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Isocyanate-based sealing agents and isocyanates protected by said sealing agents

An isocyanate group, blocking isocyanate technology, applied in the field of isocyanate, can solve the problems such as lowering, unrecorded deblocking temperature, and reaction rate constant only slightly increased

Pending Publication Date: 2022-07-08
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In Non-Patent Document 2, although the reactivity was investigated by the reaction rate theory using liquid chromatography, it does not describe the expression of a clear effect such as a large decrease in the deblocking temperature, but only slightly improves the reaction rate constant. the subject of

Method used

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  • Isocyanate-based sealing agents and isocyanates protected by said sealing agents
  • Isocyanate-based sealing agents and isocyanates protected by said sealing agents
  • Isocyanate-based sealing agents and isocyanates protected by said sealing agents

Examples

Experimental program
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Embodiment

[0074] Synthesis Examples, Examples, and Comparative Examples are shown below to describe the present invention in more detail, but the present invention is not limited to the following Examples.

Synthetic example 1

[0076] Synthesis of 3-allyldimethylsilyl propanol

[0077] A 500 ml four-necked flask including a dropping funnel, a Dimroth type cooling condenser, a stirrer, and a thermometer was fully nitrogen-substituted. Diallyldimethylsilane (7.6 g), tetrahydrofuran (THF) (150 ml) were charged and nitrogen purged while cooling the contents of the flask with an ice bath. Next, a 0.5M solution of 9-borabicyclo[3.3.1]nonane (54 ml) was added dropwise. The mixture takes on a clear and uniform appearance. After stirring at room temperature for 3 hours, the contents of the flask were again cooled in an ice bath, and 3M-NaOH aqueous solution (27 ml) and 30% hydrogen peroxide water (33 ml) were added and shaken. After stirring at room temperature for 1 hour, 100 ml of water and 150 ml of hexane were added. The organic layer containing hexane was separated, anhydrous sodium sulfate (20 g) was added, and after filtration, volatile components were removed by a vacuum pump to obtain a transpar...

Synthetic example 2

[0080] Synthesis of 3-(4-methylphenyl)dimethylsilylpropanol

[0081] A 200 ml four-necked flask including a dropping funnel, a Dimroth-type cooling condenser, a stirrer, and a thermometer was fully replaced with nitrogen. Charge allyloxytrimethylsilane (13.0g), 1,5-cyclooctadiene (8ml), di-μ-chlorobis(μ-1,5-cyclooctadiene)diiridium (0.06g) ), and nitrogen ventilation was carried out, while the temperature was raised to 80 °C. Next, chlorodimethylsilane (9.5 g) was added dropwise, and it was made to react at 80 degreeC for 6 hours. A 0.7M THF solution of 4-methylphenylmagnesium bromide was added dropwise thereto, followed by heating under reflux for two hours again. After cooling to room temperature, 100 ml of 1N aqueous hydrochloric acid and 150 ml of ethyl acetate were added. The organic layer containing ethyl acetate was separated, anhydrous sodium sulfate (20 g) was added, and after filtration, the volatile matter was evaporated under reduced pressure. To this, 20 ml ...

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Abstract

The purpose of the present invention is to provide an isocyanate compound which can harden with another polymerizable compound at a relatively low temperature and has excellent water resistance, and to provide a blocking agent capable of blocking an isocyanate group, and to provide a blocked isocyanate having a structure in which an isocyanate group is blocked by the blocking agent. The present invention provides a blocking agent capable of blocking an isocyanate group, the blocking agent being a silicone alcohol characterized by having an organic group bonded to a silicon atom and being capable of forming a ss-silyl cation using the organic group and the silicon atom. It is preferable to provide a sealing agent that is a silicone alcohol represented by general formula (1). (In the formula, R1 is an alkylene group having 3-5 carbon atoms and may have a substituent (wherein the number of carbon atoms of the substituent is not included in the 3-5 carbon atoms), R2 is an alkyl group having 1-10 carbon atoms, Z is an organic group that forms a beta-silyl cation using adjacent silicon atoms and Z, and n is an integer of 1-3). Also provided are: a blocked isocyanate having a structure in which an isocyanate group is blocked by the blocking agent; and a thermosetting composition containing the blocked isocyanate.

Description

technical field [0001] The present invention relates to an isocyanate-based blocking agent and an isocyanate protected by the blocking agent. In more detail, it relates to a silicon-substituted alcohol-containing isocyanate-based blocking agent and a blocked isocyanate using the same. Background technique [0002] Isocyanates are widely used as raw materials of polyurethanes, but they have problems in water resistance and toxicity, so they are used as so-called blocked isocyanates. By using a blocked isocyanate, it is an industrially very important compound because the single liquefaction and stability of the coating material are realized. [0003] Compounds used as blocking agents for blocking isocyanates are compounds having active protons, and oximes, amides, alcohols, malonates, pyrazoles and the like are known. However, there are problems in the blocked isocyanates used previously. For example, oximes such as methyl ethyl ketoxime are widely used due to their stabili...

Claims

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Application Information

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IPC IPC(8): C08G18/80
CPCC08G18/246C08G18/289C08G18/73C08G18/809C08G18/677C08G18/6229C09D175/04C08G18/6225
Inventor 麻生史拓増田幸平
Owner SHIN ETSU CHEM IND CO LTD
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