GB727996A - Pigment dyestuffs of the anthraquinone series - Google Patents
Pigment dyestuffs of the anthraquinone seriesInfo
- Publication number
- GB727996A GB727996A GB19445/52A GB1944552A GB727996A GB 727996 A GB727996 A GB 727996A GB 19445/52 A GB19445/52 A GB 19445/52A GB 1944552 A GB1944552 A GB 1944552A GB 727996 A GB727996 A GB 727996A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthraquinone
- nitrobenzene
- reacting
- diamine
- diamino
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Pigment dyestuffs are made by reacting an anthraquinone derivative of the formula <FORM:0727996/IV (c)/1> wherein R and R1 stand for organic radicals or hydrogen, at most one of the radicals R and R1 being hydrogen, and wherein the said radicals contain together at least two amino groups, with a polyfunctional compound capable of reacting with the external amino groups. Polyfunctional compounds specified are aliphatic and aromatic diisocyanates, pyromellitic acid dianhydride, bis-ethylene oxide compounds, dicarboxylic phenyl esters, oxalic esters, diphenyl carbonate, methane-tricarboxylic esters, melamine-hexamethylol methylether, benzene disulphochloride, cyanuric chloride, terephthaloyl chloride, 1.3.5 - triacryloyl perhydro-s-triazine, and benzene disulpho-di-N.N1-ethylene imide. The reaction is preferably effected in a solvent such as chlorbenzene, nitrobenzene, or water at temperatures up to 200 DEG C. In examples, (1) 1.4-bis-aminoethylamino-anthraquinone (obtained by mixing leuco - 1.4 - diamino - anthraquinone and excess ethylene diamine followed by oxidation) is heated in nitrobenzene with diphenyl carbonate to give a polyurea, or with oxalic acid dimethyl ester, or with terephthalic acid chloride in presence of pyridine; (2) 1.4-di-(p-aminohexahydrophenylamino) - anthraquinone (obtained by heating leuco-1.4-diaminoanthraquinone and excess hexahydro-p-phenylene diamine), 1.4 - bis - aminoethylaminoanthraquinone, or 1.4 - di - (p - aminophenylamino)-anthraquinone is heated in nitrobenzene with a mixture of 2.4- and 2.6-toluylene diisocyanate or in water with the bisulphite addition compound of hexamethylene diisocyanate; (3) 1.4 - di - (p - aminohexahydrophenylamino)-anthraquinone is reacted in dilute acetic acid with 1.3.5-triacryloylperhydro-s-triazine. Other anthraquinone starting materials specified are those obtained by reacting quinizarin, leucoquinizarin, or leuco-1.4-diaminoanthraquinone with hexamethylene diamine, 1.2-diamino-3-hydroxypropane, hexahydrobenzidine, perhydronaphthalene diamines, N-methyl-1.3-propylene diamine, 3 - amino - 1 - a - aminoethylbenzene, and o .o 1 - diaminodipropyl - diamino-butane.ALSO:Pigment dyestuffs are made by reacting an anthraquinone derivative of the formula <FORM:0727996/IV (a)/1> wherein R and R1 stand for organic radicals or hydrogen, at most one of the radicals R and R1 being hydrogen, and wherein the said radicals contain together at least two amino groups, with a polyfunctional compound capable of reacting with the external amino groups. Polyfunctional compounds specified are aliphatic and aromatic diisocyanates, pyromellitic acid dianhydride, bis-ethylene oxide compounds, dicarboxylic phenyl esters, oxalic esters, diphenyl carbonate, methane-tricarboxylic esters, melamine-hexamethylol methyl-ether, benzene disulphochloride, cyanuric chloride, terephthaloyl chloride, 1,3,5-triacryloyl perhydro-s-triazine, and benzene disulpho di-N.N1-ethylene imide. The reaction is preferably effected in a solvent such as chlorbenzene, nitrobenzene or water at temperatures up to 200 DEG C. In examples, (1) 1.4-diamino-anthraquinone and excess ethylene diamine followed by oxidation) is heated in nitrobenzene and diphenyl carbonate to give a polyurea, or with oxalic acid dimethyl ester, or with terephthalic acid chloride in presence of pyridine; (2) 1.4-di-(p-amino hexahydro - phenyl - amino) - anthraquinone (obtained by heating leuco-1.4-diaminoanthraquinone and excess hexahydro-p-phenylene diamine), 1.4 - bis - aminoethylaminoanthraquinone, or 1.4 - di - (p - aminophenylamino)-anthraquinone is heated in nitrobenzene with a mixture of 2.4- and 2.6-toluylene diisocyanate or in water with the bisulphite addition compound of hexamethylene diisocyanate; (3) 1.4-di-(p-aminohexahydrophenylamino)-anthraquinone is reacted in dilute acetic acid with 1,3,5-triacryloylperhydro-s-triazine. Other anthraquinone starting materials specified are those obtained by reacting quinizarin, leucoquinizarin, or leuco-1.4-diaminoanthraquinone with hexamethylene diamine, 1.2-diamino-3-hydroxypropane, hexahydro - benzidine, perhydronaphthalene diamines, N - methyl - 1.3 - propylene diamine, 3 - amino - 1 - aminoethyl - benzene, and w.w1-diaminodipropyl-diaminobutane.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE727996X | 1951-08-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB727996A true GB727996A (en) | 1955-04-13 |
Family
ID=6635584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19445/52A Expired GB727996A (en) | 1951-08-01 | 1952-07-31 | Pigment dyestuffs of the anthraquinone series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB727996A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0339421A2 (en) * | 1988-04-29 | 1989-11-02 | Bayer Ag | Dye |
WO1998010022A1 (en) * | 1996-09-03 | 1998-03-12 | Eastman Chemical Company | Anthraquinone polysulfonamide colorants |
CN108586274A (en) * | 2018-05-25 | 2018-09-28 | 苏州大学 | A kind of presoma and preparation method thereof of blue anthraquinone reactive disperse dyes |
-
1952
- 1952-07-31 GB GB19445/52A patent/GB727996A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0339421A2 (en) * | 1988-04-29 | 1989-11-02 | Bayer Ag | Dye |
EP0339421A3 (en) * | 1988-04-29 | 1991-11-06 | Bayer Ag | Dye |
WO1998010022A1 (en) * | 1996-09-03 | 1998-03-12 | Eastman Chemical Company | Anthraquinone polysulfonamide colorants |
US6140517A (en) * | 1996-09-03 | 2000-10-31 | Eastman Chemical Company | Anthraquinone polysulfonamide colorants |
CN108586274A (en) * | 2018-05-25 | 2018-09-28 | 苏州大学 | A kind of presoma and preparation method thereof of blue anthraquinone reactive disperse dyes |
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