CA1115881A - Process for pigmenting organic material of high molecular weight - Google Patents
Process for pigmenting organic material of high molecular weightInfo
- Publication number
- CA1115881A CA1115881A CA285,900A CA285900A CA1115881A CA 1115881 A CA1115881 A CA 1115881A CA 285900 A CA285900 A CA 285900A CA 1115881 A CA1115881 A CA 1115881A
- Authority
- CA
- Canada
- Prior art keywords
- molecular weight
- high molecular
- organic material
- formula
- parts
- 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
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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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
- C08K5/235—Diazo and polyazo compounds
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
Abstract
Abstract of the Disclosure A process for pigmenting organic material of high molecular weight which comprises the use of a disazo compound of the formula whereln X represents a hydrogen or chlorlne atom, an alkyl or alkoxy group of 1 to 6 carbon atoms, a nltro or trifluoro-methyl group and A represents an alkyl group of 1 to 6 carbon atoms.
The yellow to orange coloratlons obtained hnve good fastness to migration and unusually good fastness to hight and weathering.
The yellow to orange coloratlons obtained hnve good fastness to migration and unusually good fastness to hight and weathering.
Description
~ilS~l The present invention is based on the observation that colourations of outstanding fastness are obtained in organic material of high molecular weight by using as pigments disazo compounds of the formula =N-CHCONH ~ NHCOCH-N-Cl RO
wherein X represents a chlorlne atom, methyl or a tri-fluoromethyl group and R represents an alkyl group of 1 to 3 carbon atoms, in a finely dispersed form.
Preferred disazo compounds are those of the indicated formula wherein R represents an ethyl group and X repre-sents a chlorine atom.
The disazo compound of the formula N=N-CHCONH ~ NHCO-CH-N-Cl C2H5 Cl is also of particular interest.
The dlsazo colourants to be used according to the lnvention are known compounds which are obtained by coupling the diazo-component of an amine of the formula X
~ NN~ ~
with a bisacetoacetyl-phenylenediamine of the formula D ~
1~15~1 ~R
CH3COCH2COHN ~ NHCOCH2COCH3 OR
in the molar ratio 2:1.
The following diamines may be cited as examples of diazo components.
wherein X represents a chlorlne atom, methyl or a tri-fluoromethyl group and R represents an alkyl group of 1 to 3 carbon atoms, in a finely dispersed form.
Preferred disazo compounds are those of the indicated formula wherein R represents an ethyl group and X repre-sents a chlorine atom.
The disazo compound of the formula N=N-CHCONH ~ NHCO-CH-N-Cl C2H5 Cl is also of particular interest.
The dlsazo colourants to be used according to the lnvention are known compounds which are obtained by coupling the diazo-component of an amine of the formula X
~ NN~ ~
with a bisacetoacetyl-phenylenediamine of the formula D ~
1~15~1 ~R
CH3COCH2COHN ~ NHCOCH2COCH3 OR
in the molar ratio 2:1.
The following diamines may be cited as examples of diazo components.
2,5-dichloroaniline and 2-methyl-5-chloroaniline.
The coupling components are obtained by reacting a diamine of the formula qR
2 ~ 2 R
wherein R has the indicated meanings, with diketene. The following diamines may be cited as examples:
2,5-dimethoxy-1,4-phenylenediamine 2,5-diethoxy-1,4-phenylenediamine 2,5-dipropoxy-1,4-phenylenediamine 2,5-diisopropoxy-1,4-phenylenediamine The coupling preferably takes place in a weakly acid medium, advantageously in the presence of conventional agents that promote the coupling. Such agents are in par-tlcular dispersants, for example aralkylsulphonates, such as dodecylbenzenesulphonate, or l,l'-dinaphthylmethane-2,2'-disulphonic acid or polycondensation product,s of alkylene oxides. The dispersion of the coupling component can also ~15~1 advantageously contain protecti~e colloids, for exa~ple methyl ceL~ulose or ~inor amounts of inert organic solvents which are sparingly soluble or insoluble in water, for example optionally halogenated or nitrated aromatic hydrocarbons, for example, benzene, toluene, xylene, chlorobenzene, dichloro-benzene or nitrobenzene, and also aliphatic halogenated hydro-carbons, for example carbon tetrachloride or trichloro-ethylene, as well as organic solvents which are miscible with water, for example, acetone, ethylene glycol monomethyl ether, methyl ethyl ketone, methanol, ethanol or isopropanol.
The coupling can also advantageously be carried out by continuously combining an acid solution of the diazonium salt with an alkaline solution of the coupling component in a mixing nozzle, whereupon an immediate coupling of the component occurs. Care must be taken that the diazo component and the coupling component are present in equimolecular amounts in the mixlng nozzle, although a slight excess of coupling component proves to be advantageous. This is most simply accomplished by controlling the pH of the liquid in the mixing nozzle.
Furthermore, intense turbulent mixing of the two solutions in the mixing nozzle must be ensured. The resultant colourant dispersion is continuously drawn off from the mixing nozzle and the colourant separated by filtration.
Finally, the coupling can also be carried out by suspending the diazo component with the coupling component in the D -~-i~15~1 molar ratio 2:1 in an organic solvent and treating the coup-ling mixture with a diazotising agent, in particular with an ester of nitrous acid, such as methyl, ethyl, butyl, amyl or octyl nitrite.
The pigments usually precipitate at elevated temperature and can be isolated in pure form by filtration and subsequent removal of any impurities by washing them with an organic solvent.
The pigments have in general a good texture and can be widely 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 ab-sence of organic solvents. After the grinding procedure, the assistants are removed in the conventional manner: soluble inorganic salts for example with water, and water-insoluble assistants for example by steam distillation The properties of the crude pigments can often be improved by treating them with organic solvents, preferably those having a boiling point above 100C. Particularly suitable organic solvents are: benzenes which are substituted by halogen atoms, alkyl ornitro groups, for example ~ylene, chlorobenzene, o-dichlorobenzene or nitrobenzene, as well as pyridine bases, such as pyridine, picoline or quinoline, and also ketones, for example, cyclohexanone; ethers, for example ~_~
Bi~l ethyl~ne glycol monomethyl and monoeth~l ether; amides, such as dimethyl formamide or N-methylpyrrolidone, as well as dimethyl sulphoxide or water under pressure.
The aftertreatment is effected preferably by heating the pigment in ~he solvent to 100-150C, when in many cases an increase in the granular size occurs. The fastness to light and migration of the resultant pigments are thereby favourably influenced.
Suitable material of high molecular weight comprises preferably synthetic resins, for example cellulose ethers and esters, such as acetyl cellulose, nitrocellulose, and amino-plasts, in particular ureajformaldehyde and melamine/formal-dehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, poly-ethylene, polypropylene, polyacrylonitrile, polyacrylates.
Of particular interest are lacquers, for example those based on alkyd/melamine/formaldehyde resins, alkyd/urea/
formaldehyde resins, as well as thermoplastic and thermocuring acrylic resins.
The colourants to be used according to the invention are also of great interest for use in printing inks.
The pigments of the present invention have good dispersibility and thermostability. The colourations obtained therewith are distinguished by good fastness to migration and unu~ually good fastness to light and ~7ea~hering.
1~5~ 1 The disazo compounds to be used according to the invention are described in par~ in German patent specification ~50,039. However, no mention at all is made therein of their use as pigments.
Swiss patent specification 557,407 describes similar disazo c~ourants which are used for pigmenting organic material of high molecular weight. However, the colourations obtained therewith have less good fastness to light and weathering.
The invention is illustrated by the following Examples, in which the parts and percentages are by weight unless otherwise indicated.
, 1~15Wi Example 1 5.1 parts of 2,S-dichloroaniline are dissolved in 40 parts by volume of glacial acetic acid at room temperature.
The brown solution is stirred with 8 parts by volume of conc.
hydrochloric acid and the thick suspension which forms (chlorohydrate) is diluted with 16 parts of water, cooled to 5C, treated dropwise in the course of 15 minutes and at 5C
with 8.3 parts by volume of 4N sodium nitrite solution and the resultant brown diazo solution is filtered clear.
Subsequently, 5.5 parts of 2,5-diethoxy-1,4-bis-acetoacetyl-aminobenzene are dissolved in 60 parts of water ~ith the addition of 7.5 parts by volume of 30% sodium hydroxide solution. The pale yellow solution is treated at 5C in the course of 15 minutes with the above diazo solution, whereupon an orange precipitate forms. The resultant suspension is adjusted to a pH value of 5 by the slow addition of 26 parts of 30% aqueous sodium hydroxide solution. It is stirred for 4 hour8 at a temperature rising to 20C, diluted with 400 parts of water, heated in the course of 1 hour to 75C and filtered hot by suction. The residue is washed free of salt and dried in vacuo at 60C, affording 10.14 parts (98% of theory) of a red powder of the formula i~15~
Cl &l `N ~ ~ =N ~>
¦ O` ¦ Cl CH3CO--CII-CO~H ~ I~HCO-CH-COCH~
C~H5 After an aftertreatment in N-methylpyrrolidone (1 hour at 162C), this pigment colours polyvinyl chloride in fast, orange shades when incorporated thereinto on a roll mill.
The pigment also colours polyester resins in bright and very fast orange shades.
nalysis: calculated: C 50.72 H 3.97 N 11.83 Cl 19.96%
found: C 50.5 H 3.9 N 12.1 Cl 19.8 %
The 2,5-diethoxy-1,4-bis~acetoacetylaminobenzene can be prepared as follows: 9.8 parts of 2,5-diethoxy-1,4-phenylene-diamine are heated in 100 parts by volume of glacial acetic acid to 40C. The resultant brown solution is treated dropwise in the course of 10 minutes with 8.5 parts of diketene, whereupon the temperature rises to 73C and a beige precipitate forms. The slurry is heated to 98C over the course of 10 minutes, stirred for 1 hour at this temperature, allowed to cool to xoom temperature, and the precipitate is collected by suction filtration. The produ~ is washed with 40% acetic acid and then with cold water ana dried, affording l~S~l 14.9 p~rts (~1% of theory) of a pale yellow powder with a melting pOillt of 214~-216~C.
nalysis: calclllated: C 59.33 H 6.64 N 7.69%
ound: C 59.2 H 6.6 N 7.7%
The following table lis~s further pigments which are obtained by coupling the diazotised bases of column I with the bis-acetoaceticarylides of the diamines of column II in the molar ratio 2:1. Column III indicates the shade of polyvinyl chloride sheeting which is coloured with 0.2% of these pigments.
f~
l~S~i Example II III
2 2-methyl-5- 2,5-diethoxy-1,4- yellowish chloraniline phenylenediamine orange
The coupling components are obtained by reacting a diamine of the formula qR
2 ~ 2 R
wherein R has the indicated meanings, with diketene. The following diamines may be cited as examples:
2,5-dimethoxy-1,4-phenylenediamine 2,5-diethoxy-1,4-phenylenediamine 2,5-dipropoxy-1,4-phenylenediamine 2,5-diisopropoxy-1,4-phenylenediamine The coupling preferably takes place in a weakly acid medium, advantageously in the presence of conventional agents that promote the coupling. Such agents are in par-tlcular dispersants, for example aralkylsulphonates, such as dodecylbenzenesulphonate, or l,l'-dinaphthylmethane-2,2'-disulphonic acid or polycondensation product,s of alkylene oxides. The dispersion of the coupling component can also ~15~1 advantageously contain protecti~e colloids, for exa~ple methyl ceL~ulose or ~inor amounts of inert organic solvents which are sparingly soluble or insoluble in water, for example optionally halogenated or nitrated aromatic hydrocarbons, for example, benzene, toluene, xylene, chlorobenzene, dichloro-benzene or nitrobenzene, and also aliphatic halogenated hydro-carbons, for example carbon tetrachloride or trichloro-ethylene, as well as organic solvents which are miscible with water, for example, acetone, ethylene glycol monomethyl ether, methyl ethyl ketone, methanol, ethanol or isopropanol.
The coupling can also advantageously be carried out by continuously combining an acid solution of the diazonium salt with an alkaline solution of the coupling component in a mixing nozzle, whereupon an immediate coupling of the component occurs. Care must be taken that the diazo component and the coupling component are present in equimolecular amounts in the mixlng nozzle, although a slight excess of coupling component proves to be advantageous. This is most simply accomplished by controlling the pH of the liquid in the mixing nozzle.
Furthermore, intense turbulent mixing of the two solutions in the mixing nozzle must be ensured. The resultant colourant dispersion is continuously drawn off from the mixing nozzle and the colourant separated by filtration.
Finally, the coupling can also be carried out by suspending the diazo component with the coupling component in the D -~-i~15~1 molar ratio 2:1 in an organic solvent and treating the coup-ling mixture with a diazotising agent, in particular with an ester of nitrous acid, such as methyl, ethyl, butyl, amyl or octyl nitrite.
The pigments usually precipitate at elevated temperature and can be isolated in pure form by filtration and subsequent removal of any impurities by washing them with an organic solvent.
The pigments have in general a good texture and can be widely 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 ab-sence of organic solvents. After the grinding procedure, the assistants are removed in the conventional manner: soluble inorganic salts for example with water, and water-insoluble assistants for example by steam distillation The properties of the crude pigments can often be improved by treating them with organic solvents, preferably those having a boiling point above 100C. Particularly suitable organic solvents are: benzenes which are substituted by halogen atoms, alkyl ornitro groups, for example ~ylene, chlorobenzene, o-dichlorobenzene or nitrobenzene, as well as pyridine bases, such as pyridine, picoline or quinoline, and also ketones, for example, cyclohexanone; ethers, for example ~_~
Bi~l ethyl~ne glycol monomethyl and monoeth~l ether; amides, such as dimethyl formamide or N-methylpyrrolidone, as well as dimethyl sulphoxide or water under pressure.
The aftertreatment is effected preferably by heating the pigment in ~he solvent to 100-150C, when in many cases an increase in the granular size occurs. The fastness to light and migration of the resultant pigments are thereby favourably influenced.
Suitable material of high molecular weight comprises preferably synthetic resins, for example cellulose ethers and esters, such as acetyl cellulose, nitrocellulose, and amino-plasts, in particular ureajformaldehyde and melamine/formal-dehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, poly-ethylene, polypropylene, polyacrylonitrile, polyacrylates.
Of particular interest are lacquers, for example those based on alkyd/melamine/formaldehyde resins, alkyd/urea/
formaldehyde resins, as well as thermoplastic and thermocuring acrylic resins.
The colourants to be used according to the invention are also of great interest for use in printing inks.
The pigments of the present invention have good dispersibility and thermostability. The colourations obtained therewith are distinguished by good fastness to migration and unu~ually good fastness to light and ~7ea~hering.
1~5~ 1 The disazo compounds to be used according to the invention are described in par~ in German patent specification ~50,039. However, no mention at all is made therein of their use as pigments.
Swiss patent specification 557,407 describes similar disazo c~ourants which are used for pigmenting organic material of high molecular weight. However, the colourations obtained therewith have less good fastness to light and weathering.
The invention is illustrated by the following Examples, in which the parts and percentages are by weight unless otherwise indicated.
, 1~15Wi Example 1 5.1 parts of 2,S-dichloroaniline are dissolved in 40 parts by volume of glacial acetic acid at room temperature.
The brown solution is stirred with 8 parts by volume of conc.
hydrochloric acid and the thick suspension which forms (chlorohydrate) is diluted with 16 parts of water, cooled to 5C, treated dropwise in the course of 15 minutes and at 5C
with 8.3 parts by volume of 4N sodium nitrite solution and the resultant brown diazo solution is filtered clear.
Subsequently, 5.5 parts of 2,5-diethoxy-1,4-bis-acetoacetyl-aminobenzene are dissolved in 60 parts of water ~ith the addition of 7.5 parts by volume of 30% sodium hydroxide solution. The pale yellow solution is treated at 5C in the course of 15 minutes with the above diazo solution, whereupon an orange precipitate forms. The resultant suspension is adjusted to a pH value of 5 by the slow addition of 26 parts of 30% aqueous sodium hydroxide solution. It is stirred for 4 hour8 at a temperature rising to 20C, diluted with 400 parts of water, heated in the course of 1 hour to 75C and filtered hot by suction. The residue is washed free of salt and dried in vacuo at 60C, affording 10.14 parts (98% of theory) of a red powder of the formula i~15~
Cl &l `N ~ ~ =N ~>
¦ O` ¦ Cl CH3CO--CII-CO~H ~ I~HCO-CH-COCH~
C~H5 After an aftertreatment in N-methylpyrrolidone (1 hour at 162C), this pigment colours polyvinyl chloride in fast, orange shades when incorporated thereinto on a roll mill.
The pigment also colours polyester resins in bright and very fast orange shades.
nalysis: calculated: C 50.72 H 3.97 N 11.83 Cl 19.96%
found: C 50.5 H 3.9 N 12.1 Cl 19.8 %
The 2,5-diethoxy-1,4-bis~acetoacetylaminobenzene can be prepared as follows: 9.8 parts of 2,5-diethoxy-1,4-phenylene-diamine are heated in 100 parts by volume of glacial acetic acid to 40C. The resultant brown solution is treated dropwise in the course of 10 minutes with 8.5 parts of diketene, whereupon the temperature rises to 73C and a beige precipitate forms. The slurry is heated to 98C over the course of 10 minutes, stirred for 1 hour at this temperature, allowed to cool to xoom temperature, and the precipitate is collected by suction filtration. The produ~ is washed with 40% acetic acid and then with cold water ana dried, affording l~S~l 14.9 p~rts (~1% of theory) of a pale yellow powder with a melting pOillt of 214~-216~C.
nalysis: calclllated: C 59.33 H 6.64 N 7.69%
ound: C 59.2 H 6.6 N 7.7%
The following table lis~s further pigments which are obtained by coupling the diazotised bases of column I with the bis-acetoaceticarylides of the diamines of column II in the molar ratio 2:1. Column III indicates the shade of polyvinyl chloride sheeting which is coloured with 0.2% of these pigments.
f~
l~S~i Example II III
2 2-methyl-5- 2,5-diethoxy-1,4- yellowish chloraniline phenylenediamine orange
3 2,5-dichloro- 2,5-dimethoxy- orange aniline 1,4-phenylene-diamine
4 2,5-dichloro- 2,5-dipropoxy- orange aniline 1,4-phenylene-diamine 2-methyl-5- ,. yellowish chloroaniline orange 6 2,5-dichloro- 2,5-diisopropoxy- yellow aniline 1,4-phenylenedi-amine Example 7 3.5 parts of 2,5-dichloroaniline and 3.6 parts of 2,5-diethoxy-1,4-bisacetoacetylaminobenzene are dissolved at 50C in 200 parts of ethyl cellosolve and 20 parts of glacial acetic acid. After cooling to room temperature,2.5 parts of tert-butylnitrite in 100 parts of dichlorobenzene are added dropwise, whereupon the temperature ri~es to 40C and the pigment formation commences. The batch is subsequently stirred for 2 hours at 40 to 50C and for 5 hours at 130 to 140C, in thecourse of which the colourant assumes a homogeneous crystalline form. Microscopic exami-nation reveals orange crystalline aggregates having a 1~15~1 length of 5 to 10 ,u. After filtration at 140C, washing with hot dichlorobenzene until the filtrate runs colour-less, expelling the dichlorobenzene by methanol and finally washing with hot water and drying, 6 parts of an orange pigment are obtained.
Example 8 0.2 g of the pigment obtained in Example 1 and 100 g of polystyrene granules are mixed and processed on a roll mill at 130C until the colouration appears homogeneous.
The composition is then pressed between chromed plates to sheets. The orange colouration of the sheets is of good lightfastness. The pigmentation can also be carried out in an extruder instead of on a roll mill. In addition, it is also possible to granulate the homogeneously pigmented composition and to mould it in an injection moulding machine.
Example 9 0.2 g of the pigment prepared in accordance with Example 1, 1 g of titanium dioxide (rutile) and 100 g of polyethylene granules are mixed in a drum mixer and the mixture is subsequently processed on a roll mill at 130C. The composition ls pressed hot to sheets or formed ln an extruder. The sheet~ have a fine orange shade of excellent lightfastness.
lil5~}1 Example 10 0.1 g of the pigment prepared in accordance with Example 1, 0.5 g of titanium dioxide (rutile) and 100 g of polypropylene granules are mixed in a drum mixer and the mixture is subsequently processed on a roll mill at 130C
until it is homogenously coloured. The composition ls pressed hot to rough sheets of 1 mm. These sheets have a fine orange shade of good lightfastness.
Example 11 100 g of a formaldehyde/urea resin in powder form which is suitable for moulding materials, 10 g of lithopone and 1 g of the pigment prepared in accordance with Example 1, are ground for 16 hours in a ball mill. The composition is subsequently pressed at 140-160C into moulds. The orange samples have good lightfastness and heat resistance.
Example 12 24.5 g of an unesterified epoxide resin, 10.5 g of an oil-reactive alkylphenol resin, 35 g of xylene and 30 g of diacetone alcohol are processed to a lacquer and ground for 24 hours ln a ball mill with 4 g of the pigment obtaln~d accordlng to example 1. After spraying on~o alumlnlum sheets and stovlng at 120C, orange coatlngs of very good fastness to heat, overstripe bleeding and light are obtained.
D
~15~
Example 13 Acrylic resin stoving enamel 4 parts of the finely divided pigment of Example 1 are stirred into 20 parts of solvent of the following composition: 50 parts of Solvesso 150 !mixture of aromatic carbons), 15 parts of butyl acetate, 5 parts of Exkin II
(levelling agent based on ketoxime), 25 parts of methyl isobutyl ketone and 5 parts of silicone oil (1 % in Solvesso 150). After complete dispersion has been attained (in approx. 15 to 60 minutes, depending on the type of stlrrer), the following binders are added: 48.3 parts of 8aycryl L 530 (acrylic resin; 51 % in xylene/butanol 3:1) and 23.7 parts of Maprenal TTX (melamine resin; 55 % in butanol). After brief homogenisation, the lacquer is applled by conventional methods, such as spraying and immersing, or in the coil coating method specially for the continuous coating of metal sheets, and stoves ~stoving for 30 minutes at 130C). The orange finishes are distinguished by very good levelness, high gloss and excellent fine distribution of the pigment as well as by excellent weather fastness properties.
Example 14 4 g of the pigment obtained according to Example 1, 35 g of a 60 % solution of an alkyd resin, modified with urea/formaldehyde, in xylene/butanol 1:1, 10 g of oil of terpentine and 5 g of xylene, are ground for 48 ~ours in a ball mill. After spraying the resultant coloured lacquer onto an aluminium sheet and stoving at 120C, an orange finish of very good fastness to light, heat and overstripe bleeding is obtained D
1~5~1 Example 15 80 g of an unsaturated liquid polyester resin, 19.72 g of monostyrene and 0.28 g of a cobalt siccative which contains 16 ~ of cobalt, are ground for 48 hours-in a ball mill with 1 g of the pigment obtained according to Example 1 and 5 g of titanium dioxide ~rutile).
Shortly before the application of this lacquer, a mixture consisting of 4.15 g of cumene hydroperoxide (70 %), 2.42 g of ethyl acetate and 13.33 g butyl acetate is added. Card-board is coated with this mixture and dried in the air to give an orange coating of very good fastness to light, heat and overstripe bleeding.
Example 16 67 g of polyvinyl chloride powder (suspension polymer), 33 g of dioctyl phthalate, 2 g of dibutyl tin dilaurate, 0.3 g of a stabiliser on phosphate basis and 0.7 g of the pigment prepared according to Example 1, are mixed and processed for 15 minutes at 160C on a roll mill. Subsequently a sheet having a thickness of 0.4 mm is prepared on the calender. It is coloured ln a bright orange shade which is heat-reslstant and fast to migra-tlon.
.,;
i',
Example 8 0.2 g of the pigment obtained in Example 1 and 100 g of polystyrene granules are mixed and processed on a roll mill at 130C until the colouration appears homogeneous.
The composition is then pressed between chromed plates to sheets. The orange colouration of the sheets is of good lightfastness. The pigmentation can also be carried out in an extruder instead of on a roll mill. In addition, it is also possible to granulate the homogeneously pigmented composition and to mould it in an injection moulding machine.
Example 9 0.2 g of the pigment prepared in accordance with Example 1, 1 g of titanium dioxide (rutile) and 100 g of polyethylene granules are mixed in a drum mixer and the mixture is subsequently processed on a roll mill at 130C. The composition ls pressed hot to sheets or formed ln an extruder. The sheet~ have a fine orange shade of excellent lightfastness.
lil5~}1 Example 10 0.1 g of the pigment prepared in accordance with Example 1, 0.5 g of titanium dioxide (rutile) and 100 g of polypropylene granules are mixed in a drum mixer and the mixture is subsequently processed on a roll mill at 130C
until it is homogenously coloured. The composition ls pressed hot to rough sheets of 1 mm. These sheets have a fine orange shade of good lightfastness.
Example 11 100 g of a formaldehyde/urea resin in powder form which is suitable for moulding materials, 10 g of lithopone and 1 g of the pigment prepared in accordance with Example 1, are ground for 16 hours in a ball mill. The composition is subsequently pressed at 140-160C into moulds. The orange samples have good lightfastness and heat resistance.
Example 12 24.5 g of an unesterified epoxide resin, 10.5 g of an oil-reactive alkylphenol resin, 35 g of xylene and 30 g of diacetone alcohol are processed to a lacquer and ground for 24 hours ln a ball mill with 4 g of the pigment obtaln~d accordlng to example 1. After spraying on~o alumlnlum sheets and stovlng at 120C, orange coatlngs of very good fastness to heat, overstripe bleeding and light are obtained.
D
~15~
Example 13 Acrylic resin stoving enamel 4 parts of the finely divided pigment of Example 1 are stirred into 20 parts of solvent of the following composition: 50 parts of Solvesso 150 !mixture of aromatic carbons), 15 parts of butyl acetate, 5 parts of Exkin II
(levelling agent based on ketoxime), 25 parts of methyl isobutyl ketone and 5 parts of silicone oil (1 % in Solvesso 150). After complete dispersion has been attained (in approx. 15 to 60 minutes, depending on the type of stlrrer), the following binders are added: 48.3 parts of 8aycryl L 530 (acrylic resin; 51 % in xylene/butanol 3:1) and 23.7 parts of Maprenal TTX (melamine resin; 55 % in butanol). After brief homogenisation, the lacquer is applled by conventional methods, such as spraying and immersing, or in the coil coating method specially for the continuous coating of metal sheets, and stoves ~stoving for 30 minutes at 130C). The orange finishes are distinguished by very good levelness, high gloss and excellent fine distribution of the pigment as well as by excellent weather fastness properties.
Example 14 4 g of the pigment obtained according to Example 1, 35 g of a 60 % solution of an alkyd resin, modified with urea/formaldehyde, in xylene/butanol 1:1, 10 g of oil of terpentine and 5 g of xylene, are ground for 48 ~ours in a ball mill. After spraying the resultant coloured lacquer onto an aluminium sheet and stoving at 120C, an orange finish of very good fastness to light, heat and overstripe bleeding is obtained D
1~5~1 Example 15 80 g of an unsaturated liquid polyester resin, 19.72 g of monostyrene and 0.28 g of a cobalt siccative which contains 16 ~ of cobalt, are ground for 48 hours-in a ball mill with 1 g of the pigment obtained according to Example 1 and 5 g of titanium dioxide ~rutile).
Shortly before the application of this lacquer, a mixture consisting of 4.15 g of cumene hydroperoxide (70 %), 2.42 g of ethyl acetate and 13.33 g butyl acetate is added. Card-board is coated with this mixture and dried in the air to give an orange coating of very good fastness to light, heat and overstripe bleeding.
Example 16 67 g of polyvinyl chloride powder (suspension polymer), 33 g of dioctyl phthalate, 2 g of dibutyl tin dilaurate, 0.3 g of a stabiliser on phosphate basis and 0.7 g of the pigment prepared according to Example 1, are mixed and processed for 15 minutes at 160C on a roll mill. Subsequently a sheet having a thickness of 0.4 mm is prepared on the calender. It is coloured ln a bright orange shade which is heat-reslstant and fast to migra-tlon.
.,;
i',
Claims
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for pigmenting organic material of high molecular weight which comprises incorporating into said material a disazo compound of the formula wherein X represents a chlorine atom, methyl or a tri-fluoromethyl group and R represents an alkyl group of 1 to 3 carbon atoms, in a finely dispersed form.
2. A process according to claim 1 which comprises the incorporation of the compound of the formula 3. A process according to claim 1 which comprises the incorporation of the compound of the formula 4. A process according to claim 1 which comprises the incorporation of the compound of the formula .
5. A process according to claim 1 which comprises the incorporation of the compound of the formula .
6. A process according to claim 1 wherein the organic material of high molecular weight is a plastlc.
7. A process according to claim 1 wherein the organic material of high molecular weight is a lacquer.
8. A process according to claim 1 wherein the organic material of high molecular weight is a printing ink.
9. An organic material of high molecular weight which contains a disazo pigment of the formula given in
claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH11136/76 | 1976-09-02 | ||
| CH1113676A CH623069A5 (en) | 1976-09-02 | 1976-09-02 | Process for pigmenting high molecular-weight organic material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1115881A true CA1115881A (en) | 1982-01-05 |
Family
ID=4370431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA285,900A Expired CA1115881A (en) | 1976-09-02 | 1977-08-31 | Process for pigmenting organic material of high molecular weight |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5331748A (en) |
| CA (1) | CA1115881A (en) |
| CH (1) | CH623069A5 (en) |
| DE (1) | DE2739041A1 (en) |
| FR (1) | FR2363597A1 (en) |
| GB (1) | GB1552514A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS562213A (en) * | 1979-06-15 | 1981-01-10 | Nippon Denso Co Ltd | Car air conditioner |
| CH654018A5 (en) * | 1982-05-29 | 1986-01-31 | Sandoz Ag | Disazo PIGMENT DYE. |
| US4952617A (en) * | 1987-11-06 | 1990-08-28 | Columbian Chemicals Company | Dispersion of pigments in resins and coatings systems |
| US5266110A (en) * | 1991-11-01 | 1993-11-30 | Hoechst Aktiengesellschaft | Crystal modification of C.I. Pigment Yellow 16 |
| EP2038339A2 (en) * | 2006-07-10 | 2009-03-25 | Ciba Holding Inc. | Method of protecting organic material from light |
-
1976
- 1976-09-02 CH CH1113676A patent/CH623069A5/en not_active IP Right Cessation
-
1977
- 1977-08-30 DE DE19772739041 patent/DE2739041A1/en not_active Withdrawn
- 1977-08-31 CA CA285,900A patent/CA1115881A/en not_active Expired
- 1977-09-01 GB GB3649877A patent/GB1552514A/en not_active Expired
- 1977-09-01 FR FR7726531A patent/FR2363597A1/en active Granted
- 1977-09-02 JP JP10575477A patent/JPS5331748A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1552514A (en) | 1979-09-12 |
| FR2363597B1 (en) | 1980-08-22 |
| JPS5331748A (en) | 1978-03-25 |
| DE2739041A1 (en) | 1978-03-09 |
| CH623069A5 (en) | 1981-05-15 |
| FR2363597A1 (en) | 1978-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |