CN103601656B - A kind of tetrazo compound and comprise the complex black dye of this compound - Google Patents
A kind of tetrazo compound and comprise the complex black dye of this compound Download PDFInfo
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- CN103601656B CN103601656B CN201310544833.XA CN201310544833A CN103601656B CN 103601656 B CN103601656 B CN 103601656B CN 201310544833 A CN201310544833 A CN 201310544833A CN 103601656 B CN103601656 B CN 103601656B
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Abstract
The invention discloses a kind of tetrazo compound and comprise the complex black dye of this compound, this tetrazo compound molecular formula is such as formula shown in I or formula II:
this complex black dye comprises the compound of above-mentioned formula I and formula II, also comprises the compound of formula III:
Description
Technical field
The present invention relates to a kind of tetrazo compound and comprise the complex black dye of this compound.
Background technology
In the last few years, ink for ink-jet print and digital printing technology obtain tremendous development, particularly require more and more higher to black dyes component, the plurality of advantages such as specific conductivity is low, surface tension is moderate, degree of fixation is high, sun-resistant and washing fastness is high that the selection of dyestuff need dyestuff have.The compound of existing dye well composition dyestuff still has part of properties not reach necessary requirement.
Summary of the invention
In order to solve the aforementioned problems in the prior, the invention provides a kind of tetrazo compound, and comprise the complex black dye of this compound.
Tetrazo compound provided by the invention, molecular formula is such as formula shown in I or formula II:
The preparation method of above-mentioned tetrazo compound, step is as follows:
(1) get 365 ~ 375 weight part DSD acid to add water after stirring to pulp and be cooled to 5 DEG C, continue stirring 20 ~ 40 minutes, then add hydrochloric acid 220 ~ 250 weight part of massfraction 30%, stir and obtain acid mixture;
(2) 130 ~ 150 weight part Sodium Nitrites are mixed with the aqueous solution of massfraction 30%, join in acid mixture, adjust ph is 1.2 ~ 1.5, and control temperature is between 5 ~ 10 DEG C, carry out diazotization reaction, add thionamic acid after reaction terminates and eliminate unnecessary Sodium Nitrite and obtain diazonium salt;
(3) in the diazonium salt of step (2), 300 ~ 310 weight part 2-hydroxy-3-methyl phenylformic acid are added, react after disappearing to 2-hydroxy-3-methyl phenylformic acid under temperature 5 ~ 8 DEG C of conditions, pH value is adjusted to 5.0 ~ 6.0, reaction is continued to can't detect diazonium salt under temperature is 8 ~ 10 DEG C of conditions, reaction terminates, cross nanofiltration membrane to purify, last spraying dry obtains formula I dyestuff; Or
145 ~ 155 weight part 2-hydroxy-3-methyl phenylformic acid are added in the diazonium salt of step (2), react after disappearing to 2-hydroxy-3-methyl phenylformic acid under temperature 5 ~ 8 DEG C of conditions, pH value is adjusted to 5.0 ~ 6.0, add 230 ~ 245 weight part γ acid again, adjust the temperature to 8 ~ 12 DEG C, pH value 6.0 ~ 6.5, continue reaction to can't detect diazonium salt, reaction terminates, and cross nanofiltration membrane and purify, last spraying dry obtains formula II dyestuff.
Preferably, the preparation method of above-mentioned tetrazo compound, step (3) uses the soda ash water adjust ph of saleratus power or massfraction 20%.
Above-mentioned tetrazo compound is preparing the application in dyestuff or ink.
A kind of complex black dye, comprises with the compound of following formula I, formula II and formula III:
Preferably, above-mentioned complex black dye, the compound quality percentage composition of described formula I, formula II and formula III is respectively 30 ~ 40%, 10 ~ 30% and 30 ~ 60%.
The preparation method of above-mentioned complex black dye is the compound of modus ponens I, formula II and formula III, and mechanical stirring mixes.
The application of above-mentioned complex black dye in preparation textile dye or ink.
Compared with prior art, the present invention has following beneficial effect:
1, tetrazo compound provided by the invention, has linear levelling and longer conjugate system altogether preferably, especially high to the avidity of fiber, is mainly used in cotton, fiber crops, viscose glue, silk dyeing and stamp, can also be used for the making of ink.
2, complex black dye provided by the invention, has following characteristics:
1. high-dissolvability: because in dye structure, sulfonic acid group is many, solubleness can reach 250g/L.2. high colour-fast rate: because three kinds of dye structures are close, basically identical to dyeing condition susceptibility, and the individual difference on molecular structure causes the strong and weak difference in their polarity, make they fabric is dyeed or stamp time, to utilize in polarity complementary synergistic effect to improve the fastness ability of the compound dyestuff of dyestuff formula I and formula II structure.3. stability is strong: the features such as the close intermiscibility of structure is good, make its composite obtained composite dye light fastness reach 5 grades, washing fastness index reaches 4 ~ 5 grades.4. specific conductivity is low: this complex black dye all adopted film mode to purify to dyestuff, and in dyestuff, salt, metal ion and calcium ions and magnesium ions are all less, thus caused specific conductivity low, makes this dyestuff be more applicable for digit printing and ink making.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, and to make those skilled in the art the present invention may be better understood and can be implemented, but illustrated embodiment is not as a limitation of the invention.
The tetrazo compound preparation of embodiment 1 formula I and formula II structure
370 weight part DSD acid are added appropriate water pull an oar 1 hour, be on the rocksly cooled to 5 DEG C and stir 30 minutes, then hydrochloric acid 240 weight part adding massfraction 30% continues stirring 30 minutes to evenly obtaining acid mixture.After 140 weight part Sodium Nitrites are made into the aqueous solution of massfraction 30%, join in the acid mixture of DSD acid and hydrochloric acid carry out diazotization reaction about 60 minutes (after namely obtaining acid mixture), holding temperature 5 ~ 10 DEG C, pH value is 1.2 ~ 1.5 reaction 2 hours, reaction terminates rear thionamic acid and eliminates unnecessary Sodium Nitrite and obtain diazonium salt, then 304 weight part 2-hydroxy-3-methyl phenylformic acid are added, holding temperature 5 ~ 8 DEG C reaction 4 is little disappears (available profit circle detects) up to 2-hydroxy-3-methyl phenylformic acid, pH value saleratus power is adjusted to 5.0 ~ 6.0, holding temperature 8 ~ 10 DEG C, pH value 5.0 ~ 6.0 reaction 3 is little of can't detect diazonium salt, reaction terminates.Purified by nanofiltration membrane remove portion salt and secondary dyestuff, spraying dry can obtain type I compound:
370 weight part DSD acid are added appropriate water pull an oar 1 hour, be on the rocksly cooled to 5 DEG C and stir 30 minutes, then the hydrochloric acid 240 parts adding massfraction 30% continues stirring 30 minutes to evenly obtaining acid mixture.After 140 weight part Sodium Nitrites are made into the aqueous solution of massfraction 30%, join in the acid mixture of DSD acid and hydrochloric acid carry out diazotization reaction about 60 minutes (after namely obtaining acid mixture), holding temperature 5 ~ 10 DEG C, pH value is 1.2 ~ 1.5 reaction 2 hours, and reaction terminates rear thionamic acid and eliminates unnecessary Sodium Nitrite and obtain diazonium salt.Then 152 weight part 2-hydroxy-3-methyl phenylformic acid are added, holding temperature 5 ~ 8 DEG C reaction 4 is little disappears (available profit circle detects) up to 2-hydroxy-3-methyl phenylformic acid, pH value saleratus power is adjusted to 5.0 ~ 6.0, add 239 weight part γ acid holding temperatures 8 ~ 12 DEG C again, pH value 6.0 ~ 6.5 reaction 6 is little of can't detect diazonium salt, reaction terminates.Purified by nanofiltration membrane remove portion salt and secondary dyestuff, spraying dry can obtain the compound of formula II structure:
The preparation of embodiment 2 complex black dye
565 weight part 4-sulfovinic acid sulfuryl aniline are added appropriate water pull an oar 1 hour, on the rocks be cooled to 8 DEG C stir 30 minutes, maintain the temperature of 8 DEG C, hydrochloric acid 240 weight part adding massfraction 30% continues stirring 30 minutes, after 140 weight part Sodium Nitrites are made into the aqueous solution of massfraction 30%, joined in 30 minutes in the mixture of 4-sulfovinic acid sulfuryl aniline and hydrochloric acid and carry out diazotization reaction.Holding temperature is at 5 ~ 8 DEG C, and pH value 1.0 ~ 1.2 is reacted after 1.5 hours and eliminated unnecessary Sodium Nitrite with thionamic acid.341 weight part 1-amino-8-naphthol-3.6-disulfonate sodiums will be added in diazonium salt after eliminating unnecessary Sodium Nitrite, pH value was adjusted to 6.0 ~ 6.5 with saleratus power after 5 hours by holding temperature 0 ~ 5 DEG C reaction, holding temperature 8 ~ 12 DEG C, pH value 6.0 ~ 6.5 react 3 hours, purified by nanofiltration membrane remove portion salt and secondary dyestuff, spraying dry can obtain formula III compound:
By 40 weight part type I compound, 30 weight part formula II compounds and 30 weight part formula III compounds, fully machinery mixing, complex black dye of the present invention can be obtained.
Embodiment 3
By the fully machinery mixing of formula III compound of 30 weight part type I compound of the present invention, 10 weight part formula II compounds and 60 parts by weight of example 2, complex black dye of the present invention can be obtained.
Embodiment 4
By the fully machinery mixing of formula III compound of 30 weight part type I compound of the present invention, 20 weight part formula II compounds and 50 parts by weight of example 2, complex black dye of the present invention can be obtained.
Embodiment 5 performance test
Carry out properties test to complex black dye prepared by embodiment 2,3,4, result is as table 1:
Table 1 complex black dye detected result
The composite Mixed Pinyin technical process of embodiment 6 complex black dye
After being prepared by the complex black dye of embodiment 4, control temperature is less than 30 DEG C, adds the dust-proofing agent accounting for dyestuff gross weight 0.5%, stirs, and after sampling detection is qualified, carries out packing by customer requirement.
The tetrazo compound preparation of embodiment 7 formula I and formula II structure
With the tetrazo compound of different material consumption preparation formula I and formula II structure, in different numbering group, each raw material dosage sees the following form 2 and table 3 respectively, and other preparation conditions are consistent with embodiment 1.
The each raw material dosage of tetrazo compound of table 2 structure shown in formula I
The each raw material dosage of tetrazo compound of table 3 formula II structure
Each group also can obtain tetrazo compound product above, but productive rate and purity are all lower than embodiment 1, cannot reach optimum by its composite complex black dye quality.
The above embodiment is only that protection scope of the present invention is not limited thereto in order to absolutely prove the preferred embodiment that the present invention lifts.The equivalent alternative or conversion that those skilled in the art do on basis of the present invention, all within protection scope of the present invention.Protection scope of the present invention is as the criterion with claims.
Claims (4)
1. a complex black dye, is characterized in that, comprises with the compound of following formula I, formula II and formula III:
formula I;
formula II;
formula III.
2. complex black dye according to claim 1, is characterized in that, the compound quality percentage composition of described formula I, formula II and formula III is respectively 30 ~ 40%, 10 ~ 30% and 30 ~ 60%.
3. the preparation method of the complex black dye described in claim 1 or 2, is characterized in that the compound of modus ponens I, formula II and formula III, and mechanical stirring mixes.
4. the application of the complex black dye described in claim 1 or 2 in preparation textile dye or ink.
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| CN201310544833.XA CN103601656B (en) | 2013-11-06 | 2013-11-06 | A kind of tetrazo compound and comprise the complex black dye of this compound |
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| CN201310544833.XA CN103601656B (en) | 2013-11-06 | 2013-11-06 | A kind of tetrazo compound and comprise the complex black dye of this compound |
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| CN103601656B true CN103601656B (en) | 2015-10-28 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5980623A (en) * | 1997-01-29 | 1999-11-09 | Fuji Xerox Co., Ltd. | Ink set for ink jet recording and ink jet recording method |
| CN102040855A (en) * | 2010-12-01 | 2011-05-04 | 平顶山市凯斯特染料有限公司 | Method for preparing direct yellow G |
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- 2013-11-06 CN CN201310544833.XA patent/CN103601656B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5980623A (en) * | 1997-01-29 | 1999-11-09 | Fuji Xerox Co., Ltd. | Ink set for ink jet recording and ink jet recording method |
| CN102040855A (en) * | 2010-12-01 | 2011-05-04 | 平顶山市凯斯特染料有限公司 | Method for preparing direct yellow G |
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