BE408553A

BE408553A -

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Publication number: BE408553A
Authority: BE; Belgium
Prior art keywords: sep; amino; dyes; red; parts
Prior art date

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English (en)

French (fr)

Publication of BE408553A publication Critical patent/BE408553A/fr

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239000000975 dye Substances 0.000 claims description 56
230000001808 coupling Effects 0.000 claims description 16
238000010168 coupling process Methods 0.000 claims description 16
238000005859 coupling reaction Methods 0.000 claims description 16
238000004043 dyeing Methods 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
230000001034 aminogenic Effects 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
230000002152 alkylating Effects 0.000 claims 1
239000000463 material Substances 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 205
239000002253 acid Substances 0.000 description 19
-1 methylcarboxy ester Chemical class 0.000 description 16
239000000243 solution Substances 0.000 description 16
229920000297 Rayon Polymers 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000006193 diazotization reaction Methods 0.000 description 10
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000027326 copulation Effects 0.000 description 9
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 9
239000000843 powder Substances 0.000 description 9
210000002268 Wool Anatomy 0.000 description 8
239000000047 product Substances 0.000 description 8
239000006185 dispersion Substances 0.000 description 7
229910052500 inorganic mineral Inorganic materials 0.000 description 6
239000011707 mineral Substances 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000010979 ruby Substances 0.000 description 6
229910001750 ruby Inorganic materials 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
FYXJXUMICYGRKV-UHFFFAOYSA-N 2-[(2-amino-5-nitrophenyl)methylsulfonylmethyl]-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CS(=O)(=O)CC1=CC([N+]([O-])=O)=CC=C1N FYXJXUMICYGRKV-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
239000000203 mixture Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
230000002378 acidificating Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000875 corresponding Effects 0.000 description 4
230000001264 neutralization Effects 0.000 description 4
239000002964 rayon Substances 0.000 description 4
239000000020 Nitrocellulose Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000001045 blue dye Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
229920001220 nitrocellulos Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 description 3
MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical class CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 2
241000974482 Aricia saepiolus Species 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N Methylsulfonylmethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
HSZCJVZRHXPCIA-UHFFFAOYSA-N N-benzyl-N-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 2
GEYRZILBLWWDNB-UHFFFAOYSA-N NC1=C(C=C(C=C1)[N+](=O)[O-])CCS(=O)(=O)CCC1=C(C=CC(=C1)[N+](=O)[O-])N Chemical compound NC1=C(C=C(C=C1)[N+](=O)[O-])CCS(=O)(=O)CCC1=C(C=CC(=C1)[N+](=O)[O-])N GEYRZILBLWWDNB-UHFFFAOYSA-N 0.000 description 2
WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
RCTGMCJBQGBLKT-PAMTUDGESA-N Scarlet Red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
229940095076 benzaldehyde Drugs 0.000 description 2
239000003086 colorant Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229960005369 scarlet red Drugs 0.000 description 2
239000008149 soap solution Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
125000000547 substituted alkyl group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
150000003457 sulfones Chemical group 0.000 description 2
UBSRDVFWZYVGNE-UHFFFAOYSA-N (1-acetyloxy-2-anilinoethyl) acetate Chemical compound CC(=O)OC(OC(C)=O)CNC1=CC=CC=C1 UBSRDVFWZYVGNE-UHFFFAOYSA-N 0.000 description 1
SOAAGHDAWFEEPP-JZJYNLBNSA-N (4Z)-4-[(2,4-dimethylphenyl)hydrazinylidene]-3-oxonaphthalene-2,7-disulfonic acid Chemical compound CC1=CC(C)=CC=C1N\N=C/1C2=CC=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C\1=O SOAAGHDAWFEEPP-JZJYNLBNSA-N 0.000 description 1
PYODWRMWWIOCST-UHFFFAOYSA-N (N-ethylanilino) acetate Chemical compound CC(=O)ON(CC)C1=CC=CC=C1 PYODWRMWWIOCST-UHFFFAOYSA-N 0.000 description 1
VJRDSTPLJRAJPL-UHFFFAOYSA-N 1-(5,6-diaminonaphthalen-1-yl)ethanone Chemical compound NC1=CC=C2C(C(=O)C)=CC=CC2=C1N VJRDSTPLJRAJPL-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-Xylidine Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
OHDRFZNFKNAOGA-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,3-diamine Chemical compound COC1=C(N)C=C(C)C=C1N OHDRFZNFKNAOGA-UHFFFAOYSA-N 0.000 description 1
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
241000208195 Buxaceae Species 0.000 description 1
DVHTZYZBKUFUOA-UHFFFAOYSA-N N-(2-ethoxyethyl)-N-ethylaniline Chemical compound CCOCCN(CC)C1=CC=CC=C1 DVHTZYZBKUFUOA-UHFFFAOYSA-N 0.000 description 1
JLYJJRHBGXOWSQ-UHFFFAOYSA-N N-(2-ethoxyethyl)aniline Chemical compound CCOCCNC1=CC=CC=C1 JLYJJRHBGXOWSQ-UHFFFAOYSA-N 0.000 description 1
IBRLRCIVUSLMRB-UHFFFAOYSA-N N-(2-methoxyethyl)-N-methylaniline Chemical compound COCCN(C)C1=CC=CC=C1 IBRLRCIVUSLMRB-UHFFFAOYSA-N 0.000 description 1
XTTMNDFFWSZHCZ-UHFFFAOYSA-N N-(2-methoxyethyl)aniline Chemical compound COCCNC1=CC=CC=C1 XTTMNDFFWSZHCZ-UHFFFAOYSA-N 0.000 description 1
PEMGGJDINLGTON-UHFFFAOYSA-N N-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N N-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
UBCKKDUHVZNHMG-UHFFFAOYSA-N N-ethoxy-N-ethylaniline Chemical compound CCON(CC)C1=CC=CC=C1 UBCKKDUHVZNHMG-UHFFFAOYSA-N 0.000 description 1
NDDVNVNAPACOLF-UHFFFAOYSA-N N-ethyl-N-(2-methoxyethyl)aniline Chemical compound COCCN(CC)C1=CC=CC=C1 NDDVNVNAPACOLF-UHFFFAOYSA-N 0.000 description 1
KDFFXYVOTKKBDI-UHFFFAOYSA-N N-ethylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCC)=CC=CC2=C1 KDFFXYVOTKKBDI-UHFFFAOYSA-N 0.000 description 1
NUBFYWSWKHIFJK-UHFFFAOYSA-N NC1=C(C=C(C=C1)NC(C)=O)C(C1=CC=CC=C1)S(=O)(=O)C(C1=CC=CC=C1)C1=C(C=CC(=C1)NC(C)=O)N Chemical compound NC1=C(C=C(C=C1)NC(C)=O)C(C1=CC=CC=C1)S(=O)(=O)C(C1=CC=CC=C1)C1=C(C=CC(=C1)NC(C)=O)N NUBFYWSWKHIFJK-UHFFFAOYSA-N 0.000 description 1
ZJCDZIDXIHRGCI-UHFFFAOYSA-N NC1=C(C=C(C=C1)NC(C)=O)CCS(=O)(=O)CCC1=C(C=CC(=C1)NC(C)=O)N Chemical compound NC1=C(C=C(C=C1)NC(C)=O)CCS(=O)(=O)CCC1=C(C=CC(=C1)NC(C)=O)N ZJCDZIDXIHRGCI-UHFFFAOYSA-N 0.000 description 1
YEURGKLTFGBTAK-UHFFFAOYSA-N NC1=C(C=C(C=C1)NC(C)=O)CS(=O)(=O)CC1=C(C=CC(=C1)NC(C)=O)N Chemical compound NC1=C(C=C(C=C1)NC(C)=O)CS(=O)(=O)CC1=C(C=CC(=C1)NC(C)=O)N YEURGKLTFGBTAK-UHFFFAOYSA-N 0.000 description 1
NEJFSDBMRHUIQV-UHFFFAOYSA-N NC1=C(C=C(C=C1)[N+](=O)[O-])C(C1=CC=CC=C1)S(=O)(=O)C(C1=CC=CC=C1)C1=C(C=CC(=C1)[N+](=O)[O-])N Chemical compound NC1=C(C=C(C=C1)[N+](=O)[O-])C(C1=CC=CC=C1)S(=O)(=O)C(C1=CC=CC=C1)C1=C(C=CC(=C1)[N+](=O)[O-])N NEJFSDBMRHUIQV-UHFFFAOYSA-N 0.000 description 1
SSDVVOYFXKTULZ-UHFFFAOYSA-N NC1=C(C=C(C=C1)[N+](=O)[O-])OCCS(=O)(=O)CCOC1=C(C=CC(=C1)[N+](=O)[O-])N Chemical compound NC1=C(C=C(C=C1)[N+](=O)[O-])OCCS(=O)(=O)CCOC1=C(C=CC(=C1)[N+](=O)[O-])N SSDVVOYFXKTULZ-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
MWFMCZWMLLCBJH-UHFFFAOYSA-N O-naphthalen-1-ylhydroxylamine Chemical compound C1=CC=C2C(ON)=CC=CC2=C1 MWFMCZWMLLCBJH-UHFFFAOYSA-N 0.000 description 1
240000000358 Viola adunca Species 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000240 adjuvant Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
JNIGYQOBELCEIZ-MAKDUZDQSA-L barium(2+);5-chloro-4-methyl-2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O JNIGYQOBELCEIZ-MAKDUZDQSA-L 0.000 description 1
SLXZZXJPFRYIKN-UHFFFAOYSA-N benzyl-(2-ethylphenyl)sulfamic acid Chemical compound CCC1=CC=CC=C1N(S(O)(=O)=O)CC1=CC=CC=C1 SLXZZXJPFRYIKN-UHFFFAOYSA-N 0.000 description 1
AWHNUHMUCGRKRA-UHFFFAOYSA-N benzylsulfonylmethylbenzene Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC1=CC=CC=C1 AWHNUHMUCGRKRA-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 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
239000011630 iodine Substances 0.000 description 1
WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000001047 purple dye Substances 0.000 description 1
239000001044 red dye Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1