CN105111774B - 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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- CN105111774B CN105111774B CN201510278525.6A CN201510278525A CN105111774B CN 105111774 B CN105111774 B CN 105111774B CN 201510278525 A CN201510278525 A CN 201510278525A CN 105111774 B CN105111774 B CN 105111774B
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- 239000000975 dye Substances 0.000 title claims abstract description 111
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 238000004043 dyeing Methods 0.000 claims abstract description 19
- 239000002657 fibrous material Substances 0.000 claims abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 5
- 239000000986 disperse dye Substances 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000004744 fabric Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 8
- 239000001045 blue dye Substances 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000009413 insulation Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 0 CC(N(*)C(C=C1)=CC(*)[C@]1N=Nc1c(cc(cc2)[N+]([O-])=O)c2n[s]1)=C Chemical compound CC(N(*)C(C=C1)=CC(*)[C@]1N=Nc1c(cc(cc2)[N+]([O-])=O)c2n[s]1)=C 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000013329 compounding Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- -1 Naphthalene sulfonic acids Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical class OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 2
- 229920004934 Dacron® Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 description 1
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SQBCSDZTDXLTLE-UHFFFAOYSA-N Nc1c(cc(cc2)[N+]([O-])=O)c2n[s]1 Chemical compound Nc1c(cc(cc2)[N+]([O-])=O)c2n[s]1 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009990 desizing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
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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 black disperse dye composition and its dye preparations
And its application in (particularly polyester and its blend fabric material) dyeing of hydrophobic fiber material or stamp.
(2) background technology
Disperse dyes are applied under the conditions of high temperature (125 DEG C～135 DEG C), there is a chemical stability problems.As dye bath pH
In the range of 3～6, acid-resistant stability is good, does not easily cause obvious aberration for value.But under the conditions of dye bath pH ＞ 6, many commonly-used point
Scattered dyestuff can occur hydrolysis so that discoloration is shallow, and coloured light mutation, alkali stability is very poor.
In traditional dacron dyeing and finishing processing, pre-treatment desizing, refining (including lax) and Alkali reduction operation are in alkalescence
Under the conditions of carry out, and disperse dyeing is carried out in acid bath mostly.The slurry do not cleaned due to pre-treatment, finish and
Other catabolites are separated out in acid bath, cause to produce many dye defects.Therefore, disperse dyes alkali is developed in the mid-80
Property decoration method.The basic Dyeing of disperse dyes has the advantages that chelant, dispersion, level dyeing, solubilized and greasy property, so as to reach
To protecting fabric from abrading corrugation, prevent the contamination of oligomer, omit or mitigate reduction cleaning etc., dyer is optimized
Skill, and realize that refining one-pass bath method for dyeing creates condition for part dacron.
Additionally, dyeing the Eleventh Five-Year Plan period realizes that energy consumption declines 20%, water consumption declines 30%, under pollutant emission
The final goal of drop 10%, it is necessary to set about from beginning of production, realizes short liquor ratio, reduces pollutant emission.Therefore, alkali resistance it is good,
Excellent performance, it is adaptable to short liquor dyeing, and the disperse dyes of reasonable price need further research and development.
(3) content of the invention
First purpose of the present invention is the blue disperse dye compound for providing a kind of alkali resistance,
Second object of the present invention is to provide a kind of containing the dark blue to black of the blue disperse dye compound
Disperse dye composition.
Third object of the present invention is to provide one kind dye preparations by obtained in the blue disperse dye compound.
Fourth object of the present invention be provide it is a kind of by it is described it is dark blue to black disperse dye composition obtained in contaminate
Material products.
5th purpose of the present invention is to provide the dispersed blue dye compound and especially gathers in hydrophobic fiber material
Application in the dyeing of ester and its blend fabric or stamp.
For achieving the above object, the present invention is adopted the following technical scheme that：
The invention provides the blue disperse dye compound shown in a kind of formula (I),
Wherein, X1For H, halogen, C1～C4Alkyl or C1～C4Alkoxyl.
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：
Appropriate water, raw material a, soda ash, chloropropene are put into in reactor, at 80-90 DEG C insulation reaction 16-20h are stirred,
After reaction end is arrived, 25-35 DEG C is cooled to, stops stirring, stand 20～60min, point liquid extracts upper strata grease input and burns
Bottle, adds a certain amount of 30% liquid caustic soda, and control temperature is added dropwise the acrylonitrile for measuring at 20-25 DEG C, and time for adding control exists
1-2h, in 20-25 DEG C of insulation reaction 12-16h, obtains compound of the structure as shown in formula (V)；
Wherein, described raw material a is N- hydroxyethyl meta-aminotoluenes or N- hydroxyethylanilines；
Molar ratio is raw material a：Chloropropene：Acrylonitrile=1:1～1.2:1.05～1.2；Raw material a：Soda ash mole
Than for 1:0.4～0.6；Raw material a：The mol ratio of liquid caustic soda is 1:0.05；
(2) diazo reaction：
Sulfuric acid, the phosphoric acid for measuring is put in the reactor, and control temperature adds natrium nitrosum, is cooled at 15-25 DEG C
0-5 DEG C, the compound of structural formula (IV) is slowly added to, in 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：Natrium nitrosum=1:2～3:0.2～1:1～
1.5；
(3) coupling reaction：
Appropriate water, sulfuric acid are added in flask, be poured slowly into step (1) synthesis formula (V) compound, beating 0.5～
2h；Control temperature is maintained at 0-5 DEG C, and the diazo liquid that step (2) is obtained is added dropwise, and after completion of dropping, is kept for 0-5 DEG C continue to stir 4-
6h, is warming up to 70-75 DEG C and turns 1～3h of crystalline substance, and suction filtration, 50-70 DEG C of hot wash obtains disperse dyes to neutrality；
Formula (V) compound：The mol ratio of formula (IV) compound is 1～1.1:1；Structural formula (V) compound：Sulfuric acid rubs
You are than being 1:0.5～1；
In formula (V), X1The same formula of definition (I).
Further, formula (V) is preferably as follows：
Present invention also offers a kind of dark blue to black disperse dye composition, said composition contain dye component A and
Dye component B and/or dye component C, the dye component A are selected from one or more in the dye composition shown in formula (I),
The dye component B is selected from one or more in the dye composition shown in formula (II), and the dye component C is selected from formula (III)
One or more in shown dye composition；Based on the gross weight of described dye component A, B and C, wherein dye component A's
Weight percentage is 30-95% (preferably 50～90%), the weight percentage of dye component B be 0-50% (preferably 0～
35%), the weight percentage of dye component C is 0-30% (preferably 0～20%), and dye component B, dye component C contain
It is 0 when amount is different；
In formula (I), X1It is defined as above；
In formula (II), R1For H, halogen or-CN；R2For H, halogen or-NO2；R3For unsubstituted C1-C4Alkyl, or quilt
Cyano group or C1～C4The C that alkoxyl replaces1-C4Alkyl；R4For benzyl, phenethyl, unsubstituted C1-C4Alkyl or by cyanogen
Base or C1～C4The C that alkoxyl replaces1-C4Alkyl, X2For H or C1～C4Alkyl；
In formula (III), R5、R6、R7Each stand alone as H, halogen or nitro；X3For H, halogen or C1～C4Alkyl；R8For cyanogen second
Base, C1-C6Alkyl or by C1-C6The C that alkoxyl replaces1-C6Alkyl；R9For cyanoethyl, benzyl, phenethyl, C1-C6Alkyl or quilt
C1-C6The C that alkoxyl replaces1-C6Alkyl.
Further, halogen preferred F, Cl or Br.
Further, the dye component A be preferably the one kind in the dye composition shown in above formula (I -1)～(I -2) or
Two kinds of mixture；
The dye component B is preferably one or more in the dye composition shown in following formula (II -1)～(II -14)
Mixture；
The dye component C is preferably one or more in the dye composition shown in following formula (III -1)～(III -20)
Mixture：
Used as particularly preferred, disperse dark blue of the present invention to black dye composition, dye component A is formula (I -1)
Shown dye composition, dye component B is the dye composition shown in formula (II -1), and dye component C is shown in formula (III -1)
Dye composition, based on the gross weight of described dye component A, B, 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 of dye component C
Amount percentage composition is 0-30% (preferably 0～20%), and is 0 during the content difference of dye component B, dye component C.
Blue disperse dye compound of the present invention and composition, are applied to the productization process that need to engage in trade during dyeing, from
And obtain disperse dyes product, in other words, described disperse dyes product, containing described blue disperse dye compound or
It is described dark blue to black disperse dye composition.Further, described disperse dyes product mainly contains described blue dispersion
Dye composition is described dark blue to black disperse dye composition and auxiliary agent.The auxiliary agent for being added is disperse dyes commercialization
The conventional dispersant of process, diffusant and its surfactant etc., preferred auxiliary agent is one of following or its mixture：Naphthalene sulfonic acids
Formaldehyde condensation products, lignosulfonates, alkyl naphthalene sulfonic acid formaldehyde condensation products are (such as condensation compound of methyl naphthalene sulfonic acid and formaldehyde (dispersant
MF)), naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent CNF), sodium lignin sulfonate
(lignin 85A, lignin 83A) etc..Generally, auxiliary agent and former dye component (i.e. dispersed blue dye compound or dark blue to black
Color disperse dye composition) gross weight ratio be 0.2～5:1.
The commercial treatment (i.e. the preparations of dye preparations) of blue disperse dye compound of the present invention and composition
Can be carried out with following methods：For example the disperse dye compound shown in formula (I) with sand mill or is ground in the presence of auxiliary agent, water
The pulverizers such as grinding machine carry out corpusculed；Or, the dye composition represented by component A, component B, component C is matched somebody with somebody by above-mentioned
After than mixing, corpusculed is carried out with pulverizers such as sand mill or grinders in the presence of auxiliary agent, water；In addition also can be by component
Dye composition represented by A, component B, component C uses respectively the pulverizer such as sand mill or grinder in the presence of auxiliary agent, water
Carry out being mixed with above-mentioned ratio after corpusculed process.Dispersed blue dye compound of the present invention and composition,
Can be powdery, graininess after spray drying with being liquid after sand mill or grinder grinding.
Dispersed blue dye compound of the present invention and composition, also allow and the further compound synergic system of other dyestuffs
The composition of Cheng Xin, or the shading components such as add other red, blue or orange.
In the present invention formula (II) and the dye composition shown in formula (III) can according to patent CN101845234A,
Prepared by the method or similar method described in CN102504596A, CN1036974, CN101117446, commercially available product may also be employed
Product.
Present invention also offers the dispersed blue dye compound is in hydrophobic fiber material especially polyester and its blending
Application in the dyeing of fabric or stamp, the application includes dispersed blue dye compound is used alone or by itself and other
Dyestuff compounding is made composition and is applied again.
The beneficial effects of the present invention is：Described alkali resistance Disperse blue dye compound and composition, it is adaptable to little
Bath ratio dyeing, every fastness is excellent, resistance to pH wide ranges, can dye in pH is for the dye bath of 3.5-14, and alkali resistance is projected.
(4) illustrate
Fig. 1 and Fig. 2 are lifting force comparison diagram.
(5) specific embodiment scheme
With reference to specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to
This.
Embodiment l:
(1) preparation of coupling component：
Water, 98%N- hydroxyethylaniline 16.8g, 98% soda ash 6.8g, 98% chlorine of 200ml are put into in 1000mL flasks
Propylene 5.5g, at 80-90 DEG C insulation reaction 16-20h is stirred.After reaction end is arrived, 25-35 DEG C is cooled to, stops stirring, stood
0.5h, point liquid extracts upper strata grease input flask, adds 30% liquid caustic soda 8g, and control temperature is added dropwise 98% the third at 20-25 DEG C
Alkene nitrile 7.7g, time for adding is controlled in 1-2h, in 20-25 DEG C of insulation reaction 12-16h, obtains structural formula (V -1) compound.
(2) diazo reaction：
98% sulfuric acid 35.8g, 85% phosphatase 79 .2g are put in flask, control temperature adds 15% nitrous at 15-25 DEG C
Sour sodium 56.6g, is cooled to 0-5 DEG C, is slowly added to the compound of structural formula (IV), in 0-5 DEG C of insulated and stirred reaction 5-6h, obtains
Diazo liquid.
(3) coupling reaction：
Water, the 98% sulfuric acid 6g of 200mL are added in flask, the structural formula (V -1) for being poured slowly into step (1) synthesis is changed
Compound, is beaten 0.5h.Control temperature is maintained at 0-2 DEG C, and the diazo liquid that step (2) is obtained is added dropwise, and after completion of dropping, keeps 0-5
DEG C continue to stir 4-6h, be warming up to 70-75 DEG C and turn crystalline substance 2h, suction filtration, 50-70 DEG C of hot wash obtains formula (I -1) shown to neutrality
Disperse dyes, λ max=590nm.
Embodiment 2:
(1) preparation of coupling component：
Put into in 1000mL flasks the water of 200ml, 98%N- hydroxyethyl meta-aminotoluene 16.6g, 98% soda ash 6.2g,
100% chloropropene 5.1g, at 80-90 DEG C insulation reaction 16-20h is stirred.After reaction end is arrived, 25-35 DEG C is cooled to, stops stirring
Mix, stand 0.5h, divide liquid, extract upper strata grease input flask, add 30% liquid caustic soda 7.3g, control temperature to drip at 20-25 DEG C
Plus 98% acrylonitrile 7.1g, time for adding controlled in 1-2h, in 20-25 DEG C of insulation reaction 12-16h, obtains structural formula (V -2)
Compound.
(2) diazo reaction：
98% sulfuric acid 32.8g, 85% phosphoric acid 8.5g are put in flask, control temperature adds 15% nitrous at 15-25 DEG C
Sour sodium 51.9g, is cooled to 0-5 DEG C, is slowly added to the compound of structural formula (IV), in 0-5 DEG C of insulated and stirred reaction 5-6h, obtains
Diazo liquid.
(3) coupling reaction：
Water, the 98% sulfuric acid 5.5g of 200mL are added in flask, the structural formula (V -2) of step (1) synthesis is poured slowly into
Compound, is beaten 0.5h.Control temperature is maintained at 0-2 DEG C, and the diazo liquid that step (2) is obtained is added dropwise, and after completion of dropping, keeps 0-
5 DEG C are continued to stir 4-6h, are warming up to 70-75 DEG C and are turned crystalline substance 2h, and suction filtration, 50-70 DEG C of hot wash obtains formula (I -2) institute to neutrality
Show disperse dyes.λ max=600nm.
Embodiment 3:
By 82 grams of formula (I-1) compounds, after 150 grams of Dispersant MF, plus 200 grams of water blendings, grinding distribution, spraying is dry
It is dry, get product, the finished product can provide fabric blue color.
Embodiment 4:
100 grams of formula (I-2) compounds, 50 grams of Dispersant MF after 100 grams of dispersing agent NNOs, plus 200 grams of water blendings, are ground
Mill dispersion, is spray-dried, and gets product, and the 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) components B, 3.2 grams of formula (III -1) components C, 250 grams
After Dispersant MF, plus 200 grams of water blendings, grinding distribution is spray-dried, and gets product, and the finished product can provide fabric dark blue tone.
Embodiment 6～30
According to the method described in embodiment 1 or 2, except for the difference that adopt component A in table 1, component B, the weight of component C ratio with
And auxiliary agent, slurries are made after the blending that adds water, the solid content for controlling slurries is advisable for 35～45%, grinding distribution, is dried, and is obtained into
Product, fabric can be supplied to uniform and the good blueness of fastness ability to black tone.85A, 83A in table 1 is respectively lignin
85A, lignin 83A.
Table 1
Tint applications 1：
Disperse dye compound obtained in weighing 4 grams of embodiments 1 is dispersed in 100 milliliters of water, with 21 millis after drawing 3 milliliters
The water mixing for rising, with piece adjusting PH with base to 12.5, is put into 4 grams of polyester textiles, is warming up to 70 DEG C, continues with about 2 DEG C/min gradient liters
Temperature to 130 DEG C, dye 45 minutes by insulation.Then 80 DEG C or so are cooled to and use hot water wash 10min, dried.Observation sample cloth coloured light, adopts
With GB/T 3921-2008, GB/T 3920-2008 and GB/T 5718-1997 test respectively its it is resistance to soap, antifriction scrape along it is resistance to
Sub-limation fastness, as a result see the table below 2.
Table 2
According to the method described in above-mentioned Dyeing Example, carried out respectively using the dyestuff prepared in embodiment 2～30
Bath raio 1:6 dyeing, dye level 3.0% except for the difference that changes dyeing pH value, and the basically identical indigo plant of dyeability is equally obtained
Color is specifically shown in Table 3 to dark blue to black fabric.
Table 3
Tint applications 2：
Comparative example 1：By (c-a) in patent CN101265369A embodiment 1 as a comparison；
Comparative example 2：The compounding disperse dyes that patent CN101265369A embodiment 25 is obtained are implemented as a comparison
Example 2；
Comparative example 3：By the dye shown in the dye monomer shown in patent CN104371366A formula (I -1), formula (II -1)
Dye monomer shown in material list body and formula (III -7), according to the method for the embodiment of the present application 1 black dyes is made, real as a comparison
Apply example 3；
Comparative example 4：The compounding disperse navy blue dyestuff that patent CN102746713A embodiment 2 is obtained is real as a comparison
Apply example 4；
Comparative example 5：The compounding dispersed deep blue dye that patent CN101649129A embodiment 1 is obtained is real as a comparison
Apply example 5；
By embodiment in the present invention 1, embodiment 2, comparative example 1, comparative example 2, comparative example 3, contrast are real
Apply the method (bath raio 1 of obtained composite disperse dye in example 4, comparative example 5 according to tint applications 1:6) difference is carried out respectively
Dye level is dyeed, and dye level is respectively 0.5%, 1%, 2%, 4%, 6%, 8%.Survey according to GB/T2397-2003 standards
Its lifting force is tried, gained lifting force result is as shown in Figure 1 and Figure 2.
From Fig. 1 and Fig. 2, dispersion of the present invention is blue to black dye composition not only washing fastness, distillation
The items fastness ability such as fastness, crock fastness is excellent, and better than the enhancing of existing common alkali resistance dispersion blue-black dyestuff, on
Dye rate is fast, and tinctorial yield is high, cost-effective, and is suitable for short liquor dyeing, energy-conserving and environment-protective.
Claims (10)
1. the blue disperse dye compound shown in a kind of formula (I),
Wherein, X1For H, halogen, C1～C4Alkyl or C1～C4Alkoxyl.
2. blue disperse dye compound as claimed in claim 1, it is characterised in that：The blue disperse dye compound is
It is one of following：
3. a kind of dark blue to black disperse dye composition, it is characterised in that：The composition contains dye component A and dyestuff
Component B and/or dye component C, the dye component A is selected from one or more in the dye composition shown in formula (I), described
Dye component B is selected from one or more in the dye composition shown in formula (II), and the dye component C is selected from shown in formula (III)
Dye composition in one or more；Based on the gross weight of described dye component A, B and C, the wherein weight of dye component A
Percentage composition is 30-95%, and the weight percentage of dye component B is 0-50%, and the weight percentage of dye component C is 0-
30%, and be 0 during the content difference of dye component B, dye component C；
In formula (I), X1For H, halogen, C1～C4Alkyl or C1～C4Alkoxyl；
In formula (II), R1For H, halogen or-CN；R2For H, halogen or-NO2；R3For unsubstituted C1-C4Alkyl, or by cyano group
Or C1～C4The C that alkoxyl replaces1-C4Alkyl；R4For benzyl, phenethyl, unsubstituted C1-C4Alkyl or by cyano group or C1
～C4The C that alkoxyl replaces1-C4Alkyl, X2For H or C1～C4Alkyl；
In formula (III), R5、R6、R7Each stand alone as H, halogen or nitro；X3For H, halogen or C1～C4Alkyl；R8For cyanoethyl,
C1-C6Alkyl or by C1-C6The C that alkoxyl replaces1-C6Alkyl；R9For cyanoethyl, benzyl, phenethyl, C1-C6Alkyl or by C1-C6
The C that alkoxyl replaces1-C6Alkyl.
4. as claimed in claim 3 dark blue to black disperse dye composition, it is characterised in that：The weight hundred of dye component A
Content is divided to be 50～90%, the weight percentage of dye component B is 0～35%, the weight percentage of dye component C is 0
～20%, and be 0 during the content difference of dye component B, dye component C.
5. dark blue to black disperse dye composition as described in claim 3 or 4, it is characterised in that：The dye component A is
One or two the mixture in 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, it is characterised in that：The dye component B is
The mixture of one or more in 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, it is characterised in that：The dye component C is
The mixture of one or more in dye composition shown in following formula (III -1)～(III -20)：
8. a kind of blue disperse dye product, containing described blue disperse dye compound as claimed in claim 1.
9. a kind of dark blue to black disperse dye product, containing as claimed in claim 3 dark blue to black disperse dye combination
Thing.
10. blue disperse dye compound as claimed in claim 1 in the dyeing of hydrophobic fiber material or stamp should
With.
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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 |
| 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 |
| 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 |
| CN110643197B (en) * | 2019-10-10 | 2020-11-27 | 济南大学 | Disperse black dye composition, disperse black dye and preparation method and application thereof |
| CN111978756B (en) * | 2020-08-27 | 2021-10-08 | 青岛大学 | Method for enhancing alkali resistance and oxidation resistance of benzothiazole 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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| CN102757660B (en) * | 2012-07-10 | 2013-12-11 | 浙江龙盛集团股份有限公司 | Benzisothiazole thiazole dye monomer compound and disperse dye |
| CN102746713B (en) * | 2012-07-10 | 2015-04-01 | 浙江龙盛集团股份有限公司 | Blue-to-black disperse dye composition |
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