CN1328326C - Disperse red dye composition - Google Patents
Disperse red dye composition Download PDFInfo
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- CN1328326C CN1328326C CNB2004100933626A CN200410093362A CN1328326C CN 1328326 C CN1328326 C CN 1328326C CN B2004100933626 A CNB2004100933626 A CN B2004100933626A CN 200410093362 A CN200410093362 A CN 200410093362A CN 1328326 C CN1328326 C CN 1328326C
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- dye composition
- red dye
- grades
- dye
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000001044 red dye Substances 0.000 title claims abstract description 21
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 title abstract 4
- 239000000975 dye Substances 0.000 claims abstract description 57
- 239000006185 dispersion Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 8
- 239000002657 fibrous material Substances 0.000 abstract description 8
- 229920000728 polyester Polymers 0.000 abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 9
- 239000012752 auxiliary agent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 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
- 238000000034 method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 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 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- -1 alkyl naphthalene sulfonic acid Chemical compound 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 238000002156 mixing 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
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229920001577 copolymer 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
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 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
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- Coloring (AREA)
Abstract
The invention relates to a disperse red dye composition, which contains a dye A shown as a formula and a dye B shown as a formula (II); when the disperse red dye composition is used for dyeing hydrophobic fiber materials, particularly polyester materials and polyamide fiber materials, the disperse red dye composition has the characteristics of high dye uptake, excellent dyeing fastness, good lifting property, good leveling property and the like, and is also very suitable for dyeing superfine polyester fiber materials.
Description
(1) technical field
The present invention relates to a kind of disperse dye composition, relate in particular to a kind of painted dispersion red dye composition of hydrophobic fiber material that is applied to.
(2) background technology
As everyone knows, azo disperse dye can be used for the dyeing of synthetic or semi-synthetic hydrophobic fiber material.But along with the development of new synthon, polyester superfine fibre weaving face fabric, these dyestuffs can't satisfy higher dyeing demand, especially show dye uptake, heat-resisting migration fastness, color fastness to water, colour fastness to light, equalization aspect.For this reason, develop the heat subject that bright-coloured dyestuff of a class dyeing behavior excellence, coloured light or dye composite have become dyestuff circle.
(3) summary of the invention
In order to overcome the deficiency of existing dispersive red dye dyeing behavior, the invention provides a kind of dispersion red dye composition.
Described dispersion red dye composition contains suc as formula the dyestuff A shown in (I) with suc as formula the dyestuff B shown in (II);
Wherein, X
1For H or-CN, be preferably-CN; X
2For H ,-CN or-NO
2, be preferably H;
R
1Be H or halogen, be preferably H or chlorine;
R
2For-CH
3,-NHCOCH
3Or-NHCOC
2H
5, be preferably-NHCOCH
3
R
3, R
4Independently be-CH separately
3Or-C
2H
5, be preferably-CH
3
R
5For H or-CH
3, be preferably H;
R
6For-OC
3H
7Or-OCH
2COOC
2H
4OCH
3, be preferably-OC
3H
7
Described dye composite is preferably as shown in the formula (III) especially and the composition of two kinds of dyestuffs of structure (IV) (is X
1For-CN, X
2Be H, R
1Be H, R
2For-NHCOCH
3, R
3, R
4Be respectively-CH
3, R
5Be H, R
6For-OC
3H
7):
Based on dyestuff A and dyestuff B, the weight percentage of described dyestuff A is 60～96%, is preferably 70～95%, most preferably is 80～95%; The weight percentage of dyestuff B is 4～40%, is preferably 5～30%, most preferably is 5～20%.
When preparing dispersion red dye composition of the present invention, employed dyestuff A and dyestuff B are respectively disclosed dyestuff such as patent EP555179 and patent EP146269 or similar these dyestuff, with the method for wherein record or similarly method can make at an easy rate.
When using dispersion red dye composition of the present invention preparation dispersed dye, generally need to add auxiliary agent and disperse.For example that structural formula (I) and structural formula (II) is represented former dyestuff carries out corpusculed with pulverizers such as sand mill or shredders after mixing by above-mentioned proportioning in the presence of auxiliary agent, water or other wetting agent; Also structural formula (I) and the represented former dyestuff of structural formula (II) can be carried out mixing with above-mentioned ratio after corpusculed is handled with pulverizers such as sand mill or shredders respectively in the presence of auxiliary agent, water or other wetting agent in addition.Usually, auxiliary agent is 1～5: 1 with the ratio of former dyestuff weight.
Described auxiliary agent is dyestuff dispersion agent commonly used, diffusant etc. when composite, comprise one of following or its several mixture arbitrarily: anionic dispersing agents such as the formaldehyde condensation products of the formaldehyde condensation products of naphthene sulfonic acid and alkyl benzene sulphonate (ABS), the formaldehyde condensation products of alkyl naphthalene sulfonic acid, benzyl naphthalenesulfonate formaldehyde condensation compound, cresol sulfonic acid, sulfonated lignin, the perhaps non-ionic dispersing agents such as ethylene oxide adduct of the ethylene oxide adduct of the segmented copolymer of oxyethane, propylene oxide, alkylphenol, polystyrene phenol.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 naphthalenesulfonate formaldehyde condensation compound such as dispersing agent CNF etc., sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
Use the dispersed dye of dispersion red dye composition of the present invention preparation, the liquid state after can corpusculed, emulsifiable paste attitude or with spray-drying process etc. carry out dried powdery, graininess is supplied with dyeing.The dispersed dye that are mixed with dispersion red dye composition of the present invention dye hydrophobic fiber material, particularly when polyester material, polyamide fiber material, characteristics such as have dye uptake height, dyefastness excellence, enhancing is good, equalization is good also are fit to dye the hyperfine polyester fiber material very much.
(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
Dyestuff B20 gram shown in dyestuff A30 shown in the formula (III) gram, the formula (IV), dispersion agent Reax 83A 60 grams, pure water 135 grams one are reinstated sand mill and carried out corpusculed (making dispersion treatment), and spraying drying promptly gets dispersive red dye again.
Embodiment 2～10
According to the preparation method of embodiment 1, defined dyestuff A of each substituting group and B structure are as shown in table 1, and described dye composite is pieced together dyestuff A, dyestuff B mixed by the continuous data shown in the table 2.
Table 1
| The embodiment title | Dyestuff A | Dyestuff B | |||||
| X 1 | X 2 | R 1 | R 2 | R 3＝R 4 | R 5 | R 6 | |
| Embodiment 2 | -CN | H | H | -NHCOCH 3 | -CH 3 | -CH 3 | -OCH 2COOC 2H 4OCH 3 |
| Embodiment 3 | H | -NO 2 | H | -NHCOCH 3 | -CH 3 | H | -OC 3H 7 |
| Embodiment 4 | H | -CN | H | -CH 3 | -C 2H 5 | H | -OC 3H 7 |
| Embodiment 5 | H | -CN | H | -NHCOC 2H 5 | -C 2H 5 | -CH 3 | -OCH 2COOC 2H 4OCH 3 |
| Embodiment 6 | -CN | H | Cl | -NHCOCH 3 | -CH 3 | H | -OC 3H 7 |
| Embodiment 7 | -CN | H | H | -NHCOCH 3 | -C 2H 5 | H | -OC 3H 7 |
| Embodiment 8 | -CN | H | Cl | -NHCOCH 3 | -C 2H 5 | -CH 3 | -OCH 2COOC 2H 4OCH 3 |
| Embodiment 9 | H | -CN | H | -CH 3 | -CH 3 | -CH 3 | -OCH 2COOC 2H 4OCH 3 |
| Embodiment 10 | H | NO 2 | H | -NHCOCH 3 | -C 2H 5 | -CH 3 | -OCH 2COOC 2H 4OCH 3 |
Table 2
| The embodiment title | Dyestuff A (gram) | Dyestuff B (gram) | Auxiliary agent (gram) | Pure water (gram) | |
| Embodiment 2 | 32 | 18 | Dispersant MF | 60 | 135 |
| Embodiment 3 | 34 | 16 | 60 | 135 | |
| Embodiment 4 | 36 | 14 | 60 | 135 | |
| Embodiment 5 | 38 | 12 | Dispersing agent CNF | 60 | 135 |
| Embodiment 6 | 40 | 10 | 60 | 135 | |
| Embodiment 7 | 42 | 8 | 60 | 135 | |
| Embodiment 8 | 44 | 6 | Dispersing agent NNO | 60 | 135 |
| Embodiment 9 | 46 | 4 | 60 | 135 | |
| Embodiment 10 | 48 | 2 | 60 | 135 | |
Embodiment 11
Respectively getting 0.5 dispersed dye that make of gram embodiment 1～10 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 ℃ put into simultaneously 2 the gram trevira dye, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 40 minutes, begin sampling when being cooled to 90 ℃.Adopt GB GB/T3921-1997, GB/T3920-1997, GB/T5718-1997 to survey its dyefastness.Test result sees Table 3.
Table 3
| The embodiment title | Washing fastness (60 ℃) | Crock fastness | 180 ℃ of sublimation fastness |
| Embodiment 1 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 2 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 3 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 4 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 5 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 6 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 7 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 8 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 9 | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 10 | 4～5 grades | 4～5 grades | 4～5 grades |
Claims (7)
1, a kind of dispersion red dye composition comprises that suc as formula the dyestuff A shown in (I) with suc as formula the dyestuff B shown in (II), based on dyestuff A and dyestuff B, the weight percentage of described dyestuff A is 60～96%, and the weight percentage of dyestuff B is 4～40%:
Wherein, X
1For H or-CN; X
2For H ,-CN or-NO
2
R
1Be H or halogen; R
2For-CH
3,-NHCOCH
3Or-NHCOC
2H
5
R
3, R
4Independently be-CH separately
3Or-C
2H
5
R
5For H or-CH
3
R
6For-OC
3H
7Or-OCH
2COOC
2H
4OCH
3
2, dispersion red dye composition as claimed in claim 1 is characterized in that described R
1Be H or Cl, R
2For-NHCOCH
3, R
3, R
4Be respectively-CH
3
3, dispersion red dye composition as claimed in claim 1 is characterized in that described X
1For-CN, X
2Be H.
4, dispersion red dye composition as claimed in claim 1 is characterized in that described R
5Be H, R
6For-OC
3H
7
5, dispersion red dye composition as claimed in claim 4 is characterized in that basically by forming suc as formula the dyestuff A shown in (III) with suc as formula the dyestuff B shown in (IV):
6, as the described dispersion red dye composition of one of claim 1～5, it is characterized in that: based on dyestuff A and dyestuff B, the weight percentage of described dyestuff A is 70～95%, and the weight percentage of dyestuff B is 5～30%.
7, dispersion red dye composition as claimed in claim 6 is characterized in that: based on dyestuff A and dyestuff B, the weight percentage of described dyestuff A is 80～95%, and the weight percentage of dyestuff B is 5～20%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100933626A CN1328326C (en) | 2004-12-16 | 2004-12-16 | Disperse red dye composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100933626A CN1328326C (en) | 2004-12-16 | 2004-12-16 | Disperse red dye composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1640942A CN1640942A (en) | 2005-07-20 |
| CN1328326C true CN1328326C (en) | 2007-07-25 |
Family
ID=34869403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100933626A Active CN1328326C (en) | 2004-12-16 | 2004-12-16 | Disperse red dye composition |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1328326C (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101333343B (en) * | 2008-07-30 | 2011-06-01 | 浙江闰土股份有限公司 | Red disperse dyes composition of synthetic high fastness series |
| CN101899229B (en) * | 2010-06-29 | 2013-01-16 | 浙江龙盛染料化工有限公司 | Disperse red dye composition |
| CN101983993A (en) * | 2010-07-30 | 2011-03-09 | 江苏亚邦染料股份有限公司 | Dispersed scarlet dye composite with high washing fastness |
| CN102277012B (en) * | 2011-04-29 | 2014-10-29 | 浙江闰土股份有限公司 | Disperse purplish-red dye composition |
| CN106883641B (en) * | 2016-12-31 | 2019-03-29 | 浙江龙盛集团股份有限公司 | A kind of dispersed ruby dye composition and dye preparations |
| CN108165051B (en) * | 2018-02-05 | 2019-11-12 | 浙江山峪科技股份有限公司 | A kind of high distillation is high to wash yellowish-brown disperse dye composition, dye preparations and application |
| CN109535769B (en) * | 2018-12-19 | 2020-08-07 | 浙江龙盛化工研究有限公司 | Disperse red dye composition and dye product |
| CN111303661B (en) * | 2020-03-02 | 2021-06-08 | 上海贝通色彩科技有限公司 | Disperse red dye composition, disperse red dye preparation and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0146269A2 (en) * | 1983-12-16 | 1985-06-26 | Imperial Chemical Industries Plc | Hetero-polycyclic aromatic compound |
| JPH0762260A (en) * | 1993-08-31 | 1995-03-07 | Sumitomo Chem Co Ltd | Coloring composition for hydrophobic material and coloring of hydrophobic material using the composition |
| US5529586A (en) * | 1993-08-26 | 1996-06-25 | Sumitomo Chemical Company, Limited | Compositions containing a benzodifuranone compound and methods for coloring hydrophobic materials using the same |
| US5550217A (en) * | 1992-02-03 | 1996-08-27 | Ciba-Geigy Corporation | Azo dyes |
-
2004
- 2004-12-16 CN CNB2004100933626A patent/CN1328326C/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0146269A2 (en) * | 1983-12-16 | 1985-06-26 | Imperial Chemical Industries Plc | Hetero-polycyclic aromatic compound |
| US5550217A (en) * | 1992-02-03 | 1996-08-27 | Ciba-Geigy Corporation | Azo dyes |
| US5529586A (en) * | 1993-08-26 | 1996-06-25 | Sumitomo Chemical Company, Limited | Compositions containing a benzodifuranone compound and methods for coloring hydrophobic materials using the same |
| JPH0762260A (en) * | 1993-08-31 | 1995-03-07 | Sumitomo Chem Co Ltd | Coloring composition for hydrophobic material and coloring of hydrophobic material using the composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1640942A (en) | 2005-07-20 |
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