CN116200050A - Disperse blue-to-black dye composition and dye product thereof - Google Patents
Disperse blue-to-black dye composition and dye product thereof Download PDFInfo
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- CN116200050A CN116200050A CN202211699046.8A CN202211699046A CN116200050A CN 116200050 A CN116200050 A CN 116200050A CN 202211699046 A CN202211699046 A CN 202211699046A CN 116200050 A CN116200050 A CN 116200050A
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- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 239000000975 dye Substances 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000000986 disperse dye Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 239000012752 auxiliary agent Substances 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- -1 cyano, phenyl Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 13
- 238000005406 washing Methods 0.000 abstract description 12
- 239000002657 fibrous material Substances 0.000 abstract description 4
- 230000002209 hydrophobic effect Effects 0.000 abstract description 4
- 238000005859 coupling reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 230000008878 coupling Effects 0.000 description 19
- 238000010168 coupling process Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000004744 fabric Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000000227 grinding Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- DUEGOHNPUBPUIV-UHFFFAOYSA-N 3-methyl-4-nitrobenzoyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=C1[N+]([O-])=O DUEGOHNPUBPUIV-UHFFFAOYSA-N 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 238000004537 pulping Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- KHZRTXVUEZJYNE-UHFFFAOYSA-N 3-[4-[(2,6-dichloro-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl KHZRTXVUEZJYNE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000006149 azo coupling reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 2
- WZJJWQVBLSPALW-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)anilino]propanenitrile Chemical compound N#CCCN(CCO)C1=CC=CC=C1 WZJJWQVBLSPALW-UHFFFAOYSA-N 0.000 description 2
- WAYVZRALCRKXTF-UHFFFAOYSA-N 5-methyl-2-nitrobenzoyl chloride Chemical group CC1=CC=C([N+]([O-])=O)C(C(Cl)=O)=C1 WAYVZRALCRKXTF-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 241000872198 Serjania polyphylla Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 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
- 239000003995 emulsifying agent Substances 0.000 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 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VMIORCIXXWGAGI-UHFFFAOYSA-N 2-(n-benzylanilino)ethanol Chemical group C=1C=CC=CC=1N(CCO)CC1=CC=CC=C1 VMIORCIXXWGAGI-UHFFFAOYSA-N 0.000 description 1
- KRNUKKZDGDAWBF-UHFFFAOYSA-N 2-(n-ethyl-n-m-toluidino)ethanol Chemical group OCCN(CC)C1=CC=CC(C)=C1 KRNUKKZDGDAWBF-UHFFFAOYSA-N 0.000 description 1
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical group OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical group OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-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
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010017 direct printing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 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 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WFFKSTRPZWRBEW-UHFFFAOYSA-N n-[2-[(2-bromo-4,6-dinitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O WFFKSTRPZWRBEW-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000000843 powder Substances 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
- 239000002002 slurry Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 239000004753 textile Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a disperse blue-to-black dye composition and a dye product thereof. The disperse blue-to-black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), and the component C is selected from at least one of the following formulas (III), wherein the mass percent of the component A is 5-70%, the mass percent of the component B is 20-85%, and the mass percent of the component C is5 to 50 percent. The invention provides a dye product containing the disperse blue-to-black dye composition, which has high lifting force, good dyeing darkness and excellent color fastness, particularly prominent washing fastness and rubbing fastness when being applied to dyeing of hydrophobic fiber materials.
Description
Technical Field
The invention relates to a disperse dye composition, in particular to a disperse blue-to-black dye composition suitable for dyeing and printing hydrophobic fiber materials and a product thereof.
Background
The maximum amount of blue-black series dye is used in disperse dyes, and the traditional dye composition of blue-black by C.I. disperse blue 291:1, C.I. disperse violet 93 and C.I. disperse orange 76 is classified as forbidden dye by European countries such as Germany because the C.I. disperse orange 76 can be cracked under certain specific conditions to generate aromatic amine harmful to human body, generate allergy to human body. In recent years, there have been many disperse blue-black dye compositions replacing c.i. disperse orange 76, but there is still room for further improvement.
Disclosure of Invention
The invention provides a blue-to-black disperse dye composition and a dye product, which are high in lifting force, good in deep dyeing property, excellent in various color fastness, and particularly outstanding in washing fastness and rubbing fastness when being applied to dyeing of hydrophobic fiber materials.
The technical scheme adopted by the invention is as follows:
a disperse blue-to-black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), and the component C is selected from at least one of the following formulas (III), wherein the mass percent of the component A is 5-70%, the mass percent of the component B is 20-85%, and the mass percent of the component C is 5-50%:
in formula (I):
R 1 、R 2 each independently hydrogen, nitro, cyano or halogen;
R 3 is hydrogen or C 1 ～C 4 An alkoxy group;
R 4 is hydrogen, C 1 ～C 4 Alkyl or-NHCOR 16 ，R 16 Is C 1 ～C 4 An alkyl group;
R 5 is hydrogen, C 1 ～C 4 Alkyl, R 17 -CN、R 18 -Ph or R 19 OCOR 20 ，R 17 ～R 19 Each independently is C 1 ～C 4 Alkylene group, R 20 Is C 1 ～C 4 An alkyl group;
in formula (II):
X 1 is-Cl, -Br or cyano;
R 6 、R 7 each independently is C 1 ～C 4 Alkyl of (a);
R 8 、R 9 each independently is C 1 ～C 4 Alkyl, -CH of (C) 2 CH＝CH 2 Or by cyano groups, C 1 ～C 4 Alkoxy, -COOR 21 Substituted C 1 ～C 4 Alkyl, wherein R is 21 Is C 1 ～C 4 Alkyl of (a);
in formula (III):
X 2 is-Cl, -Br or cyano;
R 10 is C 1 ～C 4 Alkyl of (a);
R 11 、R 12 each independently is C 1 ～C 4 Or by alkyl groups of cyano, C 1 ～C 4 Alkoxy, -COOR 22 Substituted C 1 ～C 4 Alkyl, wherein R is 22 Is C 1 ～C 4 Is a hydrocarbon group.
In the invention, the C 1 ～C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Further, the nitro position on the right-hand benzene ring in formula (I) is either the 4-position or the 6-position.
Further, the nitro position on the right-hand benzene ring in formula (I) is the 6-position.
Further, R 1 、R 2 Each independently is preferably hydrogen, nitro, cyano, chloro or bromo.
Further, R 1 、R 2 Each independently is preferably hydrogen, nitro or chlorine.
Further, R 3 Preferably hydrogen or methoxy.
Further, R 4 Preferably hydrogen, methyl or-NHCOCH 3 。
Further, R 4 Preferably hydrogen or-NHCOCH 3 。
Further, R 5 Preferably hydrogen, ethyl, cyanoethyl, benzyl or-CH 2 CH 2 OCOCH 3 。
Further, R 5 Preferably cyanoethyl or-CH 2 CH 2 OCOCH 3 。
Further, X 1 preferably-Cl or-Br.
Further, R 6 、R 7 Each independently is preferably methyl.
Further, R 8 、R 9 Each independently is preferably ethyl or-CH 2 CH＝CH 2 。
Further, X 2 preferably-Cl or-Br.
Further, R 10 Preferably methyl.
Further, R 11 、R 12 Each independently is preferably ethyl.
As an implementation mode, the blue-to-black disperse dye composition consists of a component A, a component B and a component C, wherein the mass percent of the component A is 5-70%, the mass percent of the component B is 20-85%, and the mass percent of the component C is 5-50%.
As another embodiment, the blue to black disperse dye composition of the invention can further comprise a component D, wherein the component D is at least one selected from compounds shown in a formula (IV), the mass percent of the component A is 5-70%, the mass percent of the component B is 20-85%, the mass percent of the component C is 5-50%, and the mass percent of the component D is 5-50%:
in the above formula (IV):
X 3 、X 4 each independently hydrogen, cl or Br, preferably hydrogen;
R 13 is hydrogen, C 1 ～C 4 Alkyl, C of (2) 1 ～C 4 Alkoxy or halogen of (2), preferably hydrogen, methyl, methoxy or Cl;
R 14 、R 15 each independently is C 1 ～C 4 Or by cyano, phenyl, -OCOR 23 Substituted C 1 ～C 4 Alkyl, wherein R is 23 Is C 1 ～C 4 Alkyl of R 14 、R 15 Each independently is preferably ethyl, cyanoethyl, -CH 2 -Ph or-C 2 H 4 -Ph, wherein Ph is phenyl.
As a further embodiment, the blue-to-black disperse dye composition consists of a component A, a component B, a component C and a component D, wherein the mass percent of the component A is 5-70%, the mass percent of the component B is 20-85%, the mass percent of the component C is 5-50%, and the mass percent of the component D is 5-50%.
Specifically, the component A is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
further, component A is at least one compound selected from the group consisting of the compounds represented by the formulae (I-1) to (I-14), the formulae (I-57) to (I-64) and the formulae (I-71) to (I-78).
Further, component A is at least one selected from the group consisting of compounds of formula (I-1), formula (I-3), formula (I-6) and formula (I-8).
Specifically, the component B is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
further, the component B is at least one selected from the compounds represented by the formulas (II-1) to (II-4). Specifically, the component C is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
further, the component C is at least one selected from the compounds represented by the formula (III-1) or the formula (III-2). Specifically, the component D is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
further, component D is at least one selected from the group consisting of compounds represented by formula (IV-1) and formula (IV-2).
Preferably, the blue-to-black disperse dye composition comprises a component A, a component B and a component C, wherein the mass percentage of the component A is 5-60%, the mass percentage of the component B is 20-80%, and the mass percentage of the component C is 5-45%.
Preferably, the blue-to-black disperse dye composition comprises 5-60% by mass of a component A, 20-80% by mass of a component B, 5-45% by mass of a component C and 5-45% by mass of a component D.
A particularly preferred embodiment 1 of the present invention is: the blue to black disperse dye composition comprises a component A, a component B and a component C, wherein:
the component A is at least one selected from the group consisting of compounds represented by the formulae (I-1) to (I-14), (I-57) to (I-64), and (I-71) to (I-78), and more particularly at least one of the formulae (I-1), (I-3), (I-6) and (I-8) is preferable;
the component B is at least one selected from the formulas (II-1) to (II-4);
component C is selected from at least one of formula (III-1) or formula (III-2);
in the composition, the mass percentage of the component A is 5-60%, the mass percentage of the component B is 20-80%, and the mass percentage of the component C is 5-45%.
A particularly preferred embodiment 2 of the present invention is: the blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D, wherein:
the component A is at least one selected from the group consisting of compounds represented by the formulae (I-1) to (I-14), (I-57) to (I-64), and (I-71) to (I-78), and more particularly at least one of the formulae (I-1), (I-3), (I-6) and (I-8) is preferable;
the component B is at least one selected from the formulas (II-1) to (II-4);
component C is selected from at least one of formula (III-1) or formula (III-2);
component D is selected from at least one of the formula (IV-1) or the formula (IV-2);
in the composition, the mass percentage of the component A is 5-60%, the mass percentage of the component B is 20-80%, the mass percentage of the component C is 5-45%, and the mass percentage of the component D is 5-45%.
The disperse dye compositions according to the invention, in which the dye compounds (II) to (IV) are known dyes, can be synthesized by conventional methods, for example by using suitable components known to the person skilled in the art and using the necessary proportions by means of customary diazotisation and coupling reactions, or by reference to the process or analogous processes in patent EP0038527A, GB2123845A, CN 104059377A.
The reactive dye compounds of formula (I) can also be prepared according to conventional diazo coupling methods for reactive dyes, for example:
(1) Preparation of the coupling component of formula (I-b):
A：R 5 is hydrogen, C 1 ～C 4 Alkyl, R 17 -CN or R 18 at-Ph, R 17 、R 18 Is defined as formula (I)
Esterifying the compound of formula (I-c 1) with acyl chloride in an organic solvent at 0-30 ℃ to obtain the compound of formula (I-b).
B：R 5 Is R 19 OCOR 20 When R is 19 、R 20 Is defined as formula (I)
Esterifying a compound of formula (I-c 2) with an acyl chloride in an organic solvent at a temperature of 0-5 ℃ to obtain a compound of formula (I-c 3), and then reacting the compound of formula (I-c 3) with (R) 20 CO) 2 O is esterified at 70-80 ℃ to obtain the compound of the formula (I-b).
(2) Diazotization:
diazotizing a compound of formula (I-a) with nitrosylsulfuric acid in an acidic medium, and controlling the temperature between 0 and 20 ℃.
(3) Coupling reaction:
stirring and pulping a compound of the formula (I-b) in water, adding diazonium salt obtained in the step (2), controlling the temperature between 0 and 20 ℃ for coupling reaction, heating the material to 45-65 ℃ after the reaction is finished, preserving the heat for 1-2 hours, and then carrying out suction filtration and washing to neutrality to obtain the disperse dye compound of the formula (I).
In the formula (I-a), the formula (I-b) and the formulas (I-c 1) to (I-c 3), R 1 ～R 6 、R 17 ～R 20 Is defined as in formula (I).
The disperse blue-to-black dye composition can be directly sold as a commodity or can be sold as a commodity after adding a conventional auxiliary agent or applied to coloring textile materials. Therefore, the invention also provides a disperse blue-to-black dye product, which mainly comprises the disperse blue-to-black dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5:1. Preferably, the disperse dye product consists of the disperse 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 preferably one or a mixture of more than two of the following components in any proportion: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate [ such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF) ], naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), sodium sulfate (sodium sulfate), and the like.
The preparation method of the disperse dye product provided by the invention comprises the following steps: mixing dye monomer compounds (raw dyes) forming disperse blue to black dye composition according to a proportion, and then carrying out micropellet by using a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent, water or other wetting agents; alternatively, the dye monomer compounds may be subjected to a fine particle formation treatment by a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively, and then mixed in proportion. The blue to black dye dispersion product of the present invention is liquid after grinding by a sand mill or a grinding machine, and can be powder or granule after spray drying, which is a preparation method well known to those skilled in the art.
The disperse dye prepared according to the invention can be dyed by adopting a common dip dyeing method and a pad dyeing method, and can also be used for direct printing. The common dip dyeing method comprises the steps of pretreating polyester fabric, putting the polyester fabric into a dye vat for dip dyeing, washing the polyester fabric to be neutral by cold water after dyeing, wringing the polyester fabric, carrying out reduction washing, and drying the polyester fabric; 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.
When the disperse blue to black dye prepared by the invention is used for dyeing hydrophobic fiber materials, each color fastness is excellent, and particularly, the disperse blue to black dye has excellent washing fastness and rubbing fastness.
Drawings
FIG. 1 is a mass spectrum of a compound of formula (I-1) obtained in example 1;
FIG. 2 is a mass spectrum of the compound of formula (I-2) obtained in example 2.
Detailed Description
The present invention will be further illustrated with reference to examples, but the scope of the present invention is not limited thereto.
Example 1:
preparing a coupling component: 0.1mol of N-cyanoethyl-N-hydroxyethyl aniline and 100mL of 1, 2-dichloroethane are added into a 250mL four-necked flask, 0.25mol of triethylamine is added as an acid binding agent after stirring and dissolving, 0.1mol of 3-methyl-4-nitrobenzoyl chloride is slowly added under the condition of room temperature, the temperature of a system is controlled between 20 ℃ and 30 ℃ in a feeding process, the total feeding time is 30min, the stirring reaction is carried out for 30min after the feeding is finished, the end point (ethyl acetate: petroleum ether=1:1) is detected by TLC, and if the raw materials are completely reacted, 100mL of clear water is added for washing and separating liquid, and the oil phase is reserved. The oil phase was distilled off under reduced pressure at 70℃to give the coupling component shown as (I-b 1), which was diluted with 30mL of acetic acid.
Diazo synthesis: adding 24.84g of water into a 250ml container, cooling, adding 88g of 98% concentrated sulfuric acid, continuously cooling to 10 ℃, adding 0.1mol of paranitroaniline, and stirring for 4 hours at 20-30 ℃; slowly dripping 0.105mol of nitrosylsulfuric acid at the temperature of 10-15 ℃ for 6-7 h, and continuously stirring for 4h after the dripping is finished to obtain diazonium solution (for later use).
Coupling reaction: 600g of water, 2g of emulsifier TX-15 and 0.1mol (I-b 1) of coupling component are added into a 1000mL container, pulping is carried out at room temperature for 30min, and then 2g of sulfamic acid is added and the temperature is reduced to 10 ℃. Dropwise adding the prepared diazonium solution within 1-2 h, controlling the coupling temperature to be 10-15 ℃ for 2h, after the reaction is completed (detecting the reaction end point by using a permeation ring experiment), heating the material to 55 ℃, preserving heat for 1h, carrying out suction filtration, and washing to neutrality to obtain the dye compound shown in the formula (I-1), wherein the lambda max in the obtained dye DMF solution is 450nm. Adding an auxiliary agent MF and water, grinding uniformly, drying and dehydrating to obtain the disperse dye, wherein the weight ratio of the MF to the dye compound is 0.6:1, and the water amount is 1.5 times of the sum of the weight of the auxiliary agent MF and the dye compound.
Example 2:
preparing a coupling component: the coupling component (I-b 2) was prepared as described in example 1, and diluted with 30mL of acetic acid.
Diazo synthesis: 30.5g of 98% sulfuric acid and 0.105mol of nitrosylsulfuric acid are added into a 150mL container, after stirring and cooling to 10 ℃,0.1 mol of 2, 4-dinitro-6-chloroaniline is slowly added, the system temperature is controlled between 10 ℃ and 20 ℃ during the feeding period, the total feeding time is 1h, and after the feeding is completed, the 15 ℃ to 20 ℃ heat preservation reaction is carried out for 7h to 8h, so as to obtain a diazonium solution (for standby).
Coupling reaction: 600g of water, 2g of emulsifier TX-15 and 0.1mol (I-b 2) of coupling component are added into a 1000mL container, pulping is carried out at room temperature for 30min, and then 2g of sulfamic acid is added and the temperature is reduced to 10 ℃. Dropping the prepared diazonium solution within 1-2 h, controlling the coupling temperature to be 10-15 ℃ for 2h, after the reaction is completed (detecting the reaction end point by using a permeation ring experiment), heating the material to 55 ℃, preserving the heat for 1h, carrying out suction filtration, and washing to be neutral to obtain the dye compound shown in the formula (I-2). And adding an auxiliary agent MF and water into the obtained dye DMF solution, grinding uniformly, and drying and dehydrating to obtain the disperse dye, wherein the weight ratio of the MF to the dye compound is 0.6:1, and the water amount is 1.5 times of the sum of the weights of the auxiliary agent MF and the dye compound.
Example 3:
preparing a coupling component: 0.1mol of 3- [ N, N- (dihydroxyethyl) amino ] -4-methoxyacetanilide and 80mL of acetonitrile are added into a 250mL four-necked flask, 0.25mol of triethylamine is added as an acid binding agent after stirring and dissolving, 0.103mol of 3-methyl-4-nitrobenzoyl chloride is slowly added under the condition of room temperature, the temperature of a feeding process is controlled between 0 ℃ and 5 ℃, the total feeding time is 1h, the stirring reaction is carried out for 1h after the feeding is finished, the finishing point (ethyl acetate: petroleum ether=4:1) is detected by TLC, if the raw materials are completely reacted, 0.11mol of acetic anhydride is added, and the temperature is raised to 70 ℃ for 5h after heat preservation reaction. After completion of the reaction (endpoint of the reaction was detected by HPLC), acetonitrile was distilled off under reduced pressure at 70℃to obtain a coupling component represented by (I-b 4) which was diluted with 30mL of acetic acid for use.
Diazo synthesis: 30.5g of 98% sulfuric acid and 0.105mol of nitrosylsulfuric acid are added into a 150mL container, after stirring and cooling to 10 ℃,0.1 mol of 2, 4-dinitro-6-chloroaniline is slowly added, the system temperature is controlled between 10 ℃ and 20 ℃ during the feeding period, the total feeding time is 1h, and after the feeding is completed, the 15 ℃ to 20 ℃ heat preservation reaction is carried out for 7h to 8h, so as to obtain a diazonium solution (standby).
Coupling reaction: 600g of water, 2g of emulsifier-15 and 0.1mol (I-b 4) of coupling component are added into a 1000mL container, pulping is carried out at room temperature for 30min, and then 2g of sulfamic acid is added and cooled to 0-5 ℃. Dropping the prepared diazonium solution within 1-2 h, controlling the coupling temperature to be 0-5 ℃ for 2h, after the reaction is completed (detecting the reaction end point by using a permeation ring experiment), heating the material to 55 ℃, preserving the heat for 1h, carrying out suction filtration, and washing to be neutral to obtain the target product. And adding an auxiliary agent MF and water into the obtained dye DMF solution, grinding uniformly, and drying and dehydrating to obtain the disperse dye, wherein the weight ratio of the MF to the dye compound is 0.6:1, and the water amount is 1.5 times of the sum of the weights of the auxiliary agent MF and the dye compound.
Examples 4 to 47:
preparation of the coupling component: according to the preparation method of the coupling component described in example 1 or 2, the intermediate raw material N-cyanoethyl-N-hydroxyethyl aniline is replaced with N-ethyl-N-hydroxyethyl aniline, N-ethyl-N-hydroxyethyl-3-methylaniline, N-hydroxyethyl aniline or N-benzyl-N-hydroxyethyl aniline as required, and 3-methyl-4-nitrobenzoyl chloride is replaced with 3-methyl-6-nitrobenzoyl chloride as required, and the intermediates represented by the structures of formula (I-b) in examples 4 to 47 in Table 1 below can be prepared, respectively.
Preparation of the dye: the diazo coupling procedure described in example 1 or 2 was followed, except that the starting diazo component, the coupling component were replaced by the compounds of formula (I-a), formula (I-b) in Table 1 below, to give the dye compounds shown in the table and λmax in DMF.
TABLE 1 raw materials and dye Compounds
Examples 48 to 102:
preparation of the coupling component: according to the preparation method of the coupling component described in example 3, the intermediate raw material 3- [ N, N- (dihydroxyethyl) amino ] -4-methoxyacetanilide was replaced with 3- [ N, N- (dihydroxyethyl) amino ] acetanilide, N-dihydroxyethylanilide, 3-methyl-N, N-dihydroxyethylanilide, 3-methyl-4-nitrobenzoyl chloride was replaced with 3-methyl-6-nitrobenzoyl chloride as needed, and the intermediates shown by the structure of the formula (I-b) in examples 48 to 102 in Table 2 below were each prepared.
Preparation of the dye: the diazo coupling procedure described in example 3 was followed, except that the starting diazo component, the coupling component, were replaced by the compounds of formula (I-a), formula (I-b) in Table 1 below, to give the dye compounds shown in the table and λmax in DMF.
TABLE 2 raw materials and dye Compounds
Example 103:
10 g of a component A of a compound of a formula (I-6), 23 g of a compound of a formula (II-1) and 7 g of a component B of a compound of a formula (II-2), 25 g of a component C of a compound of a formula (III-1), 35 g of a component D of a compound of a formula (IV-1) and 250 g of a dispersing agent MF are mixed together by adding 650 g of water, and then the mixture is ground, dispersed and dried to obtain a finished product, wherein the dye can provide black with excellent fastness properties for polyester and blended fabrics thereof.
Example 104:
the dye can provide black with excellent fastness performance for polyester and blended fabrics thereof, and is prepared by blending 25 g of component A of a compound of formula (I-1), 20 g of a compound of formula (II-1), 10 g of component B of a compound of formula (II-2), 25 g of component C of a compound of formula (III-2), 20 g of component D of a compound of formula (IV-1) and 250 g of dispersing agent MF with 650 g of water, grinding, dispersing and drying.
Examples 105 to 170:
according to the method described in example 103 or 104, except that the structure and weight of components A-D in the table are adopted, 250 g of auxiliary agent (dispersing agent MF is 200 g, sodium lignin sulfonate is 50 g) is added, 800 g of water is added to prepare slurry after blending, grinding and dispersing are carried out, and drying are carried out, so that the finished product is obtained, and the dye can provide blue to black color tone with excellent fastness properties for polyester and blended fabrics thereof:
TABLE 1
Dyeing examples:
2g of the disperse dyes prepared in examples 103 to 170 are weighed respectively, dispersed in 500 ml of water, sucked 90 ml and mixed with 30ml of water, pH is adjusted to 4.5 by acetic acid, 6 g of polyester-ammonia fabric is put in, the temperature is raised to 60 ℃, the temperature is continuously raised to 130 ℃ in a gradient of about 1 ℃/min, and the heat preservation and dyeing are carried out for 60 minutes. After cooling to 80 ℃, the fabric is placed in 240 ml of 80 ℃ reduction cleaning liquid for cleaning for 20min. Finally, the mixture is washed with 240 ml of 2g/L acetic acid solution at 40 ℃ for 15min, dried and heat-set at 180 ℃ for 30 seconds, and the washing fastness and the rubbing fastness are respectively measured by adopting the methods described in ISO105-C03 and ISO105-X12, and the results are shown in the following table 2:
TABLE 2
Claims (10)
1. A disperse blue to black dye composition characterized by: the disperse blue-to-black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the mass percentage of the component A is 5-70%, the mass percentage of the component B is 20-85%, and the mass percentage of the component C is 5-50%:
in formula (I):
R 1 、R 2 each independently hydrogen, nitro, cyano or halogen;
R 3 is hydrogen or C 1 ～C 4 An alkoxy group;
R 4 is hydrogen, C 1 ～C 4 Alkyl or-NHCOR 16 ，R 16 Is C 1 ～C 4 An alkyl group;
R 5 is hydrogen, C 1 ～C 4 Alkyl, R 17 -CN、R 18 -Ph or R 19 OCOR 20 ，R 17 ～R 19 Each independently is C 1 ～C 4 Alkylene group, R 20 Is C 1 ～C 4 An alkyl group;
in formula (II):
X 1 is-Cl, -Br or cyano;
R 6 、R 7 each independently is C 1 ～C 4 Alkyl of (a);
R 8 、R 9 each independently is C 1 ～C 4 Alkyl, -CH of (C) 2 CH＝CH 2 Or by cyano groups, C 1 ～C 4 Alkoxy, -COOR 21 Substituted C 1 ～C 4 Alkyl, wherein R is 21 Is C 1 ～C 4 Alkyl of (a);
in formula (III):
X 2 is-Cl, -Br or cyano;
R 10 is C 1 ～C 4 Alkyl of (a);
R 11 、R 12 each independently is C 1 ～C 4 Or by alkyl groups of cyano, C 1 ～C 4 Alkoxy, -COOR 22 Substituted C 1 ～C 4 Alkyl, wherein R is 22 Is C 1 ～C 4 Is a hydrocarbon group.
2. The disperse blue to black dye composition according to claim 1, wherein: the blue-to-black disperse dye composition consists of a component A, a component B and a component C, wherein the mass percentage of the component A is 5-70%, the mass percentage of the component B is 20-85%, and the mass percentage of the component C is 5-50%.
3. The disperse blue to black dye composition according to claim 1, wherein: the disperse blue-to-black dye composition further comprises a component D, wherein the component D is at least one selected from compounds shown in a formula (IV), the mass percentage of the component A is 5-70%, the mass percentage of the component B is 20-85%, the mass percentage of the component C is 5-50%, and the mass percentage of the component D is 5-50%:
in the above formula (IV):
X 3 、X 4 each independently hydrogen, cl or Br, preferably hydrogen;
R 13 is hydrogen, C 1 ～C 4 Alkyl, C of (2) 1 ～C 4 Alkoxy or halogen of (2), preferably hydrogen, methyl, methoxy or Cl;
R 14 、R 15 each independently is C 1 ～C 4 Or by cyano, phenyl, -OCOR 23 Substituted C 1 ～C 4 Alkyl, wherein R is 23 Is C 1 ～C 4 Alkyl of R 14 、R 15 Each independently is preferably ethyl, cyanoethyl, -CH 2 -Ph or-C 2 H 4 -Ph, wherein Ph is phenyl.
4. A disperse blue to black dye composition according to any one of claims 1 to 3, wherein: the nitro position on the right benzene ring in the formula (I) is 4-position or 6-position.
5. A disperse blue to black dye composition according to any one of claims 1 to 3, 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:
6. a disperse blue to black dye composition according to any one of claims 1 to 3, wherein: 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:
7. a disperse blue to black dye composition according to any one of claims 1 to 3, wherein: 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:
8. a disperse blue to black dye composition according to claim 3, wherein: the component D is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
9. a disperse blue to black dye composition according to any one of claims 1 to 3, wherein: the disperse blue to black dye composition:
the component A is at least one selected from the group consisting of compounds represented by the formulae (I-1) to (I-14), (I-57) to (I-64), and (I-71) to (I-78), and more particularly at least one of the formulae (I-1), (I-3), (I-6) and (I-8) is preferable;
the component B is at least one selected from the formulas (II-1) to (II-4);
component C is selected from at least one of formula (III-1) or formula (III-2);
component D is selected from at least one of the formula (IV-1) or the formula (IV-2);
in the composition, the mass percentage of the component A is 5-60%, the mass percentage of the component B is 20-80%, the mass percentage of the component C is 5-45%, and the mass percentage of the component D is 5-45%.
10. A disperse blue to black dye article comprising a disperse blue to black dye composition according to any one of claims 1 to 3 and an auxiliary agent in a weight ratio of auxiliary agent to disperse dye composition of from 0.2 to 5:1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092615A (en) * | 1959-07-01 | 1963-06-04 | Cfmc | Azo dyestuffs containing a quaternized pyrazolone radical |
| FR1356648A (en) * | 1963-05-09 | 1964-03-27 | Bayer Ag | Water insoluble azo dyes and processes for their preparation |
| DE2446213A1 (en) * | 1974-09-27 | 1976-04-08 | Basf Ag | P-AMINOAZO DISPERSION DYES |
| CN113583468A (en) * | 2021-09-03 | 2021-11-02 | 上海安诺其集团股份有限公司 | Dispersed brown and preparation method thereof |
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2022
- 2022-12-28 CN CN202211699046.8A patent/CN116200050A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092615A (en) * | 1959-07-01 | 1963-06-04 | Cfmc | Azo dyestuffs containing a quaternized pyrazolone radical |
| FR1356648A (en) * | 1963-05-09 | 1964-03-27 | Bayer Ag | Water insoluble azo dyes and processes for their preparation |
| DE2446213A1 (en) * | 1974-09-27 | 1976-04-08 | Basf Ag | P-AMINOAZO DISPERSION DYES |
| CN113583468A (en) * | 2021-09-03 | 2021-11-02 | 上海安诺其集团股份有限公司 | Dispersed brown and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| TOSHIKUNI KAINO 等: "《Third-Order Nonlinear Optical Properties of Organic Materials》", 《MATERIALS FOR NONLINEAR OPTICS: CHEMICAL PERSPECTIVES》, vol. 455, pages 704 - 721 * |
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