CN105647224A - Phthalimide-azo disperse dye monomeric compound and preparing method and application thereof - Google Patents
Phthalimide-azo disperse dye monomeric compound and preparing method and application thereof Download PDFInfo
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- CN105647224A CN105647224A CN201610058677.XA CN201610058677A CN105647224A CN 105647224 A CN105647224 A CN 105647224A CN 201610058677 A CN201610058677 A CN 201610058677A CN 105647224 A CN105647224 A CN 105647224A
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- compound
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- phthalimide
- azo dispersion
- dispersion dyes
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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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
-
- 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
- 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
Abstract
The invention relates to a phthalimide-azo disperse dye monomeric compound and a preparing method and application thereof. The structural formula of the compound is shown as the formula I in the specification. According to the preparing method, a diazotization and coupling reaction mode is adopted for preparation. The phthalimide-azo disperse dye monomeric compound is independently applied to preparing disperse dyes or forms dye compositions with other dye monomers to prepare disperse dyes. The preparing process is simple, cost is low, and the phthalimide-azo disperse dye monomeric compound has the advantages of being good in reproducibility and resistant to washing, friction and sublimation.
Description
Technical field
The invention belongs to nonionic dye field, particularly to a kind of phthalimide-azo dispersion dyes monomer 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 WO9520014, WO2005056690 and WO2008049758 connect the azo dispersion dyes that 2-oxoalkyl group esters replace, there is excellent washability and splendid resistance to sublimability. CN1711319 discloses the azo dispersion dyes of the phthalimide that a series of cyano group replaces, and has good washability. But, the printing and dyeing effect that these known dyes produce still cannot meet all demands. Therefore the new dye of superperformance is remained a need for.
Summary of the invention
The technical problem to be solved is to provide a kind of phthalimide-azo dispersion dyes monomer compound and its preparation method and application, preparation technology is simple for this compound, cost is low, for the dyestuff prepared, there is the advantage of favorable reproducibility, water-fastness, rub resistance, resistance to distillation.
A kind of phthalimide-azo dispersion dyes monomer compound of the present invention, the structure of described compound shown in formula I:Wherein, wherein, R1It is C1-C4Alkyl; R2And R3It is individually by one or more C1-C4Alkyl-carbonyl replace C1-C4Alkyl.
Preferably, described R1It is methyl or ethyl; R2And R3It is individually the C replaced by methoxycarbonyl or ethoxy carbonyl1-C4Alkyl.
Most preferred, the structure of described compound is such as shown in Formulas I-1:
The preparation method of the present invention prepares the intermediate shown in formula (II) with reference to method disclosed in CN1288461 and CN1711319, for instance, phthalimide is carried out in acid condition nitrated, halogenation and reduction.
Wherein X represents halogen, it is preferable that bromine.
By formula (II) intermediate conventionally diazotising and and formula (III) coupling compounds, then replace halogen with cyano group,
Described halogenation is when such as hydrobromic acid and hydrogen peroxide, or in acetic acid with acetic acid sodium reaction, then with bromine reaction obtain corresponding bromide.
Described diazo-reaction is known conventional method, for instance react with nitrosyl sulfuric acid, can add other acid, such as sulphuric acid, hydrochloric acid etc. in reaction.
Described coupling reaction is known conventional method, for instance, in acid condition, in water-bearing media, carry out lower than under 10 DEG C of conditions.
It is known method that described cyano group replaces, for instance in the presence of CuCN or CuCN and the mixture of alkali metal cyanide, carry out in a solvent.
Concrete, the preparation method of Formulas I-1 monomeric compound of the present invention, comprise the steps:
(1) formula 1 compound, hydrogen peroxide, hydrobromic acid solution and water are mixed, be stirred at room temperature 8��10 hours, obtain Formula II-1 compound; Wherein,
The structural formula of formula 1 compound is
The structural formula of Formula II-1 compound is
(2) at 0 DEG C, in sulphuric acid, drip mixture of ice and water, at 25 DEG C, then add Formula II-1 compound, stir, add nitrosyl sulfuric acid, stirring 2��4 hours at 20��30 DEG C, the complete addition sulfamic acid of question response processes, and obtains diazotising liquid;
(3) in frozen water mixed liquor, add sulphuric acid and formula III-1 compound, below 0 DEG C, add above-mentioned diazo liquid, stirring reaction 2��4 hours at 5 DEG C, filter, washing, dry, it is thus achieved that Formula V-1 compound; Wherein,
The structural formula of formula III-1 compound is
The structural formula of Formula V-1 compound is
(4) Formula V-1 compound, sodium bromide and cyaniding Asia ketone are added in DMF, be warming up to 80��85 DEG C, stirring reaction 1��2 hour, filter, washing, dry, obtain phthalimide-azo dispersion dyes monomer compound.
Compound shown in formula (II) and formula (III) obtains also by the mode of commercially available purchase.
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 phthalimide-azo dispersion dyes 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 the advantage of favorable reproducibility, water-fastness, rub resistance, resistance to distillation.
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
Reaction equation is as follows:
(1) by formula (1) compound 19g, 20.4ml hydrogen peroxide, the hydrobromic acid solution of 11.4ml and 50ml water mix, and are stirred at room temperature 8 hours, it is thus achieved that the compound shown in formula (II-1).
(2) at 0 DEG C, in the sulphuric acid of 56ml96%, 20ml mixture of ice and water it is slowly added dropwise, by 26.9g formula (II-1) compound at 25 DEG C, stir, add 15g nitrosyl sulfuric acid, stir 2 hours at 20 DEG C, add sulfamic acid to process, prepare diazo liquid, i.e. compound shown in formula (IV-1).
(3) in the mixed liquor of 25g water and 50g ice, 2g sulphuric acid and formula (III-1) compound 28.1g are added, above-mentioned diazo liquid it is slowly added to below 0 DEG C, stirring reaction 2 hours at 5 DEG C, filter, clear water washing is dry, it is thus achieved that the compound shown in formula (V-1).
(4) formula (V-1) compound 6g, 0.35g sodium bromide, 1.3g cyaniding Asia ketone are added in 20mlDMF, be warming up to 80 DEG C, stirring reaction 1 hour, filter, washing, dry, obtain the compound shown in 4.9g formula (I-1). Fusing point 168 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 pink dyestuff.
Embodiment 3
The disperse dyes of the compound containing formula are prepared according to the method for embodiment 1 and 2:
Embodiment 4
The disperse dyes of the compound containing formula are prepared according to the method for embodiment 1 and 2:
Embodiment 5
The disperse dyes of the compound containing formula are prepared according to the method for embodiment 1 and 2:
Embodiment 6
Take the 2.0g embodiment 2-5 disperse dyes prepared respectively, 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 colour fastness to rubbing of GB pertinent regulations testing example 2, water-fastness color fastness and color 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 and color fastness to sublimation.
Table 1
Table 2
Table 3
Claims (10)
1. phthalimide-azo dispersion dyes monomer compound, it is characterised in that: the structure of described compound shown in formula I:
Wherein, wherein, R1It is C1-C4Alkyl; R2And R3It is individually by one or more C1-C4Alkyl-carbonyl replace C1-C4Alkyl.
2. a kind of phthalimide-azo dispersion dyes monomer compound according to claim 1, it is characterised in that: described R1It is methyl or ethyl; R2And R3It is individually the C replaced by methoxycarbonyl or ethoxy carbonyl1-C4Alkyl.
3. a kind of phthalimide-azo dispersion dyes monomer compound according to claim 1, it is characterised in that: the structure of described compound is such as shown in Formulas I-1:
4. a preparation method for phthalimide-azo dispersion dyes monomer compound, comprises the steps:
(1) formula 1 compound, hydrogen peroxide, hydrobromic acid solution and water are mixed, be stirred at room temperature 8��10 hours, obtain Formula II-1 compound; Wherein,
The structural formula of formula 1 compound is
The structural formula of Formula II-1 compound is
(2) at 0 DEG C, in sulphuric acid, drip mixture of ice and water, at 25 DEG C, then add Formula II-1 compound, stir, add nitrosyl sulfuric acid, stirring 2��4 hours at 20��30 DEG C, the complete addition sulfamic acid of question response processes, and obtains diazotising liquid;
(3) in frozen water mixed liquor, add sulphuric acid and formula III-1 compound, below 0 DEG C, add above-mentioned diazo liquid, stirring reaction 2��4 hours at 5 DEG C, filter, washing, dry, it is thus achieved that Formula V-1 compound; Wherein,
The structural formula of formula III-1 compound is
The structural formula of Formula V-1 compound is
(4) Formula V-1 compound, sodium bromide and cyaniding Asia ketone are added in DMF, be warming up to 80��85 DEG C, stirring reaction 1��2 hour, filter, washing, dry, obtain phthalimide-azo dispersion dyes monomer compound.
5. the application of phthalimide-azo dispersion dyes monomer 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.
6. the application of a kind of phthalimide-azo dispersion dyes monomer compound according to claim 5, 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.
7. the application of a kind of phthalimide-azo dispersion dyes monomer compound according to claim 6, it is characterised in that: described auxiliary agent is one or both in dispersant, diffusant, surfactant.
8. the application of a kind of phthalimide-azo dispersion dyes monomer compound according to claim 6, 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.
9. the application of a kind of phthalimide-azo dispersion dyes monomer compound according to claim 6, it is characterised in that: described disperse dyes are applied to hydrophobic material or blended material are dyeed or stamp.
10. the application of a kind of phthalimide-azo dispersion dyes monomer compound according to claim 8, 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 |
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| CN201610058677.XA CN105647224A (en) | 2016-01-28 | 2016-01-28 | Phthalimide-azo disperse dye monomeric compound and preparing method and application thereof |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980734A (en) * | 1972-07-06 | 1976-09-14 | Hoechst Aktiengesellschaft | Thermoplastic moulding compositions based on poly (oxymethylene) |
| CN1331730A (en) * | 1998-12-31 | 2002-01-16 | 西巴特殊化学品控股有限公司 | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
| CN1491258A (en) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | Phthalimidyl azo dyes, process for preparation thereof and the use thereof |
| CN1711319A (en) * | 2002-11-11 | 2005-12-21 | 西巴特殊化学品控股有限公司 | Phthalimidyl-azo dyes, process for their preparation and their use |
| CN101454402A (en) * | 2006-06-14 | 2009-06-10 | 德意志戴斯达纺织品及染料两合公司 | Disperse dyes, production and their use |
| CN102876068A (en) * | 2012-10-22 | 2013-01-16 | 浙江万丰化工有限公司 | Preparation method of phthaloyl azo dye |
| CN104403348A (en) * | 2014-11-18 | 2015-03-11 | 李百春 | Purple disperse dye with high washing fastness and sublimation fastness and preparation method of purple disperse dye |
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-
2016
- 2016-01-28 CN CN201610058677.XA patent/CN105647224A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980734A (en) * | 1972-07-06 | 1976-09-14 | Hoechst Aktiengesellschaft | Thermoplastic moulding compositions based on poly (oxymethylene) |
| CN1331730A (en) * | 1998-12-31 | 2002-01-16 | 西巴特殊化学品控股有限公司 | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
| CN1491258A (en) * | 2001-02-07 | 2004-04-21 | �������⻯ѧƷ�ع�����˾ | Phthalimidyl azo dyes, process for preparation thereof and the use thereof |
| CN1711319A (en) * | 2002-11-11 | 2005-12-21 | 西巴特殊化学品控股有限公司 | Phthalimidyl-azo dyes, process for their preparation and their use |
| CN101454402A (en) * | 2006-06-14 | 2009-06-10 | 德意志戴斯达纺织品及染料两合公司 | Disperse dyes, production and their use |
| CN104520498A (en) * | 2012-07-27 | 2015-04-15 | 亨斯迈先进材料（瑞士）有限公司 | Disperse azo dyes, a process for the preparation thereof and the use thereof |
| CN102876068A (en) * | 2012-10-22 | 2013-01-16 | 浙江万丰化工有限公司 | Preparation method of phthaloyl azo dye |
| CN104403348A (en) * | 2014-11-18 | 2015-03-11 | 李百春 | Purple disperse dye with high washing fastness and sublimation fastness and preparation method of purple disperse dye |
Non-Patent Citations (2)
| Title |
|---|
| JAE-HONG CHOI 等: "Coloration properties and clearability of phthalimide-derived monoazo disperse dyes containing ester groups", 《COLORATION TECHNOLOGY》 * |
| JAE-HONG CHOI等: "Synthesis and spectroscopic properties of novel phthalimide-derived monoazo disperse dyes containing ester groups", 《COLORATION TECHNOLOGY》 * |
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Application publication date: 20160608 |