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Cation-polymerizable resin composition and cured product thereof

A cationic polymerization, resin composition technology, applied in other chemical processes, epoxy resin coatings, chemical instruments and methods, etc., can solve the problems of heat resistance, poor transparency, difficult application, lack of flexibility, etc., to achieve easy processing. , Excellent workability, excellent safety effect

Inactive Publication Date: 2012-02-29
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although this compound is excellent in heat resistance, transparency, and curing speed, it lacks flexibility, making it difficult to apply to fields that require flexibility, such as flexible optical waveguides.
[0006] In addition, in the same manner, Japanese Patent Application No. 2007-078858 and Japanese Patent Application No. 2007-076219 respectively disclose alicyclic epoxy group-containing vinyl ether compounds, oxetane ring-containing vinyl ether compounds, and oxetane ring-containing vinyl ether compounds. Ether compounds, these compounds are also excellent in heat resistance, transparency, and curing speed, but lack flexibility, making it difficult to apply to fields requiring flexibility such as flexible optical waveguides
Further, in Japanese Patent Laid-Open No. 2006-232988, an example of adding epoxidized polybutadiene having hydroxyl groups at both ends to a cyclic ether compound containing a vinyl ether structure is exemplified, but since only vinyl ether As a reactive group, heat resistance and transparency are inferior to vinyl ethers containing reactive cyclic ethers in the same molecule

Method used

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  • Cation-polymerizable resin composition and cured product thereof
  • Cation-polymerizable resin composition and cured product thereof
  • Cation-polymerizable resin composition and cured product thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0202] Raise the temperature of 280 mL of a mixture of 24.9 g (0.23 mol) of sodium carbonate and toluene to 95° C., add 1.4 g of propionic acid, and dropwise add 16 g of vinyl acetate while keeping the temperature at 95° C. After 15 minutes, add di-μ- Chlorobis(1,5-cyclooctadiene)diiridium(|)[Ir(cod)Cl] 2 1.27g (1.9mmol). Next, 40 g (0.19 mol) of oxetane-3,3-dimethanol was added dropwise over 3 hours, and 79.8 g of vinyl acetate was added dropwise while maintaining the temperature at 95° C. under a nitrogen atmosphere to perform a reaction. After the dropwise addition was completed, stir for 1 hour, and analyze the reaction solution by gas chromatography, 3,3-bis(vinyloxymethyl)oxetane represented by the following formula (13) was generated with a yield of 90%. , (3-vinyloxymethyloxetan-3-yl)methanol was produced in 2% yield. The reaction solution was purified by distillation to obtain 31 g of 3,3-bis(vinyloxymethyl)oxetane with a purity of 99%.

[0203] 1 H-NMR (CDCl 3 )...

Synthetic example 2

[0206] 3-chloromethyl-3 ethyl oxetane (0.1mol) and 1,4-cyclohexanediol (0.5mol), tetrabutylammonium bromide (0.01mol) were added in toluene (500g), After heating up to 90°C, 5N-NaOH aqueous solution (100 g) was added dropwise, followed by stirring for 5 hours. The toluene solution (toluene layer) was washed with water, concentrated, and purified by silica gel chromatography to obtain 4-(3-ethyl-oxetan-3-yl-methoxy)cyclohexanol with a purity of 99%.

[0207] 100 mL of a mixture of sodium carbonate (0.06 mol) and toluene was heated to 95°C. While keeping the temperature at 95°C, 4.2 g of vinyl acetate was added dropwise, and after 15 minutes, di-μ-chlorobis(1,5-cyclooctadiene)diiridium(|)[Ir(cod)Cl] was added 2 (0.5 mmol). Next, 4-(3-ethyloxetan-3-yl-methoxy)cyclohexanol (0.05 mmol) was added dropwise over 2 hours, under a nitrogen atmosphere while maintaining the temperature at 95°C, While adding 12.6 g of vinyl acetate dropwise, the reaction was carried out. After the drop...

Synthetic example 3

[0210] 12.6 g (0.1 mol) of (4-methylcyclohex-3-enyl)methanol was epoxidized at 65° C. using a 5% by weight peracetic acid-ethyl acetate solution. Purification by distillation yielded 12 g of (6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methanol with a purity of 98%.

[0211] 100 mL of a mixture of sodium carbonate (0.06 mol) and toluene was heated to 95°C. While keeping the temperature at 95°C, 4.2 g of vinyl acetate was added dropwise, and after 15 minutes, di-μ-chlorobis(1,5-cyclooctadiene)diiridium(|)[Ir(cod)Cl] was added 2 (0.5 mmol). Next, (6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methanol (0.05 mmol) was added dropwise over 2 hours, and the temperature was kept at 95°C under a nitrogen atmosphere. 12.6 g of vinyl acetate was dripped and reacted. After the dropwise addition was completed, stir for 1 hour, analyze the reaction solution by gas chromatography, and generate 1-methyl-4-vinyloxy-7-oxabicyclo[ 4.1.0] Heptane. determine its 1 H-NMR (CDCl 3 ), as in Synthesis Exampl...

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Abstract

A cation-polymerizable resin composition is provided which has a low viscosity, is easy to work with, and cures extremely rapidly when irradiated with light to obtain a cured product with excellent transparency, flexibility, heat resistance and post heat-treatment flexion. The cation-polymerizable resin composition of the present invention is characterized by containing: (A) an oxetane ring-containing vinyl ether compound, and / or (B) an alicyclic epoxy group-containing vinyl ether compound; (C) an oligomer or polymer having a molecular weight of at least 500 and having at least one of an oxetane group, epoxy group, hydroxyl group, vinyl ether group, an aliphatic or alicyclic unsaturated hydrocarbon group within the molecule; and (D) an oxetane compound having at least 6 carbon atoms and not having a vinyl ether group.

Description

technical field [0001] The present invention is useful in the fields of waveguides (optical waveguides, photoelectric composite wiring boards, etc.), optical fibers, transparent sealants, inkjet inks, color filters, nanoimprints, flexible substrates, etc., especially in flexible optical waveguides, transparent sealing A cationic polymerizable resin composition useful in the fields of agents and nanoimprints and its cured product. In addition, it also relates to a method for producing an optical waveguide using the above-mentioned cationically polymerizable resin composition, an optical waveguide obtained by the production method, an optoelectronic composite wiring board provided with electrical wiring on the surface of the optical waveguide, and an optical waveguide using the above-mentioned cationically polymerizable resin composition. A method for producing a fine structure of a resin composition. Background technique [0002] In the fast and high-density signal transmiss...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/18C08G65/14C09D4/00C09D163/00C09K3/10G02B6/12G02B6/122H01L21/027G02B6/13G02B6/132G02B6/138
CPCC08G59/027C08G65/14C08L63/08C09D4/00G02B6/02033C08G65/18C09D163/00C09K3/10
Inventor 吉田司舩木克典大和洋
Owner DAICEL CHEM IND LTD
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