CN106590027A - Disperse dye composition, and preparation method and application thereof - Google Patents
Disperse dye composition, and preparation method and application thereof Download PDFInfo
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- CN106590027A CN106590027A CN201611269697.8A CN201611269697A CN106590027A CN 106590027 A CN106590027 A CN 106590027A CN 201611269697 A CN201611269697 A CN 201611269697A CN 106590027 A CN106590027 A CN 106590027A
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- disperse dye
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- 0 *c(cc(cc1*)[N+]([O-])=O)c1N Chemical compound *c(cc(cc1*)[N+]([O-])=O)c1N 0.000 description 2
Classifications
-
- 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo 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
- D06P1/18—Azo 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
- D06P1/19—Nitro 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
- 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
- D06P3/004—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using dispersed 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
- 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
- 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
- D06P3/82—Textiles which contain different kinds of fibres
Abstract
Disclosed are a disperse dye composition, and a preparation method and application thereof. The disperse dye composition comprises a component A composed of one or more of compounds shown as a formula (1) (please see the specifications for the formula), a component B composed of one or more of compounds shown as a formula (2) (please see the specifications for the formula), forbidden aromatic amine compounds, chlorinated phenols, chlorobenzene and chlorotoluene, optional auxiliaries, and other unavoidable impurities. The total content of the forbidden aromatic amine compounds is 10 ppm or below, the respective content of the various chlorinated phenols is 0.5 ppm or below, and the total content of the chlorobenzene and chlorotoluene is 1 ppm or below. The various environment protection indexes of the disperse dye composition meet the requirements of Oeko-Tex Standard 100(2016). In addition, after fabric is dyed through the disperse dye composition, the dyed fabric meets the baby level requirements of Oeko-Tex Standard 100(2016).
Description
Technical field
The present invention relates to a kind of disperse dye composition and its production and use.The disperse dye composition is suitable for
Dyeing or stamp in terylene and its blend fabric.
Background technology
Environment-friendly dye is restricted for the content of harmful material, however, being mostly to carry out ring to weaving face fabric
Control is protected, i.e., the dyestuff on weaving face fabric is measured, control the content of its harmful substance.Thus, however it remains dyeing institute
Harmful substance contents are high in dyestuff chemistry product, cause the sewage of printing and dyeing mill, sludge to have a strong impact on the problem of ecological environment.Together
When because of the difference of textile printing and dyeing process, or the difference of dye dosage causes the content of contained harmful substance in textile dye
Also different, environmentally friendly result is undesirable.So dyeing waste water, sludge and part do not reach the weaving face fabric of environmental requirement to as under
The printing and dyeing mill of trip causes larger loss.To prevent the generation of above-mentioned thing, preferably environmental protection, the health of consumer is ensured
Safety, enables that enterprise is long-term, stable, sustainably develops, and the high-environmental type for developing the chemicals environmental protection level needed for dyeing is produced
Product are the task of top priority in disperse dyes market, are also the only way which must be passed of enterprise's existence and development, even more the certainty of disperse dyes development
Trend.
The content of the invention
The present invention is intended to provide the disperse dye composition of chemicals environmental protection level, its not only every environmental protection index meet
The limitation requirement of Oeko-Tex Standard 100 (2016), and aromatic amine in the dye composite chemical productss of dyeing
The content of compound (AZO), chlorinated phenol (CPs) and chlorobenzene and chlorotoluene (COCs) is low.Fabric meets Oeko-Tex after dye
The requirement of the baby's levels of Standard 100 (2016).In addition, sewage also reaches the environmental requirement of current country after dye, using more just
It is prompt, trust.
For this purpose, the present invention provides a kind of disperse dye composition, it is characterised in that including a kind of in formula (1) compound or
Multiple compounds composition component A, formula (2) compound in one or more compound group into component B, disabling aromatic amine chemical combination
Thing, chlorophenic acid, chlorophenesic acid, trichlorophenol, 2,4,6,-T, tetrachlorophenol, pentachlorophenol, chlorobenzene and chlorotoluene, optional adjuvant and
Other inevitable impurity,
In formula (1),
X1、X2It is each independently H, NO2, halogen or CN；Preferably, the halogen is selected from Cl or Br；
R1For C1～C4Alkyl；
R2、R3It is each independently hydrogen, C1～C4Alkyl, replace C1～C4Alkyl or C2～C4Alkenyl, it is described
Substituted C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1
～C4Alkoxyl, each R is each independently C1～C4Alkyl；
In formula (2),
X3、X4It is each independently-H ,-Br ,-Cl ,-CN ,-NO2；
R4、R5It is each independently hydrogen, C1～C4Alkyl, replace C1～C4Alkyl or C2～C4Alkenyl, it is described
Substituted C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、-OC6H5、-C6H5、-
CH2CH2OCH2CH2CN or C1～C4Alkoxyl, each R is each independently C1～C4Alkyl；Work as R4、R5Respectively-
CH2CH3With-CH2CH2During CN, X3、X4It is asynchronously-Cl；
Wherein, the disabling aromatic amine compound is selected from 4- aminobphenyls (CAS NO.92-67-1), benzidine (92-87-
5), 4- chloro-o-toluidines (95-69-2), 2- naphthylamines (91-59-8), o-aminoazotoluene (97-56-3), 2- amino -4- nitre
Base toluene (99-55-8), parachloroanilinum (106-47-8), 2,4- diamino anisoles (615-05-4), 4,4 '-diaminourea hexichol
Methane (101-77-9), DCB 3,3' dichlorobenzidine (91-94-1), 3,3 '-dimethoxy benzidine (119-90-4), 3,3 '-two
Methyl biphenyl amine (119-93-7), 3,3 '-dimethyl -4,4 '-MDA (838-88-0), 2- methoxyl group -5- first
Base aniline (120-71-8), 4,4 '-diaminourea -3,3 '-dichloro diphenyl methane (101-14-4), 4,4 '-benzidine ether
(101-80-4), 4,4 '-diaminodiphenyl sulfide (139-65-1), ortho-aminotoluene (95-53-4), 2,4 di amino toluene (95-
80-7), 2,4,5- trimethylanilines (137-17-7), o-aminoanisole (90-04-0), P-aminoazobenzene (60-09-3),
One or more in 2,4- dimethylanilines (95-68-1), 2,6- dimethylanilines (87-62-7).
According to EN14362:The method of 2012 (gas chromatograph-mass spectrometer (GC-MS) GC-MS and high performance liquid chromatograph HPLC)
Detected, the total content that aromatic amine compound is disabled described in the dye composite of the present invention is 0-10ppm.That is, the present invention
Dye composite in can not contain the aromatic amine compound, or containing one kind in the aromatic amine compound or many
Kind, but the total content of the aromatic amine compound is less than 10ppm.
The chlorinated phenol is selected from chlorophenic acid (2- chlorophenols, 3- chlorophenols, 4- chlorophenols), chlorophenesic acid (2,6- bis-
Chlorophenol, 2,4 dichloro phenol, 2,5- chlorophenesic acids, 3,5- chlorophenesic acids, 2,3- chlorophenesic acids, 3,4- chlorophenesic acids), trichlorine
Phenol (2,4,6- trichlorophenol, 2,4,6,-Ts, 2,3,6- trichlorophenol, 2,4,6,-Ts, 2,3,5- trichlorophenol, 2,4,6,-Ts, 2,4,5- trichlorophenol, 2,4,6,-Ts, 2,3,4- trichloro-benzenes
Phenol, 3,4,5- trichlorophenol, 2,4,6,-Ts), tetrachlorophenol (2,3,4,6- tetrachlorophenols, 2,3,5,6- tetrachlorophenols, 2,3,4,5- tetrachlorobenzenes
Phenol) and pentachlorophenol in one or more.
With reference to ISO17070:The method of 2015 (gas chromatograph-mass spectrometer (GC-MS) GC-MS) is measured, the dye of the present invention
Each total content is 0- for chlorophenic acid described in feed composition, chlorophenesic acid, trichlorophenol, 2,4,6,-T, tetrachlorophenol, pentachlorophenol
0.5ppm.The chlorinated phenol can not be contained in dye composite i.e. of the invention, or containing in the chlorinated phenol
Plant or various, but the respective total content of the chlorophenic acid, chlorophenesic acid, trichlorophenol, 2,4,6,-T, tetrachlorophenol, pentachlorophenol does not surpass
Cross 0.5ppm.Preferably 0-0.05pm.
The chlorobenzene and chlorotoluene are selected from monochloro-benzene, dichloro-benzenes, trichloro-benzenes, tetrachlorobenzene, pentachlorobenzene, Perchlorobenzene, a chloromethane
One or more in benzene, dichlorotoleune, benzotrichloride, toluene tetrachloride, toluene pentachloride.
It is measured with reference to the method for GB/T24167-2009 (solvent extraction, gas chromatograph-mass spectrometer (GC-MS) GC-MS),
The total content of chlorobenzene and chlorotoluene described in the dye composite of the present invention is 0-1ppm.Can in dye composite i.e. of the invention
With without the chlorobenzene and chlorotoluene, or containing one or more in the chlorobenzene and chlorotoluene, but the chlorobenzene and chlorine
The total content of toluene is less than 1ppm.Preferably 0-0.1ppm.
Preferably, component A is selected from one or more in (1-1)～(1-4) compounds,
Preferably, component B is selected from one or more in formula (2-1)～(2-10) compound,
The disperse dye composition can further include one or more compound group in formula (3) compound into
In component C and optional formula (4) compound one or more compound group into component D,
In formula (3),
X5For halogen or CN, it is preferable that the halogen is selected from Cl or Br；
R6For C1～C4Alkoxyl；
R7For C1～C4Alkyl；
R8、R9It is each independently hydrogen, C1～C4Alkyl or substituted C1～C4Or C2～C4Alkenyl, the replacement
C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1～C4
Alkoxyl, it is C that each R is each independently1～C4Alkyl；
In formula (4),
X6、X7It is each independently-H ,-NO2、-Cl、-OCH3、-OSO2-Ph、-COOC2H4OC2H4OCH3, wherein, Ph generations
Table phenyl；
R10For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl.
Preferably, component C is selected from one or more in formula (3-1)～(3-12) compound,
Preferably, component D is selected from one or more in formula (4-1)～(4-9) compound,
Preferably, in the disperse dye composition, the content of component A is 1-99 weight portions, preferably 20-99 weight
Part, more preferably 40-95 weight portions；The content of component B is 1-99 weight portions, preferably 1-80 weight portions, more preferably 5-60
Weight portion；The content of component C is 0-90 weight portions, preferably 10-87 weight portions；The content of component D is 0-20 weight portions, preferably
For 0.1-10 weight portions.
Preferably, the disperse dye composition include formula (1-1)～(1-2) compound in one or two, formula (2-
1) one or more in compound and optional formula (3-1)～(3-4) compound.
Preferably, the disperse dye composition includes formula (1-1) compound and formula (2-9) compound.
Preferably, the disperse dye composition includes：One or more change in formula (1) compound of 10-40 weight portions
Compound composition component A, in formula (2) compound of 3-50 weight portions one or more compound group into component B and 10-87 weight
Amount part formula (3) compound in one or more compound group into component C；
Preferably, the adjuvant includes auxiliary agent and water.Preferably, the weight of the auxiliary agent and component A, component B, optional
Component C and optional component D gross weight ratio be 0.3～6.5:1.
Preferably, the dispersant is selected from naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), condensation compound of methyl naphthalene sulfonic acid and formaldehyde
(Dispersant MF), benzyl naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent CNF), lignosulfonates (lignin 83A, lignin 85A)
In one or more.Preferably, the dyeing auxiliaries is Matrii Sulfas Exsiccatus.
The disperse dye composition can be with sand mill or grinder grinding after liquid, solid content be 20～
50%, or powdery or graininess are made for after the disperse dye composition is spray-dried, solid content is 87～96%.
The present invention also provides the method for preparing the disperse dye composition, it is characterised in that comprise the following steps：(1)
Compound shown in formula (P) is added to the water into beating, plus it is 10～13 that alkali adjusts pH, is warmed up to 50～80 DEG C, insulation 30～60
Filter after minute, wash, be dried, then carry out diazotising, then coupling reaction is carried out with the compound shown in formula (Q), produced
Thing I；Preferably, the alkali selected from sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide,
One or more in potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine；
Or, by the compound diazotising shown in formula (P), temperature is diluted and controlled with ice and/or water for less than 5 DEG C, plus
The stirring of kieselguhr, bentonite or activated carbon, filtration, then coupling reaction is carried out with the compound shown in formula (Q), product I is obtained；Its
In, in formula (P), X1、X2It is as defined above；In formula (Q), R1、R2、R3, it is as defined above；
(2) by the compound diazotising shown in formula (Z), on the rocks and/or water dilutes and cools to less than 5 DEG C, plus kieselguhr,
Bentonite or activated carbon stirring, filtration, then product II is obtained by coupling reaction with the compound shown in formula (H)；Wherein, formula
(Z) in, X3、X4As defined in claim 1-6；In formula (H), R4、R5As defined in claim 1-6；
One or more in products therefrom I is mixed with one or more in the product II and optional adjuvant,
Gained mixture is used as disperse dye composition；
Alternatively, it is further comprising the steps of：Compound shown in formula (X) is added to the water into beating, plus it is 10 that alkali adjusts pH
～13, be warmed up to 50～80 DEG C, insulation is filtered after 30～60 minutes, washing, be dried, and then carries out diazotising, then with formula (Y) institute
The compound for showing carries out coupling reaction, obtains product III；Preferably, the alkali is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, carbon
In potassium hydrogen phthalate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine
One or more；Wherein, in formula (X), X5It is as defined above；In formula (Y), R6、R7、R8、R9It is as defined above；
By one or more in products therefrom III with one or more in the product I and selected from product II
In one or more and optional adjuvant mixed, gained mixture is used as disperse dye composition；
Alternatively, it is further comprising the steps of：Compound shown in formula (M) is added to the water into beating, plus it is 10 that alkali adjusts pH
～13, be warmed up to 50～80 DEG C, insulation is filtered after 30～60 minutes, washing, be dried, and then carries out diazotising, then with formula (N) institute
The compound for showing carries out coupling reaction, obtains product IV；Wherein, in formula (M), X6、X7It is each independently-OSO2-Ph、-
COOC2H4OC2H4OCH3, in formula (N), R10For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl；Preferably, the alkali choosing
From sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, hydrogen
One or more in aluminium oxide, methylamine, ethamine and triethylamine；
Or, by the compound shown in formula (M) add water crushing, distillation, when fraction reaches more than the 20% of amount of water, stop
Only distill, cool to less than 40 DEG C, add hydrochloric acid beating, then diazotising obtains diazol, then with the compound shown in formula (N)
Coupling reaction is carried out, product IV is obtained；Wherein, in formula (M), X6、X7It is each independently-H ,-NO2、-Cl、-OCH3, formula (N)
In, R10For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl,
By one or more in products therefrom IV with one or more in product I and selected from the one of product II
Kind or various and optional one or more selected from product III, optional adjuvant mixed, gained mixture conduct
Disperse dye composition.
In above-mentioned preparation method, can by one or more in the product I and the one kind in product II or
One or more in product III various, optional and optional one or more depositing in adjuvant selected from product IV
Particlized process is carried out under, liquid is made or is dried, disperse dye composition is obtained；
Or by one or more in product I and one or more in product II and optional selected from product
One or more, optional one or more selected from product IV of thing III carries out respectively particlized process in the presence of adjuvant,
Mixed again, make liquid or be dried, disperse dye composition is obtained.
Preferably, the particlized is processed and carried out using sand mill or grinder.
Preferably, it is described dry using spray drying.
It is highly preferred that the preparation method of the disperse dye composition is comprised the following steps：
A) compound shown in formula (P) is added to the water into beating, plus it is 10～13 that alkali adjusts pH, is warmed up to 50～80 DEG C,
Filter after insulation 30-60 minutes, wash, be dried；Preferably, the alkali is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, bicarbonate
In potassium, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine one
Plant or various；
B) sulphuric acid is added in diazonium kettle, the stirring of diazonium kettle is opened, then is slowly added into nitrosyl sulfuric acid, control temperature does not surpass
40 DEG C are crossed, are finished, cool to 20～30 DEG C, the compound being slowly uniformly added into shown in the formula (P) that (a) step process is crossed is finished,
20～30 DEG C of insulation reaction 4-8 hours, obtain diazo component, stand-by；
C) water, sulphuric acid, emulsifying agent are added in coupling kettle, it is preferable that the emulsifying agent is selected from fatty alcohol-polyoxyethylene ether
In one or more, add the coupling component shown in formula (Q), stir 30-60 minutes, on the rocks, defoamer, it is preferable that described
One or more in isooctanol or organic silicon compound thing of defoamer, control temperature below 10 DEG C, the stand-by weight of Deca
Nitrogen component, time for adding 3～6 hours, finishes, and controls 10～15 DEG C of temperature insulation reaction 2～4 hours, slowly it is warmed up to 50～
80 DEG C turn crystalline substance, filter, wash, and product I is obtained；
Or,
A) sulphuric acid is added in diazonium kettle, the stirring of diazonium kettle is opened, then is slowly added into nitrosyl sulfuric acid, control temperature does not surpass
40 DEG C are crossed, is finished, cool to 20～30 DEG C, the intermediate being slowly uniformly added into shown in formula (P) is finished anti-in 20～30 DEG C of insulations
Answer 4～8 hours, obtain diazo component, it is stand-by；
B) water, ice, sulphuric acid are added in diazonium dilution kettle, cools to less than 5 DEG C, the press-in diazo component carries out dilute
Release, control dilution temperature is less than 5 DEG C, and pressure finishes, and adds kieselguhr, bentonite or activated carbon, stirs 30～60 minutes, filters,
Diazonium filtrate is squeezed into into coupling kettle；
C) diazonium filtrate is squeezed into and is finished, and opens coupling kettle stirring, adds ice, carbamide or sulfamic acid, emulsifying agent, preferably
Ground, the emulsifying agent is selected from one or more in fatty alcohol-polyoxyethylene ether, stirs 15～60 minutes, adds defoamer, excellent
Selection of land, one or more in isooctanol or organic silicon compound thing of the defoamer, control temperature below 10 DEG C, Deca
Coupling component shown in formula (Q), time for adding 2～5 hours, finishes, and controls 10～15 DEG C of temperature insulation reaction 2～5 hours, delays
Slowly 50～80 DEG C are warmed up to and turn crystalline substance, filtered, wash, product I is obtained；
And, comprise the following steps：
A) sulphuric acid is added in diazonium kettle, the stirring of diazonium kettle is opened, then is slowly added into nitrosyl sulfuric acid, control temperature does not surpass
40 DEG C are crossed, is finished, cool to 20～30 DEG C, the intermediate being slowly uniformly added into shown in formula (Z) is finished anti-in 20～30 DEG C of insulations
Answer 4～8 hours, obtain diazo component, it is stand-by；
B) water, ice, sulphuric acid are added in diazonium dilution kettle, cools to less than 5 DEG C, the press-in diazo component carries out dilute
Release, control dilution temperature is less than 5 DEG C, and pressure finishes, and adds kieselguhr, bentonite or activated carbon, stirs 30～60 minutes, filters,
Diazonium filtrate is squeezed into into coupling kettle；
C) diazonium filtrate is squeezed into and is finished, and opens coupling kettle stirring, adds ice, carbamide or sulfamic acid, emulsifying agent, preferably
Ground, the emulsifying agent is selected from one or more in fatty alcohol-polyoxyethylene ether, stirs 15～60 minutes, adds defoamer, excellent
Selection of land, one or more in isooctanol or organic silicon compound thing of the defoamer, control temperature below 10 DEG C, Deca
Coupling component shown in formula (H), time for adding 2～5 hours, finishes, and controls 10～15 DEG C of temperature insulation reaction 2～5 hours, delays
Slowly 50～80 DEG C are warmed up to and turn crystalline substance, filtered, wash, product II is obtained；
One or more in products therefrom II is mixed with one or more in the product I and optional adjuvant,
Gained mixture is used as disperse dye composition.
Optionally, it is further comprising the steps of：
A) compound shown in formula (X) is added to the water into beating, plus it is 10～13 that alkali adjusts pH, is warmed up to 50～80 DEG C,
Filter after insulation 30-60 minutes, wash, be dried；Preferably, the alkali is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, bicarbonate
In potassium, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine one
Plant or various；
B) sulphuric acid is added in diazonium kettle, the stirring of diazonium kettle is opened, then is slowly added into nitrosyl sulfuric acid, control temperature does not surpass
40 DEG C are crossed, are finished, cool to 20～30 DEG C, the compound being slowly uniformly added into shown in the formula (X) that a) step process is crossed is finished,
25～30 DEG C of insulation reaction 4～8 hours, obtain diazo component, stand-by；
C) water, sulphuric acid, emulsifying agent are added in coupling kettle, it is preferable that the emulsifying agent is selected from fatty alcohol-polyoxyethylene ether
In one or more, add the coupling component shown in formula (Y), stir 30～60 minutes, on the rocks, defoamer, it is preferable that described
One or more in isooctanol or organic silicon compound thing of defoamer, control temperature below 10 DEG C, the stand-by weight of Deca
Nitrogen component, time for adding 3～6 hours, finishes, and controls 10～15 DEG C of temperature insulation reaction 2～4 hours, slowly it is warmed up to 50～
80 DEG C turn crystalline substance, filter, wash, and product III is obtained；
By one or more in one or more in products therefrom III and the product I and in product II
One or more and optional adjuvant are mixed, and gained mixture is used as disperse dye composition；
Optionally, it is further comprising the steps of：
A) compound shown in formula (M) is added to the water into beating, plus it is 10～13 that alkali adjusts pH；50～80 DEG C are warmed up to,
Insulation is filtered after 30～60 minutes, washes, is dried；
B) compound by water, shown in the formula (M) that a) step process is crossed is put into diazonium kettle, adds hydrochloric acid beating 1～3 little
When, add water adjustment volume, on the rocks to cool to less than 5 DEG C, is slowly added into the sodium nitrite solution that mass concentration is 20～30%, plus
Finish, at 8 DEG C 1～3 hour is incubated, obtain diazo component, it is stand-by；
C) addition water, the buffer agent (such as sodium acetate, disodium hydrogen phosphate) of pH value 9 or so in kettle is coupled, stirring 15～
60 minutes, the coupling component shown in throw-in type (N) was beaten 30～60 minutes, on the rocks to cool to less than 15 DEG C, the stand-by weight of Deca
Nitrogen component, time for adding 1～3 hour, drop finish 15～20 DEG C be incubated 1～3 hour, be warmed up to 50～80 DEG C turn crystalline substance, filter, wash
Wash, product IV is obtained；
Or,
A) water is added in kettle, the compound shown in formula (M) is ground by colloid mill, in adding refining kettle, risen
Temperature distillation, when fraction for amount of water 20%, stops distillation, cools to less than 40 DEG C, adds hydrochloric acid, is beaten 1～3 hour；
B) compound shown in the formula (M) crossed a) step process adds diazonium kettle, adds water, on the rocks to cool to less than 5 DEG C,
The sodium nitrite solution that mass concentration is 20～30% is slowly added into, is finished, insulation reaction 1～3 hour, obtains below 8 DEG C
Diazo component, it is stand-by；
C) water, sodium acetate are added in coupling kettle, is stirred 15～60 minutes, the coupling component shown in throw-in type (N), beating
30～60 minutes, on the rocks to cool to less than 15 DEG C, the stand-by diazo component of Deca, time for adding was 1～3 hour, and drop finishes 15
～20 DEG C are incubated 1～3 hour, are warmed up to 50～80 DEG C and turn crystalline substance, filter, wash, and product IV is obtained；
By one or more in obtained product IV with one or more in above-mentioned product I and selected from above-mentioned
One or more and optional one or more in product III in product II, optional adjuvant mixed,
Gained mixture is used as disperse dye composition.
The present invention also provides the disperse dye composition for the dyeing of fabric or the purposes of stamp；Preferably, it is described
Fabric is terylene or polyester blended fabric.
The present invention also provides a kind of fabric, it is characterised in that dyeed using the disperse dye composition or stamp
Prepare；Preferably, the fabric is terylene or polyester blended fabric.
Invention effect
The disperse dye composition of the present invention is the disperse dye composition of chemicals environmental protection level, its not only every environmental protection refer to
Reference symbol closes the limitation requirement of Oeko-Tex Standard 100 (2016), and the content for particularly disabling aromatic amine compound does not surpass
Cross 10ppm, chlorophenic acid, chlorophenesic acid, trichlorophenol, 2,4,6,-T, tetrachlorophenol, the respective total content of pentachlorophenol to be less than
The total content of 0.5ppm, chlorobenzene and chlorotoluene (COCs) is less than 1ppm.Sewage also meet the requirement of environmental protection after dye, using more just
It is prompt, trust.
On the other hand, in the case of disperse dye composition meet the requirement of environmental protection of the invention, no matter downstream printing and dyeing enterprise pair
How dyeing and printing process is changed, or the maximum of dye dosage uses, can the omnibearing environmental protection for ensureing textile.Using this
After the disperse dye composition of invention is dyeed to fabric, fabric meets Oeko-Tex Standard 100 (2016) after dye
The requirement of baby's level, the total content for particularly disabling aromatic amine compound can reach below 5ppm, chlorophenic acid, chlorophenesic acid,
The respective total content of trichlorophenol, 2,4,6,-T, tetrachlorophenol, pentachlorophenol is the total content of below 0.05ppm, chlorobenzene and chlorotoluene
Below 0.1ppm.Simultaneously dyeing and printing sewage, sludge meet the requirement of environmental protection, save environmental protection treatment cost, are enterprise development and protection life
Solid foundation is established in state environment and sustainable development.
Specific embodiment
Make further exemplary illustration to the present invention with reference to embodiments, but protection scope of the present invention is not limited to
This.
Preparation example 1
A) by intermediate 2,4- dinitro -6- chloroanilines are added to the water beating, plus 30% sodium hydroxide solution, adjust pH and are
11,60 DEG C are warmed up to, insulation is filtered after 30 minutes, washes, is dried；
B) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 20 DEG C are cooled to, 2, the 4- dinitro -6- chloroanilines after a) step process are slowly uniformly added into, finish 25～30
DEG C insulation diazo-reaction 6 hours, obtains diazo component, stand-by；
C) addition water, sulphuric acid, peregal in coupling kettle, addition coupling component N, N- diethyl m-acetamidoanilines,
Stirring 30 minutes, on the rocks, isooctanol, control temperature below 10 DEG C, the stand-by diazo component of Deca, time for adding about 5 hours,
Finish, control 10～15 DEG C of temperature insulation reaction 2 hours, be slowly warmed up to 60 DEG C and turn crystalline substance, filter, wash, product (I- is obtained
1).Products therefrom (I-1) is containing formula (1-1) structure as component A.
Preparation example 2
According to the identical method of preparation example 1, except that, by the intermediate 2 in preparation example 1,4- dinitro -6- chlorobenzenes
Amine adopts 2,4- dinitro -6- bromanilines to be substituted, and prepares product (I-2).Products therefrom (I-2) contains as component
Formula (1-2) structure of A.
Preparation example 3
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 10 DEG C are cooled to, slowly it is uniformly added into intermediate paranitroanilinum within about 3 hours, finish, 2.5 hours are incubated, obtain
Diazo component, it is stand-by；
B) add water, ice to cool to less than 5 DEG C in diazonium dilution kettle, be pressed into the diazo liquid and be diluted, control dilute
It is that, less than 5 DEG C, pressure finishes to release temperature, adds activated carbon, is stirred 30 minutes, is filtered, and diazonium filtrate is squeezed into into coupling kettle；
C) diazonium filtrate is squeezed into and is finished, and opens coupling kettle stirring, adds carbamide, peregal, adds coupling component N, N- bis-
Acetoxyethyl m-acetamidoaniline, adjusts coupling and expects acidity for 10% (acidity of sulfuric acid), 15～25 DEG C of controlling reaction temperature,
Insulation reaction 4 hours, is slowly warmed up to 30～35 DEG C, is incubated 3 hours, then is warmed up to 40～45 DEG C, is incubated 2 hours, filters, water
Wash, product (I-3) is obtained.Products therefrom (I-3) is containing formula (1-3) structure as component A.
Preparation example 4
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 22 DEG C are cooled to, intermediate 2 cyano 4 nitro aniline is slowly uniformly added into, finish in 25～30 DEG C of insulation reaction
It is 6 hours, stand-by.
B) water, ice are added in diazonium dilution kettle, cool to less than 5 DEG C, the stand-by diazo liquid being pressed into above is diluted,
Control dilution temperature is less than 5 DEG C, and pressure finishes, and adds kieselguhr, stirs 30 minutes, filters.Filtrate squeezes into coupling kettle.
C) it is coupled：Diazonium is squeezed into and finished, and opens coupling kettle stirring, adds ice, carbamide, peregal, is stirred 15 minutes, is added
Isooctanol, control temperature below 10 DEG C, Deca coupling component N, N- oxalic acid carbomethoxy m-acetamidoaniline, time for adding
About 3 hours, finish, control 10～15 DEG C of temperature insulation reaction 2 hours, be slowly warmed up to 70 DEG C and turn crystalline substance, filter, wash, be obtained
Product (I-4).Products therefrom (I-4) is containing formula (1-4) structure as component A.
Preparation example 5-15
The method that preparation example 5,7,8,11,12,14 adopts preparation example 3, except that, by the coupling component of preparation example 3
N, N- diacetyl oxy ethyl m-acetamidoaniline is substituted using the coupling component shown in table 1.
And preparation example 6,9,10,13 is using the method for preparation example 4, except that, intermediate 2- cyano group -4- Nitrobenzol
Amine, coupling component N, N- oxalic acid carbomethoxy m-acetamidoanilines are carried out using the intermediate and coupling component of depicted in table 1
Substitute.
Table 1
Successively products therefrom (II-1) is respectively formula (2-1) extremely to preparation example 5-14 to component B contained in product (II-10)
Formula (2-10) compound.
Preparation example 15-18 and 20-26
According to the identical method of preparation example 1, except that, by the intermediate 2 in preparation example 1,4- dinitro -6- chlorobenzenes
Amine, coupling component N, the intermediate and coupling component that N- diethyl m-acetamidoanilines are respectively adopted in table 2 is substituted, system
It is standby to obtain product (III-1)～(III-4) and (III-6)～(III-12).
Table 2
Preparation example 20
According to the identical method of preparation example 1, except that, by the intermediate 2 in preparation example 1,4- dinitro -6- chlorobenzenes
Amine, coupling component N, N- diethyl m-acetamidoanilines are respectively adopted intermediate 2,4 dinitro 6 bromo aniline and coupling group
Divide N, N- oxalic acid carbomethoxy -2- methoxyl group -5- acetylaminoanilines to be substituted, formula (3-5) raw material filter cake is obtained；Then enter
Row cyaniding：DMF is added in cyaniding kettle, 80 DEG C are warmed up to, cyaniding Asia ketone, Cyanogran. is added, 100 DEG C is warmed up to and is incubated 1 hour,
80 DEG C are cooled to, formula (3-5) the raw material filter cake is put into, 100～110 DEG C are warmed up to, 3 hours are incubated, reaction end are surveyed in sampling,
25 DEG C are cooled to after qualified, filtered, washed, obtain cyaniding filter cake；Then except ketone, except cyanogen：Water, hydrochloric acid, ferric chloride are beaten into it
Ferric chloride is entirely molten, adds cyaniding filter cake, is beaten 10 hours, filters, washes, and product (III-5) is obtained.
Preparation example 15-26 obtains successively product (III-1) to product (III-12), and component C contained therein is respectively formula
(3-1) to formula (3-12) compound.
Preparation example 27
A) intermediate isophthalic sulfonate group aniline is added to the water into beating, plus 30% sodium hydroxide solution, it is 12 to adjust pH,
55 DEG C are warmed up to, insulation is filtered after 30 minutes, washes, is dried；
B) the isophthalic sulfonate group aniline by water, a) after step process is put into diazonium kettle, adds hydrochloric acid to be beaten 2 hours, plus
Water adjusts volume, on the rocks to cool to 5 DEG C, is slowly added into the sodium nitrite solution that mass concentration is 30%, finishes, in 4～8 DEG C of guarantors
Temperature 2 hours, obtains diazo component, stand-by；
C) water, sodium acetate are added in coupling kettle, is stirred 15 minutes, put into coupling component 3- cyano group -4- methyl -6- hydroxyls
Base-N- methylpyridones, are beaten 60 minutes, and on the rocks to cool to 5 DEG C, the stand-by diazo component of Deca, time for adding about 1.5 is little
When, drop finish 15～20 DEG C be incubated 2 hours, be warmed up to 50 DEG C turn crystalline substance, filter, washing, be obtained product (IV-1).
Preparation example 28
According to the identical method of preparation example 27, except that, by the coupling component 3- cyano group -4- first in preparation example 27
Base -6- hydroxy-N-methvls pyridone is substituted using 3- cyano group -4- methyl -6- hydroxy-ns-ethylpyridine ketone, is prepared
Product (IV-2).
Preparation example 29
A) water is added in kettle, ortho-nitraniline is ground by colloid mill, in adding kettle, heat up distillation, when evaporating
When dividing 20% more than amount of water, stop distillation, cool to less than 40 DEG C, add hydrochloric acid, beating 1 hour；
B) by after a) step process ortho-nitraniline add diazonium kettle, add water adjustment volume, it is on the rocks cool to 5 DEG C with
Under, the sodium nitrite solution that mass concentration is 20% is slowly added into, finish, 2 hours are incubated below 5～8 DEG C, obtain diazonium group
Point, it is stand-by；
C) water, sodium acetate are added in coupling kettle, is stirred 15 minutes, put into coupling component 3- cyano group -4- methyl -6- hydroxyls
Base-N- methylpyridones, are beaten 30 minutes, on the rocks to cool to 7 DEG C, the stand-by diazo component of Deca, time for adding about 2 hours,
Drip to finish and be incubated 2 hours at 15～20 DEG C, be warmed up to 50 DEG C and turn crystalline substance, filter, wash, product (IV-3) is obtained.
Preparation example 30-34
According to the identical method of preparation example 29, except that, by the intermediate ortho-nitraniline in preparation example 29, coupling
The intermediate and coupling component that component 3- cyano group -4- methyl -6- hydroxy-N-methvl pyridones are respectively adopted in table 3 is substituted,
Prepare product (IV-4)～(IV-8).
Table 3
Preparation example 35
According to the identical method of preparation example 27, except that, by the intermediate isophthalic sulfonate group benzene in preparation example 27
Amine, coupling component 3- cyano group -4- methyl -6- hydroxy-N-methvl pyridones be respectively adopted to diethylene glycol dimethyl ether formic acid esters aniline,
3- cyano group -4- methyl -6- hydroxy-ns-ethylpyridine ketone is substituted, and prepares product (IV-9).
Preparation example 27-35 products therefrom (IV-1) to component D contained in product (IV-9) is respectively formula (4-1) to formula
(4-9) compound.
Contrast preparation example 1
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 20 DEG C are cooled to, chloro- 2, the 4- dinitroanilines of diazo component 6- are slowly uniformly added into, finish in 25～30 DEG C of insulations
Diazo-reaction 6 hours, obtains diazo component, stand-by；
B) addition water, sulphuric acid, peregal in coupling kettle, addition coupling component N, N- diethyl m-acetamidoanilines,
Stirring 30 minutes, on the rocks, isooctanol, control temperature below 10 DEG C, the stand-by diazo component of Deca, time for adding about 5 hours,
Finish, control 10～15 DEG C of temperature insulation reaction 2 hours, be slowly warmed up to 60 DEG C turn crystalline substance, filter, washing, be obtained product (I '-
1)。
Contrast preparation example 2
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 22 DEG C are cooled to, intermediate 2 cyano 4 nitro aniline is slowly uniformly added into, finish in 25～30 DEG C of insulation reaction
It is 6 hours, stand-by.
B) water, ice are added in diazonium dilution kettle, cool to less than 5 DEG C, the stand-by diazo liquid being pressed into above is diluted,
Control dilution temperature is less than 5 DEG C, and pressure finishes, and stirs 30 minutes, filters.Filtrate squeezes into coupling kettle.
C) filtrate is squeezed into and is finished, and opens coupling kettle stirring, adds ice, carbamide, peregal, is stirred 15 minutes, is added different pungent
Alcohol, below 10 DEG C, Deca coupling component N, N- diacetyl oxy ethyl aniline, time for adding about 3 hours is finished control temperature,
Control 10～15 DEG C of temperature insulation reaction 2 hours, is slowly warmed up to 70 DEG C and turns crystalline substance, filters, washes, and product II ' -9 is obtained).
Contrast preparation example 3
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 10 DEG C are cooled to, slowly it is uniformly added into intermediate paranitroanilinum within about 3 hours, finish, 2.5 hours are incubated, obtain
Diazo component, it is stand-by；
B) add water, ice to cool to less than 5 DEG C in diazonium dilution kettle, be pressed into the diazo liquid and be diluted, control dilute
It is that, less than 5 DEG C, pressure finishes to release temperature, is stirred 30 minutes, is filtered, and diazonium filtrate is squeezed into into coupling kettle；
C) diazonium filtrate is squeezed into and is finished, and opens coupling kettle stirring, adds carbamide, peregal, adds coupling component N- cyanogen second
Base-Phenhenzamine, adjusts coupling and expects acidity for 10% (acidity of sulfuric acid), 15～25 DEG C of controlling reaction temperature, and insulation reaction 4 is little
When, slowly it is warmed up to 30～35 DEG C, 3 hours are incubated, then be warmed up to 40～45 DEG C, 2 hours are incubated, filter, washing, product is obtained
(II’-1)。
Contrast preparation example 4
A) sulphuric acid is added in diazonium kettle, stirring is opened, then is slowly added into nitrosyl sulfuric acid, control temperature is less than 40
DEG C, finish, 20 DEG C are cooled to, diazo component 2 is slowly uniformly added into, 4- dinitro -6- chloroanilines are finished in 25～30 DEG C of insulations
Diazo-reaction 6 hours, obtains diazo component, stand-by；
B) water, sulphuric acid, peregal are added in coupling kettle, adds coupling component N, N- diallyl -2- methoxyl group -5- second
Acylamino- aniline, stir 30 minutes, on the rocks, isooctanol, control temperature below 10 DEG C, the stand-by diazo component of Deca, Deca
About 5 hours time, finish, control 10～15 DEG C of temperature insulation reaction 2 hours, be slowly warmed up to 60 DEG C and turn crystalline substance, filter, wash,
Prepared product (III ' -1).
Embodiment 1：
Product (II-9), 50 grams of dispersants that the product (I-1) and 10 grams of preparation examples 13 that 90 grams of preparation examples 1 are obtained is obtained
MF, 80 grams of lignin 85A, add water 345 grams after stirring, and are ground with sand mill, are then spray-dried, i.e.,
Obtain disperse dye composition.
Comparative example 1：
According to the identical method of embodiment 1, except that, by the product (I-1) and (II-9) in embodiment 1 using right
Substituted than obtained product (I ' -1) in preparation example 1 and contrast preparation example 2 and (II ' -9).
The dyestuff finished product of embodiment 1 and comparative example 1 is carried out into following test, concrete method of testing is as follows：
EN14362 is respectively referred to the dye product of embodiment 1 and comparative example 1:2012 (gas chromatograph-mass spectrometer (GC-MS)s
GC-MS and high performance liquid chromatograph HPLC), with reference to ISO17070:2015 (gas chromatograph-mass spectrometer (GC-MS) GC-MS), reference
The method of GB/T24167-2009 (solvent extraction, gas chromatograph-mass spectrometer (GC-MS) GC-MS), carries out dividing for AZO, CPs, COCs
Analysis test, test result is shown in Table 4：
Table 4
Note：(1) detection limit in dye composite product：
AZO：ND=is not detected, detection limit=10ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs, similarly hereinafter；
CPs：ND=is not detected, detection limit=0.05ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs, under
Together；
COCs：ND=is not detected, detection limit=0.1ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs, under
Together.
(2) data of CPs are the detection data of the class of content highest one in five class chlorinated phenols, similarly hereinafter.
As can be seen from Table 4, every environmental protection index of the disperse dye composition product that embodiment 1 is obtained is better than contrast
The disperse dye composition product that example 1 is obtained.
Embodiment 2：
By 20 grams of products (I-1), 44 grams of products (II-1), 36 grams of product (III-1) dye components and 30 grams of Dispersant MFs,
30 grams of lignin 85A, add water 450 grams and stir, and are ground with sand mill, are then spray-dried, and obtain final product black
Color fine work disperse dye composition.
Comparative example 2
Using the method for embodiment 2, except that, the product (I-1), product (II-1), product (III-1) are respectively
The product (I ' -1) that obtained using contrast preparation example 1,3,4, product (II ' -1), product (III ' -1) are replaced.
To the dyestuff of embodiment 2 and comparative example 2 according to the method for embodiment 1, the analysis test of AZO, CPs, COCs is carried out,
Test result is shown in Table 5：
Table 5
As can be seen from Table 5, every environmental protection index of the disperse dye composition product that embodiment 2 is obtained is better than contrast
The disperse dye composition product that example 2 is obtained.
Embodiment 3-18
According to the identical method of embodiment 1, according to the compositing formula in table 6, the disperse dye composition such as institute of table 6 is made
Show.
Table 6：Unit of weight：g
The disperse dye composition product of embodiment 3-18 is carried out into following test, concrete test is as follows：
To the disperse dye composition product of embodiment 3-18 respectively according to EN14362:2012 (gas chromatography-mass spectrometries
With instrument GC-MS and high performance liquid chromatograph HPLC), with reference to ISO17070:2015 (gas chromatograph-mass spectrometer (GC-MS) GC-MS), ginseng
According to the method for GB/T24167-2009 (solvent extraction, gas chromatograph-mass spectrometer (GC-MS) GC-MS), its AZO, CPs, COCs is tested
Content, test result is shown in Table 7：
Table 7
The disperse dye composition product as obtained in the method for preparation example of the present invention and embodiment, although batch is different, ring
Protect index and slightly have difference, but all below required limitation, and environmental protection index is unrelated with institute's adding assistant and Ginding process.
By the dyestuff finished product of the embodiment 4,5,6,7,8,9,11,14 in table 7, according to the method for GB/T2394-2006, point
In the water of the disperse dye composition product to 500ml that another name takes 1 gram of embodiment 4,5,6,7,8,9,11,14, dispersion dye is made
Pulp suspension.100ml disperse dyes suspensions are drawn, with acetic acid dye bath pH to 5 is adjusted, be then warmed up to 60 DEG C, while respectively
Being put into 2g polyster fibres carries out high-temperature pressure dyeing, and 130 DEG C were warmed up in 35 minutes, is incubated 45 minutes, is cooled to 80 DEG C and takes
Sample.
Respectively according to EN14362:2012 (gas chromatograph-mass spectrometer (GC-MS) GC-MS and high performance liquid chromatograph HPLC), ginseng
According to ISO17070:2015 (gas chromatograph-mass spectrometer (GC-MS) GC-MS), reference GB/T24167-2009 (solvent extraction, gas phase color
Spectrum-GC-MS GC-MS) method, the content of Textile AZO after dye, CPs, COCs is tested, test result is shown in Table
8。
Table 8
| Title | AZO | CPs | COCs |
| Embodiment 4 | ND | ND | ND |
| Embodiment 5 | ND | ND | ND |
| Embodiment 6 | ND | ND | ND |
| Embodiment 7 | ND | ND | ND |
| Embodiment 8 | ND | ND | ND |
| Embodiment 9 | ND | ND | ND |
| Embodiment 11 | ND | ND | ND |
| Embodiment 14 | ND | ND | ND |
Remarks：Detection limit in textile：
AZO:ND=is not detected, detection limit=5ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs,
CPs ND=are not detected, detection limit=0.05ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs,
COCs ND=are not detected, detection limit=0.1ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs,
From table 6,7,8 as can be seen that embodiment 3-18 items environmental protection index it is excellent, and embodiment 4,5,6,7,8,9,
11st, 14 dyestuffs are used for after textile dyeing, do not detect AZO, CPs, COCs after dye in fabric.
The preferred embodiment of the present invention described in detail above, but, the present invention is not limited in above-mentioned embodiment
Detail, the present invention range of the technology design in, various simple variants can be carried out to technical scheme, this
Plant simple variant and belong to protection scope of the present invention.
Claims (10)
1. a kind of disperse dye composition, it is characterised in that including one or more compound group in formula (1) compound into group
In point A, formula (2) compound one or more compound group into component B, disabling aromatic amine compound, chlorophenic acid, dichloro-benzenes
Phenol, trichlorophenol, 2,4,6,-T, tetrachlorophenol, pentachlorophenol, chlorobenzene and chlorotoluene, optional adjuvant and other inevitable impurity,
In formula (1),
X1、X2It is each independently H, NO2, halogen or CN；Preferably, the halogen selects Cl or Br；
R1For C1～C4Alkyl；
R2、R3It is each independently hydrogen, C1～C4Alkyl, replace C1～C4Alkyl or C2～C4Alkenyl, the replacement
C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1～C4
Alkoxyl, each R is each independently C1～C4Alkyl；
In formula (2),
X3、X4It is each independently-H ,-Br ,-Cl ,-CN ,-NO2；
R4、R5It is each independently hydrogen, C1～C4Alkyl, replace C1～C4Alkyl or C2～C4Alkenyl, the replacement
C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、-OC6H5、-C6H5、-
CH2CH2OCH2CH2CN or C1～C4Alkoxyl, each R is each independently C1～C4Alkyl；Work as R4、R5Respectively-
CH2CH3With-CH2CH2During CN, X3、X4It is asynchronously-Cl；
Wherein, the disabling aromatic amine compound is selected from 4- aminobphenyls, benzidine, 4- chloro-o-toluidines, 2- naphthylamines, adjacent ammonia
Base azotoluene, 2- amino -4- Methylnitrobenzenes, parachloroanilinum, 2,4- diamino anisoles, 4,4 '-MDA, 3,
3 '-dichloro-benzidine, 3,3 '-dimethoxy benzidine, 3,3 '-dimethylbenzidine, 3,3 '-dimethyl -4,4 '-diaminourea two
Phenylmethane, 2- methoxyl group -5- monomethylaniline .s, 4,4 '-diaminourea -3,3 '-dichloro diphenyl methane, 4,4 '-benzidine ether, 4,
4 '-diaminodiphenyl sulfide, ortho-aminotoluene, 2,4 di amino toluene, 2,4,5- trimethylanilines, o-aminoanisole, to ammonia
One or more in base diphenyl diimide, 2,4- dimethylanilines, 2,6- dimethylanilines；
The chlorophenic acid be selected from 2- chlorophenols, 3- chlorophenols, one or more of 4- chlorophenols；The chlorophenesic acid is choosing
From 2,6- chlorophenesic acids, 2,4 dichloro phenol, 2,5- chlorophenesic acids, 3,5- chlorophenesic acids, 2,3- chlorophenesic acids, 3,4- dichloro-benzenes
One or more in phenol；The trichlorophenol, 2,4,6,-T is selected from 2,4,6- trichlorophenol, 2,4,6,-Ts, 2,3,6- trichlorophenol, 2,4,6,-Ts, 2,3,5- trichloro-benzenes
One or more in phenol, 2,4,5- trichlorophenol, 2,4,6,-Ts, 2,3,4- trichlorophenol, 2,4,6,-Ts, 3,4,5- trichlorophenol, 2,4,6,-Ts；The tetrachlorophenol is
One or more in 2,3,4,6- tetrachlorophenols, 2,3,5,6- tetrachlorophenols, 2,3,4,5- tetrachlorophenols；
The chlorobenzene and chlorotoluene be selected from monochloro-benzene, dichloro-benzenes, trichloro-benzenes, tetrachlorobenzene, pentachlorobenzene, Perchlorobenzene, monochlorotoluene,
Dichlorotoleune, benzotrichloride, toluene tetrachloride, one or more of toluene pentachloride；
Also, it is described disabling aromatic amine compound total content be 0-10ppm, the chlorophenic acid, chlorophenesic acid, trichloro-benzenes
Phenol, tetrachlorophenol, the pentachlorophenol total content that each total content is 0-0.5ppm, chlorobenzene and chlorotoluene is 0-1ppm；
Preferably, component A is selected from one or more in (1-1)～(1-4) compounds,
Preferably, component B is selected from one or more in formula (2-1)～(2-10) compound,
2. disperse dye composition according to claim 1, it is characterised in that also including a kind of in formula (3) compound or
Multiple compounds composition component C and optional formula (4) compound in one or more compound group into component D,
In formula (3),
X5For halogen or CN, it is preferable that the halogen is selected from Cl or Br；
R6For C1～C4Alkoxyl；
R7For C1～C4Alkyl；
R8、R9It is each independently hydrogen, C1～C4Alkyl, replace C1～C4Alkyl or C2～C4Alkenyl, the replacement
C1～C4The substituent group of alkyl is selected from-OH ,-CN ,-OCOR ,-OCOC6H5、-COOR、OCOOR、-OC6H5、-C6H5Or C1～C4
Alkoxyl, each R is each independently C1～C4Alkyl；
In formula (4),
X6、X7It is each independently-H ,-NO2、-Cl、-OCH3、-OSO2-Ph、-COOC2H4OC2H4OCH3, wherein, Ph represents benzene
Base；
R10For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl.
3. disperse dye composition according to claim 2, it is characterised in that component C is selected from formula (3-1)～(3-
12) one or more in compound,
Preferably, component D is selected from one or more in formula (4-1)～(4-9) compound,
4. the disperse dye composition according to any one of claim 1-3, it is characterised in that the disperse dyes combination
In thing, the content of component A is 1-99 weight portions, preferably 20-99 weight portions, more preferably 40-95 weight portions；Component B contains
Measure as 1-99 weight portions, preferably 1-80 weight portions, more preferably 5-60 weight portions；The content of component C is 0-90 weight portions, excellent
Elect 10-87 weight portions as；The content of component D is 0-20 weight portions, preferably 0.1-10 weight portions；
Preferably, the disperse dye composition include formula (1-1)～(1-2) compound in one or two, formula (2-1) change
One or more in compound and optional formula (3-1)～(3-4) compound；
Preferably, the disperse dye composition includes formula (1-1) compound and formula (2-9) compound.
5. the disperse dye composition according to any one of claim 1-4, it is characterised in that the disperse dyes combination
Thing includes：In formula (1) compound of 10-40 weight portions one or more compound group into component A, the formula of 3-50 weight portions
(2) in compound one or more compound group into component B and 10-87 weight portions formula (3) compound in one or more
Compound group into component C.
6. the disperse dye composition according to any one of claim 1-5, it is characterised in that the adjuvant includes auxiliary agent
And water, one or more in dispersant, dyeing auxiliaries, surfactant, the antibacterial of the auxiliary agent；
Alternatively, the dispersant is selected from naphthalene sulfonic acid-formaldehyde condensation product, condensation compound of methyl naphthalene sulfonic acid and formaldehyde, benzyl LOMAR PWA EINECS 246-676-2 first
One or more in aldehyde condensate, lignosulfonates；
Alternatively, the dyeing auxiliaries is Matrii Sulfas Exsiccatus.
7. the preparation method of the disperse dye composition any one of a kind of claim 1-6, it is characterised in that include with
Lower step：(1) compound shown in formula (P) is added to the water into beating, plus it is 10～13 that alkali adjusts pH, is warmed up to 50～80 DEG C,
Insulation is filtered after 30～60 minutes, washes, is dried, and then carries out diazotising, then carries out being coupled instead with the compound shown in formula (Q)
Should, obtain product I；Preferably, the alkali selected from sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide,
One or more in ammonium hydroxide, potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine；
Or, by the compound diazotising shown in formula (P), temperature is diluted and controlled with ice, water for less than 5 DEG C, plus it is kieselguhr, swollen
Profit soil or activated carbon stirring, filtration, then coupling reaction is carried out with the compound shown in formula (Q), product I is obtained；Wherein, formula (P)
In, X1、X2As defined in claim 1-6；In formula (Q), R1、R2、R3, as defined in claim 1-6；
(2) by the compound diazotising shown in formula (Z), on the rocks and/or water dilutes and cools to less than 5 DEG C, plus kieselguhr, swelling
Soil or activated carbon, stirring, filtration, then product II is obtained by coupling reaction with the compound shown in formula (H)；Wherein, formula (Z)
In, X3、X4As defined in claim 1-6；In formula (H), R4、R5As defined in claim 1-6；
One or more in products therefrom I is mixed with one or more in the product II and optional adjuvant, gained
Mixture is used as disperse dye composition；
Alternatively, it is further comprising the steps of：Compound shown in formula (X) is added to the water into beating, plus it is 10～13 that alkali adjusts pH,
Be warmed up to 50～80 DEG C, insulation is filtered after 30～60 minutes, washing, be dried, then carry out diazotising, then with shown in formula (Y)
Compound carries out coupling reaction, obtains product III；Preferably, the alkali is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, bicarbonate
In potassium, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, aluminium hydroxide, methylamine, ethamine and triethylamine one
Plant or various；Wherein, in formula (X), X5As defined in claim 1-6；In formula (Y), R6、R7、R8、R9Such as claim 1-6
Defined in；
By one or more in products therefrom III with one or more in the product I and in product II
One or more and optional adjuvant are mixed, and gained mixture is used as disperse dye composition；
Alternatively, it is further comprising the steps of：Compound shown in formula (M) is added to the water into beating, plus it is 10～13 that alkali adjusts pH,
Be warmed up to 50～80 DEG C, insulation is filtered after 30～60 minutes, washing, be dried, then carry out diazotising, then with shown in formula (N)
Compound carries out coupling reaction, obtains product IV；Wherein, in formula (M), X6、X7It is each independently-OSO2-Ph、-
COOC2H4OC2H4OCH3, in formula (N), R10For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl；Preferably, the alkali choosing
From sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonia, sodium hydroxide, ammonium hydroxide, potassium hydroxide, Lithium hydrate, hydrogen
One or more in aluminium oxide, methylamine, ethamine and triethylamine；
Or, by the compound shown in formula (M) add water crushing, distillation, when fraction reaches more than the 20% of amount of water, stop steam
Evaporate, cool to less than 40 DEG C, add hydrochloric acid beating, then diazotising obtains diazol, then carries out with the compound shown in formula (N)
Coupling reaction, obtains product IV；Wherein, in formula (M), X6、X7It is each independently-H ,-NO2、-Cl、-OCH3, in formula (N), R10
For optionally by C1～C4The C that alkoxyl replaces1～C4Alkyl,
By one or more in products therefrom IV and one or more in product I and the one kind or many selected from product II
Kind and optional one or more selected from product III, optional adjuvant mixed, gained mixture as dispersion dye
Feed composition.
8. preparation method according to claim 7, it is characterised in that by one or more in the product I and be selected from
One or more in product II, optional one or more in product III and optional one kind selected from product IV
Or it is various particlized process is carried out in the presence of adjuvant, make liquid or be dried, be obtained disperse dye composition；
Or by one or more in product I and one or more selected from product II and optional selected from product III's
One or moreth, carry out particlized process in the presence of adjuvant respectively optional one or more selected from product IV, then carry out
Mixing, makes liquid or is dried, and disperse dye composition is obtained；
Preferably, the particlized is processed and carried out using sand mill or grinder；
Preferably, it is described dry using spray drying.
9. the disperse dye composition any one of a kind of claim 1-6 is used for the dyeing of fabric or the purposes of stamp；
Preferably, the fabric is terylene or polyester blended fabric.
10. a kind of fabric, it is characterised in that the fabric is using the disperse dye composition described in any one of claim 1-6
Dyeed or stamp is prepared；Preferably, the fabric is terylene or polyester blended fabric.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107345083A (en) * | 2017-06-28 | 2017-11-14 | 浙江龙盛化工研究有限公司 | It is a kind of blue to black disperse dye composition and dye preparations |
| KR20180021022A (en) * | 2017-05-02 | 2018-02-28 | 프레이리안트 스페셜티 컴퍼니., 리미티드 | Brilliant blue azo dye and method of preparation thereof, and its use |
| KR20180021752A (en) * | 2017-09-22 | 2018-03-05 | 프레이리안트 스페셜티 컴퍼니., 리미티드 | Black dye composition with high fastness and dispersion property |
| CN107892824A (en) * | 2017-10-26 | 2018-04-10 | 浙江闰土研究院有限公司 | A kind of preparation method of environment-friendly type azo dispersion dyes |
| CN108047762A (en) * | 2017-12-29 | 2018-05-18 | 东营安诺其纺织材料有限公司 | A kind of disperse dyes, disperse dye composition and disperse dyes feedstock composition and its application |
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| CN115160818A (en) * | 2022-08-11 | 2022-10-11 | 江苏迪安化工有限公司 | Efficient synthesis method of disperse dye R-4BS |
Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2336852A (en) * | 1998-05-01 | 1999-11-03 | Yorkshire Chemicals Plc | Dye composition for dyeing fibres based on mixture of at least three N-ethyl-N-substituted 4-(2-halo-4-nitro-6-[halo/nitro]phenyl)azoaniline derivatives |
| CN1693301A (en) * | 2004-05-07 | 2005-11-09 | 杨宝德 | Process for preparing ortho nitrophenylamine |
| CN1696205A (en) * | 2005-05-20 | 2005-11-16 | 浙江闰土股份有限公司 | Composite environmental protection type disperse dyes |
| CN1793240A (en) * | 2005-09-28 | 2006-06-28 | 杭州吉华化工有限公司 | Dispersing dye mixture and dye products |
| CN1844260A (en) * | 2006-04-29 | 2006-10-11 | 浙江闰土股份有限公司 | Combined disperse dye consisting of blended black and blue series |
| CN101020789A (en) * | 2007-02-14 | 2007-08-22 | 浙江龙盛染料化工有限公司 | Disperse azo dye composition |
| CN101094895A (en) * | 2005-01-04 | 2007-12-26 | 克莱里安特财务(Bvi)有限公司 | Disperse azo dye mixtures |
| CN101314677A (en) * | 2008-07-18 | 2008-12-03 | 天津市亚东化工染料厂 | Process for preparing red novel substantive dye |
| CN101768376A (en) * | 2009-12-30 | 2010-07-07 | 浙江闰土股份有限公司 | Environment-friendly disperse dye composition |
| CN101792615A (en) * | 2010-03-09 | 2010-08-04 | 江苏吉华化工有限公司 | Environment-friendly dark blue and black series compound disperse dye and production method thereof |
| CN102344695A (en) * | 2011-11-14 | 2012-02-08 | 浙江闰土股份有限公司 | Composite dye composition, composite disperse dye and preparation method thereof |
| CN102516811A (en) * | 2011-10-31 | 2012-06-27 | 浙江龙盛集团股份有限公司 | Disperse black dye composition |
| CN102604426A (en) * | 2012-01-20 | 2012-07-25 | 江苏之江化工有限公司 | Compound disperse black azo dye |
| CN103113758A (en) * | 2012-12-14 | 2013-05-22 | 杭州吉泉投资管理合伙企业（有限合伙） | Dispersed dye mixture and application thereof |
| CN103194093A (en) * | 2013-03-29 | 2013-07-10 | 浙江龙盛集团股份有限公司 | Composition of blue to black disperse dyes |
| CN103709791A (en) * | 2013-12-23 | 2014-04-09 | 浙江花蝶染料化工有限公司 | Method and device for preparing disperse dye and obtained disperse dye |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN104725897A (en) * | 2013-12-23 | 2015-06-24 | 浙江龙盛集团股份有限公司 | Ecological environment-friendly treatment method of dye or dye intermediate |
| CN105255216A (en) * | 2015-11-04 | 2016-01-20 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye as well as preparation method and application of disperse dye |
-
2016
- 2016-12-30 CN CN201611269697.8A patent/CN106590027B/en active Active
Patent Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2336852A (en) * | 1998-05-01 | 1999-11-03 | Yorkshire Chemicals Plc | Dye composition for dyeing fibres based on mixture of at least three N-ethyl-N-substituted 4-(2-halo-4-nitro-6-[halo/nitro]phenyl)azoaniline derivatives |
| CN1693301A (en) * | 2004-05-07 | 2005-11-09 | 杨宝德 | Process for preparing ortho nitrophenylamine |
| CN101094895A (en) * | 2005-01-04 | 2007-12-26 | 克莱里安特财务(Bvi)有限公司 | Disperse azo dye mixtures |
| CN1696205A (en) * | 2005-05-20 | 2005-11-16 | 浙江闰土股份有限公司 | Composite environmental protection type disperse dyes |
| CN1793240A (en) * | 2005-09-28 | 2006-06-28 | 杭州吉华化工有限公司 | Dispersing dye mixture and dye products |
| CN1844260A (en) * | 2006-04-29 | 2006-10-11 | 浙江闰土股份有限公司 | Combined disperse dye consisting of blended black and blue series |
| CN101020789A (en) * | 2007-02-14 | 2007-08-22 | 浙江龙盛染料化工有限公司 | Disperse azo dye composition |
| CN101314677A (en) * | 2008-07-18 | 2008-12-03 | 天津市亚东化工染料厂 | Process for preparing red novel substantive dye |
| CN101768376A (en) * | 2009-12-30 | 2010-07-07 | 浙江闰土股份有限公司 | Environment-friendly disperse dye composition |
| CN101792615A (en) * | 2010-03-09 | 2010-08-04 | 江苏吉华化工有限公司 | Environment-friendly dark blue and black series compound disperse dye and production method thereof |
| CN102516811A (en) * | 2011-10-31 | 2012-06-27 | 浙江龙盛集团股份有限公司 | Disperse black dye composition |
| CN102344695A (en) * | 2011-11-14 | 2012-02-08 | 浙江闰土股份有限公司 | Composite dye composition, composite disperse dye and preparation method thereof |
| CN102604426A (en) * | 2012-01-20 | 2012-07-25 | 江苏之江化工有限公司 | Compound disperse black azo dye |
| CN103113758A (en) * | 2012-12-14 | 2013-05-22 | 杭州吉泉投资管理合伙企业（有限合伙） | Dispersed dye mixture and application thereof |
| CN103194093A (en) * | 2013-03-29 | 2013-07-10 | 浙江龙盛集团股份有限公司 | Composition of blue to black disperse dyes |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN103709791A (en) * | 2013-12-23 | 2014-04-09 | 浙江花蝶染料化工有限公司 | Method and device for preparing disperse dye and obtained disperse dye |
| CN104725897A (en) * | 2013-12-23 | 2015-06-24 | 浙江龙盛集团股份有限公司 | Ecological environment-friendly treatment method of dye or dye intermediate |
| CN105255216A (en) * | 2015-11-04 | 2016-01-20 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye as well as preparation method and application of disperse dye |
Non-Patent Citations (2)
| Title |
|---|
| 朱云: "《化学实验基础》", 31 March 2006, 上海交通大学出版社 * |
| 袁红萍: "《纺织精细化学品》", 31 May 2012, 东华大学出版社 * |
Cited By (18)
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|---|---|---|---|---|
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| KR102137478B1 (en) * | 2017-05-02 | 2020-07-27 | 항저우 프라리언트 컴퍼니., 리미티드 | Brilliant blue azo dye and method of preparation thereof, and its use |
| CN107345083A (en) * | 2017-06-28 | 2017-11-14 | 浙江龙盛化工研究有限公司 | It is a kind of blue to black disperse dye composition and dye preparations |
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| CN109971213A (en) * | 2018-12-21 | 2019-07-05 | 浙江龙盛集团股份有限公司 | A kind of disperse blue is to black dye composition, dye preparations and its application |
| CN113308132A (en) * | 2021-06-10 | 2021-08-27 | 约克夏(浙江)染化有限公司 | Disperse dye composition, disperse dye, preparation method and application thereof |
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| CN114773876A (en) * | 2022-05-20 | 2022-07-22 | 上海鸿源鑫创材料科技有限公司 | Disperse red dye composition and product thereof |
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| CN115160818A (en) * | 2022-08-11 | 2022-10-11 | 江苏迪安化工有限公司 | Efficient synthesis method of disperse dye R-4BS |
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