CN108530941A - A kind of dark blue reactive dye and application thereof - Google Patents

A kind of dark blue reactive dye and application thereof Download PDF

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Publication number
CN108530941A
CN108530941A CN201710117968.6A CN201710117968A CN108530941A CN 108530941 A CN108530941 A CN 108530941A CN 201710117968 A CN201710117968 A CN 201710117968A CN 108530941 A CN108530941 A CN 108530941A
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CN
China
Prior art keywords
dyestuff
dyeing
reactive dye
dark blue
present
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Pending
Application number
CN201710117968.6A
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Chinese (zh)
Inventor
沙振中
刘振国
严钦华
祝超
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Hubei Color Root Technology Co Ltd
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Hubei Color Root Technology Co Ltd
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Priority to CN201710117968.6A priority Critical patent/CN108530941A/en
Publication of CN108530941A publication Critical patent/CN108530941A/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/465Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
    • C09B62/47Azo dyes
    • C09B62/475Disazo or polyazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507Azo dyes
    • C09B62/513Disazo or polyazo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/38General 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
    • D06P1/384General 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 reactive group not directly attached to heterocyclic group
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/148Wool using reactive dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes
    • D06P3/666Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

It is described that there is such as general formula (1) compound represented or its salt for dyestuff the invention discloses a kind of dark blue reactive dye.Invention dyestuff is suitable for dyeing and printed cellulosic materials, such as dyeing and printing for hydroxyl or nitrogenous fibre materials, and dyestuff of the invention is especially suitable for dyeing processes material, and dyeing has good fastness ability.

Description

A kind of dark blue reactive dye and application thereof
Technical field
The invention belongs to dye fields, and in particular to a kind of preparation method and applications of dark blue reactive dye.
Background technology
Recently, the application practice of reactive dye proposes higher want to the economy of dyeing quality and colouring method It asks.In addition, the textile used outdoors, as it is necessary to have good solarizations for sportswear, soldier or the training clothes of police dress Fastness, crock fastness, perspiration fastness, washing fastness, the improved seeds in current reactive dye are each when often light in dye Item fastness is preferable, and cannot meet its needs when contaminating dark.Extensive, the more excellent Tibetan of properties is used currently on the market Cyan kind is the dyestuff of following formula
But there are still defects in application process for above-mentioned dye mixture, therefore it is a kind of with excellent to be badly in need of exploitation in the market Good sun-resistant, perspiration resistance, rub resistance and water-fastness performance, more particularly to the same dye with excellent performance when contaminating dark Material.
Invention content
It is an object of the present invention to overcome the deficiencies of existing technologies, a kind of new dyestuff and preparation method thereof is provided. Another object of the present invention is to provide new dyeing and the nitrogenous method with hydroxyl fibrous material of printing.
Reactive dye provided by the invention are the compound or its salt with following structure:
Wherein D1For the group of following general formula:
Wherein R1Can be Or-HNCH2CH2OCH2CH2SO2CH2CH2Cl;
X1For F or Cl
Wherein D2For the group with structure shown in following general formula:
Wherein R2、R3、R4And R5It can be-SO to be independently3H、-OCH3、-CH3、-HNCOCH3、- HNCOCH2CH2CH2SO2CH2CH2Cl、-SO2CH2CH2OSO3H、–H。
One kind as above-mentioned technical proposal is preferred, the D1For:
One kind as above-mentioned technical proposal is preferred, the D2For:
In one embodiment of the present of invention, a kind of atroceruleous reactive dye are produced as follows:
(i) compound of formula (27) and formula (28) compound represented are coupled to obtain the first intermediate of diazonium compound, Shown in structure such as formula (29);
D1-NH2
(28)
(ii) the first intermediate and formula (30) compound represented are coupled to obtain diazonium compound.
D2-NH2
(30)
The present invention reactive dye can in the form of free acid or in a salt form offer, the salt can be alkali gold Category, alkali salt, ammonium salt and organic ammonium salt.
The dark blue reactive dye of the present invention is suitable for dyeing and prints very wide range of material, such as hydroxyl or nitrogenous Fibrous material, the nitrogenous fibre materials can be that silk is thick, leather, wool, Fypro and polyurethane.The work of the present invention Containing cellulose fiber material of the property dyestuff particularly suitable for dyeing and printing all kinds.The cellulose-containing fibrous material can be with For native cellulose fibre, such as cotton, flax and hemp and cellulose and regenerated cellulose, such as cotton.The work of the present invention Property dyestuff be also suitable for dyeing or printing cellulosic mixed goods, such as cotton and Fypro mixture, especially cotton/ Polyester mixed fiber.
The dark blue reactive dye of the present invention can in various ways, especially with aqueous dye solutions and dye print pastes Form be applied to fibrous material and be fixed on fiber.They are suitable for exhaust processes and the dyeing according to pad dyeing method, can Using preceding method aqueous dye solutions (optional saliferous) dipping articles, and after handling with alkali process or in the presence of a base, Heat effect can be used or by being dyed in room temperature storage a few hours in the fixing of dye if necessary.After dyestuff is fixed, it can adopt With cold and hot water rinsing dyeing or printed matter, this process is optionally added with peptizaiton and promotes unlocked dyestuff diffusion Reagent.
The reactive dye of the present invention have high activity, good crystallized ability and extraordinary deep dyeing energy, they can be with It is used in low dyeing temperature according to exhaust processes and short rolling only is needed to steam the time in rolling steaming method.The reactive dye of the present invention Degree of fixation is high and unlocked dyestuff can easily wash off, and the difference between Infection Rate and degree of fixation is very small, soaping loss It is very low.The dyestuff of the present invention is also especially suitable for printing, and is especially printed in cotton fiber and nitrogen-containing fiber, such as sheep Hair or silk are thick or containing the thick mixed goods of wool or silk.
It is all had in acid and alkaline range using the dyeing and printed matter of the reactive dye production of the present invention high Intensity of colour and high fibre-dye binding stability, and there is the good fastness to light and extraordinary wet fastness properties, example As to washing lotion, to water, to seawater and to cross dyeing and to sweat light fastness and it is good to pleating, to hot pressing and to friction Fastness.
The reactive dye of the present invention also are suitable as the colorant for recording system, are used for example as being commercially for paper or spinning The ink-jet printer of fabric printing, the colorant of writing instrument (such as pen or annulus pen), and particularly useful as ink-jet printer Colorant.The reactive dye of the present invention can provide in the form of suitable for record system, such as can with the reactive dye of the present invention It is made as the colorant of water-based inks.The water-based inks can be in a usual manner by will be in ink jet printing in the desired amount of water Each normal constituent mix and prepare.The substrate for ink-jet printing is also wrapped other than paper or plastic film It includes such as above-mentioned hydroxyl or nitrogenous fibrous material, especially cellulose-containing fibrous material, such as textile fibre materials.
Dyestuff of the present invention is suitable for dyeing and printed cellulosic materials, such as hydroxyl or nitrogenous fibre materials dyeing and Printing, dyestuff of the invention is especially suitable for dyeing processes material, and dyeing has good fastness ability.
Specific implementation mode
The following example is for illustrating the present invention, and unless otherwise specified, for temperature degree Celsius to indicate, part is weight Part, percentage is weight percentage, and parts by weight are related to parts by volume of the kg/L than expression.The product prepared in following examples Characterized through HNMR and/or MS.
Following examples prepare dyestuff by following method:
(i) substrate A and substrate B obtain the first intermediate of diazonium compound through coupling;
(ii) the first intermediate and substrate C obtain reactive dye through coupling.
Embodiment 1
A, 56.4 parts are added in 200 parts of waterMashing one hour, so 24 part 30% of hydrochloric acid is added afterwards to stir 30 minutes, it is on the rocks to cool to 0 DEG C, at 30 minutes by 7.2 parts of sodium nitrite wiring solution-formings It is added, adds reaction and complete a diazo-reaction in.Then by 34.1 partsWith 100 parts of water It is made into neutral solution to be added at 40 minutes in a diazonium object, add with sodium bicarbonate adjusting material pH=2-4. at T=5-10 DEG C, It is reacted under conditions of pH=2-4 3-8 hours and completes a coupling reaction.
B, 54.7 parts are added in 200 parts of waterMashing one hour, so 24 part 30% of hydrochloric acid is added afterwards to stir 30 minutes, it is on the rocks to cool to 0 DEG C, at 30 minutes by 7.2 parts of sodium nitrite wiring solution-formings It is added, adds reaction and complete a secondary diazo-reaction in.It is then added in the conjugates obtained according to A, adds Material pH=4-8 is adjusted with sodium bicarbonate, and the secondary coupling of completion in 2-6 hours is reacted under conditions of T=5-15 DEG C, pH=4-8 instead It answers, you can obtain meeting dyestuff (1-1) of general formula (1) this dyestuff to be dark blue tone, tool by hydroxyl or nitrogen-containing fiber dyeing There is good comprehensive fastness ability.
Embodiment 2-21
According to the preparation method of example 1, the hereinbefore definition to each group is pressed, the formula for meeting general formula (1) can be equally obtained 1-2-1-21 dyestuffs.Hydroxyl or nitrogen-containing fiber dyeing can be dark blue tone and all had good by obtained dyestuff Comprehensive fastness ability.
The dyestuff number and corresponding structure that above-described embodiment prepares are referring to following table:
Embodiment 22:Dyeing
Staining procedure I:100 parts of cotton fabrics are added at 60 DEG C and are obtained according to embodiment 1 containing 45g/l sodium chloride and 2 parts In 1500 parts of dye baths of the reactive dye obtained.After 60 DEG C, 45 minutes, 20g/l natrium carbonicum calcinatums are added.Continue in this temperature It dyes other 45 minutes.Then the article for rinsing dyeing is soaped a quarter hour in boiling with phenanthrene ion detergent, again It rinses and dries.Above step can also be dyed at 80 DEG C.
Staining procedure II.0.1 part of dyestuff according to embodiment 1 is dissolved in 200 parts of water, and 0.5 part of sodium sulphate of addition, 0.1 part of Levelling assistants (condensation product based on higher aliphatic amine and ethylene oxide) and 0.5 part of sodium acetate.Then acetic acid is used (80%) pH is adjusted to 5.5 value.Dye bath is heated 10 minutes at 50 DEG C, and 10 parts of wool fabrics are then added, then It is heated, reached 100 DEG C by about 50 minutes, and dyeing 60 minutes is carried out in this temperature, so that dye bath is cooled to 90 thereafter DEG C, and take out tinted article.With hot and cold water washing wool fabric, then rotate and dry.
By the dyestuff of embodiment 2-21, using the colouring method of embodiment 22, it can equally reach identical effect.
23 stamp of embodiment
The dyestuff that 3 parts obtain according to embodiment 1 is sprayed under fast stirring and contains 50 part of 5% sodium alginate into 100 parts Thickener, 27.8 parts of water, 20 parts of ureas, 1 part of m-nitrobenzene sodium sulfonate and 1.2 parts of sodium bicarbonates stock thickener in.Using such as This print paste obtained prints cotton fabric, and the printed material of dry gained simultaneously steams 2 minutes in 102 DEG C of saturated vapors.So After rinse printed fabric, if it is desired, soap and rinse again at the boil, be subsequently dried.
By the dyestuff of embodiment 2-21, using the printing method of embodiment 23, it can equally reach identical effect.
It is that colouring method and the implementation of embodiment 22 is respectively adopted in the dyestuff of embodiment 1-21 in formula (a) and the present invention below Every application performance index correction data of fabric after the printing method fixation of example 23.
The dyestuff that number is 1 is that the wide dyestuff (a) of purposes, the dyestuff that number is 2-22 are the present invention currently on the market Dyestuff described in embodiment 1-21, for the dyestuff that number is 2-22 compared with the dyestuff of number 1, properties have prodigious carry It rises, is showed obviously especially in this several washing fastness, light fastness, perspiration fastness, fastness to wet rubbing performances, illustrate the present invention The dyestuff properties all increase significantly.
It should be noted last that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting.Although ginseng It is described the invention in detail according to embodiment, it will be apparent to an ordinarily skilled person in the art that the technical side of the present invention Case is modified or replaced equivalently, and without departure from the spirit and scope of technical solution of the present invention, should all be covered in the present invention Right in.

Claims (4)

1. a kind of dark blue reactive dye, it is characterised in that:
The dyestuff is with such as general formula (1) compound represented or its salt:
Wherein D1For the group with structure shown in formula (2):
Wherein R1For Or-HNCH2CH2OCH2CH2SO2CH2CH2Cl;
X1For F or Cl;
Wherein D2For the group with structure shown in formula (3):
Wherein R2、R3、R4And R5It is independently-SO3H、-OCH3、-CH3、-HNCOCH3、-HNCOCH2CH2CH2SO2CH2CH2Cl、- SO2CH2CH2OSO3H or-H.
2. dark blue reactive dye according to claim 1, it is characterised in that:
The D1For:
3. dark blue reactive dye according to claim 1, it is characterised in that:
The D2For:
4. purposes of any reactive dye of claim 1-3 in dyeing and printing nitrogenous and hydroxyl fibrous material.
CN201710117968.6A 2017-03-01 2017-03-01 A kind of dark blue reactive dye and application thereof Pending CN108530941A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114085547A (en) * 2021-11-22 2022-02-25 湖北丽源科技股份有限公司 Green intermediate-temperature reactive dye and preparation method thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60130652A (en) * 1983-12-16 1985-07-12 Mitsui Toatsu Chem Inc Trisazo reactive dye
US5964900A (en) * 1997-06-24 1999-10-12 Ciba Specialty Chemicals Corporation Process for dyeing or printing cellulosic fibre materials and novel reactive dyes
CN1580132A (en) * 2003-08-15 2005-02-16 上海染料化工八厂 Blue dye composition preparation and use
CN101368008A (en) * 2007-08-15 2009-02-18 上海雅运纺织化工有限公司 Navy blue reactive dye composition and dyeing uses in fibrous material thereof
CN103342901A (en) * 2013-07-09 2013-10-09 沈钢 High-performance polyazo green reactive dye and synthesis and application of dye mixture
CN103627206A (en) * 2013-11-21 2014-03-12 天津德凯化工股份有限公司 Novel active navy blue dye

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60130652A (en) * 1983-12-16 1985-07-12 Mitsui Toatsu Chem Inc Trisazo reactive dye
US5964900A (en) * 1997-06-24 1999-10-12 Ciba Specialty Chemicals Corporation Process for dyeing or printing cellulosic fibre materials and novel reactive dyes
CN1580132A (en) * 2003-08-15 2005-02-16 上海染料化工八厂 Blue dye composition preparation and use
CN101368008A (en) * 2007-08-15 2009-02-18 上海雅运纺织化工有限公司 Navy blue reactive dye composition and dyeing uses in fibrous material thereof
CN103342901A (en) * 2013-07-09 2013-10-09 沈钢 High-performance polyazo green reactive dye and synthesis and application of dye mixture
CN103627206A (en) * 2013-11-21 2014-03-12 天津德凯化工股份有限公司 Novel active navy blue dye

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
何瑾馨: "《染料化学》", 30 June 2004, 中国纺织出版社 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114085547A (en) * 2021-11-22 2022-02-25 湖北丽源科技股份有限公司 Green intermediate-temperature reactive dye and preparation method thereof
CN114085547B (en) * 2021-11-22 2024-07-09 湖北丽源科技股份有限公司 Green medium-temperature reactive dye and preparation method thereof

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