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WO2018163940A1 - Composition colorante, encre pour impression à jet d'encre, procédé d'impression à jet d'encre et cartouche pour imprimante à jet d'encre - Google Patents

Composition colorante, encre pour impression à jet d'encre, procédé d'impression à jet d'encre et cartouche pour imprimante à jet d'encre Download PDF

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Publication number
WO2018163940A1
WO2018163940A1 PCT/JP2018/007604 JP2018007604W WO2018163940A1 WO 2018163940 A1 WO2018163940 A1 WO 2018163940A1 JP 2018007604 W JP2018007604 W JP 2018007604W WO 2018163940 A1 WO2018163940 A1 WO 2018163940A1
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WIPO (PCT)
Prior art keywords
group
general formula
ink
compound
substituent
Prior art date
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PCT/JP2018/007604
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English (en)
Japanese (ja)
Inventor
立石　桂一
藤江　賀彦
貴志 齊藤
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富士フイルム株式会社
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Publication date
Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to JP2019504509A priority Critical patent/JP6839754B2/ja
Publication of WO2018163940A1 publication Critical patent/WO2018163940A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • aralkyl group examples include a substituted or unsubstituted aralkyl group, and the substituted or unsubstituted aralkyl group is preferably an aralkyl group having 7 to 30 carbon atoms. Examples thereof include a benzyl group and a 2-phenethyl group.
  • cycloalkenyl group examples include Is a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as a 2-cyclopenten-1-yl group, 2-cyclohexen-1-yl group and the like.
  • silyloxy group examples include substituted or unsubstituted silyloxy groups having 0 to 20 carbon atoms, such as trimethylsilyloxy group and diphenylmethylsilyloxy group.
  • the alkoxycarbonylamino group is preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, or an n-octadecyloxycarbonylamino group. Group, N-methyl-methoxycarbonylamino group and the like.
  • heterocyclic thio group examples include substituted or unsubstituted heterocyclic thio groups having 2 to 30 carbon atoms, such as 2-benzothiazolylthio group and 1-phenyltetrazol-5-ylthio group.
  • Heterocyclic carbonyl groups bonded to carbonyl groups at substituted carbon atoms eg, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridyl
  • Examples thereof include a carbonyl group and a 2-furylcarbonyl group.
  • the carbamoyl group is preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, or an N, N-di-n-octyl group.
  • a carbamoyl group, an N- (methylsulfonyl) carbamoyl group, and the like can be given.
  • the ionic hydrophilic group examples include a sulfo group, a carboxyl group, a thiocarboxyl group, a sulfino group, a phosphono group, a dihydroxyphosphino group, and a quaternary ammonium group. Particularly preferred are a sulfo group and a carboxyl group.
  • the ionic hydrophilic group may contain a cation or an anion, and a state containing the cation or anion is called a salt state.
  • the carboxyl group, phosphono group and sulfo group may be in the form of a salt.
  • Examples of counter cations that form salts include ammonium ions, alkali metal ions (eg, lithium ions, sodium ions, potassium ions) and organic cations. (Eg, tetramethylammonium ion, tetramethylguanidinium ion, tetramethylphosphonium) are included, lithium salts, sodium salts, potassium salts, and ammonium salts are preferable, and mixed salts containing sodium salts or sodium salts as main components are included. More preferred is the sodium salt.
  • R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 each independently represent a hydrogen atom or a substituent. However, R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 satisfy the following condition (iii) or (iv). * Represents a bond bonded to a sulfur atom.
  • R 4 , R 9 , R 12 and R 15 each independently represent a hydrogen atom or a substituent.
  • an alkyl group or an ionic hydrophilic group is preferable.
  • the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
  • ionic hydrophilic group a carboxyl group, a sulfo group or a phosphono group is preferable.
  • R 2 , R 3 , R 7 and R 8 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituent represented by the above general formula (A); At least one of 2 , R 3 , R 7 and R 8 represents a substituent represented by the general formula (A). If R 2, R 3, R 7 and R 8 represents an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group.
  • R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 each independently represent a hydrogen atom or a substituent.
  • R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 satisfy the following condition (iii) or (iv).
  • R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 represent a substituent includes a substituent selected from the above substituent group A, and an alkyl group or an alkoxy group Is more preferable, an alkyl group having 1 to 6 carbon atoms or an alkoxy group is more preferable, an alkyl group having 1 to 3 carbon atoms or an alkoxy group is still more preferable, and a methyl group or a methoxy group is particularly preferable.
  • R 401 , R 402 , R 403 , R 404 and R 405 satisfy the following condition (i-1) or (ii-1).
  • R 406 , R 407 , R 408 , R 409 and R 410 each independently represent a hydrogen atom or a substituent.
  • R 406 , R 407 , R 408 , R 409 and R 410 satisfy the following condition (i-2) or (ii-2).
  • Condition (ii-1) At least two of R 401 , R 402 , R 403 , R 404 and R 405 represent a carboxyl group.
  • R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R in the general formula (2) 19 and R 20 are R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R in General Formula (1), respectively. 17 , R 18 , R 19 and R 20 have the same meaning, and the preferred range is also the same.
  • R 3 and R 8 in the general formula (2) each independently represent a hydrogen atom or an alkyl group, and preferably represents an alkyl group.
  • R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 represents a hydroxyl group and at least one represents a carboxyl group.
  • the preferred ranges of R 501 , R 502 , R 503 , R 504 , R 505 , R 506 and R 507 are respectively R 501 , R 502 , R 503 , R 504 , R 505 , R 506 in general formula (X2).
  • R 508 , R 509 , R 510 , R 511 , R 512 , R 513 and R 514 in the general formula (3) preferably satisfy the above condition (iii-2).
  • the range of 0.1 to 80/20 is particularly preferable, and the range of 99.0 / 0.1 to 90/10 is most preferable from the hue and saturation on the recording medium when printed.
  • antifungal agent examples include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, ethyl p-hydroxybenzoate, 1,2-benzisothiazolin-3-one and salts thereof. These are preferably used in an amount of 0.02 to 1.00% by mass in the ink.
  • the ink for ink jet recording of the present invention can be used in inks of various colors, but is preferably used for magenta inks. Further, it can be used not only for forming a single color image but also for forming a full color image. In order to form a full color image, a magenta color ink, a cyan color ink, and a yellow color ink can be used, and a black color ink may be further used to adjust the color tone.
  • a polymer fine particle dispersion (also referred to as polymer latex) may be used in combination for the purpose of imparting glossiness and water resistance or improving weather resistance.
  • the timing of applying the polymer latex to the image receiving material may be before, after, or simultaneously with the application of the colorant, and therefore the addition place may be in the image receiving paper. It may be in ink or may be used as a liquid material of polymer latex alone.
  • the method described in the specification can be preferably used.
  • the ink jet printer cartridge of the present invention is filled with the ink for ink jet recording described above.
  • the ink-jet recorded matter is obtained by forming a colored image on a recording material using the ink-jet recording ink of the present invention described above.
  • Exemplary compound (1-26) can be synthesized, for example, according to the following scheme.
  • FIG. 5 shows the 1 H-NMR spectrum of Exemplified Compound (2-1) in dimethyl sulfoxide-d6.
  • Example 2 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore diameter of 0.20 ⁇ m to prepare an ink jet recording ink 2 for magenta.
  • Example 16 Ink jet recording ink 16 was prepared in the same manner as in Example 1, except that Exemplified Compound (1-35) was used instead of Exemplified Compound (1-11).
  • Example 19 Ink jet recording ink 19 was prepared in the same manner as in Example 2, except that Exemplified Compound (2-5) was used instead of Exemplified Compound (2-1).
  • Example 25 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore diameter of 0.20 ⁇ m to prepare an ink jet recording ink 25 for magenta.
  • Example 26 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore size of 0.20 ⁇ m to prepare an ink jet recording ink 26 for magenta.
  • Example 29 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L sodium hydroxide aqueous solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore size of 0.20 ⁇ m to prepare an ink jet recording ink 29 for magenta.
  • Example 40 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore size of 0.20 ⁇ m to prepare an ink jet recording ink 40 for magenta.
  • Example 43 Deionized water was added to the following ingredients to make 100 g, followed by stirring for 1 hour while heating at 30 to 40 ° C. Thereafter, the pH was adjusted to 8.5 with a 10 mol / L aqueous sodium hydroxide solution, and the mixture was filtered under reduced pressure through a microfilter having an average pore diameter of 0.20 ⁇ m, thereby preparing an ink jet recording ink 43 for magenta.
  • Compound X 0.50g Compound of general formula (D) (Exemplary Compound (2-1)) 0.50 g Proxel XLII (preservative, manufactured by LONZA) 0.11 g Glycerin 10.00g 2.00 g of triethylene glycol Triethylene glycol monobutyl ether 10.00g 2-pyrrolidone 2.00g Surfinol (Air Products and Chemicals) 1.00g
  • ⁇ Print density> A solid image (printed image at an applied voltage of 100%) was recorded using each inkjet recording ink with the combination of the above-described inkjet printer and recording paper.
  • the density of the printed solid image is measured using a reflection densitometer (trade name: X-Rite 310TR, manufactured by X-Rite).
  • the case of B, the case of 1.7 or more and less than 1.8 was designated as C, and the case of less than 1.7 was designated as D.
  • ⁇ Ozone resistance> While passing dry air through the double glass tube of the Siemens type ozonizer, 5 kV AC voltage was applied, and using this, ozone gas concentration was 5 ⁇ 0.1 ppm, room temperature (20 ° C), in a box set in a dark place.
  • the image-formed paper is allowed to stand for 3 days, and the image density after being left under ozone gas is measured using a reflection densitometer (trade name: X-Rite 310TR, manufactured by Xrite), and left under the initial image density Ci and ozone gas.
  • the dye residual ratio was calculated and evaluated from the subsequent image density Cf2. The dye residual ratio was measured using an image portion having an initial image density of 1.0 ⁇ 0.2.
  • the ozone gas concentration in the box was set using an ozone gas monitor (model: OZG-EM-01) manufactured by APPLICS.
  • the dye residual ratio was determined from the following formula, and ozone resistance was evaluated according to the following criteria.
  • Dye remaining rate (%) (Cf2 / Ci) ⁇ 100

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet (AREA)

Abstract

La présente invention concerne une composition colorante qui présente une excellente teinte, une excellente saturation de couleur et une excellente puissance colorante, et qui est capable de former des images ayant une excellente résistance à la lumière, une excellente résistance à l'ozone et une excellente résistance à l'humidité, tout en ayant une excellente stabilité d'éjection dans une imprimante à jet d'encre, une encre pour impression à jet d'encre, qui utilise cette composition colorante, un procédé d'impression à jet d'encre qui utilise cette encre pour impression à jet d'encre, et une cartouche pour imprimante à jet d'encre qui est remplie avec cette encre pour impression à jet d'encre au moyen d'une composition colorante qui contient un composé représenté par la formule générale (1) et un composé représenté par la formule générale (D) tel que décrit dans la description, une encre pour impression à jet d'encre, qui utilise cette composition colorante, un procédé d'impression à jet d'encre qui utilise cette encre pour impression à jet d'encre, et une cartouche pour imprimante à jet d'encre qui est remplie avec cette encre pour impression à jet d'encre.
PCT/JP2018/007604 2017-03-06 2018-02-28 Composition colorante, encre pour impression à jet d'encre, procédé d'impression à jet d'encre et cartouche pour imprimante à jet d'encre WO2018163940A1 (fr)

Priority Applications (1)

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JP2019504509A JP6839754B2 (ja) 2017-03-06 2018-02-28 着色組成物、インクジェット記録用インク、インクジェット記録方法、及びインクジェットプリンタカートリッジ

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JP2017-042074 2017-03-06
JP2017042074 2017-03-06

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015105108A1 (fr) * 2014-01-10 2015-07-16 富士フイルム株式会社 Composé, composition colorante, encre d'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre, matériau imprimé par jet d'encre, filtre de couleur, encre en poudre de couleur et encre de transfert
WO2016052687A1 (fr) * 2014-09-30 2016-04-07 富士フイルム株式会社 Composition colorante, encre d'impression à jet d'encre, et procédé d'impression à jet d'encre
JP2016047908A (ja) * 2014-03-27 2016-04-07 富士フイルム株式会社 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、及び転写用インク
JP2016069655A (ja) * 2014-09-30 2016-05-09 富士フイルム株式会社 インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、及びインクジェット記録物
WO2017006939A1 (fr) * 2015-07-09 2017-01-12 富士フイルム株式会社 Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, cartouche pour imprimante à jet d'encre, et article enregistré par jet d'encre
WO2017146070A1 (fr) * 2016-02-25 2017-08-31 富士フイルム株式会社 Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche pour imprimante à jet d'encre

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015105108A1 (fr) * 2014-01-10 2015-07-16 富士フイルム株式会社 Composé, composition colorante, encre d'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre, matériau imprimé par jet d'encre, filtre de couleur, encre en poudre de couleur et encre de transfert
JP2016047908A (ja) * 2014-03-27 2016-04-07 富士フイルム株式会社 化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、インクジェット記録物、カラーフィルタ、カラートナー、及び転写用インク
WO2016052687A1 (fr) * 2014-09-30 2016-04-07 富士フイルム株式会社 Composition colorante, encre d'impression à jet d'encre, et procédé d'impression à jet d'encre
JP2016069655A (ja) * 2014-09-30 2016-05-09 富士フイルム株式会社 インクジェット記録用インク、インクジェット記録方法、インクジェットプリンタカートリッジ、及びインクジェット記録物
WO2017006939A1 (fr) * 2015-07-09 2017-01-12 富士フイルム株式会社 Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, cartouche pour imprimante à jet d'encre, et article enregistré par jet d'encre
WO2017146070A1 (fr) * 2016-02-25 2017-08-31 富士フイルム株式会社 Composé, composition colorante, encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre, et cartouche pour imprimante à jet d'encre

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