GB1039926A - Improvements relating to dyestuffs of the dioxazine series and their use - Google Patents
Improvements relating to dyestuffs of the dioxazine series and their useInfo
- Publication number
- GB1039926A GB1039926A GB3508163A GB3508163A GB1039926A GB 1039926 A GB1039926 A GB 1039926A GB 3508163 A GB3508163 A GB 3508163A GB 3508163 A GB3508163 A GB 3508163A GB 1039926 A GB1039926 A GB 1039926A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- aryl
- radicals
- aryl radicals
- primary
- 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
- 150000005125 dioxazines Chemical class 0.000 title 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 5
- 150000005840 aryl radicals Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- 239000000049 pigment Substances 0.000 abstract 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 naphthyl radicals Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- BVLLNHZIXWWTEW-UHFFFAOYSA-N CCCCCCCCOC(C1=CC=CC=C1C(OCCCCCCCC)=O)=O.Cl Chemical compound CCCCCCCCOC(C1=CC=CC=C1C(OCCCCCCCC)=O)=O.Cl BVLLNHZIXWWTEW-UHFFFAOYSA-N 0.000 abstract 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- IIGAELMXVLEZPM-GRVYQHKQSA-L cobalt(2+);(9z,12z)-octadeca-9,12-dienoate Chemical compound [Co+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O IIGAELMXVLEZPM-GRVYQHKQSA-L 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000012975 dibutyltin dilaurate Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Abstract
Dioxazine dyes and pigments are obtained by reacting a compound of formula <FORM:1039926/C4-C5/1> with a primary aryl amine to yield a compound of formula <FORM:1039926/C4-C5/2> which compounds are then ring closed to form the dioxazine dyes of formula <FORM:1039926/C4-C5/3> The intermediates of Formula II and the dyes of Formula III are novel and are claimed per se. In the above, R1 and R2 are aryl radicals, X1 and X2 are halogen or nitro substituents, especially bromine, A1 and A2 are aryl radicals of primary aryl amines and on ring closure give A11 and A12. The aryl amines preferably contain a replaceable alkoxy or aryloxy group in the o-position to the amino group. The first stage condensation is preferably carried out in presence of an acid binding agent both stages being carried out in an inert diluent either separately or in the same process. In Example 12, the pigment of formula <FORM:1039926/C4-C5/4> is mixed with alumina hydrate, linseed oil varnish and cobalt linoleate, the printing paste obtained having good colour strength and fastness to light.ALSO:Di-anils of general formula <FORM:1039926/C2/1> are prepared from compounds of formula <FORM:1039926/C2/2> by condensing with 2 moles of the same or different primary arylamines optionally in the presence of an inert organic diluent and/or a condensing agent. In the above Formulae II and I, X1 and X2 are halogen atoms or nitro groups, R1 and R2 are aryl radicals, A1 and A2 are the aryl radicals of the primary arylamines. The aryl radicals R1 and R2 are phenyl or naphthyl radicals which may be substituted, A1 and A2 are phenyl or naphthyl radicals which may be substituted.ALSO:In Example 13 the dioxazine pigment of formula <FORM:1039926/C3/1> is rolled with polyvinyl chloride dioctyl phthalate, dibutyl tin dilaurate and titanium dioxide. Red polyvinyl chloride sheets of good fastness to migration and light are obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1061062A CH417817A (en) | 1962-09-06 | 1962-09-06 | Process for the preparation of dyes of the dioxazine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1039926A true GB1039926A (en) | 1966-08-24 |
Family
ID=4365015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3508163A Expired GB1039926A (en) | 1962-09-06 | 1963-09-05 | Improvements relating to dyestuffs of the dioxazine series and their use |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH417817A (en) |
| DE (1) | DE1444772A1 (en) |
| DK (1) | DK107631C (en) |
| GB (1) | GB1039926A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014181348A2 (en) | 2013-04-26 | 2014-11-13 | Keki Hormusji Gharda | Carbazole dioxazine pigments |
| EP3008133A4 (en) * | 2013-06-11 | 2016-11-02 | Keki Hormusji Gharda | Carbazole dioxazine pigment and a method for its preparation |
-
1962
- 1962-09-06 CH CH1061062A patent/CH417817A/en unknown
-
1963
- 1963-09-05 GB GB3508163A patent/GB1039926A/en not_active Expired
- 1963-09-05 DK DK419163A patent/DK107631C/en active
- 1963-09-05 DE DE19631444772 patent/DE1444772A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014181348A2 (en) | 2013-04-26 | 2014-11-13 | Keki Hormusji Gharda | Carbazole dioxazine pigments |
| EP2989102A4 (en) * | 2013-04-26 | 2016-10-19 | Keki Hormusji Gharda | Carbazole dioxazine pigments |
| EP3008133A4 (en) * | 2013-06-11 | 2016-11-02 | Keki Hormusji Gharda | Carbazole dioxazine pigment and a method for its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DK107631C (en) | 1967-06-19 |
| DE1444772A1 (en) | 1969-03-20 |
| CH417817A (en) | 1966-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3867404A (en) | New isoindolinone pigments and process for their manufacture | |
| US1821043A (en) | Hydroaryl amino anthraquinone compounds and process of making the same | |
| GB1111037A (en) | Disperse dyestuffs of the anthrapyridone and anthrapyrimidone series | |
| US3022298A (en) | Dioxazine dyestuffs | |
| GB1039926A (en) | Improvements relating to dyestuffs of the dioxazine series and their use | |
| US2954378A (en) | Dioxazine dyestuffs | |
| US3030353A (en) | Conversion products of azo dyestuffs containing heavy metal bound in complex linkage | |
| US4016157A (en) | Metal complexes of bis-hydrazones | |
| US3320279A (en) | Reaction product of naphtholactams and indole derivatives as dyestuffs | |
| US2176630A (en) | Alkyl sulphone dyestuffs of the anthraquinone series | |
| US2134505A (en) | Dyestuff-sulphonic acids of the dioxazine series and process of preparing them | |
| US2099673A (en) | 1-acyl-amino-anthraquinone-6-thiazoles | |
| US2792397A (en) | Quinazoline-amino-anthraquinone dyestuffs | |
| US1901048A (en) | Preparation of new dyestuffs of the anthraquinone series | |
| US2628230A (en) | Azo dyes of the anthraquinone series | |
| US2049189A (en) | Carbon compounds of the anthraquinone series | |
| US2101094A (en) | Arylamino anthraquinone dyestuffs and process for their manufacture | |
| US2001737A (en) | Anthraquinone derivatives | |
| DE2614201A1 (en) | UNSYMMETRIC 1 TO 2 CHROME COMPLEXES CONTAINING AN AZO AND AN AZOMETHINE COMPLEX | |
| US1838270A (en) | Azo dyestuffs from 2.3-hydroxynaphthoic acid arylids and process of making the same | |
| US3935248A (en) | Anthraquinone dyes | |
| US1908099A (en) | Dye of the naphtho-phenazine series and process of making it | |
| CH620237A5 (en) | ||
| US2555973A (en) | Halogenated derivatives of the naphthoquinone-imine series and a process of making same | |
| DE2342815A1 (en) | NEW DIOXAZINE DYES |