CN105623298B - A kind of orange disperse dye compound and its application - Google Patents
A kind of orange disperse dye compound and its application Download PDFInfo
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- CN105623298B CN105623298B CN201610104848.8A CN201610104848A CN105623298B CN 105623298 B CN105623298 B CN 105623298B CN 201610104848 A CN201610104848 A CN 201610104848A CN 105623298 B CN105623298 B CN 105623298B
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- disperse dye
- orange disperse
- dye compound
- orange
- compound
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 238000007639 printing Methods 0.000 claims abstract description 13
- -1 Hydrogen Chemical class 0.000 claims abstract description 9
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 9
- 239000002657 fibrous material Substances 0.000 claims abstract description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007859 condensation product Substances 0.000 claims description 8
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 claims description 3
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical group O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 238000005406 washing Methods 0.000 abstract description 6
- 238000000859 sublimation Methods 0.000 abstract description 5
- 230000008022 sublimation Effects 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052794 bromium Inorganic materials 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000005859 coupling reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 239000004744 fabric Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 0 *c1ccc(CN(*)c(cc2)ccc2N=NC(C(Cl)=CC(C2)[N+]([O-])=O)=C2Cl)cc1 Chemical compound *c1ccc(CN(*)c(cc2)ccc2N=NC(C(Cl)=CC(C2)[N+]([O-])=O)=C2Cl)cc1 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical class COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- BBJZIVDFAGBWHH-UHFFFAOYSA-N C=CC.N#CC#N Chemical compound C=CC.N#CC#N BBJZIVDFAGBWHH-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 235000012544 Viola sororia Nutrition 0.000 description 1
- 241001106476 Violaceae Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
The invention discloses a kind of orange disperse dye compound and its application, orange disperse dye compounds, shown in structure such as formula (I), wherein X1、X2Hydrogen, chlorine or bromine are respectively stood alone as, R is methyl, ethyl, methoxyl group, chlorine or bromine.The present invention provides application of the orange disperse dye compound in hydrophobic fiber material printing and dyeing, the application is bright in colour when hydrophobic fiber material is printed and dyed, lifting force is good, every color fastness is excellent, and special fastness to sublimation and washing fastness protrude.
Description
(1) technical field
The present invention relates to a kind of orange disperse dye compound and its application, especially a kind of azo-type orange disperse dye
Compound and its application in hydrophobic fiber material printing and dyeing.
(2) technical background
With the development of super fine denier polyester fiber ,/the development of the high-grade blended fabric such as ammonia, polyester cotton and is washed, existing point
Scattered dyestuff has been unable to meet its dyeing demand in printing and dyeing, and such as dyeing color fastness is bad, when especially washing fastness is short of, dyes
Loose colour is more etc..288 usage amount of C.I. disperse oranges is larger in orange disperse dye, because of its simple production process, at low cost, color and luster
The advantages that bright-coloured and be widely used, but it is still to be improved in terms of fastness to sublimation and washing fastness.
(3) invention content
Present invention aims at：A kind of orange disperse dye compound is provided, the application is in hydrophobic fiber material
It is bright in colour when printing and dyeing, lifting force is good, every color fastness is excellent, special fastness to sublimation and washing fastness protrude.
The technical solution adopted by the present invention is：
A kind of orange disperse dye compound, shown in structure such as formula (I)：
In formula (I), X1、X2Hydrogen, chlorine or bromine are respectively stood alone as, R is methyl, ethyl, methoxyl group, chlorine or bromine.
Further, R is ortho position or para-orientating group.
Further, the orange disperse dye compound is one of following formula：
Again further, the orange disperse dye compound is formula (I-1).
Orange disperse dye compound of the present invention can be by diazotising well known in the art, coupling reaction mode system
It is standby, specifically comprise the following steps：(1) formula (II) compound is carried out in acid medium with nitrosyl sulfuric acid to diazotising, control
Temperature is between 0~20 DEG C；(2) diazonium that step (1) obtains is added in formula (III) compound stirring to pulp in acid medium
Salt, control temperature carry out coupling reaction between 0~10 DEG C；(3) after reaction by material be warming up to 70~80 DEG C heat preservation 2~
4 hours, then filter, wash to neutrality, the orange disperse dye compound is made；
In formula (II) and formula (III), X1、X2, R the same formula of definition (I).
In the present invention, formula (II) and formula (III) compound can be prepared by method well known in the art, and commercially available quotient can also be used
Product.
The present invention provides application of the orange disperse dye compound in hydrophobic fiber material printing and dyeing.
The orange disperse dye compound is applied to that when dyeing, stamp commercial treatment need to be carried out, and generally requires and adds
Enter auxiliary agent to be disperseed, such as corpusculed is carried out with pulverizers such as sand mill or grinders in the presence of auxiliary agent, water.Therefore this
Invention provides a kind of orange disperse dye, including the orange disperse dye compound and auxiliary agent.The auxiliary agent is point
Common dispersant, diffusant, wetting agent and surfactant etc. when commercialization of dyes are dissipated, it is preferably one of following or in which arbitrary
Several mixtures：It is naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic acid-formaldehyde condensation product, wooden
The anionic dispersing agents such as plain sulfonate.Specifically, naphthalene sulfonic acid-formaldehyde condensation product such as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation
Object such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalene sulfonic acid-formaldehyde condensation product such as dispersing agent CNF etc., sulfomethylated lignin
Hydrochlorate such as sodium lignin sulfonate (such as commercial dispersants Reax83A, Reax85A).It the orange disperse dye compound and helps
Agent mass ratio is 1:0.2~5.The present invention orange disperse dye can with after corpusculed liquid, emulsifiable paste state or with spray
Mist seasoning etc. be dried after powdery, graininess supply printing and dyeing.
Common dip method can be used in orange disperse dye manufactured according to the present invention, pad-dyeing method is dyed, it can also be used to
Direct printing.Wherein, common dip method such as pre-processes polyester textile, is put into dye vat and is disseminated, and dye finishes, and cold water is clear
It is washed till neutrality, is squeezed out, cleaning is restored again, is dried；Fabric is such as carried out dye pre-treatment by direct printing, is dried, and setting is printing
Disperse dyes mill base is printed on flower machine, then is evaporated, the dye fixing on fabric is made in the way of decatize, is finally washed, tentering
Sizing.
Printing and dyeing using orange disperse dye produced by the present invention especially suitable for hydrophobic fiber material, including it is semi-synthetic
Or the blended printing and dyeing of hydrophobic fibre of synthesis, the printing and dyeing of polyester fiber are particularly suitable for, uniform hue, Ge Xiangse can be obtained
Fastness is excellent, especially has excellent washability and splendid resistance to sublimability, is also applied for medium-to-high grade fabric such as super fine denier and knits
Object, polyester cotton wash the/printing and dyeing of the blended fabric such as ammonia.
In addition, orange disperse dye compound of the present invention can also compound to obtain respectively with other disperse dye compounds
The dye species of kind tone, such as can be with C.I. disperse violets 93, C.I. disperse blues 291, C.I. disperse blues 291:1, C.I. disperses
The dyestuffs compoundings such as indigo plant 79 obtain the dye species such as the disperse blue haveing excellent performance, black.
Compared with prior art, the beneficial effects of the present invention are：Orange disperse dye compound provided by the invention is answered
It is bright in colour, lifting force is good, every color fastness is excellent when printing and dyeing for hydrophobic fiber material, special fastness to sublimation and resistance to
Washing fastness protrudes.
(4) specific implementation mode
With reference to embodiment, the invention will be further described, but protection scope of the present invention is not limited to that.
Embodiment 1：
The preparation of coupling component：The aniline of input 0.1mol in 250ml containers, the propylene cyanogen of 0.12mol, 50mol's
Water is warming up to 90 DEG C, keeps the temperature 10h, cooling while the methanol that 30mol is added, and in 0~5 DEG C of insulated and stirred 12h, crystallization filtering is used
The methanol of 20mol washs, and is dried after washed, it is spare to obtain single cyanogen compound；In to 250ml containers put into 0.1mol to methyl
Benzyl chloride, the soda ash of 0.2mol, 0.05mol single cyanogen compounds obtained above are warming up to 80 DEG C, put into the KI of 0.1mol, protect
Warm 12h cools to 40 DEG C, and the water of 50mol, crystallization filtering is added to obtain coupling component shown in formula (III -1).
Diazotising：To in the container of 250ml, the water of 1.38mol is put into, 98% concentrated sulfuric acid of 0.88mol is added in cooling, after
It is continuous to be cooled to 10 DEG C, the paranitroanilinum of 0.1mol is added, 4h is stirred in temperature control at 20~30 DEG C；It is slowly dripped at 10~15 DEG C
Add the nitrosyl sulfuric acid of 0.105mol, control time for adding continues to stir 4h after dripping, it is (standby to obtain diazo liquid in 6~7h
With).
Coupling reaction：The water of 55.5mol, 98% concentrated sulfuric acid of 0.5mol, the formula (III-of 0.1mol are put into 2L containers
1) coupling component is beaten half an hour；The diazo liquid of the above-mentioned preparation of dropwise addition in 20min, 0~5 DEG C of coupling reaction 5 of control temperature~
Material is warming up to 75 DEG C, then keep the temperature 3h, filtered, washed in by 6h (with circle experiment detection reaction end is oozed) after the reaction was complete
Property, dye composition shown in formula (I -1) is obtained, λ max are 465nm in DMF solution.Then auxiliary agent MF, water grinding is added
Even, drying and dehydrating is up to disperse dyes, wherein the weight ratio of MF and dye composition is 1.6:1, water is auxiliary agent MF and dyestuff
2 times of the sum of compound by weight.
Embodiment 2~15：
The preparation of coupling component：According to the preparation method of coupling component described in embodiment 1, by intermediate feed to methyl
Benzyl chloride replaces with 4- methoxybenzyl chlorides, 4- bromines benzyl chloride, 4- chlorine benzyl chloride, 2- ethylmercury chloride benzyls respectively, can be made respectively
Intermediate shown in embodiment 2,3,4 and 13 Chinese styles (III) structure in the following table 1.
The preparation of dyestuff：According to the diazo coupling method described in embodiment 1, the difference is that by raw material diazo component, idol
It is combined formula (II), the compound of formula (III) point being substituted in the following table 1, obtains dye composition shown in table and its in DMF
Then auxiliary agent MF, water grinding is added uniformly in λ max in solution, drying and dehydrating is up to disperse dyes, wherein MF and dyestuff chemical combination
The weight ratio of object is 1.6:1, water is 2 times of the sum of auxiliary agent MF and dye composition weight, and being applied to can be by fabric when dyeing
It dyes orange：
1 raw material of table and dye composition
Embodiment 16：
The preparation of coupling component：By coupling component shown in method formula described in embodiment 1 (III -1).
Diazotising：98% concentrated sulfuric acid of 0.88mol, the nitrosyl sulfuric acid of 0.105mol, cooling are added into 250ml containers
To 0~5 DEG C, 2, the 6- dichloro paranitroanilinum for adding 0.1mol in 3~4h is controlled, 3h is kept the temperature after adding, it is (standby to obtain diazo liquid
With).
Coupling reaction：The water of 55mol, 98% concentrated sulfuric acid of 0.2mol, the formula (III -1) of 0.1mol are put into 2L containers
Coupling component, mashing half an hour, the interior diazo liquids that above-mentioned preparation is added dropwise of 1~2h of control, 0~5 DEG C of coupling reaction 5 of control temperature~
Material is warming up to 75 DEG C, then keep the temperature 3h, filtered, washed in by 6h (with circle experiment detection reaction end is oozed) after the reaction was complete
Property, dye composition shown in formula (I -16) is obtained, λ max are 420nm in DMF solution.Then auxiliary agent MF, water grinding is added
Uniformly, drying and dehydrating is up to disperse dyes, wherein the weight ratio of MF and dye composition is 1.6:1, water is auxiliary agent MF and dye
Expect the sum of compound by weight 2 times.
Embodiment 17~25：
According to the preparation method described in embodiment 16, the difference is that raw material diazo component, coupling component are substituted for the following table 2
In formula (II), the compound of formula (III), obtain dye composition shown in table and its λ max in DMF solution, then
Auxiliary agent MF, water grinding is added uniformly, drying and dehydrating is up to disperse dyes, wherein the weight ratio of MF and dye composition is 1.6:
1, water is 2 times of the sum of auxiliary agent MF and dye composition weight, can be dyed fabric when applied to dyeing orange：
2 raw material of table and dye composition
Comparative example 1：
It will as a comparison case, structure be as follows for common C.I. disperse oranges 288 on the market：
Disperse dyes are prepared according to the method for embodiment 1.
Tint applications example 26：
Disperse dyes made from 3 grams of embodiment 1-25, disperse dyes shown in comparative example 1 are weighed respectively, are dispersed in 500 millis
It rises in water, is mixed with 80 milliliters of water after drawing 20 milliliters, with acetic acid tune pH to 4.5, be put into 4 grams of polyester textiles, be warming up to 60
DEG C, continue with about 1 DEG C/min gradient increased temperatures to 130 DEG C, heat preservation dyeing 45 minutes.Then 80 DEG C or so are cooled to and uses hot water wash
10min, drying, the method described in GB/T 5718-1997, GB/T 3921-2008 that is respectively adopted measure its it is resistance to distillation and it is resistance to
Washing, measurement result see the table below 1：
Table 1
Tint applications example 27：
Disperse dyes made from 4 grams of embodiment 1-25, disperse dyes shown in comparative example 1 are weighed respectively, are dispersed in 500 millis
It rises in water, is mixed with 80 milliliters of water after drawing 20 milliliters, with acetic acid tune pH to 4.5, be put into 4 grams of super fine polyester cloth, be warming up to
60 DEG C, continue with about 1 DEG C/min gradient increased temperatures to 130 DEG C, heat preservation dyeing 45 minutes.Then 80 DEG C or so are cooled to and uses hot water wash
10min, drying, the method described in ISO105-P01, GB/T 3921-2008 that is respectively adopted measure its it is resistance to distillation and it is water-fastness
Color fastness, measurement result see the table below 2：
Table 2
By above-mentioned table 1, table 2 it is found that orange disperse dye provided by the invention, using polyester textile or ultra-fine polyester textile
When dyeing, fastness to sublimation terylene staining fastness, water-fastness vinegar fibre staining fastness, nylon staining fastness and wool staining fastness are equal
It is substantially better than C.I. disperse oranges 288.
Claims (5)
1. a kind of orange disperse dye compound, the orange disperse dye compound is one of following formula：
2. application of the orange disperse dye compound as described in claim 1 in hydrophobic fiber material printing and dyeing.
3. a kind of orange disperse dye, including orange disperse dye compound as described in claim 1 and auxiliary agent.
4. orange disperse dye as claimed in claim 3, it is characterised in that：The auxiliary agent is one of following or in which arbitrary
Several mixtures：It is naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic acid-formaldehyde condensation product, wooden
Plain sulfonate.
5. orange disperse dye as described in claim 3 or 4, it is characterised in that：It the orange disperse dye compound and helps
Agent mass ratio is 1:0.2~5.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2105361A (en) * | 1981-08-05 | 1983-03-23 | Yorkshire Chemicals Ltd | Azo disperse dyes and processes for their preparation |
| DE19816056A1 (en) * | 1998-03-23 | 1999-09-30 | Dystar Textilfarben Gmbh & Co | Dispersion azo dye mixtures |
| ES2172266T3 (en) * | 1998-03-23 | 2002-09-16 | Dystar Textilfarben Gmbh & Co | BLENDS OF DISPERSED MONOAZOIC COLORS. |
| CN101265369B (en) * | 2008-05-14 | 2010-06-09 | 浙江汇德隆化工有限公司 | Azo dye composition and application thereof |
| CN102660145B (en) * | 2012-04-28 | 2014-06-25 | 浙江万丰化工有限公司 | Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof |
| CN102660146B (en) * | 2012-04-28 | 2013-12-11 | 浙江万丰化工有限公司 | Oxidation-resistant disperse dye composition and preparation and application thereof |
| KR101416893B1 (en) * | 2012-06-08 | 2014-07-08 | 공명도 | Orange disperse dye composition having excellent moisture resistance |
| CN103450706A (en) * | 2013-09-07 | 2013-12-18 | 张家港市杨舍丝印工艺厂 | Dye composition (red brown) and preparation method thereof |
| CN104151866B (en) * | 2014-07-22 | 2016-06-08 | 俞杏英 | A kind of alkaline-proof disperse dyes compositions based on the thiazole heterocycle orchil containing benzoyloxy and application thereof |
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