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Radical polymerizable resin, radical polymerizable resin composition, and cured product thereof

A technology of resin composition and polymeric compound, which is applied in the field of radically polymerizable resin composition and its cured product, can solve the problems of low curability, insufficient flexibility, toxicity, etc., and achieve thermal deterioration prevention, excellent flexibility, Excellent workability

Inactive Publication Date: 2012-12-19
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although cured products obtained by polymerization of these compounds are excellent in heat resistance, they have a problem of insufficient flexibility.
In addition, Patent Document 3 also discloses compounds having oxetane rings and (meth)acryloyl groups per molecule, but the cured products obtained by polymerizing these compounds are not sufficient in terms of heat resistance and flexibility. fulfil requirements
[0006] In addition, Patent Documents 4 and 5 disclose that glycidyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, etc. have an epoxy group and a (meth)acryloyl group in each molecule. Epoxy compounds, but epoxy compounds have problems in processability due to low curability, skin irritation, and toxicity
In addition, in terms of flexibility, cured products obtained by polymerization of these compounds cannot fully meet the requirements.
Therefore, currently, no resin has been found that is excellent in processability and can form a cured product with excellent flexibility and heat resistance.

Method used

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  • Radical polymerizable resin, radical polymerizable resin composition, and cured product thereof
  • Radical polymerizable resin, radical polymerizable resin composition, and cured product thereof
  • Radical polymerizable resin, radical polymerizable resin composition, and cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1 (manufacture of radically polymerizable resin)

[0098] Add 3.78 g of toluene and 3-ethyl-3-(3-acryloyloxy-2,2-dimethylpropane represented by the following formula A mixed solution (monomer mixed solution) of 8.82 g (34.67 mmol) of oxymethyl)oxetane (EOXTM-NPAL) and 0.039 g of 4-methoxyphenol was adjusted to 25°C. Next, a liquid mixture of 0.093 g of toluene and 0.016 g (0.11 mmol) of boron trifluoride diethyl ether complex was quantitatively added dropwise over 2 hours using a liquid delivery pump. After the dropwise addition, keep it for 4 hours, then use 5 times the amount of methanol (containing 0.1% 4-methoxyphenol) to carry out precipitation purification to the mixed solution, and keep it in a vacuum dryer (40°C, full vacuum). After 20 hours, a colorless and transparent liquid resin (1) was thus obtained.

[0099] The polystyrene conversion weight average molecular weight of this liquid resin (1) was 24800.

[0100] [chemical formula 7]

[0101]

Embodiment 2

[0102] Example 2 (manufacture of radically polymerizable resin)

[0103] Add toluene 19.98g, EOXTM-NPAL 8.82g (34.67mmol), 3-ethyl-3-(2-ethylhexyloxymethyl ) oxetane (trade name "OXT-212", manufactured by Toagosei Co., Ltd.) 23.56g (0.10mol), 4-methoxyphenol 0.039g mixed solution (monomer mixed solution), and the temperature Adjust to 25°C. Next, a liquid mixture of 5.60 g of toluene and 0.95 g (6.60 mmol) of boron trifluoride diethyl ether complex was quantitatively added dropwise over 2 hours using a liquid delivery pump. After the dropwise addition, keep it for 4 hours, then use 5 times the amount of methanol (containing 0.1% 4-methoxyphenol) to carry out precipitation purification to the mixed solution, and keep it in a vacuum dryer (40°C, full vacuum). After 20 hours, a colorless and transparent liquid resin (2) was thus obtained.

[0104] The polystyrene conversion weight average molecular weight of this liquid resin (2) was 8200.

Embodiment 3

[0105] Example 3 (manufacture of radically polymerizable resin)

[0106] Add toluene 20.40g, EOXTM-NPAL 8.82g (34.67mmol), OXT-212 39.26g (0.17mol), 4-methoxyphenol 0.039g in the three-necked flask that initiator dripping line, nitrogen line, thermometer are installed g of the mixed solution (monomer mixed solution), and adjust the temperature to 25 ° C. Next, a liquid mixture of 5.60 g of toluene and 0.95 g (6.60 mmol) of boron trifluoride diethyl ether complex was quantitatively added dropwise over 2 hours using a liquid delivery pump. After the dropwise addition, keep it for 4 hours, then use 5 times the amount of methanol (containing 0.1% 4-methoxyphenol) to carry out precipitation purification to the mixed solution, and keep it in a vacuum dryer (40°C, full vacuum). After 20 hours, a colorless and transparent liquid resin (3) was thus obtained.

[0107] The polystyrene conversion weight average molecular weight of this liquid resin (3) was 8300.

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Abstract

Provided is a radical polymerizable resin which has a low viscosity, has excellent workability, rapidly cures by exposure to heat and / or light, and forms a cured product having excellent pliability and heat resistance. A radical polymerizable resin composition is obtained by cation polymerization of an oxetane ring-containing (meth)acrylic acid ester compound represented by formula (1) (where R1 is a hydrogen atom or a methyl group, R2 is a hydrogen atom or an alkyl group, and A is a C4-20 straight-chain or branched-chain alkylene group) alone or together with another compound having cation polymerizability.

Description

technical field [0001] The present invention relates to waveguides (optical waveguides, hybrid substrates, etc.), optical fibers, stress-relieving adhesives, sealants, underfills, inkjet inks, color filters, nanoimprints, flexible substrates, etc. Radical polymerizable resins, radical polymerizable resin compositions, and cured products thereof useful in the fields of flexible optical waveguides, flexible adhesives, underfills, and the like. Background technique [0002] With the spread of online video (movie distribution) using the Internet, communication capacity in switchboards (boards) used for servers and routers has increased, and research has progressed to replace some high-speed signal lines from electrical wiring to optical wiring. Compared with quartz-based optical waveguides, polymer optical waveguides are expected to be used as optical wiring for optoelectronic hybrid substrates due to their lower cost. As one of the characteristics required for optical wiring, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/18C08F2/44C08F265/06
CPCC08F265/06C08G65/18C08G65/22C08F220/32C08F283/105C08F220/30C08F2/44C08F20/26C08J5/18
Inventor 新木直子船木克典堤圣晴间彦智明
Owner DAICEL CHEM IND LTD
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