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CN102504595B - Azo dye composition, preparation method thereof and use method thereof - Google Patents

Azo dye composition, preparation method thereof and use method thereof Download PDF

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Publication number
CN102504595B
CN102504595B CN201110359680.2A CN201110359680A CN102504595B CN 102504595 B CN102504595 B CN 102504595B CN 201110359680 A CN201110359680 A CN 201110359680A CN 102504595 B CN102504595 B CN 102504595B
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China
Prior art keywords
dye composition
general formula
former
composition
azo dye
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CN201110359680.2A
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Chinese (zh)
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CN102504595A (en
Inventor
王敬敏
李诗杰
刘春德
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DONGYING ANNUOQI TEXTILE MATERIAL Co Ltd
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DONGYING ANNUOQI TEXTILE MATERIAL Co Ltd
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Abstract

The invention relates to the fine chemical engineering filed, and especially relates to a dark-blue disperse azo dye composition, a preparation method thereof and a use method thereof. The composition comprises two optimized azo disperse dyes with different general formulas according to a certain ratio, and a certain amount of a disperse assistant is added when the composition is applied. The composition has the characteristics of high dye uptake rate, high deep dyeing, excellent dyeing fastness, good promotion property, good leveling property and the like when a hydrophobic material fiber is taken up by the composition. The composition accords with environmentally-friendly and ecological requirements; and one dye comprised in the composition is a compound of the general formula (I), and the other dye comprised in the composition is a compound of the general formula (II).

Description

A kind of azo dye composition and preparation method thereof, using method
Technical field
The present invention relates to field of fine chemical, relate in particular to a kind of dark dark blue azo dye composition and preparation method thereof, using method of disperseing.
Background technology
Along with the raising of people's living standard and the enhancing of environmental consciousness, the requirement of the many aspects such as healthy comfortable, environment amenable textiles is more and more subject to human consumer's favor, and this just requires to be applied to, and dyestuff on textiles has good stability at corresponding production, storage, dyeing and printing process, in taking process, coloring intensity is high, dyefastness is good, nontoxic non-carcinogenesis, three waste discharge are few.And, along with the formulation of international and domestic every statutory standard, the requirement that limits the use of material for various forbiddings such as forbidding dyestuff, carcinogenic aromatic amines is increasingly strict, the quantity of showing great attention to material (SVHC) that Europe chemical management board (ECHA) announces is also constantly newly-increased, and these high-performance environment-friendly type dyes that all force dye industry exploitation to make new advances are forbidden dyestuff with Substitute For Partial.Environmental protection type dye should meet following condition: do not contain and do not produce harmful aromatic amine, dyestuff itself is without carcinogenic, sensitization, anxious toxicity, after using formaldehyde and can extracting heavy metal content below limited volume, not containing environmental hormone and AOX, not containing persistence organic pollutant, can not produce the chemical substance of contaminate environment, colour fastness and tint applications performance are better than forbidding dyestuff.
Summary of the invention
Object of the present invention is exactly the defect existing for prior art, especially a kind of dark dark blue azo dye composition and preparation method thereof, using method of disperseing, when it is applied to textile dyeing, there is very high coloring intensity and good dyefastness, meet the requirement of high-performance environment-friendly type dye.
The present invention is achieved by the following technical solutions:
A kind of azo dye composition of given first, its component comprises the former dye composition of general formula (I) and the former dye composition of general formula (II);
Described general formula (I) is ,
Described general formula (II) is ;
Wherein R1 is H ,-CH 3,-NHCOCH 3or-NHCOC 2h 5, R2 be H or-OCH 3, R3, R4 are-C 2h 5,-C 3h 7,-C 2h 4oCOCH 3,-CH 2cOOCH 3,-C 2h 4cOOCH 3or-C 2h 4oCH 3, R5 is-CH 3,-NHCOCH 3or-NHCOC 2h 5, R6, R7 are-C 2h 5,-C 2h 4oCOCH 3or-C 2h 4oCH 3, X is-Cl or-Br, Y is-NO 2or-CN.
Substituting group is wherein preferably: described R1 is-CH 3or-NHCOCH 3, described R2 is H, described R3 is-C 2h 5,-C 2h 4oCOCH 3or-C 2h 4cOOCH 3, described R4 is-C 2h 4oCH 3or-C 2h 4cOOCH 3, described R5 is-CH 3or-NHCOCH 3, described R6 is-C 2h 5or-C 2h 4oCH 3, described R7 is-C 2h 4oCOCH 3or-C 2h 4oCH 3, described X is-Br that Y is-CN.
Substituting group is more preferably: described R1 is-NHCOCH 3, described R3-C 2h 4cOOCH 3, described R4 is-C 2h 4cOOCH 3, described R5 is-CH 3, described R6 is-C 2h 5, described R7 is-C 2h 4oCOCH 3.
Be that general formula (I) compound is
General formula (II) compound is
In the time that one of former dye composition is selected the compound of above-mentioned general formula (I), it is 25 ~ 50% that its weight accounts for former dye composition total content, be preferably 30-45%, when one of former dye composition is selected above-mentioned general formula (II), compound time, its weight content that accounts for former dye composition is 25 ~ 60%, is preferably 35 ~ 50%.
Next provides the preparation method of above-mentioned azo dye composition, is, after (I) and former dye composition (II) are mixed in proportion, under the existence of auxiliary agent, water or other wetting agent, to carry out corpusculed with pulverizer by general formula; Or under the existence of auxiliary agent, water or other wetting agent, be respectively to mix with above-mentioned ratio after (I) and compound (II) carry out corpusculed processing with pulverizer general formula; Finally be dried by spraying, obtain azo dye composition.
The ratio of auxiliary agent and former dyestuff (being that general formula is (I) and compound gross weight weight (II)) is 0.7 ~ 5:1.The auxiliary agent adopting is dispersed dye conventional dispersion agent, diffusant, tensio-active agents etc. when composite, all can adopt commercially available prod, comprise one of following or its mixture: the anionic dispersing agents such as formaldehyde condensation products, sulfonated lignin of the formaldehyde condensation products of naphthalene sulfonic acidformaldehyde condensation product, alkyl benzene sulphonate (ABS), the formaldehyde condensation products of alkyl naphthalene sulfonic acid, cresol sulfonic acid, or oxyethane, the segmented copolymer of propylene oxide, the non-ionic dispersing agent such as ethylene oxide adduct, the ethylene oxide adduct of polystyrene phenol of alkylphenol.Particularly, naphthalene sulfonic acidformaldehyde condensation product is as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products is as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), dispersing agent CNF (benzyl naphthalene sulfonic formaldehyde condensation compound) etc., and sulfonated lignin are as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
When auxiliary agent is chosen as the combination of condensation compound of methyl naphthalene sulfonic acid and formaldehyde or sodium lignosulfonate Reax 85A one or both wherein, it is 1 ~ 1.2:1 with the ratio of former dye composition gross weight.
In the time that auxiliary agent is chosen as the combination of condensation compound of methyl naphthalene sulfonic acid and formaldehyde and sodium lignosulfonate Reax 85A, the ratio of the two is 5:2.
Finally provide the using method of above-mentioned azo dye composition, getting 1.5 ~ 3 weight part azo dye compositions is dispersed in 300 ~ 600 weight parts waters, draw 12-24 weight part from dispersion liquid after, mix with the water of 48-96 weight part, adjusting dye bath pH with acetic acid is 4 ~ 5, being warming up to 60 ~ 80 DEG C puts into 3 ~ 6 weight part cloth specimens simultaneously and dyes, be warming up to 120 ~ 140 DEG C, insulation 30-60 minute, is cooled to 90 DEG C of following drainings and cleans; Again cloth specimen is put into the reduction clearing liquid that contains 0.5-2 grams per liter caustic soda and 1.5-6 grams per liter vat powder, cleaned 15-40 minute in 60 ~ 80 DEG C, complete dyeing.
The dark dark blue dye composition of dispersion of the present invention, meet environmental protection and the ecological requirement of Oeko-Tex Standard 100, liquid state after can corpusculed, emulsifiable paste shape or carry out dried powdery, particulate state state and be applied to the dyeing of textiles by spray-drying process etc.While dying hydrophobic material fiber, particularly trevira, hyperfine polyester fiber with the dark dark blue composition of dispersion of the present invention, there is the features such as dye uptake is high, depth good, dyefastness is excellent, enhancing is good, good level-dyeing property.
Embodiment
Embodiment:
Below in conjunction with example, the invention will be further described, but protection scope of the present invention is not limited to this.
Embodiment 1-12
By the former dyestuff A of general formula (I) and and after the former dyestuff B of general formula (II) mixes, under the effect of dispersion agent, pure water, carry out corpusculed with the pulverizer such as sand mill or shredder and carry out corpusculed (making dispersion treatment), spraying is dry again, obtains dark dark blue dye composition of the present invention.R in its Central Plains dyestuff A, B 1-R 7and each substituting group of X, Y selects in Table 1-2, the composition of former dyestuff A, B and dispersion agent, pure water and consumption are in table 3.
Table 1
Table 2
Table 3
Embodiment 14
Respectively getting the dispersed dye that 2.5 grams of embodiment 1 ~ 13 make is dispersed in 500 ml waters, drawing respectively 20 milliliters mixes with the water of 80 milliliters, adjusting dye bath pH with acetic acid is 4 ~ 5, being warming up to 70 DEG C puts into 5 grams of polyester fiber cloths simultaneously and dyes, in 30 minutes, be warming up to 130 DEG C by 70 DEG C, be incubated 50 minutes, be cooled to 90 DEG C of following drainings and clean.Cloth specimen is put into 100 milliliters of reduction clearing liquid containing 1 grams per liter caustic soda and 3 grams per liter vat powders again and cleaned in 80 DEG C, the time is 20 minutes.Adopt that GB GB/T 3921-2008, GB/T 3920-2008, GB/T 8427-2008, GB/T 5718-1997 test respectively that it is water-fastness, rub resistance, colour fastness to light and sub limation fastness.Test result is in table 4.
Table 4
Embodiment title Water-fastness (60 DEG C) Rub resistance Fast light Sublimation fastness (180 DEG C)
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 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 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 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
Embodiment 13 4 ~ 5 grades 4 ~ 5 grades 5 ~ 6 grades 4 ~ 5 grades
In above-described embodiment, former dye composition A, B are not limited to aforesaid combination, meeting the reconfiguring of various ingredients of requirement of general formula (I) and general formula (II), can reach equally above-mentioned technique effect, just do not enumerate at this.

Claims (7)

1. an azo dye composition, is characterized in that: component comprises the former dye composition of general formula (I) and the former dye composition of general formula (II);
Described general formula (I) is ,
Described general formula (II) is ;
Wherein R1 is-NHCOCH 3, R2 be H, R3 is-C 2h 4cOOCH 3, R4 is-C 2h 4cOOCH 3, R5 is-CH 3, R6 is-C 2h 5, R7 is-C 2h 4oCOCH 3, X Wei – Br, Y be-CN; The former dye composition of described general formula (I) accounts for 25 ~ 50% of former dye composition gross weight, and the former dye composition of described general formula (II) accounts for 25 ~ 60% of former dye composition gross weight.
2. a kind of azo dye composition according to claim 1, is characterized in that: the former dye composition of described general formula (I) accounts for the 30-45% of former dye composition gross weight.
3. a kind of azo dye composition according to claim 1, is characterized in that: the former dye composition of described general formula (II) accounts for 35 ~ 50% of former dye composition gross weight.
4. the preparation method of the azo dye composition described in any one in claim 1-3, is characterized in that: be, after (I) and former dye composition (II) are mixed in proportion, under the existence of auxiliary agent, to carry out corpusculed with pulverizer by general formula; Or under the existence of auxiliary agent, be respectively to mix with above-mentioned ratio after (I) and compound (II) carry out corpusculed processing with pulverizer general formula; Then be dried by spraying, obtain azo dye composition; Described auxiliary agent and general formula are that the ratio of (I) and former dye composition gross weight (II) is 0.7 ~ 5:1.
5. the preparation method of azo dye composition according to claim 4, it is characterized in that: described auxiliary agent is the combination of condensation compound of methyl naphthalene sulfonic acid and formaldehyde or sodium lignosulfonate Reax 85A one or both wherein, and it is 1 ~ 1.2:1 with the ratio of former dye composition gross weight.
6. the preparation method of azo dye composition according to claim 5, is characterized in that: when described auxiliary agent is the combination of condensation compound of methyl naphthalene sulfonic acid and formaldehyde and sodium lignosulfonate Reax 85A, the ratio of the two is 5:2.
7. the using method of the azo dye composition described in any one in claim 1-3, it is characterized in that: get the azo dye composition described in any one in 1.5 ~ 3 weight part claim 1-3 and be dispersed in 300 ~ 600 weight parts waters, draw 12-24 weight part from dispersion liquid after, mix with the water of 48-96 weight part, adjusting dye bath pH with acetic acid is 4 ~ 5, being warming up to 60 ~ 80 DEG C puts into 3 ~ 6 weight part cloth specimens simultaneously and dyes, be warming up to 120 ~ 140 DEG C, insulation 30-60 minute, is cooled to 90 DEG C of following drainings and cleans; Again cloth specimen is put into the reduction clearing liquid that contains 0.5-2 grams per liter caustic soda and 1.5-6 grams per liter vat powder, cleaned 15-40 minute in 60 ~ 80 DEG C, complete dyeing.
CN201110359680.2A 2011-11-15 2011-11-15 Azo dye composition, preparation method thereof and use method thereof Expired - Fee Related CN102504595B (en)

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CN104710837A (en) * 2013-12-31 2015-06-17 江苏吉华化工有限公司 Disperse blue dye composition
CN104499307A (en) * 2014-12-18 2015-04-08 太湖亚太精化有限公司 Dispersing type dye with high dyeing fastness, and preparation method thereof
CN104530758A (en) * 2014-12-18 2015-04-22 太湖亚太精化有限公司 Heterocyclic disperse dye and preparation method thereof
CN105647235A (en) * 2016-01-20 2016-06-08 俞杏英 High dye uptake disperse dye composition and preparation method and application thereof
CN105623309A (en) * 2016-01-20 2016-06-01 俞杏英 High-dye-uptake disperse dye composition as well as preparation method and application thereof
CN114773877B (en) * 2022-05-20 2023-12-22 上海鸿源鑫创材料科技有限公司 Disperse blue dye composition and product thereof

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CN1317338C (en) * 2004-12-28 2007-05-23 浙江龙盛集团股份有限公司 Monoazo dye composition
CN101550286B (en) * 2009-05-06 2012-10-10 浙江闰土股份有限公司 Disperse dye composition with high washing fastness
CN101914309B (en) * 2010-07-19 2013-04-24 浙江闰土股份有限公司 Environment-friendly composite disperse dye composition capable of performing discharge printing
CN101982511B (en) * 2010-09-18 2013-12-04 浙江万丰化工有限公司 Blue disperse dye complex

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