CH529203A - Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen - Google Patents

Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen

Info

Publication number: CH529203A
Authority: CH; Switzerland
Prior art keywords: parts; formula; optionally substituted; radical; water
Prior art date: 1969-11-19

Application number

CH588872A

Other languages

German (de)

English (en)

Inventor

Altermatt Ruedi

Willy Dr Steinemann

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.)

1969-11-19

Filing date

1969-11-19

Publication date

1972-10-15

1969-11-19 Application filed by Sandoz Ag filed Critical Sandoz Ag

1969-11-19 Priority to CH588872A priority Critical patent/CH529203A/de

1972-10-15 Publication of CH529203A publication Critical patent/CH529203A/de

Links

239000001005 nitro dye Substances 0.000 title abstract 2
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
150000001450 anions Chemical class 0.000 claims abstract description 14
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 7
229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
-1 benzoate ions Chemical class 0.000 claims description 40
150000001875 compounds Chemical class 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
239000000975 dye Substances 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
125000000547 substituted alkyl group Chemical group 0.000 claims description 12
229920002239 polyacrylonitrile Polymers 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
229960000583 acetic acid Drugs 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
238000004043 dyeing Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
238000004040 coloring Methods 0.000 claims description 4
239000012362 glacial acetic acid Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
239000001043 yellow dye Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
239000004744 fabric Substances 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 claims description 2
RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 claims description 2
QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
229920001353 Dextrin Polymers 0.000 claims description 2
239000004375 Dextrin Substances 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
ZXYNGLRGFYLTQZ-UHFFFAOYSA-M [Zn]Cl Chemical compound [Zn]Cl ZXYNGLRGFYLTQZ-UHFFFAOYSA-M 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 2
229940089960 chloroacetate Drugs 0.000 claims description 2
235000019425 dextrin Nutrition 0.000 claims description 2
238000010790 dilution Methods 0.000 claims description 2
239000012895 dilution Substances 0.000 claims description 2
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
229910001410 inorganic ion Inorganic materials 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
229940001447 lactate Drugs 0.000 claims description 2
239000010985 leather Substances 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000010186 staining Methods 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
229940086735 succinate Drugs 0.000 claims description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
229940095064 tartrate Drugs 0.000 claims description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract description 2
229910006069 SO3H Inorganic materials 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 abstract 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
150000003254 radicals Chemical class 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
MZUSCVCCMHDHDF-UHFFFAOYSA-N P(=O)(=O)[W] Chemical compound P(=O)(=O)[W] MZUSCVCCMHDHDF-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
125000002252 acyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002091 cationic 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
125000004663 dialkyl amino group Chemical group 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
HGRDUZITLBEBJY-UHFFFAOYSA-N phenyl-(2-phenyldiazenylphenyl)diazene Chemical group C1=CC=CC=C1N=NC1=CC=CC=C1N=NC1=CC=CC=C1 HGRDUZITLBEBJY-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
239000000088 plastic resin Substances 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
239000004753 textile Substances 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 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
- C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group
- 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
- C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH588872A 1969-11-19 1969-11-19 Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen CH529203A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH588872A CH529203A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH1717969A CH523954A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppenfreier basischer Verbindungen
CH588872A CH529203A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen
CH1718069A CH529202A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppen freier basischer Nitroverbindungen

Publications (1)

Publication Number	Publication Date
CH529203A true CH529203A (de)	1972-10-15

Family

ID=62495390

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH588872A CH529203A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen
CH1717969A CH523954A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppenfreier basischer Verbindungen
CH1718069A CH529202A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppen freier basischer Nitroverbindungen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1717969A CH523954A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppenfreier basischer Verbindungen
CH1718069A CH529202A (de)	1969-11-19	1969-11-19	Verfahren zur Herstellung sulfonsäuregruppen freier basischer Nitroverbindungen

Country Status (4)

Country	Link
CH (3)	CH529203A (fr)
DE (2)	DE2055963A1 (fr)
FR (2)	FR2070716B3 (fr)
GB (2)	GB1328237A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0723794D0 (en)	2007-12-05	2008-01-16	Lectus Therapeutics Ltd	Potassium ion channel modulators and uses thereof

1969
- 1969-11-19 CH CH588872A patent/CH529203A/de not_active IP Right Cessation
- 1969-11-19 CH CH1717969A patent/CH523954A/de not_active IP Right Cessation
- 1969-11-19 CH CH1718069A patent/CH529202A/de not_active IP Right Cessation
1970
- 1970-10-29 GB GB5139670A patent/GB1328237A/en not_active Expired
- 1970-10-29 GB GB5139570A patent/GB1328236A/en not_active Expired
- 1970-11-13 DE DE19702055963 patent/DE2055963A1/de active Pending
- 1970-11-13 DE DE19702055962 patent/DE2055962A1/de active Pending
- 1970-11-19 FR FR707041563A patent/FR2070716B3/fr not_active Expired
- 1970-11-19 FR FR7041564A patent/FR2073389B4/fr not_active Expired

Also Published As

Publication number	Publication date
FR2070716A7 (fr)	1971-09-17
DE2055962A1 (de)	1971-05-27
CH523954A (de)	1972-06-15
FR2070716B3 (fr)	1973-08-10
CH529202A (de)	1972-10-15
GB1328237A (en)	1973-08-30
FR2073389B4 (fr)	1974-10-11
GB1328236A (en)	1973-08-30
FR2073389A8 (fr)	1971-10-01
DE2055963A1 (de)	1971-05-27

Legal Events

Date	Code	Title	Description
1979-08-15	PL	Patent ceased
1979-09-14	PL	Patent ceased

Publication	Publication Date	Title
DE1644101A1 (de)	1970-09-24	Verfahren zur Herstellung von basischen Azofarbstoffen
DE1150652B (de)	1963-06-27	Faerben von Polyacrylnitrilfasern
DE2228792A1 (de)	1972-12-21	Sulfonsauregruppenfreie basische Azofarbstoffe, ihre Herstellung und Ver wendung
DE1569748C3 (de)	1975-05-07	Sulfonsäure- und carbonsäuregruppenfreie Aminodiphenyl-indolyl-methanfarbstoffe, deren Herstellung und Verwendung
CH529203A (de)	1972-10-15	Verfahren zur Herstellung von sulfonsäuregruppenfreier basischer Nitroverbindungen
DE2055918A1 (de)	1971-05-27	Sulfonsauregruppenfreie basische Chmo phthalonfarbstoffe, ihre Herstellung und Verwendung »
CH523955A (de)	1972-06-15	Verfahren zur Herstellung sulfonsäuregruppenfreier Azoverbindungen
CH513953A (de)	1971-10-15	Verfahren zur Herstellung von Azofarbstoffen
CH542267A (de)	1973-09-30	Verfahren zur Herstellung von sulfonsäuregruppenfreien basischen Azoverbindungen
CH509387A (de)	1971-06-30	Verfahren zur Herstellung von basischen Farbstoffen
CH569765A5 (en)	1975-11-28	Basic nitro dyestuffs prepn
CH616441A5 (en)	1980-03-31	Process for the preparation of sulphonic acid group-free basic anthraquinone dyestuffs
CH525934A (de)	1972-07-31	Verfahren zur Herstellung von basischen Verbindungen der Azoreihe
DE2023632C3 (de)	1975-07-10	Basische Anthrachinonfarbstoffe, ihre Herstellung und Verwendung
CH553241A (de)	1974-08-30	Verfahren zur herstellung von basischen azoverbindungen.
CH511924A (de)	1971-08-31	Verfahren zur Herstellung von basischen Farbstoffen Gegenstand der Erfindung ist im Verfahren zur Herstellung von basischen Farbstoffen der Formel
DE2061964A1 (de)	1971-09-02	Basische Azofarbstoffe, ihre Her stellung und Verwendung
DE1903058B (de)		Verfahren zur Herstellung von basischen Azofarbstoffen und deren Verwendung zum Farben u Bedrucken
CH554399A (de)	1974-09-30	Verfahren zur herstellung sulfonsaeuregruppenfreier basischer azoverbindungen.
CH569761A5 (en)	1975-11-28	Basic quinophthalone dyes
DE2724540A1 (de)	1977-12-15	Naphtholaktam-farbstoffe
CH531033A (de)	1972-11-30	Verfahren zur Herstellung von basischen Monoazofarbstoffen
CH516622A (de)	1971-12-15	Verfahren zur Herstellung von basischen Farbstoffen
CH567060A5 (en)	1975-09-30	Sulphonic acid-free basic dyes - for dyeing and printing acrylonitrile or vinylidene cyanide polymer-contg textiles polyesters and polyamides
CH517144A (de)	1971-12-31	Verfahren zur Herstellung von basischen Azoverbindungen