BE544959A

BE544959A -

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Publication number: BE544959A
Authority: BE; Belgium
Prior art keywords: group; groups; formula; residue; alkyl
Prior art date

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English (en)

French (fr)

Publication of BE544959A publication Critical patent/BE544959A/fr

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239000000975 dye Substances 0.000 claims description 67
125000001424 substituent group Chemical group 0.000 claims description 22
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 20
230000001808 coupling Effects 0.000 claims description 19
238000010168 coupling process Methods 0.000 claims description 19
238000005859 coupling reaction Methods 0.000 claims description 19
239000011780 sodium chloride Substances 0.000 claims description 19
239000000835 fiber Substances 0.000 claims description 18
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
230000001034 aminogenic Effects 0.000 claims description 16
229920002239 polyacrylonitrile Polymers 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
238000004043 dyeing Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 12
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 11
150000001875 compounds Chemical class 0.000 claims description 10
125000004433 nitrogen atoms Chemical group N* 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
125000004432 carbon atoms Chemical group C* 0.000 claims description 5
238000006193 diazotization reaction Methods 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical class OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000002253 acid Substances 0.000 description 17
150000001299 aldehydes Chemical class 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
-1 amino - Chemical class 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical class NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000007859 condensation product Chemical group 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
HHSBHVJQXZLIRW-UHFFFAOYSA-N 3-N,3-N-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(N)=C1 HHSBHVJQXZLIRW-UHFFFAOYSA-N 0.000 description 2
229920002972 Acrylic fiber Polymers 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical class O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
210000002268 Wool Anatomy 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
230000000397 acetylating Effects 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000027326 copulation Effects 0.000 description 2
230000000875 corresponding Effects 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
GWXQTTKUYBEZBP-UHFFFAOYSA-N 1H-benzimidazol-1-ium-2-sulfonate Chemical class C1=CC=C2NC(S(=O)(=O)O)=NC2=C1 GWXQTTKUYBEZBP-UHFFFAOYSA-N 0.000 description 1
YNAKESQZGPZDDZ-UHFFFAOYSA-N 2-N,2-N-diethylbenzene-1,2-diamine Chemical compound CCN(CC)C1=CC=CC=C1N YNAKESQZGPZDDZ-UHFFFAOYSA-N 0.000 description 1
VJTZHXQAZLGBHV-UHFFFAOYSA-N 3-N-phenylbenzene-1,3-diamine Chemical compound NC1=CC=CC(NC=2C=CC=CC=2)=C1 VJTZHXQAZLGBHV-UHFFFAOYSA-N 0.000 description 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
241000273930 Brevoortia tyrannus Species 0.000 description 1
FLVYFLKKPKRCBJ-UHFFFAOYSA-N C(C)C1=C(N)C=CC=C1.NC1=CC=CC=C1 Chemical compound C(C)C1=C(N)C=CC=C1.NC1=CC=CC=C1 FLVYFLKKPKRCBJ-UHFFFAOYSA-N 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
LEQAOMBKQFMDFZ-UHFFFAOYSA-N Glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
229940015043 Glyoxal Drugs 0.000 description 1
VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
CXTXIQGPWDLUBE-UHFFFAOYSA-N NC(C)C1=C(C=CC=C1)NCCO Chemical compound NC(C)C1=C(C=CC=C1)NCCO CXTXIQGPWDLUBE-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000001143 conditioned Effects 0.000 description 1
SQSPRWMERUQXNE-UHFFFAOYSA-N diaminomethylideneurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable Effects 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000003165 hydrotropic Effects 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000717 retained Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1