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Fluorinated dyes or colorants and their uses

A colorant, fluorinated solvent technology, applied in organic dyes, azo dyes, organic chemistry, etc., can solve the problems of limited solubility and high viscosity of electrophoretic dispersions

Inactive Publication Date: 2009-07-08
SIPIX IMAGING INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of fluorinated silicon phthalocyanine and naphthalocyanine dyes in perfluorinated solvents such as HT-200 is still limited, and the resulting electrophoretic dispersions containing this type of dyes have relatively high viscosities

Method used

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  • Fluorinated dyes or colorants and their uses
  • Fluorinated dyes or colorants and their uses
  • Fluorinated dyes or colorants and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0185] Preparation of Substituted Copper Phthalocyanine (C3)

[0186]

[0187] m, n, p and q are independently 0-4, and m+n+p+q≤4

[0188] C3

[0189] Copper phthalocyanine (1.4gm, 2.4mmole, Aldrich) and Krytox A mixture of iodides (16.32 gm, 9.6 mmole, DuPont) was charged to a 72 mL glass-lined pressure reactor (Parr Instruments). The reactor was vacuum sealed at 1 Torr and heated at 350°C for 38 hours. Use 250 mL of PFS-2 in a Soxhlet extractor TM The resulting crude product was extracted (extracted) for 1 day. The dark blue solution thus obtained was washed 3 times with 250 mL of acetone and evaporated to a slurry by rotary evaporation (60 °C) under vacuum (~5 Torr) and then under high vacuum (~1 Torr) overnight. The syrupy compound was further purified by refluxing with diethyl ether (250 mL) for 1 day and the resulting mixture was separated. The dark blue syrup was evaporated again by rotary evaporation (60 °C) under vacuum (~5 Torr) and then under high vacuum...

Embodiment 12

[0191] Preparation of Substituted Copper Tetra-tert-butyl Phthalocyanine (CB2)

[0192]

[0193] m, n, p and q are independently 0-3, and m+n+p+q≤2 or 3

[0194] CB2

[0195] 1. Synthesis of copper(II) bromide 2,9,16,23-tetra-tert-butyl-29H,31H-phthalocyanine

[0196] At room temperature, in trifluoroacetic acid (50mL, Aldrich) and H 2 SO 4 (15 mL, Fisher Scientific) was stirred with copper(II) 2,9,16,23-tetra-tert-butyl-29H,31H-phthalocyanine (1.00 gm, 1.24 mmol, Aldrich) and N-bromosuccinimide (1.00 gm, 5.61 mmol, Aldrich) for 24 hours. The resulting dark blue solution was poured into 200 mL of ice water. The resulting solid was washed with water, removed by filtration, and dried (60°C, 60 Torr) overnight. A dark blue solid (1.22 gm, 86%) was obtained.

[0197] 2. Synthesis of Substituted Copper(II) Tetra-tert-Butyl Phthalocyanine (CB2)

[0198] Add 25 mL (11.25 mmole) of a 0.45-0.50 M solution of 9-boronbicyclo[3.3.1]nonane (9-BBN) in THF into 4 gm of Kr...

Embodiment 13

[0200] Preparation of Substituted Copper Tetrakis(4-cumylphenoxy)phthalocyanine (CC1)

[0201]

[0202] m, n, p and q are independently 0-4, and m+n+p+q≤2 or 3

[0203] CC1

[0204] 1. Synthesis of Copper(II) Bromide Tetrakis(4-cumylphenoxy)phthalocyanine

[0205] At room temperature, in trifluoroacetic acid (50mL, Aldrich) and H 2 SO 4 (15mL, Fisher Scientific) was stirred in a solution of copper(II) tetrakis(4-cumylphenoxy)phthalocyanine (1.00gm, 0.71mmol, Aldrich) and N-bromosuccinimide (0.60gm, 3.37mmol, Aldrich) mixture for 24 hours. The resulting dark blue solution was poured into 200 mL of ice water. The resulting solid was washed with water, removed by filtration, and dried (60°C, 60 Torr) overnight. A dark blue solid (1.10 gm, 89%) was obtained.

[0206] 2. Synthesis of substituted copper tetrakis(4-cumylphenoxy)phthalocyanines (CC1) to make

[0207] At 0°C, 25mL (11.25mmol) of 9-borabicyclo[3.3.1]nonane (9-BBN) 0.45-0.50M solution in tetrahydrofur...

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Abstract

This invention relates to novel fluorinated dyes or colorants having high solubility and low viscosity in halogenated, especially fluorinated, solvents. The dyes or colorants of the present invention have shown to improve the performance of electrophoretic displays.

Description

[0001] This application is a divisional application of the patent application with the application number 200480027897.1 (PCT / US2004 / 024932) and the title of the invention "Fluorinated dyes or colorants and their applications". This application claims priority to US Provisional Application No. 60 / 493,703, filed August 8, 2003, and US Provisional Application No. 60 / 501,921, filed September 10, 2003. Both prior applications are hereby incorporated by reference in their entirety. technical field [0002] The present invention relates to novel fluorinated dyes or colorants having high solubility and low viscosity in halogenated, especially fluorinated solvents. The dyes or colorants of the invention have been shown to improve the performance of electrophoretic displays. Background technique [0003] An electrophoretic display (EPD) is a non-emissive device based on the electrophoretic phenomenon affecting the migration of charged pigment particles in a solvent, preferably a col...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B47/04C07D487/22G02F1/167
Inventor 杨进方凯加李英熙臧宏玫王红周建宏梁荣昌
Owner SIPIX IMAGING INC
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