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Adamantane derivative, resin composition using the same, and resin cured product

A technology of adamantane and derivatives, applied in the field of adamantane derivatives and its preparation, can solve the problems that have not yet been obtained, and achieve the effect of excellent dielectric constant and excellent mechanical properties

Inactive Publication Date: 2010-02-17
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, monomers for producing cured resins that can obtain cured products excellent in transparency, heat resistance, solvent resistance, etc., have good storage stability, and can be used in various ways have not yet been obtained.

Method used

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  • Adamantane derivative, resin composition using the same, and resin cured product
  • Adamantane derivative, resin composition using the same, and resin cured product
  • Adamantane derivative, resin composition using the same, and resin cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0134] Synthesis of 3-[(3-ethyloxetan-3-yl)methoxy]-1-adamantyl methacrylate

[0135] Add 50.4g (0.160mol) 3-methylsulfonyloxy-1-adamantyl methacrylate, 27.2g (0.344mol) Pyridine, 0.01 g of methoquinone, and 200 g of (3-ethyloxetan-3-yl)methanol (manufactured by Ube Industries, trade name: Ethanacol EHO) were used for nitrogen substitution. Then the temperature was raised to 120° C., and heated and stirred for 4 hours. The reaction solution was cooled, extracted with toluene, and washed with saturated brine. The solvent was distilled off under reduced pressure to obtain 42.7 g (yield 74%) of the target product. given below 1 H-NMR, 13 Respective data of C-NMR and GC-MS.

[0136]

[0137] 1 H-NMR (500MHz): 0.85(3H), 1.55(2H), 1.67-1.78(4H), 1.89(2H), 2.06-2.20(6H), 2.33(2H), 3.53(2H), 4.35-4.40( 4H), 5.48(1H, a2), 6.00(1Ha1)

[0138] 13 C-NMR(125MHz): 8.25(q), 18.39(c), 26.64(p), 31.06(g), 35.26(h), 40.35(f or j), 40.51(f or j), 43.18(m) , 45.32(i), 62.95(k), 73.85...

Embodiment 2

[0141] Synthesis of 3-[(3-ethyloxetan-3-yl)methoxy]-1-adamantyl acrylate

[0142] Add 50.4g (0.167mol) 3-methylsulfonyloxy-1-adamantyl acrylate, 27.2g (0.344mol) pyridine, Nitrogen substitution was carried out with 0.01 g of methylbenzoquinone and 200 g of (3-ethyloxetan-3-yl)methanol (manufactured by Ube Industries, trade name: Ethanacol EHO). Then the temperature was raised to 120° C., and heated and stirred for 4 hours. The reaction solution was cooled, extracted with toluene, and washed with saturated brine. The solvent was distilled off under reduced pressure to obtain 38 g (yield 71.2%) of the target product. given below 1 H-NMR and 13 Each data of C-NMR.

[0143]

[0144] 1 H-NMR (500MHz): 0.85(3H), 1.55(2H), 1.67-1.78(4H), 1.89(2H), 2.06-2.20(6H), 2.33(2H), 3.53(2H), 4.35-4.40( 4H), 5.69 (dd, J=1.6, 10.7Hz, 1H, a2), 5.97 (dd, J=10.7, 17.6Hz, 1H, b), 6.24 (dd, J=1.6, 17.6Hz, 1H, a1)

[0145] 13 C-NMR (125MHz): 8.25(p), 26.64(o), 30.96(f), 35.04(g), 40.20(e o...

Embodiment 3

[0147] Synthesis of 3-[(3-oxiran-2-yl)methoxy]-1-adamantyl methacrylate

[0148] Add 50.4g (0.160mol) 3-methylsulfonyloxy-1-adamantyl methacrylate, 27.2g (0.344mol) Pyridine, 0.01 g of methylbenzoquinone, and 200 g of 2-chloro-1,3-propanediol were used for nitrogen substitution. Then the temperature was raised to 80° C., and heated and stirred for 2 hours. The reaction solution was cooled, then extracted with 500 ml of toluene, and washed twice with 500 ml of saturated brine. 20 g of sodium hydroxide was added to the solution after washing, and after heating and stirring at 110° C. for 2 hours, the solvent was cooled. Then, it was washed twice with 300 mL of saturated brine, and the solvent was distilled off under reduced pressure to obtain 40 g (yield 82%) of the target product. given below 1 H-NMR and 13 Each data of C-NMR.

[0149]

[0150] 1 II-NMR (500MIIz): 1.67-1.78(4II), 1.89(2II), 2.06-2.20(6II), 2.33(2H), 2.38(1H), 2.63(1H), 2.86(1H), 3.53(2H) , 5.48(1H, a...

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Abstract

Disclosed is a cured product of an adamantane derivative having a specific structure, which is excellent in transparency, optical characteristics such as (long-term) light resistance, long-term heat resistance, dielectric constant and mechanical properties. This resin cured product is suitably used in the fields of electronic / optical material.

Description

technical field [0001] The present invention relates to a novel adamantane derivative and a preparation method thereof, more specifically, to an adamantane derivative suitable for use in preparing useful resin compositions and cured resin monomers in the fields of electronics and optical materials, and Its preparation method, as well as the resin composition and resin cured product using the adamantane derivative. Background technique [0002] It is known that adamantane has a structure in which four cyclohexane rings are condensed into a cage, and is a highly symmetrical and stable compound. Its derivatives show specific functions, so they can be used as raw materials for pharmaceuticals or high-functional industrial materials, etc. . Since adamantane has, for example, optical properties and heat resistance, it has been attempted to be used in optical disk substrates, optical fibers, lenses, and the like (see Patent Documents 1 and 2). [0003] An attempt has also been ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/28C07D303/12C07D305/06C08G59/32C08G65/22
CPCC07D303/12C08F220/32C08G65/105C08G65/18C08L63/00C07D305/06C08F220/28C08F220/282C08F20/28C08G59/32
Inventor 伊藤克树冈田保也山根秀树山尾忍
Owner IDEMITSU KOSAN CO LTD
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