CN115093723B - Amino naphthol type disazo heterocyclic disperse dye - Google Patents
Amino naphthol type disazo heterocyclic disperse dye Download PDFInfo
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- CN115093723B CN115093723B CN202210863661.1A CN202210863661A CN115093723B CN 115093723 B CN115093723 B CN 115093723B CN 202210863661 A CN202210863661 A CN 202210863661A CN 115093723 B CN115093723 B CN 115093723B
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- disperse dye
- heterocyclic
- amino
- naphthol type
- amino naphthol
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 55
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 title claims abstract description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 63
- 238000004043 dyeing Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000012954 diazonium Substances 0.000 claims abstract description 25
- 238000005859 coupling reaction Methods 0.000 claims abstract description 23
- -1 amino naphthol compound Chemical class 0.000 claims abstract description 20
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 6
- 239000000975 dye Substances 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 19
- 239000004753 textile Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 239000002270 dispersing agent Substances 0.000 claims description 12
- 238000000227 grinding Methods 0.000 claims description 12
- 239000003086 colorant Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- 238000001694 spray drying Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004576 sand Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 238000007639 printing Methods 0.000 claims description 3
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 229920004934 Dacron® Polymers 0.000 claims description 2
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 229940127554 medical product Drugs 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 17
- 230000008878 coupling Effects 0.000 abstract description 13
- 238000010168 coupling process Methods 0.000 abstract description 13
- 150000001989 diazonium salts Chemical class 0.000 abstract description 12
- 229920004933 Terylene® Polymers 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 30
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004537 pulping Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 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 5
- 229920002472 Starch Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CJLUXPZQUXVJNF-UHFFFAOYSA-N 6-fluoro-1,3-benzothiazol-2-amine Chemical compound C1=C(F)C=C2SC(N)=NC2=C1 CJLUXPZQUXVJNF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- LMOFFYMADRWIHG-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazole Chemical compound C1=C(Cl)C(Cl)=CC2=C1SC=N2 LMOFFYMADRWIHG-UHFFFAOYSA-N 0.000 description 2
- LDTCWISGJYTXDC-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NSC2=C1 LDTCWISGJYTXDC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000009991 scouring Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009990 desizing Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000002759 woven fabric 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention discloses an amino naphthol type disazo heterocyclic disperse dye, and belongs to the technical field of fine chemical engineering. Firstly, preparing heterocyclic aromatic amine diazonium salt by using heterocyclic aromatic amine derivative as diazonium component, and carrying out coupling reaction with amino naphthol compound under acidic condition to prepare amino naphthol type monoazo heterocyclic disperse dye; and then the prepared monoazo heterocyclic disperse dye is used as a coupling component, and is subjected to coupling reaction with another part of diazonium salt under alkaline conditions to prepare the amino naphthol type bisazo heterocyclic disperse dye. The amino naphthol type disazo heterocyclic disperse dye can be used under the condition of 0.5-5g/L NaOH, has better color fastness, and can realize the short-process dyeing and finishing processing of terylene and blended fabrics thereof.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to an amino naphthol type disazo heterocyclic disperse dye.
Background
The current situation of high water consumption, high energy consumption and high pollution discharge of textile printing and dyeing is an important subject to be solved currently. Polyester fiber is widely applied to clothing, home textiles, military special fabrics and industrial textiles due to the excellent physical and chemical properties, and becomes the synthetic fiber variety with the largest yield and the most wide application in the world at present.
However, in dyeing and finishing of terylene and blended fabrics thereof, the pretreatment of fabrics (including desizing, scouring, alkali reduction and other procedures) and the reduction and cleaning after dyeing are all carried out under alkaline conditions, especially the scouring and alkali reduction are all carried out under strong alkaline (NaOH) conditions, and the disperse dye dyeing in the middle link is an acid bath (ph=4-4.5). The whole dyeing process has repeated neutralization and washing, long process flow and high energy and water consumption. The disperse dye dyed under the strong alkaline condition is developed, the pretreatment and the dyeing of the polyester fabric can be carried out in the same bath, and the method has the advantages of remarkable energy conservation and emission reduction.
The conventional disperse dye is not alkali-proof, and partial disperse dye has certain stability under certain alkaline conditions. The existing method mainly adopts alkaline agents such as sodium carbonate, sodium phosphate, sodium dihydrogen phosphate, disodium hydrogen phosphate and the like, and has weak alkalinity. However, the alkaline agent adopted in the pretreatment of terylene and blended fabrics thereof is NaOH and has higher concentration. Therefore, development of disperse dyes capable of stably dyeing under NaOH conditions has a large application market.
Disclosure of Invention
[ problem ]
The technical problems to be solved in practice of the invention are as follows: provides an amino naphthol type disazo heterocyclic disperse dye which has better alkali-resistant stability and better dyeability under strong alkaline condition and is suitable for short-process alkaline dyeing.
[ technical solution ]
The invention aims to provide an amino naphthol type disazo heterocyclic disperse dye, which is used for solving the problems that the existing alkali-resistant disperse dye can be applied under the condition that the pH value is more than or equal to 7 and less than or equal to 14, but the alkali agent can only be sodium carbonate, sodium bicarbonate, trisodium phosphate, sodium dihydrogen phosphate or disodium hydrogen phosphate and the like, but not can be strong alkali sodium hydroxide, and the application of the dye in a pretreatment/dyeing one-bath dyeing method of polyester fabrics is limited.
The first object of the invention is to provide an amino naphthol type disazo heterocyclic disperse dye, wherein the structural general formula of the dye is shown as follows:
or alternatively
Wherein R is 1 Is C1-4 alkyl, R 2 、R 3 Is hydrogen; or R is 2 Is C1-4 alkoxy, halogen (F, cl, br), R 1 、R 3 Is hydrogen; or R is 3 ＝-NO 2 ，R 1 、R 2 Is hydrogen; or R is 2 、R 3 Halogen (F, cl, br), R 1 Is hydrogen;
R 4 = -H or-NO 2 。
In one embodiment of the invention, R 2 ＝-OCH 3 ，R 1 、R 3 Is hydrogen; or R is 2 ＝-F，R 1 、R 3 Is hydrogen; or R is 3 ＝R 2 -Cl, the others being hydrogen; or R is 1 ＝-CH 3 The others are hydrogen.
A second object of the present invention is to provide a process for preparing the above-mentioned aminonaphthol-type disazo heterocyclic disperse dye, characterized by comprising the steps of: firstly, preparing heterocyclic diazonium salt by using heterocyclic derivative as diazonium component, and carrying out coupling reaction with amino naphthol under acidic condition to prepare amino naphthol type monoazo heterocyclic disperse dye filter cake; and secondly, taking the prepared monoazo heterocyclic disperse dye as a coupling component and carrying out coupling reaction with another part of diazonium salt under alkaline conditions to prepare the amino naphthol type bisazo heterocyclic disperse dye.
In one embodiment of the invention, the method comprises the steps of:
(1) Preparation of aminonaphthol type monoazo heterocyclic disperse dye:
dissolving a heterocyclic aromatic primary amine derivative in acid, adding a diazotizing reagent at 0-5 ℃, and carrying out diazotization reaction at the temperature of the solution to prepare heterocyclic aromatic primary amine diazonium salt; dissolving 1-amino-7-naphthol in acid at 50-80 ℃, cooling to 10-15 ℃, adding heterocyclic aromatic primary amine diazonium salt, adjusting the pH value to 3 by adopting sodium carbonate, and carrying out acid coupling reaction; after the completion, solid-liquid separation, collection, washing and drying are carried out to obtain the amino naphthol type monoazo heterocyclic disperse dye;
(2) Preparation of amino naphthol type disazo heterocyclic disperse dye:
dissolving the obtained amino naphthol type monoazo heterocyclic disperse dye in a mixed solution of sodium hydroxide and a surfactant, slowly adding heterocyclic aromatic primary amine diazonium salt, and performing alkaline coupling reaction at the temperature of 10-15 ℃; after the completion, the solid is separated, collected, washed and dried to obtain the amino naphthol type disazo heterocyclic disperse dye.
In one embodiment of the present invention, preferably, in the step (1), the heterocyclic aromatic primary amine derivative may have the structure:
wherein R is 3 ＝-NO 2 The others are hydrogen; or R is 2 ＝-OCH 3 The others are hydrogen; or R is 2 -F, the others being hydrogen; or R is 3 ＝R 2 -Cl, the others being hydrogen; or R is 1 ＝-CH 3 The others are hydrogen;
or alternatively
Wherein R is 4 = -H or-NO 2 。
In one embodiment of the present invention, the heterocyclic aromatic primary amine derivative of step (1) is dissolved in an acid, which may be any one or more of the following: hydrochloric acid, propionic acid, concentrated sulfuric acid (98%) or dilute sulfuric acid (40-70%), phosphoric acid, etc.
In one embodiment of the present invention, the heterocyclic aromatic primary amine derivative in step (1) is dissolved in an acid, and the mass ratio of the heterocyclic aromatic primary amine derivative to the acid is 1: (2.5-3.5) to ensure complete dissolution of the diazo component.
In one implementation method of the present invention, in the step (1), the diazotizing agent is sodium nitrite or nitrosylsulfuric acid; the molar ratio of the heterocyclic aromatic primary amine derivative to the diazotizing agent is 1: (1.1-1.2) to ensure complete diazotization of the diazotisation component.
In one embodiment of the present invention, the diazotisation reaction time in step (1) is 0.5 to 4 hours.
In one embodiment of the present invention, in step (1), the coupling component is 1-amino-7-naphthol.
In one embodiment of the present invention, the 1-amino-7-naphthol of step (1) is dissolved in an acid, which may be any one or more of hydrochloric acid, acetic acid, or dilute sulfuric acid.
In one embodiment of the present invention, the 1-amino-7-naphthol of step (1) is dissolved in an acid, the molar/volume ratio of 1-amino-7-naphthol to acid being 0.02mol: (2-5 mL) to dissolve the coupling component sufficiently.
In one embodiment of the present invention, in step (1), the mass ratio of 1-amino-7-naphthol to the primary heterocyclic aromatic amine diazonium salt is 1:1.
In one embodiment of the invention, in step (1), the acidic coupling reaction is carried out for a period of time of from 1 to 5 hours.
In one embodiment of the present invention, in the step (2), the molar/volume ratio of the amino naphthol type monoazo heterocyclic disperse dye to the mixed solution is 0.02mol: (25-50 mL) to dissolve the monoazo disperse dye sufficiently.
In one implementation method of the invention, in the step (2), the mass ratio of the heterocyclic aromatic primary amine diazonium salt to the amino naphthol type monoazo heterocyclic disperse dye is 1:1.
In one implementation method of the invention, in the step (2), the surface active group is one or more of nekal BX, tween-80, NNO, 85A, MF and the like, and the dosage is 0.05-1.5% wt.
In one embodiment of the invention, the concentration of sodium hydroxide in the mixed solution is 8 to 35wt%.
In one embodiment of the present invention, in step (2), the concentration of the coupling component amino naphthol type monoazo heterocyclic disperse dye relative to the mixed solution is 0.02 mol/(5 to 50 mL).
In one embodiment of the present invention, the diazonium salt selected in step (2) may be the same as or different from the diazonium salt selected in step (1).
In one embodiment of the invention, in step (2), the alkaline coupling reaction is carried out for a period of time of from 2 to 5 hours.
It is a third object of the present invention to provide a colorant containing the above-mentioned amino naphthol type disazo heterocyclic disperse dye.
In one embodiment of the present invention, a colorant is prepared by uniformly mixing a certain amount of the above-described aminonaphthol-type bisazo heterocyclic disperse dye with a high-temperature type dispersant, uniformly grinding in a sand mill, and spray-drying.
In one implementation method of the invention, the high-temperature dispersant is one or more of MF, NNO, 85A, AD-4600, styrene maleic anhydride, acrylate high-molecular type dispersant or polyhexamethylene glycol-polyethyleneimine block copolymer type dispersant, and the high-temperature dispersant is used in the following amount: the dosage of the disperse dye is 1.0, w/w= (0.45-0.85).
A fourth object of the present invention is to provide the use of the above amino naphthol type disazo heterocyclic disperse dye or the above colorant in textile dyeing or printing.
In one embodiment of the present invention, the textile comprises any one of terylene and blended fabrics, fibers, yarns, velvet fabrics, woven fabrics, knitted fabrics, thermal insulation wadding, fillers, nonwoven fabrics, industrial conveyor belts, military clothing, military tents, military sleeping bags, sanitary and medical supplies, fire-fighting clothing, security clothing, police clothing.
In one embodiment of the invention, a method of dyeing a textile material comprises the steps of:
uniformly mixing a certain amount of amino naphthol type disazo heterocyclic disperse dye with a high-temperature dispersing agent, uniformly grinding in a sand mill, and drying to obtain a colorant; and then dyeing the textile material by adopting a dyeing system containing the colorant through a high-temperature high-pressure dyeing method.
In one embodiment of the invention, the dyeing system further comprises 0.5-5g/L NaOH.
The beneficial effects are that:
the invention provides an amino naphthol type disazo heterocyclic disperse dye, which is used for solving the problems that the existing alkali-resistant disperse dye can be applied under the condition that the pH value is more than or equal to 7 and less than or equal to 14, but the alkali agent can only be sodium carbonate, sodium bicarbonate, trisodium phosphate, sodium dihydrogen phosphate or disodium hydrogen phosphate and the like but not can be strong alkali sodium hydroxide, and the application of the dye in a pretreatment/dyeing one-bath dyeing method of polyester fabrics is limited. The amino naphthol type disazo heterocyclic disperse dye has better alkali-resistant stability under the strong alkaline condition, and is suitable for short-process alkaline dyeing.
Drawings
FIG. 1 is a flow chart of an alkaline dyeing process.
FIG. 2 is a flow chart of a conventional acid dyeing process.
Detailed Description
The outstanding advantages and salient features of the invention are further illustrated by the following examples, but the invention is by no means limited to the examples of implementation.
The testing method comprises the following steps:
1. structural characterization: using deuterated DMSO as solvent, and adopting advanced III 400MHzZ full-digital nuclear magnetic resonance spectrometer to test dye 1 H-NMR。
2. K/S value: the apparent color yield (K/S) of the dyed polyester fabric is measured by using a CI7800 computer color measuring and matching instrument. K/S values were calculated according to the Kubelkae-Munk equation: K/S= (1-R) 2 2R; where K and S are the absorption and scattering coefficients of the matrix and R is the reflectance of the dye at the maximum absorption wavelength of the dyed fabric.
3. Color fastness:
fastness to washing: the soaping-resistant color fastness of the dyed fabric is tested according to GB/T3921-2008 "textile color fastness test soaping-resistant color fastness";
rubbing fastness: the rubbing color fastness of the dyed fabric is tested according to GB/T3920-2008 "rubbing color fastness for textile color fastness test";
sublimation fastness: the dye was tested for sublimation fastness according to GB/T5718-1997 "fastness to hot pressing for textile colour fastness test".
Example 1 preparation of an Aminonaphthol-type disazo dye
The structure of the amino naphthol type disazo dye is as follows:
the corresponding synthetic route is as follows:
the preparation process comprises the following steps:
(1) Preparation of amino naphthol monoazo dyes
Into a 500mL three-necked flask, 8mL of a 98% concentrated sulfuric acid solution and 20mL of a propionic acid solution were added, and 3.43g (0.02 mol) of 2-amino-6-fluorobenzothiazole was slowly added under stirring, followed by stirring to completely dissolve the materials. At 0-5 ℃, 6.35g of 40% nitrosylsulfuric acid solution is slowly added, and the starch potassium iodide test paper is detected to be slightly blue. The reaction was maintained at t=0-5 ℃ for 3h and excess nitrous acid was eliminated with sulfamic acid. 1-amino-7-naphthol (3.494 g,0.02 mol) and 30mL of water were added to a 400mL beaker and stirred well, 2.5mL of 36% HCl was added and dissolved to complete dissolution with stirring at 60 ℃. Cooling to 10-15 ℃, adding diazonium salt dropwise into the coupling component, and adjusting the pH value to 3 by adopting sodium carbonate. The reaction was incubated and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, carrying out suction filtration, washing with water and drying to obtain the solid powder of the amino naphthol type monoazo dye.
(2) Preparation of amino naphthol type disazo dye
After grinding the powder, 30mL of a mixed solution of 30% NaOH and 0.8% wt. of nekal BX was added and stirred at 50℃until completely dissolved. The temperature was reduced to 10-15℃and another portion of diazonium salt (0.02 mol) and caustic soda (10%, 10 mL) was slowly added dropwise to the coupling component. The reaction was incubated for 3H and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, carrying out suction filtration, washing with water and drying to obtain the amino naphthol type disazo dye.
Structural characterization:
1 H-NMR(400MHz,DMSO-d6)：δ9.04(s,1H,-OH),8.05(s,2H,-Ar),7.96-7.94(d,2H,-Ar),7.66-7.64(d,2H,-Ar),7.28-7.26(d,2H,-Ar),7.03-7.01(d,1H,-Ar),6.91-6.89(d,1H,-Ar),5.77(s,2H,-NH 2 )。
13 C NMR(100MHz,DMSO-d6)：δ165.98，165.93，160.73，158.71，158.51，144.36，144.36，142.03，136.79，136.78，130.45，130.29，129.15，123.29，123.25，123.18，117.46，116.24，115.67，113.96，113.94，109.86，108.06，108.03。
commercial processing applications of dyes: the dye obtained by the method is recrystallized in absolute ethyl alcohol, filtered and dried. Weighing 10g of prepared dye filter cake and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a finished product.
Example 2 preparation of an Aminonaphthol-type disazo dye
The structure of the amino naphthol type disazo dye is as follows:
the corresponding synthetic route is as follows:
the preparation process comprises the following steps:
(1) Preparation of amino naphthol monoazo dyes
15.6g of 98% sulfuric acid is added into a 250mL three-neck flask, 3.9g (0.02 mol) of 3-amino-5-nitrobenzoisothiazole is slowly added, stirring is carried out for 1h below 50 ℃ to fully dissolve, 6.35g of 40% nitrosylsulfuric acid is slowly added dropwise below 0 ℃, 3.9g of propionic acid is slowly added dropwise at 0-5 ℃ to finish the reaction for 3-4 h. Sulfamic acid is added to eliminate excess nitrous acid. 1-amino-5-naphthol (3.494 g,0.02 mol) and 30mL of water were added to a 400mL beaker and stirred well, 2.5mL of 36% HCl was added and dissolved to complete dissolution with stirring at 60 ℃. Cooling to 10-15 deg.c, adding diazonium salt dropwise to the coupling component and regulating pH value to 3. The reaction was incubated and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, carrying out suction filtration, washing with water and drying to obtain the solid powder of the amino naphthol type monoazo dye.
(2) Preparation of amino naphthol type disazo dye
After grinding the powder, 40ml of a 30% mixed solution of NaOH and nekal BX was added and stirred at 60 ℃ until dissolved. Cooling to 10-15 deg.c, and adding one other part of diazonium salt and caustic soda (10%, 10 mL) slowly to the coupling component. The reaction was incubated and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, carrying out suction filtration, washing with water and drying to obtain the amino naphthol type disazo dye.
Structural characterization:
1 H-NMR(400MHz,DMSO-d6)：δ9.03(s,1H,-OH),8.38-8.34(m,4H,-Ar),8.26(s,2H,-Ar),7.99-7.97(d,2H,-Ar),7.03-7.01(d,1H,-Ar),6.85-6.83(d,1H,-Ar),5.79(s,2H,-NH 2 )。
13 C NMR(100MHz,DMSO-d6)：δ165.12，165.02，164.01，158.17，157.06，157.03，147.96，147.92，129.83，129.42，129.12，129.06，125.23，124.33，124.31，123.96，123.45，123.12，120.37，118.93，112.43，111.17，109.87，109.13。
commercial processing of dyes: the obtained dye is recrystallized in absolute ethyl alcohol, filtered and dried. Weighing 10g of prepared dye filter cake and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a finished product.
Comparative example 1
Dye structure:
the synthesis method comprises the following steps: into a 500mL three-necked flask, 19.50g (0.10 mol) of 3-amino-5-nitrobenzoisothiazole and 78.00g of 98% concentrated sulfuric acid were charged and stirred to dissolve completely. 31.75g (m=127, 40%) of nitrosylsulfuric acid was slowly added at-5-0 ℃, followed by 19.5g of propionic acid, and the starch potassium iodide paper was detected to appear bluish. The reaction was kept at t=0-5 ℃ for 4 hours, and excess nitrous acid was eliminated with sulfamic acid. 5.50g (0.05 mol) of 1, 3-dinaphthol are weighed out in 10g of 10% sodium hydroxide and 0.11g of JFC, the nitrogen salt is added dropwise to the coupling component, and the reaction temperature is kept at 10-15 ℃. The reaction endpoint was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, the mixture is filtered, washed and dried. The obtained dye is recrystallized in absolute ethyl alcohol, filtered and dried. Weighing 10g of prepared naphthol-type disazo disperse dye and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a dye finished product.
Comparative example 2
Dye structure:
the synthesis method comprises the following steps: a150 mL beaker was taken, 6.24g of ice and 37.38g of 98% strength by mass concentrated sulfuric acid were added thereto, and 8.76g of 5, 6-dichlorobenzothiazole (0.04 mol) was slowly added thereto, and stirred until complete dissolution. The beaker was placed in an ice bath environment and after the temperature had fallen to 0-5 c 13.97g of 40% by mass nitrosylsulfuric acid (0.044 mol) was slowly added. 44.38g of ice and 44.38g of concentrated sulfuric acid with the mass fraction of 98% are additionally weighed, and the temperature is reduced to 0-5 ℃ by an ice bath. The 5, 6-dichlorobenzothiazole solution is slowly added to the diluted sulfuric acid solution and reacted at 0-5℃for 3 hours. The reaction endpoint was determined by adding a drop of diazonium solution to an ice water solution and observing the presence or absence of solid particles. After the diazotization reaction reaches the end point, urea is added to eliminate excess nitrous acid. 2.20g (0.02 mol) of 1, 3-dinaphthol are weighed out in 5g of 10% sodium hydroxide and 0.55g of JFC, the nitrogen salt is added dropwise to the coupling component, and the reaction temperature is kept at 10-15 ℃. The reaction endpoint was detected with H acid. After the reaction is finished, the mixture is filtered, washed and dried. The obtained dye is recrystallized in absolute ethyl alcohol, filtered and dried. Weighing 10g of the prepared naphthol type disazo disperse dye and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a dye finished product.
Comparative example 3
Dye structure:
the synthesis method comprises the following steps: into a 500mL three-necked flask, 8mL of a 98% concentrated sulfuric acid solution and 20mL of a propionic acid solution were added, and 3.43g (0.02 mol) of 2-amino-6-fluorobenzothiazole was slowly added under stirring, followed by stirring to completely dissolve the materials. At 0-5 ℃, 6.35g of 40% nitrosylsulfuric acid solution is slowly added, and the starch potassium iodide test paper is detected to be slightly blue. The reaction was maintained at t=0-5 ℃ for 3h and excess nitrous acid was eliminated with sulfamic acid. 1, 5-naphthalenediamine (1.58 g,0.01 mol) and 30mL of water were added to a 400mL beaker and stirred well, 10mL of 36% HCl and 10mL of absolute ethanol were added, and the mixture was stirred and dissolved at 60℃until complete dissolution. Cooling to 10-15 deg.c, adding diazonium salt dropwise to the coupling component and regulating pH value to 3. The reaction was incubated and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, filtering, washing with water and drying to obtain a dye filter cake. Weighing 10g of prepared dye filter cake and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a dye finished product.
Comparative example 4
Dye structure:
the synthesis method comprises the following steps: into a 500mL three-necked flask, 8mL of a 98% concentrated sulfuric acid solution and 20mL of a propionic acid solution were added, and 3.43g (0.02 mol) of 2-amino-6-fluorobenzothiazole was slowly added under stirring, followed by stirring to completely dissolve the materials. At 0-5 ℃, 6.35g of 40% nitrosylsulfuric acid solution is slowly added, and the starch potassium iodide test paper is detected to be slightly blue. The reaction was maintained at t=0-5 ℃ for 3h and excess nitrous acid was eliminated with sulfamic acid. 1, 7-dihydroxynaphthalene (1.60 g,0.02 mol) and 30mL of water were added to a 400mL beaker and stirred well, 15mL of a 30% mixed solution of NaOH and nekal BX was added, and stirred to dissolve until complete. The temperature is reduced to 10-15 ℃, and diazonium salt and caustic soda (10% and 10 mL) are slowly added dropwise to the coupling component. The reaction was incubated and the end point of the reaction was detected with H acid (1-amino-8-naphthol-3, 6-disulfonic acid). After the reaction is finished, filtering, washing with water and drying to obtain a dye filter cake. The obtained dye is recrystallized in absolute ethyl alcohol, filtered and dried. Weighing 10g of prepared dye filter cake and 6g of 85A, adding water, pulping, uniformly mixing, grinding and dispersing by a grinder, and spray drying to obtain a dye finished product.
The disperse dyes obtained in the examples and the comparative examples are processed commercially, and the polyester fabrics are dyed under alkaline and weak acid conditions respectively by adopting a high-temperature high-pressure dyeing method. The formulas and procedures of the alkaline and acid dyeing processes are shown in table 1, table 2 and fig. 1 and 2, respectively (the purpose of the acid bath reduction cleaning is to wash off the flooding, the alkaline bath may dispense with the reduction cleaning step). Specific staining results are shown in tables 3-4.
Table 1 basic dyeing process recipe
Table 2 acid dyeing process recipe
TABLE 3 alkaline dyeing Properties of the dyes obtained in examples 1-2 and comparative examples 1-4
| Sample of | Highest NaOH-resistant concentration (g/L) |
| Example 1 | 5 |
| Example 2 | 5 |
| Comparative example 1 | 2 |
| Comparative example 2 | 2 |
| Comparative example 3 | 2 |
| Comparative example 4 | 2 |
Note that: highest NaOH-resistant concentration: the K/S value of the dyed fabric under the conditions of the alkaline dyeing process and the acid dyeing process is measured respectively, and when the K/S value of the former is higher than or equal to the latter under a certain concentration and the K/S value of the next concentration is lower than the latter, the concentration is called the highest NaOH-resistant concentration.
TABLE 4 dyeing Dacron fastness Properties (dye usage 2% o.w.f,5 g/LNaOH)
Note that: SP denotes the wet-on, SC denotes the viscose cotton, and SA denotes the wet-on acetate fiber.
Claims (9)
1. An amino naphthol type disazo heterocyclic disperse dye, which is characterized in that the dye has the following structure:
，
or alternatively。
2. The aminonaphthol type disazo heterocyclic disperse dye according to claim 1, characterized in that the dye is prepared by a process comprising:
(1) Preparation of aminonaphthol type monoazo heterocyclic disperse dye:
dissolving a heterocyclic aromatic primary amine derivative in acid, adding a diazotizing reagent at 0-5 ℃, and carrying out diazotization reaction at the temperature of the solution to prepare heterocyclic aromatic primary amine diazonium salt; dissolving 1-amino-7-naphthol in acid at 50-80 ℃, cooling to 10-15 ℃, adding heterocyclic aromatic primary amine diazonium salt, adjusting the pH value to 3 by adopting sodium carbonate, and carrying out acid coupling reaction; after the completion, solid-liquid separation, collection, washing and drying are carried out to obtain the amino naphthol type monoazo heterocyclic disperse dye;
(2) Preparation of amino naphthol type disazo heterocyclic disperse dye:
dissolving the obtained amino naphthol type monoazo heterocyclic disperse dye in a mixed solution of sodium hydroxide and a surfactant, slowly adding heterocyclic aromatic primary amine diazonium salt, and performing alkaline coupling reaction at the temperature of 10-15 ℃; after the completion, the solid is separated, collected, washed and dried to obtain the amino naphthol type disazo heterocyclic disperse dye.
3. The amino naphthol type disazo heterocyclic disperse dye according to claim 2, wherein in the first step, the mass ratio of 1-amino-7-naphthol to heterocyclic aromatic primary amine diazonium salt is 1:1; in the second step, the mass ratio of the heterocyclic aromatic primary amine diazonium salt to the amino naphthol type monoazo heterocyclic disperse dye is 1:1.
4. A colorant comprising the amino naphthol type disazo heterocyclic disperse dye according to any one of claims 1 to 3.
5. The colorant according to claim 4, wherein the preparation method comprises: uniformly mixing the amino naphthol type disazo heterocyclic disperse dye according to any one of claims 1 to 3 and a high-temperature type dispersing agent, uniformly grinding in a sand mill, and spray-drying.
6. The colorant of claim 5 wherein the high temperature dispersant is one or more of MF, NNO, 85A, AD-4600, styrene maleic anhydride, acrylate polymeric dispersants, polyhexamethylene glycol-polyethylenimine block copolymer dispersants; the dosage ratio of the high-temperature dispersing agent to the disperse dye is (0.45-0.85): 1.0, w/w.
7. Use of an aminonaphthol-type disazo heterocyclic disperse dye according to any of claims 1 to 3 or a colorant according to any of claims 4 to 6 for dyeing or printing textiles.
8. The use according to claim 7, wherein the textile comprises any one of dacron and its blends, fibers, yarns, velvet, woven, knitted, thermal wadding, padding, non-woven, industrial conveyor belts, military clothing, military tents, military sleeping bags, sanitary and medical products, fire-fighting clothing, security clothing, police clothing.
9. A method of dyeing textile material, comprising the steps of:
uniformly mixing the amino naphthol type disazo heterocyclic disperse dye according to any one of claims 1 to 3 with a high-temperature dispersing agent, uniformly grinding in a sand mill, and drying to obtain a colorant; and then dyeing the textile material by adopting a dyeing system containing the colorant material through a high-temperature high-pressure dyeing method.
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| GB0027151D0 (en) * | 2000-11-07 | 2000-12-27 | Clariant Int Ltd | Hetero-anellated ortho-aminophenols |
| WO2009013122A2 (en) * | 2007-07-20 | 2009-01-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes |
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| JPS6017753A (en) * | 1983-07-12 | 1985-01-29 | Ricoh Co Ltd | Printing plate for electrophotographic plate making |
| US5633355A (en) * | 1994-01-17 | 1997-05-27 | Sandoz Ltd. | Monoazo disperse dyes from selected (aromatic amino)propionates or selected (aromatic amino)butyrates |
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