BE574446A

BE574446A -

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Publication number: BE574446A
Authority: BE; Belgium
Prior art keywords: sep; amino; acid; parts; residue
Prior art date

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English (en)

French (fr)

Publication of BE574446A publication Critical patent/BE574446A/fr

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239000002253 acid Substances 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 20
230000001808 coupling Effects 0.000 claims description 12
238000010168 coupling process Methods 0.000 claims description 12
238000005859 coupling reaction Methods 0.000 claims description 12
230000027326 copulation Effects 0.000 claims description 10
239000000987 azo dye Substances 0.000 claims description 9
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 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
229960001663 sulfanilamide Drugs 0.000 claims description 6
150000001412 amines Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 3
150000001875 compounds Chemical group 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 3
229920001184 polypeptide Polymers 0.000 claims description 3
HDQWKODISDGAGX-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonamide Chemical compound C1=CC=CC2=C(S(N)(=O)=O)C(N)=CC=C21 HDQWKODISDGAGX-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
150000002790 naphthalenes Chemical class 0.000 claims description 2
238000000034 method Methods 0.000 claims 5
FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 223
239000000975 dye Substances 0.000 description 33
210000002268 Wool Anatomy 0.000 description 19
ZMCHBSMFKQYNKA-UHFFFAOYSA-N Orthanilic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 18
-1 2-amino-phenyl 1- -naphthyl-sulfone Chemical compound 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
238000006193 diazotization reaction Methods 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000000243 solution Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XRMLOZSMCSUBTL-UHFFFAOYSA-N phenylazanide Chemical compound [NH-]C1=CC=CC=C1 XRMLOZSMCSUBTL-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 8
229960000583 Acetic Acid Drugs 0.000 description 7
229910052921 ammonium sulfate Inorganic materials 0.000 description 7
235000011130 ammonium sulphate Nutrition 0.000 description 7
230000001264 neutralization Effects 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000001166 ammonium sulphate Substances 0.000 description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
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 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000000843 powder Substances 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
239000001187 sodium carbonate Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
125000003277 amino group Chemical group 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
230000000875 corresponding Effects 0.000 description 4
238000004043 dyeing Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000002378 acidificating Effects 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 2
BJYPLHFAPRTHLY-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonamide Chemical class C1=C(S(N)(=O)=O)C=C(O)C2=CC(N)=CC=C21 BJYPLHFAPRTHLY-UHFFFAOYSA-N 0.000 description 2
DJMBGZLVYLOSGM-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonamide Chemical class C1=CC(S(N)(=O)=O)=CC2=CC(N)=CC=C21 DJMBGZLVYLOSGM-UHFFFAOYSA-N 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N Diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
GWFRSQBGIGLMFD-BBKOCAQVSA-N N-[9-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,4-dihydroxyoxolan-2-yl]purin-6-yl]-2-phenoxyacetamide Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)(C=1C=CC=CC=1)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC(=O)COC=4C=CC=CC=4)=C3N=C2)O1 GWFRSQBGIGLMFD-BBKOCAQVSA-N 0.000 description 2
210000004940 Nucleus Anatomy 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000010410 dusting Methods 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
230000000269 nucleophilic Effects 0.000 description 2
239000001044 red dye Substances 0.000 description 2
150000003335 secondary amines Chemical group 0.000 description 2
125000000565 sulfonamide group Chemical group 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
RWOGBGSRUYDQAM-UHFFFAOYSA-N 2-amino-N,N-dicyclohexylbenzenesulfonamide Chemical compound NC1=CC=CC=C1S(=O)(=O)N(C1CCCCC1)C1CCCCC1 RWOGBGSRUYDQAM-UHFFFAOYSA-N 0.000 description 1
URDSZUCCEUWAHY-UHFFFAOYSA-N 2-amino-N-benzyl-N-methylbenzenesulfonamide Chemical compound C=1C=CC=C(N)C=1S(=O)(=O)N(C)CC1=CC=CC=C1 URDSZUCCEUWAHY-UHFFFAOYSA-N 0.000 description 1
YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
BOJXVYVIGCXZJY-UHFFFAOYSA-N 2-nitrobenzenesulfinic acid Chemical class OS(=O)C1=CC=CC=C1[N+]([O-])=O BOJXVYVIGCXZJY-UHFFFAOYSA-N 0.000 description 1
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
XQVJSGRZOXGXSP-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-sulfonamide Chemical class NS(=O)(=O)C1C=CC=CC1=[N+]=[N-] XQVJSGRZOXGXSP-UHFFFAOYSA-N 0.000 description 1
KLWOLLZUNJZMLH-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-sulfonic acid Chemical class OS(=O)(=O)C1C=CC=CC1=[N+]=[N-] KLWOLLZUNJZMLH-UHFFFAOYSA-N 0.000 description 1
ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical class C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
JPYQFYIEOUVJDU-UHFFFAOYSA-N Beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
JRLMJIQXYZMMEO-UHFFFAOYSA-N C1(=CC=C(C=C1)[N-]C)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)[N-]C)C1=CC=CC=C1 JRLMJIQXYZMMEO-UHFFFAOYSA-N 0.000 description 1
OCTCIYNBOFACIO-UHFFFAOYSA-N C1(=CC=CC=C1)[N-]CC Chemical compound C1(=CC=CC=C1)[N-]CC OCTCIYNBOFACIO-UHFFFAOYSA-N 0.000 description 1
SUSGHUIAEYFPLD-UHFFFAOYSA-N C=1C=CC=CC=1C[N-]C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C[N-]C1=CC=CC=C1 SUSGHUIAEYFPLD-UHFFFAOYSA-N 0.000 description 1
MFQDPUGVRHXCON-UHFFFAOYSA-N CCCCNS(=O)=O Chemical compound CCCCNS(=O)=O MFQDPUGVRHXCON-UHFFFAOYSA-N 0.000 description 1
XOVFZYLMQKXAFU-UHFFFAOYSA-N CN(S(=O)(=O)C1=C(C=CC(=C1)CCCCC)N)C1=CC=CC=C1 Chemical compound CN(S(=O)(=O)C1=C(C=CC(=C1)CCCCC)N)C1=CC=CC=C1 XOVFZYLMQKXAFU-UHFFFAOYSA-N 0.000 description 1
210000004013 Groin Anatomy 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium Ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
DATAGRPVKZEWHA-YFKPBYRVSA-N N(5)-ethyl-L-glutamine zwitterion Chemical group CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 description 1
IZQAHEFFPVEFRF-UHFFFAOYSA-N NC1=C(C=CC=C1)CCCCCCCCS(=O)(=O)CCCCCCCCC1=C(C=CC=C1)N Chemical compound NC1=C(C=CC=C1)CCCCCCCCS(=O)(=O)CCCCCCCCC1=C(C=CC=C1)N IZQAHEFFPVEFRF-UHFFFAOYSA-N 0.000 description 1
VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ZMCUELWKGIZNPM-UHFFFAOYSA-N S(=O)(=O)(O)C1=CC=C(C=C1)N(S(=O)=O)CC1=CC=CC=C1 Chemical compound S(=O)(=O)(O)C1=CC=C(C=C1)N(S(=O)=O)CC1=CC=CC=C1 ZMCUELWKGIZNPM-UHFFFAOYSA-N 0.000 description 1
ALNAZWBQCVCXTE-UHFFFAOYSA-N S(=O)(=O)(O)C1=CC=C(CN(S(=O)=O)C)C=C1 Chemical compound S(=O)(=O)(O)C1=CC=C(CN(S(=O)=O)C)C=C1 ALNAZWBQCVCXTE-UHFFFAOYSA-N 0.000 description 1
QKOUJQVAASNTNI-UHFFFAOYSA-N S(=O)(=O)(O)C1=CC=C(CNS(=O)(=O)N)C=C1 Chemical compound S(=O)(=O)(O)C1=CC=C(CNS(=O)(=O)N)C=C1 QKOUJQVAASNTNI-UHFFFAOYSA-N 0.000 description 1
239000000980 acid dye Substances 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
125000005362 aryl sulfone group Chemical group 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
CRXBVOPMGFCEHK-UHFFFAOYSA-N cyclohexyl(methyl)azanide Chemical compound C[N-]C1CCCCC1 CRXBVOPMGFCEHK-UHFFFAOYSA-N 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009963 fulling Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000005181 nitrobenzenes Chemical class 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
239000001048 orange dye Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
DELFPZLNAZAZRE-UHFFFAOYSA-N phenyl 2-aminobenzenesulfonate Chemical compound NC1=CC=CC=C1S(=O)(=O)OC1=CC=CC=C1 DELFPZLNAZAZRE-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
235000021178 picnic Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000004964 sulfoalkyl group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1