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Flame retardant for thermosetting resin including aromatic phosphoric acid ester, thermosetting resin composition including same, and cured material and application of same

An aromatic phosphate ester and resin composition technology, which is applied in the direction of compounds of Group 5/15 elements of the periodic table, phosphorus organic compounds, synthetic resin layered products, etc., to achieve the suppression of dielectric constant and dielectric loss tangent. The effect of increasing and suppressing the decrease of heat resistance

Active Publication Date: 2021-03-19
DIAHACHI CHEMICAL INDUSTRY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

DOPO in Patent Document 3 and the phosphazene compound in Patent Document 4 tend to increase the dielectric constant and dielectric loss tangent of the laminate, and improvement is a problem

Method used

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  • Flame retardant for thermosetting resin including aromatic phosphoric acid ester, thermosetting resin composition including same, and cured material and application of same
  • Flame retardant for thermosetting resin including aromatic phosphoric acid ester, thermosetting resin composition including same, and cured material and application of same
  • Flame retardant for thermosetting resin including aromatic phosphoric acid ester, thermosetting resin composition including same, and cured material and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0154] The present invention will be more specifically described by the following synthesis examples and test examples (Examples and Comparative Examples), but the scope of the present invention is not limited to the examples in these test examples.

[0155] [Identification of aromatic phosphates]

[0156] Using the following measuring devices and conditions, by 1 The aromatic phosphoric acid ester obtained in the synthesis example was identified by H-NMR.

[0157] ・Measuring device: manufactured by JEOL Ltd., 1 H-NMR device (model: JNM-ECS-400)

[0158] Solvent: CDCl 3

[0159] [Evaluation of thermosetting resin cured product]

[0160] The cured thermosetting resins obtained in Examples and Comparative Examples were evaluated by the following methods using the following measurement apparatus and conditions.

[0161] (flame retardant)

Synthetic example 1

[0196] (Synthesis Example 1) Synthesis of Di(xylyl) Chlorophosphate

[0197] 767 g of phosphorus oxychloride, 1,200 g of 2,6-xylenol, and 140 g of xylene as a solvent were filled into a 2-liter four-necked flask equipped with a stirrer, a thermometer, and a hydrochloric acid recovery device (a condenser connected to a water scrubber). and 6.2 g of magnesium chloride as a catalyst.

[0198] While stirring the obtained mixed solution, it was gradually heated up to a temperature of 160°C over about 3 hours to allow a reaction to occur, and the generated hydrogen chloride (hydrochloric acid gas) was recovered by a water scrubber. Thereafter, at the temperature (160° C.), the pressure in the flask was gradually reduced to 20 kPa, and xylene, unreacted phosphorus oxychloride, 2,6-xylenol, and by-produced hydrogen chloride were removed to obtain 1700 g of a reaction mixture containing di(xylyl chlorophosphate) of the following structural formula as a main component. In addition, th...

Synthetic example 2

[0200] (Synthesis Example 2) Synthesis of Aromatic Phosphate 1

[0201] 460 g of di(xylyl chlorophosphate) obtained in Synthesis Example 1, 196 g of bisphenol 1, 540 g of toluene as a solvent, and tetrahydrofuran were charged into a four-neck flask with a capacity of 2 liters equipped with a stirrer, a thermometer, a dropping funnel, and a condenser. 140g. In addition, 151 g of triethylamine as a hydrogen halide scavenger was filled in the dropping funnel.

[0202] The mixed solution in the four-necked flask was heated to a temperature of 65° C. while stirring, and triethylamine in the dropping funnel was added dropwise over 1 hour and 30 minutes while maintaining the temperature (65° C.). After completion of the dropwise addition, stirring was carried out at the temperature (65° C.) for 2 hours to obtain a reaction product.

[0203] The obtained reaction product was washed with dilute hydrochloric acid and water, neutralized and washed with an aqueous sodium hydroxide solut...

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Abstract

A flame retardant for a thermosetting resin including an aromatic phosphoric acid ester represented by general formula (I): [in the formula, R1-R4 each independently represent a hydrogen atom, a C1-4alkyl group, or a C1-4 alkoxy group, R5, R6, and R9 each independently represent a C1-10 alkyl group or a C1-10 alkoxy group, R7 and R8 each independently represent a C1-4 alkyl group or a C1-4 alkoxygroup, n is an integer of 1 to 10, n1 and n2 are each independently an integer of 0 to 3, m1 and M2 are each independently an integer of 0 to 4, p is an integer of 0 to 26, k is an integer of 1 to 12, and, when p is 2 or greater, any two R9 groups may connect to form another ring together with the carbon atoms of a ring to which the R9 groups are bonded].

Description

technical field [0001] The present invention relates to a flame retardant for thermosetting resins containing an aromatic phosphate, a thermosetting resin composition containing the same, a cured product thereof, and uses thereof. Background technique [0002] Laminates made of various materials such as thermosetting resins and synthetic resins such as thermoplastic resins are used in computers, cameras, mobile phones, LCD displays, TFT displays, and other electronic devices. Among these, thermosetting resins such as epoxy resins have excellent properties and have been used in general. [0003] The material of the laminated board is required to have various characteristics depending on its application, usage conditions, etc., one of which is flame retardancy. [0004] Generally, as a method of imparting flame retardancy to a resin material, there is a method of adding (adding) a halogenated compound such as a brominated flame retardant to the resin. However, in recent year...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08L101/00B32B5/28B32B27/18C07F9/09C08J5/24C08K5/523H05K1/03
CPCC08K5/523C07F9/094B32B5/024B32B2255/02B32B2457/08B32B5/26B32B2307/3065B32B2262/0261B32B2260/021B32B2255/26B32B2262/0276B32B2262/10B32B2250/20B32B5/022B32B2260/046B32B2262/101B32B2262/02C08J5/249C08J2363/00H05K1/0373H05K1/0366H05K2201/012C09K21/12C08L63/00C08K5/0066B32B27/20B32B2305/076C08J5/24C07F9/095
Inventor 矢羽田骏介
Owner DIAHACHI CHEMICAL INDUSTRY CO LTD
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