BE518168A

BE518168A -

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Publication number: BE518168A
Authority: BE; Belgium
Prior art keywords: parts; dyes; dye; acid; methyl
Prior art date

Application number

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English (en)

French (fr)

Publication of BE518168A publication Critical patent/BE518168A/fr

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239000000975 dye Substances 0.000 claims description 62
210000002268 Wool Anatomy 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
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 claims description 17
-1 fatty alcohol esters Chemical class 0.000 claims description 11
230000000875 corresponding Effects 0.000 claims description 9
125000004432 carbon atoms Chemical group C* 0.000 claims description 8
RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 7
230000001808 coupling Effects 0.000 claims description 7
238000010168 coupling process Methods 0.000 claims description 7
238000005859 coupling reaction Methods 0.000 claims description 7
238000006193 diazotization reaction Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
150000002191 fatty alcohols Chemical class 0.000 claims description 4
239000000835 fiber Substances 0.000 claims description 4
150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
150000002790 naphthalenes Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000000987 azo dye Substances 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
238000004043 dyeing Methods 0.000 claims 1
239000000463 material Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
230000001264 neutralization Effects 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating Effects 0.000 description 8
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
239000000843 powder Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4H-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
HWYHBUBPBUKOJI-UHFFFAOYSA-N S(=O)(=O)(O)C=1C=C2C=CC=C(C2=CC1)N1NC(C=C1C)=O Chemical compound S(=O)(=O)(O)C=1C=C2C=CC=C(C2=CC1)N1NC(C=C1C)=O HWYHBUBPBUKOJI-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
239000001043 yellow dye Substances 0.000 description 2
HRBCDVLFVGOSIC-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-1H-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(Cl)=C1 HRBCDVLFVGOSIC-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
UWLNKHDLVZEYKQ-UHFFFAOYSA-N 4-chloro-3-(3-methyl-5-oxo-4H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(S(O)(=O)=O)=CC=C1Cl UWLNKHDLVZEYKQ-UHFFFAOYSA-N 0.000 description 1
GWHZXIMAQAFUCP-UHFFFAOYSA-N 5-methyl-2-(3-methylphenyl)-4H-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC(C)=C1 GWHZXIMAQAFUCP-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
UOJPASZFBRYVFR-UHFFFAOYSA-N CC1=NN(C(C1)=O)C1=CC=C(C2=CC=CC=C12)S(=O)(=O)O Chemical compound CC1=NN(C(C1)=O)C1=CC=C(C2=CC=CC=C12)S(=O)(=O)O UOJPASZFBRYVFR-UHFFFAOYSA-N 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
240000006669 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
230000001034 aminogenic Effects 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000027326 copulation Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
DFLRTTRPSHIDGC-UHFFFAOYSA-N dodecyl 2-aminobenzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1N DFLRTTRPSHIDGC-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000009963 fulling Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XKUUMWKWUZRRPD-UHFFFAOYSA-N heptan-2-amine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CCCCCC(C)[NH3+].CCCCCC(C)[NH3+] XKUUMWKWUZRRPD-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000001788 irregular Effects 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008274 jelly Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-N o-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
FFZFHRYMHDWKAX-UHFFFAOYSA-N octyl 2-aminobenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1N FFZFHRYMHDWKAX-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1