CH393585A - Verfahren zur Herstellung von wasserunlöslichen, metallhaltigen Azofarbstoffen - Google Patents

Verfahren zur Herstellung von wasserunlöslichen, metallhaltigen Azofarbstoffen

Info

Publication number: CH393585A
Authority: CH; Switzerland
Prior art keywords: sep; oxynaphthoylamino; gray; green; blue
Prior art date: 1958-07-18

Application number

CH1160761A

Other languages

German (de)

English (en)

Inventor

Ulrich Dr Dreyer

Werner Dr Kirst

Original Assignee

Hoechst 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.)

1958-07-18

Filing date

1959-07-15

Publication date

1965-06-15

1958-07-18 Priority claimed from DEF26196A external-priority patent/DE1086832B/de

1959-05-15 Priority claimed from DEF28442A external-priority patent/DE1132271B/de

1959-07-15 Application filed by Hoechst Ag filed Critical Hoechst Ag

1965-06-15 Publication of CH393585A publication Critical patent/CH393585A/de

Links

229910052751 metal Inorganic materials 0.000 title claims description 9
239000002184 metal Substances 0.000 title claims description 9
239000000987 azo dye Substances 0.000 title claims description 7
238000000034 method Methods 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 12
-1 aryl amides Chemical group 0.000 claims description 11
229910052759 nickel Inorganic materials 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 5
239000000975 dye Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
235000011054 acetic acid Nutrition 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
150000001989 diazonium salts Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000000758 substrate Substances 0.000 claims description 2
150000003460 sulfonic acids Chemical class 0.000 claims description 2
239000004753 textile Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000005749 Copper compound Substances 0.000 claims 1
125000004442 acylamino group Chemical group 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
150000001880 copper compounds Chemical class 0.000 claims 1
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
150000003459 sulfonic acid esters Chemical class 0.000 claims 1
244000172533 Viola sororia Species 0.000 description 57
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 44
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 32
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
240000007817 Olea europaea Species 0.000 description 25
OHBQPCCCRFSCAX-UHFFFAOYSA-N Hydroquinone dimethyl ether Natural products COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 22
QMXZSRVFIWACJH-UHFFFAOYSA-N 1-chloro-2,5-dimethoxybenzene Natural products COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 18
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 18
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 17
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 15
OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 11
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 10
OACCRGFGCIQFNR-UHFFFAOYSA-N 1-chloro-2,4-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C(OC)=C1 OACCRGFGCIQFNR-UHFFFAOYSA-N 0.000 description 10
ZMZVVVASCILFJL-UHFFFAOYSA-N 2-chloro-4-methoxy-1-methylbenzene Chemical compound COC1=CC=C(C)C(Cl)=C1 ZMZVVVASCILFJL-UHFFFAOYSA-N 0.000 description 10
YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 description 8
NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 8
150000004699 copper complex Chemical class 0.000 description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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 5
238000001465 metallisation Methods 0.000 description 5
YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical class C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000004700 cobalt complex Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
SDGMUBWPXBSKCT-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Cl)C(C)=C1 SDGMUBWPXBSKCT-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000003857 carboxamides Chemical class 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000003973 paint Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
YUKILTJWFRTXGB-UHFFFAOYSA-N 1-chloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1 YUKILTJWFRTXGB-UHFFFAOYSA-N 0.000 description 2
OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 description 2
FWOPJXVQGMZKEP-UHFFFAOYSA-N 3-methyl-2h-indazole Chemical compound C1=CC=CC2=C(C)NN=C21 FWOPJXVQGMZKEP-UHFFFAOYSA-N 0.000 description 2
DDJYYJIWIYUTRV-UHFFFAOYSA-N 3-sulfonylindazole Chemical compound C1=CC=C2C(=S(=O)=O)N=NC2=C1 DDJYYJIWIYUTRV-UHFFFAOYSA-N 0.000 description 2
HNOSKPXFWPKCPP-UHFFFAOYSA-N 6-methoxy-1h-indazol-3-amine Chemical compound COC1=CC=C2C(N)=NNC2=C1 HNOSKPXFWPKCPP-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
235000021388 linseed oil Nutrition 0.000 description 2
239000000944 linseed oil Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012209 synthetic fiber Substances 0.000 description 2
229920002994 synthetic fiber Polymers 0.000 description 2
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000012463 white pigment Substances 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
PEFVPWQEMVFNPP-UHFFFAOYSA-N 1-(3-amino-1h-indazol-6-yl)ethanone Chemical compound CC(=O)C1=CC=C2C(N)=NNC2=C1 PEFVPWQEMVFNPP-UHFFFAOYSA-N 0.000 description 1
MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
KEJFADGISRFLFO-UHFFFAOYSA-N 1H-indazol-6-amine Chemical compound NC1=CC=C2C=NNC2=C1 KEJFADGISRFLFO-UHFFFAOYSA-N 0.000 description 1
OTFFCAGPSWJBDK-UHFFFAOYSA-N 1h-indazol-7-amine Chemical compound NC1=CC=CC2=C1NN=C2 OTFFCAGPSWJBDK-UHFFFAOYSA-N 0.000 description 1
VCMCQLGNGHMKFB-UHFFFAOYSA-N 3-amino-1H-indazole-6-carboxamide Chemical compound NC1=NNC2=CC(=CC=C12)C(=O)N VCMCQLGNGHMKFB-UHFFFAOYSA-N 0.000 description 1
HHHLAUONASKYKT-UHFFFAOYSA-N 3-amino-N,N-diethyl-1H-indazole-5-sulfonamide Chemical compound C(C)N(S(=O)(=O)C=1C=C2C(=NNC2=CC=1)N)CC HHHLAUONASKYKT-UHFFFAOYSA-N 0.000 description 1
HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
QPLXQNVPEHUPTR-UHFFFAOYSA-N 4-chloro-1H-indazol-3-amine Chemical compound C1=CC(Cl)=C2C(N)=NNC2=C1 QPLXQNVPEHUPTR-UHFFFAOYSA-N 0.000 description 1
ZXZTZRVCWTWKCH-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=C(C(F)(F)F)C=C2C(N)=NNC2=C1 ZXZTZRVCWTWKCH-UHFFFAOYSA-N 0.000 description 1
QCSQTZOPSNFNNX-UHFFFAOYSA-N 5-chloro-1h-indazol-3-amine Chemical compound C1=C(Cl)C=C2C(N)=NNC2=C1 QCSQTZOPSNFNNX-UHFFFAOYSA-N 0.000 description 1
BZMRACNPNBEQJQ-UHFFFAOYSA-N 5-methoxy-1h-indazol-3-amine Chemical compound COC1=CC=C2NN=C(N)C2=C1 BZMRACNPNBEQJQ-UHFFFAOYSA-N 0.000 description 1
WZIPYVDSECTYQW-UHFFFAOYSA-N 5-methylsulfonyl-1h-indazol-3-amine Chemical compound CS(=O)(=O)C1=CC=C2NN=C(N)C2=C1 WZIPYVDSECTYQW-UHFFFAOYSA-N 0.000 description 1
SWZRTDLKPZAFDT-UHFFFAOYSA-N 5-nitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NNC2=C1 SWZRTDLKPZAFDT-UHFFFAOYSA-N 0.000 description 1
ZMPFPQFXUYYHSJ-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-indazol-3-amine Chemical compound FC(F)(F)C1=CC=C2C(N)=NNC2=C1 ZMPFPQFXUYYHSJ-UHFFFAOYSA-N 0.000 description 1
BPTYMRSBTUERSW-UHFFFAOYSA-N 6-chloro-1h-indazol-3-amine Chemical compound ClC1=CC=C2C(N)=NNC2=C1 BPTYMRSBTUERSW-UHFFFAOYSA-N 0.000 description 1
VUZQHUVRBPILAX-UHFFFAOYSA-N 6-chloro-1h-indazole Chemical compound ClC1=CC=C2C=NNC2=C1 VUZQHUVRBPILAX-UHFFFAOYSA-N 0.000 description 1
XKOTZNANCGZGPN-UHFFFAOYSA-N 6-chloro-5-methoxy-1h-indazol-3-amine Chemical compound C1=C(Cl)C(OC)=CC2=C1NN=C2N XKOTZNANCGZGPN-UHFFFAOYSA-N 0.000 description 1
FENSIVQLZNKXRC-UHFFFAOYSA-N 6-ethoxy-1h-indazol-3-amine Chemical compound CCOC1=CC=C2C(N)=NNC2=C1 FENSIVQLZNKXRC-UHFFFAOYSA-N 0.000 description 1
HWDZUCCQXHQYHS-UHFFFAOYSA-N 6-methyl-1h-indazol-3-amine Chemical compound CC1=CC=C2C(N)=NNC2=C1 HWDZUCCQXHQYHS-UHFFFAOYSA-N 0.000 description 1
GUQMGUUEHIUELS-UHFFFAOYSA-N 6-nitro-1h-indazol-3-amine Chemical compound [O-][N+](=O)C1=CC=C2C(N)=NNC2=C1 GUQMGUUEHIUELS-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
NHMFXERCWBPTCW-UHFFFAOYSA-N N-(3-amino-1H-indazol-5-yl)benzamide Chemical compound NC1=NNC2=CC=C(C=C12)NC(C1=CC=CC=C1)=O NHMFXERCWBPTCW-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229910052770 Uranium Inorganic materials 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
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
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 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
239000001044 red dye Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- 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
- C09B45/00—Complex metal compounds of azo dyes
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/18—Monoazo compounds containing copper
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1160761A 1958-07-18 1959-07-15 Verfahren zur Herstellung von wasserunlöslichen, metallhaltigen Azofarbstoffen CH393585A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF26196A DE1086832B (de)	1958-07-18	1958-07-18	Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen
DEF28442A DE1132271B (de)	1959-05-15	1959-05-15	Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen

Publications (1)

Publication Number	Publication Date
CH393585A true CH393585A (de)	1965-06-15

Family

ID=25974148

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1160761A CH393585A (de)	1958-07-18	1959-07-15	Verfahren zur Herstellung von wasserunlöslichen, metallhaltigen Azofarbstoffen
CH7581059A CH363421A (de)	1958-07-18	1959-10-01	Verfahren zur Herstellung von wasserunlöslichen metallhaltigen Azofarbstoffen auf der Faser

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH7581059A CH363421A (de)	1958-07-18	1959-10-01	Verfahren zur Herstellung von wasserunlöslichen metallhaltigen Azofarbstoffen auf der Faser

Country Status (2)

Country	Link
BE (1)	BE580836A (fr)
CH (2)	CH393585A (fr)

1959
- 1959-07-15 CH CH1160761A patent/CH393585A/de unknown
- 1959-07-18 BE BE580836A patent/BE580836A/fr unknown
- 1959-10-01 CH CH7581059A patent/CH363421A/de unknown

Also Published As

Publication number	Publication date
CH363421A (de)	1962-03-30
BE580836A (fr)	1960-01-18

Publication	Publication Date	Title
DE842981C (de)	1952-07-03	Verfahren zur Herstellung metallhaltiger, sulfonsaeuregruppenfreier Azofarbstoffe
DE2533958A1 (de)	1977-02-17	Wasserunloesliche azo-azomethin- verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel sowie aminoarylenazo-verbindungen, ihre herstellung und verwendung zur herstellung von azo-azomethin-verbindungen
DE2901121A1 (de)	1979-11-08	Azopigmente
DE2236250A1 (de)	1973-02-08	Neue diazo-pigmente, deren herstellung und verwendung
CH393585A (de)	1965-06-15	Verfahren zur Herstellung von wasserunlöslichen, metallhaltigen Azofarbstoffen
DE2203094C3 (de)	1974-12-19	Monoazopigmente, Verfahren zu deren Herstellung und Verwendung
DE949309C (de)	1956-09-20	Verfahren zur Herstellung von gefaerbtem Polyvinylharzpulver
DE592088C (de)	1934-02-01	Verfahren zur Herstellung von metallhaltigen Azofarbstoffen
AT223722B (de)	1962-10-10	Verfahren zur Herstellung von neuen metallhaltigen Azofarbstoffen
DE594326C (de)	1934-03-15	Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen
DE618748C (de)	1935-09-14	Verfahren zur Herstellung von carboxylgruppenfreien metallhaltigen Azofarbstoffen
AT227853B (de)	1963-06-10	Verfahren zur Herstellung von neuen metallhaltigen, wasserunlöslichen Azofarbstoffen
DE959042C (de)	1957-02-28	Verfahren zur Herstellung metallhaltiger Azofarbstoffe
DE723435C (de)	1942-08-06	Verfahren zur Herstellung von komplex gebundenes Chrom enthaltenden Monoazofarbstoffen
DE866704C (de)	1953-02-12	Verfahren zur Herstellung von Polyazofarbstoffen der Stilbenreihe
DE1086832B (de)	1960-08-11	Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen
DE842976C (de)	1952-07-03	Verfahren zur Herstellung von Monoazofarbstoffen
CH625821A5 (en)	1981-10-15	Process for preparing asymmetrical 1:2 chromium complexes containing an azo compound and an azomethine compound
DE739908C (de)	1943-10-15	Verfahren zur Herstellung von Trisazofarbstoffen
AT234243B (de)	1964-06-25	Verfahren zur Herstellung neuer chrom- bzw. kobalthaltiger Azofarbstoffe
DE1150768B (de)	1963-06-27	Verfahren zur Herstellung von metallhaltigen, wasserunloeslichen Azofarbstoffen
DE1644356C3 (de)	1976-10-07	1 zu 2-Chrom- oder Kobalt-Mischkomplexfarbstoffe, ihre Herstellung und Verwendung zum Färben, Klotzen oder Bedrucken von natürlichen und synthetischen Polyamiden oder Leder
DE1151612B (de)	1963-07-18	Verfahren zur Herstellung basischer Farbstoffe
DE886946C (de)	1953-08-20	Verfahren zur Herstellung indigoider Kuepenfarbstoffe
AT239934B (de)	1965-05-10	Verfahren zur Herstellung von neuen unsymmetrischen Chrommischkomplex-Azofarbstoffen