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WO 2013/069816 Al 16 May 2013 (16.05.2013) P O P C T

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WO 2013/069816 Al 16 May 2013 (16.05.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2013/069816 Al 16 May 2013 (16.05.2013) P O P C T (51) International Patent Classification: ON KABUSHIKI KAISHA, 30-2 Shimomaruko 3-chome, G03G 9/09 (2006.01) G03G 9/087 (2006.01) Ohta-ku, Tokyo, 1468501 (JP). (21) International Application Number: (74) Agents: ABE, Takuma et al; C/O CANON KABUSHIKI PCT/JP2012/079591 KAISHA, 30-2, Shimomaruko 3-chome, Ohta-ku, Tokyo, 1468501 (JP). (22) International Filing Date: 8 November 2012 (08.1 1.2012) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (25) Filing Language: English AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (26) Publication Language: English BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (30) Priority Data: HN, HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR, 201 1-246928 10 November 201 1 (10. 11.201 1) JP KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (71) Applicant: CANON KABUSHIKI KAISHA [JP/JP]; 30- MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 2, Shimomaruko 3-chome, Ohta-ku, Tokyo, 1468501 (JP). OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (72) Inventors: HASEGAWA, Yuki; C/O CANON KA TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. BUSHIKI KAISHA, 30-2, Shimomaruko 3-chome, Ohta- ku, Tokyo, 1468501 (JP). MURAI, Yasuald; C/O CAN (84) Designated States (unless otherwise indicated, for every ON KABUSHIKI KAISHA, 30-2, Shimomaruko 3-chome, kind of regional protection available): ARIPO (BW, GH, Ohta-ku, Tokyo, 1468501 (JP). TANAKA, Masatake; GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, C/O CANON KABUSHIKI KAISHA, 30-2, Shimomaruko UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 3-chome, Ohta-ku, Tokyo, 1468501 (JP). TOYODA, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, Takayuki; C/O CANON KABUSHIKI KAISHA, 30-2, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Shimomaruko 3-chome, Ohta-ku, Tokyo, 1468501 (JP). KAWAMURA, Masashi; C/O CANON KABUSHIKI TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). KAISHA, 30-2, Shimomaruko 3-chome, Ohta-ku, Tokyo, 1468501 (JP). HASEGAWA, Waka; C/O CANON KA Published: BUSHIKI KAISHA, 30-2, Shimomaruko 3-chome, Ohta- — with international search report (Art. 21(3)) ku, Tokyo, 1468501 (JP). HIROSE, Masashi; C/O CAN 00 © o (54) Title: TONER AND METHOD FOR MANUFACTURING TONER PARTICLES (57) Abstract: The present invention provides a toner that contains an azo pigment well-dispersed in a binder resin and has a satis - factory color tone. The toner contains toner particles each containing a binder resin and a colorant. Each of the toner particles con tains a compound having a polyester moiety and a bisazo structure moiety. The colorant is the azo pigment. DESCRIPTION TONER AND METHOD FOR MANUFACTURING TONER PARTICLES Technical Field [0001] The present invention relates to a toner for use in electrophotography, electrostatic recording, electrostatic printing, or toner jet recording, and a method for manufacturing toner particles of the toner. Background Art [0002] PTL 1 discloses the use of an azo pigment as a toner colorant. In order to improve spectral characteristics, such as tinting strength and transparency, a pigment must be finely dispersed in a toner binder resin or a polymerizable monomer. However, a reduction in the size of azo pigment particles generally results in an increase in the growth or transformation of crystals caused by thermal history or contact with a solvent in a dispersion process and subsequent processes. This results in a decrease in the tinting strength and transparency of the toner. Furthermore, in a toner manufacturing process using an azo pigment, particularly utilizing a polymerization method, the reaggregation of fine azo pigment particles may cause an increase in the viscosity of the pigment dispersion. [0003] Various pigment dispersants have been proposed in order to solve these problems. PTL 2 discloses a polymer dispersant in which a moiety having a high affinity for an azo pigment colorant is covalently bonded to an oligomer or polymer moiety having a high affinity for a solvent and a binder resin. PTL 3 discloses the use of a comb polymer dispersant havi'ng an acidic or basic portion known as Solsperse (registered trademark) . Citation List Patent Literature [0004] PTL 1 Japanese Patent No. 3917764 PTL 2 Japanese Patent No. 3984840 PTL 3 International Publication WO 99-42532 Summary o f Invention [0005] However, the pigment dispersants disclosed in PTL 2 and PTL 3 have insufficient affinity for an azo pigment, provide insufficient pigment dispersion, and therefore cannot achieve the toner color tone required for high- resolution images. Furthermore, when a toner is manufactured by a polymerization method using these pigment dispersants and an azo pigment, a reduction in the size of the azo pigment particles may cause an increase in the viscosity of the pigment dispersion in a pigment dispersion process . [0006] The present invention provides a toner with which these problems can be solved. More specifically, the present invention provides a toner that contains an azo pigment well dispersed in a binder resin and has a satisfactory color tone and a method for manufacturing toner particles of the toner. [0007] The present invention relates to a toner that contains toner particles each containing a binder resin and a colorant. Each of the toner particles contains a compound having a polyester moiety and a bisazo structure moiety represented by the following formula (1) or (2) . The colorant is an azo pigment. [Chem. 1 ] ormula ( 1 ) [0008] In the formulae (1) and (2), Ri to R independently denote a hydrogen atom or a halogen atom, R5 and R independently denote an alkyl group having 1 to 6 carbon atoms or a phenyl group, R7 to R independently denote a hydrogen atom, a COOR12 group, or a CO 13R 4 group, provided that at least one of R7 to denotes the COOR12 group or the CO R 3R group, R12 to R1 independently denote a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and L i denotes a divalent linking group to be bonded to the polyester moiety. [0009] The present invention also relates to a method for manufacturing toner particles of the toner. [0010] Further features of the present invention will become apparent from the following description of exemplary embodiments with reference to the attached drawings. Brief Description of Drawings [0011] Fig. 1 is a H NMR spectrum of a polyester (35) having a bisazo dye skeleton measured at 400 MHz in CDC1 3 at room temperature. Fig. 2 is a H NMR spectrum of a polyester (38) having a bisazo dye skeleton measured at 400 MHz in CDCI 3 at room temperature . Description of Embodiments [0012] The present invention will be described in detail in the following embodiments. A compound having a bisazo structure moiety represented by the formula (1) or (2) and a polyester moiety is hereinafter referred to a s a "polyester having a bisazo dye skeleton". The polyester moiety refers to a polyester resin moiety other than the bisazo structure moiety in the compound. A toner according to an embodiment of the present invention will b e described below. [0013] A toner according to an embodiment o f the present invention contains toner particles, each o f which contains a binder resin, a compound having a polyester moiety and a bisazo structure moiety represented by the following formula (1) or (2), and an azo pigment colorant. [Chem. 1 ] W 7 Formula (1) Formula (2) [0014] In the formulae (1) and (2), Ri to R independently denote a hydrogen atom or a halogen atom, R and R independently denote an alkyl group having 1 to 6 carbon atoms or a phenyl group, R7 to R independently denote a hydrogen atom, a COOR12 group, or a CONR 13R 14 group, provided that at least one of R7 to R denotes the COOR12 group or the CO R 3R 4 group, R12 to R independently denote a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and L denotes a divalent linking group to be bonded to the polyester moiety. [0015] The components of a polyester having the bisazo dye skeleton represented by the formula (1) or (2) will be described below. A polyester having a bisazo dye skeleton includes the bisazo structure moiety represented by the formula (1) or (2) having a high affinity for an azo pigment and a polyester moiety having a high affinity for a water- insoluble solvent. Thus, the polyester has a high affinity for a water-insoluble solvent, a polymerizable monomer, and a toner binder resin, as well as an azo pigment, particularly an acetoacetanilide pigment. Use of such a polyester having a bisazo dye skeleton as a toner pigment dispersant allows an azo pigment, such as C.I. Pigment Yellow 155, to be well dispersed in a binder resin, thereby providing a toner having a satisfactory color tone. In the manufacture of a toner, such a polyester can improve the dispersion stability of an azo pigment in a water-insoluble solvent and prevent an increase in the viscosity of the pigment dispersion.
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