CH616952A5 - Process for the preparation of new water-soluble trisazo dyes - Google Patents

Process for the preparation of new water-soluble trisazo dyes Download PDF

Info

Publication number: CH616952A5
Authority: CH; Switzerland
Prior art keywords: mole; dyes; aniline; parts; coupler
Prior art date: 1976-08-03

Application number

CH873677A

Other languages

English (en)

French (fr)

Inventor

Alain Aurozo

Andre Sailer

Original Assignee

Ugine Kuhlmann

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.)

1976-08-03

Filing date

1977-07-14

Publication date

1980-04-30

1977-07-14 Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann

1980-04-30 Publication of CH616952A5 publication Critical patent/CH616952A5/fr

Links

239000000975 dye Substances 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 38
239000010985 leather Substances 0.000 claims abstract description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 3
XAUGWFWQVYXATQ-UHFFFAOYSA-N n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 XAUGWFWQVYXATQ-UHFFFAOYSA-N 0.000 claims description 4
CHQNGSJEKNJUBX-UHFFFAOYSA-N 1-amino-8-hydroxy-2h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC(O)=C2C(N)(S(O)(=O)=O)C(S(O)(=O)=O)C=CC2=C1 CHQNGSJEKNJUBX-UHFFFAOYSA-N 0.000 claims description 2
238000004043 dyeing Methods 0.000 claims description 2
239000002253 acid Substances 0.000 abstract description 8
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
238000003756 stirring Methods 0.000 description 2
238000011282 treatment Methods 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
GTIQTKQGARVKSI-UHFFFAOYSA-N C(C)(=O)CC(C)=O.[N+](=O)([O-])C1=CC=C(N)C=C1 Chemical compound C(C)(=O)CC(C)=O.[N+](=O)([O-])C1=CC=C(N)C=C1 GTIQTKQGARVKSI-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
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
-1 benzene amines Chemical class 0.000 description 1
230000027326 copulation Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
IDAQSADEMXDTKN-UHFFFAOYSA-L ethyl green Chemical compound [Cl-].[Br-].C1=CC([N+](C)(C)CC)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C1C=CC(=[N+](C)C)C=C1 IDAQSADEMXDTKN-UHFFFAOYSA-L 0.000 description 1
235000013305 food Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
239000001648 tannin Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)
Treatment And Processing Of Natural Fur Or Leather (AREA)

CH873677A 1976-08-03 1977-07-14 Process for the preparation of new water-soluble trisazo dyes CH616952A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7623725A FR2360634A1 (fr)	1976-08-03	1976-08-03	Nouveaux colorants trisazoiques hydrosolubles

Publications (1)

Publication Number	Publication Date
CH616952A5 true CH616952A5 (en)	1980-04-30

Family

ID=9176510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH873677A CH616952A5 (en)	1976-08-03	1977-07-14	Process for the preparation of new water-soluble trisazo dyes

Country Status (10)

Country	Link
AU (1)	AU503935B2 (it)
BE (1)	BE857082A (it)
BR (1)	BR7705043A (it)
CH (1)	CH616952A5 (it)
DE (1)	DE2734806A1 (it)
ES (1)	ES461298A1 (it)
FR (1)	FR2360634A1 (it)
GB (1)	GB1545681A (it)
IT (1)	IT1083036B (it)
NL (1)	NL7708411A (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3618265A1 (de) *	1986-05-30	1987-12-03	Basf Ag	Neue heterocyclenhaltige trisazofarbstoffe
ES2068915T3 (es) *	1989-01-02	1995-05-01	Ciba Geigy Ag	Procedimiento para teñir el cuero.
ES2049014T3 (es) *	1989-12-11	1994-04-01	Ciba Geigy Ag	Procedimiento de tintura del cuero.
CH685251A5 (de) *	1992-05-26	1995-05-15	Ciba Geigy Ag	Verfahren zum Färben von Leder.
EP1375732A3 (de) *	2002-06-11	2004-02-04	Car Trim Biermann, Marktfort und Dr. Rau GbR	Verfahren zur Herstellung eines Bezugsmaterials für Fahrzeuge, insbesondere eines Sitzbezuges für Kraftfahrzeuge
CN103145593A (zh) *	2013-03-26	2013-06-12	河北永泰柯瑞特化工有限公司	4，4’-二氨基苯磺酰替苯胺的制备方法

1976
- 1976-08-03 FR FR7623725A patent/FR2360634A1/fr active Granted
1977
- 1977-07-14 CH CH873677A patent/CH616952A5/fr not_active IP Right Cessation
- 1977-07-25 BE BE1008288A patent/BE857082A/xx unknown
- 1977-07-29 NL NL7708411A patent/NL7708411A/xx not_active Application Discontinuation
- 1977-07-29 AU AU27447/77A patent/AU503935B2/en not_active Expired
- 1977-07-29 IT IT6876777A patent/IT1083036B/it active
- 1977-08-01 BR BR7705043A patent/BR7705043A/pt unknown
- 1977-08-02 DE DE19772734806 patent/DE2734806A1/de not_active Withdrawn
- 1977-08-02 GB GB3231577A patent/GB1545681A/en not_active Expired
- 1977-08-02 ES ES461298A patent/ES461298A1/es not_active Expired

Also Published As

Publication number	Publication date
NL7708411A (nl)	1978-02-07
IT1083036B (it)	1985-05-21
BR7705043A (pt)	1978-05-02
BE857082A (fr)	1978-01-25
FR2360634B1 (it)	1978-12-22
AU2744777A (en)	1979-02-01
AU503935B2 (en)	1979-09-27
FR2360634A1 (fr)	1978-03-03
ES461298A1 (es)	1978-09-01
DE2734806A1 (de)	1978-02-09
GB1545681A (en)	1979-05-10

Legal Events

Date	Code	Title	Description
1982-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH616952A5 (en)	1980-04-30	Process for the preparation of new water-soluble trisazo dyes
JPS5910394B2 (ja)	1984-03-08	水溶性の繊維反応性アゾ染料の製法
JPS58180558A (ja)	1983-10-22	ジスアゾ染料
DE3142608A1 (de)	1983-05-05	Polyazofarbstoffe
EP0068245B1 (de)	1984-10-31	Sulfonsäuregruppenhaltige Farbstoffe
CN1104470C (zh)	2003-04-02	四偶氮染料、其生产和用途
EP0005207B1 (de)	1981-12-09	Bis-1:2-chrom-disazo-bisazomethinfarbstoffe, deren Herstellung und deren Verwendung zum Färben von Leder
JPS6334905B2 (it)	1988-07-12
JPS633909B2 (it)	1988-01-26
FR2612523A1 (fr)	1988-09-23	Procede pour la preparation de colorants monoazoiques metallables
FR2572085A1 (fr)	1986-04-25	Melanges de composes trisazoiques et tetrakisazoiques, leur preparation et leur utilisation comme colorants
JPS5855274B2 (ja)	1983-12-08	染色方法
FR2723368A1 (fr)	1996-02-09	Composes azoiques, leur preparation et leur utilisation comme colorants.
BE552910A (it)
CH333931A (fr)	1958-11-15	Procédé de préparation de colorants azoïques métallifères
FR2562552A1 (fr)	1985-10-11	Colorants a complexes chromiferes, leur preparation et leur utilisation
BE562937A (it)
FR2692273A1 (fr)	1993-12-17	Nouveaux complexes du chrome, leur préparation et leur utilisation comme colorants.
BE554509A (it)
BE526208A (it)
BE506933A (it)
BE561511A (it)
BE494716A (it)
BE568297A (it)
BE355928A (it)