CN1274769C - Composite disperse orange dye - Google Patents
Composite disperse orange dye Download PDFInfo
- Publication number
- CN1274769C CN1274769C CN 200410068169 CN200410068169A CN1274769C CN 1274769 C CN1274769 C CN 1274769C CN 200410068169 CN200410068169 CN 200410068169 CN 200410068169 A CN200410068169 A CN 200410068169A CN 1274769 C CN1274769 C CN 1274769C
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- Prior art keywords
- disperse orange
- dye
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- formula
- composite
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002131 composite material Substances 0.000 title claims abstract description 18
- 239000001048 orange dye Substances 0.000 title claims abstract description 17
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 title claims description 16
- 239000000975 dye Substances 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 claims description 9
- MUERWWKQVXXPML-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 MUERWWKQVXXPML-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000007859 condensation product Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 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 claims description 5
- 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 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 4
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 235000019357 lignosulphonate Nutrition 0.000 claims description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 4
- 229920000728 polyester Polymers 0.000 abstract description 4
- 238000000859 sublimation Methods 0.000 abstract description 4
- 230000008022 sublimation Effects 0.000 abstract description 4
- 238000005406 washing Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000007639 printing Methods 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 6
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 230000007812 deficiency Effects 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
- 238000009973 dope dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001089 thermophoresis Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000009970 yarn dyeing Methods 0.000 description 1
Abstract
The present invention relates to a composite monoazo dye composition which basically comprises the following components by the weight proportion: 5 to 35% of dye monomer A, 5 to 35% of dye monomer B and an auxiliary agent as the rest, wherein the dye monomer A is represented by a formula (I); the dye monomer B is represented by a formula (II). The composite dispersing orange dye is particularly suitable for dyeing polyester material and yarn and printing and has the advantages of outstanding coloring performance by hot melting at high temperature, good fastness, such as light fastness, sublimation fastness and washing fastness.
Description
(1) technical field
The present invention relates to a kind of compound Monoazo-dyes composition.
(2) background technology
From the weaving face fabric present situation, the shared ratio of lining that is formed by multiple fiber combinations increases year by year, and some the medium-to-high grade linings as domestic comprise polyester blended lining etc.Gong Ying dispersed dye in the market, can't satisfy the printing and dyeing needs of such textiles well: its thermophoresis fastness and water washing fastness are all not ideal enough, have influenced the various wet fastness of dope dyeing, have also brought the pollution to surrounding environment.
(3) summary of the invention
For overcoming the deficiency of existing dispersed dye, the object of the invention is to provide a kind of composite disperse orange dye of excellent property, is suitable for the dyeing of multifilament lining such as polyester blended lining.
Composite disperse orange dye of the present invention, form by following component basically:
Weight fraction is 5～35% the dye monomer A suc as formula (I),
Weight fraction is 5～35% the dye monomer B suc as formula (II),
Surplus is an auxiliary agent;
Wherein, R is methyl or cyanoethyl in the formula (I), is preferably cyanoethyl; X is a chlorine or bromine in the formula (II), is preferably chlorine.
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 content and trace when composite disperse orange dye of the present invention is made finished product.
The weight fraction of described dye monomer A is preferably 10～30%, and the weight fraction of dye monomer B is preferably 10～30%.
Described auxiliary agent can be one of following or the mixture of two or more arbitrary proportions: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin, benzyl naphthalenesulfonate formaldehyde condensation compound.Described 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 naphthalenesulfonate formaldehyde condensation compound such as dispersing agent CNF etc.; Sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
Composite disperse orange dye of the present invention can prepare by the following method:
After dye monomer A, dye monomer B, auxiliary agent, water or the mixing of other wetting agent with the metering ratio, grind dispersion with shredder, then spraying drying.Above-mentioned dye monomer A and monomers B can adopt the commercially available prod respectively, as the C.I. DISPERSE ORANGE 30 200 73 former dyestuffs and the C.I. DISPERSE YELLOW 163 former dyestuffs of Zhejiang Province Longsheng Group Co., Ltd's production.
Composite disperse orange dye of the present invention also can prepare by the following method:
With the metering C.I. DISPERSE ORANGE 30 200 73 (main ingredient is dye monomer A (R is a cyanoethyl) and auxiliary agent) of ratio and C.I. DISPERSE YELLOW 163 (main ingredient is dye monomer B (X is a chlorine) and auxiliary agent), auxiliary agent add water piece together mix after, grind dispersion, then spraying drying; Also C.I. DISPERSE ORANGE 30 200 73, C.I. DISPERSE YELLOW 163 and auxiliary agent directly can be pieced together mixedly, be ground to and be uniformly dispersed.Equally, above-mentioned C.I. DISPERSE ORANGE 30 200 73 and C.I. DISPERSE YELLOW 163 also can adopt the commercially available prod, as the C.I. DISPERSE ORANGE 30 200 73 and the C.I. DISPERSE YELLOW 163 of Zhejiang Province Longsheng Group Co., Ltd's production.
Composite disperse orange dye of the present invention is very suitable for dying polyester material, yarn dyeing and stamp, and high temperature hot melt dyeing behavior is splendid, and the fastness excellent property is all good as sun-resistant fastness, fastness to sublimation, wash resistant fastness.
(4) embodiment
The invention will be further described below in conjunction with embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1～7
According to continuous data shown in the table 1, after dye monomer A, dye monomer B, auxiliary agent (dispersion agent condensation compound of methyl naphthalene sulfonic acid and formaldehyde (MF), diffusant benzyl naphthalenesulfonate formaldehyde condensation compound (CNF), diffusant naphthalene sulfonic acidformaldehyde condensation product (NNO), sodium lignosulfonate) added water and piece together to mix, grind dispersion with shredder, spraying drying gets final product.
Table 1
| The embodiment title | Dye monomer A (gram) | Dye monomer B (gram) | Auxiliary agent (gram) | Water (gram) | |||||
| Dispersant MF | Dispersing agent CNF | Dispersing agent NNO | Sodium lignosulfonate | ||||||
| R is a methyl | R is an ethyl | X＝Cl | X＝Br | ||||||
| Embodiment 1 | 34 | 0 | 7 | 0 | 24 | 35 | 0 | 0 | 120 |
| Embodiment 2 | 30 | 0 | 0 | 10 | 30 | 0 | 30 | 0 | 120 |
| Embodiment 3 | 0 | 25 | 0 | 15 | 25 | 0 | 0 | 35 | 120 |
| Embodiment 4 | 0 | 19 | 19 | 0 | 0 | 0 | 0 | 62 | 120 |
| Embodiment 5 | 0 | 15 | 25 | 0 | 0 | 0 | 60 | 0 | 120 |
| Embodiment 6 | 0 | 10 | 25 | 0 | 0 | 65 | 0 | 0 | 120 |
| Embodiment 7 | 0 | 8 | 30 | 0 | 62 | 0 | 0 | 0 | 120 |
Embodiment 8～11
According to continuous data shown in the table 2, with C.I. DISPERSE ORANGE 30 200 73 (commercial dyes, monomer A content 35%), C.I. DISPERSE YELLOW 163 (commercial dyes, monomers B content 40%), after auxiliary agent (dispersion agent condensation compound of methyl naphthalene sulfonic acid and formaldehyde (MF), diffusant benzyl naphthalenesulfonate formaldehyde condensation compound (CNF), diffusant naphthalene sulfonic acidformaldehyde condensation product (NNO)) adds water and piece together to mix, grind dispersion with shredder, then spraying drying;
Table 2
| The embodiment title | C.I. DISPERSE ORANGE 30 200 73 (gram) | C.I. DISPERSE YELLOW 163 (gram) | Dispersant MF (gram) | Dispersing agent CNF (gram) | Dispersing agent NNO (gram) | Water (gram) |
| Embodiment 8 | 40 | 60 | 0 | 0 | 0 | 0 |
| Embodiment 9 | 60 | 59 | 5 | 0 | 0 | 140 |
| Embodiment 10 | 70 | 50 | 0 | 10 | 0 | 150 |
| Embodiment 11 | 80 | 55 | 0 | 0 | 5 | 160 |
Embodiment 12
Respectively getting 0.5 dispersed dye that make of gram embodiment 1～11 is dispersed in 500 ml waters, mix with 60 milliliters water after drawing 20 milliliters, transferring dye bath PH with acetic acid is 5, be warming up to 70 ℃ to put into 2 grams simultaneously and wash/cotton dyes, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 30 minutes, begin sampling when being cooled to 90 ℃.Adopt that GB GB/T3921-1997, GB/T3920-1997, GB/T8427-1998, GB/T5718-1997 test respectively that it is water-fastly washed, rub resistance, colour fastness to light and sub limation fastness.Test result sees Table 3.
Table 3
| The embodiment title | Water-fast washing | Rub resistance | Fast light | 180 ℃ of sublimation fastness |
| Embodiment 1 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 2 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 3 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 4 | 5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 5 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 6 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 7 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 8 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 9 | 5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 10 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
| Embodiment 11 | 4～5 grades | 4～5 grades | 6 grades | 4～5 grades |
Claims (8)
1, a kind of composite disperse orange dye, form by following component basically:
Weight fraction is 5～35% the dye monomer A suc as formula (I),
Weight fraction is 5～35% the dye monomer B suc as formula (II),
Surplus is an auxiliary agent;
Wherein, R is methyl or cyanoethyl in the formula (I); X is a chlorine or bromine in the formula (II).
2, composite disperse orange dye according to claim 1 is characterized in that R is a cyanoethyl in the described formula (I), and X is a chlorine in the formula (II).
3, composite disperse orange dye according to claim 1 is characterized in that described auxiliary agent is one of following or the mixture of two or more arbitrary proportions: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.
4, composite disperse orange dye according to claim 3 is characterized in that described alkyl naphthalene sulfonic acid formaldehyde condensation products is a condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
5, composite disperse orange dye according to claim 3 is characterized in that described sulfonated lignin are sodium lignosulfonate.
6, according to the described composite disperse orange dye of one of claim 1～5, the weight fraction that it is characterized in that described dye monomer A is 10～30%, and the weight fraction of dye monomer B is 10～30%.
7, composite disperse orange dye according to claim 1 and 2 is characterized in that described dyestuff is made up of following component: C.I. DISPERSE ORANGE 30 200 73 and C.I. DISPERSE YELLOW 163.
8, composite disperse orange dye according to claim 1 and 2 is characterized in that described dyestuff is made up of following component: C.I. DISPERSE ORANGE 30 200 73, C.I. DISPERSE YELLOW 163 and auxiliary agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410068169 CN1274769C (en) | 2004-11-10 | 2004-11-10 | Composite disperse orange dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410068169 CN1274769C (en) | 2004-11-10 | 2004-11-10 | Composite disperse orange dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1631989A CN1631989A (en) | 2005-06-29 |
| CN1274769C true CN1274769C (en) | 2006-09-13 |
Family
ID=34846747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410068169 Expired - Fee Related CN1274769C (en) | 2004-11-10 | 2004-11-10 | Composite disperse orange dye |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1274769C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1995154B (en) * | 2006-12-21 | 2010-05-19 | 浙江龙盛集团股份有限公司 | Dispersing orange dye composition and dispersing dye |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101654566A (en) * | 2009-09-10 | 2010-02-24 | 董源 | Monoazo type composition dye |
| CN102516815B (en) * | 2011-12-30 | 2013-06-05 | 吴江市绿洲染料化工有限公司 | Disperse orange dye mixture |
| CN107974102A (en) * | 2017-10-30 | 2018-05-01 | 安徽凯奇化工科技股份有限公司 | A kind of composite disperse orange dye |
| CN109181362B (en) * | 2018-08-07 | 2020-06-02 | 江苏之江化工有限公司 | Orange disperse dye mixture with high washing fastness |
-
2004
- 2004-11-10 CN CN 200410068169 patent/CN1274769C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1995154B (en) * | 2006-12-21 | 2010-05-19 | 浙江龙盛集团股份有限公司 | Dispersing orange dye composition and dispersing dye |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1631989A (en) | 2005-06-29 |
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Assignee: Zhejiang Shanyu Dyestuff Chemical Co., Ltd. Assignor: Zhejiang Longsheng Group Co., Ltd. Contract record no.: 2011330000160 Denomination of invention: Admixture of composite dispersed orange dye Granted publication date: 20060913 License type: Exclusive License Open date: 20050629 Record date: 20110330 |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060913 Termination date: 20171110 |
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| CF01 | Termination of patent right due to non-payment of annual fee |