BE514008A - - Google Patents

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Publication number: BE514008A
Authority: BE; Belgium
Prior art keywords: amino; parts; naphthalene; stilbyl; acid
Prior art date

Application number

Other languages

Publication of BE514008A publication Critical patent/BE514008A/fr

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239000002253 acid Substances 0.000 claims description 55
150000001875 compounds Chemical class 0.000 claims description 38
-1 1,2,3-triazole compound Chemical class 0.000 claims description 18
239000000975 dye Substances 0.000 claims description 17
239000000987 azo dye Substances 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 14
230000001808 coupling Effects 0.000 claims description 13
238000010168 coupling process Methods 0.000 claims description 13
238000005859 coupling reaction Methods 0.000 claims description 13
230000001034 aminogenic Effects 0.000 claims description 10
230000000875 corresponding Effects 0.000 claims description 10
QBHYFEWQILVXEN-UHFFFAOYSA-N 5-amino-2-(2-phenylethenyl)benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=CC=C1 QBHYFEWQILVXEN-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
150000001555 benzenes Chemical class 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000000177 1,2,3-triazoles Chemical class 0.000 claims 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
238000004061 bleaching Methods 0.000 claims 1
125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 43
239000000047 product Substances 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 22
239000000843 powder Substances 0.000 description 20
159000000000 sodium salts Chemical class 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000011780 sodium chloride Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 16
239000000835 fiber Substances 0.000 description 14
239000000344 soap Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
239000007844 bleaching agent Substances 0.000 description 12
230000003647 oxidation Effects 0.000 description 12
238000007254 oxidation reaction Methods 0.000 description 12
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 11
238000007792 addition Methods 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
238000005406 washing Methods 0.000 description 9
SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 8
239000005708 Sodium hypochlorite Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
150000008049 diazo compounds Chemical class 0.000 description 8
239000004744 fabric Substances 0.000 description 8
230000003287 optical Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
229920003043 Cellulose fiber Polymers 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
QWENRTYMTSOGBR-UHFFFAOYSA-N 1,2,3-triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 5
QGSPHUSCHLYIBI-UHFFFAOYSA-N 2-[2-(2-phenylethenyl)phenyl]benzo[e]benzotriazole Chemical class C=1C=CC=C(N2N=C3C4=CC=CC=C4C=CC3=N2)C=1C=CC1=CC=CC=C1 QGSPHUSCHLYIBI-UHFFFAOYSA-N 0.000 description 5
JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
238000006193 diazotization reaction Methods 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
239000004753 textile Substances 0.000 description 4
YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 3
210000002268 Wool Anatomy 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229910000365 copper sulfate Inorganic materials 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000004435 hydrogen atoms Chemical group [H]* 0.000 description 3
150000003839 salts Chemical class 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
GHBWBMDGBCKAQU-OWOJBTEDSA-N 5-amino-2-[(E)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-OWOJBTEDSA-N 0.000 description 2
JCOOFZSBYJRINH-UHFFFAOYSA-N 5-amino-2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O JCOOFZSBYJRINH-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 2
239000004677 Nylon Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
150000007860 aryl ester derivatives Chemical class 0.000 description 2
230000027326 copulation Effects 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
229920001778 nylon Polymers 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000271 synthetic detergent Substances 0.000 description 2
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
APWZAIZNWQFZBK-UHFFFAOYSA-N 1-ethoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=CC2=C1 APWZAIZNWQFZBK-UHFFFAOYSA-N 0.000 description 1
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
XGQWHHCZIMXNHG-UHFFFAOYSA-N 4-aminonaphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 XGQWHHCZIMXNHG-UHFFFAOYSA-N 0.000 description 1
NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 1
ZDTXQHVBLWYPHS-UHFFFAOYSA-N 4-nitrotoluene-2-sulfonic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O ZDTXQHVBLWYPHS-UHFFFAOYSA-N 0.000 description 1
HQAXAXDMDWIERX-UHFFFAOYSA-N 5-amino-2-[2-(4-chloro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(Cl)C=C1S(O)(=O)=O HQAXAXDMDWIERX-UHFFFAOYSA-N 0.000 description 1
KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
MIANIURAXXBWRH-UHFFFAOYSA-N BrC=1C=C(C(C=CC=2C(=CC(=CC2)N)S(=O)(=O)O)=CC1)S(=O)(=O)O Chemical compound BrC=1C=C(C(C=CC=2C(=CC(=CC2)N)S(=O)(=O)O)=CC1)S(=O)(=O)O MIANIURAXXBWRH-UHFFFAOYSA-N 0.000 description 1
BWFPGXWASODCHM-UHFFFAOYSA-N Copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
QMMHJHBLDTZONQ-UHFFFAOYSA-N NC=1C=C(C(=CC1)C=CC1=C(C=CC=C1)C(C)C)S(=O)(=O)O Chemical compound NC=1C=C(C(=CC1)C=CC1=C(C=CC=C1)C(C)C)S(=O)(=O)O QMMHJHBLDTZONQ-UHFFFAOYSA-N 0.000 description 1
BZJLIIBBRXMRPN-UHFFFAOYSA-N NC=1C=C(C(=CC1)C=CC1=C(C=CC=C1)Cl)S(=O)(=O)O Chemical compound NC=1C=C(C(=CC1)C=CC1=C(C=CC=C1)Cl)S(=O)(=O)O BZJLIIBBRXMRPN-UHFFFAOYSA-N 0.000 description 1
JIYUPIOSDBXUDK-UHFFFAOYSA-N NC=1C=C(C(=CC1)C=CC1=CC=C(C=C1)C)S(=O)(=O)O Chemical compound NC=1C=C(C(=CC1)C=CC1=CC=C(C=C1)C)S(=O)(=O)O JIYUPIOSDBXUDK-UHFFFAOYSA-N 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000000240 adjuvant Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
238000006149 azo coupling reaction Methods 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000002349 favourable Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/22—Luminous paints

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

BE514008D BE514008A (da)

Publications (1)

Publication Number	Publication Date
BE514008A true BE514008A (da)

Family

ID=151950

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE514008D BE514008A (da)

Country Status (1)

Country	Link
BE (1)	BE514008A (da)

0
- BE BE514008D patent/BE514008A/fr unknown

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