GB1299080A - Water-soluble quarternary ammonium salts of basic azo dyes - Google Patents
Water-soluble quarternary ammonium salts of basic azo dyesInfo
- Publication number
- GB1299080A GB1299080A GB5162369A GB5162369A GB1299080A GB 1299080 A GB1299080 A GB 1299080A GB 5162369 A GB5162369 A GB 5162369A GB 5162369 A GB5162369 A GB 5162369A GB 1299080 A GB1299080 A GB 1299080A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- dyes
- alkenyl
- hydroxy
- halogen
- Prior art date
- 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.)
- Expired
Links
- 239000000987 azo dye Substances 0.000 title abstract 3
- 150000003863 ammonium salts Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- -1 acetoacetylamino Chemical group 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- DNGPFRDDEWZQKJ-UHFFFAOYSA-N N-[4-amino-4-(3-oxobutanoylamino)cyclohexa-1,5-dien-1-yl]-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1(N)CC=C(C=C1)NC(CC(=O)C)=O DNGPFRDDEWZQKJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 238000006149 azo coupling reaction Methods 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Abstract
1299080 Basic azo dyes STERLING DRUG Inc 21 Oct 1969 [21 Nov 1968] 51623/69 Heading C4P [Also in Division C2] New basic water-soluble azo dyes of formula wherein C is 1 or 2, R‹ is H, alkyl or hydroxyalkyl, R<SP>1</SP> is alkyl, alkenyl or hydroxy-alkyl, R<SP>2</SP> is alkyl, alkenyl, hydroxy-alkyl or -alkylene- NR‹Y or R<SP>1</SP> and R<SP>2</SP> together with the N atom are pyrrolidine, piperidine or 4-alkanoyl-piperazine, Y is H or -COR, R is H, alkyl, alkenyl, phenyl or phenylalkyl, An is an anion, Y<SP>1</SP> is a phenylene or phenylene-aminocarbonyl radical, Z is the radical of a coupling component derived from 1,4 - bis - (acetoacetylamino) - aniline, acetoacetanilide, 1,4 - bis - (2<SP>1</SP> - hydroxy - 3<SP>1</SP>- naphthoylamino) - benzene, 2,4 - dihydroxyquinoline, 1 - (2<SP>1</SP> - hydroxy - 3<SP>1</SP> - naphthoylamino) - naphthalene, 4,4<SP>1</SP> - bis - (acetoacetylamino)-diphenyl wherein R<SP>6</SP> is H, halogen or alkyl, R<SP>5</SP> is H, halogen, alkyl, benzoxazol-2-yl or benzimidazol-2-yl, R<SP>4</SP> is alkyl, alkoxycarboxamido or alkoxycarbonyl, Q<SP>2</SP>, Q<SP>3</SP> and Q<SP>4</SP> are H, halogen, alkyl, alkoxy, OH, NO 2 , amino, alkoxycarbonyl, carboxamido or sulphamyl, Q<SP>5</SP>, Q<SP>6</SP> and Q<SP>7</SP> are H, halogen, alkyl or alkoxy (and the phenyl residues in the specific coupling components listed may contain these substituents) and the alkyl, alkenyl, alkylene and alkoxy radicals contain 1-6 C atoms, are described. The dyes are prepared by azo coupling using appropriate components (see Division C2). When Y is -COR the dyes may be hydrolysed. The dyes may be used to colour wool, silk, nylon, rayon, polyacrylonitrile and, in particular, cotton and paper in yellow to red shades.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77788468A | 1968-11-21 | 1968-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1299080A true GB1299080A (en) | 1972-12-06 |
Family
ID=25111594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5162369A Expired GB1299080A (en) | 1968-11-21 | 1969-10-21 | Water-soluble quarternary ammonium salts of basic azo dyes |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA925854A (en) |
| GB (1) | GB1299080A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981003179A1 (en) * | 1980-05-13 | 1981-11-12 | Sandoz Ag | Improvements in or relating to organic compounds |
| EP0041040A1 (en) * | 1980-05-08 | 1981-12-02 | Sandoz Ag | Sulphofree basic azo compounds in metal complex form, in metal-free form and method for preparing the same |
| EP0306452A3 (en) * | 1987-09-03 | 1991-03-20 | Ciba-Geigy Ag | Cationic disazo stilbene dyes |
| EP0696619A1 (en) * | 1994-07-15 | 1996-02-14 | Ciba-Geigy Ag | Process for dyeing of paper |
| JP3379966B2 (en) | 1997-07-16 | 2003-02-24 | ロレアル | Novel chaotic oxidation base, its use for oxidative dyeing of keratin fibers, dyeing composition and dyeing method |
| WO2005085362A1 (en) * | 2004-03-06 | 2005-09-15 | Wella Aktiengesellschaft | Cationic naphthyldiazo dyes and agents containing said dyes used to colour keratin fibres |
| WO2008141012A3 (en) * | 2007-05-11 | 2008-12-31 | Mpex Pharmaceuticals Inc | Quaternary alkyl ammonium bacterial efflux pump inhibitors and therapeutic uses thereof |
| US8178490B2 (en) | 2007-05-11 | 2012-05-15 | Rempex Pharmaceuticals, Inc. | Polybasic bacterial efflux pump inhibitors and therapeutic uses thereof |
| KR20250167276A (en) * | 2024-05-22 | 2025-12-01 | (주)필로스톤 | Dichroic dye composition for polymer dispersed liquid crystal device and polymer dispersed liquid crystal device including the same |
-
1969
- 1969-10-21 CA CA065436A patent/CA925854A/en not_active Expired
- 1969-10-21 GB GB5162369A patent/GB1299080A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041040A1 (en) * | 1980-05-08 | 1981-12-02 | Sandoz Ag | Sulphofree basic azo compounds in metal complex form, in metal-free form and method for preparing the same |
| EP0093828A1 (en) * | 1980-05-08 | 1983-11-16 | Sandoz Ag | Sulpho-free basic azo compounds in metal-free or 1:1 or 1:2 metal complex form |
| EP0093829A1 (en) * | 1980-05-08 | 1983-11-16 | Sandoz Ag | Sulphofree basic azo compounds in metal-free 1:1 or 1:2 metal complex form |
| US4550158A (en) * | 1980-05-08 | 1985-10-29 | Sandoz Ltd. | Metal-free disazo compounds containing at least two basic water-solubilizing groups and having a 1-phenylpyrazole middle component radical and a 6-hydroxyprid-2-one terminal coupling component |
| US4587292A (en) * | 1980-05-08 | 1986-05-06 | Sandoz Ltd. | Sulfo group-free azo compounds having on average at least 1.3 basic water-solubilizing groups in metal-free, 1:1 metal complex or 1:2 metal complex form |
| US4665162A (en) * | 1980-05-08 | 1987-05-12 | Sandoz Ltd. | 1:1 and 1:2 metal complexes of sulfo group-free azo compound having on average at least 1.3 basic water-solubilizing groups |
| WO1981003179A1 (en) * | 1980-05-13 | 1981-11-12 | Sandoz Ag | Improvements in or relating to organic compounds |
| EP0306452A3 (en) * | 1987-09-03 | 1991-03-20 | Ciba-Geigy Ag | Cationic disazo stilbene dyes |
| EP0696619A1 (en) * | 1994-07-15 | 1996-02-14 | Ciba-Geigy Ag | Process for dyeing of paper |
| US5674299A (en) * | 1994-07-15 | 1997-10-07 | Ciba-Geigy Corporation | Process for dyeing paper |
| AU701595B2 (en) * | 1994-07-15 | 1999-02-04 | Ciba Specialty Chemicals Holding Inc. | Process for dyeing paper |
| JP3379966B2 (en) | 1997-07-16 | 2003-02-24 | ロレアル | Novel chaotic oxidation base, its use for oxidative dyeing of keratin fibers, dyeing composition and dyeing method |
| US6565614B1 (en) | 1997-07-16 | 2003-05-20 | L'oreal | Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods |
| WO2005085362A1 (en) * | 2004-03-06 | 2005-09-15 | Wella Aktiengesellschaft | Cationic naphthyldiazo dyes and agents containing said dyes used to colour keratin fibres |
| US7517367B2 (en) | 2004-03-06 | 2009-04-14 | Wella Ag | Cationic naphthyldiazo dyes and keratin fibers-coloring agents containing these dyes |
| WO2008141012A3 (en) * | 2007-05-11 | 2008-12-31 | Mpex Pharmaceuticals Inc | Quaternary alkyl ammonium bacterial efflux pump inhibitors and therapeutic uses thereof |
| US8178490B2 (en) | 2007-05-11 | 2012-05-15 | Rempex Pharmaceuticals, Inc. | Polybasic bacterial efflux pump inhibitors and therapeutic uses thereof |
| KR20250167276A (en) * | 2024-05-22 | 2025-12-01 | (주)필로스톤 | Dichroic dye composition for polymer dispersed liquid crystal device and polymer dispersed liquid crystal device including the same |
| KR102896400B1 (en) | 2024-05-22 | 2025-12-05 | (주)필로스톤 | Dichroic dye composition for polymer dispersed liquid crystal device and polymer dispersed liquid crystal device including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CA925854A (en) | 1973-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |