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Wo 2007/060255 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date (10) International Publication Number 31 May 2007 (31.05.2007) PCT WO 2007/060255 A2 (51) International Patent Classification: Not classified (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (21) International Application Number: AT,AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, PCT/EP2006/069009 CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, (22) International Filing Date: JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, 28 November 2006 (28.1 1.2006) LT, LU, LV,LY,MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, (25) Filing Language: English RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 051 11356.1 28 November 2005 (28.1 1.2005) EP GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 60/749,792 13 December 2005 (13.12.2005) US ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (71) Applicant (for all designated States except US): AGFA European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, GRAPHICS NV [BE/BE] ; Septestraat 27, B-2640 Mortsel FR, GB, GR, HU, IE, IS, IT, LT, LU, LV,MC, NL, PL, PT, (BE). RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (72) Inventor; and (75) Inventor/Applicant (for US only): DEROOVER, Geert Published: [BE/BE]; c/o AGFA Graphics NV, IP Department 3800, — without international search report and to be republished Septestraat 27, B-2640 Mortsel (BE). upon receipt of that report (74) Common Representative: AGFA GRAPHICS NV; In For two-letter codes and other abbreviations, refer to the "G uid tellectual Property Department - 3622, Septestraat 27, 2640 ance Notes on Codes and Abbreviations" appearing at the beg in Mortsel (BE). ning of each regular issue of the PCT Gazette. (54) Title: NON-AQUEOUS DISPERSIONS OF NAPHTHOL AS PIGMENTS (57) Abstract: A non-aqueous pigment dispersion comprising a Naphthol AS pigment or a mixed crystal thereof and a Naphthol AS colorant according to Formula (I): Formula (I) wherein R , R , R , R and R are each independently selected from the group consisting of hydrogen, methyl, ethyl, halogen, methoxy, ethoxy, -CONH-phenyl and -NO2, characterized in that the group Q is phenyl substituted by either one sulphonic acid group, two carboxylic acid groups or salts thereof. Non-aqueous inkjet inks and use of the non-aqueous pigment dispersions for making colored layers is also disclosed. Description Non-aqueous dispersions of Naphthol AS pigments Technical Field [0001] The present invention relates to non-aqueous pigment dispersions of Naphthol AS pigments, especially to inkjet inks of Naphthol AS pigments exhibiting high dispersion quality and stability. Background Art [0002] Pigment dispersions are made using a dispersant. A dispersant is a substance for promoting the formation and stabilization of a dispersion of pigment particles in a dispersion medium. Dispersants are generally surface-active materials having an anionic, cationic or non-ionic structure. The presence of a dispersant substantially reduces the dispersing energy required. Dispersed pigment particles may have a tendency to re-agglomerate after the dispersing operation, due to mutual attraction forces. The use of dispersants also counteracts this re-agglomeration tendency of the pigment particles. [0003] The dispersant has to meet particularly high requirements when used for inkjet inks. Inadequate dispersing manifests itself as increased viscosity in liquid systems, loss of brilliance and/or hue shifts. Moreover, particularly good dispersion of the pigment particles is required to ensure unimpeded passage of the pigment particles through the nozzles of the print head in an inkjet printer, which are usually only a few micrometers in diameter. In addition, pigment particle agglomeration and the associated blockage of the printer nozzles has to be avoided in the standby periods of the printer. [0004] Many polymeric dispersants contain in one part of the molecule so-called anchor groups, which adsorb onto the pigments to be dispersed. In a spatially separate part of the molecule, polymeric dispersants have polymer chains sticking out whereby pigment particles are made compatible with the dispersion medium, i.e. stabilized. [0005] In aqueous inkjet inks, the polymeric dispersants generally contain hydrophobic anchor groups exhibiting a high affinity for the pigment surface and hydrophilic polymer chains for stabilizing the pigments in the aqueous dispersion medium. [0006] The preparation of good thermally stable dispersions with submicron particles is more difficult for non-aqueous inkjet inks, such as solvent based, oil based and radiation curable inkjet inks. The pigments are especially difficult to disperse when they have a non-polar surface. [0007] These problems have lead to the design of very specific polymeric dispersants wherein the anchor groups are pigment derivatives. For example, EP 0763378 A (TOYO INK) discloses a pigment composition comprising a non-aqueous type pigment dispersing agent having a portion which has a high affinity with a pigment and which has at least one type selected from the group consisting of an organic dye, anthraquinone and acridone only at a terminal end or at both terminal ends of at least one polymer selected from a linear urethane polymer and a linear acrylic polymer, and a pigment. [0008] Another approach for dispersing pigments with non-polar surfaces in non¬ aqueous dispersion media is changing the surface to a more polar surface by addition of compounds known as dispersion synergists. A dispersion synergist is a compound that promotes the adsorption of the polymeric dispersant on the surface of the pigment. It is suggested that the synergist should possess the pigment structure substituted by one or more sulphonic acid groups or ammonium salts thereof. [0009] US 4461647 (ICI) discloses a dispersion of a pigment in an organic liquid containing a water-insoluble asymmetric disazo compound comprising a central divalent group free from acidic and other ionic substituents linked through azo groups to two monovalent end groups characterized in that one end group, the first, is free from acidic and other ionic substituents and the other end group, the second, carries a single substituted ammonium- acid salt group. [0010] US 4057436 (ICI) discloses pigment dispersions in organic liquids using polymeric or resinous dispersing agents in the presence of a substituted ammonium salt of a colored acid wherein there are between 16 and 60 carbon atoms contained in at least 3 chains attached to the N-atom of the substituted ammonium ion. [001 1] US 6641655 (AVECIA) discloses the use of a diquatemary ammonium salt of a coloured acid as fluidising agent wherein the diquatemary ammonium cation contains two or more nitrogen atoms. [0012] Although these dispersion synergists work fine for some pigments, many other pigments can not be dispersed to an acceptable quality in a non¬ aqueous medium. This is the case for Naphthol AS pigments, for which it is difficult to obtain stable non-aqueous pigment dispersions, especially stable non-aqueous inkjet inks. [0013] JP 59-227951 (TOYO INK) discloses diazo compounds prepared by coupling a 3-phenylcarbamoyl-2-Naphthol compound with a diazonium salt of an arylamine wherein these diazo compounds comprise carboxylic acid groups and salts thereof. The diazo compounds are used as dispersants for a wide range of pigments in offset inks, gravure inks and paints. [0014] For consistent image quality, inkjet inks require a dispersion stability capable of dealing with high temperatures (above 6 O0C) during transport of the ink to a customer, jetting at elevated temperatures and changes in the dispersion medium of the inkjet ink during use, for example, evaporation of solvent and increasing concentrations of humectants, penetrants and other additives. [0015] Therefore, it is highly desirable to be able to manufacture pigment inkjet inks using Naphthol AS pigments in a non-aqueous medium exhibiting a high dispersion quality and stability. Disclosure of Invention Objects of the invention [0016] It is an object of the present invention invention to provide non-aqueous pigments dispersions of Naphthol AS pigments with high dispersion quality and stability. [0017] Further objects of the invention will become apparent from the description hereinafter. Summary of the invention [0018] It has been surprisingly found that non-aqueous Naphthol AS pigment dispersions of high dispersion quality and stability were obtained by using a specific Naphthol AS colorant containing either one sulphonic acid group, two carboxylic acid groups or salts thereof. [0019] Objects of the present invention have been realized with a non-aqueous pigment dispersion comprising a Naphthol AS pigment or a mixed crystal thereof and a Naphthol AS colorant according to Formula (I): R 4 Formula (I) wherein R1, R2, R3, R4 and R5 are each independently selected from the group consisting of hydrogen, methyl, ethyl, halogen, methoxy, ethoxy, - CONH-phenyl and -NO2 , characterized in that the group Q is phenyl substituted by either one sulphonic acid group, two carboxylic acid groups or salts thereof. Definitions [0020] The term "colorant", as used in disclosing the present invention, means dyes and pigments. [0021] The term "dye", as used in disclosing the present invention, means a colorant having a solubility of 10 mg/L or more in the medium in which it is applied and under the ambient conditions pertaining.
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