BE489377A

BE489377A -

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Publication number: BE489377A
Authority: BE; Belgium
Prior art keywords: parts; acid; derivatives; dye; dyes
Prior art date

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English (en)

French (fr)

Publication of BE489377A publication Critical patent/BE489377A/fr

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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 66
239000000975 dye Substances 0.000 claims description 64
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 37
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 33
239000000987 azo dye Substances 0.000 claims description 32
150000004820 halides Chemical class 0.000 claims description 23
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 20
VRHSKNLJTFSZHK-UHFFFAOYSA-N 2-chloro-2-sulfoacetic acid Chemical compound OC(=O)C(Cl)S(O)(=O)=O VRHSKNLJTFSZHK-UHFFFAOYSA-N 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
230000002378 acidificating effect Effects 0.000 claims description 14
230000007935 neutral effect Effects 0.000 claims description 10
239000007787 solid Substances 0.000 claims description 10
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 8
LUKWLIGSXPGYPJ-UHFFFAOYSA-N 2-bromo-2-sulfoacetic acid Chemical compound OC(=O)C(Br)S(O)(=O)=O LUKWLIGSXPGYPJ-UHFFFAOYSA-N 0.000 claims description 8
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
238000004043 dyeing Methods 0.000 claims description 8
210000002268 wool Anatomy 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
239000000835 fiber Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
230000003381 solubilizing effect Effects 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000003086 colorant Substances 0.000 claims description 4
238000004090 dissolution Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
238000006193 diazotization reaction Methods 0.000 claims description 3
239000004753 textile Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 5
125000004122 cyclic group Chemical group 0.000 claims 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
230000006866 deterioration Effects 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 61
239000000203 mixture Substances 0.000 description 49
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 41
239000011541 reaction mixture Substances 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 30
239000011780 sodium chloride Substances 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
239000007795 chemical reaction product Substances 0.000 description 28
238000003756 stirring Methods 0.000 description 27
239000000047 product Substances 0.000 description 23
239000000049 pigment Substances 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
-1 cyclic radical Chemical group 0.000 description 18
230000010933 acylation Effects 0.000 description 15
238000005917 acylation reaction Methods 0.000 description 15
239000000843 powder Substances 0.000 description 13
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
239000002002 slurry Substances 0.000 description 10
238000011282 treatment Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
239000004744 fabric Substances 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000007127 saponification reaction Methods 0.000 description 7
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000010908 decantation Methods 0.000 description 6
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
239000003513 alkali Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
241000416162 Astragalus gummifer Species 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
229920001615 Tragacanth Polymers 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229940106681 chloroacetic acid Drugs 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
239000000196 tragacanth Substances 0.000 description 4
229940116362 tragacanth Drugs 0.000 description 4
235000010487 tragacanth Nutrition 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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
239000003292 glue Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000000344 soap Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
JAOZKJMVYIWLKU-UHFFFAOYSA-N sodium 7-hydroxy-8-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)O)N=NC3=C(C=CC4=CC(=CC(=C43)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] JAOZKJMVYIWLKU-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 3
239000003760 tallow Substances 0.000 description 3
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
229950006389 thiodiglycol Drugs 0.000 description 3
229910006069 SO3H Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000001172 regenerating effect Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007921 spray Substances 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZCZNOGFTNRXIDI-UHFFFAOYSA-N 1-amino-2H-naphthalene-1-carbaldehyde Chemical compound NC1(CC=CC2=CC=CC=C12)C=O ZCZNOGFTNRXIDI-UHFFFAOYSA-N 0.000 description 1
OIPRCKCTAOCWJG-UHFFFAOYSA-N 2,3-diethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1OCC OIPRCKCTAOCWJG-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
VXWYQEYFYNAZOD-UHFFFAOYSA-N 2-[3-[(4,4-difluoropiperidin-1-yl)methyl]-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group FC1(F)CCN(CC2=NN(CC(=O)N3CCC4=C(C3)N=NN4)C=C2C2=CN=C(NC3CC4=C(C3)C=CC=C4)N=C2)CC1 VXWYQEYFYNAZOD-UHFFFAOYSA-N 0.000 description 1
YNKDSVFVVIOKIL-UHFFFAOYSA-N 2-chloro-2-sulfopropanoic acid Chemical compound OC(=O)C(Cl)(C)S(O)(=O)=O YNKDSVFVVIOKIL-UHFFFAOYSA-N 0.000 description 1
VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
240000009038 Viola odorata Species 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
150000001555 benzenes Chemical class 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
229940092714 benzenesulfonic acid Drugs 0.000 description 1
238000009835 boiling Methods 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
KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
235000015220 hamburgers Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
229950006098 orthocaine Drugs 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229940070891 pyridium Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
239000012261 resinous substance Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229960005369 scarlet red Drugs 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1