CN106867274B - A kind of dispersion red dye composition and dye preparations - Google Patents

A kind of dispersion red dye composition and dye preparations Download PDF

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Publication number
CN106867274B
CN106867274B CN201611268732.4A CN201611268732A CN106867274B CN 106867274 B CN106867274 B CN 106867274B CN 201611268732 A CN201611268732 A CN 201611268732A CN 106867274 B CN106867274 B CN 106867274B
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Prior art keywords
component
dye composition
red dye
formula
dispersion red
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CN106867274A (en
Inventor
高怀庆
汤亦军
李世华
张海斌
张友珍
祝培明
赵广明
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Zhejiang Longsheng Group Co Ltd
Zhejiang Longsheng Dyestuff Chemical Co Ltd
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Zhejiang Longsheng Group Co Ltd
Zhejiang Longsheng Dyestuff Chemical Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs

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

Abstract

The invention discloses a kind of dispersion red dye composition and dye preparations.The dispersion red dye composition, including component A and component B, the component A is selected from least one of compound shown in formula (I), and the component B is selected from least one of compound shown in formula (II) and/or (III);Based on the component A and component B, the mass percentage of component A is 10~90%, and the mass percentage of component B is 10~90%.The dispersive red dye product, including the dispersion red dye composition and and auxiliary agent, the weight ratio of auxiliary agent and dispersion red dye composition is 0.2~5:1.Dispersion red dye composition and dye preparations provided by the invention, when being applied to hydrophobic fiber material dyeing, when being applied to hydrophobic fiber material dyeing, every color fastness is excellent, and especially water-fastness staining fastness is prominent.

Description

A kind of dispersion red dye composition and dye preparations
(1) technical field
The present invention relates to a kind of dispersion red dye composition and dye preparations, especially a kind of suitable printing hydrophobic fiber The dispersion red dye composition and dye preparations of material.
(2) background technique
Existing red disperse dyes, it is functional to polyester textile (terylene) colorfastness in spite of part, still For polyester blend fabric it is for example popular wash/dyeing of ammonia blended yarn weaved fabric when, at high-temperature process (such as thermal finalization), due to fiber The auxiliary agent of outer layer generates dissolution to dyestuff at high temperature, and dyestuff is widened by fiber capillary high temperature from fibrous inside and moved Fiber sheath is moved on to, dyestuff is accumulated in fiber sheath, causes a series of influence, such as color fastness decreased.
The applicant has been provided a kind of with excellent lifting force, reproducibility and brilliance in CN101215245A The Monoazo compound of wet colour fastness, high-incidence intensity of colour.Even to this day, applicants have discovered that the Monoazo compound is used for Colorant match can solve the above problem, and obtain one group of dispersion red dye composition haveing excellent performance.
(3) summary of the invention
To solve the above problems, being applied to hydrophobic the present invention provides a kind of dispersion red dye composition and dye preparations Property fibrous material dyeing when, every color fastness is excellent, and especially water-fastness staining fastness is prominent.
The technical solution adopted by the present invention is that:
A kind of dispersion red dye composition, including component A and component B, the component A are selected from compound shown in formula (I) At least one of, the component B is selected from least one of compound shown in formula (II) and/or (III);Based on described The mass percentage of component A and component B, component A are 10~90%, and the mass percentage of component B is 10~90%:
In formula (I):
X1、X2Respectively stand alone as hydrogen, halogen or cyano;
R1For hydrogen, C1~C4Alkyl or acetylamino;
R2For C1~C4Alkyl or benzyl.
In formula (II) and formula (III):
M, n is 1 or 2 independently of one another;
R3For hydrogen, hydroxyl, acetylamino, C1~C4Alkyl or C1~C4Alkoxy;
R4、R5It is independently of one another C1~C4Alkyl;
X3、X4Respectively stand alone as nitro, halogen or hydrogen;X5For nitro or halogen.
Dispersion red dye composition of the present invention can also be optionally added into a certain amount of shading components, such as C.I. Disperse violet 93, C.I. disperse blue 366, C.I. disperse blue 165, C.I. disperse orange 288, C.I. disperse yellow 118 etc..
Preferably, the dispersion red dye composition includes component A and component B, based on the component A and component B, The mass percentage of the component A is 20~90% (more preferably 30~85%), the mass percentage of component B is 10~ 80% (preferably 15~70%).
Preferably, the dispersion red dye composition is made of component A and component B, and wherein the quality percentage of component A contains Amount is 10~90% (preferably 20~90%, more preferably 30~85%), and the mass percentage of component B is 10~90% (excellent Select 10~80%, more preferably 15~70%).
Dispersion red dye composition of the present invention, also can further include component C, and the component C is selected from formula (IV) One of shown compound is a variety of, and based on the gross weight of the component A and component B, the mass percentage of component C is 1 ~100%, preferably 5~90%:
In formula (IV):
P, q is 1 or 2 independently of one another;
R6For C1~C4Alkyl, C1~C4Alkoxy, phenyl or amino;
R7、R8It is independently of one another C1~C4Alkyl;
X7、X6Respectively stand alone as hydrogen, nitro, cyano or halogen.
Preferably, the dispersion red dye composition is made of component A, component B and component C, based on the component A With the gross weight of component B, wherein the mass percentage of component A be 10~90% (preferably 20~90%, more preferably 30~ 85%), the mass percentage of component B is 10~90% (preferably 10~80%, more preferably 15~70%), the matter of component C Amount percentage composition is 1~100% (preferably 5~90%).
In the present invention, the C1~C4Alkyl can be methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, Tert-butyl etc., the C1~C4Alkoxy can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutyl Oxygroup, tert-butoxy etc., the halogen can be fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.
Further, X1、X2One of be chlorine, bromine or cyano, it is another be hydrogen.
Further, R1For hydrogen, methyl or acetylamino.
Further, R2For ethyl or benzyl.
Further, R3For hydrogen, hydroxyl, acetylamino, methyl or methoxy.
Further, R4、R5Methyl or ethyl independent of one another.
Further, X3、X4Respectively stand alone as nitro, chlorine, bromine or hydrogen;X5For nitro, chlorine or bromine.
Further, R6For methyl, ethyl, methoxyl group, ethyoxyl, phenyl or amino.
Further, R7、R8It is independently of one another methyl or ethyl.
Further, X7、X6One of be nitro, cyano, chlorine or bromine, it is another be hydrogen, chlorine or bromine.
Further, the dye component A preferably is selected from least one in dye composition shown in following formula (I -1)~(I -7) Kind:
Again further, component A is selected from least one of formula (I -1), (I -4), (I -5).
Further, the dye component B preferably is selected from dyestuff shown in formula (II -1)~(II -13), (III -1)~(III -7) At least one of compound;
Again further, component B is selected from least one of formula (II -1)~(II -3), (III -1)~(III -3).
Further, the dye component C preferably is selected from least one in dye composition shown in formula (IV -1)~(IV -18) Kind:
Again further, component C is selected from least one of formula (IV -1), (IV -8), (IV -14).
Dispersion red dye composition of the present invention preferably comprises component A and component B, in which:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3).
Mass percentage based on the above component A and component B, the component A is 20~90%, the quality hundred of component B Dividing content is 10~80%.
Alternatively, dispersion red dye composition of the present invention, is preferably made of component A and component B, in which:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3).
Mass percentage based on the above component A and component B, the component A is 20~90%, the quality hundred of component B Dividing content is 10~80%.
Alternatively, dispersion red dye composition of the present invention, preferably comprises component A, component B and component C, in which:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3);
Component C is selected from least one of formula (IV -1), (IV -8), (IV -14).
Based on the above component A and component B, the mass percentage of component A is 20~90%, and the quality percentage of component B contains Amount is 10~80%, and the mass percentage of component C is 1~100%.
Alternatively, dispersion red dye composition of the present invention, is made of component A, component B and component C, in which:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3);
Component C is selected from least one of formula (IV -1), (IV -8), (IV -14);
Based on the above component A and component B, the mass percentage of component A is 20~90%, and the quality percentage of component B contains Amount is 10~80%, and the mass percentage of component C is 1~100%.
Dispersion red dye composition of the present invention, when as commodity selling or being applied to textile material coloring, usually It also needs that auxiliary agent is added and is post-processed.Therefore, the present invention also provides a kind of dispersive red dye product, contain point The weight ratio of scattered red dye composition and auxiliary agent, auxiliary agent and disperse dye composition is 0.2~5:1.Preferably, point Red dye product is dissipated to be made of the dispersion red dye composition and auxiliary agent.The auxiliary agent is that disperse dyes are common when compounding Dispersing agent, diffusant and other surfactants etc., preferably be selected from one of following or in which two or more mixture: lignin Sulfonate (such as sodium lignin sulfonate (lignin 85A, lignin 83A)), alkyl naphthalene sulfonic acid formaldehyde condensation products (such as methyl naphthalene sulfonic acid Formaldehyde condensation products (Dispersant MF)), naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic acid-formaldehyde condensation product (diffusant CNF) etc..
Dispersive red dye product of the present invention the preparation method is as follows:
After the dye monomer compound (former dyestuff) for forming dispersion red dye composition is mixed according to the ratio, in auxiliary agent, water In the presence of with pulverizers such as sand mill or grinders carry out corpusculed;In addition dye monomer compound can also helped respectively It is mixed in proportion after carrying out corpusculed processing with pulverizers such as sand mill or grinders in the presence of agent, water.The present invention The dispersive red dye product, with sand mill or grinder grinding after be liquid, after spray drying can be powdery, graininess, This is well known to those skilled in the art preparation method, due in spray-drying process can not by the removing of moisture 100%, because This still allows there are a certain amount of moisture, preferably more than dye preparations are total even in powdery or granular dye preparations The 10% of weight.
In addition, it is necessary to which explanation makes the promotion of dyeing effect when dye preparations are applied to the printing and dyeing of textile fabric Contribution is technically characterized in that dye component contained in the product and ratio.
In the present invention, dye composition shown in formula (I) to (IV) is convenient to by side well known to those skilled in the art Formula synthesis, is also referred to the method introduced in patent CN101522816A, CN101215245A, US5550217A or similar Method preparation, can also use commercial goods.Formula (III) compound is the by-product during formula (II) Dyestuff synthesis, usual feelings Do not have to separate the two under condition, conventional DMF solvent can also be used when necessary repeatedly refines the two is separated.
It, can be by ways customary in industry to hydrophobic fiber material using dyestuff made of dye composite of the invention (such as polyester and its blended fabric) is dyed, and is such as dyed using common dip method or high-temperature and high pressure dyeing process, can also For direct printing.Wherein, common dip method such as pre-processes hydrophobic fiber material, is put into dye vat and is disseminated, Dye finishes, and cold water wash to neutrality squeezes out, and restores again cleaning, dries;Fabric is such as carried out dye pre-treatment by direct printing, is dried Dry, setting prints disperse dyes mill base on printing machine, then is evaporated, and the dye fixing on fabric is made in the way of decatize, most After wash, stentering forming.
Dispersion red dye composition and dye preparations provided by the invention are answered when being applied to hydrophobic fiber material dyeing When for hydrophobic fiber material dyeing, every color fastness is excellent, and especially water-fastness staining fastness is prominent.
(4) specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in This:
Embodiment 1:
By 63 grams of formulas (I -1) compound, 25 grams of formula (II -2) compounds, 12 grams of formula (III -1) compounds and 200 grams of point Powder MF, after adding 850 grams of blendings of water, grinding distribution is simultaneously dry to get finished product, which can be supplied to fabric items fastness ability Excellent ruby.
Embodiment 2:
By 60 grams of formulas (I -1) compound, 18 grams of formula (II -3) compounds, 22 grams of formula (IV -1) compounds and 185 grams of point Powder MF, after adding 850 grams of blendings of water, grinding distribution is simultaneously dry to get finished product, which can be supplied to fabric items fastness ability Excellent ruby.
Embodiment 3:
By 21 grams of formulas (I -1) compound, 36 grams of formula (II -2) compounds, 43 grams of formula (IV -8) compounds and 200 grams of point Powder MF, after adding 650 grams of blendings of water, grinding distribution is simultaneously dry to get finished product, which can be supplied to fabric items fastness ability Excellent ruby.
Embodiment 4~50:
According to method described in embodiment 1,2 or 3, the difference is that being added using the structure and weight of component A~C in table 1 200 grams of auxiliary agent (Dispersant MF is 150 grams, and lignin 85A is 50 grams), adds and slurries is made after 850 grams of blendings of water, grinding distribution, Dry, finished product, the dyestuff can be supplied to the excellent carbuncle tone of fabric items fastness ability.
Table 1
Dyeing Example:
Disperse dyes made from above-described embodiment 1~50 are chosen respectively, using conventional high temperature high-pressure dyeing and thermal finalization Polyester fibre/spandex intertexture is handled, in treatment process, controls dye level (o.w.f) 4.0%, bath raio 1: 25 adjusts Value in Dyeing Process 4 ~5, room temperature enters dye, is warming up to 130 DEG C with 1 DEG C/min, keeps the temperature 45min, restores washing, washing, drying, 180 DEG C of heat by well-established law Sizing 60 seconds, obtains dyeing and weaving object rubied/rubious.Rub resistance and water-fastness color jail are tested respectively according to AATCC 8, AATCC 61-2A It spends, as a result the following table 2:
Table 2
By upper table 2 it is found that the disperse red composition in the present invention, dyed fabric are resistance to after final finishing high temperature thermal finalization Friction and water-fastness staining fastness can satisfy the printing and dyeing that high fastness requires fabric.

Claims (9)

1. a kind of dispersion red dye composition, including component A and component B, the component B are selected from formula (II) and/or (III) institute Show at least one of compound;Based on the component A and component B, the mass percentage of component A is 10~90%, group The mass percentage for dividing B is 10~90%:
In formula (II) and formula (III):
M, n is 1 or 2 independently of one another;
R3For hydrogen, hydroxyl, C1~C4Alkyl or C1~C4Alkoxy;
R4、R5It is independently of one another C1~C4Alkyl;
X3、X4Respectively stand alone as nitro, halogen or hydrogen;X5For nitro or halogen;
The dye component A is selected from least one of dye composition shown in following formula (I -1)~(I -7):
2. dispersion red dye composition as described in claim 1, it is characterised in that: the dispersion red dye composition, also Further include component C, the component C is selected from one of compound shown in formula (IV) or a variety of, based on the component A and The mass percentage of the gross weight of component B, component C is 1~100%:
In formula (IV):
P, q is 1 or 2 independently of one another;
R6For C1~C4Alkyl, C1~C4Alkoxy, phenyl or amino;
R7、R8It is independently of one another C1~C4Alkyl;
X7、X6Respectively stand alone as hydrogen, nitro, cyano or halogen.
3. dispersion red dye composition as claimed in claim 2, it is characterised in that: the dispersion red dye composition is by group Divide A, component B and component C composition.
4. dispersion red dye composition as described in claim 1, it is characterised in that: the dispersion red dye composition is by group Divide A and component B composition.
5. the dispersion red dye composition as described in one of Claims 1 to 4, it is characterised in that: component B be selected from formula (II -1)~ At least one of dye composition shown in (II -7), (II -9)~(II -13), (III -1)~(III -7);
6. dispersion red dye composition as claimed in claim 2 or claim 3, it is characterised in that: component C is selected from formula (IV -1)~(IV - 18) at least one of dye composition shown in:
7. dispersion red dye composition as described in claim 1 or 4, it is characterised in that: the dispersion red dye composition In:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3);
Mass percentage based on the above component A and component B, the component A is 20~90%, and the quality percentage of component B contains Amount is 10~80%;
8. dispersion red dye composition as claimed in claim 2 or claim 3, it is characterised in that: the dispersion red dye composition In:
Component A is selected from least one of formula (I -1), (I -4), (I -5);
Component B is selected from least one of formula (III -1)~(III -3), (II -1)~(II -3);
Component C is selected from least one of formula (IV -1), (IV -8), (IV -14);
Based on the above component A and component B, the mass percentage of component A is 20~90%, and the mass percentage of component B is The mass percentage of 10~80%, component C are 1~100%;
9. a kind of dispersive red dye product, including dispersion red dye composition as described in claim 1 and and auxiliary agent, auxiliary agent and The weight ratio of dispersion red dye composition is 0.2~5:1.
CN201611268732.4A 2016-12-31 2016-12-31 A kind of dispersion red dye composition and dye preparations Active CN106867274B (en)

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CN110373046B (en) * 2019-07-24 2024-02-23 孚美科(绍兴)染料科技有限公司 Disperse red FS150% dye composition
CN111518414B (en) * 2020-04-29 2021-07-16 约克夏(浙江)染化有限公司 Red disperse dye composition, red disperse dye and preparation method and application thereof

Citations (5)

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Publication number Priority date Publication date Assignee Title
CN105001663A (en) * 2015-07-10 2015-10-28 俞杏英 Beta-ketonic ester and benzyl contained high-sublimation-fastness disperse dye compound, and preparation and application thereof
CN105462292A (en) * 2015-12-24 2016-04-06 俞杏英 Disperse dye composition and preparation method and application thereof
CN105602283A (en) * 2015-12-24 2016-05-25 俞杏英 High-fastness disperse dye composition as well as preparation method and application thereof
CN105647235A (en) * 2016-01-20 2016-06-08 俞杏英 High dye uptake disperse dye composition and preparation method and application thereof
CN105733290A (en) * 2016-01-28 2016-07-06 俞杏英 Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105001663A (en) * 2015-07-10 2015-10-28 俞杏英 Beta-ketonic ester and benzyl contained high-sublimation-fastness disperse dye compound, and preparation and application thereof
CN105462292A (en) * 2015-12-24 2016-04-06 俞杏英 Disperse dye composition and preparation method and application thereof
CN105602283A (en) * 2015-12-24 2016-05-25 俞杏英 High-fastness disperse dye composition as well as preparation method and application thereof
CN105647235A (en) * 2016-01-20 2016-06-08 俞杏英 High dye uptake disperse dye composition and preparation method and application thereof
CN105733290A (en) * 2016-01-28 2016-07-06 俞杏英 Monomeric compound of orange disperse dye with high perspiration fastness as well as preparation method and application thereof

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