PL57827B1 - - Google Patents

Info

Publication number

PL57827B1

PL57827B1 PL116359A PL11635966A PL57827B1 PL 57827 B1 PL57827 B1 PL 57827B1 PL 116359 A PL116359 A PL 116359A PL 11635966 A PL11635966 A PL 11635966A PL 57827 B1 PL57827 B1 PL 57827B1

Authority

PL

Poland

Prior art keywords

amino

dyes

parts

dyeing

dye

Prior art date

1966-09-06

Links

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• 238000000034 method Methods 0.000 claims description 17
• 229910052794 bromium Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 239000001000 anthraquinone dye Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 230000031709 bromination Effects 0.000 claims description 2
• 238000005893 bromination reaction Methods 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical group 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 1
• 239000000975 dye Substances 0.000 description 32
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
• 238000004043 dyeing Methods 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 239000000835 fiber Substances 0.000 description 9
• -1 1-amino-5-m-methoxybenzoyl aminoanthraquinone Chemical compound 0.000 description 8
• 239000004744 fabric Substances 0.000 description 8
• 229920000728 polyester Polymers 0.000 description 7
• 239000000203 mixture Substances 0.000 description 6
• 239000002253 acid Substances 0.000 description 5
• FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• 238000000859 sublimation Methods 0.000 description 5
• 230000008022 sublimation Effects 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• 238000000227 grinding Methods 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 239000000984 vat dye Substances 0.000 description 4
• 229920000742 Cotton Polymers 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• 210000002268 wool Anatomy 0.000 description 3
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
• KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
• VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 2
• NGAKQDFKEQYVTL-UHFFFAOYSA-N N-(5-amino-6-bromo-9,10-dioxoanthracen-1-yl)benzamide Chemical group NC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(C1=CC=CC=C1)=O)=O)Br NGAKQDFKEQYVTL-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000000985 reactive dye Substances 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 238000009736 wetting Methods 0.000 description 2
• RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
• HOHPWSPZJKCCDU-UHFFFAOYSA-N 1,2-diamino-5-(4-chlorobenzoyl)anthracene-9,10-dione Chemical compound NC1=C(C=CC=2C(C3=C(C=CC=C3C(C1=2)=O)C(C1=CC=C(C=C1)Cl)=O)=O)N HOHPWSPZJKCCDU-UHFFFAOYSA-N 0.000 description 1
• FOJKHZNFRQSIPY-UHFFFAOYSA-N 1,2-diamino-5-(4-methylbenzoyl)anthracene-9,10-dione Chemical compound NC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)C(C1=CC=C(C=C1)C)=O)=O)N FOJKHZNFRQSIPY-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
• IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical group ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 239000004604 Blowing Agent Substances 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 229920003043 Cellulose fiber Polymers 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
• LLKXONMBGXUVGK-UHFFFAOYSA-N NC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)C(C1=CC=C(C=C1)OC)=O)=O)N Chemical compound NC1=C(C=CC=2C(C3=C(C=CC=C3C(C12)=O)C(C1=CC=C(C=C1)OC)=O)=O)N LLKXONMBGXUVGK-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 239000004952 Polyamide Substances 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical class O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 239000007859 condensation product Substances 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
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 238000005552 hardfacing Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• QMTDZZMSWVNEBX-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)-2-chlorobenzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1Cl QMTDZZMSWVNEBX-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229920002647 polyamide Polymers 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 239000012264 purified product Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 239000000344 soap Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 239000002699 waste material Substances 0.000 description 1