CN1224092A - Process for ink-jet printing textile fibre materials - Google Patents

Process for ink-jet printing textile fibre materials Download PDF

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Publication number
CN1224092A
CN1224092A CN98127147A CN98127147A CN1224092A CN 1224092 A CN1224092 A CN 1224092A CN 98127147 A CN98127147 A CN 98127147A CN 98127147 A CN98127147 A CN 98127147A CN 1224092 A CN1224092 A CN 1224092A
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hydrogen
acid
alkyl
substituted
group
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M·布尔格林
M·梅德勒
P·沙伊布利
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BASF Schweiz AG
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Ciba Spezialitaetenchemie Holding AG
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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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • 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
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • 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
    • 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5221—Polymers of unsaturated hydrocarbons, e.g. polystyrene polyalkylene
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5242—Polymers of unsaturated N-containing compounds
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257—(Meth)acrylic acid
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)

Abstract

The present invention relates to a process for printing textile fibre materials by the ink-jet printing process, wherein the fibre materials are printed with an aqueous ink comprising at least one disperse dye, an anionic copolymer and/or a nonionic block polymer and/or a dispersant, and to the inks comprising these components.

Description

Ink-jet printing method for textile fibre material
The invention relates to a method for printing textile fibre materials with disperse dyes by means of inkjet printing processes (jet and inkjet processes), and to the corresponding printing inks.
In the textile industry, inkjet printing processes have been used for some years. They enable the printing to be carried out without the use of other customary engraved template products. Thus, considerable savings will be achieved in both cost and time. Especially in the manufacture of original patterns (originals), can accommodate variations in a much shorter time.
Suitable inkjet printing processes should in particular have optimum performance characteristics. For this reason, it may be relevant to use printing inks such as: viscosity, stability, surface tension and conductivity properties. Furthermore, higher demands are made on the quality of the prints produced, in terms such as: higher demands are made on the quality of the colour depth, the fibre-dye binding stability and the various wet-fastness properties. The existing processes do not meet each of these characteristics, and therefore, a need continues to exist for new processes for inkjet printing textiles.
The invention provides a process for the manufacture of printed textile fibre materials by the ink-jet printing process, wherein the fibre material is printed with an aqueous printing ink containing at least one disperse dye, an anionic copolymer and/or a non-ionic block polymer and/or a dispersant.
Suitable disperse dyes for use in the process of the present invention are those described in the "disperse dyes" in the Color Index, 3 rd edition (3 rd revision, 1987, including the additions and supplements to No. 85). For example: nitro, amino, aminoketone, ketimine, methine, polymethine, diphenylamine, quinoline, benzimidazole, xanthene, oxazine or coumarin dyes which are free of carboxyl and/or sulfo groups, and especially anthraquinone dyes and azo dyes, for example monoazo or disazo dyes.
In the process of the invention, disperse dyes of the formulaWherein
R16Is a halogen, a nitro group or a cyano group,
R17is hydrogen, halogen, nitro or cyano,
R18is a halogen or a cyano group, or a salt thereof,
R19is hydrogen, halogen, C1-C4Alkyl or C1-C4An alkoxy group,
R20is hydrogen, halogen or amido, and
R21and R22Independently of one another, hydrogen or C which is unsubstituted or substituted by hydroxy, cyano, acetoxy or phenoxy1-C4An alkyl group, a carboxyl group,
wherein,
R23is hydrogen, phenyl or phenylsulfonyl (phenyl sulfonyl), the phenyl ring of which is unsubstituted or substituted by C1-C4Alkyl, sulfo (sulfo) or C of1-C4An alkylsulfonyloxy (alkylsulfuryl) substituted benzene ring,
R25is unsubstituted or C1-C4An alkyl-substituted amino group or a hydroxyl group,
R26is hydrogen or C1-C4An alkoxy group,
R27is hydrogen or-O-C6H5-SO2-NH-(CH2)3-O-C2H5The radical(s) is (are),
R36is hydrogen, hydroxy or nitro, and
R37is hydrogen, hydroxyl or nitro,
Figure A9812714700092
wherein R is28Is unsubstituted or substituted by hydroxy C1-C4Alkyl radical, C29Is C1-C4Alkyl radical, R30Is cyano, R31Is of the formula- (CH)2)3-O-(CH2)2-O-C6H5Group of (A), R32Is halogen, nitro or cyano, and R33Is hydrogen, halogen, nitro or cyano,
Figure A9812714700101
wherein R is34Is C1-C4Alkyl radical, R35Is unsubstituted or substituted by C1-C4Alkoxy-substituted C1-C4Alkyl, W is a radical-COOCH2CH2OC6H5And W1Is hydrogen, or W is hydrogen and W is1is-N = N-C6H5，
Figure A9812714700102
Where ring A "and ring B" are rings which are unsubstituted or substituted one or more times by halogen,
Figure A9812714700103
wherein R is34Is unsubstituted or substituted by hydroxy, C1-C4Alkoxy or C1-C4alkoxy-C1-C4Alkoxy-substituted C1-C4Alkyl radical, and
Figure A9812714700111
in the process of the invention, particular preference is given to using dyes of the formula:
Figure A9812714700113
Figure A9812714700114
Figure A9812714700122
Figure A9812714700123
Figure A9812714700131
Figure A9812714700132
Figure A9812714700133
Figure A9812714700135
Figure A9812714700137
Figure A9812714700141
and
Figure A9812714700142
the disperse dyes of the formulae (1) to (23) are known or can be prepared from similarly known compounds by known general techniques, for example by the customary diazotisation, coupling, addition and condensation reactions.
The total content of disperse dyes of the formulae (1) to (23) indicated above in the printing inks is generally from 1 to 35%, in particular from 1 to 20%, in particular from 1 to 10%, by weight, based on the total printing ink.
In the inks of the invention, it is advantageous for the disperse dyes to be present in finely divided form. For this purpose, the disperse dyes are ground to granules having an average particle size of from 0.1 to 10 μm, preferably from 1 to 5 μm, particularly preferably from 0.5 to 2 μm. The milling may be carried out in the presence of a dispersant. For example: the dried disperse dye is ground together with the dispersant or kneaded into a paste together with the dispersant and, if necessary, dried under reduced pressure or by spray drying. The resulting preform can be used to prepare the ink of the invention by adding water and, if desired, further auxiliaries.
Copolymers which are particularly suitable as anionic copolymers for the process of the invention are: those based on acrylic acid, methacrylic acid or maleic acid. Among these polymersPreference is given to those polymers which are obtained by polymerization of acrylic acid and/or methacrylic acid with one or more copolymerizable monomers. The copolymerizable monomer is selected from the group consisting of maleic acid, N-vinylformamide, N-vinylacetamide, derivatives of allylamine and diallylamine, N-vinylpyrrolidone, N-vinyl-N-methylformamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, vinyl acetate, vinyl propionate, acrylonitrile, styrene, methacrylonitrile, acrylamide, methacrylamide and N-mono/N, N-bis-C1-C10Alkyl (meth) acrylamides.
Particularly preferred anionic copolymers are those obtained by copolymerization of acrylic or methacrylic acid and styrene.
Particularly preferred are acrylic and methacrylic acid-styrene copolymers having a molecular weight of 3000 to 16000, especially 3000 to 10000.
Nonionic block copolymers particularly suitable for the process of the present invention are alkylene oxide condensates such as adducts of ethylene oxide and polypropylene oxide (referred to as EO-OP block copolymers) and adducts of propylene oxide and polyethylene oxide (referred to as anti-EO-OP block copolymers), and block polymers obtained by adding styrene (addition styrene) to polypropylene oxide and/or polyethylene oxide.
The preferred molecular weight is 2000-20000 ethylene oxide-propylene oxide block copolymer, especially 8000-16000 ethylene oxide-propylene oxide block copolymer, and the ethylene oxide content in the whole molecule is 30-80%, especially 60-80%.
Particularly suitable dispersants are anionic dispersants selected from the group consisting of:
(ba) acid esters of alkylene oxide adducts of the formula or salts thereof,
Figure A9812714700151
in the formula, X is an acid group of an inorganic oxoacid, for example: sulfuric acid or, preferably, phosphoric acid, or another organic acid group, Y being C1-C12Alkyl, aryl or aralkyl, "Alkylen" is ethylene or propylene, and m is 1 to 4 and n is 4 to 50,
(bb) polystyrene sulfonates (polystyrene sulfonates)
(bc) fatty acid taurinic anhydride (fatty acid taurides)
(bd) alkylated diphenyl oxide (alkylated diphenyl oxide) mono-or disulfonates (mono-or disulphonates),
(be) a sulfonate of a polycarboxylate,
(bf) 1 to 60 moles, preferably 2 to 30 moles, of ethylene oxide and/or propylene oxide with fatty amines, fatty amides, fatty acids or fatty alcohols each having 8 to 22 carbon atoms; or with a tri-to hexa-basic alkanol having 3 to 6 carbon atoms, converting the addition compound into an acidic ester with an organic dicarboxylic acid or with an inorganic polybasic acid,
(bg) a lignosulfonate salt,
(bh) naphthalenesulfonate, and
(bi) a condensate of formaldehyde.
The lignosulfonates (bg) used are mainly those with a sulfonic acid group content of not more than 25% by weight, or their alkali metal salts. Preferred lignosulfonates are those containing 5-15% by weight of sulphonic acid groups.
Examples of suitable condensates of formaldehyde (bi) are: condensates of lignosulfonates and/or phenols with formaldehyde, condensates of formaldehyde with aromatic sulphonic acids, for example: condensates of ditolyl ether sulfonates with formaldehyde, condensates of naphthalenesulfonic acid with formaldehyde and/or condensates of naphthol-or naphthol-sulfamic acid with formaldehyde, condensates of phenolsulfonic acid and/or sulfonated dihydroxydiphenylsulfones with phenol or cresol with formaldehyde and/or urea, and condensates of diphenyloxydisulfonic acid derivatives with formaldehyde.
Preferred products (bi) are:
condensates of ditolyl ether sulfonate with formaldehyde, as described in the examples of US-A-4,386,037.
Condensates of phenol and formaldehyde with lignosulphonates, as described in the examples of US-A-3,931,072.
-condensates of 2-naphthol-6-sulfonic acid, cresol, sodium bisulfite and formaldehyde [ see FIAT report 1013(1946) ], and
condensates of biphenyl derivatives and formaldehyde, as described in the examples of US-A-4,202,838.
Particularly preferred compounds (bi) are those of the formula:wherein
X is a direct bond or is oxygen,
a is an aromatic compound group and is bonded to the methylene group by a ring carbon atom,
m is hydrogen or a salt-forming cation, for example: alkali metal, alkaline earth metal or aluminum, and
n and p are, independently of one another, the numbers 1 to 4.
More particularly preferred compounds (bi) are those based on sulfonated condensates, the condensates being the condensates of chloromethyl biphenyl isomer mixtures and naphthalene, of the formula:
wherein (SO)3Na)1,4-1,6Represents the average degree of sulfonation of 1,4 to 1, 6.
The above-mentioned dispersants are known or can be prepared in comparison with known compounds obtained by well-known methods.
In the printing ink, the total content of the anionic copolymer, the nonionic block polymer and the dispersant is 3-9% of the total weight of the printing ink.
In the ready-to-use inks, the ratio of anionic copolymer to nonionic block polymer to dispersant can vary within wide limits; for example: 1.5: 0.5: 1; 1: 0.5: 1.5; 1: 1; 1: 0: 1; 1: 0; 1: 0; 0: 1 or 0: 1.
Preferred inks for use in the process of the present invention are those which comprise an anionic copolymer and a nonionic block polymer or an anionic copolymer and a dispersant or a nonionic block polymer and a dispersant.
Particularly preferred printing inks are those containing an anionic copolymer, a nonionic block polymer and a dispersant.
In addition to the disperse dyes of the formulae (1) to (23), the anionic copolymers, the nonionic block polymers and the dispersants, the inks may judiciously (Judiciosuly) comprise thickeners of natural or synthetic origin, some examples being commercial alginate thickeners, starch ethers or locust bean gum ethers, in particular sodium alginate on its own or in a mixture with modified cellulose, particularly preferably with 20 to 25% by weight of carboxymethyl cellulose.
In the inks of the invention, preference is given to using synthetic thickeners such as those based on poly (meth) acrylic acid or poly (meth) acrylamide.
In the process of the invention, preference is given to inks having a viscosity of from 1 to 40mPa.s (millipascal seconds), in particular from 1 to 20mPa.s, especially from 1 to 10 mPa.s.
Also preferably, the ink used in the method of the present invention is an ink having a surface tension of 60 to 30 newtons per centimeter (N/cm), particularly 50 to 40N/cm.
Important inks for use in the process of the invention are those having an electrical conductivity of from 0 to 3000. mu.S/cm, in particular from 100 to 700. mu.S/cm, measured on a 10% aqueous suspension basis.
The printing ink may also comprise a buffer substance, such as borax, borate or citrate. Some examples are borax, sodium borate, sodium tetraborate and sodium citrate. In particular, they are used in an amount of 0.1 to 3%, especially 0.1 to 1%, by weight of the entire ink, so that the pH is, for example, 4 to 10, preferably 5 to 8.
Further additives which may be present in the ink are surfactants, redispersing agents and wetting agents.
Suitable surfactants are the anionic or nonionic surfactants which are generally commercially available. Betaine monohydrate may be mentioned as an example of a redispersing agent. As humectants there are preferably used mixtures of sodium lactate (advantageously in the form of 50-60% strength aqueous solutions) and glycerol and/or propylene glycol, which are preferably used in amounts of from 7 to 20% by weight, based on the printing ink used according to the invention.
The ink may also include, if desired, acid donors, such as butyrolactone or sodium hydrogen phosphate, preservatives, substances which prevent bacterial and/or fungal growth, foam inhibitors, sequestering agents, emulsifiers, water-insoluble solvents, oxidising agents or degassing agents.
Suitable preservatives are, in particular, formaldehyde donors, such as paraformaldehyde and trioxane (trioxane), in particular aqueous formaldehyde solutions having a concentration of from 30 to 40% by weight; suitable sequestering agents are, for example, sodium nitrilotriacetate, sodium ethylenediaminetetraacetate and sodium polymetaphosphate, in particular sodium hexametaphosphate; suitable emulsifiers are, in particular, adducts of alkylene oxides and fatty alcohols, especially of oleoyl alcohols and ethylene oxide; suitable water-insoluble solvents are high-boiling saturated hydrocarbons, especially paraffins having a boiling point in the range of 160-210 ℃ (known as naphtha for paints and lacquers); suitable oxidizing agents are, for example, aromatic nitro compounds, in particular aromatic mono-or dinitrocarboxylic acids or sulfonic acids, which may be in the form of alkylene oxide adducts, in particular nitrobenzenesulfonic acids; suitable degassing agents are, for example, high-boiling solvents, in particular turpentine, higher alcohols, preferably C8-10Of a terpene alcohol or a mineral oil and/or silicone oil based degassing agent, especially a commercial formulation consisting of approximately 15-25% by weight of a mixture of mineral oil and silicone oil and 75-85% by weight of C8An alcohol (e.g., 2-ethyl-n-hexanol).
The printing ink can be prepared in a customary manner by mixing the components in the required amount of water.
The ink is preferably prepared, for example, by stirring one or more disperse dyes of the formulae (1) to (23) and a dispersant/copolymer/block polymer mixture and grinding the resulting mixture with a wet grinder to a defined degree of grinding corresponding to an average particle size of 0.2 to 1.0. mu.m. The concentrated millbase is then adjusted to the desired concentration with or without, for example, suitable thickeners, dispersants, copolymers, surfactants, wetting agents, redispersing agents, sequestering agents and/or preservatives, and water. In order to remove any coarse components present, it may be advantageous to filter the ready-to-use ink using a micro-molecular sieve of about 0.1 μm.
The process according to the invention for printing textile fibre materials can be carried out with an inkjet printing machine, which is known per se and is suitable for textile printing.
In the ink-jet printing method, individual droplets of printing ink are ejected in a controlled manner from a nozzle located above the object to be printed. In this case, the methods used are mainly the continuous ink jet method and the drop-on-demand (drop-on-demand) method. In the case of the continuous inkjet method, droplets are produced continuously, and the droplets which are not required in the print carried along are diverted into a collecting container and generally recycled. On the other hand, in the case of drop-on-demand (drop) methods, drops are generated and used in printing when needed; in other words, a droplet is only generated when it is desired to print with a droplet. The generation of the droplets can advantageously be carried out, for example, by means of a piezoelectric ink-jet head or by means of the use of thermal energy (known as bubble jet). The process of the invention is preferably printed using the continuous ink jet process or using the drop-on-demand (drop-on-demand) process.
After printing, the fibre material is dried at a temperature of up to 150 ℃, preferably 80 ℃ to 120 ℃.
The fixing of the fibre material is generally carried out by the dry-heat method (thermal fixing) or by the superheated steam method at atmospheric pressure (HT fixing), followed by fixing. The fixation was carried out under the following conditions:
-heat set colour: 1-2 minutes at 190-230 ℃;
-HT fixation: 4-9 minutes at 170-190 ℃.
The ink used in the present invention can be applied to various types of fiber materials such as wool, silk, cellulose, polyvinyl, polyacrylonitrile, polyamide, aramid, polypropylene, polyester, or polyurethane.
Polyester-containing fibrous materials are preferred.
Suitable polyester-containing fiber materials are those which consist wholly or partly of polyester. Examples are cellulose ester fibers, such as cellulose diacetate and cellulose triacetate fibers, especially linear polyester fibers, acid-modified or not, which are obtained by a process such as: fibers made by the condensation of terephthalic acid with ethylene glycol, or the condensation of isophthalic acid or terephthalic acid with 1, 4-bis-hydroxymethyl-cyclohexane, and copolymers of terephthalic acid and isophthalic acid with ethylene glycol. Suitably expanded to polyester-containing mixed fiber materials; in other words to blends of polyester and other fibers.
The invention further provides an aqueous printing ink for an inkjet printing process, which contains 1 to 35% by weight of at least one disperse dye of the formulae (1) to (23) described above, an anionic copolymer and/or a nonionic block polymer and/or a dispersant.
The printing ink and the disperse dye of the structural formulae (1) to (23) for the printing ink of the present invention, the anionic copolymer, the nonionic block polymer and the dispersant obey the aforementioned definitions and preferred ranges.
The printed product obtained by the invention has good all-round fastness property; for example: they have high fiber-dye bond stability in both the acidic and basic range, good optical stability, good wet fastness properties, for example: water fastness, wash fastness, salt water fastness, cross-dyeing resistance and perspiration fastness. Good fastness to chlorine bleaching, rubbing, ironing and dry heat setting, and also good appearance and high colour strength. The printing inks used exhibit good stability and good viscosity characteristics.
The following examples illustrate the invention. In these embodiments, temperature refers to degrees celsius; unless otherwise indicated, percentages are by weight. The relationship between parts by weight and parts by volume is a kilogram to liter relationship.
Example 1:
2.0 parts by weight of disperse dye with a structural formula of the following formula
Figure A9812714700201
With 0.3 part by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene, and
3.0 parts by weight of an anionic copolymer of acrylic acid and styrene were stirred together, and then the mixture was ground with a wet grinder to an average particle size of 0.2 to 1.0. mu.m.
Thereafter, to this was added, with stirring:
1.0 part by weight of a commercial surfactant,
3.7 parts by weight of a commercial redispersing agent,
0.2 parts by weight of a commercial preservative,
20.0 parts by weight of a commercial wetting agent, and
69.8 parts by weight of water, the dye content of the ink being adjusted to 2% by weight.
Example 2:
the printing ink prepared as in example 1 was printed on a polyester fabric with an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The final product is a bright yellow print with good all-round fastness properties, especially wet and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a bright yellow print is likewise obtained with good allround fastness properties, in particular wet fastness and light fastness.
Example 3:
3.0 parts by weight of disperse dye with a structural formula of the following formula
With 2.0 parts by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene, and
6.5 parts by weight of an anionic copolymer of acrylic acid and styrene (from National Starch)&Of Chemical chemicalsNarlex DX2020) were stirred together and then the mixture was ground by a wet grinder to an average particle size of 0.2 to 1.0 μm.
Thereafter, to this was added, with stirring:
12.0 parts by weight of 85% glycerol,
5.0 parts by weight of diethylene glycol,
3.0 parts by weight of betaine monohydrate,
0.1 part by weight of N-methylolchloroacetamide, and
68.4 parts by weight of water, the dye content of the ink being adjusted to 3% by weight.
Example 4:
the printing ink prepared as in example 3 was printed on a polyester fabric with an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The end product is a blue print which has good allround fastness properties, in particular wet fastness and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a blue print with good allround fastness properties, in particular wet fastness and light fastness, is likewise obtained.
Example 5:
2.0 parts by weight of disperse dye with a structural formula of the following formula
Figure A9812714700221
With 1.0 part by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene, and
0.3 part by weight of a nonionic alkylene oxide block polymer (produced from Albright)&Of WilsonPluronic F108) were stirred together and the mixture was then milled using a wet mill to an average particle size of 0.2-1.0 μm.
Thereafter, to this was added, with stirring:
12.0 parts by weight of 85% glycerol,
5.0 parts by weight of diethylene glycol,
3.0 parts by weight of betaine monohydrate,
0.1 part by weight of N-methylolchloroacetamide, and
76.6 parts by weight of water, the dye content of the ink being adjusted to 2% by weight.
Example 6:
the printing ink prepared as in example 5 was printed on a polyester fabric with an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The end product is a blue print which has good allround fastness properties, in particular wet fastness and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a blue print with good allround fastness properties, in particular wet fastness and light fastness, is likewise obtained.
Example 7:
1.2 parts by weight of disperse dye with a structural formula as follows
Figure A9812714700231
And 2.2 parts by weight of a disperse dye having a structural formula of
Stirred with 1.0 part by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene. The mixture was then ground with a wet grinder to an average particle size of 0.2-1.0. mu.m.
Thereafter, to this was added, with stirring:
12.0 parts by weight of 85% glycerol,
5.0 parts by weight of diethylene glycol,
3.0 parts by weight of betaine monohydrate,
0.1 part by weight of N-methylolchloroacetamide, and
75.5 parts by weight of water, so that the dye content of the ink was adjusted to 3.4% by weight.
Example 8:
the printing ink prepared as in example 7 was printed on a polyester fabric with an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The end product is a pink print which has good allround fastness properties, especially wet fastness and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a pink print with good allround fastness properties, in particular wet fastness and light fastness, is likewise obtained.
Example 9:
4.0 parts by weight of disperse dye with a structural formula of the following formula
Figure A9812714700241
With 2.0 parts by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene, and
1.0 part by weight of a nonionic alkylene oxide block polymer (produced from Albright)&Of WilsonPluronic F108), and
8.0 parts by weight of an anionic copolymer of acrylic acid and styrene (from National Starch)&Of Chemical chemicalsNarlex DX2020) were stirred together,
then, a wet mill grinds the mixture to an average particle size of 0.2 to 1.0. mu.m.
Thereafter, to this was added, with stirring:
5.0 parts by weight of 85% glycerol,
15.0 parts by weight of diethylene glycol,
2.0 parts by weight of betaine monohydrate,
0.1 part by weight of N-methylolchloroacetamide, and
62.9 parts by weight of water, so that the dye content of the ink was adjusted to 2% by weight.
Example 10:
the ink prepared as in example 9 was printed on a polyester fabric using an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The end product is a violet print which has good all-round fastness properties, especially wet fastness and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a violet print with good all-round fastness properties, in particular wet fastness and light fastness, is likewise obtained.
Example 11:
4.0 parts by weight of disperse dye with a structural formula of the following formula
Figure A9812714700251
With 1.0 part by weight of a dispersant based on sulfonated condensates of chloromethylbiphenyl isomer mixture and naphthalene, and
3.0 parts by weight of an anionic copolymer based on partially sulfated octylphenol ethoxylate having 25 ethylene oxide units per mole of octylphenol (from BASF)Emulphor OPS 25) were stirred together,
the mixture was then ground with a wet grinder to an average particle size of 0.2-1.0. mu.m.
Thereafter, to this was added, with stirring:
10.0 parts by weight of 85% glycerol,
10.0 parts by weight of diethylene glycol,
1.7 parts by weight of betaine-hydrate,
0.1 part by weight of N-methylolchloroacetamide, and
70.2 parts by weight of water, so that the dye content of the ink was adjusted to 2% by weight.
Example 12:
the printing ink prepared as in example 11 was printed on a polyester fabric with an inkjet printing machine operated by the piezo-electric technique by drop-on-demand (drop-on-demand).
The print was dried and fixed in superheated steam at 180 ℃ for 8 minutes.
The end product is a blue print which has good allround fastness properties, in particular wet fastness and light fastness.
If the dried print is fixed with hot air at 200 ℃ for 1 minute, a blue print with good allround fastness properties, in particular wet fastness and light fastness, is likewise obtained.
If the inks prepared in examples 1,3,5,7,9 and 11 are printed on a polyester fabric using an ink-jet printing machine operated by the drop-on-demand bubble jet technique and finished in the manner indicated above, prints having good all-round fastness properties, in particular wet fastness and light fastness, are likewise obtained.
If the inks prepared as in examples 1,3,5,7,9 and 11 are printed on a polyester fabric by a continuous inkjet process and finished as indicated above, the result is still a print having good all-round fastness properties, in particular wet fastness and light fastness.

Claims (9)

1. A process for printing textile fibre materials by the ink-jet printing process, wherein the textile fibre materials are printed with an aqueous printing ink which contains at least one disperse dye, an anionic copolymer and/or a nonionic block polymer and/or a dispersant.
2. The process of claim 1, wherein a disperse dye having the following structural formula is used:
Figure A9812714700021
wherein R is16Is halogen, nitro, or cyano, R17Is hydrogen, halogen, nitro or cyano, R18Is halogen or cyano, R19Is hydrogen, halogen, C1-C4Alkyl or C1-C4Alkoxy radical, R20Is hydrogen, halogen or amido, R21And R22Independently of one another, hydrogen, or C which is unsubstituted or substituted by hydroxy, cyano, acetoxy or phenoxy1-C4An alkyl group, a carboxyl group,
wherein R is23Is hydrogen, phenyl or phenylsulfinyl (phenyl) in which the phenyl ring is unsubstituted or substituted by C1-C4Alkyl, sulfo or C1-C4Alkyl sulfonyloxy (alkylsulfo) substituted benzene ring, R25Is unsubstituted or C1-C4Alkyl-substituted amino or hydroxy, R26Is hydrogen or C1-C4Alkoxy radical, R27Is hydrogen or-O-C6H5-SO2-NH-(CH2)3-O-C2H5Group, R36Is hydrogen, hydroxy or nitro, R37Is hydrogen, hydroxyl or nitro,
wherein R is28Is unsubstituted or substituted by hydroxy C1-C4Alkyl radical, R29Is C1-C4Alkyl radical, R30Is cyano, R31Is of the formula- (CH)2)3-O-(CH2)2-O-C6H5Group of (A), R32Is halogen, nitro or cyano, R33Is hydrogen, halogen, nitro or cyano,
Figure A9812714700032
wherein,
R34is C1-C4Alkyl radical, R35Is unsubstituted or substituted by C1-C4Alkoxy-substituted C of1-C4Alkyl, W is a radical-COOCH2CH2OC6H5And W1Is hydrogen, or W is hydrogen and W is1is-N = N-C6H5，
Figure A9812714700033
Where ring A "and ring B" are rings which are unsubstituted or substituted one or more times by halogen,
wherein R is34Is unsubstituted or substituted by hydroxy, C1-C4Alkoxy or C1-C4alkoxy-C1-C4Alkoxy-substituted C1-C4Alkyl radical, and
Figure A9812714700043
Figure A9812714700045
Figure A9812714700051
or
3. The process according to any one of claims 1 or 2, wherein the anionic copolymer used is a copolymer based on acrylic acid, methacrylic acid or maleic acid.
4. A process as claimed in claim 3, wherein the anionic copolymer used is a copolymer of acrylic acid and/or methacrylic acid with one or more of the group of copolymerizable monomers consisting of maleic acid, N-vinylformamide, N-vinylacetamide, derivatives of allylamine and diallylamine, N-vinylpyrrolidone, N-ethyleneaminealkenyl-N-methylformamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, vinyl acetate, vinyl propionate, acrylonitrile, styrene, methacrylonitrile, acrylamide, methacrylamide and N-mono/N, N-bis-C1-C10Alkyl (meth) acrylamides.
5. The process according to one of claims 1 to 4, wherein the nonionic block polymer used is an alkylene oxide condensate or a block polymer obtained by addition (byaddtion of) styrene to polypropylene oxide and/or polyethylene oxide.
6. The process according to one of claims 1 to 5, wherein the dispersant used is an anionic dispersant from the group consisting of:
(ba) acid esters of alkylene oxide adducts of the formula or salts thereof,
Figure A9812714700061
wherein X is an acid group of an inorganic oxoacid, or an organic acid group, and Y is C1-C12Alkyl, aryl or aralkyl, "Alkylen" is ethylene or propylene, and m is 1 to 4 and n is 4 to 50,
(bb) polystyrene sulfonates (polystyrene sulfonates)
(bc) fatty acid taurinic anhydride (fatty acid taurides)
(bd) alkylated diphenyl oxide (alkylated diphenyl oxide) mono-or disulfonates (mono-or disulphonates),
(be) a sulfonate of a polycarboxylate,
(bf) an addition compound of 1 to 60 mol of ethylene oxide and/or propylene oxide to fatty amines, fatty amides, fatty acids or fatty alcohols each having 8 to 22 carbon atoms, or to trihydric to hexahydric alkanols having 3 to 6 carbon atoms, said addition compound being converted into an acidic ester with an organic dicarboxylic acid or with an inorganic polybasic acid,
(bg) a lignosulfonate salt,
(bh) naphthalenesulfonate, and
(bi) a condensate of formaldehyde.
7. A process as claimed in claim 6, wherein the dispersant used is of the formula
The anionic dispersant of (1), wherein
X is a direct bond or oxygen, a is an aromatic compound group and is attached to the methylene group at a ring carbon atom, M is hydrogen or a salt-forming cation, for example: an alkali metal, an alkaline earth metal or aluminium, and n and p are, independently of one another, the numbers 1 to 4.
8. An aqueous printing ink for inkjet printing processes, which contains 1 to 35% by weight of at least one disperse dye of the formulae (1) to (23), an anionic copolymer and/or a nonionic block polymer and/or a dispersant.
9. A textile fibre material which has been printed by the inkjet printing process with an aqueous printing ink according to claim 8.
CN98127147A 1997-12-17 1998-12-16 Process for ink-jet printing textile fibre materials Pending CN1224092A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101407750B (en) * 2001-08-13 2011-03-23 宝洁公司 Novel oligomeric hydrophobic dispersants
CN102127333A (en) * 2011-01-12 2011-07-20 郑州鸿盛数码科技股份有限公司 Direct ink-jet printing disperse dye ink and use method thereof
CN108530947A (en) * 2018-05-29 2018-09-14 绍兴金绿洲新材料科技有限公司 A kind of environmental protection and economy type disperse red dye mixture
CN109914130A (en) * 2019-03-06 2019-06-21 常州纺织服装职业技术学院 A kind of terylene digital ink-jet printed antistatic preprocessing solution and application
CN110256868A (en) * 2019-06-12 2019-09-20 无锡颐景丰科技有限公司 A kind of preparation method of high-performance liquid disperse dyes
CN110804880A (en) * 2019-12-03 2020-02-18 郑州鸿盛数码科技股份有限公司 Ink-jet ink for polyester-cotton blended fabric and preparation method thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101407750B (en) * 2001-08-13 2011-03-23 宝洁公司 Novel oligomeric hydrophobic dispersants
CN102127333A (en) * 2011-01-12 2011-07-20 郑州鸿盛数码科技股份有限公司 Direct ink-jet printing disperse dye ink and use method thereof
CN108530947A (en) * 2018-05-29 2018-09-14 绍兴金绿洲新材料科技有限公司 A kind of environmental protection and economy type disperse red dye mixture
CN109914130A (en) * 2019-03-06 2019-06-21 常州纺织服装职业技术学院 A kind of terylene digital ink-jet printed antistatic preprocessing solution and application
CN109914130B (en) * 2019-03-06 2021-11-02 常州纺织服装职业技术学院 Antistatic pretreatment solution for digital ink-jet printing of terylene and application thereof
CN110256868A (en) * 2019-06-12 2019-09-20 无锡颐景丰科技有限公司 A kind of preparation method of high-performance liquid disperse dyes
CN110804880A (en) * 2019-12-03 2020-02-18 郑州鸿盛数码科技股份有限公司 Ink-jet ink for polyester-cotton blended fabric and preparation method thereof

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