CN102433012A - Red disazo dye compound, preparation method and composition thereof - Google Patents

Red disazo dye compound, preparation method and composition thereof Download PDF

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CN102433012A
CN102433012A CN2011102618293A CN201110261829A CN102433012A CN 102433012 A CN102433012 A CN 102433012A CN 2011102618293 A CN2011102618293 A CN 2011102618293A CN 201110261829 A CN201110261829 A CN 201110261829A CN 102433012 A CN102433012 A CN 102433012A
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hydrogen
disazo dye
halogen
red disazo
formula
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秦杰峰
孟胜锋
王高峰
贾建洪
蒋志平
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ZHEJIANG YIDE CHEMICAL CO Ltd
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ZHEJIANG YIDE CHEMICAL CO Ltd
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Abstract

The invention discloses a red disazo dye compound, a preparation method and a composition thereof, and is characterized in that the structure of the compound is shown in the formula (I); in the general formula (I), Z is SO2CH=CH2, OCH2CH2SO2CH=CH2, OCH2CH2SO2CH2CH2R3 or SO2CH2CH2R3, wherein R3 is hydrogen, halogen or hydroxide radical, M is hydrogen or alkali metal, R1 is hydrogen, C1-C4 alkyl radicals or halogen, R2 is hydrogen or sulfo radical, and X is halogen. The invention has good light fastness and obvious wet fastness and particularly can be applicable to dyeing cotton polyamide with high requirements on washing fastness, rubbing fastness and perspiration fastness, and also dyeing wool fibre and cotton fibre. The obtained dyed fabric has excellent performances, such as stable thermal sensitivity, light resistance, washing fastness, water-cleaning resistance, etc.

Description

A kind of red disazo dye compound, preparation method and compsn thereof
One, technical field
The present invention relates to a kind of red disazo dye compound, preparation method, compsn and the tint applications on textile fibres thereof.
Two, background technology
Along with the development of world textile fiber and printing technology, tinctorial property, economic performance and the environmental-protecting performance of dyestuff to be had higher requirement, orchil is general because of its monochrome and colorant match kind application party, becomes the improved focus of research in the industry.Azo class orchil compound disclosed in documents such as patent JP63243166, US5354849, US5075428, US4645832, US5359042; Though these dyestuffs can dye more bright-coloured color and luster; But Exposure to Sunlight, crockfastness are not good; Not only make this book of textiles outward appearance outmoded, simultaneously dyestuff splits away off on the fiber that can stain white or other color and lusters, produces staining, phenomenon cuts marks.
Three, summary of the invention
The object of the invention provides one type of red disazo dye, preparation method and the tint applications on textile fibres thereof with good light fastness and crockfastness.
The technical scheme that the present invention adopts is:
A kind of red disazo dye compound, structure is suc as formula shown in (I):
Figure BDA0000089228420000011
In the above-mentioned general formula (I): Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
Described red disazo dye compound is characterized in that: in the formula (I): R 1Be hydrogen, methyl, ethyl or chlorine; R 2Be hydrogen or sulfonic group; X is chlorine or fluorine; Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, wherein M is hydrogen or basic metal, R 3Be hydrogen, halogen, hydroxyl.
Described red disazo dye compound is characterized in that said red disazo dye compound is one of following:
Figure BDA0000089228420000021
Figure BDA0000089228420000031
Figure BDA0000089228420000041
Figure BDA0000089228420000051
The preparation of described red disazo dye compound has following two kinds of methods; Method one: the azoamines compound shown in the formula (II) is carried out diazotization earlier obtain diazonium salt; Diazonium salt carries out coupled reaction with the J acid shown in the formula (III) again; The coupled reaction product carries out the condensation reaction first time with the trimerization halogen cyanogen shown in the formula (IV) again; Condensation product carries out the condensation reaction second time with the aminated compounds shown in the formula V more for the first time, and reaction finishes afterreaction liquid and obtains said look red disazo dye compound through separation and purification; Method two: the azoamines compound shown in the formula (II) is carried out diazotization earlier obtain diazonium salt; Diazonium salt carries out coupled reaction with the J acid shown in the formula (III) again; The coupled reaction product carries out the condensation reaction first time with the trimerization halogen cyanogen shown in the formula (IV) again; Condensation product carries out the condensation reaction second time with the aminated compounds shown in the formula V more for the first time; The condensation product second time that reaction obtains carries out carrying out under the weak basic condition de-ester reaction, and reaction finishes afterreaction liquid and obtains said look red disazo dye compound through separation and purification.
Figure BDA0000089228420000061
Wherein, Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
The preparation method of described red disazo dye compound is characterized in that: said coupled reaction is carried out under PH=5-7, temperature T=8-15 ℃ condition.
The preparation method of described red disazo dye compound is characterized in that: the said condensation reaction first time is carried out under PH=2-6, temperature T=5-15 ℃ condition.
The preparation method of described red disazo dye compound is characterized in that: the said condensation reaction second time is carried out under PH=5-8, temperature T=30-50 ℃ condition.
The preparation method of described red disazo dye compound is characterized in that: said de-ester reaction carries out under PH=8-9, temperature T=40-60 ℃ condition.
Red disazo dye of the present invention is applicable to the printing and dyeing of hydroxyl or amido material, is specially adapted to the dyeing of wool, silk and tynex, and its fixation rate is high, crockfastness is excellent.Dyeing to above-mentioned substance is to carry out according to known normal dyeing method, can obtain light fastness, washing fastness, depth red right fabric excellent and beautiful in colour.
All represent for the description of this water-soluble dye molecular formula or for example, and dyestuff form general separated and that use is the basic metal form, particularly sodium salt, sylvite or lithium salts with the form of free acid.
The present invention for convenience of explanation; Compound is all represented with the form of free acid in specification sheets; But the dyestuff among the present invention is when being made or being used; Regular meeting exists with the form of water-soluble salt, and acceptable acid addition salts can be basic metal, earth alkali metal, ammonium salt or organic amine salt, and wherein the preferably is sodium salt, sylvite.
The invention still further relates to a kind of red disazo dye compsn, form suc as formula the red disazo dye compound shown in (I) by one or more structures basically:
Figure BDA0000089228420000071
Wherein: Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
Described red disazo dye compsn, it is characterized in that said red disazo dye compsn by one of following formula or wherein two or more red disazo dye compound form:
Figure BDA0000089228420000072
Figure BDA0000089228420000081
Figure BDA0000089228420000091
Described red disazo dye compsn; It is characterized in that said red disazo dye compsn is made up of suc as formula red disazo dye compound and auxiliary agent shown in (I) one or more structures; Auxiliary agent is 1-30 with the ratio of red disazo dye compound quality: 10, and said auxiliary agent is Sodium sulfate anhydrous.min(99) or sodium metnylene bis-naphthalene sulfonate or both mixtures.
Here said implication basically is meant in the compsn and also inevitably has some impurity, like the electrolytic salt of band in the raw material itself etc.The existence of these impurity does not influence effect of the present invention.
Because the singularity of dye industry is difficult to also there is no need to process pure article, can when processing finished product, dye composite of the present invention also allow to contain the impurity of a spot of moisture and trace with the impurity in some preparation processes usually.
Red disazo dye compound of the present invention, after commercialization is handled, the liquid state after can corpusculed, emulsifiable pasteization or with spray-drying process etc. carry out dried powdery, graininess is supplied with dyeing.This dyestuff is the product innovation that a matching stain and reactive dyestuffs combine.It has good light fastness and significant wet fastness, is specially adapted to washing fastness, crockfastness and perspiration fastness are had the cotton synthetic fibre dyeing of high request, also is applicable to the dyeing of hair fibre and cotton fibre simultaneously.The dyeing and weaving thing that obtains has that thermo-sensitivity is stable, sun-proof, washable, water-fast premium properties such as wash.Dyestuff has bright-coloured color and luster degree, equalization and good fastness at coloured fibre.This dyestuff is applicable to that cellulosic fibre, protein fibre and tynex are contaminated, tie dyeing-gas steams, tie dyeing-bake and explode and dye-bank up and jet dyeing.
Four, embodiment
Below in conjunction with the practical implementation example the present invention is done further description, but not therefore for limiting scope of the present invention, explanation for ease; Dye composition will be represented with the form of free acid; But its actual being formed with possibly be a metal base, more likely is metal-salt, especially sodium salt.
Embodiment 1
1, condensation for the first time
Add the aminated compounds shown in the 12.76g formula (III) in the 130ml water, regulate PH=6.0-7.0, stir complete dissolving and obtain aminated compounds solution with liquid caustic soda.Cyanuric chloride, 50ml water, 80g ice and the 0.2g Dispersant MF of 10g formula (IV-1) are mixed making beating about 40-60 minute; Controlled temperature T=0-2 ℃; Stir and slowly add above-mentioned aminated compounds solution down; Add the back and regulate PH=2.0-2.5, and, obtain the condensation product first time of formula (A-1) in 5-10 ℃ of following stirring reaction 2-3 hour with the sodium bicarbonate powder.
Figure BDA0000089228420000121
2, coupled reaction
P-aminoazobenzene-4-the sulfonic acid that in 150ml 60-70 ℃ hot water, adds 15.24g formula (II-1), stirring and dissolving adds the sodium nitrite solution of 4.2g 30% then, stirs, cool to simultaneously 15-20 ℃ subsequent use.Stir down aforesaid P-aminoazobenzene-4-sulfonic acid reserve liquid evenly to be added drop-wise to be diluted in advance and carry out diazotization reaction in the 60ml diazonium hydrochloric acid (30% hydrochloric acid 23g, 50ml water), P-aminoazobenzene-4-sulfonic acid reserve liquid adds back system control PH=0.9-1.2; T=10-15 ℃ of temperature control; Insulation reaction 1-1.5 hour, obtain P-aminoazobenzene-4-sulfonic acid diazonium salt, the diazonium terminal point is with the micro-indigo plant of KI-starch test paper; Remove excessive Sodium Nitrite with an amount of thionamic acid, subsequent use.
Figure BDA0000089228420000122
Stir down this P-aminoazobenzene-4-sulfonic acid diazonium salt is evenly joined first time of making in the step 1 in the condenses; Carry out coupled reaction; Add the back with 10g sodium bicarbonate powder regulation system PH=6.0-6.5; And the adjustment temperature is 5-10 ℃, and PH reaction 2-3 hour is protected in insulation, can obtain the conjugates of (B-1).
Figure BDA0000089228420000123
(B-1)
3, condensation for the second time
After the coupling terminal point arrives, add 9.8g formula (V-1) aminated compounds and carry out two reactions of contracting, slowly two systems of contracting are heated to 35-40 ℃; And with 12g sodium bicarbonate adjusting PH=4.0-4.5; PH reaction 4 hours is protected in insulation, and then is warming up to 45-50 ℃, and regulates PH=6.0-6.5 with sodium bicarbonate; PH reaction 2-3 hour is protected in insulation, can obtain two products that contract.
Figure BDA0000089228420000131
4, further degreasing and aftertreatment
What in step 3, obtain two contracts in the product, is warmed up to 50 ℃ again, regulates PH=8.2-8.5 with 15g soda ash powder, and insulation reaction 4-5 hour, reaction was hydrolyzed.After the hydrolysis terminal point arrives, add 30% hydrochloric acid adjusting PH=6.0-6.5, reduce the temperature to 40-45 ℃ simultaneously.And adding sodium-chlor 30g saltouts the clear spot after-filtration.Filter cake is recovered in 80 ℃ of oven dry down, grinds, and can obtain the about 52g of water-soluble red powder shape dyestuff, through UV test λ Max=476nm, the form of its free acid is represented as shown in the formula shown in (I-1):
Figure BDA0000089228420000132
Embodiment 2-11
According to the preparation method of embodiment 1, use the trimerization halogen cyanogen and the J acid of table 1 Chinese style (IV) to carry out the condensation first time; Diazonium salt with azoamines compound shown in the formula (II) carries out coupled reaction again; Aminated compounds shown in coupling product and the formula V carries out the condensation second time; Further, aftertreatment two thing that contracts is proceeded hydrolysis degreasing reaction, does the dyestuff aftertreatment again, can obtain corresponding red disazo dye compound suc as formula (I) institute formula.
Table 1
Figure BDA0000089228420000151
Figure BDA0000089228420000161
Figure BDA0000089228420000171
Embodiment 12
In step 3, in the condensation reaction for the second time, will substitute suc as formula the aminated compounds shown in (V-1) suc as formula the aminated compounds shown in (V-3), add sodium-chlor 30g after reaction finishes and saltout the clear spot after-filtration.Filter cake is recovered in 80 ℃ of oven dry down, grinds, and can obtain the about 52g of water-soluble red powder shape dyestuff, through UV test λ Max=480nm, the form of its free acid is represented as shown in the formula shown in (I-12):
Embodiment 13-19
According to the preparation method of embodiment 12, use the trimerization halogen cyanogen and the J acid of table 2 Chinese style (IV) to carry out the condensation first time; Diazonium salt with azoamines compound shown in the formula (II) carries out coupled reaction again; Aminated compounds shown in coupling product and the formula V carries out carrying out the dyestuff aftertreatment after the condensation second time, can obtain corresponding red disazo dye compound suc as formula (I) institute formula.
Table 2
Figure BDA0000089228420000191
Figure BDA0000089228420000201
The test procedure of red disazo dye compound is following:
Take by weighing dye composition that 1g the foregoing description 1-19 makes and place and dye in the cup, add water 200ml and dissolve, add the 0.5g Sodium sulfate anhydrous.min(99) again, 0.1g paregal O, stirring and dissolving.Transfer dye liquor PH=6-6.5 with acetic acid, put into the 10g nylon fibre, will dye glass normal temperature and be placed in the proof press; Be heated to 40 ℃, be incubated 15 minutes, the speed with 1 ℃/min is warming up to 100 ℃ then; Be incubated 45 minutes, dye completely, be cooled to 90 ℃; To dye cup and take out, cool off 15 minutes, take out dyeing and weaving thing washing oven dry.Adopt its colour fastness to light of method test, colour fastness to washing, colour fastness to perspiration, the colour fastness to rubbing confirmed among GB/T 8427-1998, GB/T 3921.3-1997, GB/T 3922-1995, the GB/T 3920-1997.Test result is seen table 3.
The test procedure of red disazo dye compsn is following:
Taking by weighing two kinds of dye compositions that total amount 1g the foregoing description 1-19 makes or multiple dyestuff places and dyes in the cup [like 0.5g (I-1)+0.5g (I-2), 0.2g (I-5)+0.8g (I-8) etc.].Add water 200ml and dissolve, add the 0.5g Sodium sulfate anhydrous.min(99) again, 0.1g paregal O, stirring and dissolving.Transfer dye liquor PH=6-6.5 with acetic acid, put into the 10g nylon fibre, will dye glass normal temperature and be placed in the proof press; Be heated to 40 ℃, be incubated 15 minutes, the speed with 1 ℃/min is warming up to 100 ℃ then; Be incubated 45 minutes, dye completely, be cooled to 90 ℃; To dye cup and take out, cool off 15 minutes, take out dyeing and weaving thing washing oven dry.Adopt its colour fastness to light of method test, colour fastness to washing, colour fastness to perspiration, the colour fastness to rubbing confirmed among GB/T 8427-1998, GB/T 3921.3-1997, GB/T 3922-1995, the GB/T 3920-1997.Test result is seen table 4.
Table 3
Figure BDA0000089228420000231
Can find out that from above-mentioned test result red disazo dye each item fastness provided by the invention is good.
Table 4
Can find out that from above-mentioned test result red disazo dye each item fastness provided by the invention is good.

Claims (10)

1. red disazo dye compound, structure is suc as formula shown in (I):
Figure FDA0000089228410000011
In the above-mentioned general formula (I): Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
2. red disazo dye compound as claimed in claim 1 is characterized in that: in the formula (I): R 1Be hydrogen, methyl, ethyl or chlorine; R 2Be hydrogen or sulfonic group; X is chlorine or fluorine; Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, wherein M is hydrogen or basic metal, R 3Be hydrogen, halogen, hydroxyl.
3. red disazo dye compound as claimed in claim 1 is characterized in that said red disazo dye compound is one of following:
Figure FDA0000089228410000012
Figure FDA0000089228410000021
Figure FDA0000089228410000041
4. the preparation method of red disazo dye compound as claimed in claim 1 is following: the azoamines compound shown in the formula (II) is carried out diazotization earlier obtain diazonium salt; Diazonium salt carries out coupled reaction with the J acid shown in the formula (III) again; The coupled reaction product carries out the condensation reaction first time with the trimerization halogen cyanogen shown in the formula (IV) again; Condensation product carries out the condensation reaction second time with the aminated compounds shown in the formula V more for the first time, and reaction finishes afterreaction liquid and obtains said look red disazo dye compound through separation and purification.
Figure FDA0000089228410000042
Wherein, Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
5. the preparation method of red disazo dye compound as claimed in claim 4; It is characterized in that the condensation product second time that condensation reaction for the second time obtains carries out the de-ester reaction under the weak basic condition, reaction finishes afterreaction liquid and obtains look red disazo dye compound through separation and purification.
6. like the preparation method of claim 4 or 5 described red disazo dye compounds; It is characterized in that: said coupled reaction is carried out under PH=5-7, temperature T=8-15 ℃ condition; The said condensation reaction first time is carried out under PH=2-6, temperature T=5-15 ℃ condition, and the said condensation reaction second time is carried out under PH=5-8, temperature T=30-50 ℃ condition.
7. method as claimed in claim 5 is characterized in that: described de-ester reaction carries out under PH=8-9, temperature T=40-60 ℃ condition.
8. red disazo dye compsn, form suc as formula the red disazo dye compound shown in (I) by one or more structures:
Figure FDA0000089228410000051
Wherein: Z is SO 2CH=CH 2, OCH 2CH 2SO 2CH=CH 2, OCH 2CH 2SO 2CH 2CH 2R 3, or SO 2CH 2CH 2R 3, R wherein 3Be hydrogen, halogen, hydroxyl; M is hydrogen or basic metal; R 1Be hydrogen, C1-C4 alkyl or halogen; R 2Be hydrogen or sulfonic group; X is a halogen.
9. red disazo dye compsn as claimed in claim 8 is characterized in that being made up of following formula any two or two or more red disazo dye compounds:
Figure FDA0000089228410000052
Figure FDA0000089228410000061
Figure FDA0000089228410000081
10. red disazo dye compsn as claimed in claim 9; It is characterized in that said red disazo dye compsn also comprises auxiliary agent; Described auxiliary agent is 1-30 with the ratio of red disazo dye compound quality: 10, and said auxiliary agent is Sodium sulfate anhydrous.min(99) or sodium metnylene bis-naphthalene sulfonate or both mixtures.
CN2011102618293A 2011-09-06 2011-09-06 Red disazo dye compound, preparation method and composition thereof Pending CN102433012A (en)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61272269A (en) * 1985-05-28 1986-12-02 Mitsubishi Chem Ind Ltd Disazo compound
US4645832A (en) * 1984-04-09 1987-02-24 Mitsubishi Chemical Industries Limited Cellulose fiber-reactive disazo or trisazo dyes having a triazine ring substituted by A(B-sulfatoethyl) sulfonylanilino group
JPS63243166A (en) * 1987-03-31 1988-10-11 Nippon Kayaku Co Ltd Disazo compound and dyeing of substrate using same
EP0357915A1 (en) * 1988-07-30 1990-03-14 Bayer Ag Disazo dyes
US5354849A (en) * 1991-03-30 1994-10-11 Sandoz Ltd. Sulfo group-containing disazo compounds containing substituted amino-1,3,5-triazinil or- chloropyrimidyl
CN1229108A (en) * 1998-03-17 1999-09-22 美国永光公司 Red dyestuffs and making method thereof
CN1292811A (en) * 1998-03-13 2001-04-25 Basf公司 Reactive dyes with combination anchor
CN1884388A (en) * 2005-06-24 2006-12-27 明德国际仓储贸易(上海)有限公司 Red disazo dyes
CN101307186A (en) * 2008-06-20 2008-11-19 上虞新晟化工工业有限公司 Red disazo dye compound, preparation method and composition thereof
CN102040862A (en) * 2010-08-30 2011-05-04 天津德凯化工股份有限公司 Nylon reactive red dye and preparation method thereof

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4645832A (en) * 1984-04-09 1987-02-24 Mitsubishi Chemical Industries Limited Cellulose fiber-reactive disazo or trisazo dyes having a triazine ring substituted by A(B-sulfatoethyl) sulfonylanilino group
JPS61272269A (en) * 1985-05-28 1986-12-02 Mitsubishi Chem Ind Ltd Disazo compound
JPS63243166A (en) * 1987-03-31 1988-10-11 Nippon Kayaku Co Ltd Disazo compound and dyeing of substrate using same
EP0357915A1 (en) * 1988-07-30 1990-03-14 Bayer Ag Disazo dyes
US5354849A (en) * 1991-03-30 1994-10-11 Sandoz Ltd. Sulfo group-containing disazo compounds containing substituted amino-1,3,5-triazinil or- chloropyrimidyl
CN1292811A (en) * 1998-03-13 2001-04-25 Basf公司 Reactive dyes with combination anchor
CN1229108A (en) * 1998-03-17 1999-09-22 美国永光公司 Red dyestuffs and making method thereof
CN1884388A (en) * 2005-06-24 2006-12-27 明德国际仓储贸易(上海)有限公司 Red disazo dyes
CN101307186A (en) * 2008-06-20 2008-11-19 上虞新晟化工工业有限公司 Red disazo dye compound, preparation method and composition thereof
CN102040862A (en) * 2010-08-30 2011-05-04 天津德凯化工股份有限公司 Nylon reactive red dye and preparation method thereof

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Application publication date: 20120502