GB1460860A - Production of 1-amino-4-hydroxyanthraquinone-2-alkyl ethers - Google Patents
Production of 1-amino-4-hydroxyanthraquinone-2-alkyl ethersInfo
- Publication number
- GB1460860A GB1460860A GB1400874A GB1400874A GB1460860A GB 1460860 A GB1460860 A GB 1460860A GB 1400874 A GB1400874 A GB 1400874A GB 1400874 A GB1400874 A GB 1400874A GB 1460860 A GB1460860 A GB 1460860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- basic reaction
- dihydroxyanthraquinone
- ethoxy
- march
- 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
- -1 alkenylene radical Chemical class 0.000 abstract 5
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- QUXBARPXUAPKDG-UHFFFAOYSA-N 1-amino-2,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(O)=C2N QUXBARPXUAPKDG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 239000002798 polar solvent Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 125000005159 cyanoalkoxy group Chemical group 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Abstract
1460860 Preparing anthraquinone dyes BASF AG 29 March 1974 [31 March 1973] 14008/74 Heading C4P Compounds of the general formula wherein A is a chemical bond, a C 1 -C 11 alkylene or alkenylene radical which may contain the bridging member -O-, R is H, Cl, Br, OH, alkoxy, cyanoalkoxy or hydroxyalkoxy having 1-4 carbon atoms in the alkoxy radical, phenyl or phenoxy optionally substituted once or twice by Cl, Br, methyl, methoxy and/or ethoxy or is a -COOR<SP>1</SP>, -OCOR<SP>1</SP>, -CON(R<SP>2</SP>)- R<SP>3</SP> or group wherein R<SP>1</SP> is H or a C 1 -C 6 alkyl group, R<SP>2</SP> and R<SP>3</SP> are H or C 1 -C 4 alkyl optionally substituted by OH, methoxy or ethoxy or R<SP>2</SP> and R<SP>3</SP> together may complete a 5- or 6-membered heterocyclic ring which may also contain one or more oxygen, sulphur, or further nitrogen atoms, n is 1 or 2 and m is 3 or 4 are prepared by reacting 1-amino-2,4-dihydroxyanthraquinone with a compound wherein Hal is Cl or Br and A, R and n are as above in a polar solvent in presence of an agent having a basic reaction. In preferred embodiments, the reaction takes place at 40-180‹ C. using 1À0 to 1À5 moles of the haloalkyl compound per mole of 1-amino-2,4-dihydroxyanthraquinone and 1À0 to 1À2 equivalents of the agent having a basic reaction per mole of haloalkyl compound. The agents having basic reaction include alkali metal hydroxides, alcoholates, carbonates and hydrogen carbonates and mixtures thereof. The polar solvents include dimethylacetamide, dimethylformamide, dimethylsulphone, dimethylsulphoxide and N-methylpyrrolidone. The dyes dye or print secondary acetate rayon, polyamides and polyesters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2316291A DE2316291A1 (en) | 1973-03-31 | 1973-03-31 | PROCESS FOR THE PREPARATION OF 1-AMINO4-HYDROXY-ANTHRAQUINONE-2-ALKYL ETHER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1460860A true GB1460860A (en) | 1977-01-06 |
Family
ID=5876707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1400874A Expired GB1460860A (en) | 1973-03-31 | 1974-03-29 | Production of 1-amino-4-hydroxyanthraquinone-2-alkyl ethers |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS49127961A (en) |
| CH (1) | CH605628A5 (en) |
| DE (1) | DE2316291A1 (en) |
| FR (1) | FR2223358B3 (en) |
| GB (1) | GB1460860A (en) |
| IT (1) | IT1004422B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4691059A (en) * | 1985-08-30 | 1987-09-01 | Minnesota Mining And Manufacturing Company | Copolymerizable UV stabilizers |
| DE3726983A1 (en) * | 1987-08-13 | 1989-02-23 | Basf Ag | METHOD FOR PRODUCING 1-AMINO-4-HYDROXY-2- (6'-HYDROXYHEXOXY) ANTHRACHINONE |
-
1973
- 1973-03-31 DE DE2316291A patent/DE2316291A1/en active Pending
-
1974
- 1974-03-25 FR FR7410126A patent/FR2223358B3/fr not_active Expired
- 1974-03-27 CH CH424774A patent/CH605628A5/xx not_active IP Right Cessation
- 1974-03-28 IT IT49786/74A patent/IT1004422B/en active
- 1974-03-29 GB GB1400874A patent/GB1460860A/en not_active Expired
- 1974-03-29 JP JP49034757A patent/JPS49127961A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1004422B (en) | 1976-07-10 |
| CH605628A5 (en) | 1978-10-13 |
| DE2316291A1 (en) | 1974-10-10 |
| FR2223358A1 (en) | 1974-10-25 |
| FR2223358B3 (en) | 1977-01-07 |
| JPS49127961A (en) | 1974-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1312536A (en) | Hydantoin derivatives | |
| ES405983A1 (en) | N-fluoroalkylated phenylethylamine | |
| ES8403444A1 (en) | Substituted phenylsulfonyl urea derivatives, process and intermediates for their preparation, and their use as herbicides. | |
| GB1460860A (en) | Production of 1-amino-4-hydroxyanthraquinone-2-alkyl ethers | |
| ES475423A1 (en) | Anthraquinone compounds and the production and use thereof | |
| ES455074A1 (en) | 3-Indolyl-3-bis-amino-phenyl-phthalide compounds | |
| GB1323119A (en) | Arylimino-oxazolidines and their use as acaricides | |
| ES485457A1 (en) | New Process for the Preparation of 6-piperidino-2,4- diaminopyrimidine-3-oxide | |
| GB1416574A (en) | Acrylonitrile polymers with antistatic properties | |
| KR830004263A (en) | Method for preparing pyridine and pyrimidine, novel anti-inflammatory and immunomodulators | |
| GB1124539A (en) | New substituted-hydrazino benzisothiazoles and process for preparing same | |
| GB1469006A (en) | 2-phenylhydrazinothiazolines or-thiazines and a process for the preparation thereof | |
| GB1477957A (en) | Heterocyclic substituted styrenes and their use as optical brighteners | |
| GB1194598A (en) | Benzofuran Derivatives | |
| GB1412546A (en) | Morpholine derivatives | |
| ES8506605A1 (en) | Process for the preparation of basic oxime ethers | |
| SE8300432L (en) | REACTIVE CINNIC ACID DERIVATIVES FOR THE PREPARATION OF BIOLOGICALLY ACTIVE AMIDES | |
| ES347893A1 (en) | Biologically active substituted-s-triazines | |
| GB1501795A (en) | Phenylsulphonyl formamidine derivatives and their preparation and use | |
| IE41827L (en) | Organo-copper compounds | |
| ES8506606A1 (en) | Process for the preparation of basic oxime ethers | |
| GB1109310A (en) | Heterocyclic ethanols | |
| ES441437A1 (en) | 3-Methoxy crotonanilides as herbicides | |
| GB1450862A (en) | 6-triazolyl-2-benzofurans and optical brighteners | |
| KR830001839B1 (en) | Process for preparing phenyl quinolizidines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |