GB2216537A - Basic triphenodioxazine dyes with sulphonate ester groups - Google Patents
Basic triphenodioxazine dyes with sulphonate ester groups Download PDFInfo
- Publication number
- GB2216537A GB2216537A GB8903652A GB8903652A GB2216537A GB 2216537 A GB2216537 A GB 2216537A GB 8903652 A GB8903652 A GB 8903652A GB 8903652 A GB8903652 A GB 8903652A GB 2216537 A GB2216537 A GB 2216537A
- Authority
- GB
- United Kingdom
- Prior art keywords
- optionally substituted
- radical
- independently
- alkyl
- lower alkyl
- 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- Withdrawn
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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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
-
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Abstract
Novel triphenodioxazine dyes which are free from suphonic acid groups and have the formula: <IMAGE> wherein each of T<1> and T<2>, independently, represent H, C1, Sr, F or an optionally substituted alkyl or aryl radical; (A)n represents n substituents A each of which, independently, is lower alkyl, lower alkoxy, C1 or COOH and n is 0 or 1; R represents an optionally substituted hydrocarbon radical, preferably aryl; R<1> represents hydrogen or an optionally substituted lower alkyl radical; X represents an optionally substituted alkylene, aralkylene or arylene radical; each of R<2> and R<3>, independently, represents hydrogen or an optionally substituted hydrocarbon radical; R<4> represents hydrogen or an optionally substituted alkyl or aralkyl radical; Z<-> represents an anion, and a is 0 or 1. The dyes impart blue shades to textiles, leather, ink, lacquers, and cellulose, especially paper.
Description
TRIPHENODIOXAZINE DYES
This invention relates to triphenodioxazine dyes, to methods for their manufacture and to their use for dyeing cellulosic substrates.
According to the invention, there are provided triphenodioxazine dyes which are free from sulphonic acid groups and have the formula:
wherein each of T and T, independently, represents H, C1, Br, F or an optionally substituted alkyl or aryl radical; (A) represents n substituents A each of which, independently, is lower alkyl, lower alkoxy, C1 or COOH and n is O or 1;
R represents an optionally substituted hydrocarbon radical;
R represents hydrogen or an optionally substituted lower alkyl radical;
X represents an optionally substituted alkylene, aralkylene or arylene radical; each of R and R , independently, represents hydrogen or an optionally substituted hydrocarbon radical;
R4 represents hydrogen or an optionally substituted alkyl or aralkyl radical;
Z represents an anion, and a is O or 1.
The terms "lower alkyl" and "lower alkoxy" as used herein refer to alkyl and alkoxy groups having from 1 to 6 carbon atoms.
In general, lower alkyl and lower alkoxy groups having from 1 to 4 carbon atoms are preferred.
Examples of optionally substituted alkyl radicals which may be represented by T and T particularly include lower alkyl radicals. Examples of optionally substituted aryl radicals which may be so represented particularly include optionally substituted phenyl radicals, for example phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, dimethoxyphenyl, chlorophenyl, dichlorophenyl, methylchlorophenyl, methoxymethylphenyl, methoxychlorophenyl, aminophenyl and acetylaminophenyl. It is preferred thafl T and T2 are both chlorine.
In the groups (A) , n is preferably 0.
n The optionally substituted hydrocarbon radicals represented by R, R2 and R3 include optionally substituted alkyl, cycloalkyl, aralkyl and aryl radicals. In the case of R, the preferred radicals 2 and 3 are optionally substituted aryl radicals; R and R are preferably optionally substituted alkyl radicals, especially lower alkyl radicals.
The radicals represented by X are preferably alkylene or aralkylene radicals and as typical examples there may be mentioned ethylene, 1,2- and 1,3-propylene, 2-E-droxy-1,3-propylene, 1- and 2-phenyl-1,3-propylene, 1,4-, 2,3- and 2,4-butylene, 2-methyl1,3-propylene, 2-methyl-2,4-pentylene, 2,2-dimethyl-1,3-propylene, l-phenylethylene, l-chloro-2,3-propylene, 1,6- and 2,5-hexylene, 2,3-diphenyl-1,4-butylene, 1 (met".oxycarbonyl)- 1,5-pentylene, l-carboxy-1,5-pentylene, 2,7-heptylene, 3-methyl-1,6-hexylene, -CH2CH20CH2CR2-, -CH2CH2SCH2CH2-, -CH2CH2SSCH2CH2-,
R may be linked to both nitrogen atoms in the structure: 1 - X - NR2-.As examples of such a grouping there may be mentioned
Y is preferably a linear or branched chain alkylene radical containing from 2 to 6 carbon atoms and optionally containing one or more hydroxy or alkoxy substituents, for example an ethylene or propylene group optionally containing one hydroxy or methoxy substituent.
R4, when present, is preferably hydrogen or a lower alkyl radical.
The nature of the anion Z is not critical. Typical anions include halide, hydroxide, sulphate and acetate.
The dyes of Formula I may be prepared by the desulphonation of compounds of the formula:
with conversion to the salt or quaternary ammonium compound, the symbols T, T, n, R, X, R and R having the meanings already given; A1 representing lower alkyl, lower alkoxy, C1, COOH or S03H and R5 being an optionally substituted hydrocarbon radical, the nature of the substituents being such that the dye contains at least two SO3H groups.
Desulphonation of the compound of Formula (2) may be achieved by heating in the presence of a mineral acid, for example sulphuric acid, and preferably in the presence of sulphuric acid having a concentration in excess of 80% by weight. Suitable reaction temperatures are in the range of about 900C to about 1500C.
Conversion to the salt or quaternary ammonium compound may be achieved, either before or after desulphonation, by conventional weans, for example by treatment with the appropriate dialkyl sulphate or alkyl iodide. If substituents such as R and R are hydrogen, these may be converted to alkyl on treatment with an alkylating agent.
The dyes of Formula (2) may themselves be prepared by reacting 2,3,5,6-tetrachloro-1,4-benzoquinone (or a corresponding compound wherein T1 and T2 have the other meanings given above) with 2 moles of a diamine of the formula:
and heating the resulting dianilide in the presence of a strongly acid condensing agent, for example oleum, to effect ring closure.
The dyes of Formula (1), which may be isolated and, if necessary, purified by conventional means are basic triphenodioxazine dyes of blue shades useful for the coloration of materials such as textiles, leather, ink and lacquers. They have high tinctorial strengths and good light fastness on cellulosic substrates and have especially high affinity for paper, the backwaters from paper dyeing frequently being substantially clear.
Claims (3)
1. Triphenodioxazine dyes which are free from sulphonic acid groups and have the formula:
wherein each of T and T, independently, represents H, C1, Br, F or an optionally substituted alkyl or aryl radical; (A) n represents n substituents A each of which, independently, is lower alkyl, lower alkoxy, C1 or COOH and n is 0 or 1;
R represents an optionally substituted hydrocarbon radical;
R1 represents hydrogen or an optionally substituted lower alkyl radical;
X represents an optionally substituted alkylene, aralkylene or arylene radical; each of R and R , independently, represents hydrogen or an optionally substituted hydrocarbon radical;
R4 represents hydrogen or an optionally substituted alkyl or aralkyl radical; Z represents an anion, and a is 0 or 1.
2. A method for the preparation of a triphenodioxazine dye as defined in claim 1 which comprises desulphonating a compound of the formula:
followed by conversion to the appropriate salt form, the symbols T1, T, n, R, X, R and R having the meanings given in claim 1; A1 representing lower alkyl, lower alkoxy, C1, COOH or S03H and R5 being an optionally substituted hydrocarbon radical, the nature of the substituents being such that the dye contains at least two S03H groups.
3. A method of dyeing paper which comprises applying thereto a triphenodioxazine dye as defined in claim 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888805566A GB8805566D0 (en) | 1988-03-09 | 1988-03-09 | Triphenodioxazine dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8903652D0 GB8903652D0 (en) | 1989-04-05 |
| GB2216537A true GB2216537A (en) | 1989-10-11 |
Family
ID=10633101
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB888805566A Pending GB8805566D0 (en) | 1988-03-09 | 1988-03-09 | Triphenodioxazine dyes |
| GB8903652A Withdrawn GB2216537A (en) | 1988-03-09 | 1989-02-17 | Basic triphenodioxazine dyes with sulphonate ester groups |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB888805566A Pending GB8805566D0 (en) | 1988-03-09 | 1988-03-09 | Triphenodioxazine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB8805566D0 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2131823A (en) * | 1982-05-24 | 1984-06-27 | Ici Plc | Triphendioxazine dyes, methods for their manufacture and their use for dying cecculosic substrates |
| EP0279122A2 (en) * | 1987-01-20 | 1988-08-24 | Imperial Chemical Industries Plc | Reactive dyes |
-
1988
- 1988-03-09 GB GB888805566A patent/GB8805566D0/en active Pending
-
1989
- 1989-02-17 GB GB8903652A patent/GB2216537A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2131823A (en) * | 1982-05-24 | 1984-06-27 | Ici Plc | Triphendioxazine dyes, methods for their manufacture and their use for dying cecculosic substrates |
| EP0279122A2 (en) * | 1987-01-20 | 1988-08-24 | Imperial Chemical Industries Plc | Reactive dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8903652D0 (en) | 1989-04-05 |
| GB8805566D0 (en) | 1988-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |