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WO2018198887A1 - Encres - Google Patents

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Publication number
WO2018198887A1
WO2018198887A1 PCT/JP2018/015916 JP2018015916W WO2018198887A1 WO 2018198887 A1 WO2018198887 A1 WO 2018198887A1 JP 2018015916 W JP2018015916 W JP 2018015916W WO 2018198887 A1 WO2018198887 A1 WO 2018198887A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
reactive
parts
weight
component
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2018/015916
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English (en)
Inventor
Masao Ikoshi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Corp
Original Assignee
Fujifilm Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fujifilm Corp filed Critical Fujifilm Corp
Publication of WO2018198887A1 publication Critical patent/WO2018198887A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
    • 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
    • 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
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or 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
    • C09D11/54—Inks based on two liquids, one liquid being the ink, the other liquid being a reaction solution, a fixer or a treatment solution for the ink
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/30—Ink jet printing

Definitions

  • This invention relates to inks, a process for ink-jet printing, ink-jet ink containers, ink sets and ink-jet printers.
  • Ink-jet printing is a non-impact printing technique in which droplets of an ink are ejected through fine nozzles onto a substrate without bringing the nozzles into contact with the substrate.
  • Ink-jet printing is increasingly being used in the industrial sector where industrial ink-jet printers are required to work at high speeds.
  • a print-head for an industrial ink-jet printer will have multiple minute nozzles arranged at a high density on a face plate to enable high productivity single-pass printing with acceptable print resolutions.
  • This new print-head technology has enabled ink-jet printing to be used in all printing applications including the printing of reactive dyes on to textiles.
  • the applicant has developed ink-jet inks based on low boiling solvents which are not only able to fire reliably through all types of single-pass print-head but also show the following benefits: - use of the inks of the present disclosure minimises face-plate wetting; - use of the inks of the present disclosure results in less frequent head replacement; - use of the inks of the present disclosure results in less clogging on printer filters; - use of the inks of the present disclosure lowers the energy required to dry the print in an online process; - the inks of the present disclosure display excellent stability and resistance to crystal formation at low temperatures; and - the inks of the present disclosure display excellent stability to hydrolysis which is crucial in their global transport.
  • the present invention provides: (1) an aqueous ink-jet printing ink comprising: (a) from 8 to 18 parts by weight of one or more dyes selected from the group consisting of C.I. Reactive Blue 72, C.I. Reactive Red 245, C.I. Reactive Yellow 95, C.I. Reactive Orange 13 and C.I.
  • Reactive Blue 49 (b) from 15 to 40 parts by weight of a water-miscible solvent with a boiling point lower than 240°C and comprising at least 40% ethylene glycol; (c) from 0.1 to 10 parts by weight of a buffer; (d) from 0.01 to 2.5 parts by weight of a non-ionic surfactant; (e) from 4 to 14 parts by weight of urea; (f) from 0 to 5 parts by weight of biocide; (g) from 0 to 12 parts by weight of a solvent having a boiling point higher than 270°C; (h) from 0 to 10 parts by weight of a solvent having a boiling point in a range of from 240°C to 270°C; and (i) a balance to 100 parts by weight of water. All parts and percentages herein (unless stated otherwise) are by weight. All boiling points (bp) are at 1 atmosphere pressure.
  • aqueous ink-jet printing ink as defined in (1), which is: a cyan ink in which component (a) comprises C.I. Reactive Blue 72; a magenta ink in which component (a) comprises C.I. Reactive Red 245; a yellow ink in which component (a) comprises C.I. Reactive Yellow 95; an orange ink in which component (a) comprises C.I. Reactive Orange 13; a blue ink in which component (a) comprises C.I. Reactive Blue 49; or a red ink in which component (a) comprises a mixture of C.I. Reactive Red 245 and C.I. Reactive Orange 13.
  • component (b) comprises, in addition to the at least 40% ethylene glycol, one or more selected from the group consisting of dipropylene glycol, 1,3-butanediol and propylene glycol.
  • component (c) is a compound of the following Formula (1): R 1 R 2 N-Ar-(Z) n Formula (1) wherein: R 1 is H or an alkyl group and R 2 is an alkyl group, or R 1 and R 2 together with the N atom to which they are attached form a 5- or 6- membered ring; Ar is a phenylene group; Z is SO 3 X or CO 2 X; X is H or a cation; and n is 1 or 2.
  • component (c) is N:N-diethylsulfanilic acid.
  • component (d) is 2,4,7,9-tetramethyl-5-decyne-4,7-diol or an ethylene oxide condensate thereof.
  • Reactive Blue 49 from 15 to 40 parts by weight of a water-miscible solvent selected from the group consisting of ethylene glycol, dipropylene glycol, 1,3 butanediol and propylene glycol and comprising at least 40% ethylene glycol; (c’) from 0.2 to 1 part by weight of N:N-diethylsulfanilic acid; (d’) from 0.1 to 1.5 parts by weight of 2,4,7,9-tetramethyl-5-decyne-4,7-diol or an ethylene oxide condensate thereof; (e’) from 4 to 14 parts of urea; (f’) from 0 to 1 part by weight of biocide; (g’) from 0 to 12 parts by weight of glycerol or triethylene glycol or a mixture thereof; (h’) from 0 to 8 parts by weight of 2-pyrrolidone; and (j’) a balance to 100 parts water.
  • a water-miscible solvent selected from the group consisting of
  • a multicolour ink-set comprising: a cyan ink that is the ink of (1) in which component (a) comprises C.I. Reactive Blue 72; a magenta ink that is the ink of (1) in which component (a) comprises C.I. Reactive Red 245; a yellow ink that is the ink of (1) in which component (a) comprises C.I. Reactive Yellow 95; an orange ink that is the ink of (1) in which component (a) comprises C.I. Reactive Orange 13 a blue ink that is the ink of (1) in which component (a) comprises C.I. Reactive Blue 49; and a red ink that is the ink of (1) in which component (a) comprises a mixture of C.I. Reactive Red 245 and C.I. Reactive Orange 13.
  • An ink-jet printing process comprising printing the ink as described in any one of (1) to (8) or the inks of the multicolour ink-set as described in (9) onto a substrate using an ink-jet printer with single-pass print-head.
  • An ink-jet printer ink container tank comprising the ink-jet printing ink as described in any one of (1) to (8).
  • a range of numerical values described using “(from) ... to ...” means a range including the numbers listed before and after “to” as a minimum value and a maximum value respectively.
  • the upper limit or the lower limit of one range of numerical values that is gradationally described may be substituted with the upper limit or the lower limit of another range of numerical values that is gradationally described.
  • the upper limit or the lower limit of a range of numerical values described herein may be substituted with the values shown in Examples.
  • the amount of the component means a total amount of the plural substances which are present in the composition, unless otherwise specified.
  • Percent (%) by mass” and “percent (%) by weight” have the same meaning, and “parts by mass” and “parts by weight” have the same meaning.
  • step includes not only an independent process, but also one that cannot be clearly distinguished from other process, as long as the predetermined action of this step is achieved thereby.
  • a description that does not indicate substitution or unsubstitution is meant to include a group that does not have a substituent, as well as a group having a substituent.
  • an "alkyl group” is meant to include an alkyl group that does not have a substituent (unsubstituted alkyl group) as well as an alkyl group that has a substituent (substituted alkyl group).
  • the aqueous ink-jet printing ink according to a first aspect of the present disclosure includes: a) from 8 to 18 parts by weight of a one or more dyes selected from the group consisting of C.I. Reactive Blue 72, C.I. Reactive Red 245, C.I. Reactive Yellow 95, C.I. Reactive Orange 13 and C.I.
  • Reactive Blue 49 b) from 15 to 40 parts by weight of water-miscible solvent with a boiling point less than 240°C including at least 40% ethylene glycol; c) from 0.1 to 10 parts by weight of a buffer; d) from 0.01 to 2.5 parts by weight of a non-ionic surfactant; e) from 4 to 14 parts by weight of urea; f) from 0 to 5 parts by weight of biocide; g) from 0 to 12 parts by weight of a solvent with a boiling point greater than 270oC; h) from 0 to 10 parts by weight of a solvent with a boiling point in the range of from 240°C to 270°C; and i) the balance to 100 parts by weight water. All parts and percentages herein (unless stated otherwise) are by weight. All boiling points (bp) are at 1 atmosphere pressure.
  • the ink of the present disclosure contains a dye, component (a), as a colorant.
  • the ink is preferably a cyan ink which includes C.I. Reactive Blue 72 as a colorant, a magenta ink which includes C.I. Reactive Red 245 as a colorant, a yellow ink which includes C.I. Reactive Yellow 95 as a colorant, an orange ink which includes C.I. Reactive Orange 13 as a colorant, a blue ink which includes C.I. Reactive Blue 49 as a colorant or a red ink which includes a mixture of C.I. Reactive Red 245 and C.I. Reactive Orange 13 as colorants.
  • the dye is present in an amount of from 8 to 18 parts by weight of the ink.
  • the ink may provide sufficient color optical density of printed images by including the dye at 8 parts by weight or more.
  • the ink may sufficiently prevent undesired color transfer from printed images formed thereby by limiting the amount of the dye to 18 parts by weight or less.
  • component (b) Water-miscible solvent having bp ⁇ 240°C
  • the ink contains 15 to 40 parts by weight of a low boiling point solvent as component (b).
  • Component (b) may be any low boiling point solvent or mixture thereof, including at least 40% ethylene glycol, having a boiling point lower than 240°C which is suitable for use in an ink-jet ink.
  • the ink may sufficiently prevent blockage or failure of nozzles of a recording head in an inkjet recording apparatus and thus provide fire reliability.
  • component (b) includes in addition to the at least 40% ethylene glycol (bp 197°C) one or more of dipropylene glycol (bp 232°C), 1,3-butanediol (bp 203°C) and propylene glycol (bp 188°C).
  • Buffer Component (c) may be any compatible buffer able to maintain the pH of the ink in the required range of pH 7 to 8.5
  • buffers include trishydroxymethylaminomethane (THAM), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), morpholinoethanesulfonic acid (MES), carbamoylmethyliminobisacetic acid (ADA), piperazine-1,4-bis(2-ethanesulfonic acid) (PIPES), N-(2-acetamido)-2-aminoethanesulfonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES), N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (TES), phosphate buffer solution, and tris(hydroxymethyl)aminomethane (Tris) buffer.
  • THAM trishydroxymethylaminomethane
  • the buffer is a compound of Formula (1):
  • R 1 is H or an alkyl group and R 2 is an alkyl group, or R 1 and R 2 together with the N atom to which they are attached form a 5- or 6- membered ring;
  • Ar is a phenylene group;
  • Z is SO 3 X or CO 2 X;
  • X is H or a cation; and
  • n is 1 or 2.
  • R 1 and R 2 are each independently alkyl, or R 1 and R 2 together with the N atom to which they are attached form a 5- or 6- membered ring. More preferably R 1 and R 2 are each independently C 1-6 -alkyl, especially ethyl.
  • the ring is preferably an optionally substituted morpholine, piperazine or piperidine.
  • Preferred optional substituents are carboxy and sulfo.
  • the total number of carbon atoms in R 1 and R 2 added together is from 3 to 18, more preferably 3 to 12, especially 3 to 6.
  • Ar is preferably phenylene.
  • Z is preferably CO 2 X.
  • X is preferably a cation, more preferably an alkali metal (especially Na + , K + or Li + ), ammonium or substituted ammonium cation.
  • Examples of compounds of Formula (1) include 4-chloro-N:N-diethylaniline sulfonic acid, N:N-di-n-hexylaniline-3-sulfonic acid, N-ethyl-N-n-hexylaniline disulfonic acids, 2-N:N-diethylaminonaphthalene-6-sulfonic acid, 2-(N-ethyl-N-benzylamino)-toluene-4-sulfonic acid, 2-N:N-diethylaminotoluene-4-sulfonic acid, N-ethyl-N-cyclohexylaniline-sulfonic acid, N-ethyl-N-betahydroxyethylaniline-sulfonic acid, N-ethyl-N-phenylbenzylaminomonosulfonic acid, 2-(N-ethyl-N-phenylamino)-ethanesulfonic acid,
  • the preferred compounds of Formula (1) are the lower N:N-dialkyl-derivatives of metanilic acid (aniline 3-sulfonic acid) and sulfanilic acid (aniline 4-sulfonic acid) especially N:N-diethylmetanilic acid, N:N-diethylsulfanilic acid, or the mixture of the two obtained by the sulfonation of diethylaniline with oleum.
  • N:N-diethylsulfanilic acid is also known as N:N-diethyl-3-sulfoaminobenzene (DEAS).
  • component (c), the buffer is N:N-diethylsulfanilic acid.
  • the amount of the buffer present in the ink may be arbitrarily set as long as it can maintain the pH of the ink in the required range, but it is typically from 0.1 to 10 parts by weight of the ink.
  • the buffer is present in an amount of from 0.1 parts to 5 parts, more preferably of from 0.2 parts to 1 part, and especially of from 0.5 parts to 0.7 parts by weight of the ink composition.
  • Non-ionic surfactant The non-ionic surfactant, component (d), is not particularly limited. In embodiments, component (d) is preferably an acetylenic surfactant.
  • acetylenic surfactant may be used as component (d).
  • 2,4,7,9-tetramethyl-5-decyne-4,7-diol and ethylene oxide condensates thereof and 2,5,8,11-tetramethyl-6-dodecyne-5,8-diol and ethylene oxide condensates thereof are preferred.
  • the acetylenic surfactant is 2,4,7,9-tetramethyl-5-decyne-4,7-diol or an ethylene oxide condensate thereof.
  • the surfactants 2,4,7,9-tetramethyl-5-decyne-4,7-diol and ethylene oxide condensates thereof are available as the SURFYNOL (registered trademark) range of surfactants from Air Products.
  • a single kind of surfactant or mixtures containing different surfactants may be used as the non-ionic surfactant.
  • the amount of the non-ionic surfactant present in the ink may be arbitrarily set as long as it can suitably adjust surface tension of the ink, but it is typically from 0.01 to 2.5 parts by weight of the ink.
  • Component (d), the non-ionic surfactant is preferably present in the range of from 0.1 parts to 1.5 parts by weight of the ink.
  • the ink contains 4 to 14 parts by weight of urea as component (e).
  • the ink may sufficiently provide fire reliability by including 4 to 14 parts by weight of urea, in which blockage or failure in an inkjet recording due to drying of nozzles of a recording head apparatus may be prevented.
  • the ink may display resistance to dye crystal formation at low temperatures by including 4 parts by weight or more of urea, and the ink may sufficiently prevent color shade change which may occur due to aging of the ink.
  • the ink may contain a biocide, as component (f), if necessary.
  • Component (f), the biocide may be any biocide (or mixture of biocides) which is stable in the ink. It is particularly preferred that the biocide includes 1,2-benzisothazolin-3-one which is available as a 20% active solution from Lonza as PROXEL (registered trademark) GXL and BIOBAN (registered trademark) DXN (2,6-dimethyl-1,3-dioxan-4-yl acetate), from Dow Chemical Company.
  • the level of biocide in the ink depends on which biocide is used. However, typically the biocide is present in a range of 0 to 5 parts by weight of the ink, and preferably in a range of 0 to 1 part by weight of the ink, and more preferably in a range of from 0.01 to 1 part by weight of the ink.
  • a biocide may not be required (namely, the content of a biocide in the ink can be zero parts) if the ink is prepared immediately before use but will be an essential component if the ink is to be stored or kept for any length of time.
  • (g) Solvent with bp>270°C
  • the ink may be free of a solvent having a boiling point higher than 270°C, the ink may contain such a solvent, as component (g), in embodiments if necessary.
  • Component (g) may be any solvent having a boiling point higher than 270°C which is suitable for use in an ink-jet ink. A single kind of the solvent or mixture of these solvents may be used in the inks of the present disclosure.
  • component (g) includes glycerol (bp 290°C) or triethylene glycol (bp 287°C) or a mixture thereof. More preferably component (g) includes glycerol.
  • component (h) Solvent with bp: 240-270°C
  • the ink may be free of a solvent having a boiling point in the range of from 240°C to 270°C, the ink may contain such a solvent, as component (h), in embodiments as necessary.
  • Component (h) may be any solvent having a boiling point in the range of from 240°C to 270°C which is suitable for use in an ink-jet ink.
  • Component (h) is not particularly limited.
  • component (h) preferably includes 2-pyrrolidone (bp 245°C). A single kind of the solvent or mixture of these solvents may be used in the inks of the present disclosure.
  • component (h) is present in the range of from 3 to 7 parts by weight of the ink.
  • the ink-jet printing ink of the present disclosure includes water.
  • a content of water in the ink is not particularly restricted.
  • the ink preferably includes at least 20% water and more preferably at least 25% water. Any source of precipitate free high quality water may be used in the inks of the present disclosure.
  • the water is deionised water.
  • the pH of the ink-jet printing ink is in the range of from between pH 6 to 9 and more preferably of from between pH 7 to 8.5.
  • the ink-jet printing ink preferably has a surface tension of from 20 dynes/cm to 50 dynes/cm, more preferably of from 25 dynes/cm to 50 dynes/cm and especially of from 30 dynes/cm to 40 dynes/cm, when measured at 25°C using a tensiometer AquaPi (trade name, manufactured by Kibron Inc.).
  • the ink-jet printing ink has been filtered through a filter having a mean pore size of less than 10 microns, more preferably less than 5 microns and especially less than 1 micron.
  • the ink-jet printing ink has a total concentration of Ca plus Mg in the ink of less than 300 ppm, more preferably less than 100 ppm and especially less than 50 ppm.
  • the ink-jet printing ink composition may optionally include one or more ink additives.
  • Preferred additives suitable for ink-jet printing inks are anti-kogation agents, rheology modifiers, corrosion inhibitors and chelating agents.
  • the total amount of additives is no more than 10 parts by weight of the ink.
  • additives and additional dyes are added to and include part of component (i), the water added to the ink-jet printing ink.
  • the ink-jet printing ink includes: a’) from 8 to 18 parts by weight of one or more dyes selected from the group consisting of C.I. Reactive Blue 72, C.I. Reactive Red 245, C.I. Reactive Yellow 95, C.I. Reactive Orange 13 and C.I.
  • Reactive Blue 49 from 15 to 40 parts by weight of a water-miscible solvent selected from one or more of the group consisting of dipropylene glycol, 1,3 butanediol and propylene glycol and including at least 40% ethylene glycol; c’) from 0.2 to 1 part by weight of N:N-diethylsulfanilic acid; d’) from 0.1 to 1.5 parts by weight of 2,4,7,9-tetramethyl-5-decyne-4,7-diol or an ethylene oxide condensate thereof; e’) from 4 to 14 parts of urea; f’) from 0 to 1 part by weight of biocide; g’) from 0 to 12 parts by weight of glycerol or triethylene glycol or a mixture thereof; h’) from 0 to 8 parts by weight of 2-pyrrolidone; and i’) a balance to 100 parts of water.
  • a water-miscible solvent selected from one or more of the group
  • a more preferred ink-jet printing ink of the present disclosure includes: a’) from 8 to 18 parts by weight of one or more dyes selected from the group consisting of C.I. Reactive Blue 72, C.I. Reactive Red 245, C.I. Reactive Yellow 95, C.I. Reactive Orange 13 and C.I.
  • Reactive Blue 49 from 15 to 40 parts by weight of a water-miscible solvent selected from the group consisting of dipropylene glycol, 1,3 butanediol and propylene glycol and including at least 40% ethylene glycol; c’) from 0.2 to 1 part by weight of N:N-diethylsulfanilic acid; d’) from 0.1 to 1.5 parts by weight of 2,4,7,9-tetramethyl-5-decyne-4,7-diol or an ethylene oxide condensate thereof; e’) from 4 to 14 parts of urea; f’) from 0.1 to 1 part by weight of biocide; g’) from 0 to 12 parts by weight of glycerol or triethylene glycol or a mixture thereof; h’) from 3 to 7 parts by weight of 2-pyrrolidone; and i’) a balance to 100 parts of water.
  • a water-miscible solvent selected from the group consisting of dipropylene glycol
  • a second aspect of present disclosure includes a multicolour ink-set including at least two inks, at least one ink among which being the ink as described in the first aspect of present disclosure.
  • the ink-set is a multicolour ink-set including inks as described in the first aspect of present disclosure where a cyan ink includes C.I. Reactive Blue 72 as a colorant, a magenta ink includes C.I. Reactive Red 245 as a colorant, a yellow ink includes C.I. Reactive Yellow 95 as a colorant, an orange ink includes C.I. Reactive Orange 13 as a colorant, a blue ink which includes C.I. Reactive Blue 49 as a colorant and a red ink which includes a mixture of C.I. Reactive Red 245 and C.I. Reactive Orange 13 as colorants.
  • the multicolour ink-set of the second aspect of present disclosure may include additional inks as described in the first aspect of present disclosure.
  • the multicolour ink-set of the second aspect of present disclosure may also include additional inks not as described in the first aspect of present disclosure.
  • additional inks may also contain a black ink, a grey ink, a green ink and variants on the ink described above with alternate colorants.
  • a third aspect of present disclosure provides an ink-jet printing process wherein the ink-jet printing ink according to the first aspect of present disclosure or the inks of the multicolour ink-set according to the second aspect of present disclosure is/are printed onto a substrate by means of an ink-jet printer.
  • the process of the present disclosure may use any ink-jet printer, preferably with a single-pass print-head.
  • the third aspect of present disclosure provides an ink-jet printing process wherein the ink as described in the first aspect of present disclosure or the multicolour ink-set according to the second aspect of present disclosure is printed onto a substrate using an ink-jet printer with single-pass print-head.
  • One preferred type of single-pass print-head has an ink re-circulation channel in the ink supply system. This channel allows for fresh ink to be available for jetting and can be part of the ink supply system or even specially engineered channels which run behind the nozzle plate. It is preferred that the ink supply system runs behind the nozzle plate as this allows for the use of more volatile inks whilst not compromising restart/latency behaviour.
  • Print-heads of this type are available from Fujifilm Dimatix.
  • Recirculating print-heads are usually equipped with a reservoir heater and a thermistor to control the jetting temperature. It is preferred that the viscosity of the ink-jet printing ink at the jetting temperature is in the range of from 3 to 20 mPa s and more preferably in a range of from 3 to 12 mPa s.
  • the ink-jet printer has a single-pass ink recirculating print-head.
  • a second preferred type of single-pass print-head is a non-recirculating print-head.
  • Print-heads of this type are available from Kyocera.
  • Non-recirculating print-heads are also usually equipped with a reservoir heater and a thermistor to control the jetting temperature. It is preferred that the viscosity of the ink-jet printing ink at the jetting temperature for print-heads of this type is in the range of from 3 to 7 mPa s.
  • Viscosity is as would be measured using a Brookfield DV-II or DV-II+ digital viscometer with UL-adapter and water jacket and spindle S00 at 3 rpm.
  • DV-II, DV-II+, UL-adapter and S00 are all trade names from Brookfield Engineering Laboratories Inc.
  • the ink-jet printer has a single-pass ink non-recirculating print-head.
  • the ink-jet printing ink of the first aspect of present disclosure is applied at a temperature in excess of 30°C.
  • the substrate is preferably paper, plastic, metal or glass and more preferably a textile material.
  • the textile material may be of natural or synthetic fibers including blends thereof.
  • it may be cellulose, including viscose rayon and regenerated viscose rayon, wool, acrylic, polyamide such as nylon, polyester such as polyethyleneglycolterephthalate or polyurethane. It is, however, preferably cellulose or a blend thereof.
  • the textile material is preferably woven or knitted or in the form of dry or wet laid fibers. It may be in the form of sheets, webs, threads or ready made up garments such as drapes, shirting, toweling, underwear, socks and sheeting.
  • the textile material has been impregnated with a pre-treatment composition including components such as a color enhancing agent; an alkali metal hydroxide, carbonate, bicarbonate or a mixture thereof; a thickener, such as sodium alginate and water.
  • a pre-treatment composition including components such as a color enhancing agent; an alkali metal hydroxide, carbonate, bicarbonate or a mixture thereof; a thickener, such as sodium alginate and water.
  • the pre-treatment step requires that the textile material is treated with a pre-treatment liquid containing at least one of an alkali agent, such as sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, trisodium phosphate, and sodium acetate, and a hydrotropic agent such as urea.
  • an alkali agent such as sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, trisodium phosphate, and sodium acetate
  • a hydrotropic agent such as urea
  • the pre-treatment liquid may also contain a sizing agent, for example: starch materials such as corn and wheat; cellulose based materials such as carboxymethyl cellulose and hydroxymethyl cellulose; polysaccharides such as sodium alginate, gum arabic, locust bean gum, gum tragacanth, guar gum, and tamarind seed; proteins such as gelatin and casein; natural water-soluble polymers such as tannin and lignin; and synthetic water-soluble polymers such as polyvinyl alcohol-based compounds, polyethylene oxide-based compounds, acrylic acid-based compounds, and maleic anhydride-based compounds.
  • a sizing agent for example: starch materials such as corn and wheat; cellulose based materials such as carboxymethyl cellulose and hydroxymethyl cellulose; polysaccharides such as sodium alginate, gum arabic, locust bean gum, gum tragacanth, guar gum, and tamarind seed; proteins such as gelatin and casein; natural water-soluble polymers such as tannin and lignin;
  • pre-treatment liquid examples include an anti-reduction agent, a preservative, a fungicide, a chelating agent, a pH adjusting agent, a thickening agent such as an alginate and a surfactant.
  • composition of the pre-treatment liquid will depend on the printing regime and nature of the textile material.
  • the pre-treatment liquid may be applied to the textile material by any suitable method.
  • the textile material may be immersed in the pre-treatment liquid, coated by means of a pad batch method, roll coater or the like, sprayed, or applied by an ink-jet printer.
  • the pre-treated textile material is then allowed to dry.
  • the textile material is then printed using an ink-jet printer, preferably an ink-jet printer with a single-pass head as described above.
  • the printed textile material is preferably subjected to a heat treatment step.
  • the heat treatment step may utilize any method known in the art such as a high temperature steaming or high pressure steaming.
  • the temperature in the heat treatment step is preferably in a range of from 90°C to 110°C.
  • the printed textile material is then washed to remove any excess dye.
  • the washing step uses water though soaping treatment may be used in some instances.
  • a preferred ink-jet printing process of the third aspect of present disclosure is a textile material printing process including the following steps: a) optionally pre-treating a textile material; b) ink-jet printing the textile material with an ink-jet printing ink as described in the first aspect of present disclosure or a multicolour ink-set according to the second aspect of present disclosure, preferably using an ink-jet printer with a single-pass print-head, as described and preferred above; c) heat treating the printed textile material; and d) washing the heat treated printed textile material.
  • a fourth aspect of the present disclosure provides a substrate printed by an ink-jet printing process as described in the third aspect of present disclosure using an ink-jet printing ink as described in the first aspect of present disclosure or a multicolour ink-set according to the second aspect of present disclosure.
  • the substrate is as described and preferred in the third aspect of present disclosure.
  • the preferred printed substrate is a textile material.
  • an ink-jet printer ink container e.g. a cartridge or a larger ink tank
  • an ink-jet printing ink as described in the first aspect of the present disclosure.
  • a sixth aspect of the present disclosure provides an ink-jet printer with a single-pass print-head, as described in the third aspect of present disclosure, containing an ink-jet printing ink as described in the first aspect of present disclosure or a multicolour ink-set according to the second aspect of present disclosure.
  • ink compositions 1 to 34 and comparative ink compositions C1 to C14 shown in Tables 1-1 to 1-9 were prepared, filtered through a 1.0 ⁇ m pore size membrane and evaluated using the following test protocols.
  • Ink composition C13 was prepared and evaluated in the same manner as ink composition C10 except that ink composition C13 was heated at 60°C for 7 days before being subject to the evaluations.
  • SURFYNOL (registered trademark) 440 is 2,4,7,9-tetramethyl-5-decyne-4,7-diol from Air Products.
  • SURFYNOL (registered trademark) 465 is an ethylene oxide condensate of 2,4,7,9-tetramethyl-5-decyne-4,7-diol from Air Products.
  • C.I. Reactive Blue 72, C.I. Reactive Red 245, C.I. Reactive Yellow 95, C.I. Reactive Orange 13 and C.I. Reactive Blue 49 were obtained from Dystar.
  • the pre-coat solution was applied to the front and back of a 100% cotton fabric by Pad Batch (60% wet pick-up) and dried at ambient condition overnight.
  • the substrate was printed using a printer with a Fujifilm Dimatix Samba single-pass print-head. Three different drop volumes (2.3pl, 4.5pl, 9.0pl) were applied at 100% duty solid image (1200 x 1200dpi).
  • the printed samples were dried at 25°C for 30min. The samples were then steam treated at 100°C for 10min. They were then washed with cold water for 2 min, with 90°C hot water for 10min and finally with cold water for 2 min. The samples were then allowed to dry at room temperature.
  • optical density: OD optical density
  • spectrophotometer trade name: X-Rite eXact, manufactured by X-Rite Inc.
  • the pre-coat solution was applied to the front and back of a 100% cotton fabric by Pad Batch (60% wet pick-up) and dried at ambient condition overnight.
  • the substrate was printed using a printer with a Fujifilm Dimatix Samba single-pass print-head. Three different drop volumes (2.3pl, 4.5pl, 9.0pl) were applied at 100% duty solid image (1200 x 1200dpi). The printed samples were dried at 25°C for 1min. An unprinted white substrate was then placed on the printed sample and a pressure of 0.98N/cm 2 was applied for 3 seconds. Colour transfer to the white substrate was assed visually, in which grade B or higher is deemed as acceptable.
  • Colour Shade Change Print samples on a cotton substrate were prepared as described in protocol 1, above, using freshly made ink and ink aged for 7 days at 60°C. The optical properties of the printed substrates (OD, L*, a* and b*) were then measured with a X-Rite eXact (trade name). The change in the color shade ⁇ E was then calculated as shown below. Herein, grade A or higher is deemed as acceptable.
  • Dye Crystallization test Ink (20g) was placed in 20ml glass sample bottle and stored at 0°C for 14 days, and crystal formation was assessed visually. Herein, grade A or higher is deemed as acceptable.

Landscapes

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

Abstract

L'invention concerne une encre d'impression aqueuse pour jet d'encre, comprenant au moins : (a) 8 à 18 parties en poids (PP) d'un ou de plusieurs colorants choisis dans le groupe constitué par le C.I. Reactive Blue 72, le C.I. Reactive Red 245, le C.I. Reactive Yellow 95, le C.I. Reactive Orange 13 et le C.I. Reactive Blue 49; (b) 15-40 PP d'un solvant miscible à l'eau présentant un point d'ébullition inférieur à 240°C et comprenant au moins 40 % d'éthylèneglycol; (c) 0,1-10 PP d'un tampon; (d) 0,01-2,5 PP d'un tensioactif non ionique; (e) 4-14 PP d'urée; (f) 0-5 PP de biocide; (g) 0-12 PP d'un solvant présentant un point d'ébullition supérieur à 270°C; (h) 0-10 PP d'un solvant présentant un point d'ébullition dans une plage allant de 240°C à 270°C; et (i) le reste jusqu'à 100 PP d'eau. L'invention concerne également des procédés d'impression par jet d'encre, des récipients d'encre pour jet d'encre, des substrats imprimés, des ensembles d'encre et des imprimantes à jet d'encre.
PCT/JP2018/015916 2017-04-28 2018-04-17 Encres Ceased WO2018198887A1 (fr)

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US4677445A (en) * 1983-02-10 1987-06-30 Canon Kabushiki Kaisha Recording method
US4732613A (en) * 1984-11-08 1988-03-22 Canon Kabushiki Kaisha Recording liquid
US20030116058A1 (en) * 2000-02-26 2003-06-26 Hopper Alan John Inks
JP2004285162A (ja) * 2003-03-20 2004-10-14 Konica Minolta Holdings Inc インクジェット捺染用インク、インクジェット捺染用インクセットとそれらを用いたインクジェット記録方法
EP2957607A1 (fr) * 2014-06-17 2015-12-23 Konica Minolta, Inc. Procédé de formation d'images
JP2016190930A (ja) * 2015-03-31 2016-11-10 コニカミノルタ株式会社 顔料捺染インクおよびインクジェット捺染方法
JP2017071683A (ja) * 2015-10-06 2017-04-13 セイコーエプソン株式会社 インクジェット捺染用インク組成物および捺染方法
WO2017061265A1 (fr) * 2015-10-05 2017-04-13 コニカミノルタ株式会社 Dispositif d'impression à jet d'encre

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US4677445A (en) * 1983-02-10 1987-06-30 Canon Kabushiki Kaisha Recording method
US4732613A (en) * 1984-11-08 1988-03-22 Canon Kabushiki Kaisha Recording liquid
US20030116058A1 (en) * 2000-02-26 2003-06-26 Hopper Alan John Inks
JP2004285162A (ja) * 2003-03-20 2004-10-14 Konica Minolta Holdings Inc インクジェット捺染用インク、インクジェット捺染用インクセットとそれらを用いたインクジェット記録方法
EP2957607A1 (fr) * 2014-06-17 2015-12-23 Konica Minolta, Inc. Procédé de formation d'images
JP2016190930A (ja) * 2015-03-31 2016-11-10 コニカミノルタ株式会社 顔料捺染インクおよびインクジェット捺染方法
WO2017061265A1 (fr) * 2015-10-05 2017-04-13 コニカミノルタ株式会社 Dispositif d'impression à jet d'encre
JP2017071683A (ja) * 2015-10-06 2017-04-13 セイコーエプソン株式会社 インクジェット捺染用インク組成物および捺染方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113529446A (zh) * 2021-07-29 2021-10-22 浙江海印数码科技有限公司 适合桑巴喷头的高温分散直喷墨水及其制备方法和应用
CN113529446B (zh) * 2021-07-29 2024-03-26 浙江海印数码科技有限公司 适合桑巴喷头的高温分散直喷墨水及其制备方法和应用

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