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Organosilicon compounds, production processes thereof, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers and liquid crystal displays

a technology of organosilicon and organic compounds, applied in the field of organic compounds, can solve the problems of high potential risk of breaking the costly liquid cell, difficulty in increasing the size beyond 20 inches, and increasing the move toward larger panels, etc., to achieve excellent rework capability, excellent long-term durability, and excellent coordination property

Inactive Publication Date: 2010-03-11
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides an organosilicon compound that can be used in a pressure-sensitive adhesive composition, which has low initial adhesive force but high adhesive force under high temperature or high humidity conditions. This compound has excellent rework capability and long-term durability when bonded to optical films or other substrates. The invention also provides a production process for this compound and a pressure-sensitive adhesive composition, self-adhesive polarizer, and liquid crystal display that use this compound.

Problems solved by technology

In the case of LCDs, there is an ever-increasing move toward larger panels, contrary to the early-stage expectation that a size increase beyond 20 inches would be difficult.
If a conventional pressure-sensitive adhesive having high adhesiveness is used, this high adhesiveness makes it difficult to remove the optical film upon its separation due to the high adhesiveness force and moreover, is accompanied by a high potential risk of breaking the costly liquid cell.
As a consequence, the use of such a conventional pressure-sensitive adhesive leads to a significant increase in manufacturing cost.
Otherwise, there is a potential problem that bubbling, separation and / or the like may take place to lower the durability.
However, the silane coupling agent is obtained by reacting an isocyanatosilane and 2-pyridinol in the presence of a catalyst, and a hydroxyl group of 2-pyridinol non-selectively reacts to both the isocyanato group and hydrolyzable silyl group of the silane.
Accordingly, the silane coupling agent does not have such a single structure as the disclosed silane, and is insufficient in the improvements of various self-adhesion properties.

Method used

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  • Organosilicon compounds, production processes thereof, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers and liquid crystal displays
  • Organosilicon compounds, production processes thereof, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers and liquid crystal displays
  • Organosilicon compounds, production processes thereof, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers and liquid crystal displays

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

[0091]In a 1-L separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 31.4 g (0.33 mol) of 2-aminopyridine was placed, followed by charging of 150 g of tetrahydrofuran. The resultant mixture was stirred into a solution. Into the solution, 82.5 g (0.33 mol) of 3-isocyanatopropyltriethoxysilane was charged dropwise, and the thus-obtained mixture was stirred under heating at 70° C. for 4 hours. Subsequently, it is confirmed by IR measurement that an absorption peak attributable to the isocyanato group in the reactant 3-isocyanatopropyltriethoxy-silane had disappeared completely and instead, an absorption peak attributable to a urea bond had been formed, the reaction was determined to be completed. The solvent was then distilled off to obtain the reaction product, which was a pale yellow liquid and had a viscosity of 184 mm2 / s, a specific gravity of 1.094 and a refractive index of 1.4975. The reaction product was confirmed by GPC to be consiste...

synthesis example 2

[0092]In a 1-L separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 31.7 g (0.33 mol) of 2-aminopyrimidine was placed, followed by charging of 150 g of tetrahydrofuran. The resultant mixture was stirred into a solution. Into the solution, 82.5 g (0.33 mol) of 3-isocyanatopropyltriethoxysilane was charged dropwise, and the thus-obtained mixture was stirred under heating at 70° C. for 4 hours. Subsequently, it is confirmed by IR measurement that an absorption peak attributable to the isocyanato group in the reactant 3-isocyanatopropyltriethoxy-silane had disappeared completely and instead, an absorption peak attributable to a urea bond had been formed, the reaction was determined to be completed. The solvent was then distilled off to obtain the reaction product, which was an orange solid. The reaction product was confirmed by NMR spectroscopy to have the below-described chemical structural formula (9). Its NMR spectral data are as follows:

[...

synthesis example 3

[0096]In a 1-L separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 89.4 g (0.75 mol) of 2-mercaptothiazoline and 1.3 g of dioctyltin oxide were placed, followed by charging of 300 g of ethyl acetate. The resultant mixture was stirred into a solution. Into the solution, 185.5 g (0.75 mol) of 3-isocyanatopropyl-triethoxysilane was charged dropwise, and the thus-obtained mixture was stirred under heating at 80° C. for 4 hours. Subsequently, it is confirmed by IR measurement that an absorption peak attributable to the isocyanato group in the reactant 3-isocyanatopropyltriethoxysilane had disappeared completely and instead, an absorption peak attributable to a thiourethane bond had been formed, the reaction was determined to be completed. The solvent was then distilled off to obtain the reaction product, which was a pale yellow liquid and had a viscosity of 38 mm2 / s, a specific gravity of 1.164 and a refractive index of 1.5218. The reaction p...

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Abstract

Organosilicon compounds are represented by the following formula:wherein R is a hydrolyzable group, R′ is an alkyl having 1 to 4 carbon atoms, A is an alkylene having 1 to 6 carbon atoms, X is O or S, Y is —NH— or S, L1 and L2 are C or N, Z and M are —NH—, O or S, R1 to R11 are H, alkyl having 1 to 6 carbon atoms, alkoxy or fluoroalkyl, or amino, m is 1 to 3, and n is 0 to 3. R1 and R2 or R2 and R3 may bonded together. R5 and R6 or R9 and R10 may directly bond together. R4 and R7 or R8 and R11 may form a ring skeleton. Their production processes, pressure-sensitive adhesive compositions, self-adhesive polarizers and LCDs are also disclosed.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This non-provisional application claims priority under 35 U.S.C. §119(a) on Patent Application No. 2008-227777 filed in Japan on Sep. 5, 2008, the entire contents of which are hereby incorporated by reference.TECHNICAL FIELD[0002]This invention relates to organosilicon compounds, and more specifically to organosilicon compounds capable of producing excellent bonding force with hydroxyl-containing matrix resins owing to the inclusion of two or more functional groups having coordination property with active hydrogen atoms in hydroxyl groups or the like and hence, significantly improving the adhesion and rework capability between pressure-sensitive adhesives containing the matrix resins and base materials. The present invention is also concerned with their production processes, pressure-sensitive adhesive compositions containing the organosilicon compounds, self-adhesive polarizers having pressure-sensitive adhesive layers formed from the pre...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G02F1/1335C07F7/10C09J133/04G02B5/30
CPCC07F7/1836C08G18/6254C08G18/718G02B5/3033C08G2170/40C09J135/00C08G18/8009C07F7/1804C07F7/10C09J133/10G02B5/30
Inventor TSUCHIDA, KAZUHIRO
Owner SHIN ETSU CHEM IND CO LTD
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