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Hardenable composition, hardened film and forming method thereof, and compound

A composition and hardening technology, applied in chemical instruments and methods, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., can solve the problem of insufficient solvent resistance and storage stability of the hardened film Excellent storage stability and low-temperature curability, excellent storage stability, and excellent low-temperature curability

Inactive Publication Date: 2015-04-15
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, these conventional base generators cannot achieve both storage stability at room temperature and a temperature close to room temperature and curability at relatively low temperatures when used as a resin composition for forming a cured film.
In addition, properties such as solvent resistance of a cured film formed from a resin composition using a conventional base generator are insufficient.

Method used

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  • Hardenable composition, hardened film and forming method thereof, and compound
  • Hardenable composition, hardened film and forming method thereof, and compound
  • Hardenable composition, hardened film and forming method thereof, and compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0159]

[0160] The curable composition is prepared by uniformly mixing [A] compound and [B] polymerizable compound, preferably [C] alkali-soluble resin, [D] solvent, and other optional components. The curable composition is preferably used in a solution state by being dissolved in the [D] solvent, but the solvent may be omitted.

[0161] The solid content concentration (ratio of components other than the solvent in the composition solution) in the curable composition can be set according to the purpose of use, desired film thickness, and the like. The prepared solution of the curable composition may be used after being filtered using a millipore filter having a pore diameter of about 0.05 μm to 0.5 μm or the like.

[0162]

[0163] The cured film of this invention is formed from this curable composition. This cured film has excellent solvent resistance. Such a cured film can be suitably used for applications requiring high surface hardness, for example, it can be suitab...

Embodiment

[0200] Hereinafter, based on an Example, this invention is demonstrated more concretely. The present invention is not limited by these Examples.

[0201] First, the measurement method and evaluation method of the physical properties will be described.

[0202] [ 1 Determination of H-NMR]

[0203] 1 H-NMR (Nuclear Magnetic Resonance, NMR) was measured at 25° C. using a nuclear magnetic resonance apparatus (“JNM-ECS400” (trade name) (400 MHz) of JEOL Ltd.).

[0204] [Measurement of weight average molecular weight Mw]

[0205] The weight average molecular weight Mw is a polystyrene equivalent molecular weight measured using a gel permeation chromatography (GPC) apparatus (Showa Denko's "GPC-101" (trade name)). The measurement with the GPC device uses a combination of "GPC-KF-801", "GPC-KF-802", "GPC-KF-803" and "GPC-KF-804" (the above are trade names, Showa Denko Corporation) The resulting column was used as a GPC column, and tetrahydrofuran (tetrahydrofuran, THF) was used ...

Synthetic example 1

[0208] A compound represented by the following formula (A-1) (hereinafter also referred to as "compound (A-1)") was synthesized according to the following synthesis scheme.

[0209] [chemical 5]

[0210]

[0211] Add o-phenylenediamine (Sigma-Aldrich (Sigma-Aldrich) company) 3.24g (30.0mmol), salicylaldehyde (Sigma-Aldrich company) 3.67g (30.0mmol), sodium metabisulfite (Sigma-Aldrich company) in single-necked flask Derich Company) 5.70 g (30.0 mmol) and N, N-dimethylformamide (Sigma-Aldrich Company) 270 mL, heated to 80° C. in an oil bath, and reacted for 24 hours. After the reaction, the temperature was returned to room temperature, and the reaction solution was added to 300 mL of water at 0°C. The precipitate was collected by filtration, and purified by silica gel column chromatography to obtain compound (A-1).

[0212] Determination of compound (A-1) 1 H-NMR, the result is as described below.

[0213] 1 H-NMR (DMSO-d 6 );

[0214] δ7.00-7.04(2H, m), δ7.24-7.40(3H...

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Abstract

The invention aims to provide a hardenable composition, a hardened film and a forming method thereof, and a compound. The curable composition can both storage stability and low-temperature hardenability, and can form a hardened film with excellent solvent resistance. The hardenable composition provided by the invention includes at least one of groups formed by compounds represented by formula(1-1) and formula(1-2), and a polymerizable compound. R1-R5 and R11-R15 are hydrogen atom, halogen atom, carboxyl, hydroxyl, cyano, sulpho, formyl, sulfydryl, nitryl, trialkylsilanyl. R6-R10 and R16-18 are hydrogen atom, halogen atom, alkyl, alicyclic alkylor aromatic alkyl, heterocyclic group, alkoxy, thiophenyl, amino, nitroso, sulfydryl, trialkylsilanyl, acyl, trifluoromethyl, hydroxyl, cyano, nitryl, carboxyl and sulfo.

Description

technical field [0001] The present invention relates to a curable composition, a cured film, a method for forming the same, and a compound. Background technique [0002] The curable composition can form a cured film in large quantities and easily through a simple coating process, so it is currently widely used. In particular, radiation-sensitive curable compositions are widely used in photocurable inks, photosensitive printing plates, and the like in addition to materials such as liquid crystal elements and semiconductor elements because the cured film pattern formation is easy. Such a curable composition usually contains a resin and a hardener. [0003] A typical example of the curing agent is a base generator that generates a base by the action of heat or radiation. Using this base generator, the base generated by the action of heat or radiation can be used as a catalyst to chemically modify the resin to harden the resin to form a cured film. In addition, the difference...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004G03F7/027C07D235/18C07F7/10
CPCC08K5/3445C08K5/3447C08L101/00C09K2003/1062
Inventor 石部彻远藤刚
Owner JSR CORPORATIOON
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