CH534723A - Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen - Google Patents

Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen

Info

Publication number: CH534723A
Authority: CH; Switzerland
Prior art keywords: sep; ch2ch2cn; formula; blue; ch2ch3
Prior art date: 1970-07-02

Application number

CH1001770A

Other languages

German (de)

English (en)

Inventor

Alfred Dr Courtin

Wolfgang Dr Groebke

Eckart Dr Schleusener

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.)

1970-07-02

Filing date

1970-07-02

Publication date

1973-03-15

1970-07-02 Application filed by Sandoz Ag filed Critical Sandoz Ag

1970-07-02 Priority to CH1001770A priority Critical patent/CH534723A/de

1971-05-05 Priority to BE766771A priority patent/BE766771A/fr

1973-03-15 Publication of CH534723A publication Critical patent/CH534723A/de

Links

230000002209 hydrophobic effect Effects 0.000 title description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 7
230000008878 coupling Effects 0.000 claims abstract description 6
238000010168 coupling process Methods 0.000 claims abstract description 6
238000005859 coupling reaction Methods 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
-1 azo compound Chemical class 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 5
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
239000000987 azo dye Substances 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 8
238000004043 dyeing Methods 0.000 abstract description 4
229920000728 polyester Polymers 0.000 abstract description 4
239000003513 alkali Substances 0.000 abstract description 3
229920002284 Cellulose triacetate Polymers 0.000 abstract description 2
239000004952 Polyamide Substances 0.000 abstract description 2
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract description 2
229920002678 cellulose Polymers 0.000 abstract description 2
239000001913 cellulose Substances 0.000 abstract description 2
239000000986 disperse dye Substances 0.000 abstract description 2
229920002647 polyamide Polymers 0.000 abstract description 2
229920000098 polyolefin Polymers 0.000 abstract description 2
239000002904 solvent Substances 0.000 abstract description 2
VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 abstract 1
238000011282 treatment Methods 0.000 abstract 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 25
239000000975 dye Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
125000004442 acylamino group Chemical group 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000010949 copper Substances 0.000 description 2
QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000004753 textile Substances 0.000 description 2
ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
239000008096 xylene Substances 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
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 1
241000974482 Aricia saepiolus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910006074 SO2NH2 Inorganic materials 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 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
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
229930007927 cymene Natural products 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000013535 sea water Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/06—Preparation of azo dyes from other azo compounds by oxidation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1001770A 1970-07-02 1970-07-02 Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen CH534723A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH1001770A CH534723A (de)	1970-07-02	1970-07-02	Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen
BE766771A BE766771A (fr)	1970-07-02	1971-05-05	Procede de production de composes azoiques a radicaux sulfonyle

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1001770A CH534723A (de)	1970-07-02	1970-07-02	Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen

Publications (1)

Publication Number	Publication Date
CH534723A true CH534723A (de)	1973-03-15

Family

ID=4358452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1001770A CH534723A (de)	1970-07-02	1970-07-02	Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen

Country Status (2)

Country	Link
BE (1)	BE766771A (fr)
CH (1)	CH534723A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4320661A1 (de) *	1993-06-22	1995-01-05	Basf Ag	Phenylazo- oder Naphthylazobenzole mit Thioethergruppen

1970
- 1970-07-02 CH CH1001770A patent/CH534723A/de not_active IP Right Cessation
1971
- 1971-05-05 BE BE766771A patent/BE766771A/fr unknown

Also Published As

Publication number	Publication date
BE766771A (fr)	1971-10-01

Legal Events

Date	Code	Title	Description
1980-05-14	PL	Patent ceased

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CH689353A5 (de)	1999-03-15	Dispersionsfarbstoffe.
DE2115756A1 (de)	1971-11-11	Verbindungen mit färbenden, optisch aufhellenden und/oder U.V.-Licht absorbierenden Eigenschaften
CH534723A (de)	1973-03-15	Verfahren zur Herstellung von Sulfonylgruppen enthaltenden Azoverbindungen
CH527881A (de)	1972-09-15	Verfahren zur Herstellung von Azoverbindungen
CH637416A5 (de)	1983-07-29	Verfahren zur herstellung von neuen sulfonsaeuregruppenfreien nitroaminoazofarbstoffen.
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DE2222639A1 (de)	1972-11-16	In Wasser schwer loesliche Azoverbindungen,ihre Herstellung und Verwendung als Dispersionsfarbstoffe
CH638551A5 (de)	1983-09-30	Monoazofarbstoffe und verfahren zu deren herstellung.
DE1276844B (de)	1968-09-05	Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen
DE2116315A1 (de)	1971-10-28	Azoverbindungen
AT165298B (de)	1950-02-10	Verfahren zur Herstellung von esterartigen Derivaten aus o,o'-Dioxymonoazofarbstoffen
DE1810063A1 (de)	1970-06-04	In Wasser schwer loesliche Azoverbindungen
DE964975C (de)	1957-05-29	Verfahren zur Herstellung von Monoazofarbstoffen
DE1810063C (de)	1971-09-02	In Wasser schwer lösliche Azoverbm düngen
DE1278042B (de)	1968-09-19	Verfahren zur Herstellung von kationischen Farbstoffen
AT57616B (de)	1913-02-10	Verfahren zur Darstellung von Küpenfarbstoffen der Anthrazenreihe.
CH534722A (de)	1973-03-15	Verfahren zur Herstellung von Azoverbindungen
CH517157A (de)	1971-12-31	Verfahren zur Herstellung von Verbindungen der heterocyclischen Reihe
DE1804070C (de)	1971-06-16	Disazofarbstoffe
CH517812A (de)	1972-01-15	Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen
DE1184438B (de)	1964-12-31	Verfahren zur Herstellung von carbonsaeure- und sulfonsaeuregruppenfreien Mono- und Disazofarbstoffen
DE1221746B (de)	1966-07-28	Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe
CH523958A (de)	1972-06-15	Verfahren zur Herstellung in Wasser schwer löslicher Azoverbindungen