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Azo Compound, Aqueous Solution, Ink Composition, Ink for Inkjet Recording, Inkjet Recording Method, Ink Cartridge for Inkjet Recording, and Inkjet Recorded Material

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Azo Compound, Aqueous Solution, Ink Composition, Ink for Inkjet Recording, Inkjet Recording Method, Ink Cartridge for Inkjet Recording, and Inkjet Recorded Material (19) TZZ _ _T (11) EP 2 712 894 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 02.04.2014 Bulletin 2014/14 C09B 31/153 (2006.01) C09D 11/00 (2014.01) (21) Application number: 13185960.5 (22) Date of filing: 25.09.2013 (84) Designated Contracting States: • Hayashi, Shinya AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Kanagawa 258-8577 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Iizumi, Takashi PL PT RO RS SE SI SK SM TR Kanagawa 258-8577 (JP) Designated Extension States: • Yamada, Hiroshi BA ME Kanagawa 258-8577 (JP) • Norizuki, Yutaro (30) Priority: 26.09.2012 JP 2012212754 Kanagawa 258-8577 (JP) 14.03.2013 JP 2013051807 • Amasaki, Ichiro 20.09.2013 JP 2013196181 Kanagawa 258-8577 (JP) • Tanaka, Shigeaki (71) Applicant: Fujifilm Corporation Kanagawa 258-8577 (JP) Minato-ku Tokyo (JP) (74) Representative: Morpeth, Fraser Forrest Fujifilm Imaging Colorants Limited (72) Inventors: Intellectual Property Group • Yagi, Kazunari P.O. Box 42 Kanagawa 258-8577 (JP) Hexagon Tower Blackley, Manchester M9 8ZS (GB) (54) Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material (57) There is provided a compound represented by the following formula (1): wherein each of R1a to R1k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M1a and M1b independently represents a hydrogen atom or a monovalent counter cation, Y1 represents a nitrogen atom or a carbon atom having a hydrogen atom or monovalent substituent,1 A represents an aromatic group, and the aromatic group represented by A 1 may contain a heteroatom or may have a substituent. EP 2 712 894 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 712 894 A1 Description BACKGROUND OF THE INVENTION 5 1. Field of the Invention [0001] The present invention relates to an azo compound, an aqueous solution, an ink composition, an ink for inkjet recording, an inkjet recording method, an ink cartridge for inkjet recording, and an inkjet recorded material. 10 2. Description of the Related Art [0002] An inkjet recording method enjoys a low material cost and a capability of highspeed recording, low-noise recording and easy color recording and therefore, is rapidly spread and further growing. [0003] The inkjet recording method includes a continuous system of continuously flying a liquid droplet and an on- 15 demand system of flying a liquid droplet according to image information signals, and the ejection system therefor includes a system of ejecting a liquid droplet by applying a pressure from a piezoelectric element, a system of ejecting a liquid droplet by generating a bubble in the ink by heat, a system using an ultrasonic wave, and a system of suctioning and ejecting a liquid droplet by an electrostatic force. As the ink for inkjet recording, an aqueous ink, an oil-based ink or a solid (fusion-type) ink is used. 20 [0004] The coloring agent used in such an ink for inkjet recording is required to exhibit good solubility or dispersibility for a solvent, allow for high-density recording, provide a good hue, be fast to light, heat and active gases in the environment (for example, an oxidative gas such as NOx and ozone, and SOx), be excellent in the resistance against water and chemicals, ensure good fixing and less blurring on an image-receiving material, give an ink with excellent storability, have high purity and no toxicity, and be available at a low cost. 25 [0005] In particular, there is a strong demand for an ink composition having a good black hue, being fast to light, humidity and heat, and ensuring that the molar extinction coefficient is high, the storage stability is excellent, the letter quality in document printing is high, bronze gloss is suppressed, and at the printing on an image-receiving material having an ink-receiving layer containing a porous white inorganic pigment particle, resistance to an oxidative gas such as ozone in the environment is developed. 30 [0006] In International Publication No. 2012/014954 and International Publication No. 2012/014955, an ink composition containing an azo compound having a specific structure capable of resolving the above-described task is described. Summary of the Invention 35 [0007] The ink composition described in International Publication No. 2012/014954 and International Publication No. 2012/014955 exhibits an excellent performance as stated above, but with respect to the color tone and suppression of bronze gloss in a recorded image when various recording materials are used, a higher level of performance is sometimes required. [0008] An object of the present invention is to provide a compound capable of providing for an ink having a good color 40 tone as an ink for black color and exerting that the color tone is little changed when observed under various light sources (the dependency on observation light source is small) and exerting excellent suppression of bronze gloss in a recorded image when various recording materials are used. Also, the present invention relates to an aqueous solution, an ink composition, an ink for inkjet recording, each containing the compound, an inkjet recording method using the ink for inkjet recording, an ink cartridge for inkjet recording filled with the ink for inkjet recording, and an inkjet recorded materi al 45 formed using the ink for inkjet recording. [0009] The present inventors have made detailed studies with an aim to resolve the above-described task, as a result, it has been found that in a diazo compound having a specific structure containing a pyridine coupler substituted with a sulfophenylamino group, when the sulfo group is substituted on the meta-position with respect to the amino group, the solubility of the dye in water can be enhanced, making it possible to avoid dye precipitation on the printing paper surface 50 and in turn, suppress bronze gloss, and also, the electron-withdrawing property of the sulfo group in the aniline moiety is reduced due to meta-substitution, leading to shift of the absorption wavelength to the long wavelength side and enhancement in the color tone as an ink for black color and the dependency on observation light source becomes good, whereby the task above can be resolved. [0010] That is, the above-described object can be attained by the following techniques. 55 [1] A compound represented by the following formula (1): 2 EP 2 712 894 A1 5 10 15 wherein each of R1a to R1k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M1a and M1b independently represents a hydrogen atom or a monovalent counter cation, 20 Y1 represents a nitrogen atom or a carbon atom having a hydrogen atom or monovalent substituent, A1 represents an aromatic group, and the aromatic group represented by A 1 may contain a heteroatom or may have a substituent. [2] The compound as described in [1], wherein the compound represented by formula (1) is a compound represented by the following formula (2): 25 30 35 40 wherein each of R 2a to R 2h and R 2k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M2a and M2b independently represents a hydrogen atom or a monovalent counter cation, 45 Y2 represents a nitrogen atom or a carbon atom having a hydrogen atom or a monovalent substituent, A2 represents an aromatic group, and the aromatic group represented by A 2 may contain a heteroatom or may have a substituent. [3] The compound as described in [2], wherein the compound represented by formula (2) is a compound represented by the following formula (3): 50 55 3 EP 2 712 894 A1 5 10 15 wherein each of R 3a to R 3h and R 3k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M3a and M3b independently represents a hydrogen atom or a monovalent counter cation, 20 A3 represents an aromatic group, and the aromatic group represented by A 3 may contain a heteroatom or may have a substituent. [4] The compound as described in [3], wherein the compound represented by formula (3) is a compound represented by the following formula (4): 25 30 35 wherein 40 each of R 4a to R 4h and R 4k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M4a and M4b independently represents a hydrogen atom or a monovalent counter cation, and each of X1 to X5 independently represents a hydrogen atom or a monovalent substituent. [5] The compound as described in [3], 45 wherein the compound represented by formula (3) is a compound represented by the following formula (5): 50 55 4 EP 2 712 894 A1 5 10 15 wherein each of R 5a to R 5h and R 5k independently represents a hydrogen atom or a monovalent substituent, the substituents may combine with each other to form a ring, each of M5a and M5b independently represents a hydrogen atom or a monovalent counter cation, and 20 each of Y11 to Y17 independently represents a hydrogen atom or a monovalent substituent. [6] The compound as described in [3], wherein the compound represented by formula (3) is a compound represented by the following formula (6): 25 30 35 wherein each of R 6a to R 6h and R 6k independently represents a hydrogen atom or a monovalent substituent, the substituents 40 may combine with each other to form a ring, each of M6a and M6b independently represents a hydrogen atom or a monovalent counter cation, and each of Z1 to Z4 independently represents a hydrogen atom or a monovalent substituent.
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