CN101265370A - Medium-temperature-type environmental protection dispersion orange dyes - Google Patents
Medium-temperature-type environmental protection dispersion orange dyes Download PDFInfo
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- CN101265370A CN101265370A CNA2008100607894A CN200810060789A CN101265370A CN 101265370 A CN101265370 A CN 101265370A CN A2008100607894 A CNA2008100607894 A CN A2008100607894A CN 200810060789 A CN200810060789 A CN 200810060789A CN 101265370 A CN101265370 A CN 101265370A
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Abstract
The invention discloses a moderate-temperature environment-friendly disperse orange dye, which comprises a dye monomer A as shown by the formula (1) and accounting for 10 to 50 percent; a dye monomer B as shown by the formula (2) and accounting for 8 to 45 percent; and an accessory ingredient accounting for the rest. The disperse orange dye can further comprise a dye monomer C as shown by formula (3) and accounting for 0.01 to 2 percent. The environment-friendly dye disclosed by the invention can substitute for the mixing color of No.30 C.I.DISP.ORANGE in black and blue of 300 percent, and can be applied in wide PH values when used for dyeing with high build-up, high color yield, excellent level-dyeing property and overall firmness.
Description
Technical field
The present invention relates to a kind of middle warm type environmental protection dispersion orange dyes, be specially adapted to the dyeing and the stamp of terylene and BLENDED FABRIC thereof.
Background technology
Dispersed dye are mainly used in the dyeing and the stamp of trevira, present fast development along with trevira, demands for higher performance to dispersed dye: at first must be the environmental protection dyestuff, it is excellent that next is that the heat-resisting migration of dyestuff and every fastness index are all wanted, and is that the compatibleness between dyestuff is good once more.Patent EP0491386, JP10251534, JP08100132 all are that the dyestuff assembly mixes to such an extent that use, and purpose is to promote the printing and dyeing performance of dyestuff.But, still can not satisfy the demands aspect the application performances such as lifting force and dyefastness from existing azo splicing dye species.
Summary of the invention
It is all excellent to the invention provides a kind of environmental protection, economy, every fastness ability, particularly can be used to piece together black, the blue serial middle warm type disperse orange dye composition of system.
Warm type environmental protection dispersion orange dyes in a kind of comprises following component by weight percentage:
10%～50% dye monomer A as the formula (1)
R
1Be Cl or Br;
R
2Be Cl or Br;
R
3For-CH
2CH=CH
2Or-CH
3Or-(CH
2)
nCH
3, n=1～3;
8%～45% dye monomer B as the formula (2)
R
4For-(CH
2)
n-Ph, n=1～2 or-C
2H
4OCO-Ph;
Surplus is an auxiliary agent.
The warm type environmental protection dispersion orange dyes also comprises 0.01%～2% dye monomer C as the formula (3) in described, is used for regulating coloured light:
X is Cl or Br or I or NO
2Or CN;
Y is NHCOCH
3Or NHCOC
2H
5
R
5, R
6Independent separately is C
1～C
4Alkyl.
A kind of preferred middle warm type environmental protection dispersion orange dyes, comprise following component by weight percentage: 15%～45% dye monomer A as the formula (1), 10%～25% dye monomer B as the formula (2), 0.05%～0.3% dye monomer C as the formula (3).
Described dye composition A is one or more the mixture in the formula (1-1) to (1-9):
Described dye composition B is one or more the mixture in the formula (2-1) to (2-3):
Described dye composition C is one or more the mixture in the formula (3-1) to (3-6):
Described auxiliary agent is dispersed dye dispersion agent, diffusant and tensio-active agents thereof etc. commonly used when composite, preferably includes one of following or its mixture: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products.As condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF), naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (xylogen 85A, 83A) etc.
Warm type environmental protection dispersion orange dyes composition can be used by the below method and prepare in of the present invention:
After dye monomer A, dye monomer B, dye monomer C mixed by said ratio, in the presence of auxiliary agent, water or other tensio-active agent, carry out corpusculed with pulverizers such as sand mill or shredders; Also the former dyestuff of dye monomer A, dye monomer B, dye monomer C can be carried out corpusculed with pulverizers such as sand mill or shredders respectively in the presence of auxiliary agent, water or other tensio-active agent, mix by said ratio again.
Described dye monomer A, dye monomer B, dye monomer C all can adopt the commercially available prod.
Warm type environmental protection dispersion orange dyes composition is to be formed by middle warm type dyestuff compatibility in of the present invention, aqueous with can be after sand mill or the shredder grinding, can be powdery, particulate state after the spraying drying, the colorant match of alternative C.I.DISP.ORANGE 30# in 300% black, basket.This dye composite is the environmental protection dyestuff, and when dyeing pH value subject range relatively broadness, lifting force is high, dye yield is high, good level-dyeing property, every fastness are all good.
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 1～18
According to the data in the table 1, dye monomer A, dye monomer B, dye monomer C, auxiliary agent and water are mixed the back grind dispersion with sand mill, carry out spraying drying then.Dye monomer wherein all can adopt commercially available prod or preparation voluntarily.
The preparation method of structural formula (1-1) is: by 2, after the 6-two bromo-4 N-methyl-p-nitroaniline diazotization, form with N-butyl-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-2) is: after 2-chloro-6 bromo-4 N-methyl-p-nitroaniline diazotization, form with N-butyl-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-3) is: after 2-chloro-6 bromo-4 N-methyl-p-nitroaniline diazotization, form with N-methyl-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-4) is: by 2, after the 6-two bromo-4 N-methyl-p-nitroaniline diazotization, form with N-methyl-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-5) is: after 2-chloro-6 bromo-4 N-methyl-p-nitroaniline diazotization, form with N-allyl group-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-6) is: by 2, after the 6-two bromo-4 N-methyl-p-nitroaniline diazotization, form with N-allyl group-N-cyanoethyl aniline coupling again.
The preparation method of structural formula (1-7) is: after 2-chloro-6 bromo-4 N-methyl-p-nitroaniline diazotization, form with the coupling of N-ethyl-N-cyanoethyl aniline again.
The DISPERSE ORANGE 30 200 61# that structural formula (1-8) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The DISPERSE ORANGE 30 200 76# that structural formula (1-9) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The preparation method of structural formula (2-1) is: after p-Nitroaniline diazotization, form with N-cyanoethyl-N-styroyl aniline coupling again.
The DISPERSE ORANGE 30 200 288# that structural formula (2-2) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The preparation method of structural formula (2-3) is: after p-Nitroaniline diazotization, form with N-cyanoethyl-N-benzoyl oxygen ethylaniline coupling again.
The EX-SF DISPERSE BLUE EX-SF 300 183:1# that structural formula (3-1) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The preparation method of structural formula (3-2) is: after 2-cyano group-4-nitro-6 chloroaniline diazotization, again with N, the coupling of N-diethyl m-acetamino aniline forms.
The preparation method of structural formula (3-3) is: after 2-cyano group-4-nitro-6 Iodoaniline diazotization, again with N, the coupling of N-diethyl m-acetamino aniline forms.
The EX-SF DISPERSE BLUE EX-SF 300 165# that structural formula (3-4) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The EX-SF DISPERSE BLUE EX-SF 300 165:1# that structural formula (3-5) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
The EX-SF DISPERSE BLUE EX-SF 300 183# that structural formula (3-6) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce.
Table 1
The dispersed dye that the foregoing description is made carry out performance test, and testing method is as follows:
Respectively get the dispersed dye that 1 gram embodiment 1-25 makes, it is 1g/500ml dispersion suspension liquid that water is mixed with concentration respectively.(1) water of drawing 10ml and 90ml mixes; (2) water of drawing 50ml and 50ml mixes; (3) draw the 100ml dye liquor; (4) drawing some ml, to be used for piecing together system black, blue, regulates dye bath pH value to 5 with acetic acid, is warmed up to 60 ℃ then, puts into the 2g trevira simultaneously respectively and carry out high-temperature pressure dyeing, was warmed up to 130 ℃ in 35 minutes, be incubated 30 minutes, takes a sample when being cooled to 80 ℃.Survey its lifting force, observe itself and 300% black, blue compatibility, and adopt GB GB/T3921-1997, GB/T3920-1997, GB/T5718-1997 to measure its washing fastness, crock fastness, sublimation fastness, test result shows: the every fastness index of disperse orange dye composition provided by the invention is all excellent, especially all be better than C.I.DISP ORANGE 30# with 300% black, blue lifting force, compatibleness when composite and piece together black, the blue effect of system, and not only economy but also material benefit.Test result is as shown in table 2.
Table 2
| The embodiment title | Lifting force | With black blue compatibility | Washing fastness | Crock fastness | Sublimation fastness (180 ℃) |
| 1 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 2 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 3 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 4 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 5 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 6 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 7 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 8 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 9 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 10 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 11 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 12 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 13 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 14 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 15 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 16 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 17 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 18 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 19 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 20 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 21 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 22 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 23 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 24 | A | Excellent | 4-5 | 4-5 | 4-5 |
| 25 | A | Excellent | 4-5 | 4-5 | 4-5 |
Claims (7)
1. warm type environmental protection dispersion orange dyes in a kind comprises following component: 10%～50% dye monomer A as the formula (1) by weight percentage
R
1Be Cl or Br;
R
2Be Cl or Br;
R
3For-CH
2CH=CH
2Or-CH
3Or-(CH
2)
nCH
3, n=1～3;
8%～45% dye monomer B as the formula (2)
R
4For-(CH
2)
n-Ph, n=1～2 or-C
2H
4OCO-Ph;
Surplus is an auxiliary agent.
2. warm type environmental protection dispersion orange dyes in as claimed in claim 1, it is characterized in that: comprise 10%～50% dye monomer A as the formula (1) by weight percentage, 8%～45% dye monomer B as the formula (2), 0.01%～2% dye monomer C as the formula (3)
X is Cl or Br or I or NO
2Or CN;
Y is NHCOCH
3Or NHCOC
2H
5
R
5, R
6Independent separately is C
1～C
4Alkyl;
Surplus is an auxiliary agent.
3. warm type environmental protection dispersion orange dyes in as claimed in claim 2, it is characterized in that: comprise following component by weight percentage: 15%～45% dye monomer A as the formula (1), 10%～25% dye monomer B as the formula (2), 0.05%～0.3% dye monomer C as the formula (3).
4. warm type environmental protection dispersion orange dyes in as claimed in claim 2 is characterized in that: described dye composition C is one or more the mixture in the formula (3-1) to (3-6):
5. warm type environmental protection dispersion orange dyes in as claimed in claim 1 is characterized in that: described dye composition A is one or more the mixture in the formula (1-1) to (1-9):
6. warm type environmental protection dispersion orange dyes in as claimed in claim 1 is characterized in that: described dye composition B is one or more the mixture in the formula (2-1) to (2-3):
7. warm type environmental protection dispersion orange dyes in as claimed in claim 1, it is characterized in that: described auxiliary agent is one of naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products or its mixture.
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|---|---|---|---|
| CN2008100607894A CN101265370B (en) | 2008-04-22 | 2008-04-22 | Medium-temperature-type environmental protection dispersion orange dyes |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100607894A CN101265370B (en) | 2008-04-22 | 2008-04-22 | Medium-temperature-type environmental protection dispersion orange dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101265370A true CN101265370A (en) | 2008-09-17 |
| CN101265370B CN101265370B (en) | 2010-04-14 |
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ID=39988069
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103571229A (en) * | 2013-10-18 | 2014-02-12 | 浙江山峪染料化工有限公司 | Intermediate temperate type high-fastness dispersed orange dye |
| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN111320880A (en) * | 2018-12-14 | 2020-06-23 | 东营安诺其纺织材料有限公司 | Disperse blue dye and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100341953C (en) * | 2005-05-20 | 2007-10-10 | 浙江闰土股份有限公司 | Composite environmental protection type disperse dyes |
| CN100569866C (en) * | 2008-01-28 | 2009-12-16 | 吴江市绿洲染料化工有限公司 | A kind of environment-friendly type and alkaline-resisting type disperse orange dyes mixture |
| CN101275039B (en) * | 2008-03-21 | 2010-12-15 | 上虞市金冠化工有限公司 | Disperse orange dye composition |
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2008
- 2008-04-22 CN CN2008100607894A patent/CN101265370B/en active Active
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN104087017B (en) * | 2013-05-16 | 2016-05-25 | 上海安诺其集团股份有限公司 | A kind of preparation method of orange disperse dye |
| CN104087010B (en) * | 2013-05-16 | 2016-06-01 | 上海安诺其集团股份有限公司 | A kind of admixture of disperse dyes |
| CN104088165B (en) * | 2013-05-16 | 2017-02-08 | 上海安诺其集团股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN103571229A (en) * | 2013-10-18 | 2014-02-12 | 浙江山峪染料化工有限公司 | Intermediate temperate type high-fastness dispersed orange dye |
| CN111320880A (en) * | 2018-12-14 | 2020-06-23 | 东营安诺其纺织材料有限公司 | Disperse blue dye and preparation method thereof |
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|---|---|
| CN101265370B (en) | 2010-04-14 |
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