KR101705613B1 - Siloxane resin composition for coating and cured materials for coating using the same - Google Patents
Siloxane resin composition for coating and cured materials for coating using the same Download PDFInfo
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- KR101705613B1 KR101705613B1 KR1020160023266A KR20160023266A KR101705613B1 KR 101705613 B1 KR101705613 B1 KR 101705613B1 KR 1020160023266 A KR1020160023266 A KR 1020160023266A KR 20160023266 A KR20160023266 A KR 20160023266A KR 101705613 B1 KR101705613 B1 KR 101705613B1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
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- 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
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- 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
Abstract
There is provided an optical material or a coating siloxane resin composition for an electric material obtained by copolymerizing a monomer containing a silane compound containing a cyclic siloxane group and a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group. The siloxane resin composition can exhibit excellent light transmittance and heat resistance. Accordingly, it can be easily used as an optical material and an electric material, and can be particularly useful as a film coating material, an LED encapsulating material, and the like. In addition, the siloxane resin composition for coating can show an excellent curing degree of 8H or more. Accordingly, when a cured product manufactured using the cured product is used, it can be widely used in various industries such as a display, an optical lens, a transparent plate of a large building, and an automobile industry in place of conventional glass.
Description
The present invention relates to a novel siloxane resin composition for coating, and a cured product for coating using the same.
Silicon molecules having a hydrogen-silicon bond can be cured through a hydrogen-silylation reaction, and thus they have been actively studied as cross-linking agents capable of producing organosilicon compounds having various structures. The hydrogen-silylation reaction is one of the very simple and useful methods for producing a silicone cured product by heat, and can be used to produce a cured product having few by-products under a small amount of catalyst. Specifically, various hydrogenated organosilicon monomers having a desired functional group can be synthesized through the hydrogen-silylation reaction, and cured products can be prepared through cross-linking of the organic hydrogen-silicon monomers.
On the other hand, a composition having various shapes can be prepared by adding an organic material or an inorganic material to the hydrogen-silicon compound, and a composition having various physical properties can be produced through cross-linking between different molecules. Accordingly, optical and / or electrical materials such as high refractive index and high strength can be prepared by using the composition containing the hydrogen-silicon compound, the organic substance and / or the inorganic substance. In particular, the composition comprising the organohydrogensilicon compound is very transparent without any by-products and can be readily used as an optical and / or electrical material.
Accordingly, studies on a siloxane resin composition that can be used as an optical and / or electric material have been actively carried out, but it is not enough to realize a siloxane resin composition exhibiting excellent light transmittance, heat resistance and hardness.
Therefore, it is urgently required to develop a novel coating siloxane resin composition having excellent physical properties and a cured product for coating using the same.
Embodiments of the present invention are intended to provide a coating siloxane resin composition exhibiting excellent physical properties.
In another embodiment of the present invention, there is provided a cured product for coating prepared using the siloxane resin composition.
According to still another embodiment of the present invention, there is provided a process for preparing the coating siloxane resin composition and the coated cured product.
In one embodiment of the present invention, an optical material obtained by copolymerizing a monomer containing a silane compound containing a cyclic siloxane group and a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group, or a siloxane for coating for an electric material As the resin composition, the monomer containing the cyclic siloxane group-containing cyclic siloxane group has at least one structure selected from the group consisting of the structures represented by the following formulas (1), (2) and (3), and includes the aliphatic epoxy group and the alkoxy group Wherein the monomer containing a silane compound having a structure represented by the following formula (4) is provided.
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
(Wherein R 1 is a C1 to C7 linear, branched or cyclic alkyl group containing an aliphatic cyclic epoxy group, the alicyclic epoxy group is a structure in which the C3 to C6 cycloalkyl group has an epoxy group, and R 2 is a C1 to C7 linear, branched or cyclic alkyl group, and m is an integer of 0 to 3.)
In an exemplary embodiment, the silane compound having an aliphatic cyclic epoxy group and an alkoxy group represented by the general formula (4) is 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane or 2- (3,4-epoxycyclo Hexyl) ethyl triethoxysilane.
In an exemplary embodiment, the coating siloxane resin composition comprises a monomer containing a silane compound containing the cyclic siloxane group, a monomer containing a silane compound containing the aliphatic epoxy group and an alkoxy group, Lt; RTI ID = 0.0 > alkoxysilane < / RTI >
[Chemical Formula 5]
(Wherein R 3 represents a C 1 to C 20 alkyl group, a C 3 to C 8 cycloalkyl group, a C 2 to C 20 alkenyl group, a C 2 to C 20 alkynyl group, a C 6 to C 20 aryl group, an acrylic group, a methacrylic group, A halogen group and an amino group, R 4 is a C1 to C7 linear, branched or cyclic alkyl group, and q is an integer of 0 to 3.)
In an exemplary embodiment, the alkoxysilane compound represented by Formula 5 may be at least one selected from the group consisting of tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, dimethyldimethoxysilane , Dimethyldiethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, triphenylmethoxysilane, triphenylethoxysilane, ethyltriethoxy Silane, propylethyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, N- (3-acryloxy-2-hydroxypropyl) -3-aminopropyltrimethoxysilane 3-aminopropyltriethoxysilane, N- (3-acryloxy-2-hydroxypropyl) -3-aminopropyltripropoxysilane, 3 - acryloxypropylmethylbis (trimethoxy) silane, 3-acryl (Meth) acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, 3-acryloxypropyltripropoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, 3- (Meth) acryloxypropyltrimethoxy silane, N- (2-aminoethyl) -3-aminopropyltriethoxy silane, N- At least one member selected from the group consisting of silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, chloropropyltrimethoxysilane, chloropropyltriethoxysilane and heptadecafluorodecyltrimethoxysilane, .
In an exemplary embodiment, the siloxane resin composition may include 1 to 50 parts by weight of an acid anhydride compound containing at least one acid anhydride group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
In an exemplary embodiment, the acid anhydride compound comprises at least one member selected from the group consisting of phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nadic methyl anhydride, clorodic anhydride and pyromellitic anhydride. can do.
In an exemplary embodiment, 1 to 50 parts by weight of a compound having an alicyclic epoxy group per 100 parts by weight of the silane compound containing the cyclic siloxane group may be further included.
In an exemplary embodiment, the compound having an aliphatic cyclic epoxy group is selected from the group consisting of 4-vinylcyclohexene dioxide, cyclohexene vinyl monoxide, (3,4-epoxycyclohexyl) methyl 3,4-epoxycyclohexylcarboxylate, 3 Epoxycyclohexylmethyl methacrylate, bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexanecarboxylate and 2- (3,4-epoxycyclohexyl) -1, Dioxolane, and 3-dioxolane.
In an exemplary embodiment, 1 to 50 parts by weight of a compound having an oxetane group per 100 parts by weight of the silane compound containing the cyclic siloxane group may be further included.
In an exemplary embodiment, the compound having an oxetane group is selected from the group consisting of 3-methyloxetane, 2-methyloxetane, 3-oxethanol, 2-methylene oxetane, 3,3-oxetane dimethanethiol, 4- (2,2-dimethylpropyl) -3-methyl-3-oxetanemethanamine, N- (1,2-dimethylbutyl) -3-methyl (3-ethyloxetan-3-yl) methoxy] butan-1-ol, 3- Ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, xylenes bisoxetane and 3-ethyl-3 [[[3-ethyloxetan-3-yl] methoxy] methyl] One or more selected from the group.
In an exemplary embodiment, 0.1 to 10 parts by weight of a polymerization initiator may be further added to 100 parts by weight of the silane compound containing the cyclic siloxane group.
In an exemplary embodiment, the polymerization initiator may include at least one member selected from the group consisting of an onium salt, an organic metal salt, an amine, and an imidazole.
In an exemplary embodiment, the siloxane resin composition may further include at least one member selected from the group consisting of an organic solvent, an antioxidant, a leveling agent, and a coating aid.
In an exemplary embodiment, the copolymerization can be carried out under water and catalytic conditions.
In an exemplary embodiment, the catalyst is selected from the group consisting of hydrochloric acid, acetic acid, hydrogen fluoride, nitric acid, sulfuric acid, chlorosulfonic acid, iodic acid, pyrophosphoric acid, ammonia, potassium hydroxide, sodium hydroxide, barium hydroxide, imidazole, And may include at least one selected.
In another embodiment of the present invention, there is provided a polymerization method of a coating siloxane resin composition for polymerizing the coating siloxane resin composition.
In an exemplary embodiment, the polymerization can be performed by light irradiation or heating.
In another embodiment of the present invention, there is provided a coating cured product formed by curing the coating siloxane resin composition.
In an exemplary embodiment, the coating cured product may be used as a film coating or an LED encapsulant.
In another embodiment of the present invention, there is provided a process for producing a cured product for coating to cure the coating siloxane resin composition.
The siloxane resin composition for coating according to one embodiment of the present invention can exhibit excellent light transmittance and heat resistance. Accordingly, it can be easily used as an optical material and an electric material, and can be particularly useful as a film coating material, an LED encapsulating material, and the like.
When the above-mentioned siloxane resin composition for coating is cured, an excellent curing degree of 5H or more can be obtained. Accordingly, when a cured product prepared using the coating siloxane resin composition is used, it can be widely used in various industries such as a display, an optical lens, a transparent plate of a large building, and an automobile industry in place of conventional glass.
In the present specification, the hydrolysis-condensation reaction is a generic term for the hydrolysis and condensation reaction which proceeds in succession. The fact that a substance undergoes a hydrolysis-condensation reaction means that the substance is hydrolyzed to produce a hydrolysis product, Means that the decomposition product is condensation-reacted.
As used herein, the term "alkyl" means a linear or branched, unsubstituted or substituted saturated hydrocarbon group, such as methyl, ethyl, propyl, isopropyl, isobutyl, sec- tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, tridecyl, pentadecyl and heptadecyl and the like. Alkyl may be one that does not include carbon atoms of the case may include an alkyl group having an alkylene unit having a carbon number of 1 to 30, C 1 ~ C30 alkyl substituted with a substituent.
As used herein, the term "alkoxy" may include, for example, a C1 to C20 alkoxy group in the form of an alkyl group and an oxygen atom as defined above, and includes, for example, methoxy, ethoxy, propoxy, Butoxy, pentoxy, hexyloxy, heptyloxy, octoxy, nonoxy, decoxy, and the like, or all possible isomers thereof.
In one embodiment of the present invention, an optical material obtained by copolymerizing a monomer containing a silane compound containing a cyclic siloxane group and a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group, or a siloxane for coating for an electric material A resin composition is provided.
The siloxane resin composition for coating according to an embodiment of the present invention is obtained by copolymerizing a silane compound containing a cyclic siloxane group and a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group, - condensation reaction. At this time, the siloxane resin composition is formed through dense crosslinking of the silane compound containing the cyclic siloxane group and the silane compound containing the aliphatic epoxy group and the alkoxy group, so that a compound having high surface hardness, excellent light transmittance and heat resistance is obtained Loses.
In an exemplary embodiment, the silane compound containing the cyclic siloxane group may have a structure represented by the following formulas (1) to (3).
[Chemical Formula 1]
(2)
(3)
On the other hand, the monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group may have a structure represented by the following formula (4).
[Chemical Formula 4]
Wherein R 1 is a C1 to C7 linear, branched or cyclic alkyl group containing an aliphatic cyclic epoxy group, the aliphatic cyclic epoxy group is a structure in which the C3 to C6 cycloalkyl group has an epoxy group, and R 2 Is a C1 to C7 linear, branched or cyclic alkyl group, and m is an integer of 0 to 3.
In an exemplary embodiment, the silane compound having an aliphatic cyclic epoxy group and an alkoxy group represented by the general formula (4) is 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane or 2- (3,4-epoxycyclo Hexyl) ethyl triethoxysilane.
On the other hand, in an exemplary embodiment, the coating siloxane resin composition comprises a monomer containing a silane compound containing the cyclic siloxane group, a monomer containing a silane compound containing the aliphatic epoxy group and an alkoxy group, May be a material obtained by ternary copolymerizing a monomer containing an alkoxysilane compound represented by the formula
[Chemical Formula 5]
In the general formula (5), R 3 represents a C1 to C20 alkyl group, a C3 to C8 cycloalkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C20 aryl group, an acrylic group, a methacrylic group, a halogen And R 4 is a C1 to C7 linear, branched or cyclic alkyl group, and q is an integer of 0 to 3.
In an exemplary embodiment, the alkoxysilane compound represented by Formula 5 may be at least one selected from the group consisting of tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, dimethyldimethoxysilane , Dimethyldiethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, triphenylmethoxysilane, triphenylethoxysilane, ethyltriethoxy Silane, propylethyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, N- (3-acryloxy-2-hydroxypropyl) -3-aminopropyltrimethoxysilane 3-aminopropyltriethoxysilane, N- (3-acryloxy-2-hydroxypropyl) -3-aminopropyltripropoxysilane, 3 - acryloxypropylmethylbis (trimethoxy) silane, 3-acryl (Meth) acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, 3-acryloxypropyltripropoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, 3- (Meth) acryloxypropyltrimethoxy silane, N- (2-aminoethyl) -3-aminopropyltriethoxy silane, N- At least one member selected from the group consisting of silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, chloropropyltrimethoxysilane, chloropropyltriethoxysilane and heptadecafluorodecyltrimethoxysilane, .
As described above, the coating siloxane resin composition of the present invention comprises at least one selected from the group consisting of the silane compound containing the cyclic siloxane group, the silane compound containing the aliphatic epoxy group and the alkoxy group, and the alkoxysilane compound represented by the formula (5) And the like. Preferably, the coating siloxane resin composition of the present invention contains at least one silane compound selected from the group consisting of the silane compound containing the cyclic siloxane group, the silane compound containing the aliphatic epoxy group and the alkoxy group, and the alkoxysilane compound represented by the formula Can be obtained by hydrolysis-condensation reaction with the above-mentioned water under catalytic conditions.
In an exemplary embodiment, the hydrolysis-condensation reaction may be conducted by stirring at room temperature for about 12 hours to about 7 days, and may be carried out at a temperature of about 60 ° C to about 100 ° C for about 2 hours to about 72 hours Lt; / RTI >
On the other hand, the hydrolysis-condensation reaction involves the formation of by-products, alcohol and water. By removing it, the reverse reaction can be reduced and the reaction can be induced, thereby controlling the reaction rate.
In addition, the alcohol and water remaining at the end of the hydrolysis-condensation reaction may be removed by heating to a temperature of about 60 ° C to about 150 ° C for about 10 minutes to about 60 minutes under reduced pressure.
In an exemplary embodiment, the catalyst used in the hydrolysis-condensation reaction includes an acid catalyst such as hydrochloric acid, acetic acid, hydrogen fluoride, nitric acid, sulfuric acid chlorosulfonic acid, iodic acid, and phosphorous acid; Basic catalysts such as ammonia, potassium hydroxide, sodium hydroxide, barium hydroxide and imidazole; And ion exchange resins such as Amberite IRA-400 and IRA-67.
In the case of the acid catalyst and the base catalyst, about 0.0001 to about 0.1 part by weight of the cyclic siloxane group-containing silane compound may be added in an amount of about 0.0001 to about 0.1 part by weight, But may not be limited to, about 1 to about 10 parts by weight based on about 100 parts by weight of the silane compound containing the cyclic siloxane group.
Meanwhile, the coating siloxane resin composition of the present invention may further comprise an acid anhydride compound containing at least one acid anhydride group. As a result, the viscosity and curing rate of the silane compound containing the cyclic siloxane group and / or the siloxane resin composition for coating can be improved.
Exemplary Embodiments The siloxane resin composition for coating may contain 1 to 50 parts by weight of the acid anhydride compound per 100 parts by weight of the silane compound containing the cyclic siloxane group.
In an exemplary embodiment, the acid anhydride compound is at least one selected from the group consisting of phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nadic methyl anhydride, clorenedic anhydride, and pyromellitic anhydride However, the present invention is not limited thereto.
The coating siloxane resin composition of the present invention may further comprise a compound having an aliphatic cyclic epoxy group. Thus, the viscosity of the silane compound containing the cyclic siloxane group and / or the siloxane resin composition for coating can be controlled and the processing can be more easily controlled.
The compound having an aliphatic cyclic epoxy group may be a photopolymerizable or thermally polymerizable monomer, and the compound having an aliphatic cyclic epoxy group is, for example, 4-vinylcyclohexene dioxide, cyclohexene vinyl monoxide, (3,4 (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexylmethyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, 3,4-epoxycyclohexylmethyl methacrylate, Carboxylate, and 2- (3,4-epoxycyclohexyl) -1,3-dioxolane.
In an exemplary embodiment, the coating siloxane resin composition may include 1 to 50 parts by weight of the compound having the aliphatic cyclic epoxy group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
In addition, the coating siloxane resin composition of the present invention may further contain a compound having an oxetane group. As a result, the viscosity, curing rate and the like of the coating siloxane resin composition can be improved.
In an exemplary embodiment, the coating siloxane resin composition may further contain 1 to 50 parts by weight of the compound having an oxetane group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
In an exemplary embodiment, the compound having an oxetane group is selected from the group consisting of 3-methyloxetane, 2-methyloxetane, 3-oxethanol, 2-methylene oxetane, 3,3-oxetane dimethanethiol, 4- (2,2-dimethylpropyl) -3-methyl-3-oxetanemethanamine, N- (1,2-dimethylbutyl) -3-methyl (3-ethyloxetan-3-yl) methoxy] butan-1-ol, 3- Ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, xylenes bisoxetane and 3-ethyl-3 [[[3-ethyloxetan-3-yl] methoxy] methyl] And may include, but are not limited to, one or more selected from the group.
In one embodiment of the present invention, the coating siloxane resin composition may further comprise a polymerization initiator for polymerization of the silane compound containing the cyclic siloxane group and / or polymerization of the siloxane resin composition for coating, For example, a photopolymerization initiator such as an onium salt or an organic metal salt and a thermal polymerization initiator such as amine or imidazole can be used.
In an exemplary embodiment, the coating siloxane resin composition may include about 0.1 to about 10 parts by weight of the polymerization initiator relative to about 100 parts by weight of the siloxane resin having the cyclic siloxane group.
In an exemplary embodiment, in the case of the photopolymerization initiator, an arylsulfonium hexafluoroantimonate salt, an arylsulfonium hexafluorophosphate salt, a diphenyliodonium hexafluorophosphate salt, diphenyliodonium But are not limited to, hexafluoroantimonate salts, ditolyl iodonium hexafluorophosphate salts, and 9- (4-hydroxyethoxyphenyl) cyan sulfonium hexafluorophosphate salts. have.
On the other hand, in the case of the thermal polymerization initiator, 3-methyl-2-butenyltetramethylenesulfonium hexafluoroantimonate salt, ytterbium (III) trifluoromethanesulfonate salt, samarium (III) (III) trifluoromethanesulfonate salts, dicyclopentanylsulfonate salts, dicyclopentadiene sulfonate salts, dicyclopentadiene sulfonate salts, dicyclopentadiene sulfonate salts, Ethyl-4-methylimidazole, and the like. Examples of the salt include, but are not limited to, ethyltriphenylphosphonium bromide, benzyldimethylamine, dimethylaminomethylphenol, triethanolamine, N-butylimidazole, .
In one embodiment of the present invention, the coating siloxane resin composition further comprises an organic solvent for controlling the viscosity of the silane compound containing the cyclic siloxane group to facilitate workability and to control the thickness of the coating film .
In an exemplary embodiment, examples of the organic solvent include ketones such as acetone, methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, and cyclohexanone, and organic solvents such as methyl cellosolve, ethyl cellosolve, cellosolve acetate, butyl cell An ether such as ethyl ether, dioxane or tetrahydrofuran, or an ether such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, isopentyl acetate Alcohols such as butanol, 2-butanol, isobutyl alcohol and isopropyl alcohol; and alcohols such as dichloromethane, chloroform, dichloroethane, trichloroethane, tetrachloroethane, dichloroethylene, trichlorethylene, Halogenated hydrocarbons such as tetrachlorethylene, chlorobenzene and ortho-dichlorobenzene, and halogenated hydrocarbons such as n-hexane, cyclohexanol, methylcyclohexanol, benzene, toluene, There may be mentioned hydrocarbons such as alkylene example.
In one embodiment of the present invention, the coating siloxane resin composition may further include an antioxidant for suppressing an oxidation reaction resulting from the polymerization reaction of the silane compound containing the cyclic siloxane group.
In an exemplary embodiment, the antioxidant may include, but not limited to, at least one selected from the group consisting of phenolic, phosphite, aminium, thioester, and the like.
Specifically, the phenolic antioxidant may be tetrakis [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane, 1,2- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- ( Di-tert-butyl-4-hydroxyphenyl) propionate, isotridecyl-3- (3,5- (3,5-di-tert-butyl-4-hydroxyhydrocinnamamide), benzenepropanoic acid, 3,5-bis (1,1-dimethylethyl) -4- Butylidene bis (4,6-di-tert-butylphenol), 1,3,5-trimethyl-2,4,6-tris (3,5- ) Benzene, 4,6-bis (octylthiomethyl) -o-cresol, 1,3,5-tris (2,6-dimethyl-3-hydroxy- , 2'-methylenebis (4-methyl-6-tert-butylphenol), triethylene glycol 2,5-di-tert-amyl-hydroquinone, hexamethylene bis [3- (3,5-di-tert-butylphenyl) butyl-4-hydroxyphenyl) propionate], tris- (3,5-di-tert- butylhydroxybenzyl) isocyanurate, 4,4'-thiobis (6-tert- m-cresol), 4,4'-butylidenebis (6-tert-butyl-3-methylphenol), and the phosphite antioxidant may be tris (2,4- (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, triphenylphosphite, triisodecylphosphite, diphenyl isodecylphosphite, 2 -Ethylhexyldiphenylphosphite, poly (dipropylene glycol) phenylphosphite, tris (nonylphenyl) phosphite, etc. The aminic antioxidant may be 2,2,4-trimethyl-1,2-dihydroquinoline Oligo And the thioester antioxidant may be selected from the group consisting of pentaerythritol tetrakis (3-laurylthiopropionate), distearyl thiodipropionate, dilauryl thiodipropionate, ditridecyl thiodipropionate And so on.
In an exemplary embodiment, the coating siloxane resin composition may comprise from about 0.1 to about 10 parts by weight of the antioxidant, relative to about 100 parts by weight of the silane compound comprising the cyclic siloxane group.
In one embodiment of the present invention, the coating siloxane resin composition may further include a leveling agent or a coating aid.
As described above, the siloxane resin composition for coating according to one embodiment of the present invention can exhibit excellent light transmittance and heat resistance. Accordingly, it can be easily used as an optical material and an electric material, and can be particularly useful as a film coating material, an LED encapsulating material, and the like.
In addition, the above-mentioned siloxane resin composition for coating can show an excellent curing degree of 5H, more specifically 8H or more. Accordingly, when a cured product prepared using the coating siloxane resin composition is used, it can be widely used in various industries such as a display, an optical lens, a transparent plate of a large building, and an automobile industry in place of conventional glass.
Further, in one embodiment of the present invention, there is provided a polymerization method of a coating siloxane resin composition for polymerizing the coating siloxane resin composition. Thereby, the polymerized coating siloxane resin composition can be formed.
In an exemplary embodiment, the polymerization may comprise a light irradiation or heating step.
Also, in one embodiment of the present invention, there is provided a cured product for coating formed by curing the above-mentioned coating siloxane resin composition and a method for producing the same.
In an exemplary embodiment, the polymerized coating siloxane resin composition may be subjected to a molding step such as coating, casting, or molding, followed by a photo-curing step or a heat treatment step to produce a cured product for coating having a high surface hardness have.
In the exemplary embodiment, in the case of the photocuring process, the homogeneous curing density can be obtained through light irradiation and subsequent heat treatment, which can be performed at a temperature in the range of about 50 ° C to 250 ° C.
On the other hand, in the case of the heat treatment process, the heat treatment may be performed at a temperature ranging from about 50 ° C to 250 ° C. If the heat treatment temperature is higher than about 250 ° C, the bonds of the organic period of action may be destroyed, and if the temperature is lower than about 50 ° C, the polymerization may not be performed well.
In an exemplary embodiment, the coating cured product may be used as a film coating, an LED encapsulant, or the like.
The siloxane resin composition for coating according to one embodiment of the present invention can exhibit excellent light transmittance and heat resistance. Accordingly, it can be easily used as an optical material and an electric material, and can be particularly useful as a film coating material, an LED encapsulating material, and the like.
Further, when the above-mentioned siloxane resin composition for coating is cured, excellent curing degree of 8H or more can be shown. Accordingly, when a cured product prepared using the coating siloxane resin composition is used, it can be widely used in various industries such as a display, an optical lens, a transparent plate of a large building, and an automobile industry in place of conventional glass.
Hereinafter, embodiments of the present invention will be described in detail. The embodiments of the present invention are described for illustrative purposes only, and the technical idea of the present invention and its constitution and application are not limited thereby.
(1) Example 1: Synthesis of Siloxane Resin Composition a (Binary Copolymer)
Bis (2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane (Formula 4) (100 g, 406 mmol) (30 g, 41 mmol) was placed in a 1000-ml three-neck round-bottomed flask, to which barium hydride A solution obtained by dissolving a solution of a solution of the compound (10 g, 556 mmol) in water (0.1 g, 0.528 mmol) was added at room temperature, and then the temperature was raised to 70 ° C. and the mixture was stirred for 7 hours. Subsequently, methyl isobutyl ketone (200 g) was added to dilute the reaction product, and water (200 g) was added thereto. The mixture was stirred at room temperature for 30 minutes, and the water layer and the organic layer were separated. Water (200 g) was added to the organic layer once again and stirred at room temperature for 30 minutes. The water layer and the organic layer were separated, and the water layer was discarded and only the organic layer was taken. The obtained organic layer was filtered using a 1 μm Teflon filter, and the volatile components and the organic solvent were removed by reducing the pressure at 120 ° C. to obtain an epoxy siloxane resin (siloxane resin composition a, 61 g).
(2) Example 2: Synthesis of Siloxane Resin Composition b (Binary Copolymer)
Methyl-3,7-bis [(2-trimethoxysilylethyl) -methyl] cyclotetrasiloxane having the structure of the formula (I) Methyl] -3,7-bis (methyl) -5 - [(2- (3,4-epoxycyclohexyl) ethyl] Trimethyloxysilylethyl) -methyl] cyclotetrasiloxane (21 g, 41 mmol) was used in place of the siloxane resin composition (b) (57 g).
(3) Example 3: Synthesis of Siloxane Resin Composition c (Binary Copolymer)
Methyl-3,7-bis [(2-trimethoxysilylethyl) -methyl] cyclotetrasiloxane having the structure of the formula (I) (3,4-epoxycyclohexyl) ethyl-methyl] -3,7-bis (octyl-methyl) -5 - [( Trimethylsilylacetyl) -methyl] cyclotetrasiloxane (30 g, 41 mmol) was used as the initiator in the same manner as in Example 1 to obtain an epoxy siloxane resin (siloxane resin composition c, 59 g) .
(4) Example 4: Siloxane resin composition d Synthesis (terpolymer)
(100 g, 406 mmol), methyltrimethoxysilane (5) (5 g, 37 mmol) and the compound of formula (1) as a reactant were added to a solution of 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane Methyl] -3,7-bis [(2-trimethoxysilylethyl) -methyl] cyclotetrasiloxane (30 g, 41 mmol) was placed in a 1000-ml three-necked round-bottom flask and a solution of barium hydroxide monohydrate (0.1 g, 0.528 mmol) in water (H2O, 10.2 g, 566.7 mmol) was added at room temperature, The temperature was raised to 70 DEG C and the mixture was stirred for 7 hours. Subsequently, methyl isobutyl ketone (200 g) was added to dilute the reaction product, and water (200 g) was added thereto. The mixture was stirred at room temperature for 30 minutes, and the water layer and the organic layer were separated. Water (200 g) was added to the organic layer once again and stirred at room temperature for 30 minutes. The water layer and the organic layer were separated, and the water layer was discarded and only the organic layer was taken. The obtained organic layer was filtered using a 1 μm Teflon filter, and the volatile components and the organic solvent were removed by reducing the pressure at 120 ° C. to obtain an epoxy siloxane resin (siloxane resin composition d, 62 g).
(5) Example 5: Synthesis of siloxane resin composition e (terpolymer)
(100 g, 406 mmol), methyltrimethoxysilane (5) (5 g, 37 mmol) and the compound of formula (3) as a reactant were added to a solution of 2- (3,4- (Octyl-methyl) -5 - [(2-trimethoxysilylethyl) -methyl] cyclotetrasiloxane having the structure of 1- [2- (3,4-epoxycyclohexyl) ethyl- Polymerization was conducted in the same manner as in Example 4 except that siloxane (30 g, 41 mmol) was used to obtain an epoxy siloxane resin (siloxane resin composition e, 63 g).
(6) Comparative Example 1: Synthesis of siloxane resin compound
(100 g, 406 mmol) of 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane (Formula 4) was placed in a 1000-ml three-necked round-bottomed flask, and barium hydroxide monohydrate , 0.528 mmol) in water (10 g, 556 mmol) was added at room temperature, the temperature was raised to 70 ° C and the mixture was stirred for 7 hours. Subsequently, methyl isobutyl ketone (200 g) was added to dilute the reaction product, and water (200 g) was added thereto. The mixture was stirred at room temperature for 30 minutes, and the water layer and the organic layer were separated. Water (200 g) was added to the organic layer once again and stirred at room temperature for 30 minutes. The water layer and the organic layer were separated, and the water layer was discarded and only the organic layer was taken. The obtained organic layer was filtered using a 1 μm Teflon filter, and the volatile components and the organic solvent were removed by reducing the pressure at 120 ° C. to obtain an epoxy siloxane resin (45 g of the siloxane resin composition of Comparative Example 1).
(7) Comparative Example 2: Synthesis of siloxane resin compound
Methyl-3,7-bis [(2-trimethoxysilylethyl) -methyl] cyclotetrasiloxane having the structure of the formula (I) A solution of barium hydroxide monohydrate (0.05 g, 0.264 mmol) in water (5 g, 278 mmol) was added thereto at room temperature, followed by addition of a siloxane (100 g, 136 mmol) The temperature was raised to 70 ° C and the mixture was stirred for 7 hours. Subsequently, methyl isobutyl ketone (200 g) was added to dilute the reaction product, water (200 g) of H 2 O was added thereto, stirred at room temperature for 30 minutes, and the water layer and the organic layer were separated. . Water (200 g) was added to the organic layer once again and stirred at room temperature for 30 minutes. The water layer and the organic layer were separated, and the water layer was discarded and only the organic layer was taken. The obtained organic layer was filtered using a 1 μm Teflon filter, and the volatile component and the organic solvent were removed by reducing the pressure at 120 ° C. to obtain an epoxy siloxane resin (37 g of the siloxane resin composition of Comparative Example 2).
(8) Comparative Example 3
PC-1000 (Polyset Company), a siloxane resin containing aliphatic cyclic epoxy, was used.
Experimental Example 1
To photopolymerize the siloxane resin compositions (a, b, c, d, and e), triphenylsulfonium hexafluoroantimonate salt as a polymerization initiator was added in an amount of 3 parts by weight relative to the resin. Octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate and tris (nonylphenyl) phosphite as an antioxidant to inhibit the oxidation reaction that may occur in the polymerization reaction 1.5 parts by weight and 3.5 parts by weight, respectively, were added to obtain a mixture containing each siloxane resin composition.
The mixture containing the siloxane resin composition according to Examples 1 to 5 was coated with methyl ethyl ketone, an organic solvent, on the PET surface in a thickness of 20 μm and 50 μm, cured at 80 ° C. for 10 minutes, UV curing lamp at 400 mj for 3 minutes for 1 minute and photo-cured. Then, additional heat treatment was carried out at 85 ℃ and 85% RH for 1 hour to prepare siloxane coated cured product Respectively.
The surface hardness of the siloxane-coated cured product obtained in the above Example was measured using a pencil hardness meter according to JIS K5600 and the initial light transmittance at a wavelength of 550 nm and the initial light transmittance at 120 nm using a UV / VIS / NIR spectrum analyzer Nippon Denshoku Corporation Lt; 0 > C for 500 hours in air, and the results are shown in Table 1 below.
As a comparative example, the resin compound obtained in Comparative Examples 1 and 2 and the siloxane resin of Comparative Example 3 were used instead of the siloxane resin compositions (a, b, c, d and e) used in Experimental Example 1, The mixture was prepared in the same manner and coated to prepare a coated cured product. Then, their hardness and light transmittance were measured and shown together in Table 1 below.
Resin composition
The monomer of the resin composition
Light transmittance
(1) As shown in Table 1, when the siloxane resin composition obtained by two-component polymerization of a monomer containing a silane compound containing a cyclic siloxane group and a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group is cured (Examples 1 to 5) were confirmed to have much superior surface hardness and light transmittance as compared with the case where the material obtained by polymerizing the monomer alone was cured (Comparative Examples 1 to 3).
Specifically, when the siloxane resin composition prepared according to Examples 1 to 3 was cured, it had a surface hardness of 8H to 9H and a light transmittance after heat treatment of about 90%, showing excellent hardness and transparency, It can be used effectively as a material or an electric material.
On the contrary, in the case of using the siloxane resin composition prepared using only the monomer represented by the formula (3) and the siloxane resin composition prepared using only the monomer represented by the formula (5) (Comparative Examples 1 and 2) 3, and the light transmittance after the heat treatment was also about 81% to 85%.
This is especially because it is not easy in the industry to increase the surface hardness of 1H and to increase the light transmittance of 1%, and it is considered that the siloxane resin composition as a two-component copolymer shows a remarkable effect.
Therefore, as described in Experimental Example 1, the monomer containing the cyclic siloxane group-containing silane compound (Formulas 1 to 3) and the silane compound containing the aliphatic epoxy group and the alkoxy group (Formula 4) The material obtained by the two-component copolymerization is superior in the surface hardness and the light transmittance than the material produced by homopolymerizing a monomer containing a silane compound containing a cyclic siloxane group or a monomer containing a silane compound containing an aliphatic epoxy group and an alkoxy group . ≪ / RTI >
(1) to (3) containing a silane compound containing a cyclic siloxane group, a silane compound (4) containing an aliphatic epoxy group and an alkoxy group, and an alkoxysilane compound In Examples 3 and 4, which were obtained by ternary copolymerization of the monomers containing monomers including the monomers including the monomers including the monomers including the monomers including the monomer, It was confirmed that it had remarkably excellent effects.
Experimental Example 2
(3,4'-epoxycyclohexyl) methyl 3,4-epoxycyclohexylcarboxylate was added to the silane compounds (a, b, c, d, and e) obtained in Examples 1 to 5 above, 10 parts by weight of the resin was added and 2 parts by weight of triphenylsulfonium hexafluoroantimonate salt as a polymerization initiator was added to the resin in order to perform photopolymerization. (Octadecylphenyl) propionate and tris (nonylphenyl) phosphite as an antioxidant to inhibit the oxidation reaction that may occur in the polymerization reaction 1.5 parts by weight and 3.5 parts by weight, respectively, of the resin were added to obtain a mixture (Examples 6 to 10) for each siloxane resin composition.
As a comparative example, the resin compound obtained in Comparative Examples 1 and 2 and the siloxane resin of Comparative Example 3 were used in place of the siloxane resin compositions (a, b, c, d, and e) (Comparative Examples 4 to 6)
Thereafter, the surface hardness and the light transmittance of the coated cured products prepared by using Examples 6 to 10 and Comparative Examples 4 to 6 were measured after the cured products were prepared in the same manner as described above, and the results are shown in Table 2 below.
Example
The monomer of the resin composition
Experimental Example 3
Ethyl 3 - [[(3-ethyloxetan-3-yl) methoxy] methyl] -1,3-dioxaborolane was added to the siloxane resin compositions (a, b, c, d, and e) obtained in Examples 1 to 5, 20 parts by weight of oxetane was added to the resin and 2 parts by weight of triphenylsulfonium hexafluoroantimonate salt as a polymerization initiator was added to the resin in order to photopolymerize the resin. Octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate and tris (nonylphenyl) phosphite as an antioxidant to inhibit the oxidation reaction that may occur in the polymerization reaction 1.5 parts by weight and 3.5 parts by weight, respectively, were added to obtain a mixture (Examples 11 to 15) for each siloxane resin composition.
Thereafter, a coating cured product was prepared in the same manner as described above.
As a comparative example, the resin compound obtained in Comparative Examples 1 and 2 and the siloxane resin of Comparative Example 3 were used in place of the siloxane resin compositions (a, b, c, d, and e) A mixture of compositions was prepared (Comparative Examples 7 to 9)
Thereafter, the surface hardness and the light transmittance of Examples 11 to 15 and Comparative Examples 7 to 9 were measured in the same manner as described above, and the results are shown in Table 3 below.
The monomer of the resin composition
Example 12
Comparative Example 9
Experimental Example 4
Methyl-1,2-cyclohexenedicarboxylic anhydride as a monomer capable of thermopolymerizing the siloxane resin composition (a, b, c, d, and e) obtained in the above Examples 1 to 5, 50 parts by weight of the resin was added, and 3 parts by weight of 2-ethyl-4-methylimidazole as a polymerization initiator was added to the resin for thermal polymerization. Octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate and tris (nonylphenyl) phosphite as an antioxidant to inhibit the oxidation reaction that may occur in the polymerization reaction 1.5 parts by weight and 3.5 parts by weight, respectively, were added to obtain a mixture (Examples 16 to 20) for each siloxane resin composition.
Subsequently, the mixture of the siloxane resin composition was coated with an organic solvent methyl ethyl ketone to a thickness of 20 μm and 50 μm on the surface of PET, cured at 80 ° C. for 10 minutes, and cured at 90 ° C. for 3 hours And then subjected to further heat treatment at 85 ° C and 85% relative humidity for 1 hour to prepare a cured product of the mixture.
The surface hardness of the siloxane-coated cured product obtained in the above Example was measured using a pencil hardness meter according to JIS K5600 and the initial light transmittance at a wavelength of 550 nm and the initial light transmittance at 120 nm using a UV / VIS / NIR spectrum analyzer Nippon Denshoku Corporation Lt; 0 > C for 500 hours in air, and the results are shown in Table 4 below.
As a comparative example, the resin compound obtained in Comparative Examples 1 and 2 and the siloxane resin of Comparative Example 3 were used instead of the siloxane resin compounds (a, b, c, d, and e) The hardness and the light transmittance were measured.
The monomer of the resin composition
Example 17
Example 18
Comparative Example 10
Comparative Example 12
As shown in Tables 2 to 4, it is preferable to use a composition comprising i) monomers (Formulas 1 to 3) containing a silane compound containing a cyclic siloxane group and silane compounds (Formula 4) containing an aliphatic epoxy group and an alkoxy group A mixture containing a siloxane resin composition obtained by two-component copolymerization of monomers, or ii) a monomer containing a silane compound containing cyclic siloxane groups (Formula 1 to 3, silane compound containing an aliphatic epoxy group and an alkoxy group (Formula 4) And a siloxane resin composition obtained by ternary copolymerizing a monomer containing an alkoxysilane compound represented by the general formula (5) is cured, the siloxane resin composition preferably contains an acid anhydride compound, an aliphatic cyclic epoxy group Compound or oxetane group, it is preferable to use a cyclic It was confirmed that the polymer produced by homopolymerization of a monomer containing a silane compound containing a siloxane group or a silane compound containing an aliphatic epoxy group and an alkoxy group exhibits superior surface hardness and light transmittance there was.
That is, it was confirmed that the siloxane resin composition obtained by the two-way copolymerization and the resin composition obtained by the ternary copolymerization exhibited excellent surface hardness and light transmittance as compared with the individual polymers of the respective simple structures. This indicates that the siloxane resin composition is an acid anhydride compound, And the compound having a cyclic epoxy group or a compound having an oxetane group.
Claims (20)
The monomer containing the cyclic siloxane group-containing silane compound has at least one structure selected from the group consisting of the structures represented by the following formulas (1), (2) and (3)
The monomer containing the aliphatic epoxy group and the alkoxy group-containing silane compound has a structure represented by the following formula (4)
Wherein the monomer containing the alkoxysilane compound is represented by the following formula (5).
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
(Wherein R 1 is a C1 to C7 linear, branched or cyclic alkyl group containing an aliphatic cyclic epoxy group, the alicyclic epoxy group is a structure in which the C3 to C6 cycloalkyl group has an epoxy group, and R 2 is a C1 to C7 linear, branched or cyclic alkyl group, and m is an integer of 0 to 3.)
[Chemical Formula 5]
(Wherein R 3 represents a C 1 to C 20 alkyl group, a C 3 to C 8 cycloalkyl group, a C 2 to C 20 alkenyl group, a C 2 to C 20 alkynyl group, a C 6 to C 20 aryl group, an acrylic group, a methacrylic group, A halogen group and an amino group, R 4 is a C1 to C7 linear, branched or cyclic alkyl group, and q is an integer of 0 to 3.)
The silane compound containing an aliphatic cyclic epoxy group and an alkoxy group represented by the above-mentioned formula (4) may be obtained by reacting 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane or 2- (3,4-epoxycyclohexyl) ethyltriethoxy Silane. ≪ / RTI >
The alkoxysilane compound represented by Formula 5 may be at least one selected from the group consisting of tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, dimethyldimethoxysilane, dimethyldiethoxy Silane, phenyltrimethoxysilane, phenyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, triphenylmethoxysilane, triphenylethoxysilane, ethyltriethoxysilane, propylethyltrimethoxysilane, Vinyltriethoxysilane, vinyltripropoxysilane, N- (3-acryloxy-2-hydroxypropyl) -3-aminopropyltrimethoxysilane, N- (3- Acryloxy-2-hydroxypropyl) -3-aminopropyltriethoxysilane, N- (3-acryloxy-2- hydroxypropyl) -3-aminopropyltripropoxysilane, 3-acryloxypropylmethylbis (Trimethoxy) silane, 3-acryloxypropyl trimethoxy (Meth) acryloxypropyltriethoxysilane, 3-acryloxypropyltriethoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, 3- (Meth) acryloxypropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- And at least one member selected from the group consisting of propyltrimethoxysilane, 3-aminopropyltriethoxysilane, chloropropyltrimethoxysilane, chloropropyltriethoxysilane, and heptadecafluorodecyltrimethoxysilane. By weight of the siloxane resin composition.
Wherein the siloxane resin composition comprises 1 to 50 parts by weight of an acid anhydride compound containing at least one anhydride group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
Wherein the acid anhydride compound comprises at least one selected from the group consisting of phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nadic methyl anhydride, clorenedic anhydride and pyromellitic anhydride. Siloxane resin composition.
Further comprising 1 to 50 parts by weight of a compound having an aliphatic cyclic epoxy group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
The compound having an aliphatic cyclic epoxy group is preferably at least one compound selected from the group consisting of 4-vinylcyclohexene dioxide, cyclohexene vinyl monoxide, (3,4-epoxycyclohexyl) methyl 3,4-epoxycyclohexylcarboxylate, 3,4-epoxycyclohexyl (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexanecarboxylate and 2- (3,4-epoxycyclohexyl) -1,3-dioxolane ≪ RTI ID = 0.0 > 1, < / RTI >
And 1 to 50 parts by weight of a compound having an oxetane group per 100 parts by weight of the silane compound containing the cyclic siloxane group.
The oxetane group-containing compound may be at least one compound selected from the group consisting of 3-methyloxetane, 2-methyloxetane, 3-oxetanole, 2-methylene oxetane, 3,3-oxetane dimethanethiol, 4- (2,2-dimethylpropyl) -3-methyl-3-oxetanemethanamine, N- (1,2-dimethylbutyl) -3-methyl- Amine, (3-ethyloxetan-3-yl) methyl methacrylate, and 4 - [(3-ethyloxetan-3- yl) methoxy] butan- At least one member selected from the group consisting of methyloxetane, 2-ethylhexyloxetane, xylenes bisoxetane and 3-ethyl-3 [[[3-ethyloxetan-3-yl] methoxy] methyl] By weight based on the total weight of the coating composition.
And 0.1 to 10 parts by weight of a polymerization initiator based on 100 parts by weight of the silane compound containing the cyclic siloxane group.
Wherein the polymerization initiator comprises at least one member selected from the group consisting of an onium salt, an organic metal salt, an amine and an imidazole.
Wherein the siloxane resin composition further comprises at least one selected from the group consisting of an organic solvent, an antioxidant, a leveling agent, and a coating aid.
Wherein said copolymerization is carried out under water and catalytic conditions.
Wherein the catalyst comprises at least one member selected from the group consisting of hydrochloric acid, acetic acid, hydrogen fluoride, nitric acid, sulfuric acid, chlorosulfonic acid, iodic acid, phosphorous acid, ammonia, potassium hydroxide, sodium hydroxide, barium hydroxide, imidazole, ≪ / RTI >
Wherein the polymerization is carried out by light irradiation or heating.
Characterized in that it is used as a film coating material or an LED encapsulating material.
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| KR20190135828A (en) * | 2018-05-29 | 2019-12-09 | 주식회사 신아티앤씨 | Quantum dot film for display comprising siloxane resin binder and InP based quantum dots and method preparing the same |
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