CN116925567A - Reactive dark blue to black dye composition and dye product - Google Patents
Reactive dark blue to black dye composition and dye product Download PDFInfo
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- CN116925567A CN116925567A CN202310783565.0A CN202310783565A CN116925567A CN 116925567 A CN116925567 A CN 116925567A CN 202310783565 A CN202310783565 A CN 202310783565A CN 116925567 A CN116925567 A CN 116925567A
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- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 alkali metal salt Chemical class 0.000 claims abstract description 38
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000000217 alkyl group Chemical group 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
- 238000002360 preparation method Methods 0.000 claims description 4
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002947 alkylene group Chemical group 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 32
- 238000005406 washing Methods 0.000 abstract description 10
- 239000002657 fibrous material Substances 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 80
- 238000000034 method Methods 0.000 description 25
- 239000004744 fabric Substances 0.000 description 12
- 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
- 239000012752 auxiliary agent Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 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
- 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
- 239000002253 acid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 229920006052 Chinlon® Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 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
- 229920001778 nylon Polymers 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
- 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
- 229920001732 Lignosulfonate Polymers 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
- 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
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 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
- 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
- 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
- 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
- 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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
- C09B67/0057—Mixtures of two or more reactive disazo dyes
- C09B67/0059—Mixtures of two or more reactive disazo dyes all the reactive groups are 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 dark blue to black dye composition and a dye product. The active dark blue-to-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 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 active dark 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%. The reactive navy blue to black dye product contains the reactive navy blue to black dye composition. The active navy 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 and a dye product, in particular to a reactive navy blue-black dye composition and a dye product suitable for printing and dyeing of nitrogen-containing and/or hydroxyl-containing fiber materials.
Background
The navy reactive dye is subjected to the process from single component to mixed splicing, the performances are perfected from the aspects of deep dyeing, color fastness, fixation rate and the like, the navy reactive dye is mainly prepared from active black KNB, and yellow, orange and/or red varieties are added for compounding, so that the navy reactive dye is actually a navy blue dye with higher gray scale, and in order to obtain the dark full color, the industry is focused on screening and evaluating orange components, such as common active black WNN and the like, and along with the improvement of the dyeing requirements of the textile dyeing industry on the dye, more high-quality navy reactive navy dyes are necessary to be searched for meeting the market demands of middle and high ends.
Disclosure of Invention
In order to meet the market demands of middle-end and high-end dyes, the inventor provides an active dark 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 dark blue to 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 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 active dark 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 the substituent is sulfonic acid group, carboxyl group, phenyl group or hydroxyl 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) or (c):
in the above formulas (a), (b) and (c): r is R 8 、R 9 、R 11 、R 12 、R 14 、R 15 Each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonic acid groups; x and y are each independently a natural number between 1 and 3, each R 10 Each independently selected from H, sulfonic acid group, ureido group or C 1 ～C 4 Alkanoylamino groups of (2); each R 13 Each independently selected from H, hydroxy or sulfonate;
X 1 、X 2 、X 3 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 p and q are each independently selected from natural numbers between 1 and 3, Y 3 ～Y 5 Each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-CH 2 CH 2 Cl。
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 All from the group of formula (a), the substituents may be the same or different; or D 1 Selected from the group represented by formula (a), D 2 Selected from the group represented by formula (b) or formula (c).
Further, R 8 、R 9 、R 11 、R 12 、R 14 、R 15 Each independently is preferably H, methyl, methoxy or a sulfonate group.
Further, R 10 Preferably hydrogen, a sulfonic acid group, a ureido group or an acetamido group.
As a first preferred scheme of the invention, the active navy blue-black dye composition consists of a component A and a component B, wherein the mass percentage of the component A is 45-95%, and the mass percentage of the component B is 5-55%.
As a second preferred embodiment of the present invention, the reactive navy blue to black dye composition may further include 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 18 ～R 21 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 16 、R 17 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 23 ～R 26 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably H, methyl, methoxy or sulfonate;
R 22 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 navy to black dye composition of the present invention preferably comprises the following dye components:
component A: at least one dye compound selected from the group consisting of dye compounds represented by formula (I) and alkali metal salts 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 navy blue to black dye composition consists of a component A, a component B and a component C.
Still further, the reactive navy to black dye composition of the present invention is preferably composed of the following dye components:
component A: at least one dye compound represented by formula (I) or an alkali metal salt thereof;
component B: at least one dye compound represented by the formula (II) or an alkali metal salt thereof; and
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-42) 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-2) to (II-8) and the formulae (II-20) to (II-24) 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 navy to black dye compositions according to the invention, the dye compounds (I) to (IV) used, 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 the process or analogous processes according to patent CN 101250334A.
In addition, the reactive navy 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 preparation method of the active navy blue to black dye composition comprises the steps of mixing the dye components according to the proportion, wherein the mixing can be carried out in a conventional mechanical mode, such as a grinder, a kneader or a homogenizer, single dye compounds can exist in the form of powder, granules, aqueous solution or synthetic solution in the mixing process, and when the single dye compounds are mixed in the form of the synthetic solution, the separation of the composite active navy blue to black dye according to the invention from the synthetic solution can be carried out in a commonly known method, such as salting out the dye from a reaction medium by using electrolyte (such as sodium chloride or potassium chloride), or evaporating and spray-drying the mixed solution, so that each dye component and the dye composition thereof usually comprise conventional electrolyte salts (such as sodium chloride, sodium sulfate and the like) in the active dye.
The active navy 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. Thus, the present invention also provides a reactive navy to black dye preparation comprising the reactive navy to black dye composition. Preferably, the active navy blue to black dye product contains the active navy blue to black dye composition and an auxiliary agent. The weight of the auxiliary does not exceed 45%, preferably not more than 40% of the weight of the active navy 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 navy 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 navy blue to black dye product is used for printing and dyeing the fiber materials, 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 active navy 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:
70 parts of dye compound shown in formula (I-2), 30 parts of dye compound shown in formula (II-20) and 10 parts of anhydrous sodium sulfate are mechanically mixed, and the obtained composite dye is dyed into black by adopting a conventional dip dyeing method, has excellent lifting power (see GB/T21875-2016) and has high fixation rate (see GB/T2391-2014), and particularly has high color fastness to washing, especially nylon and wool reaching more than 4 levels (see ISO 105C 10-2006).
Example 2:
70 parts of dye compound shown in formula (I-2), 25 parts of dye compound shown in formula (II-21), 5 parts of dye compound shown in formula (III-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 washing fastness, especially the nylon and wool fastness, 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 80% (refer to GB/T2391-2014).
Example 3:
45 parts of dye compound shown in formula (I-1), 15 parts of dye compound shown in formula (II-3), 25 parts of dye compound shown in formula (II-20), 15 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 fastness to washing and staining, especially 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 82% (refer to GB/T2391-2014).
Examples 4 to 75
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, the dyed cotton is dark 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 dark 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. An active navy blue to black dye composition, which is characterized in that: the active dark blue-to-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 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 active dark 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 the substituent is sulfonic acid group, carboxyl group, phenyl group or hydroxyl group; preferably R 1 Is hydrogen, R 2 Methyl, ethyl, hydroxyethyl, methyl sulfonate, ethyl sulfonate, methyl carboxylate or ethyl carboxylate;
R 3 ～R 6 each independently is hydrogen, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonic acid groups; 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) or (c), preferably D 1 、D 2 All from the group of the formula (a), the substituents may be identical or different, or D 1 Selected from the group represented by formula (a), D 2 A group selected from the group represented by formula (b) or formula (c):
in the above formulas (a), (b) and (c): r is R 8 、R 9 、R 11 、R 12 、R 14 、R 15 Each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonic acid groups; preferably R 8 、R 9 、R 11 、R 12 、R 14 、R 15 Each independently is H, methyl, methoxy or sulfonate;
x and y are each independently a natural number between 1 and 3, each R 10 Each independently selected from H, sulfonic acid group, ureido group or C 1 ～C 4 Preferably each R 10 Each independently hydrogen, sulfonate, ureido, or acetamido; each R 13 Each independently selected from H, hydroxy or sulfonate;
X 1 、X 2 、X 3 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 p and q are each independently selected from natural numbers between 1 and 3, Y 3 ～Y 5 Each independently is-ch=ch 2 、-C 2 H 4 OSO 3 H or-CH 2 CH 2 Cl。
2. The reactive navy to black dye composition of claim 1, wherein: the active dark blue-to-black dye composition consists of a component A and a component B, wherein the mass percentage of the component A is 45-95%, and the mass percentage of the component B is 5-55%.
3. The reactive navy to black dye composition of claim 1, wherein: the active dark blue-to-black dye composition further comprises 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, in the composition, the mass percentage of the component A is 45-95%, the mass percentage of the component B is 5-50%, and the mass percentage of the component C is 1-40%;
in formula (III):
R 18 ～R 21 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy, carboxyl or sulphonic acid groups, preferably R 18 ～R 21 Each independently is H, methyl, methoxy, carboxyl or sulfonate;
R 16 、R 17 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 R 16 、R 17 Each independently is 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 23 ～R 26 each independently H, C 1 ～C 4 Alkyl, C 1 ～C 4 Alkoxy or sulfonate, preferably R 23 ～R 26 Each independently is H, methyl, methoxy or sulfonate;
R 22 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 R 22 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 Y 8 、Y 9 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 H；
c is 0 or 1.
4. The reactive navy to black dye composition of claim 3, wherein: the active dark blue-to-black dye composition consists of a component A, a component B and a component C.
5. The reactive navy to black dye composition of claim 3 or 4, wherein: in the active dark blue to black dye composition,
the component A is selected from at least one of dye compounds shown in a formula (I) and alkali metal salts 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. The reactive navy to black dye composition according to any one of claims 1 to 4, wherein: 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. the reactive navy to black dye composition according to any one of claims 1 to 4, wherein: the component B is at least one dye compound shown in the following formulas (II-1) to (II-42) and alkali metal salt thereof:
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8. the reactive navy to black dye composition according to any one of claims 1 to 4, wherein: the component C is selected from at least one of the following dye compounds and alkali metal salts thereof:
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9. the reactive navy to black dye composition according to any one of claims 1 to 4, wherein: the alkali metal salt is sodium salt or potassium salt.
10. An active navy blue to black dye product, which is characterized in that: the reactive navy to black dye preparation comprises the reactive navy to black dye composition according to any one of claims 1 to 4.
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| CN107501997A (en) * | 2017-07-28 | 2017-12-22 | 浙江科永化工有限公司 | A kind of reactive navy blue is to black dye composition and dye preparations |
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