CN106380891B - 4- oxyquinoline base heterocycle azo disperse dyes and preparation method thereof - Google Patents
4- oxyquinoline base heterocycle azo disperse dyes and preparation method thereof Download PDFInfo
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- CN106380891B CN106380891B CN201610805313.3A CN201610805313A CN106380891B CN 106380891 B CN106380891 B CN 106380891B CN 201610805313 A CN201610805313 A CN 201610805313A CN 106380891 B CN106380891 B CN 106380891B
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 229960003540 oxyquinoline Drugs 0.000 title claims abstract description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 60
- 239000000975 dye Substances 0.000 claims abstract description 47
- 239000007787 solid Substances 0.000 claims abstract description 47
- -1 methylene compound Chemical class 0.000 claims abstract description 42
- 238000005859 coupling reaction Methods 0.000 claims abstract description 41
- 230000008878 coupling Effects 0.000 claims abstract description 40
- 238000010168 coupling process Methods 0.000 claims abstract description 40
- 238000004043 dyeing Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000000835 fiber Substances 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 239000003381 stabilizer Substances 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000004743 Polypropylene Substances 0.000 claims abstract description 4
- 229920000728 polyester Polymers 0.000 claims abstract description 4
- 229920001155 polypropylene Polymers 0.000 claims abstract description 4
- 229920006221 acetate fiber Polymers 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 23
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 15
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 10
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 10
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical group CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 8
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 claims description 7
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 6
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 6
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 6
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 239000004246 zinc acetate Substances 0.000 claims description 6
- LOVAOFAFMFWSKC-UHFFFAOYSA-N 4-[(4-sulfonaphthalen-1-yl)methyl]naphthalene-1-sulfonic acid Chemical compound C12=CC=CC=C2C(S(=O)(=O)O)=CC=C1CC1=CC=C(S(O)(=O)=O)C2=CC=CC=C12 LOVAOFAFMFWSKC-UHFFFAOYSA-N 0.000 claims description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 241000255964 Pieridae Species 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 54
- 125000001309 chloro group Chemical group Cl* 0.000 description 30
- 239000000243 solution Substances 0.000 description 20
- 125000001246 bromo group Chemical group Br* 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 12
- 239000005457 ice water Substances 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 229920004933 Terylene® Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 9
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical class CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 9
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- 239000004576 sand Substances 0.000 description 7
- BCXSVFBDMPSKPT-UHFFFAOYSA-N 5-amino-1,3-dihydrobenzimidazol-2-one Chemical class NC1=CC=C2NC(=O)NC2=C1 BCXSVFBDMPSKPT-UHFFFAOYSA-N 0.000 description 6
- 229960003116 amyl nitrite Drugs 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 235000013904 zinc acetate Nutrition 0.000 description 6
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 5
- NTOZWWRQYAJWGC-UHFFFAOYSA-N 1,2,3-benzothiadiazol-5-amine Chemical class NC1=CC=C2SN=NC2=C1 NTOZWWRQYAJWGC-UHFFFAOYSA-N 0.000 description 4
- KXCMMWVIUWBFCD-UHFFFAOYSA-N 1,3,3,4,4,5-hexahydroxypyridin-2-one Chemical compound OC=1C(C(C(N(C=1)O)=O)(O)O)(O)O KXCMMWVIUWBFCD-UHFFFAOYSA-N 0.000 description 4
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical class NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 4
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical class NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 4
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical class CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 4
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- RTNPPPQVXREFKX-UHFFFAOYSA-N 4-hydroxy-1-methylquinolin-2-one Chemical class C1=CC=C2C(O)=CC(=O)N(C)C2=C1 RTNPPPQVXREFKX-UHFFFAOYSA-N 0.000 description 3
- VWOYPUVIGCTVSC-UHFFFAOYSA-N 5-amino-3-methyl-1-phenylpyrazole-4-carbonitrile Chemical class NC1=C(C#N)C(C)=NN1C1=CC=CC=C1 VWOYPUVIGCTVSC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000790917 Dioxys <bee> Species 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 3
- 150000002829 nitrogen Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical class NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 2
- JDOLPAMOKSAEMD-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-4h-pyrazol-3-one Chemical class CC1=NN(C=2C=CC=CC=2)C(=O)C1C(=O)C1=CC=CC=C1 JDOLPAMOKSAEMD-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1c(*)[n]c(C)c1N Chemical compound Cc1c(*)[n]c(C)c1N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical class OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical class NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 1
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical class N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- PSRZQUKEUSRHJJ-UHFFFAOYSA-N 5-nitrothiophen-2-amine Chemical class NC1=CC=C([N+]([O-])=O)S1 PSRZQUKEUSRHJJ-UHFFFAOYSA-N 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MENZZFSZXHJONY-QZQOTICOSA-N CC(C(C1=O)/N=N/c(c(C)c2)c(C)cc2[N+]([O-])=C)=NN1c1ccccc1 Chemical compound CC(C(C1=O)/N=N/c(c(C)c2)c(C)cc2[N+]([O-])=C)=NN1c1ccccc1 MENZZFSZXHJONY-QZQOTICOSA-N 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- YQYFZDIQNASDSH-UHFFFAOYSA-N N1N=CC=C1.NC=1SC(=CC1[N+](=O)[O-])[N+](=O)[O-] Chemical class N1N=CC=C1.NC=1SC(=CC1[N+](=O)[O-])[N+](=O)[O-] YQYFZDIQNASDSH-UHFFFAOYSA-N 0.000 description 1
- FYLIHAKOUALMIS-UHFFFAOYSA-N N1N=CC=C1.NC=1SC(=CN1)[N+](=O)[O-] Chemical class N1N=CC=C1.NC=1SC(=CN1)[N+](=O)[O-] FYLIHAKOUALMIS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical class CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000000215 hyperchromic effect Effects 0.000 description 1
- WAYMLHJBBABLLS-UHFFFAOYSA-N imidazol-2-one 1H-pyrazole Chemical compound N1N=CC=C1.N=1C(N=CC1)=O WAYMLHJBBABLLS-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical class C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
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- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0037—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with two nitrogen atoms
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- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
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- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
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- C09B29/0077—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 one nitrogen and one sulfur as heteroatoms
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- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—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 one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
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- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—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 one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
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- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—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 one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
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- 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
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- 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
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0848—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by NO2
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- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
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- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
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- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
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- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
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- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
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- C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
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- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3682—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only sulfur as heteroatom
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- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom
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- 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
- C09B67/008—Preparations of disperse dyes or solvent dyes
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- 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
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- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
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Abstract
The present invention relates to a kind of 4 oxyquinoline base heterocycle azo disperse dyes and preparation method thereof, the 4 oxyquinoline base heterocycle azo disperse dyes are made of diazo component and coupling component two parts, the wherein described coupling component is the heterocycle active methylene compound being coupled under alkaline condition or heterocycle phenolic compound, the diazo component alkalescent heterocycle arylamine or alkalescent anil.The preparation method is in the presence of a stabilizer, to carry out diazotising to alkalescent heterocycle arylamine or alkalescent anil in organic solvent, stable diazosalt solid is precipitated, and after solid is obtained by filtration, it is applied to alkaline coupling, obtains target dyestuff.The dyestuff can be applied to polyester fiber, Fypro, acid fiber by polylactic, polypropylene fibre, acetate fiber dyeing, have excellent dyeing brightness.
Description
Technical field
The present invention relates to a kind of heterocycle azo disperse dyes and preparation method thereof.
Background technology
Synthetic fibers close structure, crystallinity is high, and dyeing is more difficult, is generally dyed using disperse dyes, to improve
The binding force of dyestuff and hydrophobic fibre.
Without containing water soluble groups such as sulfonic group or carboxyls in disperse dyes structure, it is insoluble in water.It need to be with when being commercialized
Dispersant is ground together, and when application is dispersed in water by dispersant with insoluble minuteness particle, is used for the high temperature of synthetic fibers
High pressure or high temperature pad-dry-cure dyeing.Synthetic fibers include mainly the classes such as azo, anthraquinone, nitrodiphenylamine by structure point with disperse dyes
Type, and azo type disperse dyes cover red, yellow, blue whole chromatogram system due to simple in structure, occupy in disperse dyes extremely heavy
The status wanted.Disperse dyes containing heterocyclic group have bright in color light, coloring intensity high, have preferable hyperchromic effect and compared with
The characteristics such as high molar extinction coefficient are dye species important in disperse dyes.
Azo type heterocyclic disperse dyes are made of diazo component and coupling component two parts.When diazo component can be in hydrochloric acid
When middle progress diazotising (diazo component is aniline, chlorine substituted aniline, 1- nitros substituted aniline at this time), coupling component can be
Heterocycle arylamine, phenol or heterocycle active methylene compound, (at this time when diazo component is merely able to carry out diazotising in concentrated sulfuric acid
Diazo component is alkalescent arylamine, such as：Aminothiophene, aminothiazole, aminobenzothiazole, 2,4- dinitroanilines, 4- nitros-
2- cyano-anilines, 4- nitros -2,6-DCA etc.), coupling component can only be the aniline derivatives being coupled in acid condition
Object or heterocycle arylamine.And heterocycle active methylene compound, heterocycle phenolic compound need to be coupled under alkaline condition, alkalescent
Arylamine carries out diazotising in concentrated sulfuric acid, when system is transferred to alkalinity, will generate a large amount of inorganic salts, it is difficult to obtain corresponding dyestuff.
Therefore, the purpose of the present invention is to develop a new class of heterocycle azo disperse dyes and its technology of preparing, such dyestuff
Coupling component be the heterocycle active methylene compound being coupled under alkaline condition, heterocycle phenolic compound；Diazo component is
Alkalescent arylamine；Preparation method is to carry out diazotising to alkalescent arylamine in organic solvent, and it is solid that stable diazol is precipitated
It after solid is obtained by filtration, is applied to alkaline coupling, obtains target dyestuff by body.
Invention content
The first aspect of the present invention provides a kind of new heterocycle azo disperse dyes, and the dyestuff is by diazo component and coupling
Group is divided into two parts composition, wherein the coupling component is the heterocycle active methylene compound or miscellaneous being coupled under alkaline condition
Ring phenolic compound, the diazo component are that can carry out diazotizing heterocycle arylamine or alkalescent aniline derivatives in concentrated sulfuric acid
Object.
A kind of heterocycle azo type disperse dyes, the structure with general formula (I)：
A-N=N-B
(Ⅰ)
The diazol and the residue after coupling component coupling that A is the diazo component that diazo component is obtained through diazotising in formula I,
The diazo component be selected from general formula (II -1), (II -2), (II -3), (II -4), (II -5), (II -6), (II -7), (II -8),
The structure of (II -9) and (II -10)：
In formula (II -1)：
Ra 1For-H ,-CN ,-NO2、-COR、-COAr、-CONH2、-CONHR、-SO2,-COOR or-COAr；
Ra 2For-H ,-R ,-OR ,-NO2,-Cl or-Br；
Ra 3For-H ,-CN ,-NO2、-Ar、-COR、-COAr、-COOR、-COOAr、-CONH2、-CONHR、-SCN、-
OCOR ,-CONHAr or-CHO；
In formula (II -2)：
Rb 1For-H ,-R ,-Ar ,-CF3、-CN、-COOR、-CONH2Or-CH2OH；
Rb 2For-H ,-NO2、-R、-ROH、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar or-CN；
In formula (II -3)：
RC 1And RC 2It is each independently selected from-H ,-Cl ,-Br ,-NO2、-R、-OR、-CN、-SO2R、-SO2NR and-CF3；
RC 2For in 1,2 or 3 substituent group；
In formula (II -4)：
Rd 1For-NO2,-Cl ,-Br or-H；
Rd 2For-H ,-Cl or-Br；
In formula (II -5)：
ReFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -6)：
RfFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -7)：
RgFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-NO2, CN ,-Cl or-CCl3；
In formula (II -8)：
Rh 1For-CN ,-H ,-COOH or-COOCH3；
Rh 2For-SCH ,-H ,-CONH2Or-CH2CN；
Rh 3For-H, phenyl or cyclohexyl；
In formula (II -9)：
Ri 1For-CN ,-NO2,-Cl ,-Br or-I；
Ri 2For-H ,-CN ,-NO2,-Cl ,-Br or-I, and work as Ri 1For-Cl ,-Br or-I when, Ri 2Cannot be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
B is the residue after the diazol coupling of coupling component and diazo component in formula (I), and the coupling component is selected from logical
Structure shown in formula (III -1), (III -2), (III -3), (III -4), (III -5), (III -6), (III -7) and (III -8)：
In formula (III -1)：
Rj 1For-H ,-CH3、-Ar、-CF3,-CN ,-COOR or-CONHR；
Rj 2For-H ,-Ar ,-ArCl or-ArSO2NHR；
In formula (III -2)：
Rk 1For-R ,-OR ,-NHR, COOR ,-Ar or-CN；
Rk 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
Rk 3For-R ,-Ar or cyclohexyl；
In formula (III -3)：
RLFor-R ,-OR ,-NO2,-CN ,-Cl ,-Br ,-COOR or-Ar；
In formula (III -4)：
Rm 1For-R ,-OR, COOR ,-Ar or-CN；
Rm 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -5)：
Rn 1For-R ,-OR, COOR ,-Ar or-CN；
Rn 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -6)：
Ro 1For-R ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Ro 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -7)：
Rp 1For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Rp 2For-H ,-NO2、-CN、-Cl、-Br、-COOR、-SO2NHR or-CONHR；
In formula (III -8)：
Rq 1For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Rq 2For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
In formula (II -1) to formula (II -7) and formula (III -1) to formula (III -8)：
R is hydrogen, C1-4Alkyl or C1-4Alkoxy；
Ar is phenyl.
The second aspect of the present invention provides the system of the heterocycle azo type disperse dyes of the present invention shown in general formula (I)
Preparation Method, this method comprises the following steps：
(1) diazo component described in claim 1, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A,
After being cooled to 0010 DEG C, diazo reagent is added portionwise, reacts 0.1010h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component described in claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value
To 8012, coupling component is made to dissolve, be cooled to 0010 DEG C, the diazol for being added with stirring the diazo component that step (1) obtains is solid
Body, while being reacted 1010h in 8010 ranges with the pH value of 10% sodium carbonate liquor control reaction at 0010 DEG C, obtaining formula (I)
Compound；
The wherein described diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite,
Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid
One or both of.
Further, the molar ratio of the diazo reagent described in step (1) and diazo component is 101.05:1.
Further, the molar ratio of the diazo component described in step (1), the concentrated sulfuric acid and stabilizer is 1:103:
103
Further, the total amount that the diazo component described in step (1), the concentrated sulfuric acid are added with stabilizer accounts for reaction system
The 5030% of total weight.
Further, the molar ratio of the diazosalt solid of the coupling component described in step (2) and diazo component
It is 0.801:0.801.05.
Further, in step (1), the addition time of diazo reagent is 0.101h.
Further, in step (2), the time for being added with stirring the diazosalt solid of diazo component is 5060min.
Further, the organic solvent is ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, second two
One kind in diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxane,
Two or three.
Further, the stabilizer be fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd,
One kind in 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 1,5-, bis- naphthalene sulfonic acids of 2,6-, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid
Or two kinds.
The third aspect of the present invention provide heterocycle azo type dye of the present invention polyester fiber, Fypro,
Application in acid fiber by polylactic, polypropylene fibre, acetate fiber dyeing.
Compared with the existing technology, beneficial effects of the present invention：
1. its coupling component is heterocycle active methylene compound, heterocycle phenols chemical combination in the structure of the compound of the present invention
Object, diazo component are alkalescent arylamine, and the dyeing brightness of acquisition is high.
2. being to carry out diazotising to alkalescent arylamine in organic solvent in the preparation method of the compound of the present invention, it is precipitated
Stable diazosalt solid, after solid is obtained by filtration, by it applied to alkaline coupling, acquisition target dyestuff, this method and in sulphur
It carries out diazotizing conventional method in acid to compare, sulfuric acid dosage is down to 2 moles times of amounts hereinafter, reducing 8 moles of sulfuric acid times amount or more；
And the diazol that this method obtains is stable solid, can be used for alkaline coupling, obtains Novel disperse dyestuff.
3. the compounds of this invention can be used for polyester fiber, Fypro, acid fiber by polylactic, polypropylene fibre, acetic acid
The dyeing of fiber, part of compounds can be additionally used in pH sensitivity detection fields.
Description of the drawings
Fig. 1 is the mass spectrogram of dye composition 1#；
The FT-IR that Fig. 2 is dye composition 1# schemes；
Fig. 3 is the nuclear magnetic spectrogram of dye composition 1#；
Fig. 4 is the mass spectrogram of dye composition 2#；
The FT-IR that Fig. 5 is dye composition 2# schemes；
Fig. 6 is the nuclear magnetic spectrogram of dye composition 2#；
Fig. 7 is the mass spectrogram of dye composition 3#；
The FT-IR that Fig. 8 is dye composition 3# schemes；
Fig. 9 is the nuclear magnetic spectrogram of dye composition 3#；
Figure 10 is uv-visible absorption spectras of the dye composition 3# at different pH；
Figure 11 is the mass spectrogram of dye composition 4#；
The FT-IR that Figure 12 is dye composition 4# schemes；
Figure 13 is the nuclear magnetic spectrogram of dye composition 4#.
Specific implementation mode
In order to keep the purpose of the present invention, scheme, flow and advantage more clear apparent, in conjunction with the accompanying drawings and embodiments to this hair
It is bright to be described in further detail, it is notable that specific embodiment is not used to only as the present invention is illustrated herein
Limit the present invention.In following embodiments, unless otherwise specified, used experimental method is conventional method, material therefor, examination
Agent etc. can chemically company be bought.
Unless otherwise stated, the technical term used in the present invention has following meaning.
The term " alkyl " used in the present invention includes straight chained alkyl and branched alkyl.Such as refer to single alkyl such as " third
Base ", then only refer in particular to straight chained alkyl, such as refers to that single branched alkyl such as " isopropyl ", then only refers in particular to branched alkyl.For another example " C1-4Alkane
Base " includes C1-3Alkyl, methyl, ethyl, n-propyl, isopropyl and tertiary butyl.Similar rule is also suitable to be made in this manual
Other groups.
In formula (II -1)：Ra 1Preferably-H ,-CN ,-NO2、-COR、-COAr、-CONH2；More preferably-H ,-CN ,-NO2；
Most preferably-H ,-NO2；Ra 2Preferably-H ,-R ,-OR ,-NO2、-Cl；More preferably-H ,-R ,-OR ,-NO2；Most preferably-H ,-
NO2；Ra 3Preferably-H ,-CN ,-NO2,-Ar ,-COR ,-COAr, more preferably-H ,-CN ,-NO2、-Ar、-COAr；Most preferably-
H、-NO2、-Ar。
In formula (II -2)：Rb 1Preferably-H ,-R ,-Ar ,-CF3、-CN、-COOR；More preferably-H ,-R ,-Ar ,-CF3、-
CN；Most preferably-H ,-Ar ,-CF3、-CN；Rb 2Preferably-H ,-NO2、-R、-ROH、-Ar、-COOR、-SO2Ar or-CN；It is more excellent
It is selected as-H ,-NO2、-Ar、-COOR、-SO2Ar or-CN；Most preferably-H ,-NO2、-Ar、-SO2Ar。
In formula (II -3)：It is preferred that RC 1And RC 2It is each independently selected from-H ,-Cl ,-Br ,-NO2、-R、-OR；More preferably-
H、-Cl、-NO2、-OR；Most preferably-H ,-Cl ,-NO2；RC 2It is preferably located on 1,2 positions；More preferably it is located in 1.
In formula (II -4)：Rd 1Preferably-NO2,-Cl or-H；More preferably-NO2Or-H；Most preferably-NO2；Rd 2It is preferred that
For-H ,-Cl；More preferably-H.
In formula (II -5)：RePreferably-H ,-Ar ,-OR ,-CN ,-Cl or-CCl3；More preferably-H ,-Ar ,-CN or-
CCl3；Most preferably-H ,-CN or-CCl3。
In formula (II -6)：RfPreferably-H ,-R ,-Ar ,-OR ,-CN,；More preferably-H ,-Ar ,-OR ,-CN；Most preferably
For-H ,-Ar ,-CN.
In formula (II -7)：RgPreferably-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl；More preferably-H ,-R ,-Ar ,-CN ,-
Cl；Most preferably-H ,-Ar ,-CN.
In formula (II -8)：Rh 1Preferably-CN ,-H ,-COOCH3；More preferably-CN ,-H；Rh 2Preferably-CONH2、-H、
Or-CH2CN；More preferably-H or-CH2CN；Rh 3Preferably-H, phenyl；More preferably phenyl.
In formula (II -9)：Ri 1Preferably-CN ,-NO2,-Br or-Cl；More preferably-CN ,-NO2Or-Cl；Most preferably-
NO2Or-Cl；Ri 2Preferably-H ,-CN ,-NO2,-Br or-Cl, more preferably-H ,-NO2、-Cl；Most preferably-H ,-Cl；And work as
Ri 1For Cl, Br or I when, Ri 2Cannot be H.
In formula (II -10)：RjPreferably-H ,-CN ,-NO2、-Br；More preferably-H ,-NO2；Most preferably-H.
In formula (III -1)：Rj 1Preferably-H ,-CH3,-Ar ,-COOR or-CONHR；More preferably-H ,-CH3,-Ar or-
CONHR；Most preferably-H ,-Ar；Rj 2Preferably-H ,-Ar or-ArSO2NHR；More preferably-H ,-Ar；Most preferably-Ar.
In formula (III -2)：Rk 1Preferably-R ,-OR ,-NHR, COOR or-CN；More preferably-R ,-NHR, COOR or-CN；Most
Preferably-R, COOR or-CN；Rk 2Preferably R ,-Ar ,-CN or-CONHR；More preferably R ,-Ar ,-CN；Most preferably R ,-Ar；
Rk 3Preferably-R ,-Ar；More preferably-R.
In formula (III -3)：RLPreferably-R ,-OR ,-NO2,-COOR or-Ar；More preferably-R ,-NO2,-COOR or-Ar；
Most preferably-R ,-NO2、-COOR。
In formula (III -4)：Rm 1Preferably-R ,-OR, COOR；More preferably-R, COOR；Most preferably-R；Rm 2For-H, R ,-
Ar、-CN、-COOR；More preferably-H ,-Ar ,-CN ,-COOR；Most preferably-H ,-Ar.
In formula (III -5)：Rn 1Preferably-R ,-OR, COOR ,-Ar；More preferably-R ,-OR, COOR；Most preferably-R ,-
OR；Rn 2Preferably-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar or-CONHR；Most preferably-H, R.
In formula III -6：Ro 1Preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Ro 2It is preferred that
For-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar ,-CONHR；Most preferably-H ,-Ar.
In formula (III -7)：Rp 1Preferably-R, cyclohexyl ,-CH2CH2CH2OH、CH2CH2CN；More preferably-R ,-
CH2CH2CH2OH、CH2CH2CN；Most preferably-R, CH2CH2CN；Rp 2Preferably-H ,-NO2、-CN、-Cl、-Br；More preferably-
H、-NO2、-CN、-Cl；Most preferably-H ,-NO2。
In formula (III -8)：Rq 1Preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Rq 2It is excellent
It is selected as-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH。
In formula (II -1) to formula (II -7) and formula (III -1) to formula (III -8)：R is preferably-H, C1-4Alkyl or C1-4Alcoxyl
Base；More preferably hydrogen, C1-2Alkyl or C1-2Alkoxy；Further preferably-H, ethyl, methoxyl group.
Ar is phenyl.
On the other hand, the present invention also provides the preparation method of compound described above, which is in dense sulphur
In the presence of acid, diazotising is carried out to diazo component in organic solvent, stable diazosalt solid is precipitated, the solid is obtained by filtration
Afterwards, coupling reaction is carried out with coupling component under alkaline condition, obtains target dyestuff.Specifically comprise the following steps：
(1) diazo component of the present invention, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, cooling
To after 0010 DEG C, diazo reagent is added portionwise, reacts 0.1010h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component described in claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value
To 8012, coupling component is made to dissolve, be cooled to 0010 DEG C, the diazol for being added with stirring the diazo component that step (1) obtains is solid
Body is dissolved in control pH value in reaction to 8010 ranges with 10% sodium carbonate, reacts 1010h at 0010 DEG C, obtain the chemical combination of formula (I)
Object；
The wherein described diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite,
Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid
One or both of.
In preferred technical solution, the diazo reagent is nitrosyl sulfuric acid, butyl nitrite, the tertiary fourth of nitrous acid
One or both of ester, isoamyl nitrite, amyl nitrite, isobutyl nitrite；More preferably nitrosyl sulfuric acid, nitrous
Tert-butyl acrylate, isoamyl nitrite, isobutyl nitrite；Most preferably nitrosyl sulfuric acid, nitrite tert-butyl.
In preferred technical solution, the molar ratio of diazo reagent and diazo component described in step (1)
It is 1.0501:1, more preferably 1.0201:1, most preferably 1:1；The molar ratio of diazo component and the concentrated sulfuric acid is 1:103,
More preferably 1:102.5 most preferably 1:102.
In preferred technical solution, diazo component, the concentrated sulfuric acid and stabilizer described in step (1) feed intake mole
Than being 1:103:103, more preferably 1:102.5:102.5 most preferably 1:102:102.
In preferred technical solution, total amount that diazo component, the concentrated sulfuric acid described in step (1) are added with stabilizer
Account for the 5030% of reaction system total weight, more preferably 5020%, most preferably 5015%.
In preferred technical solution, the diazosalt solid of coupling component and diazo component described in step (2)
Molar ratio is 1:101.05；More preferably 1:101.03 most preferably 1:1.
In preferred technical solution, in step (1), the time that diazo reagent is added dropwise is 0.101h, more preferably
0.100.5h。
In preferred technical solution, in step (2), the time for being added with stirring the diazosalt solid of diazo component is
5060min, more preferably 10040min.
In preferred technical solution, the organic solvent is ethyl acetate, ether, glycol monoethyl ether, ethylene glycol
Dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy six
One kind, two or three, more preferably ethyl acetate, glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl in ring
One kind in ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, two or three, most preferably
For ethyl acetate, glycol monoethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, ethylene glycol diethyl
One kind in ether, two or three.
In preferred technical solution, the stabilizer is fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulphur
One or both of acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5-, bis- naphthalene sulfonic acids, 2,6-, bis- naphthalene sulfonic acids, NNO, MF, more preferably
Fluoboric acid, zinc chloride, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 1,5-, bis- naphthalene sulfonic acids of 2,6-, methylene dinaphthalene sulfonic acid, methylene
The double methyl naphthalene sulfonic acids of base are one or two kinds of, most preferably fluoboric acid, 1,5-, bis- naphthalene sulfonic acids, 2,6-, bis- naphthalene sulfonic acids, methylene dinaphthalene
Sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid are one or two kinds of.
The preparation of 1 compound 1# of embodiment
(1) by 1.5g 5-Amino-2-benzimidazolinones, the 1g concentrated sulfuric acids, 80ml ethylene glycol diethyl ethers, 5g 1,5- naphthalenedisulfonic acids
It is added in there-necked flask, 5 DEG C is cooled in ice-water bath, 3g nitrite tert-butyls are added dropwise, time for adding 0.5h is anti-after being added dropwise
It answers 2 hours；Diazosalt solid is obtained after filtering；(2) 1.34g 3- methyl-1s--5 pyrazolone of phenyl, 100ml water are added anti-
It answers in device, with 10% sodium hydroxide solution tune pH value to 10, is cooled to 5 DEG C, be added with stirring the 5- aminobenzenes that step (1) obtains
And imidazolone diazol, it is used in combination 10% sodium carbonate liquor control ph to be added in 9, half an hour, and react 2hr at 5 DEG C；Reaction
It finishes, filters, it is neutrality to be washed till filtrate using ice water, obtains heterocycle azo disperse dyes (compound 1#) after dry, is coupled
Rate is 95%.
Occurs [M-H]-quasi-molecular ions of compound 1# in mass spectrum (Fig. 1) at m/z 333.1, in infrared spectrum (Fig. 2)
In 1700cm-1For carbonyl characteristic peak, 8.5-10ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 3).
The preparation of 2 compound 2# of embodiment
(1) by 1.83g 2,4- dinitroanilines, the 2g concentrated sulfuric acids, 40ml glycol dimethyl ethers, 4g 1,5- naphthalenedisulfonic acids add
Enter in there-necked flask, 3 DEG C are cooled in ice-water bath, 3g nitrosyl sulfuric acids are added dropwise, time for adding 0.5h reacts 2 after being added dropwise
Hour；Diazosalt solid is obtained after filtering；(2) 0.81g 3- Methyl-5-pyrazolones, 80ml water are added in reactor, are used
10% sodium hydroxide solution tune pH value is cooled to 4 DEG C to 11, is added with stirring 2, the 4- dinitroaniline weights that step (1) obtains
Nitrogen salt is used in combination 10% sodium carbonate liquor control ph to be added in 9, half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, filtering,
It is neutrality to be washed till filtrate using ice water, and heterocycle azo disperse dyes (compound 2#) are obtained after dry, and coupling yield is 99%.
Occur [M-H] of compound 2# at m/z 291 in mass spectrum (Fig. 4)-Quasi-molecular ions, in infrared spectrum (Fig. 5)
1690cm-1For carbonyl characteristic peak, 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 6).
The preparation of 3 compound 3# of embodiment
(1) by 1.45g 2- amino -5- nitrothiazoles, 60ml ethyl acetate, the 5g concentrated sulfuric acids, (30% is water-soluble for 5g zinc acetates
Liquid) be added in there-necked flask, be cooled to 005 degree Celsius in ice-water bath, 2g nitrosyl sulfuric acids be added, after react 2 hours；Filtering
After obtain diazosalt solid；(2) 0.97g 8-hydroxyquinolines, 80ml water are added in reactor, with 10% sodium hydroxide solution
It adjusts pH value to 10, is cooled to 5 DEG C, is added with stirring the 2- amino -5- nitrothiazole diazols obtained in step (1), is used in combination
10% sodium carbonate liquor control ph adds in 9, half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, and filtering utilizes ice water
It is neutrality to be washed till filtrate, and heterocycle azo disperse dyes (compound 3#) are obtained after dry, and coupling yield is 80%.
Occur [M-H] of compound 3# at m/z 300 in mass spectrum (Fig. 7)-Quasi-molecular ions, in infrared spectrum (Fig. 8)
1550cm-1With 1350cm-1For nitro characteristic peak, 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 9).
It is purple in its uv-visible absorption spectra (Figure 10) as can be seen that when solution ph is 6, when solution ph is 8,
The a length of 626nm of maximum absorption wave, for blue, color change is notable, has pH sensitive color change characteristics, can be used for the bore hole inspection of pH
It surveys.
The preparation of 4 compound 4# of embodiment
(1) by 2.07g 4- nitros -2,6-DCA, the 3g concentrated sulfuric acids, 50ml glycol dimethyl ethers, 3g 1,5- naphthalenes two
Sulfonic acid is added in there-necked flask, is cooled to 4 degrees Celsius in ice-water bath, be added dropwise sodium nitrite solution (30%, institute's dripping quantity and diazonium group
The molar ratio divided is 1.05：1), time for adding 0.5h reacts 1 hour after being added dropwise；Diazosalt solid is obtained after filtering；
(2) 1.24g 3- methyl-1s--5 pyrazolone of phenyl, 50ml water are added in reactor, with 10% sodium hydroxide solution tune pH
Value is cooled to 6 DEG C, is added with stirring 4- nitros -2,6-DCA diazol to 11, and 10% sodium carbonate liquor is used in combination to control pH
Value adds in 10, half an hour, and 2h is reacted at 8 DEG C；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, after dry
Heterocycle azo disperse dyes (compound 4#) are obtained, coupling yield is 92%.
Occur [M-H] of compound 3# at m/z 390 in mass spectrum (Figure 11)-Quasi-molecular ions, in infrared spectrum (Figure 12)
It is carbonyl characteristic peak 1660,7-8.6ppm is Hydrogen Proton peak on aromatic ring in nuclear magnetic spectrogram (Figure 13).
Embodiment 5
(1) by 1.96g 2- amino -3,5- dinitro thiophenes, the 1g concentrated sulfuric acids, 60ml glycol dimethyl ethers, 5g 2,6- naphthalenes
Disulfonic acid is added in there-necked flask, and 3 DEG C are cooled in ice-water bath, and 4g isoamyl nitrites are added dropwise, and time for adding 0.5h is dripped
It is reacted 2 hours after finishing；Diazosalt solid is obtained after filtering；(2) by 1.74g N- ethyl -3- cyano -4- methyl -6- hydroxyls -2-
Pyridone, 100ml water are added in reactor, with 10% sodium hydroxide solution tune pH value to 11, are cooled to 5 DEG C, are added with stirring
In 2- amino -3,5- dinitro thiophene diazols that step (1) obtains, it is used in combination 10% sodium carbonate liquor control ph small 9, half
When it is interior add, and at 5 DEG C react 2hr；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, and heterocycle idol is obtained after dry
Nitrogen disperse dyes.
Embodiment 6
(1) by 1.0g thiazolamines, 60ml ethyl acetate, the 5g concentrated sulfuric acids, 5g fluoboric acid (40% aqueous solution) addition three
In mouthful bottle, 5 DEG C are cooled in ice-water bath, 0.7g sodium nitrites are added, after react 2 hours；It is solid that diazol is obtained after filtering
Body；(2) 1.62g 4 hydroxy coumarins, 80ml water are added in reactor, it is cold with 10% sodium hydroxide solution tune pH value to 11
But to 8 DEG C, it is added with stirring the thiazolamine diazol that step (1) obtains, 10% sodium carbonate liquor control ph is used in combination to exist
9, it adds in half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, is obtained after dry
Heterocycle azo disperse dyes.
Embodiment 7-22
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, N- ethyl -3- cyano -4- methyl -6- hydroxyl -2- pyridines
Ketone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxy-ns-ethylpyridine ketone, 4 hydroxy coumarin, 7- nitros -4-
Hydroxycoumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyls quinoline, N- first
Base -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4- hydroxyl -1,8- naphthalimides, 1-
(4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyl -5- pyrazolones, 3- methyl -5- pyrroles
Oxazolone replace embodiment 1 in 3- methyl-1s--5 pyrazolone of phenyl, under alkaline condition respectively with 5-Amino-2-benzimidazolinone
Diazosalt solid coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 23-30
Utilize 2,4- dinitroanilines, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines, 2- amino benzo thiophenes
Azoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyano -5- amino
Pyrazoles replaces the 5-Amino-2-benzimidazolinone in embodiment 1, carries out diazotising, corresponding diazosalt solid is obtained, in alkaline condition
It is lower respectively with 3- methyl-1s--5 pyrazolone of phenyl, obtain corresponding heterocycle azo disperse dyes.
Embodiment 31-38
Utilize ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy
Six rings replace the ethylene glycol diethyl ether in embodiment 1 as the diazotizing solvent of 5-Amino-2-benzimidazolinone, obtain corresponding diazonium
Salt solid is coupled with 3- methyl-1s--5 pyrazolone of phenyl respectively under alkaline condition, obtains corresponding heterocycle azo dispersion dye
Material.
Embodiment 39-46
Using fluoboric acid, sodium fluoborate, zinc acetate, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 2,6-, NNO,
MF replaces stabilizer of 1, the 5- naphthalenedisulfonic acids as 5-Amino-2-benzimidazolinone in embodiment 1, obtains corresponding diazosalt solid,
It is coupled respectively with 3- methyl-1s--5 pyrazolone of phenyl under alkaline condition, obtains corresponding heterocycle azo disperse dyes.
Embodiment 47-54
Utilize nitrosyl sulfuric acid, butyl nitrite, isoamyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid
Isopropyl ester replaces diazo reagent of the nitrite tert-butyl as 5-Amino-2-benzimidazolinone in embodiment 1, obtains corresponding weight
Nitrogen salt solid obtains corresponding heterocycle azo disperse dyes with 3- methyl-1s--5 pyrazolone of phenyl respectively under alkaline condition.
Embodiment 55-70
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls
Base-N- ethylpyridines ketone, 4 hydroxy coumarin, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- hydroxyl quinolines
Quinoline, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, two formyl of 4- hydroxyls -1,8- naphthalene
Imines, N- methyl -4- hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3-
Methyl -4- benzoyl -5- pyrazolones, 3- Methyl-5-pyrazolones replace the 3- Methyl-5-pyrazolones in embodiment 2, in alkali
Property under the conditions of respectively with the diazosalt solid of 2,4- dinitroanilines be coupled, obtain corresponding heterocycle azo disperse dyes.
Embodiment 71-78
Utilize 2- amino -3,5- dinitro thiophenes, 4- nitro -2,6- dibromo anilines, 4- nitro -2- cyano-anilines, 2- ammonia
Base benzothiazole, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyanogen
Base -5- amino-pyrazols replace 2, the 4- dinitroanilines in embodiment 2, carry out diazotising, corresponding diazosalt solid are obtained, in alkali
Property under the conditions of respectively with 3- Methyl-5-pyrazolones be coupled, obtain corresponding heterocycle azo disperse dyes.
Embodiment 79-86
Utilize ethyl acetate, ether, glycol monoethyl ether, ethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy
Six rings replace the glycol dimethyl ether in embodiment 2 as the diazotizing solvent of 2,4- dinitroanilines, obtain corresponding diazol
Solid is coupled respectively with 3- Methyl-5-pyrazolones, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 87-94
Utilize fluoboric acid, sodium fluoborate, zinc acetate, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 2,6-, methylene
Two naphthalene sulfonic acids of base, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid replace 1, the 5- naphthalenedisulfonic acids in embodiment 2 as 2,4- dinitroaniline weights
The stabilizer of nitrogen salt obtains corresponding diazosalt solid, is coupled respectively with 3- Methyl-5-pyrazolones under alkaline condition, obtains phase
Answer heterocycle azo disperse dyes.
Embodiment 95-102
Utilize isoamyl nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, isobutyl nitrite, nitrous
Isopropyl propionate replaces diazo reagent of the nitrosyl sulfuric acid as 2,4- dinitroanilines in embodiment 2, obtains corresponding diazonium
Salt solid is coupled respectively with 3- Methyl-5-pyrazolones, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 103-118
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls
Base-N- ethylpyridines ketone, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy
Quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4-
Hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyls
Base -5- pyrazolones, 3- Methyl-5-pyrazolones replace embodiment 3 in 8-hydroxyquinoline, under alkaline condition respectively with 2- ammonia
The diazosalt solid of base -5- nitrothiazoles is coupled, and obtains corresponding heterocycle azo disperse dyes.
Embodiment 119-126
Utilize 2,4- dinitroanilines, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines, 2- amino benzo thiophenes
Azoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyano -5- amino
Pyrazoles replaces the 2- amino -5- nitrothiazoles in embodiment 3, carries out diazotising, corresponding diazosalt solid is obtained, in alkaline condition
It is lower to be coupled respectively with 8-hydroxyquinoline, obtain corresponding heterocycle azo disperse dyes.
Embodiment 127-134
Using glycol dimethyl ether, ether, glycol monoethyl ether, ethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol,
Dioxane replaces the conduct diazotizing solvent of 2- amino -5- nitrothiazoles of ethyl acetate in embodiment 3, obtains corresponding diazonium
Salt solid is coupled respectively with 8-hydroxyquinoline, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 135-142
Utilize 1,5- naphthalenedisulfonic acids, sodium fluoborate, fluoboric acid, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 2,6- dinaphthyl sulphurs
Acid, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid replace the zinc acetate in embodiment 3 as 2- amino -5- nitro thiophenes
The stabilizer of azoles diazol obtains corresponding diazosalt solid, is coupled respectively with 8-hydroxyquinoline under alkaline condition, obtains corresponding
Heterocycle azo disperse dyes.
Embodiment 143-150
It is different using isoamyl nitrite, sodium nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, nitrous acid
Butyl ester, Isopropyl Nitrite replace diazo reagent of the nitrosyl sulfuric acid as 2- amino -5- nitrothiazoles in embodiment 3,
Corresponding diazosalt solid is obtained, is coupled respectively with 8-hydroxyquinoline under alkaline condition, obtains corresponding heterocycle azo disperse dyes.
Embodiment 151-166
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls
Base-N- ethylpyridines ketone, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy
Quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4-
Hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyls
Base -5- pyrazolones, 3- Methyl-5-pyrazolones replace 3- methyl-1s--5 pyrazolone of phenyl in embodiment 4, in alkaline item
It is coupled respectively with the diazosalt solid of 4- nitros -2,6-DCA under part, obtains corresponding heterocycle azo disperse dyes.
Embodiment 167-174
Using 2,4- dinitroanilines, thiazolamine, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines,
2- aminobenzothiazoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4-
Cyano -5- amino-pyrazols replace 4- nitros -2,6-DCA in embodiment 4, carry out diazotising, and it is solid to obtain corresponding diazol
Body is coupled respectively with 3- methyl-1s--5 pyrazolone of phenyl, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Application examples 1
Experiment is sanded in the dyestuff that embodiment 1 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 1 of 0.50g is obtained
It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 1 obtains
Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 2
Experiment is sanded in the dyestuff that embodiment 2 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 2 of 0.50g is obtained
It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 2 obtains
Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 3
Experiment is sanded in the dyestuff that embodiment 4 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 4 of 0.50g is obtained
It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 4 obtains
Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 4
The dyestuff that embodiment 1 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：
20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion >=98%, dyeing are carried out at 130 DEG C
Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 71.65.
The dyestuff that embodiment 2 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：
20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion >=98%, dyeing are carried out at 130 DEG C
Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 80.51.
The dyestuff that embodiment 4 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：
20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion 98.2%, dyeing are carried out at 130 DEG C
Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 80.88.The brightness of this coloured fibre is apparently higher than with N,
N- diethylanilines are the brightness after dyestuff (the Comparison study embodiment 1) dyeing of coupling component；The brightness of this coloured fibre is bright
The aobvious brightness higher than after being dyed as the dyestuff (Comparison study embodiment 2) of coupling component using N- ethyl-N-cyanoethyl anilines shows
Using alkalescent arylamine serving as diazotization ingredient, using heterocycle active methylene compound or heterocycle phenols as coupling component, it is even to obtain heterocycle
Nitrogen disperse dyes have excellent dyeing brightness.
Comparison study embodiment 1
Sand milling experiment is carried out using the dyestuff of such as lower structure A：By 0.50g dyestuffs, the dispersant NNO and 2.80g of 1.00g
Water is placed in equipped with pearl is sanded and is sanded in the sand milling pipe of stick, and 1h is sanded in stirring, and dyestuff diffusion reaches HGT3399-2001 rule
Fixed 5 grades.Above-mentioned dyestuff is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：20, coloration
1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion 97.9%, coloured fibre warp are carried out at 130 DEG C
The brightness of cloth specimen is 38.24 after the measurement dyeing of electronics color measurement and color match instrument.
Comparison study embodiment 2
Sand milling experiment is carried out using the dyestuff of such as lower structure B：By 0.50g dyestuffs, the dispersant NNO and 2.80g of 1.00g
Water is placed in equipped with pearl is sanded and is sanded in the sand milling pipe of stick, and 1h is sanded in stirring, and dyestuff diffusion reaches HGT3399-2001 rule
Fixed 5 grades.Above-mentioned dyestuff is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：20, coloration
1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing at 130 DEG C, degree of exhaustion 98.5%, coloured fibre is through electronics
The brightness of cloth specimen is 40.91 after the measurement dyeing of color measurement and color match instrument.
Claims (5)
1. a kind of preparation method of 4- oxyquinolines base heterocycle azo disperse dyes, which is characterized in that this method includes following step
Suddenly：
(1) diazo component, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, after being cooled to 0~10 DEG C, in batches
Diazo reagent is added, reacts 0.1~10h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value to 8~12, keep coupling component molten
Solution, is cooled to 0~10 DEG C, is added with stirring the diazosalt solid for the diazo component that step (1) obtains, while with 10% sodium carbonate
The pH value of solution control reaction reacts 1~10h at 0~10 DEG C, obtains the compound of formula (I) in 8~10 ranges；
The wherein described diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, nitrous
In sour pentyl ester, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid
It is one or two kinds of；
Wherein：The molar ratio of diazo component, the concentrated sulfuric acid and stabilizer described in step (1) is 1:1~3:1~3；
The molar ratio of diazo reagent and diazo component described in step (1) is 1~1.05:1；
The total amount that diazo component, the concentrated sulfuric acid described in step (1) are added with stabilizer account for reaction system total weight 5~
30%；
The organic solvent is ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethyl
One kind in glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxane, two or three；Institute
The stabilizer stated is fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5- dinaphthyl sulphurs
One or both of acid, bis- naphthalene sulfonic acids of 2,6-, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid；
A-N=N-B (I)
A is diazol and the residue after coupling component coupling, the institute for the diazo component that diazo component is obtained through diazotising in formula (I)
State diazo component be selected from general formula (II -1), (II -2), (II -3), (II -4), (II -5), (II -6), (II -7), (II -8),
The structure of (II -9) and (II -10)：
In formula (II -1)：
Ra 1For-H ,-CN ,-NO2、-COR、-CONHR、-SO2,-COOR or-COAr；
Ra 2For-R ,-OR ,-NO2,-Cl or-Br；
Ra 3For-H ,-CN ,-NO2,-Ar ,-COR ,-COAr ,-COOR ,-COOAr ,-CONHR ,-SCN ,-OCOR ,-CONHAr or-
CHO；
In formula (II -2)：
Rb 1For-R ,-Ar ,-CF3、-CN、-COOR、-CONH2Or-CH2OH；
Rb 2For-NO2、-R、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar or-CN；
In formula (II -3)：
RC 1And RC 2It is each independently selected from-Cl ,-Br ,-NO2、-R、-OR、-CN、-SO2R、-SO2N or-CF3；
RC 2For in 1,2 or 3 substituent group；
In formula (II -4)：
Rd 1For-NO2,-Cl ,-Br or-H；
Rd 2For-H ,-Cl or-Br；
In formula (II -5)：
ReFor-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -6)：
RfFor-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -7)：
RgFor-R ,-Ar ,-OR ,-CN ,-SCN ,-NO2, CN ,-Cl or-CCl3；
In formula (II -8)：
Rh 1For-CN ,-H ,-COOH or-COOCH3；
Rh 2For-SCH ,-H ,-CONH2Or-CH2CN；
Rh 3For-H, phenyl or cyclohexyl；
In formula (II -9)：
Ri 1For-CN ,-NO2,-Cl ,-Br or-I；
Ri 2For-H ,-CN ,-NO2,-Cl ,-Br or-I, and work as Ri 1For-Cl ,-Br or-I when, Ri 2Cannot be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
B is the residue after the diazol coupling of coupling component and diazo component in formula (I), and the coupling component is selected from general formula
Structure shown in (III -4)：
In formula (III -4)：
Rm 1For-R ,-OR, COOR ,-Ar or-CN；
Rm 2For R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (II -1) to formula (II -7) and formula (III -4)：
R is C1-4Alkyl or C1-4Alkoxy；
Ar is phenyl.
2. preparation method according to claim 1, which is characterized in that the coupling component described in step (2) and diazonium
The molar ratio of the diazosalt solid of component is 0.8~1:0.8~1.05.
3. preparation method according to claim 1, which is characterized in that in step (1), the addition time of diazo reagent
For 0.1~1h.
4. preparation method according to claim 1, which is characterized in that in step (2), be added with stirring diazo component
The time of diazosalt solid is 5~60min.
5. the 4- oxyquinoline base heterocycle azos dispersion being prepared such as any one of them preparation method of Claims 1 to 4
Application of the dyestuff in the dyeing of polyester fiber, Fypro, acid fiber by polylactic, polypropylene fibre or acetate fiber.
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| CN106380892A (en) * | 2016-08-16 | 2017-02-08 | 上海贝通色彩科技有限公司 | A dispersed dye composition used for triacetate fibers |
| CN107501988B (en) * | 2017-08-26 | 2020-09-25 | 宁波德欣科技有限公司 | Preparation method of solvent red 195 |
| CN108034278A (en) * | 2017-12-27 | 2018-05-15 | 沈阳化工研究院有限公司 | A kind of method that coupling prepares azo dyes |
| CN113683903B (en) * | 2021-07-10 | 2024-03-15 | 青岛理工大学 | Thiazole heterocycle azo type reactive dye and preparation method thereof |
| CN114933818B (en) * | 2022-06-28 | 2024-01-16 | 绍兴文理学院 | Indoline disperse dye and preparation method thereof |
| CN115612309B (en) * | 2022-10-14 | 2023-07-21 | 浙江博澳新材料股份有限公司 | Double-heterocycle diester azo disperse dye and preparation method thereof |
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| CN106380891A (en) | 2017-02-08 |
| CN105038316A (en) | 2015-11-11 |
| CN106398309A (en) | 2017-02-15 |
| CN106433184A (en) | 2017-02-22 |
| CN106433181A (en) | 2017-02-22 |
| CN106433182B (en) | 2018-09-04 |
| CN106433183B (en) | 2018-11-09 |
| CN106433184B (en) | 2018-09-04 |
| CN106433182A (en) | 2017-02-22 |
| CN106433183A (en) | 2017-02-22 |
| CN106433181B (en) | 2018-11-09 |
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