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Novel trisphenol compound

A compound, triphenol technology, applied in the field of new polyphenol compounds, can solve the problems of unobtained sensitivity, resolution residual film rate, heat-resistant storage stability, etc., and achieves excellent storage stability, improved heat resistance, dissolved Excellent effect

Active Publication Date: 2014-11-12
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in recent years, in the raw materials of photoresists, especially the raw materials of positive resists, no satisfactory results have been obtained for many characteristics such as sensitivity, resolution, residual film rate, heat resistance, and storage stability. Enhanced properties are strongly expected by novel structures of triphenols

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0117] (1) Measuring method of glass transition temperature

[0118] In a scanning differential calorimeter, the temperature was raised to a temperature 20°C higher than the melting point of the crystal of each compound, melted and cooled, and then heated to measure the glass transition point. The measurement conditions at this time are that the initial measurement temperature is 40°C, the measurement end temperature is the melting point + 20°C, and the heating rate is 10.0°C / min.

[0119] (2) Method for measuring solubility in solvents

[0120] Regarding the solubility, 10 g of propylene glycol monomethyl ether acetate was added to the container, and while maintaining at 28° C., 1 g of the triphenol compound was added and stirred for 10 minutes to confirm whether it was completely dissolved. If it is completely dissolved, add 1g as well, and repeat the dissolution operation until it is no longer dissolved. The solubility is calculated based on the g number that is most dissolved w...

reference example 1

[0122] (Synthesis of raw material carbonyl compound 4-acetyl-4'-hydroxybiphenyl)

[0123] (Synthesis of 4-acetoxybiphenyl)

[0124] In a 3L four-necked flask equipped with a reflux condenser, 373.8 g of acetic anhydride and 248.0 g (1.46 mol) of 4-phenylphenol were added, and the reaction was carried out for 3 hours while keeping the internal temperature at 130°C while raising the temperature. After the reaction, the reflux tube was replaced with a distillation tube, acetic anhydride and acetic acid were removed by vacuum distillation, n-heptane was added, and then cooled. The precipitated crystals were filtered and dried to obtain 296.8 g of white crystals of 4-acetoxybiphenyl. The yield with respect to the raw material 4-phenylphenol was 96% (mole).

[0125] (Synthesis of 4-acetyl-4'-hydroxybiphenyl)

[0126] In a 3L four-necked flask equipped with a reflux device and a dropping funnel, 314 g of aluminum chloride and 628 g of chloroform were added, and 120 g of acetic anhydride wa...

Embodiment 1

[0129] Synthesis of 1-[4-(4-hydroxyphenyl)phenyl]-1,1-bis(4-hydroxyphenyl)ethane

[0130] In a 500 ml four-necked flask equipped with a stirring device, a reflux condenser, and a dropping funnel, 6.8 g of methanol and 46.0 g (0.489 mol) of phenol were added, and after replacing the flask with hydrogen chloride gas, hydrogen chloride gas was blown to a saturated state. Then, while keeping the inside of the flask at 30 to 35°C, 9.0 g of 21% methyl mercaptan sodium salt aqueous solution was dropped over 1.5 hours under stirring. Furthermore, while keeping the internal temperature at 30-35°C, 30.0 g (0.141 mol) of 4-acetyl-4'-hydroxybiphenyl obtained in Reference Example 1 and 60.0 g of phenol were dropped over 1 hour while stirring. (0.637 mol) A mixed solution dissolved in 25 g of methanol. After completion of the dropping, the reaction was further performed for 2.5 hours while keeping the internal temperature at 30°C under stirring.

[0131] After the completion of the reaction, i...

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Abstract

A trisphenol compound is expressed by formula (1), wherein R represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, phenyl group or hydroxyl group; R1 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, or phenyl group; R2 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms; R3 represents a hydrogen atom or alkyl group with 1 to 8 carbon atoms; a represents 0, 1, 2, or 3; b represents 1 or 2; and c and d represent 0, 1, 2, 3, or 4; where the sum of b and c is 5 or less; R's may be either the same or different when a is 2 or more; R1's may be either the same or different when c is 2 or more; and R2's may be either the same or different when d is 2 or more.

Description

Technical field [0001] The present invention relates to a new type of polyphenol compound. In particular, it relates to a new type of triphenol compound in which a hydroxyphenyl group is directly bonded with a single bond to the phenyl nucleus of a phenylalkylene group in the center of the molecule. Background technique [0002] Triphenol compounds have been widely used in the past as raw materials for photoresists, raw materials for epoxy resins used in electrical insulating materials, branching agents for aromatic polycarbonates, and thermal recording materials Used as the raw material of the developer, the anti-fading agent, and the raw material of the bactericide and the bactericidal anti-fungal agent. [0003] As such a triphenol compound, for example, 1-[α-methyl-α-(4'-hydroxyphenyl)ethyl]-4-[α',α'-bis(4"-hydroxyphenyl) is known. )Ethyl]benzene (hereinafter also referred to as TrisP-PA) (Patent Document 1), 2,2'-[(4-hydroxy-3-methoxyphenyl)methylene]bis[3,5-di A triphenol c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/15C07C37/20
CPCC07C39/15C07C37/20
Inventor 良知照中野史保子
Owner HONSHU CHEM INDAL