BE571742A

BE571742A -

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Publication number: BE571742A
Authority: BE; Belgium
Prior art keywords: chloro; parts; water; hydroxypropyl; insoluble
Prior art date

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English (en)

French (fr)

Publication of BE571742A publication Critical patent/BE571742A/fr

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239000000975 dye Substances 0.000 claims description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
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 14
MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical group NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 claims description 13
-1 3-bromo-2-hydroxypropyl group Chemical group 0.000 claims description 12
125000002843 carboxylic acid group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
239000000987 azo dye Substances 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000004753 textile Substances 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 4
238000004043 dyeing Methods 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
QXLOEXSDZJNHKK-UHFFFAOYSA-N 1-(2-aminophenyl)-3-chloropropan-2-ol Chemical compound ClCC(CC1=C(C=CC=C1)N)O QXLOEXSDZJNHKK-UHFFFAOYSA-N 0.000 claims 1
QCEKQQUIWSQBLP-UHFFFAOYSA-N NC1=C(CC(CBr)O)C=CC=C1 Chemical compound NC1=C(CC(CBr)O)C=CC=C1 QCEKQQUIWSQBLP-UHFFFAOYSA-N 0.000 claims 1
239000004744 fabric Substances 0.000 description 19
239000004677 Nylon Substances 0.000 description 14
229920000297 Rayon Polymers 0.000 description 14
239000000203 mixture Substances 0.000 description 14
229920001778 nylon Polymers 0.000 description 14
239000000243 solution Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
239000000835 fiber Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000012736 aqueous medium Substances 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
XRMROANJXRJLPD-UHFFFAOYSA-N 1-anilino-3-chloropropan-2-ol Chemical compound ClCC(O)CNC1=CC=CC=C1 XRMROANJXRJLPD-UHFFFAOYSA-N 0.000 description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
241000974482 Aricia saepiolus Species 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
150000001989 diazonium salts Chemical class 0.000 description 4
238000006193 diazotization reaction Methods 0.000 description 4
VDXZPXIEEVOGLV-UHFFFAOYSA-N hydron;3-methylaniline;chloride Chemical compound [Cl-].CC1=CC=CC([NH3+])=C1 VDXZPXIEEVOGLV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
NDWBXTNRCBNGAK-UHFFFAOYSA-N 4-methyl-5-nitro-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1[N+]([O-])=O NDWBXTNRCBNGAK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
241000208818 Helianthus Species 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920006297 regenerated protein fiber Polymers 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229920002994 synthetic fiber Polymers 0.000 description 2
238000005406 washing Methods 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
MWCADZVQNIHFGT-UHFFFAOYSA-N 1-anilinopropan-2-ol Chemical compound CC(O)CNC1=CC=CC=C1 MWCADZVQNIHFGT-UHFFFAOYSA-N 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
YKBXWAQJCNUBTG-UHFFFAOYSA-N 2-amino-5-nitro-1,3-thiazole-4-carbonitrile Chemical compound NC1=NC(C#N)=C([N+]([O-])=O)S1 YKBXWAQJCNUBTG-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
AMKUKQWAGRSEGF-UHFFFAOYSA-N 3-methylaniline;hydrobromide Chemical compound Br.CC1=CC=CC(N)=C1 AMKUKQWAGRSEGF-UHFFFAOYSA-N 0.000 description 1
LHVMMXVJJLIPJB-UHFFFAOYSA-N 4-(2-chlorophenyl)-5-nitro-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O LHVMMXVJJLIPJB-UHFFFAOYSA-N 0.000 description 1
NDKYVRQAANNPQD-UHFFFAOYSA-N 4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=CSC=2)=C1 NDKYVRQAANNPQD-UHFFFAOYSA-N 0.000 description 1
ZFEZXBSASUIGPK-UHFFFAOYSA-N 4-ethyl-5-nitro-1,3-thiazol-2-amine Chemical compound CCC=1N=C(N)SC=1[N+]([O-])=O ZFEZXBSASUIGPK-UHFFFAOYSA-N 0.000 description 1
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
APOCIEHULBMMKH-UHFFFAOYSA-N 5-nitro-4-(trifluoromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC(C(F)(F)F)=C([N+]([O-])=O)S1 APOCIEHULBMMKH-UHFFFAOYSA-N 0.000 description 1
SRSNXASTSVBKPJ-UHFFFAOYSA-N 5-nitro-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1[N+]([O-])=O SRSNXASTSVBKPJ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PHZHZWGAYZEXHJ-UHFFFAOYSA-N CC(CN(C1=CC=CC=C1)Cl)O Chemical compound CC(CN(C1=CC=CC=C1)Cl)O PHZHZWGAYZEXHJ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
229950003476 aminothiazole Drugs 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000027326 copulation Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1