CN104194385B - A kind of azo group 1:2 premetallized dye composition and tint applications thereof - Google Patents
A kind of azo group 1:2 premetallized dye composition and tint applications thereof Download PDFInfo
- Publication number
- CN104194385B CN104194385B CN201410409169.2A CN201410409169A CN104194385B CN 104194385 B CN104194385 B CN 104194385B CN 201410409169 A CN201410409169 A CN 201410409169A CN 104194385 B CN104194385 B CN 104194385B
- Authority
- CN
- China
- Prior art keywords
- dye composition
- group
- azo group
- general formula
- dyestuff
- 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.)
- Active
Links
Landscapes
- Coloring (AREA)
Abstract
The invention provides a kind of azo group 1:2 premetallized dye composition and tint applications thereof. The dye composition that the dye composition that this dye composite comprises one or more general formulas (1) expression and one or more general formulas (2) represent. Azo group 1:2 premetallized dye composition provided by the invention, compared with the dyestuff representing with its composition general formula (I), the homochromatism of its nylon/wool blend fabric one-bath process is significantly improved and improves, its compatibility is also significantly improved, be particularly suitable for the dyeing of responsive colour system, thereby greatly expand the tint applications scope of dye composite of the present invention.
Description
Technical field
The present invention relates to a kind of azo group 1:2 premetallized dye composition and tint applications thereof. Particularly, the present invention relates toA kind of azo group 1:2 chromium complex dyestuff composition and tint applications thereof.
Background technology
The present invention relates to a kind of single sulfonic acid type 1:2 premetallized dye composition and tint applications thereof.
By China's classification, it is (two that 1:2 premetallized dye can be divided into K type (without sulfonic group), S type (single sulfonic group) and M typeSulfonic group) 1:2 premetallized dye. S type (single sulfonic group) 1:2 premetallized dye, compared with another 2 class dyestuffs, hasGood comprehensive quality index, such as level-dyeing property, water-soluble, wet colour fastness etc. This class dyestuff due to synthetic with low cost, dyeThe pollution of look simple process, non-hexavalent chromium, thereby be widely used in the printing and dyeing of the fibers such as silk, wool and polyamide fibre and fabric.
In practice of the present invention, the inventor notices some black S type 1:2 chromium complex dyestuff kinds. These kinds are as thisDye composition shown in invention general formula (1). Its Representative Cultivars is C.I.AcidBlack107 (neutral black BGL) and C.I.AcidBlack168 (neutral black BL). These dye compositions have good dyeability and fastness. But practice shows, is cited as something lostRegret, these dye compositions and of the same type or foreign peoples's type dye kind compatibility is poor, thereby it is numerous greatly to limit its blendingThe tint applications scope of each color and luster.
The inventor, on the basis of lot of experiments research, finds to contain a certain proportion of one or more general formulas (1) table pleasantly surprisedlyThe composition of the dye composition that the dye composition showing and one or more general formulas (2) represent, not only keeps original every excellentDifferent dyefastness, level-dyeing property and water-soluble, and there is good compatibility, particularly it is bathed at nylon/wool blend fibre oneIn dyeing, there is splendid dyeing homochromatism. Thereby expand widely the tint applications scope of dye composite of the present invention.
Summary of the invention
The inventor, on the basis of a large amount of development tests, finds pleasantly surprisedly, the azo group that one or more general formulas (1) representThe groups such as the azo group 1:2 premetallized dye compound that 1:2 premetallized dye compound and one or more general formulas (2) representThe dye composite becoming, has excellent dyeability and dyefastness.
It should be noted that azo group 1:2 premetallized dye composition of the present invention improves and improve the azo that general formula (1) representsCompatibility and the level-dyeing property of base 1:2 premetallized dye compound, thus the latter's tint applications field greatly expanded.
Azo group 1:2 premetallized dye composition provided by the invention, comprise that certain proportion mixes be selected from below shown in logicalThe dye composition that formula (1) represents and be selected from below shown in the dye composition that represents of general formula (2).
In formula:
R1Be selected from hydrogen atom or NHCOCH3Group;
R2And R3Respectively independently selected from H, Cl or NO2Group;
Q is selected from alkali metal cation, is preferably sodium or potassium ion;
In formula:
R4、R5And R6Respectively independently selected from H, Cl or NO2Group;
Q is selected from alkali metal cation, is preferably sodium or potassium ion.
Azo group 1:2 premetallized dye composition provided by the invention, compared with the dyestuff representing with its composition general formula (I),The homochromatism of its nylon/wool blend fabric one-bath process is significantly improved and improves, and its compatibility has also obtained changing significantlyKind, be particularly suitable for the dyeing of responsive colour system, thereby greatly expand the tint applications scope of dye composite of the present invention.
The present invention also provides above-mentioned azo group 1:2 premetallized dye composition to knit in wool fabric, polyamide fabric and blending thereofTint applications on thing.
Specific implementation method
One preferred embodiment in, azo group 1:2 premetallized dye composition of the present invention is by general formula (1) and general formula (2)The dye composition representing forms in certain proportion.
In azo group 1:2 premetallized dye composition of the present invention, the dye composition that general formula (1) represents and general formula (2) tableThe weight ratio of the dye composition showing is 10～60%:90～40%, is preferably 15～55%:85～45%, more preferably 20～50%:50～80％。
One preferred embodiment in, the R in general formula (1)2Group, be positioned at azo group on benzene nucleus between position or contraposition;R in general formula (1)3Group, is positioned at 5 or 6 on naphthalene core; R in general formula (1)1Group, is respectively H or NHOCH3Group.
Another preferred embodiment in, the R in general formula (2)4Group, be positioned at azo group on benzene nucleus between position or contraposition;R in general formula (2)5And R6Group, be separately located in respectively azo group on benzene nucleus between position or contraposition.
In the present invention, the dye composition that general formula (1) represents, for example, comprise following example:
In the present invention, the dye composition that general formula (2) represents, for example, comprise following example:
The azo group 1:2 premetallized dye compound that general formula (1) and general formula (2) represent is all known dye.
The azo group 1:2 premetallized dye compound that general formula (1) represents, its structural formula composition and synthetic method can be consulted followingPaper:
1) Zhang Shanzhong, synthetic [J] dye industry of neutral black BGL (C.I.AcidBlack107), 2000,37 (2): 4-6;
2) Zhang Manli, Zhao Jinyu, neutral black BL synthetic technology report [J] Dandong chemical industry, 1995,4,5-8,12;
The azo group 1:2 premetallized dye compound that general formula (2) represents, its structural formula composition and synthetic method can be consulted followingPaper:
Sun Guichun, synthetic [J] dyestuff and the dyeing 2008,45 (6) of asymmetric 1:2 premetallized dye (C.I. acid blue 3 17): 1-3。
The full content of above-mentioned document is referred in the present invention.
Azo group 1:2 premetallized dye composition of the present invention also can contain various in dyeing and dye formulations routine makeWith dye additive, its consumption can be selected according to actual needs, there is no particular limitation, is generally no more than 20 % by weight. For example,Electrolyte salt, as sodium sulphate or potassium chloride, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as phosphorusAcid dihydride sodium or sodium hydrogen phosphate, content 0～5 % by weight, preferably 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight,Preferably 0.1～2 % by weight; Cosolvent 1～15 % by weight, preferred 0.1～3 % by weight. The present composition also can be substantiallyBy general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff forms or by general formula (1) dyestuff and the general formula of above-mentioned weight ratio(2) dyestuff composition.
The preparation method of azo group 1:2 premetallized dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula(2) dyestuff weight ratio is in accordance with regulations mixed. Mix available various conventional method, as mechanical mixture method. When mixing, logicalFormula (1) dyestuff and general formula (2) dyestuff can powder types, or with particle form, or exist with aqueous solution form. For example,Blend step can suitable grinder as ball mill or needle mill in and in kneader or mixer, carry out.
Azo group 1:2 premetallized dye composition of the present invention can be applied to fiber material by several different methods as known in the artExpect and be fixed on fiber, for example, can dye by dip-dye method or printing method.
Embodiment
Every method of testing of embodiment
The properties of the present embodiment is tested by following every method of testing
1, wool/nylon blend fabric homochromatism test: by proportion of composing 80W/20N, wool/nylon blending of grammes per square metre 600g/m is knittedThing (felt cloth (purchased from Hangzhou Hua Beina company)), after acid dyes normal dyeing technique co-bathing dyeing, to the cloth cover of fabricGrade with chromatic effect, be divided in good and differ from 4 ranks, wherein excellently represent that cloth cover Dry Sack is even, not significantly heterochromaticTrace; Poor expression cloth cover has significant heterochromatic phenomenon.
2, enhancing rate test: nylon knitting fabric is pressed to 98 DEG C of constant temperature dyeings of acid dyes, and dyeing concentration is 0.1%, 0.5%,1%, 2%, 4%o.w.f (dyestuff is to fabric weight). After dyeing, fabric is after constant temperature and humidity is processed, with the survey of Datacolor colour photometerTry its Apparent Depth K/S value record.
3, solubility: take a certain amount of dyestuff in the beaker of 250ml, add the hot water of 100ml80 DEG C, stir with mechanical agitatorMix after 5 minutes and carry out suction filtration (when suction filtration, pressure 0.075Mpa, 5A qualitative filter paper), observe filter paper residual condition. Reduction is dyedMaterial concentration (G/L), until residual without dyestuff on filter paper, dye strength (G/L) is now the solubility of dyestuff.
4, dyeing nylon exhaustion rate test: dye liquor preparation, by the acid dyeing dyeing of nylon. After dyeing finishes, test is dyed respectivelyThe absorbance (MTD 1%o.w.f.) of dye liquor before the absorbance of look raffinate and dyeing.
Exhaustion rate=(absorbance of the front dye liquor of absorbance/dyeing of dye liquor after 1-dyeing) * 100%
6, colour fastness to chlorinated water test: by dyeing nylon fabric, measure by international standard ISO105E03.
7, sunlight fastness test: by dyeing nylon fabric, measure by international standard ISO105-B02.
8, compatibility test: dyestuff of the present invention and Indian yellow and acid red are combined into coffee color, by the acid dyeing dyeing of nylon. ?Sectional sampling in dyeing course, according to the colouring situation of dying each stage in process on whole, dyes the quality of synchronism in judge,Be divided into successively in good and differ from 4 ranks. On whole, dye in process, the form and aspect of each stage sampling do not have obvious difference, onlyBe the difference of the depth, can be assessed as excellent; If there is obvious form and aspect difference, represent that the colouring synchronism of three kinds of dyestuffs is inconsistent,It is poor to be assessed as.
Dye type shown according to the form below 1 and consumption thereof evenly mix various dye components by conventional method in this area, joinThe various acid dye compositions of the embodiment of the present invention processed.
" % " in table 1 all represents % by weight, taking the gross weight of dye composite as benchmark.
Table 1
| Numbering | Dyestuff title | Composition |
| 1 | A | 35% dyestuff 1-1+65% dyestuff 2-1 |
| 2 | B | 20% dyestuff 1-3+80% dyestuff 2-1 |
| 3 | C | 20% dyestuff 1-1+20% dyestuff 1-2+60% dyestuff 2-1 |
| 4 | D | 15% dyestuff 1-3+15% dyestuff 1-5+70% dyestuff 2-1 |
| 5 | E | 25% dyestuff 1-3+25% dyestuff 1-5+50% dyestuff 2-1 |
| 6 | Reference X | Dyestuff 1-1 |
| 7 | Reference Y | Dyestuff 2-1 |
Embodiment 1
The coloured light of azo group 1:2 premetallized dye composition of the present invention
Azo group 1:2 premetallized dye composition of the present invention, the dyestuff representing by fine setting general formula (1) and general formula (2) tableThe ratio of the dyestuff showing, can obtain the dye composite of the color and lusters such as dark navy, pewter, grey black, applicable to dead colorAdjust the dyeing and printing process of the textile of system. The concrete color and luster of the present embodiment dye composite refers to described in following table 2:
Table 2
| Numbering | Dyestuff title | Composition | Color and luster |
| 1 | A | 35% dyestuff 1-1+65% dyestuff 2-1 | Pewter |
| 2 | B | 20% dyestuff 1-3+80% dyestuff 2-1 | Navy blue |
| 3 | C | 20% dyestuff 1-1+20% dyestuff 1-2+60% dyestuff 2-1 | Grey black |
| 4 | D | 15% dyestuff 1-3+15% dyestuff 1-5+70% dyestuff 2-1 | Pewter |
| 5 | E | 25% dyestuff 1-3+25% dyestuff 1-5+50% dyestuff 2-1 | Black |
Embodiment 2
The test of wool/nylon blend fabric homochromatism
Be determined as follows as stated above wool/nylon blend fabric homochromatism, test result is recorded in table 3
Table 3
From table 3:
Azo group 1:2 premetallized dye composition of the present invention is compared compared with reference dyestuff, extremely remarkable with chromatic effect, in this performanceThe significant synergy phenomenon of upper existence.
Embodiment 3
Enhancing rate test (the K/S value at absorbing wavelength 590nm place)
The enhancing rate that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
From table 4:
Azo group 1:2 premetallized dye composition of the present invention, has still kept splendid dyeing enhancing rate.
Embodiment 4
Solubility test
The solubility that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From table 5:
Azo group 1:2 premetallized dye composition of the present invention, has good solubility, and level-dyeing property is better.
Embodiment 5
Dyeing nylon exhaustion rate is measured
The exhaustion rate that is determined as follows as stated above dyestuff, test result is recorded in table 6
Table 6
From table 6:
Azo group 1:2 premetallized dye composition of the present invention has splendid dyeing exhaustion rate.
Embodiment 6
Chlorinated water resist fastness
The colour fastness to chlorinated water that is determined as follows as stated above dyestuff, test result is recorded in table 7
Table 7
From table 7:
Azo group 1:2 premetallized dye composition of the present invention has splendid chlorinated water resist fastness.
Embodiment 7
Sunlight fastness
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 8
Table 8
From table 8:
Azo group 1:2 premetallized dye composition of the present invention has splendid sunlight fastness.
Embodiment 8
Dyeing compatibility test
Measure as stated above dyeing compatibility, test result is recorded in table 9
Table 9
From table 9:
Azo group 1:2 premetallized dye composition of the present invention has splendid dyeing compatibility.
Claims (8)
1. an azo group 1:2 premetallized dye composition, the dyestuff that said composition is represented by one or more general formulas (1)The dye composition that compound and one or more general formulas (2) represent and in dyeing and dye formulations conventional dying of usingFeed additives composition:
In formula:
R1Be selected from hydrogen atom or NHCOCH3Group;
R2And R3Respectively independently selected from H, Cl or NO2Group;
Q is selected from alkali metal;
In formula:
R4、R5And R6Respectively independently selected from H, Cl or NO2Group;
Q is selected from alkali metal.
2. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that, what general formula (1) represented dyesThe weight ratio of the dye composition that material compound and general formula (2) represent is 10～60%:90～40%.
3. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that the R in general formula (1)2Group, be positioned at azo group on benzene nucleus between position or contraposition; R in general formula (1)3Group, is positioned at 5 or 6 on naphthalene corePosition.
4. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that the R in general formula (2)4Group, be positioned at azo group on benzene nucleus between position or contraposition; R in general formula (2)5And R6Group, is separately located in respectively benzenePosition or contraposition between the azo group on core.
5. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that the R in general formula (1)1Group is H.
6. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that, what general formula (1) represented dyesMaterial compound is selected from dye composition as follows:
7. azo group 1:2 premetallized dye composition claimed in claim 1, is characterized in that, what general formula (2) represented dyesMaterial compound is selected from dye composition as follows:
8. in claim 1-7, the azo group 1:2 premetallized dye composition described in any one is knitted at wool fabric, polyamideThing with and the application of blended fabric dyeing aspect.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410409169.2A CN104194385B (en) | 2014-08-19 | 2014-08-19 | A kind of azo group 1:2 premetallized dye composition and tint applications thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410409169.2A CN104194385B (en) | 2014-08-19 | 2014-08-19 | A kind of azo group 1:2 premetallized dye composition and tint applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104194385A CN104194385A (en) | 2014-12-10 |
| CN104194385B true CN104194385B (en) | 2016-05-11 |
Family
ID=52079766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410409169.2A Active CN104194385B (en) | 2014-08-19 | 2014-08-19 | A kind of azo group 1:2 premetallized dye composition and tint applications thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104194385B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104559314B (en) * | 2014-12-12 | 2017-01-25 | 青岛双桃精细化工（集团）有限公司 | Black dye composition and application thereof in polyamide microfiber leather dyeing |
| CN105970688B (en) * | 2016-06-17 | 2018-11-02 | 优纤科技（丹东）有限公司 | A kind of acid bath dyeing method of 56 fabric lining of polyamide fibre |
| CN106433214B (en) * | 2016-10-12 | 2018-04-13 | 苏州科法曼化学有限公司 | Black dye composition and its tint applications and method on fiber |
| CN107841894A (en) * | 2017-10-18 | 2018-03-27 | 马多浩 | A kind of water-based levelling agent of superfine fiber synthetic leather dyeing |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756771A (en) * | 1967-10-09 | 1973-09-04 | Geigy Ag J R | Composite chromium complex azo dyes |
| CN101128545A (en) * | 2005-03-19 | 2008-02-20 | 德意志戴斯达纺织品及染料两合公司 | Metal complex dye mixtures |
| CN102634235A (en) * | 2012-03-27 | 2012-08-15 | 河北永泰柯瑞特化工有限公司 | Neutral dye composition |
| CN103694740A (en) * | 2014-01-13 | 2014-04-02 | 上海雅运纺织化工股份有限公司 | Navy acid dye composition and dyeing application thereof |
-
2014
- 2014-08-19 CN CN201410409169.2A patent/CN104194385B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756771A (en) * | 1967-10-09 | 1973-09-04 | Geigy Ag J R | Composite chromium complex azo dyes |
| CN101128545A (en) * | 2005-03-19 | 2008-02-20 | 德意志戴斯达纺织品及染料两合公司 | Metal complex dye mixtures |
| CN102634235A (en) * | 2012-03-27 | 2012-08-15 | 河北永泰柯瑞特化工有限公司 | Neutral dye composition |
| CN103694740A (en) * | 2014-01-13 | 2014-04-02 | 上海雅运纺织化工股份有限公司 | Navy acid dye composition and dyeing application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 不对称1B2金属络合染料( C.I.酸性蓝317)的合成;孙桂春;《染料与染色》;20081231;第45卷(第6期);第1-3页 * |
| 中性黑BGL(C.I.Acid Black 107)的合成;张善忠;《染料工业》;20001231;第37卷(第2期);第4-6页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104194385A (en) | 2014-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103694740B (en) | Navy acid dye composition and dyeing application thereof | |
| CN104194385B (en) | A kind of azo group 1:2 premetallized dye composition and tint applications thereof | |
| CN104371358B (en) | Disperse dye composition and disperse dye and preparation method and use thereof | |
| CN106479221B (en) | It is a kind of dark blue to black disperse dye mixture | |
| CN101125966A (en) | Composite reactive black dye used for cellulose fibre coloring | |
| CN104356688B (en) | A kind of yellow disperse dye composition and its production and use | |
| CN103740135B (en) | A kind of low-temperature environment-friendly type disperse yellow dye composition | |
| CN102485802B (en) | Navy blue reactive dye composition and its application in fiber dyeing | |
| CN105985663A (en) | Black acid dye composition and dyeing application thereof | |
| CN110128848A (en) | A kind of carmoisine composition and its tint applications on fiber | |
| CN103709787A (en) | Azo type disperse dye composition synthesis method | |
| CN104592788B (en) | A kind of blue disperse dye composition of stamp | |
| CN106928749B (en) | A kind of disperse dye composition, disperse dyes and its preparation method and purposes | |
| CN101007907A (en) | High humidity treatment fastness dispersible dye mixture and its product | |
| CN105504875A (en) | Double-face leather dye and preparation method thereof | |
| CN101983999A (en) | Compound disperse blue dye for direct printing | |
| CN105385191B (en) | Water-soluble dye composition and its tint applications | |
| CN108276801A (en) | A kind of disperse dye composition and its application | |
| CN104371363A (en) | Yellow disperse dye and preparation method and use thereof | |
| CN104371369B (en) | Disperse dye composition and disperse dye, and preparation method and use thereof | |
| CN102634230B (en) | Red 1:2 chromium-complexed acidic dye composition, and synthesis and dyeing application thereof | |
| CN103275519B (en) | Yellow acid dye composition and dyeing application thereof | |
| CN104371364B (en) | Disperse dye composition and disperse dye, and preparation method and use thereof | |
| CN107778919A (en) | A kind of less C.I. Red 167s dyestuff substitute of metameric index | |
| CN106349753A (en) | Novel disperse dye composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220809 Address after: No.388, Jinyuan 6th Road, Jiading District, Shanghai, 201812 Patentee after: ARGUS (SHANGHAI) TEXTILE AUXILIARY Co.,Ltd. Address before: Room 275-278, Building 16, No. 388, Yindu Road, Xuhui District, Shanghai, 200231 Patentee before: SHANGHAI ARGUS TEXTILE CHEMICAL Co.,Ltd. |