CN1631991A - Composite disperse red dye - Google Patents
Composite disperse red dye Download PDFInfo
- Publication number
- CN1631991A CN1631991A CN 200410068171 CN200410068171A CN1631991A CN 1631991 A CN1631991 A CN 1631991A CN 200410068171 CN200410068171 CN 200410068171 CN 200410068171 A CN200410068171 A CN 200410068171A CN 1631991 A CN1631991 A CN 1631991A
- Authority
- CN
- China
- Prior art keywords
- grades
- dye
- disperse red
- red dye
- monomer
- 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.)
- Granted
Links
- 239000001044 red dye Substances 0.000 title claims description 18
- 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 claims description 15
- 239000002131 composite material Substances 0.000 title claims description 13
- 239000000975 dye Substances 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000012752 auxiliary agent Substances 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 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
- 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
- 239000000203 mixture Substances 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
- 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 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 4
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 4
- 235000019357 lignosulphonate Nutrition 0.000 claims description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 claims 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 2
- 239000000987 azo dye Substances 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
- 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 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 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
- 238000004043 dyeing Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 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 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000009973 dope dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 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
- 239000002075 main ingredient Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001048 orange dye Substances 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
Landscapes
- Coloring (AREA)
Abstract
The invention relates to a combiner of compound azo color, mainly be comprised of monomer of color A shown as (I) (10-35%) and monomer of color B shown as (II) (1-15%) and others as assistant . The compound dispersed red color is especially suitable for coloring polyester materials, yarn and dye printing, with outstanding coloring performance in high temperature and stability such as resistance to sunshine, sublimation and washing.
Description
(1) technical field
The present invention relates to a kind of 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 red dye of excellent property, is suitable for the dyeing of multifilament combination lining such as polyester blended lining.
Composite disperse red dye of the present invention, form by following component basically:
Weight fraction is 10～35% the dye monomer A suc as formula (I),
Weight fraction is 1～15% the dye monomer B suc as formula (II),
Surplus is an auxiliary agent.
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 15～30%, and the weight fraction of dye monomer B is preferably 1～10%.
Described auxiliary agent can be one of following or its mixture: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.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), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound) etc.; Sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax85A) etc.
Composite disperse red 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 former dyestuff of Disperse Red TRHNF and the C.I. DISPERSE ORANGE 30 200 73 former dyestuffs of Zhejiang Province Longsheng Group Co., Ltd's production.
Composite disperse red dye of the present invention also can prepare by the following method:
Earlier make finished product dispersive red dye C by dye monomer A and auxiliary agent, will measure again the finished product dispersive red dye C of ratio and C.I. DISPERSE ORANGE 30 200 73 (main ingredient is dye monomer B and auxiliary agent), auxiliary agent add water piece together mix after, grind dispersion, then spraying drying; Also this finished product dispersive red dye C, C.I. DISPERSE ORANGE 30 200 73 and auxiliary agent directly can be pieced together mixedly, be ground to and be uniformly dispersed.Equally, above-mentioned finished product dispersive red dye C and C.I. DISPERSE ORANGE 30 200 73 also can adopt the commercially available prod, as the Disperse Red TRHNF and the C.I. DISPERSE ORANGE 30 200 73 of Zhejiang Province Longsheng Group Co., Ltd's production.
Composite disperse red 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 | ||||
| Embodiment 1 | ????12 | ????4.5 | ????60 | ????23.5 | ????0 | ????0 | ???120 |
| Embodiment 2 | ????15 | ????5 | ????60 | ????0 | ????20 | ????0 | ???120 |
| Embodiment 3 | ????21 | ????3 | ????50 | ????0 | ????0 | ????26 | ???120 |
| Embodiment 4 | ????22 | ????5 | ????0 | ????0 | ????0 | ????73 | ???120 |
| Embodiment 5 | ????22 | ????7 | ????0 | ????0 | ????71 | ????0 | ???120 |
| Embodiment 6 | ????30 | ????10 | ????0 | ????60 | ????0 | ????0 | ???120 |
| Embodiment 7 | ????32 | ????11 | ????57 | ????0 | ????0 | ????0 | ???120 |
Embodiment 8～11
According to continuous data shown in the table 2, with dispersive red dye C (commercial dye, monomer A content 35%), C.I. DISPERSE ORANGE 30 200 73 (commercial dyes, monomers B content 35.4%), 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 | Disperse Red C (gram) | C.I. DISPERSE ORANGE 30 200 73 (gram) | Auxiliary agent (gram) | Water (gram) | ||
| Dispersant MF | Dispersing agent CNF | Dispersing agent NNO | ||||
| Embodiment 8 | ???40 | ?????15 | ???61 | ????0 | ????0 | ????0 |
| Embodiment 9 | ???50 | ?????16.5 | ???0 | ????50 | ????0 | ????140 |
| Embodiment 10 | ???60 | ?????14 | ???0 | ????0 | ????26 | ????120 |
| Embodiment 11 | ???65 | ?????20 | ???18 | ????0 | ????0 | ????125 |
| Embodiment 12 | ???70 | ?????28 | ???0 | ????0 | ????0 | ????110 |
Embodiment 13
Respectively getting 0.5 dispersive red dye that makes of gram embodiment 1～12 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 | 5～6 grades | 4～5 grades |
| Embodiment 2 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 3 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 4 | 5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 5 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 6 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 7 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 8 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 9 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 10 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 11 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 12 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
Claims (5)
1, a kind of composite disperse red dye, form by following component basically:
Weight fraction is 10～35% the dye monomer A suc as formula (I),
Weight fraction is 1～15% the dye monomer B suc as formula (II),
Surplus is an auxiliary agent.
2, composite disperse red dye according to claim 1 is characterized in that described auxiliary agent is one of following or its two or more mixture: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.
3, composite disperse red dye according to claim 2 is characterized in that described alkyl naphthalene sulfonic acid formaldehyde condensation products is condensation compound of methyl naphthalene sulfonic acid and formaldehyde or benzyl naphthalenesulfonate formaldehyde condensation compound.
4, composite disperse red dye according to claim 2 is characterized in that described sulfonated lignin are sodium lignosulfonate.
5, according to the described composite disperse red dye of one of claim 1～4, the weight fraction that it is characterized in that described dye monomer A is 15～30%, and the weight fraction of dye monomer B is 1～10%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100681714A CN1305972C (en) | 2004-11-10 | 2004-11-10 | Composite disperse red dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100681714A CN1305972C (en) | 2004-11-10 | 2004-11-10 | Composite disperse red dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1631991A true CN1631991A (en) | 2005-06-29 |
| CN1305972C CN1305972C (en) | 2007-03-21 |
Family
ID=34846749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100681714A Expired - Fee Related CN1305972C (en) | 2004-11-10 | 2004-11-10 | Composite disperse red dye |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1305972C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101125959B (en) * | 2007-08-13 | 2010-07-14 | 江苏亚邦染料股份有限公司 | Modified synthesis technique for disperse red 92 |
| 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 |
| CN104710840A (en) * | 2013-12-31 | 2015-06-17 | 江苏吉华化工有限公司 | Disperse red dye composition |
| CN105385192A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Green and environment-friendly red reactive dye composite |
| CN106833023A (en) * | 2016-12-30 | 2017-06-13 | 浙江闰土研究院有限公司 | A kind of disperse dye composition and its production and use |
| CN106893356A (en) * | 2017-01-10 | 2017-06-27 | 泉州市希姆色彩研究院有限公司 | A kind of disperse orange dye of water fastness high and preparation method thereof |
| CN111004524A (en) * | 2019-12-24 | 2020-04-14 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye, and preparation method and application thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0745636B2 (en) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | Disperse dye mixture |
| JP3115106B2 (en) * | 1992-06-30 | 2000-12-04 | ダイスタージャパン株式会社 | Disperse dye mixture |
| JPH0762258A (en) * | 1993-08-26 | 1995-03-07 | Sumitomo Chem Co Ltd | Red coloring composition containing benzodifuranone and coloring of hydrophobic material using the composition |
| JP3310471B2 (en) * | 1994-02-04 | 2002-08-05 | 日本化薬株式会社 | Red disperse dye composition and method for dyeing hydrophobic fiber material using the same |
| TW324021B (en) * | 1994-03-08 | 1998-01-01 | Daistar Japan Kk | Mono-azo dyestuff |
| JPH07304973A (en) * | 1994-05-09 | 1995-11-21 | Mitsubishi Kasei Hoechst Kk | Benzisothiazole monoazo dye |
-
2004
- 2004-11-10 CN CNB2004100681714A patent/CN1305972C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101125959B (en) * | 2007-08-13 | 2010-07-14 | 江苏亚邦染料股份有限公司 | Modified synthesis technique for disperse red 92 |
| 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 |
| CN104710840A (en) * | 2013-12-31 | 2015-06-17 | 江苏吉华化工有限公司 | Disperse red dye composition |
| CN104710840B (en) * | 2013-12-31 | 2016-10-12 | 江苏吉华化工有限公司 | A kind of dispersion red dye composition |
| CN105385192A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Green and environment-friendly red reactive dye composite |
| CN106833023A (en) * | 2016-12-30 | 2017-06-13 | 浙江闰土研究院有限公司 | A kind of disperse dye composition and its production and use |
| CN106833023B (en) * | 2016-12-30 | 2020-05-01 | 浙江闰土研究院有限公司 | Disperse dye composition and preparation method and application thereof |
| CN106893356A (en) * | 2017-01-10 | 2017-06-27 | 泉州市希姆色彩研究院有限公司 | A kind of disperse orange dye of water fastness high and preparation method thereof |
| CN111004524A (en) * | 2019-12-24 | 2020-04-14 | 浙江闰土股份有限公司 | Disperse dye composition, disperse dye, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1305972C (en) | 2007-03-21 |
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Owner name: SHANGYU JILONG CHEMICALS BUILDING MATERIALS CO., L Free format text: FORMER OWNER: ZHEJIANG PROVINCE LONGSHENG GROUP CO., LTD. Effective date: 20090814 |
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Effective date of registration: 20090814 Address after: Zhejiang city of Shangyu Province town of Shangyu Jilong chemical building materials Co., zip code: 312368 Co-patentee after: Zhejiang Longsheng Group Co., Ltd. Patentee after: Shangyu Jilong chemical building materials Co., Ltd. Address before: Shangyu City, Zhejiang Province town of dragon road Sheng group postcode: 312368 Patentee before: Zhejiang Longsheng Group Co., Ltd. |
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Effective date of registration: 20160811 Address after: 312369 Zhejiang Hangzhou Bay Shangyu Industrial Park Patentee after: Zhejiang Jisheng Chemical Building Materials Co.,Ltd. Patentee after: Zhejiang Longsheng Group Co., Ltd. Address before: 312368 Zhejiang city of Shangyu Province town of Shangyu Jilong chemical building materials Co. Ltd. Patentee before: Shangyu Jilong Chemical Building Materials Co.,Ltd. Patentee before: Zhejiang Longsheng Group Co., Ltd. |
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Granted publication date: 20070321 Termination date: 20171110 |
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| CF01 | Termination of patent right due to non-payment of annual fee |