JP2970015B2 - Inkjet recording liquid - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a recording liquid using a pigment suitable for ink jet recording.

[0002]

2. Description of the Related Art Ink jet recording systems have characteristics such as low noise, low running cost, and easy colorization, and are rapidly spreading in recent years.
As a coloring agent of a recording liquid used for inkjet recording,
Usually, water-soluble dyes such as acid dyes and direct dyes are used, but light-fastness, water-fastness and other fastnesses are not sufficient, and improvement is being studied. To improve the light fastness and water fastness of the water-soluble dye, for example, JP-A-64-62372,
JP-A-64-48873, JP-A-64-16880
And many proposals have been made as described in JP-A-63-289079, etc., but are not yet sufficient.

On the other hand, a method of using a pigment as a coloring agent has been studied for a long time, for example, Japanese Patent Application Laid-Open No. 47-12104.
JP-A-56-147859, JP-A-56-147
863, JP-A-56-147869, JP-A-56-147869
157468, JP-A-57-21466, JP-A-67-14
A number of applications have been filed, such as 2-74773. When a pigment is used as a colorant, light resistance and water resistance are remarkably improved as compared with dyes, but storage stability as a recording liquid is inferior, so that it has not been put to practical use.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an ink jet recording liquid having high light resistance and water resistance of a recorded image, and excellent storage stability and discharge stability as a recording liquid. This purpose is based on the novel finding that it can be achieved by using a specific dispersant.

[0005]

The gist of the present invention is to provide an aqueous medium, a pigment and a compound represented by the general formula [I],
[II] In an inkjet recording liquid containing at least one of the compounds represented by [III] and [IV]. Hereinafter, the present invention will be described in detail. The general formulas [I] and [I
In I], [III] and [IV], R ₁ , R ₂ , R ₃
And the alkyl group and alkenyl group for R ₄ may be linear or branched, and in the case of an alkenyl group, the position of the double bond is not limited.

As the pigment in the recording liquid of the present invention, azo, phthalocyanine, quinacridone and carbon black can be used.
Yellow-74, -154, Pigment Re
d-5, -122 and Pigment Blue-15 are preferred. The content of the pigment is in the range of 0.5 to 10% by weight, preferably 1 to 7% by weight based on the total weight of the recording liquid.
Range.

The aqueous medium used in the recording liquid of the present invention includes water and water-soluble organic solvents such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, (# 200), polyethylene glycol. , (# 400), glycerin, N-methyl-pyrrolidone, N-ethyl-pyrrolidone, N-vinyl-pyrrolidone, 1,3-dimethyl-imidazolidine, ethylene glycol monoallyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, etc. It is preferable that the content of the water-soluble organic solvent is in the range of 0 to 50% by weight based on the total amount of the recording liquid.

[0008] Examples of compounds of the general formula [I] used in the recording liquid as dispersing agent of the present _{invention, No. I-1 CH 2 -CONHC} 18 H 37 | NaO 3 S-CH-COONa No. I _{-2 CH 2 -CONHC 12 H 25 |} NaO 3 S-CH-COONa No. I-3 CH-CONHC 17 H 35 | NH 4 O 3 S-CH-COONH 4 No. I-4 CH 2 -CONHC 18 H _{35 | NaO 3 S-CH-} COONa No. I-5 CH 2 CONHC 11 H 21 | examples of NH ₄ O ₃ S-CHCOONH ₄ the compound of the general formula [II], Examples of the compound of the general formula (III) include Is mentioned. As the compound of the general formula _{[IV], No.IV -1 CH 2 COOC 8 H} 17 | NaO 3 S-CHCOOC 8 H 17 No.IV -2 CH 2 COOC 11 H 21 | NaO 3 S-CHCOOC 11 H _{21 No.IV -3 CH 2 COOC 9 H} 17 | H 4 NO 3 S-CHCOOC 9 H 17 No.IV -4 CH 2 COOC 11 H 21 | NaO 3 S-CHCOOC 6 H 13 and the like.

As such a compound, lapizol B-
80 (manufactured by NOF CORPORATION), Diaserver PN-19
70J (manufactured by Hoechst) and the like are commercially available, and these can be used as appropriate. In the recording liquid of the present invention,
The content of these dispersants may be in the range of 30 to 100% by weight, preferably 30 to 70% by weight, alone or in combination with the weight of the pigment. These dispersants may be used alone in the same general formula,
Further effects can be obtained by using them together. Further, by adding 0.5 to 20% by weight of a surfactant to the recording liquid of the present invention, quick drying after printing and print quality can be improved. Also, urea,
By adding caprolactam, the ejection stability can be further improved.

[0010]

The recording liquid of the present invention is used for ink jet recording and has excellent light fastness and water resistance of a recorded image, and also has extremely excellent storage stability and discharge stability as a recording liquid.

[0011]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Example 1 Composition of Recording Liquid Amount Used (g) Polyethylene Glycol (# 200) 15 Compound of No. I-1 1.5 Pigment Red 122 4 Water Total Remaining 100 The above components were placed in a container and averaged 0.5 mm in diameter. Was ground for 20 hours using a sand grinder (manufactured by Igarashi Machine Manufacturing Co., Ltd.) together with 130 ml of the glass beads. After filtration under pressure with a Teflon filter having a pore size of 3 μm, the recording solution was prepared by deaeration using a vacuum pump and an ultrasonic cleaner. Using the obtained recording liquid, ink jet recording was performed on electrophotographic paper (manufactured by Fuji Xerox Co., Ltd.) using an ink jet printer (IO-735, manufactured by Sharp Corporation), and the following (a), (b) and Various evaluations were performed according to the method (c). (A) Light fastness of recorded image Discoloration and discoloration after irradiating the printed matter with a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.) for 100 hours were small. (B) Storage stability Even after the recording solution was sealed in a Teflon container and stored at 60 ° C. for 2 months, no gelation was observed, and no sediment was observed. (C) Discharge stability Continuous discharge was performed at room temperature for 48 hours, but stable high-quality recording was performed throughout.

Comparative Example 1 Instead of the compound of No. I-1 in Example 1, Discol 30 (trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), which is a naphthalenesulfonic acid formalin condensate-based dispersant, was used. The recording liquid was adjusted, and the same evaluation as in Example 1 was performed.
A sediment is formed in 3 days at 0 ° C., and 1
Discharge became impossible in 5 hours. Comparative Example 2 A recording liquid was prepared by using Pronone-204 (trade name, manufactured by NOF Corporation), which is an oxyethylene / oxypropylene block polymer type dispersant, instead of the compound of No. I-1 in Example 1. However, as a result of performing the same evaluation as in Example 1, a sediment was generated at 60 ° C. for 7 days, and in a continuous discharge at room temperature, discharge became impossible in 20 hours.

Example 2 Composition of recording liquid Used amount (g) Diethylene glycol 20 No.II-3 compound 1 Pigment Blue 153 Water Total remaining amount 100 Using the above composition, a recording liquid was prepared in the same manner as in Example 1. After adjustment, various evaluations (a), (b), and (c) were performed.

Comparative Example 3 A recording liquid was prepared by using Polynas PS-1 (manufactured by Toyo Soda Kogyo Co., Ltd.) which is a sodium polystyrene sulfonate dispersant instead of the compound of No. II-3 in Example 2. As a result of performing the same evaluation as in Example 1, a sediment was formed at 60 ° C. for 4 days, and discharge became impossible in 13 hours in continuous discharge at room temperature.

Example 3 Composition of Recording Solution Used Amount (g) Compound of No. I-2 0.5 Compound of No. II-1 0.5 Glycerin 10 Pigment Yellow-74 2 Water Remaining amount 100 Example 4 Composition of recording liquid Amount used (g) Compound of No. I-3 0.5 Compound of No. II-3 1.0 Compound of No. III-3 1.5 Carbon black 6 ε-caprolactam 5 Water Total remaining amount 100 Using the ink compositions of Examples 3 and 4, a recording liquid was prepared in the same manner as in Example 1, and various evaluations were performed. As a result, all were good as in Example 1. Example 5 Composition of Recording Solution Amount Used (g) Glycerin 15 Compound of No. IV-1 1.0 Pigment Yellow-74 2 Water Total Remaining 100 The above components were placed in a container, and 130 ml of glass beads having an average diameter of 0.5 mm was taken. Together with a sand glider (manufactured by Igarashi Machine Manufacturing Co., Ltd.) for 20 hours. After filtration under pressure with a Teflon filter having a pore size of 3 μm, the recording solution was prepared by deaeration using a vacuum pump and an ultrasonic cleaner. Using the obtained recording liquid, ink jet recording was performed on electrophotographic paper (manufactured by Fuji Xerox Co., Ltd.) using an ink jet printer (IO-735, manufactured by Sharp Corporation), and the following (a), (b) and Various evaluations were performed according to the method (c). (A) Light fastness of recorded image The discoloration and discoloration after irradiating the printed matter with a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.) for 100 hours were small. (B) Storage stability Even after the recording solution was sealed in a Teflon container and stored at 60 ° C. for 2 months, no gel was formed, and no sediment was observed. (C) Ejection stability Although continuous ejection was performed at room temperature for 48 hours, stable high-quality recording was performed throughout.

Comparative Example 3 A recording liquid was prepared by using Discol 30 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), which is a dispersant of a naphthalenesulfonic acid formalin condensate, instead of the compound of No. IV-1 in Example 5. Adjustment was performed and the same evaluation as in Example 1 was carried out. As a result, sediment was formed at 60 ° C. for 3 days, and discharge became impossible in 15 hours in continuous discharge at room temperature. Comparative Example 4 The recording liquid was prepared by using Pronone 204 (manufactured by NOF CORPORATION), which is an oxyethylene / oxypropylene block polymer type dispersant, instead of the compound of No. IV-1 in Example 5. As a result of performing the same evaluation as that of No. 1, 60
A sediment is generated at 7 ° C. for 7 days.
Discharge became impossible in a time.

Example 6 Composition of recording liquid Amount used (g) Diethylene glycol 20 No. IV-3 compound 1 Pigment Blue 15 3 Water Remaining amount 100 Using the above composition, a recording liquid was prepared in the same manner as in Example 1. After adjustment, various evaluations of (a), (b) and (c) were performed, and all were good.

Example 7 Composition of recording liquid Amount used (g) Compound No. IV-2 1.0 Compound No. IV-4 1.0 Polyethylene glycol (# 200) 15 Pigment Red-5 4 Water Remaining amount Using the above composition, a recording liquid was prepared in the same manner as in Example 1 and various evaluations were performed. As a result, all were good as in Example 1.

Continuation of front page (58) Field surveyed (Int.Cl. ⁶ , DB name) C09D 11/00-11/20

Claims (1)

(57) [Claims] 1. An ink jet recording liquid comprising an aqueous medium, a pigment and at least one compound represented by the following general formulas [I], [II], [III] and [IV]. CH ₂ -CONHR ₁ | ... [I] _{MO 3 S-CH-COOM CH} 2 -CONHR 2 | ... (II) _{MO 3 S-CH-CONHR 2} CH 2 -COOR 3 | ... [III] MO ₃ S-CH —COOM CH ₂ COOR ₄ |... [IV] MO ₃ S—CHCOOR ₄ (wherein each of R ₁ and R ₃ represents an alkyl group or an alkenyl group having 10 to 20 carbon atoms, and R ₂ and R ₄ each represent a carbon number. 6 to 16 alkyl or alkenyl groups,
M represents Na or NH ₄ . )