JP2000169482A - Hydroxyphenyl group-containing organosilicon compound and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new hydroxyphenyl group-containing organosilicon compound containing hydroxyphenyl group and an aliphatic unsaturated bond in a same molecule and useful as an adhesive-providing agent for bonding a cured material of addition reaction type silicone composition to various kinds of organic resins and containing hydroxyphenyl group and an aliphatic unsaturated bond in same molecule. SOLUTION: This organosilicon compound is represented by formula I [X is an aliphatic unsaturated group-containing monovalent hydrocarbon; Z is a carbonyloxy of the formula C(O)O or phenylene; Y is an (alkyl or alkoxy- substituted)hydroxyphenyl; R1 is a >=2C divalent hydrocarbon or the like; (m) and (p) are each 0 or 1; (n) is 0-2; (q) is 0-7], e.g. a compound of formula II. The compound of formula I is obtained by subjecting a silicon atom-bonded hydrogen atom-containing organosilicon compound of formula III (X is an alkenyl) to addition reaction with an aliphatic unsaturated bond-containing compound of the formula R3-Y1 [R3 is an aliphatic unsaturated bond-containing hydrocarbon group; Y1 is a (substituted) hydroxyphenyl] in the presence of a hydrosilylated catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organosilicon compound containing a hydroxyphenyl group and an aliphatic unsaturated bond in the same molecule and a method for producing the same.

[0002]

2. Description of the Related Art Silicone compositions which are based on alkenyl-containing organopolysiloxanes and organohydrogenpolysiloxanes and which cure in the presence of a platinum-based catalyst are called addition-curable silicone compositions.
Used in many industrial fields. However, since the surface of a cured product of this type of silicone composition is inactive, it has been extremely difficult to bond various organic resins such as an epoxy resin and a phenol resin to the cured product. Therefore, a method has been attempted in which the surface of a cured product of the addition-reaction-curable silicone composition is treated with ozone, and various organic resins are brought into contact with and cured with the ozone-treated surface, and the two are bonded and integrated. However, this method has a drawback that the adhesiveness decreases with time, and is not a practically satisfactory method. Therefore, the appearance of an adhesion imparting agent for adhering a cured product of the addition reaction type silicone composition to various organic resins has been desired. As such an adhesion-imparting agent, for example, a hydroxyphenyl group as a functional group for improving adhesion to an organic resin and an alkenyl group as a functional group for being incorporated into an addition reaction cured product have the same molecule. Although the organosilicon compound contained therein is considered to be effective, such an organosilicon compound has not been known. Incidentally, hydroxyphenyl group-containing organosilicon compounds are known (see JP-A-2-166123 and JP-A-2-225524), but hydroxyphenyl group-containing organosilicon containing an aliphatic unsaturated bond. The compound is not known.

[0003]

The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have reached the present invention. That is, an object of the present invention is to provide a novel organosilicon compound containing a hydroxyphenyl group and an aliphatic unsaturated bond in the same molecule, and a method for producing the same.

[0004]

According to the present invention, there is provided a compound represented by the general formula:

Embedded image [Wherein X is a monovalent hydrocarbon containing an aliphatic unsaturated group, and Z is -C (O)
A carbonyloxy group or a phenylene group represented by O-,
Y is a hydroxyphenyl group, an alkyl-substituted hydroxyphenyl group or an alkoxy-substituted hydroxyphenyl group, R ¹ is a same or different divalent hydrocarbon group having 2 or more carbon atoms, and R does not contain an aliphatic unsaturated bond same or different monovalent hydrocarbon group, a is the number of carbon atoms of one or more divalent hydrocarbon group, or a group of the formula: -R ² -O-R ² - (in the formula, R ² is a divalent hydrocarbon radical ). m and p are 0
Or 1, n is 0 to 2, and q is an integer of 0 to 7. And a method for producing the same.

First, the hydroxyphenyl group-containing organosilicon compound of the present invention will be described. The hydroxyphenyl group-containing organosilicon compound of the present invention is a compound represented by the above general formula. It contains a monovalent hydrocarbon containing an aliphatic unsaturated bond. In the above formula,
X is an alkenyl group, and examples include a vinyl group, an allyl group, an isopropenyl group, and a hexenyl group. Z is a carbonyloxy group or a phenylene group represented by -C (O) O-, and examples of the phenylene group include an o-phenylene group, an m-phenylene group, and a p-phenylene group. Y is a substituted or unsubstituted hydroxyphenyl group, and examples thereof include a hydroxyphenyl group, an alkyl group-substituted hydroxyphenyl group and an alkoxy group-substituted hydroxyphenyl group. The substitution positions of the hydroxyl group, alkyl group and alkoxy group are not particularly limited. Examples of such an alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group, and examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group. Further, as a substituted or unsubstituted hydroxyphenyl group, a 2-hydroxyphenyl group,
Hydroxyphenyl group such as 4-hydroxyphenyl group, 3,4-dihydroxyphenyl group, 3,5-dihydroxyphenyl group; 3,5-ditert-butyl-4-hydroxyphenyl group, 3-methyl-4-hydroxyphenyl group And the like. Alkyl-substituted hydroxyphenyl groups such as 4-hydroxy-3-methoxyphenyl group and 3,5-dimethoxy-4-hydroxyphenyl group are exemplified. Y is preferably a 2-hydroxyphenyl group and a 4-hydroxy-3-methoxyphenyl group. R ¹ is a same or different divalent hydrocarbon group having two or more carbon atoms containing no aliphatic unsaturated bond, and an alkylene group such as an ethylene group, a propylene group, a butylene group, and a hexylene group, and an arylene group such as a phenylene group. Groups are exemplified. R is the same or different monovalent hydrocarbon group containing no aliphatic unsaturated bond, methyl group, ethyl group,
Alkyl groups such as butyl, pentyl and hexyl;
Aryl groups such as phenyl, tolyl and xylyl;
An aralkyl group such as a benzyl group and a phenethyl group is exemplified. A is a divalent hydrocarbon group having 1 or more carbon atoms or a formula: -R ² -O-R ^2- (wherein R ² is a divalent hydrocarbon group, and an alkylene group or an arylene group as described above. And an ethylene group, a propylene group, a butylene group, a hexylene group, and an ethyleneoxypropylene group. m and p are 0 or 1. n is 0 to 2 and q
Is an integer of 0 to 7.

The hydroxyphenyl group-containing organosilicon compound of the present invention includes, for example, a compound represented by the following formula.

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Next, a method for producing the hydroxyphenyl group-containing organosilicon compound of the present invention will be described. The method for producing a hydroxyphenyl group-containing organosilicon compound of the present invention according to the present invention comprises:

Embedded image Wherein X is an alkenyl group, Z is a carbonyloxy group or a phenylene group represented by -C (O) O-, R is the same or different monovalent hydrocarbon group containing no aliphatic unsaturated bond, and A is 1 or more divalent hydrocarbon group, or a group of the formula carbon atoms: -R ² -O
—R ² — (wherein, R ² is a divalent hydrocarbon group). m and p are 0 or 1, n is 0 to 2, and q is an integer of 0 to 7. And an organosilicon compound containing a silicon-bonded hydrogen atom represented by the formula: (B) a general formula: R ³ -Y ^{1 wherein} R ³ is an aliphatic unsaturated bond-containing monovalent hydrocarbon group; ¹ is a substituted or unsubstituted hydroxyphenyl group. The method for producing a hydroxyphenyl group-containing organosilicon compound according to claim 1, wherein the aliphatic unsaturated bond-containing compound represented by the formula (1) is subjected to an addition reaction in the presence of a hydrosilylation catalyst. formula:

Embedded image Wherein X is an alkenyl group, Z is a carbonyloxy group or a phenylene group represented by -C (O) O-, R is the same or different monovalent hydrocarbon group containing no aliphatic unsaturated bond, and A is 1 or more divalent hydrocarbon group, or a group of the formula carbon atoms: -R ² -O
—R ² — (wherein, R ² is a divalent hydrocarbon group). m and p are 0 or 1, n is 0 to 2, and q is an integer of 0 to 7. A silicon-bonded hydrogen atom-containing organosilicon compound represented by the formula: (B) a general formula: R ³ -Y ^{2 wherein} R ³ is an aliphatic unsaturated bond-containing monovalent hydrocarbon group; ² is a substituted or unsubstituted triorganosiloxyphenyl group. A method for producing a hydroxyphenyl group-containing organosilicon compound, comprising subjecting an aliphatic unsaturated bond-containing compound represented by the formula: to an addition reaction in the presence of a hydrosilylation catalyst, followed by a desilylation reaction. .

[0008] In these methods, the component (A)
The organosilicon compound containing a hydrogen atom bonded to a hydrogen atom is represented by the above formula
X, Z, A, R, n, m, and p are the same as described above. These organic silicon
The compound can be produced by a conventionally known method. For example,
In the presence of a mixed solvent of water and ether, the formula: CH_Two= C (CH_Three) COO (CH_Two)_ThreeSi (OCH_Three)_Three  In a silane represented by the formula: H (CH_Three)_TwoBy dropping silane represented by SiCl, the formula: CH_Two= C (CH_Three) COO (CH_Two)_ThreeSi {OSi (CH_Three)_TwoH}_Three  A silicon-bonded hydrogen-containing organosilicon compound represented by
Products are known to occur (U.S. Pat.
No. 17). In addition, methacrylic functional group-containing
Rosilane in the presence of 1,1,3,3-tetramethyldisiloxane
Hydrolyzed to methacrylic
After hydrolyzing the silane to silanol,
It can be manufactured by reacting with luganochlorosilane.
it can. At this time, in order to suppress condensation of silanol groups,
Triethylamine and pi
It is desirable to use amines such as lysine. Also,
1,1,3,3-Tetramethyldise in the presence of strong acids and carboxylic acids
Loxane and formula: CH_Two= C (CH_Three) COO (CH_Two)_ThreeSi (OCH_Three)_Three Indicated by
Can also be synthesized by reacting
Hei 9-117573).

In the phenolic compound containing an aliphatic unsaturated bond as the component (B), in the above formula, R ³ is a monovalent hydrocarbon group containing an aliphatic unsaturated bond, and is a vinyl group, an allyl group, a butenyl group, or a hexenyl group. Is exemplified. Among these, an allyl group is preferable from the viewpoint of availability and economy. Y ¹ is a substituted or unsubstituted hydroxyphenyl group. Examples of such Y ¹ include the hydroxyphenyl groups exemplified for Y described above. Y ² is a substituted or unsubstituted triorganosiloxyphenyl group, and examples of such an organic group include a group in which the hydroxyl group of the hydroxyphenyl group exemplified by Y is trimethylsiloxy. As such a component (B),
2-Allylphenol, eugenol or their trimethylsilyl ethers are preferred. In addition, since the phenolic hydroxyl group causes a dehydrocondensation reaction with a silicon-bonded hydrogen atom in the presence of a hydrosilylation reaction catalyst, a phenolic hydroxyl group is used as the component (B) especially when a high-purity target product is required. Preference is given to using triorganosiloxylated compounds containing aliphatic unsaturated bonds.

As the catalyst for the hydrosilylation reaction, for example, a transition metal complex catalyst belonging to Group 8 of the periodic table can be used. Of these, platinum-based catalysts are particularly effective, and platinum compounds such as chloroplatinic acid and its alcohol solution, olefin complexes of platinum, and complexes of platinum with vinyl group-containing siloxanes are preferred.

In reacting the component (A) with the component (B), the component (B) is reacted with the hydrosilylation compound in order to suppress the rate of the addition reaction between the alkenyl group and the silicon-bonded hydrogen atom in the component (A). A method is preferred in which the reaction catalyst is mixed in advance and the component (A) is slowly added dropwise thereto. (A)
As for the ratio of the amount of the component to the amount of the component (B), the ratio of the equivalent of the aliphatic unsaturated bond in the component (B) to the equivalent of the silicon-bonded hydrogen atom in the component (A) is usually 0.8 or more. It is in the range, preferably in the range of 0.8 to 2.00, and more preferably in the range of 0.9 to 1.5. This reaction is preferably performed in the presence of an organic solvent, but may be performed without a solvent. Solvents used include aromatics such as benzene, toluene, xylene; pentane, hexane,
Aliphatics such as heptane, octane and decane; ethers such as tetrahydrofuran, diethyl ether and dibutyl ether; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; carbon tetrachloride and trichloroethane , Dichloromethylene, and chlorinated hydrocarbons such as chloroform. The reaction can be carried out at room temperature, but usually 50 to 20
It is preferable to carry out within a temperature range of 0-C. During the reaction, the reaction solution is analyzed using gas chromatography analysis (GLC) or infrared spectroscopy (IR), and the time when the characteristic absorption of the silicon-bonded hydrogen atom-containing oligosiloxane of the component (A) disappears. The reaction is terminated. After completion of the reaction, the unreacted component (B) and low-boiling substances such as an organic solvent are removed by a method such as distillation under reduced pressure by heating, so that the aliphatic unsaturated bond and hydroxyphenyl group-containing organosilicon compound of the present invention can be obtained. can get.

When an aliphatic unsaturated bond compound in which a phenolic hydroxyl group is triorganosiloxyl is used as the component (B), an adduct in which the phenolic hydroxyl group is triorganosiloxylized is obtained. It is necessary to remove the group and regenerate the hydroxyphenyl group. As the desilylation method, a conventionally known method can be used, but a method of desilylation of the triorganosiloxylated adduct in the presence of a protic solvent using an amine compound or ammonia as a catalyst is preferable (the present inventors). Et al., Filed on Aug. 28, 1998, entitled "Title of Invention" Method for Desilylation of Aryl Silyl Ether Compound and Method for Production of Hydroxyphenyl Group-Containing Silicon Compound "). According to this method, the desired hydroxyphenyl group-containing organosilicon compound is obtained in high yield without side reactions.

The hydroxyphenyl group-containing organosilicon compound of the present invention contains an aliphatic unsaturated bond-containing monovalent hydrocarbon group in the same molecule, so that it is compatible with an addition reaction-curable silicone composition. And reacts with the organohydrogenpolysiloxane in the addition reaction-curable silicone composition to cure. In addition, since the compound contains a hydroxyphenyl group in the molecule, a cured product of the addition reaction-curable silicone composition containing the organosilicon compound becomes a cured silicone having a hydroxyphenyl group on the surface thereof, and an epoxy resin or the like. It has the property of bonding to various organic resins such as phenolic resins. Therefore, the hydroxyphenyl group-containing organosilicon compound of the present invention is useful as an application requiring such properties, for example, as an adhesion imparting agent for adhering an addition reaction-curable silicone composition to various substrates.

[0014]

[Reference Example] In a 1-liter flask equipped with a stirrer, a thermometer, a condenser, and a dropping funnel, 73.7 g (0.55 mol) of 1,1,3,3-tetramethyldisiloxane, 18 g of ice, and 100 g of water were placed.
Grams and 50 grams of concentrated hydrochloric acid. To this, 215.7 g (1 mol) of methacryloxypropyldimethylchlorosilane was added dropwise while cooling in an ice bath so that the reaction temperature did not exceed 10 ° C. After completion of the dropping, the flask was allowed to stand, and the aqueous layer was separated, and the obtained organic layer was washed twice with water. The organic layer was washed twice with a 5% aqueous sodium hydrogen carbonate solution,
Further, it was washed twice with water. After sodium sulfate was added to the organic layer from which the aqueous layer had been removed in this way and dried, sodium sulfate was separated by filtration. Then, 0.6 g of phenothiazine was added thereto and distilled under reduced pressure to obtain 198 g of a fraction of 71-80-C / 1 mmHg. The obtained fraction was subjected to nuclear magnetic resonance analysis (hereinafter referred to as N
Analysis by MR) and infrared spectroscopy (hereinafter, IR) revealed that the disiloxane was represented by the following formula 1. Gas chromatography of this disiloxane
(Hereinafter, GLC) was 99%. Equation 1:

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[0015]

Example 1 In a 100 ml three-necked flask equipped with a reflux condenser, a thermometer and a dropping funnel, a rotor, 28.66 g (0.1212 mol) of a compound represented by the following formula 2, and a polymerization inhibitor represented by the following formula 3 0.030 g and chloroplatinic acid and 1,3
17 microliters of a toluene solution of a complex of -divinyltetramethyldisiloxane (platinum metal content 2% by weight) was charged. Then, after heating to 80-C, 30.03 g (0.1153 mol) of the disiloxane synthesized in Reference Example 1 was added dropwise. After completion of the dropwise addition, the mixture was stirred at 80-C for 40 minutes. The reaction solution was analyzed by GLC and IR, and the reaction was terminated when the signal of the starting disiloxane by GLC and the signal by the silicon-bonded hydrogen atom by IR disappeared. The unreacted compound of the following formula 2 was distilled off from the reaction solution by heating under reduced pressure to obtain 54.54 g of a residue. Equation 2:

Embedded image Equation 3:

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Next, a reflux condenser and a thermometer were installed.
In a 0 ml 4-neck flask, the residue obtained above was 53.9
0 g, methanol 45.0 g, tetrahydrofuran 3
0.0 g, 1.24 g of diethylamine and a rotor were charged, and the mixture was heated and refluxed at 60 ° C. for 2 hours. Thereafter, low-boiling substances were distilled off to obtain 46.73 g of a residue. When this was analyzed by NMR and IR, it was found to be a hydroxyphenyl group-containing methacryl-functional organosilicon compound represented by the following formula 4. In addition, G of this organosilicon compound
The purity by LC was 93.9%. Equation 4:

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[0017]

Example 2 In a 50 ml two-necked flask equipped with a thermometer and a dropping funnel, a rotor, 54.54 g (0.2643 mol) of a compound represented by the following formula 5, and a polymerization inhibitor represented by the following formula 6 0.005 grams and chloroplatinic acid plus 1,3-
3 microliters of a toluene solution of a divinyltetramethyldisiloxane complex (platinum metal content: 2% by weight) was charged. Then, after heating to 80-C, 4.02 g (0.0125 mol) of trisiloxane represented by the following formula 7 was added dropwise. After completion of the dropwise addition, the mixture was stirred at 80-C for 90 minutes. Reaction solution G
The reaction was analyzed by LC and IR, and it was judged that the reaction was completed when the signal of the raw material disiloxane by GLC and the signal by the silicon-bonded hydrogen atom disappeared by IR. The resulting compound was evaporated under reduced pressure with heating. Then, a reflux condenser was attached, 3.00 g of methanol and 0.20 g of diethylamine were added, and the mixture was heated and refluxed at 55 ° C. for 2 hours. Thereafter, low-boiling substances were distilled off to obtain 5.85 g of a residue. This is NMR
And IR analysis, it was found to be a hydroxyphenyl group-containing methacryl-functional organosilicon compound represented by the following formula 8. The purity of this organosilicon compound determined by GLC was 93.0%. Equation 5:

Embedded image Equation 6:

Embedded image Equation 7:

Embedded image Equation 8:

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[0018]

Example 3 A 300 ml four-necked flask equipped with a thermometer and a dropping funnel was charged with the compound 9 represented by the formula 2 above.
5.56 grams (0.4043 mole) and chloroplatinic acid
75 microliters of a toluene solution of a complex of 1,3-divinyltetramethyldisiloxane (a platinum metal concentration of 2% by weight) was charged. Then, the mixture was heated to 90 ° C., and 147.10 g of allyldimethylsilane in tetrahydrofuran (0.2666 mol of allyldimethylsilane) was added dropwise. After dropping, the mixture was stirred at 90-C for 90 minutes,
Analysis by LC and IR revealed that the signal due to the silicon-bonded hydrogen atom disappeared in the IR. Thus, it was judged that the reaction was completed. Then, after cooling, a reflux condenser was attached, 40 g of methanol and 2 g of diethylamine were added, and the mixture was heated and refluxed at 55 ° C. for 2 hours. Thereafter, low-boiling substances were distilled off by heating under reduced pressure to obtain a residue.
94 grams were obtained. When this was analyzed by NMR and IR, it was found to be a hydroxyphenyl group-containing allyl-functional organosilicon compound represented by the following formula 9. The purity of this organosilicon compound determined by GLC was 81.7%, and the remainder was represented by the following formula 10 (where r is 0.2, 3). Equation 9

Embedded image Equation 10

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[0019]

[Application Example 1] Polydimethylsiloxane 1 having a viscosity of 2,000 mm ² / s at 25 ° C and vinyldimethylsiloxy groups at both ends.
0.01 g (vinyl group content 0.74 mmol), 0.2272 g (methyl silicon-bonded hydrogen atom content 3.56 mmol) of methyl hydrogen polysiloxane having trimethylsiloxy groups at both ends blocked at 25 ° C, phenylbutynol 0.499
Milligram, hydroxyphenyl group-containing methacryl-functional organosilicon compound of formula 4 obtained in Example 1
A composition consisting of 0.638 grams was prepared. Next, a complex of chloroplatinic acid and 1,3-divinyltetramethyldisiloxane was added to the composition in an amount such that the amount of platinum metal was 1 ppm based on the total amount of the composition, and the addition reaction-curable silicone rubber was added. A composition was prepared. This silicone rubber composition is placed in a polytetrafluoroethylene dish (60 mm × 60 mm ×
10 mm), and then left in an oven at 150 ° C. for 1 hour to cure to obtain a 10 mm thick silicone rubber sheet. Then, on this silicone rubber sheet surface,
Place a 1mm thick polytetrafluoroethylene sheet with a rounded center (diameter 10mm), and put a commercially available curable epoxy resin [KONISHI]
(Trade name: Epoxy resin bond E39). Next, a sheet made of polytetrafluoroethylene was overlaid thereon, and a weight of 600 g was placed thereon. The test body was placed in an oven at 150 ° C. and left for 1 hour to cure the epoxy resin, thereby obtaining a molded body in which the epoxy resin and the silicone rubber were integrated. When the epoxy resin was peeled off from the molded body and the fracture interface between the epoxy resin and the silicone rubber was visually observed, the fracture interface was entirely broken by the silicone rubber layer, and it was found that the fracture interface was cohesive failure. . This proved that the epoxy resin and the silicone rubber were firmly adhered. Further, in the above, the adhesion of the phenol / epoxy resin to the silicone rubber was examined in the same manner as above, except that a phenol / epoxy resin having an epoxy resin / phenol resin as a main component was used instead of a commercially available epoxy resin. Was. The phenol / epoxy resin is an epoxy resin [Yuka Shell Epoxy Co., Ltd., trade name Y
DF-8170] 100 parts by weight, phenol resin [Ouchi Shinko Chemical
Nocrack NS-510 (trade name), 10 parts by weight, γ
-5 parts by weight of glycidoxypropyltrimethoxysilane and 20 parts by weight of an imidazole-based curing agent (trade name: NOVACURE HX-3721 manufactured by Asahi Kasei Kogyo KK) were uniformly mixed and prepared. As a result, the fracture interface was entirely fractured by the silicone rubber layer, and it was found that cohesive failure occurred.

[0020]

The hydroxyphenyl group-containing organosilicon compound of the present invention is a novel compound having an aliphatic unsaturated bond-containing monovalent hydrocarbon group and a hydroxyphenyl group in the same molecule. It is effective as an adhesive for a silicone composition. Further, the production method of the present invention has a feature that such a compound can be produced with high productivity.

[Brief description of the drawings]

FIG. 1 is a nuclear magnetic resonance analysis chart of a hydroxyphenyl group-containing methacryl-functional organosilicon compound synthesized in Example 1.

FIG. 2 is an infrared spectroscopic analysis chart of the hydroxyphenyl group-containing methacryl-functional organosilicon compound synthesized in Example 1.

FIG. 3 is a nuclear magnetic resonance analysis chart of a hydroxyphenyl group-containing methacryl-functional organosilicon compound synthesized in Example 2.

FIG. 4 is an infrared spectroscopic analysis chart of a methacryl-functional organosilicon compound having a hydroxyphenyl group synthesized in Example 2.

FIG. 5 is a nuclear magnetic resonance analysis chart of a hydroxyphenyl group-containing methacryl-functional organosilicon compound synthesized in Example 3.

FIG. 6 is an infrared spectroscopic analysis chart of a hydroxyphenyl group-containing methacryl-functional organosilicon compound synthesized in Example 3.

Claims (5)

[Claims] (1) A general formula: [In the formula, X is an alkenyl group, Z is a carbonyloxy group or a phenylene group represented by -C (O) O-, Y is a substituted or unsubstituted hydroxyphenyl group, and R ¹ is the same having 2 or more carbon atoms. or different divalent hydrocarbon radical, R represents monovalent hydrocarbon groups free of aliphatic unsaturation, a is the number of carbon atoms of one or more divalent hydrocarbon group, or a group of the formula: -R ² - O—R ² — (wherein, R ² is a divalent hydrocarbon group). m and p are 0 or 1, n is 0 to 2, and q is an integer of 0 to 7. A hydroxyphenyl group-containing organosilicon compound represented by the formula: 2. X is an isopropenyl group or an allyl group, and Y is a 2-hydroxyphenyl group or 3-methoxy-4.
2. The hydroxyphenyl group-containing organosilicon compound according to claim 1, which is a -hydroxyphenyl group. (A) A general formula: Wherein X is an alkenyl group, Z is a carbonyloxy group or a phenylene group represented by -C (O) O-, R is the same or different monovalent hydrocarbon group containing no aliphatic unsaturated bond, and A is 1 or more divalent hydrocarbon group, or a group of the formula carbon ^{atoms: -R 2 -O-R 2 -} ( wherein, R ² is a divalent hydrocarbon group.) a group represented by. m and p are 0 or 1, n is 0 to 2, and q is an integer of 0 to 7. And an organosilicon compound containing a silicon-bonded hydrogen atom represented by the formula: (B) a general formula: R ³ -Y ^{1 wherein} R ³ is an aliphatic unsaturated bond-containing monovalent hydrocarbon group; ¹ is a substituted or unsubstituted hydroxyphenyl group. 2. The method for producing a hydroxyphenyl group-containing organosilicon compound according to claim 1, wherein the aliphatic unsaturated bond-containing compound is subjected to an addition reaction in the presence of a hydrosilylation catalyst. (A) A general formula: Wherein X is an alkenyl group, Z is a -C (O) O-carboxy group or a phenylene group, R is the same or different monovalent hydrocarbon group containing no aliphatic unsaturated bond, and A is the number of carbon atoms. One or more divalent hydrocarbon groups or a formula: —R ² —O—R ² — (wherein R ²
Is a divalent hydrocarbon group). m and p are 0 or 1, n is 0 to 2, q is 0 to 7
Is an integer. A silicon atom-bonded hydrogen atom-containing oligosiloxane represented by the formula: (B) a general formula: R ³ -Y ^{2 wherein} R ³ is an aliphatic unsaturated bond-containing monovalent hydrocarbon group, and Y ² is It is a triorganosiloxylated substituted or unsubstituted hydroxyphenyl group. 2. The hydroxyphenyl group-containing organosilicon compound according to claim 1, wherein the aliphatic unsaturated bond-containing compound is subjected to an addition reaction in the presence of a hydrosilylation catalyst, followed by a desilylation reaction. Manufacturing method. 5. The hydroxyphenyl group-containing organosilicon compound according to claim 1, which is an adhesion-promoting agent for an addition reaction-curable silicone composition.