KR101719340B1 - A Silicone Coupling Agent having Hydrophilic and Hydrophobic Groups for Invisible Fingerprint Coating and a Method for Producing the Same - Google Patents

Abstract

The present invention relates to a silicone binder for a fingerprint conspicuousness preventing film, and to a method for producing the same, and specifically, to a silicone binder for a fingerprint conspicuousness preventing film, and to a method for producing the same for improving performance by modification of a lipophilic group. The silicone binder is prepared by sequentially reacting methoxyethanol on one end of alpha, omega-dihaloalkane and undecenol on the other end, so as to remove HX and synthesize an alkene having an ether bond, and by making the alkene again react with trichlorosilane under a tetrabutylphosphonium chloride catalyst, so as to simultaneously synthesizing a silane compound by a double-hydrogenation reaction.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hydrophilic and lipophilic group-containing silicone bonding agent for a fingerprint-preventing coating film, and a method for producing the same. 2. Description of the Related Art A Silicone Coupling Agent Having Hydrophilic and Hydrophobic Groups for Invisible Fingerprint Coating and a Producing the Same

The present invention relates to a silicone binder for a fingerprint appearance preventing coating and a method for producing the same, and more particularly, to a silicone binder for a fingerprint appearance preventing coating and a method for manufacturing the silicone binder for improving the performance by modification of a lipophilic group.

A display and a touch panel are mounted on the input / output portion of an information terminal such as a portable telephone, a personal computer, a navigation or an ATM, which is a necessity of daily life. The display surface of such a device is manipulated by a finger, and as a result, the fingerprint remains on the display surface, resulting in poor appearance. In order to solve this problem, a coating is required to prevent the display surface and the touch panel from adhering the display surface of the fingerprint.

In order to solve the above problems, a method using a silicone binder containing a fluorine-substituted alkyl group that is both water-repellent and oil-repellent can be applied. However, such a method has a problem in that it is not suitable for use such as direct contact with the sebum of the face like a mobile phone or repeatedly touching the finger like a touch panel. The water-repellent or oil repellent coating has a purpose of easily wiping a buried fingerprint, not a purpose of preventing adhesion of lipid, which is a main component of the fingerprint. Also, the attached fingerprints are more likely to have dirt on the eyes in the oil-repellent film, and the display surface becomes apparently dirty. Another method is to make the surface water-repellent and lipophilic at the same time. This method has an advantage that the affinity with the fingerprint and the sebum component is improved, and it is not conspicuous even when attached.

In order to measure the performance of such a film, the degree of hydrophilicity and lipophilicity of the film formed on the substrate by the water contact angle and the diiodo methane contact angle can be evaluated. Generally, the fingerprints formed on the film are composed of the substance that the body basically emits and the oil or the fat substance which is discharged from the skin. Therefore, in order to prevent the appearance of fingerprints, the properties of the film should not be one-sided, such as hydrophilic or lipophilic, and the degree of affinity for the two components included in the fingerprint should be optimized .

For example, a silicone coupling agent having a unique property having a lipophilic group and a hydrophilic group at the end of a lipophilic group suited for this purpose is substituted with a hydrophilic group, and for example, an alkoxy alcohol or polyether is substituted at the end of an undecyl group having a carbon number of 11 . (K. L. Mittal, "Silane and Other Coupling Agents ", Koninklijke Brill N V, Leiden, The Natherlands, 2009). The undecyl group having carbon number 11 is a lipophilic group and the alkoxy alcohol or polyether is a hydrophilic group. When treated with such a silicone binder, there is a lipophilic layer on the surface, and a hydrophilic layer on top of the hydrophilic layer makes the water spread well and has good affinity with the hydrophilic material, which is convenient for the purpose of anti-fogging or for capturing hydrophilic substances such as proteins (Randy De Palma et al., U. S. Patent 7,285, 674 (Dec. 23, 2007)).

Korean Patent Laid-Open No. 10-2012-0080880 discloses that the water contact angle of the fingerprint appearance preventing film is, for example, 60 degrees or more, preferably 65 to 100 degrees, so that most of the water component of the fingerprint is adsorbed on the film, To evaporate without forming the film. In addition, the contact angle of diiodo methane in the finger print preventing film is, for example, 45 degrees or less, preferably 30 to 43 degrees. When the diiodo methane contact angle is satisfied, the film has a lipophilic property, and if the fingerprint is adhered on the film, affinity with the fingerprint composed mainly of the lipid may be strong. As a result, the attached fingerprints are wetted and widened at the interface of the film, and a thin layer mainly composed of fat is formed on the fingerprint-attached portion, so that the fingerprints themselves are not conspicuous and the dirtiness due to the fingerprint of the substrate can be prevented. do. The prior art discloses methoxyethoxydecyltrimethoxysilanes as a material for this purpose. It is disclosed that methoxyethoxy at the molecular end of the compound is a hydrophilic group and has a water contact angle of 70 degrees or more and an undecyl group is a lipophilic group and has a diiodo methane contact angle of 40 degrees or less. In addition, the fingerprint appearance preventing film may further include an additive for imparting lubricity so as to impart more lubrication without affecting the basic properties of the film, and examples thereof include an unsaturated fatty acid, a saturated fatty acid, and a hydrocarbon- ≪ / RTI > and at least one additive selected from the group consisting of < RTI ID = 0.0 >

Suitable methoxyethoxyd undecyltrimethoxysilanes suitable for forming a fingerprint-proofing film are already industrially produced materials. Alkoxy-terminated polyethylene glycol may be treated with metal sodium or sodium hydride to form an anion, react with bromoundecene to introduce the alkenyl group, and add triethoxysilane to the alkenyl group through the hydrogen silylation reaction (B. Arkels et al, US Patent Application 0105817 (Apr. 29, 2010)). Therefore, if the silane coupling agent is produced by using undecenol, which is a raw material of bromoundecene and is produced industrially and the price is lower than bromoundecene, the process is omitted in one step, so that the production cost can be lowered, .

The applicant of the present invention has found that the use of undecenol without directly using bromo undecene while synthesizing a silicone compound which is bonded to an undecyl group which is a lipophilic group and which is initiated by an alkoxy group, (Korean Patent Registration No. 10-1459507, published on Mar. 26, 2014). Undecenol was used as a starting material to make an undecene alkoxide anion with metal sodium and reacted with alkoxyalkyl chloride. Alkoxyalkyl chloride, for example, 2-chloroethylmethylether, is reacted with an undecene alcohol anion having an ether group corresponding to a hydrophilic group to synthesize 11- (2-methoxyethoxy) -1-undecene Respectively. 2-chloroethyl methyl ether or 3-chloropropyl methyl ether is a commercial product and can be easily synthesized by reacting methoxyethanol or methoxypropanol with thionyl chloride (Japan Kokai Tokkyo Koho, 04021646, 24 Jan 1992, PCT Int. Appl., 2010021680, 25 Feb 2010).

In the process of manufacturing the silicon binder for the anti-fingerprint film, when an anion is made by reacting the alkanol with the metal sodium, an anhydrous solvent should be used and the risk of explosion of generated hydrogen is very high, so other methods need to be used. For example, in this process, using KOH under tetrabutylammonium bromide catalyst to remove KX and form an ether bond, there is no danger of hydrogen explosion and an economical method can be used. U.S. Patent No. 6,841,079 discloses a process for the synthesis of KOH under tetrabutylammonium bromide catalyst without the use of metal sodium in the process of reacting allyl bromide with fluorine-substituted alkyl alcohols. Therefore, other general alkyl halides may be applied instead of allyl bromide using such reaction conditions.

This improved process improves the economical efficiency and reduces the risk of existing products that are produced by combining the hydrophilic group of the alkoxy alcohol and the undecyl group of the carbon-11 having a lipophilic group, and the production of alpha, omega-dihaloalkane, alpha, omega - A new silicone bonding agent can be produced which can increase the weight of the octahedral group in the middle of the dihaloalkane to improve the fingerprint appearance preventing performance.

An object of the present invention is to solve the problems of the prior art and has the following purpose.

Prior Art 1: Patent Publication No. 10-2012-0080880 (Samsung Electronics Co., Ltd., published on July 18, 2012) A composition for preventing fingerprint appearance, a fingerprint appearance preventing film using the composition, and an article Prior Art 2: United States Patent Number 6,841,079 (3M Innovative Properties Company, published December 11, 2003) Fluorochemical treatment for silicon articles

It is an object of the present invention to provide silicone binders for a fingerprint appearance preventive coating in which a hydrophilic group and a lipophilic group are simultaneously substituted, and a method for producing the same.

According to a preferred embodiment of the present invention, HX is removed by sequentially reacting methoxyethanol represented by the formula (2) and undecenol at one end with one mole of the alpha, omega-dihaloalkane represented by the formula (1) Synthesized to have an ether bond represented by the general formula (3)

Formula 1

X- (R) -X

In the above R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or (CH _{2) 3} -O- (CH _{2) 6 -O- (CH 2)} 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O- (CH 2) 6 -O- (CH ₂ ) ₆ , (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is Cl, Br or I,

(2)

Me- (OCH ₂ CH ₂₎ mOH

M is 1 or 3,

(3)

And in which m is 1, 2 or 3, n is 0 or 1 and in wherein R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2 ) _8, (CH _{2) 10} or _{(CH 2) 3 -O- (CH} 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2 _{) 8, (CH 2) 6} -O- (CH 2) 6 -O- (CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X is Cl , Br or I, wherein the hydrophilic group and the lipophilic group are simultaneously substituted.

According to another preferred embodiment of the present invention, the compound represented by the general formula (3) is synthesized simultaneously with trichlorosilane in the presence of a tetrabutylphosphonium chloride catalyst in a double-

Formula 4

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O - (CH ₂ ) ₆ -O- (CH ₂ ) ₆ , (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , wherein the hydrophilic group and the lipophilic group are simultaneously substituted A silicone binder for a fingerprint-preventing coating film is provided.

According to another preferred embodiment of the present invention, there is provided a process for producing a chlorosilane compound represented by Chemical Formulas 6 and 7, which is obtained by reacting a chlorosilane compound represented by Chemical Formulas 4 and 5 with an alcohol,

6

Formula 7

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O _{- (CH 2) 6 -O- (} CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X is a Cl, Br or I, R1 is carbon Wherein the hydrophilic group and the lipophilic group are simultaneously substituted with an alkyl group having 1 to 3 carbon atoms.

According to another preferred embodiment of the present invention, methoxyethanol represented by the general formula (2) is sequentially reacted with undecenol at one end of the alpha, omega-dihaloalkane represented by the general formula (1) And is synthesized to be represented by the formula (3) having an ether bond,

Formula 1

X- (R) -X

In the above R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or (CH _{2) 3} -O- (CH _{2) 6 -O- (CH 2)} 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O- (CH 2) 6 -O- (CH ₂ ) ₆ , (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is Cl, Br or I,

(2)

Me- (OCH ₂ CH ₂₎ mOH

M is 1 or 3,

(3)

And in which m is 1, 2 or 3, n is 0 or 1, R is R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6 In the above, ( _{CH 2) 8, (CH 2} ) 10 or _{(CH 2) 3 -O- (CH} 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- ( _{CH 2) 8, (CH 2} ) 6 -O- (CH 2) 6 -O- (CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X Is Cl, Br or I,

Wherein the compound of formula (3) is synthesized by using tetrabutylammonium chloride or tetrabutylammonium bromide as a catalyst in a methoxyethyl chloride and undecenol DME solution and KOH as a base, wherein the hydrophilic group and the lipophilic group are simultaneously substituted There is provided a method for producing a silicone binder for a fingerprint-preventing coating film.

According to another preferred embodiment of the present invention, the compound of formula (III) is synthesized with a compound represented by formula (4) or (5) by hydrogen silylation reaction with trichlorosilane under a platinum catalyst,

Formula 4

Formula 5

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O (CH ₂ ) ₆ -O- (CH ₂ ) ₆ , (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ and X is Cl, Br or I. There is provided a process for producing a silicone binder for a fingerprint antistatic coating film in which a hydrophilic group and a lipophilic group are simultaneously substituted.

According to another preferred embodiment of the present invention, there is provided a method for producing a silicone binder for a fingerprint appearance preventing coating, wherein the temperature of the double reaction is from room temperature to 200 DEG C, wherein the hydrophilic group and the lipophilic group are simultaneously substituted.

According to another preferred embodiment of the present invention, there is provided a process for producing a silicone binder for a fingerprint appearance preventing coating, wherein the hydrophilic group and the lipophilic group are simultaneously substituted, wherein the reaction solvent is hexane, toluene or THF.

According to another preferred embodiment of the present invention, there is provided a process for preparing a silicone binder for a fingerprint appearance preventing coating, wherein the hydrophilic group and the lipophilic group are simultaneously substituted, wherein the reaction proceeds without a reaction solvent.

In the present invention, instead of reacting methoxyethanol or undecenol with metal sodium to form an anion, tetrabutylammonium bromide is used as a catalyst to form an anion with KOH and reacted with an alkyl halide to form an ether bond Which is economically inexpensive and reduces risk. With this method, various alkyl undecene substituted methoxyethoxy groups can be obtained, which is advantageous for mass production. In this process, two trichlorosilyl groups are added to the alkyl undecene in the step of double-cyclization with trichlorosilane in the presence of tetrabutylphosphonium catalyst, and by-products in which only one trichlorosilyl group is added as a by-product are simultaneously obtained. This trichlorosilyl group reacts with an alcohol to give the corresponding trialkoxysilane. Compounds in which two trialkoxysilyl groups are substituted are an improved method because they have a stronger adhesion to the coated substrate and a lower rate of abrasion compared to a single substituted compound.

Hereinafter, the present invention will be described in detail with reference to exemplary embodiments, but the present invention is not limited thereto.

According to the present invention, there is provided a compound represented by formula (3)

(3)

And in which m is 1, 2 or 3, n is 0 or 1, R is R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6 In the above, ( _{CH 2) 8, (CH 2} ) 10 or _{(CH 2) 3 -O- (CH} 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- ( _{CH 2) 8, (CH 2} ) 6 -O- (CH 2) 6 -O- (CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X Cl < / RTI >

The compound represented by the general formula (3)

(a) As shown in Scheme 1 below, tetrabutylammonium bromide, KOH, and alpha, omega-dihaloalkane, which are catalysts, are added to DME solution to react undecenol to produce haloalkoxy undecene Synthesizing;

Formula 1

X- (R) -X

In the above R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or (CH _{2) 3} -O- (CH _{2) 6 -O- (CH 2)} 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O- (CH 2) 6 -O- (CH ₂ ) ₆ , (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is Cl, Br or I,

Scheme 1

(b) synthesizing methoxyethoxyalkylene undecene by reacting methoxyethanol represented by the formula (2) with tetrabutylammonium bromide, KOH and haloalkoxydecene as catalysts in a DME solution;

(2)

Me- (OCH ₂ CH ₂₎ mOH

M is 1 or 3,

(3)

And in which m is 1, 2 or 3, n is 0 or 1, R is R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6 In the above, ( _{CH 2) 8, (CH 2} ) 10 or _{(CH 2) 3 -O- (CH} 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- ( _{CH 2) 8, (CH 2} ) 6 -O- (CH 2) 6 -O- (CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X Is Cl, Br or I,

Scheme 2

(c) reacting the alkoxyalkyl undecene represented by the formula (3) with trichlorosilane under a tetrabutyl phosphonium chloride catalyst to obtain a trichlorosilane-added compound represented by the formula (4) and a double- step.

Formula 4

Formula 5

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O _{- (CH 2) 6 -O- (} CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X is a Cl, Br or I.

It has been found by the Applicant that when a compound having a double bond is reacted with trichlorosilane using tetrabutylphosphonium chloride as a catalyst, two silyl groups are added to the double bond (IN Jung et al, Organometallics, 2006, 25 , 318). In this reaction, a hydrogen-scylated compound having only one silyl group as a by-product in addition to the double-quenched compound is obtained. The reaction temperature is 180 ° C, which is much higher than the distillation point of trichlorosilane. Therefore, the reaction can be carried out smoothly by using a pressurizing device. As shown in Formula 3, the unsaturated bond of carbon and carbon can be added by a hydrogen silylation reaction of a silane having a Si-H bond, and a platinum compound is widely used as a catalyst. This method is used when only Compound 4 is desired to be synthesized except Compound 5. If the compound of formula (3) has a high boiling point and a fast hydrosilylation reaction, the reaction can proceed at normal pressure, which can be represented by the following reaction formula (3).

Scheme 3

Alkoxyalkyldecylchlorosilanes represented by Formulas (4) and (5) may be reacted with an alcohol to synthesize alkoxysilanes represented by Formulas (6) and (7).

6

Formula 7

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10 or ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O _{- (CH 2) 6 -O- (} CH 2) 6, (CH 2) 3 -O- (CH 2) 10 -O- (CH 2) 3, X is a Cl, Br or I, R1 is carbon Is an alkyl group of 1 to 3 carbon atoms.

Chlorosilanes react with alcohols to generate hydrogen chloride and convert to alkoxysilane. When amine is used, ammonium chloride salt is formed, so it is easy to complete the reaction and the by-product salt can be dried. According to the present invention, an organic undecene having a polyether bonded to a hydrophilic group can be synthesized, and an organosilane having an undecyl group, which is a lipophilic group having a hydrophilic group, alkoxy alcohol or polyether group bonded in one molecule, can be produced.

An example of the compound of formula (1) is as follows. Dichlorobutane, 1-bromo-4-chlorobutane, 1,6-dichlorohexane, 1,6-dichlorohexane, Dibromohexane, 1,6-diiodohexane, 1,8-dichlorooctane, 1,10-dichlorodecane, 1,10-dibromodecane, all commercialized materials, According to the technology provided by the invention, tetrabutylammonium bromide in a DME solvent can be synthesized by removing KCl from an alkane diol and a dichloroalkane with KOH and forming an ether bond. Specifically, _{Cl (CH 2) 3 -O- (} CH 2) 6 -O- (CH 2) 3 Cl was synthesized by the reaction of 1,6-hexanediol and 1,3-dichloropropane, Cl (CH _{2) 8} -O- (CH ₂ ) ₆ -O- (CH ₂ ) ₈ Cl was synthesized by the reaction of 1,6-hexanediol with 1,8-dichlorooctane and was synthesized by the reaction of Cl (CH ₂ ) ₆ -O- (CH _{2 ) 6 -O- (CH 2) 6} Cl was synthesized by the reaction of 1,6-hexanediol and 1,6-dichloro _{hexane, Cl (CH 2) 8 -O-} (CH 2) 6 -O- (CH _{2) 8} Cl was synthesized by the reaction of 1,6-hexanediol and _{1,8-dichloro-octane, Cl (CH 2) 3 -O-} (CH 2) 10 -O- (CH 2) 3 Cl is 1, It was easily synthesized by the reaction of 10-decanediol with 1,3-dichloropropane.

The present invention will be described in more detail as follows. In the course of the reaction, it is advantageous to use a polar solvent because KOH anions the alcohol and the organic compounds substituted with halogens undergo nucleophilic substitution reaction. A solvent such as DME may be used. Since the reaction between the alcohol and the halogen-substituted organic compound takes place between 50 and 100 ° C, it is not necessary to apply pressure and the reaction can be performed at normal pressure. In this reaction, potassium halide is formed as a by-product and becomes a solid. The container to be used for the reaction of the present invention may be a glass-coated container or a container made of stainless steel.

The double-normalization reaction for addition to various organic compounds can be carried out in a reaction vessel equipped with a pressurizing apparatus usually used in a laboratory. The reaction apparatus may be a device capable of slowly injecting the raw material under an inert gas, and may be a device capable of heating or cooling with an agitator. Since the breaking point of trichlorosilane is low, it is necessary to apply pressure to the reaction tank. However, this reaction process does not depend on the apparatus or the reaction pressure. Solvents may be used in the course of the reaction, but most can be done without the use of solvents. A typical synthesis process is carried out by slowly introducing an organic compound having an unsaturated bond in an inert gas into a reaction vessel containing chlorosilane and a catalyst. In some cases, the order of injection of chlorosilanes and organic compounds can be changed. Some reactions are considerable exothermic reactions and can be refluxed without heating from the outside by controlling the injection rate of chlorosilane. After the injection of chlorosilane is completed, stirring may be performed for a predetermined time to complete the reaction. When the reaction is completed, the solution is fractionally distilled to recover the product.

An embodiment according to the present invention will be described below.

Example 1: Synthesis of 11- (2-methoxyethoxy) undecene

A 5000 ml three-necked flask was equipped with a condenser and a mechanical stirrer. 2 L of dimethoxyethane, 1581.6 g (2 mol) of potassium hydroxide, 2400 g (1 mol) of undecene alcohol and 681.5 g (2 mol) of tetrabutylammonium bromide were placed in a flask and stirred with a mechanical stirrer and methoxyethyl chloride 2664 g (2 mol) was slowly added via a dropping funnel. The solution was stirred at 85 ° C on a mechanical stirrer and further reacted for 16 hours. The mixture was cooled to room temperature, filtered, and then distilled under reduced pressure to remove starting materials. Hydrochloric acid was added to this solution to remove tributylamine from the byproduct, water was added, and the organic layer was separated using a separatory funnel, followed by removing water with MgSO ₄ and filtering. This solution was subjected to vacuum distillation to obtain 2177.6 g (9.54 mol, yield 68.1%) of 11- (2-methoxyethoxy) -1-undecene. The obtained product 300 MHz 1H magnetic resonance analysis, 1.25 ppm (s, 12H) in _{CH 2 = CHCH 2 (CH 2} ) 6 CH 2 CH 2 O, 1.57 ppm (m, 2H) from the CH ₂ CH ₂ CH ₂ O, 2.05 ppm (m, 2H ) from the _{CH 2 = CH CH 2, 3.39} ppm (s, 3H) from _{OCH 3, 3.45 ppm (t,} 2H) in _{CH 2 CH 2 CH 2 O,} 3.55 ppm (m, 4H ) from _{OCH 2 CH 2 OCH 3, 4.95} ppm (d, 1H) in _{HtransHcisC = CHCH 2, 5.10 ppm (} d, 1H) CH at _{HtransHcisC = CHCH 2, 5.80 ppm (} ddt, 1H) in ₂ = CH CH _2, The peak was confirmed.

Example 2: Synthesis of 11- (2-methoxyethoxy) undecyltrichlorosilane

A 5000 mL flask was equipped with a condenser and a magnetic stirrer, and nitrogen was passed through the end of the condenser, so that the entire apparatus was kept under a nitrogen atmosphere. 2177.6 g of 11- (2-methoxyethoxy) (9.54 mol) and 100 ppm of the total weight of the reaction product were placed in a flask, and 1937.4 g (14.3 mol) of trichlorosilane was slowly added thereto through a dropping funnel while stirring. This solution was stirred at 85 ° C for 3 hours to complete the reaction and 2856 g (7.79 mol, yield 81.7%) of 11- (2-methoxyethoxy) undecyltrichlorosilane was obtained by distillation under reduced pressure. The obtained product 300 MHz 1H magnetic resonance analysis, 1.36 ppm (m, 14H) from _{OCH 2 CH 2 - (CH 2} ) 7 -CH 2, 1.41 ppm (t, 2H) Si- CH 2, 1.57 ppm in the ( _{CH 2, 3.39 ppm (s,} 3H) Me OCH 2 CH 2 O-, was confirmed OCH ₂ CH ₂ -O, peaks at 3.44 ppm (m, 4H) in - m, 2H) SiCH ₂ in.

Example 3: Synthesis of 11- (2-methoxyethoxy) undecyltrimethoxysilane

A 5000 ml three-necked flask was equipped with a condenser and a mechanical stirrer, allowing the dried nitrogen to pass through the end of the condenser so that the entire apparatus was kept under a nitrogen atmosphere. To the flask was added 1066.5 g (2.91 mol) of 11- (2-methoxyethoxy) undecyltrichlorosilane, 1L of n-hexane, and stirred vigorously with a mechanical stirrer, and 419.2 g (13.08 mol) of methanol was added dropwise The mixture was put through a funnel and stirred at room temperature for 30 minutes. Triethylamine was added to the solution to precipitate the precipitate, and then the consumption of the starting material and the product were confirmed by gas chromatography. The reaction product was filtered and vacuum distilled to obtain 913.6 g (2.61 mol, yield 89.7%) of 11- (2-methoxyethoxy) undecyltrimethoxysilane. The obtained product 300 MHz 1H magnetic resonance analysis, 0.63 ppm (m, 2H) OCH 2 CH 2 in the _{Si- CH 2, 1.25 ppm (m} , 14H) in the _{- (CH 2) 7 -CH 2} , 1.40 ppm ( _{CH 2, 1.58 ppm (m,} 2H) from _{OCH 2 - - CH 2 -CH 2} , 3.38 ppm (s, 3H) CH 2 -O- CH 3, 3.44 ppm (m, 2H at m, 2H) SiCH ₂ from _{) MeOCH 2 CH 2 O- CH 2} , 3.54 ppm (m, 4H) O- CH 2 CH 2 -O, it was confirmed to 3.55 ppm (s, 9H) Si -O CH 3, peak in.

Example 4: Synthesis of 11- (6-chlorohexyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 910.3 g (5.87 mol) of dichlorohexane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1 and stirred with a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 501 g (1.73 mol, yield 59.8%) of 11- (6-chlorohexyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) Cl from _{O- CH 2 -C, 3.52 ppm (} m, 2H) from - CH ₂ -C was, confirmed that C- CH = C, peaks at 4.96 ppm (t, 2H) C = CH 2, 5.81 ppm (m, 1H) in.

Example 5: Synthesis of 11- (10-chlorodecyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 1239.6 g (5.87 mol) of dichlorodecane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1 and stirred with a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 601.3 g (1.74 mol, yield 60.1%) of 11- (10-chlorodecyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO, 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) at 1.3 ppm (m, 22H) _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 6: Synthesis of 11- (6-bromohexyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 1380 g (5.87 mol) of dibromohexane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1, 500 g (2.9 mol) of undecene alcohol was poured into the flask through a dropping funnel and reacted to obtain 527 g (1.58 mol, yield: 54.5%) of 11- (6-bromohexyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 1.33 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) _{Br-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.15 ppm (t, 2H) O in _{Br- CH 2 -C, 3.38 ppm (} t, 4H) from - CH ₂ -C was, confirmed that C- CH = C, peaks at 4.96 ppm (t, 2H) C = CH 2, 5.81 ppm (m, 1H) in.

Example 7 Synthesis of 11- (8-chlorooctyloxy) undecene

In the same manner as in Example 1, 500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 1074.9 g (5.87 mol) of dichlorooctane and 142 g (0.44 mol) of tetrabutylammonium bromide were poured into a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 531.3 g (1.67 mol, yield: 57.8%) of 11- (8-chlorooctyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 8: Synthesis of 11- (5-chloropentyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 827.9 g (5.87 mol) of dichloropentane and 142 g (0.44 mol) of tetrabutylammonium bromide were placed in a manner similar to that of Example 1 and stirred with a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 497.5 g (1.81 mol, yield 62.5%) of 11- (5-chloropentyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO, 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) at 1.3 ppm _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) O- CH 2 -C, Cl at 3.52ppm (t, 2H) from C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -C.

Example 9: Synthesis of 11- (4-chlorobutoxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 745.5 g (5.87 mol) of dichlorobutane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1 and stirred with a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 453.9 g (1.74 mol, yield 60.1%) of 11- (4-chlorobutoxy) undecene. The obtained product was analyzed by C- CH ₂ -CO, 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) at 1.3 ppm _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 10: Synthesis of 11- (3-chloropropoxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 663.3 g (5.87 mol) of dichloropropane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1 and stirred with a mechanical stirrer 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 466.5 g (1.89 mol, yield 65.2%) of 11- (3-chloropropoxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 4H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 11 Synthesis of 11- (3-bromopropoxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 663.3 g (5.87 mol) of dibromopropane and 142 g (0.44 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1, 500 g (2.9 mol) of undecene alcohol was poured through a dropping funnel and reacted to obtain 466.5 g (1.89 mol, yield 65.2%) of 11- (3-bromopropoxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 1.33 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 4H) _{Br-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.15 ppm (t, 2H) O in _{Br- CH 2 -C, 3.38 ppm (} t, 4H) from - CH ₂ -C was, confirmed that C- CH = C, peaks at 4.96 ppm (t, 2H) C = CH 2, 5.81 ppm (m, 1H) in.

Example 12: Synthesis of 11- (3- (6- (3-chloropropoxy) hexyloxy) propoxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 1592.1 g (5.87 mol) of 1,6-bis (3-chloropropoxy) hexane and 142 g of tetrabutylammonium bromide (3-chloropropoxy) hexyloxy) propoxy) -phenol (0.44 mol) was added thereto, and the mixture was stirred with a mechanical stirrer and 500 g (2.9 mol) of undecene alcohol was added thereto through a dropping funnel. 603.5 g (1.49 mol, yield: 51.5%) of undecene was obtained. The obtained product was analyzed by C- CH ₂ -CO, 1.63 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm _{OC- CH 2 -CO, 1.75 ppm (} m, 2H) from the _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, O at 3.38 ppm (t, 12H) in _{- CH 2 -C, 3.52 ppm (} t, 2H) from _{Cl- CH 2 -C, 4.96 ppm (} m, 2H) from the C- CH = C, peaks in the _{C = CH 2, 5.81 ppm (} m, 1H) Respectively.

Example 13: Synthesis of 11- (8- (6- (8-chlorooctyloxy) hexyloxy) octyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 2415.4 g (5.87 mol) of 1,6-bis (8-chlorooctyloxy) hexane and 142 g of tetrabutylammonium bromide 0.44 mol) was added thereto, and the mixture was stirred with a mechanical stirrer. 500 g (2.9 mol) of undecene alcohol was placed in a dropping funnel and reacted to obtain 11- (8- (6- (8- chlorooctyloxy) hexyloxy) octyloxy) 818 g (1.5 mol, yield: 53.8%) of cesium was obtained. The obtained product was analyzed by C- CH ₂ -CO at 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 12H) at 1.3 ppm _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 12H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 14: Synthesis of 11- (6- (6- (6-chlorohexyloxy) hexyloxy) hexyloxy) undecene

500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 2086.14 g (5.87 mol) of 1,6-bis (6-chlorohexyloxy) g (0.44 mol), and 500 g of undecene alcohol (2.9 mol) was added to the mixture through a dropping funnel. The mixture was reacted to obtain 11- (3- (6- (3-chlorohexyloxy) hexyloxy) hex 733.8 g (1.5 mol, yield 51.8%) of siloxylundecene was obtained. The obtained product was analyzed by C- CH ₂ -CO, 1.75 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 12H) at 1.3 ppm (m, 24H) _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, 3.38 ppm (t, 12H) Cl from _{O- CH 2 -C, 3.52 ppm (} t, 2H) from _{- CH 2 -C, C- CH =} C, it was confirmed a peak in the _{C = CH 2, 5.81 ppm (} m, 1H) at 4.96 ppm (m, 2H).

Example 15: Synthesis of 11- (3- (10- (3-chloropropoxy) desilyloxy) propoxy) undecene

In the same manner as in Example 1, 500 ml of dimethoxyethane, 329.5 g (5.87 mol) of potassium hydroxide, 1921.4 g (5.87 mol) of 1,10-bis (3-chloropropoxy) decane, 142 g of tetrabutylammonium bromide (3- (10- (3-chloropropoxy) desilyloxy) propoxy) -phenol (0.44 mol) was added to the reaction mixture and stirred with a mechanical stirrer. 500 g (2.9 mol) of undecene alcohol was added thereto through a dropping funnel. 682.5 g (1.48 mol, yield 51%) of undecene was obtained. The obtained product was analyzed by C- CH ₂ -CO, 1.63 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm (m, 24H) _{OC- CH 2 -CO, 1.75 ppm (} m, 2H) from the _{Cl-C- CH 2 -C, 2.01} ppm (m, 2H) C- CH 2 -C = C, O at 3.38 ppm (t, 12H) in _{- CH 2 -C, 3.52ppm (t} , 2H) CH = C- to C, a peak from _{Cl- CH 2 -C, 4.96 ppm (} m, 2H) C = CH 2, 5.81 ppm (m, 1H) from Respectively.

Example 16: Synthesis of 11- (6- (2-methoxyethoxy) hexyloxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 177 g (3.16 mol) of potassium hydroxide, 527 g (1.58 mol) of 11- (6-bromohexyloxy) undecene, 101.8 g of tetrabutylammonium bromide 0.32 mol) was added thereto and stirred with a mechanical stirrer. 241 g (2.9 mol) of 2-methoxyethanol was put in a dropping funnel and reacted to obtain 316 g of 11- (6- (2-methoxyethoxy) hexyloxy) undecene (0.96 mol, yield 60.8%). The obtained product was analyzed by C- CH ₂ -CO at 2.03 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm in _{C- CH 2 -C = C, 3.38} ppm (s, 3H) O- CH 2 -C, 3.57 ppm (s, 4H) from _{O- CH 3, 3.45 ppm (t} , 6H) from O- CH ₂ - C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -O.

Example 17: Synthesis of 11- (10- (2-methoxyethoxy) disiloxy) undecene

In the same manner as in Example 1, 100 ml of dimethoxyethane, 67 g (1.2 mol) of potassium hydroxide, 208 g (0.6 mol) of 11- (10- chlorodecyloxy) undecene, 58 g of tetrabutylammonium bromide 0.18 mol) was added thereto and stirred with a mechanical stirrer. 91 g (1.2 mol) of 2-methoxyethanol was placed in a dropping funnel and reacted to obtain 160 g of 11- (10- (2- methoxyethoxy) disiloxy) undecene (0.41 mol, yield 69.3%). The obtained product was analyzed by C- CH ₂ -CO at 2.03 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm (m, 24H) in _{C- CH 2 -C = C, 3.38} ppm (s, 3H) O- CH 2 -C, 3.57 ppm (s, 4H) from _{O- CH 3, 3.45 ppm (t} , 6H) from O- CH ₂ - C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -O.

Example 18: Synthesis of 11- (8- (3-methoxypropoxy) octyloxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 380.3 g (1.2 mol) of 11- (8-chlorooctyloxy) undecene, 116.1 g of tetrabutylammonium bromide and 216.3 g (2.4 mol) of 3-methoxypropanol were placed in a dropping funnel and reacted to obtain 270.6 g (0.73 mol) of 11- (8-methoxypropoxy) octyloxy) undecene mol, yield: 61.1%). The obtained product was analyzed by C- CH ₂ -CO, 1.63 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm _{OC- CH 2 -CO, 2.01 ppm (} m, 2H) O- CH at _{C- CH 2 -C = C, 3.38ppm} (s, 3H) O- CH 3, 3.45 ppm (t, 10H) in _2- C, CH = C, peak at C = CH ₂ , 5.81 ppm (m, 1H) at 4.96 ppm (m, 2H).

Example 19: Synthesis of 11- (5- (1-methoxymethoxy) pentyloxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 329.8 g (1.2 mol) of 11- (5-chloropentyloxy) undecene, 116.1 g of tetrabutylammonium bromide and the mixture was stirred with a mechanical stirrer. 149 g (2.4 mol) of methoxymethanol was placed in a dropping funnel and reacted to obtain 234.4 g (0.78 mol, 1 mol) of 11- (5- (2- methoxymethoxy) pentyloxy) Yield: 64.9%). The obtained product 300MHz 1H magnetic resonance analysis, 1.3 ppm (m, 14H) C- CH 2 -C, 1.53 ppm (m, 9H) C- CH 2 -CO, 2.01 ppm (m, 2H) C on the in _{- CH 2 -C = C, 3.38} ppm (s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 4.96 ppm (} m, 2H) from the C = CH _2, 5.45 ppm (s, 2H) C- CH = C, it was confirmed a peak at a _{O- CH 2 -O, 5.81 ppm (} m, 1H) in.

Example 20: Synthesis of 11- (4- (2-methoxyethoxy) butoxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 313 g (1.2 mol) of 11- (4-chlorobutoxy) undecene, 116.1 g of tetrabutylammonium bromide The reaction mixture was stirred with a mechanical stirrer and 182.6 g (2.4 mol) of 2-methoxyethanol was added thereto through a dropping funnel and reacted to obtain 228.4 g of 11- (4- (2-methoxyethoxy) butoxy) undecene 0.76 mol, yield: 63%). The obtained product was analyzed by C- CH ₂ -CO at 2.03 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm in _{C- CH 2 -C = C, 3.38} ppm (s, 3H) O- CH 2 -C, 3.57 ppm (s, 4H) from _{O- CH 3, 3.45 ppm (t} , 6H) from O- CH ₂ - C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -O.

Example 21: Synthesis of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 486.1 g of 11- (3- (6- (3-chloropropoxy) hexyloxy) propoxy) undecene (1.2 mol) of tetrabutylammonium bromide and 116.1 g (0.36 mol) of tetrabutylammonium bromide were placed and stirred with a mechanical stirrer. 182.6 g (2.4 mol) of 2-methoxyethanol was placed in a dropping funnel and reacted to obtain 11- (3- 324.6 g (0.73 mol, yield: 61.1%) of 3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecene was obtained. The obtained product was analyzed by C- CH ₂ -CO at 1.33 ppm (m, 4H) at C- CH ₂ -C, 1.53 ppm (m, 9H) in _{OC- CH 2 -CO, 2.01 ppm (} m, 2H) C- CH 2 -C = C, 3.38 ppm (s, 3H) O- CH 3, 3.45 ppm (t, 14H) from O- CH ₂ - C, 3.57 ppm (s, 4H ) from _{O- CH 2 - CH 2 -O,} 4.96 ppm (m, 2H) from the check C- CH = C, peaks in the _{C = CH 2, 5.81ppm (m} , 1H) Respectively.

Example 22: Synthesis of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 654.4 g of 11- (8- (6- (8-chlorooctyloxy) hexyloxy) octyloxy) undecene (1.2 mol) of tetrabutylammonium bromide and 116.1 g (0.36 mol) of tetrabutylammonium bromide. The mixture was stirred with a mechanical stirrer and 182.6 g (2.4 mol) of 2-methoxyethanol was added thereto through a dropping funnel. To obtain 391.9 g (0.67 mol, yield 55.5%) of 8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecene. The obtained product was analyzed by C- CH ₂ -CO at 2.03 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 14H) at 1.3 ppm in _{C- CH 2 -C = C, 3.38} ppm (s, 3H) O- CH 2 -C, 3.57 ppm (s, 4H) from _{O- CH 3, 3.45 ppm (t} , 14H) from O- CH ₂ - C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -O.

Example 23 Synthesis of 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g of potassium hydroxide (2.4 mol), 11- (6- (6- (6-chlorohexyloxy) hexyloxy) hexyloxy) undecene (2-methoxyethanol) (182.6 g, 2.4 mol) was added thereto through a dropping funnel and reacted to obtain 11- (6- (6-chloropyrimidin- - (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecene was obtained in an amount of 375.5 g (0.71 mol, yield 58.9%). The obtained product was analyzed by C- CH ₂ -CO at 2.03 ppm (m, 2H) at C- CH ₂ -C, 1.53 ppm (m, 14H) at 1.3 ppm in _{C- CH 2 -C = C, 3.38} ppm (s, 3H) O- CH 2 -C, 3.57 ppm (s, 4H) from _{O- CH 3, 3.45 ppm (t} , 14H) from O- CH ₂ - C- CH = C, peak at C = CH ₂ at 5.96 ppm (m, 2H) and 5.81 ppm (m, 1H) at CH ₂ -O.

Example 24: Synthesis of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecene

In the same manner as in Example 1, 250 ml of dimethoxyethane, 134.7 g (2.4 mol) of potassium hydroxide, 553.4 g of 11- (3- (10- (3- chloropropoxy) disiloxy) propoxy) undecene (1.2 mol) of tetrabutylammonium bromide and 116.1 g (0.36 mol) of tetrabutylammonium bromide were placed and stirred with a mechanical stirrer. 182.6 g (2.4 mol) of 2-methoxyethanol was placed in a dropping funnel and reacted to obtain 11- To obtain 360.6 g (0.72 mol, yield 60%) of 3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecene. The obtained product was analyzed by C- CH ₂ -CO, 1.63 ppm (m, 4H) at C- CH ₂ -C, 1.53 ppm (m, 6H) at 1.3 ppm (m, 12H) in _{OC- CH 2 -CO, 2.01 ppm (} m, 2H) C- CH 2 -C = C, 3.38 ppm (s, 3H) O- CH 3, 3.45 ppm (t, 14H) from O- CH ₂ - C, 3.57 ppm (s, 4H ) from _{O- CH 2 - CH 2 -O,} 4.96 ppm (m, 2H) from the check C- CH = C, peaks in the _{C = CH 2, 5.81 ppm (} m, 1H) Respectively.

Example 25: Synthesis of 11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane

In the same manner as in Example 2, 296 g (0.9 mol) of 11- (6- (2-methoxyethoxy) hexyloxy) undecene, 244 g (1.8 mol) of Spiria catalyst and trichlorosilane were added, 280 g (0.6 mol, yield 67%) of 11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane was obtained by distillation. The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 20H) from _{C- CH 2 -C, 1.46 ppm (} t, 2H) Si- CH 2 -C, 1.53 ppm (m, 6H) in _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.57 ppm (} s, 4H) O- CH 2 in the - CH ₂ -O and peak were confirmed.

Example 26: Synthesis of 11- (10- (2-methoxyethoxy) decyloxy) undecyltrichlorosilane

180 g (0.46 mol) of 11- (10- (2-methoxyethoxy) disiloxy) undecene, 126.7 g (0.93 mol) of Spiria catalyst and trichlorosilane were placed in the same manner as in Example 2, 177 g (0.34 mol, yield 74%) of 11- (10- (2-methoxyethoxy) disiloxy) undecyltrichlorosilane was obtained by distillation. The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 28H) from _{C- CH 2 -C, 1.46 ppm (} t, 2H) Si- CH 2 -C, 1.53 ppm (m, 6H) in _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.57 ppm (} s, 4H) O- CH 2 in the - CH ₂ -O and peak were confirmed.

Example 27: Synthesis of 11- (8- (3-methoxypropoxy) octyloxy) undecyltrichlorosilane

333.5 g (0.9 mol) of 11- (8- (3-methoxypropoxy) octyloxy) undecene, 324 g (1.8 mol) of Spiria catalyst and trichlorosilane were charged in the same manner as in Example 2, 313.8 g (0.62 mol, yield 68.8%) of 11- (8- (3-methoxypropoxy) octyloxy) undecyltrichlorosilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy and found to be Si- CH ₂ -C, 1.53 ppm (m, 6H) at C- CH ₂ -C at 1.33 ppm (m, 24H) _{C- CH 2 -CO, 1.63 ppm (} m, 2H) from the _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 10H) in, The peak was confirmed.

Example 28: Synthesis of 11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane

270.4 g (0.9 mol) of 11- (5- (1-methoxymethoxy) pentyloxy) undecene and 244 g (1.8 mol) of trichlorosilane were charged in the same manner as in Example 2, 279 g (0.64 mol, yield 71.1%) of 11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy. The results were as follows: Si- CH ₂ -C, 1.53 ppm (m, 6H) at C- CH ₂ -C at 1.33 ppm (m, 18H) _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -O from _{O- CH 2 -C, 5.45 ppm (} s, 2H) from _{O- CH 3, 3.45 ppm (t} , 6H) at, The peak was confirmed.

Example 29: Synthesis of 11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane

270.4 g (0.9 mol) of 11- (5- (2-methoxyethoxy) butoxy) undecene and 244 g (1.8 mol) of trichlorosilane were charged in the same manner as in Example 2, 274.6 g (0.63 mol, yield 70%) of 11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy. The results were as follows: Si- CH ₂ -C, 1.53 ppm (m, 4H) at C- CH ₂ -C at 1.33 ppm (m, 16H) _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.57 ppm (} s, 4H) O- CH 2 in the - CH ₂ -O and peak were confirmed.

Example 30: Synthesis of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrichlorosilane

400.2 g (0.9 mol) of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecene was obtained in the same manner as in Example 2, 244 g (1.8 mol) of silane was reacted to obtain 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrichlorosilane 330.7 g (0.57 mol, yield 63.5%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 20H) from _{C- CH 2 -C, 1.46 ppm (} t, 2H) Si- CH 2 -C, 1.53 ppm (m, 6H) in _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 14H) in, O- CH ₂ -CH ₂ -O, peak was confirmed at 3.57 ppm (s, 4H).

Example 31: Synthesis of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyl trichlorosilane

526.5 g (0.9 mol) of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecene was obtained in the same manner as in Example 2, 244 g (1.8 mol) of silane was added and reacted to obtain 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyltrichlorosilane 417.8 g (0.58 mol, yield 64.2%). The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy and found to be Si- CH ₂ -C, 1.53 ppm (m, 14H) at C- CH ₂ -C at 1.33 ppm (m, 36H) _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) from _{O- CH 2 -C, 3.57 ppm (} s, 4H) O- CH 2 in the - CH ₂ -O and peak were confirmed.

Example 32: Synthesis of 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyl trichlorosilane

476 g (0.9 mol) of 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy undecene, Spire catalyst, 244 g (1.8 mol) of trichlorosilane was added to the reaction mixture and the mixture was reacted under reduced pressure to obtain 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyl 418.5 g (0.63 mol, yield 69.7%) of trichlorosilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy. The results were as follows: C- CH ₂ -C at 1.3 ppm (m, 28H), Si- CH ₂ -C at 1.54 ppm (t, 2H) _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) from _{O- CH 2 -C, 3.57 ppm (} s, 4H) O- CH 2 in the - CH ₂ -O and peak were confirmed.

Example 33: Synthesis of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrichlorosilane

450.7 g (0.9 mol) of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecene was obtained in the same manner as in Example 2, 244 g (1.8 mol) of silane was reacted to obtain 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrichlorosilane 356.3 g (0.56 mol, yield 62.7%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 28H) from _{C- CH 2 -C, 1.46 ppm (} t, 2H) Si- CH 2 -C, 1.53 ppm (m, 6H) in _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 14H) in, O- CH ₂ -CH ₂ -O, peak was confirmed at 3.57 ppm (s, 4H).

Example 34: Synthesis of 2- (trichlorosilyl) -11- (2-methoxyethoxy) undecyltrichlorosilane

22.8 g (0.1 mol) of 11- (2-methoxyethoxy) undecene, 54.18 g (0.4 mol) of trichlorosilane, 0.2 g of tetrabutylphosphonium chloride (0.1 mol) were placed in a 300 ml stainless steel high- 3 g (0.01 mol) of chloride were added and reacted at 180 ° C for 16 hours. The solution was poured into a round bottom flask, and n-hexane was added to the catalyst. The catalyst was removed, and 20.4 g (0.041 mol, 0.25 mol) of 2- (trichlorosilyl) Yield: 41%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 14H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 2H) from the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 2H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 35: Synthesis of 2- (trichlorosilyl) -11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane

32.9 g (0.1 mol) of 11- (6- (2-methoxyethoxy) hexyloxy) undecene, 54.18 g (0.4 mol) of trichlorosilane and 3 g of tetrabutylphosphonium chloride in the same manner as in Example 34 (0.045 mol, 45% yield) of 2- (trichlorosilyl) -11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane was obtained . The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy. The results were as follows: C- CH ₂ -C at 1.3 ppm (m, 18H), Si- CH ₂ -C at 1.54 ppm (d, 2H) Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 36: Synthesis of 2- (trichlorosilyl) -11- (10- (2-methoxyethoxy) decyloxy) undecyltrichlorosilane

38.5 g (0.1 mol) of 11- (10- (2-methoxyethoxy) disiloxy) undecene, 54.18 g (0.4 mol) of trichlorosilane and 3 g of tetrabutylphosphonium chloride in the same manner as in Example 34 (0.041 mol, yield 40.8%) of 2- (trichlorosilyl) -11- (10- (2-methoxyethoxy) disiloxyl) undecyltrichlorosilane was obtained . The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 26H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 37: Synthesis of 2- (trichlorosilyl) -11- (8- (3-methoxypropoxy) octyloxy) undecyltrichlorosilane

37.1 g (0.1 mol) of 11- (8- (3-methoxypropoxy) octyloxy) undecene, 54.18 g of trichlorosilane (0.4 mol) and 3 g of tetrabutylphosphonium chloride 0.01 mol) was added and reacted to obtain 26.2 g (0.041 mol, 41% yield) of 2- (trichlorosilyl) -11- (8- (3- methoxypropoxy) octyloxy) undecyltrichlorosilane. The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 22H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 1.63 ppm (} m, 2H) from the _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the in ppm (t, 10H) O- CH 2 -C was, confirmed that the peak.

Example 38: Synthesis of 2- (trichlorosilyl) -11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane

(0.1 mol) of 11- (5- (1-methoxymethoxy) pentyloxy) undecene, 54.18 g (0.4 mol) of trichlorosilane and 3 g of tetrabutylphosphonium chloride in the same manner as in Example 34 (0.01 mol) was added and reacted to obtain 26.7 g (0.047 mol, yield: 47.1%) of 2- (trichlorosilyl) -11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane. The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 16H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 10H) O- CH 2 -C, 5.45 in in ppm (s, 2H) O- CH 2 was -O, determine the peak.

Example 39: Synthesis of 2- (trichlorosilyl) -11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane

30.1 g (0.1 mol) of 11- (4- (2-methoxyethoxy) butoxy) undecene, 54.18 g (0.4 mol) of trichlorosilane and 3 g of tetrabutylphosphonium chloride in the same manner as in Example 34 (0.043 mol, 43% yield) of 2- (trichlorosilyl) -11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane was obtained. The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 14H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 40: Synthesis of 2- (trichlorosilyl) -11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrichlorosilane

44.5 g (0.1 mol) of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecene was obtained in the same manner as in Example 34, 54.18 g of trichlorosilane (Trichlorosilyl) -11- (3- (6- (3- (2-methoxyethoxy) propoxy) -1,3,4-tetrahydroisoquinoline (0.4 mol) and tetrabutylphosphonium chloride (3 g ) Hexyloxy) propoxy) undecyl trichlorosilane (0.041 mol, yield 40.8%). The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy. The results were as follows: C- CH ₂ -C at 1.3 ppm (m, 18H), Si- CH ₂ -C at 1.54 ppm (d, 2H) Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the O- CH ₂ -CH ₂ -O peak at O- CH ₂ -C, 3.57 ppm (s, 4H) at ppm (t, 14H)

Example 41: Synthesis of 2- (trichlorosilyl) -11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyl trichlorosilane

58.5 g (0.1 mol) of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy undecene and 54.18 g of trichlorosilane (Trichlorosilyl) -11- (8- (6- (8- (2-methoxyethoxy) octyloxy) -1,3,4-tetrahydroisoquinoline (0.4 mol) and tetrabutylphosphonium chloride ) Hexyloxy) octyloxy) undecyl trichlorosilane (0.039 mol, yield 39.4%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 34H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 14H) from _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 42: Synthesis of 2- (trichlorosilyl) -11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyl trichlorosilane

52.9 g (0.1 mol) of 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecene was obtained in the same manner as in Example 34, (Trichlorosilyl) -11- (6- (6- (6- (2-methoxyethoxy) ethyl) -1,3,4-tetrahydroisoquinoline (54.18 g, 0.4 mol) and tetrabutylphosphonium chloride (3 g, Hexyloxy) hexyloxy) hexyloxy) undecyl trichlorosilane was obtained in an amount of 31.9 g (0.04 mol, yield 40%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 26H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 14H) from _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) O- CH 2 -C, 3.57 in in ppm (s, 4H) O- CH 2 - CH 2 -O was, confirmed that the peak.

Example 43: Synthesis of 2- (trichlorosilyl) -11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrichlorosilane

50.1 g (0.1 mol) of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecene, 54.18 g of trichlorosilane (Trichlorosilyl) -11- (3- (10- (3- (2-methoxyethoxy) propoxy) -1,3,4-tetrahydroisoquinoline (0.4 mol) and tetrabutylphosphonium chloride (3 g ) Decyloxy) propoxy) undecyltrichlorosilane (0.042 mol, yield 42.1%). The obtained product 300 MHz 1H magnetic resonance analysis, 1.3 ppm (m, 26H) from _{C- CH 2 -C, 1.46 ppm (} d, 2H) Si- CH 2 -C, 1.5 ppm (t, 1H) from Si- CH -C, 1.53 ppm (m , 14H) from _{C- CH 2 -CO, 1.63 ppm (} m, 6H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the O- CH ₂ -CH ₂ -O peak at O- CH ₂ -C, 3.57 ppm (s, 4H) at ppm (t, 14H)

Example 44: Synthesis of 11- (6- (2-methoxyethoxy) hexyloxy) undecyltrimethoxysilane

170 g (0.37 mol) of 11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane and 60 g (1.83 mol) of methanol were added thereto in the same manner as in Example 3, And the mixture was reacted under reduced pressure to obtain 124 g (0.27 mol, yield 75%) of 11- (6- (2-methoxyethoxy) hexyloxy) undecyltrimethoxysilane. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 20H) C- CH 2 -C, 1.53 ppm (m, 6H) In _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) O- CH 2 in the - CH ₂ from -O, 3.55 ppm (s, 9H ) confirmed the Si-O- CH _3, peak.

Example 45: Synthesis of 11- (10- (2-methoxyethoxy) disiloxy) undecyltrimethoxysilane

90 g of n-hexane, 30 g (57 mmol) of 11- (10- (2-methoxyethoxy) disiloxyl) undecyltrichlorosilane and 9.2 g (0.29 mol) of methanol were added thereto in the same manner as in Example 3 The reaction mixture was distilled under reduced pressure to obtain 20 g (039 mmol, yield 69.2%) of 11- (10- (2-methoxyethoxy) disiloxyl) undecyltrimethoxysilane. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy at C- CH ₂ -C, 1.53 ppm (m, 6H) at Si- CH ₂ -C, 1.3 ppm (m, 28H) at 0.63 ppm _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) O- CH 2 in the - CH ₂ from -O, 3.55 ppm (s, 9H ) confirmed the Si-O- CH _3, peak.

Example 46: Synthesis of 11- (8- (3-methoxypropoxy) octyloxy) undecyltrimethoxysilane

500 ml of n-hexane, 506.1 g (1 mol) of 11- (8- (3-methoxypropoxy) octyloxy) undecyltrichlorosilane and 160.2 g (5 mol) of methanol were placed in the same manner as in Example 3 And 354.8 g (0.72 mol, yield 72.1%) of 11- (8- (3-methoxypropoxy) octyloxy) undecyltrimethoxysilane was obtained by distillation under reduced pressure. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 24H) C- CH 2 -C, 1.53 ppm (m, 6H) In _{C- CH 2 -CO, 1.63 ppm (} m, 2H) from the _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 10H) in, The peak of Si-O- CH ₃ was confirmed at 3.55 ppm (s, 9H).

Example 47: Synthesis of 11- (5- (1-methoxymethoxy) pentyloxy) undecyltrimethoxysilane

500 ml of n-hexane, 435.9 g (1 mol) of 11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane and 160.2 g (5 mol) of methanol were placed in the same manner as in Example 3 The reaction mixture was distilled under reduced pressure to obtain 329.7 g (0.78 mol, 77.8% yield) of 11- (5- (1-methoxymethoxy) pentyloxy) undecyltrimethoxysilane. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 18H) C- CH 2 -C, 1.53 ppm (m, 6H) In _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 ppm (t, 6H) Si-O- CH 3 from _{O- CH 2 -C, 3.55 ppm (} s, 9H) in, O- CH ₂ -O, peak was confirmed at 3.53 ppm (s, 2H).

Example 48: Synthesis of 11- (4- (2-methoxyethoxy) butoxy) undecyltrimethoxysilane

500 ml of n-hexane, 435.9 g (1 mol) of 11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane and 160.2 g (5 mol) of methanol were placed in the same manner as in Example 3 The reaction mixture was distilled under reduced pressure to obtain 317 g (0.75 mol, yield 75%) of 11- (4- (2-methoxyethoxy) butoxy) undecyltrimethoxysilane. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 16H) C- CH 2 -C, 1.53 ppm (m, 6H) In _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 6H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) O- CH 2 in the - CH ₂ from -O, 3.55 ppm (s, 9H ) confirmed the Si-O- CH _3, peak.

Example 49: Synthesis of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrimethoxysilane

500 ml of n-hexane, 580.1 g of 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrichlorosilane 1 mol) and 160.2 g (5 mol) of methanol were charged and reacted to obtain 11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyl 442.2 g (0.78 mol, yield: 78.1%) of trimethoxysilane was obtained. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 20H) C- CH 2 -C, 1.53 ppm (m, 6H) In _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 14H) in, CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 9H) - 3.53 ppm (s, 4H) O- CH 2 in.

Example 50: Synthesis of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyltrimethoxysilane

In the same manner as in Example 3, 700 ml of n-hexane and 720.4 g of 11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyltrichlorosilane 1 mol) and 160.2 g (5 mol) of methanol were added to the reaction mixture and the mixture was distilled under reduced pressure to obtain 11- (8- (6- (8- (2- methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyl 537.4 g (0.76 mol, yield 75.6%) of trimethoxysilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy and found to be C- CH ₂ -C, 1.53 ppm (m, 14H) at Si- CH ₂ -C at 1.3 ppm (t, 2H) _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) O- CH 2 in the - CH ₂ from -O, 3.55 ppm (s, 9H ) confirmed the Si-O- CH _3, peak.

Example 51: Synthesis of 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyltrimethoxysilane

In the same manner as in Example 3, 700 ml of n-hexane, 11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyltrichlorosilane 664.3 g (1 mol) and methanol (160.2 g, 5 mol) were added and the mixture was distilled under reduced pressure to obtain 11- (6- (6- (6- (0.74 mol, yield: 73.7%) of the title compound was obtained. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (t, 2H) from the _{Si- CH 2 -C, 1.3 ppm (} m, 28H) C- CH 2 -C, 1.53 ppm (m, 14H) from _{C- CH 2 -CO, 3.38 ppm (} s, 3H) from _{O- CH 3, 3.45 ppm (t} , 14H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) O- CH 2 in the - CH ₂ from -O, 3.55 ppm (s, 9H ) confirmed the Si-O- CH _3, peak.

Example 52: Synthesis of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrimethoxysilane

In the same manner as in Example 3, 700 ml of n-hexane, 636.3 g of 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrichlorosilane 1 mol) and 160.2 g (5 mol) of methanol were added and reacted to obtain 11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyl 461 g (0.74 mol, yield: 73.7%) of trimethoxysilane was obtained. The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance (NMR) spectroscopy at C- CH ₂ -C, 1.53 ppm (m, 6H) at Si- CH ₂ -C, 1.3 ppm (m, 28H) at 0.63 ppm _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, O- CH 2 -C at 3.45 ppm (t, 14H) in, CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 9H) - 3.53 ppm (s, 4H) O- CH 2 in.

Example 53: Synthesis of 2- (trimethoxysilyl) -11- (2-methoxyethoxy) undecyltrimethoxysilane

500 ml of n-hexane, 497.3 g (1 mol) of 2- (trichlorosilyl) -11- (2-methoxyethoxy) undecyltrichlorosilane and 256.3 g (8 mol) of methanol were reacted in the same manner as in Example 3, And the mixture was reacted under reduced pressure to obtain 338.9 g (0.72 mol, yield 72%) of 2- (trimethoxysilyl) -11- (2-methoxyethoxy) undecyltrimethoxysilane. The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 14H) from Si- CH -C, 1.53 ppm (m , 2H) from the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 ppm (t, 2H) O- CH 2 -C, 3.53 in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 54: Synthesis of 2- (trimethoxysilyl) -11- (6- (2-methoxyethoxy) hexyloxy) undecyltrimethoxysilane

(1 mol) of 2- (trichlorosilyl) -11- (6- (2-methoxyethoxy) hexyloxy) undecyltrichlorosilane was obtained in the same manner as in Example 3, And 256.3 g (8 mol) of methanol were added to the reaction mixture. The reaction mixture was distilled under reduced pressure to obtain 405.3 g of 2- (trimethoxysilyl) -11- (6- (2-methoxyethoxy) hexyloxy) undecyltrimethoxysilane 0.71 mol, yield 70.9%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 18H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.53 from _{O- CH 3, 3.45 ppm (t} , 6H) in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 55: Synthesis of 2- (trimethoxysilyl) -11- (10- (2-methoxyethoxy) disiloxy) undecyltrimethoxysilane

600 ml of n-hexane, 653.5 g (1 mol) of 2- (trichlorosilyl) -11- (10- (2-methoxyethoxy) disiloxy) undecyltrichlorosilane, The reaction was carried out by adding 256.3 g (8 mol) of methanol and the mixture was distilled under reduced pressure to obtain 464 g of 2- (trimethoxysilyl) -11- (10- (2- methoxyethoxy) disiloxy) undecyltrimethoxysilane 0.74 mol, yield 73.5%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 26H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.53 from _{O- CH 3, 3.45 ppm (t} , 6H) in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 56: Synthesis of 2- (trimethoxysilyl) -11- (8- (3-methoxypropoxy) octyloxy) undecyltrimethoxysilane

600 ml of n-hexane, 639.5 g (1 mol) of 2- (trichlorosilyl) -11- (8- (3- methoxypropoxy) octyloxy) undecyltrichlorosilane, And 256.3 g (8 mol) of p-toluenesulfonic acid were added and reacted to obtain 472 g of 2- (trimethoxysilyl) -11- (8- (3- methoxypropoxy) octyloxy) undecyltrimethoxysilane , Yield: 77%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 22H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 1.63 ppm (} m, 2H) from the _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the in ppm _{(t, 10H) O- CH 2} -C, 3.55 ppm (s, 18H) was confirmed in the Si-O- CH _3, peak.

Example 57: Synthesis of 2- (trimethoxysilyl) -11- (5- (1-methoxymethoxy) pentyloxy) undecyltrimethoxysilane

(1 mol) of 2- (trichlorosilyl) -11- (5- (1-methoxymethoxy) pentyloxy) undecyltrichlorosilane in 600 ml of n-hexane, And 256.3 g (8 mol) of p-toluenesulfonic acid were added and reacted to obtain 396.3 g (0.73 mol) of 2- (trimethoxysilyl) -11- (5- (1- methoxymethoxy) pentyloxy) undecyltrimethoxysilane , Yield: 73.3%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 16H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.55 from _{O- CH 3, 3.45 ppm (t} , 6H) in ppm (s, 18H) O- CH 2 -O was, confirmed that the peak in _{Si-O- CH 3, 5.45 ppm} (s, 2H) in.

Example 58: Synthesis of 2- (trimethoxysilyl) -11- (4- (2-methoxyethoxy) butoxy) undecyltrimethoxysilane

In the same manner as in Example 3, 569.4 g (1 mol) of 2- (trichlorosilyl) -11- (4- (2-methoxyethoxy) butoxy) undecyltrichlorosilane, And 256.3 g (8 mol) of p-toluenesulfonic acid were added and reacted to obtain 385.4 g (0.71 mol) of 2- (trimethoxysilyl) -11- (4- (2- methoxyethoxy) butoxy) undecyltrimethoxysilane , Yield: 70.8%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 14H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.53 from _{O- CH 3, 3.45 ppm (t} , 6H) in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 59: Synthesis of 2- (trimethoxysilyl) -11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) undecyltrimethoxysilane

(Trichlorosilyl) -11- (3- (6- (3- (2-methoxyethoxy) propoxy) hexyloxy) propoxy) n-hexane was obtained in the same manner as in Example 3, (Trimethoxysilyl) -11- (3- (6- (3- (2- (2-methylpiperazin-1- (Methoxyethoxy) propoxy) hexyloxy) propoxy) undecyl trimethoxysilane was obtained in an amount of 446.6 g (0.71 mol, yield 71.2%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 18H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the ppm (t, 14H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) from O- CH ₂ - CH ₂ -O, check for Si-O- CH _3, peaks at 3.55 ppm (s, 18H) Respectively.

Example 60: Synthesis of 2- (trimethoxysilyl) -11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) undecyltrimethoxysilane

(Trichlorosilyl) -11- (8- (6- (8- (2-methoxyethoxy) octyloxy) hexyloxy) octyloxy) (Trimethylsilyl) -11- (8- (6- (8- (2-morpholin-2-ylmethyl) (Methoxymethoxy) octyloxy) hexyloxy) octyloxy) undecyl trimethoxysilane (0.7 mol, yield 69.5%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 34H) from Si- CH -C, 1.53 ppm (m , 14H) from _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.53 from _{O- CH 3, 3.45 ppm (t} , 14H) in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 61: Synthesis of 2- (trimethoxysilyl) -11- (6- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyltrimethoxysilane Synthesis of

In the same manner as in Example 3, 900 ml of n-hexane, 100 mg of 2- (trichlorosilyl) -11- (6- (6- (6- (2- methoxyethoxy) hexyloxy) hexyloxy) 797.7 g (1 mol) of undecyl trichlorosilane and 256.3 g (8 mol) of methanol were added and reacted to obtain 2- (trimethoxysilyl) -11- (6- (6- (2-methoxyethoxy) hexyloxy) hexyloxy) hexyloxy) undecyltrimethoxysilane was obtained in an amount of 539.9 g (0.7 mol, yield 70%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 26H) from Si- CH -C, 1.53 ppm (m , 14H) from _{C- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 2 -C, 3.53 from _{O- CH 3, 3.45 ppm (t} , 14H) in CH ₂ -O, it was confirmed the Si-O- CH _3, peaks at 3.55 ppm (s, 18H) - ppm (s, 4H) O- CH 2 in.

Example 62: Synthesis of 2- (trimethoxysilyl) -11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrimethoxysilane

(Trichlorosilyl) -11- (3- (10- (3- (2-methoxyethoxy) propoxy) decyloxy) propoxy) n-hexane was obtained in the same manner as in Example 3, (Trimethoxysilyl) -11- (3- (10- (3- (2-methylpiperazin-1-yl) (Methoxyethoxy) propoxy) decyloxy) propoxy) undecyltrimethoxysilane was obtained in an amount of 535.1 g (0.72 mol, yield 71.7%). The obtained product is 300 MHz in a hydrogen nuclear magnetic resonance analysis, 0.63 ppm (d, 2H) C- CH 2 -C, 1.5 ppm (t, 1H) in a _{Si- CH 2 -C, 1.3 ppm (} m, 26H) from Si- CH -C, 1.53 ppm (m , 6H) in the _{C- CH 2 -CO, 1.63 ppm (} m, 4H) in _{OC- CH 2 -CO, 3.38 ppm (} s, 3H) O- CH 3, 3.45 at the ppm (t, 14H) from _{O- CH 2 -C, 3.53 ppm (} s, 4H) from O- CH ₂ - CH ₂ -O, check for Si-O- CH _3, peaks at 3.55 ppm (s, 18H) Respectively.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention . The invention is not limited by these variations and modifications, but is limited only by the claims appended hereto.

Claims (8)

The methoxyethanol represented by the general formula (2) and the undecenol at the other end are sequentially reacted with one mole of the alpha, omega-dihaloalkane represented by the general formula (1), and HX is removed therefrom to synthesize an ether linkage To have,
Formula 1
X- (R) -X
In the above R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10, (CH 2) 3 -O- (CH _{2) 6 -O- (CH 2)} 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O- (CH 2) 6 -O- (CH ₂ ) ₆ and (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , and X is one selected from the group consisting of Cl, Br and I And,
(2)
Me- (OCH ₂ CH ₂₎ mOH
M is 1 or 3,
(3)

And in which m is 1, 2 or 3, n is 0 or 1 and in wherein R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2 _{) 8, (CH 2) 10} , (CH 2) 3 -O- (CH 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2 ) _8, (from _{CH 2) 6 -O- (CH 2} ) 6 -O- (CH 2) 6 , and _{(CH 2) 3 -O- (CH} 2) 10 -O- (CH 2) groups of ₃ Wherein the hydrophilic group and the lipophilic group are simultaneously selected. The process according to claim 1, wherein the compound represented by the general formula (3) is simultaneously synthesized by trichlorosilane with a trichlorosilane under a tetrabutylphosphonium chloride catalyst to produce a compound represented by the general formula (4) or (5)
Formula 4

Formula 5

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10, ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O - (CH ₂ ) ₆ -O- (CH ₂ ) ₆ and (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is selected from the group consisting of Cl, Br And I, wherein the hydrophilic group and the lipophilic group are simultaneously substituted. The method according to claim 2, wherein the chlorosilane compound represented by the general formula (4) and the compound represented by the general formula (5) is reacted with an alcohol,
6

Formula 7

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10, ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O - (CH ₂ ) ₆ -O- (CH ₂ ) ₆ and (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is selected from the group consisting of Cl, Br And I, and R1 is an alkyl group having 1 to 3 carbon atoms, wherein the hydrophilic group and the lipophilic group are simultaneously substituted. The methoxyethanol represented by the formula (2) and the undecenol at the other end are sequentially reacted with one mole of the alpha, omega-dihaloalkane represented by the formula (1) Displayed,
Formula 1
X- (R) -X
In the above R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10, (CH 2) 3 -O- (CH _{2) 6 -O- (CH 2)} 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O- (CH 2) 6 -O- (CH ₂ ) ₆ and (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , and X is one selected from the group consisting of Cl, Br and I And,
(2)
Me- (OCH2CH2) mOH
M is 1 or 3,
(3)

And in which m is 1, 2 or 3, n is 0 or 1, R is R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6 In the above, ( _{CH 2) 8, (CH 2} ) 10, (CH 2) 3 -O- (CH 2) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- ( consisting of _{CH 2) 8, (CH 2} ) 6 -O- (CH 2) 6 -O- (CH 2) 6 , and _{(CH 2) 3 -O- (CH} 2) 10 -O- (CH 2) 3 X is one selected from the group consisting of Cl, Br and I,
Wherein the compound of formula (3) is synthesized by using tetrabutylammonium chloride or tetrabutylammonium bromide as a catalyst in a methoxyethyl chloride and undecenol DME solution and KOH as a base, wherein the hydrophilic group and the lipophilic group are simultaneously substituted A method for producing a silicone binder for a fingerprint sealant coating. [Claim 4] The process according to claim 4, wherein the compound of formula (3) is synthesized by the hydrogen silylation reaction with trichlorosilane in the presence of a platinum catalyst,
Formula 4

And in which m is 1, 2 or 3, R is _{(CH 2) 3, (CH} 2) 4, (CH 2) 5, (CH 2) 6, (CH 2) 8, (CH 2) 10, ( _{CH 2) 3 -O- (CH 2} ) 6 -O- (CH 2) 3, (CH 2) 8 -O- (CH 2) 6 -O- (CH 2) 8, (CH 2) 6 -O - (CH ₂ ) ₆ -O- (CH ₂ ) ₆ and (CH ₂ ) ₃ -O- (CH ₂ ) ₁₀ -O- (CH ₂ ) ₃ , X is selected from the group consisting of Cl, Br And I, wherein the hydrophilic group and the lipophilic group are simultaneously substituted with the hydrophilic group and the lipophilic group. The method of claim 4 or 5, wherein the temperature of the double reaction is from room temperature to 200 占 폚. The method for producing a silicone bonding agent for a fingerprint appearance preventing coating, wherein the hydrophilic group and the lipophilic group are simultaneously substituted. The method for producing a silicone bonding agent for a fingerprint display preventing film according to claim 4 or 5, wherein the reaction solvent is hexane, toluene or THF, wherein the hydrophilic group and the lipophilic group are simultaneously substituted. The method of claim 4 or 5, wherein the reaction proceeds without a reaction solvent, wherein the hydrophilic group and the lipophilic group are simultaneously substituted.