GB487878A - Improvements in the manufacture and production of compounds of the anthraquinone and anthrapyrimidine series - Google Patents
Improvements in the manufacture and production of compounds of the anthraquinone and anthrapyrimidine seriesInfo
- Publication number
- GB487878A GB487878A GB3575436A GB3575436A GB487878A GB 487878 A GB487878 A GB 487878A GB 3575436 A GB3575436 A GB 3575436A GB 3575436 A GB3575436 A GB 3575436A GB 487878 A GB487878 A GB 487878A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- shades
- artificial silk
- silk
- phosphorus
- 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
- 150000004056 anthraquinones Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 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 title abstract 2
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical class C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 8
- 229920002955 Art silk Polymers 0.000 abstract 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 4
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 4
- 210000002268 wool Anatomy 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 3
- -1 phosphorus halide Chemical class 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- FEQNHKAASLXNKQ-UHFFFAOYSA-N 1,2-diamino-4-(4-aminophenyl)anthracene-9,10-dione Chemical class C1=CC(N)=CC=C1C1=CC(N)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O FEQNHKAASLXNKQ-UHFFFAOYSA-N 0.000 abstract 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002497 iodine compounds Chemical class 0.000 abstract 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 abstract 1
- CQGDBBBZCJYDRY-UHFFFAOYSA-N methoxyanthraquinone Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OC CQGDBBBZCJYDRY-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- ZKQJQQYORRFUAZ-UHFFFAOYSA-N naphtho[2,3-f]quinazolin-1-amine Chemical class C1=CC=CC2=CC3=C4C(N)=NC=NC4=CC=C3C=C21 ZKQJQQYORRFUAZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
Dyes are made by reacting anthraquinones or anthrapyrimidines having at least one primary amino group but no carboxylic or esterifiable hydroxy group with a phosphorus halide and treating the resulting compounds with aqueous alkaline agents. Amino compounds specified are 1-aminoanthraquinones, 1.4 - diaminoanthraquinones, 1.4.5.8 - tetraminoanthraquinones, 1 - amino - 4 - anilidoanthraquinones, 1 - amino - 4 - (p - aminophenyl)-aminoanthraquinones, aminoanthrapyrimidines, 1.4 - diamino - 2 - methoxyanthraquinone and 1.4 - diaminoanthraquinone - 2 - carboxylic acid amide. Phosphorus halides specified are phosphorus trichloride, pentachloride, oxychloride and the corresponding bromine and iodine compounds. Acid-binding agents which may be used are ammonia and organic bases such as pyridine, quinoline or dimethylaniline, which may also serve as solvents. The intermediate compounds, which contain halogen, may be converted to salts of phosphamic acids free from halogen by the use of aqueous alkaline agents such as caustic alkalies, or alkali carbonates. The products are soluble in water and dye acetate artificial silk, wool, silk, and viscose artificial silk fast shades. In examples: (1) 1.4 - diamino - 2 p - methoxyanthraquinone is reacted with phosphorus oxychloride, followed by treatment with sodium carbonate solution to give the sodium salt of the phosphamic acid; the free acid may be reconverted to the anthraquinone by heating with mineral acid and dyes acetate artificial silk, wool, or viscose artificial silk bluish-red shades; 1.4-diaminoanthraquinone (violet shades) or 1-amino-4-(p-aminophenyl)-aminoanthraquinone (blue shades) may also be used; (2) 1-amino-4-p-anisididoanthraquinone is reacted with phosphorus oxychloride, followed by treatment with caustic soda and sodium carbonate (blue shades); (3) phosphorus oxychloride is reacted with 1.4.5.8-tetraminoanthraquinone in pyridine, followed by treatment with caustic soda (blue shades on acetate artificial silk, wool, or silk); (4) phosphorus oxychloride is reacted with 4-amino-1.9-anthrapyrimidine in pyridine, followed by treatment with caustic soda (greenish-yellow shades on acetate artificial silk, wool or silk); (5) 1-aminoanthraquinone is reacted with phosphorus pentachloride in nitrobenzene, followed by treatment with caustic soda (yellow-red shades on acetate artificial silk).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3575436A GB487878A (en) | 1936-12-30 | 1936-12-30 | Improvements in the manufacture and production of compounds of the anthraquinone and anthrapyrimidine series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3575436A GB487878A (en) | 1936-12-30 | 1936-12-30 | Improvements in the manufacture and production of compounds of the anthraquinone and anthrapyrimidine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB487878A true GB487878A (en) | 1938-06-28 |
Family
ID=10381203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3575436A Expired GB487878A (en) | 1936-12-30 | 1936-12-30 | Improvements in the manufacture and production of compounds of the anthraquinone and anthrapyrimidine series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB487878A (en) |
-
1936
- 1936-12-30 GB GB3575436A patent/GB487878A/en not_active Expired
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