BE516998A

BE516998A -

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Publication number: BE516998A
Authority: BE; Belgium
Prior art keywords: amino; sep; benzene; parts; hydroxy
Prior art date

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English (en)

French (fr)

Publication of BE516998A publication Critical patent/BE516998A/fr

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239000000975 dye Substances 0.000 claims description 180
-1 amino azo compound Chemical class 0.000 claims description 97
239000002253 acid Substances 0.000 claims description 95
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 78
238000005859 coupling reaction Methods 0.000 claims description 72
230000001808 coupling Effects 0.000 claims description 66
238000010168 coupling process Methods 0.000 claims description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 53
150000001875 compounds Chemical class 0.000 claims description 48
239000010949 copper Substances 0.000 claims description 46
229910052802 copper Inorganic materials 0.000 claims description 46
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 45
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 42
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 40
230000000875 corresponding Effects 0.000 claims description 35
150000003254 radicals Chemical class 0.000 claims description 32
125000003277 amino group Chemical group 0.000 claims description 30
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
150000001412 amines Chemical class 0.000 claims description 26
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 25
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 17
239000000987 azo dye Substances 0.000 claims description 16
239000000835 fiber Substances 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
150000001555 benzenes Chemical class 0.000 claims description 14
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 13
150000004985 diamines Chemical class 0.000 claims description 12
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000004043 dyeing Methods 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
238000007127 saponification reaction Methods 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
230000027326 copulation Effects 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 4
238000005755 formation reaction Methods 0.000 claims description 4
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000004696 coordination complex Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004432 carbon atoms Chemical group C* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
YZCKVEUIGOORGS-UHFFFAOYSA-N hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
150000002790 naphthalenes Chemical class 0.000 claims description 2
125000004427 diamine group Chemical group 0.000 claims 2
150000005204 hydroxybenzenes Chemical class 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 264
239000000243 solution Substances 0.000 description 67
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 60
229920000742 Cotton Polymers 0.000 description 48
229920003043 Cellulose fiber Polymers 0.000 description 41
239000004627 regenerated cellulose Substances 0.000 description 41
229940076134 Benzene Drugs 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
239000001187 sodium carbonate Substances 0.000 description 30
229910000029 sodium carbonate Inorganic materials 0.000 description 30
VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 29
SXBOEBVXYQFVJM-UHFFFAOYSA-L copper;2-azanidylpentanedioate Chemical compound [Cu+2].[O-]C(=O)C([NH-])CCC([O-])=O SXBOEBVXYQFVJM-UHFFFAOYSA-L 0.000 description 27
ZLYYJUJDFKGVKB-OWOJBTEDSA-N (E)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 26
239000000843 powder Substances 0.000 description 26
238000007747 plating Methods 0.000 description 25
RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 21
238000007792 addition Methods 0.000 description 21
MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
229940075566 Naphthalene Drugs 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 16
238000009833 condensation Methods 0.000 description 16
230000005494 condensation Effects 0.000 description 16
150000001879 copper Chemical class 0.000 description 14
239000000047 product Substances 0.000 description 14
QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 13
235000011121 sodium hydroxide Nutrition 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 11
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 11
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000005406 washing Methods 0.000 description 11
239000001530 fumaric acid Substances 0.000 description 10
235000011087 fumaric acid Nutrition 0.000 description 10
MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 9
QIQCZROILFZKAT-UHFFFAOYSA-N Tetracarbon dioxide Chemical group O=C=C=C=C=O QIQCZROILFZKAT-UHFFFAOYSA-N 0.000 description 9
ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 8
QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 8
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
239000001632 sodium acetate Substances 0.000 description 8
235000017281 sodium acetate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical group OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 7
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 7
LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
238000004040 coloring Methods 0.000 description 7
QUIIUKFPLUUSGQ-UHFFFAOYSA-N 2-amino-6-chlorophenol Chemical compound NC1=CC=CC(Cl)=C1O QUIIUKFPLUUSGQ-UHFFFAOYSA-N 0.000 description 6
SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 6
WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 6
238000005185 salting out Methods 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 5
PEMGGJDINLGTON-UHFFFAOYSA-N N-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 5
XRMLOZSMCSUBTL-UHFFFAOYSA-N phenylazanide Chemical compound [NH-]C1=CC=CC=C1 XRMLOZSMCSUBTL-UHFFFAOYSA-N 0.000 description 5
GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 4
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 4
VNKYTQGIUYNRMY-UHFFFAOYSA-N Methoxypropane Chemical group CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating Effects 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
239000000470 constituent Substances 0.000 description 4
PBTUTICKCLVZAB-ZJVSAGCXSA-H copper;tetrasodium;7-[[4-(2-hydroxyethylamino)-6-[[(6E)-6-[(2-oxido-5-sulfonatophenyl)hydrazinylidene]-5-oxo-7-sulfonatonaphthalen-2-yl]amino]-1,3,5-triazin-2-yl]amino]-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]-4-oxidonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].[O-]S(=O)(=O)C1=CC(OC)=CC=C1N=NC(C(=CC1=C2)S([O-])(=O)=O)=C([O-])C1=CC=C2NC1=NC(NCCO)=NC(NC=2C=C3C=C(C(=N/NC=4C(=CC=C(C=4)S([O-])(=O)=O)[O-])/C(=O)C3=CC=2)S([O-])(=O)=O)=N1 PBTUTICKCLVZAB-ZJVSAGCXSA-H 0.000 description 4
238000006193 diazotization reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000001465 metallisation Methods 0.000 description 4
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 description 4
239000002994 raw material Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
235000021286 stilbenes Nutrition 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
230000002194 synthesizing Effects 0.000 description 4
230000001131 transforming Effects 0.000 description 4
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 3
ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 3
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 3
QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 3
RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 3
HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
NCBZRJODKRCREW-UHFFFAOYSA-N M-Anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 3
241001024304 Mino Species 0.000 description 3
ITXUJUMBUWYFCW-UHFFFAOYSA-N OC1=C2C=CC(=CC2=CC(=C1)S(=O)(=O)O)[N-]C1=CC2=CC(=CC(=C2C=C1)O)S(=O)(=O)O Chemical compound OC1=C2C=CC(=CC2=CC(=C1)S(=O)(=O)O)[N-]C1=CC2=CC(=CC(=C2C=C1)O)S(=O)(=O)O ITXUJUMBUWYFCW-UHFFFAOYSA-N 0.000 description 3
HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
239000003518 caustics Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910000365 copper sulfate Inorganic materials 0.000 description 3
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 2
RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-Amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 2
ZYTFGZVRDCIESJ-UHFFFAOYSA-N 3-acetamido-2-acetylbenzoic acid Chemical compound CC(=O)NC1=CC=CC(C(O)=O)=C1C(C)=O ZYTFGZVRDCIESJ-UHFFFAOYSA-N 0.000 description 2
FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 2
YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 description 2
DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FHIVAFMUCKRCQO-UHFFFAOYSA-N Diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
KBOPZPXVLCULAV-UHFFFAOYSA-N Mesalazine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 2
NCKPQOUTAMSEAO-UHFFFAOYSA-N Nc1ccc(cc1)N=Nc1ccc(O)cc1 Chemical compound Nc1ccc(cc1)N=Nc1ccc(O)cc1 NCKPQOUTAMSEAO-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000003086 colorant Substances 0.000 description 2
QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
FYVOPPWTSVAJIF-UHFFFAOYSA-N methyl(phenyl)azanide Chemical compound C[N-]C1=CC=CC=C1 FYVOPPWTSVAJIF-UHFFFAOYSA-N 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
230000002035 prolonged Effects 0.000 description 2
229910000679 solder Inorganic materials 0.000 description 2
YNFHJFSDSDEMFG-UHFFFAOYSA-N (4-methylphenyl)azanide Chemical compound CC1=CC=C([NH-])C=C1 YNFHJFSDSDEMFG-UHFFFAOYSA-N 0.000 description 1
FSQQTNAZHBEJLS-OWOJBTEDSA-N (E)-4-amino-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C\C(O)=O FSQQTNAZHBEJLS-OWOJBTEDSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (N-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
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