CN103275519B - Yellow acid dye composition and dyeing application thereof - Google Patents

Yellow acid dye composition and dyeing application thereof Download PDF

Info

Publication number
CN103275519B
CN103275519B CN201310221877.9A CN201310221877A CN103275519B CN 103275519 B CN103275519 B CN 103275519B CN 201310221877 A CN201310221877 A CN 201310221877A CN 103275519 B CN103275519 B CN 103275519B
Authority
CN
China
Prior art keywords
dye composition
general formula
yellow acid
acid dye
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
Application number
CN201310221877.9A
Other languages
Chinese (zh)
Other versions
CN103275519A (en
Inventor
曾建平
谢兵
郑怡华
徐田刚
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SHANGHAI ARGUS TEXTILE CHEMICAL CO Ltd
Original Assignee
SHANGHAI ARGUS TEXTILE CHEMICAL CO Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SHANGHAI ARGUS TEXTILE CHEMICAL CO Ltd filed Critical SHANGHAI ARGUS TEXTILE CHEMICAL CO Ltd
Priority to CN201310221877.9A priority Critical patent/CN103275519B/en
Publication of CN103275519A publication Critical patent/CN103275519A/en
Application granted granted Critical
Publication of CN103275519B publication Critical patent/CN103275519B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Coloring (AREA)

Abstract

The invention provides a yellow acid dye composition used for wool, polyarmide fibers and fabrics, and a dyeing application thereof. The yellow acid dye composition comprises the following two known dyes of a yellow acid dye and a yellow 1:2 metal complex dye. The yellow acid dye composition can play a synergetic effect with significant improvement of any single dye compound as well as take various dyeing quality indexes such as brightness, solubility, dye uptake, compatibility, levelness and various fastnesses. A general formula (1) and a general formula (2) are shown in the specification.

Description

Yellow acid dye composition and tint applications thereof
Technical field
The present invention relates to a kind of acid dye composition.Particularly, the present invention relates to a kind of yellow acid dye composition and tint applications thereof being formed by matching stain and neutral dye.
Background technology
The present invention is intended to develop a kind of yellow acid dye composition for wool, tynex and fabric.
For a long time, for the yellow matching stain of wool, tynex and fabric be one of the focus of dyestuff circle research and development always.This is because compared with the yellow matching stain of current use and the dyestuff of other color and luster, there is many defects and deficiency, suddenly waits to improve.Be mainly manifested in vividness, the aspects such as every fastness, solubleness, dye uptake and level-dyeing property dye.Particularly, for yellow color and luster, the consistency of vividness and other color and luster blendings is again the distinctive important indicator of yellow matching stain.Practice shows, takes into account above-mentioned numerous every dyeing quality index, should be the direction and goal that the present invention researchs and develops.
The inventor under study for action, by lot of experiments, notices a kind of yellow neutral dye.This dyestuff is 1:2 chromium complex dyestuff, is represented by general formula (1).The structural formula of its Representative Cultivars is as follows:
Figure BDA00003305539000011
In formula:
R 1for H, Cl, CH 3or OCH 3;
R 1for H, Cl, CH 3or OCH 3;
R 1for H, Cl, CH 3or OCH 3;
Q +for alkali metal cation
This dye composition and derivative thereof synthetic as far back as last century the fifties announced by following patent.
US2681338（1954）（ICI）
US2832762（1958）（Ciba）
GB819314（1959）（Geigy）
GB823393（1959）（Badische?Anilin&Soda-Fabrik）
US2921061（1960）（Geigy）
In state-owned many dyestuff enterprise produce in a large number this class dyestuff.
This class dyestuff is well good at level-dyeing property and fastness.But the deficiency that also has the aspects such as vividness, solubleness, depth, has a strong impact on it and applies.
The inventor passes through lot of experiments, find pleasantly surprisedly, the dye composition that general formula (2) is represented adds the yellow acid dye composition of the dye composition composition of general formula (1) expression, take into account above-mentioned numerous every dyeing index, the feature such as have that coloured light is bright-coloured, dyefastness is excellent, depth, consistency, dye uptake are good, can meet the day by day harsh demand of current printing and dyeing.
The Representative Cultivars of the dye composition that general formula (2) represents, its structural formula is as follows:
Figure BDA00003305539000021
In formula:
R 4for H, Cl or CH 3;
M is alkalimetal ion.
This dye species as far back as earlier 1800s by U.S. Pat 791524(1905) (Hugo Witter) announce.China Duo Jia dyestuff enterprise is still in a large amount of production.
The inventor tests confirmation by extensive application, two components of the yellow acid dye composition of the present invention, and its dyeing behavior mutual is augmented, and reaches the effect of mutual synergy.
Current for restriction metallized dye dyeing waste liquid metallic pollution, require dyestuff dye uptake should reach 93%.The yellow acid dye composition of the present invention, the ratio of attenuating metallized dye, meets the strict demand of current environmental protection.
The inventor is there are no the patent of same or similar content of the present invention and delivering and announcing of document.
Inventor's confirmation, the present invention has broad application prospects.
Summary of the invention
The inventor is on the basis of a large amount of research trials, find pleasantly surprisedly, the yellow acid dye composition of one or more matching stains that one or more metallized acid dyes that comprise general formula (1) expression and general formula (2) represent, has very excellent dyeing behavior and every fastness.
The matching stain that the metallized acid dye that general formula (1) represents and general formula (2) represent is all mass-produced ancient kind still, the yellow acid dye composition of the present invention makes two kinds of complementary synergy of ancient dye species, again radiate the vigour of youth, meet the day by day harsh demand of current printing and dyeing.
The yellow acid dye composition of the present invention, takes into account numerous every dyeing quality indexs, the dyeing behavioies such as such as vividness, consistency, depth, level-dyeing property, dye uptake.
The yellow acid dye composition of the present invention, the dye composition that the dye composition that the general formula (1) of one or more that mix containing certain proportion shown in being selected from below represents and one or more general formula (2) shown in being selected from below represents.
Figure BDA00003305539000031
In formula:
R 1for H, Cl, C 1-3alkyl or C 1-3alkoxyl group, as CH 3or OCH 3;
R 2for H, Cl, C 1-3alkyl or C 1-3alkoxyl group, as CH 3or OCH 3;
R 3for H, Cl, C 1-3alkyl or C 1-3alkoxyl group, as CH 3or OCH 3;
Q +for alkali metal cation,, as potassium or sodium ion;
In formula:
R 4for H, Cl, C 1-3alkyl or C 1-3alkoxyl group, as CH 3or OCH 3;
M is alkalimetal ion, as potassium or sodium ion.
The application of yellow acid dye composition provided by the invention in wool, tynex and textile dyeing.
The present invention should have broad application prospects.
Specific implementation method
Yellow acid dye composition of the present invention comprises the dyestuff of one or more general formulas (1) expression and the dyestuff that one or more general formulas (2) represent.
In yellow acid dye composition of the present invention, the weight ratio of the dyestuff that the dyestuff that general formula (1) represents and general formula (2) represent is 90～40:10～60; Be preferably 80～50:20～50.
One preferred embodiment in, the R in general formula (1) 1and R 2group, contraposition, a position and the ortho position of be separately located in respectively on phenyl ring-N=N-group.
Another preferred embodiment in, the R in general formula (1) 3group, is positioned on phenyl ring
Figure BDA00003305539000042
contraposition, a position or the ortho position of group.
One preferred embodiment in, the R in general formula (2) 4group, is positioned on phenyl ring contraposition, a position or the ortho position of group.
Another preferred embodiment in, the following groups of general formula (1) and general formula (2):
R 1, R 2and R 3for H, Cl, CH 3or OCH 3;
R 4for H, Cl, CH 3or OCH 3;
M is alkalimetal ion, as potassium or sodium ion;
Q +for alkali metal cation, as potassium or sodium ion.
The dyestuff that general formula of the present invention (1) represents, for example, comprise following example:
Figure BDA00003305539000051
Figure BDA00003305539000052
Figure BDA00003305539000061
Figure BDA00003305539000071
Figure BDA00003305539000072
Figure BDA00003305539000081
Figure BDA00003305539000082
The dyestuff that general formula of the present invention (2) represents, for example, comprise following example:
Figure BDA00003305539000083
Figure BDA00003305539000091
The dye composition that general formula (1) represents is known dye.
Its Representative Cultivars C.I. acid yellow 59, can be buied by market.
The synthetic of its derivative can be consulted following patent:
US2681338（1954）（ICI）
US2832762（1958）（Ciba）
GB819314（1959）（Geigy）
GB823393（1959）（Badische?Anilin&Soda-Fabrik）
US2921061（1960）（Geigy）
The dye composition that general formula (2) represents is also known dye.
Its Representative Cultivars C.I. turmeric yellow 42, can be buied by market.
It synthesizes can consult following patent:
US791524（1905）（Hugo?Witter）
Yellow acid dye composition of the present invention also can contain the dye additive of various conventional uses in dyeing and dye formulations, and its consumption can be selected according to actual needs, and there is no particular limitation, is generally no more than 20 % by weight.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 % by weight, preferably 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight, preferred 0.1～2 % by weight; Solubility promoter 1～15 % by weight, preferred 0.1～3 % by weight.The present composition also can be substantially by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff forms or be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of yellow acid 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 ordinary method, as mechanically mixing method.When mixing, general formula (1) dyestuff and general formula (2) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Yellow acid dye composition of the present invention can be applied to filamentary material and be fixed on fiber by several different methods as known in the art, for example, can dye by dip-dye method or printing method.
Embodiment
Every testing method of embodiment
The properties of the present embodiment is tested by following every testing method
1, solubleness: take a certain amount of dyestuff in the beaker of 250ml, add the hot water of 100ml80 ℃, carry out suction filtration (when suction filtration, pressure 0.075Mpa, 5A qualitative filter paper) with mechanical stirrer stirring after 5 minutes, observe filter paper residual condition.Reduce dye strength (G/L), until residual without dyestuff on filter paper, dye strength (G/L) is now the solubleness of dyestuff.
2, woolen dyed exhaustion rate test: dye liquor preparation, by the acid dyeing dyeing of wool.After dyeing finishes, test respectively the absorbancy of dyeing residual liquid and the absorbance of the front dye liquor of dyeing.
Exhaustion rate=(absorbance of the front dye liquor of absorbance/dyeing of dye liquor after 1-dyeing) * 100%
3, migration property test: by dyeing cloth specimen and equal size, the cloth specimen surrounding stitching of being unstained that shape is consistent, put into the blank solution that is added with auxiliary agent, buffered soln but there is no dyestuff, dye according to common process.Test moves the power part of dying rear calico Dry Sack and accounting for former stained cloth, and it more than 60% is outstanding that migration property reaches, and it is 30% poor to be less than.
4, colour fastness to chlorinated water test: by dyeing nylon fabric, measure by international standard ISO105E03.
5, colour fastness to perspiration test: by dyeing nylon fabric, measure by international standard ISO105-E04.
6, fastness to soaping test: by dyeing nylon fabric, measure by international standard ISO105-C10.
7, resistance to DC processes look change: by the fabric of using after dyeing of the present invention, after processing, observe look and become big or small by DC treatment process, what look diminished is excellent.
DC treatment process: treatment solution Basolan DC5%o.w.f.; Woolen dyed fabric is put into treatment solution in 25～30 ℃, be incubated 15 minutes, be warming up to 35 ℃, add trisodium phosphate 5%o.w.f., insulation 20min, takes out clear water and cleans, dries, and the grading of ash card, is preferably 5 grades, and the poorest is 1 grade.
Dye type shown according to the form below 1 and consumption thereof evenly mix various dye components by ordinary method in this area, the various yellow acid dye composition of the preparation embodiment of the present invention.
" % " in table 3 all represents % by weight, take the gross weight of dye composite as benchmark.
Table 1
Numbering Dyestuff title Composition
1 A 80% dyestuff 1-1+20% dyestuff 2-1
2 B 70% dyestuff 1-1+30% dyestuff 2-1
3 C 50% dyestuff 1-1+50% dyestuff 2-1
4 D 80% dyestuff 1-2+20% dyestuff 2-3
5 E 70% dyestuff 1-2+30% dyestuff 2-3
6 F 50% dyestuff 1-2+50% dyestuff 2-3
7 Reference X 100% dyestuff 1-1
8 Reference Y 100% dyestuff 2-1
9 Reference M 100% dyestuff 1-2
10 Reference N 100% dyestuff 2-3
Embodiment 1
The coloured light of the yellow acid dye composition of the present invention
The yellow acid dye composition of the present invention can obtain the coloured light of bright-coloured lemon yellow, and the gorgeous yellow dyes of the present invention can be effectively uses with together with sapphire blue, bright blue dyestuff with deep red, obtains the textiles of bright-coloured beautiful various color and lusters in printing and dyeing.
Embodiment 2
Solubleness test
The solubleness that is determined as follows as stated above dyestuff, test result is recorded in table 1
Table 1
Figure BDA00003305539000121
From table 1:
The yellow acid dye composition of the present invention, still has good solubleness, and level-dyeing property is better.
Embodiment 3
Woolen dyed exhaustion rate is measured
The exhaustion rate that is determined as follows as stated above dyestuff, test result is recorded in table 2
Table 2
Figure BDA00003305539000122
Figure BDA00003305539000131
From table 2:
The yellow acid dye composition of the present invention there is splendid dyeing exhaustion rate.
Embodiment 4
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 3
Table 3
From table 3:
The yellow acid dye composition of the present invention still has good chlorinated water resist fastness.
Embodiment 5
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
Figure BDA00003305539000141
From table 4:
The yellow acid dye composition of the present invention has improved the poor defect of dyestuff perspiration fastness that general formula (2) represents effectively.。
Embodiment 6
Fastness to soaping
The fastness to soaping that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
Figure BDA00003305539000151
From table 5:
The present invention yellow acid dye composition has improved dyestuff that general formula (2) the represents poor defect of soaping effectively.
Embodiment 7
Resistance to DC processes look and becomes
The resistance to DC that is determined as follows as stated above dyestuff processes look and becomes, and test result is recorded in table 6
Table 6
From table 6:
The yellow acid dye composition of the present invention still has excellent resistance to DC and processes look sex change energy.

Claims (10)

1. a yellow acid dye composition, the dye composition that the dye composition that it contains at least one general formula (1) expression and at least one general formula (2) represent.
In formula:
R 1for H, Cl, C 1-3alkyl or C 1-3alkoxyl group;
R 2for H, Cl, C 1-3alkyl or C 1-3alkoxyl group;
R 3for H, Cl, C 1-3alkyl or C 1-3alkoxyl group;
Q +for alkali metal cation
Figure FDA0000434090830000012
In formula:
R 4for H, Cl, C 1-3alkyl or C 1-3alkoxyl group;
M is alkalimetal ion.
2. yellow acid dye composition claimed in claim 1, is characterized in that, the weight ratio of the dye composition that the dye composition that said composition formula of (1) represents and general formula (2) represent is 90～40:10～60.
3. yellow acid dye composition claimed in claim 1, is characterized in that, the R in general formula (1) 1and R 2group, contraposition, a position and the ortho position of be separately located in respectively on phenyl ring-N=N-group.
4. yellow acid dye composition claimed in claim 1, is characterized in that, the R in general formula (1) 3group, is positioned on phenyl ring
Figure FDA0000434090830000021
contraposition, a position or the ortho position of group.
5. yellow acid dye composition claimed in claim 1, is characterized in that, the R in general formula (2) 4group, is positioned on phenyl ring
Figure FDA0000434090830000022
contraposition, a position or the ortho position of group.
6. yellow acid dye composition claimed in claim 1, is characterized in that, the dye composition that general formula (1) represents is that the dye composition and the chromic salts complex reaction that are represented by general formula (3) make;
Figure FDA0000434090830000023
In formula: R 1, R 2and R 3in the same general formula of group (1), represent.
7. yellow acid dye composition claimed in claim 1, is characterized in that, the dye composition that general formula (1) represents comprises:
Figure FDA0000434090830000031
Figure FDA0000434090830000041
Figure FDA0000434090830000051
Figure FDA0000434090830000061
8. yellow acid dye composition claimed in claim 1, is characterized in that, the dye composition that general formula (2) represents comprises:
Figure FDA0000434090830000062
9. yellow acid dye composition claimed in claim 2, is characterized in that, the weight ratio of the dye composition that the dye composition that said composition formula of (1) represents and general formula (2) represent is 80～50:20～50.
10. the application of the yellow acid dye composition described in any one aspect the dyeing of protein fibre and tynex and BLENDED FABRIC thereof in claim 1～9.
CN201310221877.9A 2013-06-05 2013-06-05 Yellow acid dye composition and dyeing application thereof Active CN103275519B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201310221877.9A CN103275519B (en) 2013-06-05 2013-06-05 Yellow acid dye composition and dyeing application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201310221877.9A CN103275519B (en) 2013-06-05 2013-06-05 Yellow acid dye composition and dyeing application thereof

Publications (2)

Publication Number Publication Date
CN103275519A CN103275519A (en) 2013-09-04
CN103275519B true CN103275519B (en) 2014-05-14

Family

ID=49058152

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201310221877.9A Active CN103275519B (en) 2013-06-05 2013-06-05 Yellow acid dye composition and dyeing application thereof

Country Status (1)

Country Link
CN (1) CN103275519B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128849B (en) * 2019-05-18 2020-08-21 上海雅运纺织化工股份有限公司 Yellow acid dye composition and dyeing application thereof on fibers

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2652071B2 (en) * 1990-01-25 1997-09-10 日本化薬株式会社 Color filter
JPH11281813A (en) * 1998-03-30 1999-10-15 Sony Corp Manufacture of color filter for solid image pickup element
JP2005055585A (en) * 2003-08-01 2005-03-03 Fuji Photo Film Co Ltd Dye-containing negative type curing composition, color filter, and manufacturing method therefor
JP4883299B2 (en) * 2004-10-14 2012-02-22 日産化学工業株式会社 Resist composition containing organic solvent-soluble dye and color filter using the same
DE102005012730A1 (en) * 2005-03-19 2006-09-21 Dystar Textilfarben Gmbh & Co. Deutschland Kg Metal complex dye mixtures
CN100384945C (en) * 2006-01-16 2008-04-30 大连理工大学 Acid dye composition
CN102796400B (en) * 2011-05-25 2013-12-04 上海雅运纺织化工股份有限公司 Yellow azo metallized dye composition, method and application thereof

Also Published As

Publication number Publication date
CN103275519A (en) 2013-09-04

Similar Documents

Publication Publication Date Title
CN102585553B (en) Navy-blue reactive dye composition and dyeing application thereof
CN103694740B (en) Navy acid dye composition and dyeing application thereof
CN101368008B (en) Navy blue reactive dye composition and dyeing uses in fibrous material thereof
CN102115613B (en) Blue reactive dye composition and dyeing application to fiber material thereof
CN101323709B (en) Red reactive dye composition and dyeing application thereof to fibre material
CN106479223B (en) Yellow active dye composition and its tint applications and method on fiber
KR101871556B1 (en) Acid dye composition,and dyeing method using same
CN101457032B (en) Dark blue reactive dye composition for cotton and dyeing use thereof
CN102504593B (en) Blue dye composition and use thereof for fiber dyeing
CN104194385B (en) A kind of azo group 1:2 premetallized dye composition and tint applications thereof
CN101440227B (en) Yellow reactive dye composition and use thereof
CN102485802B (en) Navy blue reactive dye composition and its application in fiber dyeing
CN106433215B (en) Red dye composition and its tint applications and method on fiber
CN103275519B (en) Yellow acid dye composition and dyeing application thereof
CN102115612B (en) Dark blue active dye composition and application thereof in dyeing fibers
CN103554993B (en) Red reactive dye composition and the tint applications on fiber thereof
CN101323710A (en) Red reactive dye composition and dyeing application thereof
CN103952013B (en) A kind of compound reactive brilliant blue K-GR composition and use thereof and using method
CN102807773B (en) Blue dye composition, and dyeing application of blue dye composition on fiber
CN102304299A (en) Tricolor reactive dye composition and application thereof in dyeing fibers
CN102311668B (en) Blue reactive dye composition and dying application thereof on fiber
CN101418138B (en) Navy blue reactive dyes composite for low salt dyeing and dyeing application thereof
TWI736794B (en) Reactive dye composition and dyeing method using the same
CN102766355B (en) Anthraquinone blue dye composition and dyeing applications of same to fibers
CN102634230B (en) Red 1:2 chromium-complexed acidic dye composition, and synthesis and dyeing application thereof

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