CN116925564A - Reactive deep blue-to-black dye composition and dye product - Google Patents
Reactive deep blue-to-black dye composition and dye product Download PDFInfo
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- CN116925564A CN116925564A CN202310783536.4A CN202310783536A CN116925564A CN 116925564 A CN116925564 A CN 116925564A CN 202310783536 A CN202310783536 A CN 202310783536A CN 116925564 A CN116925564 A CN 116925564A
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- black dye
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 alkali metal salt Chemical class 0.000 claims abstract description 45
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 159000000000 sodium salts Chemical group 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 6
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 150000003254 radicals Chemical class 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 36
- 238000005406 washing Methods 0.000 abstract description 9
- 239000002657 fibrous material Substances 0.000 abstract description 8
- 238000007639 printing Methods 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 86
- 239000004744 fabric Substances 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 11
- 239000012752 auxiliary agent Substances 0.000 description 7
- 239000000985 reactive dye Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000009980 pad dyeing Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- 229920006052 Chinlon® Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 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 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 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
- 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 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011487 hemp Substances 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 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
- 229920001778 nylon Polymers 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber 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
- 239000002562 thickening 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0047—Mixtures of two or more reactive azo dyes
- C09B67/005—Mixtures of two or more reactive azo dyes all the reactive groups being not directly attached to a heterocyclic system
-
- 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
- C09B67/0072—Preparations with anionic dyes or reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses an active deep blue-black dye composition and a dye product, wherein the active deep blue-black dye composition comprises a component A and a component B, the component A is selected from at least one of a dye compound shown in a formula (I) and an alkali metal salt thereof, and the component B is selected from at least one of a dye compound shown in a formula (II) and an alkali metal salt thereof; in the reactive deep blue-black dye composition, the mass percentage of the component A is 45-95%, and the mass percentage of the component B is 5-55%. The reactive deep blue to black dye preparation contains the reactive deep blue to black dye composition. The reactive deep blue-to-black dye composition and the product thereof are used for printing and dyeing of fiber materials containing nitrogen and/or hydroxyl, and have the characteristics of good lifting property, good compatibility, high fixation rate, excellent color fastness, particularly outstanding washing fastness and the like.
Description
Technical Field
The invention relates to a reactive dye composition, in particular to a reactive deep blue-to-black dye composition and a dye product suitable for printing and dyeing of nitrogen-containing and/or hydroxyl-containing fiber materials.
Background
At present, the work of developing a novel dye structure on a large scale is not common, and a great deal of work is turned to research on application performance of the dye, between the dyes and the compound synergy of the dye and the auxiliary agent. The reactive dye molecule comprises a parent dye and an active group, along with the continuous increase of fiber varieties and the continuous development of dyeing technology, the dyeing performance and technological requirements of the dye market on the reactive dye are higher and higher, the reactive blue-black dye is used as a large-application-amount dye species in the market, good color fastness is required to be dyed, the lifting power and the fixation rate are high, the blue and orange dye is usually compounded in the industry, and the C.I. reactive black 5 is mainly used for screening and evaluating the orange component, such as common reactive black WNN and the like, and along with the improvement of the dyeing requirements of the textile printing and dyeing industry on the dye, more high-quality reactive deep blue to black dyes are necessary to be searched for so as to meet the middle-end and high-end market requirements.
Disclosure of Invention
In order to meet the market demands of middle-end and high-end dyes, the invention provides an active deep blue-to-black dye composition and a dye product by optimizing the active black KNB structure of a main component and then screening novel active orange, active yellow and/or active red as compound components, has the characteristics of good washing fastness, high fixation rate, good lifting power and the like, and is suitable for printing and dyeing of nitrogen-containing and/or hydroxyl-containing fiber materials and blended fabrics thereof.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
the invention provides an active deep blue-black dye composition, which comprises a component A and a component B, wherein the component A is selected from at least one of a dye compound shown in a formula (I) and an alkali metal salt thereof, and the component B is selected from at least one of a dye compound shown in a formula (II) and an alkali metal salt thereof; in the reactive deep blue-to-black dye composition, the mass percentage of the component A is 45-95%, and the mass percentage of the component B is 5-55%:
in formula (I):
R 1 h, C of a shape of H, C 1 ～C 4 Alkyl or-R 7 COOH, wherein R is 7 Is C 1 ～C 4 An alkylene group of (a); r is R 2 Is unsubstituted or substituted C 1 ～C 4 Alkyl, wherein, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl, phenyl or hydroxy 1 ～C 4 An alkyl group;
R 3 ～R 6 each independently is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonic acid groups;
Y 1 、Y 2 each independently is-ch=ch 2 、-CH 2 CH 2 OSO 3 H or-CH 2 CH 2 Cl；
In formula (II):
D 1 、D 2 each independently is a group represented by the following formula (a) or (b):
R 8 is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, carboxyl or sulfonic groups;
R 9 、R 10 each independently is hydrogen, oxygen, -COR 14 、C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, wherein, substituted C 1 ～C 4 Alkyl being C substituted by hydroxy, sulfo or carboxyl 1 ～C 4 Alkyl, R 14 Is C 1 ～C 4 Alkyl, C 2 ～C 4 Alkenyl or-NH 2 ；
R 11 ～R 13 Each independently is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonic acid groups;
X 1 、X 2 each independently is-SO 2 Y 3 、-NHCO(CH 2 ) p SO 2 Y 4 or-CONH (CH) 2 ) q SO 2 Y 5 Wherein Y is 3 ～Y 5 Each independently is-ch=ch 2 、-CH 2 CH 2 OSO 3 H or-CH 2 CH 2 Cl, p and q are each independently selected from natural numbers between 1 and 3.
In the invention, the C 1 ～C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; the C is 1 ～C 4 The alkoxy group may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy and the like.
Further, R 1 Is hydrogen, R 2 Is methyl, ethyl, hydroxyethyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate.
Further, R 3 ～R 6 Each independently is preferably hydrogen, methyl, methoxy or a sulfonate group.
Further, D 1 、D 2 And is also preferably a group represented by the formula (a) or (b).
Further, D 1 、D 2 And is also preferably a group represented by the formula (a).
Further, R 8 Preferably H, methyl, methoxy, carboxyl or sulfonate.
Further, R 9 、R 10 Each independently is preferably hydrogen or-COR 14 Wherein R is 14 Is methyl or-NH 2 。
Further, R 11 ～R 13 Each independently is preferably hydrogen, methyl, methoxy or a sulfonate group.
Further, X 1 、X 2 Each independently is preferably-SO 2 Y 3 、-NHCOCH 2 CH 2 SO 2 Y 4 or-CONHCH 2 CH 2 SO 2 Y 5 Wherein Y is 3 ～Y 5 Each independently is-ch=ch 2 or-CH 2 CH 2 OSO 3 H。
As a first group of preferred embodiments of the present invention, the reactive deep blue to black dye composition consists of component A and component B.
As a second preferred embodiment of the present invention, the reactive deep blue to black dye composition may further comprise a component C, wherein the component C is at least one selected from the group consisting of a compound represented by formula (III), a compound represented by formula (IV) and an alkali metal salt thereof, the composition comprises 45 to 95% by mass of component A, 5 to 50% by mass of component B, and 1 to 40% by mass (preferably 1 to 30% by mass) of component C;
in formula (III):
R 16 ～R 19 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, carboxyl or sulfonic acid groups, preferably H, methyl, methoxy, carboxyl or sulfonic acid groups;
R 14 、R 15 each independently is hydrogen, C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl, phenyl or hydroxy 1 ～C 4 An alkyl group; preferably hydrogen, methyl, ethyl, hydroxyethyl, benzyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate;
Y 6 、Y 7 each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-C 2 H 4 Cl, preferably-ch=ch 2 or-C 2 H 4 OSO 3 H；
m is 0 or 1;
n is 0 or 1;
a. b are each independently 0 or 1;
each D 3 、D 4 Are independently substituted phenyl, unsubstituted phenyl, substituted naphthyl or unsubstituted naphthyl, the number of substituents of the substituted phenyl and the substituted naphthyl is respectively 1-3, and each substituent is independently selected from amino, sulfonic acid group, ureido and C 1 ～C 4 Alkanoylamino, C 1 ～C 4 Alkoxy or hydroxy, preferably 1 to 2 substituents each, each independently selected from amino, sulfonate, ureido, acetamido, methoxy or hydroxy;
in formula (IV):
R 21 ～R 24 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably H, methyl, methoxy or sulfonate;
R 20 is hydrogen, C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl or hydroxy 1 ～C 4 An alkyl group; preferably hydrogen, methyl, ethyl, hydroxyethyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate;
Y 8 、Y 9 each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-C 2 H 4 Cl, preferably-ch=ch 2 or-C 2 H 4 OSO 3 H；
c is 0 or 1.
Further, the reactive deep blue to black dye composition according to the present invention preferably comprises the following dye components:
component A: at least one selected from the group consisting of a dye compound represented by the formula (I) and an alkali metal salt thereof;
component B: at least one selected from the group consisting of a dye compound represented by the formula (II) and an alkali metal salt thereof;
component C: the component C is selected from at least one of a compound shown in a formula (III), a compound shown in a formula (IV) and alkali metal salts thereof, wherein m and n are 0, or one of m and n is 0, the other is 1, a is 1, b is 0 or 1, and C is 0 or 1.
Further, the reactive deep blue to black dye composition consists of a component A, a component B and a component C.
Still further, the reactive deep blue to black dye composition of the present invention preferably consists of the following dye components:
component A: at least one selected from the group consisting of a dye compound represented by the formula (I) and an alkali metal salt thereof;
component B: at least one selected from the group consisting of a dye compound represented by the formula (II) and an alkali metal salt thereof;
component C: the component C is selected from at least one of a compound shown in a formula (III), a compound shown in a formula (IV) and alkali metal salts thereof, wherein m and n are 0, or one of m and n is 0, the other is 1, a is 1, b is 0 or 1, and C is 0 or 1.
Specifically, the component A is preferably at least one dye compound represented by the following formulas (I-1) to (I-15) and an alkali metal salt thereof:
further, the component A is preferably at least one selected from the group consisting of the compounds represented by the formulae (I-1) to (I-7), the formulae (I-10), and the formulae (I-12) and alkali metal salts thereof.
Specifically, the component B is preferably at least one dye compound represented by the following formulas (II-1) to (II-39) and an alkali metal salt thereof:
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further, the component B is preferably at least one selected from the group consisting of compounds represented by the formulae (II-1) to (II-9) and alkali metal salts thereof. In particular, the component C is preferably at least one of the following dye compounds and their alkali metal salts:
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the reactive deep blue to black dye compositions according to the invention, the dye compounds (I) to (IV) used, can be synthesized by conventional methods, for example by means of customary diazotisation and coupling reactions using suitable components and using the necessary proportions known to the person skilled in the art.
In addition, the reactive deep blue to black dye composition of the present invention may be an alkali metal salt, preferably a sodium salt or a potassium salt. It is clear to the person skilled in the art that the dye compounds in the free acid form and the dye compounds in the alkali metal salt form (e.g. sodium salt, potassium salt, etc.) have substantially the same dyeing properties, and that the structural formula of each single-color dye compound is generally defined in the free acid form, whereas in the actual synthesis process, the preparation and isolation is generally carried out in the alkali metal salt form (e.g. sodium salt or potassium salt) and also in the salt form for dyeing, as is well known to the person skilled in the art.
The reactive deep blue to black dye composition of the present invention is prepared by mixing the dye components in the above-mentioned proportions, and the mixing may be performed by conventional mechanical means, such as in a grinder, kneader or homogenizer, during which the individual dye compounds may be present in the form of powder, granules, aqueous solutions or synthetic solutions, and when the individual dye compounds are blended in the form of synthetic solutions, the separation of the reactive deep blue to black dye of the present invention from the synthetic solutions may be performed by generally known methods, such as salting out the dye from the reaction medium with an electrolyte (e.g., sodium chloride or potassium chloride), or evaporating, spray-drying the mixed solution, and thus each dye component and its dye composition usually contain conventional electrolyte salts (e.g., sodium chloride, sodium sulfate, etc.) in the reactive dye.
The reactive deep blue to black dye composition provided by the invention can be used as a commodity to be sold without adding auxiliary agents, and can also be added with conventional auxiliary agents in commercial dyes, such as cosolvent, dispersing agent, alkali resistance auxiliary agent, dust-proof agent, surfactant, buffering agent, accelerating agent and the like. Accordingly, the present invention also provides a reactive deep blue to black dye preparation comprising said reactive deep blue to black dye composition. Preferably, the reactive deep blue to black dye preparation comprises the reactive deep blue to black dye composition and an auxiliary agent. The auxiliary is present in an amount of not more than 45%, preferably not more than 40% by weight of the reactive deep blue to black dye composition. The auxiliary agent is preferably one or a combination of any of the following: naphthalene sulfonic acid formaldehyde condensate (NNO), methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), diffusant CNF (benzyl naphthalene sulfonate formaldehyde condensate), anhydrous sodium sulfate (industrial sodium sulfate), lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, thickener, and the like. The auxiliary agents are all commercially available conventional varieties.
The reactive deep blue to black dye product is suitable for printing and dyeing nitrogen-containing and/or hydroxyl-containing fiber materials, wherein the nitrogen-containing and/or hydroxyl-containing fiber materials can be cellulose fibers, polyamide fibers and fabrics thereof, and the cellulose fibers are preferably cotton fibers or regenerated fibers, and can also comprise other plant fibers such as hemp fibers or fabrics; the polyamide fibers are preferably animal fiber materials including sheath, fur or filament, and synthetic fiber materials such as nylon 6 and nylon 66. When the reactive deep blue to black dye product is used for printing and dyeing the fiber material, the method can be carried out according to the known reactive dye dyeing method, such as the common reactive dye dip dyeing method and pad dyeing method, wherein the dip dyeing method is a method for dipping the fabric in a dye solution to gradually dye the fabric, and the working procedures of dyeing, fixation, washing, soaping, washing, dehydration, drying and the like are generally required.
The pad dyeing is a dyeing method that firstly, fabrics are immersed in dye liquor, then the fabrics pass through a roller, the dye liquor is uniformly padded into the fabrics, and then the fabrics are subjected to steaming or hot melting treatment and the like, and the dyeing method generally needs the procedures of padding dye liquor-drying- (padding color fixing liquor) -steaming or baking-washing-soaping-washing-drying and the like.
Generally, due to different dyeing requirements on fabrics, the dye usage amount is also different, when the dip dyeing method is used for dyeing, the dyeing depth (owf) is generally 0.1-10 percent (the dye accounts for the weight percentage of the fabric), the bath ratio is 1:2-1:60 (the weight ratio of the fabric to the dye liquor is preferably 1:10-1:30), the primary dyeing temperature is controlled to be 30-60 ℃, the dyeing time is 10-30 minutes, the soaping temperature is 85-95 ℃, the soaping time is 10-15 minutes, the fixation temperature is 60-100 ℃, the fixation time is 10-50 minutes, and the fixation pH value is 9-11. When the pad dyeing method is used for dyeing, the pad ratio of the cellulose fiber is generally 60-80%, the steaming temperature is 100-103 ℃, and the steaming time is 1-3 minutes. In the pad dyeing method, a cold pad-batch dyeing method is used at present, dye and alkaline substances are introduced into a pad dyeing machine, and are coiled and piled for 2-30 hours at room temperature to fix colors, and then thoroughly rinsed.
The beneficial effects of the invention are mainly as follows: the reactive deep blue-to-black dye composition and the product thereof are used for printing and dyeing of fiber materials containing nitrogen and/or hydroxyl, and have the characteristics of good lifting property, good compatibility, high fixation rate, excellent color fastness, particularly outstanding washing fastness and the like.
Detailed Description
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
the dye compounds used in the examples of the present invention were prepared and isolated in the form of their sodium salts during the actual synthesis and also used for dyeing in the form of their sodium salts, but for convenience of writing, all chemical formulas of the dye compounds in the examples were embodied in the form of free acids, the actual dyeing properties being equivalent to the sodium salt form.
Example 1:
the composite dye is prepared by mechanically mixing 65 parts of dye compound shown in formula (I-2), 35 parts of dye compound shown in formula (II-1) and 10 parts of anhydrous sodium sulfate, and the obtained composite dye is dyed into black by adopting a conventional dip dyeing method, has excellent lifting force (see GB/T21875-2016) and has a fixation rate of 78% (see GB/T2391-2014), and particularly has the color fastness of chinlon and wool reaching more than 4 levels (see ISO 105C 10-2006).
Example 2:
the dyeing method comprises the steps of mechanically mixing 60 parts of dye compound shown in a formula (I-2), 25 parts of dye compound shown in a formula (II-2), 15 parts of dye compound shown in a formula (III-1) and 10 parts of anhydrous sodium sulfate, dyeing cotton into black by adopting a conventional dip dyeing method to obtain a composite dye, wherein the dyeing fastness of washing resistance, particularly chinlon and wool reaches more than 4 levels (refer to ISO 105C 10-2006), the lifting force is excellent (refer to GB/T21875-2016), and the fixation rate reaches 79% (refer to GB/T2391-2014).
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Example 3:
45 parts of dye compound shown in formula (I-1), 10 parts of dye compound shown in formula (II-1), 25 parts of dye compound shown in formula (III-1), 20 parts of dye compound shown in formula (IV-1) and 10 parts of anhydrous sodium sulfate are mechanically mixed, the obtained composite dye is dyed into black by adopting a conventional dip dyeing method, the color fastness of washing-resistant color, especially nylon and wool reaches more than 4 levels (refer to ISO 105C 10-2006), the lifting force is excellent (refer to GB/T21875-2016), and the color fixation rate reaches 81% (refer to GB/T2391-2014).
Examples 4 to 72
According to the method of one of the embodiments 1 to 3, the dyes with the proportions listed in the table 1 are mechanically mixed, and according to the conventional dyeing method of reactive dyes, dyed cotton is deep blue to black, the fastness to washing and staining, especially chinlon and wool staining, reaches more than 4 levels (refer to ISO 105C 10-2006), the lifting force is excellent (refer to GB/T21875-2016), and the fixation rate reaches more than 80% (refer to GB/T2391-2014).
TABLE 1
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Compared with the existing black dye in the market, the reactive deep blue-to-black dye provided by the invention has obviously improved washing fastness and fixation rate, and can meet the printing and dyeing requirements of medium-grade or high-grade textiles.
Claims (10)
1. A reactive deep blue to black dye composition characterized by: the reactive deep blue-black dye composition comprises a component A and a component B, wherein the component A is selected from at least one of a dye compound shown in a formula (I) and alkali metal salts thereof, and the component B is selected from at least one of a dye compound shown in a formula (II) and alkali metal salts thereof; in the reactive deep blue-to-black dye composition, the mass percentage of the component A is 45-95%, and the mass percentage of the component B is 5-55%:
in formula (I):
R 1 h, C of a shape of H, C 1 ～C 4 Alkyl or-R 7 COOH, wherein R is 7 Is C 1 ～C 4 Alkylene of (C), preferably R 1 Is hydrogen, R 2 Is a armorA radical, ethyl, hydroxyethyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate;
R 2 is unsubstituted or substituted C 1 ～C 4 Alkyl, wherein, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl, phenyl or hydroxy 1 ～C 4 An alkyl group;
R 3 ～R 6 each independently is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably R 3 ～R 6 Each independently is hydrogen, methyl, methoxy, or sulfonate;
Y 1 、Y 2 each independently is-ch=ch 2 、-CH 2 CH 2 OSO 3 H or-CH 2 CH 2 Cl；
In formula (II):
D 1 、D 2 each independently is a group represented by the following formula (a) or (b):
R 8 is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, carboxyl or sulphonic acid groups, preferably R 8 Is H, methyl, methoxy, carboxyl or sulfonic group;
R 9 、R 10 each independently is hydrogen, oxygen, -COR 14 、C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, wherein, substituted C 1 ～C 4 Alkyl being C substituted by hydroxy, sulfo or carboxyl 1 ～C 4 Alkyl, R 14 Is C 1 ～C 4 Alkyl, C 2 ～C 4 Alkenyl or-NH 2 The method comprises the steps of carrying out a first treatment on the surface of the Preferably R 9 、R 10 Each independently is hydrogen or-COR 14 Wherein R is 14 Is methyl or-NH 2 ；
R 11 ～R 13 Each independently is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably R 11 ～R 13 Each independently is hydrogen, methyl, methoxy, or sulfonate;
X 1 、X 2 each independently is-SO 2 Y 3 、-NHCO(CH 2 ) p SO 2 Y 4 or-CONH (CH) 2 ) q SO 2 Y 5 Wherein Y is 3 ～Y 5 Each independently is-ch=ch 2 、-CH 2 CH 2 OSO 3 H or-CH 2 CH 2 Cl, p and q are each independently selected from natural numbers between 1 and 3; preferably X 1 、X 2 Each independently is-SO 2 Y 3 、-NHCOCH 2 CH 2 SO 2 Y 4 or-CONHCH 2 CH 2 SO 2 Y 5 Wherein Y is 3 ～Y 5 Each independently is-ch=ch 2 or-CH 2 CH 2 OSO 3 H。
2. The reactive deep blue to black dye composition according to claim 1, wherein: the reactive deep blue-to-black dye composition consists of a component A and a component B.
3. The reactive deep blue to black dye composition according to claim 1, wherein: the reactive deep blue-black dye composition can also comprise a component C, wherein the component C is selected from at least one of a compound shown in a formula (III), a compound shown in a formula (IV) and alkali metal salts thereof, the mass percent of the component A is 45-95%, the mass percent of the component B is 5-50%, and the mass percent of the component C is 1-40%;
in formula (III):
R 16 ～R 19 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, carboxyl or sulfonic acid groups, preferably H, methyl, methoxy, carboxyl or sulfonic acid groups;
R 14 、R 15 each independently is hydrogen, C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl, phenyl or hydroxy 1 ～C 4 An alkyl group; preferably hydrogen, methyl, ethyl, hydroxyethyl, benzyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate;
Y 6 、Y 7 each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-C 2 H 4 Cl；
m is 0 or 1;
n is 0 or 1;
a. b are each independently 0 or 1;
each D 3 、D 4 Are independently substituted phenyl, unsubstituted phenyl, substituted naphthyl or unsubstituted naphthyl, the number of substituents of the substituted phenyl and the substituted naphthyl is respectively 1-3, and each substituent is independently selected from amino, sulfonic acid group, ureido and C 1 ～C 4 Alkanoylamino, C 1 ～C 4 Alkoxy or hydroxy, preferably 1 to 2 substituents each, each independently selected from amino, sulfonate, ureido, acetamido, methoxy or hydroxy;
in formula (IV):
R 21 ～R 24 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably H, methyl, methoxy or sulfonate;
R 20 is hydrogen, C 1 ～C 4 Alkyl or substituted C 1 ～C 4 Alkyl, substituted C 1 ～C 4 Alkyl being C substituted by sulfo, carboxyl or hydroxy 1 ～C 4 An alkyl group; preferably hydrogen, methyl, ethyl, hydroxyethyl, methyl sulfonate, ethyl sulfonate, methyl carboxylateA radical or carboxylic acid ethyl group;
Y 8 、Y 9 each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-C 2 H 4 Cl；
c is 0 or 1.
4. A reactive deep blue to black dye composition according to claim 3, wherein: the reactive deep blue-to-black dye composition consists of a component A, a component B and a component C.
5. The reactive deep blue to black dye composition according to claim 3 or 4, wherein: in the reactive deep blue to black dye composition,
the component A is at least one dye compound shown in a formula (I) and alkali metal salt thereof;
the component B is at least one dye compound shown in a formula (II) and alkali metal salt thereof;
the component C is selected from at least one of a compound shown in a formula (III), a compound shown in a formula (IV) and alkali metal salts thereof, wherein m and n are 0, or one of m and n is 0, the other is 1, a is 1, b is 0 or 1, and C is 0 or 1.
6. Reactive deep blue to black dye composition according to one of claims 1 to 4, characterized in that: the component A is selected from at least one of the following dye compounds shown in the formulas (I-1) to (I-15) and alkali metal salts thereof:
7. reactive deep blue to black dye composition according to one of claims 1 to 4, characterized in that: the component B is at least one dye compound shown in the following formulas (II-1) to (II-39) and alkali metal salt thereof:
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8. reactive deep blue to black dye composition according to one of claims 1 to 4, characterized in that: the component C is selected from at least one of the following dye compounds and alkali metal salts thereof:
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9. reactive deep blue to black dye composition according to one of claims 1 to 4, characterized in that: the alkali metal salt is sodium salt or potassium salt.
10. A reactive deep blue to black dye preparation characterized by: the reactive deep blue to black dye preparation comprising the reactive deep blue to black dye composition according to any one of claims 1 to 4.
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