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Azomethine compound and oily magenta ink

Inactive Publication Date: 2002-09-12
FUJIFILM HLDG CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006] An object of the present invention is to provide an oil-soluble dye excellent in color reproduction and color stability.
[0013] The azomethine compound represented by the formula (I) has excellent characteristics suitable for a magenta dye. Accordingly, the azomethine compound can be advantageously used in a preparation of an oily magenta ink for ink-jet recording.
[0014] Further, the azomethine compound represented by the formula (I) is excellent in stability to light and heat. Accordingly, the azomethine compound can be used a magenta dye that is excellent in a light resistance and in a heat resistance.

Problems solved by technology

Water-soluble dyes for ink-jet recording have poor resistance against water and light, while oil-soluble dyes are unsatisfactory in color reproduction and color stability.

Method used

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  • Azomethine compound and oily magenta ink
  • Azomethine compound and oily magenta ink
  • Azomethine compound and oily magenta ink

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0252] 8

[0253] [Synthesis of azomethine compound (Ia-12)]

[0254] In 1,000 ml of ethyl acetate, 87.9 g of 2-[4-{3-(tetradecyloxycarbo- nyl) propanoylamino}phenyl]-6-tert-butyl-7-chloropyrazolo[1,5-b][1,2,4]-tr- iazole was dissolved. Independently, 400 ml of methanol and 100 g of sodium carbonate were dissolved in 750 ml of water. The prepared two solutions were mixed, and 39.1 g of 4-amino-N-butyl-N-(2-cyanoethyl) aniline was further added. The obtained solution was dropwise added for 1.5 hour to a solution in which 50.0 g of ammonium persulfate was dissolved in 300 ml of water. The resulting solution was made to react for 1 hour. After 1,000 ml of ethyl acetate and 1,000 ml of water were added, the organic phase was collected. The collected liquid was twice washed with 1,500 ml of water, and the solvent was distilled off. To the obtained oil, 300 ml of acetonitrile was added to precipitate a crystalline product. The product was collected and air-dried, and then recrystallized from 30...

example 2

[0256] 9

[0257] [Synthesis of azomethine compound (Ia-4)]

[0258] N-butylaniline and ethylacrylate were made to react to prepare N-butyl-N-(2-ethoxycarbonylethyl)aniline, which was then nitrosoated and reduced to synthesize 4-amino-N-butyl-N-(2-ethoxycarbonylethyl)aniline.

[0259] From the prepared compound, the azomethine compound (Ia-4) was synthesized in the same manner as described in Example 1.

example 3

[0260] 10

[0261] [Synthesis of azomethine compounds]

[0262] The azomethine compounds (Ia-1), (Ia-6), (Ia-13), (Ia-14) and (Ia-15) were synthesized in a similar manner to Example 1 or 2.

[0263] The melting points of the compounds (Ia-1) and (Ia-6) are lower than room temperature (i.e., they are in the form of oily liquid at room temperature). The melting point of the compound (Ia-13) was 132-133.degree. C. , the melting point of the compound (Ia-14) was 119-120.degree. C. , and the melting point of the compound (Ia-15) was 118-120.degree. C.

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Abstract

An azomethine compound is represented by the formula (I). 1 and R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to 50 carbon atoms in total.

Description

FIELD OF THE INVENTION[0001] The present invention relates to an azomethine compound. In detail, the invention relates to an azomethine compound suitable for a jet printing ink of magenta color.BACKGROUND OF THE INVENTION[0002] In an ink-jet recording method, images or characters are printed on image-receiving material with ink ejected from very fine nozzles. The ink-jet recording method can be conducted by using a relatively inexpensive apparatus (i.e., an ink-jet printer), as compared with other printing methods. Further, in proportion to improvement of the method, images of high qualities have been given recently. Now, the ink-jet recording method is one of the most popular image-recording methods.[0003] Ink for the ink-jet recording method (i.e., jet printing ink) must not choke the fine nozzles. Since aqueous inks (aqueous solutions of dyes) hardly choke the nozzles, they are widely used. However, the aqueous inks have poor water resistance. Various means (described in Japanese...

Claims

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Application Information

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IPC IPC(8): C09B55/00C09D11/00
CPCC09B55/009C09D11/32C09D11/328
Inventor YAMAKAWA, KATSUYOSHIMOTOKI, MASUJIASANUMA, NAOKISUZUKI, RYOSATO, TADAHISAMIKOSHIBA, HISASHI
Owner FUJIFILM HLDG CORP
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