CN105733290A - Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof - Google Patents
Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN105733290A CN105733290A CN201610063771.4A CN201610063771A CN105733290A CN 105733290 A CN105733290 A CN 105733290A CN 201610063771 A CN201610063771 A CN 201610063771A CN 105733290 A CN105733290 A CN 105733290A
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- CN
- China
- Prior art keywords
- perspiration
- disperse dye
- monomeric compound
- color fastness
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- NCYIYMGWCMYYGQ-PWAKNHQASA-N N=NC(C=C1)=CC/C1=C\[N+]([O-])=O Chemical compound N=NC(C=C1)=CC/C1=C\[N+]([O-])=O NCYIYMGWCMYYGQ-PWAKNHQASA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N Nc(cc1)ccc1N Chemical compound Nc(cc1)ccc1N CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
-
- 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
- C09B67/008—Preparations of disperse dyes or solvent 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
Abstract
The invention relates to a monomeric compound of an orange disperse dye with high perspiration fastness as well as a preparation method and application thereof. A structure of the compound is shown in a formula I in the specification. The compound is prepared by adopting diazotization and coupling reaction. The compound is individually applied to preparation of disperse dyes or forms dye compositions with other dye monomers to prepare disperse dyes. The preparation process is simple and is low in cost. The dye has the advantages of good reproducibility and resistance to washing, friction and sublimation and especially has the characteristic of high perspiration fastness.
Description
Technical field
The invention belongs to nonionic dye field, particularly to a kind of high color fastness to perspiration orange disperse dye monomeric compound and its preparation method and application.
Background technology
Disperse dyes are the nonionic dyes that a class water solublity is relatively low.Disperse dyes for the dyeing of acetate fiber, are called cellulose acetate dye the earliest.Along with the development of synthetic fibers, chinlon, terylene occur in succession, especially terylene, high owing to having permutation degree, the characteristics such as fiber gap is few, and hydrophobicity is strong.This fiber to make swelling of fiber, dyestuff could enter fiber upper dye under high temperature, thermosol.Along with the development of synthetic fibers, dyestuff be it is also proposed new requirement by people, and conventional dyestuff has applied defect, for instance dye-uptake is low, and fastness makes it difficult for people's acceptance etc..In order to promote every fastness such as the washing of dyestuff, have been developed for various new dyestuff.
A series of disclosed in patent GB909843, CN102816453 connect the azo dispersion dyes that 2-oxoalkyl group esters replace, there is excellent washability and fastness to ironing.But in other performances, for instance sweat stain or spell and still suffer from defect in white fastness, lack broad applicability.
Summary of the invention
The technical problem to be solved is to provide a kind of high color fastness to perspiration orange disperse dye monomeric compound and its preparation method and application, preparation technology is simple for this compound, cost is low, for the dyestuff prepared, there is favorable reproducibility, water-fastness, rub resistance, resistance to distillation advantage, especially there is the feature that color fastness to perspiration is high.
The high color fastness to perspiration orange disperse dye monomeric compound of one of the present invention, the structure of described compound shown in formula I:
The preparation method of a kind of high color fastness to perspiration orange disperse dye monomeric compound of the present invention, comprises the steps:
(1) by aniline, acrylic acid, water mixing, 90-100 DEG C of stirring reaction 20-24 hour, cooling, adding methanol, 0-5 DEG C is stirred 12-18 hour；Filter, be subsequently added water, soda and benzyl chloride, mix and blend, add potassium iodide at 80-100 DEG C, react 12-18 hour, cooling, adding methanol, 0-5 DEG C is stirred 12-18 hour, by filter cake and DMF, soda and bromacetone mixing after filtration, it is warming up to 60-65 DEG C, add potassium iodide, stirring reaction 12-18 hour, be cooled to 40-45 DEG C, add water, filter and obtain carboxylate；
(2) water, hydrochloric acid and paranitroanilinum being mixed, add ice, less than 0 DEG C drips sodium nitrite in aqueous solution, at 5-6 DEG C diazo-reaction 2-4 hour, is subsequently adding the nitrite that sulfamic acid process unreacted is complete, it is thus achieved that diazotising liquid；
(3) adding above-mentioned diazotising liquid in frozen water mixed liquor, stirring, 5-10 DEG C adds carboxylate, and 10-15 DEG C is stirred 3-4 hour, filters, washing, it is thus achieved that orange disperse dye monomeric compound.
Described compound is applied individually to any to prepare disperse dyes or form dye composite with other dye monomers prepares disperse dyes.Compositions refers to according to printing color needs, formula I and other dye monomers is combined with arbitrary proportion.Described compositions can also contain auxiliary agent.Compositions can apply the printing and dyeing for different colours.
The preparation method of described disperse dyes, particularly as follows: mixed homogeneously under the existence of water or wetting agent with auxiliary agent 1:0.8-5 in mass ratio by compound and grind, then carries out spray drying, to obtain final product.
Described auxiliary agent is one or both in dispersant, diffusant, surfactant.
Described auxiliary agent is one or both in naphthalene sulfonic acid-formaldehyde condensation product, the resistance to sulfonic formaldehyde condensation compound of alkyl, benzyl naphthalene sulfonic formaldehyde condensation compound, lignosulfonates.Such as NNO, MF, CNF, Reax85A.
Described high color fastness to perspiration orange disperse dye is applied to hydrophobic material or blended material are dyeed or stamp.
Described hydrophobic material or blended material are acetate fiber, cotton, nylon, polyester fiber, acrylon, Pilus Caprae seu Ovis or spandex.
Described hydrophobic material or blended material can be thread, staple in bulk, and yarn is woven or the form of knitting fabric.
Described disperse dyes can adopt common dip method, pad-dyeing method to print and dye, it is also possible in direct printing.Described dyeing method is this area conventional method.
Beneficial effect
Preparation technology of the present invention is simple, and cost is low, for the dyestuff prepared, has a favorable reproducibility, water-fastness, rub resistance, resistance to distillation advantage, especially there is the feature that color fastness to perspiration is high.
Accompanying drawing explanation
Fig. 1 is the H1-NMR spectrogram of formula (I) compound.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is expanded on further.Should be understood that these embodiments are merely to illustrate the present invention rather than restriction the scope of the present invention.In addition, it is to be understood that after having read the content that the present invention lectures, the present invention can be made various changes or modifications by those skilled in the art, and these equivalent form of values fall within the application appended claims limited range equally.
Embodiment 1
The preparation of the carboxylate shown in formula (II)
Aniline 37g, acrylic acid 28.8g and water 100g being mixed, 90 DEG C of stirring reactions 20 hours, cooling, add methanol 200g, 0 DEG C is stirred 12 hours, filters, obtains the compound shown in formula (V).
Compound 16g shown in formula (V), water 150g, soda 11g, benzyl chloride 20g are mixed, stirring, adds potassium iodide 2g at 80 DEG C, reacts 12 hours, cooling, adding methanol 100g, 0 DEG C is stirred 12 hours, filters, obtains the compound shown in formula (IV).
By the compound shown in 25.5g formula (IV) and 100gDMF, soda 11g, bromacetone 14g mixing, it is warming up to 60 DEG C, adds potassium iodide 1g, stirring reaction 12 hours, is cooled to 40 DEG C, and add water 200g, filter, it is thus achieved that the carboxylate shown in formula (II).
The preparation of diazonium compound (III):
Water 8.7g, hydrochloric acid 17.8g and paranitroanilinum 5.2g are mixed, adds 18g trash ice, the aqueous solution of less than 0 DEG C dropping sodium nitrite 2.9g, diazo-reaction 2 hours at 5 DEG C, it is subsequently adding sulfamic acid 3.5g and processes the nitrite that unreacted is complete, it is thus achieved that diazotising liquid.
Coupling reaction:
Being slowly added into below 5 DEG C in the mixed liquor of 600g water and 350g trash ice by this diazotising liquid, stirring, 5 DEG C add the carboxylate 10.5g shown in formula (II), 10 DEG C are stirred 3 hours, filter, washing, it is thus achieved that the compound shown in 14.9g formula (I).Fusing point: 108 DEG C.H1-NMR (deuterated DMSO) spectrogram is shown in Fig. 1.
Embodiment 2
Formula (I) compound 40g and MF60g is added water after mixing, use grinder grinding distribution, then carry out spray drying, it is thus achieved that orange.
Embodiment 3
Respectively take the disperse dyes that 2.0g embodiment 2 prepares, the disperse dyes suspension that concentration is 2g/L it is made into respectively with water, take the water mixing of 2ml and 8ml, regulating dye bath pH with acetic acid is 5, then heats to 60 DEG C, is respectively put into fibrous material as shown in the table for 2g simultaneously and carries out high-temperature pressure dyeing, 130 DEG C it are warmed up in 30 minutes, it is incubated 30 minutes, cooling, sampling.Detection dye-uptake.And respectively according to the rub resistance of GB pertinent regulations testing example 2, water-fastness, sun-resistant and fastness to sublimation.
As shown in the table, the disperse dyes that the compounds of this invention prepares all are significantly better than prior art on colour fastness to rubbing, water-fastness color fastness, color fastness to perspiration, sun-resistant and color fastness to sublimation.
Table 1
Table 2
Table 3
Table 4
Claims (8)
1. one kind high color fastness to perspiration orange disperse dye monomeric compound, it is characterised in that: the structure of described compound shown in formula I:
2. a preparation method for high color fastness to perspiration orange disperse dye monomeric compound, comprises the steps:
(1) by aniline, acrylic acid, water mixing, 90-100 DEG C of stirring reaction 20-24 hour, cooling, adding methanol, 0-5 DEG C is stirred 12-18 hour；Filter, be subsequently added water, soda and benzyl chloride, mix and blend, add potassium iodide at 80-100 DEG C, react 12-18 hour, cooling, adding methanol, 0-5 DEG C is stirred 12-18 hour, by filter cake and DMF, soda and bromacetone mixing after filtration, it is warming up to 60-65 DEG C, add potassium iodide, stirring reaction 12-18 hour, be cooled to 40-45 DEG C, add water, filter and obtain carboxylate；
(2) water, hydrochloric acid and paranitroanilinum being mixed, add ice, less than 0 DEG C drips sodium nitrite in aqueous solution, at 5-6 DEG C diazo-reaction 2-4 hour, is subsequently adding the nitrite that sulfamic acid process unreacted is complete, it is thus achieved that diazotising liquid；
(3) adding above-mentioned diazotising liquid in frozen water mixed liquor, stirring, 5-10 DEG C adds carboxylate, and 10-15 DEG C is stirred 3-4 hour, filters, washing, it is thus achieved that orange disperse dye monomeric compound.
3. the application of a high color fastness to perspiration orange disperse dye monomeric compound as claimed in claim 1, it is characterised in that: described compound is applied individually to any to prepare disperse dyes or form dye composite with other dye monomers prepares disperse dyes.
4. the application of a kind of high color fastness to perspiration orange disperse dye monomeric compound according to claim 3, it is characterized in that: the preparation method of described disperse dyes particularly as follows: mix homogeneously compound with auxiliary agent 1:0.8-5 in mass ratio and grind under the existence of water or wetting agent, then carry out spray drying, to obtain final product.
5. the application of a kind of high color fastness to perspiration orange disperse dye monomeric compound according to claim 4, it is characterised in that: described auxiliary agent is one or both in dispersant, diffusant, surfactant.
6. the application of a kind of high color fastness to perspiration orange disperse dye monomeric compound according to claim 4, it is characterised in that: described auxiliary agent is one or both in naphthalene sulfonic acid-formaldehyde condensation product, the resistance to sulfonic formaldehyde condensation compound of alkyl, benzyl naphthalene sulfonic formaldehyde condensation compound, lignosulfonates.
7. the application of a kind of high color fastness to perspiration orange disperse dye monomeric compound according to claim 3, it is characterised in that: described disperse dyes are applied to hydrophobic material or blended material are dyeed or stamp.
8. the application of a kind of high color fastness to perspiration orange disperse dye monomeric compound according to claim 7, it is characterised in that: described hydrophobic material or blended material are acetate fiber, cotton, nylon, polyester fiber, acrylon, Pilus Caprae seu Ovis or spandex.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610063771.4A CN105733290A (en) | 2016-01-28 | 2016-01-28 | Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610063771.4A CN105733290A (en) | 2016-01-28 | 2016-01-28 | Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof |
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| CN105733290A true CN105733290A (en) | 2016-07-06 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610063771.4A Pending CN105733290A (en) | 2016-01-28 | 2016-01-28 | Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106497140A (en) * | 2016-09-14 | 2017-03-15 | 浙江龙盛集团股份有限公司 | A kind of high fastness indigo plant is to black disperse dye composition and dye preparations |
| CN106867274A (en) * | 2016-12-31 | 2017-06-20 | 浙江龙盛集团股份有限公司 | A kind of dispersion red dye composition and dye preparations |
| CN115806496A (en) * | 2022-12-28 | 2023-03-17 | 浙江闰土股份有限公司 | Disperse yellow-brown dye intermediate and preparation method thereof |
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| CN104919006A (en) * | 2013-01-14 | 2015-09-16 | 德司达染料分销有限公司 | AOX-free navy and black disperse dye mixtures |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106497140A (en) * | 2016-09-14 | 2017-03-15 | 浙江龙盛集团股份有限公司 | A kind of high fastness indigo plant is to black disperse dye composition and dye preparations |
| CN106497140B (en) * | 2016-09-14 | 2020-10-27 | 浙江龙盛集团股份有限公司 | High-fastness blue-to-black disperse dye composition and dye product |
| CN106867274A (en) * | 2016-12-31 | 2017-06-20 | 浙江龙盛集团股份有限公司 | A kind of dispersion red dye composition and dye preparations |
| CN106867274B (en) * | 2016-12-31 | 2019-06-28 | 浙江龙盛集团股份有限公司 | A kind of dispersion red dye composition and dye preparations |
| CN115806496A (en) * | 2022-12-28 | 2023-03-17 | 浙江闰土股份有限公司 | Disperse yellow-brown dye intermediate and preparation method thereof |
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