CA1140130A - Isoindoline pigments, production and use thereof - Google Patents
Isoindoline pigments, production and use thereofInfo
- Publication number
- CA1140130A CA1140130A CA000364234A CA364234A CA1140130A CA 1140130 A CA1140130 A CA 1140130A CA 000364234 A CA000364234 A CA 000364234A CA 364234 A CA364234 A CA 364234A CA 1140130 A CA1140130 A CA 1140130A
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- group
- carbon atoms
- formula
- pigments
- alkoxy
- Prior art date
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- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Abstract
Abstract Isoindoline pigments of the formula wherein R is an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl. cyano, phenyl or carbamoyl group, by an alkoxy group of 1 to 4 carbon atoms, an aryloxy, aryloxycarbonyl, aroyloxy or aroylamino group, by an alkoxy-carbonyl, alkanoyloxy, alkylcarbamoyl or alkanoylamino group of 2 to 6 carbon atoms, or by a phthalimido group, or is a cycloalkyl group of 5 to 8 carbon atoms, and X is a radical of the formula or
Description
11~0130 Case 3-12596/+
Isoindoline pi~ments, production and use thereof The present invention relates to isoindoline pigments of the formula ?~C-~-CO~riR
.~ \,/ \
./ \./
o~ s ~_,x wherein R is an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl, cyano, phenyl or carbamoyl group, by an alkoxy group of 1 to 4 carbon atoms, an aryloxy, aryloxycarbonyl, aroyloxy or aroylamino group, by an alkoxy-carbonyl, alkanoyloxy, alkylcarbamoyl or alkanoylamino group of 2 to 6 carbon atoms, or by a phthalimido group, or is a cycloalkyl group of 5 to 8 carbon atoms, and X is a radical of the formula ~N~ or \.~ ~.
. ~ I ~z o wherein Y and Z are hydrogen or halogen atoms, or alkyl or alkoxy groups of 1 to 4 carbon atoms.
In the above definition, the term "aryl" denotes e.g.
~- or ~-naphthyl or diphenylyl, but preferably an unsub-stituted or a substituted phenyl radical. Possible sub-stituents are: halogen, especiall.y chlorine, and alkyl or alkoxy of 1 to 4 carbon atoms.
~S ~
Preferred pigments are those of the indicated formula wherein R is a methyl or ethyl group and X is the radical of the formula ~H
O
The pigments of the present invention are obtained by condensing 1,3-diiminoisoindoline, in any order, ~ith 1 mole each of acyanoacetamide of the formula NCCH2CONHR and barbituric acid or with a dihydroxyquinoline of the formula OH
Y~. ,!
~! !
OH
Z
Rep,resentative examples of cyanoacetamides are:
cyanoacetomethylamide, cyanoacetethylamide, cyanoaceto-n-propylamide, cyanoacetisopropylamide, cyanoaceto-n-butyl-amide, cyanoaceto-~-methoxyethylamide, cyanoaceto-~-ethoxy-ethylamide, cyanoaceto-~-methoxy-n-propylamide, cyanoaceto-~-cyanoethylamide, cyanoacetobenzylamide, cyanoaceto-a-phenyl-ethylamide, cyanoaceto-~-phenylethylamide, cyanoacetocyclo-hexylamide, cyanoaceto-~-hydroxyethylamide, cyanoaceto-~-acetyloxyethylamide, cyanoaceto-~-benzoyloxyethylamide, cyanoacetethoxycarbonylmethylamide.
Representative examples of dihydroxyquinolines are:
Isoindoline pi~ments, production and use thereof The present invention relates to isoindoline pigments of the formula ?~C-~-CO~riR
.~ \,/ \
./ \./
o~ s ~_,x wherein R is an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl, cyano, phenyl or carbamoyl group, by an alkoxy group of 1 to 4 carbon atoms, an aryloxy, aryloxycarbonyl, aroyloxy or aroylamino group, by an alkoxy-carbonyl, alkanoyloxy, alkylcarbamoyl or alkanoylamino group of 2 to 6 carbon atoms, or by a phthalimido group, or is a cycloalkyl group of 5 to 8 carbon atoms, and X is a radical of the formula ~N~ or \.~ ~.
. ~ I ~z o wherein Y and Z are hydrogen or halogen atoms, or alkyl or alkoxy groups of 1 to 4 carbon atoms.
In the above definition, the term "aryl" denotes e.g.
~- or ~-naphthyl or diphenylyl, but preferably an unsub-stituted or a substituted phenyl radical. Possible sub-stituents are: halogen, especiall.y chlorine, and alkyl or alkoxy of 1 to 4 carbon atoms.
~S ~
Preferred pigments are those of the indicated formula wherein R is a methyl or ethyl group and X is the radical of the formula ~H
O
The pigments of the present invention are obtained by condensing 1,3-diiminoisoindoline, in any order, ~ith 1 mole each of acyanoacetamide of the formula NCCH2CONHR and barbituric acid or with a dihydroxyquinoline of the formula OH
Y~. ,!
~! !
OH
Z
Rep,resentative examples of cyanoacetamides are:
cyanoacetomethylamide, cyanoacetethylamide, cyanoaceto-n-propylamide, cyanoacetisopropylamide, cyanoaceto-n-butyl-amide, cyanoaceto-~-methoxyethylamide, cyanoaceto-~-ethoxy-ethylamide, cyanoaceto-~-methoxy-n-propylamide, cyanoaceto-~-cyanoethylamide, cyanoacetobenzylamide, cyanoaceto-a-phenyl-ethylamide, cyanoaceto-~-phenylethylamide, cyanoacetocyclo-hexylamide, cyanoaceto-~-hydroxyethylamide, cyanoaceto-~-acetyloxyethylamide, cyanoaceto-~-benzoyloxyethylamide, cyanoacetethoxycarbonylmethylamide.
Representative examples of dihydroxyquinolines are:
2,4-dihydroxyquinoline, 2,4-dihydroxy-6-chloroquinoline, 2,4-dihydroxy-6-methylquinoline, 2,4,7,8-dichloroquinoline, 2,4-dihydroxy-6,8-dichloroquinoline, 2,4-dihydroxy-6,8-di-bromoquinoline.
The diiminoisoindoline is conveniently reacted first with the cyanoacetamide to give the l-cyano-carbamoylmethylene-
The diiminoisoindoline is conveniently reacted first with the cyanoacetamide to give the l-cyano-carbamoylmethylene-
3-iminoisoindoline. This reaction is carried out advantageously in water or an organic solvent at elevated temperature, preferably in the range from 40 to 120C. Examples of suitable organic solvents are: aliphatic alcohols such as methanol, ethanol, isopropanol, isobutanol, amyl alcohol or ethylene glycol monoethyl ether, o-dichlorobenzene, dimethyl formamide, dimethyl acetamide, dimethyl sulfoxide, N-methyl-pyrrolidone, acetonitrile, dioxane, nitrobenzene or sulfolane.
The reaction of l-cyanocarbamoylmethylene-3-imino-isoindoline with barbituric acid or with the dihydroxy-quinoline is preferably carried out in the presence of an aliphatic carboxylic acid such as formic acid, acetic acid, propionic acid, mono- or dichloroacetic acid. The reaction temperature is advantageously in the range from 60 to 180C.
Both steps can also be carried out without isolation of the intermediate, in which case it is advantageous to use ethylene glycol and water as solvent.
The resultant pigments usually precipitate at elevated temperature and can be isolated in pure form by filtration and, if desired, by washing the filter cake with an organic solvent.
The pigments of the present invention can usually be used as crude products. If necessary or desired, the crude products can be converted into a finely dispersed form by grinding or kneading, advantageously using grinding assistants, such as inorganic and/or organic salts in the presence or absence of organic solvents. It is often possible to achieve an improvement in the properties of the crude pigmentsby treating them with organic solvents. After the grinding procedure, the assistants are removed in the conventional manner: soluble inorganic salts for example with water, and water-insoluble organic assistants for example by steam distillation.
During the production of the pigments, the particle form can be significantly influenced by the choice of solvent and of conditioning temperature. Thus it is possible to obtain from the same pigment a productive, transparent form, and a dull form which is somewhat redder in shade with improved fastness to light and atmospheric influences. In order to obtain the coarser, duller form it is advantageous in particular to carry out the conditioning, after the condensation, in water or a mixture of water and acid in the temperature range from 100-150C under pressure. The increase in the crystal size proceeds under technically simple conditions and is therefore also of interest from the economic viewpoint.
The dull as well as the transparent form of the pigments of the present invention have good application properties, especially good rheological properties, good dispersibility and excellent colour strength. Both forms are suitable for colouring organic material of high molecular weight of natural or synthetic origin. Such material can comprise for example natural resins, drying oils or rubber. However, it can also comprise modified natural materials, for example chlorinated rubber, oil-modified alkyd resins or cellulose derivatives, such as viscose, acetyl cellulose and nitro-cellulose, and in particular man-made organic polyplastics, that is to say, plastics which are obtained by polymerisation, polycondensation and polyaddition. The following produc~s may be mentioned in particular as belonging to this class of plastics: polyethylene, polypropylene, polyisobutylene, polystyrene, polyvinyl chloride, polyvinyl acetate, poly-acrylonitrile, polyacrylates and polymethacrylates; polyesters, ~140~3~
;
in particular high molecular esters of aromatic poly-carboxylic acids and polyfunctional alcohols; polyamides;
the condensation products of formaldehyde and phenols (phenolic plastics), and the condensation products of formaldehyde and urea, thiourea and melamine (aminoplasts);
the polyesters used as film-forming resins, namely both saturated polyesters, for example alkyd resins, and unsaturated polyesters, for example maleic resins, and also the polyaddition and polycondensation products of epichlorohydrin with diols or polyphenols known as epoxide resins; in addition thermoplasts, i.e. the non-curable polyplastics. It must be emphasised that not only the homogeneous compounds can be pigmented in the practice of this invention, but also mixtures of polyplastics, as well as co-condensates and copolymers, for example those based on butadiene.
Fur,ther compounds of high molecular weight are: vinyl, polyolefin and styrene polymers, such as polyplastics, especially the film formers or binders known as vehicles, in particular boiled linseed oil, nitrocellulose, alkyd resins, melamine resins and urea-formaldehyde resins. The pigmenting of the organic substances of high molecular weight with the pigments of the invention is effected f~r example by mixing such a pigment, optionally in the form of a master-batch, with these substrates, using roll mills, mixing or grinding devices. The pigmented material is there-after broughtinto the desired final form by known methods, such as calendering, pressing, extruding, coating, casting, or by injection moulding. It is often desirable to add plasticisers to the compounds of high molecular weight before forming them in order to obtain non-rigid moulded articles or to diminish their brittleness. Examples of such plasticisers are esters of phosphoric acid, phthalic acid or ~14~30 sebacic acid. The plasticisers can be added in the process of the invention before or after the incorporation of the pigment dye in the polyplastics. In order to obtain different shades it is also possible to add, in addition to the pigments of the invention, fillers or other colouring constituents, such as white, coloured or black pigments, in any amounts to the organic substances.
For pigmenting lacquers and prin~ing inks, the organic material of high molecular weight and the pigments, optionally together with additives such as fillers, other pigments, siccatives or plasticisers, are finely dispersed or disso~ved in a joint organic solvent or solvent mixture. The procedure can consist for example in dispersing or dissolving each of the components individually or also several jointly, and thereafter combining all the components.
The, pigmented organic materials of high molecular weight contain normally amounts from 0.001 to 30% by weight of pigment, based on the organic substance of high molecular weight to be pigmented. Polyplastics and lacquers contain preferably 0.1 to 5% by weight, and printing inks contain preferably 10 to 30% by weight. The amount of pigment to be chosen depends primarily on the desired colour strength, on the layer thickness of the moulded article, and finally also on the content of white pigment, if any, in the poly-plastic.
The very fast yellow colourations obtained with both the transparent and the dull pigments are distinguished by purity of shade, and good fastness to light, atmospheric influences, migration, overspraying and solvents, as well as heat resistance. The pigments have such good colour strength that they still produce strong colourations even after conversion to a dull form.
1 1 4~ 1 3~
The invention is illustrated by the following Examples.
Example 1: 14.5 g of 1-amino-3-iminoisoindolenine and 4.9 g of cyanoacetomethylamide are heated in 50 ml of methanol for 2 hours to reflux temperature. The reaction product is filtered off hot and dried, affording 10 g of a light yellow monocondensation product. 4.52 g of this compound and 2.52 g of barbituric acid are heated to reflux temperature in 80 ml of acetic acid. The pigment is filtered hot with suction after 1 hour, washed with methanol, acetone and water, and dried, affording 6.6 g of a yellow powder which, in this form, can be incorporated direct as pigment in paints and plastics. The colourations obtained are distinguished by a pure yellow shade with outstanding fastness to migration and overspraying.
Examples 2 to 13: The monocondensation products obtained from cyanoacetamides of the formula NCCH2CONHR are reacted with barbituric acid as in Example 1. The pigments can be incorporated direct in paints. The colourations obtained are strong and distinguished by a pure yellow shad0 and good fastness properties. The meaning of the radical R is indicated in columns 2 and 4 of the following table.
xample Example 2 5 8 -c2H4oa
The reaction of l-cyanocarbamoylmethylene-3-imino-isoindoline with barbituric acid or with the dihydroxy-quinoline is preferably carried out in the presence of an aliphatic carboxylic acid such as formic acid, acetic acid, propionic acid, mono- or dichloroacetic acid. The reaction temperature is advantageously in the range from 60 to 180C.
Both steps can also be carried out without isolation of the intermediate, in which case it is advantageous to use ethylene glycol and water as solvent.
The resultant pigments usually precipitate at elevated temperature and can be isolated in pure form by filtration and, if desired, by washing the filter cake with an organic solvent.
The pigments of the present invention can usually be used as crude products. If necessary or desired, the crude products can be converted into a finely dispersed form by grinding or kneading, advantageously using grinding assistants, such as inorganic and/or organic salts in the presence or absence of organic solvents. It is often possible to achieve an improvement in the properties of the crude pigmentsby treating them with organic solvents. After the grinding procedure, the assistants are removed in the conventional manner: soluble inorganic salts for example with water, and water-insoluble organic assistants for example by steam distillation.
During the production of the pigments, the particle form can be significantly influenced by the choice of solvent and of conditioning temperature. Thus it is possible to obtain from the same pigment a productive, transparent form, and a dull form which is somewhat redder in shade with improved fastness to light and atmospheric influences. In order to obtain the coarser, duller form it is advantageous in particular to carry out the conditioning, after the condensation, in water or a mixture of water and acid in the temperature range from 100-150C under pressure. The increase in the crystal size proceeds under technically simple conditions and is therefore also of interest from the economic viewpoint.
The dull as well as the transparent form of the pigments of the present invention have good application properties, especially good rheological properties, good dispersibility and excellent colour strength. Both forms are suitable for colouring organic material of high molecular weight of natural or synthetic origin. Such material can comprise for example natural resins, drying oils or rubber. However, it can also comprise modified natural materials, for example chlorinated rubber, oil-modified alkyd resins or cellulose derivatives, such as viscose, acetyl cellulose and nitro-cellulose, and in particular man-made organic polyplastics, that is to say, plastics which are obtained by polymerisation, polycondensation and polyaddition. The following produc~s may be mentioned in particular as belonging to this class of plastics: polyethylene, polypropylene, polyisobutylene, polystyrene, polyvinyl chloride, polyvinyl acetate, poly-acrylonitrile, polyacrylates and polymethacrylates; polyesters, ~140~3~
;
in particular high molecular esters of aromatic poly-carboxylic acids and polyfunctional alcohols; polyamides;
the condensation products of formaldehyde and phenols (phenolic plastics), and the condensation products of formaldehyde and urea, thiourea and melamine (aminoplasts);
the polyesters used as film-forming resins, namely both saturated polyesters, for example alkyd resins, and unsaturated polyesters, for example maleic resins, and also the polyaddition and polycondensation products of epichlorohydrin with diols or polyphenols known as epoxide resins; in addition thermoplasts, i.e. the non-curable polyplastics. It must be emphasised that not only the homogeneous compounds can be pigmented in the practice of this invention, but also mixtures of polyplastics, as well as co-condensates and copolymers, for example those based on butadiene.
Fur,ther compounds of high molecular weight are: vinyl, polyolefin and styrene polymers, such as polyplastics, especially the film formers or binders known as vehicles, in particular boiled linseed oil, nitrocellulose, alkyd resins, melamine resins and urea-formaldehyde resins. The pigmenting of the organic substances of high molecular weight with the pigments of the invention is effected f~r example by mixing such a pigment, optionally in the form of a master-batch, with these substrates, using roll mills, mixing or grinding devices. The pigmented material is there-after broughtinto the desired final form by known methods, such as calendering, pressing, extruding, coating, casting, or by injection moulding. It is often desirable to add plasticisers to the compounds of high molecular weight before forming them in order to obtain non-rigid moulded articles or to diminish their brittleness. Examples of such plasticisers are esters of phosphoric acid, phthalic acid or ~14~30 sebacic acid. The plasticisers can be added in the process of the invention before or after the incorporation of the pigment dye in the polyplastics. In order to obtain different shades it is also possible to add, in addition to the pigments of the invention, fillers or other colouring constituents, such as white, coloured or black pigments, in any amounts to the organic substances.
For pigmenting lacquers and prin~ing inks, the organic material of high molecular weight and the pigments, optionally together with additives such as fillers, other pigments, siccatives or plasticisers, are finely dispersed or disso~ved in a joint organic solvent or solvent mixture. The procedure can consist for example in dispersing or dissolving each of the components individually or also several jointly, and thereafter combining all the components.
The, pigmented organic materials of high molecular weight contain normally amounts from 0.001 to 30% by weight of pigment, based on the organic substance of high molecular weight to be pigmented. Polyplastics and lacquers contain preferably 0.1 to 5% by weight, and printing inks contain preferably 10 to 30% by weight. The amount of pigment to be chosen depends primarily on the desired colour strength, on the layer thickness of the moulded article, and finally also on the content of white pigment, if any, in the poly-plastic.
The very fast yellow colourations obtained with both the transparent and the dull pigments are distinguished by purity of shade, and good fastness to light, atmospheric influences, migration, overspraying and solvents, as well as heat resistance. The pigments have such good colour strength that they still produce strong colourations even after conversion to a dull form.
1 1 4~ 1 3~
The invention is illustrated by the following Examples.
Example 1: 14.5 g of 1-amino-3-iminoisoindolenine and 4.9 g of cyanoacetomethylamide are heated in 50 ml of methanol for 2 hours to reflux temperature. The reaction product is filtered off hot and dried, affording 10 g of a light yellow monocondensation product. 4.52 g of this compound and 2.52 g of barbituric acid are heated to reflux temperature in 80 ml of acetic acid. The pigment is filtered hot with suction after 1 hour, washed with methanol, acetone and water, and dried, affording 6.6 g of a yellow powder which, in this form, can be incorporated direct as pigment in paints and plastics. The colourations obtained are distinguished by a pure yellow shade with outstanding fastness to migration and overspraying.
Examples 2 to 13: The monocondensation products obtained from cyanoacetamides of the formula NCCH2CONHR are reacted with barbituric acid as in Example 1. The pigments can be incorporated direct in paints. The colourations obtained are strong and distinguished by a pure yellow shad0 and good fastness properties. The meaning of the radical R is indicated in columns 2 and 4 of the following table.
xample Example 2 5 8 -c2H4oa
4 -CH(CH3) 2 9 -CH2CH20CH3 -CH2CH ( CH3 ) 2 10 -C2H40COCH3 _ 13 _ -cyclohexyl 114~)130 Examples 14 and 15: The procedure of Example 1 is repeated, except that the moist crude pigment is suspended in a mixture of 20 ml of glacial acetic acid and 80 ml of water. The sus-pension is then heated under pressure for 3 hours to 120C, affording 6.4 g of a pigment which is a dull greenish yellow in tint and has improved fastness to light and atmospheric influences. The above procedure is repeated using the moist crude pigment of Example 3 instead of the pigment of Example 1, and heating the suspension to 110C. The resultant pigment is also a dull greenish yellow in tint and has improved fastness to light and atmospheric influences.
Example 16: A solution of 7.25 g of amino-iminoisoindolenine and 40 ml of ethylene glycol, which has been warmed to 60C, is run into a suspension of 4.9 g of cyanoacetomethylamide and 6.4 g of barbituric acid in 55 ml of water. The reaction mixture is stirred for 2 hours at 60C and then acidified with 15 ml of formic acid. Stirring is continued for a further 2 hours, then the reaction mixture is filtered with suction and the filter cake is dried, affording 14.5 g of the pigment described in Example 1.
Example 17: 4.52 g of the monocondensation product described in Example 1 and 2.52 g of barbituric acid are heated for
Example 16: A solution of 7.25 g of amino-iminoisoindolenine and 40 ml of ethylene glycol, which has been warmed to 60C, is run into a suspension of 4.9 g of cyanoacetomethylamide and 6.4 g of barbituric acid in 55 ml of water. The reaction mixture is stirred for 2 hours at 60C and then acidified with 15 ml of formic acid. Stirring is continued for a further 2 hours, then the reaction mixture is filtered with suction and the filter cake is dried, affording 14.5 g of the pigment described in Example 1.
Example 17: 4.52 g of the monocondensation product described in Example 1 and 2.52 g of barbituric acid are heated for
5 hours to reflux temperature in a mixture of 80 ml of water and 20 ml of acetic acid. The pigment is collected hot by filtration, washed with water and dried, affording 6.2 g of pigment which, in this form, can be incorporated direct in printing inks with good dispersibility. The colourations obtained are distinguished by high colour strength and a brilliant yellow shade of excellent lightfastness.
Example 18: 2.26 g of the monocondensation product obtained according to Example 1 and 1.61 g of 2,4-dihydroxyquinoline are hea~ed to reflux temperature in 50 ml of acetic acid.
1 1 4~ ~ 3~
The reaction mixture is diluted with 20 ml of o-dichloro-benzene and the pigment is collected hot by filtration after 2 hours. The filter cake is washed with methanol, acetone and water and dried, affording 2.5 g of an orange powder which, in this form, can be incorporated direct as pigment in paints. The colourations obtained are distinguished by a pure shade and good fastness to overspraying.
Examples 19 to 29: The procedure of Example 18 is repeated using equimolar amounts of compounds of the formula C~ ~CONXR
~\-/~X
il NH
instead of the monocondensate of Example l. The respective meanings of R are indicated in column 2 of the following table, and the dihydroxyquinolines listed in column 3 are used in equimolar amounts. Pigments with similarly good properties are obtained.
Example Dihydroxyquinoline Shade 19 -C2H5 2,4-dihydn~yquinoline reddish yellow 2 4 3 ,. ,.
21 -C2H40COCH3 ,. orange 22 -C2H40COC6H5 ,. yellowish orange 23 C~2C6H5 ,. reddish yellow 24 -CH3 7-chloro-294-dihydroxy- reddish yellow quinoline -C2H5 7-chloro-2,4-dihydroxy-~yellow _ quinoline ¦
114()130 Example Dihxydroxyquinoline Shade .. . .
26 C2~5 6,8-dibromo-2,4- yellow dihydroxyquinoline 27 -C2H40H 6,8-dibromo-2,4- redish yellow dihydroxyquinoline 28 -CH3 6-methyl-2,4-di- ye~owish ora~e hydroxyquinoline 29 -CH3 6,8-dichloro-2,4- reddish yellow dihydroxyquinoline Example 30: 0.6 g of the pigment obtained in Example 17 is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyl tin dilaurate and 2 g of titanium dioxide and the mixture is processed to a thin sheet for 15 minutes a~ 160C on a roll mill. The yellow colouration obtained is strong and fast to migration and light.
Example 31: 1 g of the pigment obtained in Example 17 is finely ground in an Engelsmann grinding machine with 4 g of a litho varnish of the 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).
Using a stereotype block, this varnish is printed in an amount of 1 g/m on art paper by letterpress printing.
Strong, yellow prints of good transparency, good gloss, and good lightfastness are obtained.
The pigment is also suitable for other printing methods, such as intaglio printing, offset printing, flexographic printing, with equally good results.
114(~130 Example 32: To lO0 g of a stoving lacquer consisting of 58.5 g of a 60% solution of a coconut alkyd resin in xylene, 23 g of a 65% solution of a melamine varnish gum in butanol, 17 g of xylene and 1.5 g of butanol, are added 1 g of the pigment of Example 1 and 5 g of titanium dioxide. The mixture ls ground for 48 hours in a ball mill and the pigmented lacquer is sprayed onto a clean metal surface. After stoving at 120C, a yellow finish of good colour strength and good fastness to light and overspraying and good resistance to atmospheric influences is obtained.
Example 18: 2.26 g of the monocondensation product obtained according to Example 1 and 1.61 g of 2,4-dihydroxyquinoline are hea~ed to reflux temperature in 50 ml of acetic acid.
1 1 4~ ~ 3~
The reaction mixture is diluted with 20 ml of o-dichloro-benzene and the pigment is collected hot by filtration after 2 hours. The filter cake is washed with methanol, acetone and water and dried, affording 2.5 g of an orange powder which, in this form, can be incorporated direct as pigment in paints. The colourations obtained are distinguished by a pure shade and good fastness to overspraying.
Examples 19 to 29: The procedure of Example 18 is repeated using equimolar amounts of compounds of the formula C~ ~CONXR
~\-/~X
il NH
instead of the monocondensate of Example l. The respective meanings of R are indicated in column 2 of the following table, and the dihydroxyquinolines listed in column 3 are used in equimolar amounts. Pigments with similarly good properties are obtained.
Example Dihydroxyquinoline Shade 19 -C2H5 2,4-dihydn~yquinoline reddish yellow 2 4 3 ,. ,.
21 -C2H40COCH3 ,. orange 22 -C2H40COC6H5 ,. yellowish orange 23 C~2C6H5 ,. reddish yellow 24 -CH3 7-chloro-294-dihydroxy- reddish yellow quinoline -C2H5 7-chloro-2,4-dihydroxy-~yellow _ quinoline ¦
114()130 Example Dihxydroxyquinoline Shade .. . .
26 C2~5 6,8-dibromo-2,4- yellow dihydroxyquinoline 27 -C2H40H 6,8-dibromo-2,4- redish yellow dihydroxyquinoline 28 -CH3 6-methyl-2,4-di- ye~owish ora~e hydroxyquinoline 29 -CH3 6,8-dichloro-2,4- reddish yellow dihydroxyquinoline Example 30: 0.6 g of the pigment obtained in Example 17 is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyl tin dilaurate and 2 g of titanium dioxide and the mixture is processed to a thin sheet for 15 minutes a~ 160C on a roll mill. The yellow colouration obtained is strong and fast to migration and light.
Example 31: 1 g of the pigment obtained in Example 17 is finely ground in an Engelsmann grinding machine with 4 g of a litho varnish of the 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).
Using a stereotype block, this varnish is printed in an amount of 1 g/m on art paper by letterpress printing.
Strong, yellow prints of good transparency, good gloss, and good lightfastness are obtained.
The pigment is also suitable for other printing methods, such as intaglio printing, offset printing, flexographic printing, with equally good results.
114(~130 Example 32: To lO0 g of a stoving lacquer consisting of 58.5 g of a 60% solution of a coconut alkyd resin in xylene, 23 g of a 65% solution of a melamine varnish gum in butanol, 17 g of xylene and 1.5 g of butanol, are added 1 g of the pigment of Example 1 and 5 g of titanium dioxide. The mixture ls ground for 48 hours in a ball mill and the pigmented lacquer is sprayed onto a clean metal surface. After stoving at 120C, a yellow finish of good colour strength and good fastness to light and overspraying and good resistance to atmospheric influences is obtained.
Claims (7)
1. An isoindoline pigment of the formula wherein R is an alkyl radical of 1 to 4 carbon atoms which can be substituted by a hydroxyl, cyano, phenyl or carbamoyl group, by an alkoxy group of 1 to 4 carbon atoms, an aryloxy, aryloxycarbonyl, aroyloxy or aroylamino group, by an alkoxy-carbonyl, alkanoyloxy, alkylcarbamoyl or alkanoylamino group of 2 to 6 carbon atoms, or by a phthalimido group, or is a cycloalkyl group of 5 to 8 carbon atoms, and X is a radical of the formula or wherein Y and Z are hydrogen or halogen atoms, or alkyl or alkoxy groups of 1 to 4 carbon atoms.
2. An isoindoline pigment according to claim 1, wherein R is the methyl or ethyl group.
3. An isoindoline pigment according to claim 1, wherein X is the radical of the formula
4. The compound according to claim 1 of the formula
5. The compound according to claim 1 of the formula
6. The compound according to claim 1 of the formula
7. Organic material of high molecular weight which is pigmented with an isoindoline according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1004679 | 1979-11-09 | ||
| CH10046/79-8 | 1979-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140130A true CA1140130A (en) | 1983-01-25 |
Family
ID=4358728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000364234A Expired CA1140130A (en) | 1979-11-09 | 1980-11-07 | Isoindoline pigments, production and use thereof |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0029007A1 (en) |
| JP (1) | JPS5681369A (en) |
| CA (1) | CA1140130A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4746740A (en) * | 1985-07-22 | 1988-05-24 | Basf Aktiengesellschaft | Isoindoline colorants |
| US4785114A (en) * | 1985-09-20 | 1988-11-15 | Basf Aktiengesellschaft | Quinophthalone dyes |
| US5177209A (en) * | 1991-04-22 | 1993-01-05 | Miles Inc. | Process for preparation of asymmetric isoindoline pigments |
| US5326872A (en) * | 1991-04-22 | 1994-07-05 | Miles Inc. | Process for preparation of asymmetric isoindoline pigments |
| US8026361B2 (en) | 2006-07-18 | 2011-09-27 | Basf Aktiengesellschaft | Isoindoline pigments |
| US9809723B2 (en) | 2012-09-11 | 2017-11-07 | Toyo Ink Sc Holdings Co., Ltd. | Active energy ray-curable inkjet ink composition |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH669388A5 (en) * | 1985-07-09 | 1989-03-15 | Basf Ag | |
| US6143067A (en) * | 1998-01-28 | 2000-11-07 | Ciba Specialty Chemicals Corporation | Isoindoline pigment having improved low shear dispersibility |
| ATE541900T1 (en) * | 2007-12-10 | 2012-02-15 | Basf Se | ISOMETRIC ISOINDOLINE YELLOW PIGMENT |
| JP6051706B2 (en) * | 2012-09-11 | 2016-12-27 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable inkjet ink composition |
| JP7055677B2 (en) * | 2017-03-29 | 2022-04-18 | 住友化学株式会社 | Method for manufacturing isoindoline pigment |
| TWI754733B (en) * | 2017-03-29 | 2022-02-11 | 日商住友化學股份有限公司 | Isoindoline dye and method for producing the same |
| JP7105024B1 (en) | 2021-08-03 | 2022-07-22 | 東洋インキＳｃホールディングス株式会社 | Pigment compositions, coloring compositions, paints, inks, ink sets, printed matter, and packaging materials |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1537299A (en) * | 1966-09-09 | 1968-08-23 | Bayer Ag | Process for the preparation of new isoindoline derivatives |
| DE1670748A1 (en) * | 1966-09-09 | 1973-05-30 | Bayer Ag | PROCESS FOR PRODUCING NEW ISOINDOLINE DERIVATIVES |
| DE2121524C3 (en) * | 1971-05-03 | 1979-02-01 | Basf Ag, 6700 Ludwigshafen | Disperse dyes from o-phthalonitrile, their production and their use |
| CH614457A5 (en) * | 1975-04-11 | 1979-11-30 | Ciba Geigy Ag | |
| DE2800815C2 (en) * | 1978-01-10 | 1986-12-11 | Basf Ag, 6700 Ludwigshafen | Process for the production of easily distributable and opaque isoindoline pigment dyes |
| DE2831673A1 (en) * | 1978-07-19 | 1980-02-07 | Basf Ag | HETEROCYCLIC COMPOUNDS |
| DE2914086B1 (en) * | 1979-04-07 | 1980-09-18 | Basf Ag | Isoindoline dyes and their use |
-
1980
- 1980-11-03 EP EP80810337A patent/EP0029007A1/en not_active Withdrawn
- 1980-11-07 CA CA000364234A patent/CA1140130A/en not_active Expired
- 1980-11-08 JP JP15755380A patent/JPS5681369A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4746740A (en) * | 1985-07-22 | 1988-05-24 | Basf Aktiengesellschaft | Isoindoline colorants |
| US4785114A (en) * | 1985-09-20 | 1988-11-15 | Basf Aktiengesellschaft | Quinophthalone dyes |
| US5177209A (en) * | 1991-04-22 | 1993-01-05 | Miles Inc. | Process for preparation of asymmetric isoindoline pigments |
| US5326872A (en) * | 1991-04-22 | 1994-07-05 | Miles Inc. | Process for preparation of asymmetric isoindoline pigments |
| US8026361B2 (en) | 2006-07-18 | 2011-09-27 | Basf Aktiengesellschaft | Isoindoline pigments |
| US9809723B2 (en) | 2012-09-11 | 2017-11-07 | Toyo Ink Sc Holdings Co., Ltd. | Active energy ray-curable inkjet ink composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0029007A1 (en) | 1981-05-20 |
| JPS5681369A (en) | 1981-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |