DE1279253B - Verfahren zur Herstellung von 1-Amino-2-benzoyl-4-hydroxyanthrachinonen - Google Patents
Verfahren zur Herstellung von 1-Amino-2-benzoyl-4-hydroxyanthrachinonenInfo
- Publication number
- DE1279253B DE1279253B DET27088A DET0027088A DE1279253B DE 1279253 B DE1279253 B DE 1279253B DE T27088 A DET27088 A DE T27088A DE T0027088 A DET0027088 A DE T0027088A DE 1279253 B DE1279253 B DE 1279253B
- Authority
- DE
- Germany
- Prior art keywords
- amino
- benzoyl
- hydroxyanthraquinones
- dyes
- dye
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- ZTHMZQSTLOYYDF-UHFFFAOYSA-N 1-amino-2-benzoyl-4-hydroxyanthracene-9,10-dione Chemical class C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1C(=O)C1=CC=CC=C1 ZTHMZQSTLOYYDF-UHFFFAOYSA-N 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WKLRPYQQRZSYPI-UHFFFAOYSA-N 1-amino-2-benzoylanthracene-9,10-dione Chemical compound C1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1C(=O)C1=CC=CC=C1 WKLRPYQQRZSYPI-UHFFFAOYSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 27
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 239000004744 fabric Substances 0.000 description 6
- -1 p-fluorobenzoyl Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- DBRWLQUGUQVOCR-UHFFFAOYSA-N 1,4-diamino-2-benzoylanthracene-9,10-dione Chemical class NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=1C(=O)C1=CC=CC=C1 DBRWLQUGUQVOCR-UHFFFAOYSA-N 0.000 description 1
- VJFLKWCQBYAZJM-UHFFFAOYSA-N 1-amino-2-benzoyl-4-bromoanthracene-9,10-dione Chemical compound C1=C(Br)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1C(=O)C1=CC=CC=C1 VJFLKWCQBYAZJM-UHFFFAOYSA-N 0.000 description 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004338 hydroxy anthraquinones Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000004048 vat dyeing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US311986A US3211755A (en) | 1963-09-27 | 1963-09-27 | 1-amino-2-benzoyl-4-hydroxy anthraquinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1279253B true DE1279253B (de) | 1968-10-03 |
Family
ID=23209352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET27088A Pending DE1279253B (de) | 1963-09-27 | 1964-09-25 | Verfahren zur Herstellung von 1-Amino-2-benzoyl-4-hydroxyanthrachinonen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3211755A (enrdf_load_stackoverflow) |
| BE (1) | BE653575A (enrdf_load_stackoverflow) |
| CH (1) | CH448337A (enrdf_load_stackoverflow) |
| DE (1) | DE1279253B (enrdf_load_stackoverflow) |
| GB (1) | GB1033269A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617173A (en) * | 1968-06-24 | 1971-11-02 | Toms River Chemical Corp | 2-benzoylanthraquinone dyes for polyester fibers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE628695A (enrdf_load_stackoverflow) * | 1962-02-21 | |||
| GB661045A (en) * | 1948-01-30 | 1951-11-14 | Ciba Ltd | Manufacture of anthraquinone derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773071A (en) * | 1954-01-26 | 1956-12-04 | Interchem Corp | Anthraquinone dyes |
| BE579161A (enrdf_load_stackoverflow) * | 1958-05-30 |
-
0
- BE BE653575D patent/BE653575A/xx unknown
-
1963
- 1963-09-27 US US311986A patent/US3211755A/en not_active Expired - Lifetime
-
1964
- 1964-07-30 CH CH1000564A patent/CH448337A/de unknown
- 1964-09-16 GB GB37900/64A patent/GB1033269A/en not_active Expired
- 1964-09-25 DE DET27088A patent/DE1279253B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB661045A (en) * | 1948-01-30 | 1951-11-14 | Ciba Ltd | Manufacture of anthraquinone derivatives |
| BE628695A (enrdf_load_stackoverflow) * | 1962-02-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH448337A (de) | 1967-12-15 |
| GB1033269A (en) | 1966-06-22 |
| BE653575A (enrdf_load_stackoverflow) | |
| US3211755A (en) | 1965-10-12 |
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