GB926998A - New water-soluble azo dyestuffs containing phosphonium groups - Google Patents
New water-soluble azo dyestuffs containing phosphonium groupsInfo
- Publication number
- GB926998A GB926998A GB1438860A GB1438860A GB926998A GB 926998 A GB926998 A GB 926998A GB 1438860 A GB1438860 A GB 1438860A GB 1438860 A GB1438860 A GB 1438860A GB 926998 A GB926998 A GB 926998A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- amino
- chloroethyl
- toluidine
- tri
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Quaternary phosphonium halides for use in the preparation of water soluble azo dyes (see Group IV(c)) are obtained by reacting substituted alkyl halides with tertiary phosphines, the substituted alkyl halides being selected from p-aminophenacyl chloride, p-nitrobenzyl chloride, b -(p-aminophenyl-oxycarbonyl) ethyl chloride, p-nitrophenyl beta-chloroethyl sulphone or sulphoxide, p-aminophenyl b -chloroethyl ether, p-acetamidophenyl b -chloroethyl ketone, N-ethyl-N-b -bromo-ethyl-aniline, N-methyl-N-b -(chloroacetoxy) ethyl-aniline, N - methyl-N-b -chloroethyl-m-chloro-aniline, N - ethyl - N - (g -chloro - b -hydroxypropyl)-1-naphthylamine, N-b - methoxyethyl-N - g - chloropropyl - m - toluidine, N:N-bis (b -chloroethyl)-m-toluidine, m - (chloroaceta - mido)N:N-diethylaniline, N-ethyl-N-b -bromo-ethyl-m-toluidine, N - b - cyanoethyl - N - b 1-chloroethyl-m-toluidine and the tertiary phosphines being selected from phenyl dimethyl-, tri-n-butyl-, triethyl-, triphenyl-, tris-(hydroxymethyl)-, ethyldimethyl-, ethyl diphenyl-and triethylphosphines. The nitro compounds are reduced to the corresponding amino compounds e.g. by catalytic hydrogenation.ALSO:The invention comprises water-soluble azo dyes which are devoid of sulphonic and carboxylic groups and which contain one or more groups of the formula <FORM:0926998/IV(a)/1> wherein the phosphorus atom is directly attached to a carbon atom of the dye and wherein R1, R2 and R3 are organic radicals, the same or different, each having a carbon atom linked directly to the phosphorus atom and Z is an anion and processes for the preparation thereof wherein (a) a diazotized diazo component is coupled with a coupling component provided that both the said components are devoid of sulphonic and carboxylic acid groups and that one or both of said components contains at least one group of the formula <FORM:0926998/IV(a)/2> directly attached to a carbon atom or (b) a water-insoluble azo dye containing a halogen atom attached to an aliphatic carbon atom is reacted with a tertiary phosphine of the formula P (R1) (R2) (R3) where R1, R2 and R3 have the meanings given above. Representative of the many diazo components specified are m-amino-phenyl trimethyl-; phenyl dimethyl-p-amino-phenacyl-; triethyl-b -(p-aminophenoxy)ethyl; triallyl-p-aminophenacyl-; 2-thienyl diethyl-p-aminophenacyl-; triethyl-b -(p-aminophenylsulphoxy- and sulphonyl)ethyl-; trimethyl-b -(p-aminophenyl-sulphonamido)ethyl-; tri-n-butyl-b -(p-aminophenylcarbonyloxy)ethyl-; phenyldimethyl p-aminophenyloxycarbonylmethyl-; trimethyl-b -amino-1-naphthylsulphonamido)ethyl-; and (p-aminobenzyl)tri-n-butyl phosphonium chlorides, trimethyl-p-aminophenacylphosphonium bromide and trischloromethyl-p-aminophenacylphosphonium iodide. Representative of the coupling components specified are Y-[N-ethyl-N-(3-methylphenyl)amino] propyldimethyl phenyl-; b -[N-b 1methoxyethyl-N-(3- methylphenyl) amino]ethyl dimethyl-; tri-n-butyl-g -(N-ethyl-N-1-naphthylamino)b -hydroxypropyl;- b -[N ethyl-N-(3-trifluoromethylphenyl)amino) ethyl] tri-n-butyl- and b -(N-cyanoethyl-N-m-tolylamino)ethyl] triethylphosphonium chlorides, N:N-bis-[b -di-n-butylphosphino)ethyl]m - toluidine P:P1-di-n-butochloride and [b -(N-b -cyanoethyl-N-m-tolylamino)ethyl] triethylphosphonium chloride. Additional coupling component specified include 2-amino- and 2-amino-6-cyano-, nitro, thiocyano and -methylsulphonylbenzythiazole, N:N-diacetoxyethylaniline, phenols, ketomethylene coupling components such as acetoacetanilide and 1-phenyl-3-methyl-pyrazolone and its derivatives. Representative of the phosphines specified are tris(hydroxyethyl)-; 2-thionyldiethyl-, phenyldiethyl, ethylphenyl-benzyl and triallyl phosphines. The dyes are particularly suitable for textile materials comprising polymers and copolymers of acrylonitrile and dicyanoethylene. Examples are furnished. The preparation of quaternary phosphonium halides for use in the processes is described (see Group IV(b)).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1438860A GB926998A (en) | 1960-04-25 | 1960-04-25 | New water-soluble azo dyestuffs containing phosphonium groups |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1438860A GB926998A (en) | 1960-04-25 | 1960-04-25 | New water-soluble azo dyestuffs containing phosphonium groups |
Publications (1)
Publication Number | Publication Date |
---|---|
GB926998A true GB926998A (en) | 1963-05-22 |
Family
ID=10040291
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1438860A Expired GB926998A (en) | 1960-04-25 | 1960-04-25 | New water-soluble azo dyestuffs containing phosphonium groups |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB926998A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3320321A (en) * | 1963-06-28 | 1967-05-16 | American Cyanamid Co | Phosphonium ethyl amine derivatives |
CN105873936A (en) * | 2013-11-22 | 2016-08-17 | 医药研究委员会 | Mitochondria-targeted dicarbonyl sequestering compounds |
EP4055018A4 (en) * | 2019-11-06 | 2024-01-10 | Nocion Therapeutics Inc | Phosphonium ion channel blockers and methods for use |
-
1960
- 1960-04-25 GB GB1438860A patent/GB926998A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3320321A (en) * | 1963-06-28 | 1967-05-16 | American Cyanamid Co | Phosphonium ethyl amine derivatives |
CN105873936A (en) * | 2013-11-22 | 2016-08-17 | 医药研究委员会 | Mitochondria-targeted dicarbonyl sequestering compounds |
US9963474B2 (en) * | 2013-11-22 | 2018-05-08 | Medical Research Council | Mitochondria-targeted dicarbonyl sequestering compounds |
CN105873936B (en) * | 2013-11-22 | 2018-09-14 | 医药研究委员会 | Mitochondrially targeted dicarbapentaborane chelate compound |
EP4055018A4 (en) * | 2019-11-06 | 2024-01-10 | Nocion Therapeutics Inc | Phosphonium ion channel blockers and methods for use |
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