GB832400A - New anthraquinonoid dyestuffs - Google Patents
New anthraquinonoid dyestuffsInfo
- Publication number
- GB832400A GB832400A GB23090/57A GB2309057A GB832400A GB 832400 A GB832400 A GB 832400A GB 23090/57 A GB23090/57 A GB 23090/57A GB 2309057 A GB2309057 A GB 2309057A GB 832400 A GB832400 A GB 832400A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthraquinone
- reacted
- amino
- cyanuric chloride
- formula
- 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
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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/082—Azo dyes dyes containing in the molecule at least one azo group and at least one other chromophore 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- General Factory Administration (AREA)
Abstract
The invention comprises dyestuffs which in the form of their free acids are of the formula <FORM:0832400/IV(c)/1> where X is a bridging group containing at least one anionic solubilizing group, Y is a chlorine or bromine atom, Q is an oxygen or sulphur atom or -NR1-, and R and R1 may be the same or different and R is hydrogen or a hydrocarbon or substituted hydrocarbon radical having no dyestuff character and R1 is hydrogen, alkyl or substituted alkyl, and a process for making the dyestuffs by interacting a cyanuric chloride or bromide on the one hand with a compound of the formula <FORM:0832400/IV(c)/2> and on the other hand with a compound of the formula H-Q-R, under such conditions that the product still contains a halogen atom attached to the triazine ring. Hydrocarbon or substituted hydrocarbon radicals represented by R include methyl, beta-ethoxyethyl, cyclohexyl, benzyl, phenyl, tolyl, chlorophenyl and sulphophenyl, radicals represented by R1 include methyl and beta-ethoxyethyl, and R and R1 may be joined to form an N-morpholino radical. Bridging groups represented by X include phenylene and diphenylene radicals and the radical -C6H4- -N = N-C6H4- each of which is substituted by at least one anionic water-solubilizing groups such as sulphonic acid or carboxylic acid and may be further substituted by methyl, methoxy or chloro groups. Compounds of the formula H-Q-R include methanol, ethanol, iso-butanol, octanol, beta-ethoxyethanol, cyclohexanol, benzyl alcohol, phenylethyl alcohol, phenol, o-, m- and p-cresols, xylenols, chlorophenols, sulphophenols, dialkylaminophenols, sulphonaphthols, ammonia, methylamine, diethylamine, hydroxyethylamine, taurine, glycine, benzylamine, cyclohexylamine, aniline, toluidine, chloroaniline, anisidine, aminoacetanilide, orthanilic, metanilic and sulphanilic acids, thiophenol, thiocresol and p-sulphothiophenol. The reaction may be conducted at between 15 DEG and 50 DEG C. at a pH between 4 and 7 in aqueous medium in the presence of an acid-binding agent. The dyes colour cellulose textiles, wool, silk, and fibres of ardein, casein, polyamide or modified polyacrylonitrile greenish blue and green shades. In examples: 1-amino-4-(41-aminoanilino) anthraquinone - 2 : 31 : 5 - trisulphonic acid is reacted with cyanuric chloride; and (2) ammonia, (5) sodium 4-acetylamino phenate, (6) phenol, (7) thio - p - cresol, (8) o - cresol, (9) 4 - methoxyphenol, (10) 3 - (N : N - diethylamino)-phenol and (11) 3-sulphoaniline, or with (1) 2 : 4 - dichloro - 6 - methoxy - s - triazine; in further examples, (3) sodium 1-amino-4-(41-[411 - aminostyryl]anilino) - anthraquinone-2 : 211 : 31 : 5 - tetrasulphonate is reacted with 2 - betamethoxyethoxy - 4 : 6 - dichloro - s-triazine: (4) sodium 1 - amino - 4 - (41 - [411-aminophenyl] - anilino) - anthraquinone - 2 : 311 : 5-trisulphonate is reacted with cyanuric chloride and sodium metanilate; (12) 1-amino-4-(41-aminoanilino) anthraquinone - 2 : 31 : 6 - trisulphonic acid is reacted with cyanuric chloride and methanol; and (13) 1 - amino - 4 - (41-[411 - aminobenzeneazo] anilino) anthraquinone - 2 : 211 : 5 - tri sulphonic acid is reacted with cyanuric chloride and 3-sulphoaniline. The Provisional Specification also relates to dyestuffs of the above general formula where Q is a direct linkage and where R may be a hydrocarbon or substituted hydrocarbon radical in general. Specification 798,121 also is referred to.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB23090/57A GB832400A (en) | 1954-11-29 | 1957-07-22 | New anthraquinonoid dyestuffs |
NL229473D NL229473A (en) | 1957-07-22 | 1958-07-10 | |
FR770481A FR73851E (en) | 1954-11-29 | 1958-07-17 | Anthraquinonoid coloring matter |
CH6193658A CH362777A (en) | 1957-07-22 | 1958-07-18 | Process for the production of new anthraquinone dyes |
US749341A US3065191A (en) | 1957-07-22 | 1958-07-18 | Disulpho-1-amino-4-(oxy-, thio-, or aminosubstituted-monohalogenotriazinylamino-aryl-or arylazo-amino) anthraquinone dyestuffs |
BE569903D BE569903A (en) | 1954-11-29 | 1958-07-19 | |
DEI15140A DE1210504B (en) | 1957-07-22 | 1958-07-22 | Process for the preparation of anthraquinone dyes |
NL2209473A NL121092C (en) | 1957-07-22 | 1964-01-27 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3450154A GB781930A (en) | 1954-11-29 | 1954-11-29 | New anthraquinonoid dyestuffs |
GB23090/57A GB832400A (en) | 1954-11-29 | 1957-07-22 | New anthraquinonoid dyestuffs |
Publications (1)
Publication Number | Publication Date |
---|---|
GB832400A true GB832400A (en) | 1960-04-13 |
Family
ID=37499976
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23090/57A Expired GB832400A (en) | 1954-11-29 | 1957-07-22 | New anthraquinonoid dyestuffs |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE569903A (en) |
FR (1) | FR73851E (en) |
GB (1) | GB832400A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2418256A1 (en) * | 1978-02-28 | 1979-09-21 | Ciba Geigy Ag | AZO (HYDRAZO) -ANTHRAQUINONE COMPOUNDS AND THEIR PREPARATION PROCESS |
US4214082A (en) * | 1978-04-22 | 1980-07-22 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4325705A (en) | 1978-12-16 | 1982-04-20 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4355163A (en) | 1978-12-06 | 1982-10-19 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4377688A (en) * | 1978-12-16 | 1983-03-22 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs, their preparation and their use for dyeing materials containing OH groups or amide groups |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4667403A (en) * | 1984-05-16 | 1987-05-26 | Siemens Aktiengesellschaft | Method for manufacturing electronic card modules |
FR2569595B1 (en) * | 1984-08-30 | 1987-02-13 | Cit Alcatel | FLEXIBLE WORKSHOP FOR MANUFACTURING MECHANICAL AND / OR ELECTRICAL ASSEMBLIES |
NL8501552A (en) * | 1985-05-30 | 1986-12-16 | Multinorm Bv | COMMUNICATION SYSTEM. |
-
1957
- 1957-07-22 GB GB23090/57A patent/GB832400A/en not_active Expired
-
1958
- 1958-07-17 FR FR770481A patent/FR73851E/en not_active Expired
- 1958-07-19 BE BE569903D patent/BE569903A/fr unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2418256A1 (en) * | 1978-02-28 | 1979-09-21 | Ciba Geigy Ag | AZO (HYDRAZO) -ANTHRAQUINONE COMPOUNDS AND THEIR PREPARATION PROCESS |
US4216146A (en) * | 1978-02-28 | 1980-08-05 | Ciba-Geigy Ag | Azo(hydrazo)-anthraquinone compounds |
US4214082A (en) * | 1978-04-22 | 1980-07-22 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4355163A (en) | 1978-12-06 | 1982-10-19 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4325705A (en) | 1978-12-16 | 1982-04-20 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
US4377688A (en) * | 1978-12-16 | 1983-03-22 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs, their preparation and their use for dyeing materials containing OH groups or amide groups |
Also Published As
Publication number | Publication date |
---|---|
BE569903A (en) | 1961-06-02 |
FR73851E (en) | 1960-09-12 |
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