Preparation method of silicon compound with oxetanyl group

A technology of silicon compounds and organic groups, applied in the field of preparation of silicon compounds with oxetanyl groups, to achieve the effect of excellent stability

Active Publication Date: 2011-11-30
TOAGOSEI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, in Comparative Example 1 of Patent Document 3, it is disclosed that a silicon compound having an oxetanyl group and three hydrolyzable groups and a silicon compound having three siloxane bond forming groups are reacted under basic conditions. Since gelation occurs during hydrolytic co-condensation, it is known that gelation occurs when a silicon compound having an oxetanyl group and three hydrolyzable groups is subjected to hydrolytic condensation under alkaline conditions
[0007] In addition, in Patent Document 3, Example 8 exemplifies a specific example of cocondensing a silicon compound having four siloxane bond-forming groups and a silicon compound having three hydrolyzable groups using an acidic catalyst, but by hydrolysis The evaluation of the cured product of the silicon compound obtained by copolycondensation was not different from the case of using a silicon compound having three siloxane bond forming groups
That is, it can be said that for the co-condensation of a silicon compound having an oxetanyl group and three hydrolyzable groups with a silicon compound having four siloxane bond forming groups under basic conditions, there are known Documents that suggest the possibility of gelation and existing documents that suggest that special effects cannot be expected

Method used

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  • Preparation method of silicon compound with oxetanyl group
  • Preparation method of silicon compound with oxetanyl group
  • Preparation method of silicon compound with oxetanyl group

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preparation example Construction

[0030] The preparation method of the silicon compound (C) of the present invention is characterized in that the method includes the following steps: the first step is to make the silicon compound (A) represented by the following general formula (1) and the silicon compound (A) represented by the following general formula (2) The silicon compound (B) shown above is subjected to an alcohol exchange reaction in 1-propanol; in the second step, the composition obtained by performing the above reaction is subjected to hydrolysis and co-condensation under alkaline conditions.

[0031]

[0032] The silicon compound (C) obtained in the present invention is produced as follows: the silicon compound (A), the silicon compound (called AP) produced from the silicon compound (A) through the first step, the silicon compound (B) and the silicon compound through the first process. Step The silicon compound (called BP) produced from the silicon compound (B) is hydrolyzed and co-polycondensed. ...

Embodiment 1

[0113] (Example 1: Preparation of Silicon Compound C1)

[0114] Add 1.1 kg (4.01 mol) of 3-ethyl-3-((3-(trimethoxysilyl) propoxy) represented by the following formula (4) in a reactor equipped with a stirrer and a thermometer Methyl) oxetane (one of the monomers forming the T structural unit in the silicon compound (C) produced, hereinafter referred to as "TMSOX"), 1.1 kg (7.24 mol) tetramethoxysilane (forming A kind of monomer of the Q structural unit, hereinafter referred to as "TMOS") and 1.1kg 1-propanol, then slowly add 0.29kg (6.8mol methanol, 0.8mol tetramethylammonium hydroxide) 25% tetramethylhydroxide ammonium solution in methanol. The reaction was carried out at 60° C. for 1 hour, and then, while stirring the reaction solution, a mixed solution of 750 g (41 mol) of water and 750 g of 1-propanol was added dropwise over 0.5 hours. After reacting at 60 degreeC for 6 hours including the time of dropping, nitric acid was added and neutralized to the reaction liquid. T...

Embodiment 2

[0122] (Example 2: Preparation of Silicon Compound C2)

[0123] Add 27.82g (0.1mol) TMOSOX, 28.19g (0.185mol) TMOS and 111.5g 1-propanol shown in formula (4) in the reactor that is provided with stirrer and thermometer, then slowly add 7.29g (0.17mol) Methanol, 20mmol tetramethylammonium hydroxide) 25% tetramethylammonium hydroxide methanol solution. After reacting at 60° C. for 1 hour, a mixed solution of 18.72 g (1.04 mol) of water and 20.0 g of 1-propanol was added dropwise over 0.5 hours. After reacting at 60 degreeC for 6 hours including the dripping time, nitric acid was added and neutralized. The organic solvent and water were distilled off under reduced pressure, and the obtained residue was dissolved in PGMEA and washed with water to remove salts and excess acid. The solvent was distilled off from the obtained PGMEA solution under reduced pressure to obtain a colorless solid (compound C2). Yield was 28.8 g. The mass yield is 90%.

[0124] For silicon compound C2 ...

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Abstract

Provided is a process for efficiently producing a cationically curable condensed silicon compound. There was an unsolved problem that, in a condensation reaction, an oxetanyl group is subjected to ring-opening under acidic conditions, while gelation is easily caused under alkaline conditions. It was found that a silicon compound (C) having an oxetanyl group can be obtained without causing gelation even at a high concentration by a production process including a first step of separately subjecting a silicon compound (A) having four siloxane bond-forming groups and a silicon compound (B) havingan oxetanyl group to an alcohol exchange reaction with 1-propanol and a second step of subjecting silicon compounds (AP) and (BP) undergone the first step to hydrolytic copolycondensation under alkaline conditions at a specific ratio.

Description

technical field [0001] The present invention relates to a preparation method of a silicon compound having an oxetanyl group. More specifically, the present invention relates to a production method capable of producing at a high concentration a silicon compound having a composition that gels during a reaction in a conventional production method without causing gelation. Background technique [0002] It has been known that both acidic and basic conditions have a catalytic effect in the hydrolytic condensation of a silicon compound having a hydrolyzable group, but the chemical mechanism of condensation differs between acidic and basic conditions. For example, Non-Patent Document 1 records that: SiX 4 Tetraethoxysilane, a type of silicon compound, will be hydrolyzed by either acid or basic catalyst, but it belongs to RSiX 3 Type monomethyltriethoxysilane reacts with acid catalysts, but basically does not react with basic catalysts. [0003] Patent Document 1 describes that an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/06C08G77/14
CPCC07F7/0874
Inventor 大池沙也加北村昭宪铃木浩
Owner TOAGOSEI CO LTD
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