JP4302721B2 - Curable organopolysiloxane composition, sealant for flat panel display containing the same, and flat panel display element - Google Patents

Description

  TECHNICAL FIELD The present invention relates to a curable organopolysiloxane composition that cures at room temperature and ultraviolet rays, and in particular, a curable organopolysiloxane suitable for use as a coating agent for electric and electronic parts and their circuits, and as a sealant for flat panel displays. The present invention relates to a composition, a sealant for a flat panel display including the composition, and a flat panel display element.

Conventionally, various types of room temperature curable silicone rubber compositions (hereinafter referred to as “RTV”) that give rubber-like elastic bodies at room temperature are known. Cured rubber obtained from RTV is used in various fields because it has excellent weather resistance, durability, heat resistance, cold resistance, etc. compared to other organic rubbers. It is often used for applications such as bonding of metal, bonding of metal and glass, and sealing of joint joints.
Also, as an adhesive / coating agent for electric / electronic parts, dealcohol-free RTV tends to be frequently used from the viewpoint of adhesion to an adherend such as epoxy resin. Similarly, dealcohol-free type RTV is also frequently used as a sealant for flat panel displays which have been rapidly increased in recent years.

By the way, with improvement in the speed of production lines in the electric and electronic industries, improvement in the curing rate is required for curable compositions used as sealing agents and the like in these lines. Therefore, an ultraviolet curable organopolysiloxane composition having a faster curing speed has been developed as compared with conventional silicone rubber curable compositions such as condensation type, heat curable type, and platinum addition reaction type. For example, as this ultraviolet curable composition, a composition comprising an acrylic group-containing polysiloxane and a sensitizer has been proposed (see Patent Document 1).
However, in the case of this composition, in order to obtain a cured product of a rubber-like elastic body, it is necessary to use a high molecular weight linear polymer as a base polymer. For this reason, the amount of acrylic groups located at the end of the organopolysiloxane is relatively very small, the curability is lowered, and the surface portion in contact with air in the composition is hardly cured due to inhibition of oxygen curing. There are drawbacks. Therefore, only a resin-like composition having a relatively large amount of acrylic groups has been put to practical use as this type of photocurable composition, and the resulting cured product is inferior in tensile strength and also preserves the composition itself. There was a problem of lack of sex.

  In order to remedy this drawback, the present inventors have first developed a novel compound called an alkoxy-α-silyl ester, a (meth) acryl-functional alkoxysilane, a divalent tin-based compound, a photopolymerization initiator, and curing. A composition combined with a catalyst has been proposed (see Patent Document 2).

Japanese Patent Publication No.53-36515 Japanese Patent No. 2639286

However, in the case of the composition described in Patent Document 2, there is an advantage of providing a practical silicone elastic body as a cured product, but there is a problem that the adhesion of the cured product to glass or metal is insufficient, It has been found that it is not suitable for various adhesive applications and seal applications.
On the other hand, in recent years, in the seal of the area including the electrode on the glass substrate of the flat panel display panel and the film circuit connected to the electrode, the cured product used for the seal is used for repair and repair of the completed panel. It is necessary to remove from the panel substrate, and at this time, it is required that the cured product can be peeled off from the substrate surface and does not remain on the surface.
However, in the prior art, a cured product that does not leave the surface after interfacial peeling from the substrate surface has not been developed. For example, in order to improve the adhesion of the composition described in Patent Document 2 to glass or metal, it is assumed that an organosilicon compound having an amino group or an acrylic group is added. It adheres to the base material, and the cured product remains on the base material surface at the time of peeling.

  Therefore, an object of the present invention is to cure at room temperature and under ultraviolet irradiation, have good storage stability, and can form a cured product having excellent adhesion and releasability to glass, metal, plastic and the like. An organopolysiloxane composition, a flat panel display sealant containing the composition, and a rat panel display element.

That is, in order to achieve the above-mentioned object, the curable organopolysiloxane composition of the present invention comprises a condensation reaction product of (A) 100 parts by mass of the following (I) component and (II) 1 to 200 parts by mass of the component. 100 parts by mass of the organopolysiloxane, wherein the component (I) is an R ₃ SiO _1/2 unit (wherein each R is independently an unsubstituted or halogen atom-substituted monovalent carbon atom having 1 to 6 carbon atoms) And a SiO _4/2 unit as a repeating unit, and the ratio of R ₃ SiO _1/2 unit to 1 mol of SiO _4/2 unit is 0.5 to 1.2 mol, and SiO _{4 / 2} units per mole of R ₂ SiO _2/2 units and RSiO _3/2 units (wherein each R is independently an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) At least one of Each unit may have 1.0 mol or less and the total of each unit may be 1.0 mol or less, and the hydroxy group bonded to the silicon atom is 0.1% by mass or more and 6.0% by mass. (II) component is a functional group-containing silyl group selected from the group consisting of a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group, and an aminoxy group. It is a diorganopolysiloxane whose chain ends are blocked, and (B) the following general formula (1)
Wherein R ¹ is a hydrogen atom or a methyl group, R ² is an alkylene group, R ³ and R ⁴ are the same or different unsubstituted monovalent hydrocarbon groups, and a is an integer of 0-2. 1 to 50 parts by mass of (meth) acryl-functional alkoxysilane, (C) 0.01 to 10 parts by mass of a catalyst for condensation reaction, and (D) 0.01 to 10 parts by mass of a photoinitiator.

The component (II) is represented by the following general formula (2)
(Wherein R ⁵ is each independently an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group) groups, and each independently functional groups selected from the group consisting of an aminoxy group, a is an integer of 1 to 3, n represents preferably a diorganopolysiloxane represented by 10 or more is an integer).

  The sealing agent for flat panel displays of this invention contains the said curable organopolysiloxane composition.

  The flat panel display element of this invention uses the said sealing agent for flat panel displays for the sealing of the area | region containing the electrode on the glass substrate of this display, and the film circuit connected on this electrode.

  According to the present invention, it is cured at room temperature and under ultraviolet irradiation, has excellent storage stability, and can form a cured product having excellent adhesion and releasability to glass, metal, plastic and the like. An organopolysiloxane composition is obtained. The present invention is particularly suitable for coating agents for electric / electronic parts or circuits, and sealing agents for flat panels.

  Hereinafter, the water repellent composition according to the embodiment of the present invention will be described. The water repellent composition of the present invention contains the following components (A) to (D) as essential components.

[(A) component]
The component (A) improves the adhesion to the adherend and the strength of the cured product, and is an organopolyester that is a condensation reaction product of 100 parts by mass of the following component (I) and 1 to 200 parts by mass of the component (II). Made of siloxane.
Component (I) consists of R ₃ SiO _1/2 units (wherein R represents each independently an unsubstituted or halogen atom- substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) and SiO _4/2 units. Is a repeating unit.
R is, for example, an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group; a cyclopentyl group, a cyclohexyl group A cycloalkyl group such as a vinyl group, an allyl group, an isopropenyl group, a butenyl group, a pentenyl group and a hexenyl group; an aryl group such as a phenyl group; a chloromethyl group, a 3-chloropropyl group, and a 1-chloro- Examples thereof include halogenated alkyl groups such as 2-methylpropyl group and 3,3,3-trifluoropropyl group. Particularly, methyl group, vinyl group and phenyl group are preferable, and methyl group is most preferable. Each R may be a different group or the same group.

The ratio of R ₃ SiO _1/2 units to 1 mol of SiO _4/2 units in component (I) must be 0.5 to 1.2 mol, preferably 0.65 to 1.15 mol. Range. When the ratio of R ₃ SiO _1/2 units is less than 0.6 mol, the strength of the obtained cured product is insufficient, and when it exceeds 1.2 mol, the transparency of the cured product is inferior. If the transparency of the cured product is inferior, it becomes difficult for UV light to reach the deep part of the cured product, and the deep part curability is lowered.

Furthermore, in the component (I), R ₂ SiO _2/2 unit and RSiO _3/2 unit (wherein R is independently an unsubstituted or halogen atom- substituted carbon atom with respect to 1 mol of SiO _4/2 unit) At least one of each unit may be 1.0 mol or less, and the total of each unit may be 1.0 mol or less. More preferably, the R ₂ SiO _2/2 unit and the RSiO _3/2 unit are 0.2 to 0.8 mol, and the total of the units is 1.0 mol or less.
As such a blending ratio, a combination of 0.2 mol of R ₂ SiO _2/2 units and 0.7 mol of RSiO _3/2 units is exemplified with respect to 1 mol of SiO _4/2 units.

In the component (I), when at least one of the R ₂ SiO _2/2 unit and the RSiO _3/2 unit is not contained, the composition becomes a resin, and the workability is lowered without becoming a solution before curing. Tend to. On the other hand, when the content of each unit of R ₂ SiO _2/2 unit and RSiO _3/2 unit exceeds 1.0 mol, or the total amount of each unit exceeds 1.0 mol, the transparency of the composition Tend to be inferior.

In the component (I), the hydroxy group bonded to the silicon atom of each unit is 1.0% by mass or more and less than 6.0% by mass. The hydroxy group is generated when the component (I) is prepared by a cohydrolysis / condensation reaction and bonded to a silicon atom. The hydroxy group is necessary for the condensation reaction between the component (I) and the following component (II), and the lower limit is 0.1% by weight or more . Preferably, the hydroxy group content is 0.2 to 3.0% by weight. When the content of the hydroxy group is 6.0% by weight or more, the hardness of the obtained cured product becomes too high and the adhesiveness is lowered. On the other hand, if the content is less than 0.1% by weight, the strength of the obtained cured product may be insufficient.

The component (I) can be obtained by a known method. For example, the component (I) is substantially free of volatile components by co-hydrolyzing and condensing an alkoxy group-containing silane compound corresponding to each unit in an organic solvent. Can be obtained as
As a specific method for obtaining the component (I), for example, R ₃ SiOMe and Si (OMe) ₄ are optionally combined with R ₂ Si (OMe) ₂ and / or RSi (OMe) ₃ as an organic solvent. It is only necessary to co-hydrolyze and condense therein (in each formula, R independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms, and Me represents a methyl group).
As said organic solvent, what can melt | dissolve the organopolysiloxane produced | generated by cohydrolysis and a condensation reaction is preferable, and toluene, xylene, a methylene chloride, a naphtha mineral spirit etc. can be mentioned typically. Instead of using the organic solvent, diorganopolysiloxane having the following component (II) and having a viscosity at 23 ° C. of 20 to 2,000 mm ² / s may be used instead.

About the content molar ratio of each unit which concerns on (I) component, it can set suitably by adjusting the preparation molar ratio of the methoxysilane compound corresponding to each unit, for example.
Moreover, content of the said hydroxy group in (I) component can be changed by adjusting the conditions of cohydrolysis and a condensation reaction.

The component (II) is a diorganopoly having a molecular chain end blocked with a functional group-containing silyl group selected from the group consisting of a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group, and an aminoxy group. Siloxane, and the component (II) undergoes a condensation reaction with the component (I).
The functional group is not particularly limited as long as it undergoes a condensation reaction with the hydroxy group bonded to the silicon atom of the component (I). For example, a hydroxy group; and a methoxy group, an ethoxy group, a propoxy group, a butoxy group Alkoxy groups such as methoxyethoxy group, ethoxyethoxy group and methoxypropoxy group; alkenyloxy groups such as vinyloxy group, isopropenyloxy group and isobutenyloxy group; dimethyl ketoxime group, methylethyl ketoxime group, Ketooxime groups such as diethyl ketoxime group and cyclohexanoxime; Acyloxy groups such as acetoxy group, propionyloxy group, butyryloxy group, octanoyloxy group, benzoyloxy group; N, N-dimethylaminoxy group, N, N-diethylamino Xyl group It includes hydrolyzable groups such as aminoxy groups are preferably hydroxy group, an alkoxy group, particularly preferably a hydroxy group.

(II) component is the following general formula (2)
(Wherein R ⁵ is each independently an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group) groups, and each independently functional groups selected from the group consisting of an aminoxy group, a is an integer of 1 to 3, n represents preferably a diorganopolysiloxane represented by 10 or more is an integer).
As R ⁵ , for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group Alkyl groups such as decyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, isopropenyl group, butenyl group, pentenyl group and hexenyl group; phenyl group, tolyl group and xylyl group Aryl groups such as naphthyl group; aralkyl groups such as benzyl group, phenethyl group and phenylpropyl group; chloromethyl group, 3-chloropropyl group, 1-chloro-2-methylpropyl group, 3,3,3-trifluoro Examples include halogenated alkyl groups such as propyl group, and among these, methyl group is preferable.
As X, for example, the functional groups described above can be used.

N in the formula (2) is an integer of 10 or more, but the viscosity of the diorganopolysiloxane (component (II)) at 23 ° C. is 300,000 mm ² / s or less, preferably 100 to 100,000 mm ² / The number is preferably such that the fluid is in the range of s.

  Specific examples of the diorganopolysiloxane represented by the general formula (2) include, for example, molecular chain both-end silanol group-blocked polydimethylsiloxane, molecular chain both-end silanol group-blocked dimethylsiloxane / methylphenylsiloxane copolymer, Molecular chain both ends trimethoxysiloxy group-blocked polydimethylsiloxane, Molecular chain both ends trimethoxysiloxy group-blocked dimethylsiloxane / methylphenylsiloxane copolymer, Molecular chain both ends methyldimethoxysiloxy group-blocked polydimethylsiloxane, Molecular chain both ends tri Examples thereof include ethoxysiloxy group-blocked polydimethylsiloxane. These can be used alone or in combination of two or more.

<Condensation reaction between component (I) and component (II)>
(A) component is 1-200 mass parts of (II) component with respect to 100 mass parts of (I) component, Preferably 5-II-150 mass parts of (II) component, Most preferably, (II) component is 70- It can be obtained by blending 120 parts by mass and causing a condensation reaction. (II) When the compounding quantity of a component is less than 1 mass part, and when it exceeds 200 mass parts, the adhesiveness of the obtained hardened | cured material will be impaired.
As described above, when the component (II) is used instead of the organic solvent when the component (I) is produced, the condensation reaction between the component (I) and the component (II) is also terminated at that time. . Therefore, in this case, it is not necessary to add another component (II) to the component (I) after production as long as the blending amount of the component (II) at the time of manufacturing the component (I) is within the above range.

In the condensation reaction between component (I) and component (II), it is preferable to use a condensation reaction catalyst. Examples of the condensation reaction catalyst include titanium compounds, tin compounds, amine compounds, alkali metal compounds, and the like, but it is preferable to use amine compounds. Specific examples of the amine compound include ethylamine, propylamine, isopropylamine, butylamine, diethylamine, dibutylamine, triethylamine, and aqueous ammonia.
The blending amount of the condensation reaction catalyst may be an effective amount as a catalyst and is not particularly limited, but is usually 0.05 to 3.0 with respect to 100 parts by mass of the total of the components (I) and (II). What is necessary is just about a mass part.

The condensation reaction temperature is not particularly limited, but is usually 1 to 120 ° C, preferably 10 to 80 ° C. The reaction time is not particularly limited, but is about 0.5 to 12 hours.
After completion of the condensation reaction, the solvent and / or unreacted organopolysiloxane, diorganopolysiloxane, condensation reaction catalyst, etc. may be distilled off as necessary. Furthermore, in order to adjust the viscosity of the condensation reaction product, a low molecular cyclic siloxane such as an organopolysiloxane or an octamethylcyclotetrasiloxane whose end is blocked with a trimethylsiloxy group or a vinyl group; an aliphatic hydrocarbon; an aromatic Hydrocarbon; liquid paraffin; isoparaffin; a photoreactive diluent such as an acrylate ester may be added. As such a viscosity adjusting component, it is effective to use a component having a viscosity at 23 ° C. of about 5 to 1,000 mm ² / s.

[Component (B)]
The component (B) imparts ultraviolet curability to the composition of the present invention, and is incorporated into the base organopolysiloxane by, for example, a condensation reaction to give stable ultraviolet curability.
The component (B) has the following general formula (1)
Shown (wherein, ^{R 1} represents a hydrogen atom or a methyl group, ^{R 2} is an alkylene group, ^{R 3} and ^{R 4} are the same or different unsubstituted monovalent hydrocarbon radical, a is an integer of 0 to 2) in (Meth) acrylic functional alkoxysilane.

Examples of R ² include an alkylene group, and an alkylene group having 1 to 6 carbon atoms is particularly preferable. Specific examples of R ³ and R ⁴ include alkyl groups such as methyl group, ethyl group, propyl group, and butyl group; aryl groups such as phenyl group. Among these groups, the number of carbon atoms is 1 ~ 8 are preferred. R ³ is not an essential group.
Specific examples of the component (B) include the following formulas:
The compound shown by can be illustrated, However, It is not limited to this.
In addition, as long as a component (B) corresponds to Formula (1), you may use it individually by 1 type or in combination of 2 or more types.

  The blending ratio of the component (B) in the composition of the present invention is 1 to 50 parts by mass and preferably 5 to 30 parts by mass per 100 parts by mass of the component (A). When the blending ratio of the component (B) is less than 1 part by mass, the ultraviolet curability of the composition is lowered, and when it exceeds 50 parts by mass, only the component (B) is cured, resulting in inconvenience such as impaired adhesion.

[Component (C)]
The component (C) is a condensation reaction catalyst that selectively advances the condensation reaction between the silanol of the component (A) and the alkoxy group of the component (B).
Examples of the component (C) include known catalysts such as organotin ester compounds, organotin chelate compounds, alkoxy titanium compounds, titanium chelate compounds, organoaluminum compounds, organozirconium compounds, silicon compounds having a guanidyl group, and amine compounds. .
Specific examples of the component (C) include tin octoate, dimethyltin diversate, dimethyltin dioctoate, dibutyltin dioctoate, dibutyltin dilaurate, dioctyltin dioctoate, dioctyltin dilaurate tetrabutyltitanate, tetraisopropyl titanate, diisopropoxyxoxy Bis (acetylacetonate) titanium, diisopropoxybis (ethylacetoacetate) titanium, aluminum tris (acetylacetonate), aluminum tris (ethylacetoacetate), zirconium tetra (acetylacetonate), zirconium tetrabutyrate, hexylamine Examples thereof include, but are not limited to, dodecylamine phosphate and tetramethylguanidinepropyltrimethoxysilane. .
In addition, (C) component may be used individually by 1 type or in combination of 2 or more types.

  The blending ratio of the component (C) in the composition of the present invention is 0.01 to 10 parts by mass, preferably 0.1 to 5 parts by mass, per 100 parts by mass of the component (A). When the blending ratio of the component (C) is less than 0.01 parts by mass, the ability as a catalyst is not sufficiently exhibited, and when it exceeds 10 parts by mass, the storage stability of the composition is deteriorated. .

[(D) component]
(D) A component is a photoinitiator required in order to make an ultraviolet cure of a composition. Examples of the component (D) include benzoin and its derivatives, benzoin ethers such as benzoin acrylic ether, benzyl and its derivatives, aromatic diazonium salts, anthraquinone and its derivatives, acetophenone and its derivatives, sulfur compounds such as diphenyl disulfide, Examples include, but are not limited to, benzophenone and its derivatives.
In addition, (C) component may be used individually by 1 type or in combination of 2 or more types.
The blending ratio of the component (D) in the composition of the present invention is 0.01 to 10 parts by mass, preferably 0.1 to 5 parts by mass, per 100 parts by mass of the component (A). When the blending ratio of the component (D) is less than 0.01 parts by mass, the ability as a photoinitiator is not sufficiently exhibited, and when it exceeds 10 parts by mass, the adhesiveness of the composition is lowered. Arise.

[Other ingredients]
In addition to the above components (A) to (D), generally known fillers, additives and the like may be blended with the composition of the present invention as necessary. Examples of the filler include pulverized silica, fumed silica, calcium carbonate, zinc carbonate, and wet silica. In addition, thixotropic improvers such as polyethers, fungicides, antibacterial agents and the like may be blended.

[Preparation of composition]
The composition of the present invention can be prepared by adjusting the component (A) and then adding the components (B) to (D), preferably mixing them in an anhydrous state.

<Application of the composition of the present invention>
The composition of the present invention can be suitably used as a sealing agent for flat panel displays, and is particularly preferably used for sealing flat panel display elements as shown in FIG.
In FIG. 1, the flat panel display element is configured by bonding a glass substrate 2 and a film circuit (TCP: Tape Carrier Package) 8 with an anisotropic conductive adhesive (ACF) 10. A display image portion (for example, a liquid crystal pixel in the case of a liquid crystal display) 6 is formed at the center of one surface of the glass substrate 2, and the electrode 4 extends in a strip shape from the display image portion 6 toward the edge of the glass substrate. ing. The electrode 4 is usually made of a transparent electrode such as ITO (indium tin oxide), and a voltage is applied to each pixel under the control of the drive circuit to turn on / off each pixel. As the glass substrate, alkali-free glass or quartz glass can be preferably used.
The film circuit 8 is a flexible circuit in which the transparent electrode 4 is connected to a drive circuit (not shown) or an external power source, and for example, a copper foil circuit or IC is covered with a polyimide film or other resin.

  The sealing agent for flat panel displays of the present invention can effectively seal the glass substrate 2, the (transparent electrode) 4, and the film circuit 8 as the sealing region 20 as described above. , (Transparent) electrode, and film circuit film) are both excellent in adhesion and releasability.

<Example>
EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. Further, “parts” and “%” shown in the examples represent parts by mass and mass% unless otherwise specified.

Preparation of component (A): A four-necked separable flask equipped with a thermometer, a stirring rod, a reflux condenser, and a nitrogen inlet tube was purged with nitrogen. Then, the molar represented by a component _{(I), (CH} 3) consists _{3 SiO 1/2} units and _{SiO 4/2 units, {(CH} 3) _{3 SiO 1/2} units _{/ SiO 4/2} units} An organopolysiloxane having a ratio of 0.74 and a hydroxy group content bonded to silicon atoms of 1.62% by weight was prepared. (I) It melt | dissolved in toluene so that the solid content of a component might be 50 weight%. (I) 100 parts of the component (100 parts as a whole in toluene solution, 50 parts of component (I) alone in toluene), as a component (II) Silanol groups at both ends having a viscosity at 23 ° C. of 20000 mm ² / s After 50 parts of blocked dimethylpolysiloxane was added and uniformly stirred and mixed, 0.5 part of aqueous ammonia was added dropwise to conduct a condensation reaction at 20 ° C. for 3 hours. Subsequently, while heating this to 120 degreeC, toluene and a low molecular-weight by-product were removed, and it adjusted so that solid content might be 50 weight%, and obtained (A) component.
Preparation of composition: 150 parts of component (A) above, 20 parts of component (B) (methacryloxypropyltrimethoxysilane), 0.5 part of component (C) (tin octoate), component (D) (diethoxy) Acetophenone) 2 parts was blended to prepare a composition.

  As the component (C), a composition was obtained in the same manner as in Example 1 except that 0.1 part of dioctyltin dilaurate was blended instead of tin octoate.

Preparation of component (A): (A) Except that 50 parts of (II) component-end silanol-blocked dimethylpolysiloxane having a viscosity at 23 ° C. of 700 mm ² / s was added (A) Ingredients were obtained.
Preparation of composition: Except that this component (A) was used and, as component (B), 20 parts of acryloxypropyltrimethoxysilane was blended instead of methacryloxypropyltrimethoxysilane. A composition was obtained in the same manner.

Preparation of component (A): Component (A) was the same as Example 1 except that the amount of component (I) was changed to 60 parts and the amount of component (II) was changed to 70 parts. Got.
Preparation of composition: In place of component (A) of Example 1, component (B) to component (D) were blended in the same manner as in Example 1 except that 130 parts of component (A) were blended. A composition was obtained.

  (B) The amount of component (methacryloxypropyltrimethoxysilane) was changed to 10 parts, and a combination of 0.3 parts of dioctyltin dilaurate and 3 parts of tetraisopropyl titanate was used instead of tin octoate as component (C). Except for this, a composition was obtained exactly as in Example 1.

<Comparative Example 1>
Preparation of component (A): Except for not adding component (I), changing the amount of component (II) to 100 parts, and not dropping ammonia water in exactly the same way as in Example 1 ( A) component was obtained.
Preparation of composition: Components (B) to (D) were blended in the same manner as in Example 1, except that 100 parts of component (A) were blended instead of component (A) in Example 1. A composition was obtained.

<Comparative Example 2>
Preparation of component (A): Exactly the same as in Example 1 except that components (I) and (II) were uniformly stirred and mixed, then ammonia water was not added dropwise, and the toluene was removed by heating to 120 ° C. Thus, component (A) was obtained. In place of the component (A) in Example 1, the components (B) to (D) were added in the same manner as in Example 1 except that the component (A) containing 150 parts of the component (A) was used. The composition was obtained by blending.

<Comparative Example 3>
A composition was obtained in the same manner as in Example 1 except that the component (C) was not blended.

<Comparative Example 4>
Preparation of component (A): Except for not adding component (I), changing the amount of component (II) to 100 parts, and not dropping ammonia water in exactly the same way as in Example 1 ( A) component was obtained.
Preparation of composition: Implemented except that 100 parts of this component (A) and 1 part of 3-glycidoxypropyltrimethoxysilane (adhesion aid) were used instead of the component (A) of Example 1. In the same manner as in Example 1, the components (B) to (D) were blended to obtain a composition.

<Evaluation>
Each composition obtained was molded into a sheet of 3 mm thickness, cured at 23 ± 2 ° C. in an environment of 50 ± 5% RH for 1 day, and then subjected to high pressure by a UV irradiation device (conveyor type manufactured by Nihon Battery Co.). A mercury lamp (80 W / cm) was irradiated with ultraviolet rays three times at a distance of 10 cm and a speed of 1 m / min to be cured. The rubber physical properties (hardness and tensile strength) of this product were measured.
Separately from this, each composition obtained was applied on glass at a thickness of 1 mm, and cured under the same conditions as described above, the release properties and adhesion to glass were evaluated.
(1) Hardness
The durometer hardness A (Duro. A) of the cured product was measured according to JISK-6253.
(2) Tensile strength
Based on JISK-6251, the tensile strength (MPa) of the cured product was measured.
(3) Releasability and adhesion The determination was made according to the following criteria.
Adhesion: Hardened material cannot be easily peeled off from glass No adhesion: Hardened material can be easily peeled off from glass Releasable: Hardened material does not remain on glass surface No releasability : Hardened material remains on the glass surface

  The obtained results are shown in Table 1.

  As is clear from Table 1, in each case, the rubber properties (hardness and tensile strength), releasability, and adhesion of the cured composition were all excellent.

On the other hand, in the case of the comparative example 1 which did not mix | blend (I) component in (A) component, all of hardness, tensile strength, and adhesiveness of hardened | cured material were inferior.
In the case of Comparative Example 2 in which the (I) component and the (II) component were simply mixed in the component (A), the cured product was high in hardness, but the tensile strength and adhesion were both inferior.
In the case of the comparative example 3 which did not mix | blend (C) component, each component in a composition did not condense and the hardness, tensile strength, and adhesiveness of hardened | cured material were all inferior.
In the case of Comparative Example 4 using an adhesive as the sealant, the hardness, tensile strength, and mold release property of the cured product were all inferior.

  For the actual product of the liquid crystal display shown in FIG. 1, the composition of Example 1 was sealed in the seal region 20 and cured. Then, when the mold release property and adhesiveness were evaluated by the same method as described above, both were excellent.

It is a figure which illustrates the aspect which uses the sealing compound for flat panel displays of this invention for a flat panel display element.

Explanation of symbols

2 Glass substrate 4 Electrode 8 Film circuit 20 Sealing area

Claims (4)

(A) 100 parts by mass of an organopolysiloxane that is a condensation reaction product of 100 parts by mass of the following component (I) and 1 to 200 parts by mass of the component (II),
Component (I) consists of R ₃ SiO _1/2 units (wherein R represents each independently an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) and SiO _4/2 units. Is a repeating unit, and the ratio of R ₃ SiO _1/2 unit to 1 mol of SiO _4/2 units is 0.5 to 1.2 mol, and further, R ₂ SiO ₂ to 1 mol of SiO _4/2 units. _{/ 2} units and RSiO _3/2 units (wherein each R independently represents an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) Each of the units may be 1.0 mol or less and the total of each unit may be 1.0 mol or less, and the hydroxy group bonded to the silicon atom is 0.1% by mass or more and less than 6.0% by mass. An organopolysiloxane,
The component (II) is a diorganopoly having a molecular chain end blocked with a functional group-containing silyl group selected from the group consisting of a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group, and an aminoxy group. Siloxane,
(B) The following general formula (1)
(Wherein R ¹ is a hydrogen atom or a methyl group, R ² is an alkylene group, R ³ and R ⁴ are the same or different unsubstituted monovalent hydrocarbon groups, and a is an integer of 0 to 2) 1 to 50 parts by weight of (meth) acrylic functional alkoxysilane,
A curable organopolysiloxane composition comprising (C) 0.01 to 10 parts by mass of a catalyst for condensation reaction and (D) 0.01 to 10 parts by mass of a photoinitiator. The component (II) is represented by the following general formula (2)
(Wherein R ⁵ is each independently an unsubstituted or halogen atom-substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydroxy group, an alkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a ketoxime group, an acyloxy group) groups, and each independently functional groups selected from the group consisting of an aminoxy group, curability of claim 1 a is a diorganopolysiloxane represented by the integer of 1 to 3, n represents an integer of 10 or more) Organopolysiloxane composition. The sealing compound for flat panel displays containing the curable organopolysiloxane composition of Claim 1 or 2. The flat panel display element which used the sealing compound for flat panel displays of Claim 3 for the seal | sticker of the area | region containing the electrode on the glass substrate of this display, and the film circuit connected on this electrode.