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Adamantane derivative, process for production thereof, resin composition, and cured product of the resin composition

A technology of derivatives and adamantane, which is applied in the field of adamantane derivatives, its manufacture, resin composition and its cured products, can solve the problems of unsatisfactory heat resistance and mechanical strength, and achieve curing shrinkage or linear expansion coefficient Low heat resistance and excellent mechanical properties

Inactive Publication Date: 2009-09-09
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these acrylates cannot satisfy heat resistance and mechanical strength

Method used

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  • Adamantane derivative, process for production thereof, resin composition, and cured product of the resin composition
  • Adamantane derivative, process for production thereof, resin composition, and cured product of the resin composition
  • Adamantane derivative, process for production thereof, resin composition, and cured product of the resin composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Example 1 "Synthesis of Adamantane-1,3,5-trimethanol triacrylate"

[0112] Add 50g adamantane-1,3,5- Trimethanol (0.22 mol), 55.7 g of acrylic acid (0.77 mol), 500 mL of toluene, 1.11 g of 98% by mass sulfuric acid and 0.06 g of p-methoxyphenol were immersed in an oil bath at 130° C. and heated to reflux for 3 hours. At this time, water gradually produced as the reaction proceeds is removed from the reaction system while the reaction proceeds. Then, the reaction solution was cooled to room temperature and transferred into a separatory funnel. Subsequently, 250 mL of 5% by mass sodium chloride aqueous solution was added for washing, and then the organic layer was washed with 250 mL of 3% by mass sodium phosphate aqueous solution, and then further washed with 250 mL of 5% by mass sodium chloride aqueous solution. Next, after dehydration with anhydrous magnesium sulfate, magnesium sulfate was removed by filtration. The filtrate was evaporated to remove the solvent to ob...

Embodiment 2

[0117] In 10 g of adamantane-1,3,5-trimethanol triacrylate obtained in Example 1, 0.1 g of benzoin isobutyl ether was added as a photopolymerization initiator, mixed thoroughly and vacuum degassed to obtain a resin composition. Pour the resin composition into a glass tank, and use a mercury lamp at 3000mJ / cm 2 Under the condition of irradiation, a cured product with a thickness of 1mm was obtained. The physical property values ​​of the obtained cured product are shown in Table 1.

Embodiment 3

[0119] In the mixture of 7g of adamantane-1,3,5-trimethanol triacrylate and 3g of adamantane-1,3-dimethanol diacrylate obtained in Example 1, 0.1g of benzoin isobutyl ether was added as a light The polymerization initiator is fully mixed and then vacuum degassed to obtain a resin composition. Pour the resin composition into a glass tank, and use a mercury lamp at 3000mJ / cm 2 Under the condition of irradiation, a cured product with a thickness of 1mm was obtained. The physical property values ​​of the obtained cured product are shown in Table 1.

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Abstract

The invention relates to an adamantane derivative represented by the general formula (I) [wherein R represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; Y represents a hydrogen atom, a hydroxyl group, a group =O formed by two Y's together, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a cyclic hydrocarbon group having 3 to 20 carbon atoms; m is 13 and n is 3, or m is 12 and n is 4; and p represents an integer of 1 or more]; a process for producing the adamantane derivative; a resin composition comprising the adamantane derivative; and a cured product of the resin composition. It becomes possible to provide a cured product which is suitable as a coating agent, a microlens, a film capacitor, a coloring composition for a liquid crystal color filter, a pattern-formed article produced by nanoimprinting technique or the like and having transparency, heat resistance, good mechanical properties, a low linear expansion coefficient and a low rate of shrinkage upon curing, and also provide a liquid (meth)acrylate having an adamantyl group, a process for producing the (meth)acrylate, and a resin composition which enable to produce the cured product.

Description

technical field [0001] The present invention relates to novel adamantane derivatives, their production methods, resin compositions containing the derivatives, and cured products thereof. Specifically, the present invention relates to various coating agents, display materials, and Novel adamantyl group-containing (meth)acrylates for microlenses, film capacitors, coloring compositions for liquid crystal filters, patterned bodies formed by micro-nano imprinting, methods for producing the same, containing the ( Resin composition of meth)acrylate and cured product thereof. Background technique [0002] Adamantane has a structure in which four cyclohexane rings are condensed into a cage, and is a highly symmetrical and stable compound. Its derivatives exhibit special functions, and are known to be used as raw materials for medicines and high-functional industrial materials. For example, since it has optical properties, heat resistance, etc., it has been attempted to be used for o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/54C08F20/20G03F7/027
CPCC08F20/28C07C2103/74G03F7/027C07C67/08C07C69/54C08F20/20C07C2603/74
Inventor 冈田保也山根秀树伊藤克树松本信昭
Owner IDEMITSU KOSAN CO LTD
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