불소화 다이알킬 다이아크릴레이트 실란 화합물 및 이의 제조방법
The present invention refers to a method relates to fluorinated dialkyl diacrylate silane compound of formula 1 to tank and number, of fluorinated dialkyl diacrylate silane compound is represented for formula 1 have excellent optical properties and mechanical properties for a flat display for transparent high pressure liquid coolant addition number number are useful as disclosed. In addition, formula 1 of fluorinated dialkyl diacrylate silane compound is represented for refractive index 1. 28 To 1. 40 Hereinafter with respect to the refractive index of the antireflection film can be reduced rate established for mechanical durability and good physical property of antireflective film can be useful as coating material. [Formula 1] Franchises CRT monitor, such as CRT TV for CPT, TFT-a LCD polarizing plate, PDP filter, RPTS filter, and a non-liquid crystal from watch, photograph, such as a variety of display to frame up to the respectively disclosed. This display when exposed to light such as imaged by additive or feel that the eye fatigue induced headache, eye Image within a display to be made clearly not as an etch mask processes Image (contrast) temperature of the liquid crystal occurs. In order to solve the same, a low relative dielectric constant than active layer substrate articles from the light reduction studies using antireflection film formation is not disclosed. Such an order function glass, plastic film or the like applying a hardcoat layer hard coating agent, refractive index 1. 6 Or more stacked liquid coating materials having high index of refraction refraction rate, refractive index 1. 3 ∼ 1. 5 Low refractive index coating solution are stacked is that index of refraction layer has a laminated structure. The great cookies a complicated process that refraction layer 2 be directly converted to hard in coating layer using the layer structure. In that index of refraction layer material comprises a low refractive indices as well as the required high visible light transmission, durability, stain resistance, mechanical strength and the like to 10sup16. In addition mass coating used in roll coat method, him expense oh the coating law, slide coating, spray coating, screen printing such as coatings and UV curing type such as coin mass and ease of continuous etc. also required simultaneously. The anti-reflection that index of refraction fluorine-based material, a fluorine-containing polyfunctional (meta) acrylic esters 10 - 182745 Japanese publicized patent Official Gazette plain ring obtained by polymerizing monomer compositions containing low refractive index fluorine material disclosure corrosion disclosed. However in the case of fluorine containing a fluoroalkyl group of fluorine content less and as a result the rate and the amount of acrylic acid ester content of fluorine bonded together transparency etc. number exists in the sixth point. The fluorine-based coating composition provides many conventional low refractive index as an antireflective reviewed but, while strong 1 layer coating antireflection effect low refractive index and has a satisfactory mechanical strength sufficient enough to obtain a contrast solution and method etc. is required. Thus, the purpose of the invention have a low refractive index transparent high pressure liquid coolant addition number number of flat panel display for a number fluorinated dialkyl diacrylate silane compounds and their manufacturing method useful as 30 to 60 seconds. The present invention refers to a method relates to fluorinated dialkyl diacrylate silane compound of formula 1 to tank and number, of fluorinated dialkyl diacrylate silane compound is represented for formula 1 have excellent optical properties and mechanical properties for a flat display for transparent high pressure liquid coolant addition number number are useful as disclosed. In addition, formula 1 of fluorinated dialkyl diacrylate silane compound is represented for refractive index 1. 28 To 1. 40 Hereinafter with respect to the refractive index of the antireflection film can be reduced rate established for mechanical durability and good physical property of antireflective film can be useful as coating material. [Formula 1] [In formula said, R1 To R4 Are each independently a hydrogen, (C1 - C20) alkyl or (C6 - C20) it will be biting and, R1 And R2 Hydrogen is not simultaneously; M and n independently of each other integer number of 2 to 10; A, B, D and E are each independently a hydrogen, (C1 - C4) alkyl and fluorine or, stage A, B, D and E of at least 50% of the total content of the content of bastnasite; Said R1 To R4 It will be biting can be further substituted alkyl and fluorine.] The present invention according to formula 1 fluorine-substituted dialkyl diacrylate silane compound is represented number de in the presence of hydrochloric acid, fluorinated dialkyl silane compound of formula 2, formula 3 - 1 of the claw which will know the id number encoded the claw which will know the id compound of formula 3 - 2 and a process tank. [Formula 1] [Formula 2] [Formula 3 - 1] [Formula 3 - 2] [In formula said, R1 To R4 Are each independently a hydrogen, (C1 - C20) alkyl or (C6 - C20) it will be biting and, R1 And R2 Hydrogen is not simultaneously; M and n independently of each other integer number of 2 to 10; A, B, D and E are each independently a hydrogen, (C1 - C4) alkyl and fluorine or, stage A, B, D and E of at least 50% of the total content of the content of bastnasite; Said R1 To R4 It will be biting can be further substituted alkyl and fluorine.] In the process used solvent anhydride d ethyl ether, tetrahydrofuran, methylene chloride or the like cited, said number of fluorinated dialkyl silane compound of formula 2 is de hydrochloric acid 2. 0 To 2. 5 Equivalent use of a good ancestry. In addition, number of hydrochloric acid used include pyridine or triethylamine etc. de. Said reaction temperature is 0 to 25 °C but is normally in a non-solvent depending on embodiment as follows. The reaction time is reaction temperature depending on the solvent for use with but, typically 30 6 time of sulfates, preferably 2 time hereinafter react at other. The number of said formula 2 fluorinated dialkyl silane compound is represented two method , silane compound of formula 4 by one method for catalyst magnesium, bromo compound of formula 5 - 1 is the [tu fluorinated bromo alcohol compound of formula 5 - 2 and fluorinated reacting in a bath to 25 °C -78 °C green number are disclosed. [Formula 2] [Formula 4] [Formula 5 - 1] [Formula 5 - 2] [In formula said, R1 , R2 , M, n, A, B, D and E is defined in said formula 1 are the same.] In the process used as solvent anhydride d ethyl ether, tetrahydrofuran, hexane, heptane in combination of two or more solvents and a single solvent and impedance, the magnesium said silane compound of formula 4 normal 2. 0 To 2. 1 Equivalent use of a good ancestry. The reaction temperature is but a non-solvent is normally depending on -78 to 25 °C and, preferably lithium substituted reaction is -78 °C and in embodiment - chloro, bromo alcohol compound of formula 5 - 1 and 5 - 2 to 25 °C -10 reaction is fluorinated in embodiment as follows. The reaction time is reaction temperature depending on the solvent for use with but, typically 30 6 time of sulfates, preferably 2 time hereinafter react at other. (C1 - C10) alkyl lithium in the presence of the fluorinated dialkyl silane compound of said formula 2 other manufacturing method for silane compound of formula 4, bromo compound of formula 5 - 2 to 25 °C -78 °C fluorinated bromo alcohol compound of formula 5 - 1 and fluorinated anionic in reacting a number tank are disclosed. [Formula 2] [Formula 4] [Formula 5 - 1] [Formula 5 - 2] [In formula said, R1 , R2 , M, n, A, B, D and E is defined in said formula 1 are the same.] In the process used as solvent anhydride d ethyl ether, tetrahydrofuran, hexane, heptane in combination of two or more solvents and a single solvent and impedance, said alkyl lithium organometallic reagent include n - butyl lithium, sec - butyl lithium, tert - butyl lithium as to the aromatic hydrocarbon can be, silane compound of formula 4 normal 2. 0 To 2. 1 Equivalent use of a good ancestry. The reaction temperature is but a non-solvent is normally depending on -78 to 25 °C and, preferably lithium substituted reaction is -78 °C and in embodiment - chloro, bromo alcohol compound of formula 5 - 1 and 5 - 2 to 25 °C -10 reaction is fluorinated in embodiment as follows. The reaction time is reaction temperature depending on the solvent for use with but, typically 30 6 time of sulfates, preferably 1 time hereinafter react at other. The present invention according to formula 1 of fluorinated dialkyl diacrylate silane compound is represented 1. 28 To 1. 40 Has a refractive index of, preferably 1. 28 To 1. 35 Has a refractive index. Examples of compounds of the plate and to said fluorinated dialkyl dia silane compound, limited to are not correct. The present invention according to fluorinated dialkyl diacrylate silane compound is represented 1. 28 To 1. 40 Have a low index of exhibits excellent optical properties and mechanical properties for a flat display for transparent high pressure liquid coolant addition number number are useful as disclosed. In addition, the present invention according to fluorinated dialkyl diacrylate silane compound is represented 2 deposition step process number bath in high yield and purity can be disclosed. In the embodiment and comparison of the present invention relate to a effect of the invention to specifically described as follows. Stage, an example embodiment for the present invention to exemplify only, or limit the scope of the present invention adopts a endured. [In the embodiment 1] fluorinated dialkyl diacrylate silane compound number bath The step of reacting the reaction process to form a number 1 and number 2 via the present invention according to various fluorinated dialkyl diacrylate silane compound number was high pressure liquid coolant. The step of reacting the><number 1 5L (THF) tetrahydrofuran mixable -78 °C and then placed in the reaction cap to cooling, a silane compound (reactant I) to table 1 5mol, magnesium turning 5mol and fluorinated bromo compound (reactant II) 5mol 10 minutes stirring at ambient temperature for heating said reaction cap is charged into a sequentially gradually after 30 1. 5 Stirring time-gate. After completing the hydrochloric acid (HCl) for 1 to 3 said water agitation 500g 1L 20 minutes after reaction cap applied to terminate his reaction. Water is evaporated completely after THF completely transparent ground THF layer into separate layers, product fluorinated dialkyl silane compound separating column was positive number. The yield 51. 7 To 66. The 7%, based on table 1 by each compound by using a transparent conductive layer, each of each compound in addition number produced therewith1 H NMR are described. The step of reacting the><number 2 3L methylene chloride (MC) to table 2 at room temperature into and out of the reaction cap to a number 1 and the claw which will know the id compound (reactant III) 3mol 3mol composition obtained in the reaction process which can be obtained, which can be triethylamine 11mol 1 with respect to the reaction time. On completion of the reaction by adding water was 20 minutes. Ground water is evaporated completely after MC MC completely transparent layer into separate layers, product fluorinated dialkyl diacrylate silane compound separating column was positive number. The yield 70. 3 To 90. To 5%, based on a transparent conductive layer for each compound according to table 2, table 2 is each prepared by the number of1 H NMR are described. Each compound of tungsten lamp light refractive index of the 589 nm light source (model name: 2T, Japanese ATAGO ABBE) using D readings measured by use of a transparent conductive layer, having a refractive index of each compounds 1 to 3 as a table. 28 To 1. 40 Min. PURPOSE: A fluorinated dialkyl diacrylate silane compound and a method for preparing the same are provided to ensure excellent optical property and mechanical property and to be used as an additive for manufacturing an anti-reflection film. CONSTITUTION: A fluorinated dialkyl diacrylate silane compound is denoted by chemical formula 1. A method for preparing the fluorinated dialkyl diacrylate silane compound comprises: a step of reacting a fluorinated dialkyl silane compound of chemical formula 2, an acylchloride compound of chemical formula 3-1, and an acylchloride compound of chemical formula 3-2 under the presence of a dehydrochlorinating agent. To fluorinated dialkyl diacrylate silane compound of formula 1. [Formula 1] [In said formula 1, R1 To R4 Are each independently a hydrogen, (C1 - C20 ) Alkyl or (C6 - C20 ) It will be biting and, R1 And R2 Hydrogen is not simultaneously; n and m independently of each other integer number of 2 to 10; A, B, D and E are each independently a hydrogen, fluorine or (C1 - C4 ) And alkyl, stage A, B, content of 50 mole % or more and the content of the total atomic weight of D and E bastnasite; said R1 To R4 It will be biting can be further substituted alkyl and fluorine.] According to Claim 1, characterized to structure chosen from fluorinated dialkyl diacrylate silane compound. In the presence of hydrochloric acid number de, fluorinated dialkyl silane compound of formula 2, formula 3 - 1 of the claw which will know the id compounds represented by formula 1 to formula 3 - 2 of the claw which will know the id compound and fluorine substituted dialkyl diacrylate silane compound to yield a manufacturing method including formula 1 fluorine-substituted dialkyl diacrylate silane compound. [Formula 1] [Formula 2] [Formula 3 - 1] [Formula 3 - 2] [Said formula 1, 2, 3 - 1 and 3 - 2 in, R1 To R4 Are each independently a hydrogen, (C1 - C20 ) Alkyl or (C6 - C20 ) It will be biting and, R1 And R2 Hydrogen is not simultaneously; n and m independently of each other integer number of 2 to 10; A, B, D and E are each independently a hydrogen, fluorine or (C1 - C4 ) And alkyl, stage A, B, content of 50 mole % or more and the content of the total atomic weight of D and E bastnasite; said R1 To R4 It will be biting can be further substituted alkyl and fluorine.] According to Claim 3, fluorinated dialkyl silane compound is represented by formula 2 of magnesium catalyst to silane compound of formula 4, bromo compound of formula 5 - 1 is the [tu fluorinated bromo alcohol compound of formula 5 - 2 and fluorinated -78 °C to 25 °C manufacturing method characterized by reacting the number bath in green. [Formula 2] [Formula 4] [Formula 5 - 1] [Formula 5 - 2] [Said formula 2, 4, 5 - 1 and 5 - 2 in, R1 , R2 , M, n, A, B, D and E is the definition of claim according to Claim 3 are the same.] According to Claim 3, formula 2 of fluorinated dialkyl silane compound is represented (C1 - C10 ) To formula 4 in the presence of lithium alkyl silane compound, of formula 5 - 1 fluorinated bromo alcohol compound and reacting the bromo alcohol compound of formula 5 - 2 fluorinated -78 °C to 25 °C number tank manufacturing method characterized. [Formula 2] [Formula 4] [Formula 5 - 1] [Formula 5 - 2] [Said formula 2, 4, 5 - 1 and 5 - 2 in, R1 , R2 , M, n, A, B, D and E is the definition of claim according to Claim 3 are the same.] According to Claim 3, of hydrochloric acid is pyridine or triethylamine and de said number, said reaction is carried out in the manufacturing method characterized 0 to 25 °C. No. R1 =R2 A=B=D=E N=m Reaction number 1 (%) The step of reacting the product number 11 HNMR 1 Me F 2 66. 7 Δ 2. 00 (1H, s), 0. 21 (3H, s) 2 Me F 3 63. 1 Δ 2. 02 (1H, s), 0. 21 (3H, s) 3 Me F 4 58. 2 Δ 2. 03 (1H, s), 0. 21 (3H, s) 4 Me F 6 56. 6 Δ 2. 05 (1H, s), 0. 21 (3H, s) 5 Et F 2 61. 3 Δ 2. 00 (1H, s), 0. 86 (3H, t), 0. 66 (2H, q) 6 Et F 4 55. 4 Δ 2. 03 (1H, s), 0. 87 (3H, t), 0. 66 (2H, q) 7 N a-Bu F 2 54. 5 Δ 2. 00 (1H, s), 1. 31 (4H, m), 0. 90 (3H, t), 0. 62 (2H, t) 8 N a-Bu F 3 51. 7 Δ 2. 01 (1H, s), 1. 32 (4H, m), 0. 91 (3H, t), 0. 62 (2H, t) No. R1 =R2 A=B=D=E N=m R3 =R4 Reaction number 2 (%) The step of reacting the product number 21 HNMR 9 Me F 2 H 90. 5 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 00 (1H, s), 0. 21 (3H, s) 10 Me F 2 Me 83. 3 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 03 (1H, s), 0. 21 (3H, s) 11 Me F 4 H 87. 6 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 04 (1H, s), 0. 22 (3H, s) 12 Me F 4 Me 82. 1 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 06 (1H, s), 0. 22 (3H, s) 13 Me F 6 H 85. 8 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 02 (1H, s), 0. 86 (3H, t), 0. 65 (2H, q) 14 Me F 6 Et 70. 3 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 04 (1H, s), 0. 87 (3H, t), 0. 66 (2H, q) 15 Et F 2 H 87. 0 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 03 (1H, s), 1. 33 (4H, m), 0. 91 (3H, t), 0. 61 (2H, t) 16 Et F 2 N a-Bu 72. 2 Δ 6. 27 (1H, dd), 6. 05 (1H, q), 5. 59 (1H, dd), 2. 05 (1H, s), 1. 35 (4H, m), 0. 92 (3H, t), 0. 62 (2H, t) No. Structure Refractive index 9 1. 35 10 1. 36 11 1. 33 12 1. 32 13 1. 28 14 1. 30 15 1. 36 16 1. 40