SE468392B - Azopyridinoner, saett att framstaella dessa och anvaendning av dessa till faergning eller tryckning av ett underlag - Google Patents

Azopyridinoner, saett att framstaella dessa och anvaendning av dessa till faergning eller tryckning av ett underlag

Info

Publication number: SE468392B
Authority: SE; Sweden
Prior art keywords: groups; alkyl; independently; group; hydrogen
Prior art date: 1985-03-30

Application number

SE8601401A

Other languages

English (en)

Swedish (sv)

Other versions

SE8601401L (sv

SE8601401D0 (sv

Inventor

H A Moser

R Wald

Original Assignee

Sandoz 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.)

1985-03-30

Filing date

1986-03-26

Publication date

1993-01-11

1986-03-26 Application filed by Sandoz Ag filed Critical Sandoz Ag

1986-03-26 Publication of SE8601401D0 publication Critical patent/SE8601401D0/xx

1986-10-01 Publication of SE8601401L publication Critical patent/SE8601401L/

1993-01-11 Publication of SE468392B publication Critical patent/SE468392B/sv

Links

239000000758 substrate Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 84
229910052739 hydrogen Inorganic materials 0.000 claims description 64
239000001257 hydrogen Substances 0.000 claims description 63
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 38
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
-1 methoxy, hydroxy, ethoxy Chemical group 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
239000011651 chromium Substances 0.000 claims description 16
239000010941 cobalt Substances 0.000 claims description 15
229910017052 cobalt Inorganic materials 0.000 claims description 15
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 15
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 13
150000001450 anions Chemical class 0.000 claims description 13
150000004696 coordination complex Chemical class 0.000 claims description 13
239000010949 copper Substances 0.000 claims description 13
238000004043 dyeing Methods 0.000 claims description 13
229910052742 iron Inorganic materials 0.000 claims description 13
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
229910052804 chromium Inorganic materials 0.000 claims description 12
229910052802 copper Inorganic materials 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 8
229910052759 nickel Inorganic materials 0.000 claims description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229920001131 Pulp (paper) Polymers 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
239000002023 wood Substances 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 2
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
LNQUWGZAZIOHMM-UHFFFAOYSA-N ethoxy-hydroxy-methoxy-lambda3-chlorane Chemical compound CCOCl(O)OC LNQUWGZAZIOHMM-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 claims 1
101000981103 Mus musculus Carcinoembryonic antigen-related cell adhesion molecule 1 Proteins 0.000 claims 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 claims 1
241000209140 Triticum Species 0.000 claims 1
235000021307 Triticum Nutrition 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
239000004927 clay Chemical group 0.000 claims 1
101150058626 gcH3 gene Proteins 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
239000000975 dye Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000123 paper Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000002351 wastewater Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
239000001913 cellulose Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000010985 leather Substances 0.000 description 5
238000001465 metallisation Methods 0.000 description 5
239000004753 textile Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
239000000835 fiber Substances 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
150000003242 quaternary ammonium salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
229940037003 alum Drugs 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
235000010338 boric acid Nutrition 0.000 description 2
229960002645 boric acid Drugs 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000000227 grinding Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011572 manganese Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000010186 staining Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000001043 yellow dye Substances 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical group CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical group N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
244000198134 Agave sisalana Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
235000018185 Betula X alpestris Nutrition 0.000 description 1
235000018212 Betula X uliginosa Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
240000000491 Corchorus aestuans Species 0.000 description 1
235000011777 Corchorus aestuans Nutrition 0.000 description 1
235000010862 Corchorus capsularis Nutrition 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
101001067188 Mus musculus Plexin-A1 Proteins 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
238000004026 adhesive bonding Methods 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
235000013334 alcoholic beverage Nutrition 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000981 basic dye Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000004699 copper complex Chemical class 0.000 description 1
JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
230000001335 demethylating effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000011487 hemp Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
229940078494 nickel acetate Drugs 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
238000005498 polishing Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000013055 pulp slurry Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011122 softwood Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010902 straw Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
- C09B44/08—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing heterocyclic rings
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
- C09B35/031—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound containing a six membered ring with one nitrogen atom as the only ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Paper (AREA)

SE8601401A 1985-03-30 1986-03-26 Azopyridinoner, saett att framstaella dessa och anvaendning av dessa till faergning eller tryckning av ett underlag SE468392B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3511733		1985-03-30

Publications (3)

Publication Number	Publication Date
SE8601401D0 SE8601401D0 (sv)	1986-03-26
SE8601401L SE8601401L (sv)	1986-10-01
SE468392B true SE468392B (sv)	1993-01-11

Family

ID=6266888

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8601401A SE468392B (sv)	1985-03-30	1986-03-26	Azopyridinoner, saett att framstaella dessa och anvaendning av dessa till faergning eller tryckning av ett underlag

Country Status (6)

Country	Link
JP (1)	JPH0662869B2 (de)
CH (1)	CH667464A5 (de)
FR (1)	FR2579606B1 (de)
GB (1)	GB2173210B (de)
IT (1)	IT1203759B (de)
SE (1)	SE468392B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH672496A5 (de) *	1986-05-14	1989-11-30	Sandoz Ag
DE3801945A1 (de) *	1988-01-23	1989-07-27	Basf Ag	Aufzeichnungsfluessigkeit fuer das ink-jet-verfahren
DE3815481A1 (de) *	1988-05-06	1989-11-16	Sandoz Ag	Sulfonsaeuregruppenfreie basische verbindung
FR2637289B1 (fr) *	1988-10-05	1992-11-06	Sandoz Sa	Composes azoiques de la serie de la pyridone, leur preparation et leur utilisation comme colorants
DE69108206T2 (de) *	1990-07-24	1995-11-09	Sunearth Co Ltd	Gerät zum einpressen von flüssigkeit zur bodenverbesserung.
DE4034060A1 (de) *	1990-10-26	1992-04-30	Basf Ag	Biskationische azofarbstoffe
DE19500203A1 (de) *	1994-01-14	1995-07-20	Sandoz Ag	Kationisch verbrückte Tetrakisazofarbstoffe mit unterschiedlichen Kupplern, ihre Herstellung und Verwendung
CH689424A5 (de) *	1994-05-06	1999-04-15	Clariant Finance Bvi Ltd	Faserreaktive Disazofarbstoffe.
GB2303634B (en) *	1995-07-21	1997-12-10	Clariant Finance Bvi Ltd	Basic azo compounds,their production and use
GB2372750B (en) *	2001-01-18	2004-09-08	Avecia Ltd	Hexa co-ordinated metal complexes of monoazo dyes for use in inks suitable for ink jet printing
FR2864781B1 (fr) *	2004-01-07	2006-02-17	Oreal	Composition tinctoriale comprenant au moins un colorant direct de la famille azo-pyridinio-pyridone et au moins un colorant de synthese different, procede de coloration des fibres keratiniques
CN101495578B (zh) *	2006-07-28	2013-06-12	克莱里安特财务(Bvi)有限公司	碱性双偶氮化合物
EP2078737A1 (de)	2008-01-11	2009-07-15	Clariant International Ltd.	Basische Monoazo-Verbindungen
EP2098573A3 (de)	2008-01-17	2009-10-07	Clariant International Ltd.	Basische Monoazo-Verbindungen
EP2103656A3 (de)	2008-01-24	2009-10-28	Clariant International Ltd.	Basische Monoazo-Verbindungen
EP2085428A1 (de)	2008-01-24	2009-08-05	Clariant International Ltd.	Basische Bisazo-Verbindungen
EP2085429A1 (de)	2008-01-25	2009-08-05	Clariant International Ltd.	Basische Bisazo-Verbindungen
TWI588214B (zh) *	2008-07-02	2017-06-21	克瑞特財力（Ｂｖｉ）有限公司	酸性染料之用途
EP2258683A1 (de) *	2009-05-14	2010-12-08	Clariant International Ltd.	Bisazoverbindungen
EP2258685B1 (de) *	2009-05-14	2013-10-23	Clariant Finance (BV) Limited	Bisazoverbindungen
JP5652823B2 (ja) *	2011-01-25	2015-01-14	株式会社日本触媒	アゾ化合物
WO2019189209A1 (ja) *	2018-03-27	2019-10-03	保土谷化学工業株式会社	錯塩化合物、染料組成物、陽極酸化アルミニウム用着色剤および着色方法、ならびに該化合物の製造方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH552661A (de) *	1968-11-12	1974-08-15	Ciba Geigy Ag	Verfahren zur herstellung neuer azofarbstoffe.
FI66893C (fi)	1975-06-30	1984-12-10	Sandoz Ag	Saosom faergaemnen anvaendbara biskatjoniska azofoereningar forfarande foer deras framstaellning och deras anvaendning
CH627201A5 (de) *	1977-03-14	1981-12-31	Sandoz Ag
CH647797A5 (en) *	1980-05-08	1985-02-15	Sandoz Ag	Organic dyes and preparation and use thereof
CH650011A5 (de) *	1981-06-26	1985-06-28	Ciba Geigy Ag	Triazinverbindungen.

1986
- 1986-03-24 CH CH1164/86A patent/CH667464A5/de not_active IP Right Cessation
- 1986-03-26 SE SE8601401A patent/SE468392B/sv not_active IP Right Cessation
- 1986-03-27 GB GB8607702A patent/GB2173210B/en not_active Expired
- 1986-03-27 FR FR8604666A patent/FR2579606B1/fr not_active Expired
- 1986-03-28 IT IT47835/86A patent/IT1203759B/it active
- 1986-03-28 JP JP61068859A patent/JPH0662869B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS61231056A (ja)	1986-10-15
JPH0662869B2 (ja)	1994-08-17
SE8601401L (sv)	1986-10-01
FR2579606B1 (fr)	1989-08-18
SE8601401D0 (sv)	1986-03-26
CH667464A5 (de)	1988-10-14
GB2173210A (en)	1986-10-08
IT8647835A0 (it)	1986-03-28
IT1203759B (it)	1989-02-23
GB2173210B (en)	1989-08-16
FR2579606A1 (fr)	1986-10-03
GB8607702D0 (en)	1986-04-30

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Publication	Publication Date	Title
SE445836B (sv)	1986-07-21	Basiska resp katjonaktiva, sulfonsyragrupphaltiga monoazo- eller diazoforeningar samt deras anvendning
JPS61231056A (ja)	1986-10-15	スルホン酸基を含まない塩基性化合物
DE3440777C2 (de)	1998-09-03	Neue sulfonsäuregruppenhaltige, basische Azoverbindungen, deren Herstellung und Verwendung als Farbstoffe
SE468391B (sv)	1993-01-11	Azopyridinoner, saett att framstaella dessa och anvaending av dessa som substrat vid faergning
US5352334A (en)	1994-10-04	The use of metal-free sulfo group free basic disazo compounds containing two identical 6-hydroxypyrid-2-one coupling component radicals for producing colored paper
CH663417A5 (de)	1987-12-15	Basische verbindungen, deren herstellung und verwendung.
JP3902672B2 (ja)	2007-04-11	スルホン酸基を含む塩基性ジスアゾ化合物
JPS6143388B2 (de)	1986-09-27
EP1360242B1 (de)	2006-11-08	Azofarbstoffe
CH653697A5 (de)	1986-01-15	Polykationische azoverbindung, ihre herstellung und verwendung.
US6302923B1 (en)	2001-10-16	Triphendioxazine compounds
JPH083044B2 (ja)	1996-01-17	塩基性アゾ化合物
GB2081734A (en)	1982-02-24	Improvements in or relating to organic compounds
DE1241014B (de)	1967-05-24	Verfahren zur Herstellung von Tetrazapolymethinfarbstoffen
US6933371B2 (en)	2005-08-23	Bisazo dyestuffs based on hydroxynaphthalene carboxylic acid
DE2022624B2 (de)	1973-09-13	Basischer Disazofarbstoff, Ver fahren zu dessen Herstellung und dessen Verwendung
DE3117127A1 (de)	1982-02-04	Organische verbindungen, deren herstellung und verwendung
EP1863885B1 (de)	2014-12-24	Konzentrierte farbstofflösung
US5077396A (en)	1991-12-31	Azo compounds containing two 6-hydroxypyrid-2-one coupling component radicals the nitrogen atoms of which are linked by a biscationic radical
SE463874B (sv)	1991-02-04	Katjoniska ftalocyaninfoereningar, anvaendbara som faergaemnen
JP2004532917A (ja)	2004-10-28	塩基性モノ及びビスアゾ化合物
CH656880A5 (de)	1986-07-31	Basische verbindungen, ihre herstellung und verwendung.
DE3340483C2 (de)	1991-11-07
US20070251030A1 (en)	2007-11-01	Concentrated Dye Solution
SE500469C2 (sv)	1994-07-04	Oxazinföreningar