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Novel polymer and diamine compound

A technology based on amine compounds and carbon numbers, which is applied in the field of new polymers and diamine compounds, can solve the problems of volume change and inability to obtain liquid crystal display characteristics, and achieve high voltage retention, high abrasion resistance, and excellent display characteristics.

Active Publication Date: 2020-06-09
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] On the other hand, in polyamic acid exhibiting high solvent solubility, there is also the problem that sufficient liquid crystal display characteristics cannot be obtained, and volume changes due to imidization are likely to occur. Solvent type is soluble polyimide
[0009] On the other hand, for diamines, as in the example of the above-mentioned acid dianhydrides, until now, no method of imparting various properties using inexpensive raw materials has been known.

Method used

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  • Novel polymer and diamine compound
  • Novel polymer and diamine compound
  • Novel polymer and diamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0188] Examples are given below to describe the present invention in more detail, but the present invention is not limited thereto.

[0189] The structures of diamine compounds used in Examples are shown below.

[0190]

[0191]

[0192]

[0193]

[0194] DA-1 to DA-8 and DA-10 to DA-15 are novel compounds not disclosed in literature etc., and their synthesis methods will be described in detail in Synthesis Examples 1 to 14 below.

[0195] DA-9 was synthesized using the synthesis method described in the patent document (WO2017-057854).

[0196] Abbreviations of organic solvents used in Examples and the like are as follows.

[0197] NMP: N-methyl-2-pyrrolidone.

[0198] BCS: butyl cellosolve.

[0199] THF: Tetrahydrofuran.

[0200] DMF: N,N-Dimethylformamide.

[0201] CH 2 Cl 2 : Dichloromethane.

[0202] CHCl 3 : Chloroform.

[0203] MeOH: Methanol.

[0204] EtOH: ethanol.

[0205] IPA: Isopropyl Alcohol.

[0206] 1,3-DMCBDA: 1,3-Dimethyl-1,2,3,4-cyclob...

Synthetic example 1

[0212] Synthesis of [DA-1]:

[0213]

[0214] Put 4-[(4-aminophenoxy)methoxy]aniline (230.0g, 999mmol) and THF (1600g) into a 3L four-necked flask, add di-tert-butyl dicarbonate (218.0g, 999 mmol), stirred at room temperature. After completion of the reaction, the reaction liquid was concentrated, and the obtained residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:1 volume ratio) to obtain 158.0 g of [DA-1-1].

[0215] [DA-1-1] (132.2 g, 400 mmol) and NMP (1300 g) were charged into a 3 L four-necked flask, and 1,3-DMCBDA (40.4 g, 180 mmol) was added to a water bath, followed by stirring at room temperature for 6 hours. Next, pyridine (85.5 g, 1081 mmol) and acetic anhydride (55.2 g, 540 mmol) were thrown into the reaction liquid, and it stirred at 60 degreeC. After completion of the reaction, the reaction system was poured into pure water (5 L), and the precipitate was filtered off. MeOH (2 L) was added to the obtained crude product, and 18...

Synthetic example 2

[0219] Synthesis of [DA-2]:

[0220]

[0221] Put 4-[3-(4-aminophenoxy)propoxy]aniline (70.0g, 271mmol) and THF (500g) into a 3L four-necked flask, add di-tert-butyl dicarbonate (59.1mmol) dropwise in a water bath g, 271 mmol), stirred at room temperature. After completion of the reaction, the reaction liquid was concentrated, and the obtained residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:1 volume ratio) to obtain 46.4 g of [DA-2-1].

[0222] [DA-2-1] (46.4g, 129mmol) and NMP (460g) were put into a 3L four-necked flask, and 1,3-DMCBDA (14.5g, 65mmol) was added to the water bath, and it stirred at room temperature for 6 hours. Next, pyridine (30.7 g, 388 mmol) and acetic anhydride (19.8 g, 194 mmol) were thrown into the reaction liquid, and it stirred at 60 degreeC. After completion of the reaction, the reaction system was poured into pure water (3 L), and the precipitate was filtered off. MeOH (400 ml) was added to the obtained crude pro...

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PUM

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Abstract

The present invention relates to a diamine compound represented by general formula (1). In formula (1), each of R1, R2, R3 and R4 independently represents H, CH3 or CF3, where at least one of R1, R2,R3 and R4 represents CH3 or CF3; W1 represents a single bond or a phenylene group; W2 represents a phenylene group; and L represents a linear or branched alkylene group having 1-10 carbon atoms, whereCH2 in the alkylene group may be substituted with an oxygen atom or the like. By using raw materials with high availability, the present invention is capable of providing a diamine compound that caneasily impart various properties and, furthermore, is capable of providing a novel polymer obtained from said diamine compound.

Description

technical field [0001] This invention relates to the polymer obtained using the novel diamine compound (it may abbreviate also "diamine" in this invention) useful as a raw material of the polymer used for a liquid crystal aligning film, and this diamine. In more detail, the present invention relates to, for example, a polyimide suitable as an electronic material and a diamine compound as a raw material monomer thereof. Background technique [0002] In general, polyimide resins are used as electronic materials such as liquid crystal display elements, protective materials in semiconductors, insulating materials, and color filters due to their characteristic high mechanical strength, heat resistance, insulation, and solvent resistance. being widely used. In addition, recently, applications as materials for optical communication such as materials for optical waveguides are expected. [0003] In recent years, the development of this field has been remarkable, and accordingly, t...

Claims

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Application Information

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IPC IPC(8): C07D487/04C08G73/10
CPCC07D487/04C08G73/10
Inventor 森内正人
Owner NISSAN CHEM IND LTD
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