CN1204711A - Pigment dyeing and pigment printing process - Google Patents

Pigment dyeing and pigment printing process Download PDF

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CN1204711A
CN1204711A CN 98115671 CN98115671A CN1204711A CN 1204711 A CN1204711 A CN 1204711A CN 98115671 CN98115671 CN 98115671 CN 98115671 A CN98115671 A CN 98115671A CN 1204711 A CN1204711 A CN 1204711A
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formula
dyestuff
group
alkyl
pigment
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P·艾施里曼
P·海尔奇格
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Novartis AG
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Ciba Geigy AG
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Abstract

The present invention describes a process for dyeing or printing fiber material by the pigment dyeing or pigment printing process, which comprises applying to the fiber material, and subsequently fixing, a dyeing liquor or a print paste comprising at least one dye of the formulaD-(X)n(1)in which D is a radical of an insoluble organic dye of the phthalocyanine, perinone, indigoid, thioindigoid, dioxazine, diketopyrrolopyrrole, isoindolinone, perylene, quinacridone, metal complex, monoazo, disazo, trisazo or anthraquinone series, X is a hydrophilic polar radical, and n is 1, 2 or 3, and at least one pigment dye binder, and also, if desired, further auxiliaries.

Description

Pigment dyeing and pigment printing process
The present invention relates to a kind ofly make fibrous material dyeing or method for printing with special dyestuff by pigment dyeing or pigment printing process.
Making fibrous material dyeing or stamp with pigment dyeing or pigment printing process is the method for knowing already.But the coating that uses in these methods usually can not satisfy the various requirement, particularly sublimation reliability of proposition at present and the requirement of drycleaning fully.
Have now found that, it is shocking, use following new method can significantly improve the sublimation reliability and the drycleaning of COAT PRINTING and pigment dyeing; And find, therefore might make these stamps or colouring method that required improvement is arranged.
So, the invention provides and a kind ofly make fibrous material dyeing or method for printing by pigment dyeing or pigment printing process, this method comprises and will contain the dyestuff and at least a paint adhesive of at least a following formula, also have the dye liquor or the printing paste of assistant to be applied on the fibrous material if desired, and then fixation
D-(X) n(1) in the formula, D is the group of following insoluble organic dyestuff: phthalocyanine, perilla ketone (perinone), indigoid, thioindigo, dioxazine, diketopyrrolo-pyrrole, iso-dihydro-indole, perylene, quinacridone, metal complex, monoazo, diazonium, nitrine or anthraquinone series, X is the hydrophilic polar gene, and n is 1,2 or 3.
Fibrous material also has the printing paste stamp of assistant if desired preferably by pigment printing process dyestuff and at least a paint adhesive that contains at least a formula (1), and then fixation.D is preferably the group of insoluble organic dyestuff monoazo, diazonium, nitrine or anthraquinone series.
Insoluble organic dyestuff preferably refers to the water-insoluble organic dyestuff.In the method for the invention, preferred following dying
Figure 98115671000512
In the formula, R is hydrogen, halogen, nitro or cyano group, R 1Be hydrogen, halogen, nitro, cyano group or X group, R 2Be hydrogen or X group, R 3Be amino or hydroxyl, R 4Be hydrogen or formula
Figure 98115671000615
Group, R wherein 5Be hydrogen, C 1-C 4Alkyl or C 1-C 4Alkoxyl, R 6Be hydrogen or halogen, R 7Be hydrogen, C 1-C 4Alkyl or C 1-C 4Alkoxyl, the dyestuff of formula (2) requires to contain at least one X group,
Figure 98115671000616
In the formula, R 12Be C 1-C 4Alkyl, R 13Be hydrogen, halogen, C 1-C 4Alkyl, C 1-C 4Alkoxyl, nitro, cyano group or X group, R 14Be hydrogen, halogen, nitro, cyano group or X group, R 15Be hydrogen, halogen, C 1-C 4Alkyl, C 1-C 4The dyestuff of alkoxyl, nitro or cyano group, formula (3) requires to contain at least one X group, In the formula, ring A ' and B ' are by halogen and/or the X group replaces 1 time or repeatedly, the dyestuff of formula (4) requires to contain at least one X group,
Figure 98115671000618
In the formula, R 16Be C 1-C 4Alkyl or X group, R 17Be hydrogen, cyano group or carbamoyl, R 18Be hydrogen, C 1-C 4Alkyl or X group, R 19For anthraquinone radicals or be unsubstituted or by C 1-C 4Alkyl, C 1-C 4Alkoxyl, halogen, nitro, cyano group, CF 3Or the phenyl or naphthyl of X group replacement, the dyestuff of formula (5) requires to contain at least one X group,
Figure 98115671000719
In the formula, R 19For anthraquinone radicals or be unsubstituted or by C 1-C 4Alkyl, C 1-C 4The phenyl or naphthyl that alkoxyl, nitro, cyano group or X group replace, R 25Be C 1-C 6Alkyl,
Figure 98115671000720
In the formula, R 20Be hydrogen, halogen, cyano group or nitro, R 21Be hydrogen or amino, R 22Be hydrogen or halogen,
Figure 98115671000721
In the formula, R 23Be hydrogen or C 1-C 4Alkyl, and R 24Be hydrogen, hydroxyl or amino, and
Figure 98115671000722
In the formula, ring A can be unsubstituted or replacement.
X group in the formula (1) is a hydrophilic polar group, as carboxamide groups, sulfoamido, and for amide groups, may be in these groups by hydroxyl-C 1-C 6The alkyl list replaces or two replacements, or is unsubstituted or the C of hydroxyl replacement 4-C 12Alkyl, alkyl chain can be by oxygen, carboxylic acid amides and/or sulfonamide interval one or many, the perhaps C that is particularly replaced by one or more hydroxyls 1-C 6Alkyl.
N in the formula (1) is 1,2 or 3, (X) nBe one, two or three identical or different radicals X.Preferred n=1.
In the method for the invention, preferably use formula (1) dyestuff of molecular weight＜550.
In the method for the invention, the dyestuff of preferred especially following formula
Figure 98115671000827
In the formula, R 8Be hydrogen, methoxyl group, halogen, nitro or CF 3, R 9Be hydrogen, methyl, ethyl or ethoxy,
Figure 98115671000828
Figure 98115671000929
In the formula, R 10Be hydrogen, methoxyl group, chlorine or nitro,
Figure 98115671000930
Figure 98115671001031
In the formula, R 11Be C 1-C 6Alkyl,
Figure 98115671001032
Figure 98115671001133
In the method for the invention, the dyestuff of formula (10), (11), (12) and (22) most preferably.
The present invention also provides the dyestuff of following formula
Figure 98115671001134
In the formula, R 26Group for following formula
Figure 98115671001236
In the formula, R 16, R 17, R 18And R 25Suc as formula (5) and (6) regulation, X is hydrophilic polar group, and the phenyl or naphthyl in the formula (27) is unsubstituted or is replaced by halogen, cyano group or nitro that the dyestuff of formula (26) requires to contain at least one X group.
The dyestuff of above-mentioned formula (26) prepares according to the following steps with known method: the compound diazotization that makes following formula
Figure 98115671001237
, then with the product coupling accepted way of doing sth (5a), (6a), (27) or the coupling component (8a) that generate.Isolate the dyestuff of generation, washing is also dry.
Also can prepare above-listed other monoazo dyes that the present invention uses with similar method.
The example that is suitable for the paint adhesive of the inventive method is an acrylate copolymer, as poly-(methyl) acrylate, poly-(methyl) acrylamide; Perhaps (methyl) acrylate or (methyl) acrylamide and suitable comonomer such as maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinyl acetic acid, ethyleneoxy acetate, the vinyl propionic acid, crotonic acid, aconitic acid, allyl acetic acid, allyloxy acetate, allyl malonic acid, 2-acrylamido-2-methyl propane sulfonic acid, the copolymer of gluconic acid or allyl butanedioic acid, perhaps with the copolymer of these sour esters, with the N-vinyl pyrrolidone, the N-vinyl formamide, the N-vinyl acetamide, (methyl) acrolein, N-vinyl-N-methylacetamide, caprolactam, the copolymer of styrene derivative or vinyl phosphoric acid; The polyamide derivative; Synthetic resin dispersion; Copolymer based on vinyl; Diamides-aldehyde precondensate; Contain the copolymer of N-vinyl lactam or based on the polymer of butadiene.
The comonomer of particularly suitable is above-mentioned acid and C 1-C 6Alcohol is as the ester of methyl alcohol, ethanol, isopropyl alcohol or butanols.
The dyestuff of formula (1) should be used for dye liquor or printing paste with the form of disperseing.In this case, preferably dyestuff being ground with decentralized medium, is 0.05-1.0 μ m so that make dye particle.In order to prepare dye dispersion liquid, may use dispersant commonly used, preferably use non-ionic dispersing agent.The non-ionic dispersing agent of particularly suitable is the compound that is selected from (ca) alkylene oxide adduct of following formula
Figure 98115671001338
In the formula, Y 1Be C 1-C 12Alkyl, aryl or aralkyl, " Alkylen " are ethylidene or propylidene, m 1Be 1-4, n 1Be 4-50, (cb) alkylene oxide adduct, adduct with the first aliphatic alcohol of (cba) saturated or unsaturated 1-6, (cbb) aliphatic acid, (cbc) fatty amine, (cbd) fatty acid amide, (cbe) diamines, (cbf) Isosorbide Dinitrate, (cc) alkylene oxide condensation product (block polymer), (cd) polymer of vinyl pyrrolidone, vinyl acetate or vinyl alcohol, and (ce) copolymer or the terpolymer of vinyl pyrrolidone and vinyl acetate and/or vinyl alcohol.
The component that is well suited for (ca) is the polymerization adduct of 4-40 moles of ethylene oxide and 1 mole of a kind of like this phenol, and this phenol has at least one C 4-C 12Alkyl, phenyl, tolyl, α-tolyl ethyl, benzyl, α-Jia Jibianji or α, α-Er Jiajibianji, for example be butylphenol, tributyl phenol, octyl phenol, nonyl phenol, binonylphenol, O-SyL, benzylphenol, dibenzyl phenol, α-tolyl ethyl phenol, dibenzyl (nonyl) phenol, α-Jia Jibianji phenol, two (α-Jia Jibianji) phenol or three (α-Jia Jibianji) phenol, it is possible using these phenol separately or using with mixture.
Significant especially component (ca) is 6-30 moles of ethylene oxide and the 1 4-nonyl phenol that rubs, with 1 mole of binonylphenol or particularly added by 1-3 mole styrene and to be incorporated into the adduct that the compound for preparing on 1 moles of phenol obtains with 1 mole.
The styrene adduct is by the preparation of known method, preferably prepares in the presence of catalyst such as sulfonic acid, p-methyl benzenesulfonic acid or particularly zinc chloride.The phenylethylene that is fit to is preferably styrene, α-Jia Jibenyixi or vinyltoluene (4-methyl styrene).The example of phenols is phenol, cresols or xylenol.
The ethylene oxide adduct of preferred especially following formula
Figure 98115671001439
In the formula, m 3Be 1-3, n 3Be 8-30.
The ethylene oxide adduct of same preferred following formula In the formula, Y 2Be C 4-C 12Alkyl, phenyl, tolyl, tolyl-C 1-C 3Alkyl or phenyl-C 1-C 3Alkyl is as α-Jia Jibianji or α, α-Er Jiajibianji, m 2Be 1-3, n 2Be 4-40.
Nonionic component (cb) is preferably--by 1-100 mole alkylene oxide such as oxirane and/or expoxy propane and 1 mole 〉=C 4Aliphatic series-unit alcohol, with 1 mole of 3-6 unit's aliphatic alcohol or with 1 mole unsubstituted or by alkyl, phenyl, α-tolyl ethyl, benzyl, α-Jia Jibianji or α, the alkylene oxide adduct of the phenol (cba) that α-Er Jiajibianji replaces;--1-100, preferred 2-80 moles of ethylene oxide (it is possible that the substituted epoxides of single ethylene oxide unit substitutes as styrene oxide and/or expoxy propane) and C 8-C 22The alkylene oxide adduct of undersaturated or saturated monohydric alcohol (cba), aliphatic acid (cbb), fatty amine (cbc) or fatty acid amide (cbd);--the adduct of alkylene oxide adduct, preferred oxireme-expoxy propane and ethylenediamine (cbe);--long-chain ester based ethoxyquin Isosorbide Dinitrate is arranged, if any the polyoxyethylene Arlacel-20 of 4-20 ethylene oxide unit or the polyoxyethylene sorbitan trioleate of 4-20 ethylene oxide unit (cbf) is arranged.
Preferred ingredients (cc) is ethylene oxide adduct (being called the EO-PO block polymer) that poly(propylene oxide) is arranged and propylene oxide adduct (being called anti-EO-PO block polymer) that poly(ethylene oxide) is arranged.
Especially preferably the molecular weight of poly-propylene oxide is that the content of oxirane in 1700-4000, the whole molecule is the epoxy ethane-epoxy propane block polymer of 30-80%, particularly 60-80%.
The dyestuff of formula (1) is applied to occasion on the fibrous material from dye liquor under, for example with containing the dyestuff of at least a formula (1) and at least a paint adhesive, also having the dye liquor of assistant to handle fibrous material if desired, dry dyed fibrous material makes dye fixing accomplish this point by heat treated subsequently.
The fibrous material that dyes is preferably handled with continuation method such as dip method commonly used in the textile industry, consumption at dye liquor Chinese style (1) dyestuff can change with desirable color depth, usually by the finished product fabric restatement that will dye, its consumption is that 0.01-15% (weight), particularly 0.1-10% (weight) are preferred.Except formula (1) dyestuff and paint adhesive, dye liquor also can contain additive commonly used usually, its example is a cross-linking agent resin, as water-soluble melamine, formaldehyde-melamine and formaldehyde-carbamide resin or precondensate, as tri methylol melamine, hexamethylol melamine or dimethylol urea, perhaps with formamide, thiocarbamide, guanidine, cyanamide, water-soluble formaldehyde (in advance) condensation product and/or the water-soluble organic sulfonate of diaminourea cyanogen, as sodium naphthalene sulfonate, or urea derivative, the N-hydroxymethyl derivative of nitrogen-containing compound particularly, melamine-formaldehyde condensation products or N-methylolurea compound as unmodified or etherificate, and sour donor, as aliphatic ammonium chloride or magnesium chloride, the aqueous solution of inorganic salts such as alkali chloride or alkali metal sulfates, the aqueous solution of alkali metal hydroxide or alkali metal sulfates, alkali metal hydroxide, urea, thickening agent and alginates thickening agent, the water-soluble cellulose Arrcostab also has levelling agent, defoamer and/or degasser, the infiltration accelerator, migration inhibitor, fabric softening and wetting agent.
The dyestuff of formula (1) preferably is applied on the fibrous material in printing paste with pigment printing process.
The consumption of formula (1) dyestuff in printing paste can be according to the change in depth of required color; Usually the per kilogram printing paste uses 0.01-400g, particularly 0.5-300g, 1-200g dyestuff most preferably.Except the dyestuff of formula (1), printing paste also includes one or more coating that is usually used in the COAT PRINTING technology.
Here the per kilogram printing paste contains 1-300, particularly 50-200g coating usually.
Preferably, except the dyestuff and paint adhesive of formula (1), printing paste also contains thickening agent, for example based on the thickening agent that gathers (methyl) acrylic acid, poly-(methyl) acrylamide and copolymer or terpolymer.
The quantity of thickening agent in printing paste is preferably 0-100, more preferably 10-60,10-40g/kg printing paste most preferably.
This printing paste can contain assistant commonly used in the COAT PRINTING equally, and crosslinking agent is suitable example.The example of the crosslinking agent that is fit to is water-soluble melamine, formaldehyde-melamine and formaldehyde-carbamide resin or precondensate, as tri methylol melamine, hexamethylol melamine or dimethylol urea, and perhaps water-soluble formaldehyde and formamide.(in advance) condensation product of thiocarbamide, guanidine, cyanamide, diaminourea cyanogen, and/or water-soluble organic sulfonate, as sodium naphthalene sulfonate, perhaps glyoxal urea derivative, as shown in the formula compound
Figure 98115671001641
, the N-hydroxymethyl derivative of nitrogen-containing compound particularly is as the melamine-formaldehyde condensation products or the N-methylolurea compound of unmodified or etherificate.
The example of the melamine-formaldehyde condensation products of unmodified or etherificate is the compound of following formula
N-methylolurea compound unmodified or etherificate for example comprises the product of formaldehyde and urea or urea derivative, this product can carry out etherificate subsequently, the urea derivative that is fit to is ethylidene-or the propylidene urea of ring-type, it also can contain substituting group in alkylidene, as hydroxyl, comprise the product of triazinone (trisazone) resin of formaldehyde and urea ketone (urones) or unsubstituted or replacement.
The example of the N-methylolurea compound that is fit to is unmodified or the N-methylol hydroxyl ethylidene-urea product of modification, and its example is the compound of following formula
Figure 98115671001743
Or based on the methylolation product of propylidene urea or ethylidene-urea/melamine.Preferred cross-linking agents is the N-methylol hydroxyl ethylidene-urea compound of unmodified or modification, based on the methylolation product of propylidene urea or ethylidene-urea/melamine, the melamine-formaldehyde condensation products of particularly unmodified or etherificate.The mixture that uses two or more water-soluble cross-linker also is possible, for example unetherified and mixture of the melamine-formaldehyde condensation products of part etherificate only.If desired, printing paste also can contain crosslinking catalyst, body such as butyrolactone or dibastic sodium phosphate, preservative agent, chelating agent, emulsifying agent, water-insoluble solvent, oxidant or degasser are given in acid.
The example that is applicable to the crosslinking catalyst of the inventive method is used as anti-crease finishing and the anti-reagent that shrinks the arrangement catalyst usually for all, as by Textilhilfsmittelkatalog[catalogue of textile auxiliaries] 1991, Konradin Verlag R.Kohlhammer, Leinfelden-Echterdingen 1991 is known.The example of the crosslinking catalyst that is fit to is an inorganic acid, as phosphoric acid; Lewis acid is as zinc chloride, basic zirconium chloride, NaBF 4, AlCl 3, MgCl 2Ammonium salt is as ammonium sulfate, ammonium chloride; Or the hydrochloride of hydrohalide, particularly organic amine, as CH 3-CH 2-CH 2-NH-CH 3HCl.Preferred Lewis acid, particularly ammonium chloride or the magnesium chloride that uses ammonium salt or contain magnesium.
The preservative agent of particularly suitable is that formaldehyde is given the body agent, as paraformaldehyde with the formalin of trioxane, particularly concentration about 30 to 40% (weight); The example of the chelating agent that is fit to is nitroso triacetic acid sodium, edetic acid sodium, particularly sodium hexametaphosphate, calgon; Particularly suitable emulsifying agent is the adduct of the adduct of alkylene oxide and fatty alcohol, particularly oleyl alcohol and oxirane; The water-insoluble solvent that is fit to is that higher boiling saturated hydrocarbons, particularly boiling range are about 160 to 210 ℃ alkane (being called varnish makers' and painters' naphtha); The example of the oxidant that is fit to is an aromatic nitro compound, particularly with alkylene oxide adduct form the aromatics list that exists-or two nitrocarboxylic acid or-sulfonic acid, particularly nitrobenzene-sulfonic acid; And the example of the degasser that is fit to is high boiling solvent, turpentine oil particularly, higher alcohols, preferred C 8-C 10Alcohol, terpenol or based on the degasser of mineral oil and/or silicone oil, the mixture of particularly about 15 to 25% (weight) mineral oil and silicone oil and about 75 to 85% (weight) C 8Alcohol is as the commercial formulation of 2-ethyl n-hexyl alcohol.
In fibrous material stamp process, preferred all surfaces and some zone that printing paste is coated directly onto fibrous material with printing machine such as dimpled grain printing machine, rotary screen printing machines, roller printing machine and the lithographic plate screen printing machine of common structure.The also available ink-jet printed technology of stamp is carried out.
Behind the stamp, fibrous material preferably 150 ℃ at the most, particularly 80-120 ℃ down dry, heat-treat then, so that stamp is finished and/or made dyeing fixing.
The heat treatment available heat pads that heap dyes method, thermosol method or preferred steam method (HT fixation) is finished.
Under the situation of steam method, in steamer, under 95-210, preferred 100-180 ℃, handle with superheated steam through the fibrous material of stamp.Under HT fixation situation, preferably handled 2-5 minute down at 150-170 ℃ through the fibrous material of stamp.
The stamp arrangement of carrying out with the thermosol method can be after the initial dyeing, for example carry out under 100-210 ℃, or carry out under the initial dyeing not having.Thermosol handle preferably 120-210 ℃, particularly carry out under 140-180 ℃.Apparent temperature and deciding, thermosol was handled sustainable 20 seconds to 5 minutes, preferred 30 seconds to 4 minutes.Thermosol is handled and was carried out under 190-210 ℃ 1-2 minute usually.After the stamp process, through the method washing commonly used of the fibrous material of stamp, so that remove the not dyestuff of fixation.For this reason, for example to boiling point, use the water treatment fibrous material, soap or synthetic detergent can be added in the water if desired at 40 ℃.
The for example available following steps of stamp process of the present invention are carried out: will contain the dyestuff of at least a formula (1) and at least a paint adhesive, also have the printing paste of assistant to be applied on the fibrous material if desired; Dry fibrous material through stamp; With heat-treating methods stamp is fixed subsequently.
Dye liquor or printing paste that the present invention uses can be applied on the various fibrous materials, as wool, silk, cellulose, polyvinyl fiber, polyacrylonitrile fibre, polyamide fiber, aramid fibre, polypropylene fibre, polyester fiber or polyurethane fiber.Preferably contain polyester and cellulosic fibre material.The fibrous material that contains polyester that is fit to be fully by or the fibrous material formed by polyester of part.Its example is a cellulose ester fiber, as two generation estron and tri acetic acid fiber cellulose fiber, straight chain polyester fiber particularly, their peracid modifications, for example by M-phthalic acid and ethylene glycol, M-phthalic acid or terephthalic acid (TPA) and 1, two (methylol) cyclohexane condensations of 4-make, and also can be the fiber that the copolymer of terephthalic acid (TPA) and M-phthalic acid and ethylene glycol makes.Another material that is fit to is the blended material that contains polyester, i.e. the mixture of polyester and other fibers.
The cellulosic fibre material that is fit to is those materials of being made up of cellulose wholly or in part.Its example is a natural fiber material, as cotton, flax or hemp; The regenerated fiber material is as viscose, viscose silk or Ku Puluo.The cellulose fibre blended material also is suitable for, i.e. the mixture of cellulose and other fibers, particularly cotton/Polyester Fibers.Main textiles, knitwear and the fibre web that uses these fibers.
The dyeing or the stamp that obtain with method of the present invention have good comprehensive fastness; For example they have good wet fastness such as good washing, water, salt solution, cross dyeing and perspiration fastness, good chlorine fastness, crock fastness and pleating fastness and dry heat-setting fastness, and significant high color intensity and light color and luster are arranged.Particularly, the dyeing that obtains with method of the present invention or the characteristics of stamp are that good light fastness, sublimation reliability and drycleaning are arranged.
Embodiment is used for illustrating the present invention.Here umber and percentage are all represented with weight.Temperature is that the heavy relation with part volume of degree centigrade part is identical with the relation of cubic centimetre with gram.
Embodiment 1
2.23g 1-amino anthraquinones is stirred in 20ml 100% acetate, and at room temperature is added dropwise to 1.7ml 40% nitrosylsulfuric acid.After the short time reaction, add the pyridinone compounds of 1.94g following formula. Subsequently, coupling is finished, isolated the following formula precipitated solid, with hot wash and dry with filtration method by being added dropwise to saturated sodium acetate solution.
Figure 98115671002045
Embodiment 2
26g aniline-4-(two-N, N-ethoxy) sulfonamide is dissolved in the water that 200ml contains the 25ml concentrated hydrochloric acid, is cooled to 0 ℃, uses the aqueous solution diazotization of 6.9g natrium nitrosum then.With in the sodium acetate solution and the diazonium compound that generates, add the solution of the coupling component of 18g following formula.
Figure 98115671002046
Make the pH value rise to 5.Filter out the following formula dyestuff of generation,
Figure 98115671002147
Wash with water, and dry.
Embodiment 3
Repeat the step of embodiment 1, but do not use the coupling component of 1.94g formula (32), and the stoichiometry coupling component of use following formula,
Figure 98115671002148
Obtain the dye powder of following formula.
Figure 98115671002149
Embodiment 4
2.23g 1-amino anthraquinones is stirred in 20ml 100% acetate, and at room temperature is added dropwise to 1.7ml 40% nitrosylsulfuric acid.After the short time reaction, add the compound of 1.41g following formula,
Figure 98115671002150
In order to finish coupling reaction, be added dropwise to saturated sodium acetate solution.Filter out precipitated solid, with hot wash and dry.Obtain the chlorine dye powder of following formula.
Embodiment 5
Repeat the step of embodiment 1, but do not use 2.23g 1-amino anthracene roller, and the use listed stoichiometric a kind of compound of table 1 (A), do not use the coupling compound of 1.94g formula (32), and use the listed stoichiometry coupling component (B) of table 1, obtain the dyestuff of the formula shown in the table 1 (12) to formula (23).Table 1
Figure 98115671002453
Embodiment 6
Cotton fabric contains the printing paste stamp of following component with the per kilogram printing paste: the moisture differential powder formula of 30.6g21.5% formula (10) dyestuff, 120g commercial acrylic ester adhesive ( _Alcoprint PBA), 5g 30% ammonia spirit.The commercial wetting agent of 3g ( _Lyoprint AP), and 16g is based on the ammonium salt of polyacrylic synthetic thickening agent, then under 120 ℃ with dry 90 seconds of the stamp that generates, then in air-oven, 160 ℃ of following fixation 4 minutes.Obtain the golden yellow stamp of good light fastness, sublimation reliability and drycleaning.
Embodiment 7
Repeat the step of embodiment 6, but moisture differential powder formula without 30.6g 21.5% formula (10) dyestuff, and use formula (11a) dyestuff, formula (12) dyestuff or formula (22a) dyestuff of equal number, obtain the stamp of good light fastness, sublimation reliability and drycleaning equally.
Embodiment 8
Repeat the step of embodiment 6, but do not use cotton fabric, and use polyester textile, obtain the golden yellow stamp of good light fastness, sublimation reliability and drycleaning equally.
Embodiment 9
Repeat the step of embodiment 6, but do not use cotton fabric, and use polyester/cotton flower (67/33) BLENDED FABRIC, obtain the golden yellow stamp of good light fastness, sublimation reliability and drycleaning equally.
Embodiment 10
Cotton fabric is contaminated (pick up about 70%) with the moisture dyestuff that contains following component: the moisture differential powder formula of 43.g/l 21.5% following formula dyestuff The commercial softening agent of 60g/l ( _Avivan MS), 40g/l commercial acrylic ester adhesive ( _Dicrylan AM), the commercial migration inhibitor of 25g/l ( _Irgepadol MP), the commercial wetting agent of 2g/l ( _Cibaflow Pad), and 20g/l polyethylene glycol PEG400,120 ℃ dry 90 seconds down, then in air-oven, 160 ℃ of following fixation 90 seconds.Obtain the golden yellow dyeing of good light fastness, sublimation reliability and drycleaning.
Embodiment 11
Make cotton/polyester (50: 50) BLENDED FABRIC contaminate the moisture differential powder formula of (pick up 70%): 43g/l 21.5% following formula dyestuff with the aqueous dye that contains following component
Figure 98115671002655
The commercial softening agent of 60g/l ( _Avivan MS), 40g/l commercial acrylic ester adhesive ( _Dicrylan AM), the commercial migration inhibitor of 25g/l ( _Irgepadol MP), the commercial wetting agent of 2g/l ( _Cibaflow Pad), 20g/l polyethylene glycol PEG400,5g/l commercial crosslinked agent resin formula ( _Knittex FEL), the 2g/l Magnesium dichloride hexahydrate, 120 ℃ dry 90 seconds down, then in air-oven, 170 ℃ of following fixation 60 seconds.Obtain the golden yellow dyeing of good light fastness, sublimation reliability and drycleaning.

Claims (15)

1. one kind makes fibrous material dyeing or method for printing with pigment dyeing method or pigment printing process, and this method comprises and will contain the dyestuff of at least a following formula
D-(X) n(1) and at least a paint adhesive, also have the dye liquor or the printing paste of other assistants to be applied on the fibrous material if desired, fixation subsequently, in the formula (1), D is the group of insoluble organic dyestuff phthalocyanine, perilla ketone, indigo, thioindigo, dioxazine, diketopyrrolo-pyrrole, iso-dihydro-indole, perylene, quinacridone, metal complex, monoazo, diazonium, nitrine or anthraquinone series, X is a hydrophilic polar group, and n is 1,2 or 3.
2. use pigment printing process according to the process of claim 1 wherein, with containing the dyestuff of at least a formula (1) and at least a paint adhesive, also having the printing paste of other assistants to make fibrous material stamp, fixation then if desired.
3. according to the method for claim 1 or 2, wherein D is the group of insoluble organic dyestuff monoazo, diazonium, nitrine or anthraquinone series.
4. according to the method for claim 1 or 2, wherein X is carboxy and amide groups, sulfo group amide groups or C unsubstituted or that hydroxyl replaces 4-C 12Alkyl, alkyl chain can be by oxygen, carboxy and amide groups and/or sulfo group amide groups interval one or many.
5. according to the method for claim 4, wherein the amide groups in carboxy and amide groups and/or the sulfo group amide groups is by hydroxyl-C 1-C 6Alkyl is mono-substituted or disubstituted.
6. according to the method for claim 1 or 2, the C of X wherein for being replaced by one or more hydroxyls 1-C 6Alkyl.
7. according to one method among the claim 1-6, wherein use formula (1) dyestuff of molecular weight＜550.
8. according to the method for claim 1 or 2, wherein used printing paste also contains thickening agent.
9. according to the method for claim 1 or 2, wherein used printing paste also contains crosslinking agent.
10. according to the method for claim 1 or 2, wherein used printing paste also contains crosslinking catalyst.
11. according to the method for claim 1 or 2, wherein used printing paste also contains one or more coating.
12. the dyestuff of a following formula
Figure 98115671000313
In the formula, R 26Group for following formula In the formula, R 16Be C 1-C 4Alkyl or X group, R 17Be hydrogen, cyano group or carbamoyl, R 18Be hydrogen, C 1-C 4Alkyl or X group, R 25Be C 1-C 6Alkyl and X are hydrophilic polar group, and the phenyl or naphthyl in formula (7a) is unsubstituted or is replaced by halogen, cyano group or nitro.
13. a method for preparing the dyestuff of claim 12 formula (26), this method comprises the compound diazotization that makes following formula,
Figure 98115671000411
Make a product coupling accepted way of doing sth (5a), (6a), (27) or coupling component (8a).
14. the dyestuff of claim 12 makes the application of fibrous material dyeing or stamp with the pigment dyeing method of claim 1 or pigment printing process.
15. one kind with the dye printing of claim 12 or the fibrous material of dyeing.
CN 98115671 1997-07-04 1998-07-03 Pigment dyeing and pigment printing process Pending CN1204711A (en)

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Cited By (7)

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CN102677487A (en) * 2012-05-22 2012-09-19 上海嘉麟杰纺织品股份有限公司 Vintage dyeing method for knitted wool fabric
CN104032605A (en) * 2014-06-17 2014-09-10 东华大学 Dyeing method of polypropylene non-woven fabric material
CN105696382A (en) * 2016-01-29 2016-06-22 安徽省安庆市天峰纺织有限公司 Textile printing process
CN108170001A (en) * 2017-12-29 2018-06-15 深圳市华星光电技术有限公司 Photoetching compositions, colored filter and display panel
CN108279455A (en) * 2018-02-05 2018-07-13 深圳市华星光电技术有限公司 Blue light cut film and blue light display device
CN109736104A (en) * 2019-01-28 2019-05-10 绍兴市天基印刷材料厂 A kind of indigo slurry dyeing of all-cotton fabric
CN112127175A (en) * 2020-09-27 2020-12-25 上海嘉麟杰纺织科技有限公司 Plant dye liquor for wool garment and dyeing method

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102677487A (en) * 2012-05-22 2012-09-19 上海嘉麟杰纺织品股份有限公司 Vintage dyeing method for knitted wool fabric
CN104032605A (en) * 2014-06-17 2014-09-10 东华大学 Dyeing method of polypropylene non-woven fabric material
CN104032605B (en) * 2014-06-17 2016-04-06 东华大学 A kind of colouring method of nonwoven polypropylene fabric material
CN105696382A (en) * 2016-01-29 2016-06-22 安徽省安庆市天峰纺织有限公司 Textile printing process
CN108170001A (en) * 2017-12-29 2018-06-15 深圳市华星光电技术有限公司 Photoetching compositions, colored filter and display panel
CN108279455A (en) * 2018-02-05 2018-07-13 深圳市华星光电技术有限公司 Blue light cut film and blue light display device
CN109736104A (en) * 2019-01-28 2019-05-10 绍兴市天基印刷材料厂 A kind of indigo slurry dyeing of all-cotton fabric
CN109736104B (en) * 2019-01-28 2021-09-10 绍兴市天基印刷材料厂 Indigo pulp dyeing process for all-cotton fabric
CN112127175A (en) * 2020-09-27 2020-12-25 上海嘉麟杰纺织科技有限公司 Plant dye liquor for wool garment and dyeing method

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