CN103450708A - Environment-friendly orange disperse dye mixture - Google Patents

Environment-friendly orange disperse dye mixture Download PDF

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CN103450708A
CN103450708A CN2013104080439A CN201310408043A CN103450708A CN 103450708 A CN103450708 A CN 103450708A CN 2013104080439 A CN2013104080439 A CN 2013104080439A CN 201310408043 A CN201310408043 A CN 201310408043A CN 103450708 A CN103450708 A CN 103450708A
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dye
formula
environment
dye monomer
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CN103450708B (en
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徐杰
叶雷
卢建平
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JIANGSU YABANG DYESTUFFS CO Ltd
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JIANGSU YABANG DYESTUFFS CO Ltd
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Abstract

The invention relates to an environment-friendly orange disperse dye mixture which comprises the following components in percentage by weight: 1%-50% of dye monomers A shown in a formula (I), 1%-70% of dye monomers B shown in a formula (II), 1%-30% of dye monomers C shown in a formula (III) and the balance being additives. According to the environment-friendly orange disperse dye mixture, the defects of C.I. disperse oranges 29 and 30 are effectively overcome, the production cost can be reduced, sewage caused by dyeing is reduced, the dye mixture is ecological and green dye meeting the European Union Reach regulatory requirements and the Oeko-Tex Standard 100 environmental certification, the disperse oranges 29 and 30 can be successfully replaced by the dye mixture, the dye mixture is good in compatibility, wide in pH value range during a dyeing process, high in dye yield, good in leveling property and more outstanding in sublimation fastness and washing fastness especially, and the dye mixture is environment-friendly orange disperse dye superior in various performance.

Description

A kind of environment-friendly type orange admixture of disperse dyes
Technical field
The present invention relates to a kind of orange disperse dye, relate in particular to a kind of environment-friendly type orange admixture of disperse dyes, these dispersed dye are applicable to the printing and dyeing of trevira.
Background technology
Along with the raising day by day of standard of living in recent years, people's environmental consciousness also improves gradually, and dyeing behavior and the environmental-protecting performance of dyestuff are also had higher requirement.As C.I. DISPERSE ORANGE 30 200 29 light permanencys and opacifying property good application comparatively extensive, but easily bring harmful aromatic amine (Ortho Anisidine) when synthetic into because of it, do not meet the Oeko-Tex Standard 100 ecological, environmental protective requirements that European Union member countries promulgate, therefore can't meet the outlet needs of textiles; And for example C.I. DISPERSE ORANGE 30 200 30, because the superiority of the aspect of performances such as its low price, equalization, opacifying property, light permanency has been widely used, becomes one of indispensable essential tone in trevira.But can not contain chlorophenosic acid and the pentachlorophenol of not environmental protection in up-to-date Reach rules and Oeko-Tex Standard 100 environmental requirement dyestuffs, this point has also limited the consumption of C.I. DISPERSE ORANGE 30 200 30, Dutch C&amp greatly; A company has listed C.I. DISPERSE ORANGE 30 200 30 in forbidding dyestuff list.
Although have in recent years the disperse orange dye of some environment-friendly types, as patent CN 102516815B, CN 101275039A, CN 1995154B, CN 101265370A, but its coloured light still can't be consistent with C.I. DISPERSE ORANGE 30 200 29,30 with colour fastness, makes printing and dyeing mill directly to substitute.Certainly, more existing patents are as also introduced the substitute of similar environment-friendly type DISPERSE ORANGE 30 200 30 in CN 102516815.B, CN 101275039A, CN 1995154 B, CN 101265370A, but its coloured light and fastness index all can't reach the requirement of C.I. DISPERSE ORANGE 30 200 30, can't directly substitute.Therefore, be badly in need of a kind of dispersed dye that can directly substitute C.I. DISPERSE ORANGE 30 200 29,30 on market, be not only required under various light sources coloured light consistent, and fast light, the washing of dyestuff, distillation, perspiration fastness also to be equal to even better, meet the customer requirement constantly changed.
Summary of the invention
The technical problem that the present invention needs be to provide a kind of cost low, pollute less, compatibleness is good, high, the good level-dyeing property of wide accommodation, the dye yield of pH value, sublimation fastness, washing fastness can substitute C.I. DISPERSE ORANGE 30 200 29,30 fully when dyeing environment-friendly type orange admixture of disperse dyes.
In order to solve the problems of the technologies described above, the present invention is achieved by the following technical solutions:
A kind of environment-friendly type orange admixture of disperse dyes, this dyestuff mainly is comprised of following component:
The dye monomer A as shown in the formula I general structure that weight fraction is 1-50%,
Figure 2013104080439100002DEST_PATH_IMAGE001
（Ⅰ）
R in formula I 1for-H or-Cl;
Dye monomer A as shown in the formula I general structure is selected from following any one or two kinds suc as formula the dye monomer shown in (I-1)-(I-2):
Figure 2013104080439100002DEST_PATH_IMAGE002
（Ⅰ-1）
Figure 2013104080439100002DEST_PATH_IMAGE003
（Ⅰ-2）
The dye monomer B as shown in the formula II general structure that weight fraction is 1-70%,
Figure 2013104080439100002DEST_PATH_IMAGE004
（Ⅱ）
R in formula II 2, R 3for-H or-Br, R 4for-CH 2cH 3or-C 2h 4cN, R 5for-C 2h 4cN or
Figure 2013104080439100002DEST_PATH_IMAGE005
;
Dye monomer B as shown in the formula II general structure is selected from any one or two kinds of dye monomer as shown in following formula (II-1)-(II-2):
Figure 2013104080439100002DEST_PATH_IMAGE006
（Ⅱ-1）
Figure 2013104080439100002DEST_PATH_IMAGE007
（Ⅱ-2）
The dye monomer C as shown in the formula III general structure that weight fraction is 1-30%,
（Ⅲ）
R in formula III 6for-CH 3or-CH 2cH 3, R 7, R 8for-Cl or-H, R 9for-NO 2or-H, R 10for-H or
Figure 2013104080439100002DEST_PATH_IMAGE009
;
Dye monomer C as shown in the formula III general structure is selected from any one or a few of dye monomer as shown in following formula (III-1)-(III-4):
Figure 2013104080439100002DEST_PATH_IMAGE010
（Ⅲ-1）
Figure 2013104080439100002DEST_PATH_IMAGE011
（Ⅲ-2）
Figure 2013104080439100002DEST_PATH_IMAGE012
（Ⅲ-3）
Figure 2013104080439100002DEST_PATH_IMAGE013
（Ⅲ-4）
All the other are auxiliary agent.
As limitation of the invention further, the weight fraction of dye monomer A of the present invention is 5-40%, and the weight fraction of described dye monomer B is 10-50%, and the weight fraction of described dye monomer C is 3-25%, and surplus is auxiliary agent; Described auxiliary agent comprises one of following or its mixture, sodium lignosulfonate (xylogen 85A, 83A), condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF).
Can prepare in accordance with the following methods by dispersed dye of the present invention: by former dye monomer A, the dye monomer B of above-mentioned metering ratio and dye monomer C after pre-dispersed smashing, add auxiliary agent and warm water dispersed with stirring to dissolve, through continuously grinding and filtration, repeat, sand milling to terminal after, send and put the spray-drying tower drying by pipeline, evenly spray into dust laying oil and dispersion agent, the end product packing simultaneously.In spraying drying, the waste gas of output is by cyclone dust collector, by the several dust removal by filtration.
The dye monomer A that the present invention adopts is C.I. DISPERSE ORANGE 30 200 44 or C.I. DISPERSE YELLOW 163; Dye monomer B is C.I. DISPERSE ORANGE 30 200 61 or C.I. DISPERSE ORANGE 30 200 288, and dye monomer C is C.I. DISPERSE Yellow 211, C.I. DISPERSE YELLOW 114 or C.I. DISPERSE YELLOW 241; Above several dye monomer all can be selected commercially available prod.
Color Index (C.I.) is the meaning of " Colour index number ", and it is international dyestuff title.
After adopting technique scheme, the beneficial effect that the present invention obtains is: the present invention has effectively improved the deficiency of C.I. DISPERSE ORANGE 30 200 29,30, can reduce production costs, reduce dyeing waste, and do not contain chlorophenosic acid, pentachlorophenol and forbidding aromatic amine composition in dyestuff, become and meet Oeko-Tex Standard 100 environmental protection and ecological green colouring material, meet the Reach of European Union laws and regulations requirement.The compatibleness of this dye mixture is good simultaneously, and the advantage aspect when dyeing pH value wide accommodation, dye yield high, good level-dyeing property, especially sublimation fastness, washing fastness is more outstanding, is the environment-friendly type orange dispersed dye of the superior DISPERSE ORANGE 30 200 of C.I. fully as an alternative 29,30 of a kind of properties.
embodiment
Below in conjunction with embodiment, the present invention is further detailed explanation, but protection scope of the present invention is not limited to this.
Embodiment 1-10
Press data shown in table 1, by metering former dye monomer A, the dye monomer B of ratio and dye monomer C after pre-dispersed smashing, add auxiliary agent and warm water dispersed with stirring to dissolve, through continuously grinding and filtration, repeat, sand milling to terminal after, send and put the spray-drying tower drying by pipeline, evenly spray into dust laying oil and dispersion agent simultaneously, the end product packing.
Table 1
Figure 2013104080439100002DEST_PATH_IMAGE014
The dispersed dye that above-described embodiment is made carry out the composite performance test, and testing method is as follows:
Respectively get the dispersed dye that 1.0g embodiment 1-10 makes, water is mixed with respectively the dispersed dye suspended substance that concentration is 1.0g/500mL, getting 20mL mixes with the water of 80mL, regulate dye bath pH to 4.5 ~ 5.0 with acetic acid, then be warmed up to 60 ℃, put into respectively trevira simultaneously and carry out high-temperature pressure dyeing, be warmed up to 130 ℃ in 35 minutes, be incubated 30 minutes, sampling while being cooled to 80 ℃.Observe cloth specimen coloured light and adopt GB/T3921, GB/T3920-1997, GB/T5718-1997 to evaluate its dyefastness.Measurement result is in Table 2.
Table 2
Figure 2013104080439100002DEST_PATH_IMAGE015
Dyestuff of the present invention is carried out to violated thing test, test report is as follows simultaneously:
1. aromatic amine test and chlorophenosic acid (TeCP) in azo colouring agent and azoic dyestuff, pentachlorophenol (PCP) content measuring report content are as follows:
Adopt gas chromatograph-mass spectrometer (GC-MS) and high performance liquid chromatograph (HPLC) to detect.
(A) measuring unit: Shanghai Intertek Verified Service Co., Ltd.
(B) sample is received the date: on July 19th, 2013
(C) the examining report date: on July 24th, 2013
(D) report number: SHAH00397198
(E) sample description: yellowish brown powder (DISPERSE ORANGE 30 200 B-LS)
(1) aromatic amine test:
Testing method: EN 14362-1:2012
EN 14362-3:2012 (P-aminoazobenzene)
Forbidding aromatic amine Cas No result
1). 4-phenylaniline 92-67-1 ND
2). p-diaminodiphenyl 92-87-5 ND
3). 4-chloro-o-toluidine 95-69-2 ND
4). 2-naphthylamines 91-59-8 ND
5). o-aminoazotoluene 97-56-3 ND
6). 2-amino-4-nitrotoluene 99-55-8 ND
7). p-Chlorobenzoic acid amide 106-47-8 ND
8). 2,4-diamino anisole 615-05-4 ND
9). 4,4 '-diaminodiphenylmethane 101-77-9 ND
10). 3,3 '-dichlorobenzidine 91-94-1 ND
11). 3,3 '-dimethoxy benzidine 119-90-4 ND
12). 3,3 '-tolidine 119-93-7 ND
13). 3,3 '-dimethyl-4,4 '-diaminodiphenylmethane 838-88-0 ND
14). 2-methoxyl group-5-monomethylaniline 120-71-8 ND
15). 4,4 '-diamino-3,3 '-dichloro diphenyl methane 101-14-4 ND
16). 4,4 '-benzidine ether 101-80-4 ND
17). 4,4 ' diaminodiphenyl sulfide 139-65-1 ND
18). Ortho Toluidine 95-53-4 ND
19). 2,4 di amino toluene 95-80-7 ND
20). 2，4，5-trimethylaniline 137-17-7 ND
21). Ortho Anisidine 90-04-0 ND
22). P-aminoazobenzene 60-09-3 ND
23). 2,4-xylidine 95-68-1 ND
24). 2,6-xylidine 87-62-7 ND
Remarks: ND=not detecting
Detection limit=10 ppm
Ppm=1,000,000/=mg/kg=mg/kg
(2) pentachlorophenol (PCP) content
Detection method: with reference to ISO 17070:2006. result (ppm): ND
Annotation: detection limit=0.5ppm
Ppm=1,000,000/=milligram every kilogram
ND=not detecting
(3) chlorophenosic acid (TeCP) content
Detection method: with reference to ISO 17070:2006.
Compound: 2,3,5,6-chlorophenosic acid
2,3,4,6-chlorophenosic acid
2,3,4,5-chlorophenosic acid
Result (summation) is (ppm): ND
Annotation: detection limit=0.5ppm
Ppm=1,000,000/=milligram every kilogram
ND=not detecting
From above-mentioned detected result, can find out, this product is not containing chlorophenosic acid, pentachlorophenol and forbidding aromatic amine composition, requirement for the Reach of European Union rules is fully satisfied, become and meet Oeko-Tex Standard 100 environmental protection and ecological green colouring material, and also can find out from table 2, the pH scope of application of this product is wider, various colour fastness are all splendid, especially the advantage of sublimation fastness, washing fastness aspect is more outstanding, is the environment-friendly type orange dispersed dye of the superior DISPERSE ORANGE 30 200 of C.I. fully as an alternative 29,30 of a kind of properties.
Above-described specific embodiment of while; purpose of the present invention, technical scheme and beneficial effect are further described; institute is understood that; above are only specific embodiments of the invention; be not limited to the present invention; within the spirit and principles in the present invention all, any modification of making, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.

Claims (6)

1. an environment-friendly type orange admixture of disperse dyes is characterized in that this dyestuff is comprised of following component:
The dye monomer A as shown in the formula I general structure that weight fraction is 1-50%,
Figure 2013104080439100001DEST_PATH_IMAGE001
（Ⅰ）
R in formula I 1for-H or-Cl;
The dye monomer B as shown in the formula II general structure that weight fraction is 1-70%,
Figure 41683DEST_PATH_IMAGE002
（Ⅱ）
R in formula II 2, R 3for-H or-Br, R 4for-CH 2cH 3or-C 2h 4cN, R 5for-C 2h 4cN or ;
The dye monomer C as shown in the formula III general structure that weight fraction is 1-30%,
（Ⅲ）
R in formula III 6for-CH 3or-CH 2cH 3, R 7, R 8for-Cl or-H, R 9for-NO 2or-H, R 10for-H or
Figure 2013104080439100001DEST_PATH_IMAGE005
;
All the other are auxiliary agent.
2. a kind of environment-friendly type orange admixture of disperse dyes according to claim 1, it is characterized in that: the weight fraction of described dye monomer A is 5-40%, the weight fraction of described dye monomer B is 10-50%, and the weight fraction of described dye monomer C is 3-25%.
3. a kind of environment-friendly type orange admixture of disperse dyes according to claim 1 and 2 is characterized in that: described auxiliary agent comprises one of following or its mixture, sodium lignosulfonate, condensation compound of methyl naphthalene sulfonic acid and formaldehyde.
4. according to the described a kind of environment-friendly type orange admixture of disperse dyes of claim 1 or 2, it is characterized in that: the dye monomer A as shown in the formula I general structure is selected from any one or two kinds of dye monomer as shown in following formula (I-1)-(I-2):
Figure 800878DEST_PATH_IMAGE006
（Ⅰ-1）
Figure 2013104080439100001DEST_PATH_IMAGE007
（Ⅰ-2）。
5. according to the described a kind of environment-friendly type orange admixture of disperse dyes of claim 1 or 2,, it is characterized in that: the dye monomer B as shown in the formula II general structure is selected from any one or two kinds of dye monomer as shown in following formula (II-1)-(II-2):
Figure 258404DEST_PATH_IMAGE008
（Ⅱ-1）
Figure 2013104080439100001DEST_PATH_IMAGE009
（Ⅱ-2）。
6. according to the described a kind of environment-friendly type orange admixture of disperse dyes of claim 1 or 2, it is characterized in that: the dye monomer C as shown in the formula III general structure is selected from any one or a few of dye monomer as shown in following formula (III-1)-(III-4):
（Ⅲ-1）
（Ⅲ-2）
Figure 957556DEST_PATH_IMAGE012
（Ⅲ-3）
Figure 2013104080439100001DEST_PATH_IMAGE013
（Ⅲ-4）。
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104530754A (en) * 2014-12-19 2015-04-22 江苏德旺化工工业有限公司 Orange disperse dye
CN106752079A (en) * 2016-12-30 2017-05-31 浙江闰土研究院有限公司 A kind of disperse dye composition and its production and use
CN106977976A (en) * 2017-04-24 2017-07-25 苏州科法曼化学有限公司 Yellow disperse dye compound and its synthetic method and tint applications
CN109679374A (en) * 2018-12-21 2019-04-26 浙江闰土股份有限公司 A kind of yellow disperse dye composition, disperse dyes and its preparation method and purposes
CN113980487A (en) * 2021-11-03 2022-01-28 菲诺染料化工(无锡)有限公司 High-fastness yellow-brown disperse dye mixture
CN114989634A (en) * 2022-07-05 2022-09-02 绍兴金绿洲新材料科技有限公司 Disperse orange dye mixture

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CN101092525A (en) * 2007-06-29 2007-12-26 浙江龙盛染料化工有限公司 Ccomposition of dispersed yellow dye
CN101275039A (en) * 2008-03-21 2008-10-01 上虞市金冠化工有限公司 Disperse orange dye composition
CN102153889A (en) * 2011-02-24 2011-08-17 浙江万丰化工有限公司 Orange disperse dye compound
CN102634233A (en) * 2012-03-27 2012-08-15 江苏之江化工有限公司 Orange mix

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101020789A (en) * 2007-02-14 2007-08-22 浙江龙盛染料化工有限公司 Disperse azo dye composition
CN101092525A (en) * 2007-06-29 2007-12-26 浙江龙盛染料化工有限公司 Ccomposition of dispersed yellow dye
CN101275039A (en) * 2008-03-21 2008-10-01 上虞市金冠化工有限公司 Disperse orange dye composition
CN102153889A (en) * 2011-02-24 2011-08-17 浙江万丰化工有限公司 Orange disperse dye compound
CN102634233A (en) * 2012-03-27 2012-08-15 江苏之江化工有限公司 Orange mix

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104530754A (en) * 2014-12-19 2015-04-22 江苏德旺化工工业有限公司 Orange disperse dye
CN106752079A (en) * 2016-12-30 2017-05-31 浙江闰土研究院有限公司 A kind of disperse dye composition and its production and use
CN106977976A (en) * 2017-04-24 2017-07-25 苏州科法曼化学有限公司 Yellow disperse dye compound and its synthetic method and tint applications
CN109679374A (en) * 2018-12-21 2019-04-26 浙江闰土股份有限公司 A kind of yellow disperse dye composition, disperse dyes and its preparation method and purposes
CN113980487A (en) * 2021-11-03 2022-01-28 菲诺染料化工(无锡)有限公司 High-fastness yellow-brown disperse dye mixture
CN114989634A (en) * 2022-07-05 2022-09-02 绍兴金绿洲新材料科技有限公司 Disperse orange dye mixture

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