CN102924960B - Benzo isothiazole azo pyrazolone disperse dye as well as preparation method and use thereof - Google Patents
Benzo isothiazole azo pyrazolone disperse dye as well as preparation method and use thereof Download PDFInfo
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- CN102924960B CN102924960B CN201210498771.9A CN201210498771A CN102924960B CN 102924960 B CN102924960 B CN 102924960B CN 201210498771 A CN201210498771 A CN 201210498771A CN 102924960 B CN102924960 B CN 102924960B
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title claims abstract description 18
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000000986 disperse dye Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000000835 fiber Substances 0.000 claims abstract description 73
- 239000000975 dye Substances 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 230000005012 migration Effects 0.000 claims abstract description 6
- 238000013508 migration Methods 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- -1 C 1~8alkyl Chemical class 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 6
- 238000003483 aging Methods 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 230000021615 conjugation Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- 239000004744 fabric Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- 239000004677 Nylon Substances 0.000 description 6
- 229920001778 nylon Polymers 0.000 description 6
- 229920004933 Terylene® Polymers 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- SQBCSDZTDXLTLE-UHFFFAOYSA-N 5-nitro-2,1-benzothiazol-3-amine Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N)SN=C21 SQBCSDZTDXLTLE-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 101150050192 PIGM gene Proteins 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002972 Acrylic fiber Polymers 0.000 description 3
- 0 COC(C(C(C1=O)=NNc2c(cc(cc3)N=O)c3n[s]2)=*1c1ccccc1)=O Chemical compound COC(C(C(C1=O)=NNc2c(cc(cc3)N=O)c3n[s]2)=*1c1ccccc1)=O 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000007705 chemical test Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000012747 synergistic agent Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 1
- YBSYYLRYPMFRNL-UHFFFAOYSA-N 2,2-bis(methylsulfonyl)propane Chemical compound CS(=O)(=O)C(C)(C)S(C)(=O)=O YBSYYLRYPMFRNL-UHFFFAOYSA-N 0.000 description 1
- CWESERWNUIUBJU-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1Cl CWESERWNUIUBJU-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- ATOKLGLFMWDISO-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]-5-methyl-4H-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=C(CN)C=C1 ATOKLGLFMWDISO-UHFFFAOYSA-N 0.000 description 1
- CBCZQJLYYRPMRI-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid Chemical compound C1=CC2=CC=CC=C2C(S(=O)(=O)O)=C1CC1=CC=CC=C1 CBCZQJLYYRPMRI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 description 1
- CAEVXLTUQCJGIL-SDXDJHTJSA-N CC(/C(/C1=O)=N/Nc2c(cc(cc3)[N+]([O-])=O)c3n[s]2)=NN1c1ccccc1 Chemical compound CC(/C(/C1=O)=N/Nc2c(cc(cc3)[N+]([O-])=O)c3n[s]2)=NN1c1ccccc1 CAEVXLTUQCJGIL-SDXDJHTJSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000012850 discrimination method Methods 0.000 description 1
- 238000010130 dispersion processing Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- XJOLZQBDMYBTEK-UHFFFAOYSA-N methyl 5-oxo-1-phenyl-4h-pyrazole-3-carboxylate Chemical compound O=C1CC(C(=O)OC)=NN1C1=CC=CC=C1 XJOLZQBDMYBTEK-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
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- 235000015067 sauces Nutrition 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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Abstract
The invention discloses a benzo isothiazole azo pyrazolone disperse dye. The benzo isothiazole azo pyrazolone disperse dye is a compound having the structure shown in a formula (I) in the specification. Conjugate migration of hydrogen connected with a heteroatom in the benzo isothiazole azo pyrazolone heterocyclic ring disperse dyes is performed among benzo isothiazole ring, azo and pyrazolone to display bright-colored yellow, red and blue; and moreover, the dye is large in hue span and rich in colors; and therefore, the benzo isothiazole azo pyrazolone disperse dye can be used for preparing a fiber identification coloring agent. The invention discloses a preparation method of the benzo isothiazole azo pyrazolone disperse dye.
Description
Technical field
The present invention relates to a kind of benzisothiazole azo pyrazolone type disperse dye and the application in textile apparel fibers is differentiated thereof.
Background technology
Fibre identification is very important to work such as the inspection of quality in the stages such as fiber process, weaving, printing and dyeing and production management and control, many people are studied, therefore produce a variety of discrimination methods, as By Birefringence Method, fluorescent method, X-ray diffraction method, infrared spectroscopy, rotational line polarization detection method, terahertz time-domain spectroscopy, density gradient method and thermogravimetry etc., analysis result accuracy is high, but instrument is expensive, and need special experimenter, laboratory adopts the simple method such as microscopic examination, burning, chemical test, staining test conventionally.
For natural fiber---cotton, wool, silk, the fiber crops sample microscopic examination method that takes a morsel, can distinguish, but man-made fiber the method resolving ability is obviously declined.Though combustion test is very simple but inaccurate, chemical test needs a set of analytical reagent with corrodibility and toxicity, and result is subject to the impact of operational condition larger, and process is loaded down with trivial details.These methods are for the fibre identification of single type and set up, and for the discriminating of mixed fibre product, are difficult to be suitable for.
Paint test differentiate fiber be a kind of easy and simple to handle, speed fast, equipment simple method again.The good tinting material of some effects is developed, as the common development of HI-1 fibre identification tinting material Shi You China Textile University and Shanghai City printing and dyeing industry company, by the substantive dyestuff of dispersed dye, anionic property, the cationic dyestuff of cationic is composite forms, the test method of differentiating textile fibres with this reagent, has been listed in GB/T 13787-92 textile fibres telling test method tinting material method.Fibre identification agent-chemical drug differentiating solvent Q and the Kayastain A of No. 4 fibre identification tinting materials of Du Pont, Nippon Kayaku K. K's exploitation are also formed by different types of dyestuff blending, and these dyestuffs, respectively to dying on specific fiber, make it to present unique color.
The known tinting material with certain application is all composited by multiple dyestuff, complicated components.Particularly anionic dyestuff and cationic dyestuff are composite, are easy to cohesion in various degree occurs in preparation, storage, use procedure, stable not.And dispersed dye component wherein has tinting strength on synthon and semi-synthetic fibre, the tinting material that mixing colouring agent forms is also not obvious in the color distinction of different fibers, as HI-1 fibre identification tinting material on terylene for rubine, vinegar fine for orange, nylon are that sauce is red, acrylic fibers are pink, wool be red lotus etc. is all red color tone, if misoperation or dye when insufficient, still easily obscures.
Garment material human consumer, is often subject to fake and forged puzzlement, need under the condition of house, differentiate quickly and easily generic and the approximate content of common fiber, is also difficult at present realize.Therefore need a kind of stable performance, common fiber as fibers such as terylene, nylon, cotton, hair, vinegar fibre, acrylic fibers on the obvious fibre identification reagent of colour development difference, and simple to operate, be easy to the fibre identification method of realization.
Summary of the invention
The object of this invention is to provide a kind of common fiber and blending product thereof, fibre identification tinting material fast and accurately.
The inventor is [(a) .W.Huang, H.F.Qian, Dyes Pigm., 2008,77,446 on the basis of dispersed dye structure effect research; (b) W.Huang, Dyes Pigm., 2008,79,69; (c) H.F.Qian and W.Huang, ActaCrystallogr.Sect.C Cryst.Struct.Commun., 2006, C62, o62; (d) T.Tao, F.Xu, X.C.Chen, Q.Q.Liu, W.Huang, X.Z.You, Dyes Pigm., 2012,92,916; (e) J.Geng, T.Tao, S.J.Fu, W.You, W.Huang, Dyes Pigm., 2011,90,65; (f) B.Hu, G.Wang, W.You, W.Huang, X.Z.You, DyesPigm., 2011,91,105; (g) W.You, H.Y.Zhu, W.Huang, B.Hu, Y.Fan and X.-Z.You, DaltonTrans., 2010,39,7876; (h) X.C.Chen, T.Tao, Y.G.Wang, Y.X.Peng, W.Huang, H.F.Qian, Dalton Trans., 2012,41,11107], designed and synthesized a kind of acid-base reagent energy variable color of meeting, the heterocycle dispersed dye of benzisothiazole azo pyrazoline ketone, are surprised to find the hydrogen being connected with heteroatoms, under certain potential of hydrogen, can be in benzisothiazole ring, azo, the migration of pyrazolone interannular generation conjugation, can demonstrate bright-coloured Huang, red and blue, form and aspect span is very large, and color performance is abundant.
Unexpectedly, such dyestuff has different painted behavior and color on each fibrid, especially on the good chemical synthetic fiber of tint permanence, shows especially complete different form and aspect, is extremely suitable as fibre identification materials'use.
For achieving the above object, technical scheme of the present invention is as follows:
A benzisothiazole azo pyrazolone type disperse dye, it is the Compound I that has following structure:
formula (I)
Wherein: R
1for hydrogen, halogen, alkyl, alkoxyl group, nitro or trifluoromethyl;
R
2for C
1～8alkyl, phenyl or COOR, wherein R is alkyl or the alkyl that replaced by oxygen;
R
3for hydrogen, C
1～8alkyl, halogen, C
1～8alkyl sulfuryl, C
1～4alkyl amido, C
1～8alkyl sulfonyl amino, phenylsulfonamido or C
1～4benzene sulfonamide amido;
R
4for hydrogen, alkyl, halogen, methylsulfonyl, alkyl amido or sulfonamido.
Above-mentioned benzisothiazole azo pyrazolone type disperse dye, it is the Compound I that has following structure:
Preferably
R wherein
1, R
2, R
3, R
4taking from following three groups with the definition of Y appoints and gets one:
1.R
1for nitro, R
2for CH
3, R
3for hydrogen, R
4for hydrogen;
2.R
1for nitro, R
2for CH
3, R
3for Cl, R
4for hydrogen;
3.R
1for nitro, R
2for CH
3, R
3for hydrogen, R
4for CH
3;
4.R
1for nitro, R
2for COOCH
3, R
3for hydrogen, R
4for hydrogen.
Above-mentioned benzisothiazole azo pyrazolone type disperse dye, can there is conjugation migration in the hydrogen atom being connected with heteroatoms of described Compound I, form isomer II or III:
Formula II formula III
R wherein
1, R
2, R
3and R
4definition and above-mentioned Compound I in R
1, R
2, R
3and R
4definition identical.
A method of preparing above-mentioned dispersed dye, it comprises the steps:
Step 1. takes 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃ (temperature can not over 80 ℃), stops heating, and cooling naturally, if salt out, can be heated a little and make its dissolving, obtains nitrosyl sulfuric acid; Take 3-amino-5-R of 3mmol
1-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves;
Step 2. is got the 5ml vitriol oil, and 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, add a little ice cube, put into cryosel and bathe, the deep brown solution that step 1 is made is added drop-wise in sulphuric acid soln, rapid stirring, after dripping, continues reaction 10～15min;
Step 3. takes the 1-(2-R of 3mmol
3-4-R
4-phenyl)-3-R
2-5-pyrazolone, puts into 250ml three-necked bottle, adds 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, and keeps temperature lower than 0 ℃, by the diazotization solution of step 2, is added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete;
After step 4. reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I;
Wherein said R
1, R
2, R
3and R
4definition and above-mentioned Compound I in R
1, R
2, R
3and R
4definition identical.
The inventor is surprised to find, the heterocycle dispersed dye of benzisothiazole azo pyrazoline ketone of the present invention, the hydrogen being connected with heteroatoms, under certain potential of hydrogen, can be in benzisothiazole ring, azo, the migration of pyrazolone interannular generation conjugation, can demonstrate bright-coloured Huang, red and blue, form and aspect span is very large, and color performance is abundant.
Therefore, benzisothiazole azo pyrazoline ketone dyestuff of the present invention can be as preparing fibre identification tinting material.
Above-mentioned fibre identification tinting material, it at least contains a kind of component A as shown in the formula (I), the total amount of the fibre identification tinting material based on described, component A massfraction is 1～100%.
The present invention relates to a kind of textile fiber identification method, it is characterized in that using described fiber dimension to differentiate tinting material.
Contriver studies discovery, shown in formula (I) generally there is the tautomerism of azo and hydrazone formula structure in structure, under room temperature, mainly with hydrazone formula configuration, exist, and the carbonyl of hydrazone hydrogen and pyrazolone forms intramolecular six-ring hydrogen bond, but the proton of hydrazone hydrogen under certain condition (as different pH values, temperature, with the supramolecule effect of solvent) can on pyrazolone ring and benzisothiazole ring, move.The characteristic of moving under certain chemical environment just because of this kind of proton, when they and different fibre-effects, can be subject to the impact of the different chemical group that fiber has, the isomer of dye composition shown in formula (I) and the migration of heteroatoms hydrogen conjugation thereof exists with different ratios, shows distinct colors.
Described component A, preferably one of following, two or more mixture:
formula (I-1),
The dye composition the present invention relates to is a class water-insoluble dye.For convenience of using, generally, fibre identification tinting material of the present invention is through case of wet attrition under auxiliary agent exists, and dispersion processing becomes wield dispersed dye goods.For example, by dye composition shown in general structure (I), general structure (II), general structure (III), under the existence of auxiliary agent, water or other wetting agent, with sand mill, grind, make its median size at 0.1 to 10 micron, obtain the dispersed dye goods of fibre identification tinting material of the present invention.The dispersed dye goods that obtain can be for the preparation of printing paste or dye bath after adding water.
Described auxiliary agent is dispersed dye when processing conventional dispersion agent, diffusant etc., preferably one of following or its several mixture arbitrarily: the anionic dispersing agents such as the ammonia solution thing of the hydrolyzate of the formaldehyde condensation products of the formaldehyde condensation products of naphthene sulfonic acid, the formaldehyde condensation products of alkyl naphthalene sulfonic acid, benzyl naphthalene sulfonic acid, sulfonated lignin, polycarboxylic acid macromolecule dispersing agent, phenylethylene-maleic anhydride resin, phenylethylene-maleic anhydride resin, the carboxylate of phenylethylene-maleic anhydride resin, poly alkylene glycol ether sulfuric ester, alkyl polyoxyethylene glycol phosphoric acid ester.Especially naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), condensation compound of methyl naphthalene sulfonic acid and formaldehyde (as Dispersant MF), benzyl naphthalenesulfonate formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A).The ratio of auxiliary agent and dye composition can change in relative broad range, and generally the weight ratio of auxiliary agent and dyestuff is (0.2～10): 1, preferably (0.5～2): 1.
The liquid state of the dispersed dye goods of fibre identification tinting material of the present invention after with corpusculed, emulsifiable paste state, by spray-drying process etc., carry out dried powdery or graininess is supplied with dyeing.In flowing product, the weight percentage of dye composition is 10～60%, and the weight percentage of auxiliary agent is 5～45%, and all the other are water or other synergistic agent.Described synergistic agent is optional frostproofer, anti-settling agent, sterilant, metal chelating agent, hyperchromicity agent, thickening material, stablizer, levelling agent, fastness elevator, defoamer and carrier (swelling agent) etc.In solid dye goods, the weight percentage of dye composition is 10～60%, and the weight percentage of auxiliary agent is 40～90%.
Fibre identification tinting material of the present invention is dying filamentary material can be realized according to known method.For example, under optional common carrier (swelling agent), conventional anionic or non-ionic dispersing agent, levelling agent, buffer reagent, reduction preventing agent etc. exist, in pH value, be by aqueous dispersion, by dip method, to be dyeed at the temperature of 4～11,95～140 ℃; Can also the slurry that dyes that contain fibre identification tinting material be applied to fabric by the mode of padding, after drying, in 180～225 ℃, carry out hot melt fixation 15 seconds～5 minutes; Can also the printing paste that contain fibre identification tinting material be applied to fabric by the method scraping, again by saturation steam (147～176KPa, 120～140 ℃, 10～45 minutes), (160～185 ℃ of superheated vapours, 4～15 minutes) or heated dry air (190～225 ℃, 0.5～5 minute) carry out fixation.
Full and uniform painted when not needing, when making fast qualitative and differentiating or only do rough qualitative analysis, can also will be impregnated with fiber or the fabric of fibre identification tinting material of the present invention, by electric iron pressing fixation or insert microwave-oven-heating fixation.
Painted thing can directly be observed after rinsing well with clear water.In order to observation, can also be by the tone of soaping or reduction clearing acquisition is distincter.
Material to be identified and known materials are bathed together, with condition, with fibre identification tinting material of the present invention, dyeed, by ratio method, can increase the accuracy of fibre identification.If parallel execution coloured differently condition, as different PH, differing temps, Different staining method carries out many conditions correlations, can significantly improve the accuracy rate of fiber identification.
By fibre identification tinting material of the present invention level dyeing for mixed fibre or fabric, in view of people's the vision acumen sensation to color, according to different tint permanences and the coloured light of xenogenesis fiber, uneven rate that can testing fiber blending, judges that whether blending is even.If coloured fiber or fabric are chosen to a minute distinct colors under the microscope, weigh in the balance respectively heavily, can detection fibers or the blending rate of fabric.
The present invention is owing to having adopted technique scheme, realized simple, differentiate exactly textile fibres, because dye component is less, also tool has the following advantages: textile fibres of the present invention differentiates that tinting material is easy to preparation, is easy to use, fibre identification recoverability is good, common fiber recognition rate is high, can also be for analyzing mixed fibre and fabric.
Embodiment
With specific embodiment, the present invention is described below, but protection scope of the present invention is not limited to this.
Embodiment 1
Take 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃ (temperature can not over 80 ℃), stops heating, and cooling naturally, if salt out, can be heated a little and make its dissolving, obtains nitrosyl sulfuric acid.Take 0.585g(3mmol) 3-amino-5-nitro-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves.
Get the 5ml vitriol oil, 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, adds a little ice cube, puts into cryosel and bathes.The above-mentioned deep brown solution preparing is added drop-wise in sulphuric acid soln to rapid stirring.After dripping, reaction 10～15min.
Take 0.523g (3mmol) 1-phenyl-3-methyl-5-pyrazolones ketone, put into 250ml three-necked bottle, add 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, keep temperature lower than 0 ℃, by above-mentioned diazotization solution, be added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete.
After reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I-1, quality is 0.94g(productive rate 82.3%).
Mp:282-283℃.Anal.Calcd.for[C
17H
12N
6O
3S]:C,53.68;H,2.18;N,22.09%.Found:C,53.45;H,2.23;N,21.98%.Main?FT-IR?absorptions(KBr?pellets,cm
-1):3249(w),1654(m),1538(m),1498(s),1319(s),1147(s).
1H?NMR(500MHz,CDCl
3)δ:8.80(s,1H,isthiazole),8.20(d,1H,isthiazole),7.95(d,2H,phen),7.72(d,1H,isthiazole),7.48(t,2H,phen),7.29(t,1H,phen),2.44(s,3H,Me).Positive?ESI-MS:m/z=379.33,[M]
+.UV-Vis?in?methonal,λ
max/ε(L·mol
-1·cm
-1)=578(22030)and?315(13470)nm.
Embodiment 2
Take 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃ (temperature can not over 80 ℃), stops heating, and cooling naturally, if salt out, can be heated a little and make its dissolving, obtains nitrosyl sulfuric acid.Take 0.585g(3mmol) 3-amino-5-nitro-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves.
Get the 5ml vitriol oil, 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, adds a little ice cube, puts into cryosel and bathes.The above-mentioned deep brown solution preparing is added drop-wise in sulphuric acid soln to rapid stirring.After dripping, reaction 10～15min.
Take 3mmol 1-phenyl-3-methoxycarbonyl-5-pyrazolone, put into 250ml three-necked bottle, add 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, keep temperature lower than 0 ℃, by above-mentioned diazotization solution, be added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete.
After reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I-2.
Embodiment 3
Take 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃ (temperature can not over 80 ℃), stops heating, and cooling naturally, if salt out, can be heated a little and make its dissolving, obtains nitrosyl sulfuric acid.Take 0.585g(3mmol) 3-amino-5-nitro-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves.
Get the 5ml vitriol oil, 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, adds a little ice cube, puts into cryosel and bathes.The above-mentioned deep brown solution preparing is added drop-wise in sulphuric acid soln to rapid stirring.After dripping, reaction 10～15min.
Take 3mmol 1-(2-chloro-phenyl-)-3-methyl-5-pyrazolone, put into 250ml three-necked bottle, add 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, keep temperature lower than 0 ℃, by above-mentioned diazotization solution, be added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete.
After reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I-3.
Embodiment 4
Take 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃ (temperature can not over 80 ℃), stops heating, and cooling naturally, if salt out, can be heated a little and make its dissolving, obtains nitrosyl sulfuric acid.Take 0.585g(3mmol) 3-amino-5-nitro-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves.
Get the 5ml vitriol oil, 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, adds a little ice cube, puts into cryosel and bathes.The above-mentioned deep brown solution preparing is added drop-wise in sulphuric acid soln to rapid stirring.After dripping, reaction 10～15min.
Take 3mmol 1-(4-aminomethyl phenyl)-3-methyl-5-pyrazolone, put into 250ml three-necked bottle, add 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, keep temperature lower than 0 ℃, by above-mentioned diazotization solution, be added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete.
After reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I-4.
Embodiment 5
By the ammonia solution thing of 2 grams of dispersion agent Reax 83A, 10 grams of macromolecule dispersing agent phenylethylene-maleic anhydride resins, 30 grams of wetting agents and antifreeze glycol, 0.1 gram of sterilant CMIT, 0.1 gram of defoamer phenylethyl alcohol oleic acid ester and 47.8 grams of water, employing homogenizer mixes, and in whipping process, to mixed solution, adds the dye composition shown in 10 grams of formulas (I-1).Then add silicon carbide, adopt shredder under the rotating speed of 3500 revs/min, to grind 40 hours, be uniformly dispersed, stable mill base.Take 30 grams of described mill bases, add 9 grams of ethylene glycol, 6 grams of glycol ethers, 3 grams of glycerol, 0.3 gram of surfactant A EO-9,11.7 grams of water, after stirring under normal temperature, employing aperture is that the strainer of 0.45 micron filters, and obtains fibre identification tinting material liquid product.
Embodiment 6
Dye composition shown in 50.0 grams of formulas (I-1), 70 grams of dispersion agent Reax 85A, 200 grams of pure water one are reinstated to sand mill and carried out corpusculed (making dispersion treatment), until particle diameter is less than 1 micron, spraying is dry again, obtains the solid-state product of fibre identification tinting material.
Embodiment 7
Get solid-state product and 0.075 gram of Glacial acetic acid of the fibre identification tinting material that 0.05 gram of embodiment 3 makes, be made into 75 milliliters of dye liquors, wherein pH value is 4～4.5, put into 1.0 gram of six fine fabric and (meet GB 7564-7568 textile color stability test STANDARD ADJACENT FABRIC specification (neq ISO 105-F:1985), fine by vinegar, cotton, nylon, terylene, six kinds of acrylic fibers and wools etc. are fibrous), the fiber needle fabric of material is known at 1.0 grams of ends, in 60 minutes, by normal temperature, be warmed up to 130 ℃, be incubated 45 minutes, in the time of below being cooled to 85 ℃, take out fabric, at 85 ℃ by V-Brite B and sodium-hydroxide treatment 20 minutes, water rinse, dry.Painted situation is as shown in table 1.
Table 1
Unknown fiber by yellowish-brown and blue two kinds fibrous, clip is a fritter wherein, folding bulk fibre, separation under amplification border, wherein yellowish brown fiber is 0.0822 gram, 0.0675 gram of blue fiber.By learning with six fiber contrasts, unknown fabric is polyester and nylon blended product, and blending rate is about 55:45.
Embodiment 8
Press embodiment 8 operations, wherein acetic acid substitutes for sodium bicarbonate, and wherein pH value is 7～8, obtains the painted result significantly different from example 5, as shown in table 2:
Table 2
The color that sample acquisition is similar with polyamide fibre (nylon) to terylene and the deep or light degree of depth.
If the comparing result in conjunction with implementing 4, shows that sample is under coloured differently condition, there is the painted behavior the same with polyamide fibre with terylene, therefore, by the different condition contrast of dye, judge that sample is polyester and nylon blended product.Obviously, such conclusion is very reliable.
Embodiment 9
By unknown fiber and six fine fabrics (specification that meets ISO 105-F:1985 STANDARD ADJACENT FABRIC), with embodiment 6 gained liquid products, infiltrate, wring out, then infiltrate and extract, then use electric iron pressing 30 seconds.With clear water, rinse, in painted sample, obviously have ruddiness grey and brown fibre, cotton with to wash painted situation similar to six fine standard fabric, then binding fiber outward appearance, the unknown fiber that is easy to determine is cotton-polyester blend thing.
Embodiment 10
By unknown fiber and six fine fabrics (specification that meets ISO 105-F:1985 STANDARD ADJACENT FABRIC), with embodiment 6 gained immersion bubbles, then insert in microwave oven, high power handling 2 minutes, cooling rinse with clear water afterwards, obtain painted thing similar to Example 10, obtain identical identification result.
In sum, utilize the present invention to differentiate that fiber is simple and quick, even can under the condition of house, implement, in addition, the diversity by fiber staining under the painted condition of difference contrasts, and can differentiate exactly fiber.
Claims (6)
1. a benzisothiazole azo pyrazolone type disperse dye, is characterized in that it is the Compound I that has following structure:
Wherein: R
1for hydrogen, halogen, alkyl, alkoxyl group, nitro or trifluoromethyl;
R
2for C
1～8alkyl, phenyl or COOR, wherein R is alkyl or the alkyl that replaced by oxygen;
R
3for hydrogen, C
1～8alkyl, halogen, C
1～8alkyl sulfuryl, C
1～4alkyl amido, C
1～8alkyl sulfonyl amino, phenylsulfonamido or C
1～4benzene sulfonamide amido;
R
4for hydrogen, alkyl, halogen, methylsulfonyl, alkyl amido or sulfonamido.
2. a benzisothiazole azo pyrazolone type disperse dye, is characterized in that it is the Compound I that has following structure:
R wherein
1, R
2, R
3, R
4definition take from following four groups and appoint and get one:
Group 1.R
1for nitro, R
2for CH
3, R
3for hydrogen, R
4for hydrogen;
Group 2.R
1for nitro, R
2for CH
3, R
3for Cl, R
4for hydrogen;
Group 3.R
1for nitro, R
2for CH
3, R
3for hydrogen, R
4for CH
3;
Group 4.R
1for nitro, R
2for COOCH
3, R
3for hydrogen, R
4for hydrogen.
3. benzisothiazole azo pyrazolone type disperse dye according to claim 1 and 2, is characterized in that: conjugation migration can occur the hydrogen atom being connected with heteroatoms of described Compound I, forms isomer II or III:
R wherein
1, R
2, R
3and R
4definition and above-mentioned Compound I in R
1, R
2, R
3and R
4definition identical.
4. a method of preparing dispersed dye described in claim 1 or 2, is characterized in that it comprises the steps:
Step 1. takes 0.227g(3.3mmol) NaNO
2, add 2.5ml(39.6mmol, 1:12) and the vitriol oil, rapid stirring, while being heated to 65-70 ℃, stops heating, and cooling naturally, if salt out, can be heated a little it is dissolved, and obtains nitrosyl sulfuric acid; Take 3-amino-5-R of 3mmol
1-2,1-benzisothiazole, dissolves with above-mentioned solution, then adds the vitriol oil of 2ml, has obtained auburn solution, and solid all dissolves;
Step 2. is got the 5ml vitriol oil, and 7.5ml Glacial acetic acid is made into sulfuric acid/acetum of 40% in 250ml three-necked bottle, add a little ice cube, put into cryosel and bathe, the deep brown solution that step 1 is made is added drop-wise in sulfuric acid/acetum, rapid stirring, after dripping, continues reaction 10～15min;
Step 3. takes the 1-(2-R of 3mmol
3-4-R
4-phenyl)-3-R
2-5-pyrazolone, puts into 250ml three-necked bottle, adds 30ml methyl alcohol, 30ml deionized water, cryosel is bathed, and keeps temperature lower than 0 ℃, by the diazotization solution of step 2, is added drop-wise in pyridone solution, and quick vigorous stirring, after dropwising, reaction 5～10min makes it complete;
After step 4. reaction finishes, mother liquor is heated to 40～50 ℃ of ageings 5 minutes, makes dye granule become large, decompress filter, water successively, ethanol/water 1:1 solution washing, dries, and obtains Compound I;
Wherein said R
1, R
2, R
3and R
4definition and above-mentioned Compound I in R
1, R
2, R
3and R
4definition identical.
5. the application of the benzisothiazole azo pyrazoline ketone dyestuff described in claim 1 or 2 in preparing fibre identification tinting material.
6. fibre identification tinting material according to claim 5, is characterized in that: it at least contains the component A shown in the Compound I described in a kind of claim 1 or 2, the total amount of the fibre identification tinting material based on described, and component A massfraction is 1～100%.
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| CN1108346C (en) * | 2000-12-04 | 2003-05-14 | 武汉大学 | Disperse blud dye and its synthetic process and application |
| US7344236B2 (en) * | 2003-09-12 | 2008-03-18 | Konica-Minolta Holdings, Inc. | Ink-jet cloth printing ink and an ink-jet recording method |
| CN1995026A (en) * | 2006-12-21 | 2007-07-11 | 浙江龙盛集团股份有限公司 | Benzisothiazole compound, preparation and application thereof, and disperse dye composition |
| CN101081838B (en) * | 2006-12-21 | 2010-12-15 | 浙江龙盛集团股份有限公司 | Benzo isothiazole compound, preparation and application and disperse dyes composition |
| ES2415929T3 (en) * | 2008-10-21 | 2013-07-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes, procedure for preparing them and using them |
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