DE2236800A1 - Pigmentfarbstoffe der 2,4-dihydroxychinolinreihe - Google Patents
Pigmentfarbstoffe der 2,4-dihydroxychinolinreiheInfo
- Publication number
- DE2236800A1 DE2236800A1 DE2236800A DE2236800A DE2236800A1 DE 2236800 A1 DE2236800 A1 DE 2236800A1 DE 2236800 A DE2236800 A DE 2236800A DE 2236800 A DE2236800 A DE 2236800A DE 2236800 A1 DE2236800 A1 DE 2236800A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- formula
- pigment dyes
- pigment
- series
- 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
- 239000000049 pigment Substances 0.000 title claims description 18
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical class C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 title claims description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 12
- 150000007857 hydrazones Chemical class 0.000 claims description 10
- 229940015043 glyoxal Drugs 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 125000005594 diketone group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000001052 yellow pigment Substances 0.000 description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 5
- IQDQMRZGMILNMQ-UHFFFAOYSA-N naphthalene-2,6-dicarbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(C=O)=CC=C21 IQDQMRZGMILNMQ-UHFFFAOYSA-N 0.000 description 5
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- YSIIHTHHMPYKFP-UHFFFAOYSA-N 2,5-dimethoxyterephthalaldehyde Chemical compound COC1=CC(C=O)=C(OC)C=C1C=O YSIIHTHHMPYKFP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- UTOJPZBVJLHYGO-UHFFFAOYSA-N 1-(2,4-Dihydroxyquinolin-3-yl)ethan-1-one Chemical class C1=CC=C2C(=O)C(C(=O)C)=C(O)NC2=C1 UTOJPZBVJLHYGO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- -1 diphenyldialdehyde Chemical compound 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XUFLAVKRRLBIMV-UHFFFAOYSA-N naphthalene-1,4-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=C(C=O)C2=C1 XUFLAVKRRLBIMV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DENJKYZPPCLOME-UHFFFAOYSA-N (5-benzoyl-2,4-dimethoxyphenyl)-phenylmethanone Chemical compound COC1=CC(OC)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 DENJKYZPPCLOME-UHFFFAOYSA-N 0.000 description 1
- WJKWZEQHHHGYTH-UHFFFAOYSA-N 1-(2,3-dimethoxyphenyl)-2-phenylethane-1,2-dione Chemical compound COC1=CC=CC(C(=O)C(=O)C=2C=CC=CC=2)=C1OC WJKWZEQHHHGYTH-UHFFFAOYSA-N 0.000 description 1
- WAHBFHUZSTXBMP-UHFFFAOYSA-N 2,3-dimethoxyterephthalaldehyde Chemical compound COC1=C(OC)C(C=O)=CC=C1C=O WAHBFHUZSTXBMP-UHFFFAOYSA-N 0.000 description 1
- XBCGIUJJUZHWMC-UHFFFAOYSA-N 2,5-dichloroterephthalaldehyde Chemical compound ClC1=CC(C=O)=C(Cl)C=C1C=O XBCGIUJJUZHWMC-UHFFFAOYSA-N 0.000 description 1
- XANHGTOPQJDHRU-UHFFFAOYSA-N 3-acetyl-6,8-dichloro-4-hydroxy-1H-quinolin-2-one Chemical compound ClC=1C=C2C(=C(C(=NC2=C(C1)Cl)O)C(C)=O)O XANHGTOPQJDHRU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002966 varnish Substances 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
- C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
- C09B23/166—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing two or more nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2236800A DE2236800A1 (de) | 1972-07-27 | 1972-07-27 | Pigmentfarbstoffe der 2,4-dihydroxychinolinreihe |
| CH999773A CH574988A5 (enrdf_load_html_response) | 1972-07-27 | 1973-07-09 | |
| AU58285/73A AU5828573A (en) | 1972-07-27 | 1973-07-19 | Pigments ofthe 2, 4-dihydroxyquinoline series |
| FR7327009A FR2194751B3 (enrdf_load_html_response) | 1972-07-27 | 1973-07-24 | |
| BR5621/73A BR7305621D0 (pt) | 1972-07-27 | 1973-07-25 | Processo para fabricao de corantes pigmentares da serie da 2,4-dihidroxi-quinolina |
| JP48083215A JPS4959835A (enrdf_load_html_response) | 1972-07-27 | 1973-07-25 | |
| ZA735062A ZA735062B (en) | 1972-07-27 | 1973-07-25 | Pigments of the 2,4-dihydroxyquinoline series |
| IT51649/73A IT990015B (it) | 1972-07-27 | 1973-07-25 | Pigmenti della serie 2,4 diidrossichinolinica |
| AR249285A AR197249A1 (es) | 1972-07-27 | 1973-07-26 | Colorantes de pigmentos de la serie de la 2,4-dihidroxiquinolina y procedimiento para preparacion |
| GB3554173A GB1429983A (en) | 1972-07-27 | 1973-07-26 | Pigments of the 2,4-dihydroxyquinoline series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2236800A DE2236800A1 (de) | 1972-07-27 | 1972-07-27 | Pigmentfarbstoffe der 2,4-dihydroxychinolinreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2236800A1 true DE2236800A1 (de) | 1974-02-07 |
Family
ID=5851818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236800A Pending DE2236800A1 (de) | 1972-07-27 | 1972-07-27 | Pigmentfarbstoffe der 2,4-dihydroxychinolinreihe |
Country Status (10)
-
1972
- 1972-07-27 DE DE2236800A patent/DE2236800A1/de active Pending
-
1973
- 1973-07-09 CH CH999773A patent/CH574988A5/xx not_active IP Right Cessation
- 1973-07-19 AU AU58285/73A patent/AU5828573A/en not_active Expired
- 1973-07-24 FR FR7327009A patent/FR2194751B3/fr not_active Expired
- 1973-07-25 ZA ZA735062A patent/ZA735062B/xx unknown
- 1973-07-25 IT IT51649/73A patent/IT990015B/it active
- 1973-07-25 BR BR5621/73A patent/BR7305621D0/pt unknown
- 1973-07-25 JP JP48083215A patent/JPS4959835A/ja active Pending
- 1973-07-26 GB GB3554173A patent/GB1429983A/en not_active Expired
- 1973-07-26 AR AR249285A patent/AR197249A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4959835A (enrdf_load_html_response) | 1974-06-11 |
| BR7305621D0 (pt) | 1974-08-29 |
| ZA735062B (en) | 1974-07-31 |
| CH574988A5 (enrdf_load_html_response) | 1976-04-30 |
| FR2194751A1 (enrdf_load_html_response) | 1974-03-01 |
| GB1429983A (en) | 1976-03-31 |
| IT990015B (it) | 1975-06-20 |
| FR2194751B3 (enrdf_load_html_response) | 1976-07-09 |
| AU5828573A (en) | 1975-01-23 |
| AR197249A1 (es) | 1974-03-22 |
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