JPH07138369A - Organopolysiloxane and its production - Google Patents

Abstract

PURPOSE:To obtain an organopolysiloxane which can be used as a modified silicone sealant or the like as well as a modified silicone oil by subjecting two specified silane compounds to a hydrolysis reaction and a condensation reaction in a hydrophilic solvent. CONSTITUTION:A tetraalkoxyl functional silane and a 3- glycidoxypropylalkyldialkoxysilane are hydrolyzed in the presence of an organotin condensation catalyst and an acid hydrolysis catalyst in a hydrophilic solvent or a mixed solvent containing a hydrophilic solvent with water in an amount 3-4 times as large as the number of moles of the silanes to obtain an organopolysiloxane represented by the formula (wherein X is 1.5-0.5; (n) and (m) are each 1-10; and R is a 1-8C saturated hydrocarbon group or alkenyl). While a conventional methylpolysiloxane is not soluble in or does not have an affinity for an organic solvent or an organic resin, the organopolysiloxane is soluble in various organic solvents and has an affinity for various organic resins. Therefore, it can find wide applications such as a silicone for release paper, an adhesive sealing material, and a modified silicone sealant as well as a modified silicone oil.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an organopolysiloxane and a method for producing the same. More specifically, it relates to an organopolysiloxane obtained by cohydrolyzing and condensing a tetraalkoxy functional silane and 3-glycidoxypropylalkyldialkoxysilane in the presence of a condensation catalyst and a hydrolysis catalyst, and a method for producing the same.

[0002]

2. Description of the Related Art Silane coupling agents have been put to practical use since 1947 for use in glass-reinforced FRP and have been manufactured by Dow Corning's E.P.
lane) is a silane compound whose application has been developed. Even today, it is widely used as a binder that acts mainly between the thermosetting resin and the feeler to suppress the improvement of hot water resistance and the deterioration of electrical properties. Recently, in addition to the purpose of improving strength, it has been used as a fiber treatment agent as a chemical for giving slimy feel and impact resilience, and added for the purpose of improving orientation and strength by being added during the manufacture of plastic magnets. In addition, vinyl silane coupling agents are suitable for coating electric wires as a simple crosslinking agent for polyethylene. The silane coupling agent having a 3-glycidoxypropyl group is added to the epoxy resin compound and effectively used for maintaining the characteristics of the IC encapsulant, and also used as a dye-type hard coat agent for plastic lenses. There is. In addition, a co-hydrolyzate of tetramethoxysilane and 3-glycidoxypropyltrimethoxysilane has been experimentally produced, but unlike the present invention described later, it is an extremely low-viscosity oil in which a considerable amount of alkoxy groups remain. This seeks development as a so-called polymerized silane coupling agent, and is completely similar in structure and function. A polymethylsiloxane main chain having an alkoxy group as a pendant has also been proposed, but in both cases, the problem of compatibility with an organic resin becomes a major bottleneck and its application cannot be developed.

[0003]

As a result of earnest research, the present inventor has found the following facts and completed the present invention based on these findings. That is, in order to convert an alkoxy group into a silanol group without leaving an alkoxy group by cohydrolysis of a tetraalkoxysilane and an organofunctional alkoxysilane coupling agent, at least 3 times the molar amount of silane, preferably water, of 3. It is necessary to react 5 times or more of water. For this purpose, the hydrophilic solvent used must be in an amount sufficient to dissolve the added water. It has been found that a silane coupling agent which satisfies the above conditions and which is hydrolyzed for a long time only with an acid catalyst like S520 can be solved by adding a condensation catalyst such as an organic tin compound. Among the reaction raw materials relating to the present invention, ethyl orthosilicate alone has a hydrolysis rate of disappearing monomers within 30 minutes at room temperature, but when hydrolysis is started by mixing with S520, a significantly delayed reaction occurs. Occurs. In the present invention, this problem is also solved by the two-step hydrolysis condensation reaction method. As is clear from the above description, the present invention does not utilize the residual alkoxy group which has been conventionally proposed, but is rich in crosslinkability and reactivity,
Moreover, it is an object of the present invention to provide a polysiloxane functionalized with 3-glycidoxypropyl group containing a silanol group and a three-dimensional structure, which is stable at room temperature, and a method for producing the same. It is also possible to obtain a cured product of this silanol group by polycondensation with a methyl polymer or polysiloxane cross-linking. Of course, the contained epoxy group can be subjected to a usual polymerization reaction, and because of its good compatibility with the epoxy resin, it is possible to carry out a homogeneous polymerization which was not possible with conventional polysiloxanes, so that a new demand can be created.

[0004]

The present invention has the following configurations (1) to (5). (1) In a mixed solvent containing a tetraalkoxy-functional silane and 3-glycidoxypropylalkyldialkoxysilane in a hydrophilic solvent or a hydrophilic solvent, in the presence of an organotin condensation catalyst and an acid hydrolysis catalyst, the total molar amount of silane is 3 to 3. A process for producing an organopolysiloxane oil represented by [Chemical Formula 5], which comprises hydrolyzing and condensing with 4-fold molar water to obtain an organopolysiloxane oil represented by [Chemical Formula 5].

[Chemical 5] (Here, x is 1.5 to 0.5, and n and m are 1 to 1 respectively.
An integer of 0 and R is a saturated hydrocarbon group having 1 to 8 carbon atoms or an alkenyl group. (2) Tetraalkoxysilane represented by the general formula Si (OR ¹ ) ₄ and 3-glycidoxypropylalkyldialkoxysilane represented by the general formula [Chemical Formula 6] in the presence of an organic tin condensation catalyst in a hydrophilic solvent. Alternatively, an organopolysiloxane obtained by co-hydrolyzing and condensing with an acid catalyst in a mixed solvent containing a hydrophilic solvent and using 3 to 4 times the molar amount of water of the silane.

[Chemical 6] (Here, the alkyl group R is a C _{1 to} C ₈ saturated hydrocarbon group or an alkenyl group.) (3) The molar ratio of the tetraalkoxysilane and the 3-glycidoxypropylalkyldialkoxysilane of the above (2) is An organopolysiloxane represented by the following [Chemical Formula 7] which is reacted at 1/1 or less.

[Chemical 7] (The silanol group x is in the range of 1.5 to 0.5 and the polymer end group is a silanol group.) (4) Cohydrolysis and condensation of tetraalkoxysilane and 3-glycidoxypropylalkyldialkoxysilane Prior to the reaction, tetraalkoxysilane was hydrolyzed by adding an acid catalyst and 3 to 4 times the molar amount of water to the total amount of silane, followed by addition of an organotin catalyst and a predetermined molar ratio of 3-glycidoxypropylalkyldialkoxysilane. A method for producing an organopolysiloxane compound represented by [Chemical Formula 8] by a two-step hydrolysis and condensation method of causing a hydrolysis and condensation reaction.

[Chemical 8] (5) The tetraalkoxysilane is tetramethoxysilane or tetraethoxasilane, and the 3-glycidoxypropyldialkoxysilane is either 3-glycidoxypropylmethyldimethoxysilane or 3-glycidoxypropylmethyldiethoxysilane. A method for producing the compound of the above (4) by combining the above.

The structure and effect of the present invention will be described in detail below. Examples of the tetraalkoxysilane used in the present invention include tetramethoxysilane, tetraethoxysilane, and tetra-n-proxysilane. Among these, tetramethoxysilane or tetraethoxysilane is advantageously used, judging from the hydrolysis rate and Si content. That is, as tetraethoxysilane, a commercially available product such as ethyl orthosilicate manufactured by Tama Chemical Co., Ltd. can be used. On the other hand, as a dialkoxy silane coupling agent containing a 3-glycidoxypropyl group, an alkyl group R is C
Saturated hydrocarbon group or an alkenyl group having ₁ -C ₈ is adapted, but particularly preferably C ₁ -C ₂ saturated hydrocarbon group or a vinyl group can be used. Two alkoxy groups are also C
Those prepared from _{1 to} C ₈ saturated alcohol are suitable, and particularly preferred are methoxy group and ethoxy group depending on the hydrolysis rate. That is, 3-glycidoxypropylmethyldimethoxysilane (Sila Ace S520 manufactured by Chisso Corporation) and 3-glycidoxypropylmethyldiethoxysilane (CF silane KBE40 manufactured by Shin-Etsu Chemical Co., Ltd.)
Commercial products such as 2) can be used.

Next, regarding an acid as a hydrolysis catalyst, the acid concentration is not particularly specified as long as a catalytic amount of acid is used. For example, there is a method in which a diluted acid is added by a specified amount of water. As the type of acid, any of an organic acid such as acetic acid, an inorganic acid such as hydrochloric acid and sulfuric acid, or a strongly acidic ion exchange resin can be used, but an inorganic acid having a high hydrolysis rate is preferably recommended.

Any of a wide variety of materials that act as silanol condensation catalysts can be used in the present invention. Such materials include, for example, organotin compounds such as dibutyltin dilaurate, stannous acetate, stannous octoate, or metal carboxylates such as zinc naphthenate, zinc octanoate, 2-ethylhexanoic acid and cobalt naphthenate. Rates, titanium esters and chelates. Preferred compounds are organotin compounds, especially tin carboxylates such as dibutyltin dilaurate, dibutyltin diacetate. The amount of condensation catalyst is not particularly limited as long as it is a catalytic amount, but is generally 0.05% or less of the total amount of silane. It is necessary to add water in an amount of 3 to 4 times mol, preferably 3.5 times mol or more based on the total mol of silane in order to sufficiently perform hydrolysis.

The reaction solvent may be a hydrophilic solvent alone, but a mixed solvent of hydrophilic solvent and a mixed solvent of lipophilic and hydrophilic solvent are also applicable. For example, hydrophilic solvents such as methanol, ethanol, acetone, tert-butanol and diacetone alcohol, or mixed solvents such as xylene / alcohol and toluene / alcohol can be used.

In the production of the organopolysiloxane according to the present invention, the two-stage hydrolytic condensation method occupies an important position in the invention. That is, when tetraalkoxysilane such as ethyl orthosilicate alone is used to measure hydrolysis under an acid catalyst by a gas chromatographic (GC) check method, the monomer disappears in several tens of minutes at room temperature. On the other hand, a dialkoxy silane coupling agent such as S520 has a significantly longer hydrolysis time than tetraalkoxysilane, and only a little less than 40% is hydrolyzed in two days. It was found that the addition of the condensation catalyst described above is effective in accelerating this. However, when an attempt is made to carry out a cohydrolysis condensation reaction by mixing ethyl orthosilicate and S520 in a batch, a significant delay occurs that the hydrolysis of ethyl orthosilicate takes several days under the condition without a condensation catalyst. Of course, the hydrolysis of S520 is slow. When the condensation catalyst is added, the hydrolysis of S520 is promoted and the hydrolysis is performed in several hours. However, after all, about 40% of the charged ethyl silicate remained after 3 days.
It is unclear why such a large reaction delay occurs.

In view of such a fact, in the present invention, ethyl orthosilicate is hydrolyzed with a specified amount of water in the presence of an acid catalyst, and then a condensation catalyst and a specified mole of S520 are added to cause a cohydrolysis condensation reaction. According to this two-step hydrolysis condensation reaction, the reaction can be completed within several hours at room temperature. Therefore, the structural form of the polymer is expected to be a block copolymer.

Further, in the present invention, a novel compound having a silanol group which is stable at room temperature and having an epoxy oxygen amount equivalent to the charged mol of organopolysiloxane which has been subjected to a cohydrolysis condensation reaction has been successfully isolated. For isolation, the organic solvent used is distilled off at low temperature as a hydrophilic solvent, at medium temperature as a lipophilic solvent and a water azeotrope of these solvents. Heat and dry at a bath temperature of 140 to 150 ° C. to remove the remaining water.

To measure the solubility of the organopolysiloxane oil obtained in the present invention, 100 mg of the silicone oil sample of the present invention was placed in a glass sample tube and 1 m
It was carried out by the method of adding 1 of each solvent and observing the solubility by visual observation. The results were displayed in 5 grades: easily soluble, soluble, slightly soluble (slightly cloudy), slightly soluble (white cloudy), and insoluble. The organopolysiloxane oil according to the present invention is soluble in many solvents such as toluene and alcohol. This property is a property that methyl silicone oil does not have.

It can be confirmed that the organopolysiloxane compound of the present invention is generally a compound represented by the above general formula by means of the following (a) to (d). (A) Analysis of infrared absorption spectrum (IR) Characteristic absorption of Si—OH around 3450 cm ⁻¹ , 300
Several absorptions due to CH bonds near 0 to 2900 cm ^{−1 and} a broad absorption of Si—O—Si near 1100 to 1000 cm ⁻¹ appear. 3450 cm ^-1 absorbance of the absorption peak and 2940 cm ^-1 vicinity of the absorption peak in the vicinity (l
The ogI ₀ / I) ratio is an index of the relative value of the silanol group content rate. That is, if this value is 1.0 or less, it is an oil having a silanol group that is stable at room temperature. When this value is 1.0 or more, it is an organopolysiloxane polymer that exhibits a resin-state solid upon heating at several tens of degrees Celsius. (B) ¹ H-nuclear magnetic resonance spectrum ( ¹ H-NMR) The number and bonding mode of hydrogen atoms in the organopolysiloxane compound of the present invention, and (Si) -OH depending on deuterium substitution.
It is possible to know the number of (Si) -OH from the ratio of hydrogen atoms. The relationship between the structural formula and the signal in Example 1 described later is as follows.

[0014]

[Chemical 9]

[0015]

[Table 1]

[0016] The oxirane oxygen content is determined by a redox titration method with iodine-potassium thiosulfate. (D) Carbon and hydrogen (CH) elemental analysis The carbon and hydrogen content can be known by the micro elemental analysis method.

Viscosity data was measured using a rotational viscometer'VISCONIC 'manufactured by Tokyo Keiki Co., Ltd. at a constant temperature of 25 ° C. In the organopolysiloxanes of Examples 1 to 3 of the present invention, the viscosity was changed in proportion to the S520 / ethyl orthosilicate molar ratio in the range of about 1000 cp to 8000 cp. That is, the higher the molar ratio of orthoethyl silicate, the higher the viscosity, and a similar relationship was observed in infrared absorption (IR). In other words, to the ethyl orthosilicate many plotting the relationship between the molar ratio per strength 2950 cm ^-1 absorption peak based on 3450 cm ^-1 absorption peak and CH based on silanol log I ₀ / I spectrophotometric taking the ratio of both peaks As the amount of relative silanol increases. This is because the ethyl orthosilicate component having a three-dimensional three-dimensional structure is increased and the S520 component, which is a linear polymer component, is relatively decreased. Therefore, the increase in ethyl orthosilicate causes increase in viscosity and increase in silanol groups. Easy to understand. Further, in the production method by the two-step hydrolysis-condensation reaction method of the present invention, at least 5 since no monomer or oligomer is detected by GC measurement due to the hydrolysis reaction of ethyl orthosilicate alone in the first step.
It is presumed that an oligomer block of a monomer or higher is formed. From the above viscosity and silanol behavior in the second reaction, it is considered to be a block copolymer.

[0018]

EFFECTS OF THE INVENTION The organopolysiloxane of the present invention has a silanol group stable at room temperature in a polymer, which is composed of tetraalkoxysilane and 3-glycidoxypropylalkyldialkoxysilane, as proved in Examples described later. It has 0.5 to 1.5 per unit depending on the charged molar ratio. Further, it has a glycidyl type epoxy group as an organic functional group in an amount corresponding to the charged molar ratio of 3-glycidoxypropylalkyldialkoxysilane. Therefore, most methyl-based polysiloxanes do not dissolve or have an affinity in organic solvents or organic resins, whereas the organopolysiloxanes of the present invention dissolve in many types of organic solvents. It also has an affinity for many kinds of organic resins. Due to these characteristics, it can be used not only as a modified silicone oil, but also in a wide range of other applications such as release agents, silicones for release paper, silicones for personal care, paint additives, silicone adhesives, adhesive sealing materials, and modified silicone silanes. It is a useful compound. The present invention will be described below in more detail with reference to Examples, but the present invention is not limited to these Examples.

[0019]

【Example】

Example 1 Synthesis of silanol group-containing polysiloxane-3-glycidoxypropylmethylpolysiloxane copolymer oil S52
0 / ethyl orthosilicate = 2/1 (mol) 70 g of ethyl orthosilicate manufactured by Tama Chemical Co., Ltd. was placed in a 1 L three-necked flask, and toluene / methanol = as a reaction solvent.
Add 500 ml of 60/40 mixed solvent. Hydrochloric acid as a hydrolysis catalyst and a catalytic amount and 64 ml of 3.5 times mol of water are added, and the mixture is stirred and reacted at room temperature for 30 minutes. The disappearance of the peak of ethyl orthosilicate is confirmed by gas chromatography (GC). 148 g of S520 manufactured by Chisso Corporation and 0.05 g of dibutyltin dilaurate as a condensation catalyst are added, and the mixture is hydrolyzed and condensed under stirring at room temperature for 3 to 5 hours. The reaction is terminated by confirming the disappearance of S520 and its oligomer peak by GC. Heat in a water bath and distill off methanol and azeotropic solvent under strong stirring. The residual liquid is transferred to a 300 ml flask, heated in an oil bath, and the water containing residual toluene and hydrochloric acid is distilled off under vigorous stirring. The oil thus obtained weighed 119 g and had a theoretical yield of 9
It was 8%, a transparent viscous liquid with a colorless and slightly sweet scent, containing oxirane oxygen of 8.7%, C46.3%, and H of 8.15%. Calculated values for the empirical formula C ₁₄ H ₂₉ O ₅ Si ₃ oxirane oxygen 8.9%, C 46.5%, H 8.1
%, O22.1%, Si24.1%. The viscosity was 7,800 centipoise (25 ° C). IR
The chart and the NMR chart are shown in FIGS. 1 and 2. The proof that the signal at 1.96 ppm in NMR was based on OH was confirmed by the deuterium substitution shown in FIG. The results of determination of solubility by visual observation are as follows: soluble in toluene, hexane, acetone, soluble in methanol, ethyl acetate, methyl ethyl ketone, chloroform, slightly soluble in ethanol (slightly cloudy), slightly soluble in isopropanol (cloudy), in water. It was insoluble. The absorbance of the absorption peak and 2940 cm ^-1 vicinity of the absorption peak around 3450 cm ^-1 (log I
₀ / I) ratios were 0.70 and 0.8 respectively in repeated experiments.
It was 2.

Example 2 Synthesis of silanol group-containing polysiloxane-3-glycidoxypropylmethylpolysiloxane copolymerized oil S52
0 / ethyl orthosilicate = 4/1 (mol) It is produced by a two-step hydrolysis condensation reaction as in Example 1.
However, the charged amount was 17.6 g of ethyl orthosilicate, 250 ml of a mixed solvent of toluene / methanol = 60/40, and 1/10.
28.3 ml of normal hydrochloric acid solution (first step), 7 of S520
After 4.0 g and 0.01 g of dibutyltin dilaurate (second step) for several hours, the disappearance of the monomer is confirmed by GC, and the solvent and water are distilled off. 55 g of oil thus obtained
95% of theoretical yield, transparent viscous liquid with colorless and slightly sweet scent, oxirane oxygen-containing 9.1%, C47.9%,
It was H 8.21%. _Empirical formula C ₂₈ H _56.8 O _9.9 Si ₅
Calculated value for oxirane oxygen 9.3%, C4
8.6%, H8.2%, O22.9%, Si20.3%
Well matched. Viscosity is 1570 centipoise (25
℃). IR chart and NMR chart are shown in FIGS. 4 and 5. The proof that the 1.63 ppm signal superimposed on the methylene group by NMR was based on OH was confirmed by the deuterium substitution shown in FIG. The 3450
cm ^-1 vicinity absorbance of the absorption peak and 2940 cm ^-1 vicinity of the absorption peak of the (logI ₀ / I) ratio was 0.30.

Example 3 Synthesis of silanol group-containing polysiloxane-3-glycidoxypropylmethylpolysiloxane copolymerized oil S52
0 / ethyl orthosilicate = 8/1 (mol) It is produced by a two-step hydrolysis condensation reaction as in Example 1.
However, the charge amount was 8.8 g of ethyl orthosilicate, 250 ml of a mixed solvent of toluene / methanol = 60/40, 26.0 ml of 1/10 normal hydrochloric acid solution (first stage), 74.
0 g and 0.01 g of dibutyltin dilaurate (second stage)
After several hours, the disappearance of the monomer is confirmed by GC, and the solvent and water are distilled off. The oil thus obtained was 53 g in 96% of the theoretical yield, a transparent viscous liquid with a colorless and slightly sweet scent, oxirane oxygen-containing 9.7%, C50.9%, H
It was 8.05%. _Empirical formula C ₅₆ H _112.6 O _17.8 Si ₉
Calculated value for oxirane oxygen 9.7%, C5
0.8%, H8.6%, O21.5%, Si19.1%
Well matched. Viscosity is 1210 centipoise (25
℃). IR chart and NMR chart are shown in FIGS. 7 and 8. The proof by NMR that the 1.63 ppm signal superimposed on the methylene group was based on OH was confirmed by the deuterium substitution shown in FIG. The 3450
cm ^-1 vicinity absorbance of the absorption peak and 2940 cm ^-1 vicinity of the absorption peak of the (logI ₀ / I) ratio was 0.23.

[Brief description of drawings]

FIG. 1 shows an infrared absorption diagram of an example of the present invention.

FIG. 4 Same as above.

FIG. 7 Same as above.

FIG. 2 shows an NMR chart of an example of the present invention.

FIG. 3 Same as above.

FIG. 5 Same as above.

FIG. 6 Same as above.

FIG. 8 Same as above.

FIG. 9 Same as above.

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[Procedure amendment]

[Submission date] May 31, 1994

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] Brief description of the drawing

[Correction method] Change

[Correction content]

[Brief description of drawings]

FIG. 1 shows an infrared absorption diagram of an example of the present invention.

FIG. 2 shows an NMR chart of an example of the present invention.

FIG. 3 shows an NMR chart of an example of the present invention.

FIG. 4 shows an infrared absorption diagram of an example of the present invention.

FIG. 5 shows an NMR chart of an example of the present invention.

FIG. 6 shows an NMR chart of an example of the present invention.

FIG. 7 shows an infrared absorption diagram of an example of the present invention.

FIG. 8 shows an NMR chart of an example of the present invention.

FIG. 9 shows an NMR chart of an example of the present invention.

Claims (5)

[Claims] 1. A total mole of silane in the presence of an organotin condensation catalyst and an acid hydrolysis catalyst in a hydrophilic solvent or a mixed solvent containing a hydrophilic solvent containing tetraalkoxy-functional silane and 3-glycidoxypropylalkyldialkoxysilane. A method for producing the oil, which comprises subjecting the organopolysiloxane oil represented by [Chemical Formula 1] to hydrolysis and condensation with 3 to 4 times the molar amount of water to obtain the organopolysiloxane oil. [Chemical 1] (Here, x is 1.5 to 0.5, and n and m are 1 to 1 respectively.
An integer of 0 and R is a saturated hydrocarbon group having 1 to 8 carbon atoms or an alkenyl group. ) 2. A tetraalkoxysilane represented by the general formula Si (OR ¹ ) ₄ and a 3-glycidoxypropylalkyldialkoxysilane represented by the general formula [Chemical Formula 2] are hydrophilic in the presence of an organotin condensation catalyst. An organopolysiloxane obtained by co-hydrolyzing and condensing a solvent or a mixed solvent containing a hydrophilic solvent with an acid catalyst in an amount of 3 to 4 times the molar amount of water of the silane. [Chemical 2] (Here, the alkyl group R is a C _{1 to} C ₈ saturated hydrocarbon group or an alkenyl group.) 3. The tetraalkoxysilane of claim 2 and 3
An organopolysiloxane of the following [Chemical Formula 3] which is obtained by reacting glycidoxypropylmethyldialkoxysilane at a molar ratio of 1/1 or less. [Chemical 3] (The silanol group x is in the range of 1.5 to 0.5 and the polymer end group is a silanol group.) 4. Tetraalkoxysilane and 3-glycidoxypropylalkyldialkoxysilane are hydrolyzed by adding an acid catalyst and water in an amount of 3 to 4 times the total silane moles prior to the cohydrolysis and condensation reaction. After that, an organotin catalyst and a predetermined molar ratio of 3-glycidoxypropylalkyldialkoxysilane are added to cause a cohydrolysis condensation reaction to produce an organopolysiloxane compound represented by [Chemical Formula 4]. Law. [Chemical 4] 5. The tetraalkoxysilane is tetramethoxysilane or tetraethoxasilane, and the 3-glycidoxypropyldialkoxysilane is 3-glycidoxypropylmethyldimethoxysilane or 3-glycidoxypropylmethyldiethoxysilane. The method for producing the compound according to claim 4, which is a combination of any of the above.