CN108102425B - A kind of spy's dark black active dyestuff, preparation method and application - Google Patents
A kind of spy's dark black active dyestuff, preparation method and application Download PDFInfo
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- CN108102425B CN108102425B CN201711417105.7A CN201711417105A CN108102425B CN 108102425 B CN108102425 B CN 108102425B CN 201711417105 A CN201711417105 A CN 201711417105A CN 108102425 B CN108102425 B CN 108102425B
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- acid
- spy
- dark black
- black active
- active dyestuff
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0047—Mixtures of two or more reactive azo dyes
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/248—Polyamides; Polyurethanes using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
Abstract
The present invention provides a kind of special dark black active dyestuff, which is characterized in that and spy's dark black active dyestuff includes at least following formula (1) and/or formula (2) compound represented,, wherein R1、R2、R3、R4It is selected from H, CH independently of one another or in the same manner3、OCH3、OC2H5、SO3H；Y1、Y2It is independently from each other-SO2CH=CH2、‑SO2CH2CH2OSO3M、‑SO2NHCH2CH2SO2CH=CH2、‑SO2NHCH2CH2SO2CH2CH2OSO3M；M is selected from the sodium or potassium of the H of the form of free acid or the form of metal salt.The features such as special dark black active dyestuff mixture of the invention has that bright in colour, color is deep, solubility is high, and compatibility is good, degree of fixation is up to 82-85%, and every fastness is excellent.The dyestuff is suitable for the dyeing, stamp and pad dyeing of cellulose fibre, protein fibre, viscose rayon and Fypro etc., and washing, fastness to rubbing are higher than the 0.5-1 grade of general kind.
Description
Technical field
The present invention relates to technical field of fine more particularly to a kind of special dark black active dyestuff mixture and its preparations
Method, application.
Background technique
Reactive dye dosage currently on the market is only second to disperse dyes, scientific and technical research it is studied it is more and more, simultaneously
Increasingly pay close attention to the application of reactive dye.Especially the research article in relation to reactive dye and patent are numerous in recent years, not only relate to
And the innovation and development of reactive dye structure, it further include the preparation process and its application performance of reactive dye, emphasis is to improve it to answer
With performance and the feature of environmental protection.Especially black reaction dyestuff, the black KN-B dosage of the reactivity as shown in formula (i) account for reactive dye
50% or more, mainly cheap, easy to wash property is good.But it is bad as black dyes its pitch black degree, depth, fastness,
It can be by the black KN-B of reactivity and orange KN-GR colorant match, or by the black KN-B of reactivity and active red in order to increase pitch black degree
WNN, active yellow WNN colorant match, greatly enhance the blackness of cotton fabric, even if there is also following critical defects in this way: (1) black
Blackness is still not ideal enough, and depth is bad；(2) the main deficiency of above-mentioned dyestuff is that dye fixing rate is low, only 60-65%, dye
Color raffinate coloration is deep.Economic benefit is not only affected, but also also results in environmental pollution.
It would therefore be highly desirable to develop a kind of utilization rate that can be improved black dyes and degree of fixation, the dye in dyeing waste liquid is reduced
The reactive dye of content are expected to solve the above problems.
Summary of the invention
The purpose of the invention is to overcome the shortcomings of existing product application performance, a kind of special aterrimus activity dye is provided
Material.
It is a further object of the present invention to provide a kind of preparation methods of above-mentioned dye composition.
A further object of the invention provides above-mentioned dye composition as a kind of special dark black active dyestuff mixture
Purposes.
The purpose of the present invention can be achieved by the following measures: in the structure design of reactive monoazo dyestuffs, still retain sour (the 1- ammonia of H
Base -8- naphthols -3,6- disulfonic acid) as coupling component, so that it is still retained original dark blue tone, while using sour (the 2- ammonia of J
Base -5- naphthols -7- sulfonic acid) or γ sour (7- amino -1- naphthols -3- sulfonic acid) not only made diazo component but also made coupling component, will be dark blue
Color and orange, red carry out intramolecular colorant match improve the depth of dyeing, while being extended with for dyestuff conjugated system is conducive to improve dye
The substantivity of material, to improve its dye-uptake, degree of fixation；In addition the introducing of alkyl and sulfonamido makes the total flat of its molecular structure
Property sharp fall in face balances the substantivity of dyestuff, changes sequence and reaction condition that sour even, alkali occasionally reacts, improves dyestuff
Washing and fastness to rubbing.Do not saltout no waste water of above two improved result product generates, and improves washing fastness and antifriction
Rubbing fastness is opposite to improve 0.5-1 grades.
The present invention relates to a series of structure such as following formula (1) and formula that can be used as special dark black active dyestuff compound
(2) shown in:
In formula, R1、R2、R3、R4It is selected from H, CH independently of one another or simultaneously3、OCH3、OC2H5、SO3H、SO3Na；Y1、Y2Each other
Independently selected from-SO2CH=CH2,-SO2CH2CH2OSO3M ,-SO2NHCH2CH2SO2CH=CH2,-
SO2NHCH2CH2SO2CH2CH2OSO3M；M is selected from H (form of free acid) or sodium or potassium (form of metal salt), preferably with alkali gold
The form for belonging to salt exists.In above formula, R1、R2、R3、R4It is preferred that H, CH3、OCH3、OC2H5、SO3H, Y1、Y2It is preferred that-
SO2CH2CH2OSO3M ,-SO2NHCH2CH2SO2CH2CH2OSO3M, group-SO2CH=CH2,-SO2NHCH2CH2SO2CH=CH2It can
By-SO2CH2CH2OSO3M ,-SO2NHCH2CH2SO2CH2CH2OSO3H by sulfate ester hydrolysis come.As in formula (1) and formula (2)
The preferred intermediate for the two sides active group being connected with azo group, it includes but be not limited to group shown in following formula (A)~formula (G)
Or other active groups with ethylene sulfuryl or fatty straight-chain ethylene sulfuryl.
The most preferred reactive dye mixture of the present invention, at least contain one or more kinds of structures such as following formula (1a)~
Dye composition shown in formula (24b):
The above-mentioned various dye compositions combined by formula (1) and/or formula (2) are as a kind of special dark black active dyestuff, tool
Have that bright in colour, color is deep, solubility is high, the features such as compatibility is good, lifting force is high, degree of fixation is high, and every fastness is excellent.It is applicable in
In the dyeing of cellulose fibre, protein fibre, viscose rayon and Fypro, stamp and pad dyeing, while can be reacted with other
Property black dyes and reactive yellow dyes as three primary colors carry out colorant match, can contaminate different depth, coloured light color, water
Wash, fastness to rubbing be higher than general kind 0.5-1 grade.
Quantitative solid nitrous acid is added the preparation method comprises the following steps: J acid or after γ acid dissolves with caustic soda in one kind of formula (1) and formula (2)
Sodium matches resulting mixture.Said mixture thread is added in hydrochloric acid and ice water and carries out the obtained diazonium salt of bob-weight nitridation reaction；J acid
Or the diazonium salt of γ acid and H acid carry out acid coupling, acid idol terminal reach after again with containing (or being free of) methyl, methoxyl group, ethyl,
The diazonium salt of sulfonic hydroxyethyl sulfone sulfate ester aniline (or sulfonamido ethyl sulfuryl hydroxide ethylsulfuric acid ester aniline) is coupled, mistake
It filters, be spray-dried to obtain semi-finished product.The spray drying granulation includes carrying out supermolecule compounding (to refer to that the dye solution that synthesis obtains is mixed
It closes, the mistake that adding assistant naphthalene sulfonic acid-formaldehyde condensation product or condensation compound of methyl naphthalene sulfonic acid and formaldehyde and sodium sulphate, potassium sulfate are standardized
Journey) and compounding dyestuff.
Heretofore described H acid is the abbreviation of 1- amino-8-naphthol -3,6- disulfonic acid, and J acid is 2- amino -5- naphthols -
The abbreviation of 7- sulfonic acid, γ acid are the abbreviations of 7- amino -1- naphthols -3- sulfonic acid.J acid, γ acid diazonium all be use anti-heavy nitrogen
Diazonium salt is prepared, reaction temperature is 0~10 DEG C, pH value is 0.7~1.4.Containing (or being free of) methyl, methoxyl group, ethyl, sulfonic group
Hydroxyethyl sulfone sulfate ester aniline (or sulfonamido ethyl sulfuryl hydroxide ethylsulfuric acid ester aniline) diazonium all be using ice mill weight
Nitriding method (referring to that diazo component, which is added to ice in ice water, to be ground, and is then added hydrochloric acid, is added sodium nitrite solution) preparation,
Reaction temperature is 5~15 DEG C, pH value is 1~1.5.Each coupling reaction diazonium salt, which must disappear just, can be carried out the anti-of next step
It answers.
The present invention relates to a kind of preparation processes of special dark black active dyestuff of formula (1) and formula (2), including following reaction:
Diazo reaction, coupling reaction, hydrolysis.
The present invention relates to above-mentioned three kinds reactions to be prepared with known reaction route, is matched by changing its coupling component
Than, and temperature, pH value, concentration raising reaction rate and the conversion ratio of reaction, obtain content not equal azo dyes, azo
Dyestuff generates that absolute degree of fixation is different and application performance changes because of component content difference, preferably optimum proportioning, reaction out
Condition, synthesis obtain a kind of special dark black active dyestuff mixture.Obtained reactive dye mixture used additives naphthalene sulfonic acids first
After being standardized before aldehyde condensate or condensation compound of methyl naphthalene sulfonic acid and formaldehyde and sodium sulphate, the wet spelling of potassium sulfate progress, then it is sprayed
It is dry.Dyestuff made from this method is uniform, and performance is more preferable.
Invention effect
Compared with the prior art, the advantages of the present invention are as follows: a kind of synthesized special dark black active dyestuff mixture tool
Have that bright in colour, color is deep, solubility is high, the features such as compatibility is good, lifting force is high, degree of fixation is high, and every fastness is excellent.It is applicable in
In the dyeing of cellulose fibre, protein fibre, viscose rayon and Fypro, stamp and pad dyeing, while can be reacted with other
Property black dyes and reactive yellow dyes as three primary colors carry out colorant match, can contaminate different depth, coloured light color, water
Wash, fastness to rubbing be higher than general kind 0.5-1 grade.
Specific embodiment
Below with reference to embodiment, the invention will be further described, but these embodiments are not constituted to protection model of the invention
The limitation enclosed.In embodiment, such as nothing especially indicates that the signified dosage of reaction is hundred parts by weight of folding (measuring with g or Kg)
Embodiment 1:
One, a diazotising of J acid
The sodium nitrite solution (0.1mol) that (0.1mol) is added 30% in the 10% of the J acid, solution of pH=6.5-8 stirs
Mix uniformly after, thread is added in the mixed liquor of hydrochloric acid (0.1mol) and 80g ice, temperature control 0-10 DEG C, KI test paper it is micro- it is blue,
Congored test paper avy blue reacts 1-1.5 hours and eliminates micro- excessive nitrous acid.
Two, the even reaction of acid
Prepared 10% H acid solution (0.1mol) is added under stiring in above-mentioned diazonium salt, temperature 0- is controlled
10 DEG C, pH≤3 disappear after adding with 10% sodium bicarbonate aqueous solution regulation pH=2-4, in 5-20 DEG C of reaction to diazonium salt.Cooling
To 10 DEG C to secondary coupling.
Three, secondary diazotising
The para-ester of 0.1mol is added in the mixed liquor of 10g water, 80g ice, 3.5g hydrochloric acid and is beaten, is then slowly added into
It is configured to the sodium nitrite solution (30%) of 6.9g, controls 0-10 DEG C of temperature, micro- blue, the Congored test paper avy blue of KI test paper,
Sodium nitrite solution keeps the micro- reaction blue of 5-10 DEG C of temperature, KI test paper 1 hour after adding, with a small amount of sulfamic acid before coupling
Eliminate micro- excessive nitrous acid.
Four, coupling and hydrolysis
It is added with stirring above-mentioned diazonium salt in sour even reactor, is kept for 5-15 DEG C of temperature, reacts 4-8 hours, use little Su
It beats and adjusts pH=6-8.5, react 2-3 hours, terminal adjusts pH=6-6.5 again after reaching, 15g naphthalene sulfonic acid-formaldehyde condensation product is added
Or sodium sulphate, potassium sulfate, filtering, filtrate is collected, dye liquor is directly concentrated or is spray-dried and to obtain aterrimus dye mixture.
Embodiment 2-24:
Reaction step and principle are substantially the same manner as Example 1, replace different diazo components, suitably fine tuning technique, according to
The normal operating in the field is implemented as required.The each component of embodiment 2-24 is shown in Table one.
Each component in (table one) embodiment 2-24
A, B, C, D, E, F, G refer to the raw material that following structures are added in secondary diazonium, three times diazonium in upper table.
A kind of a: b: c: d ratio 30-60 of dyestuff each component of spy's dark black active dyestuff mixture in embodiment 1-24:
30-50∶5-10∶5-10。
Dyeing explanation:
By 1g by dyestuff made from embodiment 1-24, first sufficiently dissolved with suitable water, then constant volume is in 250ml volumetric flask
In, it draws 50ml dye liquor and is mixed with 50ml water, 5g cotton, 6g sodium sulphate is then added, then with the heating rate of 10 DEG C/min
To 50-60 DEG C, 2g sodium carbonate is added after being kept for 30 minutes, then keep 60-70 DEG C of dyeing 30min, then takes out and used by dye cotton
Non-ionic cleaning agent boiling soap boiling 15min, is washed with water and dries at 70 DEG C or so, it is preferable to obtain good level-dyeing property, pitch black degree
Black fabric, the washing of black fabric, fastness to rubbing are higher than the 0.5-1 grade of general Reactive dye red M-3BE.Dyeing is implemented
As a result superior function is relatively shown in Table two.
In the test process of two performance indicator of table, following standard is used:
Evaluation method: the general condition regulation of GB/T2374-2007 dyeing measurement
Solubility: the measuring method of GB/T3671.1-1996 water-soluble dye solubility and stability of solution
The measurement of dyestuff lifting force: GB/T 21875-2016
Degree of fixation: the measurement of GB/T2391-2006 reactive dye degree of fixation
Fastness to rubbing: GB T 3920-2008 textile color stability tests colour fastness to rubbing
Fastness to washing: GB T 3921.2-1997 textile color stability tests color fastness to washing
(table two) Dyeing Example performance compares
Detailed Jie has been carried out to a kind of special dark black active dyestuff provided by the present invention, preparation method and applications above
It continues, used herein a specific example illustrates the principle and implementation of the invention, and the explanation of the above implementation is
It is used to help understand method and its core concept of the invention；At the same time, for those skilled in the art, according to the present invention
Thought, there will be changes in the specific implementation manner and application range, will be possible to change and improvement of the invention
, the conception and scope without exceeding accessory claim defined, in conclusion the content of the present specification should not be construed as pair
Limitation of the invention.
Claims (11)
1. it is a kind of spy dark black active dyestuff, which is characterized in that it is described spy dark black active dyestuff include at least following formula (1) and
Formula (2) compound represented:
Wherein, R1、R2、R3、R4It is selected from H, CH independently of one another or in the same manner3、OCH3、OC2H5、SO3H、SO3Na；Y1、Y2Independently of one another
Ground is selected from-SO2CH=CH2、-SO2CH2CH2OSO3M、-SO2NHCH2CH2SO2CH=CH2、-
SO2NHCH2CH2SO2CH2CH2OSO3M；M is selected from the sodium or potassium of the H of the form of free acid or the form of metal salt.
2. spy's dark black active dyestuff according to claim 1, wherein dye composition shown in formula (1) is following formula (1-
1), dye composition shown in formula (2) is following formula (2-1),
Wherein, D1And D2The represented benzene ring substitution group being connected with diazo as a whole can also be independently of one another by such as following formula
(G) substituent group-C shown in2H4SO2C2H4C1 substitution,
3. the preparation method of spy's dark black active dyestuff according to claim 1 or 2, which is characterized in that diazotation step
Quantitative sodium nitrite is added with resulting mixture in i:J acid or γ acid after being dissolved with caustic soda, be added in hydrochloric acid and ice water and carry out bob-weight
Diazonium salt is made in nitrogen；Coupling step ii: diazonium salt and H acid are coupled；Hydrolysing step iii: terminal reach after again with comprising or do not wrap
Contain or simultaneously comprising methyl, methoxyl group, ethyl, sulfonic hydroxyethyl sulfone sulfate ester aniline or sulfonamido ethyl sulfuryl hydroxyl second
The saline and alkaline coupling of the diazonium of base sulfate ester aniline；Step iv: filtrate is collected in filtering, is spray-dried to obtain semi-finished product.
4. the preparation method of spy's dark black active dyestuff according to claim 3, which is characterized in that will be collected in step iv
The filtrate suitable auxiliary agent be added mixed, then Direct spraying drying-granulating obtains finished product.
5. the preparation method of spy's dark black active dyestuff according to claim 3 or 4, which is characterized in that in step i, by J
Quantitative water mashing is added in acid or γ acid, is 7-8.5 with 30% caustic soda adjusting pH value, concentration 5-15%, quantitative nitrous is added
Resulting mixture is matched in sour sodium stirring；Mixture thread is added in hydrochloric acid and ice water and carries out the obtained diazonium salt of bob-weight nitrogen, diazonium temperature
Degree is 0~20 DEG C, eliminates micro- excessive nitrous acid before acid is even.
6. it is according to claim 3 or 4 spy dark black active dyestuff preparation method, which is characterized in that in step ii to
H acid powder is added in the diazonium salt in the 10-20 DEG C of even reaction of progress acid, until the even terminal of acid reaches.
7. the preparation method of spy's dark black active dyestuff according to claim 3 or 4, which is characterized in that institute in step iii
Diazonium salt is stated using ice mill diazonium preparation, diazonium temperature is 5~15 DEG C, pH value is 0.7~1.8, is eliminated before alkali is even micro- excessive
Nitrous acid.
8. the preparation method of spy's dark black active dyestuff according to claim 3 or 4, which is characterized in that the alkali of step iii
It occasionally include after reaction continues 2-3 hours, being disappeared with sodium bicarbonate tune pH value to diazonium salt.
9. the preparation method of spy's dark black active dyestuff according to claim 4, which is characterized in that the spray drying is made
Grain includes carrying out supermolecule compounding and compounding dyestuff.
10. the purposes of spy's dark black active dyestuff according to claim 1 or 2, which is characterized in that spy's aterrimus is living
Property dyestuff be suitable for cellulose fibre, protein fibre, viscose rayon and Fypro dyeing, stamp and pad dyeing.
11. the purposes of spy's dark black active dyestuff according to claim 10, which is characterized in that while can be reacted with other
Property black dyes and reactive yellow dyes as three primary colors carry out colorant match, contaminate different depth, coloured light color.
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| CN201711417105.7A CN108102425B (en) | 2017-12-25 | 2017-12-25 | A kind of spy's dark black active dyestuff, preparation method and application |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005220211A (en) * | 2004-02-05 | 2005-08-18 | Nippon Kayaku Co Ltd | Trisazo compound, ink composition and colored product |
| EP1777273A1 (en) * | 2005-10-20 | 2007-04-25 | Fujifilm Corporation | Ink composition, ink set and recording method |
| CN104448920A (en) * | 2014-12-03 | 2015-03-25 | 泰兴锦云染料有限公司 | Compound capable of being used as reactive navy blue dye and preparation method of compound |
| CN106566281A (en) * | 2016-09-14 | 2017-04-19 | 浙江科永化工有限公司 | Reactive navy blue-to-black dye composition and dye product |
-
2017
- 2017-12-25 CN CN201711417105.7A patent/CN108102425B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005220211A (en) * | 2004-02-05 | 2005-08-18 | Nippon Kayaku Co Ltd | Trisazo compound, ink composition and colored product |
| EP1777273A1 (en) * | 2005-10-20 | 2007-04-25 | Fujifilm Corporation | Ink composition, ink set and recording method |
| CN104448920A (en) * | 2014-12-03 | 2015-03-25 | 泰兴锦云染料有限公司 | Compound capable of being used as reactive navy blue dye and preparation method of compound |
| CN106566281A (en) * | 2016-09-14 | 2017-04-19 | 浙江科永化工有限公司 | Reactive navy blue-to-black dye composition and dye product |
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| Publication number | Publication date |
|---|---|
| CN108102425A (en) | 2018-06-01 |
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