JP3013729B2 - Fluorine-containing organosilicon compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel room temperature curable fluorine-containing organosilicon which can be effectively used as a raw material for a rubber material and a release agent material having solvent resistance and chemical resistance. For compounds.

[0002]

2. Description of the Related Art Conventionally, organic fluorine compounds have been used in various fields.
For example, a polymer of an organic fluorine compound is prepared by
An elastomer is obtained by crosslinking at a high temperature of 50 ° C. or higher, and this is used as a rubber material and a release agent.

[0003] However, conventional elastomers obtained from organic fluorine compounds may not have sufficient solvent resistance and chemical resistance in some cases, and elastomers having more excellent solvent resistance and chemical resistance are desired.

Further, elastomers used as sealants, molded parts and the like preferably have further excellent releasability and water repellency, and more desirably cure at room temperature.

[0005] The present invention has been made in view of the above circumstances,
An object of the present invention is to provide a novel fluorine-containing organosilicon compound which is excellent in solvent resistance and chemical resistance, and provides a room-temperature-curable elastomer having excellent releasability and water repellency.

[0006]

The present inventors have made intensive studies to achieve the above object, and as a result, for example, an unsaturated bonding group capable of hydrosilylation at both ends represented by the following general formula (4): And a compound represented by the following general formula (5) in the presence of an addition reaction catalyst to obtain a novel organic fluorine compound represented by the following general formula (1); Further, the present inventors have found that this organic fluorine compound has a high fluorine content, a low surface energy, and can be an elastomer which can be cured at room temperature, and has accomplished the present invention.

[0007]

Embedded image Wherein R ¹ and R ² each represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group, an alkenyl group, an aryl group or an aralkyl group, or a part or all of the hydrogen atoms of these groups are halogen atoms. A substituted group, R ³ is an alkylene group having 1 to 20 carbon atoms, a cycloalkylene group or an arylene group, or a group in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms, and R ³ ′ is hydrosilylatable. A substituted or unsubstituted monovalent hydrocarbon group having an aliphatic unsaturated bond, Q is a group represented by the following general formula (2) or the following general formula (3)

Embedded image (However, in the formula, R ⁴ represents —O—, —NR′—
(R ′ is a hydrogen atom or an alkyl group or an aryl group having 1 to 8 carbon atoms) or an alkylene group having 1 to 20 carbon atoms which may have a group represented by the following formulas (2a) to (2c); A cycloalkylene group or an arylene group, or a group in which part or all of the hydrogen atoms of these groups have been substituted with halogen atoms. R ² has the same meaning as described above. )

Embedded image (However, R ″ is an alkyl group or an aryl group having 1 to 8 carbon atoms, R ″ ′ is an alkylene group or an arylene group having 1 to 6 carbon atoms, and n is an integer of 0 to 10.)

Embedded image (However, in the formula, R ⁵ and R ⁶ represent an alkylene group, a cycloalkylene group or an arylene group having 1 to 20 carbon atoms, or a group in which part or all of the hydrogen atoms of these groups have been substituted with halogen atoms. ) And Rf are a divalent perfluoroalkylene group or a divalent perfluoropolyether group, and X is a halogen atom or a group represented by the following general formulas (i) to (v). a is an integer of 0 to 10, and b is 1, 2 or 3.

Embedded image (However, in the formula, R ⁷ and R ⁸ are each a hydrogen atom and carbon number 1
6 to 6 alkyl groups, cycloalkyl groups, alkenyl groups or aryl groups, or alkoxy-substituted alkyl groups in which hydrogen atoms of these groups are partially substituted with alkoxy groups. )]

Accordingly, the present invention provides a fluorine-containing organosilicon compound represented by the above formula (1).

Hereinafter, the present invention will be described in more detail. The fluorine-containing organosilicon compound of the present invention is represented by the following general formula (1).

[0010]

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Here, R ¹ and R ² in the above formula (1) are substituted or unsubstituted monovalent carbon atoms having 1 to 10 carbon atoms, especially 1 to 8 carbon atoms, excluding aliphatic unsaturated bonds. Hydrogen groups are preferred, for example, methyl, ethyl, propyl,
Isopropyl group, butyl group, isobutyl group, tert-
Butyl group, pentyl group, neopentyl group, hexyl group,
Heptyl group, octyl group, nonyl group, alkyl group such as decyl group, cyclopentyl group, cyclohexyl group, cycloalkyl group such as cycloheptyl group, vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, Alkenyl groups such as hexenyl group and cyclohexenyl group, aryl groups such as phenyl group, tolyl group, xylyl group and naphthyl group, aralkyl groups such as benzyl group, phenylethyl group and phenylpropyl group, or hydrogen atoms of these groups. Examples thereof include a chloromethyl group, a bromoethyl group, a chloropropyl group, a trifluoropropyl group, and the like, in which a part or all of the group is substituted with a halogen atom such as fluorine, chlorine, and bromine. Further, R ³ is not particularly limited as long as it is a substituted or unsubstituted divalent hydrocarbon group, and is preferably a hydrocarbon group having 1 to 20 carbon atoms, particularly 2 to 10 carbon atoms,
Specifically, methylene group, ethylene group, propylene group, methylethylene group, butylene group, alkylene group such as hexamethylene group, cycloalkylene group such as cyclohexylene group, phenylene group, tolylene group, xylylene group, naphthylene group, biphenylene Examples thereof include an arylene group such as a group, or a group in which part or all of the hydrogen atoms of these groups are substituted with a halogen atom, or a combination of these substituted or unsubstituted alkylene groups and arylene groups. An ethylene group and a propylene group are preferred in terms of ease of production, stability of the compound, and the like.

In the above formula (1), Q is a group represented by the following formula (2) or (3).

[0013]

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[0014] R ² in the formula (2) are the same as described above and as is R ^4, is not particularly limited as long as it is a substituted or unsubstituted divalent hydrocarbon group, the same groups as above R ³ Although R ⁴ may further include one or more of oxygen, nitrogen, and silicon atoms in the bond.

In this case, the oxygen atom is -O-, the nitrogen atom is -NR ^' -(R ^' is a hydrogen atom or a carbon atom having 1 to 8, especially 1
6 to an alkyl group or an aryl group), and the silicon atom is interposed as a group containing a linear or cyclic organosiloxane or an organosilylene group, for example, as shown below. Can be.

[0016]

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Examples of such groups include the following groups.

[0018]

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Further, as R ⁵ and R ⁶ in the above formula (3), a substituted or unsubstituted divalent hydrocarbon group having 1 to 10, especially 2 to 6 carbon atoms is preferable. Methylene group,
An alkylene group such as an ethylene group, a propylene group, a methylethylene group, a butylene group, and a hexamethylene group; a cycloalkylene group such as a cyclohexylene group; or a group in which some or all of the hydrogen atoms of these groups have been substituted with halogen atoms or the like. And the like.

The following groups are specifically exemplified as Q in the formula (1) represented by the above formula (2) or (3). In the following chemical formula, Me is a methyl group, P
h represents a phenyl group.

[0021]

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In the formula (1), Rf is a divalent perfluoroalkylene group or a divalent perfluoropolyether group, and particularly, as the divalent perfluoroalkylene group, -C _m F _2m- (where m = 1 To 10, preferably 1 to 6), and the divalent perfluoropolyether group is preferably a group represented by the following formula.

[0023]

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Specific examples of Rf include the following.

[0025]

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Further, in the above formula (1), X is a hydrolyzable group, and specific examples thereof include a halogen atom such as fluorine, chlorine, bromine and iodine and a group represented by the following general formula.

[0027]

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In the above formula (1), b is independently 1, 2 or 3, and accordingly, X of the hydrolyzable group is
From 1 to 3.

In the above formula (1), a is an integer of 0 or more. Therefore, the organic fluorine compound of the formula (1) contains a divalent perfluoroalkylene group or a divalent perfluoropolyether group in one molecule. Wherein a is preferably 0 to 10, especially 0, 1, 2, 3,
4, 5, and 6 are exemplified.

In the present invention, the above-mentioned fluorine-containing organosilicon compound includes from a low-viscosity polymer having a viscosity (25 ° C., the same applies hereinafter) to a solid raw rubber-like polymer, but from the viewpoint of easy handling. For example, a raw rubber-like polymer is preferably used for heat vulcanized rubber, and a polymer having a viscosity of about 100 to 100,000 cs is preferably used for liquid rubber. If the viscosity is too low, the resulting cured product will have a low elongation as an elastomer, and may not have balanced physical properties.

The fluorine-containing organosilicon compound of the present invention includes, for example, a compound having an unsaturated bond group capable of hydrosilylation at both terminals represented by the following general formula (4) and a compound represented by the following general formula (5) And in the presence of an addition reaction catalyst.

[0032]

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R ^{3 '} in the above formula (4) is, for example, a group having 2 to 8 carbon atoms such as a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a butenyl group, a hexenyl group and a cyclohexenyl group. And 2-6 alkenyl groups.

In the above reaction, the mixing ratio of the compound of the formula (4) and the compound of the formula (5) is 2 to 10 times the molar ratio of the compound of the formula (4) to the compound of the formula (4). Especially 2
It is preferable to set it to about 5 times. The excess amount of the compound of the formula (5) remaining after the completion of the reaction can be removed by a vacuum strip.

In this case, the catalyst may be selected from the VI of the periodic table.
Group II elements or compounds thereof, such as chloroplatinic acid, alcohol-modified chloroplatinic acid (see U.S. Pat. No. 3,220,972), complexes of chloroplatinic acid with olefins (U.S. Pat.
No. 159601, No. 3159662, No. 3775
No. 452), platinum black or palladium is alumina,
Silica, carbon-supported carrier, rhodium-olefin complex, chlorotris (triphenylphosphine) rhodium (Wilkinson's catalyst), etc.
The addition amount can be a catalyst amount. The above complex is preferably used after being dissolved in an alcohol, ketone, ether or hydrocarbon solvent.

The conditions for the above reaction are 50 to 150.
C., preferably at 80 to 120.degree. C. for 2 to 4 hours.

The organic fluorine compound of the above formula (4) can be obtained by the following method. That is, the organic fluorine compound in which a is 0 in the above formula (4) is, for example, a compound having an acid fluoride group at both terminals represented by the following general formula (6) and a secondary amine represented by the following general formula (7) The compound can be synthesized by reacting the compound with an acid acceptor such as trimethylamine.

[0038]

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Further, the organic fluorine compound in which a is an integer of 1 or more in the above formula (4) is, for example, a compound having an acid fluoride group at both terminals shown in the above formula (6) and a compound represented by the following general formula (8) -QH (8) (Q has the same meaning as described above) is reacted in the presence of an acid acceptor, and the secondary amine compound represented by the above formula (7) is further reacted with the compound. It can be synthesized by reacting.

In this case, the ratio of the charged amounts of the compound having an acid fluoride group at both terminals of the formula (6) and the secondary amine compound of the formula (7) is not particularly limited, but is calculated in terms of mol. The ratio (a) / (b) between the charged amount (a) of the compound of the formula (6) and the charged amount (b) of the compound of the formula (7) is from 0.5 to
It is suitable to be 0.2 mol / mol.

The charged amount (a) of the compound of the formula (6) and the charged amount (c) of the compound of the formula (8) are not particularly limited as long as (a) is not smaller than (c) in terms of mole. It is not limited. The repeating unit a in the formula (1) is
By adjusting (a) / (c), an appropriate value according to the purpose can be obtained. By increasing (a) / (c), a polymer having a relatively small molecular weight can be synthesized,
When the value of (a) / (c) approaches 1, a polymer having a large molecular weight can be synthesized.

The conditions for the above reaction are not particularly limited.
20 to 100 ° C for 1 to 8 hours, preferably 20 to 50 ° C
For 2 to 4 hours.

In the organic fluorine compound of the formula (4), Q is one in which a silicon atom is interposed. When R ³ of the secondary amine compound of the formula (7) is an allyl group, A compound having an allyl group at both terminals represented by the formula (9) is synthesized, and the compound is reacted with, for example, a compound represented by the following general formula (10) in the presence of the same addition reaction catalyst as described above. can do.

[0044]

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In this reaction, the ratio of the charged amount of the compound having allyl groups at both terminals represented by the above formula (9) to the compound of the formula (10) is calculated in terms of molar amount as the charged amount of the compound of the formula (9). (D) must be greater than the charge (e) of the compound of formula (10), the ratio (d) / (e) being at most 2. That is, 1 <(d) / (e) ≦ 2.

By increasing (d) / (e), a polymer having a relatively small molecular weight can be synthesized.
When the value of (d) / (e) approaches 1, a polymer having a large molecular weight can be synthesized.

The reaction conditions are 50-150 ° C.
It is preferable to set the temperature at 80 to 120 ° C. for 2 to 4 hours.

Since the fluorine-containing organosilicon compound of the present invention has a hydrolyzable silyl group at a terminal, it can be crosslinked by reacting with moisture (moisture) in the air to become an elastomer. This elastomer has a high fluorine content, so it has excellent solvent resistance and chemical resistance.It also has a low surface energy, so it has excellent mold releasability and water repellency. It can be used effectively as a mold agent and the like.

[0049]

The organic fluorine compound of the present invention has a high fluorine content, a low surface energy, and can be an elastomer which can be cured at room temperature. It is effective as a material for molding agents.

[0050]

EXAMPLES Hereinafter, the present invention will be specifically described with reference to Reference Examples and Examples, but the present invention is not limited to the following Examples.

REFERENCE EXAMPLE 189.2 g (viscosity: 430 cs; 25 ° C.) of a compound having an acid fluoride group at both terminals represented by the following formula (11): 300 ml with a stir bar, thermometer, Dim funnel, and dropping funnel The mixture was charged into a four-necked flask, and a mixture of 9.6 g of allylaniline and 6.1 g of triethylamine was added to the mixture from a dropping funnel while stirring.
It was added dropwise at ° C.

[0052]

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After the addition, the reaction was carried out at 60 ° C. for 2 hours.
The filtrate obtained by filtering the reaction mixture under pressure was subjected to 120 ° C / 3
Stripping under reduced pressure at mmHg gave 190.1 g of a pale yellow transparent liquid compound.

In addition, meta-xylene hexafluoride 5
0.0 g was charged and heated to 100 ° C. with stirring, and 0.2 g of a 2% solution of chloroplatinic acid in isopropyl alcohol was added. Thereafter, 6.96 g of cyclotetrasiloxane represented by the following formula (12) was added dropwise from a dropping funnel to carry out a reaction.

[0055]

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After the dropwise addition, the disappearance of cyclotetrasiloxane was confirmed by gas chromatography while aging. After cooling, the mixture was cooled to room temperature, charged with 1.5 g of activated carbon, and stirred for 2 hours. The filtrate obtained by filtering the reaction mixture under pressure was heated to 120 ° C.
After stripping under reduced pressure at / 3 mmHg, 193.5 g of a transparent liquid compound was obtained.

The compound obtained had a viscosity of 30700 cs
(25 ° C.) and the refractive index was 1.329. As a result of IR measurement of this compound, the following absorptions were recognized.

1100-1300 cm ^-1 ν _CF 1690 cm ^-1 ν _{C =} 1600, 1500 cm ^-1 arom. Further, when the amount of allyl group of this compound was quantified, it was found to be 0.1%.
007 mol / 100 g, and it was confirmed that the obtained compound was a polymer of an organic fluorine compound represented by the following structural formula (13).

[0059]

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EXAMPLE 1 274.8 g of a compound having an allyl group at both terminals represented by the following formula (14) and 55 g of meta-xylene hexafluoride were added to a 500 ml flask equipped with a stirring bar, a thermometer, a Dim funnel, and a dropping funnel. The mixture was charged in a one-necked flask, and heated with an oil bath while stirring so that the internal temperature became 70 ° C. Thereafter, 0.3 g of a 2% solution of chloroplatinic acid in isopropyl alcohol was added, and then a silane compound 4.9 represented by the following formula (15) was added using a dropping funnel.
g was added dropwise to carry out the reaction.

[0061]

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After dropping, allyl groups (—CH ＝ CH ₂ : δ = 4.9-5.3 pp) were obtained by ¹ H-NMR while aging.
After confirming the disappearance of m), vacuum stripping was carried out at 100 ° C. and 10 mmHg to remove unreacted silane components. 277.1 g of a pale brown transparent liquid compound was obtained.
was gotten.

The compound obtained had a viscosity of 32500 cs
(25 ° C.) and the refractive index was 1.335. This compound
As a result of ¹ H-NMR measurement, the following absorption was observed.

[0064] ¹ H-NMR (TMS standard) δ = 3.56 (s, Si -O CH 3, 18H) δ = 3.6~4.0 (m, N- CH 2 -, 16H) δ = 7 .0~7.5 (m, N- Ph, 40H ) IR ( see Fig. _{^{1) 1100~1300cm -1 ν CF 1690cm -1}} ν C = 0 1600,1500cm -1 arom. In addition, when the amount of methanol desorbed by hydrolyzing this compound was quantified, it was 0.014 mol / 100 g, which was confirmed to be a fluorine-containing organosilicon compound represented by the following structural formula (16).

[0065]

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Example 2 In the same apparatus as in Example 1, 274.8 g of a compound having an allyl group at both ends represented by the above formula (14) and 55 g of meta-xylene hexafluoride were used.
After the temperature was raised to an internal temperature of 80 ° C., 0.3 g of a 2% solution of chloroplatinic acid in isopropyl alcohol was added, and then a silane compound represented by the following formula (17) was added with a dropping funnel.
3 g was added dropwise, and the reaction and post-treatment were carried out in the same manner as in Example 1. As a result, 277.2 g of a pale brown transparent liquid compound was obtained.

[0067]

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The compound obtained had a viscosity of 32700 cs
(25 ° C.), refractive index 1.336 (25 ° C.), ¹ H
As a result of NMR and IR measurement, the following absorptions were observed.

¹ H-NMR (TMS standard) δ = 3.6 to 4.0 (m, N—CH ₂ —, 16H) δ = 4.1 to 4.2 (m, OC = CH ₂ , 2H) δ = 7.0~7.5 (m, N- Ph, 40H) IR ( see Fig. _{^{2) 1100~1300cm -1 ν CF 1690cm -1}} ν C = 0 1600,1500cm -1 arom. 1645 cm ^-1 ν _{C = C Further} , when this compound was hydrolyzed and the amount of the eliminated acetone was quantified, it was 0.021 mol / 100 g,
It was confirmed that it was a fluorine-containing organosilicon compound represented by the following structural formula (18).

[0070]

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[Embodiment 3] In the embodiment 2, the equation (17) is used.
The reaction and post-treatment were carried out in the same manner as in Example 2 except that 6.5 g of the silane compound represented by the following formula (19) was used instead of the silane compound of formula (27). was gotten.

[0072]

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The obtained compound had a viscosity of 33700 cs.
(25 ° C.), refractive index 1.338 (25 ° C.), ¹ H
As a result of NMR and IR measurement, the following absorptions were observed.

¹ H-NMR (TMS standard) δ = 1.97 (s, Si—OCCH ₃ , 12H) δ = 3.6 to 4.0 (m, N—CH ₂ −, 16H) δ = 7 .0~7.5 (m, N-Ph, 40H) IR ( see Fig. _{^{3) 1100~1300cm -1 ν CF 1690cm -1}} ν C = 0 (N-C = O) 1720cm -1 ν C = 0 ( SiOC = O) 1600, 1500 cm ^-1 arom. The amount of acetic acid released by hydrolyzing this compound was quantified to be 0.014 mol / 100 g, which was confirmed to be a fluorine-containing organosilicon compound represented by the following structural formula (20).

[0075]

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Example 4 324.1 g of a compound having an allyl group at both terminals represented by the following formula (21) and 64.8 g of meta-xylene hexafluoride were charged into the same apparatus as in Example 1, and stirred. While the internal temperature was raised to 70 ° C., 0.3 g of a 2% solution of chloroplatinic acid in isopropyl alcohol was added, and then 4.9 g of the silane compound of the above formula (15) was added dropwise using a dropping funnel to carry out a reaction. .

[0077]

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Thereafter, the reaction and post-treatment were carried out in the same manner as in Example 1. As a result, 325.8 g of a pale yellow transparent liquid compound was obtained.

The obtained compound had a viscosity of 63600 cs
(25 ° C.), refractive index 1.316 (25 ° C.), ¹ H
As a result of NMR and IR measurement, the following absorptions were observed.

¹ H-NMR (TMS standard) δ = 1.1 to 1.5 (m, CH—CH ₃ , 24H) δ = 3.21 (d, N—CH ₃ , 6H) δ = 3.54 _{(s, SiO-CH 3,} 18H) the IR (see Fig. _{^{4) 1100~1300cm -1 ν CF 1690cm -1}} ν C = 0, where the compound is hydrolyzed, and quantitated desorbed amount of methanol, 0 0.018 mol / 100 g, which was confirmed to be a fluorine-containing organosilicon compound represented by the following structural formula (22).

[0081]

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[Brief description of the drawings]

FIG. 1 is a chart showing an IR spectrum of an organic fluorine compound of Example 1.

FIG. 2 is a chart showing an IR spectrum of the organic fluorine compound of Example 2.

FIG. 3 is a chart showing an IR spectrum of the organic fluorine compound of Example 3.

FIG. 4 is a chart showing an IR spectrum of the organic fluorine compound of Example 4.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI // C10N 40:36 (72) Inventor Masatoshi Arai 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture 10 Shin-Etsu Chemical Co., Ltd. Silicone Denki (56) References JP-A-5-320178 (JP, A) JP-A-55-92393 (JP, A) JP-A-58-88391 (JP, A) JP-A-4-27161 ( JP, A) JP-A-8-165419 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07F 7/18 C07F 7/21 C08G 77/24 C08L 83/08 CAPLUS (STN ) REGISTRY (STN) WPIDS (STN)

Claims (3)

(57) [Claims] 1. A fluorine-containing organosilicon compound represented by the following general formula (1). Embedded image Wherein R ¹ and R ² each represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group, an alkenyl group, an aryl group or an aralkyl group, or part or all of the hydrogen atoms of these groups are halogen atoms. The substituted group, R ³ is an alkylene group having 1 to 20 carbon atoms, a cycloalkylene group or an arylene group, or a group in which part or all of the hydrogen atoms of these groups are substituted with halogen atoms, and Q is a group represented by the following general formula (2) ) Or a group represented by the following general formula (3): (However, in the formula, R ⁴ represents —O—, —NR′—
(R ′ is a hydrogen atom or an alkyl group or an aryl group having 1 to 8 carbon atoms) or an alkylene group having 1 to 20 carbon atoms which may have a group represented by the following formulas (2a) to (2c); A cycloalkylene group or an arylene group, or a group in which part or all of the hydrogen atoms of these groups have been substituted with halogen atoms. R ² has the same meaning as described above. ) (However, R ″ is an alkyl group or an aryl group having 1 to 8 carbon atoms, R ″ ′ is an alkylene group or an arylene group having 1 to 6 carbon atoms, and n is an integer of 0 to 10.) Chemical formula 3] (In the formula, R ⁵ and R ^{6 each} represent an alkylene group, a cycloalkylene group or an arylene group having 1 to 20 carbon atoms, or a group in which part or all of the hydrogen atoms of these groups are substituted with halogen atoms. ) And Rf are a divalent perfluoroalkylene group or a divalent perfluoropolyether group, and X is a halogen atom or a group represented by the following general formulas (i) to (v). a is an integer of 0 to 10, and b is 1, 2 or 3. Embedded image (However, in the formula, R ⁷ and R ⁸ are each a hydrogen atom and carbon number 1
To alkyl groups, cycloalkyl groups, alkenyl groups or aryl groups, or alkoxy-substituted alkyl groups in which hydrogen atoms of these groups are partially substituted with alkoxy groups. )] 2. The fluorine-containing organosilicon compound according to claim 1, wherein Rf is selected from the following formula. Embedded image 3. The fluorine-containing organosilicon compound according to claim 1, which is used for a rubber material.