CN102675915A - 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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- CN102675915A CN102675915A CN2012100975854A CN201210097585A CN102675915A CN 102675915 A CN102675915 A CN 102675915A CN 2012100975854 A CN2012100975854 A CN 2012100975854A CN 201210097585 A CN201210097585 A CN 201210097585A CN 102675915 A CN102675915 A CN 102675915A
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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 compsn that contains benzoyl-H acid and preparation method thereof.
Background technology:
At present, in ink-jet printing ink, using the most widely, magenta dyestuff mainly is 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 this type reactive dyestuffs is a difficult problem of its prolonged storage stability of puzzlement always.Reactive red 180 belongs to vinyl sulfone(Remzaol fundamental mode reactive dyestuffs with REACTIVE Red 195; Hydrolysis pH value along with the ethene sulfuryl in the prolonged storage process can constantly reduce; The pH value that thereupon causes the jetting ink that contains such water-soluble dye also constantly descends, and causes unstable and surperficial to the ink jet printing head corrosion and the damage of ink.
Summary of the invention:
The purpose of this invention is to provide a kind of water-soluble dye compsn that contains benzoyl-H acid and preparation method thereof; It is through becoming salt form and second component composition or its and become salt form to mix and the adjustment of blending ratio to first component composition or its; Obtain the pure water-soluble dye of coloured light; And removed the group of facile hydrolysis in the structure, avoided the hydrolysis of existing this type of dyestuff in water and the reduction of pH value, had excellent extended storage stability; Prolong the work-ing life of printer ink head, be very suitable for the application of spray ink Printing; And mix the adjustment of assembly ratio through first component and second component, 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 adopts following technical scheme: it comprises first component and second component; The mass percent of first component and second component is 99: 1-1: 99; And first component is compound or its one-tenth salt form, and second component is compound or its one-tenth salt form.
Preparing method of the present invention is:
One, the preparation of benzoyl-H acid
I. H acid is dissolved in the water, is adjusted to pH value neutrality with sodium hydroxide or yellow soda ash,
Ii. slowly add Benzoyl chloride 99min., under 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
With 2-naphthylamines-1, the 5-disulfonic acid is dissolved in the water, and adds HCl and stirs; Be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising; 5～10 ℃ of insulations 1～2 hour; Add thionamic acid and remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
Three, coupled reaction
With 2-naphthylamines-1,5-disulfonic acid diazonium salt solution slowly is added dropwise to benzoyl-H acid solution, and controls the pH value between 8-9 with 8%NaOH solution; The coupling temperature is controlled at normal temperature, drips to finish continued reaction 1-2 hour, filters; Desalination obtains the compound of first component;
2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out above-mentioned same processing, obtain the compound of second component;
Four, mix
Is to mix in 99: 1～1: 99 the compound of the compound of first component and second component according to mass percent, obtains containing the water-soluble dye compsn of benzoyl-H acid.
The present invention has following beneficial effect: it is through becoming salt form and second component composition or its and become salt form to mix and the adjustment of blending ratio to first component composition or its; Obtain the pure water-soluble dye of coloured light; And removed the group of facile hydrolysis in the structure, avoided the hydrolysis of existing this type of dyestuff in water and the reduction of pH value, had excellent extended storage stability; Prolong the work-ing life of printer ink head, be very suitable for the application of spray ink Printing; And mix the adjustment of assembly ratio through first component and second component, finally print coloured light and reactive red 180, REACTIVE Red 195 is consistent.
Description of drawings:
Fig. 1 is the structural formula synoptic diagram of first component among the present invention,
Fig. 2 is the structural formula synoptic diagram of second component among the present invention.
Embodiment:
Embodiment one: referring to Fig. 1-2; This embodiment adopts following technical scheme: it comprises first component and second component; The mass percent of first component and second component is 99: 1-1: 99; And first component is compound or its one-tenth salt form, and 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, is adjusted to pH value neutrality with sodium hydroxide or yellow soda ash,
Ii. slowly add Benzoyl chloride 99min., under 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
With 2-naphthylamines-1, the 5-disulfonic acid is dissolved in the water, and adds HCl and stirs; Be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising; 5～10 ℃ of insulations 1～2 hour; Add thionamic acid and remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
Three, coupled reaction
With 2-naphthylamines-1,5-disulfonic acid diazonium salt solution slowly is added dropwise to benzoyl-H acid solution, and controls the pH value between 8-9 with 8%NaOH solution; The coupling temperature is controlled at normal temperature, drips to finish continued reaction 1-2 hour, filters; Desalination obtains the compound of first component;
2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out above-mentioned same processing, obtain the compound of second component;
Four, mix
Is to mix in 99: 1～1: 99 the compound of the compound of first component and second component according to mass percent, obtains containing the water-soluble dye compsn of benzoyl-H acid.
The mass percent of described first component and second component is preferably 70: 30-30: 70, and preferred ratio is 60: 40-40: 60.
Described first 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 compsn in the water when using, and obtains the aqueous solution of water-soluble dye compsn, and this aqueous solution can be applicable in the marking ink prescription of spray ink Printing.
The mass concentration of described water-soluble dye compsn in the aqueous solution is 10%～15%.
This application comprises that also the aqueous solution with water-soluble dye compsn mixes 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, 1,3-dimethyl--2-imidazolone, N, one or more in the N-dimethyl urea.
Described water-soluble dye compsn both can exist with solid form, like dry powder or particle, also can preserve with liquid form, like the mill base or the water-soluble solution of high density.
This embodiment approaches reactive red 180, REACTIVE Red 195 through the adjustment to first component and second mixture ratio example on the coloured light, solved the extended storage stability problem that these type of reactive dyestuffs bring 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 through adjusting the coloured light of ink with the mixed assembly of first component or second component.
Have the dyestuff of the structural formula of first component and second component and can be better exist with the form of salt, positively charged ion is selected sodium ion, lithium ion, ammonium ion, tetraethyl-amine salt or trialkyl alcohol amine salt usually.
This embodiment is through becoming salt form and second component composition or its and become salt form to mix and the adjustment of blending ratio to first component composition or its; Obtain the pure water-soluble dye of coloured light; And removed the group of facile hydrolysis in the structure, avoided the hydrolysis of existing this type of dyestuff in water and the reduction of pH value, had excellent extended storage stability; Prolong 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 among the described preparation method replaces with in the step: respectively first component composition and second component composition are carried out to reactant salt; Obtain the one-tenth salt form of first component and the salt form that becomes of second component; With the one-tenth salt form of first component and the salt form that becomes of second component; According to mass percent is to mix in 99: 1～1: 99, obtains containing the water-soluble dye compsn of benzoyl-H acid; Other composition is identical with embodiment one with the preparation method.
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; Slowly be warming up to 45 ℃, under this temperature, add 10% sodium carbonate solution 230g; Be cooled to then about 20 ℃, in 3 hours, drip Benzoyl chloride 99min. 31.2g, drip and finish back adding 40% sodium hydroxide solution 20ml; Dropwise 5 .6g Benzoyl chloride 99min. in 40 minutes drips and finishes afterreaction 2 hours.Sodium hydroxide solution adjustment pH 9.5-11.5 with 20ml 40% is warmed to 80 ℃ of reactions hydrolysis in 2 hours and removes the O-acylate.Be cooled to 30 ℃, with about 35g 96% sulfuric acid adjustment pH to 4.0, and stirred overnight, there is deposition to separate out, to filter, the filter cake oven dry obtains benzoyl-H acid dry powder 104.5g, content 66.08%, yield: 82%.
The preparation of (2) first component composition
With 39 gram Sulpho Tobias Acids (2-naphthylamines-1.5-disulfonic acid, 78.34%, 0.1mol) be dispersed in the 200 gram water, the back that is uniformly dispersed adds 26 gram hydrochloric acid, slowly adds 30% sodium nitrite solution, 23 grams after stirring half a hour, carries out diazotization reaction.Controlled temperature is between 5-10 ℃ during reaction, and is incubated 1 hour.Reaction finishes back adding thionamic acid and removes excessive Sodium Nitrite.Get benzoyl-H acid 65 grams of above-mentioned preparation, be dissolved in the water.Scattered diazonium salt is slowly added in the benzoyl-H acid solution, and control between its pH8-9.After adding, continue to stir 1 hour.Reaction with the desalination of RO reverse osmosis membrane, is removed the inorganic salt that produce in the synthetic reaction process after finishing.Spraying drying finally obtains the first component composition sodium salt dry powder 80g, yield 97% then.
The preparation of (3) second component composition
With 22.8 gram TOBIAS ACID 97MIN.& 98MIN.s (2-amino-1-naphthalene sulfonic aicd, 98%, 0.1mol) be dispersed in the 200 gram water, the back that is uniformly dispersed adds 26 gram hydrochloric acid, slowly adds 30% sodium nitrite solution, 23 grams after stirring half a hour, carries out diazotization reaction.Controlled temperature is between 5-10 ℃ during reaction, and is incubated 1 hour.Reaction finishes back adding thionamic acid and removes excessive Sodium Nitrite.Filter, the filter cake that obtains is dispersed in the 200 gram water.Get benzoyl-H acid 65 grams of above-mentioned preparation, be dissolved in the water.Scattered diazonium salt is slowly added in the benzoyl-H acid solution, and control between its pH8-9.After adding, continue to stir 1 hour.Reaction with the desalination of RO reverse osmosis membrane, is removed the inorganic salt that produce in the synthetic reaction process after finishing.Spraying drying finally obtains the second component composition sodium salt dry powder 69g, yield: 95% then.
(4) the above-mentioned compound that obtains is applied to the composite of ink and test:
Mix the mass ratio shown in each following component according to the form below, the nylon membrane with 0.45 micron and 0.22 micron filters successively, obtains being fit to the ink of spray ink Printing.
Dyestuff content all calculates with dyestuff dry powder in the ink.
Dyestuff among the ink A is first component composition, the sodium-salt form of second component composition, and the two mass percent is 60: 40.
Dyestuff among the ink B is first component composition, the sodium-salt form of second component composition, and the two mass percent is 50: 50.
Reactive dyestuffs among ink C and the ink D are commercially available ink-jet dye.
Stability test:
In following table, observe the changing conditions of 4 all pH later on and have or not deposition with 60 ℃ of conditions of storage respectively with-5 ℃.
The pH changing conditions has or not deposition
Zero represents not deposition of △ pH＜0.5
⊙ represents not deposition of 1＜△ pH＜2, but a retrogradation is arranged
△ represents on 2＜△ pH＜3 filter paper and slightly a bit precipitates
* represent on △ pH＞3 filter paper obvious sediment is arranged
Can find out from test result, ink A and B 60 ℃ with-5 ℃ of conditions under store and 4 weeks still be steady state, its pH value changes all less than 0.5 and does not precipitate, and ink B, C all have in various degree hydrolysis and deposition.
Printing test:
I. fluency
Test: MIMAKI JV4, print software: cover Thailand, printing model: 720*720dpi High-8pass
Print continuously more than the 5M, printing head is tested, and broken string is not for testing through fluency.
Ink A, B, C, D are all through printing the fluency test.
Ii. coloured light: with the L.A.B value of EYE-ONE test printing color lump, the contrast color distortion, the result is following:
Can find out that from test result ink A (blending ratio of the first component sodium salt and the second component sodium salt is 60: 40) is consistent with 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 the second component sodium salt is 50: 50) is consistent with the coloured light of ink C (Reactive red 195) on two kinds of different print media, therefore can realize the different blended assembly ratio of first component composition and salt and second component composition and salt thereof is adjusted final printing coloured light.
Embodiment 2:
The preparation of the lithium salts of (1) first component composition, second component composition
After coupled reaction end in embodiment 1 step (2), the HCl with 36% slowly adjusts pH＜3, stirs after 2 hours, and dyestuff is separated out from solution gradually, filters, and with 1% Hydrogen chloride 50ml flushing, obtains dyestuff acid body filter cake.Be scattered in the dyestuff filter cake in the 500g water then, with 15%LiOH solution adjustment pH8～9, treat that dyestuff acid body dissolves fully after, with the desalination of RO reverse osmosis membrane, spraying drying finally obtains the lithium salts 70g of first component composition, yield 92%.
The lithium salts 61g that uses the same method and obtain second component composition, yield 90.4%.
(2) get the first component composition 10g and the second component composition 40g and mix (mass percent that is the two is 20: 80), make the water-soluble dye compsn that contains benzoyl-H acid.
(3) above-mentioned water-soluble dye compsn is dissolved in the 450g water; Obtain the aqueous solution of water-soluble dye compsn; The mass concentration of compsn in the aqueous solution is 10%, with 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) employing prepares first component composition and second component composition with embodiment 1 step (1)～(3) identical method.
The preparation of the tetraethyl-amine salt of (2) second component composition.
(3) the tetraethyl-amine salt 1g with the first component composition 99g, second component composition mixes (mass percent that is the two is 99: 1), makes the water-soluble dye compsn that contains benzoyl-H acid.
(4) above-mentioned water-soluble dye compsn is dissolved in the 566g water, obtains the aqueous solution of water-soluble dye compsn, the mass concentration of compsn in the aqueous solution is 15%, and this aqueous solution can be applicable in the marking ink prescription of spray ink Printing.
Claims (5)
1. one kind contains sour water-soluble dye compsn of benzoyl-H and preparation method thereof; It is characterized in that it comprises first component and second component; The mass percent of first component and second component is 99: 1-1: 99; And first component is compound or its one-tenth salt form, and second component is compound or its one-tenth salt form.
2. a kind of water-soluble dye compsn that contains benzoyl-H acid according to claim 1 and preparation method thereof is characterized in that the preparation method of described water-soluble dye compsn is:
(1), the preparation of benzoyl-H acid
(i). H acid is dissolved in the water, is adjusted to pH value neutrality with sodium hydroxide,
(ii). slowly add Benzoyl chloride 99min., under 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
With 2-naphthylamines-1, the 5-disulfonic acid is dissolved in the water, and adds HCl and stirs; Be cooled to 0～5 ℃, slowly drip sodium nitrite solution, after dropwising; 5～10 ℃ of insulations 1～2 hour; Add thionamic acid and remove unnecessary Sodium Nitrite, obtain 2-naphthylamines-1,5-disulfonic acid diazonium salt solution;
2-amino-1-naphthalene sulfonic aicd is carried out above-mentioned same processing, obtain 2-amino-1-naphthalene sulfonic aicd diazonium salt solution;
(3), coupled reaction
With 2-naphthylamines-1,5-disulfonic acid diazonium salt solution slowly is added dropwise to benzoyl-H acid solution, and controls the pH value between 8-9 with 8%NaOH solution; The coupling temperature is controlled at normal temperature, drips to finish continued reaction 1-2 hour, filters; Desalination obtains the compound of first component; 2-amino-1-naphthalene sulfonic aicd diazonium salt solution is carried out above-mentioned same processing, obtain the compound of second component;
(4), mix
Is to mix in 99: 1～1: 99 the compound of the compound of first component and second component according to mass percent, obtains containing the water-soluble dye compsn of benzoyl-H acid.
3. a kind of water-soluble dye compsn that contains benzoyl-H acid according to claim 1 and preparation method thereof; It is characterized in that the 4th step replaced with among the described preparation method: respectively first component composition and second component composition are carried out to reactant salt; Obtain the one-tenth salt form of first component and the salt form that becomes of second component; With the one-tenth salt form of first component and the salt form that becomes of second component; According to mass percent is to mix in 99: 1～1: 99, obtains containing the water-soluble dye compsn of benzoyl-H acid.
4. a kind of water-soluble dye compsn that contains benzoyl-H acid according to claim 1 and preparation method thereof is characterized in that described first component replaces with it and becomes salt form.
5. a kind of water-soluble dye compsn that contains benzoyl-H acid according to claim 1 and preparation method thereof is characterized in that described second component replaces with it and becomes salt form.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111936586A (en) * | 2018-03-28 | 2020-11-13 | 精工爱普生株式会社 | Aqueous inkjet composition |
| 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 |
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| US6395885B1 (en) * | 1998-06-05 | 2002-05-28 | Avecia Limited | Use of lithium salts of anionic dyes to enhance their light-fastness |
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| 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 |
| US20110014375A1 (en) * | 2009-07-15 | 2011-01-20 | Holloway Ann P | Magenta inkjet ink having improved print quality with porous photo media |
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| 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 |
| JP2004051750A (en) * | 2002-07-18 | 2004-02-19 | Mitsubishi Chemicals Corp | Inkjet recording method |
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| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111936586A (en) * | 2018-03-28 | 2020-11-13 | 精工爱普生株式会社 | Aqueous inkjet composition |
| CN111936586B (en) * | 2018-03-28 | 2022-04-15 | 精工爱普生株式会社 | Aqueous inkjet composition |
| 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 |
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