GB565951A - New monoazo pigments - Google Patents

New monoazo pigments

Info

Publication number
GB565951A
GB565951A GB838643A GB838643A GB565951A GB 565951 A GB565951 A GB 565951A GB 838643 A GB838643 A GB 838643A GB 838643 A GB838643 A GB 838643A GB 565951 A GB565951 A GB 565951A
Authority
GB
United Kingdom
Prior art keywords
amino
nickel
hydroxynaphthoic acid
nitro
chloride
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
Application number
GB838643A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DONOVAN ERB KVALNES
HAROLD EDWARD WOODWARD
EIDP Inc
Original Assignee
DONOVAN ERB KVALNES
HAROLD EDWARD WOODWARD
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DONOVAN ERB KVALNES, HAROLD EDWARD WOODWARD, EI Du Pont de Nemours and Co filed Critical DONOVAN ERB KVALNES
Priority to GB838643A priority Critical patent/GB565951A/en
Publication of GB565951A publication Critical patent/GB565951A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14Monoazo compounds

Abstract

Monoazo pigments, fast to light, which are metal complexes containing two atoms of metal per two molecules of monoazo compound, are obtained by coupling a diazotised arylamine free from carboxylic and sulphonic acid groups and carrying no hydroxy group in o-position to the sole diazotisable amino group, with 2 : 3-hydroxynaphthoic acid or a substitution product thereof in which the substituent is halogen, nitro, alkyl or alkoxy and is on the ring not carrying the hydroxy and carboxylic groups, at least one of the metal atoms being nickel or cobalt and the other being of atomic weight between 54 and 65, e.g. copper, nickel, cobalt, iron or manganese, or an alkaline earth metal, e.g. calcium, strontium or barium. In examples: (1) the monoazo compound, 4-nitroaniline --> (alkaline with sodium hydroxide and sodium carbonate) 2 : 3-hydroxynaphthoic acid is heated for 3 hours with an aqueous ammoniacal solution of nickel chloride at 90 DEG C.; (2) the monoazo compound of (1) produced by coupling in sodium carbonate solution buffered with sodium acetate is similarly metallised with an addition of para soap to the metallising medium; the ammonia may be replaced by sodium hydroxide added gradually during the metallisation; (3) the nickel chloride in (1) is replaced by cobaltous chloride to obtain the cobaltous complex or, by addition of hydrogen peroxide to the metallising medium, the cobaltic complex; (4) the diazo component in (1) is replaced by 3-nitroaniline; (5) the nickel chloride in (1) is partly replaced by barium chloride; (6) an ammoniacal aqueous slurry of the monoazo compound, 2 : 5 - dichloroaniline --> 2 : 3 - hydroxynaphthoic acid containing calcium chloride and nickel chloride is heated for 2 hours at 90 DEG C.; (7) the monoazo compound, aniline --> 2 : 3-hydroxynaphthoic acid is converted as in (1) into the nickel complex; the ammonia in the metallising medium may be replaced by other bases, e.g. di- or tri-ethanolamine, pyridine or morpholine; (8) the monoazo compound, 1-naphthylamine --> 2 : 3-hydroxynaphthoic acid is heated for 3 hours in an aqueous solution at 90 DEG C. containing nickel chloride and aniline, N-b -hydroxyethyl-aniline, N-di-(b -hydroxyethyl)-aniline, urea or ammonia. A table is also given showing the colours of the prints obtainable with the use of nickel or cobalt as the metal, of various additional diazo components and of 2 : 3-hydroxynaphthoic acid as the coupling component, the additional diazo components being 3- or 4-chloroaniline, 2- or 3-nitro-4-chloroaniline, 2-nitro-4-aminotoluene, 2 - amino - 5 - nitrotoluene, 2- or 4 - anisidine, 2-amino-4- or 5-nitroanisole, 4-amino-2-chlorophenetole, 4 - amino - 41 - ethoxydiphenylamine, 2-naphthylamine and 1-aminoanthraquinone. Other diazo components which may be used are 2-, 3- or 4-toluidine, 1 : 3-dimethyl-4-aminobenzene, p-xylidine, 2-chloroaniline, 2-, 3- or 4-bromoaniline, chlorotoluidines, 3-anisidine, 2-, 3- or 4-phenetidine, chloro-anisidines, other chlorophenetidines, nitrochloroanilines, nitroanisidines, dichloroanilines and nitrotoluidines, 2 : 5 - dimethoxyaniline, nitrophenetidines, 3-aminobenzotrifluoride, trichloroanilines, nitrochlorotoluidines, 3- or 4-benzoylaminoaniline, 3- or 4-aminoacetophenone, 3- or 4-aminobenzophenone, 2-, 3- or 4-aminophenyl-alkylsulphones, 4-dodecylaniline, 2-, 3- or 4-aminobenzenesulphondimethylamide, 2-, 3- or 4-cyanoaniline, 2-, 3- or 4-aminoalkylbenzoates, 2-, 3- or 4 - aminodiphenyl ether, 4 - nitro - 41 - amino - diphenyl sulphide, 4-aminodiphenylamine or its 41-ethoxy derivative, 2- or 4-aminodiphenyl, 2-aminobenzthiazole or its 6-ethoxy derivative, 2-amino-4-methylthiazole, 5-, 6- or 8-aminoquinoline and 1 - phenyl - 4 - amino - 5 - chloro - pyrazole. Other specified coupling components are the 6-chloro-, 6-bromo-, 5- or 8-nitro-, p 6-methyl- (cf. Specification 391,987), 6-methoxy-and 6-ethoxy- (cf. Specification 366,140) derivatives of 2 : 3-hydroxynaphthoic acid. The pH value of the metallisation medium is advantageously maintained above 6.5 by addition of a basic compound, specified compounds additional to those in the above examples being propylamine, mono-, di- and tri-methylamine, ethylamine, formamide, acetamide, dimethylformamide, hexylamine, cyclohexylamine, methylglycamine, taurine, b -dimethylaminopropanolsulphonic acid, toluidines, xylidines, naphthylamines, diphenylamine, piperazine, dimethylsulphanilic acid, melamine, pyrrole, indole, carbazole, hexamethyleneimine, hexamethylenetetramine, mono- and di-methylglycine, dimethylolurea, sodium formate, oxalate, citrate, maleate, succinate or chloracetate and potassium glycollate, gluconate or tartrate.
GB838643A 1943-05-26 1943-05-26 New monoazo pigments Expired GB565951A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB838643A GB565951A (en) 1943-05-26 1943-05-26 New monoazo pigments

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB838643A GB565951A (en) 1943-05-26 1943-05-26 New monoazo pigments

Publications (1)

Publication Number Publication Date
GB565951A true GB565951A (en) 1944-12-06

Family

ID=9851541

Family Applications (1)

Application Number Title Priority Date Filing Date
GB838643A Expired GB565951A (en) 1943-05-26 1943-05-26 New monoazo pigments

Country Status (1)

Country Link
GB (1) GB565951A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7291217B2 (en) 2002-01-04 2007-11-06 University Of Dayton Non-toxic corrosion-protection pigments based on rare earth elements
US7789958B2 (en) 2003-01-13 2010-09-07 University Of Dayton Non-toxic corrosion-protection pigments based on manganese

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7291217B2 (en) 2002-01-04 2007-11-06 University Of Dayton Non-toxic corrosion-protection pigments based on rare earth elements
US7833331B2 (en) 2002-01-04 2010-11-16 University Of Dayton Non-toxic corrosion-protection pigments based on cobalt
US7789958B2 (en) 2003-01-13 2010-09-07 University Of Dayton Non-toxic corrosion-protection pigments based on manganese

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