BE509558A - - Google Patents

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Publication number

BE509558A

BE509558A BE509558DA BE509558A BE 509558 A BE509558 A BE 509558A BE 509558D A BE509558D A BE 509558DA BE 509558 A BE509558 A BE 509558A

Authority

BE

Belgium

Prior art keywords

parts

dyes

dye

acid

methyl

Prior art date

Links

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• 239000000975 dye Substances 0.000 claims description 42
• 238000000034 method Methods 0.000 claims description 21
• 238000004043 dyeing Methods 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 7
• 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 4
• 239000000463 material Substances 0.000 claims description 3
• 230000008878 coupling Effects 0.000 description 15
• 238000010168 coupling process Methods 0.000 description 15
• 238000005859 coupling reaction Methods 0.000 description 15
• 210000002268 wool Anatomy 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 238000004532 chromating Methods 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
• -1 heterocyclic amines Chemical class 0.000 description 6
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 5
• 229940124530 sulfonamide Drugs 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 150000001875 compounds Chemical class 0.000 description 4
• 150000008049 diazo compounds Chemical class 0.000 description 4
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 240000007817 Olea europaea Species 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 229960003742 phenol Drugs 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 125000000565 sulfonamide group Chemical group 0.000 description 3
• 238000011282 treatment Methods 0.000 description 3
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
• FMVHOPSNTYRCRM-UHFFFAOYSA-N 3-amino-2-hydroxy-5-nitrobenzenesulfonamide Chemical class NC1=CC([N+]([O-])=O)=CC(S(N)(=O)=O)=C1O FMVHOPSNTYRCRM-UHFFFAOYSA-N 0.000 description 2
• NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 2
• DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
• 150000007513 acids Chemical class 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
• 235000011130 ammonium sulphate Nutrition 0.000 description 2
• 150000003931 anilides Chemical class 0.000 description 2
• 229950011260 betanaphthol Drugs 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 238000006193 diazotization reaction Methods 0.000 description 2
• 239000000835 fiber Substances 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
• KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 150000003456 sulfonamides Chemical class 0.000 description 2
• JZNRSOWVJXUZQO-UHFFFAOYSA-N (2-amino-7-hydroxynaphthalen-1-yl)-phenylmethanone Chemical compound NC1=CC=C2C=CC(O)=CC2=C1C(=O)C1=CC=CC=C1 JZNRSOWVJXUZQO-UHFFFAOYSA-N 0.000 description 1
• ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
• QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
• VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
• MOXDGMSQFFMNHA-UHFFFAOYSA-N 2-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1O MOXDGMSQFFMNHA-UHFFFAOYSA-N 0.000 description 1
• ZSUDUDXOEGHEJR-UHFFFAOYSA-N 4-methylnaphthalen-1-ol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=C1 ZSUDUDXOEGHEJR-UHFFFAOYSA-N 0.000 description 1
• KEGNUIZNBCHWLZ-UHFFFAOYSA-N 5,8-dichloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1Cl KEGNUIZNBCHWLZ-UHFFFAOYSA-N 0.000 description 1
• IPZJPYHEVWLBNH-UHFFFAOYSA-N 5-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1Cl IPZJPYHEVWLBNH-UHFFFAOYSA-N 0.000 description 1
• YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
• WWPKRXOOVICNJY-UHFFFAOYSA-N 6-methoxynaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(OC)=CC=C21 WWPKRXOOVICNJY-UHFFFAOYSA-N 0.000 description 1
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
• 239000003513 alkali Substances 0.000 description 1
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000001166 ammonium sulphate Substances 0.000 description 1
• 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 238000003763 carbonization Methods 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
• URCLXLVQHAJFSJ-UHFFFAOYSA-N chlorosulfonyl hypochlorite Chemical compound ClOS(Cl)(=O)=O URCLXLVQHAJFSJ-UHFFFAOYSA-N 0.000 description 1
• 229910052804 chromium Inorganic materials 0.000 description 1
• 239000011651 chromium Substances 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 230000009918 complex formation Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 150000005204 hydroxybenzenes Chemical class 0.000 description 1
• 235000015243 ice cream Nutrition 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 239000010446 mirabilite Substances 0.000 description 1
• DSEQJUPGRWESKP-UHFFFAOYSA-N n-(2-hydroxy-5-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=CC=C1O DSEQJUPGRWESKP-UHFFFAOYSA-N 0.000 description 1
• IIYVYHIILNDZLB-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=C(O)C=C12 IIYVYHIILNDZLB-UHFFFAOYSA-N 0.000 description 1
• NHWKEOWEOKNTFL-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)formamide Chemical compound C1=CC=C(NC=O)C2=CC(O)=CC=C21 NHWKEOWEOKNTFL-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 239000003760 tallow Substances 0.000 description 1