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Phthalocyanine dyes and its preparation method

The technology of phthalocyanine dye and copper phthalocyanine is applied in the field of phthalocyanine dye of optical disc and preparation method thereof, and can solve the problems of unsatisfactory recording effect and low yield of phthalocyanine dye.

Inactive Publication Date: 2003-10-08
TAIWAN FLUORO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs more than 20 hours to react, and the productive rate is not high (about 60%)
Furthermore, under the current demand for high-speed recording, the phthalocyanine dyes prepared by known methods cannot obtain satisfactory recording effects.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of brominated bis(hydroxymethyl)tetrakis(2,4-dimethyl-3-phenoxy)copper phthalocyanine and ferrocene carboxylate

[0031] Fill 250 g (213.2 mmol) bis(hydroxymethyl)tetrakis(2,4-bis Methyl-3-phenoxy)copper phthalocyanine (in 750 ml of dichlorotoluene), followed by the addition of 144 g (626.0 mmol) of ferrocenecarboxylic acid, 199 g (576.7 mmol) of dicyclohexylcarbide imide and 25 g (204.6 mmol) of 4-dimethylaminopyridine. The green solution was refluxed for 1 hour, then cooled to room temperature. The green solution was filtered while washing the residue with dichloromethane (3 x 250 mL). The filtrate was concentrated by evaporation to 750 g of solution, which was then poured into 7.5 L of acetonitrile. The precipitate was collected by filtration, washed with 500 mL of water and 500 mL of acetonitrile, and dried overnight at 100°C.

[0032] The crude product was then dissolved in 1 liter of toluene, and 250 grams of silica gel were added. The mixture was...

Embodiment 2

[0038] Discs coated with dye

[0039] 2.5% by weight of ferrocene carboxylate of brominated bis(hydroxymethyl)tetrakis(2,4-dimethyl-3-phenoxy)copper phthalocyanine obtained in Example 1 was dissolved in dibutyl ether A solution of (dibytylether) / 2,6-dimethyl-4-heptanone (2,6-dimethyl-4-heptanone) (98:2) was passed through polytetrafluoroethylene (Teflon) with a pore width of 0.2 microns ) filter paper and applied to discs by spin coating. The obtained measurement results are shown in Table 1.

Embodiment 3

[0047] Discs coated with dye

[0048] With the weight ratio of 97.5: 2.5, the ferrocene carboxylic acid ester compound of brominated bis(hydroxymethyl)tetrakis(2,4-dimethyl-3-phenoxy) copper phthalocyanine prepared in example 1 Mixed with tetrakis(2,4-dimethyl-3-phenoxy)copper phthalocyanine bromide prepared in comparative example 3. A solution of 2.5% by weight of the above mixture dissolved in dibutyl ether / 2,6-dimethyl-4-heptanone (98:2) was passed through a polytetrafluoroethylene (Teflon) filter paper with a pore width of 0.2 μm, And applied on the disc by means of spin coating method. The obtained measurement results are shown in Table 1.

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PUM

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Abstract

A phthalocyanine dye is prepared through reaction of the halogenated metal-phthalocyanine complex on ferrocenylcarboxylic acid under existance of bicyclohexyl biimide carbonate and 4-dimethylamino pyridine. A phthalocyanine dye composition contains tetra-(2,4-dimethyl-3-phenyloxy) copper phthalocyanine bromidid (1-10 wt.%), bis-(hydroxymethyl) tetra-(2,4-dimethyl-3-phenyloxy) copper phthalocyanine bromidid (1-10 wt.%), bis-(hydroxymethyl) tetra-(2,4-dimethyl-3-phenyloxy) copper phthalocyanine, and esterified ferrocenylcarboxylic acid.

Description

technical field [0001] The invention relates to a phthalocyanine dye and a preparation method thereof, in particular to a phthalocyanine dye applied to optical discs and a preparation method thereof. Background technique [0002] CD-R is a kind of optical disc with high reliability, long storage life, large capacity and low cost. It is widely used to store large-capacity data. [0003] CD-R discs must meet some specifications, such as the reflectivity of the recorded disc must be greater than 60%, the jitter (Jitter) of the recording point signal (such as 3T or 11T) must be less than 35ns and other requirements. It has been found that phthalocyanine dyes as CD-R recording materials have excellent recording characteristics in the absorption band of 770 to 790 nm. [0004] US Pat. Nos. 6,087,492 and 6,399,768 disclose a phthalocyanine dye suitable for CD-R recording materials, which can meet the requirements of high reflectivity and low jitter value when coated on optical dis...

Claims

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Application Information

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IPC IPC(8): C09B47/32
Inventor 王复兴许光美
Owner TAIWAN FLUORO TECH
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