GB803985A - Improvements relating to disazo pigments and their use - Google Patents
Improvements relating to disazo pigments and their useInfo
- Publication number
- GB803985A GB803985A GB6721/57A GB672157A GB803985A GB 803985 A GB803985 A GB 803985A GB 6721/57 A GB6721/57 A GB 6721/57A GB 672157 A GB672157 A GB 672157A GB 803985 A GB803985 A GB 803985A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzil
- diamino
- components
- coupling
- acid
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title abstract 4
- 239000000049 pigment Substances 0.000 title abstract 3
- -1 ketomethylene Chemical group 0.000 abstract 6
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 3
- 239000004800 polyvinyl chloride Substances 0.000 abstract 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 abstract 2
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical compound C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000005060 rubber Substances 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- 239000001052 yellow pigment Substances 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- TYWAOIBYSDORAH-UHFFFAOYSA-N 1,2-bis(4-aminophenyl)ethane-1,2-dione Chemical compound C1=CC(N)=CC=C1C(=O)C(=O)C1=CC=C(N)C=C1 TYWAOIBYSDORAH-UHFFFAOYSA-N 0.000 abstract 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 abstract 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 abstract 1
- XCRGXKMBFXAAQN-UHFFFAOYSA-N 4-(1-chlorocyclohexa-2,4-dien-1-yl)-5-methylpyrazol-3-one Chemical class O=C1N=NC(C)=C1C1(Cl)C=CC=CC1 XCRGXKMBFXAAQN-UHFFFAOYSA-N 0.000 abstract 1
- ARCXLHMMNLQZPG-UHFFFAOYSA-N COC1=C(N(C#N)OC)C=CC=C1.C(CC(=O)C)(=O)O Chemical compound COC1=C(N(C#N)OC)C=CC=C1.C(CC(=O)C)(=O)O ARCXLHMMNLQZPG-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- OLKDSOUAYGIJLA-UHFFFAOYSA-N ethyl 5-oxo-4H-pyrazole-1-carboxylate Chemical class C(C)OC(=O)N1N=CCC1=O OLKDSOUAYGIJLA-UHFFFAOYSA-N 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 238000006068 polycondensation reaction Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000009987 spinning Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Greenish to reddish yellow pigments of formula: <FORM:0803985/IV (a)/1> where X is a linear bridging member embracing two carbon atoms which are saturated by oxygen and hydroxyl groups and/or hydrogen atoms and A is the residue of a ketomethylene coupling component which is free from sulphonic or carboxylic acid groups are used to colour rubber and polyvinyl chloride. X may be two identical or different members of the series carbonyl, hydroxymethylene and methylene and mixtures of diazo components may be used. In examples polyvinyl chloride is coloured by dyestuffs made from the following azo and coupling components: 4,41-dichloro-3,31-diamino-benzil and -dibenzyl and acetoacetic acid-anilide, -p-toluidide, -p-chloranilide, -o- and -p-anisidides, -m-xylidide and -2,5-dimethoxy-4-chloranilide.ALSO:4,41-Dichlorbenzil treated with fuming nitric acid yields 4,41 - dichloro - 3,31 - dinitro - benzil which may be reduced with iron and hydrochloric acid to yield the corresponding diamine or hydrogenated to yield 4,41dichloro-3,31-diamino - hydrobenzoin. The diamino - benzil may be treated with hydrazine hydrate in diethylene glycol and potassium hydroxide to yield the corresponding dibenzyl or hydrogenated to the hydrobenzoin.ALSO:The invention comprises greenish to reddish yellow pigments of formula <FORM:0803985/IV (c)/1> where X is a linear bridging member embracing two carbon atoms which are saturated by oxygen and hydroxyl groups and/or hydrogen atoms and A is the residue of a ketomethylene coupling component which is free from sulphonic or carboxylic acid groups. They are made in conventional fashion by diazotizing appropriate dichlorodiamines containing X and coupling with the ketomethylene components. X may be two identical or different members of the series carbonyl, hydroxymethylene and methylene. Mixtures of diazo components may be used. Indicated ketomethylenes are acetoacetic acid anilide, chlor- and dichlor-anilides, toluidides, chlortoluidides, xylidides, anisidides, phenetidides, acetoacetic acid dimethoxy cyananilide, 2,5-dimethoxy-4-chloranilide, benzoyl acetic acid anilide, di-acetoacetic acid-o-tolidide, 1 - phenyl - 3 - methyl - and carbethoxy - 5-pyrazolones, the three 1 - chloro - phenyl - 3-methyl - 5 - pyrazolones, tolylmethyl - 5 - pyrazolones and dihydroxyquinoliens. The products pigment high molecular weight natural and synthetic substances such as rubber, paints and lacquers and organic polymerization, polycondensation and polyaddition products. Spinning masses for synthetic fibres, especially viscose, may also be coloured. In examples which illustrate the preparation of the pigments and their use in colouring polyvinyl chloride compositions the diazo components used are 4,41 - dichloro - 3,31 - diamino - benzil, hydrobenzoin and dibenzyl and the coupling components are chosen from those indicated above and 1 - (41 - methylphenyl) 3 - methyl - 5-pyrazolone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH803985X | 1956-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB803985A true GB803985A (en) | 1958-11-05 |
Family
ID=4537889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6721/57A Expired GB803985A (en) | 1956-03-02 | 1957-02-28 | Improvements relating to disazo pigments and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB803985A (en) |
-
1957
- 1957-02-28 GB GB6721/57A patent/GB803985A/en not_active Expired
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