded hydrogen atom in the component (B) is 10 mol or more relative to 1 mol of the carbon-carbon double bond in the component (a).
< component (C): photoactive hydrosilylation catalyst
The component (C) is a photoactive hydrosilylation catalyst for imparting a property of curing by irradiation of actinic light (actinic light), for example, ultraviolet light, to the curable composition of the present invention.
The component (C) is not particularly limited as long as it is a compound that becomes active as a hydrosilylation catalyst upon irradiation with ultraviolet light, and a photoactive platinum complex is preferably used. Specific examples of the photoactive platinum complex include: (methylcyclopentadienyl) trimethylplatinum (IV), (cyclopentadienyl) trimethylplatinum (IV), (1, 2,3,4, 5-pentamethylcyclopentadienyl) trimethylplatinum (IV), (cyclopentadienyl) dimethylethylplatinum (IV), (cyclopentadienyl) dimethylacetyl platinum (IV), (trimethylsilylcyclopentadienyl) trimethylplatinum (IV), (methoxycarbonyl cyclopentadienyl) trimethylplatinum (IV), (dimethylphenylsilylcyclopentadienyl) trimethylplatinum (IV), (1, 5-cyclooctadiene) dimethylplatinum (II), (1, 5-cyclooctadiene) diphenylplatinum (II), (1, 5-cyclooctadiene) dichloroplatinum (II), (2, 5-norbornadiene) dimethylplatinum (II), (2, 5-norbornadiene) dichloroplatinum (II), trimethylplatinum (acetylacetonate) platinum (IV), trimethylplatinum (3, 5-heptanedione) platinum (IV), trimethylplatinum (methylacetoacetate) platinum (IV), bis (2, 4-pentanedione) platinum (II), bis (2, 4-hexanedione) platinum (II), bis (2, 4-heptanedione) platinum (3), 5-heptanedione) platinum (II), bis (1-phenyl-1, 3-butanedione) platinum (II), bis (1, 3-diphenyl-1, 3-propanedione) platinum (II), bis (hexafluoroacetylacetone) platinum (II).
As the component (C), particularly preferred are cyclopentadienyl trialkylplatinum complexes and derivatives thereof in which the cyclopentadienyl ligand is substituted with an alkyl group, and (methylcyclopentadienyl) trimethylplatinum (IV) is preferred from the viewpoint of high versatility and easiness of obtaining. As the component (C), bis (2, 4-pentanedione) platinum (II) is also preferable in view of the high versatility and easiness of obtaining.
The amount of the component (C) used is a sufficient amount for increasing the curing speed of the ultraviolet-curable composition of the present invention to a desired level, and preferably an amount in the range of 1 to 500ppm, and preferably an amount in the range of 10 to 300ppm, of the platinum group metal atom in the compound of the component (C) relative to the ultraviolet-curable composition in terms of mass unit.
The curable composition of the present invention may contain a hydrosilylation reaction inhibitor together with the photoactive hydrosilylation reaction catalyst of the component (C), or may contain no hydrosilylation reaction inhibitor. The hydrosilylation reaction inhibitor is usually added to the curable composition in order to improve the pot life of the curable composition and to obtain a stable curable composition, but in the curable composition of the present invention, the hydrosilylation reaction inhibitor may not be added so as not to slow the curing time of the curable composition. However, in order to extend the pot life of the curable composition, a hydrosilylation reaction inhibitor may also be added to the composition. Hydrosilylation reaction inhibitors are well known in the art and specific examples include: alkynols such as 1-ethynylcyclohexane-1-ol, 2-methyl-3-butyn-2-ol, 3, 5-dimethyl-1-hexyn-3-ol, and 2-phenyl-3-butyn-2-ol; eneyne compounds such as 3-methyl-3-penten-1-yne and 3, 5-dimethyl-3-hexen-1-yne; methyl alkenyl siloxane oligomers such as 1,3,5, 7-tetramethyl-1, 3,5, 7-tetravinyl cyclotetrasiloxane and 1,3,5, 7-tetramethyl-1, 3,5, 7-tetrahexenyl cyclotetrasiloxane; alkynyloxy silanes such as dimethyl bis (1, 1-dimethyl-2-propynyloxy) silane and methyl vinyl bis (1, 1-dimethyl-2-propynyloxy) silane; triallyl isocyanurate compounds.
In the case where the hydrosilylation reaction inhibitor is used in the ultraviolet-curable composition of the present invention, the content of the hydrosilylation reaction inhibitor in the curable composition is not particularly limited, and is in the range of 0.0001 to 5 parts by mass, preferably in the range of 0.01 to 5 parts by mass, or in the range of 0.01 to 3 parts by mass, relative to 100 parts by mass of the total of the components (a) to (C).
< ultraviolet-curable polyorganosiloxane composition >
The ultraviolet-curable polyorganosiloxane composition of the present invention is characterized by containing the component (a), the component (B), and the component (C) as essential components, and by not containing an organic solvent, and by having a viscosity of 80mpa·s or less, preferably 30mpa·s or less, and particularly preferably having a viscosity of 10 to 80mpa·s, more preferably 10 to 30mpa·s, and still more preferably 10 to 20mpa·s, as measured at 25 ℃ using an E-type viscometer. The lower limit of the viscosity is not limited, but is usually 3 mPa.s or more. In the present specification, the absence of an organic solvent means that the content of the organic solvent is less than 0.05 mass% of the entire composition, and it is preferable that the content is not more than the analysis limit by an analysis method such as gas chromatography. In the present invention, by adjusting the molecular structure and molecular weight of the component (a) and the component (B), a desired viscosity of the composition can be achieved even without using an organic solvent.
The cured product obtained from the curable composition of the present invention can be designed so that the viscosity of the curable composition is a desired value, based on the molecular chain length of component (a), the number of uv-reactive functional groups per molecule, the position of the uv-reactive functional groups in the molecule, and the molecular structure, to obtain desired physical properties of the cured product and the curing speed of the curable composition. The cured product obtained by curing the curable composition of the present invention is also included in 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 the cured product may be a film-like coating, a molded product such as a sheet, or the composition may be injected into a specific site in an uncured state to be cured, thereby forming a filler, or may be used as a sealing material or an intermediate layer for a laminate, a display device, or the like. The cured product obtained from the composition of the present invention is particularly preferably in the form of a film-like coating, and is particularly preferably an insulating coating.
Furthermore, the curable composition of the present invention is suitable for use as a coating agent or potting agent, particularly as an insulating coating agent or potting agent for electronic devices and electrical devices.
The cured product obtained by curing the curable composition of the present invention can be designed to have a relative dielectric constant of less than 3.0, less than 2.8, or the like, as desired, and the curable composition of the present invention can also be used for forming a coating layer having a low relative dielectric constant.
When the curable composition of the present invention is used as a coating agent, the viscosity of the entire composition is preferably 80mpa·s or less, more preferably 5 to 60mpa·s, and even more preferably 10 to 30mpa·s, as measured at 25 ℃ using an E-type viscometer, in order to provide fluidity and workability suitable for application of the composition to a substrate. In order to adjust the viscosity of the curable composition as a whole to a desired viscosity, a compound having a suitable viscosity may be used as each component so that the viscosity of the composition as a whole has a desired viscosity.
[ component (D) ]
When the ultraviolet-curable polyorganosiloxane composition of the present invention is applied to the surface of a substrate as a coating agent by any method, a component (D) selected from the following components may be further added to the composition of the present invention containing the above components in order to improve the wettability of the composition to the substrate and form a coating film free from defects. As a method of applying the composition of the present invention to a substrate, an inkjet printing method is particularly preferably used. Therefore, the component (D) is a component that improves the wettability of the ultraviolet-curable polyorganosiloxane composition of the present invention to a substrate, particularly significantly improving the inkjet printing characteristics. The component (D) is at least one compound selected from the group consisting of (D1), (D2) and (D3) below.
(i) Component (D1)
Component (D1) is a nonionic surfactant which does not contain a silicon atom and is not acrylic, i.e., a nonionic surfactant of the non-acrylic type. Non-acrylic means that the surfactant does not have a (meth) acrylate group in its molecule. As the surfactant which can be used as the component (D1), there can be mentioned: the organic nonionic surfactant such as glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, alkyl glycoside, and acetylene glycol polyether, and the fluorine nonionic surfactant may be used singly or in combination. Specific examples of the component (D1) include: examples of the organic nonionic surfactant include EMULGEN series, rheodol series, surfynol 400 series, and Olfine E series, which are manufactured by Nissan chemical industries, inc., evonik Industries, and the fluorine nonionic surfactant: FC-4400 series manufactured by 3M, megafac 550 and 560 series manufactured by DIC Co., ltd.
Among them, the Surfynol 400 series and the Olfine E series are particularly preferable as the alkyl polyether.
(ii) The component (D2) is a nonionic surfactant having a silicon atom and an HLB value of 4 or less. The HLB value herein is a value indicating the degree of affinity of the surfactant for water and the organic compound, and a value (20×sum of formulae of hydrophilic units/molecular weight) defined by the Griffin method is used as the HLB value. As the hydrophilic portion, silicone polyether having polyether, glyceryl polysiloxane having (di) glycerin derivative as the hydrophilic portion, methanolic silicone having hydroxyethoxy group as the hydrophilic portion, and the like are known as silicon-containing nonionic surfactants. Among these surfactants, surfactants having an HLB value of 4 or less, that is, surfactants having a mass fraction of hydrophilic parts of 20 mass% or less are preferably used in the composition of the present invention. Among them, methanol silicone is particularly preferable.
(iii) The component (D3) is a silicone oil having a viscosity of 90 mPas or less at 25 ℃. The silicone oil may be: two-terminal trimethylsilyl-polydimethylsiloxane, two-terminal dimethylvinylsilyl-polydimethylsiloxane, two-terminal trimethylsilyl-dimethylsiloxy/methylvinylsiloxy copolymer, two-terminal dimethylvinylsilyl-dimethylsiloxy/methylvinylsiloxy copolymer, two-terminal trimethylsilyl-dimethylsiloxy/methylphenylsiloxy copolymer, two-terminal trimethylsilyl-dimethylsiloxy/diphenylsiloxy copolymer, two-terminal dimethylvinylsilyl-dimethylsiloxy/methylphenylsiloxy copolymer, two-terminal dimethylsiloxy-dimethylsiloxy/diphenylsiloxy copolymer, two-terminal dimethylsilyl-dimethylsiloxy/diphenylsiloxy copolymer, and the like, and two-terminal trimethylsilyl-dimethylsiloxy/dimethylvinylsiloxy copolymer is preferably used. The silicone oil preferably has a viscosity in the range of 2 to 50 mPas, more preferably 2 to 30 mPas, and still more preferably 5 to 20 mPas. The value of the viscosity herein is a value measured at 25℃using the rotational viscometer described in the examples.
One or a combination of two or more of the above components (D1) to (D3) may be used. The amount of the component (D) blended into the curable composition is not particularly limited, and the total amount of the component (a) and the component (B) is preferably 0.05 mass% or more and 1 mass% or less relative to the total amount of the components (D1) to (D3) (these are collectively referred to as the component (D)) based on 100 mass%. The reason for this is that if the amount of component (D) is less than 0.05 mass% relative to 100 mass% of the total amount of components (a) and (B), the effect of improving the wettability of the curable composition to the substrate may not be sufficiently obtained, and if the amount of component (C) exceeds 1 mass% relative to 100 mass% of the total amount of components (a) and (B), there is a possibility that bleeding of component (C) from the cured product may occur after curing.
As the component (D), silicone oil of the component (D3) is preferably used alone, or the component (D3) and one or more components selected from the group consisting of the component (D1) and the component (D2) are used in combination, and the component (D3) is particularly preferably used alone as the component (D).
< other additives >
In addition to the above components, further additives may be added to the curable composition of the present invention as desired. The additives listed below are examples of the additives, but are not limited thereto.
[ adhesive property-imparting agent ]
In the composition of the present invention, an adhesion promoter may be added to improve adhesion to a substrate in contact with the composition. When the curable composition of the present invention is used for applications requiring adhesion or adhesiveness to a substrate, such as a coating agent and a sealing material, it is preferable to add an adhesion-imparting agent to the curable composition of the present invention. Any known adhesion promoter may be used as long as the curing reaction of the composition of the present invention is not inhibited.
Examples of the adhesion promoter usable in the present invention include: an organosilane having a hydrosilyl group or an alkenyl group (e.g., vinyl group, allyl group), or an organosiloxane oligomer having a linear structure, branched structure, or cyclic structure having about 4 to 20 silicon atoms; an organosilane having a trialkoxysiloxy group or trialkoxysilylalkyl group and a methacryloxyalkyl group (for example, 3-methacryloxypropyl group), or an organosiloxane oligomer having a linear structure, branched structure or cyclic structure and having about 4 to 20 silicon atoms; an organosilane having an alkyl group in which a trialkoxysiloxy group or trialkoxysilylalkyl group is bonded to an epoxy group (for example, 3-glycidoxypropyl group, 4-glycidoxybutyl group, 2- (3, 4-epoxycyclohexyl) ethyl group, 3- (3, 4-epoxycyclohexyl) propyl group), or an organosiloxane oligomer having a linear structure, branched structure, or cyclic structure having about 4 to 20 silicon atoms; an organic compound having two or more trialkoxysilyl groups (e.g., trimethoxysilyl group, triethoxysilyl group); the reaction product of an aminoalkyl trialkoxysilane and an epoxy-bonded alkyltrialkoxysilane, and an epoxy-containing ethyl polysilicate, specifically, may be exemplified by: vinyl trimethoxysilane, allyl triethoxysilane, hydrogen triethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyl trimethoxysilane, 3-methacryloxypropyl triethoxysilane, 1, 6-bis (trimethoxysilyl) hexane, 1, 6-bis (triethoxysilyl) hexane, 1, 3-bis [2- (trimethoxysilyl) ethyl ] -1, 3-tetramethyl disiloxane, reactant of 3-glycidoxypropyl triethoxysilane with 3-aminopropyl triethoxysilane, condensation reactant of silanol-terminated methyl vinyl siloxane oligomer with 3-glycidoxypropyl trimethoxysilane, condensation reactant of silanol-terminated methyl vinyl siloxane oligomer with 3-methacryloxypropyl triethoxysilane, tris (3-trimethoxysilyl propyl) isocyanurate.
The amount of the adhesion promoter to be added to the curable composition of the present invention is not particularly limited, but is preferably in the range of 0.01 to 5 parts by mass, or in the range of 0.01 to 2 parts by mass, relative to 100 parts by mass of the total of the components (a) and (B), in view of the curing property of the curable composition and not promoting discoloration of the cured product.
[ other additives ]
In addition to the above-mentioned adhesiveness-imparting agent, other additives may be added to the composition of the present invention as needed in place of the adhesiveness-imparting agent. Examples of usable additives include: leveling agents, silane coupling agents, ultraviolet absorbers, antioxidants, polymerization inhibitors, fillers (functional fillers such as reinforcing fillers, insulating fillers, and thermally conductive fillers) and the like, which are not included in the materials listed as the adhesion imparting agents. Suitable additives may be added to the composition of the present invention as required. In addition, a thixotropic agent may be added to the composition of the present invention as needed, particularly when used as a potting agent or a sealing material.
[ refractive index of cured product of curable composition of the invention ]
The cured product obtained from the ultraviolet-curable polyorganosiloxane composition of the present invention has a low refractive index, and the refractive index is 1.45 or less, preferably 1.42 or less, when measured at 25 ℃ and a wavelength of 589 nm.
The composition can be prepared by uniformly mixing the components (A) to (C) and optionally other components (D). In the preparation of the present composition, various mixers or kneaders may be used for mixing at ordinary temperature, and if necessary, mixing may be performed under heating. The order of blending the components is not limited, and the components may be mixed in any order.
The present composition may be a one-liquid composition in which all the components are contained in the same container, or may be a multi-liquid composition such as a two-liquid composition to be mixed at the time of use, in view of storage stability. In particular, in the case of producing a two-part composition, it is preferable to produce a first liquid containing a part of the component (a) and the component (C) as a catalyst, and a second liquid containing a part of the component (a) and the component (B). The other optional component (D) may be contained in any liquid, and the hydrosilylation reaction inhibitor is preferably added to the second liquid side containing component (B) in view of reactivity at the time of mixing.
The composition can be cured in a relatively low temperature range (for example, a range of 15 to 80 ℃) including room temperature after irradiation with high energy rays such as ultraviolet rays. The curing reaction of the present composition may be adjusted to a desired rate according to the concentration of the catalyst metal in the component (C), the kind and content of the hydrosilylation reaction inhibitor.
[ use ]
The ultraviolet-curable polyorganosiloxane composition of the present invention is also one embodiment of the present invention, and can be cured not only by ultraviolet light but also by electron beam.
The curable composition of the present invention is low in viscosity and is particularly useful as a material for forming an insulating layer constituting various articles, particularly electronic devices and electric devices. The curable composition of the present invention can be applied to a substrate or can be formed into an insulating layer by irradiating the composition with ultraviolet light or electron beams by sandwiching at least one of the two substrates with a material through which ultraviolet light or electron beams pass. In this case, the composition of the present invention may be applied to a substrate to form a pattern, and then cured, or the composition may be applied to a substrate to leave a portion cured by irradiation of ultraviolet rays or electron beams and an uncured portion, and then the uncured portion may be removed by a solvent to form an insulating layer having a desired pattern. In particular, in the case where the cured layer of the present invention is an insulating layer, it can be designed to have a low relative 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 of a display device such as a touch panel or a display because the cured product obtained therefrom has good transparency. In this case, the insulating layer may be formed in any desired pattern as described above as needed. Accordingly, a display device such as a touch panel or a display including an insulating layer obtained by curing the ultraviolet-curable polyorganosiloxane composition of the present invention is also an aspect of the present invention.
Further, an article is coated with the curable composition of the present invention and then cured, whereby an insulating coating (insulating film) can be formed. Thus, the composition of the present invention can be used as an insulating coating agent. In addition, a cured product obtained by curing the curable composition of the present invention can be used as an insulating coating.
The insulating film formed from the curable composition of the present invention can be used for various applications. In particular, it can be used as a constituent member of an electronic device or as a material used in a process for manufacturing an electronic device. The electronic devices include electronic devices such as semiconductor devices and magnetic recording heads. For example, the curable composition of the present invention can be used as an insulating film for a multilayer wiring board of a D-RDRAM (DirectRambus Dynamic Random Access Memory: interface dynamic random access memory), a multi-chip Module (multi-chip Module), an interlayer insulating film for a semiconductor, an Etching Stopper (Etching Stopper) film, a surface protective film, a buffer coating film, a passivation film in LSI, a cover coat (cover coat) of a flexible copper-clad plate, a solder resist film, a surface protective film for an optical device, etc. in a semiconductor device such as LSI (Large Scale Integration: large scale integrated circuit), a system LSI, DRAM (Dynamic Random Access Memory: dynamic random access memory), SDRAM (Synchronous Dynamic Random Access Memory: synchronous dynamic random access memory), RDRAM (Rambus Dynamic Random Access Memory: bus dynamic random access memory).
The ultraviolet curable composition of the present invention is suitable for use as a potting agent in addition to a coating agent, and is particularly suitable for use as an insulating potting agent for electronic devices and electrical devices.
The composition of the present invention can be used particularly as a material for forming a coating layer on a substrate surface by an inkjet printing method, and in this case, the composition of the present invention particularly preferably contains the above-mentioned component (D).
The present invention will be further described with reference to examples, but the present invention is not limited to the examples.
Examples
The ultraviolet-curable polyorganosiloxane composition and the cured product thereof of the present invention are described in detail by examples. The measurement and evaluation in examples and comparative examples were performed as follows.
[ viscosity of polyorganosiloxane and curable polyorganosiloxane composition ]
The viscosity (mPas) at 25℃was measured using a rotational viscometer (VISCONIC EMD, manufactured by TOKIMEC Co., ltd.).
[ preparation of curable polyorganosiloxane composition ]
The materials in the amounts shown in table 1 below were placed in brown plastic containers and thoroughly mixed using a planetary mixer (planetary mixer) to prepare curable polyorganosiloxane compositions. [ evaluation of curability of curable polyorganosiloxane composition and production of cured product ]
About 0.2g of the curable polyorganosiloxane composition was injected between two glass substrates sandwiching a spacer of 0.18mm thickness. LED light with a wavelength of 365nm is irradiated stepwise through one glass substrate to a maximum of 4000mJ/cm 2 Energy amount (mJ/cm) of the curable composition at the stage of curing 2 ) As the amount of ultraviolet irradiation required for curing, the curability of the composition was evaluated.
A plate-like cured polyorganosiloxane product having a side of 30mm and a thickness of 0.18mm was produced under the irradiation conditions.
[ appearance of cured product obtained from curable polyorganosiloxane composition ]
The appearance of the cured polysiloxane obtained by the above method was evaluated visually.
[ refractive index of cured article obtained from curable polyorganosiloxane composition ]
The refractive index (nD) at 25℃was measured by a digital refractometer (manufactured by ATAGO, RX-7000. Alpha.).
Examples and comparative examples
Ultraviolet curable polyorganosiloxane compositions having compositions (parts by mass) shown in table 1 were prepared using the following components.
(A1) Dimethylvinylsilyl terminated polydimethylsiloxane at both ends. Viscosity: 60 mPas.
(A2) Dimethylvinylsilyl terminated polydimethylsiloxane at both ends. Viscosity: 6 mPas.
(A3) Dimethylvinylsilyl terminated polydimethylsiloxane at both ends. Viscosity: 350 mPas.
(A4) Terminal dimethylvinylsilyl-terminated branched tetrafunctional polydimethylsiloxane. Viscosity: 200 mPas.
(A5) 1, 3-divinyl-1, 3-tetramethyldisiloxane. Viscosity: 0.7 mPas.
(B1) MQ resin having dimethylsiloxy groups with a hydrogen group concentration of 1.2%.
(B2) Two-terminal trimethylsilyl-terminated polymethylhydrosiloxane having a hydrogen radical concentration of 1.6%.
(C) A catalyst masterbatch comprising the following components.
(C) The method comprises the following steps (C1)/(A2) =5/95 (mass ratio).
(C1) The method comprises the following steps Trimethyl (methylcyclopentadienyl) platinum.
TABLE 1
As shown in table 1, the ultraviolet-curable polyorganosiloxane compositions of the present invention (examples 1 to 11) have a viscosity suitable for application as a coating agent to a substrate at 25 ℃, and in particular, have excellent coatability by inkjet printing. The cured product obtained by ultraviolet irradiation is transparent and has a low refractive index. Therefore, by forming a structure combined with a layer made of a high refractive index material, improvement of light extraction efficiency can be expected. On the other hand, in the composition having no desired viscosity (comparative example 1) and the composition having a low viscosity and containing the component (A5) having two silicon atoms per molecule (comparative example 2), although the overall viscosity of the composition is suppressed, there is a problem that the inkjet printing characteristics are poor or the curability is poor, and sufficient ultraviolet curability cannot be achieved.
Industrial applicability
The ultraviolet-curable polyorganosiloxane composition of the present invention is particularly suitable for the above-mentioned applications, and is particularly useful as a material for forming an insulating layer of a display device such as a touch panel and a display.
Claims (13)
1. An ultraviolet curable polyorganosiloxane composition comprising:
(A) A polyorganosiloxane having two or more alkenyl-containing groups in one molecule and three or more silicon atoms per molecule;
(B) A polyorganosiloxane having two or more silicon-bonded hydrogen atoms in one molecule; and
(C) A photoactive hydrosilylation catalyst,
the composition does not contain an organic solvent, the viscosity of the entire composition is 80 mPas or less as measured at 25 ℃ using an E-type viscometer, and the refractive index of the cured product after curing is 1.45 or less as measured at 25 ℃ and a wavelength of 589 nm.
2. The ultraviolet curable polyorganosiloxane composition according to claim 1, wherein,
comprises a polyorganosiloxane having a viscosity of 60 mPas or less as measured at 25 ℃ using an E-type viscometer and having two or more alkenyl group-containing groups in one molecule as the component (A).
3. The ultraviolet curable polyorganosiloxane composition according to claim 1 or 2, wherein,
Comprises a polyorganosiloxane having a viscosity of 10 mPas or less as measured at 25 ℃ using an E-type viscometer and having two or more alkenyl group-containing groups in one molecule as the component (A).
4. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 3, wherein,
comprises a polyorganosiloxane having alkenyl-containing groups at both ends as component (A).
5. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 4, wherein,
the polyorganosiloxane having two or more alkenyl group-containing groups in one molecule of the component (a) has four or more silicon atoms on average per molecule.
6. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 5, wherein,
the organic groups bonded to the silicon atom other than the alkenyl-containing group of component (a) and the silicon-bonded hydrogen atom of component (B) are substantially only methyl groups.
7. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 6, wherein,
the viscosity of the entire composition measured at 25 ℃ is 5 to 60 mPas.
8. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 7, wherein,
The viscosity of the entire composition measured at 25 ℃ is 10 to 30 mPas.
9. The ultraviolet-curable polyorganosiloxane composition according to any one of claims 1 to 8, wherein,
the content of the polyorganosiloxane having an alkenyl group-containing group and having a boiling point of 1013.25 hundred Pa or less at 200 ℃ is less than 1% by mass of the entire composition.
10. The ultraviolet curable polyorganosiloxane composition according to any one of claims 1 to 9, wherein,
component (C) is an unsubstituted or alkyl-substituted cyclopentadienyl trialkylplatinum complex.
11. An insulating coating agent comprising the ultraviolet-curable polyorganosiloxane composition according to any one of claims 1 to 10.
12. A method of using the cured product of the ultraviolet-curable polyorganosiloxane composition according to any one of claims 1 to 10 as an insulating coating.
13. A display device comprising a layer composed of the cured product of the ultraviolet-curable polyorganosiloxane composition according to any one of claims 1 to 10.
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| JP2020-187166 | 2020-11-10 | ||
| JP2020187166 | 2020-11-10 | ||
| PCT/JP2021/041216 WO2022102622A1 (en) | 2020-11-10 | 2021-11-09 | Ultraviolet-curable organopolysiloxane composition and use therefor |
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| JP2003213132A (en) * | 2002-01-23 | 2003-07-30 | Shin Etsu Chem Co Ltd | Organopolysiloxane gel composition |
| JP2005068268A (en) * | 2003-08-22 | 2005-03-17 | Ge Toshiba Silicones Co Ltd | Curable composition for optical materials |
| JP2010285517A (en) * | 2009-06-10 | 2010-12-24 | Kaneka Corp | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
| JP2019014801A (en) * | 2017-07-05 | 2019-01-31 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Photocurable polyorganosiloxane composition |
| CN109929252A (en) * | 2017-12-19 | 2019-06-25 | 信越化学工业株式会社 | Ultraviolet-curing resin composition, bonding agent and solidfied material |
| JP2019210351A (en) * | 2018-06-01 | 2019-12-12 | 信越化学工業株式会社 | Ultraviolet-curable liquid organopolysiloxane composition for image display device and curing method of the composition, lamination method of image display device member, and image display device |
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| JPS62591U (en) | 1985-06-19 | 1987-01-06 | ||
| JP6981163B2 (en) | 2017-10-13 | 2021-12-15 | Jsr株式会社 | Curable composition |
| JP7235482B2 (en) | 2018-04-20 | 2023-03-08 | 積水化学工業株式会社 | Photocurable resin composition for electronic devices |
| JP2020026515A (en) | 2018-08-10 | 2020-02-20 | Jsr株式会社 | Curable composition and compound |
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- 2021-11-09 WO PCT/JP2021/041216 patent/WO2022102622A1/en active Application Filing
- 2021-11-09 CN CN202180070730.7A patent/CN116348556A/en active Pending
- 2021-11-09 JP JP2022561942A patent/JPWO2022102622A1/ja active Pending
- 2021-11-09 KR KR1020237018571A patent/KR20230106638A/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003213132A (en) * | 2002-01-23 | 2003-07-30 | Shin Etsu Chem Co Ltd | Organopolysiloxane gel composition |
| JP2005068268A (en) * | 2003-08-22 | 2005-03-17 | Ge Toshiba Silicones Co Ltd | Curable composition for optical materials |
| JP2010285517A (en) * | 2009-06-10 | 2010-12-24 | Kaneka Corp | Photocurable composition, and insulating thin film and thin film transistor obtained using the same |
| JP2019014801A (en) * | 2017-07-05 | 2019-01-31 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Photocurable polyorganosiloxane composition |
| CN109929252A (en) * | 2017-12-19 | 2019-06-25 | 信越化学工业株式会社 | Ultraviolet-curing resin composition, bonding agent and solidfied material |
| JP2019210351A (en) * | 2018-06-01 | 2019-12-12 | 信越化学工業株式会社 | Ultraviolet-curable liquid organopolysiloxane composition for image display device and curing method of the composition, lamination method of image display device member, and image display device |
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| JPWO2022102622A1 (en) | 2022-05-19 |
| KR20230106638A (en) | 2023-07-13 |
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