CH399628A - Verfahren zur Herstellung wasserlöslicher Azofarbstoffe - Google Patents

Verfahren zur Herstellung wasserlöslicher Azofarbstoffe

Info

Publication number: CH399628A
Authority: CH; Switzerland
Prior art keywords: groups; parts; water; amino; sulfonic acid
Prior art date: 1957-12-13

Application number

CH177965A

Other languages

German (de)

English (en)

Inventor

Guenter Dr Lange

Guenter Dr Krehbiel

Original Assignee

Basf 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.)

1957-12-13

Filing date

1959-09-02

Publication date

1965-09-30

1957-12-13 Priority claimed from DEB47131A external-priority patent/DE1211346B/de

1958-09-25 Priority claimed from DEB50485A external-priority patent/DE1244313B/de

1959-09-02 Application filed by Basf Ag filed Critical Basf Ag

1965-09-30 Publication of CH399628A publication Critical patent/CH399628A/de

Links

239000000987 azo dye Substances 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 9
HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
150000008049 diazo compounds Chemical class 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005362 aryl sulfone group Chemical group 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
125000001174 sulfone group Chemical group 0.000 claims 1
239000000975 dye Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
-1 phenylene radical Chemical class 0.000 description 7
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000004043 dyeing Methods 0.000 description 3
RRKWPXMDCPJEHS-UHFFFAOYSA-N n-(3-aminophenyl)prop-2-enamide Chemical compound NC1=CC=CC(NC(=O)C=C)=C1 RRKWPXMDCPJEHS-UHFFFAOYSA-N 0.000 description 3
239000004753 textile Substances 0.000 description 3
229920003043 Cellulose fiber Polymers 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
OBEKLVIQKRLZLV-UHFFFAOYSA-N 2-amino-5-(prop-2-enoylamino)benzenesulfonic acid Chemical compound NC1=CC=C(NC(=O)C=C)C=C1S(O)(=O)=O OBEKLVIQKRLZLV-UHFFFAOYSA-N 0.000 description 1
NGRHHTODLFNUHB-UHFFFAOYSA-N CCN(CC)S(=O)=O Chemical group CCN(CC)S(=O)=O NGRHHTODLFNUHB-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-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
GWEVASVGVKFMNJ-UHFFFAOYSA-N N-(4-amino-2-chlorophenyl)prop-2-enamide Chemical compound NC1=CC(=C(C=C1)NC(C=C)=O)Cl GWEVASVGVKFMNJ-UHFFFAOYSA-N 0.000 description 1
UTYKMJYJCSZPSN-UHFFFAOYSA-N N-(4-amino-3-methylsulfonylphenyl)prop-2-enamide Chemical compound NC1=C(C=C(C=C1)NC(C=C)=O)S(=O)(=O)C UTYKMJYJCSZPSN-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000203 mixture Substances 0.000 description 1
HFGXCYUIVSCHDN-UHFFFAOYSA-N n-(4-amino-2,5-dimethoxyphenyl)prop-2-enamide Chemical compound COC1=CC(NC(=O)C=C)=C(OC)C=C1N HFGXCYUIVSCHDN-UHFFFAOYSA-N 0.000 description 1
RXARWALVRZHWLC-UHFFFAOYSA-N n-(4-amino-3-methylphenyl)prop-2-enamide Chemical compound CC1=CC(NC(=O)C=C)=CC=C1N RXARWALVRZHWLC-UHFFFAOYSA-N 0.000 description 1
WNVPACYPJUPHON-UHFFFAOYSA-N n-(4-aminophenyl)prop-2-enamide Chemical compound NC1=CC=C(NC(=O)C=C)C=C1 WNVPACYPJUPHON-UHFFFAOYSA-N 0.000 description 1
PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
- C09B62/47—Azo dyes
- C09B62/473—Monoazo dyes

Landscapes

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

CH177965A 1957-12-13 1959-09-02 Verfahren zur Herstellung wasserlöslicher Azofarbstoffe CH399628A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEB47131A DE1211346B (de)	1957-12-13	1957-12-13	Verfahren zur Herstellung wasserloeslicher Azofarbstoffe
DEB50485A DE1244313B (de)	1958-09-25	1958-09-25	Verfahren zur Herstellung wasserloeslicher Azofarbstoffe

Publications (1)

Publication Number	Publication Date
CH399628A true CH399628A (de)	1965-09-30

Family

ID=6819213

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH177965A CH399628A (de)	1957-12-13	1959-09-02	Verfahren zur Herstellung wasserlöslicher Azofarbstoffe
CH7770959A CH398834A (de)	1957-12-13	1959-09-02	Verfahren zur Herstellung wasserlöslicher Azofarbstoffe

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH7770959A CH398834A (de)	1957-12-13	1959-09-02	Verfahren zur Herstellung wasserlöslicher Azofarbstoffe

Country Status (3)

Country	Link
CH (2)	CH399628A (fr)
FR (1)	FR76347E (fr)
GB (1)	GB879925A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2943914A1 (de) *	1979-10-31	1981-05-14	Bayer Ag, 5090 Leverkusen	Reaktivfarbstoffe, deren herstellung und verwendung zum faerben oh- oder nh-haltiger materialien

1959
- 1959-09-02 CH CH177965A patent/CH399628A/de unknown
- 1959-09-02 CH CH7770959A patent/CH398834A/de unknown
- 1959-09-18 GB GB31831/59A patent/GB879925A/en not_active Expired
- 1959-09-24 FR FR805891A patent/FR76347E/fr not_active Expired

Also Published As

Publication number	Publication date
CH398834A (de)	1966-03-15
FR76347E (fr)	1961-10-06
GB879925A (en)	1961-10-11

Publication	Publication Date	Title
DE2004487C3 (de)	1979-12-06	Wasserlösliche Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2238110A1 (de)	1973-02-15	Azoverbindungen, deren herstellung und verwendung
CH399628A (de)	1965-09-30	Verfahren zur Herstellung wasserlöslicher Azofarbstoffe
DE2804599C2 (de)	1983-03-03	Azofarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
AT220740B (de)	1962-04-10	Verfahren zur Herstellung neuer wasserlöslicher Azofarbstoffe
AT211447B (de)	1960-10-10	Verfahren zur Herstellung neuer, wasserlöslicher Azofarbstoffe
DE628462C (de)	1936-04-06	Verfahren zur Herstellung von Azofarbstoffen
DE883021C (de)	1953-07-13	Verfahren zur Herstellung von chromierbaren Monoazofarbstoffen
DE909383C (de)	1954-04-15	Verfahren zur Herstellung von Monoazofarbstoffen
DE1544527C (de)	1971-04-22	Verfahren zur Herstellung von Azofarb Stoffen
DE1794286C3 (de)	1974-07-25	Azofarbstoffe und Verfahren zu deren Herstellung. Ausscheidung aus: 1544527
AT220742B (de)	1962-04-10	Verfahren zur Herstellung von neuen Azofarbstoffen
DE2216570A1 (de)	1973-10-18	Wasserloesliche azofarbstoffe der 2.6-diamino-pyridin-reihe
DE834881C (de)	1952-03-24	Verfahren zur Herstellung von Disazofarbstoffen
DE964975C (de)	1957-05-29	Verfahren zur Herstellung von Monoazofarbstoffen
AT148468B (de)	1937-01-25	Verfahren zur Herstellung von Monoazofarbstoffen.
DE879272C (de)	1953-06-11	Verfahren zur Herstellung von Monoazofarbstoffen
DE671287C (de)	1939-02-04	Verfahren zur Herstellung von Azofarbstoffen
AT221680B (de)	1962-06-12	Verfahren zur Herstellung von neuen, zur Wollfärbung geeigneten Azofarbstoffen
AT162592B (de)	1949-03-10	Verfahren zur Herstellung von neuen Disazofarbstoffen
DE965917C (de)	1957-06-27	Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen
AT162228B (de)	1949-02-10	Verfahren zur Herstellung von neuen Monoazofarbstoffen
AT162620B (de)	1949-03-25	Verfahren zur Darstellung von neuen Azofarbstoffen
DE842985C (de)	1952-07-03	Verfahren zur Herstellung von Azofarbstoffen
DE1944699A1 (de)	1971-05-06	Monoazofarbstoffe