KR20160077963A - Perfluoro-alkyl modified organic silane - Google Patents

Abstract

The present invention relates to a method for preparing perfluoroalkyl modified organic silane, and the method for preparing perfluoroalkyl modified organic silane comprises a step for adding a pyrolytic radical initiator and a tin-based organic metal compound to a mixture of a perfluoroalkyl iodide compound and an organic silane having a double bond. The method for preparing perfluoroalkyl modified organic silane suppresses an additive reaction of the pyrolytic radical initiator and smoothens the reduction of iodine, thereby forming perfluoroalkylalkoxy silane at high efficiency and high purity, causes no chlorine gas, which is a toxic gas, thereby making less environmental loading, such as gas purification facilities, and does not use an expensive metal catalyst and hydrogen gas, thereby preparing perfluoroalkyl modified organic silane easily and economically.

Description

TECHNICAL FIELD [0001] The present invention relates to a perfluoroalkyl-modified organosilane and a perfluoroalkyl-

The present invention relates to a process for producing a perfluoroalkyl-modified organosilane, and a process for the production of a perfluoroalkyl-modified organosilane which comprises subjecting perfluoroalkyl iodide and an organosilane containing a double bond to an addition reaction will be.

Generally, perfluoroalkyl-containing compounds have physical properties such as water repellency, chemical resistance, releasability and stain resistance due to their very low surface energy. Because of these properties, perfluoroalkyl-containing compounds (typically, Teflon resins) have been widely used to produce antifouling agents for paper and fiber, and anti-adhesive coatings for cookware.

Silane coupling agents are also widely known as means for establishing a firm bond between the surface of a material such as glass or cloth and an organic compound. The silane coupling agent has an organic functional group and a reactive silyl functional group (typically, an alkoxysilyl radical) in the molecule, and the alkoxysilyl radical is hydrolyzed and self-condensed with moisture in the air to convert it to a siloxane to form a coating A strong coating film having durability can be formed by forming chemical and physical bonds with the glass or metal surface.

Therefore, a perfluoroalkyl-modified organosilane which utilizes the low surface energy of perfluoroalkyl and utilizes the adhesive ability of the silane coupling agent is used as a surface treatment agent having a function of preventing contamination.

A technique for perfluoroalkyl-modified organosilanes used as the surface treatment agent described above is disclosed in U.S. Patent No. 6255516 and Japanese Patent Laid-Open No. 2002-205995. This patent discloses a perfluoroalkyl-modified organosilane produced by preparing a perfluoroalkyl-modified chlorosilane by the addition reaction of perfluoroalkylethylene with a chlorosilane and then replacing the chlorine functional group with an alcohol functional group .

However, since the above-mentioned production method generates poisonous hydrochloric acid gas in the process of replacing the chlorine functional group of the perfluoroalkyl-modified chlorosilane with the alcohol functional group, a high cost waste hydrochloric acid gas treatment facility for treating the hydrochloric acid gas is required do. In addition, the perfluoroalkyl-modified chlorosilane formed by the above-mentioned method is too sensitive to moisture, and if the chlorosilane gas is generated, the hydrolysis reaction proceeds and the purity of the product is reduced .

Further, a method of directly producing perfluoroalkyl-modified organosilane by the addition reaction of perfluoroalkylethylene with an alkoxysilane has been proposed. However, this method has a problem that the yield of reaction is too low, and the reaction rate of the alkyl alcohol- There is a disadvantage that a product of high purity can not be obtained because a large amount of reactants are produced.

In addition, a technique for producing the perfluoroalkyl-modified organosilane by using a thermal decomposition initiator and a metal reducing agent is a technique in which an addition reaction product formed by the use of a thermal decomposition initiator and an addition reaction product of an organosilane produced during the reaction remain, The alkali metalating agent generally used has a problem in that it is not easy to remove the iodine atom at the time of purifying the product and a low yield to replace the hydrogen atom with the hydrogen atom. In addition, since the reaction is divided into the first and second reaction steps, the production cost is increased due to the diversification of production facilities, the investment cost is increased, the manufacturing process is complicated, and the process time is increased.

United States Patent No. 6255516 (Registered on July 3, 2001) Japanese Unexamined Patent Publication No. 2002-205995 (published on July 23, 2002)

It is an object of the present invention to provide a process for producing perfluoroalkylalkoxysilane which can form perfluoroalkylalkoxysilane with high yield and high purity by suppressing addition reaction of pyrolysis radical initiator and facilitating iodine reduction, And a method for producing perfluoroalkyl-modified organosilane which can be produced easily and economically because expensive metal catalyst and hydrogen gas are not used.

According to an embodiment of the present invention, there is provided a method for producing a perfluoroalkyl iodide compound, which comprises adding a thermal decomposition radical initiator and a tin-based organometal compound to a mixture of a perfluoroalkyl iodide compound and an organosilane containing a double bond, There is provided a process for producing a perfluoroalkyl-modified organosilane represented by the general formula (1).

[Chemical Formula 1]

R _f - [CH ₂ ] _n -Si (CH ₃ ) _{3- a} OR _a

(Wherein R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms, R is an alkyl group having 1 to 4 carbon atoms, n is an integer of 2 to 6, 2 or 3)

The perfluoroalkyl iodide compound may be represented by the following general formula (2).

(2)

R _f -I

(Wherein R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms)

The organosilane containing the double bond may be represented by the following formula (3).

(3)

CH ₂ CH (CH ₂ ) _m -Si (CH ₃ ) _{3- a} OR _a

(Wherein m is an integer of 0 to 4, R is an alkyl group having 1 to 4 carbon atoms, and a is 2 or 3)

The pyrolysis radical initiator and the tin-based organometallic compound may be introduced sequentially.

The pyrolysis radical initiator may be added at 55 to 60 ° C, the temperature may be lowered to 10 to 25 ° C, and then the tin-based organometallic compound may be introduced.

The pyrolysis radical initiator may be added and stirred at 60 to 80 ° C for 6 to 8 hours.

The tin-based organometallic compound may be added and stirred at 10 to 25 ° C for 4 to 8 hours.

The pyrolysis radical initiator may be added by dissolving the pyrolysis radical initiator in an amount of 10 to 20 parts by weight per 100 parts by weight of the ether-based solvent to prepare an initiator solution, and the initiator solution may be added at a rate of 0.2 to 0.5 ml / s have.

The tin-based organometallic compound may be introduced at a rate of 0.5 to 1.0 ml / s.

The tin-based organometallic compound may be a trialkyl tin hydride (wherein the alkyl is a straight or branched alkyl group having 1 to 4 carbon atoms).

The mixture of the perfluoroalkyl iodide compound and the organosilane containing the double bond may contain the perfluoroalkyl iodide compound and the organosilane containing the double bond in a molar ratio of 1: 1 to 1: 1.2 .

The pyrolysis radical initiator may be added in an amount of 0.01 to 0.1 mole based on 1 mole of the perfluoroalkyl iodide compound.

The tin-based organometallic compound may be added in an amount of 1 to 1.2 moles per mole of the perfluoroalkyl iodide compound.

The perfluoroalkyl-modified organosilane thus produced is distilled under reduced pressure at 40 to 55 ° C under a pressure of 0.5 to 1.0 torr to remove the solvent and unreacted starting material and distillation under reduced pressure at 65 to 85 ° C under a pressure of 0.5 to 1.0 torr, To obtain a perfluoroalkyl-modified organosilane.

The process for producing perfluoroalkyl-modified organosilanes according to the present invention can form perfluoroalkylalkoxysilanes with high yield and high purity by suppressing addition reaction of pyrolysis radical initiator and facilitating iodine reduction, Since chlorine gas is not generated, environmental burden such as a gas purification facility is small, and expensive metal catalyst and hydrogen gas are not used, so that it can be manufactured easily and economically.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, preferred embodiments of the present invention will be described in detail to enable those skilled in the art to easily carry out the technical idea of the present invention. However, it should be understood that the present invention is not limited to the following embodiments, and various changes and modifications may be made without departing from the scope of the present invention. Rather, the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art.

The process for preparing a perfluoroalkyl-modified organosilane according to an embodiment of the present invention includes the step of adding a thermal decomposition radical initiator and a tin-based organometallic compound to a mixture of a perfluoroalkyl iodide compound and an organosilane containing a double bond do.

That is, the process for producing the perfluoroalkyl-modified organosilane can reduce the cost of gas purification equipment due to the absence of hydrochloric acid gas, which is a toxic gas, and can obtain a perfluoroalkyl-modified organosilane having a high yield and high purity .

Also, the process for producing the perfluoroalkyl-modified organosilane can be carried out in one step without separating or purifying the intermediate product by using the tin-based organometallic compound, and the addition reaction of the decomposed pyrolysis radical initiator is suppressed And the iodine reduction is facilitated, whereby the perfluoroalkylalkoxysilane can be formed with high yield and high purity, and since expensive metal catalyst and hydrogen gas are not used, it can be easily and economically produced.

The organosilane may be an alkylalkoxysilane, and the perfluoroalkyl-modified organosilane may be represented by the following general formula (1).

[Chemical Formula 1]

R _f - [CH ₂ ] _n -Si (CH ₃ ) _{3- a} OR _a

In the above formula (1), R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms, specifically, perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl, perfluoro Pentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, perfluorododecyl.

R is an alkyl group having 1 to 4 carbon atoms, and may specifically be methyl, ethyl, propyl, n-butyl, iso-butyl or tert-butyl.

N is an integer of 2 to 6, and a is 2 or 3;

Specifically, the compound represented by the formula (1) may be a compound represented by any one of the formulas (1-1) to (1-4).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

The perfluoroalkyl iodide compound may be represented by the following general formula (2).

(2)

R _f -I

In the above formula (2), R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms, specifically, perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl, perfluoro Pentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, perfluorododecyl.

Specifically, the perfluoroalkyl iodide compound may be a perfluoroalkyl iodide such as perfluoropropyl iodide, perfluorobutyl iodide, perfluorooctyl iodide or perfluorodecyl iodide, or a perfluoroalkyl iodide such as perfluoroisopropyl iodide Iodine, and perfluoro isobutyl iodide; and the like.

More specifically, the compound represented by the formula (2) may be a compound represented by any one of the following formulas (2-1) and (2-2).

[Formula 2-1]

[Formula 2-2]

The organosilane containing the double bond may be represented by the following formula (3).

(3)

CH ₂ CH (CH ₂ ) _m -Si (CH ₃ ) _{3- a} OR _a

In Formula 3, R is an alkyl group having 1 to 4 carbon atoms, and may specifically be methyl, ethyl, propyl, n-butyl, iso-butyl or tert-butyl.

M is an integer of 0 to 4, and a is 2 or 3;

Specifically, the organosilane containing a double bond may be prepared by reacting a vinyl-substituted trialkoxysilane and a vinyl-substituted methyldialkoxysilane, an allyl functional group-substituted trialkoxysilane, an allyl functional group-substituted methyldialkoxysilane, An alkoxysilane having an alkyl functional group containing a double bond capable of reacting, and the like.

More specifically, the compound represented by the formula (3) may be a compound represented by any one of the following formulas (3-1) and (3-2).

[Formula 3-1]

[Formula 3-2]

The mixture of the perfluoroalkyl iodide compound and the organosilane containing the double bond may contain the perfluoroalkyl iodide compound and the organosilane containing the double bond in a molar ratio of 1: 1 to 1: 1.2 . If the content of the organic silane containing the double bond is less than 1 molar, an unreacted perfluoroalkyl addition reaction may occur. If the content of the organic silane exceeds 1.2 molar ratio, the double bond of the organic silane may be changed into a single bond, can do.

The pyrolysis initiator may be at least one selected from the group consisting of azobisisobutyronitrile (AIBN), benzoyl peroxide (BPO), lauryl peroxide, azobisisocapronitrile, azobisisovaleronitrile, t-butyl hydroperoxide, May be used.

The tin-based organometallic compound may be trialkyltin hydride (wherein the alkyl is a linear or branched alkyl group having 1 to 4 carbon atoms), specifically trimethyltin hydride represented by the following formula 4-1 Or a tributyl tin hydride represented by the following formula (4-2).

[Formula 4-1]

[Formula 4-2]

The perfluoroalkyl-modified organosilane may be prepared by sequentially introducing the pyrolysis radical initiator and the tin-based organometallic compound. In this case, the pyrolysis radical initiator is first introduced, and then the tin- .

At this time, it is preferable that the pyrolysis radical initiator is added at a temperature of 55 to 60 ° C in that the reactivity of the initiator can be controlled.

The pyrolysis radical initiator may be added and stirred at 60 to 80 ° C for 6 to 8 hours.

In addition, the pyrolysis radical initiator may be prepared by dissolving the pyrolysis radical initiator in an amount of 10 to 20 parts by weight in 100 parts by weight of an ether-based solvent to prepare an initiator solution, and the prepared initiator solution may be added at a rate of 0.2 to 0.5 ml / s have. In the case of using the initiator solution in which the thermal decomposition radical initiator is dissolved in the ether-based solvent as described above, the addition reaction of the radical initiator can be suppressed. If it exceeds 0.5 ml / s, .

The ether-based solvent may be selected from ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl cellosolve, butyl cellosolve and the like, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethylene glycol mono Glycol ethers such as methyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether propionate, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate and the like.

On the other hand, the tin-based organometallic compound is preferably added in such a manner that the temperature is lowered to 10 to 25 ° C and then the over-heating can be prevented.

Further, it is preferable to add the tin-based organometallic compound and stir at 10 to 25 캜 for 4 to 8 hours.

The tin-based organometallic compound can be introduced at a rate of 0.5 to 1.0 ml / s, and when the charging rate exceeds 1.0 ml / s, there may be a problem due to heat generation.

The pyrolysis radical initiator may be added in an amount of 0.01 to 0.1 mole based on 1 mole of the perfluoroalkyl iodide compound. If the content of the thermal decomposition radical initiator is less than 0.01 molar part, unreacted materials may remain. If the content of the thermal initiator exceeds 0.1 molar part, there may be a problem of removal during purification due to the addition reaction of the radical initiator.

The tin-based organometallic compound may be added in an amount of 1 to 1.2 moles per mole of the perfluoroalkyl iodide compound. If the content of the tin-based organic metal compound is less than 1 part by mole, unreacted materials may remain. If the content of the tin-based organic metal compound exceeds 1.2 parts by mole, the metal content due to decomposition of the organometallic compound may increase.

The process for preparing perfluoroalkyl-modified organosilane may further include distilling the reaction product at a temperature of from 40 to 55 ° C under a pressure of from 0.5 to 1.0 torr to remove the solvent and unreacted starting material. If the pressure of the first vacuum distillation is less than 0.5 torr, the addition reaction of the radical initiator and the double bond of the organosilane may be decomposed to remove the alkylsilane. If the pressure is more than 1.0 torr, There may be a problem that can be contained. If the temperature of the first vacuum distillation is less than 40 ° C, there may be a problem of removing the alkylsilane formed by decomposition of the double bond of the radical initiator and the double bond of the organosilane. If the temperature exceeds 55 ° C, There may be a problem that can be contained.

The process for producing the perfluoroalkyl-modified organosilane may further include the step of subjecting the final reactant remaining after the first vacuum distillation to a second vacuum distillation at a temperature of from 65 to 85 ° C under a pressure of from 0.5 to 1.0 torr to obtain a final product . If the pressure of the second vacuum distillation is less than 0.5 torr, there may be a problem of metal inclusion due to simultaneous distillation of the organometallic compound reactant used as a reducing agent and simultaneous distillation with the final material. If the pressure exceeds 1.0 torr, There may be an increasing problem. If the temperature of the second vacuum distillation exceeds 85 ° C, there may be a metal content problem because the reactants of the organometallic compound used as a reducing agent are simultaneously distilled and simultaneously received with the final material.

Hereinafter, the present invention will be described concretely with reference to Examples. However, the following Examples and Experimental Examples are merely illustrative of one form of the present invention, and the scope of the present invention is not limited by the following Examples and Experimental Examples .

( Example  One)

(TDFHI) and trimethoxyvinylsilane (TMOVS) were fed into a three-necked flask equipped with a reflux condenser at a molar ratio of 1: 1.1, and then heated to 60 DEG C while stirring. When the internal temperature of the flask was sufficiently heated, azobisbutylnitrile (AIBN), which is a pyrolysis radical initiator, was dissolved in an ether-based solvent, and 0.5 ml / sec was dropped slowly into the stirred flask, and the external heating temperature was stopped. Thereafter, when the dropwise addition was completed, the external heating temperature was again set to 60 DEG C and stirred for 6 hours. Thereafter, the internal temperature of the flask was lowered to room temperature (25 DEG C), and tributyltin hydride (TBTH) was added at a rate of 1 ml per 1 second into the flask at a ratio of 1 mol of the total reactants. After stirring for an additional 4 hours, the solvent and unreacted materials were distilled off under reduced pressure at 1 torr and 50 ° C, and the temperature of the pyrolysis radical initiator was further reduced to 20 ° C at a temperature of 1 torr. Thereafter, vacuum distillation was carried out at a temperature of 80 ° C at 1 torr to obtain 1H, H, 2H, 2H-Perfluorooctyltrimethoxysilane in a yield of 70%.

_{^{1 H-NMR (CDCl 3)}} : δ = 0.83 (m, 2H), 2.13 (m, 2H), 3.56 (s, 9H)

_{^{13 C-NMR (CDCl 3)}} : δ = 115-120 (m, FC), 50.90 (s, CH 3), 25.05 (t, CH 2), -0.5 (s, CH 2)

( Example  2)

(TDFHI) and triethoxyvinylsilane (TEOVS) were fed into a three-necked flask equipped with a reflux condenser at a molar ratio of 1: 1.1, and then heated to 60 DEG C while stirring. When the internal temperature of the flask was sufficiently heated, azobisbutylnitrile (AIBN), which is a pyrolysis radical initiator, was dissolved in an ether-based solvent, and 0.5 ml / sec was dropped slowly into the stirred flask, and the external heating temperature was stopped. Thereafter, when the dropwise addition was completed, the external heating temperature was again set to 60 DEG C and stirred for 6 hours. Thereafter, the internal temperature of the flask was lowered to room temperature (25 DEG C), and tributyltin hydride (TBTH) was added at a rate of 1 ml per 1 second into the flask at a ratio of 1 mol of the total reactants. After stirring for an additional 4 hours, the solvent and unreacted materials were removed by distillation under reduced pressure at 70 ° C under 1 torr. Thereafter, the distillation under reduced pressure was carried out at a temperature of from 1 torr to 90 ° C to obtain 1H, H, 2H, 2H-perfluorooctyltriethoxysilane in a yield of 70%.

_{^{1 H-NMR (CDCl 3)}} : δ = 0.89 (m, 2H), 1.18 (s, 9H), 2.23 (m, 2H), 3.86 (m, 6H)

_{^{13 C-NMR (CDCl 3)}} : δ = 115-120 (m, FC), 45.50 (s, CH 2), 21.05 (t, CH 2), 15.10 (s, CH 3), -0.55 (s, CH ₂ )

( Example  3)

Nonafluorobutyl iodide (NFBI) and trimethoxyvinylsilane (TMOVS) were fed into a three-necked flask equipped with a reflux condenser at a molar ratio of 1: 1.1, and then heated to 60 DEG C with stirring. When the internal temperature of the flask was sufficiently heated, azobisbutylnitrile (AIBN), which is a pyrolysis radical initiator, was dissolved in an ether-based solvent, and 0.5 ml / sec was dropped slowly into the stirred flask, and the external heating temperature was stopped. Thereafter, when the dropwise addition was completed, the external heating temperature was again set to 60 DEG C and stirred for 6 hours. Thereafter, the internal temperature of the flask was lowered to room temperature (25 DEG C), and tributyltin hydride (TBTH) was added at a rate of 1 ml per 1 second into the flask at a ratio of 1 mol of the total reactants. After further stirring for an additional 4 hours, distillation under reduced pressure at 1 Torr and 40 ° C yielded 1H, 2H, 2H-Perfluorohexyltrimethoxysilane in 75% yield.

_{^{1 H-NMR (CDCl 3)}} : δ = 0.81 (m, 2H), 2.23 (m, 2H), 3.66 (s, 9H)

_{^{13 C-NMR (CDCl 3)}} : δ = 115-120 (m, FC), 51.90 (s, CH 3), 25.15 (t, CH 2), -0.61 (s, CH 2)

( Example  4)

Nonafluorobutyl iodide (NFBI) and triethoxyvinylsilane (TEOVS) were fed into a three-necked flask equipped with a reflux condenser at a molar ratio of 1: 1.1, and then heated to 60 DEG C while stirring. When the internal temperature of the flask was sufficiently heated, azobisbutylnitrile (AIBN), which is a pyrolysis radical initiator, was dissolved in an ether-based solvent, and 0.5 ml / sec was dropped slowly into the stirred flask, and the external heating temperature was stopped. Thereafter, when the dropwise addition was completed, the external heating temperature was again set to 60 DEG C and stirred for 6 hours. Thereafter, the internal temperature of the flask was lowered to room temperature (25 DEG C), and tributyltin hydride (TBTH) was added at a rate of 1 ml per 1 second into the flask at a ratio of 1 mol of the total reactants. After further stirring for 4 hours, distillation under reduced pressure at 1 Torr and 40 ° C yielded 1H, 2H, 2H-perfluorohexyltriethoxysilane in a yield of 75%.

_{^{1 H-NMR (CDCl 3)}} : δ = 0.88 (m, 2H), 1.17 (s, 9H), 2.23 (m, 2H), 3.85 (m, 6H)

_{^{13 C-NMR (CDCl 3)}} : δ = 115-120 (m, FC), 45.51 (s, CH 2), 21.15 (t, CH 2), 15.11 (s, CH 3), -0.53 (s, CH ₂ )

Claims (11)

A process for producing a perfluoroalkyl-modified organosilane represented by the following formula (1), comprising the step of adding a thermal decomposition radical initiator and a tin-based organometallic compound to a mixture of a perfluoroalkyl iodide compound and an organosilane containing a double bond.
[Chemical Formula 1]
R _f - [CH ₂ ] _n -Si (CH ₃ ) _{3- a} OR _a
(Wherein R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms, R is an alkyl group having 1 to 4 carbon atoms, n is an integer of 2 to 6, 2 or 3) The method according to claim 1,
The perfluoroalkyl iodide compound is represented by the following general formula (2)
Wherein the double bond-containing organosilane is represented by the following general formula (3).
(2)
R _f -I
(Wherein R _f is a straight or branched perfluoroalkyl having 1 to 12 carbon atoms)
(3)
CH ₂ CH (CH ₂ ) _m -Si (CH ₃ ) _{3- a} OR _a
(Wherein m is an integer of 0 to 4, R is an alkyl group having 1 to 4 carbon atoms, and a is 2 or 3) The method according to claim 1,
The pyrolysis radical initiator and the tin-based organometallic compound are sequentially introduced,
The pyrolysis radical initiator is introduced at 55 to 60 DEG C,
Wherein the temperature is lowered to 10 to 25 占 폚, and then the tin-based organometallic compound is introduced. 3. The method of claim 2,
The pyrolysis radical initiator is added and stirred at 60 to 80 DEG C for 6 to 8 hours,
Wherein the tin-based organometallic compound is added and stirred at 10 to 25 DEG C for 4 to 8 hours. 3. The method of claim 2,
The addition of the pyrolysis radical initiator
Dissolving the pyrolysis radical initiator in 10 to 20 parts by weight in 100 parts by weight of an ether-based solvent to prepare an initiator solution,
Wherein the initiator solution is added at a rate of 0.2 to 0.5 ml / s. 3. The method of claim 2,
Wherein the introduction of the tin-based organometallic compound is carried out at a rate of 0.5 to 1.0 ml / s. The method according to claim 1,
Wherein the tin-based organometallic compound is a trialkyltin hydride (wherein the alkyl is a linear or branched alkyl group having 1 to 4 carbon atoms). The method according to claim 1,
Wherein the mixture of the perfluoroalkyl iodide compound and the organic silane containing the double bond comprises the perfluoroalkyl iodide compound and the organic silane containing the double bond in a molar ratio of 1: 1 to 1: 1.2 A process for producing a perfluoroalkyl-modified organosilane. The method according to claim 1,
Wherein the pyrolysis radical initiator is added in an amount of 0.01 to 0.1 mole based on 1 mole of the perfluoroalkyl iodide compound. The method according to claim 1,
Wherein the tin-based organometallic compound is added in an amount of 1 to 1.2 moles per mole of the perfluoroalkyl iodide compound. The method according to claim 1,
The perfluoroalkyl-modified organosilane prepared above was reacted with
Distillation under reduced pressure of 0.5 to 1.0 torr at 40 to 55 DEG C to remove the solvent and unreacted starting material,
Further comprising the step of distilling under reduced pressure at a temperature of from 65 to 85 占 폚 under a pressure of from 0.5 to 1.0 torr to obtain said perfluoroalkyl-modified organosilane.