TW201341433A - Preparation method for polysiloxane containing alkyl (meth)acrylate groups and epoxy groups and polysiloxane thereof - Google Patents

Abstract

The present invention provides a preparation method for a polysiloxane containing alkyl (meth)acrylate groups and epoxy groups, which includes: adopting a compound having structure formula (II), a compound having structure formula (III) and a compound having structure formula (IV) to carry out reaction in the presence of a platinum-containing catalyst and a solvent. The present invention also provides a polysiloxane containing alkyl (meth)acrylate groups and alkyl glycidyl ether groups and represented by the structure formula (I). The definition of structure formulae of (I), (II), (III), and (IV) is described in the description and claims. The preparation method in this invention only requires one time reaction to graft two kinds of groups. The polysiloxane containing alkyl (meth)acrylate groups and alkyl glycidyl ether groups according to the present invention has high transparency and is difficult to cause yellowing after curing. The definition of M3, B2, and M4 in the structure formula (I) is described in the description and claims.

Description

Method for preparing polyoxyalkylene containing alkyl (meth) acrylate group and epoxy group and polyoxyalkylene oxide

The invention relates to a polydecane and a preparation method thereof, in particular to a polyoxyalkylene containing an alkyl (meth) acrylate group and an epoxy group and a preparation method thereof.

Polysiloxanes have many excellent properties such as low temperature elasticity, high temperature stability, oxidation resistance, radiation resistance, extremely low shrinkage, etc., and are widely used in various fields. Among them, liquid polyoxane adhesives are commonly used in articles such as glass, fibers, tires, water pipes, and microelectronic components.

Japanese Patent Laid-Open Publication No. 2004-101636, which uses a polyoxyalkylene adhesive to bond a touch panel with a transparent cover and a liquid crystal display device, but the polyoxyalkylene adhesive must be cured at a high temperature, and the curing speed is slow and Inefficient.

The (meth) acrylate group-containing polymer can be subjected to radical polymerization under ultraviolet irradiation, and the reaction speed is fast, which is in demand of an industrial process. In view of the advantages of (meth)acrylate-based polymers, attempts have been made to combine such polymers with polyoxyalkylenes, for example, US 4,568,566, US 4,652,661, US 7,994,356, US 8,026,293, US 2002137870, US 2007025399, JP 9316085, JP 10152560, in which a hydrosilylation reaction is carried out by reacting an allyl (meth) acrylate with a polyoxyalkylene containing a hydrogen atom bonded to a ruthenium in the presence of a catalyst, The (meth) acrylate group is grafted onto the polyoxyalkylene. The modified polyoxyalkylene has photocuring properties, but is limited to mono-functional modification of polyoxyalkylene having a molecular weight of 20,000 or less or a monomer unit number of 200 or less.

When the molecular weight of the polyoxyalkylene containing the hydrogen atom bonded by the hydrazine is 20,000 or more or the number of the monomer units is 200 or more, the subsequent hydrazine hydrogenation reaction is carried out with the allyl (meth) acrylate in the presence of a catalyst. It is easy to have a gel.

No. 4,576,999 discloses an ultraviolet cured release composition comprising a modified polyoxyalkylene containing an epoxy group and an acrylate group. The modified polyoxyalkylene is prepared by a platinum-containing catalyst by first hydrogenating a limonene oxide with a hydrazine hydrogen bond in a polyoxyalkylene chain, followed by adding a methallyl group. The methallyl chloride continues to react to obtain an intermediate product of a polyoxyalkylene having a chloroalkyl group and an epoxy group; and the intermediate product is further reacted with acrylic acid/pyridine or acrylic acid/triethylamine to obtain the epoxy group-containing compound. And an acrylate-based modified polyoxyalkylene. The modified polyoxyalkylene may have a structure represented by the following formula (a), wherein x, y, and z are each a positive integer of 1 to 1,000, respectively.

The epoxy group helps to rapidly cure the peeling composition, and the acrylate group is excellent in adhesion after curing by ultraviolet light, but in order to prevent gelation of the modified polyoxyalkylene, it is required The two-stage reaction is first prepared by preparing a polyoxyalkylene having a chloroalkyl group and an epoxy group, and then reacting the chloroalkyl group with the acrylic acid to obtain the epoxy group and the acrylic group-containing polyoxyalkylene. It is complex and time consuming, and in this way a non-transparent clear liquid of the product is produced which may behave in the form of a mist or a yellow mist.

From the above, it is known how to rapidly and efficiently modify a large molecular weight polyoxyalkylene, and the obtained polyoxyalkylene has photocuring properties, and has high transparency and low yellowing index in subsequent applications (yellow index) Good quality, such as YI value, is really needed by all walks of life.

Accordingly, a first object of the present invention is to provide a process for preparing a polyoxyalkylene group containing an alkyl (meth) acrylate group and an epoxy group.

Thus, the present invention provides a process for preparing an alkyl (meth) acrylate group and an epoxy group-containing polyoxane, comprising a compound having the structure of the formula (II), a compound having the structure of the formula (III), and a formula ( IV) a compound of the structure, which is obtained by reacting in the presence of a platinum-containing catalyst and a solvent:

Where M ¹ and M ² are the same or different respectively ; Q ¹ represents H, C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ ~C ₁₃ alkaryl; B ¹ contains D ¹ and D ² repeats Unit, D ¹ means ;D ² means In formula (II), the number of D ¹ is 0~5000, the number of D ² is 1~500; when D ^{1 is} not 0, the ratio of D ¹ :D ² is 100:1~1:1 ; R ¹ to R ⁵ are the same or different and each represents a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₁₂ aryl group, a C ₇ -C ₁₃ aralkyl group, or a C ₇ -C ₁₃ alkaryl group; The epoxy group-containing group is selected from the group consisting of C ₁ -C ₄ alkyl glycidyl ether groups, C ₁ -C ₄ alkyl glycidyl ester groups, C ₁ -C ₄ alkyl glycidylamine groups, C ₁ ~C ₄ linear aliphatic epoxy group or C ₅ -C ₁₂ alicyclic epoxy group; and A represents a C ₁ -C ₄ alkyl (meth) acrylate group.

Another object of the present invention is to provide a polyoxyalkylene group having an alkyl (meth) acrylate group and an alkyl glycidyl ether group having high transparency and a low YI value after hardening. The polyoxyalkylene group containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group, having the structure of the formula (I):

M ³ -B ² -M ⁴ (I)

Where M ³ and M ⁴ are the same or different respectively ; B ² contains D ³ , D ⁴ and D ⁵ repeating units, and D ³ represents ; D ⁴ means ; D ⁵ means R ⁶ to R ¹¹ are the same or different and each represents C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ -C ₁₃ alkaryl; E ¹ represents C ₁ -C ₄ alkyl glycidyl ether group; A represents a C ₁ -C ₄ alkyl (meth) acrylate group; Q ² represents -C ₂ H ₄ E ¹ , -C ₂ H ₄ A, C ₁ ~ C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ ~C ₁₃ alkaryl; in formula (I), D ³ :(D ⁴ +D ⁵ ) The molar ratio ranges from 99.9:0.1 to 70:30, and the molar ratio of D ⁴ :D ⁵ ranges from 99:1 to 1:99, and the molecular weight of the formula (I) ranges from 20,000 to 1,000,000.

The method for preparing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane according to the invention can be connected to the polyoxy siloxane with only one reaction, and there is no gelation. The situation happened. The alkyl (meth) acrylate group and the alkyl glycidyl ether group-containing polyoxy siloxane have high transparency and low YI value after curing, and can be used as a coating or coating as a coating. ) or encapsulant for semiconductor products such as LEDs.

First of all, in the present description, the (meth)acrylate [(meth)acrylate] means acrylate and/or methacrylate.

The present invention provides a process for preparing a polyoxyxane containing an alkyl (meth) acrylate group [having a structure represented by the following formula (i) or formula (ii)] and an epoxy group, which comprises a structure having the formula (II) The compound, the compound having the structure of the formula (III) and the compound having the structure of the formula (IV) are reacted in the presence of a platinum-containing catalyst and a solvent to obtain:

Where M ¹ and M ² are the same or different respectively ; Q ¹ represents H, C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ ~C ₁₃ alkaryl; B ¹ contains D ¹ and D ² repeats Unit, D ¹ means ;D ² means In formula (II), the number of D ¹ is 0~5000, the number of D ² is 1~500; when D ^{1 is} not 0, the ratio of D ¹ :D ² is 100:1~1:1 ; R ¹ to R ⁵ are the same or different and each represents a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₁₂ aryl group, a C ₇ -C ₁₃ aralkyl group, or a C ₇ -C ₁₃ alkaryl group; The epoxy group-containing group is selected from a C ₁ -C ₄ alkyl glycidyl ether group [having a structure represented by the following formula (iii)], a C ₁ -C ₄ alkyl glycidyl ester group [having the following a structure represented by the formula (iv) or the formula (v), a C ₁ -C ₄ alkyl glycidylamine group [having a structure represented by the following formula (vi)], and a C ₁ -C ₄ linear aliphatic epoxy group [Structure having the following formula (vii)] or C ₅ -C ₁₂ alicyclic epoxy group; and A represents a C ₁ -C ₄ alkyl (meth) acrylate group [having the following formula (viii)] The structure shown, wherein X ¹ is C ₁ -C ₄ alkyl, and X ² is selected from CH or C(CH ₃ )].

The preparation method only needs to carry out a one-step reaction, that is, the hydrogen atom bonded to the hydrazine of D ^{2 in} the formula (II) can be substituted with the formula (III) and the formula (IV), and the synthesized product is a clear and transparent liquid substance. And there will be no gelation.

Preferably, the compound having the structure of the formula (III) is used in an amount of 0.01 to 20 parts by weight based on 100 parts by weight of the compound having the structure of the formula (II), and the compound having the structure of the formula (IV) is used in an amount of 0.01. ~20 parts by weight.

More preferably, the compound having the structure of the formula (III) is used in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the compound having the structure of the formula (II), and the compound having the structure of the formula (IV) is used in an amount of 0.01. ~10 parts by weight.

Preferably, the E is a C ₁ -C ₄ alkyl glycidyl ether group. More preferably, the E is a methyl glycidyl ether group.

Preferably, the compound having the structure of formula (II) may be, for example but not limited to, D ^{1 in} an amount of 305, D ^{2 in} an amount of 67, R ¹ and R ^{2 in} a methyl group, and Q ¹ as H or a methyl group.

In order to promote the completion of the reaction, preferably, the reaction is carried out at 25 to 160 °C. When the reaction temperature is lower than 25 ° C, the reaction rate is too slow or even difficult to carry out; when the reaction temperature is higher than 160 ° C, gelation easily occurs.

The platinum-containing catalyst is used for the hydrogenation reaction of a hydrazine-bonded hydrogen atom of D ² of the formula (II) with an alkenyl group of the formula (III) or (IV). The amount of the platinum-containing catalyst to be used is not particularly limited as long as the hydrazine hydrogenation reaction can be sufficiently promoted. Preferably, the platinum-containing catalyst is selected from the group consisting of chloroplatinic acid or a platinum complex, and the commercially available product may be, for example but not limited to, "SYL-OFF 4000" (a platinum content of about 0.115 wt%) manufactured by Dow Corning.

Preferably, the solvent is selected from the group consisting of an aromatic organic solvent, an aliphatic organic solvent, or a combination thereof; the aromatic organic solvent is selected from the group consisting of toluene, xylene, or a combination thereof; The family organic solvent is selected from the group consisting of hexane, heptane, or a combination thereof. More preferably, the solvent is selected from the group consisting of toluene, hexane, or a combination thereof.

Preferably, a stabilizer is added to the solvent to stabilize the reaction, and the stabilizer may be, for example but not limited to, hydroquinone monomethyl ether (MEHQ). The amount of the stabilizer added is not particularly limited as long as it does not affect the progress of the hydrogenation reaction.

The polyalkylene oxide containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group of the invention has the structure of the formula (I):

M ³ -B ² -M ⁴ (I)

Where M ³ and M ⁴ are the same or different respectively ; B ² contains D ³ , D ⁴ and D ⁵ repeating units, and D ³ represents ; D ⁴ indicates ; D ⁵ indicates R ⁶ to R ¹¹ are the same or different and each represents C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ -C ₁₃ alkaryl; E ¹ represents C ₁ -C ₄ alkyl glycidyl ether group; A represents a C ₁ -C ₄ alkyl (meth) acrylate group; Q ² represents -C ₂ H ₄ E ¹ , -C ₂ H ₄ A, C ₁ ~ a C ₁₀ alkyl group, a C ₆ -C ₁₂ aryl group, a C ₇ -C ₁₃ aralkyl group, or a C ₇ -C ₁₃ alkaryl group; wherein the alkyl (meth) acrylate group is subjected to ultraviolet irradiation In the free radical polymerization, the alkyl glycidyl ether group helps to improve the adhesion of the polyoxyalkylene in subsequent use.

In formula (I), the molar ratio of D ³ :(D ⁴ +D ⁵ ) ranges from 99.9:0.1 to 70:30, and the molar ratio of D ⁴ :D ⁵ ranges from 99:1 to 1:99. The molecular weight of formula (I) ranges from 20,000 to 1,000,000.

Preferably, the polyoxyalkylene is synthesized from the above-mentioned method for preparing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane.

Preferably, the number of D ³ is 1 to 5000, the number of D ⁴ is 1 to 150, and the number of D ⁵ is 1 to 100.

Further preferably, when D ^{3 is} not 0, the molar ratio of D ³ :(D ⁴ +D ⁵ ) ranges from 99.9:0.1 to 90:10, and the molar ratio of D ⁴ :D ⁵ ranges from 75 :25~25:75.

More preferably, the number of D ³ is 250 to 450, the number of D ⁴ is 1 to 40, and the number of D ⁵ is 1 to 40.

Preferably, E ¹ represents a methyl glycidyl ether group.

Preferably, A represents a methyl (meth)acrylate group.

The present invention further provides a polyoxyalkylene composition comprising an alkyl (meth) acrylate group having an alkyl group (meth) acrylate group and an alkyl glycidyl ether group having a structure of the formula (I), and a photoinitiator. The polyoxyalkylene composition can be used as an adhesive for coatings or adhesives such as LED encapsulants.

The kind of the photoinitiator is not particularly limited, and may be used singly or in combination of two or more. For example, but not limited to, a phosphine oxide compound, a carbonyl compound, a triazine compound, An aminocarbonyl compound, an oxime compound, or a combination thereof.

Preferably, the photoinitiator is "Darocure 1173" manufactured by Merck.

Preferably, the photoinitiator is used in an amount ranging from 0.01 to 10 parts by weight based on 100 parts by weight of the polyoxyalkylene; more preferably, the photoinitiator is used in an amount ranging from 0.5 to 1.5 parts by weight.

The polyoxyalkylene resin composition forms a cured product after illumination. Preferably, the polydecane resin composition is thoroughly mixed, vacuum defoamed, and then photocured.

Preferably, the cured product has a transparency of 99% or more at 550 nm. More preferably, the cured product has a transmittance at 550 nm of 99.6% or more.

Preferably, the cured product has an elongation of 50% or more. More preferably, the cured product has an elongation of 210% or more.

The present invention will be further illustrated by the following examples, but it should be understood that this embodiment is intended to be illustrative only and not to be construed as limiting.

<Chemicals and equipment>

1. Polyoxane: purchased from Zhejiang Jian Orange Organic Co., Ltd., trade name "L202", viscosity 194mpas, molecular weight of about 26500, hydrogen content of 0.25; wherein the number of D ¹ repeating units is about 305, D ² The number of repeating units is approximately 67.

2. Allyl (meth)acrylate: purchased from TCI.

3. Allyl glycidyl ether: purchased from TCI.

4. Platinum complex: a platinum-containing catalyst available from Dow Corning under the trade name "SYL-OFF4000".

5. Photoinitiator: purchased from Merck, under the trade name "Darocure 1173".

6. Hydroquinone monomethyl ether: referred to as MEHQ.

7. A methacrylate group-containing dimethyl polyoxane: manufactured by Shin-Etsu Chemical Co., Ltd. under the trade name "X22-164C", having a molecular weight of about 5,000, a viscosity of 90 mm ² /s, and a cerium content of 37.2%. The ratio of acrylate substitution was 2%.

8. 1-Hexene: purchased from Acros organic.

9. Toluene: purchased from Merck.

<Examples 1 to 3 and Comparative Examples 1 to 2>

[Example 1] Preparation of poly(oxyalkylene oxide) containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group

92 g of L202, 20 g of toluene, SYL-OFF 4000 0.075 g and 0.008 g of MEHQ were weighed, placed in a 500 ml round bottom reaction flask equipped with a condenser, heated in a 65 ° C oil bath and continuously stirred.

6 g of allyl (meth) acrylate, 4 g of allyl glycidyl ether, toluene 20 g and 15 g of 1-hexene were uniformly mixed and added dropwise to the above-mentioned round bottom reaction bottle, and the dropping time was 3 hours. After the completion of the dropwise addition, the reaction was further stirred for 5 hours.

Then, 10 g of 1-hexene and 10 g of toluene were uniformly mixed and added dropwise to the above-mentioned round bottom reaction bottle, and the dropping time was 1 hour; during the dropwise addition, it was monitored by IR, and when the signal of Si-H disappeared, it was changed. The mixture in the reaction flask was concentrated under reduced pressure to give the product of Example 1.

The proportion of the chemical used in Example 1 is described in detail in Table 1.

[Examples 2 to 3]

The preparation method of the alkyl (meth) acrylate group and the alkyl glycidyl ether group-containing polyoxane of Examples 2 to 3 is the same as that of Example 1, except that the ratio of the amount of each chemical is used, and examples The chemicals used in 2~3 and the detailed dosages are listed in Table 1.

[Comparative Example 1]

100 g of L202, 50 g of toluene, 0.08 g of SYL-OFF4000, 0.008 g of MEHQ and 1.4 g of allyl (meth) acrylate were placed in a 500 ml round bottom reaction flask with a condenser and heated in a 65 ° C oil bath. Stirring was continued for 2 hours. The chemicals and amounts used in Comparative Example 1 are detailed in Table 1.

[Comparative Example 2]

Weigh 100g L202, 25g toluene, 0.04g SYL-OFF4000 and 0.004g MEHQ into a 500ml round bottom reaction flask with a condenser, heat in a 65 °C oil bath and continue to stir; then add 1.2g allyl (A A mixture of acrylate and 30 g of toluene was added dropwise to the reaction flask for 10 minutes, and after the addition was completed, the reaction was continued for 2 hours. The chemicals used in Comparative Example 2 and the detailed amounts are shown in Table 1.

<Application Examples 1 to 5 and Comparative Application Example 1> Preparation of Polyoxane Composition

[Application Example 1]

9 g of the polyalkylene oxide containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group prepared in Example 1 was weighed and thoroughly mixed with 0.1 g of a photoinitiator Darocure 1173, followed by vacuum defoaming, that is, The polyoxyalkylene composition was obtained.

[Application Examples 2~5]

The polyoxane composition of Application Examples 2 to 5 was prepared in the same manner as in Application Example 1, except that different alkyl (meth) acrylate groups and alkyl glycidyl ether group-containing polyoxyalkylene groups were used. . The types and amounts of chemicals used in Application Examples 2 to 5 are detailed in Table 2.

[Comparative Application Example 1]

9 g of methacrylate group-containing dimethyl polyoxane X22-164C was weighed and thoroughly mixed with 0.1 g of photoinitiator Darocure 1173, and then vacuum defoamed to obtain the polydecane composition. .

<Physical evaluation>

The following items were evaluated for Application Examples 1 to 5 and Comparative Application Example 1. The evaluation results are detailed in Table 2:

First, the penetration and yellowing index

First, the test pieces of Application Examples 1 to 5 and Comparative Application Example 1 were produced. An alkali-free glass having a thickness of 0.63 mm is taken, and a space of 20 mm in length and 300 μm in thickness is formed on the upper surface of the alkali-free glass by other alkali-free glass, respectively, in Application Examples 1 to 5, respectively. And the polyoxane composition of Comparative Application Example 1 was filled in the space and covered with another piece of alkali-free glass. The exposure machine was set to have an illuminance of 2000 Mw/cm ² and a total exposure energy of 1000 mJ/cm ² , and exposure was performed, and the cured product was subjected to a test after being completely cured. Among them, Comparative Application Example 1 was not completely cured after illumination, and thus no subsequent test was performed.

The test pieces of Application Examples 1 to 5 were measured for the yellowing index of the cured products by ultraviolet light visible light spectrometry (wavelength range of 400 to 800 nm), and the transmittance at 550 nm and 400 nm.

Second, the haze test

Take the above test piece for testing. The haze value (Hz), the total light transmittance (Tt), and the diffuse transmittance (Dfs) were measured using a haze meter Nippon Denshaku NDH 5000 (manufactured by Nippon Denshoku Industries Co., Ltd.) and substituted by the following formula:

Haze = diffusion rate (Dfs) / total light transmittance (Tt) × 100%

Third, the elongation rate determination

According to the ASTM D-638-03 Type V standard method, the test piece has a thickness of 3.2 mm and is tested at room temperature with a universal tensile machine. The speed of the tensile machine is 6 mm/min in %.

Fourth, tensile strength (tensile strength) and modulus (modulus)

According to the ASTM D-638-03 Type V standard method, the test piece has a thickness of 3.2 mm and is tested at room temperature with a universal tension machine. The speed of the tensile machine is 6 mm/min, and the unit is kPa.

Fifth, the adhesion strength (tensile adhesion)

Providing two alkali-free glasses of 25 mm (L) x 15 mm (W) x 5 mm (H); coating one of the two alkali-free glasses with a polyoxane composition in a coating range of diameter A circular shape of 5 mm; the other alkali-free glass was attached to the alkali-free glass coated with the polyoxyalkylene composition and exposed. The exposure machine was set to have an illuminance of 2000 mJ/cm ² and a total exposure energy of 10000 mJ/cm ² , and the polydecane composition was cured by light to form an adhesive layer having a thickness of 300 μm.

The tensile strength tester was used to test the force required to separate the two substrates, and the alkali-free glass was separated in a direction parallel to the bottom surface at a speed of 2 mm/min, and the stress at that time was measured. The measured stress is divided by the coated area of the polyoxyalkylene composition, and the adhesion strength of the polyoxyalkylene composition is counted.

Referring to Table 1, Examples 1 to 3 are 100 parts by weight of polyoxyalkylene (molecular weight: about 26,500) with 16 to 16.3 parts by weight of 1-hexane and 2.4 to 6.52 parts by weight of allyl (meth)acrylic acid. The ester is subjected to a hydrazine hydrogenation reaction with 0.6 to 4.35 parts by weight of allyl glycidyl ether, and D ^{2 is} grafted with a hexane group (accounting for 76.1 to 93.5% grafted to the D ² functional group), an alkyl (meth)acrylic acid. An ester group (2.1 to 13.1% grafted to the D ² functional group) and an alkyl glycidyl ether group (3.5 to 10.8% grafted to the D ² functional group), the product thus obtained does have D ⁴ and The D ⁵ repeating unit is a polyoxyalkylene containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group. In contrast, in Comparative Example 1 and Comparative Example 2, the reactant did not contain allyl glycidyl ether, and after the reaction of the polyoxyalkylene with allyl (meth) acrylate for two hours, gelation occurred, and It is in accordance with the needs of the present invention.

Referring to Table 2, it can be seen from Comparative Application Example 1 that the commercially available product "X22-164C" is a methacrylate group-containing dimethyl polyoxyalkylene, which is a low molecular weight compound (molecular weight of about 5,000). After that, it cannot be fully cured, so subsequent measurements cannot be performed. The polyoxane composition of Application Examples 1 to 5, which contains the alkyl (meth) acrylate group and the alkyl glycidyl ether group-containing polyoxyalkylene of Examples 1 to 3, and is mixed with a photoinitiator. Cured by light. The cured materials have a penetration of more than 98% at 400 nm and 550 nm (up to 99.8%), a yellowing index of less than 0.7, a haze value of less than 0.5, good transparency, and, when used as an adhesive, Provides adhesion strength above 130 kPa.

In summary, the preparation method of the present invention can be obtained by substituting a hydrogen atom bonded to a hydrazine in the formula (II) through a terminal having a double bond at the terminal (III) and (IV). An alkyl group-containing (meth) acrylate group having a functional group and a molecular weight of 20,000 or more and an epoxy group-containing polyoxyalkylene. The poly(oxyalkylene oxide) containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group is a clear and transparent liquid, and has the advantages of low haze, low YI value, high penetration, etc. after curing, and It has good mechanical properties and can be applied to adhesives, coatings or encapsulants for semiconductor products such as LEDs.

The above is only the preferred embodiment of the present invention, and the scope of the invention is not limited thereto, that is, the simple equivalent changes and modifications made by the scope of the invention and the description of the invention are All remain within the scope of the invention patent.

Claims (10)

A method for preparing a polyoxyxane containing an alkyl (meth) acrylate group and an epoxy group, comprising a compound having the structure of the formula (II), a compound having the structure of the formula (III), and a structure having the formula (IV) The compound is obtained by reacting in the presence of a platinum-containing catalyst and a solvent: Where M ¹ and M ² are the same or different respectively ; Q ¹ represents H, C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ ~C ₁₃ alkaryl; B ¹ contains D ¹ and D ² repeats Unit, D ¹ means ;D ² means In formula (II), the number of D ¹ is 0~5000, the number of D ² is 1~500; when D ^{1 is} not 0, the ratio of D ¹ :D ² is 100:1~1:1 ; R ¹ to R ⁵ are the same or different and each represents a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₁₂ aryl group, a C ₇ -C ₁₃ aralkyl group, or a C ₇ -C ₁₃ alkaryl group; The epoxy group-containing group is selected from the group consisting of C ₁ -C ₄ alkyl glycidyl ether groups, C ₁ -C ₄ alkyl glycidyl ester groups, C ₁ -C ₄ alkyl glycidylamine groups, C ₁ ~C ₄ linear aliphatic epoxy group or C ₅ -C ₁₂ alicyclic epoxy group; and A represents a C ₁ -C ₄ alkyl (meth) acrylate group. The method for producing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane according to the first aspect of the invention, wherein the weight of the compound having the structure of the formula (II) is 100 parts by weight. The compound having the structure of the formula (III) is used in an amount of 0.01 to 20 parts by weight, and the compound having the structure of the formula (IV) is used in an amount of 0.01 to 20 parts by weight. A method for producing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane according to the first aspect of the invention, wherein the molecular weight of the formula (II) ranges from 20,000 to 1,000,000 A method for producing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane according to the first aspect of the invention, wherein the epoxy group is a C ₁ -C ₄ alkyl glycidyl ether base. A process for producing an alkyl (meth) acrylate group and an epoxy group-containing polyoxy siloxane according to the first aspect of the invention, wherein the reaction is carried out at 25 to 160 °C. A polyoxyalkylene containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group, having the structure of the formula (I): M ³ -B ² -M ⁴ (I) wherein M ³ , M ⁴ Representing the same or different ; B ² contains D ³ , D ⁴ and D ⁵ repeating units, and D ³ represents ; D ⁴ means ; D ⁵ means R ⁶ to R ¹¹ are the same or different and each represents C ₁ -C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ -C ₁₃ alkaryl; E ¹ represents C ₁ -C ₄ alkyl glycidyl ether group; A represents a C ₁ -C ₄ alkyl (meth) acrylate group; Q ² represents -C ₂ H ₄ E ¹ , -C ₂ H ₄ A, C ₁ ~ C ₁₀ alkyl, C ₆ -C ₁₂ aryl, C ₇ -C ₁₃ aralkyl, or C ₇ ~C ₁₃ alkaryl; in formula (I), D ³ :(D ⁴ +D ⁵ ) The molar ratio ranges from 99.9:0.1 to 70:30, and the molar ratio of D ⁴ :D ⁵ ranges from 99:1 to 1:99, and the molecular weight of the formula (I) ranges from 20,000 to 1,000,000. The polyoxyalkylene group containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group according to claim 6, wherein the number of D ³ is 1 to 5,000, and the number of D ⁴ is 1 ~150, the number of D ⁵ is 1~100. The polyalkylene oxide containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group according to claim 6, wherein the number of D ³ is 250 to 450, and the number of D ⁴ is 1. ~40, the number of D ⁵ is 1~40. The polyoxyalkylene group containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group according to claim 6, wherein E ¹ represents a methyl glycidyl ether group. The polyoxyalkylene group containing an alkyl (meth) acrylate group and an alkyl glycidyl ether group according to claim 6 of the invention, wherein A represents a methyl (meth) acrylate group.