CN110484017A - A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness - Google Patents
A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness Download PDFInfo
- Publication number
- CN110484017A CN110484017A CN201910781963.2A CN201910781963A CN110484017A CN 110484017 A CN110484017 A CN 110484017A CN 201910781963 A CN201910781963 A CN 201910781963A CN 110484017 A CN110484017 A CN 110484017A
- Authority
- CN
- China
- Prior art keywords
- acid
- ethyl
- sodium
- added
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000001045 blue dye Substances 0.000 title claims abstract description 13
- 239000000975 dye Substances 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims abstract description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 235000019441 ethanol Nutrition 0.000 claims description 18
- 239000012065 filter cake Substances 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- -1 inorganic acid ester Chemical class 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 235000011054 acetic acid Nutrition 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000011787 zinc oxide Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 241001062009 Indigofera Species 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- 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 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229940077388 benzenesulfonate Drugs 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- 239000011592 zinc chloride Substances 0.000 claims 2
- 235000005074 zinc chloride Nutrition 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 1
- RIFOYWHVOLSJAS-UHFFFAOYSA-N methoxyethane;oxolane Chemical compound CCOC.C1CCOC1 RIFOYWHVOLSJAS-UHFFFAOYSA-N 0.000 claims 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims 1
- 235000019796 monopotassium phosphate Nutrition 0.000 claims 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims 1
- 235000019799 monosodium phosphate Nutrition 0.000 claims 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 235000014786 phosphorus Nutrition 0.000 claims 1
- 239000001103 potassium chloride Substances 0.000 claims 1
- 235000011164 potassium chloride Nutrition 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims 1
- 229910052939 potassium sulfate Inorganic materials 0.000 claims 1
- 235000011151 potassium sulphates Nutrition 0.000 claims 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims 1
- 239000001488 sodium phosphate Substances 0.000 claims 1
- 229910000162 sodium phosphate Inorganic materials 0.000 claims 1
- 235000011008 sodium phosphates Nutrition 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 29
- 238000004043 dyeing Methods 0.000 abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 238000002156 mixing Methods 0.000 description 12
- 238000010792 warming Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- 238000010026 decatizing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical class CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000005406 washing Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0092—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B67/0075—Preparations with cationic dyes
- C09B67/0076—Preparations of cationic or basic dyes in liquid form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
Abstract
The invention discloses a kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness.The structural formula of the dyestuff is as shown in logical formula (I).It is as lead to compound shown in formula (II) and logical formula (III) by water, alcohol, acid mixed liquor in react compound shown in the logical formula (IV) of generation with sodium nitrite, then (IV) progress quaternization reaction is obtained.The present invention solves the problems, such as that existing Cationic blue dyes dawn performance after dyeing to acrylic fabric cannot be taken into account with color fastness.(I)(II)(III)(IV) in above-mentioned general formula: R1, R2: for identical group, selected from ethyl, n-propyl, isopropyl；R3, R4: while being ethyl or butyl；Or respectively ethyl and ethoxy；A are as follows: methyl or ethyl；X‑Are as follows: Cl‑、Br‑, CH3SO4 ‑、ZnCl3 ‑,SO4 2‑,ZnCl4 2‑, HCOO‑。
Description
Technical field
The present invention relates to a kind of Cationic blue dyes and its preparation process, more particularly to a kind of dawn function admirable and
The high Cationic blue dyes of color fastness and its preparation process.
Background technique
The dye of positive ion is polyacrylonitrile fibre and fabric and uses with blended fabric dyeing made of other fibers and stamp
Dedicated dye, there are the distinguishing features such as bright in colour, application performance is excellent, easy to use, exhaustion rate is high.In recent years, with
The stringent rule of the fast development of textile fiber technology and printing technology, especially countries in the world to Green Textiles and discharge of wastewater
Fixed, more stringent requirements are proposed for the technique synthesized to the dye of positive ion.Diversification with market to textile demand, cation
Dyestuff also faces increasingly higher demands using upper in fabric discharge printing, and the dyestuff needs for being able to satisfy this application requirement have
The color fastness of dawn function admirable and various aspects will be high.In current cationic blue series dyes, cationic blue 41 are
It is most common to pull out type dye, but its shortcomings that there are following aspect.
(1) color fastness refers to low, is not able to satisfy increasingly strict application requirement.
(2) in production process will use a large amount of sulfuric acid and sodium hydroxide, generate a large amount of inorganic salts, need to a large amount of water come
Washing, therefore a large amount of wastewater flow rates are generated, causing the weight ratio of final products and waste water is 1:60 ~ 80.
(3) dawn effect is unstable, dawn poor reproducibility between batch, will appear frequently and is pulled out showing for fabric background color jaundice
As.
(4) raffinate water is deeper after dyeing, and had not only wasted dyestuff but also had been unfavorable for environmental protection.
(5) the nylon staining index of dyestuff is unstable, when and it is blue when and take on a red color, stable no nylon is not achieved and is stained with
The requirement of color.
(6) production needs equipment more, and space occupied is big.
It is therefore proposed that a kind of dawn function admirable and high cationic blue dyestuff of color fastness is of great significance.
Summary of the invention
Technical problems to be solved by the invention first aspect is to propose a kind of Cationic blue dyes, with dawn property
The excellent and high color fastness feature of energy.
Technical problems to be solved by the invention second aspect is to propose the preparation method of above-mentioned Cationic blue dyes.
As the Cationic blue dyes of first aspect present invention, it has general structure (I):
(I)
In formula (I)
R1, R2: it for identical group, is selected from ethyl, n-propyl, isopropyl, preferably isopropyl, propyl；
R3, R4: while being ethyl or butyl；Or R3For methyl or ethyl, R4For cyanoethyl or ethoxy；
A are as follows: methyl or ethyl；
X-Are as follows: Cl-、Br-, CH3SO4 -、ZnCl3 -,SO4 2-,ZnCl4 2-, HCOO-.Particularly preferably CH3SO4 -, C2H5SO4 -,ZnCl4 2-。
Above-mentioned Cationic blue dyes as second aspect of the present invention can be prepared by the following method:
(1) water, acid, alcohol mixed solution in, the compound that general formula is (II) is mixed with the compound that general formula is (III)
It is even, and it is cooled to 0-20 DEG C.Wherein the acid is one or more of hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, preferably
Hydrochloric acid, acetic acid；Alcohol is methanol or ethyl alcohol；The ratio between acid and the amount of substance of water are 1:20~1:100, preferably 1:30~1:50；
The ratio between acid and the amount of substance of alcohol are 1:0.5~1:10, preferably 1:1 ~ 1:2；The ratio between the amount of substance of acid and compound (II)
For 1:0.2~1:0.7, preferably 1:0.4 ~ 1:0.6；The ratio between amount of compound (II) and compound (III) substance is 1:1~1:
1.2, preferably 1:1.05 ~ 1:1.1.
(II) (III)
(2) at 5-15 DEG C, the aqueous solution of sodium nitrite is added dropwise, keeps the temperature 1-5 hours, rising temperature reclamation goes out the alcohol in material, filters
General formula to dyestuff is the parent filter cake of (IV).Wherein mass fraction shared by sodium nitrite in the sodium nitrite in aqueous solution
It is 25%~55%, preferably 25% ~ 35%；The ratio between amount of substance of compound (II) and sodium nitrite is 1:1~1:1.2, preferably
For 1:1.03 ~ 1:1.1.
(IV)
(3) parent filter cake is added in reaction medium, acid binding agent is added, quaternizing agent is added at room temperature, at 25-55 DEG C
Insulation reaction 1-5 hours.Wherein reaction medium is in water, formic acid, acetic acid, propionic acid, butyl glycol ether, ethylene glycol monomethyl ether, N, N- bis-
Methylformamide, hexamethylene, methanol, ethyl alcohol, propyl alcohol, isopropanol, methyl ether, ether, selects one kind in ethyl methyl ether at tetrahydrofuran
Or several, preferably water, formic acid, acetic acid；Acid binding agent is in sodium carbonate, sodium bicarbonate, potassium carbonate, saleratus, ammonium hydrogen carbonate, oxygen
One kind, preferably magnesia, zinc oxide are selected in change magnesium, zinc oxide；Quaternizing agent is in dialkyl sulfates, benzene sulfonate, halogen
For selecting one kind, preferably dimethyl suflfate, dithyl sulfate, methyl benzene sulfonate in alkane, strong inorganic acid ester.Quaternizing agent
It is 1: 0.15~1:0.5 with the ratio between the amount of substance of acid binding agent, preferably 1: 0.2~0.3.Parent and quaternizing agent molar ratio
It is 1: 1~5, preferably 1: 2.5~3.5.
(4) according to final required obtained Product Status, selection uses (A) or (B) two methods,
(A): (3) step material diluent is adjusted to the cationic blue of the present invention dye that required content obtains liquid
Material；
(B): water adjustment volume is added in (3) step material and filtrate is obtained by filtration, inorganic salts are added into filtrate at 30-60 DEG C
It saltouts, is pumped filter cake, dry, obtain the cationic blue dyestuff of the present invention of solid forms.
The present invention is directed to the shortcomings that existing product, proposes a kind of Cationic blue dyes and preparation method, it has color jail
Degree is high, and dawn effect is good, and production process wastewater flow rate is small, product items quality index stable feature few using equipment.
Four, specific embodiment
In order to better implement the present invention, now enumerating following examples, the present invention is further illustrated, but embodiment is not
Limitation of the present invention.
Embodiment 1:
Dyestuff 2- ((4- (N, N- diethylamino) phenyl) azo group) -5- ((N, N- diisopropyl) amino) -3- methyl-1,3,
The preparation of four zine chloride double salt of 4- thiadiazoles.
(1) by the hydrochloric acid of 600ml water, 80 grams of 30wt%(0.66mol), 32 grams of (0.7mol) ethyl alcohol mixing are then mixed to this
It closes and 62 grams of (0.42mol) N, N- diethylanilines is added in liquid, 80 grams of (0.4mol) 5-(N are added thereto again after mixing evenly,
N- diisopropyl) amino -2- amido-1,3,4-thiadiazoles, be cooled to 5 DEG C, start be added dropwise 30(0.43mol) gram sodium nitrite with
The solution of 60 grams of water composition, as the temperature rises, makes dropping temperature control at 10-15 DEG C, after dripping, keeps the temperature 2 at 10-15 DEG C
Hour, it is warming up to 95 DEG C and recycles out ethyl alcohol, be then pumped the parent filter cake that structural formula is (V).
(2) in 180 grams of water, it is added with stirring the parent filter cake and 24 grams of (0.3mol) zinc oxide of (1), is added at room temperature
150 grams of (1.2mol) dimethyl suflfates after control temperature is slowly raised to 35 DEG C, keep the temperature 4 hours at 35-40 DEG C, then to material
Middle addition water, being adjusted to volume is 800ml, is warming up to 60-65 DEG C of stirring half an hour, filters, obtains filtrate.
(3) in the filtrate of (2), 20 grams of 30wt%(0.16mol are added) hydrochloric acid, 35-40 DEG C be added 70 grams
(1.2mol) sodium chloride stirs 2-5 hours, and thin granulated crystallization is precipitated, then filters, obtains wet feed, dry at 65-85 DEG C,
Obtain the solid cationic blue dyestuff that structural formula is (VI), dry product: 180 grams.Through detecting, the solid cationic blue dyestuffs purity
Are as follows: 95.6%, separately there are 4.2% inorganic salts.Detected through the filtrate to parent, obtain 5-(N, N- diisopropyl) amino -2-
The conversion ratio of amido-1,3,4-thiadiazoles are as follows: 98.3%, dyestuff yield is 90.0%.After being dyed using the dyestuff to fabric
Raffinate water colorless is transparent, and the fabric decatizing fastness after dyeing is 6-7 grades, and light fastness is 6-7 grades；To the fabric through dyeing into
After row dawn, fabric background color is white, and dawn effect reaches approximate grade.
(V) (VI)
Embodiment 2:
Dyestuff 2- (((4- (N- ethyl-N hydroxyethyl) amino) phenyl) azo group) -5- ((N, N- diisopropyl) amino) -3- first
Base -1,3, the preparation of four zine chloride double salt of 4- thiadiazoles.
(1) by the hydrochloric acid of 500ml water, 97 grams of 30wt%(0.8mol), 30 grams of (0.9mol) methanol mixing are then mixed to this
The N- ethyl-N hydroxyethyl aniline that 69 grams (0.42mol) is added in liquid is closed, is added 80 grams thereto again after mixing evenly
The 5-(N of (0.4mol), N- diisopropyl) amino -2- amido-1,3,4-thiadiazoles, 8 DEG C are cooled to, starts to be added dropwise 30 grams
The solution of the sodium nitrite of (0.44mol) and 65 grams of water composition, as the temperature rises, makes dropping temperature control at 8-12 DEG C, drop
After adding, 2 hours are kept the temperature at 8-12 DEG C, 95 DEG C is warming up to and recycles out methanol, being then pumped structural formula is (VII) parent filter cake.
(2) in 180 grams of water, the parent filter cake and 22 grams of (0.27mol) zinc oxide of (1) are added with stirring, at room temperature plus
Enter 190 grams of (0.9mol) methyl benzene sulfonates, after control temperature is slowly raised to 35 DEG C, 2 hours is kept the temperature at 35-40 DEG C, then to object
Water is added in material, being adjusted to volume is 1800ml, is warming up to 60-65 DEG C of stirring half an hour, filters, obtains filtrate.
(3) in the filtrate of (2), 50 grams of 30wt%(0.41mol are added) hydrochloric acid, 35-40 DEG C be added 150
(2.56mol) gram sodium chloride stirs 5-10 hours, and granulated crystallization is precipitated, then filters, obtains wet feed, dries at 60-80 DEG C
It is dry, obtain the solid cationic blue dyestuff that structural formula is (VIII), dry product: 192.5 grams.Through detecting, solid cationic blue dye
Expect purity are as follows: 94.8%, separately there are 5.1% inorganic salts.Detected through the filtrate to parent, obtain 5-(N, N- diisopropyl) ammonia
The conversion ratio of base -2- amido-1,3,4-thiadiazoles are as follows: 97.7%, dyestuff yield is 91.3%.Raffinate water after being dyed to fabric
Colorless and transparent, the fabric decatizing fastness after dyeing is 6-7 grades, and light fastness is 6-7 grades；Dawn is carried out to the fabric through dyeing
Afterwards, fabric background color is white, and dawn effect reaches approximate grade.
(VII) (VIII)
Embodiment 3:
Dyestuff 2- ((4- (N, N- dibutylamino) phenyl) azo group) -5- ((N, N- diisopropyl) amino) -3- methyl-1,3,
The preparation of 4- thiadiazoles Methylsulfate salt.
(1) by the hydrochloric acid of 550ml water, 105 grams of 30wt%(0.86mol), 35 grams of (1.1mol) methanol mixing, then to this
The N of 85 grams (0.415mol) is added in mixed liquor, 80 grams (0.4mol) is added in N- dibutyl aniline thereto again after mixing evenly
5-(N, N- diisopropyl) amino -2- amido-1,3,4-thiadiazoles, be cooled to 10 DEG C, the nitrous of 30 grams (0.44mol) be added dropwise
The solution of sour sodium and 60 grams of water composition, as the temperature rises, makes dropping temperature control at 10-15 DEG C, after dripping, in 10-15
DEG C heat preservation 4 hours, be warming up to 95 degree and recycle out methanol, then filter structural formula be (IX) parent filter cake.
(2) in 180 grams of acetic acid, the parent filter cake and 12 grams of (0.3mol) magnesia of (1) are added with stirring, at room temperature plus
Enter 139 grams of (1.1mol) dimethyl suflfates, after control temperature is slowly raised to 35 DEG C, keeps the temperature 5 hours at 35-40 DEG C.
(3) water is then added into material, being adjusted to volume is 500ml, is warming up to 60-65 DEG C of stirring half an hour, it filters,
Obtain filtrate: 550 grams of structural formulas are the liquid cation indigo plant dyestuff of (X).Through detecting, the liquid cation indigo plant dyestuffs purity are as follows:
37.6%, dyestuff yield are as follows: 95.2%.Raffinate water colorless is transparent after being dyed using the dyestuff to fabric, the fabric after dyeing
Decatizing fastness is 6-7 grades, and light fastness is 6-7 grades；After carrying out dawn to the fabric through dyeing, fabric background color is white, is pulled out
White effect reaches approximate grade.
(IX) (X)
Embodiment 4:
Dyestuff 2-(((4- (N- ethyl-N hydroxyethyl) amino) phenyl) azo group) -5- ((N, N- diη-propyl) amino) -3- first
Base -1,3, the preparation of four zine chloride double salt of 4- thiadiazoles.
(1) by the hydrochloric acid of 400ml water, 63.5 grams of 30wt%(0.52mol), 20 grams of (0.63mol) methanol mixing, then to
The N- ethyl-N hydroxyethyl aniline of 41.5 grams (0.25mol) is added in this mixed liquor, is added 48 grams thereto again after mixing evenly
The 5-(N of (0.24mol), N- diη-propyl) amino -2- amido-1,3,4-thiadiazoles, 8 DEG C are cooled to, is added dropwise 18 grams
The solution of the sodium nitrite of (0.26mol) and 40 grams of water composition, as the temperature rises, makes dropping temperature control at 8-12 DEG C, drop
After adding, 3 hours are kept the temperature at 8-12 DEG C, 95 DEG C is warming up to and recycles out methanol, being then pumped structural formula is (XI) parent filter cake.
(2) in 120 grams of water, the parent filter cake and 13 grams of (0.16mol) zinc oxide of (1) are added with stirring, at room temperature plus
Enter 95 grams of (0.75mol) dimethyl suflfates, after control temperature is slowly raised to 35 DEG C, 3 hours is kept the temperature at 35-40 DEG C, then to object
Water is added in material, being adjusted to volume is 800ml, is warming up to 60-65 DEG C of stirring half an hour, filters, obtains filtrate.
(3) in the filtrate of (2), 30 grams of 30wt%(0.24mol are added) hydrochloric acid, 35-40 DEG C be added 80 grams
(1.37mol) sodium chloride stirs 5-10 hours, and granulated crystallization is precipitated, then filters, obtains wet feed, dries at 60-80 DEG C,
Obtain the solid cationic blue dyestuff that structural formula is (XII), dry product: 116.5 grams.Through detecting, the solid cationic blue dyestuff is pure
Degree are as follows: 93.6%.Detected through the filtrate to parent, obtain 5-(N, N- diη-propyl) amino -2- amino -1,3,4- thiophene two
The conversion ratio of azoles are as follows: 97.5%.Final dyestuff yield is 91.8%.Fabric is carried out
Raffinate water colorless is transparent after dyeing, and the fabric decatizing fastness after dyeing is 6-7 grades, and light fastness is 6-7 grades；To through dyeing
After the fabric crossed carries out dawn, fabric background color is white, and dawn effect is reached up to approximate grade.
(XI) (XII)
Embodiment 5:
Dyestuff 2- ((4- (N, N- dibutylamino) phenyl) azo group) -5- ((N, N- diη-propyl) amino) -3- ethyl -1,3,
The preparation of 4- thiadiazoles ethyl-sulfate salt.
(1) by the hydrochloric acid of 350ml water, 65 grams of 30wt%(0.53mol), 20 grams of (0.43mol) ethyl alcohol and 6 grams of acetic acid
(0.1mol) mixing, then into this mixed liquor be added 44.5 grams (0.25mol) N, N- dibutyl aniline, after mixing evenly again
The 5-(N of 48 grams (0.24mol), N- diη-propyl are added thereto) amino -2- amido-1,3,4-thiadiazoles, 8 DEG C are cooled to,
Start that 18.5 grams (0.27mol) of sodium nitrite and the solution of 40 grams of water composition is added dropwise, as the temperature rises, makes dropping temperature control
System is at 8-15 DEG C, after dripping, keeps the temperature 3 hours at 8-15 DEG C, is warming up to 95 DEG C and recycles out ethyl alcohol, being then pumped structural formula is
(XIII) parent filter cake.
(2) in 100 grams of formic acid, the parent filter cake and 8 grams of (0.2mol) magnesia of (1) are added with stirring, at room temperature plus
Enter 128 grams of (0.83mol) dithyl sulfates, after control temperature is slowly raised to 40 DEG C, keeps the temperature 4 hours at 40-45 DEG C.
(3) water is then added into material, being adjusted to volume is 350ml, is warming up to 60-65 DEG C of stirring half an hour, it filters,
Obtain filtrate: 377 grams, structural formula is the liquid cation indigo plant dyestuff of (XIIII).Through detecting, which contains
Amount are as follows: 32.7%.Dyestuff total recovery is 94.7%.Raffinate water colorless is transparent after being dyed using the dyestuff to fabric, after dyeing
Fabric decatizing fastness be 6-7 grade, light fastness be 6-7 grades；After carrying out dawn to the fabric through dyeing, fabric background color is white
Color, dawn effect are reached up to approximate grade.
(XIII) (XIV)
Embodiment 6:
Dyestuff 2- ((4- (N, N- diethylamino) phenyl) azo group) -5- ((N, N- diη-propyl) amino) -3- methyl-1,3,
The preparation of four zine chloride double salt of 4- thiadiazoles.
(1) by the hydrochloric acid of 600ml water, 85 grams of 30wt%(0.7mol), 30 grams of (0.9mol) methanol mixing are then mixed to this
The N that 62.5 grams (0.42mol) is added in liquid is closed, 80 grams (0.4mol) is added in N- diethylaniline thereto again after mixing evenly
5-(N, N- diη-propyl) amino -2- amido-1,3,4-thiadiazoles, be cooled to 8 DEG C, the nitrous of 31 grams (0.45mol) be added dropwise
The solution of sour sodium and 65 grams of water composition, as the temperature rises, makes dropping temperature control at 10-15 DEG C, after dripping, in 10-15
DEG C heat preservation 2 hours, be warming up to 95 DEG C and recycle out methanol, be then pumped structural formula be (XV) parent filter cake.
(2) in 250 grams of water, the parent filter cake and 25 grams of (0.31mol) zinc oxide of (1) are added with stirring, at room temperature plus
Enter 115 grams of (0.91mol) dimethyl suflfates, after control temperature is slowly raised to 35 DEG C, 2 hours is kept the temperature at 35-40 DEG C, then to object
Water is added in material, being adjusted to volume is 1500ml, is warming up to 60-65 DEG C of stirring half an hour, filters, obtains filtrate.
(3) in the filtrate of (2), 45 grams of 30wt%(0.37mol are added) hydrochloric acid, 35-40 DEG C be added 150
(2.56mol) gram sodium chloride stirs 5-10 hours, and granulated crystallization is precipitated, then filters, obtains wet feed, dries at 60-80 DEG C
It is dry, obtain the solid cationic blue dyestuff that structural formula is (XVI), dry product: 187.5 grams.Through detecting, the solid cationic blue dyestuff
Purity are as follows: 94.3%, separately there are 5.4% inorganic salts.Detected through the filtrate to parent, obtain 5-(N, N- diη-propyl) ammonia
The conversion ratio of base -2- amido-1,3,4-thiadiazoles are as follows: 96.1%, dyestuff yield is 92.4%.Raffinate water after being dyed to fabric
Colorless and transparent, the fabric decatizing fastness after dyeing is 6-7 grades, and light fastness is 6-7 grades；Dawn is carried out to the fabric through dyeing
Afterwards, fabric background color is white, and dawn effect reaches approximate grade.
(XV) (XVI)
Claims (6)
1. a kind of dawn function admirable and the high Cationic blue dyes of color fastness, which is characterized in that have following structure general formula:
In formula
R1, R2: for identical group, selected from ethyl, n-propyl, isopropyl, particularly preferably isopropyl；
R3, R4: while being ethyl or butyl or R3For methyl or ethyl, R4For cyanoethyl or ethoxy, particularly preferably R3For second
Base, R4For ethyl or ethoxy；
A are as follows: methyl or ethyl, particularly preferably methyl；
X-Are as follows: Cl-、Br-, CH3SO4 -、ZnCl3 -, 1/2SO4 2-, 1/2ZnCl4 2-, HCOO-, particularly preferably 1/2ZnCl4 2-,
CH3SO4 -。
2. dyestuff as described in claim 1, is prepared by following steps:
(1) water, acid, alcohol mixed solution in, compound that general formula is (a) is stirred with compound that general formula is (b)
Uniformly, and it is cooled to 0-20 DEG C；
(a) (b)
(2) aqueous solution of sodium nitrite is added dropwise at 0-20 DEG C, keeps the temperature 1-5 hours, recycles out the alcohol in material in (1) step, takes out
Filter obtains the parent filter cake that general formula is (c)；
(c)
(3) step (2) filter cake is added in reaction medium, acid binding agent is added, quaternizing agent is added at room temperature, in 25-
55 DEG C insulation reaction 1-5 hours, wherein reaction medium in water, formic acid, acetic acid, propionic acid, butyl glycol ether, ethylene glycol monomethyl ether, N,
Dinethylformamide, hexamethylene, methanol, ethyl alcohol, propyl alcohol, isopropanol, methyl ether, ether, selects in ethyl methyl ether tetrahydrofuran
It is one or more of；Acid binding agent selects in sodium carbonate, sodium bicarbonate, potassium carbonate, saleratus, ammonium hydrogen carbonate, magnesia, zinc oxide
With one kind,；Quaternizing agent selects one kind in dialkyl sulfates, benzene sulfonate, halogenated alkane, strong inorganic acid ester；It is quaternized
The ratio between amount of substance of reagent and acid binding agent be 1: 0.15~1:0.5, preferably 1: 0.2~0.3；Parent rubs with quaternizing agent
You are than being 1: 1~5, preferably 1: 2.5~3.5；
(4) (A) or (B) two methods are used according to product structure and final required obtained Product Status, selection,
(A): adding diluent to be adjusted to the sun that required content obtains the liquid of the present invention of liquid (3) step material
Ion indigo plant dyestuff；
(B): water adjustment volume is added in (3) step material and filtrate is obtained by filtration, inorganic salts are added into filtrate at 30-60 DEG C
It saltouts, is pumped filter cake, dry, obtain the cationic blue dyestuff of the present invention of solid forms.
3. the preparation step of the blue dyestuff of cation as claimed in claim 2, it is characterised in that: acid as described in step (1) is
One or more of hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid；Alcohol is methanol, ethyl alcohol；The ratio between acid and the amount of substance of water are 1:
20~1:100；The ratio between acid and the amount of substance of alcohol are 1:0.5~1:10；The ratio between acid and the amount of substance of compound (a) are 1:
0.2~1:0.7；The ratio between amount of compound (a) and compound (b) substance is 1:1~1:1.2.
4. the preparation step of the blue dyestuff of cation as claimed in claim 2, it is characterised in that: nitrous described in step (2)
Mass fraction shared by sodium nitrite is 25%~55% in acid sodium aqueous solution；The amount of the substance of compound (b) and sodium nitrite it
Than for 1:1~1:1.2.
5. the preparation step of the blue dyestuff of cation as claimed in claim 2, it is characterised in that: reaction described in step (3)
Medium is in water, formic acid, acetic acid, propionic acid, butyl glycol ether, ethylene glycol monomethyl ether, n,N-Dimethylformamide, tetrahydrofuran, hexamethylene
Alkane, ethyl alcohol, propyl alcohol, isopropanol, methyl ether, ether, selects one or more of, the object of reaction medium and parent in ethyl methyl ether at methanol
The ratio between amount of matter is 20:1~50:1；Acid binding agent selects one kind in sodium carbonate, sodium bicarbonate, magnesia, zinc oxide；It is quaternized
Reagent selects one kind in dialkyl sulfates, benzene sulfonate, halogenated alkane, strong inorganic acid ester；Quaternizing agent and acid binding agent
The ratio between amount of substance is 1: 0.2~0.3；The ratio between amount of parent and quaternizing agent substance is 1: 2.5~3.5.
6. the preparation step of the blue dyestuff of cation as claimed in claim 2, it is characterised in that: institute in the method (A) of step (4)
The diluent stated selects one in water, formic acid, acetic acid, propionic acid, butyl glycol ether, ethylene glycol monomethyl ether, ethyl alcohol, propyl alcohol, isopropanol
Kind is several, preferably water, formic acid, acetic acid, propyl alcohol, isopropanol；Inorganic salts described in the method (B) of step (4) are in chlorination
Sodium, potassium chloride, sodium bromide, potassium bromide, sodium sulphate, potassium sulfate, sodium phosphate, potassium phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, phosphorus
Sour disodium hydrogen, zinc chloride, iron chloride, chooses one or more of, preferably sodium chloride, zinc chloride in aluminium chloride at dipotassium hydrogen phosphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910781963.2A CN110484017A (en) | 2019-08-23 | 2019-08-23 | A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910781963.2A CN110484017A (en) | 2019-08-23 | 2019-08-23 | A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110484017A true CN110484017A (en) | 2019-11-22 |
Family
ID=68553037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910781963.2A Pending CN110484017A (en) | 2019-08-23 | 2019-08-23 | A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110484017A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724395A (en) * | 2019-10-30 | 2020-01-24 | 河南省化工研究所有限责任公司 | Preparation method of cationic blue dye |
| CN112574587A (en) * | 2020-12-29 | 2021-03-30 | 东华大学 | Cationic dye containing ester group and polyester group and having high washing fastness |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3028168A1 (en) * | 1980-07-25 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | METHOD FOR QUATERNATING 1,3,4-THIADIAZOLE AZO DYES |
| RU2004564C1 (en) * | 1992-01-24 | 1993-12-15 | Московское научно-производственное объединение "НИОПИК" | 2-diisopropylamino-5- (4-dimethylaminophenylazo) -4-methyl-1,3,4-thiadiazolium thiocyanogenzincate as a blue cationic dye for coloring in mass of polyacrylonitrile copolymers |
| TW311089B (en) * | 1993-07-05 | 1997-07-21 | Ciba Sc Holding Ag | |
| CN1445287A (en) * | 2002-03-20 | 2003-10-01 | 上海市染料研究所 | Olive green cationic dye and its preparing method |
| CN1699686A (en) * | 2005-06-07 | 2005-11-23 | 浙江闰土股份有限公司 | White discharge cationic black dyes for dyeing and printing |
-
2019
- 2019-08-23 CN CN201910781963.2A patent/CN110484017A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3028168A1 (en) * | 1980-07-25 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | METHOD FOR QUATERNATING 1,3,4-THIADIAZOLE AZO DYES |
| RU2004564C1 (en) * | 1992-01-24 | 1993-12-15 | Московское научно-производственное объединение "НИОПИК" | 2-diisopropylamino-5- (4-dimethylaminophenylazo) -4-methyl-1,3,4-thiadiazolium thiocyanogenzincate as a blue cationic dye for coloring in mass of polyacrylonitrile copolymers |
| TW311089B (en) * | 1993-07-05 | 1997-07-21 | Ciba Sc Holding Ag | |
| CN1445287A (en) * | 2002-03-20 | 2003-10-01 | 上海市染料研究所 | Olive green cationic dye and its preparing method |
| CN1699686A (en) * | 2005-06-07 | 2005-11-23 | 浙江闰土股份有限公司 | White discharge cationic black dyes for dyeing and printing |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724395A (en) * | 2019-10-30 | 2020-01-24 | 河南省化工研究所有限责任公司 | Preparation method of cationic blue dye |
| CN110724395B (en) * | 2019-10-30 | 2021-12-21 | 河南省化工研究所有限责任公司 | Preparation method of cationic blue dye |
| CN112574587A (en) * | 2020-12-29 | 2021-03-30 | 东华大学 | Cationic dye containing ester group and polyester group and having high washing fastness |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH10279827A (en) | Reactive dye mixture and use thereof | |
| CN102603572B (en) | Monoazo compound as well as preparation method and application thereof | |
| CN110484017A (en) | A kind of dawn function admirable and the high Cationic blue dyes and preparation method of color fastness | |
| CN101445667B (en) | Nitrobenzoisothiazole dye monomer compound, application thereof and disperse dye composition | |
| JP2004521973A (en) | Azo dyes, their preparation and their use in the dyeing or printing of hydrophobic fibrous materials | |
| CN104059000A (en) | Reactive dye as well as preparation method and application thereof | |
| CN113583468A (en) | Dispersed brown and preparation method thereof | |
| CN102453348B (en) | Reactive yellow compound and application thereof | |
| CN102504596A (en) | Bi-component monoazo disperse blue dye composition | |
| CN107722667B (en) | A kind of purple active dye and its preparation method and application based on the more chromophoric groups of anthraquinone azo | |
| KR19990013824A (en) | Disperse dye | |
| KR19990076017A (en) | Black Reactive Dye Composition for Cellulose Fibers | |
| CN112341836B (en) | Weak acid red bisazo dye and preparation method thereof | |
| CN101691694A (en) | Pure cotton and blend fiber scouring and dyeing synergistic agent and manufacturing method thereof | |
| CN108250794A (en) | A kind of preparation method of red reactive dyes magma | |
| JP2004526874A (en) | Dyeing or printing of manufactured natural polymer materials and synthetic hydrophobic fiber materials | |
| JPH1046045A (en) | Three-color dyeing or three-color printing | |
| CN105038312A (en) | Red reactive dye compound as well as preparation method and application thereof | |
| KR0182290B1 (en) | Process for dyeing of polyacrylonitrile materials with cationic benzo-thiazolium azo dye | |
| CN105566940A (en) | Phthalimidyl azo dye and preparation method and application thereof | |
| CN101250333A (en) | Reactive deep red RGB diazo dyes and preparation method thereof | |
| CN104497626B (en) | Orange active dye compound, and preparation method and application thereof | |
| CN1445287A (en) | Olive green cationic dye and its preparing method | |
| CN103773072A (en) | Yellow reactive dye compound | |
| CN104448894A (en) | Greenish-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20191122 |
|
| WD01 | Invention patent application deemed withdrawn after publication |