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Process for preparing alkyladamantyl esters and compositions

A technology of adamantyl ester and gold alkyl, applied in the field of manufacture and composition of alkyl adamantyl ester, can solve the problems such as the inability to increase the molecular weight

Inactive Publication Date: 2004-04-07
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In addition, the present inventors have learned in the course of a series of research on it that, when the alkyl adamantyl ester contains a lot of the above-mentioned impurity halides, the alkyl adamantyl ester decomposes and produces coloring during storage or transportation, In addition, there is a problem that the molecular weight cannot be increased during polymerization

Method used

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  • Process for preparing alkyladamantyl esters and compositions
  • Process for preparing alkyladamantyl esters and compositions
  • Process for preparing alkyladamantyl esters and compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 5 parts by weight of methanol and 10 0.1 part by weight of % sodium hydroxide aqueous solution (2.4 mol with respect to 1 mol of 2-chloro-2-methyladamantane) was refluxed for 3 hours. After confirming the disappearance of 2-chloro-2-methyladamantane by gas chromatography, methanol was distilled off under reduced pressure. Thereafter, 5 parts by weight of hexane was added, followed by washing with 1 part by weight of water, and drying the hexane layer with magnesium sulfate, and distilling off hexane under reduced pressure. In addition, 2-chloro-2-methyladamantane in the composition after distilling off methanol was analyzed by gas chromatography, and its content was 0.06 per 100 parts by weight of 2-methyl-2-adamantyl methacrylate. parts by weight.

[0049] With respect to 1 weight part of crude 2-methyl-2-adamantyl methacrylate from which hexane was distilled off, 0.1 weight part of diethylene glycol was added, and a 5cm wool-strip type fractionation column and a ful...

Embodiment 2

[0051] With respect to 1 weight part of thick 2-methyl-2-adamantyl methacrylate (purity 78.8% by weight) used in Example 1, add 5 weight parts of ethanol and 0.1 weight part of 5% sodium hydroxide aqueous solution (relative In 1 mole of 2-chloro-2-methyladamantane, it is 1.2 moles), heated to reflux. After confirming that the peak intensity of 2-chloro-2-methyladamantane was less than 1 / 4 by gas chromatography, ethanol was distilled off under reduced pressure. Thereafter, 5 parts by weight of hexane was added, followed by washing with 1 part by weight of water, and drying the hexane layer with magnesium sulfate, and distilling off hexane under reduced pressure. In addition, 2-chloro-2-methyladamantane in the composition after distilling off ethanol was analyzed by gas chromatography, and its content was 0.43 parts by weight relative to 100 parts by weight of 2-methyl-2-adamantyl methacrylate. parts by weight.

[0052] Same as Example 1, add diethylene glycol to distill the t...

Embodiment 3

[0054] 5 parts by weight of methanol and 10 0.1 part by weight of % sodium hydroxide aqueous solution (6.2 mol with respect to 1 mol of 2-chloro-2-ethyladamantane) was refluxed for 3 hours. After confirming the disappearance of 2-chloro-2-ethyladamantane by gas chromatography, methanol was distilled off under reduced pressure. Thereafter, 5 parts by weight of hexane was added, followed by washing with 1 part by weight of water, and drying the hexane layer with magnesium sulfate, and distilling off hexane under reduced pressure. In addition, 2-chloro-2-ethyladamantane in the composition after distilling off methanol was analyzed by gas chromatography, and its content was 0.03 parts by weight relative to 100 parts by weight of 2-ethyl-2-adamantyl methacrylate. parts by weight.

[0055] For 1 part by weight of crude 2-ethyl-2-adamantyl methacrylate from which hexane was distilled, add 0.1 part by weight of diethylene glycol, and further add 0.1 part by weight of tetraethylene g...

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Abstract

A process is provided, by which high-purity alkyladamantyl esters can be efficiently obtained by simple operation from alkyladamantyl ester compositions containing significant amounts of alkyladamantyl halides, the compositions being each prepared by alkylating 2-adamantanone obtained by oxidation of adamantane with an organometallic reagent and then reacting the resulting alkylate with and acid halide. Specifically, an alkyladamantyl ester (such as 20-methyl-2-adamantyl methacrylate)having a high purity can be obtained by adding, e.g., a mixed solution consistion of methanol and an aqueous sodiumhydroxide solution to an alkyladamantyl ester composition containing an alkyladamantyl halide (such as 2-chloro-2-methyladamantane)in an amount exceding 0.5 part by weight per 100 parts by weight of the alkyladmantyl ester, bringing the alkali compound into contact with the alkyladamantyl halide in a homogeneous system to convert the halide into a cmopound not generating an acid even in heating and thereby lower the alkyladamantyl halide content of the composition to 0.5 part by weight or below per 100 parts by weight of the alkyladamantyl ester, and then distilling the resulting composition.

Description

technical field [0001] The present invention relates to a method for producing alkyladamantyl esters and compositions containing them. Specifically, it relates to a method for producing an adamantyl ester useful as a raw material for a semiconductor protective film, and a composition containing the same. Background technique [0002] It has been reported that the protective film obtained by using alkyl adamantyl ester as a raw material has high dry etching resistance in the semiconductor manufacturing process (Japanese Unexamined Patent Publication No. 5-265212), so alkyl adamantyl ester can be used as a protective film material for semiconductors. Sex gets attention. [0003] Generally speaking, compounds used for semiconductor protective film materials are required to have high purity. Among the above-mentioned alkyl adamantyl esters, high purity is also required when used as semiconductor protective film materials. In particular, it is required to strictly reduce metal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/54C07C67/60C07C67/62C07C69/013C07C69/14C07C69/54G03F7/039
CPCC07C2103/74G03F7/0397C07C67/60C07C2603/74C07C69/54C07C69/013C07C67/54
Inventor 山口真男山本博将菊地秀树广田吉洋
Owner TOKUYAMA CORP