Method for producing polymerizable hydroxydiamantyl ester compound

A technology of hydroxydiadamantyl ester and dihalogenated diamantane, which is applied in the field of preparation of polymeric hydroxydiadamantyl ester compounds, and can solve problems such as difficulties

Inactive Publication Date: 2008-12-10
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] As mentioned above, although the carbon skeletons of diamantane derivatives and adamantane derivatives are similar to each other, their reactivity, especially the reactivity of the second-stage esterification, is very different. The reactivity of derivatives is currently difficult

Method used

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  • Method for producing polymerizable hydroxydiamantyl ester compound
  • Method for producing polymerizable hydroxydiamantyl ester compound
  • Method for producing polymerizable hydroxydiamantyl ester compound

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preparation example Construction

In the production method of the present invention, first, a diadamantane compound represented by the following formula (2) is subjected to a dihalogenation reaction to obtain a 4,9-dihalogenated diadamantane compound.

[0031] [chemical 4]

[0032] In the above formula (2), R 2 and R 3 Each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

[0033] Specific examples of preferred groups among the alkyl groups having 1 to 5 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl Base, sec-pentyl, isopentyl, etc.

[0034] In this step (i), as R 2 and R 3 , as long as it matches with the target polymerizable hydroxydiamantyl ester compound and selects appropriately. Specific examples of diadamantane compounds that can be used include diadamantane, 1-methyldiamantane, 1-ethyldiamantane, 1,6-dimethyldiamantane, 1,6 -Diethyldiadamantane and the like. Among these, diamantane is particularly prefera...

Embodiment 1

[0133] Add chlorosulfonic acid 222.7g (1.912mol, be 3 mole times of raw material diadamantane) (total be 5 mole times of diadamantane) to wherein, stir again at 30 ℃ for 15 hours (reaction time of 18 hours in total) ). After 15 hours, GC analysis revealed that the product contained 1% of the raw materials diadamantane, 5% of monochlorodiamantane, 80% of dichlorodiamantane, and 14% of trichlorodiamantane. After cooling the reaction liquid to about 10°C, 262 g of water was dropped while keeping the reaction liquid at a temperature not higher than 30°C. 840 g of dichloromethane was added, stirred, left to stand, and liquid-separated, and the lower sulfuric acid aqueous solution layer was removed. Then, the organic layer was washed 2 times with 240 g of 10% aqueous sodium hydroxide solution, 1 time with 300 g of 7% aqueous sodium sulfate solution, and 2 times with 120 g of 7% aqueous sodium sulfate solution. At this time, the pH value of the organic layer had changed into neutra...

Embodiment 2～3

[0142] Table 1

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Abstract

Disclosed is a method for producing a polymerizable hydroxydiamantyl ester compound wherein a 4,9-diamantanediol compound is produced by dihalogenating and then hydrolyzing a raw material compound having a diamantane backbone such as diamantane, and then the 4,9-diamantanediol compound is esterified in the mixture of a polymerizable unsaturated carboxylic acid and a polymerizable unsaturated carboxylic acid anhydride in the presence of a polymerization inhibitor and an acid catalyst.

Description

technical field [0001] The present invention relates to a method for preparing a polymerizable hydroxydiadamantyl ester compound used as a raw material monomer of a functional material or an electronic material. Background technique [0002] Diadamantane derivatives are characterized by having a skeleton similar to that of adamantane derivatives, excellent heat resistance, and high transparency. Compared with the adamantane skeleton, the diadamantane skeleton has a larger number of condensed rings. It is believed that due to this reason, diamantane derivatives are superior to adamantane derivatives in physical properties such as heat resistance, and are expected to be applied to high-functional materials such as heat-resistant polymers and electronic materials such as photoresists for semiconductors. . Among diamantane derivatives, polymerizable hydroxydiadamantyl ester compounds are also expected to be extremely useful compounds. The compound can be used alone or togethe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/52C07C69/54
CPCC07C17/10C07C29/124C07C67/08C07C67/52C07C2603/90C07C23/46C07C31/20C07C69/54C07C69/608
Inventor 前原孝之
Owner TOKUYAMA CORP
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