GB496652A - Process for the manufacture of vat dyestuffs of the anthraquinoneacridone series - Google Patents
Process for the manufacture of vat dyestuffs of the anthraquinoneacridone seriesInfo
- Publication number
- GB496652A GB496652A GB1525737A GB1525737A GB496652A GB 496652 A GB496652 A GB 496652A GB 1525737 A GB1525737 A GB 1525737A GB 1525737 A GB1525737 A GB 1525737A GB 496652 A GB496652 A GB 496652A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ring
- closure
- followed
- aminoanthraquinone
- acridone
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 9
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 abstract 5
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 abstract 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 2
- 150000004056 anthraquinones Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 2
- CCEGIXWXBRNFOS-UHFFFAOYSA-N 1-amino-6-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2N CCEGIXWXBRNFOS-UHFFFAOYSA-N 0.000 abstract 1
- KQZGRXXFJWCJGT-UHFFFAOYSA-N 10H-acridin-9-one 3-bromo-1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=CC=2NC3=CC=CC=C3C(C12)=O.BrC=1C(=C(C=2C(C3=CC=CC=C3C(C2C1)=O)=O)Cl)Cl KQZGRXXFJWCJGT-UHFFFAOYSA-N 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000005239 aroylamino group Chemical group 0.000 abstract 1
- 238000006480 benzoylation reaction Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 235000013311 vegetables Nutrition 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/38—Compounds containing acridone and carbazole rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Dyes are made by reacting acid condensing agents with anthraquinone - 2.1(N) - 1.21(N)-benzacridones containing an a -aminoanthraquinone radical in 4-position and also in Bz.3, Bz.4, Bz.5 or Bz.6-position, and having in each nucleus one free o-position with respect to the imino group or the said o-positions being wholly or partly replaced by substituents which do not prevent ring-closure. If desired, the products may be after-oxidized, e.g. with sodium hypochlorite. The starting materials are obtained by reacting polyhalogen-anthra-quinone-benzacridones having a replaceable halogen atom in 4-position only of the anthraquinone nucleus and one or more halogens in the Bz.-positions with a -aminoanthraquinones. The Bz.-ring may contain halogen atoms, alkyl radicles or alkoxy groups, and the a -amino-anthraquinone radicles may contain halogen atoms or aroylamino groups. Condensing agents specified are aluminium chloride in solvents such as nitrobenzene, and also concentrated sulphuric acid or chlorsulphonic acid. Any aroyl residues saponified during the condensation may be reintroduced by aroylation. The products dye vegetable fibres yellowish-brown, khaki, or olive shades. In examples: (1) 4.61-dichloranthraquinone-2.1 (N)-11.21(N)-benzene acridone is reacted in naphthalene in presence of potassium carbonate and copper acetate with 1-aminoanthraquinone followed by ring-closure with aluminium chloride in nitrobenzene and oxidation with sodium hypochlorite or with 1-amino-5-benzoylaminoanthraquinone followed by ring-closure with sulphuric acid monohydrate; (2) 4.31.61-trichloranthraquinone - 2.1(N) - 11.21(N) - benzene acridone is reacted with 1-aminoanthraquinone, followed by ring-closure; (3) 31.51. 61.4 - tetrachloranthraquinone - 2.1(N) - 11.21 (N)-benzene acridone is reacted with 1-amino-anthraquinone, 6-chloro-1-aminoanthraquinone, or with 1-amino-5-benzoylaminoanthraquinone, followed by ring-closure, and in the case of the last-mentioned body by re-benzoylation; (4) 31.41.51.61.4 - pentachloranthraquinon -2.1(N)11.21(N)-benzene acridone is reacted with 1-aminoanthraquinone, followed by ring-closure; (5) 31-methoxy-61.4-dichloranthraquinone-2.1(N) -11.21(N)-benzene acridone is reacted with 1-aminoanthraquinone, followed by ring-closure; (6) the bromo-dichloro-anthraquinone-acridone obtained according to example 1 or 2 of Specification 327,758, is reacted with 1-amino-5-benzoylaminoanthraquinone in naphthalene in presence of sodium acetate, magnesium oxide, and copper chloride, followed by ring-closure; (7) the dibromochloranthraquin-one-acridone obtained according to example 4 of Specification 327,758, [Class 2 (iii)], is reacted with 1-amino-5-benzoylaminoanthraquinone or with 1-aminoanthraquinone as in (6), followed by ring-closure. Specifications 361,423, 439,180, and 451,859 also are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1525737A GB496652A (en) | 1937-06-01 | 1937-06-01 | Process for the manufacture of vat dyestuffs of the anthraquinoneacridone series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1525737A GB496652A (en) | 1937-06-01 | 1937-06-01 | Process for the manufacture of vat dyestuffs of the anthraquinoneacridone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB496652A true GB496652A (en) | 1938-12-01 |
Family
ID=10055843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1525737A Expired GB496652A (en) | 1937-06-01 | 1937-06-01 | Process for the manufacture of vat dyestuffs of the anthraquinoneacridone series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB496652A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE964976C (en) * | 1951-12-21 | 1957-05-29 | Ciba Geigy | Process for the production of anthraquinone dyes |
-
1937
- 1937-06-01 GB GB1525737A patent/GB496652A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE964976C (en) * | 1951-12-21 | 1957-05-29 | Ciba Geigy | Process for the production of anthraquinone dyes |
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