GB749308A - Manufacture of triphenylmethane dyestuffs - Google Patents
Manufacture of triphenylmethane dyestuffsInfo
- Publication number
- GB749308A GB749308A GB33022/52A GB3302252A GB749308A GB 749308 A GB749308 A GB 749308A GB 33022/52 A GB33022/52 A GB 33022/52A GB 3302252 A GB3302252 A GB 3302252A GB 749308 A GB749308 A GB 749308A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- sodium
- sulphonate
- sulpho
- methyl
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Detergent Compositions (AREA)
- Coloring (AREA)
Abstract
Asymmetrical triphenylmethane dyes are made by reacting, at raised temperature, with a primary or secondary amine other than a diarylamine, a compound of the formula:- <FORM:0749308/IV(c)/1> in which R1 represents hydrogen or an aliphatic or cycloaliphatic radical, R2 represents an aromatic radical, and X represents halogen or alkoxy, and in which the benzene nucleus carrying the sulpho group may contain substituents prepared according to Specification 749,908. The invention includes the products of the formula:- <FORM:0749308/IV(c)/2> in which R1 and R3 each represent hydrogen or an aliphatic or cycloaliphatic radical, R2 is an aromatic radical, and R4 is an acyclic, isocyclic or heterocyclic radical, in which the benzene nucleus carrying the sulpho group may contain substituents e.g. halogen, alkoxy, carboxy, or sulpho in 41-position and group <FORM:0749308/IV(c)/3> is different from <FORM:0749308/IV(c)/4> The products may be sulphonated. In examples, compounds of the first of the above formula in which X is chlorine and in which the radical <FORM:0749308/IV(c)/5> is the radical of the first of each of the following pairs of amines, are each reacted with the second amine of the same pair, the phenyl radical containing the sulpho group being otherwise unsubstituted or substituted para to the central carbon atom as indicated in squared brackets, (1) p-anisidine and 1-amino -4- methoxybenzene -3- sulphonate, (2) 1-amino -2- hydroxybenzene -3- carboxylic acid and 4-aminodiphenylamine -2- sulphonic acid, (3) o-trifluoromethylaniline and 2, 6-dimethyl-aniline, (4) o-trifluoromethylaniline and sodium methylamino ethane-sulphonate, (5) 2-amino-N-ethyl-carbazole and sodium methylamino ethane-sulphonate, (6) 2, 4, 6-trimethylaniline and 1-amino -4- cyclohexylbenzene, (7) 2-amino-N-ethylcarbazole and 1-amino -2- hydroxy -5- sulpho -3- benzoic acid, (8) 1-amino -4- hydroxybenzene -3- carboxylic acid and sodium 1-amino -2- hydroxy -5- sulpho -3- benzoate, (9) sodium 1-amino -2- hydroxy -3- carboxy -5- benzene sulphonate and p-phenetidine, (10) sodium 1-amino -2- hydroxy -3- carboxy -5- benzene sulphonate and 1-amino -2- hydroxy-benzene -3- carboxylic acid, (11) o-methyl -N- methylaniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate, [sulpho] (12) o-methyl-N-methyl-aniline and sodium 1-amino-4-methylbenzene-3-sulphonate [sulpho], (13) o-methyl-N-methyl-aniline and sodium 1-amino -4- hydroxy -3- benzoate [sulpho], (14) aniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate [sulpho], (15) 2, 6-dimethylaniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate [methoxy], (16) 2, 4, 6-trimethylaniline and 1-amino -4- methylbenzene -3- sulphonic acid [carboxy], (17) p-anisidine and sodium 1-aminobenzene -4- sulphonate, (18) p-aminoacetanilide and sodium 1-aminobenzene -4- sulphonate, (19) 1-amino -2- methoxy -N- diethyl-sulphonamide-benzene and sodium 1-aminobenzene -4- sulphonate, (20) aniline and sodium 1-aminobenzene -4- sulphonate, (21) 2. 6-dimethylaniline and sodium methylamino ethane sulphonate, (22) p-aminoazobenzene and sodium methylamino ethane sulphonate, (23) 1-aminobezene -4- (2-hydroxyethyl)-sulphone and 2, 6-dimethylaniline, (24) 4-amino -3- methyl-diphenyl and 2, 2, 6-dimethylaniline, (25) 2-methyl -6- chlor-aniline and 2, 6-dimethylaniline, (26) 4-amino -3- methyl-diphenyl and sodium 1-amino -4- methoxybenzene -3- sulphonate, (27) p-anisidine and diethylamine, (28) N-methylaniline and diisobutylamine, (29) N-ethylaniline and n-butylamine, (30) 2-methyl -N- ethylaniline and 1-amino-2, 6-dimethylbenzene, (31) N-ethylaniline and N-butyl-aniline, (32) N-butylaniline and p-phenetidine, (33) N-ethylaniline and sodium 1-aminobenzene -2- sulphonate [chlorine], (34) 4-amino -2- sulpho-diphenylether and p-phenetidine [chlorine], (35) p-anisidine and 2, 4, 6-trimethylhexahydroaniline, (36) N-methylanline and 1, 2, 3, 4-tetrahydro -1- naphthylamine, (37) N-ethylaniline and N-cyclohexyl -otoluidine, (38) N-methylaniline and cyclohexylamine. Other starting materials are referred to. The products dye wool or silk blue to red shades. Specification 744,972 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE749308X | 1951-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB749308A true GB749308A (en) | 1956-05-23 |
Family
ID=6649261
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB33022/52A Expired GB749308A (en) | 1951-12-31 | 1952-12-30 | Manufacture of triphenylmethane dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB749308A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010100595A (en) * | 2007-11-19 | 2010-05-06 | Tokyo Ohka Kogyo Co Ltd | Resist composition, resist pattern-forming method, new compound and acid generator |
JP2014009330A (en) * | 2012-07-02 | 2014-01-20 | Chugai Kasei Co Ltd | Xanthene dye and its manufacturing method |
WO2014123124A1 (en) * | 2013-02-08 | 2014-08-14 | 大日本印刷株式会社 | Colorant dispersion liquid, manufacturing method for colorant dispersion liquid, colored resin composition for color filter, color filter, liquid crystal display device, and organic light-emitting display device |
WO2014192973A1 (en) * | 2013-05-31 | 2014-12-04 | 住友化学株式会社 | Compound and colored curable resin composition |
WO2016084711A1 (en) * | 2014-11-25 | 2016-06-02 | 富士フイルム株式会社 | Coloring composition for dyeing, coloring composition for printing, printing method, inkjet printing ink, and dyed fabric |
CN108027314A (en) * | 2015-07-28 | 2018-05-11 | 加利福尼亚大学董事会 | Long wavelength's voltage sensitive dye |
-
1952
- 1952-12-30 GB GB33022/52A patent/GB749308A/en not_active Expired
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010100595A (en) * | 2007-11-19 | 2010-05-06 | Tokyo Ohka Kogyo Co Ltd | Resist composition, resist pattern-forming method, new compound and acid generator |
JP2014009330A (en) * | 2012-07-02 | 2014-01-20 | Chugai Kasei Co Ltd | Xanthene dye and its manufacturing method |
US9376571B2 (en) | 2013-02-08 | 2016-06-28 | Dai Nippon Printing Co., Ltd. | Colorant dispersion liquid, method for producing colorant dispersion liquid, color resin composition for color filters, color filter, liquid crystal display device, and organic light-emitting display device |
WO2014123124A1 (en) * | 2013-02-08 | 2014-08-14 | 大日本印刷株式会社 | Colorant dispersion liquid, manufacturing method for colorant dispersion liquid, colored resin composition for color filter, color filter, liquid crystal display device, and organic light-emitting display device |
JP2014152274A (en) * | 2013-02-08 | 2014-08-25 | Dainippon Printing Co Ltd | Colorant dispersion liquid, manufacturing method for colorant dispersion liquid, colored resin composition for color filter, color filter, liquid crystal display device, and organic light-emitting display device |
JPWO2014192973A1 (en) * | 2013-05-31 | 2017-02-23 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound and colored curable resin composition |
CN105408427A (en) * | 2013-05-31 | 2016-03-16 | 东友精细化工有限公司 | Compound and colored curable resin composition |
WO2014192973A1 (en) * | 2013-05-31 | 2014-12-04 | 住友化学株式会社 | Compound and colored curable resin composition |
CN106967037A (en) * | 2013-05-31 | 2017-07-21 | 东友精细化工有限公司 | Compound and colored curable resin composition |
CN107082772A (en) * | 2013-05-31 | 2017-08-22 | 东友精细化工有限公司 | Compound and colored curable resin composition |
CN106967037B (en) * | 2013-05-31 | 2019-12-03 | 东友精细化工有限公司 | Compound and colored curable resin composition |
WO2016084711A1 (en) * | 2014-11-25 | 2016-06-02 | 富士フイルム株式会社 | Coloring composition for dyeing, coloring composition for printing, printing method, inkjet printing ink, and dyed fabric |
CN107001811A (en) * | 2014-11-25 | 2017-08-01 | 富士胶片株式会社 | It is dyeing coloured composition, stamp coloured composition, printing method, ink-jet printed with ink and the cloth and silk being colored |
JPWO2016084711A1 (en) * | 2014-11-25 | 2017-08-31 | 富士フイルム株式会社 | Coloring composition for dyeing, coloring composition for textile printing, textile printing method, ink for ink jet textile printing, and dyed fabric |
CN107001811B (en) * | 2014-11-25 | 2019-09-27 | 富士胶片株式会社 | It is dyeing coloured composition, stamp coloured composition, printing method, ink-jet printed with ink and the cloth and silk being colored |
US10487210B2 (en) | 2014-11-25 | 2019-11-26 | Fujifilm Corporation | Coloring composition for textile printing, textile printing method, ink for ink jet textile printing, and dyed fabric |
CN108027314A (en) * | 2015-07-28 | 2018-05-11 | 加利福尼亚大学董事会 | Long wavelength's voltage sensitive dye |
US11169156B2 (en) | 2015-07-28 | 2021-11-09 | The Regents Of The University Of California | Long wavelength voltage sensitive dyes |
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