CA1038867A - Bis-(polyhalogenoanilino)-anthraquinones - Google Patents
Bis-(polyhalogenoanilino)-anthraquinonesInfo
- Publication number
- CA1038867A CA1038867A CA197,192A CA197192A CA1038867A CA 1038867 A CA1038867 A CA 1038867A CA 197192 A CA197192 A CA 197192A CA 1038867 A CA1038867 A CA 1038867A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- parts
- anthraquinone
- denotes
- anthraquinones
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZRPOLBLYTBZYPY-UHFFFAOYSA-N 1,5-bis(2,3,4,5,6-pentachloroanilino)anthracene-9,10-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=C(Cl)C(Cl)=C(Cl)C=3Cl)Cl)=C1C2=O ZRPOLBLYTBZYPY-UHFFFAOYSA-N 0.000 claims 1
- XXRYCTYMQHGNST-UHFFFAOYSA-N 1,5-bis(2,3,4,5-tetrachloroanilino)anthracene-9,10-dione Chemical compound ClC1=C(Cl)C(Cl)=CC(NC=2C=3C(=O)C4=CC=CC(NC=5C(=C(Cl)C(Cl)=C(Cl)C=5)Cl)=C4C(=O)C=3C=CC=2)=C1Cl XXRYCTYMQHGNST-UHFFFAOYSA-N 0.000 claims 1
- HSQKFBULGQNCFN-UHFFFAOYSA-N 1,5-bis(2,3,4-trichloroanilino)anthracene-9,10-dione Chemical compound ClC1=C(Cl)C(Cl)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=C(Cl)C(Cl)=CC=3)Cl)=C1C2=O HSQKFBULGQNCFN-UHFFFAOYSA-N 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 10
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 21
- 239000000975 dye Substances 0.000 description 16
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 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 12
- 150000004056 anthraquinones Chemical class 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 9
- 239000004922 lacquer Substances 0.000 description 8
- -1 alkali metal salts Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LMSJMSBCOQHNRC-UHFFFAOYSA-N 1,5-bis(2,5-dichloroanilino)anthracene-9,10-dione Chemical compound ClC1=CC=C(Cl)C(NC=2C=3C(=O)C4=CC=CC(NC=5C(=CC=C(Cl)C=5)Cl)=C4C(=O)C=3C=CC=2)=C1 LMSJMSBCOQHNRC-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 238000009434 installation Methods 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 2
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000005030 aluminium foil Substances 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910001919 chlorite Inorganic materials 0.000 description 2
- 229910052619 chlorite group Inorganic materials 0.000 description 2
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- KUWAAZMPJBFLEO-UHFFFAOYSA-N n,n,2-trichloroaniline Chemical class ClN(Cl)C1=CC=CC=C1Cl KUWAAZMPJBFLEO-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000485 pigmenting effect Effects 0.000 description 2
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- 229920000098 polyolefin Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
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- 238000005507 spraying Methods 0.000 description 2
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- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 description 1
- SHFQFVHDTGOWMU-UHFFFAOYSA-N 1,2-bis(n,2,3-trichloroanilino)anthracene-9,10-dione Chemical class C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=C(N(Cl)C=2C(=C(Cl)C=CC=2)Cl)C=1N(Cl)C1=CC=CC(Cl)=C1Cl SHFQFVHDTGOWMU-UHFFFAOYSA-N 0.000 description 1
- QGARGCPDYLOINN-UHFFFAOYSA-N 1,2-bis(n,2-dichloroanilino)anthracene-9,10-dione Chemical class C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=C(N(Cl)C=2C(=CC=CC=2)Cl)C=1N(Cl)C1=CC=CC=C1Cl QGARGCPDYLOINN-UHFFFAOYSA-N 0.000 description 1
- DHQZWSSFMMGSDE-UHFFFAOYSA-N 1,5-bis(2,4,5-trichloroanilino)anthracene-9,10-dione Chemical compound C1=C(Cl)C(Cl)=CC(Cl)=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=CC(Cl)=C(Cl)C=3)Cl)=C1C2=O DHQZWSSFMMGSDE-UHFFFAOYSA-N 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH575673A CH582207A5 (en, 2012) | 1973-04-19 | 1973-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038867A true CA1038867A (en) | 1978-09-19 |
Family
ID=4298818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA197,192A Expired CA1038867A (en) | 1973-04-19 | 1974-04-09 | Bis-(polyhalogenoanilino)-anthraquinones |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3927043A (en, 2012) |
| JP (1) | JPS5018541A (en, 2012) |
| AR (2) | AR202713A1 (en, 2012) |
| CA (1) | CA1038867A (en, 2012) |
| CH (1) | CH582207A5 (en, 2012) |
| DE (1) | DE2418379A1 (en, 2012) |
| ES (1) | ES425444A1 (en, 2012) |
| FR (1) | FR2226436B1 (en, 2012) |
| GB (1) | GB1455225A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH616442A5 (en, 2012) * | 1975-07-23 | 1980-03-31 | Ciba Geigy Ag | |
| JPS5623189U (en, 2012) * | 1979-07-28 | 1981-03-02 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH432692A (de) * | 1964-01-20 | 1967-03-31 | Sandoz Ag | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
| DE1768788A1 (de) * | 1968-06-29 | 1971-12-30 | Bayer Ag | Antrachinonfarbstoffe |
| US3752647A (en) * | 1971-07-30 | 1973-08-14 | Du Pont | Water swollen cellulose and blends dyed with insoluble, non-vattable anthraquinone dyes in a glycol ether solution |
| US3752646A (en) * | 1971-07-30 | 1973-08-14 | Du Pont | Water swollen cellulose and blends dyed with insoluble, non-vattable anthraquinone dyed in a glycol ether solution |
| US3797995A (en) * | 1972-10-02 | 1974-03-19 | American Aniline Prod | Polyester textile fibers dyed with alpha-aminoanthraquinone dyes |
-
1973
- 1973-04-19 CH CH575673A patent/CH582207A5/xx not_active IP Right Cessation
-
1974
- 1974-04-09 CA CA197,192A patent/CA1038867A/en not_active Expired
- 1974-04-16 DE DE2418379A patent/DE2418379A1/de not_active Withdrawn
- 1974-04-17 GB GB1674474A patent/GB1455225A/en not_active Expired
- 1974-04-17 US US461567A patent/US3927043A/en not_active Expired - Lifetime
- 1974-04-18 AR AR253342A patent/AR202713A1/es active
- 1974-04-18 ES ES425444A patent/ES425444A1/es not_active Expired
- 1974-04-19 JP JP49044352A patent/JPS5018541A/ja active Pending
- 1974-04-19 FR FR7413714A patent/FR2226436B1/fr not_active Expired
-
1975
- 1975-03-26 AR AR258135A patent/AR202972A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2418379A1 (de) | 1974-11-07 |
| FR2226436B1 (en, 2012) | 1978-01-20 |
| US3927043A (en) | 1975-12-16 |
| ES425444A1 (es) | 1976-12-16 |
| CH582207A5 (en, 2012) | 1976-11-30 |
| AR202713A1 (es) | 1975-07-15 |
| JPS5018541A (en, 2012) | 1975-02-27 |
| GB1455225A (en) | 1976-11-10 |
| AR202972A1 (es) | 1975-07-31 |
| FR2226436A1 (en, 2012) | 1974-11-15 |
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