CN102675915B - Water-soluble dye composition containing benzoyl H acid and preparation method thereof - Google Patents
Water-soluble dye composition containing benzoyl H acid and preparation method thereof Download PDFInfo
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- CN102675915B CN102675915B CN201210097585.4A CN201210097585A CN102675915B CN 102675915 B CN102675915 B CN 102675915B CN 201210097585 A CN201210097585 A CN 201210097585A CN 102675915 B CN102675915 B CN 102675915B
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Abstract
The invention relates to a water-soluble dye composition containing benzoyl H acid and a preparation method of the composition, and relates to a water-soluble dye. The water-soluble dye composition comprises a first component and a second component at a mass ratio of 99:1-1:99, wherein the first component is a compound or salt form thereof, and the second component is a compound or a salt form thereof. According to the water-soluble dye composition containing benzoyl H acid and a preparation method of the composition provided by the invention, an easily hydrolyzable group is removed from the structure, so that the problems that the traditional like dye is hydrolyzed in water and the pH value is decreased are solved; by adjusting the mixing ratio of the first component and the second component, the tone requirements required by ink-jet printing can be met; and the water-soluble dye composition has excellent long-term storage stability, prolongs the service life of printer ink head, and is very suitable to be applied to ink-jet printing.
Description
Technical field:
The present invention relates to a kind of water-soluble dye, be specifically related to a kind of water-soluble dye composition containing benzoyl H acid and preparation method thereof.
Background technology:
At present, in ink-jet printing ink, the magenta dyestuff being most widely used is mainly reactive red 180 (Reactive Red 180), REACTIVE Red 195 (Reactive Red 195) etc.The coloured light of this type of dyestuff is pure, is suitable for very much the composite of magenta ink.
Yet the hydrolysis of these class reactive dyestuffs is a difficult problem of its prolonged storage stability of puzzlement always.Reactive red 180 and REACTIVE Red 195 belong to vinyl sulfone(RemzaolHuo Xingranliaohuoxingjituan) fundamental mode reactive dyestuffs, hydrolysis pH value along with ethene sulfuryl in prolonged storage process can constantly reduce, the pH value that thereupon causes the ink for ink-jet print that contains such water-soluble dye also constantly declines, and causes the unstable of ink and to the corrosion on ink jet printing head surface and damage.
Summary of the invention:
The object of this invention is to provide a kind of water-soluble dye composition containing benzoyl H acid and preparation method thereof, it is by becoming salt form and second component compound or its to become salt form to mix and the adjustment of blending ratio to the first component composition or its, obtain the pure water-soluble dye of coloured light, and in structure, removed the group of facile hydrolysis, the hydrolysis of existing this type of dyestuff in water and the reduction of pH value have been avoided, there is excellent extended storage stability, extend the work-ing life of printer ink head, be very suitable for the application of spray ink Printing; And by the adjustment of the first component and second component Mixed Pinyin ratio, finally print coloured light and reactive red 180, REACTIVE Red 195 is consistent.
In order to solve the existing problem of background technology, the present invention is by the following technical solutions: it comprises the first component and second component, the mass percent of the first component and second component is 99: 1-1: 99, and the first component is compound or its one-tenth salt form, second component is compound or its one-tenth salt form.
Preparation method of the present invention is:
One, the preparation of benzoyl H acid
I. H acid is dissolved in the water, with sodium hydroxide or sodium carbonate, is adjusted to pH value neutral,
Ii. slowly add Benzoyl chloride, in neutrality, to weak basic condition, make acylation reaction,
Iii. carry out saponification reaction, remove the by product that esterification produces,
Iv. acid out, filtering separation N-acylate, obtains benzoyl H acid;
Two, diazotization reaction
By 2-naphthylamines-1,5-disulfonic acid is dissolved in the water, add HCl to stir, be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising, 5～10 ℃ of insulations 1～2 hour, add thionamic acid to remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out to above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
Three, coupled reaction
By 2-naphthylamines-1,5-disulfonic acid diazonium salt solution is slowly added dropwise to benzoyl H acid solution, and controls pH value between 8-9 with 8%NaOH solution, coupling temperature is controlled at normal temperature, drips and finishes rear continuation reaction 1-2 hour, filters, desalination, obtains the compound of the first component;
2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out to above-mentioned same processing, obtain the compound of second component;
Four, mix
By the compound of the first component, according to mass percent, be to mix for 99: 1～1: 99 with the compound of second component, obtain the water-soluble dye composition containing benzoyl H acid.
The present invention has following beneficial effect: it is by becoming salt form and second component compound or its to become salt form to mix and the adjustment of blending ratio to the first component composition or its, obtain the pure water-soluble dye of coloured light, and in structure, removed the group of facile hydrolysis, the hydrolysis of existing this type of dyestuff in water and the reduction of pH value have been avoided, there is excellent extended storage stability, extend the work-ing life of printer ink head, be very suitable for the application of spray ink Printing; And by the adjustment of the first component and second component Mixed Pinyin ratio, finally print coloured light and reactive red 180, REACTIVE Red 195 is consistent.
Accompanying drawing explanation:
Fig. 1 is the structural formula schematic diagram of the first component in the present invention,
Fig. 2 is the structural formula schematic diagram of second component in the present invention.
Embodiment:
Embodiment one: referring to Fig. 1-2, this embodiment is by the following technical solutions: it comprises the first component and second component, the mass percent of the first component and second component is 99: 1-1: 99, and the first component is compound or its one-tenth salt form, second component is compound or its one-tenth salt form.
The preparation method of this embodiment is:
One, the preparation of benzoyl H acid
I. H acid is dissolved in the water, with sodium hydroxide or sodium carbonate, is adjusted to pH value neutral,
Ii. slowly add Benzoyl chloride, in neutrality, to weak basic condition, make acylation reaction,
Iii. carry out saponification reaction, remove the by product that esterification produces,
Iv. acid out, filtering separation N-acylate, obtains benzoyl H acid;
Two, diazotization reaction
By 2-naphthylamines-1,5-disulfonic acid is dissolved in the water, add HCl to stir, be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising, 5～10 ℃ of insulations 1～2 hour, add thionamic acid to remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out to above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
Three, coupled reaction
By 2-naphthylamines-1,5-disulfonic acid diazonium salt solution is slowly added dropwise to benzoyl H acid solution, and controls pH value between 8-9 with 8%NaOH solution, coupling temperature is controlled at normal temperature, drips and finishes rear continuation reaction 1-2 hour, filters, desalination, obtains the compound of the first component;
2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out to above-mentioned same processing, obtain the compound of second component;
Four, mix
By the compound of the first component, according to mass percent, be to mix for 99: 1～1: 99 with the compound of second component, obtain the water-soluble dye composition containing benzoyl H acid.
The first described component and the mass percent of second component are preferably 70: 30-30: 70, and preferred ratio is 60: 40-40: 60.
The first described component is an alkali metal salt, ammonium salt or alkylamine salt with the salt form that becomes of the compound of second component, and wherein basic metal comprises sodium, lithium or potassium, and alkylamine comprises tetraethyl-amine or trialkyl hydramine.
This embodiment is dissolved in described water-soluble dye composition in water when application, obtains the aqueous solution of water-soluble dye composition, and this aqueous solution can be applicable in the marking ink formula of spray ink Printing.
The mass concentration of described water-soluble dye composition in the aqueous solution is 10%～15%.
This application also comprises the aqueous solution of water-soluble dye composition mixed with organic solvent, and the mass concentration of organic solvent is 25%～50%, obtains being applied to the marking ink of spray ink Printing.
Described organic solvent is selected from glycerine, glycol ether, diethylene glycol monobutyl ether, DMI, N, one or more in N-dimethyl urea.
Described water-soluble dye composition both can exist with solid form, as dry powder or particle, also can preserve with liquid form, as the mill base of high density or water-soluble solution.
This embodiment, by the adjustment to the first component and second component blending ratio, close to reactive red 180, REACTIVE Red 195, has solved the extended storage stability problem that these type of reactive dyestuffs bring on coloured light simultaneously, is very suitable for the application of spray ink Printing.In addition, other carmetta ink-jet dyes, as direct red 141, Xylene Red 52, directly red 75 etc. also can be by adjusting the coloured light of ink with the Mixed Pinyin of the first component or second component.
Have the dyestuff of the structural formula of the first component and second component and can be better with the form of salt, exist, positively charged ion is selected sodium ion, lithium ion, ammonium ion, tetraethyl-amine salt or trialkyl alcohol amine salt conventionally.
This embodiment is by becoming salt form and second component compound or its to become salt form to mix and the adjustment of blending ratio to the first component composition or its, obtain the pure water-soluble dye of coloured light, and in structure, removed the group of facile hydrolysis, the hydrolysis of existing this type of dyestuff in water and the reduction of pH value have been avoided, there is excellent extended storage stability, extend the work-ing life of printer ink head, be very suitable for the application of spray ink Printing.
Embodiment two: this embodiment is with the difference of embodiment one: the 4th step in described preparation method replaces with: respectively the first component composition and second component compound are carried out to salt-forming reaction, obtain the salt form that becomes of the one-tenth salt form of the first component and second component, by the salt form that becomes of the one-tenth salt form of the first component and second component, according to mass percent, be to mix for 99: 1～1: 99, obtain the water-soluble dye composition containing benzoyl H acid; Other composition and preparation method are identical with embodiment one.
Embodiment 1:
(1) preparation of benzoyl H acid
In there-necked flask, drop into water 100g, H acid 80g (85%, 0.2mol), 40% sodium hydroxide solution 25ml, after stirring, be slowly warming up to 45 ℃, at this temperature, add 10% sodium carbonate solution 230g, then be cooled to 20 ℃ of left and right, in 3 hours, drip Benzoyl chloride 31.2g, after dropping finishes, add 40% sodium hydroxide solution 20ml, in 40 minutes, drip 5.6g Benzoyl chloride, drip and finish rear reaction 2 hours.With the sodium hydroxide solution of 20ml 40%, adjust pH 9.5-11.5, be warmed to 80 ℃ of reactions hydrolysis in 2 hours and remove O-acylate.Be cooled to 30 ℃, adjust pH to 4.0 left and right, and stir and spend the night with 35g 96% sulfuric acid, have Precipitation, filter, filter cake is dried, and obtains benzoyl H acid dry powder 104.5g, content 66.08%, yield: 82%.
The preparation of (2) first component composition
By 39 grams of Sulpho Tobias Acids (2-naphthylamines-1.5-disulfonic acid, 78.34%, 0.1mol) be dispersed in 200 grams of water, after being uniformly dispersed, add 26 grams of hydrochloric acid, slowly add 23 grams of 30% sodium nitrite solutions after stirring half an hour, carry out diazotization reaction.During reaction, control temperature between 5-10 ℃, and be incubated 1 hour.After finishing, reaction add thionamic acid to remove excessive Sodium Nitrite.65 grams of the benzoyl H acid of getting above-mentioned preparation, are dissolved in water.Scattered diazonium salt is slowly added in benzoyl H acid solution, and control between its pH8-9.After adding, continue to stir 1 hour.After reaction finishes, with the desalination of RO reverse osmosis membrane, remove the inorganic salt that produce in synthetic reaction process.Then spraying is dry, finally obtains the first component composition sodium salt dry powder 80g, yield 97%.
(3) preparation of second component compound
By 22.8 grams of TOBIAS ACID 97MIN.& 98MIN. (2-amino-1-naphthalene sulfonic aicd, 98%, 0.1mol) be dispersed in 200 grams of water, after being uniformly dispersed, add 26 grams of hydrochloric acid, slowly add 23 grams of 30% sodium nitrite solutions after stirring half an hour, carry out diazotization reaction.During reaction, control temperature between 5-10 ℃, and be incubated 1 hour.After finishing, reaction add thionamic acid to remove excessive Sodium Nitrite.Filter, the filter cake obtaining is dispersed in 200 grams of water.65 grams of the benzoyl H acid of getting above-mentioned preparation, are dissolved in water.Scattered diazonium salt is slowly added in benzoyl H acid solution, and control between its pH8-9.After adding, continue to stir 1 hour.After reaction finishes, with the desalination of RO reverse osmosis membrane, remove the inorganic salt that produce in synthetic reaction process.Then spraying is dry, finally obtains second component compound sodium salt dry powder 69g, yield: 95%.
(4) compound obtained above is applied to the composite of ink test:
Mass ratio shown in each component according to the form below is below mixed, with the nylon membrane of 0.45 micron and 0.22 micron, filter successively, obtain being applicable to the ink of spray ink Printing.
In ink, dyestuff content all calculates with dyestuff dry powder.
Dyestuff in ink A is the first component composition, the sodium-salt form of second component compound, and the two mass percent is 60: 40.
Dyestuff in ink B is the first component composition, the sodium-salt form of second component compound, and the two mass percent is 50: 50.
Reactive dyestuffs in ink C and ink D are commercially available ink-jet dye.
Stability test:
In following table, with 60 ℃, observe the changing conditions of 4 weeks later pH and have or not precipitation with the condition of storage of-5 ℃ respectively.
PH changing conditions has or not precipitation
Zero represents not precipitation of △ pH < 0.5
⊙ represents not precipitation of 1 < △ pH < 2, but has a retrogradation
△ represents on 2 < △ pH < 3 filter paper and slightly a little precipitates
* represent on △ pH > 3 filter paper have obvious sediment
From test result, can find out, ink A and B store 4 weeks and are still steady state under 60 ℃ and-5 ℃ of conditions, and its pH value changes and is all less than 0.5 and do not precipitate, and ink B, C all have hydrolysis and precipitation in various degree.
Printing test:
I. fluency
Test printing machine: MIMAKI JV4, print software: cover Thailand, printing model: 720*720dpi High-8pass
More than printing 5M continuously, printing head test, broken string is not for to test by fluency.
Ink A, B, C, D all test by printing fluency.
Ii. coloured light: by the L.A.B value of EYE-ONE test printing color lump, contrast color distortion, result is as follows:
From test result, can find out, ink A (blending ratio of the first component sodium salt and second component sodium salt is 60: 40) is consistent from the coloured light of ink C (Reactive red 180) on two kinds of different print media; Ink B (blending ratio of the first component sodium salt and second component sodium salt is 50: 50) is consistent from the coloured light of ink C (Reactive red 195) on two kinds of different print media, therefore can realize the different Mixed Pinyin ratios of the first component composition and salt and second component compound and salt thereof are adjusted to final printing coloured light.
Embodiment 2:
The preparation of the lithium salts of (1) first component composition, second component compound
After coupled reaction as middle in embodiment 1 step (2) finishes, the HCl with 36% slowly adjusts pH < 3, stirs after 2 hours, and dyestuff is separated out gradually from solution, filters, and with 1% dilute hydrochloric acid 50ml, rinses, and obtains dyestuff acid body filter cake.Then dyestuff filter cake is scattered in 500g water, with 15%LiOH solution, adjusts pH8～9, after dyestuff acid body dissolves completely, with the desalination of RO reverse osmosis membrane, spraying is dry, finally obtains the lithium salts 70g of the first component composition, yield 92%.
Use the same method and obtain the lithium salts 61g of second component compound, yield 90.4%.
(2) get the first component composition 10g and second component compound 40g and mix (mass percent that is the two is 20: 80), make the water-soluble dye composition containing benzoyl H acid.
(3) above-mentioned water-soluble dye composition is dissolved in 450g water, obtain the aqueous solution of water-soluble dye composition, the mass concentration of composition in the aqueous solution is 10%, by this aqueous solution and glycerine 200g, glycol ether 200g, diethylene glycol monobutyl ether 100g mixes (mass concentration that is organic solvent is 50%), filters the marking ink that obtains being applied to spray ink Printing.
Embodiment 3:
(1) adopt the method identical with embodiment 1 step (1)～(3) to prepare the first component composition and second component compound.
(2) preparation of the tetraethyl-amine salt of second component compound.
(3) the tetraethyl-amine salt 1g of the first component composition 99g, second component compound is mixed to (mass percent that is the two is 99: 1), make the water-soluble dye composition containing benzoyl H acid.
(4) above-mentioned water-soluble dye composition is dissolved in 566g water, obtains the aqueous solution of water-soluble dye composition, the mass concentration of composition in the aqueous solution is 15%, and this aqueous solution can be applicable in the marking ink formula of spray ink Printing.
Claims (1)
1. contain a preparation method for the water-soluble dye composition of benzoyl H acid, it is characterized in that, comprise the following steps:
(1), the preparation of benzoyl H acid
(i). H acid is dissolved in the water, with sodium hydroxide, is adjusted to pH value neutral,
(ii). slowly add Benzoyl chloride, in neutrality, to weak basic condition, make acylation reaction,
(iii). carry out saponification reaction, remove the by product that esterification produces,
(iv). acid out, filtering separation N-acylate, obtains benzoyl H acid;
(2), diazotization reaction
By 2-naphthylamines-1,5-disulfonic acid is dissolved in the water, add HCl to stir, be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising, 5～10 ℃ of insulations 1～2 hour, add thionamic acid to remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out to above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
(3), coupled reaction
By 2-naphthylamines-1,5-disulfonic acid diazonium salt solution is slowly added dropwise to benzoyl H acid solution, and controls pH value between 8-9 with 8%NaOH solution, coupling temperature is controlled at normal temperature, drips and finishes rear continuation reaction 1-2 hour, filters, desalination, obtains the compound of the first component; 2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out to above-mentioned same processing, obtain the compound of second component;
(4), mix
By the compound of the first component, according to mass percent, be to mix for 99: 1～1: 99 with the compound of second component; or the first component composition and second component compound are carried out to salt-forming reaction; obtain the salt form that becomes of the one-tenth salt form of the first component and second component; again by the salt form that becomes of the one-tenth salt form of the first component and second component; according to mass percent, be to mix for 99: 1～1: 99, obtain the water-soluble dye composition containing benzoyl H acid.
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| JP2019172778A (en) * | 2018-03-28 | 2019-10-10 | セイコーエプソン株式会社 | Water-based composition for inkjet |
| CN115449233A (en) * | 2022-10-12 | 2022-12-09 | 浙江亿得新材料股份有限公司 | Red dye for ink-jet printing, composition and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6231653B1 (en) * | 1997-12-19 | 2001-05-15 | Zeneca Limited | Dye compositions |
| US6395885B1 (en) * | 1998-06-05 | 2002-05-28 | Avecia Limited | Use of lithium salts of anionic dyes to enhance their light-fastness |
| CN101704770A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Method for preparing purple reactive dye |
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| JP2004051750A (en) * | 2002-07-18 | 2004-02-19 | Mitsubishi Chemicals Corp | Inkjet recording method |
| US8282723B2 (en) * | 2009-07-15 | 2012-10-09 | Lexmark International, Inc. | Magenta inkjet ink having improved print quality with porous photo media |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6231653B1 (en) * | 1997-12-19 | 2001-05-15 | Zeneca Limited | Dye compositions |
| US6395885B1 (en) * | 1998-06-05 | 2002-05-28 | Avecia Limited | Use of lithium salts of anionic dyes to enhance their light-fastness |
| CN101704770A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Method for preparing purple reactive dye |
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| JP特开2004-51750A 2004.02.19 |
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