CN1145381A - 酞菁铝活性染料 - Google Patents
酞菁铝活性染料 Download PDFInfo
- Publication number
- CN1145381A CN1145381A CN96111819A CN96111819A CN1145381A CN 1145381 A CN1145381 A CN 1145381A CN 96111819 A CN96111819 A CN 96111819A CN 96111819 A CN96111819 A CN 96111819A CN 1145381 A CN1145381 A CN 1145381A
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- China
- Prior art keywords
- formula
- reactive
- group
- phenyl
- reactive dyestuffs
- Prior art date
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- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000985 reactive dye Substances 0.000 title description 2
- 238000004043 dyeing Methods 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000000835 fiber Substances 0.000 claims description 15
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- -1 sulfophenyl Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000007639 printing Methods 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 239000004411 aluminium Substances 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 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 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 150000004780 naphthols Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000004045 reactive dyeing Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000009980 pad dyeing Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 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 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UIIKZHDXGOWIAB-UHFFFAOYSA-N NC1=CC=CC(C=2N=C(N)N=C(Cl)C=2)=C1 Chemical compound NC1=CC=CC(C=2N=C(N)N=C(Cl)C=2)=C1 UIIKZHDXGOWIAB-UHFFFAOYSA-N 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 241000907663 Siproeta stelenes Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940095054 ammoniac Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- IZUPJOYPPLEPGM-UHFFFAOYSA-M sodium;hydron;phthalate Chemical compound [Na+].OC(=O)C1=CC=CC=C1C([O-])=O IZUPJOYPPLEPGM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link
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- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
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- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
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Abstract
本发明涉及下式的已改善使用性能的酞氰,其中,Z是纤维反应基,其它取代基和标示和说明书中所赋的意义相同。
Description
本发明涉及新的酞菁活性染料及其制备与用途。
例如从EP-A 611259和DE-A 3930738中大家已知用于染制棉花的基于酞菁的青绿色和绿色活性染料,特别是酞菁铜染料和酞菁镍染料。从DE-A 2812278和2812261还知道用酞氰铝染料漂白纺织品和消灭微生物。但是用于染色的酞氰染料在使用性能方面特别和其它活性发色团联合染色方面仍有缺陷。
本发明涉及相应于下式的游离酸形式的酞氰铝活性染料式中a=0至3的一个数,b=0至2的一个数,c=0.5至3的一个数,其中a+b+c的和最好不小于2但不大于4,R1和R2相互独立地为H,C1-C6烷基,取代的C1-C6烷基特
别是被OH、SO3H、CO2H或OSO3H取代的C1-C6
烷基、苯基、取代的苯基特别是被OH、SO3H和CO2H
取代的苯基,或带磺酰基的纤维反应基,特别是下面结
构的基团式中n=0至3m=0或1,但是n+m=1,2,3或4W=-(CH2)1-6,-(CH2)2-O-(CH2)2-或—直接键Y=CH=CH2,CH2CH2Cl,CH2CH2OH或CH2CH2OSO3H,或者所述基团NR1R2=饱和杂环体系的基团,诸如象B=通过-N原子与SO2基相连的含N桥接单元,Z=纤维反应基和X=OH,OR3或通过键合单元特别是氧相连的酞菁基特别是式
(II)的基团
其中在(II)中的取代基R1、R2、B和Z具有赋予式(I)中这些取代基意义的—种,优选相同的意义,或
X=阴离子,特别是硫酸根、碳酸根、醋酸根、硫酸氢和碳酸氢
根,
R3=C1-C6烷基,它可可选地被OH。卤素或C1-C4烷氧基
取代;或苯基,它可可选地被OH、SO3OH、CO2H、C1
-C4烷基、C1-C4烷氧基或卤素取代,和
PC=下式酞菁环体系的基团其中六元碳环可另外被卤素特别是氯、C1-C6烷基、C1-C6烷氧基或在芳族化合物化学中惯用的其它取代基取代。在(1)中述及的取代基SO3H、SO2NR1R2和SO2BZ正如所知的那样优选在3位。优选的式(1)的染料是那些Pc骨架的六元碳环不再含取代基且X为OH或式(II)的基团的染料。
CH2CH2CO2H和E=H,SO3H,CO2H,CH3,C2H5,CH3O或C2H5O,和
Z=纤维反应性的杂环基,特别是选自三嗪、嘧啶或喹喔啉类,并且其中取代基和标号a、b、c、R1、R2和X具有上述的意义。
优选的纤维活性基Z是只有卤素或卤素和氨基作为取代基的三嗪、嘧啶和喹喔啉。
优选的染料(1)还有定义如下的染料,其中
其中n、m、w和y和式(I)中意义相同,R4具有上面所述的意
义,
W1=-(CH2)2-3-、-(CH2)2-O-(CH2)2-或亚苯基,
R6=H、CH3、C2H5、苯基、磺苯基或m=0的式(I)的基团,其它取代基和符号a、b、c、R1、R2和X具有式(1)中所赋的意义。
优选的式(1)的染料还有那些其纤维反应基Z具有下列意义的染料: 其中A=NH2,NHR7,NR7R8,OH,OR7,SH,SR7,SO2R7,R7,R8=分别为C1-C6烷基,被OH、SO3H、OSO3H或CO2H
取代的C1-C6烷基,苯基或萘基,或被OH、SO3H或
CO2H取代(可选地多取代)的苯基或萘基,和B1=亚烷基,亚苯基或亚萘基,特别是-(CH2)2-、-(CH2)3-
R6和Y和上面所述的意义相同。
优选的式(1)的染料还有那些桥单元B具有式(VI)的基团意义的染料其中纤维反应基Z和K键合,并且K=选自吡唑啉酮、吡啶酮、萘酚、氨基萘酚和氨基苯与二氨基苯的偶合成分,特别是下面结构的吡啶酮图中星号标出和纤维反应基Z的结合位置。特别优选的新的活性染料是式(2)至(7)的那些染料式中-NH-CH2-CH2-NH-,
-NH-(CH2)3-NH-或
其中
其中
R6、B1和B2具有上面所赋的意义。
所示的各式均是游离酸形式的。一般使用在常规制备中获得的盐,特别是碱金属盐或铵盐。
q=1至4,但条件为p+q=2,3或4和式(9)的胺反应
H-B-Z (9)如合适,和式(10)的胺反应
HNR1R2 (10)然后将仍存在的磺酸氯化物基团水解。
如果使用胺(9)和(10),它们可与(8)顺序或同时反应。
Z-Hal (12)
其中Hal=Cl、Br或F,将卤化氢分离出去。
化合物(11)可通过式(8)的酸氯化物和胺(10)和/或二胺H-B-H缩合反应来获得,或通过式(8)的酸氯化物和胺(10)和/或H-B-酰基(13)缩合反应来获得,其中在二胺H-B-H中的胺官能受可水解的酰基(如甲酰基、乙酰基、苯甲酰基等)保护,之后再将酰氨基水解。
B为式(VI)的基团的式(1)的新的活性染料,通过EP 611259A1所述的方法制备。
式(9)的胺可通过相应的具Z-Hal的二胺H-B-H的一侧的转化来制备。
式(8)的Al酚菁磺酰氯和式(9)、(19)与(13)的反应最好在0至40℃的温度和2至10的pH值下在水溶液或悬浮液中进行。在(8)与(13)的反应后产生的式(14)的化合物中酰基氨基的水解既可在酸性也可在碱性介质中进行,优选在70至80℃的温度下进行。
式(11)的染料与Z-Hal的反应最好在pH4~9及0至60℃的水溶液或悬浮液中进行。
新染料非常适合于染色或印制含羟基和酰胺基的织物材料,例如纤维素、羊毛或合成聚酰胺。它们按常规方法使用。
新染的色和印迹具有很好的坚牢度水平。
新的活性染料既可以粉或颗粒的形式使用也可以浓的水溶液形式使用。本发明还涉及已用式(1)的染料染色的包括含羟基或酰胺基的材料的织物产物。
在一优选的实施方案中,所述染料是以颗粒方式使用的。所述染料的颗粒剂可按下列步骤获得:
混合制粒
在这种情况下,用基于所述粉混合物计的15-55%的水润湿干粉,然后将混合物在混合制粒机中成型并随后进行干燥并除去粉尘,将除尘剂作为气溶胶混合物喷到颗粒上。
喷雾制粒
在这种情况下,合成溶剂或悬浮液被在流化喷雾干燥器中同时干燥和制粒。
一般来说干粉或干粒各基于总组合物含(重量%)30-80%式(1)的活性染料和5-15%的水。此外,它们也可能含有无机盐如碱金属氯化物或碱金属硫酸盐、分散剂和除尘剂。
当所述混合物溶解于20倍的水(基于干成品形式的重量)中时,优选的固体混合物另外含有使pH达到3.5至7.5特别是4.5于6.5的缓冲物质。所加入的这些缓冲混合物的量是总重量的3-50%特别是5-15%。
含水的活性染料溶液一般含5-50%式(1)的染料(基于溶液的总重量计)。
优选的含水活性染料溶液另外含使pH为3.5至7.5特别是4.5至6.5的缓冲物质。这些缓冲物质的量最好为总重量的0.1-50%特别是1-20%。
所用的缓冲物对反应基是惰性的。缓冲物的例子有:磷酸二氢钠、磷酸氢二钠、磷酸二氢钾、磷酸氢二钾、醋酸钠、醋酸钾、硼酸钠、硼酸钾、草酸钠、草酸钾和邻苯二甲酸氢钠。这些缓冲液可单独使用也可混合使用。
按照本发明的染料特别适合染制织品,特别是染制含羟基或酰胺基的材料。
含羟基的材料是那些天然或合成来源的材料诸如象纤维材料或其再生产物和聚乙烯醇。纤维素纤维材料最好是棉花,但也可以是其它植物纤维如亚麻、大麻、黄麻和苎麻纤维;再生的纤维素纤维有例如粘胶短纤维和长丝粘胶丝。含羧酰胺基的材料有例如合成和天然发生的聚酰胺和聚氨基甲酸乙酯,特别是纤维形式如羊毛和其它动物毛发、丝、皮、尼龙6,6、尼龙6、尼龙11和尼龙4。
按照本发明的化合物可通过已知的水溶性染料的应用技术特别是那些已知的水溶性纤维活性染料的应用技术来施加到或固定在所述的基材上特别是在所述的纤维材料上。
这样,通过使用最多样化的酸结合剂和适当时用的中性盐如氯化钠或硫酸钠从一长液(long liquor)的吸尽过程而伴随它们染到纤维素纤维上得到非常好的色彩效果。染色最好在加压和适当时在常用染色辅剂的存在下在60至105℃之间温度的水浴中进行,适当时最高可在120℃的温度下进行。这里可采用的一种方法是将材料导入温浴中,逐渐将浴锅加热至所需的染色温度,染色过程在该温度完成。如果需要,加速染料的吸尽的中性盐也可可选地在真正的染色温度达到后加入到所述浴中。该染料由于其在由于中性盐和随后的酸结合剂的加入而导致的更和谐的性质而更出色。
由于和纯碎的乙烯砜染料相比具有更好的溶解性,通过轧染法在纤维素行维上同样获得优良的颜色效果和物品的非常好的外观,所述染料可在室温或通过汽蒸或在升高的温度如最高达约60℃的条件下以常规方式分批固定。
通过常规的纤维素纤维的印染方法获得深的印迹和好的外形状况和清楚的白色背景,所述印染方法可在一相中进行,例如通过用含碳酸氢钠或另一酸结合剂的印染浆印染并随后在100-130℃下蒸制来进行,所述印染方法也可在两相中进行,例如通过用中性或弱酸性印墨印染并随后固定来进行,固定可通过热的含电解质的碱浴来进行,或通过用碱性的含电解质的轧染液轧染,并随后分批处理即在碱性条件下所轧染材料的蒸制或干热处理来进行。其印染质量只稍稍取决于不同的固定条件。
120至200℃的热空气被用于常规热固定方法的利用热的固定。除了常规的101至103℃的蒸汽外,也可使用高至160℃的超热蒸汽和压缩蒸汽。
酸结合和在纤维素纤维上产生固定的剂是例如无机或有机酸的碱金属和同样地碱土金属的水溶性碱式盐或在热的影响下释放碱的化合物。碱金属氢氧化物和弱至中等强度的无机或有机酸的碱金属盐可被特别提出,碱金属化合物优选指钠和钾化合物。这种酸结合剂有例如氢氧化钠、氢氧化钾、碳酸钠、碳酸氢钠、碳酸钾、甲酸钠、磷酸二氢钠、磷酸氢二钠、三氯乙酸钠、硅酸钠或磷酸钠。
按照本发明的化合物(染料)可通过(如适当可在热的作用下)按照本发明的化合物和酸结合剂的处理而化学键合到纤维素纤维上;当用于染色或印染过程中时,在这些纤维材料上,它们以高的固定效果而表现优秀。特别是因为由于它们在冷水中良好的溶解性而可容易地洗掉染料的非固定部分,因此在通过漂洗除去染料的非固定部分的常规后处理后,纤维素染色显示出优良的耐湿性。
由按照本发明的化合物产生的染色和印迹在具有非常消晰的印迹方面是突出的。特别是在纤维素纤维材料上的染色和印迹具有好的对光坚牢度和非常好的耐湿性、诸如对洗、磨、水、海水、交染和酸汗与碱汗的坚牢度,还有对折叠的坚牢度,对熨烫的坚牢度和对摩擦的坚牢度。
按照本发明的化合物也可进一步用于羊毛的纤维染色。已进行无毡或低毡处理(参见例如H.Rath,Lehrbuch der Textlchemie[Textbookof Textile Chemistry],Sprenger-Verlag,3rd Edition(1972),page 295-299,in particular treatment by the so-called Hercosett process(page 298);J.Soc.Dyes和Colourists 1972 93-99,and 1975,33-44)的羊毛也可染色而具非常好的坚牢性。
羊毛的染色方法可以在酸性介质中以常规已知的程序进行。因此,例如,乙酸和/或硫酸氨或乙酸和乙酸氨或乙酸钠被加入到染色浴中以获得所需的pH。为达到合用的染色水平,建议加入常规的均染助剂,诸如象基于氰尿酰氯和3倍摩尔量的对氨基苯磺酸和/或氨基萘磺酸的反应产物那些助剂,或基于例如硬脂胺和环氧乙烷的反应产物的那些助剂。因此,例如,染色首先从pH约3.5至5.5的酸性染色通过吸尽过程来进行,同时控制pH并在快到染色结束时,将pH转变到中性,或适用时转变至最高达pH8.5的弱碱性,特别使与纤维完全反应性结合而获得良好的染色深度。同时没有反应结合的染料被溶掉。
这里所述的方法也适用于在其它天然产生的聚酰胺或合成的聚酰胺和聚氨基甲酸乙酯的纤维材料上染色的生产中。通常,被染色的材料被送到约40℃的染色浴中并搅动一会儿,然后将染色浴用优选的弱的乙酸调节到所需的弱酸性的pH并在60至98℃之间的温度下进行实际的染色。但是,染色也可在沸点温度下进行,也可在最高达106℃的密封装置中进行。
因为所述化合物的水溶解性非常好,它们可有利地用于常规的连续染色处理中。
所示的式是相应游离酸的那些式。所述染料一般以碱金属盐特别是Na盐的形式被分离和用于染色。
实施例1
在室温搅拌条件下以30分钟时间将115g氯铝酞氰投入600ml氯磺酸中。然后将该混合物在136-138℃搅拌8小时,冷却后的熔化物倾入到冰中。将该悬浮液吸滤,固态产物用冰水洗涤直到基本上不管硫酸盐和酸游离。在游离式的形式中,分离出的湿浆基本上相应于式
在吸滤器上将冰水加入到所述材料中,然后搅拌加入11g氯化铵和95g 2,4-二氯-6-(3-氨基苯基)氨基嘧啶。在2小时的过程中通过加入氢氧化钠溶液将该悬液或溶液的pH调节到9.8至10.0,同时温度被提高到25℃。当所述反应溶液在该温度下再搅拌8小时后,用稀盐酸将pH调节到7并用氯化钠盐析。将所述染料吸滤出并在60℃真空干燥。以其游离酸形式的染料基本相应于下式并将棉品染成清晰带绿色的青兰色,即在棉品上印染上带绿的青兰色。
实施例2
在实施例1和2的染料中的磺化程度和磺酰胺基的含量可以已知方式通过氯磺化作用条件的轻微变化或通过所用氨基化合物量的改变来控制。
实施例3
具上述结构的所用的染料中间产物通过酞氰铝磺酰氯和1,3-二氨基苯及(适用时)所选的一定量的氯化铵的缩合来得到。
实施例4至19
通过二氨基化合物、胺和/或具体反应体系的改变来用类似实施例1至3的方法制备下列新的有意义的青兰色活性染料:实施例4:
实施例5:
实施例6:
实施例7:
实施例8:
实施例9:
实施例10:
实施例11:
实施例12:
实施例13:
实施例14:
实施例15:
实施例16:
实施例17:
实施例18:
实施例19:
实施例20至30
通过使用脂族二氨基化合物代替类似于实施例1至3的芳族化合物得到下列重要的新的青兰色活性染料:实施例20:
实施例21:
实施例22:
实施例23:
实施例24:
实施例25:
实施例26:
实施例27:
实施例28:
实施例29:
实施例30:
实施例31
从115g按照实施例1的氯-酞氰铝制备的羟基-酞菁铝-磺酰氯在1升冰水和2ml吡啶中搅拌。量取281g 4-(β-硫酸根合乙基磺酰基)苯胺在水中的中性溶液加入其中并通过同时加入固体碳酸氢钠将pH保持恒定于5.8至6.0。然后将该混合物在10小时的过程中从0℃加温到25℃。获得约450g下列结构的绿兰色粉末。
实施例40
从115g按照实施例1的氯-酞氰铝制备的羟基-酞菁铝-磺酰氯在1升水和2ml吡啶中搅拌。量取52g N-甲基-2-(β-磺乙基磺基)乙胺和169g 4-(β-硫酸根合乙基磺酰基)苯胺在水中的溶液加入其中并通过加入20%碳酸氢钾溶液将pH保持恒定在6.5至6.7。用6至8小时将该混合物加温到25℃,然后将氯化钾加入反应溶液中直至染料完全沉淀。通过各种施用方法用该染料在棉品上染出清晰的青兰色。在棉品或粘胶丝上印染出鲜艳的青绿色同样是可能的。所述染料具有下面结构
当使用相应量的其它胺代替N-甲基-2-(β-硫酸根合乙基磺酰基)乙胺时,得到下列有意义的青兰色染料:
实施例43:
实施例44:
当实施例40中的二种胺组分不同时,获得下列双官能青绿色活性染料:
实施例49
将通过已知方法即氯-酞氰铝的氯磺化和随后与1,3-二氨基苯-4-磺酸反应制备的下式的0.025mol的发色基团和0.0026mol亚硝酸钠在150ml水中的溶液一起搅拌。将该溶液冷却至0至2℃并滴加到100g冰/水与12g 30%盐酸的混合物中。所得到的重氮化盐悬浮物在0至5℃下加入到含300g冰/水和0.025mol 1-(3-甲基氨基丙基)-2-羟基-4-甲基-2-吡啶的溶液中。同时通过加入20%氢氧化钠溶液将pH控制在9.0至9.5。得到的绿色溶液通过常规方法(类似于实施例3)和2,4,6-三氟嘧啶反应而形成下面结构的染料
这种染料将纤维素材料染成鲜绿色。
当含β-硫酸根合乙基磺酰基的吡唑啉酮被选作实施例49中的偶合组分,并省去最终的和卤代嘧啶的冷凝步骤时,可直接得到鲜绿色活性染料:
以水作为溶剂测定的λmax值小结如下:
实施例 | λmax |
1 | 609,677nm |
2 | 609,677nm |
6 | 609,678nm |
9 | 642,674nm |
31 | 608,679nn |
36 | 609,678nm |
37 | 609,678nm |
38 | 612,680nm |
45 | 609(sh),677nm |
Claims (14)
1.相应于下面结构的游离酸态的铝酞氰活性染料
式中
a=0至3的一个数,
b=0至2的一个数,
c=0.5至3的一个数,
Pc=酞菁基,
R1和R2分别为H、C1-C6烷基、取代的C1-C6烷基、苯基、
取代的苯基或带磺酰基的纤维反应基、或NR1R2一起是
饱和杂环体系的基团,
B=通过-N原子与SO2基相连的含N桥接单元,
Z=纤维反应基,
X=OH,OR3、通过键合单元或一阴离子相连的酞菁基
R3=C1-C6烷基、取代的C1-C6烷基、苯基或取代的苯基。
2.按照权利要求1的活性染料,其中a+b+c的和不小于2但不大于4。
3.按照权利要求1的活性染料,其中R1和R2分别为H,C1-C6烷基,被OH、SO3H、CO2H或OSO3H取代的C1-C6烷基,苯基或被OH、SO3H或CO2H取代的苯基。
6.如权利要求1的活性染料,其中X是OH、OR3或下式的基团其中取代基R1和R2,B和Z及符号a、b和c具有权利要求1所给出的那些意义之一。
7.权利要求1的活性染料,其中式中R4和R5互相独立地为=H,CH3,C2H5,CH2CH2OH,CH2CO2H or CH2CH2CO2H和E=H,SO3H,CO2H,CH3,C2H5,CH3O或C2H5O,和
Z=纤维反应杂环基团。
8.权利要求1的活性染料,其中Z是只有卤素或只有卤素和氨基作为取代基的纤维反应性三嗪、嘧啶或喹喔啉。
14.用活性染料染色和/或印染含羟基或酰胺基的材料的方法,它包括让权利要求1的活性染料在所述材料上作用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19529853.5 | 1995-08-14 | ||
DE19529853A DE19529853A1 (de) | 1995-08-14 | 1995-08-14 | Aluminium-Phthalocyanin-Reaktivfarbstoffe |
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Publication Number | Publication Date |
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CN1145381A true CN1145381A (zh) | 1997-03-19 |
Family
ID=7769438
Family Applications (1)
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CN96111819A Pending CN1145381A (zh) | 1995-08-14 | 1996-08-14 | 酞菁铝活性染料 |
Country Status (10)
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US (1) | US5780621A (zh) |
EP (1) | EP0761767A1 (zh) |
JP (1) | JPH0953019A (zh) |
KR (1) | KR970010888A (zh) |
CN (1) | CN1145381A (zh) |
BR (1) | BR9603410A (zh) |
CZ (1) | CZ239596A3 (zh) |
DE (1) | DE19529853A1 (zh) |
PL (1) | PL315651A1 (zh) |
TW (1) | TW412576B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19624469A1 (de) * | 1996-06-19 | 1998-01-02 | Dystar Textilfarben Gmbh & Co | Reaktive Aluminiumphthalocyaninfarbstoffe, Verfahren zu ihrer Herstellung und Verwendung |
WO2001060933A2 (en) | 2000-02-21 | 2001-08-23 | Kao Corporation | Water-based ink |
US8795422B2 (en) | 2009-08-31 | 2014-08-05 | Hewlett-Packard Development Company, L.P. | Naphthalocyanine dye and ink containing the same |
US8202358B2 (en) * | 2009-10-02 | 2012-06-19 | Hewlett-Packard Development Company, L.P. | Phthalocyanine, naphthalocyanine, and bridged phthalocyanine/naphthalocyanine dyes and inks containing the same |
US8226757B2 (en) * | 2009-10-22 | 2012-07-24 | Hewlett-Packard Development Company, L.P. | Phthalocyanine dye and ink containing the same |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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CH371540A (de) * | 1958-12-12 | 1963-08-31 | Sandoz Ag | Verfahren zur Herstellung von Phthalocyaninfarbstoffen |
CH630127A5 (de) * | 1977-03-25 | 1982-05-28 | Ciba Geigy Ag | Verfahren zum bleichen von textilien. |
FR2387658A1 (fr) * | 1977-03-25 | 1978-11-17 | Ciba Geigy Ag | Procede pour combattre les microorganismes |
MX155643A (es) * | 1980-02-29 | 1988-04-11 | Ciba Geigy Ag | Composicion blanqueadora de telas |
DE3138864A1 (de) * | 1981-09-30 | 1983-04-14 | Hoechst Ag, 6230 Frankfurt | Wasserloesliche faserreaktive phthalocyaninverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
US4566874A (en) * | 1981-12-09 | 1986-01-28 | Ciba-Geigy Corporation | Water-soluble zinc and aluminium phthalocyanines and use thereof as photoactivators |
US4497741A (en) * | 1981-12-09 | 1985-02-05 | Ciba-Geigy Corporation | Water-soluble zinc and aluminium phthalocyanines |
DE3480794D1 (de) * | 1983-07-29 | 1990-01-25 | Ciba Geigy Ag | Reaktivfarbstoffe, deren herstellung und verwendung. |
DE3918653C2 (de) * | 1988-06-14 | 2003-01-16 | Clariant Finance Bvi Ltd | Chromophore Verbindung mit heterocyclischem Reaktivrest |
DE3930738B4 (de) * | 1988-09-23 | 2004-07-29 | Clariant Finance (Bvi) Ltd. | Phthalocyanin-Reaktivfarbstoffe, ihre Herstellung und ihre Verwendung |
DE3843558A1 (de) * | 1988-12-23 | 1990-06-28 | Bayer Ag | Reaktivfarbstoffe |
EP0484027B1 (en) * | 1990-11-02 | 1996-12-18 | Zeneca Limited | Polysubstituted phthalocyanines |
DE4304242A1 (de) * | 1993-02-12 | 1994-08-18 | Sandoz Ag | Phthalocyanin-Reaktivfarbstoffe |
DE4338853A1 (de) * | 1993-11-13 | 1995-05-18 | Hoechst Ag | Wasserlösliche schwermetallfreie Phthalocyaninfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
CH688935A5 (de) * | 1994-06-15 | 1998-06-15 | Clariant Finance Bvi Ltd | Aluminium-Phthalocyanin-Reaktivfarbstoffe. |
-
1995
- 1995-08-14 DE DE19529853A patent/DE19529853A1/de not_active Withdrawn
-
1996
- 1996-08-01 EP EP96112428A patent/EP0761767A1/de not_active Withdrawn
- 1996-08-08 US US08/694,041 patent/US5780621A/en not_active Expired - Fee Related
- 1996-08-09 JP JP8226143A patent/JPH0953019A/ja active Pending
- 1996-08-09 TW TW085109650A patent/TW412576B/zh active
- 1996-08-12 PL PL96315651A patent/PL315651A1/xx unknown
- 1996-08-13 CZ CZ962395A patent/CZ239596A3/cs unknown
- 1996-08-13 KR KR1019960033536A patent/KR970010888A/ko not_active Application Discontinuation
- 1996-08-13 BR BR9603410A patent/BR9603410A/pt not_active Application Discontinuation
- 1996-08-14 CN CN96111819A patent/CN1145381A/zh active Pending
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TW412576B (en) | 2000-11-21 |
KR970010888A (ko) | 1997-03-27 |
EP0761767A1 (de) | 1997-03-12 |
PL315651A1 (en) | 1997-02-17 |
US5780621A (en) | 1998-07-14 |
CZ239596A3 (en) | 1997-03-12 |
DE19529853A1 (de) | 1997-02-20 |
JPH0953019A (ja) | 1997-02-25 |
BR9603410A (pt) | 1998-05-12 |
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