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Method for producing blocked isocyanate compound

A technology for blocking isocyanates and manufacturing methods, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of carbamic acid derivatives. It can solve problems such as environmental burdens and cost increases, and achieve the effect of simplifying manufacturing equipment and reducing burdens

Inactive Publication Date: 2018-10-26
RESONAC HOLDINGS CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the use of a solvent is not preferable because it will burden the environment, and since a purification process is required, there is a problem of increasing the cost while increasing the production process.

Method used

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  • Method for producing blocked isocyanate compound
  • Method for producing blocked isocyanate compound
  • Method for producing blocked isocyanate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150] In a 2L separate flask with a stirrer, a condenser and a thermometer, 150.0 g of 2-(O-[1'-methylpropylideneamino]oxycarbonylamino)ethyl acrylate, 2,6-di-tert- Butyl-4-methylphenol (BHT) was 0.11 g, and the temperature was adjusted to 10°C. Next, 141.1 g (1.00 mol) of 2-(acryloyloxy) ethyl isocyanate (manufactured by Showa Denko Co., Ltd.; product name Karenz AOI (registered trademark)) and 87.1 g (1.00 mol) of butanone oxime (MEKO) were separated. It was added dropwise over 5 hours using a dropping funnel. After completion of the dropwise addition, the mixture was stirred for 1 hour with the internal temperature adjusted to 20°C to obtain 2-(O-[1'-methylpropylideneamino]oxycarbonylamino)ethyl acrylate.

[0151] Table 1 shows the results of analyzing the composition of the product by HPLC and GC.

[0152] In addition, only the amount of BHT was quantified by GC, and other components were quantified using HPLC. GC analysis conditions and HPLC analysis conditions are sh...

reference example 2

[0174] Add 150.0 g of 2-(O-[1'-methylpropylideneamino]oxycarbonylamino)ethyl acrylate, 2,6-di-tert- Butyl-4-methylphenol (BHT) was 0.11 g, and the temperature was adjusted to 10°C. Next, 141.1 g (1.00 mol) of 2-(acryloyloxy) ethyl isocyanate (manufactured by Showa Denko Co., Ltd.; product name Karenz AOI (registered trademark)) and 87.1 g (1.00 mol) of butanone oxime (MEKO) were separated. Dropwise additions were performed simultaneously using a dropping funnel. At this time, the dripping was carried out at a constant dripping speed when the 2-(acryloyloxy)ethyl isocyanate could be dripped in 5 hours and the butanone oxime could be dripped in 4 hours. After the dripping of 2-(acryloyloxy)ethyl isocyanate is completed, stir for 1 hour while adjusting the internal temperature to 20°C to obtain 2-(O-[1'-methylpropylidene acrylic acid Amino]oxycarbonylamino)ethyl ester.

[0175] Table 1 shows the results of analyzing the composition of the product by HPLC and GC.

[0176] In a...

reference example 3

[0178] Add 14.3 g of 2-(O-[1'-methylpropylidene amino]oxycarbonyl amino) ethyl acrylate and 43.56 g (0.50 mol) of butanone oxime (MEKO) in a 200 mL 3-necked flask, and the temperature Adjust to 10°C. 71.0 g (0.50 ml) of 2-(acryloyloxy)ethyl isocyanate was added dropwise over 5 hours using a 50 mL dropping funnel. After completion of the dropping, the mixture was stirred for 1 hour with the internal temperature adjusted to 20°C to obtain 2-(O-[1'-methylpropylideneamino]oxycarbonylamino)ethyl acrylate.

[0179] Table 1 shows the results of analyzing the composition of the product by HPLC and GC.

[0180] In addition, only the amount of BHT was quantified by GC analysis, and other components were quantified using HPLC. GC analysis conditions and HPLC analysis conditions are the same as in Example 1.

[0181] Table 1

[0182]

[0183] According to the production methods of Example 1 and Reference Examples 2 and 3, since no solvent is used, the product does not contain a sol...

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Abstract

This method for producing a blocked isocyanate compound represented by general formula (III) is characterized in that: a (meth)acryloyl group-containing isocyanate compound represented by general formula (I) and an oxime compound represented by general formula (II) are reacted with each other; and a solvent is not used or a compound represented by general formula (III) is used in place of a solvent during the production procedure. In the formulae, R0 represents a methyl group or a hydrogen atom; R1 represents -CO- or -COOR4- (wherein R4 represents an alkylene group which has 1-10 carbon atomsand may contain an ether bond and / or a phenylene group); and each of R2 and R3 independently represents a group that is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an n-butyl group and an n-pentyl group.

Description

[0001] This application is a divisional application of a patent application with an application date of July 24, 2013, an application number of 201380023479.4, and an invention title of "Method for Producing Blocked Isocyanate Compounds". technical field [0002] The present invention relates to a method for producing a blocked isocyanate compound, which is a blocked body of isocyanate containing (meth)acryloyl group, and the blocked isocyanate compound is suitable as a raw material in various coating agents, adhesives, molding materials, etc. Body use. More specifically, it relates to a production method capable of obtaining a blocked isocyanate compound with high purity by avoiding reduction in product purity due to factors such as polymerization reaction and side reaction in industrial production. [0003] This application claims priority to Patent Application No. 2012-168544 filed in this application on July 30, 2012, and the contents thereof are cited herein. Background...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/02C07C271/60
CPCC07C269/02C07C271/60C07C265/14
Inventor 大野胜俊加藤智光古川哲弘大泽信夫万谷慎一
Owner RESONAC HOLDINGS CORPORATION