BE571743A

BE571743A -

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Publication number: BE571743A
Authority: BE; Belgium
Prior art keywords: sep; water; parts; formula; insoluble
Prior art date

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English (en)

French (fr)

Publication of BE571743A publication Critical patent/BE571743A/fr

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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 92
239000004753 textile Substances 0.000 claims description 67
239000000463 material Substances 0.000 claims description 58
239000000987 azo dye Substances 0.000 claims description 47
239000004952 Polyamide Substances 0.000 claims description 45
229920002647 polyamide Polymers 0.000 claims description 45
239000011528 polyamide (building material) Substances 0.000 claims description 45
-1 heterocyclic amine Chemical class 0.000 claims description 41
230000001808 coupling Effects 0.000 claims description 29
238000010168 coupling process Methods 0.000 claims description 29
238000005859 coupling reaction Methods 0.000 claims description 29
125000003118 aryl group Chemical group 0.000 claims description 23
150000001412 amines Chemical class 0.000 claims description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
230000000875 corresponding Effects 0.000 claims description 10
150000008049 diazo compounds Chemical class 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
150000004982 aromatic amines Chemical class 0.000 claims description 9
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
238000004043 dyeing Methods 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
229910001873 dinitrogen Inorganic materials 0.000 claims 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 187
239000000975 dye Substances 0.000 description 66
150000001408 amides Chemical class 0.000 description 65
239000000243 solution Substances 0.000 description 60
239000000203 mixture Substances 0.000 description 53
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
239000007864 aqueous solution Substances 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
238000001914 filtration Methods 0.000 description 17
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
239000000835 fiber Substances 0.000 description 15
239000001187 sodium carbonate Substances 0.000 description 14
229910000029 sodium carbonate Inorganic materials 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
235000010288 sodium nitrite Nutrition 0.000 description 11
239000000047 product Substances 0.000 description 10
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
239000001632 sodium acetate Substances 0.000 description 10
235000017281 sodium acetate Nutrition 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229920002301 Cellulose acetate Polymers 0.000 description 6
IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
239000007859 condensation product Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000007787 solid Substances 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
210000002268 Wool Anatomy 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
230000027326 copulation Effects 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
229920002239 polyacrylonitrile Polymers 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000005406 washing Methods 0.000 description 5
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
239000004677 Nylon Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
238000009835 boiling Methods 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
229920001778 nylon Polymers 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
238000007639 printing Methods 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 3
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000007792 addition Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000986 disperse dye Substances 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atoms Chemical group N* 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229960001663 sulfanilamide Drugs 0.000 description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 3
FNUKLSVGSFFSLI-UHFFFAOYSA-N 2-(3-aminophenyl)ethanol Chemical compound NC1=CC=CC(CCO)=C1 FNUKLSVGSFFSLI-UHFFFAOYSA-N 0.000 description 2
QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 2
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 2
TUOWYJFPLMIKCX-UHFFFAOYSA-N 2-ethoxynaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(OCC)=CC=C21 TUOWYJFPLMIKCX-UHFFFAOYSA-N 0.000 description 2
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 2
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
239000004604 Blowing Agent Substances 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229920002284 Cellulose triacetate Polymers 0.000 description 2
240000006669 Helianthus annuus Species 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
125000003047 N-acetyl group Chemical group 0.000 description 2
NQRLPDFELNCFHW-UHFFFAOYSA-N Nitroacetanilide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 NQRLPDFELNCFHW-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RMVRSNDYEFQCLF-UHFFFAOYSA-N Thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
GETTZEONDQJALK-UHFFFAOYSA-N Trifluorotoluene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
KNWNWWDKWKYUBB-UHFFFAOYSA-N ethyl 5-oxo-1,4-dihydropyrazole-3-carboxylate Chemical class CCOC(=O)C1=NNC(=O)C1 KNWNWWDKWKYUBB-UHFFFAOYSA-N 0.000 description 2
239000004744 fabric Substances 0.000 description 2
238000009963 fulling Methods 0.000 description 2
238000000227 grinding Methods 0.000 description 2
125000006456 halo alkyl cycloalkyl group Chemical group 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
150000004780 naphthols Chemical class 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000001681 protective Effects 0.000 description 2
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
REXYIKXSNOVYSZ-UHFFFAOYSA-N 1-(2-aminophenoxy)propan-2-one Chemical compound CC(=O)COC1=CC=CC=C1N REXYIKXSNOVYSZ-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
HLJIIZLYKMQFSS-UHFFFAOYSA-N 2-(naphthalen-1-ylamino)ethanol Chemical compound C1=CC=C2C(NCCO)=CC=CC2=C1 HLJIIZLYKMQFSS-UHFFFAOYSA-N 0.000 description 1
MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-Chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-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
DRGIDRZFKRLQTE-UHFFFAOYSA-N 2-chloroaniline;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1Cl DRGIDRZFKRLQTE-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
KXEMVGQZZLRLBE-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1S(Cl)(=O)=O KXEMVGQZZLRLBE-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
YQUBWBSLSNIUBN-UHFFFAOYSA-N 3-chloropiperidine Chemical compound ClC1CCCNC1 YQUBWBSLSNIUBN-UHFFFAOYSA-N 0.000 description 1
MNUOZFHYBCRUOD-UHFFFAOYSA-N 3-hydroxyphthalic acid Chemical compound OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
ZEUUPKVZFKBXPW-UHFFFAOYSA-N 4-amino-2-[4,6-diamino-3-[3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.NC1CC(O)C(CN)OC1OC1C(O)C(OC2C(C(N)C(O)C(CO)O2)O)C(N)CC1N ZEUUPKVZFKBXPW-UHFFFAOYSA-N 0.000 description 1
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 1
ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N Acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N Dichlorine monoxide Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
229940117389 Dichlorobenzene Drugs 0.000 description 1
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
229920000161 Locust bean gum Polymers 0.000 description 1
VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 1
FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 description 1
ZVCZLEUNRRXCAW-UHFFFAOYSA-N N-benzoylsulfamoyl chloride Chemical compound ClS(=O)(=O)NC(=O)C1=CC=CC=C1 ZVCZLEUNRRXCAW-UHFFFAOYSA-N 0.000 description 1
210000004940 Nucleus Anatomy 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
QWVGKYWNOKOFNN-UHFFFAOYSA-N O-Cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
ZQVHRADDSTYWRB-UHFFFAOYSA-N OCCC1=CC=C(C=C1)N=NC1=C(C=CC=C1)N Chemical compound OCCC1=CC=C(C=C1)N=NC1=C(C=CC=C1)N ZQVHRADDSTYWRB-UHFFFAOYSA-N 0.000 description 1
TUFRAFXUSYVQKQ-UHFFFAOYSA-N OCCC=1C=C(NCCC#N)C=CC1 Chemical compound OCCC=1C=C(NCCC#N)C=CC1 TUFRAFXUSYVQKQ-UHFFFAOYSA-N 0.000 description 1
VNQABZCSYCTZMS-UHFFFAOYSA-N Orthocaine Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
229910006069 SO3H Inorganic materials 0.000 description 1
229940005550 Sodium alginate Drugs 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N Sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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229950006389 Thiodiglycol Drugs 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
230000000397 acetylating Effects 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
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125000004429 atoms Chemical group 0.000 description 1
LMIZORQOLSLQRY-UHFFFAOYSA-N benzene;naphthalene Chemical group C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 LMIZORQOLSLQRY-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
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VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
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230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000005712 crystallization Effects 0.000 description 1
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000002950 deficient Effects 0.000 description 1
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125000005594 diketone group Chemical group 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
VBQUDDWATQWCPP-UHFFFAOYSA-N ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=CC=C1 VBQUDDWATQWCPP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920000591 gum Polymers 0.000 description 1
125000005347 halocycloalkyl group Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
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238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
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MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
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230000001264 neutralization Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical class OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
229950006098 orthocaine Drugs 0.000 description 1
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
XRMLOZSMCSUBTL-UHFFFAOYSA-N phenylazanide Chemical compound [NH-]C1=CC=CC=C1 XRMLOZSMCSUBTL-UHFFFAOYSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
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MSXHSNHNTORCAW-UHFFFAOYSA-M sodium 3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].OC1OC(C([O-])=O)C(O)C(O)C1O MSXHSNHNTORCAW-UHFFFAOYSA-M 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
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239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
230000001131 transforming Effects 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N triclene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000011089 white board Substances 0.000 description 1