CN106084874B - A kind of disperse dyes and preparation method and application - Google Patents

A kind of disperse dyes and preparation method and application Download PDF

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Publication number
CN106084874B
CN106084874B CN201610415626.8A CN201610415626A CN106084874B CN 106084874 B CN106084874 B CN 106084874B CN 201610415626 A CN201610415626 A CN 201610415626A CN 106084874 B CN106084874 B CN 106084874B
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disperse dyes
formula
diazo
fabric
fastness
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CN106084874A (en
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赵雪
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University of Shaoxing
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University of Shaoxing
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    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0836—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N=
    • C09B29/0838—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N= specific alkyl-CO-N-, aralkyl CON-, cycloalkyl CON-, alkyl OCON-
    • 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
    • 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
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention discloses fluorine-containing disperse dyes of a kind of high washing fastness and preparation method and application, structural formula is as follows：The disperse dyes dyestuff of the present invention contain hydroxyl, ester group and long chain etc. between structure, with fiber affinity it is high, make that dyestuff is more difficult to move to fiber surface, show higher color fastness, can be applied to the one-bath two-step process dyeing such as polyester-cotton blend, reduce technological process；Or the polyester fabric for washing ammonia elastic fabric, dacron ultrafine fiber fabric, having special Final finishing demand, fabric washing fastness can be improved.

Description

A kind of disperse dyes and preparation method and application
Technical field：
The present invention relates to a kind of disperse dyes, more specifically refer to a kind of fluorine-containing disperse dyes of high washing fastness and its preparation side Method and application.
Background technology：
Dacron typically uses disperse dyes high-temperature pressure dyeing, by Van der Waals force and intermolecular hydrogen bonding power and fiber With reference to therefore if washing is abundant after dyeing, surface loose colour removes clean, color fastness such as Washing, PERSPIRATION COLOR FASTNESS, water stain Color fastness can reach more than 3 grades.But with social development, new type polyester fiber more and more to polyester fabric Functional Requirement The element such as fabric and new design collocation is widely used in garment material, to the color fastness especially Washing of disperse dyes Propose new or higher requirement.
Dacron is dispersed through after dyeing to handle through high temperature setting, especially when functional arrange requires addition auxiliary agent When, such as softening agent, three-proof finishing agent, soil-releasing finishing agent, hydrophilizing agent, UV resistance agent and antistatic additive, due to finishing agent into Divide complexity, wherein the chemical composition containing aggravation dye migration, dyestuff easily moves to fiber surface from fibrous inside and occurs institute Thermophoresis is called, washing fastness will be significantly reduced.
Ammonia stockinette is washed because feel is plentiful smooth, wide to have body bone, drapability and anti-crease property are good, are usually used in high-end Dress shell fabric.But a large amount of disperse dyes can be adsorbed by washing ammonia stockinette spandex when being dyed with disperse dyes to terylene, and And loose colour also is difficult to remove through being cleaned multiple times on spandex, the problem of there is poor color fastness.Contain urea groups, ammonia in spandex macromolecular Carbamate, ester group and ether etc., disperse dyes have good colourability to it.Disperse dyes are studied and found, polyester fibre/spandex Disperse dyes content ratio for it is most be less than in 1, i.e. spandex also contain more disperse dyes, and the glass transition temperature of spandex it is low (- 50~70 DEG C), it can be discharged at a temperature of conventional water wash in water lotion, cause color fastness decreased, such as knitted with following dyeing Thing is washed under the conditions of 60 DEG C, and washing fastness is only 1.5 grades.
Fine-denier polyester fiber is made into clothes, there is preferable drapability and richness, high resilience and bulkiness, is moulded naturally Body, is unlikely to deform, and is usually used in manufacturing high-grade men and women's fashionable dress, jacket etc..But because fine-denier polyester fiber specific surface area is big, during dyeing Dye strength is again high, and the problem of washing fastness is reduced after high temperature setting is more prominent.Therefore, fine denier polyester/elastomeric polyurethane fiber fabric is adopted It is difficult to obtain high washing fastness with conventional disperse dyestuff.
At present, high washing fastness disperse dyes are paid attention to by research and development, the following knot of such as CN201410223244.6 reports The disperse dyes of structure：
The disperse dyes of the following structure of CN201410659122.1 and CN201410659443.1 reports：
The content of the invention：
The first aspect of the present invention purpose is to provide a kind of fluorine-containing disperse dyes with high washing fastness.
To reach goal of the invention, the technical scheme that the present invention is provided is as follows.
A kind of disperse dyes, its structural formula is as follows：
In formula：
X is hydrogen-based or nitro；
Y is hydrogen-based, chloro, bromo or cyano group etc..
Further, the disperse dyes are one of following structural formula；
Disperse dyes of the present invention, be in a kind of fluorine-containing disperse dyes of high washing fastness, dyestuff containing hydroxyl, ester group and Long chain etc. between structure, with fiber affinity it is high, make that dyestuff is more difficult to move to fiber surface, show higher color jail Degree, and the disperse dyes are more sensitive to alkali, can be hydrolyzed under weak basic condition water-soluble dye (as formula IV, formula V, Shown in formula VI), lose the affinity to terylene etc., it is easier to wash surface loose colour off.And alkali washing process is used only after dye, can To avoid under the conditions of sodium hydrosulfite reduction cleaning the azo group generation carcinogenic aromatic amine that is decomposed from being discharged into sewage, sewage is effectively reduced BOD values, reduce processing load.
The second aspect of the present invention purpose is to provide a kind of preparation method of foregoing disperse dyes, it is characterised in that including Following steps are as follows；
(1) compound shown in formula (II), is subjected to diazo-reaction in diazo reagent and obtains diazol；
In formula：
X is hydrogen-based or nitro；
Y is hydrogen-based, chloro, bromo or cyano group etc.；
(2) compound shown in the diazol obtained by step (1) and formula (III) is subjected to coupled reaction, produces the present invention The fluorine-containing disperse dyes of described high washing fastness；
It is preferred that：
Diazo reagent is nitro sulfuric acid and acetic acid/propionic acid (V in step (1)：V=4/1) mixture, or hydrochloric acid and nitrous The mixture of sour sodium.
The temperature of diazo-reaction is between -5 DEG C~5 DEG C in step (1).
Diazonium compound and the amount ratio of diazo reagent reactive material are 1 in step (1)：1.0~1.05.
Coupling reaction is 1 in step (2)：1(V：V) in methanol solution, carried out under the conditions of -5 DEG C~5 DEG C.
Diazonium salt dissolving and the amount ratio of coupling reagent reactive material are 1 in step (2)：1.0~1.05, adjust pH with sodium acetate =5-6.
The third aspect of the present invention purpose provides a kind of application of above-mentioned disperse dyes, and the disperse dyes can be applied to wash The one-bath two-step process dyeing such as cotton, reduces technological process；Can also be applied to wash ammonia elastic fabric, dacron ultrafine fiber fabric, There is the dyeing of the polyester fabric of special Final finishing demand, fabric washing fastness can be effectively improved.
Beneficial effects of the present invention are as follows：
1st, the water solubility for being hydrolyzed to sulfonic group, improving dyestuff of fluorine-containing disperse dyes of the invention in the basic conditions, Affinity of the dyestuff to fiber is reduced, soaping fastness is improved.
2nd, fluorine-containing disperse dyes prepared by the present invention have higher resistance to thermal mobility, and dyestuff is difficult to move under the conditions of the external world Fiber surface is moved on to, the dyestuff of fiber surface is easily moved on a small quantity to be hydrolyzed in subsequent water-washing process, entered from fibre shedding Enter water lotion, so as to improve fiber color fastness.
With reference to embodiment, the present invention is described further, but protection scope of the present invention and not only limits In this.
Brief description of the drawings：
The H NMR spectras for the chemical compounds I -1 that Fig. 1 is prepared for the present invention；
The H NMR spectras for the chemical compounds I -2 that Fig. 2 is prepared for the present invention；
The H NMR spectras for the chemical compounds I -3 that Fig. 3 is prepared for the present invention；
The H NMR spectras for the chemical compounds I -4 that Fig. 4 is prepared for the present invention；
The H NMR spectras for the chemical compounds I -5 that Fig. 5 is prepared for the present invention.
Embodiment：
Prepare embodiment 1：
(1), prepared by diazol：
In the there-necked flask with agitator, by 4- chlorosulfonic acid base phenyl acetamides (12.0g), potassium fluoride (180g) and 240 milliliters of water mixed dissolution, is stirred at reflux 3h, then adds in ice bath and precipitates, is cleaned with 40 DEG C of running water of pH value 4~5 cold But thing, collects sediment.0.1 mole of 4- fluorine sulfonanilide of sediment is dissolved in 35 milliliters of concentrated hydrochloric acids and 350.0 milliliters of water, 0.1 molar sodium nitrate is added in the calcium chloride ice bath of -5 DEG C of -5 DEG C of temperature.Sodium acetate regulation is added after 4-5 hours diazotising PH value is filtered to pH 5-6, washing.
(2), coupling reaction：
0.1 moles diazonium salt liquid is added to containing 0.1 mole of coupling component solution, in 500ml methanol and 500g ice baths, instead Answer 4-5 hours, then diazo liquid is by adding sodium acetate regulation pH value to pH 5-6.The dye filtering of precipitation, is washed with water simultaneously Dry.Dyestuff methanol obtains structural formula (I -1) dyestuff by crystallization purifying.
Embodiment 2-5：
Preparation method be the same as Example 1, difference is：Change diazo reagent, diazo-reaction temperature, diazonium compound with The amount of diazo reagent reactive material is than, diazonium salt dissolving and the amount ratio of coupling reagent reactive material, the different disperse dyes of acquisition It is as shown in the table.
Table 1,
Product confirms：
Chemical compounds I -1：
Chemical formula：
Physico-chemical parameter：It is purplish red solution, maximum absorption wavelength 523nm under brown solid particle, toluene solvant.
Structural confirmation：
1H-NMR(DMSO-d6):δ=7.05 (d, J=7.30Hz, 1H, Ar-H), 8.00 (d, J=2.50Hz, 1H, Ar- ), H 8.50 (d, J=2.50Hz, 1H, Ar-H), 3.93-4.20 (m, 2H, CH2), 3.86 (d, 3H, J=2.80, OCH3),2.62 (t, 2H, J=3.60Hz, 3.60Hz, CH2COO),2.03(s,3H,CH3CO),1.07(m,3H,CH2CH3),4.85(s,1H, OH),10.25(s,1H,NH)。
Chemical compounds I -2：
Chemical formula：
Physico-chemical parameter：It is blue-violet solution, maximum absorption wavelength 578nm under light green solid particle, toluene solvant.
Structural confirmation：
1H-NMR(DMSO-d6):δ=7.05 (d, J=7.30Hz, 1H, Ar-H), 8.40-8.93 (m, 1H, Ar-H), 3.93-4.20(m,2H,CH2), 3.86 (d, 3H, J=2.80, OCH3), 2.62 (t, 2H, J=3.60Hz, 3.60Hz, CH2COO),2.03(s,3H,CH3CO),1.07(m,3H,CH2CH3),4.85(s,1H,OH),10.25(s,1H,NH)。
Chemical compounds I -3：
Chemical formula：
Physico-chemical parameter：It is blue solution, maximum absorption wavelength 599nm under green solid particle, toluene solvant.
Structural confirmation：
1H-NMR(DMSO-d6):δ=7.05 (d, J=7.30Hz, 1H, Ar-H), 8.80 (s, 1H, Ar-H), 3.93- 4.20(m,2H,CH2), 3.86 (d, 3H, J=2.80, OCH3), 2.62 (t, 2H, J=3.60Hz, 3.60Hz, CH2COO),2.03 (s,3H,CH3CO),1.07(m,3H,CH2CH3),4.85(s,1H,OH),10.25(s,1H,NH)。
Chemical compounds I -4：
Chemical formula：
Physico-chemical parameter：It is blue solution, maximum absorption wavelength 598nm under green solid particle, toluene solvant.
Structural confirmation：
1H-NMR(DMSO-d6):δ=7.05 (d, J=7.30Hz, 1H, Ar-H), 8.70-8.87 (m, 1H, Ar-H), 3.93-4.20(m,2H,CH2), 3.86 (d, 3H, J=2.80, OCH3), 2.62 (t, 2H, J=3.60Hz, 3.60Hz, CH2COO),2.03(s,3H,CH3CO),1.07(m,3H,CH2CH3),4.85(s,1H,OH),10.25(s,1H,NH)。
Chemical compounds I -5：
Chemical formula：
Physico-chemical parameter：It is blue-green solution, maximum absorption wavelength 625nm under green solid particle, toluene solvant.
Structural confirmation：
1H-NMR(DMSO-d6):δ=7.05 (d, J=7.30Hz, 1H, Ar-H), 8.78-9.21 (m, 1H, Ar-H), 3.93-4.20(m,2H,CH2), 3.86 (d, 3H, J=2.80, OCH3), 2.62 (t, 2H, J=3.60Hz, 3.60Hz, CH2COO),2.03(s,3H,CH3CO),1.07(m,3H,CH2CH3),4.85(s,1H,OH),10.25(s,1H,NH)。
Application Example：
Take and wash/ammonia stockinette 15g, HAC regulation pH=4.5, bath raio 1：15, dye liquor concentration is 4% (owf).By fabric Enter dye at room temperature, 10min is first incubated when being rapidly heated to 80 DEG C, slowly upper dye is a certain amount of by dyestuff, then 0.75 DEG C/min Heating rate is incubated 10min, it is ensured that dyestuff level dyeing to 115 DEG C, then can be rapidly heated to 130 DEG C of dyeing 60min, after dye finishes 70 DEG C are cooled to, 50 DEG C of 1g/L sodium carbonate washings, cold water is washed, 1-5# dyeing samples are obtained, using GB/T 3921-2008, GB/T 5713-2013, GB/T 3922-2013, GB/T 3920-2008, AATCC 163-2013 distinguish the water-fastness color of test dye Fastness, resistance to colour fastness to water, colour fastness to perspiration, colour fastness to rubbing and the color fastness of resistance to thermophoresis.
Table 1, color fastness testing result

Claims (2)

1. a kind of preparation method of disperse dyes, it is characterised in that comprise the following steps as follows；
(1) compound shown in formula (II), is subjected to diazo-reaction in diazo reagent and obtains diazol；
In formula：
X is hydrogen-based or nitro；
Y is hydrogen-based, chloro, bromo or cyano group；
Diazo reagent is nitro sulfuric acid and acetic acid/propionic acid mixture in step (1), or hydrochloric acid and natrium nitrosum mixture；
The temperature of diazo-reaction is between -5 DEG C -5 DEG C in step (1)；
Diazonium compound and the amount ratio of diazo reagent reactive material are 1 in step (1)：1.0~1.05；
(2) compound shown in the diazol obtained by step (1) and formula (III) is subjected to coupling reaction, produces and divide described in formula I Dissipate dyestuff；
Coupling reaction is in V in step (2)：V=1：In 1 methanol solution, carried out under the conditions of -5 DEG C~5 DEG C；
Diazonium salt dissolving and the amount ratio of coupling reagent reactive material are 1 in step (2)：1.0~1.05, adjust pH=5 with sodium acetate ~6.
2. the disperse dyes prepared by a kind of claim 1 in polyester-cotton blend, wash ammonia, polyester fabric dyeing in application.
CN201610415626.8A 2016-06-14 2016-06-14 A kind of disperse dyes and preparation method and application Expired - Fee Related CN106084874B (en)

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