GB828052A - Linear quinacridone pigments - Google Patents
Linear quinacridone pigmentsInfo
- Publication number
- GB828052A GB828052A GB22616/56A GB2261656A GB828052A GB 828052 A GB828052 A GB 828052A GB 22616/56 A GB22616/56 A GB 22616/56A GB 2261656 A GB2261656 A GB 2261656A GB 828052 A GB828052 A GB 828052A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phase
- salt
- milling
- crude
- give
- 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
- 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 title abstract 3
- 239000000049 pigment Substances 0.000 title abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 9
- 238000003801 milling Methods 0.000 abstract 5
- 238000004519 manufacturing process Methods 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
- 239000008096 xylene Substances 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
- C09B48/00—Quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises pigments which consist of or comprise quinacridones of the formula <FORM:0828052/IV(c)/1> wherein R is hydrogen, halogen, alkyl or alkoxy of 1-4 carbon atoms and which have a surface area of at least 60 square metres per gram. The invention also comprises a method of preparing the above by oxidation of the corresponding 6,13-dihydro bodies (prepared according to Specification 828,051). The substance in which R is hydrogen, i.e. quin-(2,3b)-acridine-7,14-(5,12)-dione is stated to exist in three crystal phases, a -, b -, and g -, each characterized by a particular X-ray diffraction pattern, and the invention claims these phases separately, having the surface area above referred to, and methods of producing them which are (1) production of a -phase by salt-milling or acid-pasting the crude quinacridone, (2) production of b -phase by salt-milling in presence of an aromatic or halogenated aromatic hydrocarbon; (3) production of g -phase by (a) treating the crude with dimethylformamide after salt milling, but before separating it from the salt, or (b) treating the crude with dimethyl formamide before and during salt milling. Examples describe (1) the oxidation of quin-(2,3b)-6,13-dihydro-acridine-7,14(5,12)-dione with nitrobenzene-m-sodium sulphonate in aqueous-alcoholic or -ethylene glycol solution in presence of caustic soda (other oxidizing agents specified are air and sodium polysulphide), and also (2) the saltmilling with sodium chloride, or acid-posting with sulphuric acid of the crude quinacridone so obtained to give the a -phase, (3) the salt-milling of the crude in presence of xylene to give the b -phase, and (4) the two treatments with dimethyl formamide above specified to give the gamma phase. A further example describes the manufacture of a lake from the a -phase and hydrogenated rosin by precipitation with calcium chloride from alkaline aqueous solution.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US828052XA | 1955-07-22 | 1955-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB828052A true GB828052A (en) | 1960-02-10 |
Family
ID=22173574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22616/56A Expired GB828052A (en) | 1955-07-22 | 1956-07-20 | Linear quinacridone pigments |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB828052A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157659A (en) * | 1959-10-10 | 1964-11-17 | Basf Ag | Process for preparing 2, 9-dichloro-quinacridone |
| US3257405A (en) * | 1961-10-02 | 1966-06-21 | Allied Chem | Preparation of quinacridone pigments |
| US3264298A (en) * | 1962-02-26 | 1966-08-02 | American Cyanamid Co | Quinacridone pigments |
| US3264300A (en) * | 1963-04-30 | 1966-08-02 | American Cyanamid Co | 2, 9-dimethylquinacridone in a "yellow" crystalline form |
| US3272821A (en) * | 1962-04-26 | 1966-09-13 | Eastman Kodak Co | Delta form of quinacridone pigment |
| EP0363759A3 (en) * | 1988-10-12 | 1991-09-04 | Bayer Ag | Process for the manufacture of a possibly substituted quinacridone |
| US6402829B1 (en) | 2000-12-20 | 2002-06-11 | Sun Chemical Corporation | Process for preparing a substantially pure gamma phase quinacridone pigment of large particle size |
-
1956
- 1956-07-20 GB GB22616/56A patent/GB828052A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157659A (en) * | 1959-10-10 | 1964-11-17 | Basf Ag | Process for preparing 2, 9-dichloro-quinacridone |
| US3257405A (en) * | 1961-10-02 | 1966-06-21 | Allied Chem | Preparation of quinacridone pigments |
| US3264298A (en) * | 1962-02-26 | 1966-08-02 | American Cyanamid Co | Quinacridone pigments |
| US3272821A (en) * | 1962-04-26 | 1966-09-13 | Eastman Kodak Co | Delta form of quinacridone pigment |
| US3264300A (en) * | 1963-04-30 | 1966-08-02 | American Cyanamid Co | 2, 9-dimethylquinacridone in a "yellow" crystalline form |
| EP0363759A3 (en) * | 1988-10-12 | 1991-09-04 | Bayer Ag | Process for the manufacture of a possibly substituted quinacridone |
| US5093497A (en) * | 1988-10-12 | 1992-03-03 | Bayer Aktiengesellschaft | Process for the preparation of a substituted or unsubstituted quinacridone |
| US6402829B1 (en) | 2000-12-20 | 2002-06-11 | Sun Chemical Corporation | Process for preparing a substantially pure gamma phase quinacridone pigment of large particle size |
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