DE2140511A1 - Neue kationische Azofarbstoffe und die Zwischenprodukte für ihre Herstellung - Google Patents

Neue kationische Azofarbstoffe und die Zwischenprodukte für ihre Herstellung

Info

Publication number: DE2140511A1
Authority: DE; Germany
Prior art keywords: parts; alkyl; dyes; formula; water
Prior art date: 1970-08-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

DE19712140511

Other languages

German (de)

English (en)

Inventor

Marie Josephe Jeanne Lannemezan Sureau Robert Frederic Michel Enghien les Baine Alicot geb Calvo, (Frankreich)

Original Assignee

Fa Ugine Kuhlmann, Paris

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.)

1970-08-12

Filing date

1971-08-12

Publication date

1972-02-17

1971-08-12 Application filed by Fa Ugine Kuhlmann, Paris filed Critical Fa Ugine Kuhlmann, Paris

1972-02-17 Publication of DE2140511A1 publication Critical patent/DE2140511A1/de

Status Pending legal-status Critical Current

Links

125000002091 cationic group Chemical group 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 4
239000000987 azo dye Substances 0.000 title description 3
239000000543 intermediate Substances 0.000 title description 2
239000000975 dye Substances 0.000 claims description 29
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 15
-1 heterocyclic amine Chemical class 0.000 claims description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
239000000835 fiber Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
238000004043 dyeing Methods 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229920002239 polyacrylonitrile Polymers 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 3
229920001059 synthetic polymer Polymers 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 5
229920002972 Acrylic fiber Polymers 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
229910021529 ammonia Inorganic materials 0.000 description 4
238000009835 boiling Methods 0.000 description 4
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000010306 acid treatment Methods 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
ADMVTZCMOLFYCM-UHFFFAOYSA-N 1,2-dimethylbenzimidazol-5-ol Chemical compound OC1=CC=C2N(C)C(C)=NC2=C1 ADMVTZCMOLFYCM-UHFFFAOYSA-N 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
KAGJDYZNKZZXGU-UHFFFAOYSA-N 3-hydroxy-1H-benzimidazol-3-ium chloride Chemical compound [Cl-].O[N+]1=CNC2=C1C=CC=C2 KAGJDYZNKZZXGU-UHFFFAOYSA-N 0.000 description 2
CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
GWFPMSIIVJMYRZ-UHFFFAOYSA-N n-(4-amino-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1C GWFPMSIIVJMYRZ-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
CRRGPIBVQLNTRN-UHFFFAOYSA-N 1,2-dimethyl-5-nitrobenzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N(C)C(C)=NC2=C1 CRRGPIBVQLNTRN-UHFFFAOYSA-N 0.000 description 1
KHIGSIBNOPKCOT-UHFFFAOYSA-N 1,2-dimethylbenzimidazol-5-amine Chemical compound NC1=CC=C2N(C)C(C)=NC2=C1 KHIGSIBNOPKCOT-UHFFFAOYSA-N 0.000 description 1
SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
KEJFADGISRFLFO-UHFFFAOYSA-N 1H-indazol-6-amine Chemical class NC1=CC=C2C=NNC2=C1 KEJFADGISRFLFO-UHFFFAOYSA-N 0.000 description 1
MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
IVUQHXKKRQEFBU-UHFFFAOYSA-N 3-methyl-4-[(3-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC(N=NC=2C(=CC(N)=CC=2)C)=C1 IVUQHXKKRQEFBU-UHFFFAOYSA-N 0.000 description 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
PFUQSACCWFVIBW-UHFFFAOYSA-N [C].C1=CC=CC=C1 Chemical class [C].C1=CC=CC=C1 PFUQSACCWFVIBW-UHFFFAOYSA-N 0.000 description 1
150000001253 acrylic acids Chemical class 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000000033 alkoxyamino group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
235000019646 color tone Nutrition 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000005452 ethyl sulfates Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
LWAYASXDHDEGAO-UHFFFAOYSA-N n-(4-amino-2-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1Cl LWAYASXDHDEGAO-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
- 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
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium

Landscapes

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

DE19712140511 1970-08-12 1971-08-12 Neue kationische Azofarbstoffe und die Zwischenprodukte für ihre Herstellung Pending DE2140511A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7029640A FR2112050B1 (xx)	1970-08-12	1970-08-12

Publications (1)

Publication Number	Publication Date
DE2140511A1 true DE2140511A1 (de)	1972-02-17

Family

ID=9060114

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19712140511 Pending DE2140511A1 (de)	1970-08-12	1971-08-12	Neue kationische Azofarbstoffe und die Zwischenprodukte für ihre Herstellung

Country Status (6)

Country	Link
BE (1)	BE771106A (xx)
CH (1)	CH527883A (xx)
DE (1)	DE2140511A1 (xx)
FR (1)	FR2112050B1 (xx)
GB (1)	GB1369831A (xx)
NL (1)	NL7110927A (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7497878B2 (en)	2005-06-30	2009-03-03	L'oreal, S.A.	Azo dyes containing a sulphonamide or amide function for the dyeing of human keratin fibers and method of dyeing and dyeing compositions containing them

1970
- 1970-08-12 FR FR7029640A patent/FR2112050B1/fr not_active Expired
1971
- 1971-08-09 BE BE771106A patent/BE771106A/xx unknown
- 1971-08-09 NL NL7110927A patent/NL7110927A/xx unknown
- 1971-08-10 CH CH1173771A patent/CH527883A/fr not_active IP Right Cessation
- 1971-08-11 GB GB3765871A patent/GB1369831A/en not_active Expired
- 1971-08-12 DE DE19712140511 patent/DE2140511A1/de active Pending

Also Published As

Publication number	Publication date
CH527883A (fr)	1972-09-15
FR2112050A1 (xx)	1972-06-16
NL7110927A (xx)	1972-02-15
BE771106A (fr)	1972-02-09
GB1369831A (en)	1974-10-09
FR2112050B1 (xx)	1978-01-13

Legal Events

Date	Code	Title	Description
1978-06-15	OHJ	Non-payment of the annual fee

Publication	Publication Date	Title
DE2004487C3 (de)	1979-12-06	Wasserlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2244035C3 (de)	1979-10-04	Disazopigmente, Verfahren zu deren Herstellung und ihre Verwendung zum Pigmentieren von hochmolekularem organischen Material
DE2243955A1 (de)	1973-03-15	Neue disazopigmente und verfahren zu deren herstellung und verwendung
DE2801951A1 (de)	1979-07-19	Azofarbstoffe
DE2417922A1 (de)	1974-10-17	In wasser unloesliche azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE1719087B2 (de)	1974-07-18	Basische Azofarbstoffe
DE2140511A1 (de)	1972-02-17	Neue kationische Azofarbstoffe und die Zwischenprodukte für ihre Herstellung
DE2364476A1 (de)	1974-07-04	Azofarbstoffe und ihre verwendung
DE2239445C3 (de)	1982-03-25	Kationische Pyrazolfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2612792A1 (de)	1976-10-07	Disperse monoazofarbstoffe
DE2010491C3 (de)	1973-09-13	In Wasser lösliche Azofarbstoffe und ihre Verwendung
DE2544568C3 (de)	1979-02-08	Sulfonsäuregruppenfreie Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung als Pigmente in Lacken, Druckfarben oder Kunststoffen
DE2215789C2 (de)	1982-04-01	Alkalifeste Disazo-disulfimid-Farbstoffe
DE2631669A1 (de)	1977-02-03	Azo-benzothiazoliumfarbstoffe, verfahren zu ihrer herstellung und deren verwendung
DE2212755A1 (de)	1973-09-20	Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung
DE2424538A1 (de)	1975-12-11	Azofarbstoffe mit einem phthalazonrest
DE2159574A1 (de)	1972-06-15	Wasserunlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von hydrophoben Fasern
DE1644287C (de)	1972-02-24	Verfahren zur Herstellung von Disazofarbstoffen
DE1469678A1 (de)	1968-12-19	Neue basische Diazofarbstoffe und ihre Anwendung zur Faerbung von Acrylfasern
DE1644093A1 (de)	1971-07-01	Verfahren zur Herstellung von wasserloeslichen basischen Azofarbstoffen
CH502413A (de)	1971-01-31	Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen
DE2111734B2 (de)	1973-12-20	Azofarbstoffe und ihre Verwendung
DE2051023A1 (en)	1972-04-20	Mono and dis-azo dyes - of the benzimidazole series contg sulphonic acid gps
DE2001916C (de)	1973-03-15	Wasserunlösliche Monoazofarbstoffe und ihre Verwendung
DE1544410C (de)		Verfahren zur Herstellung basischer Farbstoffe