CN105111774A - Blue disperse dyestuff compounds, dye composition, dye product and application thereof - Google Patents
Blue disperse dyestuff compounds, dye composition, dye product and application thereof Download PDFInfo
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Abstract
The invention discloses blue disperse dyestuff compounds as shown in a formula (I) which is described in the specification, a dye composition, a dye product and application thereof. The dark blue to black disperse dyestuff composition contains a dye component A, a dye component B and/or a dye component C, wherein the dye component A is one or more selected from the compounds as shown in the formula (I), the dye component B is one or more selected from compounds as shown in a formula (II) which is described in the specification, the dye component C is one or more selected from compounds as shown in a formula (III) which is described in the specification, and the contents of the dye component B and the dye component C are not zero at the same time. The dye product contains the blue disperse dyestuff compounds or the dark blue to black disperse dyestuff composition. The invention also provides application of the blue disperse dyestuff compounds in dyeing or printing of hydrophobic fibrous materials. The blue disperse dyestuff compounds are applicable to small-bath ratio dyeing, have various excellent fastnesses and a wide pH value tolerance scope, can realize dyeing in a dye bath with a pH value of 3.5 to 14 and shows outstanding resistance to alkali.
Description
(1) technical field
The present invention relates to a kind of blue disperse dye compound, dark blue to the application in black disperse dye composition and dye preparations thereof and its (particularly polyester and BLENDED FABRIC material thereof) at hydrophobic fiber material dyeing or stamp.
(2) background technology
Dispersed dye are applied under high temperature (125 DEG C ~ 135 DEG C) condition, have a chemical stability problems.When Value in Dyeing Process is in 3 ~ 6 scopes, acid-resistant stability is good, not easily causes obvious aberration.But when under dye bath pH > 6 condition, can there is hydrolysis reaction in many conventional dispersed dye, make Dry Sack shoal, and coloured light mutation, alkali stability is very poor.
In traditional polyester piece good dyeing and finishing processing, pre-treatment destarch, refining (comprising lax) and Alkali reduction operation are carried out in the basic conditions, and disperse dyeing is carried out mostly in acid bath.Slurry, finish and other degradation productions do not cleaned due to pre-treatment are separated out in acid bath, cause producing many dye defects.Therefore, dispersed dye basic Dyeing is developed at the mid-80.The advantages such as the basic Dyeing of dispersed dye has that huge legendary turtle splitting or integrating is loose, level dyeing, solubilized and lubricity; thus reach and can protect that fabric is wrinkling from scratch, the contamination that prevents oligopolymer, omit or alleviate reduction clearing etc.; optimize dyeing, and create condition for part polyester piece good realizes refining one-pass bath method for dyeing.
In addition, dyeing the Eleventh Five-Year Plan period realizes energy consumption and declines 20%, and water consumption declines 30%, and the ultimate aim of pollutant emission decline 10%, must set about from beginning of production, realize short liquor ratio, and decreasing pollution thing discharges.Therefore, alkali resistance is good, excellent performance, is applicable to short liquor dyeing, and the dispersed dye of reasonable price need further to be researched and developed.
(3) summary of the invention
First object of the present invention is the blue disperse dye compound providing a kind of alkali resistance,
Second object of the present invention is that providing a kind of contains the dark blue to black disperse dye composition of described blue disperse dye compound.
3rd object of the present invention is to provide a kind of dye preparations obtained by described blue disperse dye compound.
4th object of the present invention is to provide a kind of by the described dark blue dye preparations obtained to black disperse dye composition.
5th object of the present invention is to provide the application of described dispersed blue dye compound in the dyeing or stamp of hydrophobic fiber material especially polyester and BLENDED FABRIC thereof.
For achieving the above object, the present invention adopts following technical scheme:
The invention provides the blue disperse dye compound shown in a kind of formula I,
Wherein, X
1for H, halogen, C
1~ C
4alkyl or C
1~ C
4alkoxyl group.
Further, blue disperse dye compound preferred structure of the present invention is as follows:
Blue disperse dye compound of the present invention, its preparation method is as follows:
(1) preparation of coupling component:
In reactor, drop into appropriate water, raw material a, soda ash, propenyl chloride, stir insulation reaction 16-20h, after reaction end arrives at 80-90 DEG C, be cooled to 25-35 DEG C, stop stirring, leave standstill 20 ~ 60min, separatory, extract upper strata oily matter and drop into flask, add the liquid caustic soda of a certain amount of 30%, control temperature is at 20-25 DEG C, drip the vinyl cyanide measured, time for adding controls at 1-2h, at 20-25 DEG C of insulation reaction 12-16h, obtains structure such as formula the compound shown in (V);
Wherein, described raw material a is N-hydroxyethyl meta-aminotoluene or N-β-anilino-ethanol;
Molar ratio is raw material a: propenyl chloride: vinyl cyanide=1:1 ~ 1.2:1.05 ~ 1.2; Raw material a: the mol ratio of soda ash is 1:0.4 ~ 0.6; Raw material a: the mol ratio of liquid caustic soda is 1:0.05;
(2) doazo reaction:
Drop into the sulfuric acid, the phosphoric acid that measure in the reactor, control temperature, at 15-25 DEG C, adds Sodium Nitrite, is cooled to 0-5 DEG C, slowly adds the compound of structure formula IV, at 0-5 DEG C of insulated and stirred reaction 5-6h, obtains diazo liquid;
Wherein, molar ratio is formula IV compound: sulfuric acid: phosphoric acid: Sodium Nitrite=1:2 ~ 3:0.2 ~ 1:1 ~ 1.5;
(3) coupled reaction:
In flask, add appropriate water, sulfuric acid, slowly pour formula (V) compound that step (1) is synthesized into, making beating 0.5 ~ 2h; Control temperature remains on 0-5 DEG C, drips the diazo liquid that step (2) obtains, and after dropwising, keep 0-5 DEG C to continue to stir 4-6h, be warming up to 70-75 DEG C and turn brilliant 1 ~ 3h, suction filtration, 50-70 DEG C of hot wash, to neutral, obtains dispersed dye;
Formula (V) compound: the mol ratio of formula (IV) compound is 1 ~ 1.1:1; Structural formula (V) compound: the mol ratio of sulfuric acid is 1:0.5 ~ 1;
In formula (V), X
1the same formula I of definition.
Further, formula (V) is preferably as follows:
Present invention also offers a kind of dark blue to black disperse dye composition, said composition contains dye component A and dye component B and/or dye component C, described dye component A be selected from the dye composition shown in formula I one or more, described dye component B be selected from the dye composition shown in formula II one or more, described dye component C be selected from the dye composition shown in formula III one or more; Based on the gross weight of described dye component A, B and C, wherein the weight percentage of dye component A is 30-95% (preferably 50 ~ 90%), the weight percentage of dye component B is 0-50% (preferably 0 ~ 35%), the weight percentage of dye component C is 0-30% (preferably 0 ~ 20%), and is 0 when the content of dye component B, dye component C is different;
In formula I, X
1definition the same;
In formula II, R
1for H, halogen or-CN; R
2for H, halogen or-NO
2; R
3for unsubstituted C
1-C
4alkyl, or by cyano group or C
1~ C
4the C that alkoxyl group replaces
1-C
4alkyl; R
4for phenmethyl, styroyl, unsubstituted C
1-C
4alkyl or by cyano group or C
1~ C
4the C that alkoxyl group replaces
1-C
4alkyl, X
2for H or C
1~ C
4alkyl;
In formula III, R
5, R
6, R
7respective is independently H, halogen or nitro; X
3for H, halogen or C
1~ C
4alkyl; R
8for cyanoethyl, C
1-C
6alkyl or by C
1-C
6the C that alkoxyl group replaces
1-C
6alkyl; R
9for cyanoethyl, benzyl, styroyl, C
1-C
6alkyl or by C
1-C
6the C that alkoxyl group replaces
1-C
6alkyl.
Further, halogen preferred F, Cl or Br.
Further, described dye component A is preferably one or both the mixture in the dye composition shown in above formula (I-1) ~ (I-2);
Described dye component B is preferably one or more the mixture in the dye composition shown in following formula (II-1) ~ (II-14);
Described dye component C is preferably one or more the mixture in the dye composition shown in following formula (III-1) ~ (III-20):
As particularly preferably, DISPERSE NAVY BLUE EXSF 300& BLUE 56 100 of the present invention is to black dye composition, dye component A is the dye composition shown in formula (I-1), dye component B is the dye composition shown in formula (II-1), dye component C is the dye composition shown in formula (III-1), based on described dye component A, B, the gross weight of C, wherein the weight percentage of dye component A is 30-95% (preferably 50 ~ 90%), the weight percentage of dye component B is 0-50% (preferably 0 ~ 35%), the weight percentage of dye component C is 0-30% (preferably 0 ~ 20%), and dye component B, the content of dye component C is 0 time different.
Blue disperse dye compound of the present invention and composition, through commercial treatment, thus dispersed dye goods need be obtained, in other words when being applied to dyeing, described dispersed dye goods, containing described blue disperse dye compound or described dark blue to black disperse dye composition.Further, described dispersed dye goods are mainly containing described blue disperse dye compound or described dark blue to black disperse dye composition and auxiliary agent.The auxiliary agent added is dispersion agent, diffusant and the tensio-active agent thereof etc. that dispersed dye commercialization is conventional, and preferred auxiliary agent is one of following or its mixture: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products (as condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF)), naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (xylogen 85A, xylogen 83A) etc.Usually, the ratio of the gross weight of auxiliary agent and former dye component (i.e. dispersed blue dye compound or dark blue to black disperse dye composition) is 0.2 ~ 5:1.
Commercial treatment (i.e. the preparation of dye preparations) the available following methods of blue disperse dye compound of the present invention and composition carries out: such as the disperse dye compound shown in formula I is carried out corpusculed with the pulverizer such as sand mill or shredder under the existence of auxiliary agent, water; Or, by the dye composition represented by component A, B component, component C by after the mixing of above-mentioned proportioning, under the existence of auxiliary agent, water, carry out corpusculed with the pulverizer such as sand mill or shredder; Also mix with above-mentioned ratio after the dye composition represented by component A, B component, component C can being carried out corpusculed process with the pulverizer such as sand mill or shredder respectively under the existence of auxiliary agent, water in addition.Dispersed blue dye compound of the present invention and composition, aqueous with can be after sand mill or shredder grinding, can be powdery, particulate state after spraying dry.
Dispersed blue dye compound of the present invention and composition, also allow to make new composition with the further compound synergic of other dyestuffs, or add other shading components such as red, blue or orange.
Dye composition shown in Chinese style of the present invention (II) and formula (III) according to the method described in patent CN101845234A, CN102504596A, CN1036974, CN101117446 or the preparation of similar method, also can adopt commercially available prod.
Present invention also offers the application of described dispersed blue dye compound in the dyeing or stamp of hydrophobic fiber material especially polyester and BLENDED FABRIC thereof, described application comprises applies dispersed blue dye compound separately or is applied by itself and other composite composition of making of dyestuff again.
Beneficial effect of the present invention is: described alkali resistance Disperse blue dye compound and composition, be applicable to short liquor dyeing, and every fastness is excellent, and resistance to pH wide ranges can be dye in the dye bath of 3.5-14 at pH, and alkali resistance is given prominence to.
(4) accompanying drawing explanation
Fig. 1 and Fig. 2 is lifting force comparison diagram.
(5) specific embodiment scheme
Below in conjunction with specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to this.
EXAMPLE l:
(1) preparation of coupling component:
In 1000mL flask, drop into the water of 200ml, 98%N-β-anilino-ethanol 16.8g, 98% soda ash 6.8g, 98% propenyl chloride 5.5g, stir insulation reaction 16-20h at 80-90 DEG C.After reaction end arrives, be cooled to 25-35 DEG C, stop stirring, leave standstill 0.5h, separatory, extract upper strata oily matter and drop into flask, add 30% liquid caustic soda 8g, control temperature is at 20-25 DEG C, drip 98% vinyl cyanide 7.7g, time for adding controls at 1-2h, at 20-25 DEG C of insulation reaction 12-16h, obtains structural formula (V-1) compound.
(2) doazo reaction:
In flask, drop into 98% sulfuric acid 35.8g, 85% phosphatase 79 .2g, control temperature, at 15-25 DEG C, adds 15% Sodium Nitrite 56.6g, be cooled to 0-5 DEG C, slowly add the compound of structure formula IV, at 0-5 DEG C of insulated and stirred reaction 5-6h, obtain diazo liquid.
(3) coupled reaction:
In flask, add the water of 200mL, 98% sulfuric acid 6g, slowly pour structural formula (V-1) compound that step (1) is synthesized into, making beating 0.5h.Control temperature remains on 0-2 DEG C, drip the diazo liquid that step (2) obtains, after dropwising, 0-5 DEG C is kept to continue to stir 4-6h, be warming up to 70-75 DEG C and turn brilliant 2h, suction filtration, 50-70 DEG C of hot wash is to neutral, obtain dispersed dye shown in formula (I-1), λ max=590nm.
Embodiment 2:
(1) preparation of coupling component:
In 1000mL flask, drop into the water of 200ml, 98%N-hydroxyethyl meta-aminotoluene 16.6g, 98% soda ash 6.2g, 100% propenyl chloride 5.1g, stir insulation reaction 16-20h at 80-90 DEG C.After reaction end arrives, be cooled to 25-35 DEG C, stop stirring, leave standstill 0.5h, separatory, extract upper strata oily matter and drop into flask, add 30% liquid caustic soda 7.3g, control temperature is at 20-25 DEG C, drip 98% vinyl cyanide 7.1g, time for adding controls at 1-2h, at 20-25 DEG C of insulation reaction 12-16h, obtains structural formula (V-2) compound.
(2) doazo reaction:
In flask, drop into 98% sulfuric acid 32.8g, 85% phosphoric acid 8.5g, control temperature, at 15-25 DEG C, adds 15% Sodium Nitrite 51.9g, be cooled to 0-5 DEG C, slowly add the compound of structure formula IV, at 0-5 DEG C of insulated and stirred reaction 5-6h, obtain diazo liquid.
(3) coupled reaction:
In flask, add the water of 200mL, 98% sulfuric acid 5.5g, slowly pour structural formula (V-2) compound that step (1) is synthesized into, making beating 0.5h.Control temperature remains on 0-2 DEG C, drips the diazo liquid that step (2) obtains, after dropwising, keep 0-5 DEG C to continue to stir 4-6h, be warming up to 70-75 DEG C and turn brilliant 2h, suction filtration, 50-70 DEG C of hot wash, to neutral, obtains dispersed dye shown in formula (I-2).λmax＝600nm。
Embodiment 3:
By 82 grams of formula (I-1) compounds, the Dispersant MF of 150 grams, after adding 200 grams of water Mixed Pinyins, grinding distribution, spraying dry, gets product, and this finished product can provide fabric blue color.
Embodiment 4:
By 100 grams of formula (I-2) compounds, the Dispersant MF of 50 grams, 100 grams of dispersing agent NNOs, after adding 200 grams of water Mixed Pinyins, grinding distribution, spraying dry, gets product, and this finished product can provide fabric blue color.
Embodiment 5:
By 80.7 grams of formula (I-2) compounds, 16.1 grams of formula (II-1) B component, 3.2 grams of formula (III-1) component C, the Dispersant MF of 250 grams, after adding 200 grams of water Mixed Pinyins, grinding distribution, spraying dry, gets product, and this finished product can provide fabric dark blue tone.
Embodiment 6 ~ 30
According to the method described in embodiment 1 or 2, unlike the weight ratio and the auxiliary agent that adopt component A, B component, component C in table 1, slurries are made after the blending that adds water, controlling the solid content of slurries is 35 ~ 45% to be advisable, grinding distribution, drying, obtained finished product, can be supplied to fabric evenly and the good blueness of fastness ability to black tone.85A, 83A in table 1 are respectively xylogen 85A, xylogen 83A.
Table 1
Tint applications 1:
The disperse dye compound taking 4 grams of embodiments 1 obtained is dispersed in 100 ml waters, mixes, with sheet adjusting PH with base to 12.5 after drawing 3 milliliters with the water of 21 milliliters, put into 4 grams of polyester textiles, be warming up to 70 DEG C, continue with about 2 DEG C/min gradient increased temperature to 130 DEG C, insulation dyeing 45 minutes.Then be cooled to about 80 DEG C and use hot water wash 10min, dry.Observe sample cloth coloured light, it is resistance toly soaped, antifriction scrape along color fastness to sublimation to adopt GB/T3921-2008, GB/T3920-2008 and GB/T5718-1997 to test respectively, the results are shown in following table 2.
Table 2
According to the method described in above-mentioned Dyeing Example, the dyestuff of preparation in embodiment 2 ~ 30 is adopted to carry out bath raio 1:6 dyeing respectively, dye level 3.0%, unlike change dyeing pH value, the basically identical blueness of dyeing behavior can be obtained equally to dark blue to black fabric, specifically in table 3.
Table 3
Tint applications 2:
Comparative example 1: by (c-a) in patent CN101265369A embodiment 1 as a comparison;
Comparative example 2: composite dispersed dye patent CN101265369A embodiment 25 obtained embodiment 2 as a comparison;
Comparative example 3: by the dye monomer shown in the dye monomer shown in patent CN104371366A formula (I-1), formula (II-1) and the dye monomer shown in formula (III-7), black dyes is made, as a comparison embodiment 3 according to the method for the embodiment of the present application 1;
Comparative example 4: the composite disperse navy blue dyestuff embodiment 4 as a comparison patent CN102746713A embodiment 2 obtained;
Comparative example 5: composite dispersed deep blue dye patent CN101649129A embodiment 1 obtained embodiment 5 as a comparison;
By embodiment in the present invention 1, embodiment 2, composite disperse dye obtained in comparative example 1, comparative example 2, comparative example 3, comparative example 4, comparative example 5 carries out coloured differently Inner dyeing respectively according to the method (bath raio 1:6) of tint applications 1, and dye level is respectively 0.5%, 1%, 2%, 4%, 6%, 8%.According to its lifting force of GB/T2397-2003 standard testing, gained lifting force result as shown in Figure 1 and Figure 2.
From Fig. 1 and Fig. 2, dispersion of the present invention is blue, and to black dye composition, not only every fastness ability such as washing fastness, sublimation fastness, crock fastness is excellent, and it is better than the enhancing of existing common alkali resistance dispersion blue-black dyestuff, dye uptake is fast, dye yield is high, cost-saving, and be suitable for short liquor dyeing, energy-conserving and environment-protective.
Claims (10)
1. the blue disperse dye compound shown in formula I,
Wherein, X
1for H, halogen, C
1~ C
4alkyl or C
1~ C
4alkoxyl group.
2. blue disperse dye compound as claimed in claim 1, is characterized in that: described blue disperse dye compound is one of following:
3. one kind dark blue to black disperse dye composition, it is characterized in that: described composition contains dye component A and dye component B and/or dye component C, described dye component A be selected from the dye composition shown in formula I one or more, described dye component B be selected from the dye composition shown in formula II one or more, described dye component C be selected from the dye composition shown in formula III one or more; Based on the gross weight of described dye component A, B and C, wherein the weight percentage of dye component A is 30-95%, the weight percentage of dye component B is 0-50%, and the weight percentage of dye component C is 0-30%, and is 0 when the content of dye component B, dye component C is different;
In formula I, X
1for H, halogen, C
1~ C
4alkyl or C
1~ C
4alkoxyl group;
In formula II, R
1for H, halogen or-CN; R
2for H, halogen or-NO
2; R
3for unsubstituted C
1-C
4alkyl, or by cyano group or C
1~ C
4the C that alkoxyl group replaces
1-C
4alkyl; R
4for phenmethyl, styroyl, unsubstituted C
1-C
4alkyl or by cyano group or C
1~ C
4the C that alkoxyl group replaces
1-C
4alkyl, X
2for H or C
1~ C
4alkyl;
In formula III, R
5, R
6, R
7respective is independently H, halogen or nitro; X
3for H, halogen or C
1~ C
4alkyl; R
8for cyanoethyl, C
1-C
6alkyl or by C
1-C
6the C that alkoxyl group replaces
1-C
6alkyl; R
9for cyanoethyl, benzyl, styroyl, C
1-C
6alkyl or by C
1-C
6the C that alkoxyl group replaces
1-C
6alkyl.
4. dark blue to black disperse dye composition as claimed in claim 3, it is characterized in that: the weight percentage of dye component A is 50 ~ 90%, the weight percentage of dye component B is 0 ~ 35%, the weight percentage of dye component C is 0 ~ 20%, and is 0 when the content of dye component B, dye component C is different.
5. dark blue to black disperse dye composition as described in claim 3 or 4, is characterized in that: described dye component A is one or both the mixture in the dye composition shown in above formula (I-1) ~ (I-2);
6. dark blue to black disperse dye composition as described in claim 3 or 4, is characterized in that: described dye component B is one or more the mixture in the dye composition shown in following formula (II-1) ~ (II-14);
7. dark blue to black disperse dye composition as described in claim 3 or 4, is characterized in that: described dye component C is one or more the mixture in the dye composition shown in following formula (III-1) ~ (III-20):
8. blue disperse dye goods, containing, for example described blue disperse dye compound according to claim 1.
9. dark blue to black disperse dye goods, containing, for example according to claim 3 dark blue to black disperse dye composition.
10. the application of blue disperse dye compound in the dyeing or stamp of hydrophobic fiber material as claimed in claim 1.
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| CN105907126A (en) * | 2016-04-20 | 2016-08-31 | 烟台利盈化工科技有限公司 | Strong-alkaline-resistant disperse blue dye, compounded mixture thereof, and preparation method thereof |
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| CN109487579A (en) * | 2018-11-19 | 2019-03-19 | 浙江乐高实业股份有限公司 | Super fine denier polyester fiber short route dyeing method |
| CN109608901A (en) * | 2019-01-16 | 2019-04-12 | 绍兴市上虞鼎诚化工有限公司 | A kind of preparation method of benzisothiazole-azo dispersed blue dye |
| CN110643197A (en) * | 2019-10-10 | 2020-01-03 | 济南大学 | Disperse black dye composition, disperse black dye and preparation method and application thereof |
| CN113913028A (en) * | 2020-08-27 | 2022-01-11 | 青岛大学 | High-alkali-resistance high-oxygen-resistance bleaching disperse dye of monochloro-substituted benzothiazole |
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| CN105907126B (en) * | 2016-04-20 | 2018-01-05 | 烟台澳土复合材料有限公司 | A kind of dispersed blue dye of resistance to highly basic, its compounding mixture and preparation method thereof |
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| CN106478543B (en) * | 2016-09-30 | 2020-03-06 | 浙江闰土研究院有限公司 | Benzisothiazole dye monomer compound and intermediate, preparation method and application thereof |
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| CN109487579A (en) * | 2018-11-19 | 2019-03-19 | 浙江乐高实业股份有限公司 | Super fine denier polyester fiber short route dyeing method |
| CN109487579B (en) * | 2018-11-19 | 2021-01-26 | 浙江乐高实业股份有限公司 | Short-process printing and dyeing method for superfine denier polyester fiber |
| CN109608901A (en) * | 2019-01-16 | 2019-04-12 | 绍兴市上虞鼎诚化工有限公司 | A kind of preparation method of benzisothiazole-azo dispersed blue dye |
| CN110643197A (en) * | 2019-10-10 | 2020-01-03 | 济南大学 | Disperse black dye composition, disperse black dye and preparation method and application thereof |
| CN113913028A (en) * | 2020-08-27 | 2022-01-11 | 青岛大学 | High-alkali-resistance high-oxygen-resistance bleaching disperse dye of monochloro-substituted benzothiazole |
| CN113913027A (en) * | 2020-08-27 | 2022-01-11 | 青岛大学 | Dichloro-substituted benzothiazole high-alkali-resistance high-oxygen-resistance bleaching-resistant disperse dye |
| CN113913028B (en) * | 2020-08-27 | 2023-12-01 | 青岛大学 | Monochloro-substituted benzothiazole high alkali resistance Gao Naiyang bleach disperse dye |
| CN113913027B (en) * | 2020-08-27 | 2023-12-05 | 青岛大学 | Dichloro substituted benzothiazole high alkali resistance Gao Naiyang bleach disperse dye |
| CN115044229A (en) * | 2022-07-04 | 2022-09-13 | 杭州迈染新材料有限公司 | Black dye composition for dyeing diacetate fibers, disperse dye and application thereof |
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