BE504783A

BE504783A -

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Publication number: BE504783A
Authority: BE; Belgium
Prior art keywords: parts; dyes; weight; dye; amino
Prior art date

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English (en)

French (fr)

Publication of BE504783A publication Critical patent/BE504783A/fr

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239000000975 dye Substances 0.000 claims description 113
230000000875 corresponding Effects 0.000 claims description 11
125000004429 atoms Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 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 5
150000004961 triphenylmethanes Chemical class 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004432 carbon atoms Chemical group C* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000003141 primary amines Chemical class 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 1
239000000835 fiber Substances 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 42
210000002268 Wool Anatomy 0.000 description 40
239000007859 condensation product Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 16
239000011780 sodium chloride Substances 0.000 description 16
-1 aliphatic radical Chemical class 0.000 description 15
GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 14
MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
239000001045 blue dye Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000000155 melt Substances 0.000 description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 7
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 7
229960001755 resorcinol Drugs 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000001044 red dye Substances 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000006277 sulfonation reaction Methods 0.000 description 6
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 6
239000000203 mixture Substances 0.000 description 5
239000003086 colorant Substances 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
GUAWMXYQZKVRCW-UHFFFAOYSA-N N,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 3
QCIFLGSATTWUQJ-UHFFFAOYSA-N N,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
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 3
238000004532 chromating Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
OIHZGFWAMWHYPA-UHFFFAOYSA-N xanthylium Chemical class C1=CC=CC2=CC3=CC=CC=C3[O+]=C21 OIHZGFWAMWHYPA-UHFFFAOYSA-N 0.000 description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-Xylidine Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
MWOUGPLLVVEUMM-UHFFFAOYSA-N N-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 2
VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
238000007792 addition Methods 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000005591 charge neutralization Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000000034 method Methods 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001226 reprecipitation Methods 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
FFDVTEHMPLVFMS-UHFFFAOYSA-N 2,3,5-trimethylaniline Chemical compound CC1=CC(C)=C(C)C(N)=C1 FFDVTEHMPLVFMS-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
LNBKJWCRFAZVLK-UHFFFAOYSA-N 3',6'-dichlorospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(Cl)C=C1OC1=CC(Cl)=CC=C21 LNBKJWCRFAZVLK-UHFFFAOYSA-N 0.000 description 1
DMVOXQPQNTYEKQ-UHFFFAOYSA-N 4-Aminobiphenyl Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-o-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-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
GXMFVMMXHKXSBI-UHFFFAOYSA-N 5-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC(Cl)=CC=C1C(F)(F)F GXMFVMMXHKXSBI-UHFFFAOYSA-N 0.000 description 1
229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
241000974482 Aricia saepiolus Species 0.000 description 1
AVYWZNHMIWLDAL-UHFFFAOYSA-N C(C)OC1=CC(=C(C(=O)OC(C2=C(C=C(C=C2)OCC)S(=O)(=O)O)=O)C=C1)S(=O)(=O)O Chemical compound C(C)OC1=CC(=C(C(=O)OC(C2=C(C=C(C=C2)OCC)S(=O)(=O)O)=O)C=C1)S(=O)(=O)O AVYWZNHMIWLDAL-UHFFFAOYSA-N 0.000 description 1
IGGIQNHBOAZPOF-UHFFFAOYSA-M C(C)OC1=CC(=C(C(=O)[O-])C=C1)S(=O)(=O)O.[K+] Chemical compound C(C)OC1=CC(=C(C(=O)[O-])C=C1)S(=O)(=O)O.[K+] IGGIQNHBOAZPOF-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
LXCAXUFXGZXECA-UHFFFAOYSA-N ClC1=CC(=C(C(=O)OC(C2=C(C=C(C=C2)Cl)S(=O)(=O)O)=O)C=C1)S(=O)(=O)O Chemical compound ClC1=CC(=C(C(=O)OC(C2=C(C=C(C=C2)Cl)S(=O)(=O)O)=O)C=C1)S(=O)(=O)O LXCAXUFXGZXECA-UHFFFAOYSA-N 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N Dichlorine monoxide Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
UUSGZWZUYJHBJS-UHFFFAOYSA-N N-butyl-3-methylaniline Chemical compound CCCCNC1=CC=CC(C)=C1 UUSGZWZUYJHBJS-UHFFFAOYSA-N 0.000 description 1
GUYMMHOQXYZMJQ-UHFFFAOYSA-N N-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
AASABFUMCBTXRL-UHFFFAOYSA-N N-ethyl-4-methylaniline Chemical compound CCNC1=CC=C(C)C=C1 AASABFUMCBTXRL-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N N-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
ZMCHBSMFKQYNKA-UHFFFAOYSA-N Orthanilic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-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
AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
JFRMYMMIJXLMBB-UHFFFAOYSA-N Xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
239000000980 acid dye Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
XEYCPDSRHJFTGU-UHFFFAOYSA-N ethanamine;toluene Chemical compound CCN.CC1=CC=CC=C1 XEYCPDSRHJFTGU-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
JMCGARBKIAJZLC-UHFFFAOYSA-M potassium;2-sulfobenzoate Chemical compound [K+].OC(=O)C1=CC=CC=C1S([O-])(=O)=O JMCGARBKIAJZLC-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ZTJNNZNTRJTRMP-UHFFFAOYSA-M sodium;2-amino-3,5-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC(C)=C(N)C(S([O-])(=O)=O)=C1 ZTJNNZNTRJTRMP-UHFFFAOYSA-M 0.000 description 1
RORBRNDIUBJZHS-UHFFFAOYSA-M sodium;3-amino-5-carboxy-4-hydroxybenzenesulfonate Chemical compound [Na+].NC1=CC(S([O-])(=O)=O)=CC(C(O)=O)=C1O RORBRNDIUBJZHS-UHFFFAOYSA-M 0.000 description 1
QSJBCWFEIGFVGB-UHFFFAOYSA-M sodium;4-(benzylamino)benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NCC1=CC=CC=C1 QSJBCWFEIGFVGB-UHFFFAOYSA-M 0.000 description 1
KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1