CN101735663B - Composite black disperse dye - Google Patents
Composite black disperse dye Download PDFInfo
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- CN101735663B CN101735663B CN 200910156655 CN200910156655A CN101735663B CN 101735663 B CN101735663 B CN 101735663B CN 200910156655 CN200910156655 CN 200910156655 CN 200910156655 A CN200910156655 A CN 200910156655A CN 101735663 B CN101735663 B CN 101735663B
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- composite black
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- 239000002131 composite material Substances 0.000 title claims abstract description 39
- 239000000986 disperse dye Substances 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 claims description 15
- UQMRAFJOBWOFNS-UHFFFAOYSA-N butyl 2-(2,4-dichlorophenoxy)acetate Chemical compound CCCCOC(=O)COC1=CC=C(Cl)C=C1Cl UQMRAFJOBWOFNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- -1 methoxyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 39
- 239000004744 fabric Substances 0.000 abstract description 7
- 239000002657 fibrous material Substances 0.000 abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 239000002932 luster Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000009877 rendering Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 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 2
- 239000012535 impurity Substances 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 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
- 229920004935 Trevira® Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention provides a composite black disperse dye, which mainly comprises one or more blue components shown by a structural formula (I), one or more of yellow component B shown by a structural formula (II), one or more blue component C shown by a structural formula (III) and one or more red component D shown by a structural formula (IV), wherein based on the total weight of the components A, B, C and D, the components A account for 30 to 85 percent, the components B account for 1 to 45 percent, the components C account for 1 to 30 percent and the components D account for 1 to 30 percent. When the composite black disperse dye of the invention is used to dye a hydrophobic fiber material, a black dyed fabric which is bright in luster, high in rubbing fastness and desirable in color can be obtained by adjusting the proportion of the components. The composite black disperse dye is economic and environmentally-friendly and has excellent dying performance.
Description
(1) technical field
The present invention relates to a kind of composite black disperse dye, particularly, relate to a kind of suitable printing and dyeing hydrophobic fiber material, particularly Polyester Fibers disperse black dye composition dyeing, that contain ad hoc structure.
(2) background technology
From the seventies in 20th century, the dispersed dye development is rapid, though slower to the dispersed dye new variety of China's exploitation in recent years, a lot of more highly difficult kinds have been succeeded in developing and industrialization, and quality is near external like product.Dark color is particularly dark blue mostly to be composite kind greatly to black disperse dye, because the kind that structure is single often exists depth and lifting force deficiency, the shortcoming of fastness ability difference, therefore adopt different dispersed dye composite, it is the effective way that obtains black disperse dye, can effectively improve depth and the color fixation fastness of dyestuff, make fabric obtain better effect.In addition, for general black-dyeing thing, when light source changes, be easy to cause colour-change phenomena, namely the color rendering aspect of dyestuff still remains to be improved.At present; because DISPERSE NAVY BLUE EXSF 300﹠ BLUE 56 100, black dyes consumption are very big; the patent report that various composite assembly mixes is also many; the technology of the composite preparation composite black of relevant employing azoic dyestuff dispersed dye is disclosed as US Patent No. 6159249, Korean Patent KR0156834B etc.; but there is still dissatisfactory problem of aspects such as dyeing behavior, economy; particularly explosion of monetary crisis is in recent years had higher requirement to the cost performance of dyestuff.
(3) summary of the invention
The present invention is the improvement of CN101323712A patent application technical scheme, and purpose is to provide the composite black disperse dye that a kind of colour fastness to rubbing is good, the color rendering energy is good, cost performance is high.
The technical solution used in the present invention is:
1. composite black disperse dye, mainly comprise one or more structures suc as formula the blue color component A shown in (I), one or more structures suc as formula the yellow color component B shown in (II), one or more structures suc as formula the blue color component C shown in (III) and one or more structures suc as formula the red component D shown in (IV), based on described component A, B, C and component D, the weight fraction of component A is 30~85%, the weight fraction of B component is 1~45%, the weight fraction of component C is 1~30%, and the weight fraction of component D is 1~30%;
In the formula (I): X
1Be cyano group or halogen; R
1, R
2Independent separately is C
1~C
4Alkyl ,-CH
2COOR
12,-C
2H
4COOR
13Or-C
2H
4OCOCH
3, R wherein
12, R
13Independent separately is C
1~C
4Alkyl, R
3, R
4Independent separately is C
1~C
4Alkyl;
In the formula (II): X
2Be nitro or hydrogen, X
3For methoxyl group ,-OSO
2-Ph ,-OSO
2-CH
3Or-CO-Ph, wherein, Ph represents phenyl, R
5Be C
1~C
4Alkyl;
In the formula (III): X
4Be O or NH; R
6For by cyano group, hydroxyl, C
1~C
4Alkoxyl group or the C that replaces of phenyl
1~C
4Alkyl.
In the formula (IV): R
7For-OCH
3,-NHCOCH
3,-NHCOC
2H
5Or-NHSO
2CH
3, n is numeral 1 or 2.
Preferably, based on described component A, B component, component C and component D, the weight fraction of described component A is 35~80%, and the weight fraction of B component is 5~40%, and the weight fraction of component C is 1~25%, and the weight fraction of component D is 1~25%.
Described composite black disperse dye also comprises the purple component E shown in the formula V, and based on described component A, B, C, D and component E, component A massfraction is 30~85%, preferred 35~80%; The B component massfraction is 1~45%, is preferably 5~40%; Component C massfraction is 1~30%, is preferably 1~25%; Component D massfraction is 1~25%, is preferably 1~20%; Component E massfraction is 1~25%, is preferably 1~20%.
Preferably, described composite black disperse dye is made up of component A, B component, component C, component D and component E, and based on described component A, B component, component C, component D and component E, component A massfraction is 35~80%; The B component massfraction is 5~40%; Component C massfraction is 1~25%; Component D massfraction is 1~20%; Component E massfraction is 1~20%.
Described blue color component A is preferably one of following formula or two or more mixture wherein:
Described yellow color component B is preferably one of following formula or two or more mixture wherein:
Described blue color component C is preferably one of following formula or two or more mixture wherein:
Described red component D is preferably one of following formula or two or more mixture wherein:
Described red component E is preferably one of following formula or two or more mixture wherein:
Preferably, described composite black disperse dye is by the blue color component A shown in the formula (I-1), yellow color component B shown in formula (II-1) and the formula (II-3), red component D shown in blue color component C shown in the formula (III-1) and the formula (IV-1) forms, the massfraction of component A is 30~85%, the massfraction of B component is 1~45%, and the massfraction of component C is 1~30%, and the massfraction of component D is 1~30%.
Perhaps, described composite black disperse dye is by the blue color component A shown in the formula (I-1), yellow color component B shown in formula (II-1) and the formula (II-3), blue color component C shown in the formula (III-1), the red component D shown in the formula (IV-1) and the purple component E (V-1) form, and the massfraction of component A is 30~85%, the massfraction of B component is 1~45%, the massfraction of component C is 1~30%, and the massfraction of component D is 1~30%, and the massfraction of component E is 1~30%.Wherein, in the B component, formula (II-1) can be mixed by arbitrary proportion with formula (II-3).
Composite disperse dye of the present invention by aforementioned specific blending ratio preparation, can obtain black tone, dyes by ways customary in the industry, can obtain that form and aspect are full, fastness to rubbing good, color rendering is good, the dyeing and weaving thing of environmental protection and economy.
The dye composition of formula used in the present invention (I)~formula V can be synthetic by mode well known to those skilled in the art easily, and wherein component A also can also can adopt the commercial goods with reference to the method preparation of introducing among the patent CN1208057; B component can also can adopt the commercial goods according to the method preparation of introducing among patent JP61019664, the JP11158402; Component C can also can adopt the commercial goods according to the method preparation of introducing among the patent US4904796; Component D can also can adopt the commercial goods according to the method preparation of introducing among the patent US5550217; Component E can also can adopt the commercial goods according to the method preparation of introducing among the patent CN1195003.
Because the singularity of dye industry is difficult to also there is no need to make pure product, can have the impurity in some preparation process usually, also allows to contain the physics impurity of a spot of moisture and trace when dye composite of the present invention is made finished product.
Composite black disperse dye of the present invention generally needs to add auxiliary agent and disperses during application.After for example with structural formula (I), (II), (III) and (IV) represented former dyestuff mixes by above-mentioned proportioning, in the presence of auxiliary agent, water or other wetting agent, carry out corpusculed with pulverizers such as sand mill or shredders; In addition also can with structural formula (I), (II), (III) and (IV) represented former dyestuff in the presence of auxiliary agent, water or other wetting agent, carry out corpusculed with pulverizers such as sand mill or shredders respectively and handle the back and mix with above-mentioned ratio.Usually, auxiliary agent is 0.8-5 with the ratio of former dyestuff weight: 1.In addition, also can directly buy each commercial dye from the market and do assembly.
Described auxiliary agent is dispersed dye dispersion agent commonly used, diffusants etc. when composite, one of preferred following or its several mixture arbitrarily: anionic dispersing agents such as naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.Particularly, naphthalene sulfonic acidformaldehyde condensation product such as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalene sulfonic formaldehyde condensation compound such as dispersing agent CNF etc., sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax83A, Reax85A) etc.
Composite black disperse dye of the present invention can adopt common dip method to dye, and also can be used for direct printing.Wherein, common dip method is put into dye vat and is contaminated as polyester textile is carried out pre-treatment, dyes completely, and cold water cleans to neutral, and strand is done, and carries out reduction clearing again, oven dry; Direct printing is as dying pre-treatment with fabric, oven dry, and setting at printing machine seal dispersed dye mill base, is evaporated again, utilizes the decatize mode to make dye fixing on the fabric, washing at last, stentering forming.
Composite black disperse dye of the present invention, the liquid state after can corpusculed, emulsifiable paste attitude or with spray-drying process etc. carry out dried powdery, graininess is supplied with dyeing.When dying hydrophobic fiber material on the composite disperse dye of the present invention, by adjusting proportion among different, can obtain to have that coloured light is gorgeous, fastness to rubbing reaches the good black dyeing and weaving thing of color well, be the good composite black disperse dye of dyeing behavior of a economic environmental protection.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
With the component A of 55 gram formulas (I-1), B component, the component C of 10 gram formulas (III-1), the component D of 10 gram formulas (IV-1) that 15 gram formulas (II-1) and 10 restrain (II-3), the Dispersant MFs of 150 grams add water and stir, and grind and disperse and drying, get product.This dyestuff can offer the good aterrimus of fabric color rendering.
Embodiment 2:
With the component D of component A, 13 gram formulas (II-1) and 13 gram formulas (II-3) and component C B component, 14 gram formulas (III-1), the 5 gram formulas (IV-1) of 50 gram formulas (I-1), the component E of 5 gram formulas (V-1), the sodium lignosulfonates of 60 grams and the dispersing agent NNOs of 100 grams, adding water stirs, grind and disperse and drying, get product.This dyestuff can offer the aterrimus that the fabric color rendering can be good.
Embodiment 3~11:
According to the data shown in the table 1, with component A, B component, component C, component D, component E, Dispersant MF 100 grams, sodium lignosulfonate 50 grams, add water and stir, grind dispersion and dry, make finished product.
Table 1
Comparative Examples 1:
Referring to CN101323712A embodiment 1, component A, the B component of 14 gram formulas (VII), component C, the component D of 20 gram formulas (IX) of 6 gram formulas (VIII), 150 sodium lignosulfonates that restrain with 60 gram formulas (VI), add water and stir, grind and disperse and drying, dyestuff gets product.
Dyeing embodiment 12:
Respectively getting the dispersed dye that 2 gram embodiment 1~11, Comparative Examples 1 make is dispersed in 500 ml waters, mix with 60 milliliters water after drawing 15 milliliters, transferring dye bath PH with acetic acid is 5, being warming up to 70 ℃ puts into 2 gram trevira cloth simultaneously and dyes, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 30 minutes, begin sampling when being cooled to 90 ℃.Adopt GB/T3920, GB/T15610 tests and evaluates its colour fastness to rubbing respectively, the color rendering energy, the result who obtains is: adopt the dyestuff of embodiment 1~11 to obtain to dye the sample colour fastness to rubbing all more than 4~5 grades, color rendering is differential all more than 4 grades, that adopts that the dyestuff of Comparative Examples 1 obtains dyes its colour fastness to rubbing of sample (4~5 grades of unlubricated frictions, wet and rub 4 grades), the color rendering evaluation is differential only to be 3 grades, and complex black dye of the present invention obviously is better than the dye composite in the Comparative Examples 1 aspect cost, therefore, dyestuff in the Comparative Examples 1, dyestuff of the present invention is more economical, and cost performance is higher, and more vast market prospect is arranged.
Claims (9)
1. composite black disperse dye, mainly comprise blue color component A, one or more structures yellow color component B, one or more structures blue color component C and one or more structure the red component D as formula IV shown in as formula III shown in as formula II shown in of one or more structures shown in formula I, based on described component A, B, C and component D, the weight fraction of component A is 30~85%, the weight fraction of B component is 1~45%, the weight fraction of component C is 1~30%, and the weight fraction of component D is 1~30%;
In the formula I: X
1Be cyano group or halogen; R
1, R
2Independent separately is C
1~C
4Alkyl ,-CH
2COOR
12,-C
2H
4COOR
13Or-C
2H
4OCOCH
3, R wherein
12, R
13Independent separately is C
1~C
4Alkyl, R
3, R
4Independent separately is C
1~C
4Alkyl;
In the formula II: X
2Be nitro or hydrogen, X
3For methoxyl group ,-OSO
2-Ph ,-OSO
2-CH
3Or-CO-Ph, wherein, Ph represents phenyl, R
5Be C
1~C
4Alkyl;
In the formula III: X
4Be O or NH; R
6For by cyano group, hydroxyl, C
1~C
4Alkoxyl group or the C that replaces of phenyl
1~C
4Alkyl;
In the formula IV: R
7For-OCH
3,-NHCOCH
3,-NHCOC
2H
5Or-NHSO
2CH
3, n is numeral 1 or 2.
2. composite black disperse dye as claimed in claim 1 is characterized in that described composite black disperse dye also comprises purple component E, and based on described component A, B, C, D and component E, component A massfraction is 30~85%, and the B component massfraction is 1~45%; Component C massfraction is 1~30%; Component D massfraction is 1~25%, and component E massfraction is 1~25%; Described component E is one of following formula or two or more mixture wherein:
3. composite black disperse dye as claimed in claim 2, it is characterized in that: described composite black disperse dye is made up of component A, B component, component C, component D and component E, based on described component A, B component, component C, component D and component E, component A massfraction is 35~80%; The B component massfraction is 5~40%; Component C massfraction is 1~25%; Component D massfraction is 1~20%; Component E massfraction is 1~20%.
8. composite black disperse dye as claimed in claim 1, it is characterized in that: described composite black disperse dye is by the blue color component A shown in the formula (I-1), yellow color component B shown in formula (II-1) and the formula (II-3), red component D shown in blue color component C shown in the formula (III-1) and the formula (IV-1) forms, the massfraction of component A is 30~85%, the massfraction of B component is 1~45%, and the massfraction of component C is 1~30%, and the massfraction of component D is 1~30%;
9. composite black disperse dye as claimed in claim 1, it is characterized in that: described composite black disperse dye is by the blue color component A shown in the formula (I-1), yellow color component B shown in formula (II-1) and the formula (II-3), blue color component C shown in the formula (III-1), purple component E shown in red component D shown in the formula (IV-1) and (V-1) forms, the massfraction of component A is 30~85%, the massfraction of B component is 1~45%, the massfraction of component C is 1~30%, the massfraction of component D is 1~30%, and the massfraction of component E is 1~30%;
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CN 200910156655 CN101735663B (en) | 2009-12-31 | 2009-12-31 | Composite black disperse dye |
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CN 200910156655 CN101735663B (en) | 2009-12-31 | 2009-12-31 | Composite black disperse dye |
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CN101735663A CN101735663A (en) | 2010-06-16 |
CN101735663B true CN101735663B (en) | 2013-07-03 |
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CN110922786B (en) * | 2019-12-13 | 2021-04-09 | 约克夏(浙江)染化有限公司 | Black disperse dye composition, disperse dye, preparation method and application thereof |
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CN101323712A (en) * | 2008-07-11 | 2008-12-17 | 浙江龙盛染料化工有限公司 | Dispersed black dye composition |
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