DE2544226A1 - Verfahren zur herstellung von gamma- chinacridon - Google Patents
Verfahren zur herstellung von gamma- chinacridonInfo
- Publication number
- DE2544226A1 DE2544226A1 DE19752544226 DE2544226A DE2544226A1 DE 2544226 A1 DE2544226 A1 DE 2544226A1 DE 19752544226 DE19752544226 DE 19752544226 DE 2544226 A DE2544226 A DE 2544226A DE 2544226 A1 DE2544226 A1 DE 2544226A1
- Authority
- DE
- Germany
- Prior art keywords
- quinacridone
- acid
- substituted
- ortho
- anilinoterephthalic
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000002253 acid Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 abstract description 20
- 239000007788 liquid Substances 0.000 abstract description 9
- 239000000049 pigment Substances 0.000 abstract description 8
- 239000003973 paint Substances 0.000 abstract description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 (ortho-substituted) anilinoterephthalic acid Chemical class 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- UCLFKAURHTUSJI-UHFFFAOYSA-N 2,3-bis(2-chloroanilino)terephthalic acid Chemical compound C=1C=CC=C(Cl)C=1NC=1C(C(=O)O)=CC=C(C(O)=O)C=1NC1=CC=CC=C1Cl UCLFKAURHTUSJI-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- YEIYQKSCDPOVNO-UHFFFAOYSA-N 5,8,9,12-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C(C=C2N3)=C1C=C2C(=O)C1=C3C=CCC1 YEIYQKSCDPOVNO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction 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
- C09B48/00—Quinacridones
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0027—Crystal modifications; Special X-ray patterns of quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51855874A | 1974-10-29 | 1974-10-29 | |
| US05/518,662 US3940399A (en) | 1974-10-29 | 1974-10-29 | Process for the production of gamma quinacridone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2544226A1 true DE2544226A1 (de) | 1976-05-13 |
Family
ID=27059512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752544226 Withdrawn DE2544226A1 (de) | 1974-10-29 | 1975-10-03 | Verfahren zur herstellung von gamma- chinacridon |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5933618B2 (ja) |
| CH (1) | CH619729A5 (ja) |
| DE (1) | DE2544226A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074587A2 (en) * | 1999-08-05 | 2001-02-07 | Ciba SC Holding AG | Gamma quinacridone pigment |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2844581A (en) * | 1957-11-22 | 1958-07-22 | Du Pont | Organic pigments |
| US3160510A (en) * | 1960-04-25 | 1964-12-08 | Du Pont | Quinacridone pigment compositions |
| US3257405A (en) * | 1961-10-02 | 1966-06-21 | Allied Chem | Preparation of quinacridone pigments |
| US3342823A (en) * | 1960-10-24 | 1967-09-19 | Allied Chem | Preparation of quinacridones using polyphosphoric acid |
-
1975
- 1975-10-03 DE DE19752544226 patent/DE2544226A1/de not_active Withdrawn
- 1975-10-14 JP JP12295775A patent/JPS5933618B2/ja not_active Expired
- 1975-10-29 CH CH1401475A patent/CH619729A5/de not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2844581A (en) * | 1957-11-22 | 1958-07-22 | Du Pont | Organic pigments |
| US3160510A (en) * | 1960-04-25 | 1964-12-08 | Du Pont | Quinacridone pigment compositions |
| US3342823A (en) * | 1960-10-24 | 1967-09-19 | Allied Chem | Preparation of quinacridones using polyphosphoric acid |
| US3257405A (en) * | 1961-10-02 | 1966-06-21 | Allied Chem | Preparation of quinacridone pigments |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074587A2 (en) * | 1999-08-05 | 2001-02-07 | Ciba SC Holding AG | Gamma quinacridone pigment |
| EP1074587A3 (en) * | 1999-08-05 | 2002-09-25 | Ciba SC Holding AG | Gamma quinacridone pigment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5165131A (ja) | 1976-06-05 |
| JPS5933618B2 (ja) | 1984-08-16 |
| CH619729A5 (en) | 1980-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8127 | New person/name/address of the applicant |
Owner name: MOBAY CHEMICAL CORP., 15205 PITTSBURGH, PA., US |
|
| 8125 | Change of the main classification |
Ipc: C09B 48/00 |
|
| 8130 | Withdrawal |