CN102206427B - Yellow reactive dye composition and its application in dyeing of fiber - Google Patents
Yellow reactive dye composition and its application in dyeing of fiber Download PDFInfo
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- CN102206427B CN102206427B CN 201010136853 CN201010136853A CN102206427B CN 102206427 B CN102206427 B CN 102206427B CN 201010136853 CN201010136853 CN 201010136853 CN 201010136853 A CN201010136853 A CN 201010136853A CN 102206427 B CN102206427 B CN 102206427B
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Abstract
The invention provides a yellow reactive dye composition and its application in dyeing of fibers. The reactive dye composition comprises one dye compound or a plurality of dye compounds represented by general formula (1) and one dye compound or a plurality of dye compounds represented by general formula (2). The yellow reactive dye composition provided in the invention has excellent dyeing performance, photosensitivity, color fastness under various conditions and compatibility to dyeing together with widely-used red and blue reactive dyes. All the substituents in the general formula (1) and (2) are as described in the specification.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and the tint applications on filamentary material thereof, particularly relate to Yellow active dye composition and the tint applications on filamentary material thereof.
Background technology
The exploitation of the new Yellow active dye with excellent dyeing behavior and dyefastness is the important topic of current dyestuff worker research always, and this is because the kind of current Yellow active dye is difficult to satisfy overcritical day by day printing and dyeing requirement.Compare with other color and luster dyestuff, the coloured light of Yellow active dye, fastness, dyeing behavior, thermo-sensitive property and photochromic properties all have higher requirement.These impel the dyestuff worker constantly to explore, the Yellow active dye kind that development research is new.
Noticeablely be that the US 2002/0069469 (2002) that Ciba SC company delivers, US 6504014 (2003) patents disclose the synthetic method of the new Yellow active dye kind of a class.This veriety adopts the aliphatic chain active group, and its demonstration structure formula is as follows:
Ciba SC company delivers US 2003/0097721 (2003), US 2005/0235435 (2005), US6 in succession later on, 930,179 (2005), US 2007/0130703 (2007) patent discloses the Yellow active dye that adopts above-mentioned similar structures is used for polyamide fabric as one of dye component dyeing.
Korea S Kyung In Synthetic Corp. and Korea S SungYong Cho etc. deliver CN 1810891 (2006), US 2006/0185103 (2006) patent in succession, disclose the component of the three-color combination novel reactive dye composition of being developed.The yellow color component of said composition adopts following similar structures:
Summary of the invention
The inventor carries out finding after a large amount of experimental studies that above-mentioned Yellow active dye has good every dyefastness and higher enhancing rate to above-mentioned yellow dyes kind.But dye shade is darker regrettably, and bright-coloured inadequately, cost of dye is higher, and level-dyeing property also remains further to be improved.
The inventor finds that pleasantly surprisedly the dyeing behavior that the dyestuff and the above-mentioned dyestuff of general formula (2) expression are pieced together the Yellow active dye composition that mixes gained all has improvement largely, and it is bright and beautiful that dye shade is tending towards, and cost reduces.Be that the photochromic properties of two kinds of Yellow active dye compositions reaches complementary, reaches perfection particularly pleasantly surprisedly.
The dyestuff demonstration structural formula of general formula (2) expression is as follows:
Above-mentioned dyestuff is the derived varieties of Yellow active dye C.I.Reactive 145.The SUMITOMO CHEMICAL company patent that the eighties is delivered last century, US 4378313 (1993), and JP 60215065 (1985) discloses the structure and the synthetic method thereof of this class dyestuff.
The inventor passes through great deal of experimental, the dye composite that one or more Yellow active dyes that are surprised to find general formula (1) expression and one or more Yellow active dyes that general formula (2) is represented are formed has very excellent dyeing behavior and every fastness.
Yellow active dye composition provided by the invention comprise the certain proportion blended one or more be selected from below shown in the dyestuff of general formula (1) expression and one or more be selected from below shown in the dyestuff of general formula (2) expression:
In the formula:
Y
1For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or basic metal;
R
1, R
2, R
3And R
4Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group, halogen, sulfo group, urea groups and carboxyl;
R
5And R
6Be H, replacement or unsubstituted C independently respectively
1-C
4Alkyl;
R
7And R
8Be H, sulfo group, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group and halogen;
M is 2 or 3;
X
1Be Cl or F;
In the formula:
Y
2For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or basic metal;
R
9And R
10Be H, replacement or unsubstituted C independently respectively
1-C
4Alkyl;
R
11And R
12Be H, sulfo group, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group and halogen;
N is 2 or 3;
X
2Be Cl or F.
The present invention also provides the tint applications of above-mentioned Yellow active dye composition on cellulosic fibre material.
Embodiment
Comprise the dyestuff of one or more general formulas (1) expression and the dyestuff of one or more general formulas (2) expression in the dye composite of the present invention.
In the dye composite of the present invention, the dyestuff of general formula (1) expression (being called for short dyestuff I) is 90-10: 10-90, preferably 80-20: 20-80 with the weight ratio of the dyestuff (being called for short dyestuff II) of general formula (2) expression.
One preferred embodiment in, general formula (1) left side-SO
3The M group when m=2, is positioned at 4,8 or 1,5 or 3,6 of naphthalene nucleus; Or be positioned on the benzene nucleus-ortho position and a position of N=N-azo group; When m=3, then be positioned at 3,6,8 or 4,6,8 of naphthalene nucleus.
Another preferred embodiment in, general formula (2) left side-SO
3The M group when n=2, is positioned at 4,8 or 1,5 or 3,6 of naphthalene nucleus; When n=3, then be positioned at 3,6,8 or 4,6,8 of naphthalene nucleus.One preferred embodiment in, general formula (1) right side-SO
2Y
1Group is positioned on the benzene nucleus
The contraposition of group or a position; General formula (1) right side-R
7Group and-R
8Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position.
Another preferred embodiment in, general formula (2) right side-SO
2Y
2Group is positioned on the phenyl ring
The contraposition of group or a position; General formula (2) right side-R
11Group and-R
12On group is separately located on the phenyl ring respectively
The contraposition of group, a position or ortho position.
One preferred embodiment in, general formula (2) middle part-SO
3The M group is positioned at 5 of naphthalene nucleus, 6 or 7.
Another preferred embodiment in, in general formula (1) and the general formula (2),
M is 2;
N is 2;
X
1And X
2Be Cl independently respectively.
One preferred embodiment in, above-mentioned basic metal comprises lithium, sodium or potassium, is preferably sodium or potassium.Halogen comprises fluorine, chlorine, bromine or iodine, is preferably chlorine or bromine.
The dyestuff of formula of of the present invention (1) expression for example comprises following example:
The dyestuff of formula of of the present invention (2) expression for example comprises following example:
The reactive dyestuffs of general formula (1) and general formula (2) expression are known dye
US?6,504,016(2003)(Ciba?SC)
US?2002/0069469(Ciba?SC)
CN 1810891 (2006) (Kyung In Synthetic Corp.)
Structure and the derived structure and the method for making thereof of the reactive dyestuffs of general formula (1) expression have been announced.
US 4,378,313 (1983) (Sumitomos)
JP 60-215065 (1985) (Sumitomo)
The reactive dyestuffs structure and the method for making of general formula (2) expression have been announced.
Yellow active 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 by actual needs, and there is no particular limitation, generally is no more than 20 weight %.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 weight %, preferred 2～6 weight %; The pH regulator agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 weight %, preferred 0.5～2.5 weight %, dust-proofing agent 0～10 weight %, preferred 0.1～2 weight %; Solubility promoter 1～15 weight %, preferred 0.1～3 weight %.The present composition also can be basically by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff is formed or be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of Yellow active 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 the mechanically mixing method.During 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 carry out in suitable shredder such as ball mill or needle mill and in kneader or mixing machine.
Yellow active dye composition of the present invention is suitable for dyeing and various widely material thereof, the material that particularly contains carboxylic acid and/or formamido-, filamentary material more especially, for example cotton, flax and hemp fibre, and Mierocrystalline cellulose and regenerated cellulose, polyester or polyamide fiber material etc.
Yellow active dye composition of the present invention can be applied to filamentary material and is fixed on the fiber with several different methods as known in the art, for example can dye with dip-dye method or pad dyeing method.
Embodiment
Every testing method of embodiment
Every performance of present embodiment is tested by following every testing method
1, enhancing rate test: pure cotton fabric is pressed 60 ℃ of constant temperature technology dyeing of reactive dyestuffs, and dyeing concentration is 0.5%, 1%, 2%, 4%, 6%o.w.f (dyestuff is heavy to fabric).Dyeing back fabric is tested its Apparent Depth K/S value and record with the Datacolor color measurement instrument after fixed temperature and humidity is handled.
2, degree of fixation test: the dye liquor preparation, press 60 ℃ of constant temperature technology dyeing of reactive dyestuffs.Preparation A, B two identical dye liquors only add cloth specimen in the B dye liquor, dyeing is carried out washing according to the following steps with the cloth specimen in the B dye bath after finishing, and with dyeing residual liquid, and the washing raffinate of each step concentrates on constant volume in the volumetric flask of a 500mL.When B dye bath cloth specimen carried out soap boiling, the detergent that also adds same amount in the A dye bath carried out soap boiling.The A dye bath is soaped and is finished postcooling to room temperature, and constant volume is 500mL.A behind the constant volume, B dyeing residual liquid are diluted to certain multiple MA, MB, test absorptance values XA, the XB of its diluent when maximum absorption wavelength (XA, XB should between 0.2～0.7).
The * 100% of degree of fixation=(1-XBMB/XAMA)
3, just dye the test of rate and degree of exhaustion: the dye liquor preparation, press 60 ℃ of constant temperature technology dyeing of reactive dyestuffs.Respectively before adding alkali and on dye and finish to take a sample before the soap boiling, measure the absorbance of dyeing residual liquid, with dye liquor absorbance before the dyeing relatively.
Just dye rate=(1-adds the absorbance of the preceding dye liquor of absorbance/dyeing of the preceding dye liquor of alkali) * 100%
Degree of exhaustion=(1-soap before the absorbance of the preceding dye liquor of absorbance/dyeing of dye liquor) * 100%
4, photochromic properties test: the fabric after will dyeing is behind light fastness tester illumination certain hour (intensity of illumination is with reference to IOS105-B05), and the data before and after the test fabric illumination are judged photochromic power according to the total color difference DE in the CIE formula.The DE value is more little, represents photochromic more little.
5, move the test of staining index MI value: two onesize A, B cloth specimen input are added with in the dye bath of dyestuff, sodium sulfate, behind 60 ℃ of dyeing 30min, take out the B cloth specimen, the B cloth specimen is put in the blank dye bath that only contains sodium sulfate, put into onesize calico C simultaneously, continue to add yellow soda ash fixation 60min behind dyeing (move and dye) 20min.The apparent dye yield (K/S) that compares B cloth specimen and C cloth specimen.
Move apparent dye yield (K/S) * 1000% of apparent dye yield (the K/S)/B cloth specimen of staining index MI=C cloth specimen
6, colour fastness to perspiration test: measure by international standard ISO 105-E04.
7, fastness to soaping test: measure by international standard ISO 105-C10.
8, color fastness to water test: measure by international standard ISO 105-E01.
9, color fastness to sea water test: measure by international standard ISO 105-E02.
10, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
11, the photochromic fastness test of sweat proof: measure by Japanese standard JIS L0888.
Dye type shown in the according to the form below 1 and consumption thereof by ordinary method uniform mixing in this area, are prepared the various Yellow active dye compositions of the embodiment of the invention with various dye components.
" % " in the table 1 all represents weight %, is benchmark with the gross weight of dye composite.
Table 1
Embodiment 1
The coloured light of Yellow active dye composition of the present invention
The dyestuff color and luster of general formula (I) expression is dark yellow, and the dyestuff color and luster of general formula (II) expression is bright-coloured golden yellow.The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (I) dyestuff and general formula (II) dyestuff as required, obtains different coloured light, is recorded in table 2
Table 2
The coloured light of Yellow active dye composition of the present invention can be adjusted the ratio of general formula (I) dyestuff and general formula (II) dyestuff as required, improve the dark partially deficiency of dyestuff color and luster of general formula (1) expression, and its cost of reduction that can be bigger, thereby make mixture constitute the three primary colors combination with other redness, blue dyes effectively, improve its actual application value.
Embodiment 3
Enhancing rate test (the K/S value at absorbing wavelength 430nm place)
Measure the enhancing rate of following dyestuff as stated above, test result is recorded in the table 3
Table 3
By table 3 as seen:
The enhancing rate measured value of Yellow active dye composition of the present invention is much higher than the weighted mean that it forms dyestuff, has embodied the effect of compound synergic.
Embodiment 4
Just dying rate and degree of exhaustion measures
Measure the first rate and the degree of exhaustion of dying of following dyestuff as stated above, test result is recorded in the table 4
Table 4
By table 4 as seen:
1) the Yellow active dye composition of the present invention reactive dyestuffs that improved general formula (1) expression greatly just dye the too high shortcoming of rate, have improved level-dyeing property, show and conventional primary colors red, blue dyestuff good consistency when dying;
2) the first rate and the degree of exhaustion measured value of dying of Yellow active dye composition of the present invention all is higher than the weighted mean that it forms dyestuff, illustrates that dye composite has better dyeing capacity, helps the set of dyestuff.
Embodiment 5
Degree of fixation is measured
Measure the degree of fixation of following dyestuff as stated above, test result is recorded in the table 5
Table 5
By table 5 as seen:
The degree of fixation measured value of Yellow active dye composition of the present invention apparently higher than its weighted mean of forming dyestuff, has embodied the effect of compound synergic, and Yellow active dye composition of the present invention has preferable degree of fixation.
Embodiment 6
Photochromism is measured
Measure the photochromic properties of following dyestuff as stated above, test result is recorded in the table 6
Table 6
By table 6 as seen:
Yellow active dye composition of the present invention is compared with the reactive dyestuffs of general formula (2) expression with general formula (1), and the DE value is littler, represents that its photochromism is littler, has embodied the characteristics of compound synergic.
Embodiment 7
Moving staining index measures
Measure the staining index that moves of following dyestuff as stated above, test result is recorded in the table 7
Table 7
By table 7 as seen:
Yellow active dye composition of the present invention has improved the shortcoming of the reactive dyestuffs migration property difference of general formula (1) expression greatly, has higher migration property energy, has improved the level dyeing performance greatly;
Embodiment 8
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 8
Table 8
By table 8 as seen:
Yellow active dye composition of the present invention has excellent fastness to perspiration.
Embodiment 9
Fastness to soaping, color fastness to water and color fastness to sea water
Measure fastness to soaping, color fastness to water and the color fastness to sea water of following dyestuff as stated above, test result is recorded in the table 9
Table 9
By table 9 as seen:
Yellow active dye composition of the present invention has excellent fastness to soaping, color fastness to water and color fastness to sea water.
Embodiment 10
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 10
Table 10
By table 10 as seen:
Yellow active dye composition of the present invention has excellent sun-resistant fastness.
Embodiment 11
The photochromic fastness of sweat proof
Measure the photochromic fastness of sweat proof of following dyestuff as stated above, test result is recorded in the table 11
Table 11
By table 11 as seen:
Yellow active dye composition of the present invention has excellent sweat proof light fastness.
Claims (9)
1. the dye composition of general formula (2) expression shown in below the dye composition of general formula (1) expression shown in below Yellow active dye composition, this dye composite are selected from by one or more and one or more are selected from and the optional conventional dye additive that uses in dyeing and dye formulations are formed:
General formula (1)
In the formula:
Y
1For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or basic metal;
R
1, R
2, R
3And R
4Be H, C independently respectively
1-C
4Alkyl or C
1-C
4Alkoxyl group;
R
5And R
6Be H or C independently respectively
1-C
4Alkyl;
R
7And R
8Be H, sulfo group, C independently respectively
1-C
4Alkyl or C
1-C
4Alkoxyl group;
M is 2 or 3;
X
1Be Cl or F;
General formula (2)
In the formula:
Y
2For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or basic metal;
R
9And R
10Be H or C independently respectively
1-C
4Alkyl;
R
11And R
12Be H, C independently respectively
1-C
4Alkyl or C
1-C
4Alkoxyl group;
N is 2 or 3;
X
2Be Cl or F;
The weight ratio of the dye composition of the dye composition of general formula (1) expression and general formula (2) expression is 80-20:20-80.
2. the described Yellow active dye composition of claim 1, its characteristic be, in general formula (1) and the general formula (2),
M is 2;
N is 2;
X
1And X
2Be Cl independently respectively.
3. the described Yellow active dye composition of claim 1, its characteristic be, in the general formula (1) left side-SO
3The M group when m=2, is positioned at 4,8 or 1,5 or 3,6 of naphthalene nucleus, or is positioned on the benzene nucleus-ortho position and a position of N=N-azo group; When m=3, then be positioned at 3,6,8 or 4,6,8 of naphthalene nucleus.
4. the described Yellow active dye composition of claim 1, its characteristic be, general formula (1) right side-SO
2Y
1Group is positioned on the benzene nucleus
The contraposition of group or a position; General formula (1) right side-R
7Group and-R
8Group is separately located on the benzene nucleus respectively
The contraposition of group, a position or ortho position.
5. the described Yellow active dye composition of claim 1, its characteristic be, general formula (2) left side-SO
3The M group when n=2, is positioned at 4,8 or 1,5 or 3,6 of naphthalene nucleus; When n=3, then be positioned at 3,6,8 or 4,6,8 of naphthalene nucleus.
6. the described Yellow active dye composition of claim 1, its characteristic be, general formula (2) middle part-SO
3The M group is positioned at 5 of naphthalene nucleus, 6 or 7.
7. the described Yellow active dye composition of claim 1, its characteristic be, general formula (2) right side-SO
2Y
2Group is positioned on the phenyl ring
The contraposition of group or a position; General formula (2) right side-R
11Group and-R
12On group is separately located on the phenyl ring respectively
The contraposition of group, a position or ortho position.
8. the described Yellow active dye composition of claim 1, its characteristic are that the dye composition of general formula (1) expression is:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8;
The dye composition of general formula (2) expression is:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4 or
Dyestuff II-5.
9. the application of each described Yellow active dye composition aspect cotton, woolen dyeing in the claim 1～8.
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|---|---|---|---|
| CN 201010136853 CN102206427B (en) | 2010-03-31 | 2010-03-31 | Yellow reactive dye composition and its application in dyeing of fiber |
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|---|---|---|---|
| CN 201010136853 CN102206427B (en) | 2010-03-31 | 2010-03-31 | Yellow reactive dye composition and its application in dyeing of fiber |
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|---|---|
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| CN102206427B true CN102206427B (en) | 2013-07-24 |
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|---|---|---|---|---|
| CN115976859A (en) * | 2022-11-29 | 2023-04-18 | 深圳全棉时代科技有限公司 | Photochromic cotton yarn and preparation method thereof, fabric and mixed dye |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4378313A (en) * | 1979-06-01 | 1983-03-29 | Sumitomo Chemical Company, Limited | Reactive yellow dye having both monochlorotriazinyl and vinylsulfone type reactive groups |
| CN1353144A (en) * | 2000-11-15 | 2002-06-12 | 西巴特殊化学品控股有限公司 | Active dyes and preparation method and use thereof |
| US6867286B1 (en) * | 2002-10-07 | 2005-03-15 | Lexmark International, Inc. | Yellow dyes and ink compositions |
| CN1810891A (en) * | 2005-01-25 | 2006-08-02 | 京仁洋行 | Novel reactive dye composition with three-color combination |
| CN101535413A (en) * | 2006-11-09 | 2009-09-16 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use in a method for trichromatic dyeing or printing |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60215065A (en) * | 1985-03-26 | 1985-10-28 | Sumitomo Chem Co Ltd | Fiber-reactive monoazo compound |
-
2010
- 2010-03-31 CN CN 201010136853 patent/CN102206427B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4378313A (en) * | 1979-06-01 | 1983-03-29 | Sumitomo Chemical Company, Limited | Reactive yellow dye having both monochlorotriazinyl and vinylsulfone type reactive groups |
| US4378313B1 (en) * | 1979-06-01 | 1994-05-03 | Sumitomo Chemical Co | Reactive yellow dye having both monochlorotriazinyl and vinylsulfone type reactive groups |
| CN1353144A (en) * | 2000-11-15 | 2002-06-12 | 西巴特殊化学品控股有限公司 | Active dyes and preparation method and use thereof |
| US6867286B1 (en) * | 2002-10-07 | 2005-03-15 | Lexmark International, Inc. | Yellow dyes and ink compositions |
| CN1810891A (en) * | 2005-01-25 | 2006-08-02 | 京仁洋行 | Novel reactive dye composition with three-color combination |
| CN101535413A (en) * | 2006-11-09 | 2009-09-16 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use in a method for trichromatic dyeing or printing |
Non-Patent Citations (1)
| Title |
|---|
| JP昭60-215065A 1985.10.28 |
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Address after: Five road 201812 Shanghai city Jiading District Jiangqiao Fengbang Po Garden No. 301 Applicant after: Shanghai Argus Textile Chemical Co., Ltd. Co-applicant after: Shanghai Argus Fine Chemical Co., Ltd. Address before: Five road 201812 Shanghai city Jiading District Jiangqiao Fengbang Po Garden No. 301 Applicant before: Shanghai Argus Textile Chemicals Co., Ltd. Co-applicant before: Shanghai Argus Fine Chemical Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: YANYUN TEXTILE CHEMICAL CO., LTD., SHANGHAI TO: SHANGHAI ARGUS TEXTILE CHEMICAL CO., LTD. |
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Address after: 200231 Shanghai city Xuhui District Yindu Road No. 388 building 16 room 275-278 Applicant after: Shanghai Argus Textile Chemical Co., Ltd. Applicant after: Shanghai Argus Fine Chemical Co., Ltd. Address before: Five road 201812 Shanghai city Jiading District Jiangqiao Fengbang Po Garden No. 301 Applicant before: Shanghai Argus Textile Chemical Co., Ltd. Applicant before: Shanghai Argus Fine Chemical Co., Ltd. |
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Free format text: FORMER OWNER: SHANGHAI ARGUS FINE CHEMICAL CO., LTD. Effective date: 20150811 |
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Effective date of registration: 20150811 Address after: 200231 Shanghai city Xuhui District Yindu Road No. 388 building 16 room 275-278 Patentee after: Shanghai Argus Textile Chemical Co., Ltd. Address before: 200231 Shanghai city Xuhui District Yindu Road No. 388 building 16 room 275-278 Patentee before: Shanghai Argus Textile Chemical Co., Ltd. Patentee before: Shanghai Argus Fine Chemical Co., Ltd. |