GB815840A - New sulphur dyestuffs of the dioxazine series - Google Patents
New sulphur dyestuffs of the dioxazine seriesInfo
- Publication number
- GB815840A GB815840A GB34552/56A GB3455256A GB815840A GB 815840 A GB815840 A GB 815840A GB 34552/56 A GB34552/56 A GB 34552/56A GB 3455256 A GB3455256 A GB 3455256A GB 815840 A GB815840 A GB 815840A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- dioxazine
- amino
- treating
- followed
- 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 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 2
- 239000005864 Sulphur Substances 0.000 title abstract 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 5
- -1 dioxazine compound Chemical class 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 abstract 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- KYPCUWHXFBFCTI-UHFFFAOYSA-N 3-methoxydibenzofuran-2-amine Chemical compound O1C2=CC=CC=C2C2=C1C=C(OC)C(N)=C2 KYPCUWHXFBFCTI-UHFFFAOYSA-N 0.000 abstract 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 abstract 1
- OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 abstract 1
- LRSYZHFYNDZXMU-UHFFFAOYSA-N 9h-carbazol-3-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3NC2=C1 LRSYZHFYNDZXMU-UHFFFAOYSA-N 0.000 abstract 1
- VDOSWXIDETXFET-UHFFFAOYSA-N Afloqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC(N)=CC=C2N=C1CF VDOSWXIDETXFET-UHFFFAOYSA-N 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- KSDIHKMNSYWRFB-UHFFFAOYSA-N chrysen-2-amine Chemical compound C1=CC=CC2=CC=C3C4=CC=C(N)C=C4C=CC3=C21 KSDIHKMNSYWRFB-UHFFFAOYSA-N 0.000 abstract 1
- UDEJDSKJVZDGHD-UHFFFAOYSA-K copper potassium acetic acid hydroxy-(oxido(dioxo)chromio)oxy-dioxochromium sulfate Chemical compound S(=O)(=O)([O-])[O-].[Cu+2].C(C)(=O)O.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)O.[K+] UDEJDSKJVZDGHD-UHFFFAOYSA-K 0.000 abstract 1
- FFYZMBQLAYDJIG-UHFFFAOYSA-N dibenzofuran-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3OC2=C1 FFYZMBQLAYDJIG-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B49/00—Sulfur dyes
- C09B49/06—Sulfur dyes from azines, oxazines, thiazines or thiazoles
-
- 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)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises sulphur dyestuffs of the dioxazine series and a process for making them by transforming a dioxazine compound of the general formula <FORM:0815840/IV (c)/1> (wherein R is an iso- or heterocyclic residue which may be substituted and X is is halogen) or a sulphonic acid thereof into a corresponding sulphochloride and treating it with an acidic reducing agent. The sulphochlorides are made by treating a dioxazine of the above formula with chlorosulphonic acid at up to 150 DEG C. or by treating a sulphonic acid thereof with phosphorus pentachloride or chlorosulphonic acid. Acid reducing agents specified are mixtures of water and hydrochloric acid with iron powder, zinc dust or stannous chloride. In examples, the dioxazines derived from chloranil and (1) aniline; (2) 1-amino-2-methoxy-5-methyl-benzene; (3) dehydrothiotoluidine followed by ring closure with organic acid halides, phosphorus halides or ferric chloride in nitrobenzene, and the corresponding dioxazine containing no methyl substituents, (4) a - and b -naphthylamine; (5) 2-aminodiphenylene oxide or 2-amino-3-methoxydiphenylene oxide; (6) p-aminodiphenyl; (7) o-aminodiphenyl ether; (8) 3-aminocarbazole and 3-amino-N-ethyl-carbazole; (9) 3-aminopyrene; (10) 2-amino-chrysene; and (11) 2-aminoflourene followed by ring closure by boiling in nitrobenzene, are treated with chlorosulphonic acid and reduced. The dyestuffs dye vegetable fibres such as cotton red, purple, violet and blue shades from a sodium sulphide vat followed by air or potassium dichromate oxidation. The shades may be brightened and fastness improved by an aftertreatment with perborates, percarbonates or potassium dichromate-acetic acid-copper sulphate. Specifications 886/1912 [Class 2 (Iii)], and 416,887 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE815840X | 1955-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815840A true GB815840A (en) | 1959-07-01 |
Family
ID=6734850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34552/56A Expired GB815840A (en) | 1955-11-23 | 1956-11-12 | New sulphur dyestuffs of the dioxazine series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815840A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3495928A (en) * | 1964-11-20 | 1970-02-17 | Ciba Ltd | Dyeing process |
| US3503880A (en) * | 1966-10-14 | 1970-03-31 | Du Pont | Yarn |
| CN104387794A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Blue reactive dye and preparation method thereof |
| CN104387796A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Reactive dye and preparation method thereof |
| CN104387795A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Reactive blue dye and preparation method thereof |
-
1956
- 1956-11-12 GB GB34552/56A patent/GB815840A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3495928A (en) * | 1964-11-20 | 1970-02-17 | Ciba Ltd | Dyeing process |
| US3503880A (en) * | 1966-10-14 | 1970-03-31 | Du Pont | Yarn |
| CN104387794A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Blue reactive dye and preparation method thereof |
| CN104387796A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Reactive dye and preparation method thereof |
| CN104387795A (en) * | 2014-09-26 | 2015-03-04 | 天津德凯化工股份有限公司 | Reactive blue dye and preparation method thereof |
| CN104387796B (en) * | 2014-09-26 | 2019-01-22 | 天津德凯化工股份有限公司 | A kind of reactive dye and preparation method thereof |
| CN104387794B (en) * | 2014-09-26 | 2019-08-13 | 天津德凯化工股份有限公司 | A kind of blue active dye and preparation method thereof |
| CN104387795B (en) * | 2014-09-26 | 2019-08-13 | 天津德凯化工股份有限公司 | A kind of reactive blue dye and preparation method thereof |
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