CA1112640A - Colorants reactifs - Google Patents

Colorants reactifs

Info

Publication number: CA1112640A
Authority: CA; Canada
Prior art keywords: alkyl; chloro; parts; formula; acid
Prior art date: 1978-04-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA325,980A

Other languages

English (en)

Inventor

Karl H. Schundehutte

Erich Klauke

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-04-22

Filing date

1979-04-20

Publication date

1981-11-17

1979-04-20 Application filed by Bayer AG filed Critical Bayer AG

1981-11-17 Application granted granted Critical

1981-11-17 Publication of CA1112640A publication Critical patent/CA1112640A/fr

Status Expired legal-status Critical Current

Links

239000000975 dye Substances 0.000 claims abstract description 57
-1 2-fluoro-5-chloro-6-methylpyrimidyl Chemical group 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 9
229910052804 chromium Inorganic materials 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000004696 coordination complex Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 11
150000001879 copper Chemical class 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
238000004043 dyeing Methods 0.000 abstract description 11
238000007639 printing Methods 0.000 abstract description 8
239000007800 oxidant agent Substances 0.000 abstract description 2
229920001184 polypeptide Polymers 0.000 abstract description 2
102000004196 processed proteins & peptides Human genes 0.000 abstract description 2
108090000765 processed proteins & peptides Proteins 0.000 abstract description 2
239000004627 regenerated cellulose Substances 0.000 abstract description 2
239000004753 textile Substances 0.000 abstract description 2
239000000243 solution Substances 0.000 description 51
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
239000002253 acid Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000005859 coupling reaction Methods 0.000 description 23
229920000742 Cotton Polymers 0.000 description 21
238000006482 condensation reaction Methods 0.000 description 21
150000001989 diazonium salts Chemical class 0.000 description 21
229910000029 sodium carbonate Inorganic materials 0.000 description 18
RMULVUFPLMJWOK-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Cl RMULVUFPLMJWOK-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000843 powder Substances 0.000 description 15
230000008878 coupling Effects 0.000 description 12
238000010168 coupling process Methods 0.000 description 12
239000000460 chlorine Substances 0.000 description 10
239000007859 condensation product Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000011651 chromium Substances 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000000725 suspension Substances 0.000 description 7
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
239000010949 copper Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
238000005185 salting out Methods 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 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 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 3
LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 3
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
244000172533 Viola sororia Species 0.000 description 3
YJVBLROMQZEFPA-UHFFFAOYSA-L acid red 26 Chemical compound [Na+].[Na+].CC1=CC(C)=CC=C1N=NC1=C(O)C(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=CC=C12 YJVBLROMQZEFPA-UHFFFAOYSA-L 0.000 description 3
238000007792 addition Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
150000003217 pyrazoles Chemical class 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
IUFVGONBAUNAOT-UHFFFAOYSA-N 2,4,5-trichloro-6-methylpyrimidine Chemical compound CC1=NC(Cl)=NC(Cl)=C1Cl IUFVGONBAUNAOT-UHFFFAOYSA-N 0.000 description 2
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
VCTKPJASNYUPMB-UHFFFAOYSA-N 2-(2-methyl-4-sulfophenyl)-3-oxo-1h-pyrazole-5-carboxylic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N1C(=O)C=C(C(O)=O)N1 VCTKPJASNYUPMB-UHFFFAOYSA-N 0.000 description 2
BHAKRVSCGILCEW-UHFFFAOYSA-N 2-chloro-4-methylpyrimidine Chemical compound CC1=CC=NC(Cl)=N1 BHAKRVSCGILCEW-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-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
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
JSBQMQFABBMNSV-UHFFFAOYSA-N 4-aminonaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 JSBQMQFABBMNSV-UHFFFAOYSA-N 0.000 description 2
LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 description 2
GBWNQBBVSVGAAL-UHFFFAOYSA-N 5-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1 GBWNQBBVSVGAAL-UHFFFAOYSA-N 0.000 description 2
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 2
CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
150000004056 anthraquinones Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000002301 combined effect Effects 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
239000003446 ligand Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-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
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
FFGBIGCLCYZUOK-UHFFFAOYSA-N 2,5-dichloro-4-fluoro-6-methylpyrimidine Chemical compound CC1=NC(Cl)=NC(F)=C1Cl FFGBIGCLCYZUOK-UHFFFAOYSA-N 0.000 description 1
VLNALQLLLGLFKJ-UHFFFAOYSA-N 2-amino-4-(pyrimidin-2-ylamino)benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(NC=2N=CC=CN=2)=C1 VLNALQLLLGLFKJ-UHFFFAOYSA-N 0.000 description 1
VWPUCKPXWQLXJC-UHFFFAOYSA-N 2-amino-5-(triazin-4-ylamino)benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1NC1=CC=NN=N1 VWPUCKPXWQLXJC-UHFFFAOYSA-N 0.000 description 1
GLABVBIYGGDCNO-UHFFFAOYSA-N 2-amino-5-methoxybenzene-1,4-disulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O GLABVBIYGGDCNO-UHFFFAOYSA-N 0.000 description 1
KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-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
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical compound FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 description 1
PBRJFOMELXZCDQ-UHFFFAOYSA-N 3-acetamido-8-hydroxynaphthalene-1,5-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C2=CC(NC(=O)C)=CC(S(O)(=O)=O)=C21 PBRJFOMELXZCDQ-UHFFFAOYSA-N 0.000 description 1
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 1
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 1
UCJKAZZVJXOLRP-UHFFFAOYSA-N 3-oxo-2-(4-sulfophenyl)-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 UCJKAZZVJXOLRP-UHFFFAOYSA-N 0.000 description 1
QUFFRITXLMVPMV-UHFFFAOYSA-N 4-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 QUFFRITXLMVPMV-UHFFFAOYSA-N 0.000 description 1
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000006149 azo coupling reaction Methods 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000004699 copper complex Chemical class 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
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 1
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
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 1
230000007935 neutral effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000009183 running Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
150000003918 triazines Chemical class 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CA325,980A 1978-04-22 1979-04-20 Colorants reactifs Expired CA1112640A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2817780A DE2817780C2 (de)	1978-04-22	1978-04-22	Reaktivfarbstoffe
DEP2817780.2		1978-05-22

Publications (1)

Publication Number	Publication Date
CA1112640A true CA1112640A (fr)	1981-11-17

Family

ID=6037795

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA325,980A Expired CA1112640A (fr)	1978-04-22	1979-04-20	Colorants reactifs

Country Status (11)

Country	Link
JP (1)	JPS54139931A (fr)
BE (1)	BE875726A (fr)
BR (1)	BR7902455A (fr)
CA (1)	CA1112640A (fr)
CH (1)	CH640557A5 (fr)
DE (1)	DE2817780C2 (fr)
ES (1)	ES479771A1 (fr)
FR (1)	FR2423520B1 (fr)
GB (1)	GB2019867B (fr)
IN (1)	IN151463B (fr)
IT (1)	IT1113356B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3010161A1 (de) *	1980-03-17	1981-09-24	Bayer Ag, 5090 Leverkusen	Farbstoffe, verfahren zu ihrer herstellung sowie ihre verwendung zum faerben hydroxylgruppen- oder stickstoffhaltiger materialien
DE3400412A1 (de) *	1984-01-07	1985-07-18	Bayer Ag, 5090 Leverkusen	Lagerstabile loesungen von reaktivfarbstoffen
DE3406232A1 (de) *	1984-02-21	1985-08-29	Bayer Ag, 5090 Leverkusen	Faserreaktive formazanfarbstoffe
DE4125754A1 (de) *	1991-08-03	1993-02-04	Bayer Ag	Fluorpyrimidin-reaktivfarbstoffe
EP0568876B1 (fr)	1992-05-04	1996-08-28	Bayer Ag	Colorants réactifs, leur préparation et leur utilisation
JP2005504871A (ja)	2001-10-08	2005-02-17	クラリアントインターナショナルリミティド	有機化合物
KR102714558B1 (ko) *	2022-03-25	2024-10-11	주식회사 아모텍	탄소섬유 강화용 열가소성 수지 조성물 및 그 제조방법, 열가소성 탄소섬유 복합체 및 그 제조방법

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1290915B (de) *	1966-02-17	1969-03-20	Bayer Ag	Verfahren zum Faerben und Bedrucken von Fasermaterialien aus aromatischen Polyestern und Celluloseacetaten
CH499604A (de) *	1966-04-22	1970-11-30	Ciba Geigy Ag	Verfahren zur Herstellung von faserreaktiven schwermetallhaltigen Formazanazofarbstoffen
CH501713A (de) *	1968-01-29	1971-01-15	Ciba Geigy Ag	Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen
DE1644171A1 (de) *	1966-09-10	1970-07-30	Bayer Ag	Reaktivfarbstoffe und Verfahren zu deren Herstellung
CH501712A (de) *	1968-01-12	1971-01-15	Bayer Ag	Verfahren zur Herstellung von Phthalocyanin-Reaktivfarbstoffen
CH515316A (de) *	1968-01-29	1971-11-15	Ciba Geigy Ag	Verfahren zur Herstellung von faserreaktiven schwermetallhaltigen Formazanfarbstoffen
DE1809388A1 (de) *	1968-11-16	1970-06-11	Bayer Ag	Azo-Reaktivfarbstoffe
DE2634497C2 (de) *	1976-07-31	1986-09-25	Bayer Ag, 5090 Leverkusen	Reaktivfarbstoffe und deren Verwendung

1978
- 1978-04-22 DE DE2817780A patent/DE2817780C2/de not_active Expired
1979
- 1979-03-21 IN IN187/DEL/79A patent/IN151463B/en unknown
- 1979-04-18 GB GB7913440A patent/GB2019867B/en not_active Expired
- 1979-04-19 IT IT22019/79A patent/IT1113356B/it active
- 1979-04-20 JP JP4808779A patent/JPS54139931A/ja active Granted
- 1979-04-20 BR BR7902455A patent/BR7902455A/pt unknown
- 1979-04-20 CA CA325,980A patent/CA1112640A/fr not_active Expired
- 1979-04-20 ES ES479771A patent/ES479771A1/es not_active Expired
- 1979-04-20 FR FR7910005A patent/FR2423520B1/fr not_active Expired
- 1979-04-20 BE BE0/194728A patent/BE875726A/fr not_active IP Right Cessation
- 1979-04-20 CH CH377179A patent/CH640557A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2423520B1 (fr)	1986-05-02
IT7922019A0 (it)	1979-04-19
GB2019867B (en)	1982-09-02
IN151463B (fr)	1983-04-23
IT1113356B (it)	1986-01-20
CH640557A5 (de)	1984-01-13
GB2019867A (en)	1979-11-07
ES479771A1 (es)	1980-10-01
JPS54139931A (en)	1979-10-30
DE2817780C2 (de)	1984-09-20
BE875726A (fr)	1979-10-22
FR2423520A1 (fr)	1979-11-16
DE2817780A1 (de)	1979-11-08
BR7902455A (pt)	1979-10-30
JPS614422B2 (fr)	1986-02-10

Legal Events

Date	Code	Title	Description
1998-11-17	MKEX	Expiry

Publication	Publication Date	Title
CA1087172A (fr)	1980-10-07	Modes de preparation et d'emploi de matieres colorantes
GB2034343A (en)	1980-06-04	Reactive dyestuffs
EP0365486A2 (fr)	1990-04-25	Colorants azo réactifs avec les fibres
EP0772652B1 (fr)	2001-08-29	Colorants monoazoiques reactifs
US5149790A (en)	1992-09-22	Bis chlorotriazine reactive dyes containing a benzylamine linking group
US6376656B1 (en)	2002-04-23	Reactive dyestuffs containing monohagenotriazine and vinylsulfone groups, their preparation and use
CA1112640A (fr)	1981-11-17	Colorants reactifs
EP0042108B1 (fr)	1984-04-04	Colorants réactifs, leur utilisation et fibres cellulosiques teintes avec ces colorants
JPS5930859A (ja)	1984-02-18	モノアゾ染料，その製法及び用途
GB2301834A (en)	1996-12-18	Fibre-reactive dyestuffs based on sulpho and sulphamoyl substituted phthalocyanines with a central aluminium atom
US3950128A (en)	1976-04-13	Disazo dyestuffs
US5059681A (en)	1991-10-22	Bis-azotriazinyl reactive dyes having an n-alkyl-phenylenediamine link
JP3446055B2 (ja)	2003-09-16	反応染料
US3936436A (en)	1976-02-03	Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals
JPS6136367A (ja)	1986-02-21	反応性染料
US5847111A (en)	1998-12-08	Aluminum phthalocyanine reactive dyes
US2951072A (en)	1960-08-30	Monoazo dyestuffs of the azo naphthalene series containing a monohalogeno-s-triazinenucleus
US4466920A (en)	1984-08-21	Disazo compounds having a further unsubstituted or substituted sulfophenyl diazo component radical and a 4-alkoxy- or arylsulfonyloxy benzene coupling component radical having an acylamina substituent
GB2085908A (en)	1982-05-06	Fibre-reactive azo dyestuffs
US4129736A (en)	1978-12-12	Triazinyl-antraquinone dyestuffs
JPH05222307A (ja)	1993-08-31	ピリドン染料
GB2039289A (en)	1980-08-06	Reactive dyestuffs
US4033944A (en)	1977-07-05	Fibre-reactive hydroxycycloalkenyl-halo triazinyl containing dyestuffs
EP0998530B1 (fr)	2002-02-27	Colorants azoiques reactifs a liaison diamine
US3803121A (en)	1974-04-09	Copper complex reactive monochloro-s-triazine azo dyestuff