JPH09241381A - Fluorinated organosilicon compound and production thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a novel fluorinated organosilicon compound which can reduce surface tension markedly by condensing a specific fluorinated organosilicon compound. SOLUTION: A novel fluorinated silicon compound of formula I is prepared by condensing a compound of formula II (wherein Rf is a 4-14 C perfluoroalkyl or 5-14 C perfluoropolyether group; Q is a polyether group in which ethylene and/or propylene groups are repeatedly bonded through ether linkages; R is H, or an allyl, 1-4 C alkyl or 2-3 C acyl group; L and m are each 0 or 1: n is 1 or 2; X is 2 or 3: Me is a methyl group; and Z is H or a hydroxy group).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel fluorine-containing organosilicon compound and a method for producing the same, and more particularly to the fluorine-containing organosilicon compound capable of remarkably reducing the surface tension when used as a fluorine-containing surfactant.

[0002]

2. Description of the Related Art Conventionally, as a fluorine-containing surfactant, for example, perfluoroalkylsulfonyl fluoride (C ₈ F
₁₇ SO ₃ F) or perfluoroalkylcarbonyl fluoride (C ₇ F ₁₆ COF) to which a polyether group is bonded via an amide group or an ester group is known. However, the fluorine-containing surfactant has problems that its structure is unstable and that the reaction yield during production is low. So for this problem the following formula:

[0003]

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[In the formula, Rf 'represents a perfluoro group having 4 to 10 carbon atoms or a perfluoropolyether group having 5 to 14 carbon atoms, and Q is composed of a polyethylene glycol chain, a polypropylene glycol chain, or both of them. Represents a polyether group, R is hydrogen atom, allyl group, carbon atom 1
To 4 alkyl group or an acyl group having 2 to 3 carbon atoms, l and m are each an integer of 0 or 1, and n is an integer of 1 to 3]. Surfactants have been proposed (JP-A-3-47190). The structure of this compound is stable, and the yield in producing this compound is high.

[0005]

However, the fluorine-containing group-modified silicone surfactant has a problem that it is inferior in the ability to lower the surface tension of the solution when added to the solution.
Accordingly, an object of the present invention is to provide a novel fluorine-containing organosilicon compound that solves the problems of the above-mentioned fluorine-containing surfactant and can significantly reduce the surface tension of the solution when added to the solution, and a method for producing the same. To do.

[0006]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that the following compounds can solve the above problems. That is, the present invention relates to the general formula
(1):

[0007]

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[In the formula, Rf is independently a perfluoroalkyl group having 4 to 14 carbon atoms or a perfluoropolyether group having 5 to 14 carbon atoms, and Q is independently an ethylene group and / or a propylene group. It is a polyether group formed by repeating an ether bond, and R is independently a hydrogen atom, an allyl group, an alkyl group having 1 to 4 carbon atoms and 2 to 2 carbon atoms.
A monovalent hydrocarbon group or atom selected from the group consisting of acyl groups of 3, L and m are each independently 0 or 1, n is independently 1 or 2, x is 2 or 3, Me is a methyl group]. Furthermore, the present invention provides a compound represented by the general formula (2):

[0009]

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A compound represented by the formula: wherein Rf, Q, R, Me, L, m, n and x have the same meanings as described above, and Z is a hydrogen atom or a hydroxyl group. A method for producing the above-mentioned fluorine-containing organosilicon compound is provided.

The present invention will be described in detail below.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION Fluorine-Containing Organosilicon Compound The fluorine-containing organosilicon compound of the present invention is represented by the general formula (1) as described above. In the general formula (1), the fluorine-containing organic group represented by Rf is a C4-14, preferably C4-10, more preferably C6-9 perfluoroalkyl group, or C5-14 carbon atom, It is preferably 8 to 11 perfluoropolyether groups. By introducing the fluorine-containing organic group, hydrophobicity is imparted to the fluorine-containing organic silicon compound of the present invention.

The perfluoroalkyl group is represented by the general formula (3): _{--C k} F _{2k + 1} (3) [wherein, k is an integer of 4 to 10, preferably 6 to 9]. Be done. Specifically, nonafluorobutyl group, undecafluoropentyl group, tridecafluorohexyl group, pentadecafluoroheptyl group, heptadecafluorooctyl group, nonadecafluorononyl group, heneicosafluorodecyl group, 7-tri Examples thereof include a fluoromethylhexadecafluorooctyl group and a 5-trifluoromethyldodecafluorohexyl group, and a tridecafluorohexyl group and a heptafluorooctyl group are preferable.

When the fluorine-containing organic group Rf is the above-mentioned perfluoroalkyl group, L in the general formula (1) is preferably 0, that is, it does not contain an ether bond. Therefore, preferred specific examples of-(CH ₂ ) _x- (CH ₂ OCH ₂ ) L -R _f include 3, 3, 4, 4, 5, 5, 6, 6, 7, 7, 8, 8,
8-tridecafluorooctyl group, 3, 3, 4, 4, 5, 5,
6, 6, 7, 7, 8, 8, 9, 9, 10, 10, 11, 11, 11-heptadecafluorododecyl group and the like.

As the perfluoropolyether group,
For example, general formula (4):

[0016]

[Chemical 6]

Examples include groups represented by the formula: [wherein y is an integer of 1 to 4]. Specifically, 1-trifluoromethyl-1, 3, 3, 4, 4, 5, 5, 5-octafluoro-2-
Oxapentyl group, 1,4-bis (trifluoromethyl)
-1, 3, 3, 4, 6, 6, 7, 7, 8, 8, 8-undecafluoro-2,5-dioxaoctyl group, 1, 4, 7-tris (trifluoromethyl) -1 , 3, 3, 4,6, 6, 7, 9, 9, 10,
10, 11, 11, 11-tetradecafluoro-2,5,8-trioxaundecyl group, 1,4,7,10-tetrakis (trifluoromethyl) -1,3,3,4,6,6 , 7, 9, 9, 10,
12, 12, 13, 13, 14, 14, 14-Heptadecafluoro-
2,5,8,11-tetraoxatetradecyl group, preferably 1,4-bis (trifluoromethyl) -1,
3, 3, 4, 6, 6, 7, 7, 8, 8, 8-Undecafluoro-
2,5-dioxaoctyl group and 1, 4, 7-tris (trifluoromethyl) -1, 3, 3, 4, 6, 6, 7, 9, 9, 10, 1
It is a 0, 11, 11, 11-tetradecafluoro-2,5,8-trioxaundecyl group.

When the fluorine-containing organic group Rf is a perfluoropolyether group, L in the general formula (1) is preferably 1. _{Thus, - (CH 2) x -} (CH 2 -OCH 2) Preferred examples of L -R _f is 6-trifluoromethyl -6,8,8,
9,9,10,10,10-octafluoro-4,7-dioxadecyl group, 6,9-bis (trifluoromethyl) -6,8,8,9,11,1
1,12,12,13,13,13-undecafluoro-4,7,10-trioxatridecyl group, 6,9,12-tris (trifluoromethyl) -6,8,8,9,11 , 11,12,14,14,15,15,16,16,16-tetradecafluoro-4,7,10,13-tetraoxadecyl group and the like.

In the general formula (1), the organic group represented by Q is a polyether group in which an ethylene group and / or a propylene group are repeatedly bonded by an ether bond, whereby the fluorine-containing organosilicon of the present invention can be obtained. Hydrophilicity is imparted to the compound. The polyether group may be a homopolymer chain of ethylene glycol, a homopolymer chain of propylene glycol, or a copolymer chain (block polymerization, random polymerization) of both, and is appropriately selected according to the use of the fluorine-containing organosilicon compound. To be done.

The degree of polymerization of this polyether group may be usually determined in consideration of the balance with the hydrophobic fluorine-containing organic group Rf, and when ethylene glycol is used as a homopolymer chain, the degree of polymerization is preferably It is 3 to 20, more preferably 3 to 12. When propylene glycol, which is less hydrophilic than ethylene glycol, is used as the homopolymer chain, a polymer chain having a relatively high degree of polymerization is preferable,
More preferably, the degree of polymerization is 100 to 200. Further, in the case of a copolymer chain of propylene glycol and ethylene glycol, the content of propylene glycol in the whole polyether group is usually in the range of 0 to 50 mol%, preferably 2 to 10 mol%. is there.

R in the general formula (1) is independently a monovalent carbon atom selected from the group consisting of a hydrogen atom, an allyl group, an alkyl group having 1 to 4 carbon atoms, and an acyl group having 2 to 3 carbon atoms. It is a hydrogen group or an atom, preferably a hydrogen atom, a methyl group and a butyl group.

The following can be exemplified as the fluorine-containing organosilicon compound of the present invention.

[0023]

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Production Method of Fluorine-Containing Organosilicon Compound To produce the fluorine-containing organosilicon compound of the present invention, for example, the compound represented by the general formula (2):

[0025]

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[Rf, Q, R, Me, Z, L, m, n and x
Has the same meaning as described above]. In the above production method, when Z in the general formula (2) is (i) a hydrogen atom,
(Ii) Two types of hydroxyl groups will be described separately.

(I) When Z is a hydrogen atom The following formula (2) ′ in which Z in the general formula (2) is a hydrogen atom:

[0028]

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[Wherein Rf, Q, R, Me, L, m, n and x have the same meanings as described above] (hereinafter, simply referred to as "fluorine-containing organosilicon compound ( H) ”) is hydrolyzed and condensed in an aqueous alkali hydroxide solution to obtain the fluorine-containing organosilicon compound of the present invention.

Examples of the alkali hydroxide include lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide and the like, with preference given to sodium hydroxide and potassium hydroxide.

In the above reaction, it is desirable to coexist with an aprotic polar solvent in order to improve the contact efficiency between the fluorine-containing organosilicon compound (H) and the aqueous alkali hydroxide solution. Examples of the solvent include ethers such as diisopropyl ether, dibutyl ether, and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and the like. Tetrahydrofuran is preferable.

The reaction temperature is appropriately determined depending on the amount and kind of the solvent and is usually 0 to 70 ° C, preferably 20 to 50 ° C. The time is not particularly limited, and the reaction may be sufficiently advanced according to the individual reaction conditions.

The fluorine-containing organosilicon compound (H) has the general formula (5):

[0034]

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[In the formula, Rf is a perfluoroalkyl group having 4 to 14 carbon atoms or a perfluoropolyether group having 5 to 14 carbon atoms, L and m are 0 or 1, and n is 1 Or 2, x is 2 or 3, and Me is a methyl group].
Simply referred to as "fluorine-containing organosilicon compound (A)")
When the general formula _{(6): CH 2 = CH} -CH 2 -O -Q -R (6) wherein, Q and R has the same meaning as above] and a polyether compound represented by platinum-type It can be obtained by carrying out a hydrosilylation reaction in the presence of a catalyst. Here, the fluorine-containing organosilicon compound (A) can be obtained, for example, from JP-A-3-1974.
It can be produced by the method described in JP-A-84.

Fluorine-containing organosilicon compound (A) and general formula
The reaction molar ratio with the polyether compound represented by (6) is
Usually a stoichiometric amount will suffice. However, when the allyl group of the polyether compound undergoes internal rearrangement depending on the reaction conditions and is not used for the addition reaction, it is desirable that the amount of the polyether compound be in excess of the stoichiometric amount. Specifically, the molar ratio of the SiH group in the fluorine-containing organosilicon compound (A) to the CH ₂ ═CH—CH ₂ group in the polyether compound is preferably in the range of 1/2 to 1/1, More preferably, it is in the range of 1 / 1.5 to 1 / 1.1.

As the above platinum-based catalyst, a conventionally known one used for hydrosilylation can be used, and examples thereof include chloroplatinic acid, alcohol-modified chloroplatinic acid, platinum vinylsiloxane, platinum black, and a complex of chloroplatinic acid with an olefin or an aldehyde. Is mentioned. Among them, chloroplatinic acid, alcohol-modified chloroplatinic acid and platinum vinylsiloxane are preferable because they are highly active. The amount of the platinum-based catalyst used is usually 1 to 100 ppm (platinum weight equivalent) based on the whole reaction solution.

In the above hydrosilylation reaction, a solvent may be used if necessary. The solvent is not particularly limited as long as it does not react with the solute, and for example, hydrocarbons such as benzene, toluene, xylene, hexane, heptane, octane, cyclohexane; diisopropyl ether,
Examples thereof include ethers such as dibutyl ether; siloxanes such as hexamethyldisiloxane.

The temperature of the above reaction is usually 60 ° C to 140 ° C.
In the range of 70 to 110 ° C.

(Ii) When Z is a hydroxyl group The following formula (2) '' in which Z is a hydroxyl group in the general formula (2):

[0041]

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[In the formula, Rf, Q, R, Me, L, m, n and x have the same meanings as described above] (hereinafter, simply referred to as "fluorine-containing organosilicon compound ( The fluorinated organosilicon compound of the present invention can also be obtained by subjecting OH) ”) to a dehydration condensation reaction in the presence of a catalyst.

As the catalyst, a catalyst used in the condensation reaction of SiOH groups, for example, tin compounds such as dibutyltin dimethoxide and dibutyltin dilaurate; the following formula:

[0044]

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Examples thereof include perfluorocarboxylic acid ammonium salts represented by [Rf has the same meaning as described above and R ′ is a hydrogen atom or an alkyl group or an aryl group having 1 to 10 carbon atoms].

The temperature of the above reaction may be determined according to the amount and kind of the solvent, and the temperature at which the reaction substrate and the product are not decomposed is preferable. Specifically, it is usually in the range of 20 to 150 ° C, preferably 80 to 120 ° C. Time is 1
~ 12 hours is enough.

The fluorine-containing organosilicon compound (O
H) is SiH in the fluorine-containing organosilicon compound (H)
The group is obtained by hydrolysis in the presence of a catalyst. As the catalyst, from the viewpoint of easiness of reaction or treatment after reaction, palladium or platinum supported on carbon, alumina or the like, and alkylhydroxylamine such as diethylhydroxylamine are preferable.

Since the novel fluorine-containing organosilicon compound of the present invention can remarkably reduce the surface tension, it is useful as a fluorine-containing surfactant. When used as a fluorinated surfactant, the fluorinated organosilicon compound represented by the general formula (1) may be used alone or in combination of two or more. The above-mentioned fluorine-containing surfactant, when added to various liquids, particularly organic solvents, exhibits wettability, penetrability, spreadability, foam stability, fluidity, emulsification, dispersibility, water and oil repellency. Because of its excellent ability to give and improve, the following uses are expected. That is, emulsifiers for polymerization in the plastic and rubber industry, stabilizers for latex,
Powder fluorocarbon polymer agglomerate preparation aid, foaming additive for controlling spreading or coating unevenness, additive for imparting water and oil repellency to grease, internal antistatic agent and antiblocking agent of polyolefin; petroleum industry field Additives for improving fluidity when recovering heavy oil from oil storage equipment, additives for improving wear resistance of lubricating oil, additives for preventing icing in gasoline vaporizers, gasoline by film formation A jet fuel evaporation inhibitor; an additive for improving fluidity for improving the melting prevention process in the textile industry,
Carbonization agent for wool, synthetic sizing agent PVA in spinning sizing process
Additives for lowering surface tension of aqueous solutions, mercerization aids, dye finishing aids; aids for improving pigment colorability and dispersibility in the dye and pigment industry, flowability and dent prevention properties for correcting paint defects. Additives, agents for adjusting the evaporation rate of solvents in paints; Additives for gloss treatment baths in the metal and machine industry, additives for metal etching, additives for solder flux, corrosion inhibitors, anti-mist agents for plating; pharmaceuticals In the field of agricultural chemicals, penetration improver for fungicides, wetting improver for promotants and insecticides, emulsification, dispersion and spreadability improver; additive for cleaner products and leveling for polish in the field of household products Improver, cosmetic additive, antistatic agent; additive for imparting fluidity and flowability of ink in the fields of photography and printing, photographic emulsion leveling agent, film antistatic agent, film drying aid It is this an example of the agent.

[0049]

The present invention will be described below with reference to examples. In the following description, Me means a methyl group.

[Synthesis Example 1] In a four-necked flask having an inner volume of 500 mL equipped with a cooling tube and a thermometer, the following formula (A-
1):

[0051]

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Fluorine-containing organosilicon compound represented by (A-
1) 140.1 g and 105.7 g of toluene were charged, and the internal temperature was raised to 70 ° C. Next, a solution of platinum vinyl siloxane in toluene with chlorine removed beforehand (containing 4.0 x 10 ^-3 g of platinum)
0.15g was added. Next, 106.2 g of polyethylene oxide having an average degree of polymerization of 3 terminated with allyl groups and methyl groups at both ends of the molecular chain and a toluene solution of the platinum vinyl siloxane.
A mixture with 0.16g was prepared. Then, this mixture was added to a toluene solution of the fluorine-containing organosilicon compound (A-1).
It was added dropwise over a period of minutes. The resulting mixture at a temperature of 75 ° C. 3.
After holding for 5 hours, toluene was distilled off under reduced pressure to obtain 233.2 g of a light brown oily product.

The product obtained above was analyzed by ¹ H-NMR and
When IR measurement and SiH group quantification were performed, the following formula:

[0054]

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It was a compound represented by: This compound was referred to as a fluorine-containing organosilicon compound (H-1) and was used in Examples. [Synthesis example 2] Inner volume 100 mL equipped with cooling pipe and thermometer
Into the three-necked flask described above, 0.029 g of a catalyst in which 5% by weight of palladium was supported on carbon, 0.52 g of pure water and 15.0 g of THF were charged, and the mixture was stirred by a magnetic stirrer and suspended.
Next, after heating under a nitrogen stream until the internal temperature reaches 50 ° C, the fluorine-containing organosilicon compound (H-
1) 30.0 g was added dropwise. And in the IR spectrum, SiH
The reaction was stopped when the group absorption (2130 cm ^-1 ) disappeared. The catalyst composed of palladium and carbon was filtered off from the resulting reaction product, and then THF was distilled off under reduced pressure to obtain 11.2 g of a light brown oily product. ¹ H-NM of this product
When R and IR measurements were performed, the following formula:

[0056]

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It was a compound represented by: This compound was referred to as a fluorine-containing organosilicon compound (OH-1) and was used in Examples. [Synthesis Example 3] In Synthesis Example 1, instead of 106.2 g of the polyethylene oxide, polyethylene oxide 210 having an average degree of polymerization of 10 in which molecular chain terminals were terminated with allyl groups and hydroxyl groups.
By the same operation as in Synthesis Example 1 except that 2 g was used, 317.5 g of a pale yellow oily product was obtained.

¹ H-NMR and IR measurements of this product, and
When the SiH group was quantified, the following formula:

[0059]

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It was a compound represented by: This compound was referred to as a fluorine-containing organosilicon compound (H-2) and was used in Examples. [Synthesis Example 4] Instead of 140.1 g of the fluorine-containing organosilicon compound (A-1) in Synthesis Example 1, the following formula (A-2):

[0061]

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The fluorine-containing organosilicon compound (A-
In the same manner as in Synthesis Example 1 except that 155.4 g of 2) was used, 253.2 g of a light brown oily product was obtained.

¹ H-NMR and IR measurements of this product, and
When the SiH group was quantified, the following formula:

[0064]

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It was a compound represented by: This compound was referred to as a fluorine-containing organosilicon compound (H-3) and was used in Examples.

Example 1 Into a three-necked flask having an internal volume of 200 mL equipped with a thermometer and a cooling tube, 70.0 g of fluorine-containing organosilicon compound (H-1) and 30.0 g of THF were charged, and the temperature was raised to 45 ° C. Heated. Next, 2.0 g of a 1 mol / L sodium hydroxide aqueous solution was added. After that, when the absorption of SiH group (2130 cm ^-1 ) disappeared in the IR spectrum, 1 mol / L
The reaction was stopped by adding 2.2 g of hydrochloric acid. The solvent was distilled off from the obtained reaction product under reduced pressure, and the precipitated salt was filtered off.
Thus, 62.9 g of a light brown oily product was obtained. By ¹ H-NMR analysis and IR analysis (the spectrum is shown in FIG. 1) of this product, the following formula:

[0067]

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It was confirmed that the fluorine-containing organosilicon compound represented by

Next, the fluorine-containing organosilicon compound was evaluated as a surfactant as follows. A 0.1 wt% methyl 3-methoxypropionate (MMP) solution of a fluorine-containing organosilicon compound was prepared, and the surface tension at 25 ° C was measured. Table 1 shows the results.

Further, the concentration of the fluorine-containing organosilicon compound in the above solution was changed between 0.001 and 1% by weight, and the temperature was adjusted to 25 ° C.
The surface tension was measured. FIG. 6 shows the result.

Example 2 Example 1 was repeated except that 70.0 g of the fluorine-containing organosilicon compound (H-2) was used instead of 70.0 g of the fluorine-containing organosilicon compound (H-1). 61.1g of light brown oily product
Obtained. By ¹ H-NMR analysis and IR analysis (the spectrum is shown in FIG. 2) of this product, the following formula:

[0072]

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The formation of the fluorine-containing organosilicon compound represented by was confirmed.

Next, 0.1 of the fluorine-containing organosilicon compound is used.
A weight% MMP solution was prepared and the surface tension at 25 ° C. was measured. Table 1 shows the results.

Example 3 Example 1 was repeated except that 70.0 g of the fluorine-containing organosilicon compound (H-3) was used instead of 70.0 g of the fluorine-containing organosilicon compound (H-1). 64.5g of light brown oily product
Obtained. By ¹ H-NMR analysis and IR analysis (the spectrum is shown in FIG. 3) of this product, the following formula:

[0076]

[Chemical 21]

The formation of the fluorine-containing organosilicon compound represented by was confirmed.

Next, 0.1% of the fluorine-containing organosilicon compound
A weight% MMP solution was prepared and the surface tension at 25 ° C. was measured. Table 1 shows the results.

Example 4 A three-necked flask having an inner volume of 100 mL equipped with an ester adapter, a condenser and a thermometer was charged with 20.0 g of a fluorine-containing organosilicon compound (OH-1) and 10.6 g of toluene and heated. did. Further, 0.2 g of dibutyltin dimethoxide was added, and the mixture was reacted for 5 hours while refluxing toluene. During this time, condensed water produced was removed using an ester adapter. The solvent was distilled off from the obtained reaction product under reduced pressure to obtain 17.4 g of a brown oily product. ¹ H-NMR analysis and IR analysis (the spectrum is shown in FIG. 4) of this product confirmed the formation of a fluorine-containing organosilicon compound having the same structure as the fluorine-containing organosilicon compound.

Next, 0.1% of the fluorine-containing organosilicon compound
A weight% MMP solution was prepared and the surface tension at 25 ° C. was measured. Table 1 shows the results.

Example 5 In Example 4, instead of 0.2 g of dibutyltin dimethoxide, the following formula:

[0082]

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A brown oily product was obtained in the same manner as in Example 4 except that 0.1 g of perfluorocarboxylic acid ammonium salt represented by the formula: p was an average value of 4 was used. 18.1 g was obtained. ¹ H-NMR analysis and I of this product
The R analysis (the spectrum of which is shown in FIG. 5) confirmed the formation of a fluorinated organosilicon compound having the same structure as the fluorinated organosilicon compound.

Next, 0.1 of the fluorine-containing organosilicon compound is used.
A weight% MMP solution was prepared and the surface tension at 25 ° C. was measured. Table 1 shows the results.

Comparative Examples 1 to 3 The following formulas:

[0086]

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Fluorine-containing organosilicon compound represented by
For each of the above, an MMP solution having a fluorine-containing organosilicon compound concentration of 0.1% by weight was prepared, and then the surface tension at 25 ° C. was measured. Table 1 shows the results. Further, regarding each of the fluorine-containing organosilicon compounds and, the fluorine-containing organosilicon compound concentration is 0.01 to 1% by weight.
The MMP solution changed to was prepared, and the surface tension at 25 ° C. was measured. FIG. 6 shows the result.

[0088]

[Table 1]

[0089]

INDUSTRIAL APPLICABILITY The novel fluorine-containing organosilicon compound of the present invention is more excellent in the ability to reduce the surface tension when added to an organic solvent or the like than a conventional surfactant comprising a fluorine-containing organosilicon compound. Therefore, it is useful as a fluorine-containing surfactant in the fields of plastic and rubber industry, petroleum industry, dye and pigment industry, metal and machinery industry, pharmaceuticals and agricultural chemicals, household products, photography and printing and the like.

[Brief description of drawings]

1 is an IR spectrum of the product obtained in Example 1. FIG.

FIG. 2 is an IR spectrum of the product obtained in Example 2.

FIG. 3 is an IR spectrum of the product obtained in Example 3.

FIG. 4 is an IR spectrum of the product obtained in Example 4.

5 is an IR spectrum of the product obtained in Example 5. FIG.

FIG. 6 Fluorine-containing organosilicon compound and MM
It is a graph which shows the surface tension of P solution.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C08G 77/46 NUL C08G 77/46 NUL (72) Inventor Hirofumi Kinoshita Daijin Matsuida-cho, Usui District, Gunma Prefecture No. 1 No. 10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Inventor Koichi Yamaguchi Osamu Matsuida-cho, Usui-gun Gunma No. 1 Hitomi No. 10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory

Claims (3)

[Claims] [Claim 1] General formula (1): [Wherein Rf is independently a perfluoroalkyl group having 4 to 14 carbon atoms or a perfluoropolyether group having 5 to 14 carbon atoms, and Q is independently an ethylene group and / or a propylene group being an ether bond. R is a polyether group formed by repeatedly bonding, and R is independently a monovalent carbon atom selected from the group consisting of a hydrogen atom, an allyl group, an alkyl group having 1 to 4 carbon atoms and an acyl group having 2 to 3 carbon atoms. A hydrogen group or an atom, L and m are each independently 0 or 1.
n is 1 or 2, x is 2 or 3, and Me is a methyl group]. 2. General formula (2): A compound represented by the formula: wherein Rf, Q, R, Me, L, m, n and x have the same meanings as described above and Z is a hydrogen atom or a hydroxyl group. Item 2. A method for producing a fluorine-containing organosilicon compound according to Item 1. 3. A fluorine-containing surfactant comprising the fluorine-containing organosilicon compound according to claim 1.