CN105111775A - Application of azo compound - Google Patents
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- CN105111775A CN105111775A CN201510642949.6A CN201510642949A CN105111775A CN 105111775 A CN105111775 A CN 105111775A CN 201510642949 A CN201510642949 A CN 201510642949A CN 105111775 A CN105111775 A CN 105111775A
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Abstract
The invention discloses application of an azo compound. Disperse dye prepared by utilizing the azo compound has excellent washing fastness and higher lifting force, the content of banned aromatic amine in a cloth specimen dyed by the disperse dye is compliance with the requirement of Oeko-Tex Standard 100-2015.
Description
Technical field
The present invention relates to a kind of application of azo-compound.
Background technology
In recent years, environmental problem is day by day serious, and country is also more and more stricter to the requirement of environmental protection aspect.Each big city, the whole nation shows environmental protection sky-high price penalty note frequently.Meanwhile, along with environment more and more worsens, people also pay attention to gradually to environment protection, and environmental consciousness is also strengthened gradually, have basically formed everybody in the whole society and have paid attention to ecotope, conscious well atmosphere of preserving the ecological environment.Therefore, current dye industry and the dyeing increasing pressure in environmental protection is large, and situation is very severe.
Dispersed dye intermediate pollutes all larger in process of production, seldom has enterprise's energy up to standard and produces in a large number.A few days ago, because pollution incident takes place frequently, directly cause some dyes intermediate famine, price straight line rises violently, thus cause dispersed dye price also straight line rise suddenly and sharply.So direct huge cost pressure is produced to dye industry and dyeing.
So, the dispersed dye kind of with low cost, technique environmental protection, excellent property be dye industry and market institute thereof in the urgent need to.
Summary of the invention
Technical problem to be solved by this invention is to alleviate dye industry and the huge environmental protection pressure of dyeing, cost pressure and improve the problem of dispersed dye poor-performing, providing a kind of application of azo-compound.Azo-compound preparation method of the present invention environmental protection, with low cost, the dispersed dye utilizing azo-compound of the present invention to obtain have excellent washing fastness and higher lifting force, and the content forbidding aromatic amine in cloth specimen after disperse dyeing meets the requirement of Oeko-TexStandard100-2015.
The invention provides a kind of azo-compound as shown in Equation 1,
Wherein, R
1for C
1-4alkyl or hydrogen; R
2for C
1-4alkyl;
D is
Described R
1and R
2in C
1-4alkyl preferable methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl independently of one another.
Described D is preferred
further preferably
When described D is
time, described R
1preferable methyl or ethyl.
When described D is
time, described R
1preferred hydrogen, methyl or ethyl.
When described D is
time, described R
1preferred hydrogen, methyl or ethyl.
When described D is
time, described R
1preferred hydrogen, methyl or ethyl.
When described D is
time, described R
1preferred hydrogen, methyl or ethyl.
Described azo-compound is preferably from following arbitrary compound:
Present invention also offers a kind of preparation method of described azo-compound, it comprises the following steps: in a solvent, under sour existent condition, compound 3 and naphthalene cycle compound 2 is carried out coupled reaction,
Wherein, A is Cl
-, CH
2cOO
-, H
2pO
4 -, HSO
4 -or NO
3 -.
In the preparation method of described azo-compound, described coupled reaction refers to that the diazonium salt (compound 3) of primary aromatic amine and arylamine (naphthalene cycle compound 2) react the reaction generating azo-compound (compound 1), and its concrete reactions steps and condition can refer to this type of reaction in this area and select.
In the preparation method of described azo-compound, described solvent is the Conventional solvents of this type of reaction of this area, is preferably water.
In the preparation method of described azo-compound, the temperature of reaction of described coupled reaction preferably 0 DEG C ~ 5 DEG C.
In the preparation method of described azo-compound, one or more in the preferred hydrochloric acid of described acid, acetic acid, phosphoric acid, nitric acid and sulfuric acid, one or more further preferably in hydrochloric acid, acetic acid and sulfuric acid, then preferably sulfuric acid and/or hydrochloric acid further.
In the preparation method of described azo-compound, the volume ratio of described acid and described solvent preferably 0.033 ~ 0.042: 1.
In the preparation method of described azo-compound, the volume mass of described solvent and described naphthalene cycle compound 2 is than preferred 6mL/g.
In the preparation method of described azo-compound, described naphthalene cycle compound 2 and compound 3 mol ratio preferably 1.1 ~ 1.2: 1.
In the preparation method of described azo-compound, the process of described coupled reaction can adopt routine monitoring method in this area to carry out monitoring (as filter paper oozes circle method), general by reaction solution point sample on filter paper, then ooze circle common factor place at the solution of a sampling point side point naphthalene cycle compound 2 with both and do not develop the color for reaction end.Wherein, (naphthalene cycle compound 2 is dissolved for utilizing the solvent that naphthalene cycle compound 2 can be dissolved conventional in this area the solution obtained by described " solution of naphthalene cycle compound 2 "), the reaction times preferred 2h of described coupled reaction.
In the preparation method of described azo-compound, also can carry out aftertreatment to product after described coupled reaction terminates and be further purified product.Described aftertreatment preferably includes following steps: filter after reaction solution being cooled to room temperature, and filter cake washes rear drying with water, namely obtains described azo-compound.Described drying temperature preferably 50 ~ 70 DEG C.
In the preparation method of described azo-compound, the preparation method of described compound 3 can comprise the following steps: under condition of no solvent, under sour existent condition, nitrosyl sulfuric acid and compound 8 is carried out diazotization reaction, obtains described compound 3,
Described diazotization reaction refers to that primary aromatic amine (compound 8) and nitrosyl sulfuric acid are under strong acid media, effect generates the reaction of diazonium salt (compound 3), and the routine that its concrete reactions steps and condition can refer to this type of reaction in this area is selected.
In described diazotization reaction, one or more in the preferred hydrochloric acid of described acid, acetic acid and sulfuric acid, further preferably sulfuric acid.
In described diazotization reaction, described compound 8 is preferably 1: 1 ~ 1.1 with the mol ratio of described nitrosyl sulfuric acid.
In described diazotization reaction, the quality mol ratio of described acid and described compound 8 is 280: 1.
The temperature of reaction of described diazotization reaction preferably 10 ~ 20 DEG C, such as 15 DEG C.
In described diazotization reaction, after preferably described acid being mixed with described nitrosyl sulfuric acid, then with described compound 8 hybrid reaction.
In described diazotization reaction, described " mixing with described compound 8 ", the described time slowly added was 1 ~ 1.5h advantageously for slowly to join in described " mixed solution of described acid and described nitrosyl sulfuric acid " by described compound 8.
The process of described diazotization reaction can be monitored, for reaction end when generally disappearing with described compound 8 by routine monitoring method (as TLC or HPLC) in this area.The reaction times preferred 3h ~ 4h of described diazotization reaction.
Preferably do not carry out aftertreatment after described diazotization reaction terminates to be directly used in the preparation of described azo-compound.
In the preparation method of described azo-compound, the preparation method of described naphthalene cycle compound 2 can comprise the following steps: compound 4 and compound 5 are reacted, obtain described naphthalene cycle compound 2;
In the preparation method of described naphthalene cycle compound 2, the routine that concrete reactions steps and condition can refer to this type of reaction in this area is selected.
In the preparation method of described naphthalene cycle compound 2, described reaction can be carried out under condition that is solvent-free or that have solvent, preferably carries out in the absence of a solvent.
In the preparation method of described naphthalene cycle compound 2, when described reaction have carry out under solvent condition time, described solvent be this area such reaction routine use solvent, preferred dehydrated alcohol.The volume mass of described solvent and described compound 4 is than preferred 1.31mL/g.
In the preparation method of described naphthalene cycle compound 2, described reaction is preferably carried out in the presence of an inorganic base, described mineral alkali can be the conventional mineral alkali used of such reaction of this area, one or more in preferred sodium hydroxide, potassium hydroxide, salt of wormwood, sodium bicarbonate, saleratus and sodium carbonate, further preferred anhydrous sodium carbonate.
In the preparation method of described naphthalene cycle compound 2, when adding mineral alkali, the mol ratio of described mineral alkali and described compound 4 preferably 0.5 ~ 0.6: 1.
In the preparation method of described naphthalene cycle compound 2, described reaction is preferably carried out under the katalysis of catalyzer, and described catalyzer is the conventional catalyst of such reaction in this area, preferred Sodium Bromide and/or potassiumiodide.
In the preparation method of described naphthalene cycle compound 2, when adding catalyzer, the mol ratio of described catalyzer and described compound 4 preferably 0.22 ~ 0.26: 1.
In the preparation method of described naphthalene cycle compound 2, the mol ratio of described compound 4 and described compound 5 preferably 1: 1.3 ~ 1.5.
In the preparation method of described naphthalene cycle compound 2, described temperature of reaction preferably 100 DEG C ~ 120 DEG C.
The preparation method of described naphthalene cycle compound 2, after adding mineral alkali and catalyzer, preferably joins " mixture of compound 4, mineral alkali and catalyzer " in compound 5 and reacts.
In the preparation method of described naphthalene cycle compound 2, the reaction process of described reaction can be monitored, for reaction end when generally disappearing with described compound 4 by monitoring method (as TLC or HPLC) conventional in this area.
In the preparation method of described naphthalene cycle compound 2, also following last handling process can be comprised: add water in reaction solution after described reaction terminates, be warming up to 70 DEG C of layerings while hot, collect organic phase, under room temperature, regulate PH to neutral after adding water, be warming up to 65 ~ 70 DEG C, layering while hot, collect organic phase, evaporate to dryness.In the last handling process of described reaction, preferably regulate PH with the aqueous solution of the sodium hydroxide of 30%.
Present invention also offers a kind of naphthalene cycle compound 2,
Wherein, R
1and R
2definition ditto described in.
Described naphthalene cycle compound 2 is preferably from following arbitrary compound:
Present invention also offers a kind of preparation method of described naphthalene cycle compound 2, it comprises the following steps: compound 4 and compound 5 are reacted, obtain described naphthalene cycle compound 2;
Condition and the step of its reaction are same as above.
Present invention also offers the application of a kind of described azo-compound in stamp and/or dyeing.
Described application, is preferably the stamp to fabric and/or dyeing.
One or more in the preferred cellulose acetate fibre of described fabric, tynex, trevira and trevira mixed fibre goods, are more preferably trevira and/or trevira mixed fibre goods.
Described trevira mixed fibre goods refer to that trevira mixes with natural fibers such as cotton, hair, silk or fiber crops the goods spinning and make.
The preferred pet fiber of described trevira.
Described trevira mixed fibre goods preferred polyester/cotton blended fiber goods or polyester/wool mixed fibre goods.
Described polyester/cotton mixed fibre goods refer to the textile fabrics that trevira and cotton fibre mix spinning are made.
Described polyester/wool mixed fibre goods refer to the textile fabrics that trevira and wool fiber mix spinning are made.
The existence form of described trevira and trevira mixed fibre goods can be the conventional existence form of this area, is preferably fiber, yarn, woven fabrics, knitted fabrics or non-woven fabric.
Described application, preferably includes following steps; Described azo-compound is carried out process according to this area conventional treatment method (as sand milling) and obtains dispersed dye, be then used in stamp and/or the dyeing of described fabric.
Described application, more preferably further comprising the steps of: described azo-compound is carried out process according to this area conventional treatment method (as sand milling) and obtains dispersed dye by (1); (2) described dispersed dye are mixed with water, in acid condition, are warming up to 70 DEG C, put into fabric, in 30 minutes, temperature is risen to 130 DEG C, be incubated 50 minutes, be cooled to 90 DEG C.
In described application, described acidic conditions regulates preferably by acetic acid, pH value preferably 4 ~ 5.
In described application, after described cooling, also can comprise reduction clearing step, preferably include: fabric is put into the aqueous solution containing 1 grams per liter sodium hydroxide and 3 grams per liter dithionic acid disodiums, clean at 80 DEG C, the time is 20 minutes.The described consumption containing the aqueous solution of 1 grams per liter sodium hydroxide and 3 grams per liter dithionic acid disodiums is not particularly limited, as long as general fabric described in submergence cleans.
Room temperature in the present invention is 10 DEG C ~ 30 DEG C.
Number in the present invention, except specified otherwise, all refers to mass fraction.
Agents useful for same of the present invention and raw material are all commercially.
Without prejudice to the field on the basis of common sense, above-mentioned each optimum condition, can arbitrary combination, obtains the preferred embodiments of the invention.
Positive progressive effect of the present invention is: azo-compound preparation method of the present invention environmental protection, with low cost, the dispersed dye utilizing azo-compound of the present invention to obtain have excellent washing fastness and higher lifting force, and the amount forbidding aromatic amine in cloth specimen after described disperse dyeing meets the requirement of Oeko-TexStandard100-2015.
Embodiment
Mode below by embodiment further illustrates the present invention, but does not therefore limit the present invention among described scope of embodiments.The experimental technique of unreceipted actual conditions in the following example, conventionally and condition, or selects according to catalogue.
LC-MS data described in the present invention are by WatersUPLC-SQD LC-MS instrument (moving phase is acetonitrile/water system, 60%-90% acetonitrile V/V, column temperature 40 DEG C) test gained.
The test condition of HPLC of the present invention is: methyl alcohol: water (V/V)=40: 60, flow velocity: 1ml/min, determined wavelength: 254nm.
Embodiment 1 naphthalene cycle compound 2-1 (R
1for hydrogen, R
2for methyl) preparation
Under room temperature condition, in the 100ml there-necked flask of a drying, add 21.7g methyl chloroacetate (compound 5, R
2for methyl), in stirring, then add 19.09g1-naphthylamines, 8.5g anhydrous sodium carbonate and 3.46g Sodium Bromide, stir, be then slowly warming up to 100 DEG C of insulation reaction.HPLC monitoring reaction is until naphthalidine reacts completely.Add about 70ml water and make dissolution of solid, slowly be warming up to 70 DEG C of layerings while hot, collect organic phase, add water 50ml again, regulates PH to neutral, be then slowly warming up to 70 DEG C under room temperature with the aqueous sodium hydroxide solution of 30%, layering while hot, collect organic phase, underpressure distillation removing moisture, obtains naphthalene cycle compound 2-1 (R
1for hydrogen, R
2for methyl) 27.35g, the purity that yield 95.3%, HPLC measures is that 96.5%, LC-MS measures naphthalene cycle compound 2-1 (R
1for hydrogen, R
2for methyl) result be [M+H]
+216.3, [M+Na]
+238.4.
Embodiment 2 naphthalene cycle compound 2-4 (R
1for methyl, R
2for ethyl) preparation
Under room temperature condition, in the 100ml there-necked flask of a drying, add 24.51g ethyl chloroacetate (compound 5, R
2for ethyl), in stirring, then add 24.19gN-methyl naphthalidine, 8.5g anhydrous sodium carbonate and 3.46g Sodium Bromide, stir, be then slowly warming up to 120 DEG C of insulation reaction.HPLC monitoring reaction is until N-methyl naphthalidine reacts completely.Add about 70ml water and make dissolution of solid, slowly be warming up to 70 DEG C of layerings while hot, collect organic phase, add water 50ml again, regulates PH to neutral, be then slowly warming up to 65 DEG C under room temperature with the aqueous sodium hydroxide solution of 30%, layering while hot, collect organic phase, underpressure distillation removing moisture, obtains naphthalene cycle compound 2-4 (R
1for methyl, R
2for ethyl) 35.14g, the purity that yield 94%, HPLC measures is that 94.9%, LC-MS measures naphthalene cycle compound 2-4 (R
1for methyl, R
2for ethyl) result be [M+H]
+244.4, [M+Na]
+266.3.
Embodiment 3 naphthalene cycle compound 2-6 (R
1for ethyl, R
2for ethyl) preparation
Under room temperature condition, in the 100ml four-hole boiling flask of a drying, add 30ml dehydrated alcohol, 21.26g ethyl chloroacetate (compound 5, R
2for ethyl), in stirring, then add 22.83gN-ethyl naphthalidine, 8.5g anhydrous sodium carbonate and 3.46g Sodium Bromide, stir, be then slowly warming up to 100 DEG C of backflow insulation reaction.HPLC monitoring reaction is until N-ethyl naphthalidine reacts completely.Be cooled to room temperature, underpressure distillation removing ethanol and excessive ethyl chloroacetate.Add about 70ml water and make dissolution of solid, slowly be warming up to 70 DEG C of layerings while hot, collect organic phase, add water 50ml again, regulates PH to neutral, be then slowly warming up to 70 DEG C under room temperature with the aqueous sodium hydroxide solution of 30%, layering while hot, collect organic phase, underpressure distillation removing moisture, obtains naphthalene cycle compound 2-6 (R
1for ethyl, R
2for ethyl) 27.5g, the purity that yield 80.15%, HPLC measures is that 91.3%, LC-MS measures naphthalene cycle compound 2-6 (R
1for ethyl, R
2for ethyl) result be [M+H]
+258.1, [M+Na]
+280.3.
Prepare naphthalene cycle compound 2-1 ~ 2-6 according to the method for embodiment 1-2, its relevant experimental data and Structural Identification data are in table 1.
The experimental data of table 1 naphthalene cycle compound 2-1 ~ 2-6 and Structural Identification data
Embodiment 4 azo-compound 1-3 (R
1for methyl, R
2for methyl, D are
) preparation
Under room temperature condition, in the 100ml there-necked flask of a drying, add the sulphuric acid soln of the sulfuric acid of 11.2g98%, the nitrosyl sulfuric acid of 13.34g40%, after stirring, ice bath is cooled to 10-15 DEG C, slowly add 7.32g2,4-dinitraniline, about adds 1h, is incubated 3h and obtains transparent diazo liquid after adding under 10-15 DEG C of condition.Then in the 2000ml beaker that 60ml water, 2ml98% sulfuric acid are housed in 1h, obtained diazo liquid and 10.05g naphthalene cycle compound 2-3 are dripped simultaneously and carries out coupled reaction, control temperature of reaction 0-5 DEG C on the rocks, and complete coupling at 0-5 DEG C of insulation 2h, be naturally stirred to room temperature, filter, washing, 50 DEG C of oven dry, obtain the dyestuff filter-cakes 21.3g of azo-compound 1-3, the purity 94.5% that yield 92.37%, HPLC is tested.The result that LC-MS measures azo-compound-13 is [M+H]
+424.4, [M+Na]
+446.6.
Embodiment 5 azo-compound 1-8 (R
1for hydrogen, R
2for ethyl, D are
) preparation
Under room temperature condition, in the 100ml there-necked flask of a drying, add the sulphuric acid soln of nitrosyl sulfuric acid of the sulfuric acid of 11.2g98%, 12.7g40% (0.04mol), after stirring, ice bath is cooled to 10-15 DEG C, slowly add 10.48g2,4-dinitrobenzene-6 bromaniline (0.04mol), about adds 1-1.5h, is incubated 4h and obtains transparent diazo liquid after adding under being warming up to 15-20 DEG C of condition.Then drip with 10.47g naphthalene cycle compound 2-2 in 1h in the 2000ml beaker that 60ml water, 2.5ml98% sulfuric acid are housed simultaneously carry out coupled reaction, control temperature of reaction 0-5 DEG C on the rocks, and complete coupling at 0-5 DEG C of insulation 2h, naturally be stirred to room temperature, filter, washing, 70 DEG C of oven dry, obtain the dyestuff filter-cakes 18.84g of azo-compound 1-8, the purity 96.2% that yield 93.8%, HPLC is tested.The result that LC-MS measures azo-compound 1-8 is [M+H]
+503.3, [M+Na]
+525.2.
According to the method for embodiment 1 ~ 5, correspondingly replace reactant, prepare azo-compound 1-1 ~ 1-30.Relevant experimental data and Structural Identification data are in table 2.
The experimental data of table 2 azo-compound 1-1 ~ 1-30 and Structural Identification data
Effect example 1
Get 5 grams of azo-compound 1-3 (R obtained by embodiment 2
1for methyl, R
2for methyl, D is
), commercialization dispersed dye are made after grinding, the dispersed dye prepared are dispersed in 500 ml waters, draw 20 milliliters to mix with the water of 80 milliliters, adjust dye bath pH to be 4 ~ 5 with acetic acid, be warming up to 70 DEG C and put into 5 grams of polyester fiber cloths simultaneously and dye, in 30 minutes, be warming up to 130 DEG C by 70 DEG C, be incubated 50 minutes, be cooled to less than 90 DEG C draining cleanings.The 100 milliliters of reduction clearing aqueous solution put into by cloth specimen again containing 1 grams per liter sodium hydroxide and 3 grams per liter V-Brite Bs clean in 80 DEG C, and the time is 20 minutes.
Effect example 2
According to the method for effect example 1, dispersed dye prepared by azo-compound 1-1 ~ 1-30 are dyeed, and adopt GB GB/T3921-2008 [C (3) method], GB/T2394-2013, GB/T2397-2012 test its washing fastness, staining power and lifting force respectively.And adopting Oeko-TexStandard100-2015 to test its forbidding aromatic amine content to dyeing cloth specimen, its test result is in table 3 and table 4.
The dyeing after washing fastness effect data of dispersed dye prepared by table 3 azo-compound-1 ~ 1-30
Note: except 2-naphthylamines, all the other forbidding aromatic amines all do not detect.
Table 3 data presentation: dispersed dye of the present invention, not only has higher washing fastness, effectively can solve the problem of washing fastness difference; And cloth specimen forbidding aromatic amine meets the requirement lower than 20mg/kg in Oeko-TexStandard100-2015 after disperse dyeing of the present invention.
The lifting force of dispersed dye prepared by table 4 azo-compound 1-1 ~ 1-30
Table 4 data presentation: dispersed dye of the present invention have excellent lifting force.
Effect comparison example 1
The washing fastness of C.I. Disperse Red 6 and C.I. EX-SF DISPERSE BLUE EX-SF 300 85, staining power and lifting force is tested respectively according to the testing method of effect example 2.Its test result is in table 5.
Table 5.C.I. Disperse Red 6 and C.I. EX-SF DISPERSE BLUE EX-SF 300 85 wash water fastness and lifting force
Table 5 data presentation: the washing fastness of C.I. Disperse Red 6 and C.I. EX-SF DISPERSE BLUE EX-SF 300 85 is all lower than the washing fastness of dispersed dye of the present invention; Lifting force is also far away from the lifting force of dispersed dye of the present invention.
Claims (10)
1. the azo-compound as shown in Equation 1 application in stamp and/or dyeing,
Wherein, R
1for C
1-4alkyl or hydrogen; R
2for C
1-4alkyl;
D is
2. apply as claimed in claim 1, it is characterized in that: described R
1and R
2in C
1-4alkyl be methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl independently of one another.
3. apply as claimed in claim 2, it is characterized in that:
When described D is
time, described R
1for methyl or ethyl;
When described D is
time, described R
1for hydrogen, methyl or ethyl;
When described D is
time, described R
1for hydrogen, methyl or ethyl;
When described D is
time, described R
1for hydrogen, methyl or ethyl;
When described D is
time, described R
1for hydrogen, methyl or ethyl.
4. apply as claimed in claim 1, it is characterized in that: described azo-compound is selected from following arbitrary compound:
5. apply as claimed in claim 1, it is characterized in that: described be applied as stamp to fabric and/or dyeing.
6. apply as claimed in claim 5, it is characterized in that: described fabric is one or more in cellulose acetate fibre, tynex, trevira and trevira mixed fibre goods.
7. apply as claimed in claim 6, it is characterized in that: described trevira is pet fiber; And/or described trevira mixed fibre goods are polyester/cotton mixed fibre goods or polyester/wool mixed fibre goods.
8. apply as claimed in claim 5, it is characterized in that comprising the following steps; Described azo-compound is carried out process and obtains dispersed dye, be then used in stamp and/or the dyeing of described fabric.
9. apply as claimed in claim 8, it is characterized in that comprising the following steps; (1) described azo-compound is obtained dispersed dye by sanded; (2) described dispersed dye are mixed with water, in acid condition, are warming up to 70 DEG C, put into fabric, in 30 minutes, temperature is risen to 130 DEG C, be incubated 50 minutes, be cooled to 90 DEG C.
10. apply as claimed in claim 9, it is characterized in that, after described cooling, also comprising reduction clearing step: fabric is put into the aqueous solution containing 1 grams per liter sodium hydroxide and 3 grams per liter dithionic acid disodiums, clean at 80 DEG C, the time is 20 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510642949.6A CN105111775A (en) | 2015-09-30 | 2015-09-30 | Application of azo compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510642949.6A CN105111775A (en) | 2015-09-30 | 2015-09-30 | Application of azo compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105111775A true CN105111775A (en) | 2015-12-02 |
Family
ID=54659902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510642949.6A Pending CN105111775A (en) | 2015-09-30 | 2015-09-30 | Application of azo compound |
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|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111849194A (en) * | 2020-07-27 | 2020-10-30 | 浙江青松轻纺股份有限公司 | Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1462178A (en) * | 1973-08-22 | 1977-01-19 | Ici Ltd | Monoazo disperse dyestuffs |
| US5723586A (en) * | 1995-06-19 | 1998-03-03 | Clariant Finance (Bvi) Limited | Disperse dyes |
| US5922089A (en) * | 1995-02-27 | 1999-07-13 | Dystar Japan Ltd. | Method of dyeing polyester and polyester-containing textile materials |
| CN103233370A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Disperse dye application |
-
2015
- 2015-09-30 CN CN201510642949.6A patent/CN105111775A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1462178A (en) * | 1973-08-22 | 1977-01-19 | Ici Ltd | Monoazo disperse dyestuffs |
| US5922089A (en) * | 1995-02-27 | 1999-07-13 | Dystar Japan Ltd. | Method of dyeing polyester and polyester-containing textile materials |
| US5723586A (en) * | 1995-06-19 | 1998-03-03 | Clariant Finance (Bvi) Limited | Disperse dyes |
| CN103233370A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Disperse dye application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111849194A (en) * | 2020-07-27 | 2020-10-30 | 浙江青松轻纺股份有限公司 | Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing |
| CN111849194B (en) * | 2020-07-27 | 2021-09-17 | 浙江青松轻纺股份有限公司 | Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing |
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