KR20140055734A - New epoxy compounds, method for preparing thereof and curable polyorganosiloxane composition containing same - Google Patents

Abstract

The present invention relates to a novel epoxy-based compound, a method for manufacturing the same, and a curable polyorganosiloxane composition comprising the same and, more specifically, to an epoxy-based compound represented by the chemical formula 1 and a curable polyorganosiloxane composition which has excellent adhesion, light transmission, heat and humidity resistance, and durability for metals and heat-resistant plastics, and has low haze by comprising the epoxy-based compound. (For the chemical formula 1, Y is O, CH2, C(CH3)2, C(CF3)2, CO, SO, or SO2.).

Description

TECHNICAL FIELD [0001] The present invention relates to a novel epoxy compound, a process for producing the same, and a curable polyorganosiloxane composition containing the same. BACKGROUND ART [0002]

The present invention relates to a novel epoxy-based compound and a curable polyorganosiloxane composition containing the same and having excellent adhesive strength, haze, and light transmittance.

The polyorganosiloxane composition forms a cured product having excellent properties such as weather resistance, heat resistance and hardness, and is used for various purposes.

Such a polyorganosiloxane composition is not only low in adhesion to noble metals such as Ag, Au, Rh, and Pd used as a frame or an electrode of a semiconductor device but also has an adherence to a heat-resistant plastic such as polyphthalic acid imide This has a low drawback.

Therefore, a semiconductor device (package) using the same as a sealing material or a diamond touch material has a problem that peeling occurs at the interface between the electrode or the heat resistant plastic and the polyorganosiloxane composition under high temperature or high temperature and high humidity conditions.

Accordingly, a method of introducing a primer layer to improve adhesion of a polyorganosiloxane composition to a substrate (frame, electrode) made of a noble metal has been proposed. However, not only is a step of applying primer, drying and the like, but also there is a drawback that a load is generated in the surrounding environment by evaporation of the organic solvent contained in the primer.

In addition, a method of using a specific isocyanurate derivative as an adhesion-imparting agent has been proposed (JP-A-2010-0650061). However, the isocyanurate derivative has a low compatibility with the polyorganosiloxane, and the amine component contained in the derivative affects the activity of the platinum catalyst, so that the effect of improving the adhesion is not remarkably exhibited.

An object of the present invention is to provide a curable polyorganosiloxane composition containing a novel epoxy compound and the above epoxy compound and having low haze and excellent adhesion to a heat-resistant plastic as well as metals and light transmittance.

In order to achieve the above object, the present invention provides an epoxy compound represented by the following general formula (1).

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

,

,

또는

일 수 있다.Preferably, the formula (1)

,

,

or

Lt; / RTI >

The present invention also provides a process for preparing a polyimide precursor, comprising: reacting a polyimide precursor of formula (2) with allyl alcohol to produce a compound of formula (3); And reacting the compound of formula (3) with epichlorohydrin to produce a compound of formula (1).

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

The present invention also provides a curable polyorganosiloxane composition containing an epoxy compound of the following formula (1).

[Chemical Formula 1]

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

The curable polyorganosiloxane composition may contain a polyorganosiloxane, a polyorganohydrogen siloxane, a platinum catalyst, and an epoxy compound of the above formula (1).

The curable polyorganosiloxane composition containing an epoxy compound according to the present invention has an advantage of excellent adhesion to metals as well as to heat-resistant plastics.

In addition, the curable polyorganosiloxane composition according to the present invention has an advantage of being excellent in compatibility with a polyorganosiloxane as a main component, having low haze and excellent light transmittance.

The present invention relates to a novel epoxy-based compound and a curable polyorganosiloxane composition containing the same and having excellent adhesive strength, haze and light transmittance.

Hereinafter, the present invention will be described in detail.

The present invention is characterized by an epoxy compound represented by the following formula (1).

[Chemical Formula 1]

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

,

,

또는

인 것이 좋다.Preferably, the formula (1)

,

,

or

.

The epoxy compound may be prepared by reacting a polyimide precursor of Formula 2 with allyl alcohol to prepare a compound of Formula 3, And a step of reacting the compound of formula (3) with epichlorohydrin to prepare a compound of formula (1).

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

The reaction of each step is generally known in the art, and the first step reaction is dropwise-bled with about 2 equivalents of allyl alcohol over 2 hours for compound 2, followed by stirring at room temperature for 20 to 30 hours.

After the completion of the first step reaction, the reaction proceeds without purification, and at least two equivalents of epichlorohydrin per molecule of the first step is added. The reaction was carried out using a quaternary ammonium salt as a catalyst at 40 to 60 DEG C for 10 to 14 hours. Thereafter, a 5 wt% aqueous KOH solution was dropwise added to the reaction mixture, and the resulting mixture was stirred at 40 to 60 ° C for 3 to 7 hours. Extraction was performed using excess toluene and water, and Compound 1 ≪ / RTI >

Further, the present invention is characterized by a curable polyorganosiloxane composition containing an epoxy compound of the following formula (1). The epoxy compound of Formula 1 serves as an adhesion enhancer for improving adhesion to metals such as Ag, Au, Rh, Pb and Al and heat resistant plastics such as polyphthalic acid amide (PPA) and liquid crystal polyester (LCP) .

[Chemical Formula 1]

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).

The curable polyorganosiloxane composition of the present invention contains a polyorganosiloxane, a polyorganohydrogen siloxane, a platinum catalyst, and an epoxy compound of the above formula (1).

The polyorganosiloxane is the major component of the composition and its molecular structure may be linear or cyclic, and they may have molecular branches. It is preferable that the main structure in which diorganosiloxane units are repeated is a straight chain type molecular structure in which both ends of the molecular chain are blocked with triosanosiloxy groups. When the molecular structure is a straight-chain type, the alkenyl group may be bonded to the silicon atom only at either the end of the molecular chain or the middle, preferably the silicon atom at both the end of the molecular chain and the middle.

Among the polyorganosiloxanes, the alkenyl group bonded to the silicon atom includes those having 2 to 10 carbon atoms, preferably 2 to 6 carbon atoms. Examples include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group and an octenyl group. Of these, the vinyl group is preferable.

A substituent other than an alkenyl group may be bonded to the silicon atom in the polyorganosiloxane. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a 1-methylethyl group, a butyl group, a 1-methylpropyl group, a 2-methylpropyl group, a 1,1-dimethylethyl group, a pentyl group, , 3-methylbutyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, hexyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, , Nonyl group, decyl group and the like; An allyl group having 6 to 14 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group and the like; An aralkyl group such as benzyl group, phenethyl group and the like; Chloromethyl group, 3-chloropropyl group, 3,3,3-trifluoropropyl group, chlorophenyl group, dichlorophenyl group, 2,2,2, -trifluoroethyl group, 2,2,3,3-tetrafluoro Propyl group, and 2,2,3,3,4,4,5,5-octafluoropentyl group. Of these, a methyl group or a phenyl group is preferable.

The polyorganosiloxane preferably has a viscosity of usually 100 to 100,000 mPa · S at 25 ° C, and more preferably 500 to 10,000 mPa · S. When the viscosity is within this range, not only the workability is good but also the physical properties of the cured product obtained by the curing are good.

The polyorganosiloxane may have a number average molecular weight (Mn) of 500 to 50,000. At this time, the number average molecular weight can be measured by gel permeation chromatography using a low angle laser light scattering detector, a refractive index detector or a standard sample of polyorganosiloxane resin.

Specific examples of the polyorganosiloxane include a dimethylsiloxane-methylvinylsiloxane copolymer in which both terminals of the molecular chain are blocked with a trimethylsiloxy group; Methylvinylpolysiloxane wherein both ends of the molecular chain are blocked with trimethylsiloxy groups; A dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymer in which both terminals of the molecular chain are blocked with trimethylsiloxy groups; Dimethylpolysiloxanes wherein both ends of the molecular chain are blocked with a dimethylvinylsiloxy group; Methylvinylpolysiloxanes wherein both ends of the molecular chain are blocked with a dimethylvinylsiloxy group; A dimethylsiloxane-methylvinylsiloxane copolymer in which both ends of the molecular chain are blocked with a dimethylvinylsiloxy group; A dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymer in which both terminals of the molecular chain are blocked with a dimethylvinylsiloxy group; Dimethylpolysiloxanes wherein both ends of the molecular chain are blocked with a trivinylsiloxy group; (R ₄ ) ₃ SiO _{0 .5} , a siloxy group unit represented by (R ₄ ) ₂ R ₅ SiO _0.5 , a siloxy group unit represented by R ₄ SiO, and a siloxy group represented by SiO ₂ A polyorganosiloxane copolymer; (R ₄ ) ₃ SiO _{0 .5} , a siloxy group unit represented by (R ₄ ) ₂ R ₅ SiO _{0 .5} , and a siloxane unit represented by SiO ₂ ; A polyorganosiloxane copolymer comprising a siloxane unit represented by (R ₄ ) ₂ R ₅ SiO _{0 .5} , a unit represented by R ₄ SiO, and a siloxane unit represented by SiO ₂ ; A polyorganosiloxane copolymer comprising a siloxane unit represented by R ₄ R ₅ SiO, a siloxane unit represented by R ₄ SiO _{1 .5} , or a siloxane unit represented by R ₅ SiO _{1 .5} . These may be used alone or in combination of two or more. In the formula, R ₄ may be the same as other substituent groups other than alkenyl groups other than the alkenyl group bonded to the silicon atom among the above-mentioned polyorganosiloxane components, and R ₅ is an alkenyl group, May be the same as the alkenyl group bonded to the atom.

The polyorganohydrogen siloxane may be one containing a silicon-bonded hydrogen atom as a crosslinking component which reacts with the polyorganosiloxane. The molecular structure of the polyorganohydrogen siloxane is not particularly limited and may be, for example, a linear, cyclic, branched, or three-dimensional network.

The polyorganohydrogensiloxane has a hydrosilyl group [Si-H] in which two or more, preferably three or more silicon atoms are bonded to a hydrogen atom in the molecule. When the polyorganosiloxane siloxane is in the form of a straight chain, the hydrosilyl group may be located at either or both of the molecular chain terminal and the middle.

The polyorganohydrogen siloxane may have a number of silicon atoms in one molecule, that is, a degree of polymerization of 2 to 1,000, preferably 3 to 100.

Examples of the polyorganohydrogen siloxane include polyorganohydrogen siloxane represented by (R ₆ ) _a H _b SiO _{(4-ab) / 2} . In the above formula, R ₆ is a hydrocarbon group having 1 to 14 carbon atoms, preferably 1 to 10 carbon atoms, excluding an aliphatic unsaturated group, specifically a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, , A pentyl group, a neopentyl group, a hexyl group, a cyclohexyl group, an octyl group, a nonyl group and a decyl group; Allyl groups such as phenyl, tolyl, xylyl and naphthyl; An aralkyl group such as a benzyl group, a phenylethyl group or a phenylpropyl group; And hydrocarbon groups in which some or all of the hydrogen atoms in the gastric hydrocarbon group are substituted with halogen atoms such as chloromethyl, 3-chloropropyl, bromoethyl and 3,3,3-trifluoropropyl groups. Among these, an alkyl group or an aryl group is preferable, and a methyl group or a phenyl group is more preferable. Also, a and b are rational numbers in the range of 0.7? A? 2.1, 0.001 b? 1.0, 0.8? A + b? 3.0, and more preferably 1.0? A + b? 2.5.

Specific examples of such polyorganohydrogen siloxane include methylhydrogen polysiloxane in which both terminals of the molecular chain are blocked with trimethylsiloxy groups; A dimethylsiloxane-methylhydrogensiloxane copolymer in which both terminals of the molecular chain are blocked with trimethylsiloxy groups; A dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymer in which both ends of the molecular chain are blocked with trimethylsiloxy groups; Dimethylpolysiloxanes wherein both ends of the molecular chain are blocked with a dimethylhydrogensiloxy group; A dimethylpolysiloxane-methylhydrogensiloxane copolymer in which both ends of the molecular chain are blocked with a dimethylhydrogensiloxy group; A dimethylsiloxane-methylphenylsiloxane copolymer in which both terminals of the molecular chain are blocked with a dimethylhydrogensiloxy group; Methylphenyl polysiloxane in which both terminals of the molecular chain are blocked with a dimethylhydrogensiloxy group; (R ₄ ) ₃ SiO _{0 .5} , a siloxy group unit represented by (R ₄ ) ₂ HSiO _{0 .5} , and a siloxane unit represented by SiO ₂ . A polyorganosiloxane copolymer comprising a siloxy group unit represented by (R ₄ ) ₂ HSiO _0.5 and a siloxy group unit represented by SiO ₂ ; A polyorganosiloxane copolymer comprising a siloxy group unit represented by R ₄ HSiO, a siloxy group unit represented by R ₄ SiO _{1 .5} , or a siloxy group unit represented by HSiO _{1 .5} . These may be used alone or in combination of two or more.

The polyorganohydrogen siloxane preferably has a viscosity of usually 1 to 500 mPa · S at 25 ° C, and more preferably 1 to 100 mPa · S.

The polyorganohydrogen siloxane may be contained in an amount such that the hydrogen atom is contained in an amount of 0.1 to 4 mol, preferably 1 to 3 mol, per 1 mol of the alkenyl group contained in the polyorganosiloxane. If the content is less than 0.1 mol, the curing reaction does not proceed sufficiently and it may be difficult to obtain a cured product. If the content exceeds 4 mol, a large amount of unreacted hydrosilyl group remains in the cured product, have.

The platinum-based catalyst is a catalyst for accelerating hydrosilation of an alkenyl group contained in the polyorganosiloxane and a hydrosilyl group contained in the polyorganohydrogen siloxane.

Examples of the platinum-based catalyst include platinum-based metals such as platinum, rhodium, ruthenium, palladium, osmium, indium, or organometallic compounds thereof. Further, there may be mentioned chloroplatinic acid, chloroplatinic acid hexahydrate, platinum dichloride, alcohol-modified chloroplatinic acid, chloroplatinic acid and olefinic compounds, coordination compounds of vinylsiloxane compounds or acetylene compounds.

The platinum-based catalyst may be contained in an amount of 0.1 to 1,000 ppm, preferably 1 to 500 ppm, more preferably 1 to 20 ppm, based on the platinum element, based on the total content of the polyorganosiloxane and the polyorganohydrogen siloxane. When the content is within the above range, the hydrosilation reaction is promoted and sufficient curing can proceed.

In addition, the curable polyorganosiloxane composition of the present invention may contain at least one additive such as fillers such as fumed silica, calcium carbonate, titanium dioxide, iron oxide, carbon black, and zinc oxide, pigments, dyes, stabilizers, flame retardants, .

The curable polyorganosiloxane composition prepared according to the present invention preferably has a viscosity of from 100 to 10,000 mPa · S, more preferably from 300 to 5,000 mPa · S as measured using a rotary viscometer at 25 ° C, .

The curable polyorganosiloxane composition can be prepared in a one-part form by mixing the components in a batch process or a continuous process using known methods such as milling, blending or stirring. In addition, a curing inhibitor such as acetylene alcohol can be added to adjust the curing arbitrarily. Two curing liquids can be mixed and cured when they are stored in two liquids so as not to proceed curing.

The curable polyorganosiloxane composition of the present invention constituted as described above is excellent in adhesion to both the metal and the heat-resistant plastic while maintaining a high transparency and a high light transmittance with almost no haze and is excellent in durability without peeling at the interface to which the composition is applied Can be improved.

The silicone elastomer can be prepared by curing the curable polyorganosiloxane composition of the present invention.

The curing conditions of the curable polyorganosiloxane composition are not particularly limited and are, for example, usually from 40 to 250 ° C, preferably from 40 to 200 ° C, more preferably from 60 to 170 ° C for 1 minute to 10 hours, Min to 6 hours.

The silicone elastomer prepared by curing the curable polyorganosiloxane composition can be used as a light emitting diode (LED), a photodiode, a charge coupled device (CCD), a complementary metal oxide semiconductor metal oxide semiconductor (CMOS), and the like. For example, as protective coatings for transistors, integrated circuits as well as electronic devices.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention. Such variations and modifications are intended to be within the scope of the appended claims.

Synthetic example  1 (Compound 1a)

0.1 mmol of the acid anhydride of the formula (Y = O) was dissolved in 100 ml of 1,4-dioxane, and 0.2 mmol of allyl alcohol was droppedwisely at room temperature for 1 hour, then the temperature of the reactor was raised to 50 ° C Stir for 24 hours. Thereafter, 0.22 mmol of epichlorohydrin and 0.001 mol of tetrabutylammonium bromide catalyst were added and reacted at 50 DEG C for 12 hours. The reaction was carried out by dropwise addition of 50 mL of a 5 wt% KOH aqueous solution and further stirring at 50 < 0 > C for 5 hours. And extracted with 300 mL of toluene and 500 mL of water. The extracted toluene layer was distilled under reduced pressure to obtain Compound 1a. The compound prepared at this time is a mixture of positional isomers in which the position of the allyl group and the epoxy group can be mutually changed.

[Reaction Scheme 1]

300Mhz / DMSO-d _6; 8.25 (2H), 7.85 (4H), 5.90 (2H), 5.41 (2H), 5.31 (2H)

Synthetic example  2 (Compound 1b)

Proceeding as in Synthesis Example 1, compound 1b was obtained by using an acid anhydride of the formula 2 [Y═C (CF ₃ ) ₂ ] in place of the compound of the formula 2 (Y═O).

[Reaction Scheme 2]

300Mhz / DMSO-d _6; (2H), 8.09 (2H), 8.05 (2H), 8.02 (2H), 8.02 2.74 (2H).

Synthetic example  3 (compound 1c)

Proceeding as in Synthesis Example 1, Compound 1c was obtained using an acid anhydride of Formula 2 (Y = CO) instead of Formula 2 (Y = O).

[Reaction Scheme 3]

300Mhz / DMSO-d _6; (M, 6H), 5.41 (2H), 5.31 (2H), 4.65 (2H), 4.17 (2H), 3.34

Synthetic example  4 (compound 1d)

Proceeding as described in Synthesis Example 1, Compound 1d was obtained using an acid anhydride of Formula 2 (Y = SO ₂ ) instead of Formula 2 (Y = O).

[Reaction Scheme 4]

300Mhz / DMSO-d _6; (2H), 8.87 (2H), 8.75 (2H), 8.35 (2H) 2.71 (2H).

Example  1-8 and Comparative Example  1-5

(1) Curability Polyorganosiloxane  Composition

Were mixed in the compositions shown in Table 1 below to prepare a curable polyorganosiloxane composition.

division
(Parts by weight) Polyorganosiloxane Polyorganohydrogen siloxane Platinum-based
catalyst
(ppm) Formula 1
(Synthesis Example) Adhesive Compound 1a Compound 1b Compound 1c Compound 1d A-1 A-2 A-3 A-4 A-5 Example 1 100 5.5 10 0.1 - - - - - - - - Example 2 100 5.5 10 0.5 - - - - - - - - Example 3 100 5.5 10 1.0 - - - - - - - - Example 4 100 5.5 10 1.5 - - - - - - - - Example 5 100 5.5 10 2.0 - - - - - - - - Example 6 100 5.5 10 - 1.0 - - - - - - - Example 7 100 5.5 10 - - 1.0 - - - - - - Example 8 100 5.5 10 - - - 1.0 - - - - - Comparative Example 1 100 5.5 10 - - - - 1.0 - - - - Comparative Example 2 100 5.5 10 - - - - - 1.0 - - - Comparative Example 3 100 5.5 10 - - - - - - 1.0 - - Comparative Example 4 100 5.5 10 - - - - - - - 1.0 - Comparative Example 5 100 5.5 10 - - - - - - - - 1.0 _{Polyorganosiloxane: (CH 3) 3 SiO 0} .5 / (CH 3) 2 (CH 2 = CH) SiO 0 .5 / SiO 2 And a dimethylpolysiloxane having both ends of the molecular chain blocked with a dimethylvinylsiloxy group
Polyorganohydrogen siloxane: methylhydrogen polysiloxane in which both terminals of the molecular chain are blocked with trimethylsiloxy groups
Platinum catalysts: complexes of chloroplatinic acid and divinyltetramethyldisiloxane
Content based on the total content of polyorganosiloxane and polyorganohydrogen siloxane (converted to platinum element)
A-1: 3-isocyanatopropyltrimethoxysilane
A-2: X-41-1053 (Shin-Etsu Chemical)
A-3: Vinyltrimethoxysilane (Shin-Etsu Chemical)
A-4: 3-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical)
A-5: Glycidyl methacrylate (aldrich)

(2) Hardened body

The joint surfaces of the two glass plates having a thickness of 5 mm were wiped with ethanol to remove foreign matter. A double-faced tape was attached to the edge of the glass plate, leaving the inlet and the air outlet at the joint surface, and the other glass plate was overlapped and clamped. The curable polyorganosiloxane composition prepared in (1) above was charged into the remaining inlet using a vinyl tube to fill the empty space, and then the open inlet and the air outlet were sealed with a hot-melt type sealant. The sealed assembly was thermally cured in an oven at 40 ° C for 4 hours to prepare a cured product.

Test Example

The physical properties of the cured products prepared in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Table 2 below.

One) Hayes (%)

The prepared cured product was measured using a haze meter (HM-150). At this time, as the numerical value increases, the visibility is considered to be low.

2) Transmittance (%)

The transmittance was measured using a spectro color meter (SE2000).

3) Adhesion ( Polyphthalic amide , Al )

A casting shape having a size of 10 mm x 4 mm (width x length) was formed on a polyphthalic amide (PPA) plate with a Teflon guard. The curable polyorganosiloxane composition of Example or Comparative Example was dispensed followed by curing at 150 ° C for 1 hour to prepare a cured product of 10 mm x 4 mm x 1 mm on the PPA.

The peel strength obtained by peeling the cured product from the interface with PPA using a TAXT analyzer was measured 10 times to calculate an average value (gf / mm).

Further, an average value (gf / mm) was calculated using an aluminum plate instead of a polyphthalic amide (PPA) plate in the same manner as above.

<Evaluation Criteria>

A peel strength of 300 (gf / mm) or more; ?

Peel strength of not less than 200 (gf / mm) and not more than 300 (gf / mm); ○

A peel strength of not less than 100 but not more than 200 (gf / mm); △

Peel strength less than 100 (gf / mm); ×

division Hayes
(%) Permeability
(%) Adhesion Al Polyphthalic amide Example 1 3.0 99.50 ○ ○ Example 2 3.2 99.45 ◎ ◎ Example 3 3.1 99.49 ◎ ◎ Example 4 3.0 99.50 ◎ ◎ Example 5 3.4 99.47 ◎ ◎ Example 6 3.2 99.45 ◎ ◎ Example 7 3.2 99.50 ◎ ◎ Example 8 3.2 99.47 ◎ ◎ Comparative Example 1 3.2 99.48 ○ × Comparative Example 2 3.1 99.50 × △ Comparative Example 3 3.0 99.48 ◎ × Comparative Example 4 3.2 99.51 △ △ Comparative Example 5 3.0 99.50 × ◎

As shown in Table 2, the curable polyorganosiloxane compositions of Examples 1 to 8 containing specific epoxy compounds according to the present invention had a lower haze than those of Comparative Examples 1 to 5, and had a lower light transmittance and an adhesion to metals and heat resistant plastics Was superior.

Claims (5)

An epoxy compound represented by the following formula (1):
[Chemical Formula 1]

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).
[2] The compound according to claim 1,

,

,

or

Lt; / RTI &gt;
Reacting a polyimide precursor of Formula 2 with allyl alcohol to produce a compound of Formula 3; And
A process for preparing an epoxy compound represented by the following formula (1), comprising: reacting a compound of the formula (3) with epichlorohydrin to prepare a compound of the formula

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).
1. A curable polyorganosiloxane composition comprising an epoxy-based compound represented by the following Formula 1:
[Chemical Formula 1]

(Wherein Y is O, CH ₂ , C (CH ₃ ) ₂ , C (CF ₃ ) ₂ , CO, SO or SO ₂ ).
5. The curable polyorganosiloxane composition according to claim 4, wherein the curable polyorganosiloxane composition contains a polyorganosiloxane, a polyorganohydrogen siloxane, a platinum catalyst, and an epoxy compound of the formula (1).