CA1061334A - Preparation of azo pigments - Google Patents
Preparation of azo pigmentsInfo
- Publication number
- CA1061334A CA1061334A CA258,624A CA258624A CA1061334A CA 1061334 A CA1061334 A CA 1061334A CA 258624 A CA258624 A CA 258624A CA 1061334 A CA1061334 A CA 1061334A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- coupling
- coupling component
- benzene
- acetoacet
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
- C09B41/007—Special methods of performing the coupling reaction characterised by process features including condition or time responsive control, e.g. automatically controlled processes; Stepwise coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
Abstract of the Disclosure Azo pigment coupling process in which the amount of excess diazo or coupling component is continuously monitored and addition of diazo component or coupling component to the reaction is automatically controlled by means of an automatic chemical analyser which incorporates a dialyser module.
Description
106~334 The present invention relates to the preparation of azo pigments and more particularly to a me~hod for the automatic control of azo coupling processes in the manufacture of azo pigments.
In the well-k~own azo eoupling process a diazonium salt is reacted with a suitable coupling component to give an azo compound as illustrated by the following e~uation:
R1 N~- NCl- R H ~ R1- N=N ~2 ~ HCl (diazonium salt~ (eoupling component) (azo compound) ~
~ .
wherein Rl and R are suitable radicals.
; The reaction i9 normally carried out in aqueous eonditions and proceeds almost quantltatively. It i9 important that the two components come together i~ the ~orreet ratio otherwise quality of the final product suffers.
If too mueh diazonium salt is added the excess which is usua~ fairly unstable can give rise to decomposition products which usually cause dirtiness of shade. If too much of the coupling component is added this is either washed down the drain during the final filtration and so is wasted, or it ls le~t in the produet where it can cause eolouristie wealuless or other property defects.
~ he COUpliIlg reaction in azo pigment manufacture is carried out in three main ways.
e dlazonium salt, as an aqueous solution or suspension, is run into a solution or suspension of the coupling ' . ., ~ - 2 ~
: , .... , ~ : , - . ,~
1C9~1334 component. l~e pH is controlled within ; oertain limits, specific ror each pi~llent, either by having a buffering agent present or by continuously measuring the pH with a pH meter and adding acid or alkali to maintain the pH within the prescribed limitsO
In the well-k~own azo eoupling process a diazonium salt is reacted with a suitable coupling component to give an azo compound as illustrated by the following e~uation:
R1 N~- NCl- R H ~ R1- N=N ~2 ~ HCl (diazonium salt~ (eoupling component) (azo compound) ~
~ .
wherein Rl and R are suitable radicals.
; The reaction i9 normally carried out in aqueous eonditions and proceeds almost quantltatively. It i9 important that the two components come together i~ the ~orreet ratio otherwise quality of the final product suffers.
If too mueh diazonium salt is added the excess which is usua~ fairly unstable can give rise to decomposition products which usually cause dirtiness of shade. If too much of the coupling component is added this is either washed down the drain during the final filtration and so is wasted, or it ls le~t in the produet where it can cause eolouristie wealuless or other property defects.
~ he COUpliIlg reaction in azo pigment manufacture is carried out in three main ways.
e dlazonium salt, as an aqueous solution or suspension, is run into a solution or suspension of the coupling ' . ., ~ - 2 ~
: , .... , ~ : , - . ,~
1C9~1334 component. l~e pH is controlled within ; oertain limits, specific ror each pi~llent, either by having a buffering agent present or by continuously measuring the pH with a pH meter and adding acid or alkali to maintain the pH within the prescribed limitsO
(2) The coupling component solution is run into a solution or suspension of the diazonium sal~. The pH
in this case i9 normally controlled by a buf~ering agent added to the diazonium salt.
.
~) 'rhe dia~o solution or suspension and coupling ~ component solu-tion are added together to the reaction vessel controlling the rates normally so that the two I components are always present together in the correct ,~ ratio to give complete reaction. The pH i9 monitored with a p~ meter and contro1led by the addition of acid or alkali as required.
Control of the cou~ling process is normally carried out manually uslng chemical spot tcsts to chack on the progress of the reaction. The operator carries out these tests at regular intervals during the reaction and manually ~ ~ .
!~ adjusts the valves controlling the additions of ~he reagents ;~~, to give the required conditions. ~iuch depends on the operator~s skill and application as to how well this is carried ou~ and it is inevitable that variations occur.
, ~ 3 -~ . .
~:P6~334 -Operating und~r batchwisc conditions these variations can usually be accommodated by modifying the process *rom batch to batch to compensate f'or them.
Working on a continuous basis this becomes impossible and ~t is necessary to maintain reaction conditions constant in order to obtain consistent quality in the product.
~he automatic controi Or azo coupling has been described in ' a) Chimia 15 - 1961 - January, pages 1~6 to 163 :in which excess o~ diazo component i9 detected b~ a potentio-mctric method using a quinhydrone electrode.
b) British Patent Specification 192~6,720 which clescrlbe~s the use oP a polarographic method for the control of azo coupling reactions again by the detection of excess of the diazo component.
The presence of excess diazo component during an azo coupling process is often undesirable since the cleanliness o~ shade of the product can be affected~
We have de~ised a system which gives a continuous quantitative indication of co~ditions in the reaction vessel by using an automatic chemical analyser incorporating a dialyser module to continuously monitor the amount of excess of the diazo or coupling co~.ponent in the reaction. This system has the advantage of avoiding the presence of excess diazo component in the coup-ing process in those cases when this would be detrimental to the product.
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In certai.~ couplings, however, notably i.n cases when the solubility of the coupling component is ve~y low, an excess of diaz,o component is present throughout coupling and in these cases the reaction can be monitored by continuously determining the concentration of diazo component present.
If,an excess of diazo component persists the analyser will show positively whether or not the reaction has stopped and whether or not it is necessary to add further coupling component to complete the reaction. : ' -.. . . . . _. . . .
According to the present in~ention there is pro~ided ' an,azo pigment coupling process in which the a~ount of excess diazo or coupling component is continuousl~ monitored and the ad~lition of diazo compon~nt or coup].in~ component to the reaction is ~utomatically controlled by means of an automatic chemical analyser incorporating a dialyser module.
The diazonium salt used in the coupling process may be prepared from any diazotisable amine which on coupling ~ith a suitable coupling component results in a water-inso'luble azo pigment. Such diazotisable amines are for example primary aromatic monoamines or diamines derived from benzen~, or from biph~nyl, or from condensed benzenoid structures such as naphthalene or anthracene, or ~rom structures in which benæene i9 condensed with a heterocyclic ring such as quinoline.
The carbocycl'ic or heterocyclic aromatic nucleus of these amines can be unsubstituted, or substituted with one Qr more of the follQwing grQups: .al~yl9 alkoxy, halo~no, ni-tro, cyano) acylamino9 . .
~3L334 sulphonamido, carboxy-alkyl, and carboxylic acid. Suitable amines may be mono-ni~roanilines, dinitroanilines, nitrotoluidines, nitroanisidines, mono-chloranilines, dichloranilines, trichloranilines, chlorotoluldines, chloranlsi-dines, chloronitroanilinesJ benzldine, dichlorbenzidines9 tetrachlorbenzidines, ; tolidines, dianisidines and dichlordianisidines, for example, N-phenyl-3-amino-phthalimide,5-amino-6-methyl-benzimidazolone, 6-methyl-7-amino-phenomorpholone
in this case i9 normally controlled by a buf~ering agent added to the diazonium salt.
.
~) 'rhe dia~o solution or suspension and coupling ~ component solu-tion are added together to the reaction vessel controlling the rates normally so that the two I components are always present together in the correct ,~ ratio to give complete reaction. The pH i9 monitored with a p~ meter and contro1led by the addition of acid or alkali as required.
Control of the cou~ling process is normally carried out manually uslng chemical spot tcsts to chack on the progress of the reaction. The operator carries out these tests at regular intervals during the reaction and manually ~ ~ .
!~ adjusts the valves controlling the additions of ~he reagents ;~~, to give the required conditions. ~iuch depends on the operator~s skill and application as to how well this is carried ou~ and it is inevitable that variations occur.
, ~ 3 -~ . .
~:P6~334 -Operating und~r batchwisc conditions these variations can usually be accommodated by modifying the process *rom batch to batch to compensate f'or them.
Working on a continuous basis this becomes impossible and ~t is necessary to maintain reaction conditions constant in order to obtain consistent quality in the product.
~he automatic controi Or azo coupling has been described in ' a) Chimia 15 - 1961 - January, pages 1~6 to 163 :in which excess o~ diazo component i9 detected b~ a potentio-mctric method using a quinhydrone electrode.
b) British Patent Specification 192~6,720 which clescrlbe~s the use oP a polarographic method for the control of azo coupling reactions again by the detection of excess of the diazo component.
The presence of excess diazo component during an azo coupling process is often undesirable since the cleanliness o~ shade of the product can be affected~
We have de~ised a system which gives a continuous quantitative indication of co~ditions in the reaction vessel by using an automatic chemical analyser incorporating a dialyser module to continuously monitor the amount of excess of the diazo or coupling co~.ponent in the reaction. This system has the advantage of avoiding the presence of excess diazo component in the coup-ing process in those cases when this would be detrimental to the product.
.
~ .
, ,.
.. . . .
f~
.
In certai.~ couplings, however, notably i.n cases when the solubility of the coupling component is ve~y low, an excess of diaz,o component is present throughout coupling and in these cases the reaction can be monitored by continuously determining the concentration of diazo component present.
If,an excess of diazo component persists the analyser will show positively whether or not the reaction has stopped and whether or not it is necessary to add further coupling component to complete the reaction. : ' -.. . . . . _. . . .
According to the present in~ention there is pro~ided ' an,azo pigment coupling process in which the a~ount of excess diazo or coupling component is continuousl~ monitored and the ad~lition of diazo compon~nt or coup].in~ component to the reaction is ~utomatically controlled by means of an automatic chemical analyser incorporating a dialyser module.
The diazonium salt used in the coupling process may be prepared from any diazotisable amine which on coupling ~ith a suitable coupling component results in a water-inso'luble azo pigment. Such diazotisable amines are for example primary aromatic monoamines or diamines derived from benzen~, or from biph~nyl, or from condensed benzenoid structures such as naphthalene or anthracene, or ~rom structures in which benæene i9 condensed with a heterocyclic ring such as quinoline.
The carbocycl'ic or heterocyclic aromatic nucleus of these amines can be unsubstituted, or substituted with one Qr more of the follQwing grQups: .al~yl9 alkoxy, halo~no, ni-tro, cyano) acylamino9 . .
~3L334 sulphonamido, carboxy-alkyl, and carboxylic acid. Suitable amines may be mono-ni~roanilines, dinitroanilines, nitrotoluidines, nitroanisidines, mono-chloranilines, dichloranilines, trichloranilines, chlorotoluldines, chloranlsi-dines, chloronitroanilinesJ benzldine, dichlorbenzidines9 tetrachlorbenzidines, ; tolidines, dianisidines and dichlordianisidines, for example, N-phenyl-3-amino-phthalimide,5-amino-6-methyl-benzimidazolone, 6-methyl-7-amino-phenomorpholone
(3), 4-methyl-6-chloro-7-aminoquinolone, 4~-2'-methoxy-4'-amino-5'-chlorophenyl-j" amino)-quinazoline, 3-aminodibenzofuran.
The coupling component may be any coupling component normally used for the production of azo pigments which is able to dissolve to some extent ; in the coupling medium and which couples wlth a suitable diazonium salt to give a water-insoluble product. Such components are for example acetoacetani-lide and derivatives thereof such as acetoacet-2-toluidide, acetoacet-4-tolu-idide, acetoacet-2-anisidide, acetoacet-2-chloranilide, acetoacet-2:4-dimethyl-anilide, acetoacet-2:5-dimethoxy-4-chloranilide; l-aryl pyrazolones such as l-phenyl-3-methyl-5-pyrazolone, 1-4'-tolyl-3-methyl-5-pyrazolone, and l-phenyl-3-carbethoxy-5-pyrazolone; 2-naphthol; 2-hydroxy-3-naphthoic acid and arylides thereof such as (2',3'-hydr~xy-naphthoylamino)-benzene, 1-(2',3'-hydroxy-naphthoylamino)-2-methyl benzene, 1-(2',3' hydroxynaphthoylamino)-2,4-di-methoxy-5-chloro-benzene, and 1-(2',3' hydroxynaphthoylamino)-2-methyl-5-chloro-benzene, 4-hydroxycoumarin, barbituric acid, 2,4-dihydroxyquinoline, ~, 4-hydroxy-N-methyl-quinolone, 4-methyl-7-acetoacetamido-quinolone, 7-aceto-acetamido-phenomorpholone (3), 5-acetoacetamido-benzimidazolone.
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An example of a suitable automatlc chemical analyser is the Technicon AutoAnalyser (Auto~;nalyser is a Registered l`rademark).
The AutoAnalyser is a train of interconnected modules that automate the step-by-step procedures of manual analysis~
In AutoAnalysis, chemical reactions take place in continuously flowing air-segmented streams. The ~Low of streams is directed through tubing from module to module,each of ~ich automatically carries out a different analytical function such as sampling of un~nowns and standards; metering of reagents; purlfication and filtration; heating and incubation and detection and recording.
~ he process of the present invention is f'urther descrihed by way of Example wlth re~erence to and ~s illus-trated by Figure 1 of the drawlngs accompanying the provisional specif`ication which is a schematic flow sketch.
A proportionating pump 10 continuously samples the pigment slurry through channel 11 from the reaction vessel.
Air in channel 12 is pumped in and this segments the pigment alurry in channel 11 which theD passes through a dialyser 13 on one side of the dialyser membrane 14 before returning ~ia tiube 18 to the reaction vessel. ~t the same time the pump 10 circulates a buffer solution through channel 15 segmented wlth air in channel t6 to the other side of the dialyser membran~ 14. If an excess of diazo or co~pling component is present it diffuses through the dialyser membrane 14 from the sample stream into the buffer solution stream ln direct proportion to its concent~ation in the sample stream. Thu~
~6~334 as the amount of e.YCess dia~o or coupling component in the reaction vessel varies during the reaction so the amount diffusing into the buffer solution varies dlrectly. A
suitable colorimetrlc reagent metered by the `, proportionating pump 10 in a channel 19 mixes with the buffer solution carrying the diazo or coupling component e~erging from the dialyser 13 in channel 15 in a ~ixing coil 20 to form a c~loured solution, usually a water-soluble azo dyestuff.
The coloured solution passes to the colorimeter 21 where the air bubbles are removed through -tube 22 to providc a continuous strea~ which pasces into the flow-through colorimeter cell 23 in which the strength of the coloured solution is contilluously measured and this is continuousl~ recorded on a chart recorder Z4.The coloured solution leaves the colorimeter by an effluent pipe 25 which i5 connected to the proportionating pump 10 to ensure efficient flow through.
The output signal from the colorimeter is then used to , control the addition of one or other of the components to the 3 reaction v~ssel by continuously regulating the valves through which the components are added to the reaction vessel.
The foilowing Examples further illustrate the present invention.
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EX~L~ 1 -In the preparation of Colour Index Pigment Yellow 1~
in which a solution of tetrazot;ised 3.3'-dichlorbenzid:ine is added to a suspension o~ aeetoacetanilide in a stirred eoupling vessel-at a pH controlled between 4.0 and 6.5 the an~ount of aeetoacetanilicle present in the çouplill~ bath is 'eontinuously monitored by pumping a sample stream from the reaetor tllrough channel 1l cn the AutoAnalyser to tlle dialyser 13. A disodium phosphate bu~fer solution is pumped through channel 15 which picks up acetoacetanilide ~di~fusing through the dialyser membrane 14. I~le buffer ~olution eontaining aeetoaeetanilide is mixed in coil Z0 wlth a solutiorl of tetrazot~sed benzidine-2.2~~disulphonie aeid addecl through ehannel l9. The yellow dre~tuf~
solution formed passes to the eolorimeter 21 where the e~ncentration is measured at a wavelength of 410 ~ and recorded on the recorder 24. An output sig~lal f`rom t71e reeorder ean be used to regulate the supply of tetrazo solution to the reaction.
When the eoneentration o~ ace-toaeetanilide present clrops below a pre-set value on the reeorder the valve through which the tetrazo solution being added is autolllati~
eally elosed and the presence of excess tetrazo in the reaction is avoided.
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~06~33~
EX~IPI,E 2 In the preparation of Colour Index Pigment Yellvw 13 a solution of tetrazotised 3.3~-dichlorben~idine and a solution of acetoacet-2:4-xylidide as its socliurn salt are added simult--ane,ously to a cou~ g;.vessel at a pH eontrolled throughout at 4.2-4~5. In order to ensure that a constant srnall excess of aeetoacet-2:4-~.ylidide is prescnt t:hroughout coupli.ng a sample stream from t.he coupling vessel is passed through ~he AutoAnalyser and the ace-toacet-2:4-xylidide which passesthroalgh the dialysis membrane is picked up in a disodi~n phosphate solu-tion and is reacted with tetrazotised benzi.cl:Lne-2.2'-Ai-sulphonic acicl to give a water-soluble yellow clyestuf~ ~lich i~ measuring on the colorimeter at 410 nm. ~n output sigrlal from the recorder can be usecl to automatically regulate either the valve through which the tetrazo solution is being added or the valve through which the acetoacet~2:4-xylidide solution is being added so that the e~cess of the coupling component is maintained at a fixed value throughout the couplirlg and the pxesence o.f excess tetrazo cornpound is avoided.
, ~_ ' ' . -- .
In the prepa.ration of a recl a~.o pigment lntermediate :.
a solution of diazotised 2:~-di.chloroaniline and a solution :-of Z-hydroxy-3-naphthoic acid as its sodium salt are addecl simultaneously to a coupling vessel maintaining the pH at 8.0 throughout.A sampl~ stream from the reaetion i.s passed through the AaltoAnalyser and the 2 h.ydroxy-3-naphthoic acid which passes .
" ~L06133~L
throug~ the dialysis membrane is picked up in a water streant and reacted with acidic ferric chloride solution to gi.ve a blue coloration measured at 570 nm on the colorimeter.
An output from the recorder is u.sed to regulate the rate of addition of 2-hydroxy-3-naphthoi.c acid to the reactio~ and so the excess present throughout can be automatically controlled at a fi~ed value.
EXAMPLES 4 to 42 Preparation of the water-insoluble azo pignlents listed in Table 1 can be carried out by controlling the excess of diaYio component or coupling component in the reaction medium of the coupling process as required using the AutoAnalyser in a similar marmer to that described in the preceding Examples I to 3.
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The coupling component may be any coupling component normally used for the production of azo pigments which is able to dissolve to some extent ; in the coupling medium and which couples wlth a suitable diazonium salt to give a water-insoluble product. Such components are for example acetoacetani-lide and derivatives thereof such as acetoacet-2-toluidide, acetoacet-4-tolu-idide, acetoacet-2-anisidide, acetoacet-2-chloranilide, acetoacet-2:4-dimethyl-anilide, acetoacet-2:5-dimethoxy-4-chloranilide; l-aryl pyrazolones such as l-phenyl-3-methyl-5-pyrazolone, 1-4'-tolyl-3-methyl-5-pyrazolone, and l-phenyl-3-carbethoxy-5-pyrazolone; 2-naphthol; 2-hydroxy-3-naphthoic acid and arylides thereof such as (2',3'-hydr~xy-naphthoylamino)-benzene, 1-(2',3'-hydroxy-naphthoylamino)-2-methyl benzene, 1-(2',3' hydroxynaphthoylamino)-2,4-di-methoxy-5-chloro-benzene, and 1-(2',3' hydroxynaphthoylamino)-2-methyl-5-chloro-benzene, 4-hydroxycoumarin, barbituric acid, 2,4-dihydroxyquinoline, ~, 4-hydroxy-N-methyl-quinolone, 4-methyl-7-acetoacetamido-quinolone, 7-aceto-acetamido-phenomorpholone (3), 5-acetoacetamido-benzimidazolone.
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An example of a suitable automatlc chemical analyser is the Technicon AutoAnalyser (Auto~;nalyser is a Registered l`rademark).
The AutoAnalyser is a train of interconnected modules that automate the step-by-step procedures of manual analysis~
In AutoAnalysis, chemical reactions take place in continuously flowing air-segmented streams. The ~Low of streams is directed through tubing from module to module,each of ~ich automatically carries out a different analytical function such as sampling of un~nowns and standards; metering of reagents; purlfication and filtration; heating and incubation and detection and recording.
~ he process of the present invention is f'urther descrihed by way of Example wlth re~erence to and ~s illus-trated by Figure 1 of the drawlngs accompanying the provisional specif`ication which is a schematic flow sketch.
A proportionating pump 10 continuously samples the pigment slurry through channel 11 from the reaction vessel.
Air in channel 12 is pumped in and this segments the pigment alurry in channel 11 which theD passes through a dialyser 13 on one side of the dialyser membrane 14 before returning ~ia tiube 18 to the reaction vessel. ~t the same time the pump 10 circulates a buffer solution through channel 15 segmented wlth air in channel t6 to the other side of the dialyser membran~ 14. If an excess of diazo or co~pling component is present it diffuses through the dialyser membrane 14 from the sample stream into the buffer solution stream ln direct proportion to its concent~ation in the sample stream. Thu~
~6~334 as the amount of e.YCess dia~o or coupling component in the reaction vessel varies during the reaction so the amount diffusing into the buffer solution varies dlrectly. A
suitable colorimetrlc reagent metered by the `, proportionating pump 10 in a channel 19 mixes with the buffer solution carrying the diazo or coupling component e~erging from the dialyser 13 in channel 15 in a ~ixing coil 20 to form a c~loured solution, usually a water-soluble azo dyestuff.
The coloured solution passes to the colorimeter 21 where the air bubbles are removed through -tube 22 to providc a continuous strea~ which pasces into the flow-through colorimeter cell 23 in which the strength of the coloured solution is contilluously measured and this is continuousl~ recorded on a chart recorder Z4.The coloured solution leaves the colorimeter by an effluent pipe 25 which i5 connected to the proportionating pump 10 to ensure efficient flow through.
The output signal from the colorimeter is then used to , control the addition of one or other of the components to the 3 reaction v~ssel by continuously regulating the valves through which the components are added to the reaction vessel.
The foilowing Examples further illustrate the present invention.
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EX~L~ 1 -In the preparation of Colour Index Pigment Yellow 1~
in which a solution of tetrazot;ised 3.3'-dichlorbenzid:ine is added to a suspension o~ aeetoacetanilide in a stirred eoupling vessel-at a pH controlled between 4.0 and 6.5 the an~ount of aeetoacetanilicle present in the çouplill~ bath is 'eontinuously monitored by pumping a sample stream from the reaetor tllrough channel 1l cn the AutoAnalyser to tlle dialyser 13. A disodium phosphate bu~fer solution is pumped through channel 15 which picks up acetoacetanilide ~di~fusing through the dialyser membrane 14. I~le buffer ~olution eontaining aeetoaeetanilide is mixed in coil Z0 wlth a solutiorl of tetrazot~sed benzidine-2.2~~disulphonie aeid addecl through ehannel l9. The yellow dre~tuf~
solution formed passes to the eolorimeter 21 where the e~ncentration is measured at a wavelength of 410 ~ and recorded on the recorder 24. An output sig~lal f`rom t71e reeorder ean be used to regulate the supply of tetrazo solution to the reaction.
When the eoneentration o~ ace-toaeetanilide present clrops below a pre-set value on the reeorder the valve through which the tetrazo solution being added is autolllati~
eally elosed and the presence of excess tetrazo in the reaction is avoided.
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~06~33~
EX~IPI,E 2 In the preparation of Colour Index Pigment Yellvw 13 a solution of tetrazotised 3.3~-dichlorben~idine and a solution of acetoacet-2:4-xylidide as its socliurn salt are added simult--ane,ously to a cou~ g;.vessel at a pH eontrolled throughout at 4.2-4~5. In order to ensure that a constant srnall excess of aeetoacet-2:4-~.ylidide is prescnt t:hroughout coupli.ng a sample stream from t.he coupling vessel is passed through ~he AutoAnalyser and the ace-toacet-2:4-xylidide which passesthroalgh the dialysis membrane is picked up in a disodi~n phosphate solu-tion and is reacted with tetrazotised benzi.cl:Lne-2.2'-Ai-sulphonic acicl to give a water-soluble yellow clyestuf~ ~lich i~ measuring on the colorimeter at 410 nm. ~n output sigrlal from the recorder can be usecl to automatically regulate either the valve through which the tetrazo solution is being added or the valve through which the acetoacet~2:4-xylidide solution is being added so that the e~cess of the coupling component is maintained at a fixed value throughout the couplirlg and the pxesence o.f excess tetrazo cornpound is avoided.
, ~_ ' ' . -- .
In the prepa.ration of a recl a~.o pigment lntermediate :.
a solution of diazotised 2:~-di.chloroaniline and a solution :-of Z-hydroxy-3-naphthoic acid as its sodium salt are addecl simultaneously to a coupling vessel maintaining the pH at 8.0 throughout.A sampl~ stream from the reaetion i.s passed through the AaltoAnalyser and the 2 h.ydroxy-3-naphthoic acid which passes .
" ~L06133~L
throug~ the dialysis membrane is picked up in a water streant and reacted with acidic ferric chloride solution to gi.ve a blue coloration measured at 570 nm on the colorimeter.
An output from the recorder is u.sed to regulate the rate of addition of 2-hydroxy-3-naphthoi.c acid to the reactio~ and so the excess present throughout can be automatically controlled at a fi~ed value.
EXAMPLES 4 to 42 Preparation of the water-insoluble azo pignlents listed in Table 1 can be carried out by controlling the excess of diaYio component or coupling component in the reaction medium of the coupling process as required using the AutoAnalyser in a similar marmer to that described in the preceding Examples I to 3.
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.
Claims (9)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An azo pigment coupling process in which the amount of excess diazo or coupling component is continuously monitored and the addition of diazo component or coupling component to the reaction is automatically controlled by means of an automatic chemical analyser which incorporates a dialyser module.
2. An azo pigment coupling process as claimed in claim 1 in which the diazonium salt used in the coupling process is prepared from any diazotisable amine which on coupling with a suitable coupling component results in a water-insoluble azo pigment.
3. A process as claimed in claim 2 in which the diazotisable amine is a primary aromatic monoamine or diamine derived from benzene, or from biphenyl, or from a condensed benzenoid structure, or from a structure in which benzene is condensed with a heterocyclic ring.
4. A process as claimed in claim 3 in which the carbocyclic or hetero-cyclic nucleus of the diazotisable amine is unsubstituted, or substituted with one or more of the following groups: alkyl, alkoxy, halogeno, nitro, cyano, acylamino, sulphonamido, carboxy-alkyl, and carboxylic acid.
5. A process as claimed in claim 3 or claim 4 in which the diazotisable amine is a mono-nitroaniline, dinitroaniline, nitrotoluidine, nitroanisidine, mono-chloraniline, dichloraniline, trichloraniline, chlorotoluidine, chloro-anisidine, chloronitroaniline, benzidine, dichlorbenzidine, tetrachlorbenzi-dine, tolidine, dianisidine or dichlordianisidine.
6. A process as claimed in any of claims 1, 2 or 3 in which the coupling component may be any coupling component normally used for the production of azo pigments, which is able to dissolve to some extent in the coupling medium and which couples with a suitable diazonium salt to give a water insoluble product.
7. A process as claimed in claim 2 in which the coupling component is acetoacetanilide, acetoacet-2-toluidide, acetoacet-4-toluidide, acetoacet-2-anisidide, acetoacet-2-chloranilide, acetoacet-2:4-dimethylanilide, aceto-acet-2:5-dimethoxy-4-chloranilide, 1-phenyl-3-methyl-5-pyrazolone, 1-4'-tolyl-3-methyl-5-pyrazolone, 1-phenyl-3-carbethoxy-5-pyrazolone, 2-naphthol;
2-hydroxy-3-naphthoic acid, (2',3'-hydroxy-naphthoylamino)-benzene, 1-(2',3' hydroxy-naphthoylamino)-2-methyl-benzene, 1-(2',3'-hydroxynaphthoylamino)-2, 4-dimethoxy-5-chloro-benzene or 1-(2',3'-hydroxynaphthoylamino)-2-methyl-5-chloro-benzene.
2-hydroxy-3-naphthoic acid, (2',3'-hydroxy-naphthoylamino)-benzene, 1-(2',3' hydroxy-naphthoylamino)-2-methyl-benzene, 1-(2',3'-hydroxynaphthoylamino)-2, 4-dimethoxy-5-chloro-benzene or 1-(2',3'-hydroxynaphthoylamino)-2-methyl-5-chloro-benzene.
8. A process as claimed in claim 2 in which the coupling component is 4-hydroxycoumarin, barbituric acid, 2,4-dihydroxyquinoline, 4-hydroxy-N-methyl-quinolone, 4-methyl-7-acetoacetamido-quiolone, 7-acetoacetamido-phenomorpho-lone (3), or 5-acetoacetamido-benzimidazolone.
9. A process as claimed in any of claims 2, 7 or 8 in which the diazo-tisable amine is N-phenyl-3-amino-phthalimide,5-amino-6-methyl-benzimidazo-lone, 6-methyl-7-amino-phenomorpholone (3), 4-methyl-6-chloro-7-aminoquinolone, 4(-2'-methoxy-4'-amino-5'-chlorophenyl-amino)-quinazoline or 3-aminodibenzo-furan.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3328475A GB1547759A (en) | 1975-08-09 | 1975-08-09 | Automatic control of azo-coupling in the preparation of pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061334A true CA1061334A (en) | 1979-08-28 |
Family
ID=10350930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA258,624A Expired CA1061334A (en) | 1975-08-09 | 1976-08-06 | Preparation of azo pigments |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5943499B2 (en) |
| CA (1) | CA1061334A (en) |
| CH (1) | CH618456A5 (en) |
| DE (1) | DE2635536C2 (en) |
| FR (1) | FR2320970A1 (en) |
| GB (1) | GB1547759A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1570292A (en) * | 1976-10-28 | 1980-06-25 | Ciba Geigy Ag | Automatic control of azo pigments |
| DE2844634A1 (en) * | 1978-10-13 | 1980-04-24 | Hoechst Ag | METHOD FOR THE CONTINUOUS PRODUCTION OF AZOPIGMENTS |
| US4341701A (en) * | 1979-11-07 | 1982-07-27 | Ciba-Geigy Corporation | Production of pigments |
| GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
| JPH0723961B2 (en) * | 1984-06-29 | 1995-03-15 | キヤノン株式会社 | Charge generation material and manufacturing method thereof |
| JPS6175359A (en) * | 1984-09-21 | 1986-04-17 | Canon Inc | Production of azo pigment and electrophotographic sensitive body using said azo pigment |
| DE3669881D1 (en) * | 1985-08-22 | 1990-05-03 | Ciba Geigy Ag | METHOD FOR DETERMINING THE DIAZONIUM ION CONCENTRATION. |
| IN172052B (en) * | 1987-12-01 | 1993-03-27 | Hoechst Ag | |
| WO1997031067A1 (en) * | 1996-02-26 | 1997-08-28 | Toyo Ink Manufacturing Co., Ltd. | Process for the preparation of disazo pigments and disazo pigments prepared by the process |
| JP2006028341A (en) * | 2004-07-16 | 2006-02-02 | Toyo Ink Mfg Co Ltd | Method for producing disazo pigment and disazo pigment |
| GB0416256D0 (en) | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797149A (en) * | 1953-01-08 | 1957-06-25 | Technicon International Ltd | Methods of and apparatus for analyzing liquids containing crystalloid and non-crystalloid constituents |
| DE1934388B2 (en) * | 1969-07-07 | 1975-01-16 | Vyzkumny Ustav Organickych Syntez, Pardubice-Rybitvi (Tschechoslowakei) | Process for the repeated batch production of azo dyes |
-
1975
- 1975-08-09 GB GB3328475A patent/GB1547759A/en not_active Expired
-
1976
- 1976-08-06 CA CA258,624A patent/CA1061334A/en not_active Expired
- 1976-08-06 CH CH1007576A patent/CH618456A5/en not_active IP Right Cessation
- 1976-08-06 DE DE19762635536 patent/DE2635536C2/en not_active Expired
- 1976-08-06 FR FR7624068A patent/FR2320970A1/en active Granted
- 1976-08-09 JP JP9474376A patent/JPS5943499B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1547759A (en) | 1979-06-27 |
| JPS5943499B2 (en) | 1984-10-22 |
| CH618456A5 (en) | 1980-07-31 |
| JPS5227433A (en) | 1977-03-01 |
| DE2635536A1 (en) | 1977-02-17 |
| FR2320970B1 (en) | 1979-06-22 |
| DE2635536C2 (en) | 1985-12-19 |
| FR2320970A1 (en) | 1977-03-11 |
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