CN104231660A - Monoazo compound as well as product and application thereof - Google Patents

Monoazo compound as well as product and application thereof Download PDF

Info

Publication number
CN104231660A
CN104231660A CN201410377742.6A CN201410377742A CN104231660A CN 104231660 A CN104231660 A CN 104231660A CN 201410377742 A CN201410377742 A CN 201410377742A CN 104231660 A CN104231660 A CN 104231660A
Authority
CN
China
Prior art keywords
monoazo compound
formula
alkyl
compound
fastness
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.)
Pending
Application number
CN201410377742.6A
Other languages
Chinese (zh)
Inventor
陈旭
袁小红
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.)
ZHEJIANG YUTAI DYEING TECHNOLOGY CO LTD
Original Assignee
ZHEJIANG YUTAI DYEING TECHNOLOGY 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 ZHEJIANG YUTAI DYEING TECHNOLOGY CO LTD filed Critical ZHEJIANG YUTAI DYEING TECHNOLOGY CO LTD
Priority to CN201410377742.6A priority Critical patent/CN104231660A/en
Publication of CN104231660A publication Critical patent/CN104231660A/en
Pending legal-status Critical Current

Links

Abstract

The invention discloses a monoazo compound as well as a product and application thereof, belonging to the technical field of disperse dyes. The monoazo compound is shown in a formula (I). The monoazo compound has the significant application in dyeing and printing on a synthetic fiber material as a disperse dye, especially has good comprehensive performance when being applied to a polyester ammonia elastic fabric, and particularly has excellent properties such as color fastness to washing, color fastness to water, dry heating sublimation resistant fastness, sun-proof fastness, deep dyeing performance and the like.

Description

A kind of Monoazo compound, goods and application
Technical field:
The present invention relates to a kind of Monoazo compound, goods and application, belong to technical field of disperse dyes.
Background technology:
The dispersed dye being coupling component with pyridinone intermediate are the important kind in the colour system such as yellow, orange, often have lovely luster, molar extinction coefficient is high, and the feature such as washing fastness is good.The kind of this class formation a large amount of has been logged in, as C.I. DISPERSE YELLOW 119,211,241 etc. in Colour Index (Color Index).But along with thin dawn, the super fine denierization processing of trevira, and functional type mixes the fast development of fabric, find that these dyestuffs are water-fastness poor with dry heat resistance sublimation fastness in the application of above-mentioned materials, also bad with the compatibleness of other dyestuff.It is-CH that Chinese patent CN102127316 discloses a class atom N substituting group 2cH 2the dispersed dye of NHCOR (wherein R is methyl, ethyl and phenyl) pyridone type, find in research that its over-all properties is still not good, especially depth is very poor, only can on a small quantity for colorant match.Therefore, need to develop at polyester superfine fibre, polyester blended product, particularly apply and be gradually extensively commonly called as the washing on ammonia elastic fabric of T+OP, over-all properties is good, the product that especially the salient features tool such as washing fastness, dry heat resistance sublimation fastness, light fastness, depth is good.
Summary of the invention:
A first aspect of the present invention object is to provide and is a kind ofly applied in polyester superfine fibre, wash good combination property on ammonia blending product, a kind of Monoazo compound of the light fastness especially had, washing fastness, sublimation fastness and lifting force.
For achieving the above object, the technical scheme that the present invention takes is as follows:
A kind of Monoazo compound, its structure is as shown in formula I:
In formula I:
R 1for hydrogen, methoxyl group, C 2 ~ 4alkoxyl group, nitro, halogen or-COOR, wherein R is C 1 ~ 4alkyl, C 1 ~ 4alkyl oxygen ethyl, C 1 ~ 4alkyl oxygen ethyl oxygen ethyl or phenyl,
R 2for hydrogen, halogen or C 6h 5sO 2o-,
R 3for hydrogen, halogen, cyano group or nitro,
R 4for hydrogen, halogen, cyano group or nitro,
R 5for-CH 2cH 2-,-CH 2cH 2cH 2-or-CH 2cH (CH 3)-,
R 6for methyl, ethyl, phenyl or C 3 ~ 6alkyl,
R 7for methyl, C 2 ~ 4alkyl, phenyl or tolyl,
Z is C or SO.
Described Monoazo compound, its particularly preferred structure is such as formula shown in (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7), (I-8), (I-9), (I-10) or (I-11):
A second aspect of the present invention object is to provide a kind of method preparing Monoazo compound described in formula I, it is characterized in that, comprises the steps:
(1), by formula IV compound and CH 3cOCH 2cOOR 10under weak basic condition, heat condensation obtains formula (V) compound;
(2), formula VI compound is carried out diazotization with nitrite or nitrosyl sulfuric acid in acidic medium;
(3) diazonium salt, by formula VI compound obtained mixes in water with the compound shown in formula (V), the Monoazo compound that coupled reaction prepares formula I occurs, wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7with Z, there is the definition of above-mentioned formula I.
Described formula IV compound can be prepared by the mode known.As by CNCH 2cOOR 9with the stirring reaction in the aqueous solution of water or hydrophilic solvent of the diamine compounds shown in formula II, prepare formula III compound;
Formula III compound and acid anhydrides (R 7zO) 2o or acyl chlorides R 7zO-Cl carries out acylation reaction in common mode, prepares formula IV compound, wherein R 5, R 6, R 7with Z, there is the definition of above-mentioned formula I, R 9for C 1 ~ 4alkyl.
A third aspect of the present invention object is to provide the purposes of a kind of described Monoazo compound as dispersed dye.When Monoazo compound of the present invention or its mixture use as dyestuff, usual dispersion processing becomes wield dispersed dye goods.Such as, grind with sand mill under Monoazo compound of the present invention or its mixture and auxiliary agent, water or other wetting agent exist, make its median size at 0.1 to 10 micron, the dispersed dye goods obtained can after the addition of water for the preparation of printing paste or dye bath.
Described auxiliary agent is the dispersion agent, diffusant etc. that dispersed dye are conventional when preparing, preferably one of following or its mixture several arbitrarily: the anionic dispersing agents such as naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin, polycarboxylic acid macromolecule dispersing agent, poly alkylene glycol ether sulfuric ester, alkyl polyoxyethylene glycol phosphoric acid ester.Especially naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), condensation compound of methyl naphthalene sulfonic acid and formaldehyde (as Dispersant MF), benzyl naphthalenesulfonate formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (as commercial dispersants Reax 85A).The ratio of auxiliary agent and the even compound of described list can change in relative broad range, and generally auxiliary agent is (0.2 ~ 10) with the weight ratio of single even compound: 1, preferably (0.5 ~ 2): 1.
The dispersed dye goods of Monoazo compound of the present invention are with the liquid state after corpusculed, emulsifiable paste state, carry out dried powdery or graininess supply dyeing by spray-drying process etc.In liquid dye goods, the weight percentage of Monoazo compound is 10 ~ 30%, and the weight percentage of auxiliary agent is 5 ~ 45%, and all the other are water or other synergistic agent.Described synergistic agent is optional frostproofer, anti-settling agent, sterilant, metal chelating agent, hyperchromicity agent, thickening material, stablizer, levelling agent, fastness elevator and defoamer etc.In solid dye goods, the weight percentage of Monoazo compound is 10 ~ 60%, and the weight percentage of auxiliary agent is 40 ~ 90%.
The mixture of Monoazo compound of the present invention or Monoazo compound can be used for dyeing and the stamp of hydrophobic synthetic filamentary material and blended material thereof, especially dyeing textiles and stamp.Described hydrophobic synthetic filamentary material is aromatic polyester, especially pet fiber and its microfibre (comprising sea island fiber), polymeric amide, especially polyhexamethylene oxamide, secondary cellulose acetate, cellulose triacetate, urethane.The blended material of described hydrophobic synthetic filamentary material is the blended material of polyester-cellulose, polyester-polyurethane, polyester-polyamide and polyester-wool.Described hydrophobic synthetic fiber and blended material thereof can be multiple form processing, such as, and the form of fibril, bulk fibre, yarn, knitted fabrics or woven fabrics.
The application of Monoazo compound of the present invention on filamentary material can realize according to known method.Such as, containing Polyester Fibers under optional common carrier (swelling agent), conventional anionic or non-ionic dispersing agent, levelling agent, buffer reagent, reduction preventing agent etc. exist, be dyeed by dip method by aqueous dispersion at the temperature of 4 ~ 4.5,100 ~ 140 DEG C in pH value; By the mode of padding, the dye slurry containing dispersed dye and migration preventing agent can also be applied to fabric, after drying, carry out hot melt fixation 15 seconds ~ 5 minutes in 180 ~ 225 DEG C; By the method scraped, the printing paste containing dispersed dye and thickening material can also be applied to fabric, again by saturation steam (147 ~ 176KPa, 120 ~ 140 DEG C, 10 ~ 45 minutes), superheated vapour (160 ~ 185 DEG C, 4 ~ 15 minutes) or heated dry air (190 ~ 225 DEG C, 0.5 ~ 5 minute) carry out fixation.Described thickening material is conventional thickening material, such as sodium alginate, treated starch, modified natural glue, carboxymethyl cellulose, Natvosol and polyacrylic synthetic thickener.Cellulose acetate and nylon are preferably contaminated at 85 ~ 115 DEG C.
In order to obtain extraordinary fastness, reduction clearing is needed after usual Monoazo compound dyeing of the present invention, as at 85 DEG C by V-Brite B and sodium-hydroxide treatment 20 minutes, fabric processes 20 minutes with acidic reduction agent (as hydroxyalkylsulfinic acids salt) at 85 DEG C again under pH value is 3.5 ~ 5.0 conditions if desired.
Monoazo compound of the present invention except being used alone, is also suitable for other dispersed dye used in combination as dispersed dye.Such as Monoazo compound of the present invention mixes with other dye composition and manufactures admixture of disperse dyes, based on the gross weight of described admixture of disperse dyes, the part by weight of Monoazo compound of the present invention is 1 ~ 99%, and the weight ratio of other dye composition is 1 ~ 99%.Or during printing and dyeing, the dispersed dye goods of Monoazo compound of the present invention use together with other dispersed dye any, composite required tone.
The invention still further relates to the coloured fibrous material containing described Monoazo compound.
The present invention is owing to have employed technique scheme, Monoazo compound of the present invention not easily staining, thermophoresis is slight, moisture-proof fastness and dry heat resistance sublimation fastness are very good, be very suitable for dyeing and the stamp of exigent polyester superfine fibre, polyester and spandex blending product, obtain good over-all properties.The present invention also has the following advantages: exhaustion when () contaminates, fixation, dyebath stability are good; (2) light fastness is good; (3) dyestuff coloring intensity is high, bright in color light.
With specific embodiment, the present invention is described below, but protection scope of the present invention is not limited in this.
Embodiment:
Embodiment 1
Frozen water and the Diamines compound shown in 5.8g formula (II-1) of 15g is added in reaction flask,
Under agitation drip 7.1gCNCH 2cOOCH 2cH 3, keep temperature≤5 DEG C reaction 4 hours, obtain formula (III-1) compound,
In reaction flask, drip 13g Benzoyl chloride, regulate PH=5 with 30% liquid caustic soda of 12g, control temperature≤10 DEG C reaction 8 hours, obtains formula (IV-1) compound,
Then, drip 30% liquid caustic soda of 4g, adjust system PH ≈ 9.5.Add 7.8g methyl acetoacetate and 6.0g70% ethylamine solution, be heated to 75 DEG C and keep reaction 12 hours, reaction solution is all poured in about 200ml cold water, system PH<2 is adjusted with sulfuric acid, Temperature fall, filters, washes twice with clear water, obtain the pyridine compounds 16.2g shown in formula (V-1)
In another reaction flask, add 10.0ml water, 15.2g30% hydrochloric acid, under agitation add the o-Nitraniline shown in 6.9g formula (VI-1),
Pull an oar half an hour, add 20g ice, add 3.8g Sodium Nitrite, keep system temperature≤5 DEG C, stirring reaction 2 hours, suction strainer, obtains o-Nitraniline diazonium salt solution.
Pyridine compounds 16.2g shown in formula (V-1) 500ml water and 1.8gNaOH dissolve, add the thionamic acid of 0.5g, o-Nitraniline diazonium salt solution is instilled, stirring reaction 2 hours, suction strainer, washing, uses DMF recrystallization, obtain such as formula the Monoazo compound 23.5g shown in (I-1)
Detect data:
CompoundⅠ-1:Anal.Calcd.for[C 24H 22N 6O 5]:C,60.75；H,4.67；N,17.71％.Found:C,60.51；H,4.44；N,17.52％.Main?FT-IR?absorptions(KBr?pellets,cm -1):3438(w),2229(w),1685(m),1637(s),1487(vs),1442(s),1326(m),1224(m). 1H?NMR(500MHz,CDCl 3)δ:15.91(d,1H,NH),8.33(m,1H,NO 2-benzene),8.08(m,1H,NO 2-benzene),7.76(m,1H,NO 2-benzene),7.36(m,1H,NO 2-benzene),8.33(m,1H,benzene),8.08(m,1H,benzene),7.76(m,1H,benzene),7.36(m,1H,benzene),7.33(m,1H,benzene),4.37(t,2H,py-NCH 2),3.89(m,2H,py-NCH 2CH 2),3.36(m,2H,-NCH 2),2.62(s,3H,py-CH 3),1.12(m,3H,-NCH 2CH 3).Negative?ESI-MS?in?methanol:m/z＝473.25,[M-H] -.λ max/ε(l·mol -1·cm -1)＝441.5/36475and?369/7977。
Embodiment 2:
By the 13g Benzoyl chloride in 10.9g Methanesulfonyl chloride alternate embodiment 1, obtained pyridine compounds 9.4g shown in formula (V-2),
By the o-Nitraniline in the p-Nitroaniline alternate embodiment 1 shown in equivalent formula (VI-2), obtain single sweep polarographic wave,
According to the coupling manner in embodiment 1, the pyridine compounds shown in formula (V-2) is mixed with the single sweep polarographic wave solution of equivalent, obtains such as formula the Monoazo compound 14.1g shown in (I-6),
Detect data:
CompoundⅠ-6:Anal.Calcd.for[C 19H 21N 5O 6S]:C,51.00；H,4.73；N,15.65％.Found:C,50.91；H,4.94；N,15.31％.Main?FT-IR?absorptions(KBr?pellets,cm -1):3420(w),2224(m),1687(m),1640(s),1591(vs),1442(s),1335(m),837(s).Negative?ESI-MS:m/z＝447.17,[M-H] -.λ max/ε(l·mol -1·cm -1)＝436.5/46003and?310/5288。
Embodiment 3
By the 13g Benzoyl chloride in 8g aceticanhydride alternate embodiment 1, obtained pyridone type heterogeneous ring compound 11.6g shown in formula (V-3),
By the o-Nitraniline in the adjacent nitro P-nethoxyaniline alternate embodiment 1 shown in 8.4g formula (VI-1), obtain adjacent nitro P-nethoxyaniline diazonium salt,
According to the coupling manner in embodiment 1, the pyridine compounds shown in formula (V-3) is mixed with the adjacent nitro P-nethoxyaniline diazonium salt solution of equivalent, obtains such as formula the Monoazo compound 19.5g shown in (I-8),
Detect data:
CompoundⅠ-8:Anal.Calcd.for[C 20H 22N 6O 6]:C,54.29；H,5.01；N,19.00％.Found:C,54.06；H,4.97；N,18.87％.Main?FT-IR?absorptions(KBr?pellets,cm -1):3450(w),2225(w),1683(m),1620(s),1504(s),1465(vs),1406(m),1269(m),1184(m). 1H?NMR(500MHz,CDCl 3)δ:15.91(d,1H,NH),8.07(m,1H,benzene),7.79(d,1H,benzene),7.38(m,1H,benzene),4.23(t,2H,py-NCH 2),3.93(s,3H,-OCH 3),3.67(t,2H,py-NCH 2),3.37(m,2H,-NCH 2),1.96(s,3H,py-CH 3),1.59(s,3H,-NCOCH 3),1.21(m,3H,-NCH 2CH 3).Negative?ESI-MS:m/z＝441.25,[M-H] -.λ max/ε(l·mol -1·cm -1)＝473.0/32277and?397/10400。
Embodiment 4:
By the Monoazo compound shown in 10 grams of formulas (I-1), 20 grams of Dispersant MFs and 50 grams of water mixing, add sand milling pearl, be ground to Monoazo compound particle diameter with sand mill and be less than 2 microns, with filter screen filtering sand milling pearl, obtain the liquid dispersed dye preparations of Monoazo compound shown in formula (I-1).Wherein containing 12.5% Monoazo compound, 25% Dispersant MF and 62.5% water.
Embodiment 5:
The liquid dye goods of Monoazo compound embodiment 4 Chinese style (I-1) Suo Shi are carried out spraying dry, obtains powder state dispersed dye goods.Wherein containing Monoazo compound shown in 30% formula (I-1), 60% Dispersant MF and 10% water.
Embodiment 6:
Get dyestuff powder state goods shown in formula (I-1) obtained in 0.5g (o.w.f.=5%) embodiment 5, be dispersed in 80ml water, be 5 with vinegar acid for adjusting pH, put into the terylene flat fabric that 10g specification is 167dtex48f (150D48F), 130 DEG C are heated to the temperature rise rate of 2 DEG C/min, be incubated 45 minutes, be cooled to less than 85 DEG C and take out fabric, be washed to clean; With the solution containing 3g/l V-Brite B and 2g/l sodium hydroxide in 85 DEG C of process 20 minutes, use water rinse, dry, in 160 DEG C of xeothermic sizings 30 seconds, obtain deeply dense gorgeous yellow colored fabric.
The method that reference example 1-6 is similar, preparation formula I-2), the colored fabric of formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), formula (I-9), formula (I-10), formula (I-11), C.I. DISPERSE YELLOW 119, C.I. DISPERSE YELLOW 126, C.I. DISPERSE Yellow 211, C.I. DISPERSE YELLOW 114, C.I. DISPERSE YELLOW 241, formula (VII) and formula (VIII).
By the 2A method specified in GB/T5718-1997 textiles dry heat resistance (distillation) colour fastness test method (being equivalent to ISO 105-P01), the resistance to family of AATCC61-2007, commercial laundering colour fastness, the GBT 8427-2008 textile color stability test _ colour fastness of resistance to artificial light (xenon arc), respectively its dry heat resistance (distillation), water-fastness, resistance to water logging, the colour fastness such as fast light are tested to described colored fabric; Utilize reflection-type spectrophotometer to test the reflectivity of colored fabric, by Kubelka-Munk formulae discovery depth factor, its maximum value is designated as K/Smax, and test result is listed in table 1.
Embodiment 7:
With the 150D48F ordinary polyester flat fabric in the 50D96F dacron ultrafine fiber flat fabric alternate embodiment 6 of equivalent, prepare the painted thing of dacron ultrafine fiber by the method dyeing of embodiment 6, and carry out performance test, test result is listed in table 2.
Embodiment 8:
The blended knitted cloth of ammonia is washed (containing terylene 90% spandex 10% with equivalent, terylene specification is 100D72F) the ordinary polyester flat fabric of 150D48F in alternate embodiment 6, the painted thing of ammonia blended yarn weaved fabric is washed by the method dyeing preparation in embodiment 6, and carry out performance test, test result is listed in table 3
From above data, present invention obtains good over-all properties, there is obvious progress compared with known dye.
Table 1: ordinary polyester fabric performance test result:
Table 2: dacron ultrafine fiber fabric performance test result:

Claims (8)

1. a Monoazo compound, its structure is as shown in formula I:
In formula I:
R 1for hydrogen, methoxyl group, C 2 ~ 4alkoxyl group, nitro, halogen or-COOR, wherein R is C 1 ~ 4alkyl, C 1 ~ 4alkyl oxygen ethyl, C 1 ~ 4alkyl oxygen ethyl oxygen ethyl or phenyl,
R 2for hydrogen, halogen or C 6h 5sO 2o-,
R 3for hydrogen, halogen, cyano group or nitro,
R 4for hydrogen, halogen, cyano group or nitro,
R 5for-CH 2cH 2-,-CH 2cH 2cH 2-or-CH 2cH (CH 3)-,
R 6for methyl, ethyl, phenyl or C 3 ~ 6alkyl,
R 7for methyl, C 2 ~ 4alkyl, phenyl or tolyl,
Z is C or SO.
2. Monoazo compound as claimed in claim 1, is characterized in that: its structure is such as formula shown in (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (I-7), (I-8), (I-9), (I-10) or (I-11):
3. liquid dye goods, is characterized in that, the weight percentage of Monoazo compound according to claim 1 is 10 ~ 30%, and the weight percentage of auxiliary agent is 5 ~ 45%, and all the other are water or other synergistic agent.
4. solid dye goods, is characterized in that, the weight percentage of Monoazo compound according to claim 1 is 10 ~ 60%, and the weight percentage of auxiliary agent is 40 ~ 90%.
5. Monoazo compound described in claim 1 is as hydrophobic synthetic fiber and blended material dyeing thereof and the purposes of stamp.
6. purposes as claimed in claim 5, is characterized in that, described Monoazo compound is as the purposes of polyester and blended material dyeing and stamp.
7. an admixture of disperse dyes, is characterized in that, based on the gross weight of described admixture of disperse dyes, the part by weight of Monoazo compound described in claim 1 is 1 ~ 99%, and the weight ratio of other dye composition is 1 ~ 99%.
8. one kind contains the articles colored of polyester material, and it is waited to levy and is to contain Monoazo compound as claimed in claim 1.
CN201410377742.6A 2014-08-01 2014-08-01 Monoazo compound as well as product and application thereof Pending CN104231660A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410377742.6A CN104231660A (en) 2014-08-01 2014-08-01 Monoazo compound as well as product and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410377742.6A CN104231660A (en) 2014-08-01 2014-08-01 Monoazo compound as well as product and application thereof

Publications (1)

Publication Number Publication Date
CN104231660A true CN104231660A (en) 2014-12-24

Family

ID=52220612

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410377742.6A Pending CN104231660A (en) 2014-08-01 2014-08-01 Monoazo compound as well as product and application thereof

Country Status (1)

Country Link
CN (1) CN104231660A (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1179446A (en) * 1997-11-06 1998-04-22 大连理工大学化工学院 Red colour composite monoazo-dyes for dyeing synthetic fibre
CN1496388A (en) * 2001-03-09 2004-05-12 �������⻯ѧƷ�ع����޹�˾ Pyridone dyes, a process for their preparation and their use in production of colorued plastics or polymeric colour particles
US20040143107A1 (en) * 2001-05-07 2004-07-22 Athanassios Tzikas Pyridone dyes, a process for the preparation and their use in the production of coloured plastics or polymeric colour particles
WO2005063592A1 (en) * 2003-12-23 2005-07-14 Ciba Specialty Chemicals Holding Inc. Method of protecting organic material from light
US20060160933A1 (en) * 2002-08-30 2006-07-20 Ian Christensen Method of producing coloured plastics or polymeric color particles
CN102127316A (en) * 2011-01-27 2011-07-20 浙江昱泰染化科技有限公司 Disperse scarlet dye composite

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1179446A (en) * 1997-11-06 1998-04-22 大连理工大学化工学院 Red colour composite monoazo-dyes for dyeing synthetic fibre
CN1496388A (en) * 2001-03-09 2004-05-12 �������⻯ѧƷ�ع����޹�˾ Pyridone dyes, a process for their preparation and their use in production of colorued plastics or polymeric colour particles
US20040143107A1 (en) * 2001-05-07 2004-07-22 Athanassios Tzikas Pyridone dyes, a process for the preparation and their use in the production of coloured plastics or polymeric colour particles
US20060160933A1 (en) * 2002-08-30 2006-07-20 Ian Christensen Method of producing coloured plastics or polymeric color particles
WO2005063592A1 (en) * 2003-12-23 2005-07-14 Ciba Specialty Chemicals Holding Inc. Method of protecting organic material from light
CN102127316A (en) * 2011-01-27 2011-07-20 浙江昱泰染化科技有限公司 Disperse scarlet dye composite

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
陈冠荣等: "《化工百科全书-第4卷》", 30 September 1993, 化学工业出版社 *

Similar Documents

Publication Publication Date Title
TWI633158B (en) Disperse dye mixtures, their preparation and use
CN100503740C (en) Dispersed black dye composition
TWI282810B (en) Disperse dye mixtures
CN101323712B (en) Dispersed black dye composition
TWI507486B (en) Disperse azo dyes, disperse dye composition, dyed material and process for preparing disperse azo dyes
CN109705618B (en) Disperse brilliant red dye composition and dye product
KR100847236B1 (en) Azo dyes, dye mixtures, a process for their preparation and a process for dyeing or printing of hydrophobic fiber materials using them
CN103468023A (en) Dispersed black azo dye mixture
CN102604426A (en) Compound disperse black azo dye
CN101067050B (en) Disperse black dye composition
KR20070054627A (en) Disperse dye mixtures
KR20020021770A (en) Azo disperse dye mixtures
CN102816453B (en) Disperse dye monomeric compound and disperse dye
JPH0579265B2 (en)
CN111269586B (en) Disperse black dye composition, disperse black dye preparation and application thereof
TWI509028B (en) Disperse dyes
JP2002531624A (en) Disperse dye mixture
TWI428399B (en) Blue anthraquinone dyes, their preparation and use
CN104231660A (en) Monoazo compound as well as product and application thereof
JP2002513869A (en) Disperse dye mixture
CN106977975B (en) Azo dispersion dyes compound and its synthetic method and tint applications
CN105111104B (en) Disperse dye monomer compound, disperse dye preparation and applications of disperse dye preparation
EP3645632A1 (en) Disperse azo dyes
EP2859051B1 (en) Anthraquinone azo dyes
TWI830702B (en) Disperse azo dyes

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20141224