KR20180012646A - A Fluorosilicone Compounds for Preventing a Fingerprint and a Method for Preparing the Same - Google Patents

Abstract

The present invention relates to a fluorosilicone compound for preventing fingerprints and a preparation method thereof and, more specifically, to a fluorosilicone compound for preventing fingerprints comprising a fluoroalkyl or perfluoropolyether compound in which hydroxyl groups are substituted on both ends of molecules as a starting material, and to a preparation method thereof. The fluorosilicone compound of the present invention is represented by chemical formula 9.

Description

[0001] Fluorosilicone Compounds for Preventing Fingerprints [0002]

The present invention relates to a fluorosilicone compound for the prevention of fingerprints and a process for producing the same, and more particularly to a fluorosilicone compound for preventing fingerprints comprising a fluoroalkyl or perfluoropolyether compound having a hydroxyl group at both ends of the molecule substituted, And a manufacturing method thereof.

Fluorine-substituted organic compounds have lower surface tension than other organic compounds and are highly stable compounds with excellent water solubility. Due to such properties, fluorine-substituted organic compounds can be widely used as water repellent agents, oil repellents or antifouling agents. For this purpose, fluorine-substituted compounds having 3 to 12 carbon atoms can be used. Due to the excellent hydrophobicity and abrasion resistance of the fluorine compound, the fluorine compound can be used for the surface treatment of a touch screen of an electronic product. For example, an organometallic compound such as perfluoropolyether alkoxysilane may be used as a coating for the treatment of the contact surface of a touch screen substrate. Fluorine-based functional materials have been attracting much attention as a core material of the next generation technology in optical communication, optoelectronics, semiconductors, automobiles or computers in high-tech industries. Especially, optical films used in outermost layers of various displays such as liquid crystal displays Industrial demand for fluorine-based functional materials is increasing rapidly. In general, the optical film may comprise a liquid crystal or polarizing function layer, a hard coating layer for protecting and flattening the liquid crystal, an antireflection layer for preventing external light interference to provide a clear image, and an antifouling layer for preventing surface contamination have. In this structure, various material technologies for manufacturing an optical film including an antifouling layer are very important in industry. According to the known technology, the antireflection film can be made into a multi-layer structure of an inorganic oxide thin film having a very high hydrophilicity in order to control the refractive index and the thickness. However, such a material layer has a problem that it is easily contaminated during use and it is difficult to remove contaminants. In addition, when solvents are used to remove contaminants, the surface of the display film may be damaged. In order to solve such a problem, there is known a method of forming a silicon or fluorocarbon polymer as a cured film on the outermost surface to prevent contamination and water repellency of a surface of a photo-functional film or glass.

Silicon coupling agents having various structures that can be used as various kinds of contamination-preventing surface treatment agents of such a substrate are known. However, when silicon alone is used in such a silicone bond, friction durability is poor or sufficient cross-linking is not performed, and therefore, the glass transition temperature is low and the contamination accumulates. . To overcome these disadvantages, the use of a fluorine compound having excellent water repellency and oil repellency may weaken adhesion to the surface. In order to solve such a problem, a fluorosilicone coupling agent in which a fluorine-substituted organic group is introduced into silicon may be used.

Patent Registration No. 10-1459507 discloses a method of synthesizing a silicone compound which bonds with an undecyl group which is a lipophilic group starting from an alkoxy group and reacting with alkoxyalkyl chloride by using undecenol directly without using bromo undecene . Also, U.S. Patent No. 6,841,079 discloses a method of synthesizing fluorine-substituted alkyl alcohol with allyl bromide using KOH in the presence of tetrabutylammonium bromide catalyst without using metal sodium. Other alkyl halides other than allyl bromide can be applied using such reaction conditions. By applying the process disclosed in the prior art, it is possible to increase the economical efficiency and reduce the risk of a known product prepared by bonding the hydrophilic group of the alkoxy alcohol and the undecyl group of the carbon having the lipophilic group of 11, and to produce the alpha, omega-dihalo A new silicone bonding agent can be prepared which increases the specific gravity of an oily group by introducing an ether in the middle of an alkane, an alpha or an omega-dihaloalkane to improve the anti-fingerprint performance. It is said that this product is suitable for the purpose of preventing the fingerprints from appearing. However, the prior art does not disclose a silicon compound with improved performance in that the fingerprint is not affected or easily wiped.

The present invention has been made to solve the problems of the prior art and has the following purpose.

Prior Art 1: Patent Registration No. 10-1459507 (registered trademark, manufactured by JASSIA Silicone Co., Ltd., registered on Nov. 03, 2014) Silicone compound having both hydrophilic and lipophilic groups and method for producing the same Prior Art 2: U.S. Patent No. 6,841,079 (registered 3M Innovative Properties Company, Jan. 11, 2005) Fluorochemical treatment for silicon articles

It is an object of the present invention to provide a fluorosilicone compound for preventing fingerprints using fluoroalkyl or perfluoroalkylether terminated with a hydroxyl group (OH) at both ends of a molecule and a process for producing the same.

According to a preferred embodiment of the present invention, a fluoro silicone compound for preventing fingerprints and a process for producing the same are represented by the formula (9)

Formula 9

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, X ³ = OR or _{(CH 2) q Si (OR} ) , and the _3, q = 1 , 2, 3, 4, 6, 8, 10 or 11, and R is Me or Et.

According to another preferred embodiment of the present invention, a compound represented by the formula (9), represented by the formula (8)

8

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o or _{F (CF 2) a ((} CF 2) 2 O) _m CF, and the _second, and is a = 1 or 2, X ² = Cl or (CH _2), and the _q SiCl _3, and a q = 1, 2, 3, 4, 6, 8, 10 or 11 , And R is Me or Et.

According to another preferred embodiment of the present invention,

6

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or F (CF ₂ ) _a ((CF ₂ ) ₂ O) _m CF ₂ , a = 1 or 2, and R is Me or Et.

According to another preferred embodiment of the present invention,

Formula 4

,

,

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p and X ¹ = Br or I is 1 to 12, Y = F, CF ₃ and p = N is 1, 2, 4, 6, 8 or 9, m = 0, 1, 2 or 3, and R is Me or Et.

According to another preferred embodiment of the present invention, the compound represented by the formula (9) is obtained by the reaction of the trimethyl / ethyl oxosuccinate of the compound represented by the formula (8)

8

Formula 9

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, and the X ² = Cl or _{(CH 2) q SiCl 3,} X 3 = OR or ( CH ₂ ) _q Si (OR) ₃ , q = 1, 2, 3, 4, 6, 8, 10 or 11, and R is Me or Et.

According to another preferred embodiment of the present invention, the compound represented by the general formula (8) is obtained by the reaction of the compounds represented by the general formulas (6) and (7)

6

Formula 7

H-SiCl ₂ -X ²

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, and the X ² = Cl or _{(CH 2) q SiCl 3,} X 3 = OR or ( CH ₂ ) _q Si (OR) ₃ , q = 1, 2, 3, 4, 6, 8, 10 or 11, and R is Me or Et.

According to another preferred embodiment of the present invention, the compound represented by the formula (6) is obtained from the compound represented by the formula (4) and the formula (5)

Formula 4

Formula 5

HO (CH ₂ ) _m (R f ¹ )

In the Rf is (CF _{2) o,} (CF ₂ OCF _{2) o,} or _{O (CF (Y) CF 2} O) , and the _{p, o = 1 ~ 12,} Y = F, CF 3, p = is a 2 ~ 200, Rf ¹ is a CH (CF _{3 ) 2, F (CF 2)} o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and ^{a = 1, 2, X 1} = is a Br or I, n = 1, 2, 4, 6, 8 or 9 , M = 0, 1, 2 or 3, and R is Me or Et.

According to another preferred embodiment of the present invention, the compound represented by the general formula (4) is obtained by a halogenation reaction of one of the compounds represented by the general formula (3)

(3)

_{CH 2 = CH (CH 2)} n O (CH 2) m (Rf) (CH 2) m O (CH 2) n CH = CH 2,

In the Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , wherein o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, m is 1, 2 or 3 , N is 0 or 1, and R is Me or Et.

According to another preferred embodiment of the present invention, the reaction solvent is methanol, ethanol, trimethylorthoformate or triethylorthoformate.

According to another preferred embodiment of the present invention, the reaction solvent comprises 1,3-bis (trifluoromethyl) benzene and the catalyst is selected from the group consisting of Spire, Carstate, Otsuko, Ashby- And is a catalyst.

The silicone compound according to the present invention can be used as a surface treating agent for a touch screen display. The silicone compound according to the present invention is excellent in friction durability and allows the coating to have improved adhesion properties while leaving fingerprints on the surface of the display.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the embodiments shown in the accompanying drawings, but the present invention is not limited thereto.

The compound according to the present invention is represented by the formula (9)

Formula 9

In the Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , 6, 8, or 9, and, m = 0, and 1, 2, or 3 Rf ¹ is _{CH (CF 3) 2, F} (CF 2) o or _{F (CF 2) a ((} CF 2) 2 o) _m CF ₂ , a = 1 or 2, X ³ = OR or (CH ₂ ) _q Si (OR) ₃ and q = 1, 2, 3, 4, 6, 8, 10 or 11, R is Me or Et.

According to the present invention, the compound represented by the formula (9) can be produced through the following steps.

The preparation process of the compound represented by the formula (9)

Step 1

The compound represented by the formula (1) is reacted with the compound represented by the formula (2) to generate the compound represented by the compound (3)

Step 2

The compound represented by the general formula (4) is produced by a halogenation reaction of one of the double bonds formed in the compound represented by the general formula (3)

Step 3

Reacting a compound represented by the formula (5) with a compound represented by the formula (4) to generate a compound represented by the formula (6)

Step 4

The compound represented by the formula (6) is reacted with the compound represented by the formula (7) to give the compound represented by the formula

Step 5

The compound represented by the formula (8) is reacted with trimethyl / ethyl osloformamide to give the compound represented by the formula (9)

In the Rf is (CF _{2) o,} (CF ₂ OCF _{2) o,} or _{O (CF (Y) CF 2} O) , and the _{p, o = 1 ~ 12,} Y = F, CF 3, p = is a 2 ~ 200, Rf ¹ is a CH (CF _{3 ) 2, F (CF 2)} o Or _{F (CF 2) a ((} CF 2) 2 O) m CF , and the _second, and is an a = 1 or 2, X = Cl, Br or I, and are X ¹ = Br or I, X ² = Cl or (CH ₂ ) _q SiCl ₃ and X ³ = OR or (CH ₂ ) _q Si (OR) ₃ and q = 1, 2, 3, 4, 6, 8, 10 or 11, n = 1, 2, 4, 6, 8, 9, m = 0, 1, 2, 3, and R is Me or Et.

In each step, the reaction may be carried out at a temperature ranging from room temperature to 180 ° C, and the solvent for the reaction may be dichloromethane, carbon tetrachloride, methanol, ethanol, dimethylsulfoxide, dimethoxyethane, toluene, THF, methoxynonafluorobutane , Ethylnonafluorobutane, tris (heptafluoropropyl) amine or 1,3-bis (trifluoromethyl) benzene. Catalysts may also be used in accordance with the need, for example, in Step 4, but not limited to, Spire, Carstate, Otsuko, Ashby-Karatsut or Lamorox catalysts.

The compounds according to the present invention can be added as binders in, for example, coatings for fingerprint protection of touch screens, but are not limited thereto and can be used as components for binders of various industrial formulations or the like. Therefore, the compounds according to the present invention are not limited by their use.

Patent Application No. 2016-0073854 filed by the present applicant discloses that a fluoroalkyl group having a hydroxyl group at only one end of a molecule or an alcohol in which a fluoroalkylpolyether group is substituted is used as a starting material and an alkene substituted with a halogen such as allyl bromide (Trichlorosilyl) alkane having Si-H bonds in its double bond between carbon and carbon to introduce an alkenylalkoxy group instead of a hydroxyl group by reacting a fluorosilicone compound . These compounds have the effect of hydrolyzing the fluorosilicone compound as compared with the known fluorosilicone compound and having two additional groups of five alkoxy groups bonded to silicon capable of participating in the coating, thereby forming a better coating. A fluoroalkyl or perfluoropolyether compound in which a hydroxyl group (OH) is substituted at both ends of a molecule may be used in the production of a fluorosilicone compound by reacting with an allyl bromide in place of a hydroxyl group to introduce an allyloxy group and adding trichlorosilane . Such compounds have economic advantages over compounds with hydroxyl groups at one end only. However, referring to " Advances in Functional Surface Technology, " Steven R. Block, " which corresponds to the technical data of Dow Corning, Inc., a compound having an alkoxysilyl group at both ends of a molecule is more resistant to abrasion resistance than a compound having only an alkoxysilyl group at one end of the molecule And the lifetime after surface treatment is short. Therefore, a raw material having a hydroxyl group at both ends of a molecule can be made into a fluorosilicone compound having a good performance by treating one side with a protecting agent and then reacting with the alkenyl halide only on the remaining side to add a silane. In addition, halogenation of only one side of the double bond substituted at both ends of the molecule with bromine or iodine, and then reacting the substituted halogen group with an alcohol substituted with a fluoroalkyl group or a fluoroalkyl ether group, To obtain a haloalkyl or fluoroalkyl ether. The compound thus synthesized may have a better effect than the silane-containing silicon compound on both sides of the known molecule. Such starting materials may be obtained commercially from Solvay D4000 or Dupont de Nenmours of the United States.

According to the present invention, a perfluoroalkyl or perfluoroalkyl ether terminated with a hydroxyl group (OH) at both ends of the molecule is reacted with an alkenyl halide to form a fluoroalkyl or perfluoroalkyl ether having an alkenyl group substituted on both ends of the molecule Can be obtained. And then reacting the substituted halogen group with an alcohol substituted with a fluoroalkyl group or a fluoroalkyl ether group by halogenating only one side of the double bond at either end of the molecule with bromine or iodine to obtain a fluoroalkyl or fluoro You can get Rochelle Ether. Then, the chloro group of the fluorosilyl-substituted chlorosilane compound prepared by adding a trichlorosilane or a bis (chlorosilyl) alkane having Si-H bonds to the hydrogen silylation reaction is reacted with trimethyl / ethyl orthosulfate to give an alkoxy group A substituted silicone compound can be obtained.

This is explained in detail below.

(OH) -containing fluoroalkyl or perfluoro (OH) -alkyl at both ends of the molecule, such as formula 1, which can be obtained commercially for the production of silicone compounds having fluorine-substituted organic groups for water- A compound of the formula (1) can be obtained by reacting an alkyl dodecane compound with a halogen alkene such as the formula (2) to obtain a fluoroalkyl or perfluoroalkyl dodecane compound in which alkene is substituted at both ends of the molecule.

Scheme 1

HO (CH ₂ ) _m (R f) (CH ₂ ) _m OH + X- (CH ₂ ) _n CH = CH ₂ ->

CH ₂ = CH (CH ₂ ) _n O (CH ₂ ) _m (R f) (CH ₂ ) _m O (CH ₂ ) _n CH = CH ₂

The halogenation of the double bond of the fluoroalkyl or perfluoroalkylidene compound substituted with alkene at both ends of the molecule obtained in Reaction Scheme 1 is halogenated to obtain an alkene substituted with a halogen group as shown in Formula 4, 2, < / RTI >

Scheme 2

The halogen group of the halogen-substituted compound obtained in Reaction Scheme 2 can be reacted with a fluoroalkyl group or a fluoroalkyl group such as the formula (5) to obtain a fluoroalkyl group or an alkenyl substituted with a perfluoroalkyl group, Can be represented by the following reaction formula 3.

Scheme 3

The fluoroalkyl group or the perfluoroalkyl group-substituted alkene obtained in the reaction formula 3 may be obtained by adding a trichlorosilane or bis (chlorosilyl) alkane having Si-H bonds as shown in the formula (7) to a hydrogen silylation reaction to form a fluoroalkyl group Or a trichlorosilane or bis (chlorosilyl) alkane substituted with a perfluoroalkyl group, and can be represented by the following Reaction Scheme 4.

Scheme 4

The corresponding alkoxy compound can be obtained from the trichlorosilane or bis (chlorosilyl) alkane substituted with the fluoroalkyl group or the perfluoroalkyl group obtained in the reaction formula 4 by reacting trimethyl / ethyl orthoformate as shown in the following reaction formula (5).

Scheme 5

The starting materials necessary for the production of the silicone compound in the present invention can be easily synthesized from commercially produced materials. The compound of formula (1) may be a compound (HO (CH ₂ ) _m O (R f) (CH ₂ ) _m OH) wherein the hydroxyl group (OH) is substituted at both ends of the molecule before the alkenyl group is bonded, have.

Perfluoro-1,5-pentanediol, 1H, 1H, 6H, 6H-perfluoro-1,4-butanediol, 1H, 1H, , 6-hexanediol, 1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane-1,8-diol, 1H, 1H, 8H, 8H-perfluoro-1,8-octanediol , 1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane-1,11-diol, 1H, 1H, 9H, 9H-perfluoro-1,9-nonanediol, 1H , 1H, 10H, 10H-perfluoro-1,10-decanediol, 1H, 1H, 12H, 12H-perfluoro-1,12-dodecanediol

Alcohols substituted with perfluoroalkyl ether groups having such a large molecular weight are fluororinks D10, D10H, D400 and D4000 (Fluorolink D10, D10H, D400 and D4000) sold by Solvay or Dupont, USA Formblin Y, and PFPE-Y. Among these products, a product having a molecular weight of 3,000 to 5,000 can be used as a material for producing a fingerprint inhibitor.

The fluorine-substituted alcohol corresponding to the compound represented by the formula (5) may include the following compounds.

(Perfluorobutyl) ethanol, 3- (perfluorobutyl) propanol, 2- (perfluorobutyl) propanol, 2- Perfluorooctyl) ethanol, 3- (perfluorooctyl) propanol, 2- (perfluorodecyl) ethanol, 2H-hexafluoro-2-propanol 1H, 1H-perfluoro-3,6-dioxadecan-1-ol, 1H, 1H-perfluoro-3,6-trioxal tridecanol- 1H-perfluoro-1-hexyl alcohol, 1H, 1H-perfluoro-1-heptyl alcohol, 1H, , 1H, 1H-perfluoro-1-decyl alcohol, 1H, 1H-perfluoro-1-undecyl alcohol

The bis (chlorosilyl) alkane corresponding to the compound represented by the general formula (7) may include the following compounds.

Bis (dichlorosilyl) (trichlorosilyl) methane, 1,2-bis (dichlorosilyl) (trichlorosilyl) ethane, 1,3-bis (dichlorosilyl) Dichlorosilyl) butane, 1,6-bis (dichlorosilyl) (trichlorosilyl) hexane, 1,8-bis (dichlorosilyl) (trichlorosilyl) ) (Trichlorosilyl) decane, 1,11-bis (dichlorosilyl) (trichlorosilyl) undecane

Some of these compounds are commercially produced and the remainder can be synthesized by redistribution with alkyl chlorosilanes with corresponding bis (trichlorosilyl) alkanes and Si-H bonds. The redistribution reaction can be carried out using tetrabutylphosphonium chloride as a catalyst.

As described above, the method for producing the silicon compound according to the present invention may include the following five steps of reactions.

Step 1: A reaction in which a fluoroalkyl or perfluoroalkylidene compound having a hydroxyl group (OH) closed on both sides of the molecule represented by the formula (1) is reacted with a halogenoalkene represented by the formula (2)

Step 2: Halogenation of only one side of the double bond to a fluoroalkyl group or a perfluoroalkyl ether compound substituted with an alkene represented by the formula (3)

Step 3: a reaction of substituting the fluoroalkyl group or the fluoroalkyl ether group represented by the formula (5) for the halogen group of the compound in which the double bond represented by the formula (4)

Step 4: A reaction in which a fluoroalkyl group or perfluoroalkyl ether group-substituted alkene represented by the formula (6) is subjected to hydrogen silylation reaction of trichlorosilane or bis (silyl) alkane represented by the formula (7)

Step 5: reacting the chloroalkyl group of the bis (chlorosilyl) alkane with a fluoroalkyl group represented by the formula (8) or a perfluoroalkylether substituted trichlorosilane or bis (chlorosilyl) alkane with methyl / Reaction

A fluoroalkyl or perfluoroalkylether compound in which the hydroxyl group (OH) is terminated on both sides of the molecule represented by formula (1) in step 1 is reacted with halogen alkenes using KOH in a dimethylsulfoxide or dimethoxyethane solution A fluoroalkyl or perfluoroalkylidene compound substituted with an alkene on both sides of the molecule represented by the formula (3) can be obtained.

Halogenated chlorine, bromine, and iodine may be used in the fluoroalkyl or perfluoroalkyl ether compound in which the alkene is substituted on both sides of the molecule in step 2, and the solvent may be carbon tetrachloride or dichloromethane. Since the fluoro compound and the halogen may not be mixed in the above reaction, methoxynonafluorobutane or ethoxynonafluorobutane may be used for mixing the two compounds. In addition, the ratio of the reactants and the amount of the solvent in the reaction are adjusted so that the halogenation reaction proceeds on only one side.

The reaction of substituting the fluoroalkyl group or the fluoroalkyl group represented by the formula (5) for the halogen group of the compound represented by the formula (4) in the step 3 can be carried out in the same or similar manner to the reaction of the step 1.

The reaction of adding the trichlorosilane or bis (chlorosilyl) alkane represented by the formula (7) having Si-H bonds to the fluoroalkyl group represented by the formula (6) or the alkenyl substituted with the perfluoroalkyl ether group represented by the formula (6) It can be a digestion reaction, and a platinum-based catalyst can be used. In this reaction, the solvent may include 1,3-bis (trifluoromethyl) benzene since the fluoro compound is not well mixed with the bis (chlorosilyl) alkane.

In step 5, the reaction of replacing the chloro substituted with silicon in the silicon atom represented by the formula (8) with an alkoxy group can be carried out using alcohol and the hydrogen chloride produced as a by-product can be trapped with triethylamine. The alcohols, amines and solvents used in the reaction should be well dried and free from moisture. Instead of methanol or ethanol, trimethylorthoformate or triethylorthoformate can be used.

Reactors with pressurization devices used in the laboratory for the synthesis of fluorosilicone compounds may be used. The reaction apparatus includes an apparatus capable of slowly injecting the raw material under an inert gas, and may include a stirrer, a heater or a cooling means. Although a solvent can be used for the hydrocyanation reaction, in most cases the reaction can proceed under conditions where no solvent is used. Under an inert gas, the chlorosilane and the catalyst can be put into the reaction vessel and the organic compound having unsaturated bonds can be slowly injected. The order of injection of chlorosilanes and organic compounds can be changed if necessary. Depending on the type of compound used, the reaction can be quite exothermic and can be refluxed without heating from the outside by controlling the rate of chlorosilane injection. After the injection of chlorosilane is completed, stirring may be continued for a certain period of time to complete the reaction. After the reaction is complete, the product can be obtained by fractional distillation of the solution.

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

Example

Example 1: Synthesis of 1,4-bis (allyloxy) -1H, 1H, 4H, 4H-perfluorobutane

A 2000 ml three-necked flask was equipped with a condenser and a mechanical stirrer. (1 mol) of 1H, 1H, 4H, 4H-perfluoro-1,4-butanediol, 168.3 g (3 mol) of potassium hydroxide, 48.3 g (0.15 mol) of tetrabutylammonium bromide, Dimethoxyethane (200 ml) was added and stirred with a mechanical stirrer. 229.6 g (3 mol) of 3-chloro-1-propene was slowly added through a dropping funnel. The solution was stirred at 85 캜 with a mechanical stirrer and reacted for 16 hours. Hydrochloric acid was added thereto to remove tributylamine and potassium chloride as byproducts, and the organic layer was separated using a separating funnel. Then, water was removed by using MgSO ₄ and filtered, and 196.7 g (0.812 mol, yield: 81.2%) of 1,4-bis (allyloxy) -1H, 1H, 4H, 4H-perfluorobutane was obtained through vacuum distillation . The obtained product was analyzed by 300 MHz 1H magnetic resonance analysis and found to be O- CH ₂ -C, 5.24ppm (d, 4H) at 3.69ppm (s, 4H) and CF ₂ -CH ₂ -O at 4.04ppm The C- CH = C peak was identified at CC = CH ₂ , 5.89 ppm (m, 2H).

Example 2: Synthesis of 1- (allyloxy) -4- (2,3-dibromopropoxy) -1H, 1H, 4H, 4H-perfluorobutane

A condenser and a magnetic stirrer were installed in a 1000 ml two-necked flask. 242.2 g (1 mol) of 1,4-bis (allyloxy) -1H, 1H, 4H, 4H-perfluorobutane and 1000 ml of methoxynonafluorobutane were placed in a flask and stirred with a magnetic stirrer, and 159.8 g ) Slowly through a dropping funnel. The solution was stirred at 50 DEG C on a magnetic stirrer and reacted for 12 hours. Water was added to remove the remaining bromine, and the organic layer was separated using a separatory funnel. Then, water was removed by using MgSO ₄ , and the filtrate was distilled under reduced pressure to obtain 290 g of 1- (allyloxy) -4- (2,3-dibromopropoxy) -1H, 1H, 4H, 4H-perfluorobutane (0.721 mol, yield 72.2%). The obtained product 300MHz 1H magnetic resonance analysis, 3.69ppm (m, 6H) O- CH 2, 3.78ppm (d, 2H) from _{Br- CH 2, 4.04ppm (d,} 2H) C = C- CH in _{2, 4.17ppm (m, 1H)} C- CH = C peak was confirmed at Br- CH, 5.24ppm (d, 2H ) CC = CH 2, 5.89ppm (m, 1H) in.

Example 3: 1 - ( Allyloxy ) -4- (2,3- Bis (perfluorodecyl-2-ethoxy) propoxy ) - 1H, < / RTI > 4H, 4H - Perfluorobutane  synthesis

(1 mol) of 1- (allyloxy) -4- (2,3-dibromopropoxy) -1H, 1H, 4H, 4H-perfluorobutane, 500 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide and 48.4 g (0.15 mol) of tetrabutylammonium bromide were placed and stirred with a mechanical stirrer. 1692.2 g (3 mol) of 2- (perfluorodecyl) ethanol was added thereto through a dropping funnel, 1097.5 g (0.802 mol, yield: 80.2%) of (-) - (allyloxy) -4- (2,3- ). The obtained product 300MHz 1H magnetic resonance analysis, 1.78ppm (t, 4H) In the CF ₂ - in _{CH 2, 3.69ppm (m, 12H} ) O- CH 2, 3.49ppm (m, 1H) from O- CH, The C- CH = C peak was identified at CC = CH ₂ , 5.89 ppm (m, 1H) at C = C- CH ₂ , 5.24 ppm (d, 2H) at 4.04 ppm (d, 2H).

Example 4: 1 - (4,4,6,6,6- Pentachloro -4,6- Di-silylhexyloxy ) -4- (2,3- Bis (perfluorooctyl-2-ethoxy) propoxy ) -1H, 1H, 4H, 4H-perfluorobutane

A 1000 ml three-necked 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. Thereafter, 1- (allyloxy) -4- (0.3 mol) of perfluorobutane and 100 ppm of platinum of the total weight of the reaction product were placed in a flask equipped with a stirrer, And 149 g (0.6 mol) of bis (dichlorosilyl) (trichlorosilyl) methane was slowly added thereto through a dropping funnel. This solution was stirred at 85 캜 for 3 hours and then subjected to vacuum distillation to obtain 1- (4,4,6,6,6-pentachloro-4,6-disilacylhexyloxy) -4- (2,3-bis (Perfluorooctyl-2-ethoxy) propoxy) -1H, 1H, 4H, 4H-perfluorobutane was obtained in an amount of 415.2 g (0.257 mol, yield 85.6%). The obtained product is in the 300MHz 1H magnetic resonance analysis, 1.35ppm (m, 4H) C- CH 2 -C, 1.78ppm (t, 4H) In _{Si- CH 2, 1.5ppm (m,} 2H) from the CF ₂ - The O- CH peak was identified at O- CH ₂ , 3.49 ppm (m, 1H) at CH ₂ , 3.51 ppm (m, 14H)

Example 5: 1 - (4,4,6,6,6- Pentamethoxy -4,6- Di-silylhexyloxy ) -4- (2,3- Bis (perfluorooctyl-2-ethoxy) propoxy ) -1H, 1H, 4H, 4H-perfluorobutane

A 500 ml three-necked flask was equipped with a condenser and a magnetic stirrer. In the end of the condenser, the dried nitrogen was allowed to pass through and kept under a nitrogen atmosphere. Then, to the flask was added 1- (4,4,6,6,6-pentachloro-4,6-disilachyloxy) -4- 323.4 g (0.2 mol) of perfluorobutane and 212.2 g (2 mol) of trimethyl orthoformate were added to a solution of (2,3-bis (perfluorooctyl-2-ethoxy) propoxy) -1H, 1H, 4H, After stirring for 12 hours at 100 ° C, the mixture was distilled under reduced pressure to give 1- (4,4,6,6,6-pentamethoxy-4,6-disilachyloxy) -4- (2 , And 3-bis (perfluorooctyl-2-ethoxy) propoxy) -1H, 1H, 4H, 4H-perfluorobutane (0.182 mol, yield 91%). The obtained product 300MHz 1H magnetic resonance analysis, 0.6ppm (s, 2H) C- CH at _{Si- CH 2 -Si, 1.30ppm (m} , 2H) Si- CH 2, 1.5ppm (m, 2H) from _{2 -C, 1.78ppm (t, 4H} ) in the _{CF 2 - CH 2, 3.49ppm (} m, 1H) O- CH, 3.51ppm (m, 14H) O- CH 2, 3.55ppm (s, 15H) in It was confirmed in the O- CH ₃ peak.

Example 6 Synthesis of 1,5-bis (4-butenyloxy) -1H, 1H, 5H, 5H-perfluoropentane

(1 mol) of 1H, 1H, 5H, 5H-perfluoro-1,5-pentanediol, 250 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, 10 g of tetrabutylammonium bromide (3 mol) of 4-chloro-1-butene was placed in a dropping funnel and reacted to obtain 1,5-bis (4-butenyloxy) -1H, 1H, 5H, 5H-perfluoropentane (0.753 mol, yield 75.3%). As a result of the 300 MHz 1H magnetic resonance analysis, the obtained product showed O- CH ₂ at OC- CH ₂ , 3.55 ppm (m, 8H) and CC = CH ₂ at 5.00 ppm (d, 4H) at 2.13 ppm The C- CH = C peak was identified at 5.70 ppm (m, 2H).

Example 7 Synthesis of 1- (4-butenyloxy) -5- (3,4-dibromobutoxy) -1H, 1H, 5H, 5H-perfluoropentane

320.2 g (1 mol) of 1,5-bis (4-butenyloxy) -1H, 1H, 5H, 5H-perfluoropentane and 1200 ml of methoxynonafluorobutane were placed in the same manner as in Example 2, 159.8 g (1 mol) of bromine was poured into the flask through a dropping funnel and reacted to give 1- (4-butenyloxy) -5- (3,4-dibromobutoxy) -1H, 1H, 5H, (0.738 mol, yield: 73.8%) was obtained. As a result of the 300 MHz 1H magnetic resonance analysis, the obtained product was analyzed by O- CH ₂ at OC- CH ₂ , 3.55 ppm (m, 8H) and Br- CH ₂ at 3.73 ppm (d, 2H) The C- CH = C peak was identified at CC = CH ₂ , 5.70 ppm (m, 1H) at 3.84 ppm (m, 1H) at Br- CH and 5.00 ppm (d, 2H).

Example 8: 1 -(4- Butenyloxy ) -5- (3,4- Bis (perfluorooctyl-3-propoxy) butoxy ) - 1H, 1H, 5H, 5H - Perfluoropentane  synthesis

480.1 g (1 mol) of 1- (4-butenyloxy) -5- (3,4-dibromobutoxy) -1H, 1H, 5H, 5H-perfluoropentane was dissolved in the same manner as in Example 1, (3 mol) of 3- (perfluorooctyl) propanol was added dropwise via a dropping funnel. The mixture was stirred with a mechanical stirrer and charged with 500 ml of ethane, 168.3 g (3 mol) of potassium hydroxide and 48.4 g (0.15 mol) of tetrabutylammonium bromide. And reacted to obtain 1043.8 g of 1- (4-butenyloxy) -5- (3,4-bis (perfluorooctyl-3-propoxy) butoxy) -1H, 1H, 5H, (0.819 mol, yield 81.9%). The obtained product was analyzed by a 300 MHz hydrogen nuclear magnetic resonance analysis. As a result, it was confirmed that C═C-C═O at OC- CH ₂ , 1.61 ppm (t, 4H) and CF ₂ -CH ₂ at 2.13 ppm (m, 2H) _{CH 2, 3.16ppm (m, 1H} ) O- CH, 3.55ppm (m, 14H) O- CH 2, 5.00ppm (d, 2H) C from _{CC = CH 2, 5.70ppm (m} , 1H) from at - CH = C peak was confirmed.

Example 9: 1 - (5,5,8,8,8- Pentachloro -5,8- Disilaoctyloxy ) -5- (3,4- Bis (perfluorooctyl-3-propoxy) butoxy ) -1H, 1H, 5H, 5H-perfluoropentane

(Perfluorooctyl-3-propoxy) butoxy) -1H, 1H, 5H, 5H-perfluoro (4-methylphenyl) propionic acid was obtained in the same manner as in Example 4, (5 mol%) was added to the reaction mixture by distillation under reduced pressure to obtain 382.3 g (0.3 mol) of triphenylphosphine, 382.3 g (0.3 mol) of pentane, (Perfluorooctyl-3-propoxy) butoxy) -1H, 1H, 5H, 5H-pyrazol- 420.2 g (0.273 mol, yield: 91.1%) of perfluoropentane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.35ppm (m, 6H) In _{Si- CH 2, 1.40ppm (m,} 2H) OC- from _{Si-C- CH 2, 1.49ppm (} m, 8H) in CH _{2, 1.61ppm (t, 4H)} CF 2 from the - CH _2, O- CH, CH ₂ O- was found to peak at 3.55ppm (m, 14H) from 3.16ppm (m, 1H).

Example 10: 1 - (5,5,8,8,8- Pentamethoxy -5,8- Disilaoctyloxy ) -5- (3,4- Bis (perfluorooctyl-3-propoxy) butoxy ) -1H, 1H, 5H, 5H-perfluoropentane

(5,5,8,8,8-pentachloro-5,8-disilaoctyloxy) -5- (3,4-bis (perfluorooctyl-3- (0.2 mol) of perfluoro pentane and 212.2 g (2 mol) of trimethyl orthoformate were placed in a reaction vessel and the mixture was subjected to distillation under reduced pressure to obtain 1- (5,5,8-trichloroethoxy) (Perfluorooctyl-3-propoxy) butoxy) -1H, 1H, 5H, 5H-pyrazol- 279 g (0.184 mol, yield: 92.1%) of perfluoropentane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 0.6ppm (t, 2H) O -Si- CH 2, 1.35ppm (t, 4H) Si-C on the _{Si- CH 2, 1.40ppm (m,} 2H) from _{- CH 2, 1.49ppm (m,} 8H) in _{OC- CH 2, 1.61ppm (t,} 4H) in the _{CF 2 - CH 2, 3.16ppm (} m, 1H) O- CH, 3.42ppm (m, 14H) from O- CH ₃ peak at O- CH ₂ , 3.55 ppm (s, 15H).

Example 11 Synthesis of 1,6-bis (6-hexenyloxy) -1H, 1H, 6H, 6H-perfluorohexane

(1 mol) of 1H, 1H, 6H, 6H-perfluoro-1,6-hexanediol, 300 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, and 200 ml of tetrabutylammonium bromide (3-mol) of 6-chloro-1-hexene was placed in a dropping funnel and reacted to obtain 1,6-bis (6-hexenyloxy) -1H, 1H, 6H, 6H-perfluorohexane (0.786 mol, yield 78.6%). The obtained product 300MHz 1H magnetic resonance analysis, 1.40ppm (m, 8H) C- CH 2 -C, 1.96ppm (m, 4H) O in _{C = C- CH 2, 3.55ppm (} m, 8H) in The C- CH = C peak was identified at CC = CH ₂ , 5.70 ppm (m, 2H) at -CH ₂ , 5.00 ppm (d, 4H)

Example 12 Synthesis of 1- (6-hexenyloxy) -6- (5,6-dibromohexyloxy) -1H, 1H, 6H, 6H-perfluorohexane

426.4 g (1 mol) of 1,6-bis (6-hexenyloxy) -1H, 1H, 6H, 6H-perfluorohexane and 1200 ml of methoxynonafluorobutane were charged in the same manner as in Example 2, (1 mol) of bromine was added via a dropping funnel and reacted to give 1- (6-hexenyloxy) -6- (5,6-dibromohexyloxy) -1H, 1H, 6H, 6H-purple 724.2 g (0.728 mol, yield 72.8%) of rurohexane was obtained. The obtained product was analyzed by a 300 MHz hydrogen nuclear magnetic resonance analysis and found to be C- CH ₂ -C, 1.46 ppm (m, 4H) at OC- CH ₂ and 1.96 ppm (m, 2H) at 1.52 ppm _{- CH 2, 3.55ppm (m,} 8H) from _{O- CH 2, 3.78ppm (d,} 2H) Br- CH 2, 3.84ppm (m, 1H) Br- CH, 5.00ppm (d, 2H) from at CC = CH _2, C- CH = C was confirmed that peaks at 5.70ppm (m, 1H).

Example 13: 1 - (6- Hexenyloxy ) -6- (5,6- Bis (perfluorooctyl-2-ethoxy) hexyloxy ) - 1H, 1H, 6H, 6H - Perfluorohexane  synthesis

(1 mol) of 1- (6-hexenyloxy) -6- (5,6-dibromohexyloxy) -1H, 1H, 6H, 6H-perfluorohexane was obtained in the same manner as in Example 1, (3 mol) of 2- (perfluorooctyl) ethanol was added dropwise via a dropping funnel to a flask equipped with a stirrer, a stirrer, a stirrer, a stirrer, a stirrer, Hexyloxy) -6- (5,6-bis (perfluorooctyl-2-ethoxy) hexyloxy) -1H, 1H, 6H, 6H-perfluorohexane 1075.4 g (0.795 mol, yield 79.5%). The obtained product in a hydrogen 300MHz nuclear magnetic resonance analysis, 1.35ppm (m, 6H) C- CH 2 -C, 1.46ppm (m, 4H) In _{OC- CH 2, 1.78ppm (t,} 4H) In the CF ₂ - _{CH 2, 1.96ppm (m, 2H} ) from the _{C = O- CH 2, 5.00ppm (} d, 2H) from the _{C- CH 2, 3.16ppm (m,} 1H) O- CH, 3.55ppm (m, 14H) from C = CH = C peak at CC = CH ₂ , 5.70 ppm (m, 1H).

Example 14: 1 - (7,7,11,11,11- Pentachloro -7,11- Di-silyldecyloxy ) -6- (5,6- Bis (perfluorooctyl-2-ethoxy) hexyloxy ) -1H, 1H, 6H, 6H-perfluorohexane Synthesis of

(Perfluorooctyl-2-ethoxy) hexyloxy) -1H, 1H, 6H, 6H-purple in the same manner as in Example 4 (0.7 mol) of 1,3-bis (dichlorosilyl) (trichlorosilyl) propane were placed in a reactor, and the mixture was reacted under reduced pressure to obtain 1- (7,7- (Perfluorooctyl-2-ethoxy) hexyloxy) -1H, 1H, 6H, 6H, To obtain 406.6 g (0.249 mol, yield: 83.2%) of 6H-perfluorohexane. The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 6H) C- CH 2 -C, 1.46ppm (m, 4H) In _{Si- CH 2, 1.35ppm (m,} 12H) from OC- CH _{2, 1.78ppm (t, 4H)} CF 2 from the - CH _2, O- CH, CH ₂ O- was found to peak at 3.55ppm (m, 14H) from 3.16ppm (m, 1H).

Example 15: 1 - (7,7,11,11,11- Pentamethoxy -7,11- Di-silyldecyloxy ) -6- (5,6- Bis (perfluorooctyl-2-ethoxy) hexyloxy ) -1H, 1H, 6H, 6H-perfluorohexane Synthesis of

In the same manner as in Example 5, 1- (7,7,11,11,11-pentachloro-7,11-dicylaldecyloxy) -6- (5,6-bis (perfluorooctyl- Hexyloxy) -1H, 1H, 6H, 6H-perfluorohexane and 212.2 g (2 mol) of trimethyl orthoformate were reacted and distilled under reduced pressure to obtain 1- (7,7 Bis (perfluorooctyl-2-ethoxy) hexyloxy) -1H, 1H, 1H-indolyldecylsilyloxy) 6H, 6H-perfluorohexane (0.183 mol, yield 91.6%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O -Si- CH 2, 1.30ppm (t, 4H) C- CH at _{Si- CH 2, 1.35ppm (m,} 12H) from _{2 -C, 1.46ppm (m, 4H} ) in _{OC- CH 2, 1.78ppm (t,} 4H) in the _{CF 2 - CH 2, 3.16ppm (} m, 1H) O- CH, 3.55ppm (m, 14H) from O- CH ₃ peak at O- CH ₂ , 3.55 ppm (s, 15H).

Example 16: Synthesis of 1,8-bis (8-octenyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane

(1 mol) of 1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane-1,8-diol, 300 ml of dimethoxyethane and 168.3 g of potassium hydroxide (3 mol) of 8-chloro-1-octene were placed in a dropping funnel and reacted to obtain 1,8-bis (8-octenyl) Hexyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane (0.779 mol, yield 77.9%). The obtained product 300MHz 1H magnetic resonance analysis, 1.37ppm (m, 16H) C- CH 2 -C, 1.96ppm (m, 4H) O in _{C = C- CH 2, 3.49ppm (} m, 8H) in The C- CH = C peak was identified at CC = CH ₂ , 5.70 ppm (m, 2H) at -CH ₂ , 5.00 ppm (d, 4H)

Example 17: Synthesis of 1- (8-octenyloxy) -8- (7,8-dibromooxyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane

(1 mol) of 1,8-bis (8-octenyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane, methoxynonafluoro (1 mol) of bromine was added thereto through a dropping funnel and reacted to give 1- (8-octenyloxy) -8- (7,8-dibromooxyloxy) -1H, 490.3 g (0.727 mol, yield 72.7%) of 1H, 8H, 8H-perfluoro-3,6-dioxaoctane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.37ppm (m, 16H) C- CH 2 -C, 1.75ppm (m, 2H) Br-C- CH 2, 1.96ppm (m, 2H) C on the in _{= C- CH 2, 3.49ppm (m} , 8H) O- CH 2, 3.78ppm (d, 2H) from _{Br- CH 2, 3.84ppm (m,} 1H) Br- CH, 5.00ppm (d, 2H in ), The C- CH = C peak was confirmed at CC = CH ₂ , 5.70 ppm (m, 1H).

Example 18: 1 -(8- Octenyloxy ) -8- (7,8- Bis (perfluorohexyl-3-propoxy) octyloxy ) - 1H, < / RTI > 8H, 8H - Perfluoro Synthesis of -3,6-dioxaoctane

(8,8-octenyloxy) -8- (7,8-dibromooxyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane (3 mol) of tetrabutylammonium bromide were added to the flask, and the mixture was stirred with a mechanical stirrer. 1134.4 g (0.15 mol) of 3- (perfluorohexyl) propanol 3 mol) was put through a dropping funnel and reacted to give 1- (8-octenyloxy) -8- (7,8-bis (perfluorohexyl-3-propoxy) -Perfluoro-3,6-dioxaoctane (0.773 mol, yield 77.3%). The obtained product 300MHz 1H magnetic resonance analysis, 1.37ppm (m, 22H) from _{C- CH 2 -C, 1.61ppm (t} , 4H) In the CF ₂ - CH _2, C = at 1.96ppm (m, 2H) _{C- CH 2, 3.16ppm (m,} 1H) O- CH, 3.49ppm (m, 14H) O- CH 2, 5.00ppm (d, 2H) CC = CH 2, 5.70ppm (m, 1H) from at The C- CH = C peak was identified.

Example 19: 1 - (9,9,14,14,14- Pentachloro -9,14- Disilatetradecyloxy ) -8- (7,8- Bis (perfluorohexyl-3-propoxy) octyloxy ) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane Synthesis of

(Perfluorohexyl-3-propoxy) octyloxy) -1H, 1H, 8H, 8H-perfluoro 380.6 g (0.3 mol) of 3,6-dioxaoctane, 173.3 g (0.6 mol) of an ash noncarst catalyst and 1,4-bis (dichlorosilyl) (trichlorosilyl) (9,9,14,14,14-pentachloro-9,14-disilatetradecylsiloxy) -8- (7,8-bis (perfluorohexyl-3-propoxy) Octyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane was obtained in an amount of 398.1 g (0.255 mol, yield 85.1%). The obtained product 300MHz 1H magnetic resonance analysis, 3.16ppm (m, 1H) from O- CH, 1.30ppm (t, 6H ) In _{Si- CH 2, 1.37ppm (m,} 30H) C- CH 2 -C in , 1.61 ppm (t, 4H), O- CH ₂ peak was confirmed at CF ₂ -CH ₂ , 3.49 ppm (m, 14H).

Example 20: 1 - (9,9,14,14,14- Pentamethoxy -9,14- Disilatetradecyloxy ) -8- (7,8- Bis (perfluorohexyl-3-propoxy) octyloxy ) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane Synthesis of

(9,9,14,14,14-pentachloro-9,14-disilatetradecylsiloxy) -8- (7,8-bis (perfluorohexyl-3 311.8 g (0.2 mol) of perfluoro-3,6-dioxaoctane and 212.2 g (2 mol) of trimethyl orthoformate were placed in a reaction vessel, and the mixture was subjected to vacuum distillation (9,9,14,14,14-Penta-methoxy-9,14-disilatetradecyloxy) -8- (7,8-bis (perfluorohexyl-3-propoxy) octyl Hexyloxy) -1H, 1H, 8H, 8H-perfluoro-3,6-dioxaoctane was obtained in an amount of 274.5 g (0.179 mol, yield 89.3%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O -Si- CH 2, 1.30ppm (t, 4H) C- CH at _{Si- CH 2, 1.37ppm (m,} 30H) from O- CH ₂ peaks at O- CH ₂ , 3.55 ppm (s, 15H) at CF ₂ -CH ₂ , 3.49 ppm (m, 14H) at _2- C and 1.61 ppm (t, 4H)

Example 21: Synthesis of 1,8-bis (10-decenyloxy) -1H, 1H, 8H, 8H-perfluorooctane

In the same manner as in Example 1, 362.1 g (1 mol) of 1H, 1H, 8H, 8H-perfluoro-1,8-octanediol, 400 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, 1-decene was put into a dropping funnel and reacted to obtain 1,8-bis (10-decenyloxy) -1H, 1H, 8H, 8H-perfluorooctane (0.809 mol, yield 80.9%). The obtained product was analyzed by 300 MHz 1H magnetic resonance analysis and found to be C- CH ₂ -C at 1.32 ppm (m, 20H), OC- CH ₂ at 1.46 ppm (m, 4H) _{- CH 2, 3.53ppm (t,} 8H) O- CH 2, 5.70ppm (m, 2H) C- CH = C, it was confirmed to CC = CH ₂ peaks at 5.00ppm (d, 4H) in.

Example 22 Synthesis of 1- (10-decenyloxy) -8- (9,10-dibromodecyloxy) -1H, 1H, 8H, 8H-perfluorooctane

638.6 g (1 mol) of 1,8-bis (10-decenyloxy) -1H, 1H, 8H, 8H-perfluorooctane and 2400 ml of methoxynonafluorobutane were placed in the same manner as in Example 2, 159.8 g (1 mol) of bromine was added via a dropping funnel and reacted to give 1- (10-decenyloxy) -8- (9,10-dibromodecyloxy) -1H, 1H, 8H, 8H- 589.5 g (0.738 mol, yield 73.8%) of rurooctane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 3.53ppm (t, 8H) from _{O- CH 2, 1.46ppm (m,} 4H) C- CH 2 in _{OC- CH 2, 1.32ppm (m,} 20H) from - C, 1.96ppm (m, 2H) from the _{C = C- CH 2, 1.75ppm (} m, 2H) from _{Br-C- CH 2, 3.73ppm (} d, 2H) from Br- CH _2, 3.84ppm (m, 1H) C- CH = C peak was confirmed at Br- CH, 5.00ppm (d, 2H ) CC = CH 2, 5.70ppm (m, 1H in) from.

Example 23: 1 - (10- Decenyloxy ) -8- (9,10- Bis (perfluorohexyl-2-ethoxy) disiloxy ) - 1H, < / RTI > 8H, 8H - Of perfluorooctane  synthesis

(1 mol) of 1- (10-decenyloxy) -8- (9,10-dibromodecyloxy) -1H, 1H, 8H, 8H-perfluorooctane was obtained in the same manner as in Example 1, (3 mol) of 2- (perfluorohexyl) ethanol was added dropwise via a dropping funnel to a flask equipped with a stirrer, a stirrer, a stirrer, a stirrer, (Perfluorohexyl-2-ethoxy) decyloxy) -1H, 1H, 8H, 8H-perfluorooctane 1039.9 g (0.762 mol, yield 76.2%). The obtained product is in the 300MHz 1H magnetic resonance analysis, 1.32ppm (m, 20H) C- CH 2 -C, 1.46ppm (m, 4H) In _{OC- CH 2, 1.78ppm (t,} 4H) In the CF ₂ - _{CH 2, 1.96ppm (m, 4H} ) from the _{C = O- CH 2, 5.00ppm (} d, 2H) from the _{C- CH 2, 3.16ppm (m,} 1H) O- CH, 3.53ppm (m, 14H) from C = CH = C peak at CC = CH ₂ , 5.70 ppm (m, 1H).

Example 24: 1 - (11,11,18,18,18- Pentachloro -11,18- Disilaoctadecyloxy ) -8- (9,10- Bis (perfluorohexyl-2-ethoxy) disiloxy ) -1H, 1H, 8H, 8H-perfluorooctane Synthesis of

(Perfluorohexyl-2-ethoxy) decyloxy) -1H, 1H, 8H, 8H-purple in the same manner as in Example 4 (11), (11), (11), (11), and (11) were obtained by reacting 409.4 g (0.3 mol) of thiourea, (Perfluorohexyl-2-ethoxy) desilyloxy) -1H, 1H, 8H (18,18,18-pentacloro-11,18-disilaoctadecyloxy) , And 450.1 g (0.267 mol, yield 89.2%) of 8H-perfluorooctane. The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 6H) C- CH 2 -C, 1.46ppm (m, 4H) In _{Si- CH 2, 1.35ppm (m,} 34H) from OC- CH _{2, 3.53ppm (m, 14H)} CF 2 from _{O- CH 2, 1.78ppm (t,} 4H) in from _{CH 2, 3.16ppm (m, 1H} ) confirmed the O- CH peak.

Example 25: 1 - (11,11,18,18,18- Pentamethoxy -11,18- Disilaoctadecyloxy ) -8- (9,10- Bis (perfluorohexyl-2-ethoxy) disiloxy ) -1H, 1H, 8H, 8H-perfluorooctane Synthesis of

(11,11,18,18,18-pentachloro-11,18-disilaoctadecylsiloxy) -8- (9,10-bis (perfluorohexyl-2 (11mol) of trimethyl orthoformate was added to the reaction mixture, and the mixture was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) (9,10-bis (perfluorohexyl-2-ethoxy) desilyloxy) -1H, 9,10,11-tetramethyldisiloxane- 1H, 8H, 8H-perfluorooctane (0.186 mol, yield 93.2%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O -Si- CH 2, 1.30ppm (t, 4H) C- CH at _{Si- CH 2, 1.35ppm (m,} 34H) from _{2 -C, 1.46ppm (m, 4H} ) in _{OC- CH 2, 1.78ppm (t,} 4H) in the _{CF 2 - CH 2, 3.16ppm (} m, 1H) O- CH, 3.53ppm (m, 14H) from O- CH ₃ peak at O- CH ₂ , 3.55 ppm (s, 15H).

Example 26: Synthesis of 1,11-bis (11-undecenyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane

(1 mol) of 1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane-1,11-diol, 450 ml of dimethoxyethane, (3 mol) of tetrabutylammonium bromide were added and the mixture was stirred with a mechanical stirrer. 533.2 g (3 mol) of 11-chloro-1-undecene was placed in a dropping funnel and reacted to obtain 1,11-bis 11-undecenyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane (0.769 mol, yield 76.9%). The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (m, 24H) C- CH 2 -C, 1.46ppm (m, 4H) In _{OC- CH 2, 1.96ppm (m,} 4H) C = C in _{- CH 2, 3.55ppm (m,} 8H) O- CH 2, C- CH = C peak was confirmed in the _{CC = CH 2, 5.70ppm (m} , 2H) from 5.00ppm (d, 4H) in.

Example 27: 1 - (11- Undecenyloxy ) -11- (10,11- Dibromo undecyloxy ) - 1H, 1H, 11H, 11H - Perfluoro -3,6,9- Trioxide undecane  synthesis

(1 mol) of 1,1-bis (11-undecenyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane, 2800 ml of nonafluorobutane was added and stirred with a magnetic stirrer. 159.8 g (1 mol) of bromine was placed in a dropping funnel and reacted to obtain 1- (11-undecenyloxy) -11- (10,11-dibromoundecyloxy ) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane (7144 mol, yield: 74.4%). The obtained product 300MHz 1H magnetic resonance analysis, 1.45ppm (m, 26H) C- CH 2 -C, 1.46ppm (m, 4H) In _{OC- CH 2, 1.96ppm (m,} 2H) C = C in _{- CH 2, 3.55ppm (m,} 8H) from _{O- CH 2, 3.78ppm (d,} 2H) Br- CH 2, 3.84ppm (m, 1H) Br- CH, 5.00ppm (d, 2H) from at CC = CH _2, C- CH = C was confirmed that peaks at 5.70ppm (m, 1H).

Example 28: 1 - (11- Undecenyloxy ) -11- (10,11-bis (perfluorobutyl-3-propoxy) undecyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane

(10,11-dibromoundecyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9- (Perfluorobutyl) tetrabutylammonium bromide was added to the flask. The flask was charged with 874.5 g (1 mol) of trioxaldehyde, 250 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide and 48.4 g (3 mol) of propanol was placed in a dropping funnel and reacted to give 1- (11-undecenyloxy) -11- (10,11-bis (perfluorobutyl-3-propoxy) undecyloxy) 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane (0.803 mol, yield 80.3%). The obtained product was analyzed by 300 MHz 1H magnetic resonance analysis and found to be C = C- CH ₂ at 1.45 ppm (m, 34H), CF ₂ -CH ₂ at 1.61 ppm (t, _{C- CH 2, 3.16ppm (m,} 1H) O- CH, 3.62ppm (m, 14H) O- CH 2, 5.00ppm (d, 2H) CC = CH 2, 5.70ppm (m, 1H) from at The C- CH = C peak was identified.

Example 29: 1 - (12,12,21,21,21- Pentachloro -12,21- Disilachenoxysiloxy ) -11- (10,11-bis (perfluorobutyl-3-propoxy) undecyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane

(Perfluorobutyl-3-propoxy) undecyloxy) -1H, 1H, 11H, 11H-purple in the same manner as in Example 4 380.6 g (0.3 mol) of ruro-3,6,9-trioxandecane, a Spire catalyst and 207.9 g (0.6 mol) of 1,8-bis (dichlorosilyl) (trichlorosilyl) (10,11-bis (perfluorobutyl-3-propoxy) undeca-1- (12,12,21,21,21-pentachloro-12,21-disilachenecoxysiloxy) Silyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane was obtained in an amount of 446.8 g (0.276 mol, yield 92.2%). The obtained product in a hydrogen 300MHz nuclear magnetic resonance analysis, 1.30ppm (t, 6H) C- CH 2 -C, 1.61ppm (t, 4H) In _{Si- CH 2, 1.45ppm (m,} 50H) from CF ₂ - from _{CH 2, 3.16ppm (m, 1H} ) from O- CH, 3.62ppm (m, 14H ) confirmed the O- CH ₂ peak.

Example 30: 1 - (12,12,21,21,21- Pentamethoxy -12,21- Disilachenoxysiloxy ) -11- (10,11-bis (perfluorobutyl-3-propoxy) undecyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane

(12,12,21,21,21-pentachloro-12,21-disilachenecoxysiloxy) -11- (10,11-bis (perfluorobutyl-3 323.1 g (0.2 mol) of perfluoro-3,6,9-trioxandecane and 212.2 g (2 mol) of trimethyl orthoformate were placed in a reactor (12,12,21,21,21,21-pentamethoxy-12,21-disilachenecoxysiloxy) -11- (10,11-bis (perfluorobutyl-3- Propyloxy) undecyloxy) -1H, 1H, 11H, 11H-perfluoro-3,6,9-trioxandecane was obtained in an amount of 287.7 g (0.18 mol, yield 90.3%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O -Si- CH 2, 1.30ppm (t, 4H) C- CH at _{Si- CH 2, 1.45ppm (m,} 50H) from _{2 -C, 1.61ppm (t, 4H} ) in the _{CF 2 - CH 2, 3.16ppm (} m, 1H) O- CH, 3.55ppm (s, 15H) O- CH 3, 3.62ppm (m, 14H) from It was confirmed in the O- CH ₂ peak.

Example 31: Synthesis of 1,9-bis (4-butenyloxy) -1H, 1H, 9H, 9H-perfluorononane

(1 mol) of 1H, 1H, 9H, 9H-perfluoro-1,9-nonanediol, 450 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, 1-butene (271.6 g, 3 mol) was added thereto through a dropping funnel and reacted to obtain 1,9-bis (4-butenyloxy) -1H, 1H, 9H, 9H-perfluorononane (0.745 mol, yield 74.5%). The obtained product 300MHz 1H magnetic resonance analysis, 2.13ppm (m, 4H) in _{C = C- CH 2, 3.55ppm (} m, 8H) O- CH 2, 5.00ppm (d, 4H) CC = CH from _2, C- CH = C peak was confirmed at 5.70ppm (m, 2H).

Example 32: Synthesis of 1- (4-butenyloxy) -9- (3,4-dibromobutoxy) -1H, 1H, 9H, 9H-perfluorononane

520.3 g (1 mol) of 1,9-bis (4-butenyloxy) -1H, 1H, 9H, 9H-perfluorononane and 2000 ml of methoxynonafluorobutane were charged in the same manner as in Example 2, 159.8 g (1 mol) of bromine was poured through a dropping funnel and reacted to give 1- (4-butenyloxy) -9- (3,4-dibromobutoxy) -1H, 1H, 9H, 9H-perfluoro (0.724 mol, yield: 72.4%) was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.92ppm (m, 2H) from the _{OC- CH 2, 2.13ppm (m,} 2H) O- CH at _{C = C- CH 2, 3.55ppm (} m, 8H) In from _2, 3.78ppm (d, 2H) from _{Br- CH 2, 3.84ppm (m,} 1H) in Br- CH, 5.00ppm (d, 2H ) CC = CH 2, 5.70ppm (m, 1H) from the C- CH = C peak was confirmed.

Example 33: 1 -(4- Butenyloxy ) -9- (3,4- Bis (perfluorobutyl-2-ethoxy) butoxy ) - 1H, < / RTI > 9H, 9H - Perfluorononane  synthesis

680.1 g (1 mol) of 1- (4-butenyloxy) -9- (3,4-dibromobutoxy) -lH, 1H, 9H, 9H-perfluorononane was obtained in the same manner as in Example 1, 250 ml of ethane, 168.3 g (3 mol) of potassium hydroxide, and 48.4 g (0.15 mol) of tetrabutylammonium bromide were charged and stirred with a mechanical stirrer. 792.23 g (3 mol) of 2- (perfluorobutyl) ethanol was added through a dropping funnel The reaction was carried out to obtain 870.6 g of (1- (4-butenyloxy) -9- (3,4-bis (perfluorobutyl-2-ethoxy) butoxy) -1H, 1H, 9H, 9H-perfluorononane 0.832 mol, yield: 83.2%). The obtained product was analyzed by a 300 MHz hydrogen nuclear magnetic resonance spectroscopy. As a result, it was confirmed that C = C-H at OC- CH ₂ , 1.78 ppm (t, 4H) and CF ₂ -CH ₂ at 2.13 ppm (m, _{CH 2, 3.16ppm (m, 1H} ) O- CH, 3.55ppm (m, 14H) O- CH 2, 5.00ppm (d, 2H) C from _{CC = CH 2, 5.70ppm (m} , 1H) from at - CH = C peak was confirmed.

Example 34: 1 - (5,5,16,16,16- Pentachloro -5,16- Disilachexadecyloxy ) -9- (3,4- Bis (perfluorobutyl-2-ethoxy) butoxy ) -1H, 1H, 9H, 9H-perfluorononane

(4-butenyloxy) -9- (3,4-bis (perfluorobutyl-2-ethoxy) butoxy) -1H, 1H, 9H, 9H-perfluoro (5 mol%) was obtained by reacting 313.9 g (0.3 mol) of 3,4'-dicyclohexylcarbodiimide, 313.9 g (0.3 mol) (Perfluorobutyl-2-ethoxy) butoxy) -1H, 1H, 9H, 9H, 9H-perfluorononane (0.259 mol, yield 86.3%). The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 6H) OC- from _{C- CH 2 -C, 1.59ppm (m} , 2H) from the _{Si- CH 2, 1.32ppm (m,} 20H) in CH _{2, 1.78ppm (t, 4H)} CF 2 from the - CH _2, O- CH, CH ₂ O- was found to peak at 3.55ppm (m, 14H) from 3.16ppm (m, 1H).

Example 35: 1 - (5,5,16,16,16- Pentaethoxy -5,16- Disilachexadecyloxy ) -9- (3,4- Bis (perfluorobutyl-2-ethoxy) butoxy ) -1H, 1H, 9H, 9H-perfluorononane

(5,5,16,16,16-pentachloro-5,16-disilachexadecylsiloxy) -9- (3,4-bis (perfluorobutyl-2 (5mol) of triethyl orthoformate was reacted with 284.2g (0.2mol) of perfluorononane and 296.4g (1mol) of triethyl orthoformate, followed by distillation under reduced pressure. (Perfluorobutyl-2-ethoxy) butoxy) -1H, 1H, 6H-tetramethylhexadecyloxy-5,16,16,16- , 9H, 9H-perfluorononane (0.186 mol, yield 93.2%). The obtained product 300MHz Si- in hydrogen nuclear magnetic resonance analysis, 0.58ppm (t, 2H) OC- CH 3, 1.30ppm (t, 4H) In the _{O-Si- CH 2, 1.22ppm (} t, 15H) in CH _{2, 1.32ppm (m, 20H)} C- CH 2 -C, 1.59ppm (m, 2H) from the _{OC- CH 2, 1.78ppm (t,} 4H) in the CF ₂ from the _{- CH 2, 3.16ppm (m,} 1H ), the Si-O- CH ₂ peak was confirmed in the O- CH, 3.55ppm (m, 14H ) O- CH 2, 3.83ppm (d, 10H) in the.

Example 36: Synthesis of 1,10-bis (8-octenyloxy) -1H, 1H, 10H, 10H-perfluorodecane

(1 mol) of 1H, 1H, 10H, 10H-perfluoro-1,10-decanediol, 500 ml of dimethoxyethane, 168.3 g of 3,3 mol of potassium hydroxide, 3 g of tetrabutylammonium bromide (3 mol) of 8-chloro-1-octene was placed in a dropping funnel and reacted to obtain 1,10-bis (8-octenyloxy) -1H, 1H, 10H, 10H-perfluorodecane (0.781 mol, yield 78.1%). The obtained product 300MHz 1H magnetic resonance analysis, 1.35ppm (m, 16H) C- CH 2 -C, 1.96ppm (m, 4H) O in _{C = C- CH 2, 3.55ppm (} m, 8H) in The C- CH = C peak was identified at CC = CH ₂ , 5.70 ppm (m, 2H) at -CH ₂ , 5.00 ppm (d, 4H)

Example 37: Synthesis of 1- (8-octenyloxy) -10- (7,8-dibromomoctyloxy) -1H, 1H, 10H, 10H-perfluorodecane

682.52 g (1 mol) of 1,10-bis (8-octenyloxy) -1H, 1H, 10H, 10H-perfluorodecane and 2800 ml of methoxynonafluorobutane were charged in the same manner as in Example 2, 159.8 g (1 mol) of bromine was poured through a dropping funnel and reacted to give 1- (8-octenyloxy) -10- (7,8-dibromomoctyloxy) -1H, 1H, 10H, 620.6 g (0.736 mol, yield 73.6%) of rurodecane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.45ppm (m, 18H) C- CH 2 -C, 1.96ppm (m, 2H) O in _{C = C- CH 2, 3.55ppm (} m, 8H) in _{- CH 2, 3.78ppm (d,} 2H) from _{Br- CH 2, 3.84ppm (m,} 1H) in Br- CH, 5.00ppm (d, 2H ) CC = CH 2, 5.70ppm (m, 1H) from C- CH = C peak was confirmed.

Example 38: 1 -(8- Octenyloxy ) -10- (7,8- Bis (1H, 1H-perfluoropropoxy) octyloxy ) - 1H, 1H, 10H, 10H - Perfluorodecane  synthesis

(1 mol) of 1- (8-octenyloxy) -10- (7,8-dibromomoctyloxy) -1H, 1H, 10H, 10H-perfluorodecane in the same manner as in Example 1, (3 mol) of potassium hydroxide and 48.4 g (0.15 mol) of tetrabutylammonium bromide were placed in a flask, and 450.1 g (3 mol) of 1H, 1H-pentafluoropropanol was poured into the flask through a dropping funnel while stirring with a mechanical stirrer. The resulting mixture was reacted to obtain 770.7 g of 1- (8-octenyloxy) -10- (7,8-bis (1H, 1H-perfluoropropoxy) octyloxy) -1H, 1H, 10H, 0.786 mol, yield: 78.6%). The obtained product 300MHz 1H magnetic resonance analysis, 1.45ppm (m, 18H) C- CH 2 -C, 1.96ppm (m, 2H) O in _{C = C- CH 2, 3.16ppm (} m, 1H) from - CH, 3.55ppm (m, 14H ) C- CH = C peak was confirmed in the _{O- CH 2, 5.00ppm (d,} 2H) CC = CH 2, 5.70ppm (m, 1H) in.

Example 39: 1 -(8- Trichlorosilyloctyloxy ) -10- (7,8- Bis (1H, 1H-perfluoropropoxy) octyloxy ) -1H, 1H, 10H, 10H-Perfluorodecane Synthesis

(1H, 1H-perfluoropropoxy) octyloxy) -1H, 1H, 10H, 10H-perfluorooctanoyloxy-10- (8-trichlorosilyloctyloxy) -10- (7,8-bis (trifluoromethyl) cyclohexanecarboxylate) was obtained by reacting 294.2 g (0.3 mol) (1H, 1H-perfluoropropoxy) octyloxy) -1H, 1H, 10H, 10H-perfluorodecane (0.268 mol, yield 89.6%). The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 2H) from the _{Si- CH 2, 1.45ppm (m,} 20H) C- CH 2 -C, 1.96ppm (m, 2H) C = C in -CH ₂ peak at O- CH , 3.55 ppm (m, 14H) at -CH ₂ , 3.16 ppm (m, 1H)

Example 40: 1 -(8- Triethoxysilyloctyloxy ) -10- (7,8- Bis (1H, 1H-perfluoropropoxy) octyloxy ) -1H, 1H, 10H, 10H-Perfluorodecane Synthesis

(1H, 1H-perfluoropropoxy) octyloxy) -1H, 1H, 10H, 10H-1-indolecarboxamide were obtained in the same manner as in Example 5, 223.2 g (0.2 mol) of perfluorodecane and 296.4 g (2 mol) of triethyl orthoformate were put into a reaction vessel and the mixture was subjected to vacuum distillation to obtain 1- (8-triethoxysilyloctyloxy) -10- (1H, 1H-perfluoropropoxy) octyloxy) -1H, 1H, 10H, 10H-perfluorodecane 213.8g (0.187 mol, yield 93.4%). As a result of the 300 MHz 1H magnetic resonance analysis, the obtained product was analyzed by OC- CH ₃ at Si- CH ₂ , 1.22 ppm (t, 9H) and C- CH ₂ - at 1.45 ppm (m, 20H) at 0.58 ppm C, at 1.96ppm (m, 2H) from the _{C = C- CH 2, 3.16ppm (} m, 1H) O- CH, 3.55ppm (m, 14H) O- CH 2, 3.83ppm (d, 6H) in It confirmed the Si-O- CH ₂ peak.

Example 41: Synthesis of 1,12-bis (11-undecenyloxy) -1H, 1H, 12H, 12H-perfluorododecane

In the same manner as in Example 1, 562.1 g (1 mol) of 1H, 1H, 12H, 12H-perfluoro-1,12-dodecanediol, 600 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, Bromo-1,3-dicarboxylic anhydride was added to the mixture, and the mixture was stirred with a mechanical stirrer, and 533.2 g (3 mol) of 11-chloro-1-undecene was added thereto through a dropping funnel and reacted to obtain 1,12- 1H, 12H, 12H-perfluorododecane (0.831 mol, yield 83.1%). The obtained product 300MHz 1H magnetic resonance analysis, 1.40ppm (m, 28H) C- CH 2 -C, 1.96ppm (m, 4H) O in _{C = C- CH 2, 3.51ppm (} m, 8H) in The C- CH = C peak was identified at CC = CH ₂ , 5.70 ppm (m, 2H) at -CH ₂ , 5.00 ppm (d, 4H)

Example 42: Synthesis of 1- (11-undecenyloxy) -12- (10,11-dibromoundecyloxy) -1H, 1H, 12H, 12H-perfluorododecane

433.3 g (0.5 mol) of 1,12-bis (11-undecenyloxy) -1H, 1H, 12H, 12H-perfluorododecane and 2000 ml of methoxynonafluorobutane were charged in the same manner as in Example 2, (0.5 mol) of bromine was added via a dropping funnel and reacted to give 1- (11-undecenyloxy) -12- (10,11-dibromoundecyloxy) -1H, 1H, 12H, 768 g (0.748 mol, yield 74.8%) of 12H-perfluorododecane was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.45ppm (m, 30H) C- CH 2 -C, 1.96ppm (m, 2H) O in _{C = C- CH 2, 3.51ppm (} m, 8H) in _{- CH 2, 3.78ppm (d,} 2H) from _{Br- CH 2, 3.84ppm (m,} 1H) in Br- CH, 5.00ppm (d, 2H ) CC = CH 2, 5.70ppm (m, 1H) from C- CH = C peak was confirmed.

Example 43: 1 - (11- Undecenyloxy ) -12- (10,11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluorododecane

(1 mol) of 1- (11-undecenyloxy) -12- (10,11-dibromoundecyloxy) -1H, 1H, 12H, 12H- perfluorododecane in the same manner as in Example 1, 250 ml of dimethoxyethane, 168.3 g (3 mol) of potassium hydroxide, and 48.4 g (0.15 mol) of tetrabutylammonium bromide were placed and stirred with a mechanical stirrer. 504.1 g (3 mol) of 2H-hexafluoro-2-propanol was added dropwise into a dropping funnel And reacted to obtain 1- (11-undecenyloxy) -12- (10,11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluoro (0.805 mol, yield 80.5%) of decane. The obtained product 300MHz 1H magnetic resonance analysis, 1.45ppm (m, 30H) C- CH 2 -C, 1.96ppm (m, 2H) O in _{C = C- CH 2, 3.16ppm (} m, 1H) from - CH, 3.51ppm (m, 10H ) O- CH 2, 4.47ppm (s, 4H) O- CH 2 -CF 3, 5.00ppm (d, 2H) CC = CH 2, 5.70ppm (m at from, 1H), the C- CH = C peak was confirmed.

Example 44: 1 - (11- Trichlorosilyl undecyloxy ) -12- (10,11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluorododecane

(1H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H- (11-trichlorosilylundecyloxy) -12 (0.3 g) was obtained by reacting 360.2 g (0.3 mol) of perfluorododecane, 81.3 g (0.6 mol) of an Ashby Carstate catalyst and trichlorosilane, - (10,11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluorododecane in an amount of 339.9 g (0.254 mol, yield 84.8%). The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 2H) from the _{Si- CH 2, 1.45ppm (m,} 32H) C- CH 2 -C, 1.96ppm (m, 2H) C = C in - CH _2, at 3.16ppm (m, 1H) O- CH , 3.51ppm (m, 10H) O- CH 2, 4.47ppm (s, 4H) in was confirmed O- CH ₂ -CF ₃ peak.

Example 45: 1 - (11- Triethoxysilyl undecyloxy ) -12- (10,11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluorododecane

(1H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H (2H, , 12H-perfluorododecane (267.2 g, 0.2 mol) and triethyl orthoformate (296.4 g, 2 mol) were placed in a reaction vessel and the mixture was subjected to vacuum distillation to obtain 1- (11-triethoxysilylundecyloxy) , 11-bis (2H-hexafluoro-2-propoxy) undecyloxy) -1H, 1H, 12H, 12H-perfluorododecane was obtained in an amount of 250.8 g (0.184 mol, yield 91.8%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) C- CH at _{Si- CH 2, 1.22ppm (t,} 9H) Si-OC- CH 3, 1.45ppm (m, 32H) from _{2 -C, 1.96ppm (m, 2H} ) from the _{C = C- CH 2, 3.16ppm (} m, 1H) O- CH, 3.51ppm (m, 10H) O- CH 2, 3.83ppm (m, 6H in ), O- CH ₂ -CF ₃ peak was confirmed at Si-O- CH ₂ , 4.47 ppm (s, 4H).

Example 46: Synthesis of CH ₂ = CHCH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH = CH ₂ Synthesis of

400 g (0.1 mol) of SOLVAY-PFPE (Fluorolink D4000), 400 ml of dimethoxyethane, 56.11 g (1 mol) of potassium hydroxide and 4.8 g (0.015 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1, stir the reaction gives into the 3-chloro-1-propene 76.5g (1mol) via a dropping funnel _{CH 2 = CHCH 2 OCH 2 O} (CF 2 CF 2 O) p CH 2 OCH 2 CH = CH 2 389g (0.09 mol, 95.5% yield). The obtained product 300MHz 1H magnetic resonance analysis, 4.04ppm (d, 4H) O- CH 2 -C = C, 5.24ppm (d, 4H) O in _{CC = CH 2, 5.54ppm (s} , 4H) from - CH ₂ -O, it was confirmed the C- CH = C peak at 5.89ppm (m, 2H).

Example 47: Preparation of CH ₂ = CHCH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CHBrCH ₂ Synthesis of Br

Carried out in the same way as the example _{2 CH 2 = CHCH 2 OCH 2} O (CF 2 CF 2 O) p CH 2 OCH 2 CH = CH 2 100g (0.025mol), into a methoxy na butane 500ml fluoro stirring with a magnetic stirrer gives bromine 3.9g (0.025mol) was added dropwise to the reaction through a funnel into _{CH 2 = CHCH 2 OCH 2 O} (CF 2 CF 2 O) p CH 2 OCH 2 CHBrCH 2 Br 97.9g (0.023mol, 94.3% yield) ≪ / RTI > The obtained product 300MHz 1H magnetic resonance analysis, 3.73ppm (d, 2H) O- CH from _{O- CH 2, 4.04ppm (d,} 2H) from _{Br- CH 2, 3.82ppm (d,} 2H) from _2- C = C, 4.17ppm (m, 1H) in Br- CH, 5.24ppm (d, 2H ) from the _{CC = CH 2, 5.45ppm (s} , 4H) O- CH 2 -O, 5.89ppm (m, 1H in ), The C- CH = C peak was confirmed.

Example 48: Synthesis of CH ₂ = CHCH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ Synthesis of

Example 1 In the same manner as in _{CH 2 = CHCH 2 OCH 2 O} (CF 2 CF 2 O) p CH 2 OCH 2 CHBrCH 2 Br 100g (0.023mol), 100ml dimethoxyethane, potassium hydroxide 12.9g (0.23mol ) And tetrabutylammonium bromide (1.1 g, 0.0035 mol) were weighed in a mechanical stirrer, and 38.6 g (0.23 mol) of 2H-hexafluoro-2-propanol was added thereto via a dropping funnel to react with CH ₂ = CHCH ₂ OCH ₂ O (0.023 mol, yield: 96.2%) of (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ . The obtained product 300MHz 1H magnetic resonance analysis, 3.52ppm (d, 2H) from _{O- CH 2, 3.73ppm (d,} 2H) from CF ₃ -CO- CH _2, O- at 3.49ppm (m, 1H) CH, 4.04ppm (d, 2H) O- CH 2 -C = C, 4.47ppm (s, 2H) O- CH -CF 3, 5.24ppm (d, 2H) CC = CH 2, 5.45ppm in from ( s, 4H) C- CH = C peak was confirmed in the _{O- CH 2 -O, 5.89ppm (m} , 1H) in.

Example 49: Synthesis of SiCl ₃ (CH ₂ ) ₃ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ Synthesis of

At high temperatures, the nitrogen gas and dried on high-pressure reactor 290mL to a stainless pipe _{CH 2 = CHCH 2 OCH 2 O} (CF 2 CF 2 O) p CH 2 OCH 2 CH (OCH (CF 3) 2) CH 2 OCH (CF _{3) 2} 50g (0.012mol), L'rocks catalyst comprising platinum 1000ppm of the total weight of the reactants, trichlorosilane 31g (0.23mol), methyl-bis (trifluoromethyl) into 50ml of benzene was 24 hours at 130 . This solution was taken out into a round bottom flask, filtered and distilled under reduced pressure to obtain 48.2 g (0.01 mol, yield 93.5%) of F (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₁₁ SiCl ₂ CH ₂ SiCl ₃ . The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 2H) O- CH at _{Si- CH 2, 1.50ppm (m,} 2H) Si-C- CH 2, 3.45ppm (m, 6H) in O- CH ₂ -O at O- CH- CF ₃ and 5.45 ppm (s, 4H) at O- CH , 4.47 ppm (s, 2H) at ₂ , 3.49 ppm (m,

Example 50: Synthesis of Si (OMe) ₃ (CH ₂ ) ₃ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ Synthesis of

50 g (0.011 mol) of SiCl ₃ (CH ₂ ) ₃ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ was obtained in the same manner as in Example 5 (OMe) ₃ (CH ₂ ) ₃ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH ₃ CF ₂ O) ₂ (OCH ₃ ) ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ (0.01 mol, yield: 93.1%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O- CH at _{Si- CH 2, 1.50ppm (m,} 2H) Si-C- CH 2, 3.45ppm (m, 6H) in _{2, 3.49ppm (m, 1H)} O- CH, 3.55ppm (s, 9H) Si-O- CH 3, 4.47ppm (s, 2H) O- CH -CF 3, 5.45ppm (s, 4H in at ) it was confirmed O- CH ₂ -O peak at.

Example 51: Synthesis of SiCl ₃ (CH ₂ ) ₃ SiCl ₂ CH ₂ CH ₂ CH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ Synthesis of

50 g (0.011 mol) of CH ₂ CHCH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) _{2 in the} same manner as in Example 49, Spiers catalyst, 1,3-bis (dichloro-silyl) to put the (trifluoromethyl) benzene and 50ml reaction (trichlorosilyl) propane, 62.7g (0.23mol), bis _{SiCl 3 (CH 2) 3 SiCl} 2 CH 2 CH (0.01 mol, yield 92.5%) of ₂ CH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ . The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 6H) In _{Si- CH 2, 1.45ppm (m,} 4H) C- CH 2 -C, 3.45ppm (m, 6H) O- in CH _2, at 3.49ppm (m, 1H) O- CH , 4.47ppm (s, 2H) O- CH -CF 3, 5.45ppm (s, 4H) in was confirmed O- CH ₂ -O peak.

Example 52: Synthesis of Si (OMe) ₃ (CH ₂ ) ₃ Si (OMe) ₂ CH ₂ CH ₂ CH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ Synthesis of

Examples 5 and SiCl in the same manner _{3 (CH 2) 3 SiCl 2} CH 2 CH 2 CH 2 OCH 2 O (CF 2 CF 2 O) p CH 2 OCH 2 CH (OCH (CF 3) 2) CH 2 OCH ( CF _{3) 2} 50g (0.011mol) and trimethyl climb parcel mate _{11.7g (Si (OMe) 3 (} CH 2) 3 OCH 2 O (CF 2 CF 2 O) to put the reaction 0.11mol) was evaporated under reduced pressure through a _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ (0.01 mol, yield 95.2%). The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) O -Si- CH 2, 1.30ppm (t, 4H) C- CH at _{Si- CH 2, 1.45ppm (m,} 4H) from _{2 -C, 3.45ppm (m, 6H} ) from _{O- CH 2, 3.49ppm (m,} 1H) O- CH, 3.55ppm (s, 15H) O- CH 3, 4.47ppm (s, 2H) from at from _{O- CH -CF 3, 5.45ppm (s} , 4H) confirmed the O- CH ₂ -O peak.

Example 53: Synthesis of CH ₂ = CH (CH ₂ ) ₉ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH = CH ₂ Synthesis of

400 g (0.1 mol) of SOLVAY-PFPE (Fluorolink D4000), 400 ml of dimethoxyethane, 56.11 g (1 mol) of potassium hydroxide and 4.8 g (0.015 mol) of tetrabutylammonium bromide were charged in the same manner as in Example 1, (1 mol) of 11-chloro-1-undecenyl was added via a dropping funnel and reacted to give CH ₂ ═CH (CH ₂ ) ₉ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) (0.095 mol, yield 94.7%) of ₉ CH = CH ₂ . The obtained product was analyzed by C- CH ₂ -C, 1.46 ppm (m, 4H) at OC = C- CH ₂ , 1.30 ppm (m, 24H) _{- CH 2, 3.37ppm (t,} 4H) O- CH 2, 5.00ppm (d, 4H) O- CH 2 -O in _{C = CH 2, 5.45ppm (s} , 4H) in, 5.70ppm (m, 2H), the C = CH- C peak was confirmed.

Example 54: Synthesis of CH ₂ = CH (CH ₂ ) ₉ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CHBrCH ₂ Synthesis of Br

Carried out the same way as in Example 2 to _{CH 2 = CH (CH 2)} 9 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) a _{9 CH = CH 2 100g (0.023mol} ), methoxy nonafluoro put butane 500ml gives stirring with a magnetic stirrer into the reaction via the dropwise addition of bromine 3.7g (0.023mol) funnel _{CH 2 = CH (CH 2)} 9 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH ₂ ) 97.2 g (0.022 mol, yield 93.7%) of ₉ CHBrCH ₂ Br was obtained. The obtained product was analyzed by 300 MHz 1H magnetic resonance analysis and found to be C- C ₂ C at 1.30 ppm (m, 26H), OC- CH ₂ at 1.46 ppm (m, 4H) _{- CH 2, 3.37ppm (t,} 4H) from _{O- CH 2, 3.73ppm (d,} 2H) Br- CH 2, 3.84ppm (m, 1H) Br- CH, 5.00ppm (d, 2H) from at C = CH _2, C = CH were identified from the peak -C _{O- CH 2 -O, 5.70ppm (m} , 1H) at 5.45ppm (s, 4H).

Example 55: Synthesis of CH ₂ = CH (CH ₂ ) ₉ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH (OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ ) CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ Synthesis of

Example 1 In the same manner as _{CH 2 = CH (CH 2)} 9 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CHBrCH 2 Br 100g (0.022mol), 100ml dimethoxyethane, potassium (Perfluorooctyl) ethanol (102.1 g, 0.22 mol) were placed in a dropping funnel, and the reaction was carried out to obtain a solution of CH _{2 = CH (CH 2) 9} OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3) CH 2 OCH 2 CH 2 (CF 2 ) ₇ CF ₃ 106 g (0.02 mol, yield 90.5%). The obtained product was analyzed by 300 MHz hydrogen nuclear magnetic resonance analysis and found to be C = C- CH ₂ at 1.30 ppm (m, 30H) and CF ₃ -CH ₂ at 1.78 ppm (t, 4H) _{C- CH 2, 3.16ppm (m,} 1H) O- CH, 3.42ppm (m, 10H) C = CH 2, 5.45ppm (s, 4H) from _{O- CH 2, 5.00ppm (d,} 2H) from C = CH were identified from the peak -C _{O- CH 2 -O, 5.70ppm (m} , 1H) in.

Example 56: Synthesis of SiCl ₃ (CH ₂ ) ₁₁ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH (OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ ) CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ Synthesis of

Carried out the same way as example 49 by _{CH 2 = CH (CH 2)} 9 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3) CH 50 g (0.01 mol) of ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF _{3, 25} g (0.19 mol) of tristrolosilane and 50 ml of bis (trifluoromethyl) benzene were reacted to prepare SiCl _{3 2} ) ₃ SiCl ₂ CH ₂ CH ₂ CH ₂ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ (0.009 mol, 93.4%). The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (t, 2H) from the _{Si- CH 2, 1.30ppm (m,} 34H) from _{C- CH 2 -C, 1.78ppm (t} , 4H) in CF ₃ - _{CH 2, 3.16ppm (m, 1H} ) O- CH 2 -O peak was confirmed in the O- CH, 3.42ppm (m, 10H ) O- CH 2, 5.45ppm (s, 4H) in.

Example 57: Synthesis of Si (OMe) ₃ (CH ₂ ) ₁₁ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH (OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ ) CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ Synthesis of

Examples 5 and SiCl in the same manner _{3 (CH 2) 11 OCH 2} O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3) CH 2 OCH _{2 CH 2 (CF 2) 7} CF 3 50g (0.0093mol) and trimethyl climb _{Si (OMe) 3 (CH 2} ) to insert the package mates 9.8g (0.093mol) via the reaction was evaporated under reduced pressure to ₃ OCH ₂ O (CF ₂ 45.0 g (0.0085 mol, yield 91.5%) of CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 0.58ppm (t, 2H) from the _{Si- CH 2, 1.30ppm (m,} 34H) from _{C- CH 2 -C, 1.78ppm (t} , 4H) in CF ₃ - _{CH 2, 3.16ppm (m, 1H} ) O- CH, 3.42ppm (m, 10H) O- CH 2, 3.55ppm (s, 9H) O from _{O- CH 3, 5.45ppm (s,} 4H) in at - CH ₂ -O peak.

Example 58: Synthesis of SiCl ₃ CH ₂ SiCl ₂ (CH ₂ ) ₁₁ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH (OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ ) CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ Synthesis of

Carried out the same way as example 49 by _{CH 2 = CH (CH 2)} 9 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3) CH 50 g (0.01 mol) of ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ , 47.5 g (0.19 mol) of bis (trichlorosilyl) methane, by the insert reaction _{SiCl 3 CH 2 SiCl 2 (CH} 2) 11 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3) CH 2 47.9 g (0.009 mol, yield 93.4%) of OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ was obtained. The obtained product 300MHz 1H magnetic resonance analysis, 1.30ppm (m, 34H) from _{C- CH 2 -C, 1.35ppm (m} , 4H) In _{Si- CH 2, 1.78ppm (t,} 4H) in CF ₃ - _{CH 2, 3.16ppm (m, 1H} ) O- CH 2 -O peak was confirmed in the O- CH, 3.42ppm (m, 10H ) O- CH 2, 5.45ppm (s, 4H) in.

Example 59: Si (OMe) ₃ CH ₂ Si (OMe) ₂ (CH ₂ ) ₁₁ OCH ₂ O (CF ₂ CF ₂ O) _p CH ₂ O (CH ₂ ) ₉ CH (OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ ) CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ of  synthesis

Examples 5 and SiCl in the same manner _{3 CH 2 SiCl 2 (CH 2} ) 11 OCH 2 O (CF 2 CF 2 O) p CH 2 O (CH 2) 9 CH (OCH 2 CH 2 (CF 2) 7 CF 3 (OMe) ₃ (CH ₂ ) ₃ OCH ₂ (OMe) ₃ was obtained by distillation under reduced pressure by adding 50 g (0.0092 mol) of CH ₂ OCH ₂ CH ₂ (CF ₂ ) ₇ CF ₃ and 9.8 g (0.093 mol) of trimethyl orthoformate, O (CF ₂ CF ₂ O) _p CH ₂ OCH ₂ CH (OCH (CF ₃ ) ₂ ) CH ₂ OCH (CF ₃ ) ₂ (0.0084 mol, yield 91.2%). The obtained product 300MHz 1H magnetic resonance analysis, 0.6ppm (m, 2H) Si in the _{C- CH 2 -C, 1.35ppm (m} , 2H) from the _{Si- CH 2 -Si, 1.30ppm (m} , 34H) from _{- CH 2, 1.78ppm (t,} 4H) in _{CF 3 - CH 2, 3.16ppm (} m, 1H) O- CH, 3.42ppm (m, 10H) O- CH 2, 3.55ppm (s, 15H) in O- CH ₂ -O peak at Si-O- CH ₃ , 5.45 ppm (s, 4H).

The silicone compound according to the present invention can be used as a surface treating agent for a touch screen display. The silicone compound according to the present invention is excellent in friction durability and allows the coating to have improved adhesion properties while leaving fingerprints on the surface of the display.

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 (10)

(9)
Formula 9

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, X ³ = OR or _{(CH 2) q Si (OR} ) , and the _3, q = 1 , 2, 3, 4, 6, 8, 10 or 11, and R is Me or Et. (8)
8

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) m CF , and the _second, and is a = 1 or 2, X ² = Cl or (CH _2), and the _q SiCl _3, q = 1, 2, 3, 4, 6, 8, 10 or 11, and R is Me or Et. (6)
6

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or F (CF ₂ ) _a ((CF ₂ ) ₂ O) _m CF ₂ , a = 1 or 2, and R is Me or Et. (4)
Formula 4

,
In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p and X ¹ = Br or I is 1 to 12, Y = F, CF ₃ and p = And n is 1, 2, 4, 6, 8 or 9, m is 0, 1, 2 or 3, and R is Me or Et. Is a compound represented by the formula (9) which is obtained by the reaction of the trimethyl / ethyl oxosuccinate of the compound represented by the formula (8)
8

Formula 9

In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, and the X ² = Cl or _{(CH 2) q SiCl 3,} X 3 = OR or ( CH ₂ ) _q Si (OR) _{3 wherein} q is 1, 2, 3, 4, 6, 8, 10 or 11 and R is Me or Et. Gt; The compound represented by the formula (8) is obtained by the reaction of the compounds represented by the formulas (6) and (7)
6

Formula 7
H-SiCl ₂ -X ²
In the above, Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , where o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, n = , and the 6, 8 or 9, m = 0, and is 1, 2 or 3, Rf ¹ is a _{CH (CF 3) 2, F} (CF 2) o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and is a = 1 or 2, and the X ² = Cl or _{(CH 2) q SiCl 3,} X 3 = OR or ( CH ₂ ) _q Si (OR) _{3 wherein} q is 1, 2, 3, 4, 6, 8, 10 or 11 and R is Me or Et. Gt; The method of claim 6,
The compound represented by the formula (6) is obtained from the compound represented by the formula (4) and the formula (5)
Formula 4

Formula 5
HO (CH ₂ ) _m (R f ¹ )
In the Rf is (CF _{2) o,} (CF ₂ OCF _{2) o,} or _{O (CF (Y) CF 2} O) , and the _{p, o = 1 ~ 12,} Y = F, CF 3, p = is a 2 ~ 200, Rf ¹ is a CH (CF _{3 ) 2, F (CF 2)} o Or _{F (CF 2) a ((} CF 2) 2 O) and the _m CF _2, and ^{a = 1, 2, X 1} = is a Br or I, n = 1, 2, 4, 6, 8 or 9 , M is 0, 1, 2 or 3, and R is Me or Et. [7] The method according to claim 7, wherein the compound represented by the general formula (4) is obtained by a halogenation reaction of one of the compounds represented by the general formula (3)
(3)
_{CH 2 = CH (CH 2)} n O (CH 2) m (Rf) (CH 2) m O (CH 2) n CH = CH 2,
In the Rf is (CF _{2) o,} (CF ₂ OCF ₂ ) _o or O (CF (Y) CF ₂ O) _p , wherein o = 1 to 12, Y = F, CF ₃ , p = 2 to 200, m is 1, 2 or 3 , N is 0 or 1, and R is Me or Et. ≪ RTI ID = 0.0 > 11. < / RTI > The method according to claim 5, wherein the reaction solvent is methanol, ethanol, trimethylorthoformate or triethylorthoformate. The process according to claim 6, wherein the reaction solvent comprises 1,3-bis (trifluoromethyl) benzene, and the catalyst is a spire, a carstate, an Otsuko, an ash- Wherein the fluoro silicone compound is a fluoro silicon compound.