CN104559315B - Yellow mixed crystal type disperse dye - Google Patents
Yellow mixed crystal type disperse dye Download PDFInfo
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- CN104559315B CN104559315B CN201410790583.2A CN201410790583A CN104559315B CN 104559315 B CN104559315 B CN 104559315B CN 201410790583 A CN201410790583 A CN 201410790583A CN 104559315 B CN104559315 B CN 104559315B
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- hydroxyquinoline
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- mixed crystal
- phthalic anhydride
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- FDTLQXNAPKJJAM-UHFFFAOYSA-N Oc1cc(cccc2)c2nc1C(C(c1ccccc11)=O)C1=O Chemical compound Oc1cc(cccc2)c2nc1C(C(c1ccccc11)=O)C1=O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a kind of be applicable to terylene and blend fibre dyeing or the yellow mixed crystal type disperse dye of stamp.Described yellow mixed crystal disperse dyes: by 2 methyl 3 hydroxyquinoline or/and the phthalic anhydride of the mixture that forms of 2 methyl 3 hydroxyquinoline 4 carboxylic acids and 2 methylquinolines and excess, under having catalyst existence condition, in the boiling point organic solvent higher than 220 DEG C, keep 6～9 hours at 190 DEG C～220 DEG C of states, obtain；Wherein, described catalyst is anhydrous zinc chloride or aluminum trichloride (anhydrous).Present invention successfully solves C.I. disperse yellow 54 present in prior art on the high side, and the problem of yellow SYJ dyeability difference.
Description
Technical field
The present invention relates to a kind of be applicable to terylene and blend fibre dyeing or the yellow mixed crystal type disperse dye of stamp.
Background technology
C.I. disperse yellow 23 (structure is as shown in Equation 1) is the big kind (being commonly called as one of old three samples) of a Yellow disperse dye, it
Because going out human body is had the aromatic amine of potential carcinogenecity (P-aminoazobenzene) and use of being banned by reductive cleavage under given conditions,
But it manufactures simplicity, cheap, and application performance is the most excellent, so to find other kinds that can replace it economically
It is not easy to.
For dyeability, as the succedaneum of C.I. disperse yellow 23, C.I. disperse yellow 54 (compound shown in formula 2) is one
Individual more suitably candidate.But, compared to C.I. disperse yellow 23, C.I. disperse yellow 54 on the high side, reason is to produce C.I.
The preparation cost of the intermediate (2-methyl-3-Hydroxy-quinolin or 2-methyl-3-Hydroxy-quinolin-4-carboxylic acid) required for disperse yellow 54 is relatively
High.
2-methyl-3-Hydroxy-quinolin, is prepared through condensation closed loop with hydroxypropanone-(being prepared by 1-bromacetone) by o-Aminobenzaldehyde.
And the method synthesizing o-Aminobenzaldehyde mainly has two kinds: the first, with 1-Formyl-2-nitrobenzene as initiation material, through reduction reaction,
Obtain o-Aminobenzaldehyde.But owing to the price of 1-Formyl-2-nitrobenzene is the highest, general manufacturing enterprise will not use the method to produce neighbour
Aminobenzaldehyde；Its two (current manufacturing enterprise is commonly used) is, with ortho-aminotoluene as initiation material, first with phosgene effect
Obtain adjacent toluene Carbimide., then obtain neighbour's (dichloromethyl) benzene Carbimide. through chlorination, after obtain o-Aminobenzaldehyde through hydrolysis.
Existing synthesis 2-methyl-3-hydroxyquinoline route is as follows:
The synthesis of 2-methyl-3-hydroxyquinoline-4-carboxylic acid, with aniline as initiation material, first with oxammonium hydrochloride. and chloral hydrate condensation,
Obtaining α-oximido antifebrin, then, α-oximido antifebrin closed loop in concentrated sulfuric acid and hydrolysis obtain isatin, finally, and isatin
Reacting with hydroxypropanone-or chlroacetone, obtain 2-methyl-3-hydroxyquinoline-4-carboxylic acid, synthetic route is as follows:
From the foregoing, it will be observed that either synthesis 2-methyl-3-hydroxyquinoline or 2-methyl-3-hydroxyquinoline-4-carboxylic acid all needs through tediously long
Process, thus cause its preparation cost to rise.
Summary of the invention
From previous analysis, the complexity preparing intermediate 2-methyl-3-hydroxyquinoline or 2-methyl-3-hydroxyquinoline-4-carboxylic acid is
Cause the one of the main reasons of C.I. disperse yellow 54 high expensive.
The scheme of a kind of C.I. of reduction disperse yellow 54 production cost is, replaces 2-methyl-3-hydroxyquinoline with 2-methylquinoline.Because
2-methylquinoline is a natural product (it is present in the wash oil fraction of coal tar), is easier to obtain, and relative low price.
But the analog that the product replacing the synthesis of 2-methyl-3-hydroxyquinoline to obtain with 2-methylquinoline is C.I. disperse yellow 54 (is named " yellow
SYJ "), its reaction equation is as follows:
Though yellow only few than C.I. disperse yellow 54 hydroxyl of SYJ, its dyeability is more far short of what is expected than C.I. disperse yellow 54,
Mainly its dyeing lifting force is the poorest, besides the coloured light more gorgeous than C.I. disperse yellow 54 (the greenest) of yellow SYJ, with it and its
His Color of dyestuff colorant match is the most undesirable.
In order to solve the problems referred to above, the present invention proposes the solution of a kind of mixed crystal dyestuff.
Mixed crystal dyestuff refers to: by component A and component B by component C with equimolar (or excess) after different mixed in molar ratio
Reaction, the product obtained is mixed crystal dyestuff, and it is a mixture.X-ray diffraction (XRD) figure of mixed crystal dyestuff is with mixed
Close X-ray diffraction (XRD) figure of dyestuff (AC+BC) incomplete same (this is because may in building-up process
New crystal is had to produce), wherein, described mixed dye (AC+BC) refers to: uses component A to react with component C and is produced
Thing AC, uses component B to react with component C and obtains product BC.By product AC and product BC through physical mixed, just obtain
Mixed dye (AC+BC).The X-ray diffraction (XRD) of mixed dye (AC+BC) is exactly that dyestuff AC and dyestuff BC is each
Superposition from X-ray diffraction behavior.
The present invention is by 2-methyl-3-hydroxyquinoline or 2-methyl-3-hydroxyquinoline-4-carboxylic acid (component A) and 2-methylquinoline (component
B) after mixing, the phthalic anhydride (component C) with equimolar or excess reacts, and obtains mixed crystal dyestuff.Coloration result shows: institute of the present invention
The dyeability of the mixed crystal dyestuff of preparation is better than C.I. disperse yellow 54, thus successfully solves problems of the prior art
(i.e. C.I. disperse yellow 54 is on the high side, and the problem of yellow SYJ dyeability difference).
Yellow mixed crystal dyestuff of the present invention, is mainly prepared by following method:
Under having catalyst existence condition, by 2-methyl-3-hydroxyquinoline (compound shown in formula Aa) or/and 2-methyl-3-hydroxyl
Mixture that Cinchonic Acid's (compound shown in formula Ab) and 2-methylquinoline (compound shown in formula B) form and equimolar
Or the phthalic anhydride (compound shown in formula C) of excess is in boiling point is higher than the organic solvent of 220 DEG C, at 190 DEG C～220 DEG C (preferably
200 DEG C～210 DEG C) 6～9 hours (preferably 7～8 hours) of reaction, obtain object (mixed crystal dyestuff of the present invention)；
Wherein, described catalyst is anhydrous zinc chloride or aluminum trichloride (anhydrous).
Accompanying drawing explanation
Fig. 1. the XRD figure spectrum of the mixed dye being made up of C.I. disperse yellow 54 and yellow SYJ；
Fig. 2. the XRD figure spectrum of the mixed crystal dyestuff prepared by embodiment 1；
Fig. 3. the XRD figure spectrum of the mixed crystal dyestuff prepared by embodiment 2；
Fig. 4. the XRD figure spectrum of the mixed crystal dyestuff prepared by embodiment 3.
Detailed description of the invention
Term illustrates:
2-methyl-3-hydroxyquinoline, compound shown in formula Aa, hereafter it is abbreviated as " Aa "；
2-methyl-3-hydroxyquinoline-4-carboxylic acid, compound shown in formula Ab, hereafter it is abbreviated as " Ab "；
2-methylquinoline, compound shown in formula B, hereafter it is abbreviated as " B "；With
Phthalic anhydride, compound shown in formula C, hereafter it is abbreviated as " C ".
In one preferred technical scheme of the present invention, the consumption of described catalyst (anhydrous zinc chloride or aluminum trichloride (anhydrous))
For Aa or/and the 20% of the summation of the molal quantity of the molal quantity of Ab and B.
In presently preferred technical scheme, the organic solvent being suitable for the present invention is: trichloro-benzenes, Nitrobenzol, quinoline
Or derivant, temperature meet the requirements the conduction oil of (boiling point be higher than 220 DEG C) or phthalic anhydride.
When organic solvent used is non-phthalic anhydride, the mol ratio of reactant is: Aa is or/and Ab:B:C=0.1～0.9:0.9～0.1:
1～2, preferred mol ratio: Aa are or/and Ab:B:C=0.3～0.7:0.7～0.3:1～1.5；
When organic solvent used is phthalic anhydride, the mol ratio of reactant is: Aa or/and the mol ratio of Ab, B and C: Aa or/
With Ab:B:C=0.1～0.9:0.9～0.1:3～10, preferred mol ratio: Aa or/and Ab:B:C=0.3～0.7:
0.7～0.3:3～5.
Below by way of example, the present invention is described in detail, but the cited case is not limiting as protection scope of the present invention, although right
The present invention elaborates, and has quoted some instantiations as proof, as long as but it will be understood by those skilled in the art that without departing from this
The spirit and scope of invention, it is obvious for doing various changes and modifications.
In the following example, the source of primary raw material is as follows:
2-methyl-3-hydroxyquinoline-4-carboxylic acid (Ab) is industrial goods, purity 97%, and Zhejiang mountain valley Dye Co., Ltd produces；
2-methylquinoline (B) is industrial goods, purity 97%, and Shanghai warm chemical science and technology Development Co., Ltd produces；
Phthalic anhydride (C) is industrial goods, purity 99%, and Changzhou Qinghong Chemical Co., Ltd. produces.
Embodiment 1 (Ab with B equimolar mixes)
Under stirring, 500ml there-necked flask is sequentially added into quinoline (350ml), 2-methylquinoline (12.0g, 0.084mol), 2-
Methyl-3-hydroxyquinoline-4-carboxylic acid (17.1g, 0.084mol), phthalic anhydride (37.3g, 0.252mol), ZnCl2(4.57g), heating
Mixture to 200 DEG C, reacts 7-8 hour, slightly after cooling, filters, and filter cake methanol washes away quinoline, then with Recrystallisation from acetic acid,
Wash away acetic acid, obtain dark yellow solid (30.9g) after drying, fusing point: 246.2 DEG C～249.2 DEG C (are abbreviated as that " yellow mixed crystal divides
Dissipate dyestuff-1 ").
Accompanying drawing 2 is shown in by X-ray diffraction (XRD) collection of illustrative plates of " yellow mixed crystal disperse dyes-1 ".
Standardization program sand milling pressed by " the yellow mixed crystal disperse dyes-1 " of undried, with the business of C.I. disperse yellow 54 in dye model machine
Product are standard specimen, and to polyster fibre dyeing, result shows: both coloured light is close, and the dyeing of " yellow mixed crystal disperse dyes-1 " is strong
Spending higher than the staining power of C.I. disperse yellow 54 by 10%, the dyeing enhancing rate of " yellow mixed crystal disperse dyes-1 " is than C.I. disperse yellow
The dyeing enhancing rate of 54 is high by 10%, the fastness to sublimation of " yellow mixed crystal disperse dyes-1 " than C.I. disperse yellow 54 resistance to distillation jail
Spend high half grade.
Embodiment 2 (Ab with B mixes with mol ratio for 1:1.5)
Under stirring, 500ml there-necked flask is sequentially added into quinoline (450ml), 2-methylquinoline (20.0g, 0.140mol), 2-
Methyl-3-hydroxyquinoline-4-carboxylic acid (19.1g, 0.094mol), phthalic anhydride (51.9g, 0.351mol), ZnCl2(6.37g), heating
Mixture to 200 DEG C, reacts 7-8 hour.Slightly after cooling, filtering, filter cake methanol washes away quinoline, then with Recrystallisation from acetic acid,
Washing remove acetic acid, obtain dark yellow solid (45.0g) after drying, fusing point: 237.6 DEG C～241.4 DEG C, (be abbreviated as " yellow mix
Brilliant disperse dyes-2 ").
Accompanying drawing 3 is shown in by X-ray diffraction (XRD) collection of illustrative plates of " yellow mixed crystal disperse dyes-2 ".
Standardization program sand milling pressed by " the yellow mixed crystal disperse dyes-2 " of undried, with the commodity of C.I. disperse yellow 54 in dye model machine
For standard specimen, to polyster fibre dyeing, result shows: both coloured light is close, the staining power of " yellow mixed crystal disperse dyes-2 "
Higher than the staining power of C.I. disperse yellow 54 by 5%, the dyeing enhancing rate of " yellow mixed crystal disperse dyes-2 " is than C.I. disperse yellow 54
Dyeing enhancing rate is high by 5%, and the fastness to sublimation of " yellow mixed crystal disperse dyes-2 " is higher than the fastness to sublimation of C.I. disperse yellow 54 half grade.
Embodiment 3 (Ab with B mixes with mol ratio for 1.5:1)
Phthalic anhydride (105g, 0.71mol), 2-methylquinoline (13.4g, 0.094mol), 2-it is sequentially added in 500ml there-necked flask
Methyl-3-hydroxyquinoline-4-carboxylic acid (28.5g, 0.14mol) and ZnCl2 (6.72g), be heated to 140 DEG C, make mixture complete
Melted, start stirring, continue reacting by heating thing to 200 DEG C, react 7-8 hour.It is cooled to 50 DEG C, adds 20% (w) NaOH
(200g), being heated to 80 DEG C and stir 1 hour, filtered while hot, filter cake to neutral, is dried to obtain dark yellow solid by hot water wash
(50.4g), fusing point: 229.7-234.1 DEG C (being abbreviated as " yellow mixed crystal disperse dyes-3 ").
Filtrate merges with cleaning mixture (volume about 800ml), is placed in 1000ml flask, is heated to 50 DEG C～80 DEG C, uses dense sulfur
PH=3 is adjusted in acid, makes the sodium phthalate being originally dissolved in alkali liquor become phthalic acid and separates out from solution, stands, natural
It is cooled to ambient temperature, filters, dried phthalic acid (70-75g), it is phthalic anhydride after drying reusable.
Yellow mixed crystal disperse dyes-3 " X-ray diffraction (XRD) collection of illustrative plates see accompanying drawing 4.
The dyestuff filter-cakes of undried presses standardization program sand milling, with the commodity of C.I. disperse yellow 54 as standard specimen in dye model machine, to washing
Synthetic fibre stock-dye, coloration result shows, both coloured light is close, and the staining power of " yellow mixed crystal disperse dyes-3 " divides than C.I.
The staining power dissipating Huang 54 is high by 15%, and the dyeing enhancing rate of " yellow mixed crystal disperse dyes-3 " carries than the dyeing of C.I. disperse yellow 54
The rate of liter is high by 10%, and the fastness to sublimation of " yellow mixed crystal disperse dyes-3 " is higher than the fastness to sublimation of C.I. disperse yellow 54 half grade.
Claims (4)
1. yellow mixed crystal disperse dyes, it is characterised in that described yellow mixed crystal disperse dyes are by the following preparation of key step
Method prepares:
Under having catalyst existence condition, by 2-methyl-3-hydroxyquinoline or/and 2-methyl-3-hydroxyquinoline-4-carboxylic acid and 2-methyl
The mixture of quinoline composition and the phthalic anhydride of excess, in boiling point is higher than the organic solvent of 220 DEG C, keep at 190 DEG C～220 DEG C of states
6～9 hours, obtain object；
Wherein, the consumption of catalyst is 2-methyl-3-hydroxyquinoline or/and the molal quantity of 2-methyl-3-hydroxyquinoline-4-carboxylic acid and 2-
The 20% of the summation of the molal quantity of methylquinoline, described catalyst is anhydrous zinc chloride or aluminum trichloride (anhydrous)；
Described organic solvent is: trichloro-benzenes, Nitrobenzol, quinoline or derivatives thereof, boiling point are higher than conduction oil or the phthalic anhydride of 220 DEG C；
When organic solvent used is non-phthalic anhydride, the mol ratio of reactant is: 2-methyl-3-hydroxyquinoline is or/and 2-methyl-3-hydroxyl
The mol ratio of Cinchonic Acid, 2-methylquinoline and phthalic anhydride is 0.1～0.9:0.9～0.1:1～2；
When organic solvent used is phthalic anhydride, the mol ratio of reactant is: 2-methyl-3-hydroxyquinoline is or/and 2-methyl-3-hydroxyl quinoline
The mol ratio of quinoline-4-carboxylic acid, 2-methylquinoline and phthalic anhydride is 0.1～0.9:0.9～0.1:3～10.
2. yellow mixed crystal disperse dyes as claimed in claim 1, it is characterised in that wherein by 2-methyl-3-hydroxyquinoline or/
The mixture formed with 2-methylquinoline with 2-methyl-3-hydroxyquinoline-4-carboxylic acid and excessive phthalic anhydride are 200 DEG C～210 DEG C of states
Keep 7～8 hours, obtain object.
3. yellow mixed crystal disperse dyes as claimed in claim 1 or 2, it is characterised in that organic solvent wherein used is benzene
Acid anhydride, 2-methyl-3-hydroxyquinoline or/and the mol ratio of 2-methyl-3-hydroxyquinoline-4-carboxylic acid, 2-methylquinoline and phthalic anhydride be 0.3～
0.7:0.7～0.3:3～5.
4. yellow mixed crystal disperse dyes as claimed in claim 1 or 2, it is characterised in that organic solvent wherein used is non-
Phthalic anhydride, 2-methyl-3-hydroxyquinoline or/and the mol ratio of 2-methyl-3-hydroxyquinoline-4-carboxylic acid, 2-methylquinoline and phthalic anhydride be 0.3～
0.7:0.7～0.3:1～1.5.
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| CN201410790583.2A CN104559315B (en) | 2014-12-18 | 2014-12-18 | Yellow mixed crystal type disperse dye |
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| CN104559315B true CN104559315B (en) | 2016-09-14 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104744969B (en) * | 2015-03-13 | 2016-12-07 | 南通恒盛精细化工有限公司 | A kind of manufacture method of the mixed crystal type Yellow disperse dye of controlled mixing ratio |
| CN112079773B (en) * | 2020-09-27 | 2022-05-20 | 湖南新合新生物医药有限公司 | Synthetic method of 2-methyl-3-hydroxyquinoline and preparation method of quinazoline-peptide-ketone disperse dye |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006022A (en) * | 1932-11-18 | 1935-06-25 | Gen Aniline Works Inc | Dyestuff of the quinophthalone series of good fastness to light |
| DE1229663B (en) * | 1964-06-27 | 1966-12-01 | Basf Ag | Process for the preparation of 4-bromo-3-hydroxyquinophthalone |
| CN1667051A (en) * | 2005-03-30 | 2005-09-14 | 吴江市绿洲染料化工有限公司 | Disperse dye mixtures |
| CN102070523B (en) * | 2010-12-30 | 2013-07-10 | 浙江山峪染料化工有限公司 | Novel method for preparing 3-hydroxylquinaldine-4-carboxylic acid |
| CN102295837B (en) * | 2011-06-02 | 2014-06-04 | 浙江龙盛集团股份有限公司 | Preparation method for disperse yellow dye |
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