CN1640941A - Dispersed red dye composition - Google Patents
Dispersed red dye composition Download PDFInfo
- Publication number
- CN1640941A CN1640941A CN 200410093363 CN200410093363A CN1640941A CN 1640941 A CN1640941 A CN 1640941A CN 200410093363 CN200410093363 CN 200410093363 CN 200410093363 A CN200410093363 A CN 200410093363A CN 1640941 A CN1640941 A CN 1640941A
- Authority
- CN
- China
- Prior art keywords
- red dye
- dyestuff
- grades
- dye composition
- dispersed red
- 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 abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 24
- 239000000975 dye Substances 0.000 claims abstract description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 abstract description 11
- 239000002131 composite material Substances 0.000 abstract description 7
- 229920000728 polyester Polymers 0.000 abstract description 7
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 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 abstract 5
- 239000002657 fibrous material Substances 0.000 abstract 3
- 229920006221 acetate fiber Polymers 0.000 abstract 1
- 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
- 239000000463 material Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 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
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 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 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 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
- 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 1
- 229920004934 Dacron® Polymers 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000004218 Orcein Substances 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
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 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
- 235000019248 orcein Nutrition 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 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
- 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
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The present invention relates to one kind of disperse red dye composite, and the disperse red dye composite comprises dye A shown in expression (I) and dye B shown in expression (II). When the disperse red dye composite of the present invention is used in dyeing hydrophobic fiber material, especially polyester fiber material, the disperse red dye composite has the features of high dyeing degree, high dye fastness, high repeatability, good level dyeing property, etc. The disperse red dye composite of the present invention is especially suitable for dyeing superfine polyester fiber material and acetate fiber.
Description
(1) technical field
The present invention relates to a kind of Monoazo-dyes composition.
(2) background technology
Development and the new printing technology superior along with the textile industry lining constantly are developed, and also improve day by day to fastness, application performance and the environmental requirement of dyestuff in weaving market, with regard to dispersed dye, especially shows in the dyeing of ultra-fine polyester material.Compare with the conventional polyester material, the dyeing of ultra-fine polyester material exists at present that level-dyeing property is relatively poor, the Dry Sack rate is not high and problem such as fastness good inadequately (dyefastness that too much causes owing to loose colour that ultra-fine fibre dyes that the large usage quantity of required dyestuff brings is poor).For this reason, develop the heat subject that high dyestuff of a class dyeing behavior excellence, fixation rate or dye composition 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 dispersed red dye composition.
Described dispersed red dye composition comprises suc as formula the dyestuff A shown in (I), suc as formula the dyestuff B shown in (II);
X wherein
1For halogen or-CF
3, be preferably Br or Cl;
X
2For H, halogen or-CH
3, be preferably H or Cl;
R
1For-CH
3Or-C
2H
5, be preferably-CH
3
R
2For-C
2H
5,-CH
2CH
2CN or-CH
2CH
2OCOCH
3
R
3For-CH
2CH
2CN or-CH
2CH
2OCOCH
3
R
4For H or-CH
3
Wherein, described dye composite be preferably especially as shown in the formula (III) and (IV) shown in dye combinations (that is: the X of structure
1Be Br, X
2Be H, R
1For-CH
3, R
2For-CH
2CH
2CN, R
3For-CH
2CH
2OCOCH
3, R
4Be H)
The weight percentage of described dyestuff A can be 1～99%, is preferably 30～70%, more preferably 40～70%, most preferably be 50～70%; The weight percentage of dyestuff B can be 1～99%, is preferably 30～70%, more preferably 30～60%, most preferably 30～50%.
When preparing dispersed red dye composition of the present invention, the dyestuff B of the dyestuff A of employed formula (I) expression and formula (II) expression is respectively disclosed dyestuff such as patent US5194598 and patent JP4370158 or similar these dyestuff, with the method for wherein record or similarly method can make at an easy rate.
Dispersion red dye composition of the present invention generally needs to add auxiliary agent and disperses during application.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, 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), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound) etc., sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
Dispersed red dye composition 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.Dye the hydrophobic material fiber with dispersed red dye composition of the present invention, particularly during the polyester material fiber, have characteristics such as dye uptake height, fastness are good, favorable reproducibility, good level-dyeing property, also be fit to very much dye ultra-fine polyester material fiber and cellulose acetate.
(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
Former dyestuff 25 grams shown in former dyestuff shown in the formula (III) 25 grams, the formula (IV), dispersion agent Reax 85A 75 grams, pure water 150 grams one are reinstated sand mill and carried out corpusculed (making dispersion treatment), spraying drying promptly gets orchil mixture of the present invention again.
Embodiment 2～10
According to the preparation method of embodiment 1, be by the data shown in the following table 2 component A, B component to be pieced together mixedly as the dye composition that is used, wherein, the defined disperse dyes structure formula of each substituting group sees the following form 1.
Table 1
| The embodiment title | Dyestuff A | Dyestuff B | ||||
| ????X 1 | ????X 2 | ??R 1 | R 2 | R 3 | ????R 4 | |
| Embodiment 2 | ????Cl | ????H | ??-CH 3 | -C 2H 5 | -C 2H 4CN | ????-CH 3 |
| Embodiment 3 | ????Br | ????H | ??-C 2H 5 | -C 2H 4CN | -C 2H 4OCOCH 3 | ????H |
| Embodiment 4 | ????Cl | ????H | ??-C 2H 5 | -C 2H 4CN | -C 2H 4OCOCH 3 | ????H |
| Embodiment 5 | ????Cl | ????Cl | ??-CH 3 | -C 2H 5 | -C 2H 4OCOCH 3 | ????H |
| Embodiment 6 | ????-CF 3 | ????H | ??-CH 3 | -C 2H 4CN | -C 2H 4OCOCH 3 | ????H |
| Embodiment 7 | ????Br | ????Cl | ??-CH 3 | -C 2H 4OCOCH 3 | -C 2H 4OCOCH 3 | ????H |
| Embodiment 8 | ????Br | ????CH 3 | ??-CH 3 | -C 2H 4OCOCH 3 | -C 2H 4OCOCH 3 | ????H |
| Embodiment 9 | ????Br | ????H | ??-CH 3 | C 2H 5 | -C 2H 4CN | ????-CH 3 |
| Embodiment 10 | ????Br | ????H | ??-CH 3 | C 2H 5 | -C 2H 4OCOCH 3 | ????H |
Table 2
| The embodiment title | Dyestuff A (gram) | Dyestuff B (gram) | Auxiliary agent (gram) | Pure water | |
| Embodiment 2 | 15 | 35 | Dispersant MF | ????75 | ??150 |
| Embodiment 3 | 18 | 32 | ????75 | ??150 | |
| Embodiment 4 | ????20 | ????30 | Dispersing agent CNF | ????75 | ????150 |
| Embodiment 5 | ????22 | ????28 | ????75 | ????150 | |
| Embodiment 6 | ????25 | ????25 | ????75 | ????150 | |
| Embodiment 7 | ????28 | ????22 | ????75 | ????150 | |
| Embodiment 8 | ????30 | ????20 | Dispersing agent NNO | ????75 | ????150 |
| Embodiment 9 | ????32 | ????18 | ????75 | ????150 | |
| Embodiment 10 | ????35 | ????15 | ????75 | ????150 |
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, being warming up to 70 ℃ puts into 2 gram dacron ultrafine fiber cloth simultaneously and dyes, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 40 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 (60 ℃) | 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 | 5～6 grades | 4～5 grades |
| Embodiment 3 | 4～5 grades | 4～5 grades | 5～6 grades | 4～5 grades |
| Embodiment 4 | 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 | 5 grades | 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 | 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 |
Claims (10)
1, a kind of dispersed red dye composition comprises suc as formula the dyestuff A shown in (I), suc as formula the dyestuff B shown in (II);
X wherein
1For halogen or-CF
3X
2For H, halogen or-CH
3
R
1For-CH
3Or-C
2H
5R
2For-C
2H
5,-CH
2CH
2CN or-CH
2CH
2OCOCH
3
R
3For-CH
2CH
2CN or-CH
2CH
2OCOCH
3R
4For H or-CH
3
2, dispersed red dye composition as claimed in claim 1 is characterized in that described X
1Be Br or Cl.
3, dispersed red dye composition as claimed in claim 1 is characterized in that described X
2Be H or Cl.
4, dispersed red dye composition as claimed in claim 1 is characterized in that described R
1For-CH
3
5, dispersed red dye composition as claimed in claim 1 is characterized in that described X
1Be Br or Cl, X
2Be H or Cl, R
1For-CH
3
6, dispersed red dye composition as claimed in claim 5 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).
7, as the described dispersed red dye composition of one of claim 1～6, the weight percentage that it is characterized in that described dyestuff A is 1～99%, and the weight percentage of dyestuff B is 1～99%.
8, dispersed red dye composition as claimed in claim 7, the weight percentage that it is characterized in that described dyestuff A is 30～70%, the weight percentage of dyestuff B is 30～70%.
9, dispersed red dye composition as claimed in claim 8, the weight percentage that it is characterized in that described dyestuff A is 40～70%, the weight percentage of dyestuff B is 30～60%.
10, dispersed red dye composition as claimed in claim 9, the weight percentage that it is characterized in that described dyestuff A is 50～70%, the weight percentage of dyestuff B is 30～50%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100933630A CN1328325C (en) | 2004-12-16 | 2004-12-16 | Dispersed red dye composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100933630A CN1328325C (en) | 2004-12-16 | 2004-12-16 | Dispersed red dye composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1640941A true CN1640941A (en) | 2005-07-20 |
| CN1328325C CN1328325C (en) | 2007-07-25 |
Family
ID=34869404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100933630A Expired - Fee Related CN1328325C (en) | 2004-12-16 | 2004-12-16 | Dispersed red dye composition |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1328325C (en) |
Cited By (4)
| 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 |
| CN104231659A (en) * | 2014-07-22 | 2014-12-24 | 俞杏英 | Red thiazole heterocyclic disperse dye compound containing benzoate group and preparation and application thereof |
| CN106189360A (en) * | 2016-08-04 | 2016-12-07 | 菲诺染料化工(无锡)有限公司 | Environment-friendly type dispersed ruby blending ingredients and disperse dyes |
| CN114989632A (en) * | 2022-07-05 | 2022-09-02 | 绍兴金绿洲新材料科技有限公司 | Disperse brilliant red dye composition with high fastness and high dyeing strength |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2759103C2 (en) * | 1977-12-30 | 1986-10-09 | Bayer Ag, 5090 Leverkusen | Azo dyes and their use |
| US5194598A (en) * | 1987-10-24 | 1993-03-16 | Bayer Aktiengesellschaft | Azo dyestuffs in which the coupling component contains an N,N-bis(alkoxy carbonylalkyl) substituent |
| JPH0745636B2 (en) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | Disperse dye mixture |
-
2004
- 2004-12-16 CN CNB2004100933630A patent/CN1328325C/en not_active Expired - Fee Related
Cited By (4)
| 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 |
| CN104231659A (en) * | 2014-07-22 | 2014-12-24 | 俞杏英 | Red thiazole heterocyclic disperse dye compound containing benzoate group and preparation and application thereof |
| CN106189360A (en) * | 2016-08-04 | 2016-12-07 | 菲诺染料化工(无锡)有限公司 | Environment-friendly type dispersed ruby blending ingredients and disperse dyes |
| CN114989632A (en) * | 2022-07-05 | 2022-09-02 | 绍兴金绿洲新材料科技有限公司 | Disperse brilliant red dye composition with high fastness and high dyeing strength |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1328325C (en) | 2007-07-25 |
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Effective date of registration: 20090605 Address after: Shangyu City, Zhejiang Province town of dragon road Sheng group postcode: 312368 Co-patentee after: Longsheng Dye Chemical Industry Co., Ltd., Zhejiang Patentee after: Zhejiang Longsheng group Limited by Share 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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