CA1047488A - Azo pigments and process for their manufacture - Google Patents
Azo pigments and process for their manufactureInfo
- Publication number
- CA1047488A CA1047488A CA220,831A CA220831A CA1047488A CA 1047488 A CA1047488 A CA 1047488A CA 220831 A CA220831 A CA 220831A CA 1047488 A CA1047488 A CA 1047488A
- Authority
- CA
- Canada
- Prior art keywords
- quinolone
- methyl
- amino
- yellow
- acetoacetylamino
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
Abstract
NOVEL AZO PIGMENTS AND PROCESS FOR THEIR MANUFACTURE
Abstract of the Disclosure Azo pigments of the formula
Abstract of the Disclosure Azo pigments of the formula
Description
` ~047~8~3 . . .
The invention provides useful novel azo pigments ~!i, of the formula =N-CIH-CO~ ~o (1) : H X CO~CH3 Z H
"' wherein Q, X, Y and Z represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 4 carbon atoms, aryl or aryl-i,::
oxy groups which are unsubstitute~ or substituted by halogen atoms or alkyl or alkoxy groups of 1 to 4 carbon atoms, and wherein Q and X and Y and Z can a].so be closed via vicinal .~ carbon atoms to form an isocyclic ring. The novel azo pig ;, .
'- 10 ments are obtained by coupling a diazo or diazoamino compound of an amine of the formula , .
~ NH2 (2) "' with an acetoacetic arylide of the formula .
.:
' ' ~ , .. --.. . .. ... .
, , ~ . , , . . :
. . ~ :~ . : . . :
'.
' . .
.-' ' y CIH3 : CH3C0-CH2C0~
~ . Z H
Azo pigments having a particularly interesting . utility are those of the formula (1) wherein Q, X, Y and Z
represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ~ 5 ethoxy, phenyl or phenoxy groups, especially those of the formula ~ N C0-CH3 H
,. . .
. wherein Xl and Yl represent hydrogen or chlorine atoms, me-thyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsubstituted or substituted by 1 or 2 ; chlorine atoms or methyl groups.
The colourant of the formula CH3 ~ CH3 ; ~ o CH30 ~ ~ (5) .
, - - ' .' ~, -. : . .: : .
-- ~ :. :
, - , . .
.:
. . ~ . .
.
10~7~88 is characterised by particularly good properties.
As diazo components there are preferably used those of the formula (2~, wherein e and X represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsubstituted or substitu-ted by 1 or 2 chlorine atoms or by methyl groups.
Examples of diazo components are:
4-methyl-6-phenoxy-7-amino-quinolone-(2) 4-methyl-6-chloro-7-amino-quinolone-(2) 4-methyl-6-methoxy-7-amino-quinolone-(2) 4,6-dimethyl-7-amino-quinolone-(2) ; ~
4-methyl-7-amino-quinolone-(2) 4-methyl-7-chloro-6-amino-quinolone-~2) 4,8-dimethyl-7-amino-quinolone-(2) There are preferably used as coupling components - acetoacetic arylides of the formula (3), wherein Y and Z re-present hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsub-stituted or substituted by 1 or 2 chlorine atoms or by me-thyl groups.
Examples of coupling components are:
4-methyl-6-methoxy-7-acetoacetylamino-quinolone-(2) 4-methyl-6-chloro-7-acetoacetylamino-quinolone-(2) 4-methyl-7-chloro-6-acetoacetylamino-quinolone-(2) , .
, ..
' : .~ : . ~ .
.
, . ' ' - ' ~047488 i 4,8-dimethyl-7-acetoacetylamino-quinolone-(2) 4-methyl-7-acetoacetylamino-quinolone-(2) 4,6-dimethyl-7-acetoacetylamino-quinolone-(2) 4-methyl-6-phenoxy-7-acetoacetylamino-quinolone-(2).
The acetoacetic arylides to be used according to the invention are obtained, for example, by addition of di- ~-ketone to the amino-quinolones-(2).
The coupling is normally effected by gradually , adding the acid solution of the diazonium salt to the aqueous r~ 10 alkaline or aqueous acetic acid solution or also aqueous acetic acid suspension of the coupling component or its solu-tion in an organic water-immiscible solvent, desirably at a pH of 4 to 7.
It is advantageous to adjust the pH by addition of a buffer. Examples of suitable buffers are the salts, espe-cially alkaline salts, of formic acid, phosphoric acid or, in particular, of acetic acid. The alkaline solution of the coupling component desirably contains a wetting agent, a ; dispersant or an emulsifier, for example an aralkylsulphonate,such as dodecylbenzenesulphonate or the sodium sa]t of 1,1'-~` dinaphthylmethanesulphonic acid, polycondensation products of alkylene oxides, for example the reaction product of ethy-lene oxide and p-tert. octylphenyl, also alkyl esters of sul-phoricinoleates, for example n-butylsulphoricinoleate. The _ , ,' . ~ ', ':. ': -: ~
- , . . .. .
. .
, ' '' ,' ': , ' ; ' , ' ' ' , .
1~47488 dispersion of the coupling component can also contain with advantage protective colloids, for example methyl cellulose , or small amounts of inert organic solvents which are spar-ingly soluble or insoluble in water, for example aromatic hydrocarbons which may be halogenated or nitrated, such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene o nitrobenzene, as well as aliphatic halogenated hydrocarbons, ; for example carbon tetrachloride or trichloroethylene, also water-miscible organic solvents, such as acetone, methyl ethyl ketone, methanol, ethanol or isopropanol, especially , dimethyl formamide.
It is also possible to carry out the coupling with advantage by continuously combining an acid solution of the diazonium salt with an alkaline solution of the coupling component in a mixing jet so as to effect an immediate coup-ling of the components. The resultant colourant dispersant is continually drawn off from the mixing jet and the colour-ant isolated by filtration.
Instead of using the diazonium salt it is also possible ~o use the corresponding diazoamino compounds. These are obtained by a known method by coupling an aryldiazonium salt with a primary or preferably with a sécondary amine.
Amines of the most diverse kinds are suitable for this pur-pose, for example aliphatic amines, such as methylamine, ethylamine, ethanolamine, propylamine, butylamine, hexylamine ~ ....... . . ....
.
. .
- ' ~ . . . " ' ' and especially dimethylamine, diethylamine, diethanolamine, methylethanolamine, dipropylamine or dibutylamine, amino-acetic acid, methylaminoacetic acid, butylaminoacetic acid, aminoethanesulphonic acid, methylaminoethanesulphonic acid, guanylethanesulphonic acid, ~-aminoethylsulphuric acid, ali-. . ~
cyclic amines, such as cyclohexylamine, N-methylcyclohexyl-amine, dicyclohexylamine, aromatic amines, such as 4-amino-benzoic acid, sulphanilic acid, 4-sulpho-2-aminobenzoic acid, (4-sulphophenyl)-guanidine, 4-N-methylaminobenzoic acid, 4-ethylaminobenzoic acid, 1-amino-naphthalene-4-sulphonic acid, l-aminonaphthalene-2,4-disulphonic acid, heterocyclic amines, such as piperidine, morpholine, pyrrolidine, dihydroindole, i and finally also sodium cyanamide or dicyandiamide.
,' As a rule, the diazoamino compounds obtained are ~ 15 sparingly soluble in water and can be isolated from the reac-, tion medium in crystallised form, if appropriate after they ~: have been salted out. In many instances the moist press cakes can be used for the further reaction. In individual cases it may prove desirable to dehydrate the diazoamides be-fore the reaction by means of vacuum drying.
The coupling of the diazoamino compound with the coupling component takes place in an organic solvent, for example chlorobenzene, o-dichlorobenzene, nitrobenzene, py-ridine, ethylene glycol, ethylene glycol monoethyl or mono-........... . .
, : ~ - --- .. _ .
, .
~047488 methyl ether, dimethyl formamicle, formic acid or acetic acid.
When using water-miscible solvents it is not necessary to use the diazoamino compounds in anhydrous form. The aqueous moist filter cakes may be used, for example.
Finally, the coupling can also be effected by sus-pending the amine with the coupling component in the ratio 1:1 in an organic solvent and treating the resultant suspen-sion with a diazotising agent, especially with an ester of nitric acid, such as methyl, ethyl, butyl, amyl or actyl nitrite.
On account of their insolubility, the resultant pigments can be isolated from the reaction mixture by fil-- tering them off. Since the by-products remain in solution, the pigments are obtained in outstanding purity. It is ex-pedient to subject the pigments, especially those obtained by the aqueous coupling method, to an aftertreatment with organic solvents. This is accomplished by heating the re-sultant crude pigments in an inert organic solvent, for ex-ample methylene glycol monomethyl ether, ethylene glycol monomethyl ether, dimethyl formamide, N-methylpyrrolidone, monochloro- or dichlorobenzene, toluene, xylene or nitro--~ benzene, after which treatment they are obtained in the form of soft-grained powders.
The colourants constitute productive and pure pig-" . , . : . - . - : - , . .
- . . . . . ~ :
~' ' '' ,' . . ' . ' . ~, ~ . -' . ~ . ' ~ " ':
.
.
i,i~, 1047~8 - ments which, on account of their favourable properties, such as fastness to migration and light, can be used for the most diverse kinds of pigment application. They are eminently suitable for use in the printing ink industry and also for ' 5 pigmenting organic material of high molecular weight, for example cellulose ethers and esters, polyamides and polyur-ethanes or polyesters, acetyl cellulose, nitrocellulose, na-tural or synthetic resins, such as polymerisation or conden-sation resins, for example aminoplasts, especially urea/
formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, such as poly-styrene, polyvinyl chloride, polyethylene, polypropylene, polyacryloDitrile, polyacrylic ester, rubber, casein, silicon , and silicone resins, individually or in mixtures.
t~ 15 It is immaterial whether the cited compounds of high molecular weight are in the form of plastics, melts or spinning solutions, paints or lacquers or printing inks.
~ Depending on the use to which they are put, it is advantage-t`'`~ ' OUS to~use the novel pigments as toners or in the form of preparations.
The resultant colourations are characterised by good general fastness properties, especially by good fastness to light, migration and overstripe bleeding.
The following Examples illustrate the invention, .
~ 04748~3 :.-the parts and percentages being by weight unless otherwise : stated.
`:
`~
,, .
' , .
.' ~'.' ' :
' .
. ' . , -:
.. _ ~_ . . . . .
, - . , . - , . .
,. . - . - , . . , ~- . .
' . ~ . ' ,' ' .
~0~7'}88 Example 1 , i j:
. .
While cooling with ice, 2.66 parts of 4-methyl-6-phenoxy-7-~- amino-quinolone-(2) are diazotised in the usual manner in ,, , 100 parts of water with 2.5 parts by volume~of 10 normal hy-drochloric acid and 2.5 parts of 4 normal sodium nitrite i~, solution. The diazo solution is clarified by filtration.
The invention provides useful novel azo pigments ~!i, of the formula =N-CIH-CO~ ~o (1) : H X CO~CH3 Z H
"' wherein Q, X, Y and Z represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 4 carbon atoms, aryl or aryl-i,::
oxy groups which are unsubstitute~ or substituted by halogen atoms or alkyl or alkoxy groups of 1 to 4 carbon atoms, and wherein Q and X and Y and Z can a].so be closed via vicinal .~ carbon atoms to form an isocyclic ring. The novel azo pig ;, .
'- 10 ments are obtained by coupling a diazo or diazoamino compound of an amine of the formula , .
~ NH2 (2) "' with an acetoacetic arylide of the formula .
.:
' ' ~ , .. --.. . .. ... .
, , ~ . , , . . :
. . ~ :~ . : . . :
'.
' . .
.-' ' y CIH3 : CH3C0-CH2C0~
~ . Z H
Azo pigments having a particularly interesting . utility are those of the formula (1) wherein Q, X, Y and Z
represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ~ 5 ethoxy, phenyl or phenoxy groups, especially those of the formula ~ N C0-CH3 H
,. . .
. wherein Xl and Yl represent hydrogen or chlorine atoms, me-thyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsubstituted or substituted by 1 or 2 ; chlorine atoms or methyl groups.
The colourant of the formula CH3 ~ CH3 ; ~ o CH30 ~ ~ (5) .
, - - ' .' ~, -. : . .: : .
-- ~ :. :
, - , . .
.:
. . ~ . .
.
10~7~88 is characterised by particularly good properties.
As diazo components there are preferably used those of the formula (2~, wherein e and X represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsubstituted or substitu-ted by 1 or 2 chlorine atoms or by methyl groups.
Examples of diazo components are:
4-methyl-6-phenoxy-7-amino-quinolone-(2) 4-methyl-6-chloro-7-amino-quinolone-(2) 4-methyl-6-methoxy-7-amino-quinolone-(2) 4,6-dimethyl-7-amino-quinolone-(2) ; ~
4-methyl-7-amino-quinolone-(2) 4-methyl-7-chloro-6-amino-quinolone-~2) 4,8-dimethyl-7-amino-quinolone-(2) There are preferably used as coupling components - acetoacetic arylides of the formula (3), wherein Y and Z re-present hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsub-stituted or substituted by 1 or 2 chlorine atoms or by me-thyl groups.
Examples of coupling components are:
4-methyl-6-methoxy-7-acetoacetylamino-quinolone-(2) 4-methyl-6-chloro-7-acetoacetylamino-quinolone-(2) 4-methyl-7-chloro-6-acetoacetylamino-quinolone-(2) , .
, ..
' : .~ : . ~ .
.
, . ' ' - ' ~047488 i 4,8-dimethyl-7-acetoacetylamino-quinolone-(2) 4-methyl-7-acetoacetylamino-quinolone-(2) 4,6-dimethyl-7-acetoacetylamino-quinolone-(2) 4-methyl-6-phenoxy-7-acetoacetylamino-quinolone-(2).
The acetoacetic arylides to be used according to the invention are obtained, for example, by addition of di- ~-ketone to the amino-quinolones-(2).
The coupling is normally effected by gradually , adding the acid solution of the diazonium salt to the aqueous r~ 10 alkaline or aqueous acetic acid solution or also aqueous acetic acid suspension of the coupling component or its solu-tion in an organic water-immiscible solvent, desirably at a pH of 4 to 7.
It is advantageous to adjust the pH by addition of a buffer. Examples of suitable buffers are the salts, espe-cially alkaline salts, of formic acid, phosphoric acid or, in particular, of acetic acid. The alkaline solution of the coupling component desirably contains a wetting agent, a ; dispersant or an emulsifier, for example an aralkylsulphonate,such as dodecylbenzenesulphonate or the sodium sa]t of 1,1'-~` dinaphthylmethanesulphonic acid, polycondensation products of alkylene oxides, for example the reaction product of ethy-lene oxide and p-tert. octylphenyl, also alkyl esters of sul-phoricinoleates, for example n-butylsulphoricinoleate. The _ , ,' . ~ ', ':. ': -: ~
- , . . .. .
. .
, ' '' ,' ': , ' ; ' , ' ' ' , .
1~47488 dispersion of the coupling component can also contain with advantage protective colloids, for example methyl cellulose , or small amounts of inert organic solvents which are spar-ingly soluble or insoluble in water, for example aromatic hydrocarbons which may be halogenated or nitrated, such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene o nitrobenzene, as well as aliphatic halogenated hydrocarbons, ; for example carbon tetrachloride or trichloroethylene, also water-miscible organic solvents, such as acetone, methyl ethyl ketone, methanol, ethanol or isopropanol, especially , dimethyl formamide.
It is also possible to carry out the coupling with advantage by continuously combining an acid solution of the diazonium salt with an alkaline solution of the coupling component in a mixing jet so as to effect an immediate coup-ling of the components. The resultant colourant dispersant is continually drawn off from the mixing jet and the colour-ant isolated by filtration.
Instead of using the diazonium salt it is also possible ~o use the corresponding diazoamino compounds. These are obtained by a known method by coupling an aryldiazonium salt with a primary or preferably with a sécondary amine.
Amines of the most diverse kinds are suitable for this pur-pose, for example aliphatic amines, such as methylamine, ethylamine, ethanolamine, propylamine, butylamine, hexylamine ~ ....... . . ....
.
. .
- ' ~ . . . " ' ' and especially dimethylamine, diethylamine, diethanolamine, methylethanolamine, dipropylamine or dibutylamine, amino-acetic acid, methylaminoacetic acid, butylaminoacetic acid, aminoethanesulphonic acid, methylaminoethanesulphonic acid, guanylethanesulphonic acid, ~-aminoethylsulphuric acid, ali-. . ~
cyclic amines, such as cyclohexylamine, N-methylcyclohexyl-amine, dicyclohexylamine, aromatic amines, such as 4-amino-benzoic acid, sulphanilic acid, 4-sulpho-2-aminobenzoic acid, (4-sulphophenyl)-guanidine, 4-N-methylaminobenzoic acid, 4-ethylaminobenzoic acid, 1-amino-naphthalene-4-sulphonic acid, l-aminonaphthalene-2,4-disulphonic acid, heterocyclic amines, such as piperidine, morpholine, pyrrolidine, dihydroindole, i and finally also sodium cyanamide or dicyandiamide.
,' As a rule, the diazoamino compounds obtained are ~ 15 sparingly soluble in water and can be isolated from the reac-, tion medium in crystallised form, if appropriate after they ~: have been salted out. In many instances the moist press cakes can be used for the further reaction. In individual cases it may prove desirable to dehydrate the diazoamides be-fore the reaction by means of vacuum drying.
The coupling of the diazoamino compound with the coupling component takes place in an organic solvent, for example chlorobenzene, o-dichlorobenzene, nitrobenzene, py-ridine, ethylene glycol, ethylene glycol monoethyl or mono-........... . .
, : ~ - --- .. _ .
, .
~047488 methyl ether, dimethyl formamicle, formic acid or acetic acid.
When using water-miscible solvents it is not necessary to use the diazoamino compounds in anhydrous form. The aqueous moist filter cakes may be used, for example.
Finally, the coupling can also be effected by sus-pending the amine with the coupling component in the ratio 1:1 in an organic solvent and treating the resultant suspen-sion with a diazotising agent, especially with an ester of nitric acid, such as methyl, ethyl, butyl, amyl or actyl nitrite.
On account of their insolubility, the resultant pigments can be isolated from the reaction mixture by fil-- tering them off. Since the by-products remain in solution, the pigments are obtained in outstanding purity. It is ex-pedient to subject the pigments, especially those obtained by the aqueous coupling method, to an aftertreatment with organic solvents. This is accomplished by heating the re-sultant crude pigments in an inert organic solvent, for ex-ample methylene glycol monomethyl ether, ethylene glycol monomethyl ether, dimethyl formamide, N-methylpyrrolidone, monochloro- or dichlorobenzene, toluene, xylene or nitro--~ benzene, after which treatment they are obtained in the form of soft-grained powders.
The colourants constitute productive and pure pig-" . , . : . - . - : - , . .
- . . . . . ~ :
~' ' '' ,' . . ' . ' . ~, ~ . -' . ~ . ' ~ " ':
.
.
i,i~, 1047~8 - ments which, on account of their favourable properties, such as fastness to migration and light, can be used for the most diverse kinds of pigment application. They are eminently suitable for use in the printing ink industry and also for ' 5 pigmenting organic material of high molecular weight, for example cellulose ethers and esters, polyamides and polyur-ethanes or polyesters, acetyl cellulose, nitrocellulose, na-tural or synthetic resins, such as polymerisation or conden-sation resins, for example aminoplasts, especially urea/
formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, such as poly-styrene, polyvinyl chloride, polyethylene, polypropylene, polyacryloDitrile, polyacrylic ester, rubber, casein, silicon , and silicone resins, individually or in mixtures.
t~ 15 It is immaterial whether the cited compounds of high molecular weight are in the form of plastics, melts or spinning solutions, paints or lacquers or printing inks.
~ Depending on the use to which they are put, it is advantage-t`'`~ ' OUS to~use the novel pigments as toners or in the form of preparations.
The resultant colourations are characterised by good general fastness properties, especially by good fastness to light, migration and overstripe bleeding.
The following Examples illustrate the invention, .
~ 04748~3 :.-the parts and percentages being by weight unless otherwise : stated.
`:
`~
,, .
' , .
.' ~'.' ' :
' .
. ' . , -:
.. _ ~_ . . . . .
, - . , . - , . .
,. . - . - , . . , ~- . .
' . ~ . ' ,' ' .
~0~7'}88 Example 1 , i j:
. .
While cooling with ice, 2.66 parts of 4-methyl-6-phenoxy-7-~- amino-quinolone-(2) are diazotised in the usual manner in ,, , 100 parts of water with 2.5 parts by volume~of 10 normal hy-drochloric acid and 2.5 parts of 4 normal sodium nitrite i~, solution. The diazo solution is clarified by filtration.
- 2.88 parts of 4-methyl-6-methoxy-7-acetoacetylaminoquinolone-(2) are added to 200 parts by volume of dimethyl formamide.
After 3 parts of anhydrous sodium acetate have been added, the above diazo solution is poured in over c. 2 mim~tes.
;. The coupling mixture is stirred for several hours at room temperature and the pigment which has formed is filtered off, washed with hot water and methanol and dried. The product is obtained as a brown, hard-grained substance which retains its colouristically useful form by treating it in boiling N-me-thylpyrrolidone over the course of half an hours. After it has been isolated at room temperature, washed with methanol and dried, the pigment is a soft-grained yellow powder which colours polyvinyl chloride in a yellow shade which is fast to light and migration and has the formula .
.
`~ 1047488 .
~ ;3 ~ O ~ H3CO
.. l H O-CH3 ~ The Table lists further pigments which are obtained by the .
same procedure by coupling the diazo compound of the amine indicated in column I with the coupling component indicated in column II. Column III indicates the shade of the resul-~: tant pigment dye in polyvinyl chloride.
,: ~
. .
., .
~, ~
,~, ", , .
. .
, ' ,, ', ' .
,:
:
04748~
_ _ II IIT
. 2 4-methyl-6-chloro- 4-methyl-7-chloro-6- yellow 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ,, . .. .
y 3 4-methyl-6-methoxy- 4-methyl-7-chloro-6- reddish 7-amino-quinolone- acetoacetylamino- yellow . (2) quinolone-(2) '.' _ , 4 4,6-dimethyl-7- 4-methyl-7-chloro-6- yellow . amino-quinolone-(2) acetoacetylamino-quinolone-(2) ., _ .
. 5 4-methyl-7-amino- 4-methyl-7-chloro-6- greenish :~ quinolone-(2) acetoacetylamino- yellow .~ quinolone-(2) .
. 6 4-methyl-7-chloro- 4-methyl-7-chloro-6- reddish 6-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) . .
: 7 4,8-dimethyl-7- 4-methyl-7-chloro-6- yellow amino-quinolone-(2) acetoacetylamino-. quinolone-(2) .'i, .. _ ..
. 8 4-methyl-7-amino- 4-methyl-6-chloro-7- greenish quinolone-(2) acetoacetylamino- yellow . . quinolone-(2) , .. _ --'-'I
. 9 4,6-dimethyl-7- 4-methyl-6-chloro-7- yellow . amino-quinolone-(2) acetoacetylamino-. . quinolone-(2) , : 10 4,8-dimethyl-7- 4-methyl-6-chloro-7- greenish amino-quinolone-(2) acetoacetylamino- yellow . _ _ quinolone-(2) _ 13 -~04748~
.
:,~ _ . I II III
, 11 4-methyl-6-methoxy- 4-methyl-6-chloro-7- yellow 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ~ 12 4-methyl-5-phenoxy- 4-methyl-6-chloro-7- greenish .: 7-amino-quinolone- acetoacetylamino- yellow ~ (2) quinolone-(2) ,, .
13 4-methyl-6-chloro- 4-methyl-6-chloro-7- greenish 7-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) . 14 4-methyl-7-chloro- 4-methyl-6-chloro-7- greenish 6-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) _ . _ . .
: . 15 4-methyl-7-amino- 4,8-dimethyl-7-aceto- greenish -: quinolone-(2) acetylamino-quinolone- yellow :
_ . _ .
: 16 4,6-dimethyl-7- 4,8-dimethyl-7-aceto- reddisn amino-quinolone-(2) acetylamino-quinolone- yellow ,' . .
:. 17 4,8-dimethyl-7- 4,8-dimethyl-7-aceto- yellow amino-quinolone-(2) acetylamino-quinolone-. 18 4-methyl-6-methoxy- 4,8-dimethyl-7-aceto- orange . . 7-amino-quinolone- acetylamino-quinolone-'.' _ ................ .. ... _ I ....
19 4-methyl-6-phenoxy- 4,8-dimethyl-7-aceto- greenish _ .. _ _ . aceeylamino-quinolone- yell~
:
,. .... .. . .
- -, - : . . . .
'- : :, .
. : . : : ' :. ':
: . .
'',- ~ ' - , ~! ~0 47 4 81~
. _ II III ~
,.,' . 20 4-methyl-6-chloro- 4,8-dimethyl-7-aceto- yellow _ 7-amino-quinolone- acetylamino-quinolone-21 4-methyl-7-chloro- 4,8-dimethyl-7-aceto- reddish 6-amino-quinolone- acetylamino-quinolone-22 4-methyl-7-amino- 4-methyl-7-aceto- greenish quinolone-(2) ace~ylamino~quinolone- ycll~w 23 4,6-dimethyl-7- 4-methyl-7-aceto- reddish amino-quinolone-(2) acetylamino-quinolone- ~1l~
24 4-methyl-6-methoxy- 4-methyl-7-aceto- reddish _ 7-amino-quinolone- acetylamino-quinolone-. 25 4-methyl-6-phenoxy- 4-methyl-7-aceto- greenisn 7-amino-quLnolone- acetylamino-quinolone- Y-llc~
26 4-methyl-6-chloro- 4-methyl-7-aceto- yellow 7-amino-quinolone- acetylamino-quinolone-27 4-methyl-7-chloro- 4-methyl-7-aceto- reddish 6-amino-quinolone- acetylamino-quinolone- y~
. 28 4-methyl-7-amino- 4,6-dimethyl-7-aceto- greenish . _ quinolone-(2) acetylamino-quinolone- ye IIA~
,...
~ .
:
I II III
29 4,8-dimethyl-7- 4,6-dimethyl-7-aceto- greenish amino-quinolone-(2) acetylamino-quinolone- yellow (2) _ ...~ ... .
4-methyl-6-methoxy- 4,6-dimethyl-7-acèto- reddish 7-amino-quinolone- acetylamino-quinolone- yellow ,~ .. _ 31 4-methyl-6-phenoxy- 4,6-dimethyl-7-aceto- greenish -: 7-amino-quinolone- acetylamino-quinolone- yellow . (2) (2) _ _ .
; 32 4-methyl-6-chloro- 4,6-dimethyl-7-aceto- greenish : 7-amino-quinolone- acetylamino-quinolone- yellow . (2) (2) ,'. _ .- 33 4-methyl-7-amino- 4-methyl-6-phenoxy-7- greenish ~: quinolone-(2) acetoacetylamino- yellow ~, quinolone-(2) , _ ._ _ .' 34 4,6-dimethyl-7- 4-methyl-6-phenoxy-7- greenish amino-quinolone-(2) acetoacetylamino- yellow .: quinolone-(2) : .
, _ .
;~ 35 4-methyl-6-methoxy- 4-methyl-6-phenoxy-7- yellow . 7-amino-quinolone- acetoacetylamino-(2) quinolone-(2) .
36 4-methyl-6-phenoxy- 4-methyl-6-phenoxy-7- greenish . 7-amino-quinolone- acetoacetylamino- yellow ; (2) quinolone-(2) 37 4-methyl-6-chloro- 4-methyl-6-phenoxy-7- greenish 7-amino-quinolone- acetoacetylamino- yellow _ _ i quinolone-(2) _ 16 -.: , . ~ , . ' ,, .. ..
, : , ,.
r ~0474~8 ; II III
., 38 4-methyl-7-chloro- 4-methyl-6-phenoxy-7- yellow : 6-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) . , .
. 39 4-methyl-7-amino- 4-methyl-6-methox~-7- yellow quinolone-(2) acetoacetylamino-.. quinolone-(2) .
40 4,6-dimethyl-7- 4-methyl-6-methoxy-7- greenish amino-quinolone-(2) acetoacetylamino- yellow . quinolone-(2) " _ .
..41 4,8-dimethyl-7- 4-methyl-6-methoxy-7- greenish ..amino-quinolone-(2) acetoacetylamino- yellow '7,'" quinolone-(2) ~" _ . ........ _ ............. .. _ . 42 4-methyl-6-methoxy- 4-methyl-6-methoxy-7- yellow- 7-amino-quinolone- acetoacetylamino-.,: (2) quinolone-(2) . ...
t~'-.. 43 4-methyl-6-chloro- 4-methyl-6-methoxy-7- yellow . 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ,.~ _ . ................ _ ~_ . 44 4-methyl-7-chloro- 4-methyl-6-methoxy-7- greenish : 6-amino-quinolone acetoacetylamino- yellow (2) quinolone-(2) :~ . - --I
45 4-methyl-6-phenoxy- 4-methyl-7-chloro-6- yellow . 7-amino-quinolone- acetoacetylamino-(2) quinolone-(2) .. . __ ..
~- 46 4-methyl-6-(4' 4-methyl-7-acetoacetyl- yellow chlorophenoxy)-7- amino-quinolone-(2) _ amino-quinolone-(2) .
,~ . .
10474E~8 ,:
. II III
:. ..
47 ¦ -methyl-6-(4' 4,6-dimethyl-7-aceto- greenish chlorophenoxy)-7- acetylamino-quinolone- yellow ':. amino-quinolone-(2) (2) ~ ' .
. 48 4-methyl-6-(4' 4,8-dimethyl-7-aceto- greenish : chlorophenoxy)-7- acetylamino-quinolone- yellow amino-quinolone-(2) (2) ~;`
.~ 49 4-methyl-6-(4' 4-methyl-6-methoxy-7- yellow . chlorophenoxy)-7- acetoacetylamino-quino-.. amino-quinolone-(2) lone-(2) _ .. _ -.- 50 -methyl-6-(4' 4-methyl-6-phenoxy-7- greenish chlorophenoxy)-7- acetoacetylamino-quino- yellow . amino-quinolone-(2) lone-(2) ".' ....
- 51 4-methyl-6-(4' 4-methyl-6-chloro-7- greenish ... chlorophenoxy)-7- acetoacetylamino-quino- yellow amino-quinolone-(2) lone-(2) .. ...__ . 52 4-methyl-6-(4' 4-methyl-7-chloro-8- greenish chlorophenoxy)-7- acetoacetylamino-quino- yellow amino-quinolone-(2) lone-(2) ' ....
53 1 -methyl-6-(4' 4-methyl-7-chloro-8- greenish hlorophenoxy)-7- acetoacetylamino-quino- yellow . l mino-quinolone-(2) lone-(2) _ .. _ 54 ¦ ,5,8-trimethyl-6- 4-methyl-7-acetoacetyl- yellow l mino-quinolone-(2) amino-quinolone-(2) _ ¦ ,5,8-trimethyl-6- 4,6-dimethyl-7-acetoace- yellow 3mino-quinolone-(2) tylamino-quinolone-(2) _ 18 ~
, , . - , , - --- . ' - ' '. ' - ' - ' ' ' , ~, ~ , , 1047~
I II III
.. ._ . 56 4,5,8-trimethyl-6- 4,8-dimethyl-7-aceto- reddish amino-quinolone-(2) acetylamino-quinolone- yellow . 57 4,5-dimethyl-8- 4,8-dimethyl-7-aceto- reddish : methoxy-6-amino- acetylamino-quinolone- yellow ~ quinolone-(2) (2) ,, 58 4,5-~imethyl-8- 4-methyl-6-phenoxy-7- yellow . methoxy-6-amino- acetoacetylamino-quino-quinolone-(2) lone-(2) ~.
59 4-methyl-5,8-dime- 4-methyl-6-phenoxy-7- yellow thoxy-6-amino- acetoacetylamino-quino-quinolone-(2) lone-(2) ., . 60 4-methyl-6-amino- 4-methyl-6-phenoxy-7- yellow . 7,8-benzo-quinolone- acetoacetylamino-quino-. (2) lone-(2) ~. ._._ 61 4-methyl-6-amino- 4-methyl-6-chloro-7- orange .~ 7,8-benzo-quinolone- acetoacetylamino-quino-(2) lone-(2) ,. _ 62 4-methyl-6-amino- 4-methyl-7-chloro-6- orange 7,8-benzo-quinolone- acetoacetylamino-quino-(2) lone-(2) _ _ 63 4-methyl-5,8-di- 4,8-dimethyl-7-acetoace- reddish etho~y-6-amino- tylamino-quinolone-(2~ yellow : _ quinolone-(2) .
.
1047~
Example 64 , :
65 parts of stabilised polyvinyl chloride, 35 parts of di-octyl phthalate and 0.2 parts of the colourant obtained ac-cording to Example 1 are stirred together and the mixture is then rolled to and from ~r 7 minutes at 140C on a two-roll calender to yield a yellow sheet of good fastness to light and migration.
s . . .
, .
Example 65 1 g of the pigment obtained according to Example 1 and 4 g of the litho varnish of the foll~wing composition - 29,4% of linseed oil/stand oil (300 poise) 67.2% of linseed oil/stand oil (20 poise) 2,1% of cobalt octoate (8% Co) and 1.3% of lead octoate (24% Pb) are finely ground in an Engelsmann grinder and subsequently printed on art paper using a block by the letterpress print-ing method (application of 1 g/m2). A strong, bright, orange yellow shade of good transparency and good gloss is obtained.
Very brilliant green shades can be obtained in three or four ' ' , ' .
,, .
. .
- . '. ' .
,': 1047488 colour printing by overprinting on blue.
. The pigment is also suitable for other printing methods, for example intaglio printing, offset printing, flexographic printing, whereby equally good results are obtained.
~, ,...
`:
: .
After 3 parts of anhydrous sodium acetate have been added, the above diazo solution is poured in over c. 2 mim~tes.
;. The coupling mixture is stirred for several hours at room temperature and the pigment which has formed is filtered off, washed with hot water and methanol and dried. The product is obtained as a brown, hard-grained substance which retains its colouristically useful form by treating it in boiling N-me-thylpyrrolidone over the course of half an hours. After it has been isolated at room temperature, washed with methanol and dried, the pigment is a soft-grained yellow powder which colours polyvinyl chloride in a yellow shade which is fast to light and migration and has the formula .
.
`~ 1047488 .
~ ;3 ~ O ~ H3CO
.. l H O-CH3 ~ The Table lists further pigments which are obtained by the .
same procedure by coupling the diazo compound of the amine indicated in column I with the coupling component indicated in column II. Column III indicates the shade of the resul-~: tant pigment dye in polyvinyl chloride.
,: ~
. .
., .
~, ~
,~, ", , .
. .
, ' ,, ', ' .
,:
:
04748~
_ _ II IIT
. 2 4-methyl-6-chloro- 4-methyl-7-chloro-6- yellow 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ,, . .. .
y 3 4-methyl-6-methoxy- 4-methyl-7-chloro-6- reddish 7-amino-quinolone- acetoacetylamino- yellow . (2) quinolone-(2) '.' _ , 4 4,6-dimethyl-7- 4-methyl-7-chloro-6- yellow . amino-quinolone-(2) acetoacetylamino-quinolone-(2) ., _ .
. 5 4-methyl-7-amino- 4-methyl-7-chloro-6- greenish :~ quinolone-(2) acetoacetylamino- yellow .~ quinolone-(2) .
. 6 4-methyl-7-chloro- 4-methyl-7-chloro-6- reddish 6-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) . .
: 7 4,8-dimethyl-7- 4-methyl-7-chloro-6- yellow amino-quinolone-(2) acetoacetylamino-. quinolone-(2) .'i, .. _ ..
. 8 4-methyl-7-amino- 4-methyl-6-chloro-7- greenish quinolone-(2) acetoacetylamino- yellow . . quinolone-(2) , .. _ --'-'I
. 9 4,6-dimethyl-7- 4-methyl-6-chloro-7- yellow . amino-quinolone-(2) acetoacetylamino-. . quinolone-(2) , : 10 4,8-dimethyl-7- 4-methyl-6-chloro-7- greenish amino-quinolone-(2) acetoacetylamino- yellow . _ _ quinolone-(2) _ 13 -~04748~
.
:,~ _ . I II III
, 11 4-methyl-6-methoxy- 4-methyl-6-chloro-7- yellow 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ~ 12 4-methyl-5-phenoxy- 4-methyl-6-chloro-7- greenish .: 7-amino-quinolone- acetoacetylamino- yellow ~ (2) quinolone-(2) ,, .
13 4-methyl-6-chloro- 4-methyl-6-chloro-7- greenish 7-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) . 14 4-methyl-7-chloro- 4-methyl-6-chloro-7- greenish 6-amino-quinolone- acetoacetylamino- yellow (2) quinolone-(2) _ . _ . .
: . 15 4-methyl-7-amino- 4,8-dimethyl-7-aceto- greenish -: quinolone-(2) acetylamino-quinolone- yellow :
_ . _ .
: 16 4,6-dimethyl-7- 4,8-dimethyl-7-aceto- reddisn amino-quinolone-(2) acetylamino-quinolone- yellow ,' . .
:. 17 4,8-dimethyl-7- 4,8-dimethyl-7-aceto- yellow amino-quinolone-(2) acetylamino-quinolone-. 18 4-methyl-6-methoxy- 4,8-dimethyl-7-aceto- orange . . 7-amino-quinolone- acetylamino-quinolone-'.' _ ................ .. ... _ I ....
19 4-methyl-6-phenoxy- 4,8-dimethyl-7-aceto- greenish _ .. _ _ . aceeylamino-quinolone- yell~
:
,. .... .. . .
- -, - : . . . .
'- : :, .
. : . : : ' :. ':
: . .
'',- ~ ' - , ~! ~0 47 4 81~
. _ II III ~
,.,' . 20 4-methyl-6-chloro- 4,8-dimethyl-7-aceto- yellow _ 7-amino-quinolone- acetylamino-quinolone-21 4-methyl-7-chloro- 4,8-dimethyl-7-aceto- reddish 6-amino-quinolone- acetylamino-quinolone-22 4-methyl-7-amino- 4-methyl-7-aceto- greenish quinolone-(2) ace~ylamino~quinolone- ycll~w 23 4,6-dimethyl-7- 4-methyl-7-aceto- reddish amino-quinolone-(2) acetylamino-quinolone- ~1l~
24 4-methyl-6-methoxy- 4-methyl-7-aceto- reddish _ 7-amino-quinolone- acetylamino-quinolone-. 25 4-methyl-6-phenoxy- 4-methyl-7-aceto- greenisn 7-amino-quLnolone- acetylamino-quinolone- Y-llc~
26 4-methyl-6-chloro- 4-methyl-7-aceto- yellow 7-amino-quinolone- acetylamino-quinolone-27 4-methyl-7-chloro- 4-methyl-7-aceto- reddish 6-amino-quinolone- acetylamino-quinolone- y~
. 28 4-methyl-7-amino- 4,6-dimethyl-7-aceto- greenish . _ quinolone-(2) acetylamino-quinolone- ye IIA~
,...
~ .
:
I II III
29 4,8-dimethyl-7- 4,6-dimethyl-7-aceto- greenish amino-quinolone-(2) acetylamino-quinolone- yellow (2) _ ...~ ... .
4-methyl-6-methoxy- 4,6-dimethyl-7-acèto- reddish 7-amino-quinolone- acetylamino-quinolone- yellow ,~ .. _ 31 4-methyl-6-phenoxy- 4,6-dimethyl-7-aceto- greenish -: 7-amino-quinolone- acetylamino-quinolone- yellow . (2) (2) _ _ .
; 32 4-methyl-6-chloro- 4,6-dimethyl-7-aceto- greenish : 7-amino-quinolone- acetylamino-quinolone- yellow . (2) (2) ,'. _ .- 33 4-methyl-7-amino- 4-methyl-6-phenoxy-7- greenish ~: quinolone-(2) acetoacetylamino- yellow ~, quinolone-(2) , _ ._ _ .' 34 4,6-dimethyl-7- 4-methyl-6-phenoxy-7- greenish amino-quinolone-(2) acetoacetylamino- yellow .: quinolone-(2) : .
, _ .
;~ 35 4-methyl-6-methoxy- 4-methyl-6-phenoxy-7- yellow . 7-amino-quinolone- acetoacetylamino-(2) quinolone-(2) .
36 4-methyl-6-phenoxy- 4-methyl-6-phenoxy-7- greenish . 7-amino-quinolone- acetoacetylamino- yellow ; (2) quinolone-(2) 37 4-methyl-6-chloro- 4-methyl-6-phenoxy-7- greenish 7-amino-quinolone- acetoacetylamino- yellow _ _ i quinolone-(2) _ 16 -.: , . ~ , . ' ,, .. ..
, : , ,.
r ~0474~8 ; II III
., 38 4-methyl-7-chloro- 4-methyl-6-phenoxy-7- yellow : 6-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) . , .
. 39 4-methyl-7-amino- 4-methyl-6-methox~-7- yellow quinolone-(2) acetoacetylamino-.. quinolone-(2) .
40 4,6-dimethyl-7- 4-methyl-6-methoxy-7- greenish amino-quinolone-(2) acetoacetylamino- yellow . quinolone-(2) " _ .
..41 4,8-dimethyl-7- 4-methyl-6-methoxy-7- greenish ..amino-quinolone-(2) acetoacetylamino- yellow '7,'" quinolone-(2) ~" _ . ........ _ ............. .. _ . 42 4-methyl-6-methoxy- 4-methyl-6-methoxy-7- yellow- 7-amino-quinolone- acetoacetylamino-.,: (2) quinolone-(2) . ...
t~'-.. 43 4-methyl-6-chloro- 4-methyl-6-methoxy-7- yellow . 7-amino-quinolone- acetoacetylamino-. (2) quinolone-(2) ,.~ _ . ................ _ ~_ . 44 4-methyl-7-chloro- 4-methyl-6-methoxy-7- greenish : 6-amino-quinolone acetoacetylamino- yellow (2) quinolone-(2) :~ . - --I
45 4-methyl-6-phenoxy- 4-methyl-7-chloro-6- yellow . 7-amino-quinolone- acetoacetylamino-(2) quinolone-(2) .. . __ ..
~- 46 4-methyl-6-(4' 4-methyl-7-acetoacetyl- yellow chlorophenoxy)-7- amino-quinolone-(2) _ amino-quinolone-(2) .
,~ . .
10474E~8 ,:
. II III
:. ..
47 ¦ -methyl-6-(4' 4,6-dimethyl-7-aceto- greenish chlorophenoxy)-7- acetylamino-quinolone- yellow ':. amino-quinolone-(2) (2) ~ ' .
. 48 4-methyl-6-(4' 4,8-dimethyl-7-aceto- greenish : chlorophenoxy)-7- acetylamino-quinolone- yellow amino-quinolone-(2) (2) ~;`
.~ 49 4-methyl-6-(4' 4-methyl-6-methoxy-7- yellow . chlorophenoxy)-7- acetoacetylamino-quino-.. amino-quinolone-(2) lone-(2) _ .. _ -.- 50 -methyl-6-(4' 4-methyl-6-phenoxy-7- greenish chlorophenoxy)-7- acetoacetylamino-quino- yellow . amino-quinolone-(2) lone-(2) ".' ....
- 51 4-methyl-6-(4' 4-methyl-6-chloro-7- greenish ... chlorophenoxy)-7- acetoacetylamino-quino- yellow amino-quinolone-(2) lone-(2) .. ...__ . 52 4-methyl-6-(4' 4-methyl-7-chloro-8- greenish chlorophenoxy)-7- acetoacetylamino-quino- yellow amino-quinolone-(2) lone-(2) ' ....
53 1 -methyl-6-(4' 4-methyl-7-chloro-8- greenish hlorophenoxy)-7- acetoacetylamino-quino- yellow . l mino-quinolone-(2) lone-(2) _ .. _ 54 ¦ ,5,8-trimethyl-6- 4-methyl-7-acetoacetyl- yellow l mino-quinolone-(2) amino-quinolone-(2) _ ¦ ,5,8-trimethyl-6- 4,6-dimethyl-7-acetoace- yellow 3mino-quinolone-(2) tylamino-quinolone-(2) _ 18 ~
, , . - , , - --- . ' - ' '. ' - ' - ' ' ' , ~, ~ , , 1047~
I II III
.. ._ . 56 4,5,8-trimethyl-6- 4,8-dimethyl-7-aceto- reddish amino-quinolone-(2) acetylamino-quinolone- yellow . 57 4,5-dimethyl-8- 4,8-dimethyl-7-aceto- reddish : methoxy-6-amino- acetylamino-quinolone- yellow ~ quinolone-(2) (2) ,, 58 4,5-~imethyl-8- 4-methyl-6-phenoxy-7- yellow . methoxy-6-amino- acetoacetylamino-quino-quinolone-(2) lone-(2) ~.
59 4-methyl-5,8-dime- 4-methyl-6-phenoxy-7- yellow thoxy-6-amino- acetoacetylamino-quino-quinolone-(2) lone-(2) ., . 60 4-methyl-6-amino- 4-methyl-6-phenoxy-7- yellow . 7,8-benzo-quinolone- acetoacetylamino-quino-. (2) lone-(2) ~. ._._ 61 4-methyl-6-amino- 4-methyl-6-chloro-7- orange .~ 7,8-benzo-quinolone- acetoacetylamino-quino-(2) lone-(2) ,. _ 62 4-methyl-6-amino- 4-methyl-7-chloro-6- orange 7,8-benzo-quinolone- acetoacetylamino-quino-(2) lone-(2) _ _ 63 4-methyl-5,8-di- 4,8-dimethyl-7-acetoace- reddish etho~y-6-amino- tylamino-quinolone-(2~ yellow : _ quinolone-(2) .
.
1047~
Example 64 , :
65 parts of stabilised polyvinyl chloride, 35 parts of di-octyl phthalate and 0.2 parts of the colourant obtained ac-cording to Example 1 are stirred together and the mixture is then rolled to and from ~r 7 minutes at 140C on a two-roll calender to yield a yellow sheet of good fastness to light and migration.
s . . .
, .
Example 65 1 g of the pigment obtained according to Example 1 and 4 g of the litho varnish of the foll~wing composition - 29,4% of linseed oil/stand oil (300 poise) 67.2% of linseed oil/stand oil (20 poise) 2,1% of cobalt octoate (8% Co) and 1.3% of lead octoate (24% Pb) are finely ground in an Engelsmann grinder and subsequently printed on art paper using a block by the letterpress print-ing method (application of 1 g/m2). A strong, bright, orange yellow shade of good transparency and good gloss is obtained.
Very brilliant green shades can be obtained in three or four ' ' , ' .
,, .
. .
- . '. ' .
,': 1047488 colour printing by overprinting on blue.
. The pigment is also suitable for other printing methods, for example intaglio printing, offset printing, flexographic printing, whereby equally good results are obtained.
~, ,...
`:
: .
Claims (8)
1. Azo pigments of the formula (1) wherein Q, X, Y and Z represent hydrogen or halogen atoms, alkyl or alkoxy groups of 1 to 4 carbon atoms, aryl or aryl-oxy groups which can be substituted by halogen atoms or alkyl or alkoxy groups of 1 to 4 carbon atoms, and wherein Q and X and Y and Z can also be closed via vicinal carbon atoms to form an isocyclic ring.
2. Azo pigments according to claim 1, wherein Q, X, Y and Z represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy, phenyl or phenoxy groups
3, Azo pigments according to claim 2, of the formula (4) wherein X1 and Y1 represent hydrogen or chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy groups which are unsubstituted or substituted by 1 or 2 chlorine atoms or by methyl groups.
4. Azo pigments according to claim 3, of the formula (5)
5. Azo pigments according to claim 3, of the formula
6. Azo pigments according to claim 3, of the formula
7. Azo pigments according to claim 3, of the formula
8. Azo pigments according to claim 3, of the formula
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH283074A CH596273A5 (en) | 1974-02-28 | 1974-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047488A true CA1047488A (en) | 1979-01-30 |
Family
ID=4242554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,831A Expired CA1047488A (en) | 1974-02-28 | 1975-02-26 | Azo pigments and process for their manufacture |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS50121324A (en) |
| AR (1) | AR205811A1 (en) |
| BE (1) | BE826051A (en) |
| BR (1) | BR7501183A (en) |
| CA (1) | CA1047488A (en) |
| CH (1) | CH596273A5 (en) |
| DE (1) | DE2508090A1 (en) |
| DK (1) | DK78575A (en) |
| ES (1) | ES435113A1 (en) |
| FR (1) | FR2262686B1 (en) |
| GB (1) | GB1445066A (en) |
| NL (1) | NL7502348A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158101A (en) * | 1961-09-28 | 1964-11-24 | Dollar Billy | Flotation device |
| DE19636483C2 (en) * | 1996-09-09 | 2000-12-14 | Dystar Textilfarben Gmbh & Co | Water-soluble azo compounds, process for their preparation and their use as dyes |
| US20060219134A1 (en) * | 2003-03-25 | 2006-10-05 | Johannes Benkhoff | Monoazoquinolone pigments, process for their preparation and their use |
| TWI698607B (en) | 2018-05-10 | 2020-07-11 | 日商Ｓｍｃ股份有限公司 | Gate valve |
-
1974
- 1974-02-28 CH CH283074A patent/CH596273A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR25776875A patent/AR205811A1/en active
- 1975-02-25 DE DE19752508090 patent/DE2508090A1/en not_active Withdrawn
- 1975-02-26 CA CA220,831A patent/CA1047488A/en not_active Expired
- 1975-02-27 BE BE153801A patent/BE826051A/en unknown
- 1975-02-27 GB GB829475A patent/GB1445066A/en not_active Expired
- 1975-02-27 FR FR7506115A patent/FR2262686B1/fr not_active Expired
- 1975-02-27 DK DK78575A patent/DK78575A/da unknown
- 1975-02-27 NL NL7502348A patent/NL7502348A/en unknown
- 1975-02-27 BR BR7501183A patent/BR7501183A/en unknown
- 1975-02-27 ES ES435113A patent/ES435113A1/en not_active Expired
- 1975-02-28 JP JP2491775A patent/JPS50121324A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AR205811A1 (en) | 1976-06-07 |
| GB1445066A (en) | 1976-08-04 |
| FR2262686B1 (en) | 1977-04-15 |
| DK78575A (en) | 1975-10-27 |
| JPS50121324A (en) | 1975-09-23 |
| DE2508090A1 (en) | 1975-09-04 |
| CH596273A5 (en) | 1978-03-15 |
| BR7501183A (en) | 1975-12-02 |
| BE826051A (en) | 1975-08-27 |
| NL7502348A (en) | 1975-09-01 |
| FR2262686A1 (en) | 1975-09-26 |
| ES435113A1 (en) | 1976-12-01 |
| AU7862875A (en) | 1976-09-02 |
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