CN111117291B - Disperse red dye composition and dye product - Google Patents
Disperse red dye composition and dye product Download PDFInfo
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- CN111117291B CN111117291B CN201911283015.2A CN201911283015A CN111117291B CN 111117291 B CN111117291 B CN 111117291B CN 201911283015 A CN201911283015 A CN 201911283015A CN 111117291 B CN111117291 B CN 111117291B
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- disperse red
- red dye
- dye composition
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- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000001044 red dye Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 239000000975 dye Substances 0.000 title claims abstract description 38
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 17
- 239000000986 disperse dye Substances 0.000 abstract description 11
- 239000004744 fabric Substances 0.000 abstract description 11
- 238000005406 washing Methods 0.000 abstract description 9
- 239000002657 fibrous material Substances 0.000 abstract description 7
- 230000002209 hydrophobic effect Effects 0.000 abstract description 7
- 229920004933 Terylene® Polymers 0.000 abstract description 6
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 6
- 229920000728 polyester Polymers 0.000 abstract description 5
- 238000000859 sublimation Methods 0.000 abstract description 5
- 230000008022 sublimation Effects 0.000 abstract description 5
- 229920002334 Spandex Polymers 0.000 abstract description 4
- 239000004759 spandex Substances 0.000 abstract description 4
- 239000000835 fiber Substances 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000227 grinding Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
- DVBLPJWQXDCAKU-UHFFFAOYSA-N 2-(4-bromo-3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=C(O)C(Br)=C2C=CC=CC2=N1 DVBLPJWQXDCAKU-UHFFFAOYSA-N 0.000 description 1
- QEORVDCGZONWCJ-UHFFFAOYSA-N 2-[[4-[2-cyanoethyl(ethyl)amino]phenyl]diazenyl]-5-nitrobenzonitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N QEORVDCGZONWCJ-UHFFFAOYSA-N 0.000 description 1
- GRMDKKJYMUDEJO-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-cyano-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCOC(C)=O)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N GRMDKKJYMUDEJO-UHFFFAOYSA-N 0.000 description 1
- MWMJPPMTXZJLIK-UHFFFAOYSA-N 3-[4-[(2,6-dibromo-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1Br MWMJPPMTXZJLIK-UHFFFAOYSA-N 0.000 description 1
- AJKOAOUQPNLZTF-UHFFFAOYSA-N 3-[n-benzyl-4-[(4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=C(N(CCC#N)CC=2C=CC=CC=2)C=C1 AJKOAOUQPNLZTF-UHFFFAOYSA-N 0.000 description 1
- MVKMKUHSGHKEDT-UHFFFAOYSA-N 3-[n-butyl-4-[(4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CCCC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 MVKMKUHSGHKEDT-UHFFFAOYSA-N 0.000 description 1
- ZSPPPAFDNHYXNW-UHFFFAOYSA-N 3-[n-ethyl-4-[(4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 ZSPPPAFDNHYXNW-UHFFFAOYSA-N 0.000 description 1
- PWUVCFDFTBWAFJ-UHFFFAOYSA-N 3-[n-ethyl-4-[(6-nitro-1,3-benzothiazol-2-yl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=NC2=CC=C([N+]([O-])=O)C=C2S1 PWUVCFDFTBWAFJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical group O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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
-
- 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
- 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
- D06P1/19—Nitro 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)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses a disperse red dye composition and a dye product, wherein the disperse red dye composition comprises 5-50 parts by mass of a component A and 50-95 parts by mass of a component B, the component A is selected from at least one of the following formulas (I), and the component B is selected from one or more of the following formulas (III), or a combination of one or more of the following formulas (III) and one or more of the following formulas (IV). The disperse red dye product comprises the disperse red dye composition and an auxiliary agent. When the disperse red dye product prepared from the disperse red dye composition is applied to dyeing of hydrophobic fiber materials such as polyester fibers and terylene/spandex fabrics, the disperse red dye product has excellent washing fastness, sublimation fastness and rubbing fastness, good lifting performance and high color yield, and overcomes the defect of poor lifting performance of general high-fastness disperse dyes.
Description
(I) technical field
The invention relates to a disperse red dye composition and a dye product, in particular to a high-fastness red disperse dye composition and a dye product suitable for printing and dyeing hydrophobic fiber materials.
(II) background of the invention
The method crosses the full-warm-up period, people pay more and more attention to the improvement of life quality, and if the purchased fabric is poor in fastness, the problems of contamination, color lapping and the like occur, so that the life quality is seriously influenced. In order to meet the market demands, various high-fastness disperse dyes appear on the market at present, but the problem of single fastness performance is generally existed, namely, the excellent fastness of various aspects such as washing fastness, light fastness, sublimation fastness, rubbing fastness and the like are difficult to achieve. In addition, the common high-fastness disperse dye often has the problems of poor promotion, low color yield, high dye cost and the like. Chinese patent application CN103589190A, CN102372932A and CN 101899229A respectively disclose a disperse bright red dye composition with high washing fastness, but still have improved space.
Disclosure of the invention
The invention aims to provide a disperse red dye composition and a dye product with excellent fastness such as washing fastness, sublimation fastness, rubbing fastness and the like, and solves the problems of poor promotion, low color yield and the like of high-fastness disperse red dyes in the current market.
The technical scheme adopted by the invention is as follows:
the invention provides a disperse red dye composition, which comprises 5-50 parts by mass of a component A and 50-95 parts by mass of a component B, wherein the component A is selected from at least one of the following formulas (I), and the component B is selected from one or more of the following formulas (II) and/or (III) and/or (IV);
in formula (I):
R1、R2each independently is C1～C18An alkyl group;
in the formula (II):
X1、X2each independently Cl, H, -NO2；
R3、R4Each independently is C1～C4Alkyl of-C2H4OCOCH3、-C2H4CN or
R5Is H or CH3；
In the formula (III):
X3is halogen, -CF3or-OCH3；
X4Is hydrogen, halogen or-CH3；
R6、R7Each independently is C1～C4Alkyl groups of (a);
n is 1 or 2;
in the formula (IV):
R8is hydrogen or C1～C4Alkyl groups of (a);
R9is C1～C4Alkyl, hydroxy-substituted C of1～C4Alkyl of (2) or
Component B, as described herein, may be selected from formula (II) or formula (III) or formula (IV); it may also be selected from one of the following combinations: formula (II) + formula (III), formula (II) + formula (IV), formula (III) + formula (IV); or a combination of three selected from formula (II), formula (III) and formula (IV).
In the present invention, said C1～C4The alkyl group may be methyl, ethyl, n-propyl,Isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl. The halogen is F, Cl, Br and the like.
Preferably, R1Is C3～C18Such as linear or branched propyl, butyl, hexyl, octyl, dodecyl, octadecyl, and the like.
Preferably, R2Is C1～C8Such as straight or branched chain methyl, propyl, butyl, hexyl, octyl, and the like.
As a further preference, the component a is selected from one of the following formulae or a mixture of two or more thereof in any ratio:
it is still further preferred that component A is at least one of the formulae (I-1), (I-2) and (I-6).
Preferably, X is1、X2Not all are H.
As a further preference, the component B is selected from one of the following formulae or a mixture of two or more thereof in any ratio:
it is further preferred that component B is at least one of the formulae (II-1), (II-2), (III-1), (III-2), (IV-1), (IV-2), (IV-6).
As still further preference, in the disperse red dye composition, the component A is selected from at least one of the formulas (I-1), (I-2) and (I-6);
the component B is at least one selected from the formulas (II-1), (II-2), (III-1), (III-2), (IV-1), (IV-2) and (IV-6).
Preferably, in the disperse red dye composition, the mass percentage of the component A is 5-50% (preferably 10-50%), and the mass percentage of the component B is 50-95% (preferably 50-90%).
The disperse red dye composition is further preferably composed of a component A and a component B, wherein the mass percentage of the component A is 5-50% (preferably 10-50%), and the mass percentage of the component B is 50-95% (preferably 50-90%).
The red disperse dye composition particularly preferably consists of a component A and a component B, wherein:
the component A is selected from at least one of the formulas (I-1), (I-2) and (I-6);
the component B is at least one selected from the formulas (II-1), (II-2), (III-1), (III-2), (IV-1), (IV-2) and (IV-6);
the mass percentage of the component A is 5-50% (preferably 10-50%), and the mass percentage of the component B is 50-95% (preferably 50-90%).
It should be emphasized that the disperse red dye compound of the present invention, the dye coupled at the ortho position of the pyridone hydroxyl group, generally exists in the form of quinone hydrazone structure, that is, the dye of the general formula (I) substantially has the quinone hydrazone structure shown in the following formula (Ia), and in consideration of the writing habit of those skilled in the art, the writing form of azo is still adopted in the summary and the examples of the invention, which does not affect the essence of the present invention:
wherein R is1、R2The same as defined above for the compound of formula (I).
Because of the particularity of the dye industry, the dye composition is difficult to prepare into a pure product without necessity, and usually has some impurities in the preparation process, and the disperse red dye composition provided by the invention is also allowed to contain a small amount of water and a trace amount of physical impurities when prepared into a finished product.
The disperse red dye composition of the present invention further allows the addition of a toning component in an amount of not more than 5% by mass, preferably not more than 3% by mass, such as a trace amount of c.i. disperse yellow 54, c.i. disperse yellow 64, c.i. disperse yellow 119, c.i. disperse yellow 143, c.i. disperse yellow 182, c.i. disperse orange 25, c.i. disperse orange 33, c.i. disperse orange 61, c.i. disperse red 73, c.i. disperse red 80, c.i. disperse red 145, c.i. disperse red 158, and the like.
In the above scheme, c.i. refers to the dye INDEX (COLOR INDEX) and is a compilation of international dye and pigment varieties published by the british dyers association (SDC) and the american association of textile chemists and dyers (AATCC). The "dye part" refers to a dye cake (crude dye) which does not include any finishing auxiliary agent, but is allowed to contain a small amount of impurities brought about in the synthesis, the impurities do not affect the service performance of the dye, and the mass percentage or the mass part of the dye is calculated by the dry weight of the dye cake.
The disperse red dye composition provided by the invention is sold as a commodity or directly applied to textile material coloring, and a conventional auxiliary agent is usually added. Therefore, the invention also provides a disperse red dye product which is sold as a commodity or directly applied to textile material coloring, and the disperse red dye product comprises the disperse red dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5: 1. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is preferably selected from one or a mixture of more than two of the following components: naphthalenesulfonic acid-formaldehyde condensates, lignosulfonates, alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), sodium lignosulfonates (lignin 85A, lignin 83A), anhydrous sodium sulfate (sodium sulfate), and the like.
The disperse red dye product can be prepared by the following method: mixing the raw dyes contained in the disperse red dye composition according to the proportion, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the crude dye contained in the disperse red dye composition may be subjected to a pulverization treatment in the presence of an auxiliary agent and water by a pulverizer such as a sand mill or a grinder, and then mixed in the above-mentioned ratio. The disperse dye red product of the invention can be liquid after being ground by a sand mill or a grinding machine, and can be powder or granular after being spray-dried.
Preferably, the disperse red dye product consists of the disperse red dye composition and an auxiliary agent.
In the present invention, the dye compounds represented by the formulae (I), (II), (III) and (IV) can be conveniently synthesized in a manner well known to those skilled in the art, and commercially available products can also be used.
The dye product prepared by the disperse red dye composition can dye hydrophobic fiber materials such as polyester fibers and terylene/spandex fabrics in a conventional mode in the industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be directly used for printing. Wherein, the common dip dyeing method comprises the following steps: pretreating a hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, carrying out reduction washing, and drying; direct printing is as follows: the method comprises the steps of carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, carrying out steaming, fixing the color of the dye on the fabric by using a steaming mode, finally washing, and tentering and setting.
Compared with the prior art, when the disperse red dye product prepared from the disperse red dye composition is applied to dyeing of hydrophobic fiber materials such as polyester fibers and terylene/spandex fabrics, the disperse red dye composition has excellent washing fastness, sublimation fastness and rubbing fastness, good promotion performance and high color yield, and overcomes the defect of poor promotion performance of general high-fastness disperse dyes.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
according to the data shown in table 1, the disperse red dye of the present invention can be obtained by blending component a, component B, and an auxiliary agent (a methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), a naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), a benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), and sodium lignosulfonate (lignin 85A, lignin 83A)) with water, followed by grinding and dispersing with a grinder, and drying. The obtained dye can provide even red with good fastness performance for terylene and blended fabrics thereof.
TABLE 1
Example 40:
45 g of the component A of the formula (I-1), 52 g of the component B of the formula (II-1), 3 g of C.I. disperse orange 288 and 250 g of sodium lignosulfonate are mixed with water, ground and dispersed by a grinding machine and dried to obtain the finished dye, and the dye can provide uniform red with good fastness for terylene and blended fabrics.
Example 41:
20 g of the component A of the formula (I-1), 57 g of the formula (III-2), 23 g of the formula (IV-1), 5 g of the C.I. disperse red 82 and 200 g of the dispersing agent MF are mixed with water, ground and dispersed by a grinding machine and dried to obtain the finished dye, and the dye can provide uniform red with good fastness for terylene and blended fabrics.
Comparative example 1:
example 1 in CN103589190a was taken as comparative example 1;
example 1 in CN102372932a was taken as comparative example 2;
example 1 in CN 101899229a was taken as comparative example 3.
Dyeing example 1:
2g of the disperse dye products prepared in the embodiments 1-39 are respectively taken, 500ml of water is added to prepare dye liquor, 20ml of dye liquor is absorbed and mixed with 80ml of water, the PH of a dye bath is adjusted to 4.5 by acetic acid, then the temperature is raised to 60 ℃, 2g of polyester/spandex cloth is simultaneously placed for high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35 minutes, the temperature is kept for 30 minutes, and the sample is taken after being cooled to 80 ℃. The sublimation fastness, rubbing fastness and washing fastness were measured using ISO 105-P01, ISO 105-X12 and AATCC 61-2A respectively, and the results are shown in Table 2 below:
TABLE 2
And (3) lifting force comparison:
the disperse red dyes prepared in examples 1 to 39 of the present invention and comparative examples 1 to 3 were dyed according to the method of dyeing example 1 except that the dyeing depth was 0.5%, 1%, 2%, 4%, 6%, 8%. According to the lifting force of the disperse red dye composition tested according to the GB/T2397-2012 standard, the apparent color depth of the fabric is obviously increased along with the increase of the dyeing depth, while the apparent color depth of the dyes of comparative examples 1-3 is not obviously increased under the condition of 4-8% of the depth, so that the lifting force is improved compared with the prior art.
Therefore, when the disperse red dye composition provided by the invention is applied to polyester/ammonia dyeing, compared with the existing disperse red dye, the disperse red dye composition has more excellent lifting force and dyeing performance, and can be further compounded with magenta and dark blue disperse dyes, so that the dye variety is enriched.
Claims (12)
1. A disperse red dye composition comprises 5-50 parts by mass of a component A and 50-95 parts by mass of a component B; the component A is selected from at least one of the following formula (I); the component B is selected from one or more of the following formulas (III), or is selected from the combination of one or more of the following formulas (III) and one or more of the following formulas (IV);
in formula (I):
R1、R2each independently is C1～C18An alkyl group;
in the formula (III):
X3is halogen, -CF3or-OCH3；
X4Is hydrogen, halogen or-CH3；
R6、R7Each independently is C1～C4Alkyl groups of (a);
n is 1 or 2;
in the formula (IV):
R8is hydrogen or C1～C4Alkyl groups of (a);
R9is C1～C4Alkyl, hydroxy-substituted C of1～C4Alkyl of (2) or
2. A disperse red dye composition according to claim 1 wherein: the component A is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
3. a disperse red dye composition according to claim 1 wherein: the specific structure of the formula (III) is as follows:
the specific structure of formula (IV) is as follows:
4. a disperse red dye composition according to claim 3 wherein: the component B is at least one of formulas (III-1) and (III-2); or the component B is a combination of at least one of the formulas (III-1) and (III-2) and at least one of the formulas (IV-1), (IV-2) and (IV-6).
5. A disperse red dye composition according to claim 4 wherein: the component A is selected from at least one of formulas (I-1), (I-2) and (I-6):
6. a disperse red dye composition according to any one of claims 1 to 5 wherein: in the disperse red dye composition, the mass percentage of the component A is 5-50%, and the mass percentage of the component B is 50-95%.
7. A disperse red dye composition according to claim 6 wherein: in the disperse red dye composition, the mass percentage of the component A is 10-50%, and the mass percentage of the component B is 50-90%.
8. A disperse red dye composition according to any one of claims 1 to 5 wherein: the disperse red dye composition is composed of a component A and a component B, wherein the component A is 5-50% by mass, and the component B is 50-95% by mass.
9. A disperse red dye composition according to claim 8 wherein: the disperse red dye composition is composed of a component A and a component B, wherein the mass percentage of the component A is 10-50%, and the mass percentage of the component B is 50-90%.
10. A disperse red dye product, comprising the disperse red dye composition as claimed in claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5: 1.
11. The dye product of claim 10, wherein: the auxiliary agent is selected from one of the following or a mixture of more than two of the following: naphthalene sulfonic acid formaldehyde condensate, lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate and anhydrous sodium sulphate.
12. The dye preparation according to claim 10 or 11, wherein: the disperse red dye product consists of the disperse red dye composition and an auxiliary agent.
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| CN113736284B (en) * | 2021-10-22 | 2023-09-05 | 浙江山峪集团股份有限公司 | Disperse red dye composition |
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| CN111117291A (en) | 2020-05-08 |
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| CN111073344A (en) | 2020-04-28 |
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