CN112724707B - Disperse orange dye composition and dye product - Google Patents
Disperse orange dye composition and dye product Download PDFInfo
- Publication number
- CN112724707B CN112724707B CN202011509357.4A CN202011509357A CN112724707B CN 112724707 B CN112724707 B CN 112724707B CN 202011509357 A CN202011509357 A CN 202011509357A CN 112724707 B CN112724707 B CN 112724707B
- Authority
- CN
- China
- Prior art keywords
- component
- iii
- disperse orange
- dye composition
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000001048 orange dye Substances 0.000 title claims abstract description 29
- 239000000975 dye Substances 0.000 title description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 239000004744 fabric Substances 0.000 claims abstract description 16
- 229920000728 polyester Polymers 0.000 claims abstract description 11
- 239000002270 dispersing agent Substances 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 10
- 239000000986 disperse dye Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 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 claims description 2
- 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 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 12
- 239000002657 fibrous material Substances 0.000 abstract description 11
- 230000002209 hydrophobic effect Effects 0.000 abstract description 11
- 238000000859 sublimation Methods 0.000 abstract description 6
- 230000008022 sublimation Effects 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 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 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 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
- 241000899749 Dypsis lutescens Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- -1 methoxy, ethoxy Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- 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
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses a disperse orange dye composition which comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in formulas (I) and/or (II), the component B is selected from one or more of compounds shown in formula (III), and the component C is selected from one or more of compounds shown in formula (IV). The disperse orange dye composition provided by the invention is excellent in sublimation resistance, washing resistance and bubble color fastness when being applied to dyeing of hydrophobic fiber materials such as polyester and blended fabrics thereof:
Description
field of the art
The invention relates to a disperse orange dye composition and a dye product, in particular to a disperse orange dye composition and a dye product which are suitable for dyeing and printing hydrophobic fiber materials.
(II) background art
C.i. disperse orange 30 is a reddish brown powdery solid, and is widely used as one of the essential basic hues in polyester fibers because of its low price, uniformity, hiding, sun-proof properties, and other properties. However, textiles dyed with c.i. disperse orange 30 dyes, which detect severe overproof of tetrachlorophenol and pentachlorophenol, have poor alkali resistance, greatly limiting the amount of c.i. disperse orange 30 used, the netherlands company C & a has listed c.i. disperse orange 30 as a forbidden dye. Some patents such as CN101275039A, CN101265370A also describe substitutes similar to environment-friendly disperse orange 30, but the color light and fastness indexes of the substitutes cannot meet the requirements of C.I. disperse orange 30, and the substitutes cannot be directly replaced. Therefore, a dye product capable of directly replacing c.i. disperse orange 30 is urgently needed in the market, and not only is consistent color light under various light sources required, but also the fastness of washing, sublimation and bubbling of the dye is equal or even better, so as to meet the changing customer requirements.
(III) summary of the invention
In order to solve the problems, the invention provides a disperse orange dye composition and a dye product, which are applied to dyeing or printing of hydrophobic fiber materials and have the characteristics of excellent washing fastness, sublimation fastness, excellent bubble staining performance and the like.
The technical scheme adopted by the invention is as follows:
a disperse orange dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in formulas (I) and/or (II), the component B is selected from one or more of compounds shown in formulas (III), the component C is selected from one or more of compounds shown in formulas (IV), the mass percent of the component A is 20-75%, the mass percent of the component B is 20-75%, and the mass percent of the component C is 5-30% based on the components A-C:
in formula (I):
R 1 is cyanoethyl, C 1 ～C 4 Alkyl or CH 2 -CH＝CH 2 ；
n is 1 or 2.
In formula (II):
X 1 、X 2 each independently hydrogen or halogen;
R 2 、R 3 each independently is C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 The substituents of the alkyl groups being selected from-CN or-OCOC 6 H 5 。
In formula (III):
X 3 、X 4 each independently is NO 2 H, halogen, C 1 ～C 4 Alkoxy, -SO of (E) 2 -Ph、-COOC 2 H 4 OC 2 H 4 OCH 3 or-OCH 2 -Ph, ph is phenyl;
R 4 is C 1 ～C 4 Is a hydrocarbon group.
In formula (IV):
X 5 h, NO of a shape of H, NO 2 Halogen or CN;
R 5 is C 1 ～C 4 Alkyl of (a);
R 6 、R 7 each independently is hydrogen, C 1 ～C 4 Alkyl or substituted C of (2) 1 ～C 4 Alkyl, substituted C 1 ～C 4 The substituents of the alkyl groups being selected from-OCOR 8 、-COOR 9 ，R 8 、R 9 Each independently is C 1 ～C 4 Is a hydrocarbon group.
In the above formulas (I), (II), (III) and (IV), the above formula C 1 ～C 4 The alkyl group may be methyl, ethyl, straight or branched propyl, straight or branched butyl. The C is 1 ～C 4 The alkoxy group may be methoxy, ethoxy, straight or branched propoxy, straight or branched butoxy. Halogen is preferably Cl or Br.
Preferably, 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:
preferably, the component B is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
preferably, the component C is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
as a further preferred aspect, the disperse orange dye composition comprises:
component A is selected from formulas (I-1), (II-1) and/or (II-3);
component B is selected from the formulae (III-1), (III-2), (III-6) and/or (III-7);
the component C is selected from at least one of formulas (IV-1) to (IV-4).
Based on the components A to C, the mass percentage of the component A is 20 to 75 percent, the mass percentage of the component B is 20 to 75 percent, and the mass percentage of the component C is 5 to 30 percent.
Further, the disperse orange dye composition consists of a component A, a component B and a component C, wherein the mass percent of the component A is 20-75%, the mass percent of the component B is 20-75%, and the mass percent of the component C is 5-30% based on the components A-C.
Further, the disperse orange dye composition provided by the invention consists of a component A, a component B and a component C, wherein:
component A is selected from formulas (I-1), (II-1) and/or (II-3);
component B is selected from the formulae (III-1), (III-2), (III-6) and/or (III-7);
the component C is selected from at least one of formulas (IV-1) to (IV-4).
Based on the components A to C, the mass percentage of the component A is 20 to 75 percent, the mass percentage of the component B is 20 to 75 percent, and the mass percentage of the component C is 5 to 30 percent.
The disperse orange dye composition of the invention generally requires the addition of conventional auxiliary agents in the commercialization process. Thus, the present invention also provides a disperse dye preparation comprising the disperse orange dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse orange dye composition is (0.2-5): 1, preferably (0.5-2): 1. Preferably, the disperse dye product consists of a disperse orange dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in disperse dye compounding, and is particularly preferably one or a mixture of more than two of the following: lignin sulfonate (such as commercial dispersant Reax 83A, reax a), methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, polycarboxylic acid type polymeric dispersant, and the like.
The disperse dye product can be obtained by the following method: mixing the component A, B, C monomer compound (raw dye) according to a proportion, and then carrying out micropellet formation by using a grinder such as a sand grinder or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compound of component A, B, C may be mixed in proportion after being subjected to a micropelletization treatment by a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively. The disperse dye preparation according to the invention is liquid after grinding by a sand mill or a grinding machine and can be in powder or granule form after spray drying, which is a preparation method known to the person skilled in the art, since 100% removal of moisture is not possible during spray drying, a certain amount of moisture is allowed to be present even in the powder or granule form of the dye preparation, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to dyeing of textile fibers, the technical feature contributing to the improvement of dyeing effect is the dye component and the proportion contained in the product.
The disperse orange dye composition provided by the invention also allows the disperse orange dye composition to be further compounded and synergized with other dyes to prepare novel orange, blue or black dye products. The dye compounds of the formulae (I), (II), (III), (IV) according to the invention can be conveniently synthesized in a manner known to the person skilled in the art, and commercially available products can also be used.
The invention provides application of the disperse orange dye composition and dye product in dyeing of hydrophobic fiber materials. The dye prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a manner conventional in industry, such as a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip dyeing method comprises the steps of pretreating the hydrophobic fiber material, putting the pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dyed hydrophobic fiber material to be neutral by cold water, wringing the hydrophobic fiber material, carrying out reduction washing and drying the hydrophobic fiber material; and (3) directly printing, namely, carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, steaming, fixing the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and setting.
The disperse orange dye composition and the dye product provided by the invention meet the requirements of the ecological environment-friendly Standard Oeko-Tex Standard l00 on textiles when being applied to dyeing or printing of hydrophobic fiber materials, and have the characteristics of excellent washing and sublimation fastness, excellent bubble staining performance and the like.
4. Detailed description of the preferred embodiments
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
example 1
25 g of dye compound of formula (I-1), 10 g of dye compound of formula (II-3), 45 g of dye compound of formula (-III 1), 10 g of dye compound of formula (IV-1) and 250 g of dispersing agent MF are mixed together by adding 2500 g of water, and then are ground, dispersed and spray-dried to obtain a finished product, and the finished product can provide orange color tone of polyester and blended fabrics thereof.
Example 2
20 g of dye compound of formula (I-1), 10 g of dye compound of formula (II-1), 50 g of dye compound of formula (III-2), 20 g of dye compound of formula (IV-2), 200 g of dispersing agent MF and 30 g of sodium lignin sulfonate are mixed together by adding 2500 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide orange color tone of polyester and blended fabrics thereof.
Example 3
15 g of dye compound of formula (II-1), 15 g of dye compound of formula (II-3), 40 g of dye compound of formula (II-7), 30 g of dye compound of formula (IV-1) and 150 g of dispersing agent MF are mixed together by adding 500 g of water, and then the mixture is ground, dispersed and spray-dried, so that a finished product is obtained, and the finished product can provide orange color tone of polyester and blended fabrics thereof.
Examples 4 to 25
According to the method described in examples 1-3, except that the structures and weights of the component A, the component B and the component C in the table 1 are adopted, 200 g of an auxiliary agent (150 g of dispersing agent MF and 50 g of sodium lignin sulfonate) is added, 2650 g of water is added and mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare a finished product, wherein the dye can provide orange color tone with excellent fastness properties for polyester and blended fabrics thereof.
TABLE 1
/>
Example 26
20 g of dye compound shown in formula (I-1), 10 g of dye compound shown in formula (II-3), 45 g of dye compound shown in formula (-III 1), 10 g of dye compound shown in formula (IV-1), 5g of C.I. disperse orange 25 shown in formula (V) and 250 g of dispersing agent MF are mixed together by adding 2500 g of water, and then are ground, dispersed and spray-dried, so that a finished product can be obtained, and the finished product can provide orange color of polyester and blended fabrics thereof.
Comparative example 1:
a commercially available disperse yellow palm S-4RL 150% (C.I. DISP. ORANGE 30) dye was used as comparative example 1.
Comparative example 2:
example 2 in CN 101880476B was taken as comparative example 2, the dye composition of which is as follows:
dyeing examples
The disperse dyes prepared in examples 1-26 and comparative examples 1-2 are respectively weighed, polyester fabrics are treated by a conventional high temperature and high pressure dyeing method, in the treatment process, the dyeing depth (o.w.f) is controlled to be 2.6%, the bath ratio is 1:25, the pH value of the dyeing bath is regulated to be 4-5, the dyeing is carried out at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the temperature is kept for 60min, and the dyed fabrics are obtained by washing, reduction washing, acid neutralization and shaping (180 ℃ for 30 s) according to the conventional method. The sublimation resistance and the wash fastness are respectively tested by ISO 105-X11 and AATCC 61-2A, and the concrete is shown in Table 2:
TABLE 2
/>
Bubble drop color fastness test
The polyester fabrics 2g dyed by the dyes in examples 1-26 and comparative examples 1-2 and white cloth 2g of the same specification are respectively put into 60 ℃ (clean water), 60 ℃ (washing powder 5 g/L), 95 ℃ (clean water) and 95 ℃ (washing powder 5 g/L) for soaking for 15min after being sewed, the bath ratio is 1:50, the color loss is light and heavy, the white cloth staining rating is judged, and the result is shown in Table 3:
TABLE 3 Table 3
/>
Therefore, when the disperse orange dye product is applied to dyeing of terylene and blended fabrics, the sublimation fastness and the washing fastness are outstanding, the bubble color fastness is excellent, and the disperse orange dye product can be further compounded with magenta and dark blue disperse dyes to enrich dye varieties.
Claims (9)
1. A disperse orange dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in formulas (I) and/or (II), the component B is selected from one or more of compounds shown in formulas (III-1) to (III-2), (III-5) to (III-11), the component C is selected from one or more of compounds shown in formula (IV), the mass percentage of the component A is 20-75%, the mass percentage of the component B is 20-75%, and the mass percentage of the component C is 5-30% based on the components A-C:
in formula (I):
R 1 is cyanoethyl, C 1 ～C 4 Alkyl or CH 2 -CH＝CH 2 ，
n is 1 or 2;
in formula (II):
X 1 、X 2 each of which is independently hydrogen or halogen,
R 2 、R 3 each independently substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 The substituents of the alkyl groups being selected from-CN or-OCOC 6 H 5 ；
In formula (IV):
X 5 h, NO of a shape of H, NO 2 Halogen or CN,
R 5 is C 1 ～C 4 Is a group comprising an alkyl group,
R 6 、R 7 each independently is hydrogen, C 1 ～C 4 Alkyl or substituted C of (2) 1 ～C 4 Alkyl, substituted C 1 ～C 4 The substituents of the alkyl groups being selected from-OCOR 8 、-COOR 9 ，R 8 、R 9 Each independently is C 1 ～C 4 Is a hydrocarbon group.
2. A disperse orange dye composition according to claim 1, wherein said C 1 ～C 4 Alkyl is methyl or ethyl, X 5 Is NO 2 Or CN.
3. A disperse orange dye composition according to claim 1, wherein component a is selected from one of the following formulas or a mixture of two or more of them in any proportion:
4. a disperse orange dye composition according to claim 1, wherein component C is selected from one of the following formulas or a mixture of two or more of them in any proportion:
5. a disperse orange dye composition according to claim 1, comprising component a, component B and component C:
component A is selected from formulas (I-1), (II-1) and/or (II-3);
component B is selected from the formulae (III-1), (III-2), (III-6) and/or (III-7);
the component C is at least one selected from formulas (IV-1) to (IV-4);
based on the components A to C, the mass percentage of the component A is 20 to 75 percent, the mass percentage of the component B is 20 to 75 percent, and the mass percentage of the component C is 5 to 30 percent;
6. the disperse orange dye composition according to claim 1, which consists of a component A, a component B and a component C, wherein the component A accounts for 20-75% of the total mass of the component A, the component B accounts for 20-75% of the total mass of the component B, and the component C accounts for 5-30% of the total mass of the component C.
7. The disperse orange dye composition of claim 5, consisting of component a, component B and component C, wherein:
component A is selected from formulas (I-1), (II-1) and/or (II-3);
component B is selected from the formulae (III-1), (III-2), (III-6) and/or (III-7);
the component C is at least one selected from formulas (IV-1) to (IV-4);
based on the components A to C, the mass percentage of the component A is 20 to 75 percent, the mass percentage of the component B is 20 to 75 percent, and the mass percentage of the component C is 5 to 30 percent.
8. A disperse dye preparation comprising the disperse orange dye composition according to any one of claims 1 to 7 and an auxiliary agent in a weight ratio of 0.2 to 5:1, wherein the auxiliary agent is one or a combination of any of the following: naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, anhydrous sodium sulfate and polycarboxylic acid polymer dispersant.
9. Use of the disperse dye article according to claim 8 for dyeing polyester and its blend fabrics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011509357.4A CN112724707B (en) | 2020-12-19 | 2020-12-19 | Disperse orange dye composition and dye product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011509357.4A CN112724707B (en) | 2020-12-19 | 2020-12-19 | Disperse orange dye composition and dye product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112724707A CN112724707A (en) | 2021-04-30 |
| CN112724707B true CN112724707B (en) | 2024-01-02 |
Family
ID=75603924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011509357.4A Active CN112724707B (en) | 2020-12-19 | 2020-12-19 | Disperse orange dye composition and dye product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112724707B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113980487A (en) * | 2021-11-03 | 2022-01-28 | 菲诺染料化工(无锡)有限公司 | High-fastness yellow-brown disperse dye mixture |
| CN116396625A (en) * | 2022-06-30 | 2023-07-07 | 浙江龙盛集团股份有限公司 | Disperse orange dye composition and product thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101880476A (en) * | 2010-06-29 | 2010-11-10 | 浙江龙盛染料化工有限公司 | Yellow-to-orange disperse dye composition |
| KR20130130966A (en) * | 2012-05-23 | 2013-12-03 | 공명도 | Black and navy blue disperse dye composition having excellent moisture resistance |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN111662569A (en) * | 2020-07-10 | 2020-09-15 | 约克夏(浙江)染化有限公司 | Orange disperse dye composition, orange disperse dye, and preparation method and application thereof |
-
2020
- 2020-12-19 CN CN202011509357.4A patent/CN112724707B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101880476A (en) * | 2010-06-29 | 2010-11-10 | 浙江龙盛染料化工有限公司 | Yellow-to-orange disperse dye composition |
| KR20130130966A (en) * | 2012-05-23 | 2013-12-03 | 공명도 | Black and navy blue disperse dye composition having excellent moisture resistance |
| CN104088165A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Use of disperse dye in polyester fiber dyeing |
| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN111662569A (en) * | 2020-07-10 | 2020-09-15 | 约克夏(浙江)染化有限公司 | Orange disperse dye composition, orange disperse dye, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112724707A (en) | 2021-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111117289B (en) | Blue-to-black disperse dye composition and dye product | |
| CN113583474B (en) | Blue-to-black disperse dye composition and dye product | |
| CN111718601B (en) | Disperse turquoise blue dye composition and dye product | |
| CN112574595B (en) | Blue-to-black disperse dye composition and dye product | |
| CN105838109A (en) | High-fastness blue to black disperse dye composition and dye product | |
| CN112724707B (en) | Disperse orange dye composition and dye product | |
| CN114106585B (en) | Blue-to-black disperse dye composition and dye product | |
| CN113563737B (en) | Blue-to-black disperse dye composition and dye product | |
| CN111718600B (en) | Disperse turquoise blue dye composition and dye product | |
| CN111484754B (en) | Disperse blue-to-black dye composition and dye product | |
| CN109535769B (en) | Disperse red dye composition and dye product | |
| CN112708286B (en) | Blue-to-black disperse dye composition and dye product | |
| CN112876876B (en) | Disperse yellow-orange dye composition and dye product thereof | |
| CN112574594B (en) | Disperse yellow-orange dye composition and product thereof | |
| CN112048190B (en) | Disperse blue-to-black dye composition and dye product thereof | |
| CN111718602B (en) | Disperse turquoise blue dye composition and dye product | |
| CN109021616B (en) | Disperse yellow dye composition, and product and application thereof | |
| CN112724704B (en) | Disperse red jade dye composition and dye product | |
| CN112679985B (en) | Blue-to-black disperse dye composition and dye product | |
| CN105348860A (en) | High-fastness blue-to-black color disperse dye composition and dye product | |
| CN112724705B (en) | Blue-to-black disperse dye composition and dye product | |
| CN112646390B (en) | Dark blue to black disperse dye composition and dye product | |
| CN115124858B (en) | Disperse orange dye composition and product thereof | |
| CN114773877B (en) | Disperse blue dye composition and product thereof | |
| CN112608622B (en) | Blue-to-black disperse dye composition and dye product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |