CN102898869A - Composite dark black reactive dye - Google Patents
Composite dark black reactive dye Download PDFInfo
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- CN102898869A CN102898869A CN2012103676303A CN201210367630A CN102898869A CN 102898869 A CN102898869 A CN 102898869A CN 2012103676303 A CN2012103676303 A CN 2012103676303A CN 201210367630 A CN201210367630 A CN 201210367630A CN 102898869 A CN102898869 A CN 102898869A
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Abstract
The invention discloses a composite dark black reactive dye. The dye is mixed by, by mass, reactive dyes of A, B and C, wherein the mass percent of the three dyes is 50-80% of A, 10-40% of B, 5-30% of C and the balance assistants, and the structural general formulas of A, B and C are presented in (1), (2) and (3). The composite dark black reactive dye is high in dye-uptake, fixation degree, alkali resistance and lifting power, low in substantivity, good in compatibility, easy to wash and wide in application; colors are guaranteed to be consistent before and after pad dyeing; and the dye is particularly suitable for dyeing of cellulosic fibers, protein fibers and polyamide fiber due to good leveling property.
Description
Technical field
The present invention relates to the compound dark black active dyestuff of a kind of cellulose fiber Wesy.
Background technology
Reactive dyestuffs have obtained fast development as the representative of modern dyestuffs industries over nearly 50 years.Black dyes is to use the look kind more, that output is larger in the dyestuff.At present, the Reactive Dye for Cellulose Fibre annual production reaches about 200,000 tons in the world, accounts for 20% of world's dyestuff annual production.When dying the responsive look such as black, grey in pad dyeing, dip-dye etc. in view of present conventional dye species, stability not, the front and back aberration is larger.The dyeing behavior of composite dyestuff is compatibility not too, between hydrophilic, lipophilicity differ very large, to the direct of fiber and water-solublely have than big difference, when in dyeing course, adding the alkali fixation especially, the easy Precipitation of yellow or orange component causes color spot, and fiber affinity is also differed larger, easily cause the look flower, the percentage of A-class goods that causes dyeing is not high.Limited to a certain extent the application of reactive dyestuffs.According to market demand, perfect by constantly its function being improved, with good colouring synchronism, high dye uptake and degree of fixation, high level-dyeing property, high lifting and easy detergency improve the class of product, clean production to satisfy various dyeing needs and realization.
Summary of the invention
The invention provides a kind of have high dye uptake and degree of fixation, high alkali resistance, high lifting force, low substantivity and good compatibleness and easy detergency, have broad applicability can the active aterrimus dyestuff of good plyability.
For this reason, the present invention takes following technical scheme: a kind of compound dark black active dyestuff comprises that A, B, three kinds of reactive dyestuffs of C mix, and A, B, three kinds of reactive dyestuffs mass percents of C are: dyestuff A accounts for 50-80%; Dyestuff B accounts for 10-40%; Dyestuff C accounts for 5-30%; Wherein, dyestuff A, B, C are respectively general formula shown in formula (1), (2), (3):
Dyestuff A comprise as the formula (1) any one or more than one:
Wherein: R
1, R
2, R
3, R
4For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H.
Dyestuff B comprise as the formula (2) any one or more than one
Wherein: R
5, R
6, R
7, R
8For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H.
Dyestuff C comprise as the formula (3) any one or more than one
Wherein: R
9, R
10, R
11, R
12For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H.
As preferably, this composite reactive dark black dye also can be only be comprised of three kinds of reactive dyestuffs of A, B, C and the auxiliary agent of above-mentioned per-cent, and auxiliary agent is a kind of or its mixture in Sodium sulfate anhydrous.min(99), Sodium hexametaphosphate 99, condensation compound of methyl naphthalene sulfonic acid and formaldehyde, the naphthalene sulfonic acidformaldehyde condensation product.
Described a kind of compound active dark black dye, it is characterized in that described dyestuff A general structure (1) in the formula of (4)～(10) any one or more than one,
Described compound active dark black dye, it is characterized in that described dyestuff B general structure (2) in the formula of (11)～(17) any one or more than one
Described a kind of compound active dark black dye, it is characterized in that described dyestuff C-structure general formula in the formula of (18)～(25) any one or more than one,
Reactive black dye of the present invention is by the compound synergic technology, utilizes its three composite hyperchromic effects of dyestuff, has improved dye uptake and the degree of fixation of dyestuff, increased the water-soluble of dyestuff, improved by a relatively large margin water-fastness, the fastness to rubbing of dyestuff, improved the quality of products, to satisfy user's needs.Also by to the design of dye molecule two dimensional structure, three dyestuffs are close to cellulosic substantivity and avidity, and three dyestuffs and water base are adsorbed in fiber synchronously.Realize good level-dyeing property, guaranteed the consistence of pad dyeing front and back color and luster.
Embodiment
Dyestuff A, B, C that the present invention adopts can be mixed in proportion the product of making liquid dye as required, also the liquid dye that are mixed can be obtained solid phase prod through spraying drying, perhaps the pressed powder of each dyestuff directly is mixed in proportion and obtain solid phase prod.
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited to this:
Embodiment 1
1. (4) formula synthetic among the reactive dyestuffs A:
1, doazo reaction: to (beta-sulfuric ester ethyl sulfonyl) aniline, (being para-ester) joins in 100ml water and the 50g trash ice solution and pulled an oar 1 hour with 29.5 g.Then add 13.5g hydrochloric acid (30%), stir after 1 minute, molten clear 30% Sodium Nitrite 24.3g slowly is added drop-wise in the good para-ester of making beating carries out diazotization reaction, the control temperature is 8-15 ℃ in the dropping process, and pH value is controlled 1-1.2.And make the micro-indigo plant of starch potassium iodide paper, the micro-indigo plant of congo-red test paper.After sodium nitrite solution dropwises, keep 8-15 ℃ of temperature, then pH value control 1-1.2 restir reaction 30 minutes uses the excessive Sodium Nitrite of thionamic acid balance.Shown in doazo reaction reaction formula following (26) formula.
2, coupled reaction: with 19.5 g 1-amino-8-naphthols-3,6-disulfonic acid (H acid) joins in the 65g water, and regulates pH value 6.0-6.5 with 6.4g sodium bicarbonate, makes H acid fully molten clear.Then molten clear H acid solution is added drop-wise in the Balanced para-ester diazonium salt fast, 10-20 ℃ of control temperature, carry out first acid coupling, after stirring reaction 2-3 hour, carry out again alkaline coupling, regulate the pH value to 6.0-7.0 with 15.6g sodium bicarbonate, after reacting 1-2 hour, diazonium salt disappears, and gets (4) formula dyestuff among the reactive dyestuffs A again, the whole magma sprays of gained dyestuff are done, and get approximately 85.8g of black-and-blue particle dry product.Shown in coupled reaction formula following (27) formula.
2. (11) formula synthetic among the reactive dyestuffs B:
1, Sulpho Tobias Acid doazo reaction: 40.2 g Sulpho Tobias Acids are joined in 100g water and the 50g trash ice making beating 1 hour, and the control temperature is at 8～12 ℃.Then add 12.4g hydrochloric acid (30%), stir after 1 minute, molten clear 30% Sodium Nitrite 24.8g slowly is added drop-wise in the good Sulpho Tobias Acid of making beating carries out diazotization reaction, the control temperature is 8-15 ℃ in the dropping process, and pH value is controlled 1-1.2.And make the micro-indigo plant of starch potassium iodide paper, the micro-indigo plant of congo-red test paper.After sodium nitrite solution dropwises, keep 8-15 ℃ of temperature, then pH value control 1-1.2 restir reaction 30 minutes uses the excessive Sodium Nitrite of thionamic acid balance.Shown in doazo reaction reaction formula following (28) formula.
2, acid coupling reaction: 52.6g 3,5-diaminobenzoic acid are added in the 200g water, regulate the pH value to 6.0-7.0 with 15.6g sodium bicarbonate, make material fully molten clear after, slowly be added drop-wise in the Balanced Sulpho Tobias Acid diazonium salt, carry out the acid coupling reaction, stirring reaction 2-3 hour, diazonium salt disappeared and is terminal point.Shown in acid coupling reaction formula following (29) formula.
3, para-ester doazo reaction: 60.5 g are joined in 150ml water and the 100g trash ice solution (beta-sulfuric ester ethyl sulfonyl) aniline (para-ester) pulled an oar 1 hour.Then add 27.6g hydrochloric acid (30%), stir after 1 minute, molten clear 30% Sodium Nitrite 50.6g slowly is added drop-wise in the good para-ester of making beating carries out diazotization reaction, the control temperature is 8-15 ℃ in the dropping process, and pH value is controlled 1-1.2.And make the micro-indigo plant of starch potassium iodide paper, the micro-indigo plant of congo-red test paper.After sodium nitrite solution dropwises, keep 8-15 ℃ of temperature, then pH value control 1-1.2 restir reaction 30 minutes uses the excessive Sodium Nitrite of thionamic acid balance.Shown in doazo reaction reaction formula following (30) formula.
4, alkaline coupling reacts: the para-ester diazo liquid that balance is good is poured into carried out coupling in the sour even liquid, temperature 10-15 ℃, regulate pH=6.0-6.2 with 18.3g sodium bicarbonate, and PH reaction 2-3 hour is protected in insulation, making the diazonium salt completely dissolve is the coupling terminal point, get (11) formula among the reactive dyestuffs B, the whole magma sprays of gained dyestuff are done, and get approximately 99.8 g of yellow particle dry product.Shown in coupled reaction formula following (31) formula.
3. (18) formula synthetic among the reactive dyestuffs C:
1, doazo reaction: the 50.3g sulfonation para-ester joined in 100ml water and the 50g trash ice solution pulled an oar 1 hour.Then add 12.5g hydrochloric acid (30%), stir after 1 minute, molten clear 30% Sodium Nitrite 24.5g slowly is added drop-wise in the good para-ester of making beating carries out diazotization reaction, the control temperature is 8-15 ℃ in the dropping process, and pH value is controlled 1-1.2.And make the micro-indigo plant of starch potassium iodide paper, the micro-indigo plant of congo-red test paper.After sodium nitrite solution dropwises, keep 8-15 ℃ of temperature, then pH value control 1-1.2 restir reaction 30 minutes uses the excessive Sodium Nitrite of thionamic acid balance.Shown in doazo reaction reaction formula following (32) formula.
2, acid coupling reaction: 18.5 g J acid are joined in the 150g water, and regulate pH value 6.0-6.5 with 8.5g sodium bicarbonate, make J acid fully molten clear.Then molten clear J acid solution is added drop-wise in the Balanced sulfonation para-ester diazonium salt fast, 5-15 ℃ of control temperature carried out acid coupling, and after stirring reaction 2-3 hour, diazonium salt disappears and is the acid coupling terminal point.Shown in coupled reaction formula following (33) formula.
3, para-ester doazo reaction: 30.2 g are joined in 10ml water and the 50g trash ice solution (beta-sulfuric ester ethyl sulfonyl) aniline (para-ester) pulled an oar 1 hour.Then add 13.6g hydrochloric acid (30%), stir after 1 minute, molten clear 30% Sodium Nitrite 25.1g slowly is added drop-wise in the good para-ester of making beating carries out diazotization reaction, the control temperature is 8-15 ℃ in the dropping process, and pH value is controlled 1-1.2.And make the micro-indigo plant of starch potassium iodide paper, the micro-indigo plant of congo-red test paper.After sodium nitrite solution dropwises, keep 8-15 ℃ of temperature, then pH value control 1-1.2 restir reaction 30 minutes uses the excessive Sodium Nitrite of thionamic acid balance.Shown in doazo reaction reaction formula following (34) formula.
4, alkaline coupling reaction:
The para-ester diazo liquid that balance is good poured in the sour even liquid carry out coupling, temperature 10-15 ℃, regulate pH=6.0-6.2 with 15.5g sodium bicarbonate, and PH reaction 2-3 hour is protected in insulation, making the diazonium salt completely dissolve is the coupling terminal point, get (18) formula among the reactive dyestuffs B, the whole magma sprays of gained dyestuff are done, and get approximately 89.4 g of red granules dry product.Shown in coupled reaction formula following (35) formula.
Other dye structures are synthetic all with reference to above-mentioned synthesis route, enumerate no longer one by one here.
Dyestuff C 10 g shown in dyestuff B 17.4g shown in dyestuff A 72.6g shown in the modus ponens (4), the formula (11), the formula (18), Sodium sulfate anhydrous.min(99) 20g, Dispersant MF 1g, dust-proofing agent 0.4g, water 400g carry out blending under 20-50 ℃ of temperature, stir, then spraying drying obtains composite reactive dark black dye of the present invention or gets the above-mentioned materials dry product and directly do to piece together and get final product.
The concrete steps of embodiment 2-9 such as embodiment 1, concrete proportioning is as shown in table 1:
Table 1
Blending operational path shown in the whole reference example 2-9 of other dye structure blending ratios is enumerated here no longer one by one.
The 100g cotton by the black dyes that embodiment 4-12 obtains, is pressed fabric and is weighed 2%, contain the 60g/l Sodium sulfate anhydrous.min(99), bath raio is in the dye bath of 20:1,60 ℃ of lower absorption 30min add soda ash (consumption 15-20g/l) fixation 45 min.DYED FABRICS is through washing, soap boiling, drying.The black cotton that obtains has black and satisfied Exposure to Sunlight and the moisture resistant fastness of homogeneous.Specific performance sees Table 2.
Table 2:
Claims (6)
1. a compound active dark black dye is characterized in that comprising that A, B, three kinds of reactive dyestuffs of C mix, and A, B, three kinds of reactive dyestuffs mass percents of C are: dyestuff A accounts for 50-80%; Dyestuff B accounts for 10-40%; Dyestuff C accounts for 5-30%; A, B, three kinds of reactive dyestuffs of C are comprised of (1), (2), (3) three kinds of general structures respectively:
Dyestuff A comprise as the formula (1) any one or more than one
Wherein: R
1, R
2, R
3, R
4For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H,
Dyestuff B comprise as the formula (2) any one or more than one
Wherein: R
5, R
6, R
7, R
8For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H,
Dyestuff C comprise as the formula (3) any one or more than one
Wherein: R
9, R
10, R
11, R
12For-H ,-CH
3,-OCH
3,-SO
3H; X is-CH=CH
2,-CH
2CH
2OSO
3M; M is Na, K or H.
2. a kind of compound active dark black dye according to claim 1 is characterized in that being comprised of three kinds of reactive dyestuffs of A, B, C and the auxiliary agent of above-mentioned degree.
3. a kind of compound active dark black dye according to claim 2 is characterized in that described auxiliary agent is a kind of or its mixture in Sodium sulfate anhydrous.min(99), Sodium hexametaphosphate 99, condensation compound of methyl naphthalene sulfonic acid and formaldehyde, the naphthalene sulfonic acidformaldehyde condensation product.
4. a kind of compound active dark black dye according to claim 1, it is characterized in that described dyestuff A general structure (1) in the formula of (4)～(10) any one or more than one,
5. compound active dark black dye according to claim 1, it is characterized in that described dyestuff B general structure (2) in the formula of (11)～(17) any one or more than one
6. a kind of compound active dark black dye according to claim 1, it is characterized in that described dyestuff C-structure general formula in the formula of (18)～(25) any one or more than one,
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012103676303A CN102898869A (en) | 2012-09-28 | 2012-09-28 | Composite dark black reactive dye |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012103676303A CN102898869A (en) | 2012-09-28 | 2012-09-28 | Composite dark black reactive dye |
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|---|---|
| CN102898869A true CN102898869A (en) | 2013-01-30 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
| CN103554983A (en) * | 2013-10-31 | 2014-02-05 | 天津德凯化工股份有限公司 | Purple reactive dye and preparation method thereof |
| CN104927394A (en) * | 2015-05-27 | 2015-09-23 | 江苏沃尔得化工有限公司 | Synthetic process for active dye black |
| CN108824034A (en) * | 2018-06-22 | 2018-11-16 | 佛山市亨特纺织有限公司 | A kind of dustless black processing method of polyester-cotton blend/cotton knitted fabric |
| CN109762367A (en) * | 2018-11-28 | 2019-05-17 | 浙江科永化工有限公司 | A kind of reactive blue is to black dye composition, dye preparations and its application |
| CN112679988A (en) * | 2020-12-26 | 2021-04-20 | 浙江科永化工有限公司 | Active navy blue to black dye composition and dye product |
| CN113563734A (en) * | 2021-08-11 | 2021-10-29 | 浙江亿得新材料股份有限公司 | Synthesis method based on recycling |
| CN115537037A (en) * | 2022-08-26 | 2022-12-30 | 浙江瑞华化工有限公司 | Black reactive dye and preparation method and application thereof |
| CN116102900A (en) * | 2023-02-13 | 2023-05-12 | 湖北华丽染料工业有限公司 | Reactive dark black dye and application thereof |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
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| CN104927394A (en) * | 2015-05-27 | 2015-09-23 | 江苏沃尔得化工有限公司 | Synthetic process for active dye black |
| CN108824034A (en) * | 2018-06-22 | 2018-11-16 | 佛山市亨特纺织有限公司 | A kind of dustless black processing method of polyester-cotton blend/cotton knitted fabric |
| CN109762367A (en) * | 2018-11-28 | 2019-05-17 | 浙江科永化工有限公司 | A kind of reactive blue is to black dye composition, dye preparations and its application |
| CN112679988A (en) * | 2020-12-26 | 2021-04-20 | 浙江科永化工有限公司 | Active navy blue to black dye composition and dye product |
| WO2022134534A1 (en) * | 2020-12-26 | 2022-06-30 | 浙江科永化工有限公司 | Active navy blue-to-black dye composition and dye product |
| CN112679988B (en) * | 2020-12-26 | 2022-09-27 | 浙江科永化工有限公司 | Active navy blue to black dye composition and dye product |
| CN113563734A (en) * | 2021-08-11 | 2021-10-29 | 浙江亿得新材料股份有限公司 | Synthesis method based on recycling |
| CN113563734B (en) * | 2021-08-11 | 2023-10-27 | 浙江亿得新材料股份有限公司 | Synthesis method based on cyclic recovery |
| CN115537037A (en) * | 2022-08-26 | 2022-12-30 | 浙江瑞华化工有限公司 | Black reactive dye and preparation method and application thereof |
| CN115537037B (en) * | 2022-08-26 | 2024-03-01 | 浙江瑞华化工有限公司 | Black reactive dye and preparation method and application thereof |
| CN116102900A (en) * | 2023-02-13 | 2023-05-12 | 湖北华丽染料工业有限公司 | Reactive dark black dye and application thereof |
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Application publication date: 20130130 |